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$1,950,000

Set on a private flag lot with approximately 250 feet of bulkhead along the Great South Bay, this extraordinary Bayport residence offers a rare combination of privacy, sophistication, and resort-style living. Panoramic water views stretch across the bay to the silhouettes of Fire Island, providing a breathtaking backdrop for both sunrises and sunsets.The waterfront grounds are designed for ultimate relaxation and entertaining, featuring an in-ground pool on the bay side, expansive patios, and generous decking that transitions to a private sandy beach. A summer "kitchen" on the lower level allows seamless indoor-outdoor living. Completely reimagined through a full interior renovation, the home blends contemporary design with coastal elegance. The state-of-the-art kitchen is appointed with Viking appliances, a wet bar, and custom cabinetry that flows into open, light-filled living spaces showcasing the home’s incredible views. Each bedroom is en suite, offering private baths for comfort and luxury, while a separate guest suite provides an inviting retreat for visitors. The primary suite is a sanctuary unto itself, featuring dual walk-in closets, a spa-inspired bath, and a spiral staircase leading to a private sitting room—perfect for quiet moments above the bay. Every detail, from the refined finishes to the architectural flow, has been executed with thoughtful precision and timeless style. This exceptional property embodies waterfront living at its finest—where every window frames the beauty of the bay, and every day feels like a getaway.

5 Beds ⋅ 7 Baths ⋅ 930696 MLS

Set on a private flag lot with approximately 250 feet of bulkhead along the Great South Bay, this extraordinary Bayport residence offers a rare combination of privacy, sophistication, and resort-style living. Panoramic water views stretch across the bay to the silhouettes of Fire Island, providing a breathtaking backdrop for both sunrises and sunsets.The waterfront grounds are designed for ultimate relaxation and entertaining, featuring an in-ground pool on the bay side, expansive patios, and generous decking that transitions to a private sandy beach. A summer "kitchen" on the lower level allows seamless indoor-outdoor living. Completely reimagined through a full interior renovation, the home blends contemporary design with coastal elegance. The state-of-the-art kitchen is appointed with Viking appliances, a wet bar, and custom cabinetry that flows into open, light-filled living spaces showcasing the home’s incredible views. Each bedroom is en suite, offering private baths for comfort and luxury, while a separate guest suite provides an inviting retreat for visitors. The primary suite is a sanctuary unto itself, featuring dual walk-in closets, a spa-inspired bath, and a spiral staircase leading to a private sitting room—perfect for quiet moments above the bay. Every detail, from the refined finishes to the architectural flow, has been executed with thoughtful precision and timeless style. This exceptional property embodies waterfront living at its finest—where every window frames the beauty of the bay, and every day feels like a getaway.

270 Edgewater Avenue, Bayport

$1,820,000

Behind stately wrought-iron gates, this distinguished Tudor-style estate unfolds like a private compound, blending timeless architecture,modern luxuries, and resort-style amenities in one extraordinary offering. The brick facade with half timber accents and diamond -pane windows sets the stage for elegance within, where a dramatic two story foyer with sweeping staircase and chandelier opens to a formal wood paneled sunken living room and oversized light filled dining area with French doors to private gardens. The octagon library with turret windows creates a dramatic backdrop for reflection. The Gourmet kitchen features stainless steel appliances and a butcher block island with wine storage. Terracotta tile floors are framed by three skylights and garden views. Stately doors open to the formal dining room w custom built ins for holiday dishes. Elegant millwork and oversized French doors invite light and offer a direct connection to garden. Relax in the family room with exposed beams, gas fireplace, parquet floors, three sets of French doors that lead to pool area. The custom crafted wood bar is an inviting space for cocktails. The primary suite is a private sanctuary featuring vaulted ceilings and dual walk in closets. The grand spa bath is complete with a steam and Jacuzzi shower. The three additional bedrooms with ample closet space offer great functionality for every lifestyle. Arrive in style by your boat to your 150 foot dock on Homans Creek, offering access to the Great South Bay and Fire Island. Designed for resort style living the property offers a pool house complete with guest accommodations, sauna, full bath all overlooking a built-in-pool. The brick patio with awning provides effortless al- fresco dining. A separate two-car garage with additional storage completes this rare waterfront retreat. Pool House is designed for entertaining guests and family complete with sauna and full bath for ultimate convenience. Additional two car garage is attached with tremendous storage on second floor. Experience the pinnacle of South Shore luxury ...blending a boater's paradise and timeless design. New roof 2025,Healthy Basement, Filtered Water System, Generac Generator

4 Beds ⋅ 5 Baths ⋅ 912990 MLS

Behind stately wrought-iron gates, this distinguished Tudor-style estate unfolds like a private compound, blending timeless architecture,modern luxuries, and resort-style amenities in one extraordinary offering. The brick facade with half timber accents and diamond -pane windows sets the stage for elegance within, where a dramatic two story foyer with sweeping staircase and chandelier opens to a formal wood paneled sunken living room and oversized light filled dining area with French doors to private gardens. The octagon library with turret windows creates a dramatic backdrop for reflection. The Gourmet kitchen features stainless steel appliances and a butcher block island with wine storage. Terracotta tile floors are framed by three skylights and garden views. Stately doors open to the formal dining room w custom built ins for holiday dishes. Elegant millwork and oversized French doors invite light and offer a direct connection to garden. Relax in the family room with exposed beams, gas fireplace, parquet floors, three sets of French doors that lead to pool area. The custom crafted wood bar is an inviting space for cocktails. The primary suite is a private sanctuary featuring vaulted ceilings and dual walk in closets. The grand spa bath is complete with a steam and Jacuzzi shower. The three additional bedrooms with ample closet space offer great functionality for every lifestyle. Arrive in style by your boat to your 150 foot dock on Homans Creek, offering access to the Great South Bay and Fire Island. Designed for resort style living the property offers a pool house complete with guest accommodations, sauna, full bath all overlooking a built-in-pool. The brick patio with awning provides effortless al- fresco dining. A separate two-car garage with additional storage completes this rare waterfront retreat. Pool House is designed for entertaining guests and family complete with sauna and full bath for ultimate convenience. Additional two car garage is attached with tremendous storage on second floor. Experience the pinnacle of South Shore luxury ...blending a boater's paradise and timeless design. New roof 2025,Healthy Basement, Filtered Water System, Generac Generator

4 Saltmeadow Court, Bayport

$1,600,000

Welcome to a rare slice of waterfront paradise on the Great South Bay, where the beach and the water are your closest neighbors and the views stretch endlessly in every direction. This elevated, contemporary beach-style residence is thoughtfully designed to capture the natural beauty of its surroundings while delivering the finest in coastal luxury. Nestled beside a pristine, untouched stretch of beach to the west, this sun-illuminated home is perfectly positioned with full east-to-west exposure—allowing you to savor both sweet sunrises and breathtaking sunsets. Gaze southward across the shimmering water to the silhouettes of Fire Island, while every room offers sweeping, uninterrupted vistas of the bay. Inside, rich Brazilian cherry hardwood flooring flows throughout, adding warmth and sophistication to the open, airy layout. The chef’s kitchen is a statement in refined craftsmanship with a French country flair, featuring buttercream cabinetry with detailed molding, a double-sized Sub-Zero refrigerator, six-burner Wolf range —designed for entertaining and everyday luxury. The homes primary suite mirrors the tranquility of a yachts stateroom- featuring private balcony access, spa inspired bath, and sweeping views from every angle. Step outside to 200 feet of your own navy-grade bulkheaded waterfront, complete with a sandy "beach", multi-level decking, stone patios, balconies, a cabana, and a built-in fire pit—perfect for long summer evenings by the bay. Tucked away at the end of a quiet, secluded lane, this home offers ultimate privacy and serenity while keeping you connected to the rhythm of the tides. Every detail, from the coastal palette to the fluid layout, is crafted to deliver the sensation of being cradled by the sea- without ever leaving home.

3 Beds ⋅ 3 Baths ⋅ 877938 MLS

Welcome to a rare slice of waterfront paradise on the Great South Bay, where the beach and the water are your closest neighbors and the views stretch endlessly in every direction. This elevated, contemporary beach-style residence is thoughtfully designed to capture the natural beauty of its surroundings while delivering the finest in coastal luxury. Nestled beside a pristine, untouched stretch of beach to the west, this sun-illuminated home is perfectly positioned with full east-to-west exposure—allowing you to savor both sweet sunrises and breathtaking sunsets. Gaze southward across the shimmering water to the silhouettes of Fire Island, while every room offers sweeping, uninterrupted vistas of the bay. Inside, rich Brazilian cherry hardwood flooring flows throughout, adding warmth and sophistication to the open, airy layout. The chef’s kitchen is a statement in refined craftsmanship with a French country flair, featuring buttercream cabinetry with detailed molding, a double-sized Sub-Zero refrigerator, six-burner Wolf range —designed for entertaining and everyday luxury. The homes primary suite mirrors the tranquility of a yachts stateroom- featuring private balcony access, spa inspired bath, and sweeping views from every angle. Step outside to 200 feet of your own navy-grade bulkheaded waterfront, complete with a sandy "beach", multi-level decking, stone patios, balconies, a cabana, and a built-in fire pit—perfect for long summer evenings by the bay. Tucked away at the end of a quiet, secluded lane, this home offers ultimate privacy and serenity while keeping you connected to the rhythm of the tides. Every detail, from the coastal palette to the fluid layout, is crafted to deliver the sensation of being cradled by the sea- without ever leaving home.

