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$3,999,000
3 Beds ⋅ 3 Baths ⋅ 1032772 MLS
SPECTACULAR 2.75-ACRE WATERFRONT CONTEMPORARY ESTATE A truly rare opportunity to own an extraordinary privately gated 3,800 sq. ft. waterfront estate set on 2.75 breathtaking acres with over 1,000 feet of bulkhead and spectacular water views. Step through the grand double glass doors into a stunning open-concept interior featuring soaring windows, beautiful ceramic flooring, and a magnificent chandelier overlooking the water. The home offers 3 bedrooms, 3 bathrooms, a second-floor loft, dining room, living room with fireplace, and a 3-car garage.The fabulous chef’s kitchen features custom wood cabinetry, a large granite island, and professional Wolf and Verona stainless-steel appliances. The luxurious primary en-suite offers a spa bath, walk-in closet, glass doors with balcony and deck with bay views, elevator access, along with a convenient second-floor laundry room. The waterfront lifestyle is truly exceptional, offering over 1,000 feet of bulkhead, a large boat slip accommodating two 65-foot yachts, a boat ramp, and a dedicated cut-out for multiple jet skis. A spacious boathouse and waterfront gazebo provide the perfect setting for enjoying the water, while a beautiful patio and pergola create an ideal space for outdoor entertaining and relaxation. Take in breathtaking sunsets with picturesque views of the Robert Moses Bridge. Additional amenities include a full-house generator, 27-zone sprinkler system, and an on-demand tankless hot water heater. Perfectly positioned approximately 60 minutes by LIRR to NYC for world-class dining, entertainment and shows, and approximately 60 minutes to the Hamptons and its renowned wineries. From your own home or the nearby local ferries, enjoy a quick 20 minute ride to Fire Island's Ocean Beach and other sought after destinations, where you can spend the day exploring charming shops, enjoying waterfront dining and live music, or relaxing on the beautiful white sand beaches. It's the perfect blend of waterfront living, convenience, and the quintessential Fire Island lifestyle. Conveniently located near shopping, transportation and everyday amenities. A magnificent waterfront estate. An extraordinary lifestyle. A rare opportunity. Call today for your private showing.

170 S Penataquit Avenue, Bay Shore

$3,350,000
5 Beds ⋅ 5 Baths ⋅ 973534 MLS
To-be-built remarkable colonial on one of the most beautiful and sought-after streets in Bay Shore, set on just shy of 1.5 acres with stunning water views of the Great South Bay from the second level. This exceptional 5-bedroom, 4 full bath, 1 half bath residence will feature thoughtfully designed living space and the rare opportunity for full customization, allowing the buyer to tailor every detail to their taste and lifestyle. Proposed features include 10ft first floor ceilings, a state-of-the-art chef's kitchen connecting to a formal dining room through the butler's pantry, additional breakfast room, family room with gas fireplace, spacious great room with gas fireplace- perfect for everyday living and entertaining. A stunning sunroom filled with abundant natural light creates the perfect place to relax while enjoying the surrounding beauty. The home will also feature a charming second-floor balcony overlooking the bay attached to a large master suite with his and her closets, walk in closets in the additional bedrooms, a laundry room on the second level, and beautiful carport, perfect for bringing in groceries, and a detached two-car garage. A truly unique opportunity to build your dream home in a premier Bay Shore location.

100 Awixa Avenue, Bay Shore

$2,200,000
10 Beds ⋅ 7 Baths ⋅ 1037620 MLS
Step back in time and experience the grandeur of this extraordinary 1850 Victorian estate, a truly one-of-a-kind residence where timeless architecture, remarkable scale, and old-world craftsmanship create something rarely found today. Set on 1.64 breathtaking, park-like acres, this magnificent property offers exceptional privacy, an inground pool, and endless possibilities. From the moment you enter, soaring ceilings, intricate crown moldings, beautiful hardwood floors, and exquisite period details capture the elegance and charm of a bygone era. Three expansive floors of living space feature a magnificent living room, grand banquet-sized formal dining room, large eat-in kitchen, and an inviting den with fireplace. The main residence offers an impressive ten bedrooms, seven full baths, and a full basement, providing extraordinary space and versatility. The estate also features a separate back house offering four additional bedrooms, two full baths, and a two-car garage, adding another remarkable dimension to this unique property. Rich in history and overflowing with character, this exceptional Victorian estate presents a rare opportunity to restore, reimagine, and create something truly spectacular. From its grand interior spaces to its sprawling grounds and resort-style pool, this is more than a home. It is a piece of history waiting for its next chapter. Make this extraordinary one-of-a-kind estate yours.

