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29400 County Road 48, Peconic
$795,000
3 Beds ⋅ 2 Baths ⋅ 1053365 MLS
Just add a farm stand to this prime high-visibility Peconic location! Set on 1.22 acres, this classic three-bedroom, one-and-a-half-bath home has the space and character that makes country living so appealing. Gorgeous vineyard views, great flexibility with a 3 bay garage perfect for a workshop, greenhouse, or storing vehicles. Owned solar panels also add to the ease of this property. A true North Fork original farmhouse with plenty of room to create memories and enjoy the North Fork country life. Could be you!

29400 County Road 48, Peconic
2555 Youngs Avenue Unit #11A
$605,000
2 Beds ⋅ 2 Baths ⋅ 1051473 MLS
Welcome to this corner residence at Founders Village, where easy, low-maintenance living meets the North Fork lifestyle. This 1,200-square-foot home offers 2 bedrooms, 2 full baths and a full basement, giving you valuable storage and extra space that can be hard to find when downsizing to condominium living. The corner location provides added green space on multiple sides, along with a rear patio that creates a comfortable spot to relax outdoors. Inside, you’ll find wood floors, an eat-in kitchen with newer appliances, comfortable living and dining areas, and high ceilings that create a real open home feel. Residents enjoy a community pool, clubhouse and beautifully maintained grounds. A stroll down the sidewalk leads toward Southold Village, with local shops, restaurants, the LIRR and Hampton Jitney all nearby. Beach access is another added benefit. The property qualifies for both Southold Town and a Southold Park District beach parking permits, offering even more opportunity to enjoy the best of The Long Island Sound and The Peconic Bay beaches. With its private corner setting, full basement, generous storage and community amenities, this home offers a comfortable way to downsize without giving up the space or North Fork lifestyle you want. This is 55+ living, reimagined: all the space and freedom you love, none of the upkeep you don't. Corner Home 11A — where downsizing feels like an upgrade.

2555 Youngs Avenue Unit #11A
2600 Boisseau Avenue, Southold
$549,999
3 Beds ⋅ 1 Baths ⋅ 1043112 MLS
Welcome to 2600 Boisseau Avenue, the best deal in all of Southold. This well-maintained 3-bedroom, 1-bath ranch situated on a spacious .39-acre property in the heart of the North Fork will not disappoint. Offering comfortable single-level living with plenty of potential, this home is a wonderful opportunity to enjoy everything the Southold lifestyle has to offer. Inside, you'll find a functional and inviting layout featuring a comfortable living area, three nicely sized bedrooms, a full bathroom, dining room and an eat-in kitchen. The full basement provides an abundance of additional space for storage, utilities, a workshop, or the potential for future finishing. A detached garage adds even more storage and convenience. Outside, the generous .39-acre property offers plenty of room to relax, entertain, garden, or create your ideal outdoor retreat. Conveniently located near Southold's charming village, local shops and restaurants, beaches, wineries, farm stands, and all that the North Fork has to offer. Whether you're looking for a year-round residence or a weekend getaway, 2600 Boisseau Avenue offers a fantastic opportunity to make Southold home! With taxes less than $5k, what more can you ask for?

2600 Boisseau Avenue, Southold
155 2nd Avenue, Peconic
$949,000
3 Beds ⋅ 2 Baths ⋅ 1036471 MLS
North Fork Coastal Living by the Sound. Welcome to 155 Second Avenue, located in the charming hamlet of Peconic. The beach retreat you've been looking for, just 500 feet from both private and town beach access at Goldsmiths Inlet Beach. Custom built in 2005 by the current owner, this thoughtfully constructed beach home reflects true pride of ownership. Featuring open-concept living, dining, and kitchen areas which flow into a HUGE outdoor second story balcony, where peekaboo water views and beautiful sunsets create the perfect backdrop for relaxing or entertaining. Ready for your personal touch, the home offers a wonderful opportunity to add your own style but gives the peace of mind of an elevated and well built home. Bring your kayak paddleboard or fishing pole, spend your days on the water and your evenings exploring nearby vineyards, farm stands, restaurants, and local landmarks including nearby Horton Point Lighthouse. Well built, wonderfully located, and surrounded by everything that makes the North Fork special, 155 Second Avenue offers an easy coastal lifestyle in the heart of Peconic.

155 2nd Avenue, Peconic
36595 County Rd 48, Peconic
$799,000
4 Beds ⋅ 3 Baths ⋅ 1034331 MLS
Lovely 4 bedroom, 2bath Ranch home lg living room, dining rm and new kitchen 2years ago. Excellent investment property. Surrounded by quite farm field.

36595 County Rd 48, Peconic
270 Opechee Avenue, Southold
$969,000
3 Beds ⋅ 2 Baths ⋅ 1019799 MLS
Welcome to North Fork living! Nestled in the desirable, private beach community of Laughing Water, this charming 3-bedroom, 2-bath Ranch sits on a 0.38-acre lot. Inside, enjoy hardwood floors throughout the living and dining areas, along with a newly updated kitchen featuring new appliances, a center island, and generous storage. A 10’ x 13’ screened-in porch provides the perfect three-season retreat overlooking the backyard. Take advantage of exclusive community amenities, including private beach access, a boat ramp, marina access (additional $900/season) , kayak storage, and a picnic area. Conveniently located just minutes from iconic North Fork farm stands, wineries, golf courses, restaurants and shopping! Don't wait! This house won't last. Call now to schedule your private showing.