42 Browns River Road Unit #3, Bayport

$1,545,000

Stately South Bayport estate with exceptional scale & privacy. Set on a quiet, private lane in the heart of South Bayport, this remarkable 5,000 square-foot residence offers grand living and luxurious amenities in one of the area’s most serene and desirable settings. Beyond the iron gates, this home opens to a dramatic entry foyer with inlaid hardwood flooring and elegant raised panel walls, setting the tone for the craftsmanship and scale found throughout. With six generously sized bedrooms, every corner of this home is designed for comfort and space. The primary suite spans the entire south wing, offering a private lounge area, an expansive walk-in closet, and a beautifully renovated en suite bathroom—creating a true retreat within the home. Entertain with ease in the richly appointed billiard room, full home bar, and sophisticated lounge area—ideal for elevated evenings with guests. A colossal, open-concept kitchen with an adjacent dining area serves as the heart of the home, perfect for everyday living and large gatherings alike. Functional features include a well-equipped mudroom and a separate laundry room with double washers and dryers, designed for convenience without compromise. Outside, the wraparound porch leads to a resort-style backyard complete with an L-shaped pool, a stunning outdoor kitchen pavilion with bar seating and a built-in television—perfect for summer entertaining. This South Bayport estate seamlessly blends elegance, privacy, and scale—offering a rare opportunity to enjoy luxury living in one of Long Island’s most charming coastal communities.

6 Beds ⋅ 4 Baths ⋅ 877944 MLS

Stately South Bayport estate with exceptional scale & privacy. Set on a quiet, private lane in the heart of South Bayport, this remarkable 5,000 square-foot residence offers grand living and luxurious amenities in one of the area’s most serene and desirable settings. Beyond the iron gates, this home opens to a dramatic entry foyer with inlaid hardwood flooring and elegant raised panel walls, setting the tone for the craftsmanship and scale found throughout. With six generously sized bedrooms, every corner of this home is designed for comfort and space. The primary suite spans the entire south wing, offering a private lounge area, an expansive walk-in closet, and a beautifully renovated en suite bathroom—creating a true retreat within the home. Entertain with ease in the richly appointed billiard room, full home bar, and sophisticated lounge area—ideal for elevated evenings with guests. A colossal, open-concept kitchen with an adjacent dining area serves as the heart of the home, perfect for everyday living and large gatherings alike. Functional features include a well-equipped mudroom and a separate laundry room with double washers and dryers, designed for convenience without compromise. Outside, the wraparound porch leads to a resort-style backyard complete with an L-shaped pool, a stunning outdoor kitchen pavilion with bar seating and a built-in television—perfect for summer entertaining. This South Bayport estate seamlessly blends elegance, privacy, and scale—offering a rare opportunity to enjoy luxury living in one of Long Island’s most charming coastal communities.

90 Poplar Lane, Bayport

$1,520,000

Welcome to this beautifully maintained custom colonial set on a sprawling, park-like property with timeless curb appeal. Nestled behind a charming white picket fence and surrounded by mature landscaping, this expansive home offers generous living space, oversized rooms, and a layout perfect for both everyday living and entertaining. Features include a bright and inviting eat-in kitchen, multiple living and gathering areas, spacious bedrooms, and abundant natural light throughout. The meticulously manicured grounds provide privacy and plenty of room for outdoor enjoyment. Conveniently located near local amenities, parks, shopping, and transportation.

5 Beds ⋅ 4 Baths ⋅ 996571 MLS

Welcome to this beautifully maintained custom colonial set on a sprawling, park-like property with timeless curb appeal. Nestled behind a charming white picket fence and surrounded by mature landscaping, this expansive home offers generous living space, oversized rooms, and a layout perfect for both everyday living and entertaining. Features include a bright and inviting eat-in kitchen, multiple living and gathering areas, spacious bedrooms, and abundant natural light throughout. The meticulously manicured grounds provide privacy and plenty of room for outdoor enjoyment. Conveniently located near local amenities, parks, shopping, and transportation.

227 Gillette Avenue, Bayport

$1,500,000

Towering Pines – A Rare South Bayport Estate Step beyond the wrought-iron gates and into Towering Pines, a remarkable 1860 Queen Anne Victorian where timeless architecture meets a storybook setting. Perfectly situated in South Bayport, this distinguished residence unfolds across lush, professionally landscaped grounds reminiscent of a private arboretum, where mature specimen trees, vibrant gardens, and curated pathways create an atmosphere of serenity and grace.The property’s exterior is a sanctuary of outdoor living—featuring a tranquil koi pond with waterfall, an in ground pool surrounded by flowering gardens, a pergola-covered fire pit area, a child’s play space, a covered hot tub, and a dedicated dog run. A circular driveway with a central fountain, porte-cochere, and motor court lead to a detached three-car garage crowned by an inviting bonus loft, ideal for studio use, or private retreat. The home’s wraparound porch—one of its most defining features—welcomes you to a residence where craftsmanship and character reign supreme. Through double doors, the grand oak-paneled foyer sets the tone for what’s within: hand-carved woodwork, coffered ceilings, crystal sconces, and built-in seating that speaks to the home’s heritage and grace. Flanked by a formal living room and dining room, each with its own fireplace, this level showcases extraordinary architectural detail. The living room’s curved windows open fully to the porch, while the dining room’s raised panel walls and French doors connect seamlessly to the solarium and garden beyond. The handsome study, with its built-in granite-topped desk and intricate millwork, offers the perfect space for working from home in style. The kitchen is a blend of form and function, offering custom cabinetry, granite surfaces, and chef-caliber appliances, flowing effortlessly into an impressive lounge with wine bar and window seating, plus dining area, creating a seamless space for entertaining and everyday living. A cathedral-ceilinged great room with skylights invites gatherings both grand and intimate. Two powder rooms, a laundry room, and a heated enclosed porch complete the first level. Ascend the grand staircase—or the charming butler’s stairs—to discover the second floor, where framed original blueprints line the walls beneath stained glass windows said to be authentic Tiffany. The primary suite features a marble-clad bathroom with soaking tub and walk-in shower, as well as a bespoke dressing room with custom closets. A junior suite, currently enjoyed as a library, includes built-in shelving, a fireplace, and access to a private balcony and full bath with original soaking tub. Two additional bedrooms each offer their own distinctive whimsical personality and comfort. The third level continues the home’s story with three additional bedrooms—one presently used as a sitting room, another as an office—and a full bath with charming tub. Every inch of Whispering Pines reflects enduring craftsmanship: curved glass windows, custom millwork, porches and balconies that invite quiet moments, and modern amenities including central air, gas heat, and an interior/exterior sound system. Towering Pines is more than a home—it’s a living piece of South Bayport’s history, gracefully blending old-world artistry with modern comfort. A rare opportunity to own one of the area’s most enchanting and storied estates.

7 Beds ⋅ 5 Baths ⋅ 919264 MLS

Towering Pines – A Rare South Bayport Estate Step beyond the wrought-iron gates and into Towering Pines, a remarkable 1860 Queen Anne Victorian where timeless architecture meets a storybook setting. Perfectly situated in South Bayport, this distinguished residence unfolds across lush, professionally landscaped grounds reminiscent of a private arboretum, where mature specimen trees, vibrant gardens, and curated pathways create an atmosphere of serenity and grace.The property’s exterior is a sanctuary of outdoor living—featuring a tranquil koi pond with waterfall, an in ground pool surrounded by flowering gardens, a pergola-covered fire pit area, a child’s play space, a covered hot tub, and a dedicated dog run. A circular driveway with a central fountain, porte-cochere, and motor court lead to a detached three-car garage crowned by an inviting bonus loft, ideal for studio use, or private retreat. The home’s wraparound porch—one of its most defining features—welcomes you to a residence where craftsmanship and character reign supreme. Through double doors, the grand oak-paneled foyer sets the tone for what’s within: hand-carved woodwork, coffered ceilings, crystal sconces, and built-in seating that speaks to the home’s heritage and grace. Flanked by a formal living room and dining room, each with its own fireplace, this level showcases extraordinary architectural detail. The living room’s curved windows open fully to the porch, while the dining room’s raised panel walls and French doors connect seamlessly to the solarium and garden beyond. The handsome study, with its built-in granite-topped desk and intricate millwork, offers the perfect space for working from home in style. The kitchen is a blend of form and function, offering custom cabinetry, granite surfaces, and chef-caliber appliances, flowing effortlessly into an impressive lounge with wine bar and window seating, plus dining area, creating a seamless space for entertaining and everyday living. A cathedral-ceilinged great room with skylights invites gatherings both grand and intimate. Two powder rooms, a laundry room, and a heated enclosed porch complete the first level. Ascend the grand staircase—or the charming butler’s stairs—to discover the second floor, where framed original blueprints line the walls beneath stained glass windows said to be authentic Tiffany. The primary suite features a marble-clad bathroom with soaking tub and walk-in shower, as well as a bespoke dressing room with custom closets. A junior suite, currently enjoyed as a library, includes built-in shelving, a fireplace, and access to a private balcony and full bath with original soaking tub. Two additional bedrooms each offer their own distinctive whimsical personality and comfort. The third level continues the home’s story with three additional bedrooms—one presently used as a sitting room, another as an office—and a full bath with charming tub. Every inch of Whispering Pines reflects enduring craftsmanship: curved glass windows, custom millwork, porches and balconies that invite quiet moments, and modern amenities including central air, gas heat, and an interior/exterior sound system. Towering Pines is more than a home—it’s a living piece of South Bayport’s history, gracefully blending old-world artistry with modern comfort. A rare opportunity to own one of the area’s most enchanting and storied estates.