45 S Penataquit Avenue, Bay Shore

$2,000,000
9 Beds ⋅ 9 Baths ⋅ 1040354 MLS
Rare Waterfront Investment Opportunity On Penataquit Canal! This Exceptional Home Offers Over 180 Feet Of Prime Waterfront With 13 Private Boat Slips, Expansive Docking, And Breathtaking Views Of Fire Island. Situated At The End Of A Quiet Cul-De-Sac, This Unique Property Features A Total Of 9 Bedrooms And 9 Bathrooms, Including 5 Bedrooms With Private En-Suite Baths. Step Outside To A True Waterfront Oasis Featuring An In-Ground Pool With An In-Ground Hot Tub, A Stunning Brick Outdoor Kitchen, Expansive Paver Patio, And Swaying Palm Trees, Creating The Ultimate Resort-Style Setting For Entertaining Or Relaxing Along The Water. Whether You're Looking To Expand Your Investment Portfolio, Generate Exceptional Rental Income, Or Own A One-Of-A-Kind Waterfront Property With Endless Possibilities, This Incredible Offering Checks Every Box. A Rare Opportunity To Own A High-Income Producing Property In An Unbeatable Waterfront Location.

64 Mowbray Avenue, Bay Shore

$2,000,000
1035730 MLS
Rare Waterfront Investment Opportunity On Penataquit Canal! This Exceptional Triplex Offers Over 180 Feet Of Prime Waterfront With 13 Private Boat Slips, Expansive Docking, And Breathtaking Views Of Fire Island. Situated At The End Of A Quiet Cul-De-Sac, This Unique Property Features A Total Of 9 Bedrooms And 9 Bathrooms, Including 5 Bedrooms With Private En-Suite Baths. Step Outside To A True Waterfront Oasis Featuring An In-Ground Pool With An In-Ground Hot Tub, A Stunning Brick Outdoor Kitchen, Expansive Paver Patio, And Swaying Palm Trees, Creating The Ultimate Resort-Style Setting For Entertaining Or Relaxing Along The Water. Whether You're Looking To Expand Your Investment Portfolio, Generate Exceptional Rental Income, Or Own A One-Of-A-Kind Waterfront Property With Endless Possibilities, This Incredible Offering Checks Every Box. A Rare Opportunity To Own A High-Income Producing Property In An Unbeatable Waterfront Location.

64 Mowbray Avenue, Bay Shore

$1,875,000
9 Beds ⋅ 5 Baths ⋅ 944725 MLS
Step into timeless elegance with this stately 9 bedroom 4.5 bath Federal Style home encompassing over 5,646 square feet of living space. Built in 1890, this grand home is steeped in rich history- once owned by George Macy, the famed tea importer. This architectural gem showcases classic period details including four fireplaces, intricate woodwork and moldings, high ceilings, and generously proportioned rooms. The gracious formal living and dining room are ideal for inside entertaining, while a specious deck allows for fabulous outdoor entertaining. This home sits on an expansive 1.4 acre lot and includes a 3-car detached garage, mature landscaping, and a commanding presence that reflects its storied past. With nine spacious bedrooms and four and a half baths, this is a rare opportunity to own a piece of history in an area known for it's prestigious homes and legacy properties.

35 S Penataquit Avenue, Bay Shore

$1,599,000
6 Beds ⋅ 4 Baths ⋅ 1045401 MLS
Lovingly restored and thoughtfully enhanced by its current owners, this remarkable 1880 residence reflects years of careful stewardship And substantial investment. Every update was made to elevate everyday living while honoring the home's character and architectural integrity. Updates: 2021 : New Siding & Windows, New PVC & Aluminum Fencing. Leaf Filter on All Gutters 2021/2022 : Basement waterproofed ( Lifetime guarantee ) 2021/2022 : Pool heater & Filter 2022 : New Split Units 2023: Generator, 15 zone Sprinklers, Alarm system with 11 Cameras hooked up to Central Station, Doors 2024: New Kitchen & Appliances, Motorized Shades in Living Room 2025: New driveway, New walkway and Stoops 2026: 2.5 New Bathrooms, with Soaker tub on 2nd floor and wonderful shower on third floor 2026: Newly sealed bricks around pool and back walkway.

