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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!

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

$1,100,000

Private Southold Retreat on 2.18 Acres- Tucked away at the end of a private lane in desirable North Fork location, this special property offers the perfect balance of privacy and convenience. Surrounded by preserved land, large properties and a horse property, the picturesque 2.18-acre setting provides a peaceful retreat while remaining just minutes from restaurants, marinas, shops, wineries, beaches, and all attractions on the North Fork. This meticulously maintained single-level home features 4 bedrooms and 3 bathrooms, offering a versatile floor plan designed for comfortable living and entertaining. The private primary en-suite includes a beautifully updated bath with elegant tile work and soaking tub. Two additional guest bedrooms and updated hall bath provide ample accommodations, while a separate wing with its own private entrance offers endless possibilities. Ideal as a home office, guest quarters, or a secondary primary suite, this space includes a sitting room, bedroom, and full bath with a handicap-accessible shower. The spacious, light-filled kitchen is designed for both everyday living and entertaining. Featuring an abundance of cabinetry, expansive counter space, and an efficient layout, the kitchen offers plenty of room for meal preparation and storage. The open design flows into the dining area and living room, creating an inviting atmosphere for casual gatherings or larger celebrations. The dining area offers sliding doors leading to a large deck overlooking the scenic grounds, the perfect setting for outdoor dining, relaxing, or entertaining. The full basement with outside entrance offers endless possibilities for expansion of the living space if desired. Every detail of this residence reflects exceptional care and pride of ownership. Beautifully maintained, the home presents with the feel and quality of new construction. A rare opportunity to own a pristine country retreat with room for a pool, where privacy, natural beauty, and convenience come together in perfect harmony.

4 Beds ⋅ 3 Baths ⋅ 1050202 MLS

Private Southold Retreat on 2.18 Acres- Tucked away at the end of a private lane in desirable North Fork location, this special property offers the perfect balance of privacy and convenience. Surrounded by preserved land, large properties and a horse property, the picturesque 2.18-acre setting provides a peaceful retreat while remaining just minutes from restaurants, marinas, shops, wineries, beaches, and all attractions on the North Fork. This meticulously maintained single-level home features 4 bedrooms and 3 bathrooms, offering a versatile floor plan designed for comfortable living and entertaining. The private primary en-suite includes a beautifully updated bath with elegant tile work and soaking tub. Two additional guest bedrooms and updated hall bath provide ample accommodations, while a separate wing with its own private entrance offers endless possibilities. Ideal as a home office, guest quarters, or a secondary primary suite, this space includes a sitting room, bedroom, and full bath with a handicap-accessible shower. The spacious, light-filled kitchen is designed for both everyday living and entertaining. Featuring an abundance of cabinetry, expansive counter space, and an efficient layout, the kitchen offers plenty of room for meal preparation and storage. The open design flows into the dining area and living room, creating an inviting atmosphere for casual gatherings or larger celebrations. The dining area offers sliding doors leading to a large deck overlooking the scenic grounds, the perfect setting for outdoor dining, relaxing, or entertaining. The full basement with outside entrance offers endless possibilities for expansion of the living space if desired. Every detail of this residence reflects exceptional care and pride of ownership. Beautifully maintained, the home presents with the feel and quality of new construction. A rare opportunity to own a pristine country retreat with room for a pool, where privacy, natural beauty, and convenience come together in perfect harmony.

61341 Route 25, Southold

$605,000

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.

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

$1,495,000

Bring your vision to the waterfront in Southold. Set along a peaceful creek with direct water access, this fully gutted home offers a rare opportunity to create a custom North Fork retreat. A newly installed bulkhead and existing private dock provide the perfect setting for boating, fishing, kayaking and unforgettable days on the water. Renovate, redesign and make it your own—all just minutes from Southold Village, beaches, vineyards and celebrated local restaurants. Property is being sold as-is.

4 Beds ⋅ 4 Baths ⋅ 1051232 MLS

Bring your vision to the waterfront in Southold. Set along a peaceful creek with direct water access, this fully gutted home offers a rare opportunity to create a custom North Fork retreat. A newly installed bulkhead and existing private dock provide the perfect setting for boating, fishing, kayaking and unforgettable days on the water. Renovate, redesign and make it your own—all just minutes from Southold Village, beaches, vineyards and celebrated local restaurants. Property is being sold as-is.

3995 Wells Avenue, Southold

$549,999

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?

