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$5,750,000
13 Beds 7 Baths 1029909 MLS
LISTING IS FOR 6 HOMES AND .77 VACANT LAND! An exceptional opportunity to own a one-of-a-kind waterfront estate featuring 6 income-producing residences plus an adjoining nearly one-acre buildable lot, offering tremendous potential to expand the rental portfolio or create a spectacular multigenerational compound. The property includes two Bayfront homes—one offering 4 bedrooms and 3 bathrooms, the other has 3 bedrooms and 1.5 bathrooms—along with four additional cottages, including two 2-bedroom cottages and two 1-bedroom cottages. The adjacent buildable parcel presents endless possibilities, whether for a custom waterfront residence, additional income-producing opportunities, or the ultimate private estate. A rare investment with multiple revenue streams, redevelopment potential, and breathtaking waterfront setting. Please do not go on the property without a scheduled appointment.

18 Smith Lane, Jamesport

$1,999,900
4 Beds 5 Baths 1025045 MLS
Experience the pinnacle of waterfront living in this exceptional newly constructed residence, perfectly situated on 1.19 acres of pristine waterfront property. Designed to capture breathtaking water views from nearly every room, this sophisticated 4-bedroom, 4.5-bathroom home seamlessly blends timeless elegance with modern luxury. The sun-filled open-concept floor plan is anchored by a stunning chef's kitchen featuring premium stainless-steel appliances, custom cabinetry, and an expansive island, all overlooking the tranquil waterfront. The spacious living and dining areas flow effortlessly to the rear deck, creating the perfect setting for indoor-outdoor entertaining while enjoying spectacular sunsets and refreshing bay breezes. Each of the four generously sized bedrooms is a private ensuite retreat, offering beautifully appointed bathrooms and exceptional comfort for family and guests. A stylish powder room adds convenience for entertaining. Outside, the expansive backyard leads to an impressive private dock capable of accommodating up to five boats, making this an extraordinary opportunity for boating enthusiasts. Whether you're setting out for a day on the water or returning home to relax on the spacious rear deck, this property offers an unparalleled waterfront lifestyle. Additional features include a two-car garage, quality craftsmanship throughout, and the peace of mind that comes with new construction. Offering privacy, luxury, and direct water access, this remarkable home is a rare opportunity to own a premier waterfront retreat minutes from the Hamptons, wineries and beaches.

255 Peconic Bay Boulevard, Aquebogue

$1,864,000
3 Beds 3 Baths 1003959 MLS
Waterfront living designed for effortless coastal comfort, ideally situated on Meeting House Creek, this boater’s dream home features a private deepwater dock equipped to accommodate a large yacht, additional watercraft, and offers quick access to Peconic Bay. This updated 3-bedroom, 3-bath contemporary residence showcases water views, spectacular sunsets, and seamless indoor-outdoor living. The light-filled main level offers an open floor plan that flows directly to the outdoor oasis, complete with a splendid heated saltwater pool with automatic cover, expansive bluestone patio, fire pit with built-in seating, luxurious mahogany outdoor shower, and a fully equipped outdoor kitchen featuring Blaze marine-grade storage cabinets, slate countertops, beverage refrigerator, and sink with hot and cold water. Generous dining and lounge areas create the perfect setting for entertaining or relaxing while enjoying breathtaking sunsets over the water. Large windows throughout the home invite in natural light and capture the stunning waterfront scenery, creating a bright and airy atmosphere. The open-concept main floor also features a chef’s kitchen with quartz countertops, high-end stainless-steel appliances, Viking range, dining area, and living room with wood-burning fireplace and hardwood oak floors throughout. A guest suite with renovated full bath , a second full bath, and a laundry room complete the first level. The second floor offers a serene primary suite with a private balcony overlooking the water, renovated spa-like bath, and additional guest bedroom. Additional amenities include radiant heated floors in the kitchen, laundry room, and all three bathrooms, a 1.5-car attached garage with ample storage room above, a Level 2 EV charger, and custom cedar fencing. A private neighborhood beach is just moments away. A truly turnkey waterfront retreat offering luxury, comfort, spectacular sunsets, and the very best of North Fork living.

81 Beach Road, Aquebogue

$1,195,000
3 Beds 2 Baths 000132 MLS
Fabulous Sunsets from All Rooms Including Expansive 92-Foot Private Deck. Located 2 Minutes from Beach & Perched on a Hill on Quiet Cul-De-Sac Street. The Main Level Features Spacious LR & FDR w/Impressive Wall of Windows, Sliding Andersen Doors to 92 Ft Deck & Hot Tub, Beautiful Vaulted Ceilings, and Anchored by a Dramatic Stone Fireplace. Modern Eat-in Chefs Kitchen with a Large Granite Island. Spacious 3 Bedrooms, Den /Office, 2 Full Baths (& Jacuzzi). Spacious Lower (Walk Out) Level with Very High Ceilings & Windows, Laundry, & Access to 2 Car Garage & Long Private Driveway. Many Upgrades Include Radiant Heated Floors, Central Vac & Central Air Conditioning. Best Location and Beach 2 Minutes Away, Vineyards, Boating, Golf, and the Best of the North Fork and Hamptons Lifestyle!