75 S Penataquit Avenue, Bay Shore

$1,500,000
2 Beds ⋅ 2 Baths ⋅ 1011815 MLS
Welcome to Admiralty, a luxury gated community this beautifully appointed waterfront residence, where boating, private beach access, and resort-style living creates an exclusive coastal lifestyle.This beautifully appointed 2-bedroom residence showcases elegant imported flooring, soaring cathedral ceilings, and a breathtaking living room centered around a warm and inviting fireplace. The spacious gourmet kitchen is designed for both everyday living and entertaining, featuring premium stainless-steel appliances, a stylish bar area, and an open, sophisticated layout. The primary suite offers a private spa-like bathroom and with two walk-in closets, while additional features include a washer and dryer, ample storage, a spacious garage, and attic space. Step outside to your private patio, perfect for hosting family gatherings or enjoying peaceful outdoor living. Boating enthusiasts will appreciate the deep-water marina with private dockage and direct access to the Great South Bay. Situated within a meticulously maintained 158-acre waterfront community, residents enjoy an unparalleled lifestyle with 24/7 gated security, a newly renovated clubhouse, fitness center with Pilates and other wellness classes, three tennis courts, a pickleball court, private gardens, kayaking, a private beach, and a resort-style swimming pool with lifeguards. Perfectly positioned across from Fire Island’s Kismet and Ocean Beach and just a short drive to the Hamptons, this rare offering delivers the ultimate blend of luxury, recreation, and waterfront elegance. It includes snow removal, grass mowing and outside maintenance.Conveniently located near public transportation and supermarkets for easy everyday living.Just minutes from Bay Shore, offering access to shopping, dining, waterfront parks,less than two miles from ferry terminals to fire island and only one hour from NYC via LIRR. Don't miss out. https://theadmiraltyhoa.org

202 Captains Way, Bay Shore

$1,499,990
5 Beds ⋅ 4 Baths ⋅ 1001324 MLS
Nestled on Long Island’s coveted South Shore in desirable Bay Shore, this stunning five-bedroom ranch offers luxury living with a true resort-style feel. Beautifully landscaped grounds create a private backyard oasis featuring an Olympic-size swimming pool, expansive patio for entertaining, and a lighted professional tennis court for day or evening play. Inside, the home blends comfort and sophistication with an oversized family room ideal for gatherings, a sunroom showcasing panoramic yard views, and a chef’s kitchen featuring premium appliances, including a full-size Sub-Zero refrigerator and separate full-size Sub-Zero freezer with abundant storage. Recent upgrades include a Brand New sprinkler system, owned solar panels, a renovated double shower in the primary suite, updated heating and A/C in the kitchen, and a newly installed 5-ton central A/C unit. An upper-level bedroom with a private roof deck overlooks the pool and tennis court, completing this exceptional Bay Shore retreat. A rare opportunity to enjoy luxury, recreation, and effortless South Shore living.

9 Dove Lane, Bay Shore

$1,400,000
951712 MLS
This offering features three structures on one deeded lot in the heart of Bay Shore’s Business District. Seventy Park Ave is a 2,600 sq ft commercial building with a current CO allowing the first floor apartment to be used as a Personal Service business and residence, and the second floor as a separate apartment. The current owner is using both floors as a one family residence with a Personal Service business. The property offers parking for 5 to 7 vehicles and includes many updates throughout including the kitchen, three full bathrooms, and a full roof replacement completed approximately six years ago. Additional building features include natural gas hook up in house for cooking, an oil heating system and exterior cellar access to a full unfinished basement. The property is connected to sewers and public water, has commercial dumpster service for rubbish removal, and contains three electrical meters: two residential panels for the first and second floors and one commercial panel servicing the basement and garage. There is also a 400 sq ft detached two car garage and an additional 1100 sq ft building at 1636 and 1636A Union Blvd, CO’d as a legal two family dwelling with a studio and a one bedroom apartment. These units are separately metered for electric, with the studio operating on electric heat and the one bedroom having its own gas heating system. Both units are currently vacant. The property presents an opportunity to reposition multiple units at once, resolve outstanding violations, and capitalize on strong rental demand for studio, one bedroom, and two bedroom apartments in the area. With flexible layouts, on site parking, and significant upside through renovation and potential expansion, this asset is well suited for investors seeking value add potential and long term income growth.