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

$1,277,000

Welcome to 1025 Seawood Drive, where space, comfort, and the North Fork lifestyle come together beautifully! Experience the relaxed sophistication of North Fork living in this beautifully, maintained, move-in-ready 4 bedroom, 3.5 bath Colonial in the heart of Southold. Filled with natural light and designed for modern living this home features 9' ceilings, hardwood floors and an easy-flowing layout designed for both everyday living and entertaining. The spacious open areas connect seamlessly to the gourmet eat in kitchen, featuring marble countertops, stainless steel appliances and abundant cabinetry, while a cozy fireplace adds warmth and character. A standout feature is the expansive lower/ground level with 10' ceilings and sliding glass doors opening directly to the backyard--offering outstanding potential for additional living space, perfect for great room, media room, gym, office and entertainment area. Outside enjoy the expansive deck and private, serene backyard ideal setting for morning coffee, summer gatherings, or quiet evenings at home. Perfectly positioned near Southold's beaches, wineries, farm stands, marinas, waterfront parks, boutique shops and top North Fork dining. This move-in-ready home delivers the space, privacy and effortless coastal living that makes the North Fork so special.

4 Beds ⋅ 4 Baths ⋅ 1032396 MLS

Welcome to 1025 Seawood Drive, where space, comfort, and the North Fork lifestyle come together beautifully! Experience the relaxed sophistication of North Fork living in this beautifully, maintained, move-in-ready 4 bedroom, 3.5 bath Colonial in the heart of Southold. Filled with natural light and designed for modern living this home features 9' ceilings, hardwood floors and an easy-flowing layout designed for both everyday living and entertaining. The spacious open areas connect seamlessly to the gourmet eat in kitchen, featuring marble countertops, stainless steel appliances and abundant cabinetry, while a cozy fireplace adds warmth and character. A standout feature is the expansive lower/ground level with 10' ceilings and sliding glass doors opening directly to the backyard--offering outstanding potential for additional living space, perfect for great room, media room, gym, office and entertainment area. Outside enjoy the expansive deck and private, serene backyard ideal setting for morning coffee, summer gatherings, or quiet evenings at home. Perfectly positioned near Southold's beaches, wineries, farm stands, marinas, waterfront parks, boutique shops and top North Fork dining. This move-in-ready home delivers the space, privacy and effortless coastal living that makes the North Fork so special.

1025 Seawood Drive, Southold

$949,000

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.

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

$799,000

Lovely 4 bedroom, 2bath Ranch home lg living room, dining rm and new kitchen 2years ago. Excellent investment property. Surrounded by quite farm field.

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

$969,000

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.

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

$1,299,000

Located in one of the most sought-after locations on the North Fork sits this quintessential cedar shake farmhouse situated on 2 private acres! This home combines timeless charm with modern comforts. The main level features hardwood floors throughout, a spacious living room with a wood-burning fireplace, formal dining room, eat-in kitchen with granite countertops and pantry, a convenient half bath, and a first-floor bedroom currently used as a home office. Andersen windows and ceiling fans throughout provide comfort and abundant natural light. Upstairs, you’ll find a spacious primary suite with a private deck, walk-in shower, and Jacuzzi tub and additional two guest bedrooms which share an updated bath. The full unfinished basement has high ceilings and is perfect for future potential finishing and offers plenty of room for storage. Enjoy the peaceful outdoor setting from the inviting mahogany wraparound front porch or screened-in side porch. Plenty of room pool, garage, guest cottage and more! Close to Southold’s Kenneys, McCabe’s and Town Beach. A rare opportunity to own a private retreat with amazing grounds, perfect for year-round or part time living!

4 Beds ⋅ 3 Baths ⋅ 1023884 MLS

Located in one of the most sought-after locations on the North Fork sits this quintessential cedar shake farmhouse situated on 2 private acres! This home combines timeless charm with modern comforts. The main level features hardwood floors throughout, a spacious living room with a wood-burning fireplace, formal dining room, eat-in kitchen with granite countertops and pantry, a convenient half bath, and a first-floor bedroom currently used as a home office. Andersen windows and ceiling fans throughout provide comfort and abundant natural light. Upstairs, you’ll find a spacious primary suite with a private deck, walk-in shower, and Jacuzzi tub and additional two guest bedrooms which share an updated bath. The full unfinished basement has high ceilings and is perfect for future potential finishing and offers plenty of room for storage. Enjoy the peaceful outdoor setting from the inviting mahogany wraparound front porch or screened-in side porch. Plenty of room pool, garage, guest cottage and more! Close to Southold’s Kenneys, McCabe’s and Town Beach. A rare opportunity to own a private retreat with amazing grounds, perfect for year-round or part time living!