661 Middle Road, Bayport

$1,405,000

Nestled on coveted Gillette Avenue in Bayport, this timeless traditional home offers the perfect blend of coastal charm, privacy, and refined living. Set on 1.02 lushly landscaped acres, the property is surrounded by mature plantings and designed for effortless indoor-outdoor living, complete with in-ground pool, expansive deck, electric awning, and serene backyard setting. Just down the road, enjoy breathtaking open bay sunset views that make this neighborhood one of Bayport’s most desirable locations.Built in 2010 and impeccably maintained, this 3-bedroom, 2.5-bath residence with a bonus room/potential 4th bedroom feels like new. A dramatic double-height entry foyer welcomes you into beautifully designed formal and casual living spaces, including a piano room, formal dining room, and an inviting family room with a wood-burning fireplace. The stunning custom kitchen features a center island and opens seamlessly to the den, creating the ideal layout for entertaining and everyday living.Upstairs, the spacious primary suite offers a private balcony overlooking the beautifully manicured grounds, a gas fireplace, and a luxurious bath with radiant heated floors. Two additional bedrooms, a full bath, laundry room, and versatile bonus room complete the second floor. Additional highlights include Brazilian cherry wood floors, full basement, 2.5-car garage, large mudroom, central air, irrigation system, house alarm, and two fireplaces. Close to Harrow School.

3 Beds ⋅ 3 Baths ⋅ 996204 MLS

Nestled on coveted Gillette Avenue in Bayport, this timeless traditional home offers the perfect blend of coastal charm, privacy, and refined living. Set on 1.02 lushly landscaped acres, the property is surrounded by mature plantings and designed for effortless indoor-outdoor living, complete with in-ground pool, expansive deck, electric awning, and serene backyard setting. Just down the road, enjoy breathtaking open bay sunset views that make this neighborhood one of Bayport’s most desirable locations.Built in 2010 and impeccably maintained, this 3-bedroom, 2.5-bath residence with a bonus room/potential 4th bedroom feels like new. A dramatic double-height entry foyer welcomes you into beautifully designed formal and casual living spaces, including a piano room, formal dining room, and an inviting family room with a wood-burning fireplace. The stunning custom kitchen features a center island and opens seamlessly to the den, creating the ideal layout for entertaining and everyday living.Upstairs, the spacious primary suite offers a private balcony overlooking the beautifully manicured grounds, a gas fireplace, and a luxurious bath with radiant heated floors. Two additional bedrooms, a full bath, laundry room, and versatile bonus room complete the second floor. Additional highlights include Brazilian cherry wood floors, full basement, 2.5-car garage, large mudroom, central air, irrigation system, house alarm, and two fireplaces. Close to Harrow School.

83 Gillette Avenue, Bayport

$1,375,000

Welcome to this Exceptional South Bayport Colonial, where classic meets modern luxury. Step through the grand entry into a expansive open floor plan that connects the living room with the dining area. The formal living room features a wood burning fireplace perfect for hosting memorable holiday celebrations. The chef's kitchen equipped with top of the line appliances and a Sub-Zero refrigerator. Anchored by a island with hand painted Kohler sink and built in ice maker. Radiant heated floors throughout offer comfort, and a walk -in pantry adds for perfect storage. Stunning family room with cathedral ceilings and a cast-iron gas fireplace creates for cozy gatherings. From here, step into the bar room complete with custom bar and full solarium views of a perfectly landscaped backyard, ideal for unwinding with evening cocktails. The main level features a large bedroom and full bath-perfect for multigenerational living. Custom staircase leads to a serene primary suite , designed to capture sweeping views of the park like property. The luxurious bath includes a freestanding clawfoot tub and dual vanities. Three additional bedrooms and a laundry center complete the second floor. Fully finished basement features spacious recreation area perfect for poker nights and video gaming. An additional laundry center and large storage keeps life organized. The meticulously maintained gardens frame every corner with color and serenity. Drip system in gardens, 16 sprinkler zones. In the center of the yard is a built in salt water pool surrounded by pavers. Gatherings can be hosted around a custom barbecue center with grill and refrigerator. Unwind beneath the pavilion, where cool shade offers relaxation. The outdoor space is paired the a two car garage. Luxury with timeless design makes this your South Bayport dream.

5 Beds ⋅ 4 Baths ⋅ 942942 MLS

Welcome to this Exceptional South Bayport Colonial, where classic meets modern luxury. Step through the grand entry into a expansive open floor plan that connects the living room with the dining area. The formal living room features a wood burning fireplace perfect for hosting memorable holiday celebrations. The chef's kitchen equipped with top of the line appliances and a Sub-Zero refrigerator. Anchored by a island with hand painted Kohler sink and built in ice maker. Radiant heated floors throughout offer comfort, and a walk -in pantry adds for perfect storage. Stunning family room with cathedral ceilings and a cast-iron gas fireplace creates for cozy gatherings. From here, step into the bar room complete with custom bar and full solarium views of a perfectly landscaped backyard, ideal for unwinding with evening cocktails. The main level features a large bedroom and full bath-perfect for multigenerational living. Custom staircase leads to a serene primary suite , designed to capture sweeping views of the park like property. The luxurious bath includes a freestanding clawfoot tub and dual vanities. Three additional bedrooms and a laundry center complete the second floor. Fully finished basement features spacious recreation area perfect for poker nights and video gaming. An additional laundry center and large storage keeps life organized. The meticulously maintained gardens frame every corner with color and serenity. Drip system in gardens, 16 sprinkler zones. In the center of the yard is a built in salt water pool surrounded by pavers. Gatherings can be hosted around a custom barbecue center with grill and refrigerator. Unwind beneath the pavilion, where cool shade offers relaxation. The outdoor space is paired the a two car garage. Luxury with timeless design makes this your South Bayport dream.

85 Fairview Avenue, Bayport

$1,220,000

Welcome to the Hamlet of desirable South Bayport! This expansive custom designed 4,000+ SF home situated on nearly half an acre offers old world grandeur, serenity and privacy. This 5 bedroom, (4 upstairs, 1 down), 3 bath home also offers a 535+ SF Great Room with high ceilings, herringbone slate floor, and oversized fireplace which is surrounded by floor to ceiling windows that overlook private backyard. A second fireplace can be enjoyed in the home's study/den. Work remotely from the Home Office, also on first floor. A very large open concept kitchen/ dining room with 9'9" ceilings with custom-made solid cherry cabinetry is accented by stainless appliances and gas cooking and 6 zone natural gas heating. The generous primary suite on the second floor has a roof deck and marble bathroom with jacuzzi tub. Detached oversized garage with 2nd floor loft space offers many possibilities. Unfinished basement with Bilco Doors. MORE PHOTOS COMING SOON Walking distance to the Great South Bay, Browns River East Marina and the Village of Sayville. Don't miss this incredible opportunity! Viewing by Appointment Only

5 Beds ⋅ 3 Baths ⋅ 970779 MLS

Welcome to the Hamlet of desirable South Bayport! This expansive custom designed 4,000+ SF home situated on nearly half an acre offers old world grandeur, serenity and privacy. This 5 bedroom, (4 upstairs, 1 down), 3 bath home also offers a 535+ SF Great Room with high ceilings, herringbone slate floor, and oversized fireplace which is surrounded by floor to ceiling windows that overlook private backyard. A second fireplace can be enjoyed in the home's study/den. Work remotely from the Home Office, also on first floor. A very large open concept kitchen/ dining room with 9'9" ceilings with custom-made solid cherry cabinetry is accented by stainless appliances and gas cooking and 6 zone natural gas heating. The generous primary suite on the second floor has a roof deck and marble bathroom with jacuzzi tub. Detached oversized garage with 2nd floor loft space offers many possibilities. Unfinished basement with Bilco Doors. MORE PHOTOS COMING SOON Walking distance to the Great South Bay, Browns River East Marina and the Village of Sayville. Don't miss this incredible opportunity! Viewing by Appointment Only

