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Perfect Weekend Escape Or Cozy Year-Round Haven! This Adorable 2 Bedroom, 1 Bath Ranch Style Home Is Nestled In A Desirable Southold Location Just Minutes From Local Beaches, The Village And All The Buzzing Restaurants, Shops And Vineyards That Make This Area So Special. Enjoy The Peaceful Backyard And Deck For Summer Bbqs Or Morning Coffee, Plus There's Ample Room For A Pool. So Whether You're Looking To Downsize, Invest In A Weekend Getaway Or Simply Soak Up The Coastal Vibes, This Gem Checks All The Boxes. With Its Unbeatable Location And Irresistible Price, It Won't Last Long--Come See Before It's Gone!

2 Beds ⋅ 1 Baths ⋅ 906933 MLS

Perfect Weekend Escape Or Cozy Year-Round Haven! This Adorable 2 Bedroom, 1 Bath Ranch Style Home Is Nestled In A Desirable Southold Location Just Minutes From Local Beaches, The Village And All The Buzzing Restaurants, Shops And Vineyards That Make This Area So Special. Enjoy The Peaceful Backyard And Deck For Summer Bbqs Or Morning Coffee, Plus There's Ample Room For A Pool. So Whether You're Looking To Downsize, Invest In A Weekend Getaway Or Simply Soak Up The Coastal Vibes, This Gem Checks All The Boxes. With Its Unbeatable Location And Irresistible Price, It Won't Last Long--Come See Before It's Gone!

550 Pine Neck Road, 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

$590,000

Southold - Jonathan Jennings House circa 1761- Moved to its current location in 1761, this clapboard home has historical and architectural significance. The original wood frame house was built with interlocking joists and carelessly dressed ceiling beams. The house has a baker's brick oven with an ash pit, two fireplaces, and a brick foundation. Reportedly the first owner, Jonathan Jennings, served as a soldier in the Revolutionary War, was captured by the British, and died on a prison ship in New York Harbor. Located at the intersection of Main Bayview Road and Baywater Road, the property was also known as "Halfway House" because of its position on the Bayview Peninsula. Subsequent ownership included Southold blacksmith Doc Billy Glover at the turn of the 20th century. Currently, the two-story house consists of a dining room with a brick floor, kitchen, office, parlor room with fireplace, living room with fireplace, three bedrooms and two bathrooms. The level treed property is .63 of an acre. In addition to the house, there are two outbuildings: a two-car garage and a storage building. The storage building has a partially finished second level. Opportunity to own and restore a property with a rich history that is ready for its next chapter. Please call for additional information or to schedule a viewing. Access to Southold Park District beaches. Enjoy the North Fork experience: restaurants, golf, beaches, shopping, farm stands, wineries, breweries, boating. It's all right here.

3 Beds ⋅ 2 Baths ⋅ 917302 MLS

Southold - Jonathan Jennings House circa 1761- Moved to its current location in 1761, this clapboard home has historical and architectural significance. The original wood frame house was built with interlocking joists and carelessly dressed ceiling beams. The house has a baker's brick oven with an ash pit, two fireplaces, and a brick foundation. Reportedly the first owner, Jonathan Jennings, served as a soldier in the Revolutionary War, was captured by the British, and died on a prison ship in New York Harbor. Located at the intersection of Main Bayview Road and Baywater Road, the property was also known as "Halfway House" because of its position on the Bayview Peninsula. Subsequent ownership included Southold blacksmith Doc Billy Glover at the turn of the 20th century. Currently, the two-story house consists of a dining room with a brick floor, kitchen, office, parlor room with fireplace, living room with fireplace, three bedrooms and two bathrooms. The level treed property is .63 of an acre. In addition to the house, there are two outbuildings: a two-car garage and a storage building. The storage building has a partially finished second level. Opportunity to own and restore a property with a rich history that is ready for its next chapter. Please call for additional information or to schedule a viewing. Access to Southold Park District beaches. Enjoy the North Fork experience: restaurants, golf, beaches, shopping, farm stands, wineries, breweries, boating. It's all right here.

3680 Main Bayview Road, Southold

$550,000

Here is a great opportunity to be part of the popular Founders Village Condo Assoc. This Bright and cozy 2- bedroom condo is located in the center of Southolds hamlet As you enter the condo there is a beautifully updated eat in kitchen to your right and a bedroom that can also be used as an office to your left. Down the hall a bit further there is a full bathroom and a large living room/dining room combo complete with a fireplace and sliding glass doors that lead to your patio. The primary bedroom en suite is quite large with walk in closets and a full bathroom. This condo offers a patio for you to sit, relax and enjoy the view. Founders Village also offers a clubhouse and an in-ground pool. If you are looking for easy living close to all that Southold has to offer such as the shops, restaurants, public transportation beaches and the wineries, this is the home for you.

2 Beds ⋅ 2 Baths ⋅ 927213 MLS

Here is a great opportunity to be part of the popular Founders Village Condo Assoc. This Bright and cozy 2- bedroom condo is located in the center of Southolds hamlet As you enter the condo there is a beautifully updated eat in kitchen to your right and a bedroom that can also be used as an office to your left. Down the hall a bit further there is a full bathroom and a large living room/dining room combo complete with a fireplace and sliding glass doors that lead to your patio. The primary bedroom en suite is quite large with walk in closets and a full bathroom. This condo offers a patio for you to sit, relax and enjoy the view. Founders Village also offers a clubhouse and an in-ground pool. If you are looking for easy living close to all that Southold has to offer such as the shops, restaurants, public transportation beaches and the wineries, this is the home for you.

