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Build Your Dream Estate in Southold. Prime 2 Acre Corner Lot Near the Beach An exceptional opportunity awaits in one of Southold’s most desirable neighborhoods. This premium 2-acre corner parcel provides the ideal setting to design and build a custom luxury residence with plenty of room for a pool, pool house, guest cottage, tennis or pickleball courts, lush gardens, and expansive outdoor living spaces. The location is unmatched; just moments from gorgeous beaches, acclaimed vineyards, farmstands, and the charming Southold village center, offering the perfect balance of tranquility and convenience. Major due diligence items have already been completed, including an updated property survey, Suffolk County Board of Health approval, and preliminary site and building plans, making this a smooth path toward your vision. With privacy, natural beauty, and endless potential, this property is the perfect canvas to craft your forever home or seasonal North Fork retreat. A rare offering in a true destination location — explore the possibilities and make your dream home a reality.

942473 MLS

Build Your Dream Estate in Southold. Prime 2 Acre Corner Lot Near the Beach An exceptional opportunity awaits in one of Southold’s most desirable neighborhoods. This premium 2-acre corner parcel provides the ideal setting to design and build a custom luxury residence with plenty of room for a pool, pool house, guest cottage, tennis or pickleball courts, lush gardens, and expansive outdoor living spaces. The location is unmatched; just moments from gorgeous beaches, acclaimed vineyards, farmstands, and the charming Southold village center, offering the perfect balance of tranquility and convenience. Major due diligence items have already been completed, including an updated property survey, Suffolk County Board of Health approval, and preliminary site and building plans, making this a smooth path toward your vision. With privacy, natural beauty, and endless potential, this property is the perfect canvas to craft your forever home or seasonal North Fork retreat. A rare offering in a true destination location — explore the possibilities and make your dream home a reality.

195 Mt Beulah Avenue, Southold

$890,000

***NEW IMPROVED PRICE**Ideal for the Self-Employed Buyer or Multigenerational family: Flexibility, and Income Potential in Southold’s Wine Country. This beautifully renovated farmhouse blends timeless charm with modern comfort—perfectly suited for self-employed professionals. With 5 spacious bedrooms and 3 elegantly updated bathrooms across 2 floors, this home offers flexibility. A comprehensive gut renovation done less than five years ago, gives buyers the opportunity to unpack and enjoy! For those looking to generate additional income or accommodate multigenerational living, the layout provides an ideal opportunity—pending proper permits—to create a separate 2-bedroom, 1-bath rental unit. This option adds a layer of flexibility and long-term value for self-employed buyers who may benefit from rental income or guest accommodations. A full basement offers generous storage and the potential for a home gym, studio, or workshop. The detached 1.5-car garage and two driveways offer parking for up to 8 vehicles! The spacious yard provides plenty of room for a pool or outdoor entertaining. Located just minutes from pristine beaches and only a mile from Southold’s quaint downtown with shops, dining, and a vibrant local scene, the home is also close to farm stands, award-winning wineries, breweries, and boating—making it the ideal base for a fulfilling and inspired lifestyle.

5 Beds ⋅ 3 Baths ⋅ 840724 MLS

***NEW IMPROVED PRICE**Ideal for the Self-Employed Buyer or Multigenerational family: Flexibility, and Income Potential in Southold’s Wine Country. This beautifully renovated farmhouse blends timeless charm with modern comfort—perfectly suited for self-employed professionals. With 5 spacious bedrooms and 3 elegantly updated bathrooms across 2 floors, this home offers flexibility. A comprehensive gut renovation done less than five years ago, gives buyers the opportunity to unpack and enjoy! For those looking to generate additional income or accommodate multigenerational living, the layout provides an ideal opportunity—pending proper permits—to create a separate 2-bedroom, 1-bath rental unit. This option adds a layer of flexibility and long-term value for self-employed buyers who may benefit from rental income or guest accommodations. A full basement offers generous storage and the potential for a home gym, studio, or workshop. The detached 1.5-car garage and two driveways offer parking for up to 8 vehicles! The spacious yard provides plenty of room for a pool or outdoor entertaining. Located just minutes from pristine beaches and only a mile from Southold’s quaint downtown with shops, dining, and a vibrant local scene, the home is also close to farm stands, award-winning wineries, breweries, and boating—making it the ideal base for a fulfilling and inspired lifestyle.

