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$1,375,000
3 Beds ⋅ 4 Baths ⋅ 934770 MLS
This beautifully styled home was thoughtfully transformed to create its own distinctive look and feel with the project completed in 2017. Storybook Tudor-A Fairytale Retreat with Carmel-by-the-Sea Charm right here in South Bayport. Just 5 houses from the Bayport beach, enter into a world of storybook elegance with this extraordinary 3-bedroom, 3.5-bath architectural masterpiece inspired by the enchanting homes of Carmel-by-the-Sea, California. Every detail of this residence exudes artistry, craftsmanship, and timeless sophistication — a perfect blend of European romance and modern luxury. From the moment you arrive, the home’s cedar shake roof, detailed windows, and Dutch front door invite you into a warm, character-filled sanctuary. Inside, white oak character plank floors flow throughout sunlit spaces adorned with antique French lighting and bespoke design details. The heart of the home is the chef’s kitchen, a true culinary masterpiece. Designed for both gourmet cooking and artisan baking, it features Italian slate countertops, dual cherry wood islands, and a dedicated Botticelli Italian stone baking island supported by antique French circa 1860 table legs. Enjoy a 60-inch ILVE range with brass fittings beneath an industrial brass-trimmed hood, a Sub-Zero refrigerator and freezer, Bosch Benchmark dishwasher, wet bar, pot filler, and dual under-counter refrigerator drawers and microwave. A shelf lined pantry and farm sink with hands-free faucet complete this dream kitchen. The den/great room impresses with 20-foot ceilings, hand-laid stone fireplace and abundant natural light, creating an inviting space for both relaxation and entertaining. A bonus room serves perfectly as a craft studio or playroom, while a dedicated exercise room and home office offer flexibility for today’s lifestyle. These rooms can easily become bedrooms if in need of more sleep space without sacrificing living space. Suitable as an en suite / in-law space as well. The south-facing sunroom, adorned with antique French tile flooring, provides a serene setting for morning coffee or afternoon tea, basking in gentle natural light. The primary suite is a romantic retreat, featuring vaulted ceilings, parrot-style windows, dual closets, and a dedicated makeup area. The spa-inspired primary bath includes a clawfoot champagne soaking tub and a Herbeau faucet shaving stand, blending antique beauty with modern comfort. Two additional bedrooms each offer huge closets and thoughtfully curated finishes. For a bit of whimsy, you will love the hidden spiral staircase leading to a cozy attic nook. Oh and lets not forget the He Shed-She Shed with adjoining hot tub room. Throughout the home, antique lighting, handcrafted details, and authentic materials create a sense of history and artistry rarely found in modern builds. This is more than a home — it’s a one-of-a-kind sanctuary where fairytale charm meets refined living.

249 Gerritsen Avenue, Bayport
$1,249,000
4 Beds ⋅ 2 Baths ⋅ 1029464 MLS
Where history meets coastal elegance, this exceptional South Bayport residence is believed to have originated as the carriage house for Captain Edward Gillettes estate. Thoughtfully reimagined, the home seamlessly blends timeless architecture with its historic character , creating a one-of-a kind retreat where heritage and modern luxury meet. At the heart of the home, the chefs kitchen features crisp white cabinetry, quartz countertops, 2023 Sub Zero Refrigerator, stainless steel appliances, two ovens , and a statement navy island with wine refrigerator. The open concept design transitions effortlessly into the inviting family room complete with radiant floor heating. The dining room is defined by custom board-and-batten wainscoting and crafted millwork that evokes a coastal aesthetic. Designed with exceptional attention to detail, the living room has custom millwork, board-and-batten walls and brick fireplace crowned by a reclaimed wood mantel. Wide plank hardwood floors lend character while a light filled bay window creates a connection to the surrounding landscape. Beyond the grounds a sparkling salt water pool create a backyard retreat ideal for entertaining. The second level offers a tranquil primary bedroom, three additional bedrooms and a full bath-offering a comfortable and versitile layout with lasting appeal. French doors open to a charming patio perfect for al fresco dining and seamless indoor outdoor living. experience the rhythm of life on the South Shore where The Great South Bay is just steps away and Fire Island serves as your backdrop. Paired with the acclaimed Bayport-BluePoint School District this coveted location offers a lifestyle defined by coastal beauty, community and timeless appeal.

22 S Gillette Avenue, Bayport
$1,199,000
3 Beds ⋅ 3 Baths ⋅ 1019745 MLS
Beautiful 3 bed/2.5 bath home set back on a large landscaped lot south of Montauk Hwy! This post modern home has a large circular driveway, detached 4 car garage, open floor plan, walk out basement (potential for rental income with the proper permits) , central air, central vacuum, duel sided gas fireplace, spacious rooms, walk in closets, gas stove and oven, 1st floor master bedroom with a shower and tub, front porch, back deck and so much more! Home is within close proximity to the great south bay, boating fishing, transportation, restaurants and shopping conveniences. All of that, plus the added bonus of being located within the award winning Bayport/ Blue Point School District.

275 S Gillette Avenue, Bayport
$999,999
3 Beds ⋅ 3 Baths ⋅ 1014448 MLS
Step into timeless elegance with this beautifully maintained Circa1890 Colonial, offering approximately 2,650 square feet of living space on a picturesque .59-acre property in the coveted Bayport-Blue Point School District and Library. Rich in character and history, this 3-bedroom, 3-full-bath home seamlessly blends original craftsmanship with thoughtful modern updates. Inside, you'll find stunning original hardwood floors, an original wood-burning fireplace, Formal living and dining rooms, a dedicated home office, and a well-appointed kitchen featuring premium Stainless Steel Viking and Sub-Zero appliances. Radiant heat adds comfort throughout the bathrooms, kitchen, laundry, and Primary bedroom. while central air conditioning provides year-round convenience. The exterior is equally impressive, showcasing a heated in-ground saltwater pool and spa, expansive deck with PVC railings, covered front porch, professionally landscaped grounds with 15-zone in-ground sprinklers, PVC fencing, and a beautifully designed driveway with pavers. Additional highlights include Andersen windows, a 2-car garage with loft, full partially finished basement, updated architectural roof, 200-amp electric service, alarm system, and all certificates of occupancy in place. A rare opportunity to own a piece of Bayport history with modern amenities, exceptional outdoor living, and pride of ownership throughout.