70 Park Avenue, Bay Shore

$1,099,999
3 Beds ⋅ 3 Baths ⋅ 1032442 MLS
Enjoy Luxury Living in this 2222 Square foot (approx.) meticulously maintained Ranch home with its own deeded dock slip, that can fit a 10' Beam, perfectly located directly across the street. With convenient water access and water views, this is must see property. This home has been raised and sits on a spacious .46-acre lot in a quiet cul-de-sac, with beautifully landscaped front and side yards. This home features comfortable one level living with water views from some rooms and the spacious Trex deck with an electric awning and deck speaker. Upon entering the front door, just off the main foyer, the home features a dedicated pub room with sink and beverage refrigerator, creating the perfect space for entertaining. The very spacious 420' (approx.) chefs kitchen features radiant heat flooring, a commercial grade DCS, 5-burner gas range, a very large center island, a pantry, plenty of counter space and cabinets, two sinks w/garbage disposal, a drawer microwave, double drawer dishwasher and stainless appliances. There is a spacious living room with a gas fireplace and built in ceiling speakers. Adjoining, is a beautiful sun room with entrance to the deck. Down the hallway is the Laundry nook, two bedrooms and a redone full bath. At the end of hallway is the redone ensuite, shiplap wall in the primary, with a full bath and a step-in closet. There are High Hat lights throughout most of home. An additional feature is a young 2-car detached heated garage, with a 200amp electric panel, a workbench and sink. A circular driveway was just top coated and sealed. The house features a whole house generator with an automatic transfer switch. The generous deck backyard offers plenty of room for outdoor gatherings, gardening, or future enhancements. Interior highlights include hardwood flooring, bright living spaces, and a functional floor plan that provides both comfort and flexibility. Sip your beverage on the deck or at the kitchen table…while your mind is afloat, gazing at the water, where your boat slip is! Do not miss this rare opportunity for premier Long Island living.

6 Montgomery Lane, Bay Shore

$995,000
3 Beds ⋅ 3 Baths ⋅ 1050538 MLS
Welcome to the Admiralty, a guard-gated townhome community set on over 230 acres attached to a Nature Conservancy with 160 Townhomes & acres and acres of beautifully maintained grounds & water views to be shared by all homeowners. This true 3 bedroom Brigantine model with 2,117 square feet is in move-in condition with tiled entry foyer, double coat closet, full bath on 1st floor, living room with tile floor, woodburning fireplace with stone surround, triple sliding Pella door to backyard patio, formal dining room with tiled floor & double Pella sliding door, eat-in-kitchen with pickled pine cabinets, electrical stove, microwave, dishwasher, refrigerator, dining area, entry into attached garage & den behind garage with skylight & pull down stairs to attic. 2nd floor features a vaulted hallway ceiling with skylight & Primary Bedroom with walk-in-closet, 2 sink areas & shower, sliding door to deck balcony, 2nd bedroom has 2 double closets with oak floor & 3rd bedroom has a walk-in closet & oak floor. Hall bathroom has a jacuzzi tub & skylight. There is a 1-Car attached garage with interior access & EE opener, whole house water filter & central vacuum system. Oil hot water & hot air heat with central air conditioning. Amenities of the Admiralty feature a clubhouse with men's and women's gyms, sauna, Har-Tru tennis & pickleball courts, swimming pool with lifeguard & a private marina for your boat with deep-water docking and direct access to the Great South Bay. Conveniently located near the Fire Island ferries, Bay Shore's vibrant downtown, Good Samaritan & Northwell Hospitals as the LIRR for easy commuting to NY City.

174 Anchor Lane, Bay Shore

$949,990
4 Beds ⋅ 5 Baths ⋅ 1017682 MLS
Custom-built and thoughtfully designed, this exceptional home offers luxury finishes, expansive living spaces, and unmatched privacy backing directly to unbuildable state land in the West Islip School District. The main level features a gourmet chef’s kitchen complete with a center island, quartz countertops, stainless steel appliances, double ovens, and a gas range. A dramatic living room highlighted by soaring 16-foot vaulted ceilings, oversized windows that flood the space with natural light, custom built-in shelving and bar area, and a wood-burning fireplace. Formal dining room. Two spacious bedrooms and two full baths are also located on the first floor. Throughout the home, you'll find custom millwork, detailed molding and trim, tray ceilings, and high-end craftsmanship that sets this residence apart from typical builder-grade construction. Upstairs, the luxurious primary suite offers a spa-inspired bath with a soaking tub, separate shower, and generous his-and-her closets. Rich hardwood flooring is accented by stunning reclaimed 100-year-old barnwood details, adding warmth and character. The second floor also includes two separate den/family room spaces, a finished loft, an additional bedroom and full bath, and access to a private second-story terrace overlooking the serene surroundings. The fully finished basement provides exceptional additional living and entertaining space, featuring a wet bar with beverage refrigerator, full bathroom, and a separate outside entrance. Designed for year-round enjoyment, the backyard is an entertainer’s dream with a custom outdoor living area complete with built-in seating, bar counter, television, cooktop, sink, and beverage refrigerator. Combined with the privacy of the adjacent state land, this remarkable property offers a rare blend of luxury, comfort, and tranquility.