4100 Youngs Avenue, Southold

$882,000

Unique opportunity in Southold to create your dream home on the North Fork. This A-frame-style house, reminiscent of a chalet, features a striking wall of windows that leads to open rafter ceilings. The main floor is perfect for entertaining, with a quaint kitchen, two bedrooms, a full bathroom, and the sunken A-frame living room that captures the essence of the home. Adjacent to the living room, sliding doors open to a wrap-around deck overlooking the side yard, which is ideal for al fresco dining or enjoying an evening gathered around the fire pit. Upstairs, you'll find a spacious loft that can serve as an office, recreational space, or lounge. The loft includes a balcony that overlooks the living room and provides access to a mini rooftop terrace with views of the backyard. The lower level, which has a private entrance, is ready for full renovation and is already framed for a potential bedroom, bathroom, laundry room, and additional storage. The two-car attached garage can be repurposed for additional living space or perhaps a gym. The property encompasses 1.37 acres, having been merged with the adjacent land, providing ample space for a potential pool, tennis court, or additional structures while ensuring plenty of privacy. Wonderful investment opportunity. You'll also enjoy convenient access to the beaches of Southold Bay, the village, and local vineyards. This listing may include images that have been digitally altered or virtually staged. Original, unedited images are available upon request.

2 Beds ⋅ 1 Baths ⋅ 983742 MLS

Unique opportunity in Southold to create your dream home on the North Fork. This A-frame-style house, reminiscent of a chalet, features a striking wall of windows that leads to open rafter ceilings. The main floor is perfect for entertaining, with a quaint kitchen, two bedrooms, a full bathroom, and the sunken A-frame living room that captures the essence of the home. Adjacent to the living room, sliding doors open to a wrap-around deck overlooking the side yard, which is ideal for al fresco dining or enjoying an evening gathered around the fire pit. Upstairs, you'll find a spacious loft that can serve as an office, recreational space, or lounge. The loft includes a balcony that overlooks the living room and provides access to a mini rooftop terrace with views of the backyard. The lower level, which has a private entrance, is ready for full renovation and is already framed for a potential bedroom, bathroom, laundry room, and additional storage. The two-car attached garage can be repurposed for additional living space or perhaps a gym. The property encompasses 1.37 acres, having been merged with the adjacent land, providing ample space for a potential pool, tennis court, or additional structures while ensuring plenty of privacy. Wonderful investment opportunity. You'll also enjoy convenient access to the beaches of Southold Bay, the village, and local vineyards. This listing may include images that have been digitally altered or virtually staged. Original, unedited images are available upon request.

600 Highwood Road, Southold

$775,000

Build your North Fork dream in the heart of Southold. This exceptional 0.96-acre parcel is nestled among mature trees and surrounded by the scenic beauty of farmland and nature. This peaceful setting with easy access to Long Island Sound beaches, with breathtaking sunsets, acclaimed wineries, farm stands, marinas, and charming village amenities. Buyer is responsible for verifying all zoning, permits, and permitted uses with the Town of Southold. Artist Rendering- For Illustrative Purposes Only. Images are artistic interpretations and should not be relied upon as representations of existing conditions, future improvements, or development potential. All land use, zoning, and building approvals are subject to review by the Town of Southold and applicable agencies.

1031247 MLS

Build your North Fork dream in the heart of Southold. This exceptional 0.96-acre parcel is nestled among mature trees and surrounded by the scenic beauty of farmland and nature. This peaceful setting with easy access to Long Island Sound beaches, with breathtaking sunsets, acclaimed wineries, farm stands, marinas, and charming village amenities. Buyer is responsible for verifying all zoning, permits, and permitted uses with the Town of Southold. Artist Rendering- For Illustrative Purposes Only. Images are artistic interpretations and should not be relied upon as representations of existing conditions, future improvements, or development potential. All land use, zoning, and building approvals are subject to review by the Town of Southold and applicable agencies.

13260 Soundview Avenue, Southold

$740,000

A great business and/or investment opportunity awaits! Once a popular Southold holistic/chiropractic office with separate living quarters and then a childcare facility and apartment, this adaptable split-level property is awaiting its next creativite live-in business venture! Located on a beautiful .83 acre, this property fronts the high visibility County Road 48/North Road and backs up to scenic preserved farmland. The ground floor has a large waiting room, offices with sinks, and a half bath. The 2nd floor is a spacious 2-bedroom 1 bath rental apartment that could also be used as the business owner's home. Its Limited Business Zoning offers many opportunities including professional office, retail operation, custom workshop, garden shop/nursery, restaurant, dog and cat care facility, repair shop, etc.