270 Opechee Avenue, Southold
725 Peconic Lane, Peconic
$789,900
3 Beds ⋅ 1 Baths ⋅ 1017498 MLS
Fall is just around the corner! Don’t miss your chance to own a home in the heart of Wine Country and experience the beauty and fun of farm country right outside your door! Imagine apple picking, pumpkin picking, fresh pies, local fruit stands, beautiful farms, vineyards, and so much more. **People drive for miles to visit this beautiful destination—you could have the opportunity to live here! ** Welcome to the Heart of North Fork Wine Country! Experience the perfect blend of peace, comfort, and convenience in one of Eastern Long Island’s most sought-after destinations. Nestled on a quiet street surrounded by picturesque vineyards, this charming ranch features brand-new kitchen with stainless-steel appliances brand new bathroom a garage and full basement, offering plenty of space for everyday living and future possibilities. Enjoy the relaxed North Fork lifestyle with farm stands, local markets, and seasonal farm attractions just minutes away. Spend your summers exploring beautiful beaches on both the Long Island Sound and Peconic Bay, and visiting the area’s renowned wineries, vineyards and dining. Outdoor enthusiasts will appreciate the nearby parks featuring tennis courts, baseball fields, and recreational spaces, all within walking distance. Conveniently located with easy access to the main roads and County Road 48, you’ll enjoy both tranquility and accessibility. Don’t miss this rare opportunity to make this your perfect North Fork living lifestyle and rare opportunity to create your dream retreat in Long Island’s celebrated wine country! Check out Tripadvisor, yelp for the best farms, restaurant and winery. So much to choose from you will always have something to do.

725 Peconic Lane, Peconic
430 Grove Road, Southold
$699,000
3 Beds ⋅ 1 Baths ⋅ 921579 MLS
Enter the Season and enjoy North Fork Serenity with the creek across the street to launch into what Southold has to offer. Discover the perfect blend of coastal charm and country tranquility at 430 Grove Road, ideally located in the heart of Southold on the beautiful North Fork of Long Island—where vineyards, farms, and waterfront serenity define the lifestyle. This inviting 3-bedroom, 1-bath ranch-style home sits just three houses from the creek, offering easy access for paddleboarding, kayaking, and peaceful waterfront strolls. The property provides a relaxed atmosphere with room to enjoy the outdoors—whether you’re savoring local wines, exploring nearby beaches, or taking in sunsets over the bay. Enjoy an amazing quality of life surrounded by nature, yet close to all the best the North Fork has to offer—boutique wineries, farm stands, marinas, and charming village shops. Perfect as a year-round residence, weekend retreat, or investment opportunity, this home captures the essence of laid-back coastal living. Come experience why so many fall in love with the Southold lifestyle—where every day feels like a getaway.

430 Grove Road, Southold
240 Lisa Drive, Southold
$895,000
4 Beds ⋅ 3 Baths ⋅ 982950 MLS
Welcome to this spacious 4-bedroom, 2.5-bath two-story home located in the desirable Highpoint Meadows community of Southold. Set on a corner lot, this property offers a welcoming front yard and a generously sized backyard with ample room for a pool and outdoor entertaining. Inside, the home features an open-concept kitchen with new refrigerator, and dining area ideal for everyday living and gatherings, complemented by a formal living room for added versatility. Additional highlights include a convenient laundry room, a two-car attached garage with brand new doors, and a full basement with 8-foot ceilings offering excellent storage and a new hot water heater, gas heat, and potential for future finishing. Perfectly situated to enjoy the North Fork lifestyle, this home is in the Founders Park and Beach Park District, with direct access to a sugar sand beach, park and playground and is just moments from wineries, farm stands, the hamlet, train station, Jitney stop and a variety of shops and restaurants. Easy access to Greenport and Mattituck makes this location both convenient and desirable. A wonderful opportunity to make this home your own and enjoy all that the North Fork has to offer.

240 Lisa Drive, Southold
150 Baywater Avenue, Southold
$850,000
3 Beds ⋅ 4 Baths ⋅ 985489 MLS
Steeped in history and set on a 1.05-acre parcel in the heart of the North Fork, this circa-1663 residence presents a rare opportunity to preserve and reimagine one of Southold’s oldest and most significant properties. Ideally positioned, it is just moments from one of the East End’s finest sandy bay beaches and Croteaux Vineyards, as well as a short drive to renowned wineries, farm stands, and the charming village of Southold, with its shops, waterfront, and access to the Long Island Sound. The land at 150 Baywater Avenue is tied to the remarkable story of Maltby Freeman, a formerly enslaved man who earned his freedom in 1807 and, through extraordinary determination, came to own this very property along Bayview near South Harbor Road. Maltby and his wife, Dorcus Benjamin, began with a single-room structure, gradually expanding it into a family homestead in the early 1800s. Their descendants continued to acquire land, eventually owning a house and 30 acres. The Freeman family’s story is one of the earliest documented examples of Black land ownership and upward mobility on Long Island, and this property stands as a tangible connection to that chapter of American history. The property is offered strictly as-is, presenting a rare opportunity for a developer, preservationist, or visionary owner-builder. Included in the sale is a complete set of fully approved architectural and construction plans, a process that required two years of review by the Historic Preservation Commission, Town Planning Department, and Building Department. This extensive approval represents significant time, cost, and expertise that the next owner will not need to replicate. With permits and plans already secured, construction can begin immediately upon closing. For those seeking a property defined by history, character, and forward potential, 150 Baywater Avenue is ready for its next chapter.

150 Baywater Avenue, Southold

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.