4408 Old North Road, Southold

$1,299,000

Classic Americana meets the North Fork lifestyle on Southold's Bayview Peninsula. Set on a level half acre backing to protected town owned land, this four bedroom, three bath Center Hall Colonial combines timeless design, thoughtful updates, and an exceptional location near Southold's most sought-after waterfront destinations. A welcoming portico leads into a home with wood floors throughout. The living room features a wood burning fireplace, while the formal dining room overlooks the rear yard through a bay window. A butler's passthrough connects to the kitchen, complete with stone countertops, a massive center island, stainless steel appliances, and a stainless-steel range hood. The first floor includes a full bath and adjacent family room that could easily become a first-floor primary suite or private guest space. Upstairs, the primary suite offers a private bath and second floor laundry. Three additional bedrooms share a hall bath. Additional features include an attached two car garage with mudroom access, a full basement with outside entrance, and recently updated roof, heating system, and central air. Life on Bayview Peninsula is all about the water. Pine Neck Boat Ramp, Goose Creek Beach, and Cedar Beach are all nearby. Enjoy award winning wineries, farm stands, and restaurants throughout the North Fork, with the Orient Point Ferry just a short drive away for easy access to New England. Whether you are looking for a year-round residence or a North Fork getaway, 1075 Ships Drive offers an outstanding opportunity to enjoy coastal living in one of Southold's most desirable neighborhoods.

4 Beds ⋅ 3 Baths ⋅ 1016785 MLS

Classic Americana meets the North Fork lifestyle on Southold's Bayview Peninsula. Set on a level half acre backing to protected town owned land, this four bedroom, three bath Center Hall Colonial combines timeless design, thoughtful updates, and an exceptional location near Southold's most sought-after waterfront destinations. A welcoming portico leads into a home with wood floors throughout. The living room features a wood burning fireplace, while the formal dining room overlooks the rear yard through a bay window. A butler's passthrough connects to the kitchen, complete with stone countertops, a massive center island, stainless steel appliances, and a stainless-steel range hood. The first floor includes a full bath and adjacent family room that could easily become a first-floor primary suite or private guest space. Upstairs, the primary suite offers a private bath and second floor laundry. Three additional bedrooms share a hall bath. Additional features include an attached two car garage with mudroom access, a full basement with outside entrance, and recently updated roof, heating system, and central air. Life on Bayview Peninsula is all about the water. Pine Neck Boat Ramp, Goose Creek Beach, and Cedar Beach are all nearby. Enjoy award winning wineries, farm stands, and restaurants throughout the North Fork, with the Orient Point Ferry just a short drive away for easy access to New England. Whether you are looking for a year-round residence or a North Fork getaway, 1075 Ships Drive offers an outstanding opportunity to enjoy coastal living in one of Southold's most desirable neighborhoods.

1075 Ships Drive, Southold

$789,900

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.

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

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.

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

$1,249,000

It's time to put your money in Real Estate! Here's a property that is in prime condition and generates an income plus appreciation! Hamlet Business (HB) zoned property, in the heart of the Hamlet of Southold! Currently a Legal two-family home - each apartment has two bedrooms, wood floors, updated eat-in kitchen, spacious living room, bathroom, window air-conditioners, with lots of natural light coming from widows on all sides of the house. A beautiful two-story, 1,100 square foot, BARN, approximately a hundred-year old, with electric and running water. This rare accessory building has been preserved, refurbished and is functional just waiting to be repurposed - we virtually staged it with an entertaining idea! There is also an active planting field behind the barn with irrigation. The property has mature trees and a substantial lawn making it private and peaceful, and at the same time centrally located for an easy walk to local restaurants, grocery, banks, post office, town hall, and other shopping. There is deeded access to beautiful Founders Landing Bay Beach and Park - very walkable on a lovely spring or summer day! And...it only a few steps to Southold's Long Island Railroad Station as well as the Hampton Jitney bus stop. The Hamlet Business Zoning offers numerous other possibilities. Buy this rental-investment property (apartments will be available to for turnover to new owner shortly) and secure an income while your investment appreciates!