1016880 MLS

A great business and/or investment opportunity awaits! Once a popular Southold holistic/chiropractic office with separate living quarters and then a childcare facility and apartment, this adaptable split-level property is awaiting its next creativite live-in business venture! Located on a beautiful .83 acre, this property fronts the high visibility County Road 48/North Road and backs up to scenic preserved farmland. The ground floor has a large waiting room, offices with sinks, and a half bath. The 2nd floor is a spacious 2-bedroom 1 bath rental apartment that could also be used as the business owner's home. Its Limited Business Zoning offers many opportunities including professional office, retail operation, custom workshop, garden shop/nursery, restaurant, dog and cat care facility, repair shop, etc.

44600 County Road 48, Southold

$740,000

A great business and/or investment opportunity awaits! Once a popular Southold holistic/chiropractic office with separate living quarters and then a childcare facility and apartment, this adaptable split-level property is awaiting its next creativite live-in business venture! Located on a beautiful .83 acre, this property fronts the high visibility County Road 48/North Road and backs up to scenic preserved farmland. The ground floor has a large waiting room, offices with sinks, and a half bath. The 2nd floor is a spacious 2-bedroom 1 bath rental apartment that could also be used as the business owner's home. Its Limited Business Zoning offers many opportunities including professional office, retail operation, custom workshop, garden shop/nursery, restaurant, dog and cat care facility, repair shop, etc.

2 Beds ⋅ 2 Baths ⋅ 1015353 MLS

A great business and/or investment opportunity awaits! Once a popular Southold holistic/chiropractic office with separate living quarters and then a childcare facility and apartment, this adaptable split-level property is awaiting its next creativite live-in business venture! Located on a beautiful .83 acre, this property fronts the high visibility County Road 48/North Road and backs up to scenic preserved farmland. The ground floor has a large waiting room, offices with sinks, and a half bath. The 2nd floor is a spacious 2-bedroom 1 bath rental apartment that could also be used as the business owner's home. Its Limited Business Zoning offers many opportunities including professional office, retail operation, custom workshop, garden shop/nursery, restaurant, dog and cat care facility, repair shop, etc.

44600 County Road 48, Southold

$733,000

Great office space with apartment! The office has 5+ exam rooms, large waiting area and 2 half baths. The 1 bedroom, 1 bath apartment has a large kitchen, loft area and large deck. The property sits on one acre and has ample parking. The office and apartment must be owner occupied, or the entire structure could be converted to all living space as well as keeping the apartment. Many uses for this property - medical property, nursery school, place or worship and many more!

1 Beds ⋅ 4 Baths ⋅ 889540 MLS

Great office space with apartment! The office has 5+ exam rooms, large waiting area and 2 half baths. The 1 bedroom, 1 bath apartment has a large kitchen, loft area and large deck. The property sits on one acre and has ample parking. The office and apartment must be owner occupied, or the entire structure could be converted to all living space as well as keeping the apartment. Many uses for this property - medical property, nursery school, place or worship and many more!

Southold

$720,000

Southold- Get ready to kick off your shoes this summer... Kenneys Beach is waiting for you. This two bedroom, one bath ranch home has been lovingly maintained. An easy, open floor plan consists of a living room, eat-in-kitchen, and separate dining room/den. Slider to a large patio perfect for entertaining and family get-togethers. Two comfortable bedrooms. One bath with a tub/shower combo. Wood floors throughout. A level .29 acre parcel features a pebble fire pit seating area, lovely plantings, gardens, and a manicured lawn. Outdoor shower. Partial basement. Situated between Kenney and McCabe's Long Island Sound beaches. This home is an exceptional value, ready to use as is, or as the starting point for your North Fork year-round or vacation home. Everything is right here...beaches, restaurants, golf, farm stands, wineries and shopping. An excellent opportunity to enter the North Fork market.

2 Beds ⋅ 1 Baths ⋅ 947455 MLS

Southold- Get ready to kick off your shoes this summer... Kenneys Beach is waiting for you. This two bedroom, one bath ranch home has been lovingly maintained. An easy, open floor plan consists of a living room, eat-in-kitchen, and separate dining room/den. Slider to a large patio perfect for entertaining and family get-togethers. Two comfortable bedrooms. One bath with a tub/shower combo. Wood floors throughout. A level .29 acre parcel features a pebble fire pit seating area, lovely plantings, gardens, and a manicured lawn. Outdoor shower. Partial basement. Situated between Kenney and McCabe's Long Island Sound beaches. This home is an exceptional value, ready to use as is, or as the starting point for your North Fork year-round or vacation home. Everything is right here...beaches, restaurants, golf, farm stands, wineries and shopping. An excellent opportunity to enter the North Fork market.

