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$589,000
4 Beds ⋅ 2 Baths ⋅ 1041740 MLS
Investor opportunity in Bayport! Spacious **4-bedroom, 1.5-bath single-family home offering approximately 3,439 sq. ft.** of living space on an impressive **0.60-acre lot**. The property features a **partial unfinished basement** and offers significant potential for renovation and value creation. Ideal for an investor, contractor, or experienced buyer looking for their next project in the desirable Bayport area. **Cash only. Property is being sold as an assignment of contract; seller is a contract vendee.** Buyer to perform all due diligence regarding property condition, permits, property information, and intended use. Sold as-is.

362 Middle Road, 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
$599,999
3 Beds ⋅ 1 Baths ⋅ 1031965 MLS
Don’t miss this rare opportunity in the highly desirable Bayport community! This home features hardwood floors, vinyl siding, an updated oil burner, and an architectural style roof. This home can be purchased as-is or with the option of being fully renovated into a beautifully updated 3 bedroom, 2 bath home. Inquire for renovation plans, pricing, and additional details. This property is currently configured as a spacious 1 bedroom, but the layout offers the opportunity to be converted back to a 3-4 bedroom home.

30 Bayview Avenue, Bayport
$869,000
4 Beds ⋅ 2 Baths ⋅ 1025909 MLS
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249 Bayport Avenue, Bayport
$950,000
989994 MLS
Exceptional Mixed-Use Opportunity in the Heart of Bayport! Modern and advanced building ideally positioned on a main road, offering prime visibility and convenience. This well-maintained property features shared parking in a common lot. The first floor offers approximately 1,248 sq ft of versatile professional/commercial space, ideal for offices or a variety of business uses. Highlights include a spacious reception area, 3 office flexible layout, a refreshment Area, and a full bathroom. Perfect for accommodating multiple professional tenants or a solo business operation. The second floor features approximately 1,140 sq ft. It includes a 3-bedroom apartment with an open floor plan, offering comfortable living with a dedicated laundry room—ideal for an owner-occupant or additional rental income. Additional features include a large basement for storage or expansion potential, natural gas heat, and central air conditioning, both with two-zone systems for efficiency and comfort. This property includes a shared outdoor space, including the parking lot, landscaping, & garbage dumpster. Whether you’re looking to operate your business while living on-site or seeking a strong income-producing investment, this property offers incredible flexibility and location appeal.

569 Middle Road, Bayport
$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

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.