2 Beds ⋅ 1 Baths ⋅ 998148 MLS

It's time to put your money in Real Estate! Here's a property that is in prime condition and generates an income plus appreciation! Hamlet Business (HB) zoned property, in the heart of the Hamlet of Southold! Currently a Legal two-family home - each apartment has two bedrooms, wood floors, updated eat-in kitchen, spacious living room, bathroom, window air-conditioners, with lots of natural light coming from widows on all sides of the house. A beautiful two-story, 1,100 square foot, BARN, approximately a hundred-year old, with electric and running water. This rare accessory building has been preserved, refurbished and is functional just waiting to be repurposed - we virtually staged it with an entertaining idea! There is also an active planting field behind the barn with irrigation. The property has mature trees and a substantial lawn making it private and peaceful, and at the same time centrally located for an easy walk to local restaurants, grocery, banks, post office, town hall, and other shopping. There is deeded access to beautiful Founders Landing Bay Beach and Park - very walkable on a lovely spring or summer day! And...it only a few steps to Southold's Long Island Railroad Station as well as the Hampton Jitney bus stop. The Hamlet Business Zoning offers numerous other possibilities. Buy this rental-investment property (apartments will be available to for turnover to new owner shortly) and secure an income while your investment appreciates!

1220 Youngs Avenue, Southold

$1,150,000

Welcome to 380 Clark Road, a sun-filled North Fork escape perfectly located near the beautiful beaches of Southold. Blending comfort, charm, and endless backyard potential, this turn key home captures the easygoing lifestyle that makes the North Fork so desirable. Natural light pours throughout the home, creating bright, cheerful interiors and a warm, welcoming feel from the moment you arrive. The updated interior offers a relaxed and effortless flow, perfect for summer weekends, entertaining friends, or cozy year-round living in front of the fireplace. Additional improvements include an updated kitchen and renovated bathrooms, thoughtfully designed to combine style, comfort, and functionality. A newer roof installed just two years ago adds further peace of mind, allowing you to simply move in and enjoy. Step outside and the fun really begins. The expansive backyard offers an incredible opportunity to create your dream outdoor retreat with plenty of room for a pool, outdoor kitchen, fire pit, gardens, or the ultimate entertaining space. Whether hosting summer barbecues, relaxing after a beach day, or enjoying evenings under the stars, the property offers the perfect backdrop for making memories. Ideally situated moments from Southold’s beaches, vineyards, farm stands, marinas, and beloved local restaurants, this home places you right in the heart of North Fork living. Beach days, bike rides to wineries, sunset dinners, and laid-back coastal charm are all just minutes away. This listing may include images that have been digitally altered or virtually staged.

2 Beds ⋅ 1 Baths ⋅ 993527 MLS

Welcome to 380 Clark Road, a sun-filled North Fork escape perfectly located near the beautiful beaches of Southold. Blending comfort, charm, and endless backyard potential, this turn key home captures the easygoing lifestyle that makes the North Fork so desirable. Natural light pours throughout the home, creating bright, cheerful interiors and a warm, welcoming feel from the moment you arrive. The updated interior offers a relaxed and effortless flow, perfect for summer weekends, entertaining friends, or cozy year-round living in front of the fireplace. Additional improvements include an updated kitchen and renovated bathrooms, thoughtfully designed to combine style, comfort, and functionality. A newer roof installed just two years ago adds further peace of mind, allowing you to simply move in and enjoy. Step outside and the fun really begins. The expansive backyard offers an incredible opportunity to create your dream outdoor retreat with plenty of room for a pool, outdoor kitchen, fire pit, gardens, or the ultimate entertaining space. Whether hosting summer barbecues, relaxing after a beach day, or enjoying evenings under the stars, the property offers the perfect backdrop for making memories. Ideally situated moments from Southold’s beaches, vineyards, farm stands, marinas, and beloved local restaurants, this home places you right in the heart of North Fork living. Beach days, bike rides to wineries, sunset dinners, and laid-back coastal charm are all just minutes away. This listing may include images that have been digitally altered or virtually staged.

380 Clark Road, Southold

$1,445,000

A new opportunity in Southold features a traditional-style home built with meticulous attention to detail and high-quality craftsmanship. This prime location is just a few blocks away from the highly sought-after Kenneys Beach, one of the most picturesque beaches on the North Fork. Upon entering the home, you are welcomed by a cathedral ceiling that showcases a stunning stone staircase with iron railings. The spacious living room includes a cozy fireplace and an open floor plan that seamlessly connects to the dining room, which is filled with natural light and offers direct access to the backyard patio. The chef's kitchen is equipped with a center island, granite countertops, custom cabinetry, high-end appliances, and a built-in pantry. A breezeway leading to the side yard provides access to the garage, a full bathroom, and a laundry room. Upstairs, the generous primary bedroom features two walk-in closets and an ensuite bathroom finished in marble, complete with radiant heated flooring. Additionally, there are three more bedrooms and a full bathroom, along with a dedicated alcove space that serves as both an office and a casual lounge. The backyard is a private retreat, perfect for al fresco dining and entertaining. It features a spacious patio and mature landscaping, with plenty of room to add a pool or lawn games. This residence also includes an outdoor shower, a two-car attached garage, and a generator. It is conveniently located near all that the East End has to offer. Please note that some photos have been digitally enhanced.