340 Pine Road, Southold

$718,000

Picture this: you’ve been walking through homes that are either way too much house… or feel like a shoebox with a mortgage. Then you walk into this one and it just clicks, not too big, not too small, and it actually makes sense for real life. It’s a two-bedroom layout that works, and the bathroom is basically begging for a remodel. The pink tile had its moment, but I’d happily retire it and put in something that feels like my style. The kind of update that instantly makes the whole house feel fresher without turning your life into a six-month construction zone. What I really love is how you get two different “hangout spaces” Up front, there’s a sunroom that keeps you connected to the neighborhood, coffee in the morning, wave to the walkers, feel like you’re actually part of a community. Then out back you’ve got a deck where you can disappear a little, because it overlooks the woods and the yard is fenced in, The kitchen is the same vibe: totally functional, but also a clear opportunity. Can use it comfortably right now, and then renovate when ready, and the fact that it could be expanded makes it feel like a smart move. And the neighborhood perk? This is the kind you can’t renovate into a house later: the park and beach at the end of the street. In the summer you get that breeze off the water, that easy “flip-flops and go” lifestyle. It’s the simple stuff that ends up being the best stuff.

2 Beds ⋅ 1 Baths ⋅ 961780 MLS

Picture this: you’ve been walking through homes that are either way too much house… or feel like a shoebox with a mortgage. Then you walk into this one and it just clicks, not too big, not too small, and it actually makes sense for real life. It’s a two-bedroom layout that works, and the bathroom is basically begging for a remodel. The pink tile had its moment, but I’d happily retire it and put in something that feels like my style. The kind of update that instantly makes the whole house feel fresher without turning your life into a six-month construction zone. What I really love is how you get two different “hangout spaces” Up front, there’s a sunroom that keeps you connected to the neighborhood, coffee in the morning, wave to the walkers, feel like you’re actually part of a community. Then out back you’ve got a deck where you can disappear a little, because it overlooks the woods and the yard is fenced in, The kitchen is the same vibe: totally functional, but also a clear opportunity. Can use it comfortably right now, and then renovate when ready, and the fact that it could be expanded makes it feel like a smart move. And the neighborhood perk? This is the kind you can’t renovate into a house later: the park and beach at the end of the street. In the summer you get that breeze off the water, that easy “flip-flops and go” lifestyle. It’s the simple stuff that ends up being the best stuff.

1000 Gin Lane, Southold

$620,000

Welcome to 265 Hummel Ave in Southold, a charming two-bedroom, one-bathroom gem that embodies the perfect balance of comfort and potential. This property is a blank canvas for your imagination, boasting a full attic that presents an exciting opportunity for expansion, allowing you to customize the loft space to your unique needs and taste. The home is situated in a vibrant community that thrives on connectivity and convenience. Just moments from your doorstep, you’ll find the local bus and train station, making your commute or weekend trips a breeze. Additionally, this location places you in close proximity to a variety of local shops, offering everything from everyday essentials to unique finds. Schedule your showing today and do not run the risk of missing out on this fantastic opportunity!

2 Beds ⋅ 1 Baths ⋅ 942515 MLS

Welcome to 265 Hummel Ave in Southold, a charming two-bedroom, one-bathroom gem that embodies the perfect balance of comfort and potential. This property is a blank canvas for your imagination, boasting a full attic that presents an exciting opportunity for expansion, allowing you to customize the loft space to your unique needs and taste. The home is situated in a vibrant community that thrives on connectivity and convenience. Just moments from your doorstep, you’ll find the local bus and train station, making your commute or weekend trips a breeze. Additionally, this location places you in close proximity to a variety of local shops, offering everything from everyday essentials to unique finds. Schedule your showing today and do not run the risk of missing out on this fantastic opportunity!

265 Hummel Avenue, Southold

$605,000

Gorgeous, light, bright, and airy, this immaculate 2-bedroom, 2-bath condominium is located in the highly desirable Founders Village 55+ community. Featuring soaring vaulted ceilings, an eat-in kitchen, spacious living and dining areas, and an inviting open layout, this home is designed for comfortable, low-maintenance living. The primary suite offers a private bath and generous closet space, while a full basement provides exceptional storage and endless possibilities. Enjoy beautifully maintained grounds, a community clubhouse, and pool, all just minutes from Southold Village, wineries, farm stands, beaches, shopping, and transportation. A wonderful opportunity to enjoy the best of the North Fork lifestyle.

2 Beds ⋅ 2 Baths ⋅ 1006443 MLS

Gorgeous, light, bright, and airy, this immaculate 2-bedroom, 2-bath condominium is located in the highly desirable Founders Village 55+ community. Featuring soaring vaulted ceilings, an eat-in kitchen, spacious living and dining areas, and an inviting open layout, this home is designed for comfortable, low-maintenance living. The primary suite offers a private bath and generous closet space, while a full basement provides exceptional storage and endless possibilities. Enjoy beautifully maintained grounds, a community clubhouse, and pool, all just minutes from Southold Village, wineries, farm stands, beaches, shopping, and transportation. A wonderful opportunity to enjoy the best of the North Fork lifestyle.

