Southold Homes under $1 million

Welcome to Southold, a picturesque gem nestled on the North Fork of Long Island, New York. Known for its charming coastal landscapes, rich history, and vibrant community, Southold offers a unique blend of tranquility and modern living. With its scenic waterfront views, lush vineyards, and quaint downtown area, this town is the perfect escape for those seeking a serene lifestyle without sacrificing convenience.

Southold is steeped in history, being one of the oldest towns in New York, founded in 1640. Today, it boasts a delightful mix of historic architecture and contemporary homes, making it a captivating place to call home. The area is a haven for outdoor enthusiasts, with numerous parks, beaches, and nature reserves to explore. Whether you enjoy kayaking in the bay, strolling along the sandy shores, or savoring local wines at one of the many nearby vineyards, Southold has something for everyone.

For those looking to invest in a piece of this idyllic paradise, Southold offers an array of homes under $1 million. From charming cottages and cozy bungalows to spacious family homes, there are plenty of options that cater to various tastes and budgets. These properties allow you to experience the beauty and charm of Southold without breaking the bank.

With its friendly community, vibrant local culture, and stunning natural surroundings, Southold is not just a place to live; it’s a lifestyle. Discover your dream home in this enchanting town and embrace all that Southold has to offer!

Newest Southold Homes under $1 million

$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

$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

$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

$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

$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

$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

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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.