4 Beds ⋅ 3 Baths ⋅ 1000846 MLS

A new opportunity in Southold features a traditional-style home built with meticulous attention to detail and high-quality craftsmanship. This prime location is just a few blocks away from the highly sought-after Kenneys Beach, one of the most picturesque beaches on the North Fork. Upon entering the home, you are welcomed by a cathedral ceiling that showcases a stunning stone staircase with iron railings. The spacious living room includes a cozy fireplace and an open floor plan that seamlessly connects to the dining room, which is filled with natural light and offers direct access to the backyard patio. The chef's kitchen is equipped with a center island, granite countertops, custom cabinetry, high-end appliances, and a built-in pantry. A breezeway leading to the side yard provides access to the garage, a full bathroom, and a laundry room. Upstairs, the generous primary bedroom features two walk-in closets and an ensuite bathroom finished in marble, complete with radiant heated flooring. Additionally, there are three more bedrooms and a full bathroom, along with a dedicated alcove space that serves as both an office and a casual lounge. The backyard is a private retreat, perfect for al fresco dining and entertaining. It features a spacious patio and mature landscaping, with plenty of room to add a pool or lawn games. This residence also includes an outdoor shower, a two-car attached garage, and a generator. It is conveniently located near all that the East End has to offer. Please note that some photos have been digitally enhanced.

2015 Kenneys Road, Southold

$895,000

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.

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

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.

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

$1,425,000

Waterfront Opportunity on Bay Home Road. Welcome to 535 Bay Home Road, a rare and flexible offering on one of the North Fork’s most coveted canal-front streets, located in the prestigious Willow Point community. With panoramic water views, a private dock, and access to a secluded beach, this property combines timeless coastal charm with modern luxury. Buyers can choose from two exclusive paths to own this exceptional property: Option 1: New Construction Package – $3,300,000 Partner with the highly regarded North Fork Building Company to create a custom 2,900 sq ft modern waterfront home, expertly designed to showcase water views and deliver a luxurious coastal lifestyle. Planned Features Include: 3 en suite bedrooms, additional full bath off the mudroom, main-floor flex room (ideal for a 4th bedroom, home office, or den), Heated waterside pool, covered outdoor living room with kitchen and wood-burning fireplace, private dock + floating swim dock, detached two-car garage with unfinished attic space and breezeway. Interior Highlights: Gourmet kitchen with custom cabinetry, quartz countertops, Thermador appliances, gas fireplace in the living room with custom built-in bookcases, 10’ ceilings on the main level, 9’ ceilings upstairs, white oak flooring throughout, Kohler fixtures, Andersen windows, and recessed lighting. Custom molding package, Walk-in closets in all bedrooms and upstairs laundry room. With final plan approvals nearing completion and permits ready to issue, now is the ideal time to customize your finishes and build your North Fork dream home. Option 2: Purchase As-Is with Approved Plans – $1,499,000 Prefer to build on your own schedule or with your own team? The existing home is also available as-is . This includes: Fully approved architectural plans, ready-to-issue building permits, .37-acre lot on a quiet canal with private dock. Prime opportunity to invest in a trophy location with a head start on construction. Whether you're ready to break ground now or planning for the future, 535 Bay Home Road is a rare chance to own one of the North Fork’s most prestigious waterfront streets — just steps to a private beach and directly across from a scenic vineyard.