2555 Youngs Avenue Unit #1D, Southold

$600,000

Ranch Style Home. This Home Features 2 Bedrooms, Full Bath, Dining Area, Eat In Kitchen & 2 Car Garage. Centrally Located To All. Don't Miss This Opportunity!

2 Beds ⋅ 1 Baths ⋅ 1007215 MLS

Ranch Style Home. This Home Features 2 Bedrooms, Full Bath, Dining Area, Eat In Kitchen & 2 Car Garage. Centrally Located To All. Don't Miss This Opportunity!

6900 Main Bayview Road, Southold

$600,000

Wonderful opportunity in prime location to build your dream home on this bright and private corner lot of 0.55 acre in the desirable community of Southold. This land has partial water view and access to ramp at the end of the road to Goose Creek for boating, kayaking, and fishing. And yes, it is only a few minutes from town, restaurants, farmstands, wineries, antique shops, and more.

996413 MLS

Wonderful opportunity in prime location to build your dream home on this bright and private corner lot of 0.55 acre in the desirable community of Southold. This land has partial water view and access to ramp at the end of the road to Goose Creek for boating, kayaking, and fishing. And yes, it is only a few minutes from town, restaurants, farmstands, wineries, antique shops, and more.

105 Mailer Court, Southold

$590,000

Come home to the quintessential historic (ca. 1938) coastal bungalow in Goose Bay Estates. This cabin meets cottage offers a rare opportunity to own a piece of paradise with peaceful water views and exclusive community beach access just 4 houses down the lane. Enjoy the feel of an upstate cabin with pine paneling and a woodburning stove, while gazing at the serene waters of Goose Creek. Whether you're into boating, kayaking, or enjoying sunset swims, the best of the North Fork is at your doorstep. The interior features an inviting open-concept living and dining area with cathedral ceilings, and a bright sunroom anchored by a cozy wood-burning stove perfect for morning coffee and renewing water views. While currently configured as a one-bedroom sanctuary, the home’s original footprint diagrams 2 small bedrooms, and holds significant potential for expansion or a creative renovation. With a little TLC, this "diamond in the rough" can be transformed into your bespoke coastal hideaway. Located minutes from Southold Town beaches, award-winning vineyards, and farm-to-table dining.

2 Beds ⋅ 1 Baths ⋅ 951212 MLS

Come home to the quintessential historic (ca. 1938) coastal bungalow in Goose Bay Estates. This cabin meets cottage offers a rare opportunity to own a piece of paradise with peaceful water views and exclusive community beach access just 4 houses down the lane. Enjoy the feel of an upstate cabin with pine paneling and a woodburning stove, while gazing at the serene waters of Goose Creek. Whether you're into boating, kayaking, or enjoying sunset swims, the best of the North Fork is at your doorstep. The interior features an inviting open-concept living and dining area with cathedral ceilings, and a bright sunroom anchored by a cozy wood-burning stove perfect for morning coffee and renewing water views. While currently configured as a one-bedroom sanctuary, the home’s original footprint diagrams 2 small bedrooms, and holds significant potential for expansion or a creative renovation. With a little TLC, this "diamond in the rough" can be transformed into your bespoke coastal hideaway. Located minutes from Southold Town beaches, award-winning vineyards, and farm-to-table dining.

875 Oak Avenue, Southold

$230,000

Seasonal Condo Near a Memorable Long Island Sound Beach (Town Beach). Studio Apartment is Located on the 2nd Floor. The Condo Offers a Community Room, Lawn with BBQ Area, Laundry, Off Street Parking, Boat Storage, Beach Storage. Electric, Water, Cable and Sewer/Cesspool included in Common Charge. SEASONAL CONDO OPEN APRIL TO NOVEMBER. NOT YEAR ROUND.

1 Baths ⋅ 946493 MLS

Seasonal Condo Near a Memorable Long Island Sound Beach (Town Beach). Studio Apartment is Located on the 2nd Floor. The Condo Offers a Community Room, Lawn with BBQ Area, Laundry, Off Street Parking, Boat Storage, Beach Storage. Electric, Water, Cable and Sewer/Cesspool included in Common Charge. SEASONAL CONDO OPEN APRIL TO NOVEMBER. NOT YEAR ROUND.

52325 County Road 48 Unit #31, Southold