202 Bayport Avenue, Bayport
$993,000
4 Beds ⋅ 3 Baths ⋅ 1028655 MLS
Welcome to this quality-built 1988 Center Hall Colonial, where timeless elegance, exceptional craftsmanship, and a thoughtfully designed floor plan come together to create the perfect place. A grand entrance foyer welcomes you into this impressive residence, while hardwood floors flow throughout most of the home, adding warmth and sophistication. (The kitchen and bathrooms feature tile flooring.) Designed for both everyday living and entertaining, this spacious home offers four generously sized bedrooms, including a luxurious primary suite with a private en-suite bath featuring a relaxing jetted soaking tub and a separate shower. The inviting family room is the heart of the home, showcasing a wood-burning fireplace and a wall of windows with sliding doors that fill the space with natural light and provide seamless access to the backyard. Situated on a beautifully landscaped, shy one-acre property, the home is set well back from the road, offering exceptional privacy and a peaceful setting. The expansive backyard features a sparkling in-ground swimming pool with a new liner, ample space for outdoor gatherings, and plenty of room to relax and enjoy your own private retreat. Additional highlights include a spacious two-car attached garage and a setting that perfectly blends tranquility with convenience. This exceptional Colonial offers the ideal combination of quality construction, generous living space, and an outdoor oasis designed for years of enjoyment.

348 Middle Road, Bayport
$824,999
4 Beds ⋅ 3 Baths ⋅ 992302 MLS
Welcome to this meticulously maintained 4 bedroom Hi Ranch home offering a bright open concept design and upgraded kitchen perfect for modern living. Generously sized bedrooms, 2.5 baths totally renovated, inviting backyard with white vinyl fencing provide the ideal space for relaxation and entertaining. Complete with garage and parking for up to 4 vehicles. Bright and airy fully finished downstairs potential extra living space , with proper permits. Newly redone stoop with pavers, Central air, sprinkler system, updated electrical panel. Move in ready! Nothing to do!

110 Stephen Road, Bayport
$799,000
4 Beds ⋅ 3 Baths ⋅ 1036830 MLS
Exceptional South Bayport location! Set at the end of a quiet cul-de-sac on a .45-acre property, this spacious 2,300-square-foot home offers privacy and plenty of outdoor space. Featuring 9 rooms, including 4 bedrooms and 2.5 beautifully updated bathrooms, the home features an ideal blend of comfort, functionality, and modern updates. The impressive eat-in kitchen, renovated in 2023, features quartz countertops, a tile backsplash, stainless steel appliances, a farmhouse sink, walk-in pantry, and a peninsula that opens to the large formal dining room, creating an ideal space for everyday living and entertaining. The spacious layout also includes a large living room, formal dining room, a private family room that provides a comfortable retreat from the main living area, and a three-season room with a Vermont-style wood burning stove. Hardwood floors, crown molding, recessed lighting, central air conditioning, and loads of storage enhance the home's appeal. Step outside to the rear deck overlooking the expansive backyard, perfect for entertaining, relaxing, or outdoor activities. Additional features include a 2-car attached garage, 200-amp electric service, and an in-ground sprinkler system. A wonderful opportunity to own this beautifully updated home in one of South Bayport's most sought-after locations… a true must see.

27 Baywood Lane, Bayport
$798,000
4 Beds ⋅ 2 Baths ⋅ 1038252 MLS
Welcome to this beautifully maintained ranch-style home in Bayport, offering approximately 1,800 square feet of comfortable, thoughtfully designed living space. Completely gutted and renovated in 2009/2010, the home features hardwood floors, custom crown molding throughout, and a warm, inviting layout ideal for everyday living and entertaining. The main living areas include a spacious living room with a wood-burning fireplace, formal dining area, eat-in kitchen, and family room with sliding patio doors opening to the rear deck and yard. A convenient mudroom with laundry adds to the home's functionality. Four bedrooms include a private primary suite with two closets and a full bath. Three additional bedrooms share a second full bathroom conveniently located nearby. The lower level provides an abundance of immaculate storage space, an egress window, utilities, and plenty of options for future use. Outside, pretty landscaping enhances the property, complemented by in-ground sprinklers, a wide driveway, rear deck, and nicely sized yard. All of this is set in desirable Bayport and within the award-winning Bayport-Blue Point School District—a wonderful opportunity for one-level living in a sought-after South Shore community.

360 Bayport Avenue, Bayport
$725,000
3 Beds ⋅ 3 Baths ⋅ 980753 MLS
Welcome to this charming home located in the award-winning Bayport-Blue Point School District, within walking distance to all schools. Situated on a corner lot in a quiet neighborhood, this property offers comfortable living with 3 bedrooms and 3 full baths, a bright living space, and an eat-in kitchen with dining area. The backyard provides a private retreat featuring a semi in-ground saltwater pool, perfect for summer entertaining and relaxing outdoors. Ideally located close to local shops, restaurants, South Shore beaches, and the Fire Island ferry, this home offers the perfect blend of convenience, community, and coastal lifestyle in the heart of Bayport.

33 2nd Street, Bayport

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.