10 Silver Beech Lane, Wading River

$1,425,000
3 Beds 2 Baths 993305 MLS
Charming 1879 Farmhouse with Waterfront Opportunity Set across 2 acres in Wading River, this beautifully preserved 1879 farmhouse offers a rare pairing of historic character and coastal lifestyle. The residence sits on .95 acres, complemented by a separate 1-acre Soundfront parcel with beach access and breathtaking views, completing this exceptional offering. Timeless details define the home, including a warm and inviting living room with wood-burning fireplace and custom built-ins. A thoughtfully designed 2012 addition introduces an open-concept kitchen, dining area, and sunlit den, creating a natural gathering space for both everyday living and entertaining. Wrapped in windows, the enclosed sunroom is a serene, light-filled retreat that invites quiet mornings, afternoon reading, or simply taking in the beauty of the surrounding property throughout the seasons, sure to become a favorite. The home offers 3 bedrooms and abundant natural light throughout. A detached 2-car garage is complemented by a versatile studio above, where a large picture window captures views of the Sound, ideal for an artist’s retreat or home office. A rare blend of historic charm, modern comfort, and coastal lifestyle.

2850 & 2856 N Wading River Road, Wading River

$1,225,000
5 Beds 2 Baths 970683 MLS
Soak up days on the Peconic Bay! Deeded boat slip and bay beach included! Tucked away in the coastal enclave of BayWoods in Aquebogue, on Long Island's North Fork this home is all about easy coastal living. Set on a peaceful, saltwater tidal pond, it's the serene setting boasting 5 spacious bedrooms, 2 of which are on the main floor. Formal dining room, sun room/den all with prime southern exposure brimming with natural light. The property includes a deeded boat slip and private bay beach access, so days on the water and sunset beach walks are a part of everyday life. Located in close proximity to North Fork wineries, restaurants, local farm stands, and charming villages. This is a welcoming retreat where nature, boating, and beach life come together perfectly. Updates: Propane heating system (2023); On-demand hot water (2019); CAC Condensers (2025); Interior of home painted (2026)

55 Leafy Way, Aquebogue

$1,525,000
3 Beds 3 Baths 948227 MLS
The Lighthouse” on Peconic Bay Welcome to 112 Pine Avenue, a waterfront home located where a peninsula meets the open expanse of Peconic Bay at the end of a calm shoreline. Surrounded by water on three sides, the property offers privacy, open views and a distinctive setting. The residence offers approximately 2,100 square feet with 3 bedrooms and 3.5 bathrooms and has been enhanced with luxury renovations that elevate modern functionality. Most rooms capture bay views that radiate with natural light throughout the day. Direct water access begins at the driveway and continues along the shoreline. The nearby Little Pines community beach provides shared access for swimming, sun and enjoying Peconic Bay. The surrounding preserve supports regular wildlife sightings, while the canal beside the home has a gentle flow and provides a setting suitable for swimming, paddling or snorkeling. Property features include keyless entry, a Briscoe alarm system, built-in fire alarms, storm shutters and a whole-house generator. A Savant sound system supports indoor and outdoor audio. A retractable awning provides shade over the back deck overlooking the landscaped lawn and water. An electric grill supports outdoor use. The main level includes a renovated bathroom with steam shower, aromatherapy, Bluetooth sound and adjustable lighting. The dedicated home office overlooks the water and includes independent AC, a professionally installed wired ethernet connection from the router to the desk, and custom shelving with designer wallpaper intentionally designed to create a polished and visually appealing backdrop for video calls. The kitchen includes stainless steel appliances, an electric stove, a whole-house water softener and a filtered water spout at the kitchen sink. The home also features an outdoor shower with rain head. The second-floor primary suite offers a private balcony with expansive panoramic views of the bay, including sunrise views over the water, a walk-in closet and an ensuite bathroom with a soaking tub designed to overlook the water at sunset. This connection to the bay continues throughout the home, reinforcing a consistent sense of flow. “The Lighthouse” at 112 Pine Avenue is a unique opportunity to own a thoughtfully renovated bayfront residence in the Township of Southampton.

112 Pine Avenue, Flanders

$675,000
929287 MLS
Approved Waterfront Build | Reeves Bay | Shovel-Ready One acre of waterfront land overlooking Reeves Bay with full building, wetland, and health department approvals in place—eliminating the typical entitlement timeline and risk. Approved plans include a 3-bedroom, 3 full bath custom residence with full basement and attached 2-car garage, along with a covered front porch, paver walkway, bayside deck, outdoor shower, and private walkway to a dock. Site is fully positioned for immediate development—ideal for builders or investors seeking a streamlined path to completion in a high-demand waterfront market. Strong end-user appeal with direct access to kayaking, paddle boarding, boating, and sunset views over the bay—supporting premium resale or rental positioning. Rare opportunity to acquire a fully approved, shovel-ready waterfront parcel—build immediately and capture value without delay. Price reflects land only. No structures or improvements included.

910 Flanders Road, Flanders

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.