133 Seaman Avenue, Bayport

$1,200,000

Welcome to 78 Oak Rd. which is located in the highly sought after South Bayport. This elevated beautifully maintained unique classic style colonial home has over 3500 sq. ft and 3 levels of spacious living. Whether is be water views, sunrise or sunset views, you will discover the privacy and timeless living with this home which is nestled on a very spacious lot in a prime secluded location and will not disappoint. Entering through the front door you're immediately greeted by the welcoming foyer that sets the tone for the rest of the home. The rich gleaming wood floors with radiant in floor heat stretch out before you offering a perfect blend of warmth and sophistication. Bathed in natural light, the formal dining room features a large elegant bay window that adds charm and enhances the spacious feel of the space. The large inviting formal living room offers abundant natural light of its own through the numerous windows and includes a lovely gas fireplace, perfect for relaxing or entertaining. A stunning great room with exposed beams awaits you centering around the unforgettable, magnificent wood burning fireplace where lasting memories are made. The open concept layout includes the EIK with center island and granite countertops, and cozy den which offers the perfect blend of comfort and charm. Just off the kitchen you'll find a thoughtfully placed pantry and very stylish half bath, for added convenience. Flowing perfectly from the great room you will find a beautiful sun-filled 3 season room with vaulted ceilings, skylights and beautiful windows. The gas burning stove will take you into the cooler days as you over look your lush extensive private backyard. With trex decking and patio, this make for the perfect relaxing entertaining outdoor space. Ascending to the second floor you're welcomed by a spacious landing leading to your very private primary en-suite that offers a very generous walk-in closet and second floor laundry area. Sunlit and spacious this primary en-suite boasts expansive windows and thoughtfully designed storage. Spa like primary bath featuring a luxurious Jacuzzi tub, spacious walk in shower and serene lighting offers radiant in floor heat, perfect for those chilly mornings. There are two additional bedrooms on this floor with ample closet space, one with a huge walk-in closet or maybe small home office area. The generously sized second full bath provides both comfort and convenience for all. Heading up to the third floor where elevated living continues, enjoy the privacy and tranquility this sun-drenched floor offers. With two bedrooms and full bath this top level retreat offers water views, skylights, walk in closet and large cedar closet for storage. This makes for the perfect guest quarters or home office area. This property features a spacious detached 2 car garage with attached carport, perfect for the car enthusiast. Complimented by a generously sized bonus room and its own private fire Island style walk up deck, this garage allows for endless possibilities. Tucked behind is a large attached shed offering ample space for tools, lawn equipment, bikes or workshop. From the unique features this home offers which includes its very own fire sprinkler and security system with panic button, built in Generac generator, updated low nitrogen septic system, access to the Great South Bay and boating, to the prime South Bayport location in the award winning Bayport-Bluepoint Schools, this home is full of surprises and you will not want to miss a single one.

5 Beds ⋅ 4 Baths ⋅ 909035 MLS

Welcome to 78 Oak Rd. which is located in the highly sought after South Bayport. This elevated beautifully maintained unique classic style colonial home has over 3500 sq. ft and 3 levels of spacious living. Whether is be water views, sunrise or sunset views, you will discover the privacy and timeless living with this home which is nestled on a very spacious lot in a prime secluded location and will not disappoint. Entering through the front door you're immediately greeted by the welcoming foyer that sets the tone for the rest of the home. The rich gleaming wood floors with radiant in floor heat stretch out before you offering a perfect blend of warmth and sophistication. Bathed in natural light, the formal dining room features a large elegant bay window that adds charm and enhances the spacious feel of the space. The large inviting formal living room offers abundant natural light of its own through the numerous windows and includes a lovely gas fireplace, perfect for relaxing or entertaining. A stunning great room with exposed beams awaits you centering around the unforgettable, magnificent wood burning fireplace where lasting memories are made. The open concept layout includes the EIK with center island and granite countertops, and cozy den which offers the perfect blend of comfort and charm. Just off the kitchen you'll find a thoughtfully placed pantry and very stylish half bath, for added convenience. Flowing perfectly from the great room you will find a beautiful sun-filled 3 season room with vaulted ceilings, skylights and beautiful windows. The gas burning stove will take you into the cooler days as you over look your lush extensive private backyard. With trex decking and patio, this make for the perfect relaxing entertaining outdoor space. Ascending to the second floor you're welcomed by a spacious landing leading to your very private primary en-suite that offers a very generous walk-in closet and second floor laundry area. Sunlit and spacious this primary en-suite boasts expansive windows and thoughtfully designed storage. Spa like primary bath featuring a luxurious Jacuzzi tub, spacious walk in shower and serene lighting offers radiant in floor heat, perfect for those chilly mornings. There are two additional bedrooms on this floor with ample closet space, one with a huge walk-in closet or maybe small home office area. The generously sized second full bath provides both comfort and convenience for all. Heading up to the third floor where elevated living continues, enjoy the privacy and tranquility this sun-drenched floor offers. With two bedrooms and full bath this top level retreat offers water views, skylights, walk in closet and large cedar closet for storage. This makes for the perfect guest quarters or home office area. This property features a spacious detached 2 car garage with attached carport, perfect for the car enthusiast. Complimented by a generously sized bonus room and its own private fire Island style walk up deck, this garage allows for endless possibilities. Tucked behind is a large attached shed offering ample space for tools, lawn equipment, bikes or workshop. From the unique features this home offers which includes its very own fire sprinkler and security system with panic button, built in Generac generator, updated low nitrogen septic system, access to the Great South Bay and boating, to the prime South Bayport location in the award winning Bayport-Bluepoint Schools, this home is full of surprises and you will not want to miss a single one.

78 Oak Road, Bayport

$1,200,000

Nestled on a cul-de-sac in South Bayport, this timeless colonial welcomes you with a wrap around porch where the scent of fragrant dogwoods in the air. Inside, a gracious foyer opens into a inviting sun-filled living room, flowing seamlessly into a oversized dining area, perfect for hosting memorable gatherings. The sunroom features French sliders that lead to a stunning Amalfi inspired poolside retreat. Dine al fresco under a vine covered arbor or relax by the pool in a setting designed for year round enjoyment. The cozy family room features a white brick fireplace framed by oversized built in shelving creating the perfect setting for relaxing evenings. The state of the art kitchen with stainless steel appliances flows seamlessly to center all occasions. The luxurious master-suite is a true retreat featuring its own private laundry center, ideal for the convenience of any busy family. The state of the art bathroom is a spa like sanctuary, complete with spacious shower and ample storage. Large closets and a additional appointed bathroom complete the restful retreat. Three additional bedrooms with large closets, one could be perfect for a in home office. A perfect blend of timeless design, modern amenities and seamless indoor-outdoor living this home offers a lifestyle of South Shore elegance.

4 Beds ⋅ 3 Baths ⋅ 884100 MLS

Nestled on a cul-de-sac in South Bayport, this timeless colonial welcomes you with a wrap around porch where the scent of fragrant dogwoods in the air. Inside, a gracious foyer opens into a inviting sun-filled living room, flowing seamlessly into a oversized dining area, perfect for hosting memorable gatherings. The sunroom features French sliders that lead to a stunning Amalfi inspired poolside retreat. Dine al fresco under a vine covered arbor or relax by the pool in a setting designed for year round enjoyment. The cozy family room features a white brick fireplace framed by oversized built in shelving creating the perfect setting for relaxing evenings. The state of the art kitchen with stainless steel appliances flows seamlessly to center all occasions. The luxurious master-suite is a true retreat featuring its own private laundry center, ideal for the convenience of any busy family. The state of the art bathroom is a spa like sanctuary, complete with spacious shower and ample storage. Large closets and a additional appointed bathroom complete the restful retreat. Three additional bedrooms with large closets, one could be perfect for a in home office. A perfect blend of timeless design, modern amenities and seamless indoor-outdoor living this home offers a lifestyle of South Shore elegance.

40 Spray Court, Bayport

$1,180,000

Tucked away in a private cul-de-sac in desirable South Bayport, this beautifully maintained Colonial is truly turn-key. A welcoming foyer is flanked by the formal living room and formal dining room, setting the tone for the home’s gracious layout. Beyond, an open-concept kitchen with a dining area flows seamlessly into the family room with a gas fireplace—both spaces enjoying peaceful views of the backyard. The main level also offers a bedroom, currently used as a den, with an attached full bathroom, plus a powder room for guests. Upstairs, the primary suite spans the entire east side of the home, complete with a walk-in closet and a spacious bathroom featuring a Jacuzzi soaking tub, and separate walk-in shower. Three additional bedrooms and a full bathroom complete the second floor. The finished basement is a versatile space with a recreation area, abundant storage, and a temperature-controlled room for your wine collection. The backyard is designed for entertaining and relaxation with an in ground pool, a poolside changing room with a full bathroom and shower, and a charming outbuilding with a kitchenette for outdoor gatherings. Mature landscaping surrounds the property, complemented by both decking and patio areas. An attached two-car garage adds convenience. Located in a sought-after, award-winning school district, this immaculate gem offers privacy, comfort, and a lifestyle to match.

5 Beds ⋅ 4 Baths ⋅ 900781 MLS

Tucked away in a private cul-de-sac in desirable South Bayport, this beautifully maintained Colonial is truly turn-key. A welcoming foyer is flanked by the formal living room and formal dining room, setting the tone for the home’s gracious layout. Beyond, an open-concept kitchen with a dining area flows seamlessly into the family room with a gas fireplace—both spaces enjoying peaceful views of the backyard. The main level also offers a bedroom, currently used as a den, with an attached full bathroom, plus a powder room for guests. Upstairs, the primary suite spans the entire east side of the home, complete with a walk-in closet and a spacious bathroom featuring a Jacuzzi soaking tub, and separate walk-in shower. Three additional bedrooms and a full bathroom complete the second floor. The finished basement is a versatile space with a recreation area, abundant storage, and a temperature-controlled room for your wine collection. The backyard is designed for entertaining and relaxation with an in ground pool, a poolside changing room with a full bathroom and shower, and a charming outbuilding with a kitchenette for outdoor gatherings. Mature landscaping surrounds the property, complemented by both decking and patio areas. An attached two-car garage adds convenience. Located in a sought-after, award-winning school district, this immaculate gem offers privacy, comfort, and a lifestyle to match.