2555 Youngs Avenue Unit #17D, Southold

$535,000

Fantastic opportunity to get into the North Fork market offered via this "move in" condition 2 bedroom/2bathroom cottage on .17 acres w/ large detached 1.5 car garage. The interior features a large and inviting living room, primary ensuite bedroom, guest ensuite bedroom with attached home office, galley kitchen and intimate dining area. The location is fantastic as you can take a short walk or bike into town or walk over to Sophie's Rest for dinner and a cocktail. Finally, the oversized 1.5 car garage could be a great work-shop, artist studio or storage space. Don't let this great property get away!

2 Beds ⋅ 2 Baths ⋅ 927676 MLS

Fantastic opportunity to get into the North Fork market offered via this "move in" condition 2 bedroom/2bathroom cottage on .17 acres w/ large detached 1.5 car garage. The interior features a large and inviting living room, primary ensuite bedroom, guest ensuite bedroom with attached home office, galley kitchen and intimate dining area. The location is fantastic as you can take a short walk or bike into town or walk over to Sophie's Rest for dinner and a cocktail. Finally, the oversized 1.5 car garage could be a great work-shop, artist studio or storage space. Don't let this great property get away!

48920 Route 25, Southold

$525,000

Welcome to Founders Village in Southold. This quiet and quaint 55+ community is located in the heart of Southold Town. This 2 bed 2 bath condo is ready for you to make it home. Just minutes away to Jitney, train station, shopping, groceries, retail, dining, post office, gym and so much more. Either enjoy the beautiful common grounds with the community pool & club house in a quaint setting, or head out to the best beaches the North Fork has to offer! Proximity to over 40 wineries, the Village of Greenport, Shelter Island, and fine dining; everyday will feel like vacation!

2 Beds ⋅ 2 Baths ⋅ 906275 MLS

Welcome to Founders Village in Southold. This quiet and quaint 55+ community is located in the heart of Southold Town. This 2 bed 2 bath condo is ready for you to make it home. Just minutes away to Jitney, train station, shopping, groceries, retail, dining, post office, gym and so much more. Either enjoy the beautiful common grounds with the community pool & club house in a quaint setting, or head out to the best beaches the North Fork has to offer! Proximity to over 40 wineries, the Village of Greenport, Shelter Island, and fine dining; everyday will feel like vacation!

2555 Youngs Avenue Unit #11D, Southold

$500,000

2BR 2Bath condo in Founders Village, Southolds premier 55+ active community. Unit features high ceilings, large primary suite, back patio and full basement. $435 monthly maintenance includes snow removal, beautiful landscaping, access to clubhouse and pool, maintenance of the roof and siding. Located about one half mile from local stores and shops as well as public transportation.

2 Beds ⋅ 2 Baths ⋅ 808158 MLS

2BR 2Bath condo in Founders Village, Southolds premier 55+ active community. Unit features high ceilings, large primary suite, back patio and full basement. $435 monthly maintenance includes snow removal, beautiful landscaping, access to clubhouse and pool, maintenance of the roof and siding. Located about one half mile from local stores and shops as well as public transportation.

2555 Youngs Unit #7D, Southold

$475,000

Here is a wonderful opportunity to build your dream home on this private shy waterfront acre on West Creek. Building plans approved for 2,900 sq ft home with 3BRs/2.5Baths with 2 car garage. This is a flag lot. Property is close to town, beaches and the North Fork has to offer. Seller has the following approvals: Zoning Board of Appeals, Southold Town Trustees wetland permit; health department and house design for the regulatory permits - construction drawings are required.

813014 MLS

Here is a wonderful opportunity to build your dream home on this private shy waterfront acre on West Creek. Building plans approved for 2,900 sq ft home with 3BRs/2.5Baths with 2 car garage. This is a flag lot. Property is close to town, beaches and the North Fork has to offer. Seller has the following approvals: Zoning Board of Appeals, Southold Town Trustees wetland permit; health department and house design for the regulatory permits - construction drawings are required.

4077 Main Bayview Road, Southold

$407,000

Property with vast potential in Prime location, close to Southold beaches, vineyards and short drive to town. Manufactured Home from the early 70's in disrepair, separate one car garage and shed., Additional information: Separate Hotwater Heater:Y

2 Beds ⋅ 2 Baths ⋅ L3562501 MLS

Property with vast potential in Prime location, close to Southold beaches, vineyards and short drive to town. Manufactured Home from the early 70's in disrepair, separate one car garage and shed., Additional information: Separate Hotwater Heater:Y

500 Summer Lane, Southold

$350,000

Turn-key 7-acre vineyard that you've been dreaming of in Southold! Perfectly situated near the village and shops. The vines are in their prime and have been meticulously maintained. Planted in 2006 is 2.2 Acres of Chardonnay and 2.5 Acres of Merlot and 1/2 acre Muscat Ottonel was planted in 2019. Producing approximately 2-3 tons per acre of grapes annually. Fully deer fenced, irrigated by well water, bird netting and connected to electric. This "right-sized" vineyard may be just what you need to create your first vintage or add an additional fruit source to your existing farm operation. This farm has all development rights sold and is for agricultural use only.

874383 MLS

Turn-key 7-acre vineyard that you've been dreaming of in Southold! Perfectly situated near the village and shops. The vines are in their prime and have been meticulously maintained. Planted in 2006 is 2.2 Acres of Chardonnay and 2.5 Acres of Merlot and 1/2 acre Muscat Ottonel was planted in 2019. Producing approximately 2-3 tons per acre of grapes annually. Fully deer fenced, irrigated by well water, bird netting and connected to electric. This "right-sized" vineyard may be just what you need to create your first vintage or add an additional fruit source to your existing farm operation. This farm has all development rights sold and is for agricultural use only.

1135 Boisseau 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