19 Joan Road, Bay Shore

$899,900
6 Beds ⋅ 5 Baths ⋅ 1013421 MLS
Large Versatile Residential Home with 6 bedrooms and 4 1/2 baths on 1.073 acre fenced property. Beautiful Paver Walkway (2024) with professional landscaping leads to front door. Electronic Gate and Driveway were added in 2022. 2nd floor has stunning updated kitchen (2023) with beautiful Silestone Quartz Countertops, Stainless Steel Appliances, Soft Close Cabinetry, Pot Filler over stovetop, Double Oven Range, Samsung Bespoke Refrigerator, Beverage Refrigerator and small Prep Sink in center island - perfect for entertaining! Upper level Master bedroom has large walk in closet. Master bath has sunken, jetted bathtub and a separate glass shower enclosure. Large Patio with Gazebo, Garden and Fountain for outdoor entertaining. Partially finished basement. Roof replaced in 2023. Home was most recently used as a FTHA (Family Type Home for Adults)and has a Concrete Handicap Ramp leading into side entryway. Located close to schools, shopping, parkways and LIRR (2 miles). Totally unique!

70 Massachusetts Avenue, Bay Shore

$849,000
4 Beds ⋅ 3 Baths ⋅ 1049887 MLS
Completely re-built in 2009: The home and property are exceptional, mid-block, great location. From quiet mornings on the welcoming front porch to relaxed evenings on the rear patio, this is a home designed to be enjoyed. Warm, inviting and thoughtfully remodeled, it blends timeless Colonial character with the comfort, convenience and modern features today’s buyers appreciate. The home is in move right in condition, the location is mid-block, not backing, siding or fronting any busy roads, yet conveniently located to allow easy access in and out of the community. Step inside through the dramatic cathedral entrance foyer, where generous room sizes, hardwood floors throughout and a gracious, flowing layout immediately set the tone. The formal living room or parlor offers a versatile setting for welcoming guests, reading, relaxing, studying or creating an elegant home office. At the heart of the home is the spacious eat-in kitchen, beautifully appointed with granite countertops, Energy Star appliances, gas cooking and a convenient butler’s service area—perfect for casual meals, holiday gatherings and effortless entertaining. A gas burning fireplace adds warmth and character to the inviting living spaces, while the conveniently located first-floor laundry and mudroom with separate outside entrance that also provides access to the basement brings everyday practicality to the home’s thoughtful design. The upper level features four generously sized bedrooms, included, the Primary with a luxurious en-suite, abundant closet space and the storage every home needs. The partially finished basement provides even more room to enjoy, with flexible space for recreation, hobbies, fitness, guests or additional work-from-home needs, additional basement space makes room for whatever your heart desires. A separate side entrance via the mudroom/laundry area allows for convenient access to the basement. The majority of the home was re-built/renovated in 2009. The home features but is not limited to the following; Andersen 400 Series windows, 200-amp electrical service and a French drain system surrounding the home—valuable improvements that enhance comfort, efficiency and peace of mind. Outside, the beautifully maintained and rear fenced property creates a wonderful private setting for relaxing, entertaining, gardening and enjoying the seasons. The front porch, rear patio and attractive grounds extend the living experience well beyond the interior. Ideally located minutes to Bay Shore’s vibrant Main Street, exceptional dining, cafes, shopping, the Great South Bay waterfront, Fire Island ferries, parks, beaches, the Long Island Railroad and major roadways, this home offers an appealing combination of neighborhood charm and everyday convenience. First time offered and an unbelievable value—this exceptional, beautifully designed Colonial is ready to welcome its next owner. Move right in, settle in and make it yours. Note: of the 1962 structure, one small closet wall, garage and (partial) original basement was kept. An additional foundation was added to create what is now, the current home!

1456 Pine Acres Boulevard, Bay Shore

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.