1 Damaris Court, Bayport

$1,100,000

Welcome to a South Bayport sanctuary, where resort style living meets Mid-Century Modern Living. With close proximity to the Great South Bay, this home is designed for the best of South Shore living. From the moment you enter, soaring cathedral ceilings, oak hardwood floors and dramatic backyard vistas create a atmosphere of light and a connection to nature. The open-flow design is ideal for both intimate gathers or grand entertaining. Highlighted by a sunken living room with a three sided fireplace and a dining area that seamlessly opens through French doors to the private outdoor oasis. The kitchen offers premium appliances, double ovens and views of the sweeping backyard vistas framed by a lush arboretum backdrop. The primary suite overlooks the pool providing a serene retreat. The master bath has ample vanity custom storage with Jacuzzi tub. On the opposite side of the ranch the split bedroom layout offers privacy for separate living zones. An additional bedroom with its own solarium offers heat and sun filled versatility. Step into your private resort-style backyard featuring a sparking inground pool surrounded by stone pavers, A charming Pergola provides shade for al fresco dining. Refresh in the private outdoor shower. For peace of mind, this home is equipped with a whole-house generator. This rare gem blends blends modern living with timeless charm in one of Bayport's most desirable locations. Come play a little Bocce!

2 Beds ⋅ 2 Baths ⋅ 906792 MLS

Welcome to a South Bayport sanctuary, where resort style living meets Mid-Century Modern Living. With close proximity to the Great South Bay, this home is designed for the best of South Shore living. From the moment you enter, soaring cathedral ceilings, oak hardwood floors and dramatic backyard vistas create a atmosphere of light and a connection to nature. The open-flow design is ideal for both intimate gathers or grand entertaining. Highlighted by a sunken living room with a three sided fireplace and a dining area that seamlessly opens through French doors to the private outdoor oasis. The kitchen offers premium appliances, double ovens and views of the sweeping backyard vistas framed by a lush arboretum backdrop. The primary suite overlooks the pool providing a serene retreat. The master bath has ample vanity custom storage with Jacuzzi tub. On the opposite side of the ranch the split bedroom layout offers privacy for separate living zones. An additional bedroom with its own solarium offers heat and sun filled versatility. Step into your private resort-style backyard featuring a sparking inground pool surrounded by stone pavers, A charming Pergola provides shade for al fresco dining. Refresh in the private outdoor shower. For peace of mind, this home is equipped with a whole-house generator. This rare gem blends blends modern living with timeless charm in one of Bayport's most desirable locations. Come play a little Bocce!

11 Saltmeadow Lane, Bayport

$1,100,000

Welcome to 7 Kent Court in beautiful South Bayport...where modern design meets tasteful luxury. A serene waterfall nestled in the landscaping sets a tranquil tone that continues throughout the home. Soaring cathedral ceilings lead you to the heart of the home...the grand kitchen. Chef-grade appliances, ample maple cabinets, architectural lighting, invite large gatherings or cozy dinners. The extra amenities include hot & cold filtered water water dispenser & vegetable steamer. The walk in pantry provides abundant storage where the kitchen planning nook offers a space to manage daily schedules. Natural light pours through three oversized windows in the living room. The adjacent family lounge features a brick fireplace & hearth mantle creating a setting for game tournaments or Netflix marathons. Solarium is perfect for growing basil. New...30 Year Timberline Architectural Roof. The additional garage with heat, electricity, and water is perfect to make into guest quarters. Come take a look!

4 Beds ⋅ 3 Baths ⋅ 867941 MLS

Welcome to 7 Kent Court in beautiful South Bayport...where modern design meets tasteful luxury. A serene waterfall nestled in the landscaping sets a tranquil tone that continues throughout the home. Soaring cathedral ceilings lead you to the heart of the home...the grand kitchen. Chef-grade appliances, ample maple cabinets, architectural lighting, invite large gatherings or cozy dinners. The extra amenities include hot & cold filtered water water dispenser & vegetable steamer. The walk in pantry provides abundant storage where the kitchen planning nook offers a space to manage daily schedules. Natural light pours through three oversized windows in the living room. The adjacent family lounge features a brick fireplace & hearth mantle creating a setting for game tournaments or Netflix marathons. Solarium is perfect for growing basil. New...30 Year Timberline Architectural Roof. The additional garage with heat, electricity, and water is perfect to make into guest quarters. Come take a look!

7 Kent Court, Bayport

$1,075,000

Welcome to this charming cedar shake traditional in the heart of South Bayport, where timeless design meets modern comfort. A teak-covered front porch invites you inside to a soaring two-story foyer with gleaming hardwood floors. Just off the entry is a convenient mudroom, and beyond, an open floor plan seamlessly connects the living room—complete with custom built-in shelving and a cozy woodburning stove—to a bright and airy kitchen with a walk-in pantry. French doors open to a versatile room that can serve as a formal dining space or den. A first-floor bedroom offers flexible use as a guest suite or home office. Upstairs, the primary suite boasts a walk-in closet and private bath with a claw foot soaking tub. Two additional generously sized bedrooms and a full bath complete this level, along with a bonus walk-up attic with lots of clean storage. The basement provides excellent recreational space, storage, and a dedicated home gym. The grounds are reminiscent of a Hamptons retreat, featuring a pea gravel driveway, bluestone patios, a beautifully landscaped yard with mature plantings including a fig tree and herb garden, and an in ground pool. Outdoor living is elevated with a fire pit, two storage sheds, and a refreshing outdoor shower. The home also includes owned solar panels for energy efficiency. Set on a picture-perfect street within an award-winning school district and close to Browns River and the Great South Bay, this property offers the perfect blend of sophistication, functionality, and coastal charm.

4 Beds ⋅ 3 Baths ⋅ 908797 MLS

Welcome to this charming cedar shake traditional in the heart of South Bayport, where timeless design meets modern comfort. A teak-covered front porch invites you inside to a soaring two-story foyer with gleaming hardwood floors. Just off the entry is a convenient mudroom, and beyond, an open floor plan seamlessly connects the living room—complete with custom built-in shelving and a cozy woodburning stove—to a bright and airy kitchen with a walk-in pantry. French doors open to a versatile room that can serve as a formal dining space or den. A first-floor bedroom offers flexible use as a guest suite or home office. Upstairs, the primary suite boasts a walk-in closet and private bath with a claw foot soaking tub. Two additional generously sized bedrooms and a full bath complete this level, along with a bonus walk-up attic with lots of clean storage. The basement provides excellent recreational space, storage, and a dedicated home gym. The grounds are reminiscent of a Hamptons retreat, featuring a pea gravel driveway, bluestone patios, a beautifully landscaped yard with mature plantings including a fig tree and herb garden, and an in ground pool. Outdoor living is elevated with a fire pit, two storage sheds, and a refreshing outdoor shower. The home also includes owned solar panels for energy efficiency. Set on a picture-perfect street within an award-winning school district and close to Browns River and the Great South Bay, this property offers the perfect blend of sophistication, functionality, and coastal charm.

44 Bay Avenue, Bayport

$1,040,000

Welcome to 222 Bay Ave. Located in the highly sought after South Bayport neighborhood, you are just a short distance away, from the neighborhood park, town beach and marina. The perfect combination for South shore living . Whether you are looking to spend your time on the Great South Bay or just relaxing at home this beautiful Traditional offers a spacious floor plan. Upon entering you will be greeted by a charming formal dining room and a fabulous great room, complete with custom mill work ,hard wood floors and a wood burning fireplace . The perfect space to create a lifetime of memories with friends and loved ones. The large open kitchen has a center island as well as another dining area. There is ample counter space and cabinetry. Through the kitchen you can enter the den and access to the sunroom . There is a full bath and a half bath on the main level , a first floor bedroom and a ( bonus room ) with sliders to deck. Upstairs there are 2 large guest bedrooms a full bath and the primary bedroom with an ensuite . This home sits on an half acre of beautifully landscaped property. Imagine quite evenings in the jacuzzi after a long day or being able to host large gatherings . The outdoor space is fantastic ! The very large deck provides plenty of space for outdoor dining , BBQ's ,morning coffee under the retractable awning and so much more . You are not going to want to miss this beauty, the homeowners have already found their next home . Call today for your private tour !

