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430 Grove Road, Southold
$699,000
3 Beds ⋅ 1 Baths ⋅ 1060683 MLS
Welcome to 430 Grove Road, Southold — Where the North Fork Lifestyle Becomes Your Everyday Life! Imagine starting your mornings with coffee on your beautiful, window-filled enclosed porch, spending your afternoons exploring local vineyards, breweries, and beaches, and ending your evenings enjoying the peaceful charm of the North Fork. This inviting 3-bedroom ranch offers the perfect opportunity to embrace a lifestyle that feels like a vacation every day. Tucked away in a wonderful Southold setting, this home features a bright, enclosed porch surrounded by windows, a detached garage, and an outdoor shower — perfect for rinsing off after a day on the water or at the beach. Just down the street, enjoy convenient water access where you can launch your paddleboard, kayak, or canoe and explore the beauty of the surrounding waterways. Whether you're looking for a year-round residence, a weekend escape, or your very own North Fork retreat, this property offers so much more than a place to call home. You're not just purchasing a house — you're purchasing the North Fork lifestyle! From award-winning vineyards and local farm stands to waterfront dining, beautiful beaches, and endless outdoor adventures, everything that makes the North Fork so special is waiting for you at 430 Grove Road.

430 Grove Road, Southold
2220 Akerly Pond Lane, Southold
$999,000
5 Beds ⋅ 2 Baths ⋅ 1054880 MLS
Steeped in history dating back to the early 1800s, this five-bedroom, two-bathroom home once served as the main farmhouse of an expansive agricultural tract. Set on two sprawling acres, the property features a large gambrel barn, sweeping lawns, and a white picket fence that complements its classic farmhouse charm. Surrounded by preserved farmland, this pastoral setting is conveniently located in the heart of Southold Hamlet.

2220 Akerly Pond Lane, Southold
Main Bayview Main Bayview, Southold
$999,000
4 Beds ⋅ 4 Baths ⋅ 1059170 MLS
Welcome to 5045 Main Bayview Road, an inviting three-bedroom retreat nestled within Southold’s prestigious Goose Neck community, where privacy, coastal charm, and the relaxed elegance of North Fork living come together. Designed for effortless indoor-outdoor living, the home’s standout feature is its resort-style backyard, a private oasis complete with a beautiful swimming pool, expansive deck, and built-in barbecue. Whether spending leisurely afternoons poolside, dining outdoors, or entertaining family and friends, this exceptional outdoor setting is perfectly suited for enjoying the best of summer on the North Fork. The primary bedroom opens to a private deck overlooking the backyard, offering a peaceful place to begin or end the day while taking in the serene surroundings. A sunroom featuring a hot tub provides an additional space to relax and unwind throughout the seasons. Located within the coveted Goose Neck community, residents enjoy the added luxury of private beach access, creating the quintessential North Fork lifestyle just moments from home. Southold’s celebrated vineyards, farm stands, beaches, restaurants, shops, and charming village destinations are all within easy reach. Perfect as a year-round residence, sophisticated weekend escape, or summer retreat, 5045 Main Bayview Road presents a special opportunity to enjoy privacy, recreation, and coastal living in one of Southold’s most desirable settings.

Main Bayview Main Bayview, Southold
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
270 Opechee Avenue, Southold
$969,000
3 Beds ⋅ 2 Baths ⋅ 1019799 MLS
Welcome to North Fork living for boaters and beach lovers! 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 an 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, two marina (additional $900/season) & kayak storage. Conveniently located just minutes from iconic North Fork farm stands, wineries, golf courses, restaurants and shopping! Call now to schedule your private showing.

270 Opechee Avenue, Southold
136 Bayview Avenue, Southold
$999,000
2 Beds ⋅ 1 Baths ⋅ 1017744 MLS
The Summer has never been sweeter in this coastal cottage right on the water. Peaceful breezes blow while you sit on the covered deck and watch the paddle boarders go by. Located on a dead-end street on Hashamomuck Pond, this home offers a private dock, 2 bedrooms, warm oak floors, spacious living room, and waterfront views galore. Enjoy boating, kayaking, paddleboarding, fishing, and swimming right out your back door. Surrounded by the gorgeous Southold beaches, over 40 wineries, and local farms, the North Fork has it all. Make it a vacation or year-round home, this is the lifestyle you have thought about, why not make it happen now!

136 Bayview Avenue, 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

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.