Southold Homes under $800,000

Welcome to Southold, New York, a charming community located in the picturesque Suffolk County on Long Island. Known for its rich history, stunning waterfront views, and a vibrant local culture, Southold is the perfect place for families and individuals seeking a peaceful yet engaging lifestyle. One of the standout features of this area is its highly regarded school district, which is dedicated to providing quality education and fostering a supportive environment for students. Southold Union Free School District is committed to academic excellence, offering a range of programs and extracurricular activities that cater to diverse interests and talents. With small class sizes and dedicated educators, students here thrive both academically and socially.

For those looking to make Southold their home, there are numerous opportunities to find charming residences under $800,000. Whether you are searching for a cozy cottage, a spacious family home, or a quaint bungalow, Southold's real estate market offers a variety of options that cater to different tastes and budgets. Many of these homes are nestled in serene neighborhoods, providing easy access to local parks, beaches, and community amenities.

Living in Southold means embracing a lifestyle that balances tranquility with access to vibrant community events, farmers' markets, and outdoor recreational activities. With its scenic beauty and strong sense of community, Southold is more than just a place to live; it's a place to call home. Discover your dream home in this idyllic setting today!

Newest Southold Homes under $800,000

$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

$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

$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

$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

$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

$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

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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.