4 Beds ⋅ 4 Baths ⋅ 898929 MLS

Welcome to 222 Bay Ave. Located in the highly sought after South Bayport neighborhood, you are just a short distance away, from the neighborhood park, town beach and marina. The perfect combination for South shore living . Whether you are looking to spend your time on the Great South Bay or just relaxing at home this beautiful Traditional offers a spacious floor plan. Upon entering you will be greeted by a charming formal dining room and a fabulous great room, complete with custom mill work ,hard wood floors and a wood burning fireplace . The perfect space to create a lifetime of memories with friends and loved ones. The large open kitchen has a center island as well as another dining area. There is ample counter space and cabinetry. Through the kitchen you can enter the den and access to the sunroom . There is a full bath and a half bath on the main level , a first floor bedroom and a ( bonus room ) with sliders to deck. Upstairs there are 2 large guest bedrooms a full bath and the primary bedroom with an ensuite . This home sits on an half acre of beautifully landscaped property. Imagine quite evenings in the jacuzzi after a long day or being able to host large gatherings . The outdoor space is fantastic ! The very large deck provides plenty of space for outdoor dining , BBQ's ,morning coffee under the retractable awning and so much more . You are not going to want to miss this beauty, the homeowners have already found their next home . Call today for your private tour !

222 Bay Avenue, Bayport

$980,000

Welcome to Gillette Ave — a beautifully updated 4-bedroom, 2.5-bath colonial just one block from the bay, offering the perfect blend of comfort, style, and coastal living. Step inside to an open-concept living and dining area that’s been thoughtfully redesigned for today’s lifestyle, featuring refinished floors that bring warmth and character to every room. The brand-new kitchen and stunning new primary bathroom add a fresh, modern touch that makes the home truly move-in ready. The first-floor laundry adds everyday convenience, and the full unfinished basement—spanning the entire length of the home—offers endless potential for storage, recreation, or future expansion. Outside, the property shines with professionally landscaped grounds, in-ground sprinklers, a manicured sod lawn, new plantings, and a border of arborvitaes that create both beauty and privacy. Summer days are made even better with a sparkling pool featuring a brand-new liner. With its prime Bayport location just steps from the water, this home delivers an inviting lifestyle where relaxation, recreation, and community come together. It’s the kind of place where memories are made, and every day feels a little like vacation.

4 Beds ⋅ 3 Baths ⋅ 967119 MLS

Welcome to Gillette Ave — a beautifully updated 4-bedroom, 2.5-bath colonial just one block from the bay, offering the perfect blend of comfort, style, and coastal living. Step inside to an open-concept living and dining area that’s been thoughtfully redesigned for today’s lifestyle, featuring refinished floors that bring warmth and character to every room. The brand-new kitchen and stunning new primary bathroom add a fresh, modern touch that makes the home truly move-in ready. The first-floor laundry adds everyday convenience, and the full unfinished basement—spanning the entire length of the home—offers endless potential for storage, recreation, or future expansion. Outside, the property shines with professionally landscaped grounds, in-ground sprinklers, a manicured sod lawn, new plantings, and a border of arborvitaes that create both beauty and privacy. Summer days are made even better with a sparkling pool featuring a brand-new liner. With its prime Bayport location just steps from the water, this home delivers an inviting lifestyle where relaxation, recreation, and community come together. It’s the kind of place where memories are made, and every day feels a little like vacation.

41 Gillette Avenue, Bayport

$972,500

Sprawling 3 Bedroom ranch on just shy of a half acre in south Bayport with blue ribbon Bayport schools! 5 Homes north of the great south bay, FLOOD ZONE X, no flood insurance required. Beautiful Hardwood floors throughout, recessed lighting, tons of natural light, granite countertops in an expansive chefs kitchen with custom octagon shaped ceiling with skylight. Pantry and laundry room just off the kitchen, single level living at its finest! The primary suite is complete with walk in closet and primary bath. The two additional bedrooms are both generously sized. Snuggle up in the winter in front of the wood burning fireplace

3 Beds ⋅ 2 Baths ⋅ 981887 MLS

Sprawling 3 Bedroom ranch on just shy of a half acre in south Bayport with blue ribbon Bayport schools! 5 Homes north of the great south bay, FLOOD ZONE X, no flood insurance required. Beautiful Hardwood floors throughout, recessed lighting, tons of natural light, granite countertops in an expansive chefs kitchen with custom octagon shaped ceiling with skylight. Pantry and laundry room just off the kitchen, single level living at its finest! The primary suite is complete with walk in closet and primary bath. The two additional bedrooms are both generously sized. Snuggle up in the winter in front of the wood burning fireplace

209 S Ocean Avenue, Bayport

$940,000

Absolutely stunning, COMPLETELY UPDATED 25'-26', condo in the highly sought-after Bayport Meadows 55+ community. This turnkey townhouse (Amelia Model, Corner) offers 3 bedrooms and 2.5 baths, including a desirable first-floor primary suite. The main level features brand-new ceramic tile flooring throughout, spanning the kitchen, dining room, living room, powder room, primary bedroom, walk-in closet, laundry room, coat closet, and basement landing. The beautifully updated kitchen includes refinished cabinetry, a new backsplash, vented hood range, and a custom-crafted breakfast nook. Designer window treatments elevate the space, including silhouette blinds in the living and dining rooms, and Hunter Douglas wicker blinds with room-darkening features in the primary suite. The luxurious primary bathroom is a true showpiece, featuring Italian marble throughout, a striking mother-of-pearl feature wall, custom StarMark cabinetry, a soaking tub, and high-end Kohler (Calista style) plumbing fixtures, all complemented by elegant crystal lighting. Upstairs, the full bathroom has been completely renovated. Bedrooms feature new carpeting with upgraded padding, and existing wood flooring has been refinished. The loft area is enhanced with new railings and balusters and the basement is fully finished with multiple additional storage closets. Additional upgrades include: Fresh interior paint throughout Two forced-air vents added to the basement for heating and cooling Full ductwork cleaning and sanitization (May 2025) Furnace and A/C condenser scheduled for maintenance (April 2026)

3 Beds ⋅ 3 Baths ⋅ 972086 MLS

Absolutely stunning, COMPLETELY UPDATED 25'-26', condo in the highly sought-after Bayport Meadows 55+ community. This turnkey townhouse (Amelia Model, Corner) offers 3 bedrooms and 2.5 baths, including a desirable first-floor primary suite. The main level features brand-new ceramic tile flooring throughout, spanning the kitchen, dining room, living room, powder room, primary bedroom, walk-in closet, laundry room, coat closet, and basement landing. The beautifully updated kitchen includes refinished cabinetry, a new backsplash, vented hood range, and a custom-crafted breakfast nook. Designer window treatments elevate the space, including silhouette blinds in the living and dining rooms, and Hunter Douglas wicker blinds with room-darkening features in the primary suite. The luxurious primary bathroom is a true showpiece, featuring Italian marble throughout, a striking mother-of-pearl feature wall, custom StarMark cabinetry, a soaking tub, and high-end Kohler (Calista style) plumbing fixtures, all complemented by elegant crystal lighting. Upstairs, the full bathroom has been completely renovated. Bedrooms feature new carpeting with upgraded padding, and existing wood flooring has been refinished. The loft area is enhanced with new railings and balusters and the basement is fully finished with multiple additional storage closets. Additional upgrades include: Fresh interior paint throughout Two forced-air vents added to the basement for heating and cooling Full ductwork cleaning and sanitization (May 2025) Furnace and A/C condenser scheduled for maintenance (April 2026)

89 Jims Trail, Bayport

$925,000

Welcome to this charming 4 bedroom, 2 bath cape in the heart of Bayport. Step into an inviting open living space anchored by a wood burning fireplace that creates a perfect setting for gatherings. The updated kitchen features white cabinetry, stainless steel appliances that flow seamlessly into an oversized family room wrapped in natural light. A wood burning fireplace with shiplap backsplash make this ideal for relaxing. The back door leads to a trex deck and fenced in built-in pool, offering a retreat for summer fun. A first floor bedroom overlooks park-like grounds. The living room with versatile options for home office or den has lots of storage space. The newly renovated bathroom showcases a light oak vanity, mixed media tile and a spa-inspired walk-in shower w modern gold handheld fixtures. Upstairs three additional bedroom with updated full bath. This Bayport gem offers the best of Southshore living...perfect for todays lifestyle.

4 Beds ⋅ 2 Baths ⋅ 952589 MLS

Welcome to this charming 4 bedroom, 2 bath cape in the heart of Bayport. Step into an inviting open living space anchored by a wood burning fireplace that creates a perfect setting for gatherings. The updated kitchen features white cabinetry, stainless steel appliances that flow seamlessly into an oversized family room wrapped in natural light. A wood burning fireplace with shiplap backsplash make this ideal for relaxing. The back door leads to a trex deck and fenced in built-in pool, offering a retreat for summer fun. A first floor bedroom overlooks park-like grounds. The living room with versatile options for home office or den has lots of storage space. The newly renovated bathroom showcases a light oak vanity, mixed media tile and a spa-inspired walk-in shower w modern gold handheld fixtures. Upstairs three additional bedroom with updated full bath. This Bayport gem offers the best of Southshore living...perfect for todays lifestyle.

115 Academy Street, Bayport

$910,000

Spacious and well-appointed over 3,000 sq ft farm ranch offering 5 bedrooms and 3 full bathrooms with a gracious layout designed for both everyday living and entertaining. The main level features a banquet-sized dining room, an expansive family room with a wood-burning stone fireplace, and a well-designed kitchen with an oversized island and adjoining dining area. The primary suite offers a private bath and walk-in closet, creating a comfortable retreat. Additional highlights include hardwood floors throughout, high ceilings, central air conditioning, a full basement, and an attached two-car garage. Outdoor features include a covered front porch welcoming you into the home and a private backyard with an in-ground pool featuring a brand new liner, ideal for summer enjoyment. The home is also topped with a brand new 50-year roof, offering long-term peace of mind. All located within a Blue Ribbon Award–winning school district. Don't miss this special home!