3 Beds ⋅ 4 Baths ⋅ 924424 MLS

Waterfront Opportunity on Bay Home Road. Welcome to 535 Bay Home Road, a rare and flexible offering on one of the North Fork’s most coveted canal-front streets, located in the prestigious Willow Point community. With panoramic water views, a private dock, and access to a secluded beach, this property combines timeless coastal charm with modern luxury. Buyers can choose from two exclusive paths to own this exceptional property: Option 1: New Construction Package – $3,300,000 Partner with the highly regarded North Fork Building Company to create a custom 2,900 sq ft modern waterfront home, expertly designed to showcase water views and deliver a luxurious coastal lifestyle. Planned Features Include: 3 en suite bedrooms, additional full bath off the mudroom, main-floor flex room (ideal for a 4th bedroom, home office, or den), Heated waterside pool, covered outdoor living room with kitchen and wood-burning fireplace, private dock + floating swim dock, detached two-car garage with unfinished attic space and breezeway. Interior Highlights: Gourmet kitchen with custom cabinetry, quartz countertops, Thermador appliances, gas fireplace in the living room with custom built-in bookcases, 10’ ceilings on the main level, 9’ ceilings upstairs, white oak flooring throughout, Kohler fixtures, Andersen windows, and recessed lighting. Custom molding package, Walk-in closets in all bedrooms and upstairs laundry room. With final plan approvals nearing completion and permits ready to issue, now is the ideal time to customize your finishes and build your North Fork dream home. Option 2: Purchase As-Is with Approved Plans – $1,499,000 Prefer to build on your own schedule or with your own team? The existing home is also available as-is . This includes: Fully approved architectural plans, ready-to-issue building permits, .37-acre lot on a quiet canal with private dock. Prime opportunity to invest in a trophy location with a head start on construction. Whether you're ready to break ground now or planning for the future, 535 Bay Home Road is a rare chance to own one of the North Fork’s most prestigious waterfront streets — just steps to a private beach and directly across from a scenic vineyard.

535 Bay Home Road, Southold

$1,249,000

Southold, North Fork: The historic Boisseau farmhouse, built around 1890, is situated on 1.75 acres (76,230 square feet) with R40 residential zoning, in a picturesque setting featuring mature trees and a sprawling lawn. The property is adjacent to fallow, and partially wooded acreage owned by the Town of Southold. The traditional home boasts a charming covered front porch, an entry foyer, and a spacious living room with a fireplace. The dining room can function as a den and includes pocket doors. The primary floor also offers an eat-in kitchen, a laundry room/pantry, a 3-season room, a full bath, and a back staircase. Upstairs, you will find three large bedrooms and another full bath. The farmhouse retains historic character and details, including original wainscoting, paneled doors, windows, and hardwood floors. Various unique features from a bygone era include a laundry chute, a built-in medicine cabinet, bench seats and cabinets, and a sewing room or nursery that could also serve as a walk-in closet. Additionally, the property includes a two-car garage, a post-and-beam barn (which previously hosted generations of local school dances), a large two-story workshop, and a tool shed, along with the 'tower' of the windmill that once pumped water for the farm. With approximately 200 linear feet of road frontage, this home offers substantial privacy and is ideal for those seeking a true North Fork residence within a village setting with access to Southold Park District amenities including use of the Wharf House. You can have it all at 2055 Boisseau Avenue, with room for a pool or tennis court, horses, or small-scale farming. The barn can accommodate multiple boats or cars. Follow your dreams and explore this incredible opportunity!

3 Beds ⋅ 2 Baths ⋅ L3590177 MLS

Southold, North Fork: The historic Boisseau farmhouse, built around 1890, is situated on 1.75 acres (76,230 square feet) with R40 residential zoning, in a picturesque setting featuring mature trees and a sprawling lawn. The property is adjacent to fallow, and partially wooded acreage owned by the Town of Southold. The traditional home boasts a charming covered front porch, an entry foyer, and a spacious living room with a fireplace. The dining room can function as a den and includes pocket doors. The primary floor also offers an eat-in kitchen, a laundry room/pantry, a 3-season room, a full bath, and a back staircase. Upstairs, you will find three large bedrooms and another full bath. The farmhouse retains historic character and details, including original wainscoting, paneled doors, windows, and hardwood floors. Various unique features from a bygone era include a laundry chute, a built-in medicine cabinet, bench seats and cabinets, and a sewing room or nursery that could also serve as a walk-in closet. Additionally, the property includes a two-car garage, a post-and-beam barn (which previously hosted generations of local school dances), a large two-story workshop, and a tool shed, along with the 'tower' of the windmill that once pumped water for the farm. With approximately 200 linear feet of road frontage, this home offers substantial privacy and is ideal for those seeking a true North Fork residence within a village setting with access to Southold Park District amenities including use of the Wharf House. You can have it all at 2055 Boisseau Avenue, with room for a pool or tennis court, horses, or small-scale farming. The barn can accommodate multiple boats or cars. Follow your dreams and explore this incredible opportunity!

2055 Boisseau Avenue, Southold