5 Beds ⋅ 3 Baths ⋅ 966740 MLS

Spacious and well-appointed over 3,000 sq ft farm ranch offering 5 bedrooms and 3 full bathrooms with a gracious layout designed for both everyday living and entertaining. The main level features a banquet-sized dining room, an expansive family room with a wood-burning stone fireplace, and a well-designed kitchen with an oversized island and adjoining dining area. The primary suite offers a private bath and walk-in closet, creating a comfortable retreat. Additional highlights include hardwood floors throughout, high ceilings, central air conditioning, a full basement, and an attached two-car garage. Outdoor features include a covered front porch welcoming you into the home and a private backyard with an in-ground pool featuring a brand new liner, ideal for summer enjoyment. The home is also topped with a brand new 50-year roof, offering long-term peace of mind. All located within a Blue Ribbon Award–winning school district. Don't miss this special home!

558 Gillette Avenue, Bayport

$887,500

Long Awaited South Bayport Gem On Desirable Street! This Rare Opportunity Has An Impressive Updated EIK On The Main Level With Radiant Heated Floor, Wet Bar, Wine Refrigerator, Stainless Steel Appliances, Granite Countertop And Cathedral Ceiling. Hardwood Floors In Adjacent Formal Dining Room And Formal Living Room. Enjoy The Window Seat In The Living Room Overlooking The Beautifully Landscaped Yard. Continue To Lower Level For Entertaining In Your Den With Wood Burning Stove, Bar, First Full Bath And An Additional Multi-purpose Room Equipped With A Murphy Bed. On The Upper Level You Will Find 2 Bedrooms And Your Second Full Bath. Continue Up To Your Primary Spacious Ensuite With A Walk In Closet, Private Full Bath With Radiant Heat, Jacuzzi Tub And Steam Shower. Suite Also Includes Separate Bonus Room For Exercise/Office Leading To Your Very Own Trex Balcony With Retractable Awning And Spiral Staircase. Your Breathtaking Fenced In Backyard Has 5 Easy Access Points. This Peaceful Oasis Has Multiple Patios, Outdoor Kitchen, Natural Gas Firepit Area, Hot Tub, Serene Koi Pond With Waterfall And An In Ground Saltwater Pool With Brand New Heater Surrounded By A Separate Fence For Safety. House Includes Full House Sound System, Substantial Amount Of Storage, One Car Garage, 2 Separate Central Air Units, 5 Zones Of Heat, In Ground Sprinkler System. Have Peace Of Mind With A Generac Whole House Generator And An Alarm System. Come See For Yourself And Make This South Bayport Gem Yours Today!!

3 Beds ⋅ 3 Baths ⋅ L3578552 MLS

Long Awaited South Bayport Gem On Desirable Street! This Rare Opportunity Has An Impressive Updated EIK On The Main Level With Radiant Heated Floor, Wet Bar, Wine Refrigerator, Stainless Steel Appliances, Granite Countertop And Cathedral Ceiling. Hardwood Floors In Adjacent Formal Dining Room And Formal Living Room. Enjoy The Window Seat In The Living Room Overlooking The Beautifully Landscaped Yard. Continue To Lower Level For Entertaining In Your Den With Wood Burning Stove, Bar, First Full Bath And An Additional Multi-purpose Room Equipped With A Murphy Bed. On The Upper Level You Will Find 2 Bedrooms And Your Second Full Bath. Continue Up To Your Primary Spacious Ensuite With A Walk In Closet, Private Full Bath With Radiant Heat, Jacuzzi Tub And Steam Shower. Suite Also Includes Separate Bonus Room For Exercise/Office Leading To Your Very Own Trex Balcony With Retractable Awning And Spiral Staircase. Your Breathtaking Fenced In Backyard Has 5 Easy Access Points. This Peaceful Oasis Has Multiple Patios, Outdoor Kitchen, Natural Gas Firepit Area, Hot Tub, Serene Koi Pond With Waterfall And An In Ground Saltwater Pool With Brand New Heater Surrounded By A Separate Fence For Safety. House Includes Full House Sound System, Substantial Amount Of Storage, One Car Garage, 2 Separate Central Air Units, 5 Zones Of Heat, In Ground Sprinkler System. Have Peace Of Mind With A Generac Whole House Generator And An Alarm System. Come See For Yourself And Make This South Bayport Gem Yours Today!!

182 Connetquot Road, Bayport

$880,000

New Construction Cape in beautiful Bayport! This stunning home features 4 bedrooms and 3.5 baths with a bright, open layout designed for modern living. The heart of the home is a gorgeous open chef's kitchen with ample cabinetry, center island, and seamless flow into the living and dining area-perfect for entertaining. Enjoy radiant heat on all three floors for exceptional comfort and efficiency. The home also offers a full basement with C/O, providing additional living space and flexibility. Set on a spacious property with a large backyard, ideal for outdoor entertaining, gardening, or future pool potential. Additional highlights include natural gas utilities, quality craftsmanship throughout, and generous room sizes. A rare opportunity to own a brand-new home in desirable Bayport close to parks, marinas, shopping, and everything that the South Shore lifestyle has to offer.

4 Beds ⋅ 4 Baths ⋅ 954580 MLS

New Construction Cape in beautiful Bayport! This stunning home features 4 bedrooms and 3.5 baths with a bright, open layout designed for modern living. The heart of the home is a gorgeous open chef's kitchen with ample cabinetry, center island, and seamless flow into the living and dining area-perfect for entertaining. Enjoy radiant heat on all three floors for exceptional comfort and efficiency. The home also offers a full basement with C/O, providing additional living space and flexibility. Set on a spacious property with a large backyard, ideal for outdoor entertaining, gardening, or future pool potential. Additional highlights include natural gas utilities, quality craftsmanship throughout, and generous room sizes. A rare opportunity to own a brand-new home in desirable Bayport close to parks, marinas, shopping, and everything that the South Shore lifestyle has to offer.

28 Locust, Bayport

$875,000

Sun-drenched and ideally situated on a highly desirable block, this expanded Cape offers the perfect blend of charm, space, and thoughtful updates. An extended driveway and welcoming front porch set the tone as you step into a cozy living room anchored by a gas fireplace with custom built-in cabinetry. Just beyond, a dedicated dining room creates an ideal setting for entertaining and everyday gatherings. The first floor features a versatile bedroom that easily functions as a bedroom or a home office, playroom, or den, complemented by gleaming newly sanded and stained oak hardwood floors and plush new carpeting throughout. Upstairs, the oversized primary bedroom provides a peaceful retreat, while the second bedroom offers the convenience of an en-suite layout. The newly finished and carpeted basement adds even more living space, featuring a relaxed den-style area plus an additional room ideal for entertaining, media, or hobbies. An unfinished section provides ample storage. Outside, the expansive property truly shines — a large backyard with a beautifully updated koi pond creates a private oasis, perfect for relaxing or hosting. The massive detached two-car garage offers incredible flexibility with room for vehicles, storage, or workspace. Additional upgrades include brand-new custom fencing around the front yard and along the sides of the property with two oversized gates, brand-new French doors to the lower-level bedroom/office, a new split unit upstairs, a brand-new rear deck, newly insulated and sheetrocked rear garage, insulated and plywood-finished front garage as well as custom crown and base moldings throughout. A rare opportunity to own a move-in-ready home with space, style, and a truly special outdoor setting.

3 Beds ⋅ 2 Baths ⋅ 961934 MLS

Sun-drenched and ideally situated on a highly desirable block, this expanded Cape offers the perfect blend of charm, space, and thoughtful updates. An extended driveway and welcoming front porch set the tone as you step into a cozy living room anchored by a gas fireplace with custom built-in cabinetry. Just beyond, a dedicated dining room creates an ideal setting for entertaining and everyday gatherings. The first floor features a versatile bedroom that easily functions as a bedroom or a home office, playroom, or den, complemented by gleaming newly sanded and stained oak hardwood floors and plush new carpeting throughout. Upstairs, the oversized primary bedroom provides a peaceful retreat, while the second bedroom offers the convenience of an en-suite layout. The newly finished and carpeted basement adds even more living space, featuring a relaxed den-style area plus an additional room ideal for entertaining, media, or hobbies. An unfinished section provides ample storage. Outside, the expansive property truly shines — a large backyard with a beautifully updated koi pond creates a private oasis, perfect for relaxing or hosting. The massive detached two-car garage offers incredible flexibility with room for vehicles, storage, or workspace. Additional upgrades include brand-new custom fencing around the front yard and along the sides of the property with two oversized gates, brand-new French doors to the lower-level bedroom/office, a new split unit upstairs, a brand-new rear deck, newly insulated and sheetrocked rear garage, insulated and plywood-finished front garage as well as custom crown and base moldings throughout. A rare opportunity to own a move-in-ready home with space, style, and a truly special outdoor setting.

94 Fairview Avenue, Bayport

$875,000

Rare opportunity to own 2.14 acres of prime land in South Bayport. This expansive parcel has been fully excavated with utilities already brought to the property, saving time and significant development costs. Approved building plans to build an approximate 5,000 square foot Home with a multi car garage are in place as well as Suffolk County Department of Health Approval. Whether you’re looking to build a different style/size home now (with Town approval) or hold for endless possibilities this property offers exceptional flexibility. Conveniently located near local amenities, beaches, and major roadways. A truly unique offering with a true blank canvas. The sky is the limit! Check with the Town for a possible subdivision/easement with proper permits.

953243 MLS

Rare opportunity to own 2.14 acres of prime land in South Bayport. This expansive parcel has been fully excavated with utilities already brought to the property, saving time and significant development costs. Approved building plans to build an approximate 5,000 square foot Home with a multi car garage are in place as well as Suffolk County Department of Health Approval. Whether you’re looking to build a different style/size home now (with Town approval) or hold for endless possibilities this property offers exceptional flexibility. Conveniently located near local amenities, beaches, and major roadways. A truly unique offering with a true blank canvas. The sky is the limit! Check with the Town for a possible subdivision/easement with proper permits.

92 Oakwood Avenue, Bayport

$870,000

Large and Beautifully Updated Ranch with a Lot of Bright and Welcoming Open Space. This Open Concept Floor Plan includes Oversized Kitchen with Extensive Cabinetry, Expansive Quartz Counters and Stainless-Steel Appliances, Butler Pantry, Formal Dining Room, Living Room, and Den with Wood Burning Fireplace. Very generously sized primary bedroom with modern bathroom. In addition, there is a junior suite with powder room, two additional bedrooms and second full bath. The finished lower level has 2 separate recreation areas, gorgeous full bathroom with walk in shower, ductless air conditioning, two egress windows and a laundry room. Other home features include hardwood floors throughout, central air conditioning, young roof, one car garage with overhead attic storage, beautiful driveway, paver front steps, and a private yard with deck nestled on quarter acre lot in the famed Blue-Ribbon Award-winning school district Bayport-Blue Point. This is an immaculate option as your next home.

4 Beds ⋅ 3 Baths ⋅ 995646 MLS

Large and Beautifully Updated Ranch with a Lot of Bright and Welcoming Open Space. This Open Concept Floor Plan includes Oversized Kitchen with Extensive Cabinetry, Expansive Quartz Counters and Stainless-Steel Appliances, Butler Pantry, Formal Dining Room, Living Room, and Den with Wood Burning Fireplace. Very generously sized primary bedroom with modern bathroom. In addition, there is a junior suite with powder room, two additional bedrooms and second full bath. The finished lower level has 2 separate recreation areas, gorgeous full bathroom with walk in shower, ductless air conditioning, two egress windows and a laundry room. Other home features include hardwood floors throughout, central air conditioning, young roof, one car garage with overhead attic storage, beautiful driveway, paver front steps, and a private yard with deck nestled on quarter acre lot in the famed Blue-Ribbon Award-winning school district Bayport-Blue Point. This is an immaculate option as your next home.

149 Barton Lane, Bayport

$846,000

Welcome to this spacious 1,800 sq. ft. home in the heart of South Bayport. This 2-story residence offers 9 rooms, including 4 (possibly 5) bedrooms and 2 full baths. Inside, you’ll find an inviting eat-in kitchen with stainless steel appliances, Corian countertops, and gas cooking, along with a comfortable living room, a formal dining room, and a great room featuring soaring ceilings and a wood-burning fireplace. Everything you need is on the ground level, with extra space upstairs. Additional highlights include central air conditioning, hardwood floors, 5 skylights, gas hot water with a young water heater, and cedar impressions vinyl siding. Outside, enjoy lush landscaping with specimen plantings, a rear deck, and an in-ground sprinkler system. The property also includes updated electric service, an oversized 2-car detached garage, and sits on a generous .39-acre lot. Located in a desirable South Bayport setting, with taxes of $15,986.97 after the basic Star credit…come see for yourself.

4 Beds ⋅ 2 Baths ⋅ 902551 MLS

Welcome to this spacious 1,800 sq. ft. home in the heart of South Bayport. This 2-story residence offers 9 rooms, including 4 (possibly 5) bedrooms and 2 full baths. Inside, you’ll find an inviting eat-in kitchen with stainless steel appliances, Corian countertops, and gas cooking, along with a comfortable living room, a formal dining room, and a great room featuring soaring ceilings and a wood-burning fireplace. Everything you need is on the ground level, with extra space upstairs. Additional highlights include central air conditioning, hardwood floors, 5 skylights, gas hot water with a young water heater, and cedar impressions vinyl siding. Outside, enjoy lush landscaping with specimen plantings, a rear deck, and an in-ground sprinkler system. The property also includes updated electric service, an oversized 2-car detached garage, and sits on a generous .39-acre lot. Located in a desirable South Bayport setting, with taxes of $15,986.97 after the basic Star credit…come see for yourself.

90 Academy Street, Bayport

$830,000

Beautiful Peltier Unit Located On The Pond In The Desirable 55+Bayport Meadows Estates . Open Floor Plan The First Floor Offers a Primary En Suite w/ 2 Walk in Closets, Tray Ceiling and Large Spa Like Bath. Living Room w/ Gas Fireplace, Granite S/S Kitchen, 1/2 Bath & Laundry Room. Second Story Offers a Den, 2 Bedrooms w/ Jack & Jill Bathroom. Plenty of Storage in Full Unfinished Basement . Enjoy Your Outside Living w/ Extended Paver Patio & The Pond. Enjoy All the Amenities This Gated Development Offers... Gorgeous Club House, Heated Indoor Pool, Heated Outdoor Pool, Bocce Court, Pool Table, & Gym . Live The Easy Life of Townhouse Living. Home comes equipped with chair lifts for easy access between levels.

3 Beds ⋅ 3 Baths ⋅ 893369 MLS

Beautiful Peltier Unit Located On The Pond In The Desirable 55+Bayport Meadows Estates . Open Floor Plan The First Floor Offers a Primary En Suite w/ 2 Walk in Closets, Tray Ceiling and Large Spa Like Bath. Living Room w/ Gas Fireplace, Granite S/S Kitchen, 1/2 Bath & Laundry Room. Second Story Offers a Den, 2 Bedrooms w/ Jack & Jill Bathroom. Plenty of Storage in Full Unfinished Basement . Enjoy Your Outside Living w/ Extended Paver Patio & The Pond. Enjoy All the Amenities This Gated Development Offers... Gorgeous Club House, Heated Indoor Pool, Heated Outdoor Pool, Bocce Court, Pool Table, & Gym . Live The Easy Life of Townhouse Living. Home comes equipped with chair lifts for easy access between levels.

37 Johnnys Path, Bayport

$825,000

This is the one you have been waiting for!!!! Upgraded Nichols 3 bedroom , 2.5 bath model offering 2190 square feet of living space plus 2 car attached garage and full basement. Brazilian cherry wood floors throughout. Extended patio . fplc and central vac are just some of the to many to list upgrades. Gated 55+ community with world class amenities.

3 Beds ⋅ 3 Baths ⋅ 976837 MLS

This is the one you have been waiting for!!!! Upgraded Nichols 3 bedroom , 2.5 bath model offering 2190 square feet of living space plus 2 car attached garage and full basement. Brazilian cherry wood floors throughout. Extended patio . fplc and central vac are just some of the to many to list upgrades. Gated 55+ community with world class amenities.

75 Jims Trail Unit #75, Bayport

$825,000

Basic Star if qualified and applied reduces taxes: $1072.99 Set on just shy of a half acre, meticulously maintained, Main level is open floor plan, light and bright with hardwood floors, lots of space, Living Room with sliders to trex, deck, Kitchen with granite and stainless steel appliances, gas cooking, hi ceilings Dining, Den with Wood burning stove, front room could be office or another sitting area, laundry on main. Ductless air cool/heat, natural gas and generator, 4 bedrooms total, large primary suite with beautiful bathroom, double sink, shower with seat and double shower heads. CVAC in home but not used Very Private property beautiful yard in ground sprinklers, there is a "storage cottage" in the yard as a bonus. Roof 8 Years old, 2x6 walls and 2x12 rafters Generac Generator - automatic powers in event of a power failure Direct wired 2EV charger

4 Beds ⋅ 2 Baths ⋅ 921350 MLS

Basic Star if qualified and applied reduces taxes: $1072.99 Set on just shy of a half acre, meticulously maintained, Main level is open floor plan, light and bright with hardwood floors, lots of space, Living Room with sliders to trex, deck, Kitchen with granite and stainless steel appliances, gas cooking, hi ceilings Dining, Den with Wood burning stove, front room could be office or another sitting area, laundry on main. Ductless air cool/heat, natural gas and generator, 4 bedrooms total, large primary suite with beautiful bathroom, double sink, shower with seat and double shower heads. CVAC in home but not used Very Private property beautiful yard in ground sprinklers, there is a "storage cottage" in the yard as a bonus. Roof 8 Years old, 2x6 walls and 2x12 rafters Generac Generator - automatic powers in event of a power failure Direct wired 2EV charger

190 Academy Street, Bayport