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Southold Real Estate

     

    Southold, is a hamlet in the township of the same name. The hamlet of Southold is 93 acres of 122 parcels of land, located on the eastern end of Long Island in an area colloquially called the North Fork. Settled in 1640, Southold was the first English Settlement in the future New York State. There has been a tug-of-war between Southold and Southampton for ages as to which town was actually settled first. Those of us in Southold, believe that since the first harvest came from Southold – it had to be first!

     

    Southold offers a more relaxed way of life, with beautiful Beaches, Vineyards, Farms and Restaurants. Homes in Southold, especially with access to waterfront, are sought-after second homes making the location a desirable resort community offering a welcomed respite from the hustle and bustle of New York City less than 100 miles away.

    Southold’s rich history can be seen through many of the Victorian homes and Farmhouses in the community. Southold’s oldest structures – some dating to pre-revolutionary war - are found on and around Main Street in the Historic District, are part of the National Register of Historic Places. The Hamlet of Southold is the most commercially active business district on the North Fork between Riverhead and Greenport, and home to Southold Town Hall.

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    Showing 11 - 20 of 101 results| view:  results per page« 1|2|3|4|5|...|last »
    • This prime Southold property offers a fantastic opportunity for subdivision and development! Spanning over 4 acres, surrounded by development rights sold land and only half a mile to McCabes Beach, this idyllic North Fork property is ready to change hands, and this rare offering has incredible potential. Some ideas include subdividing the property and building another home on the back piece or updating and expanding the current residence to create a spectacular estate! The property includes a solid, well-built home from 1967 with a modernized kitchen and updated bathrooms (2020), oak wood floors throughout the first floor (under the carpets), Central Air Conditioning (on the first floor, but can be easily added to the second floor), generator, and a cozy living room with wood burning fireplace. The dining area has sliders to a large wood deck overlooking forever farm views. Other amenities include a two-car garage and a full, dry basement. The home is currently on well water with a filtration system, but public water in the street is available for hookup if desired. The roof was replaced about 10 years ago with 30-year shingles & the driveway was repaved within the last year. This property is not only well-maintained but also ready for your vision. Opportunities like this are rare, so don’t miss out! 28
      6005 Hortons Lane Southold, NY 11971
      $2,200,000
      4 Bedrooms 2 Full Baths
      Single Family For Sale ML# 3584997
      This prime Southold property offers a fantastic opportunity for subdivision and development! Spanning over 4 acres, surrounded by development rights sold land and only half a mile to McCabes Beach, this idyllic North Fork property is ready to change hands, and this rare offering has incredible potential. Some ideas include subdividing the property and building another home on the back piece or updating and expanding the current residence to create a spectacular estate! The property includes a solid, well-built home from 1967 with a modernized kitchen and updated bathrooms (2020), oak wood floors throughout the first floor (under the carpets), Central Air Conditioning (on the first floor, but can be easily added to the second floor), generator, and a cozy living room with wood burning fireplace. The dining area has sliders to a large wood deck overlooking forever farm views. Other amenities include a two-car garage and a full, dry basement. The home is currently on well water with a filtration system, but public water in the street is available for hookup if desired. The roof was replaced about 10 years ago with 30-year shingles & the driveway was repaved within the last year. This property is not only well-maintained but also ready for your vision. Opportunities like this are rare, so don’t miss out!
      Presented By: Douglas Elliman Real Estate  631-354-8100
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Located just a stone’s throw away from Kenney’s Beach, this 6 bedroom, 4 bath stately brick beauty was built in 2007 and sits on 2+ bucolic acres. This home is adorned with luxurious features including radiant heat throughout the kitchen and foyer, designer appliances, custom cabinetry and a lovely balcony located off of one of the bedrooms. There is a grand two-story entry, a spacious eat-in kitchen adjacent to the great room with a cozy wood-burning fireplace, plus a first floor bedroom. The paved rear yard, stone fire pit and new inground pool with built in sitting area and table are to name just a few attributes of this incredible home. Come and make it your own! 30
      1820 Kenneys Rd Southold, NY 11971
      $1,985,000
      6 Bedrooms 4 Full Baths Sq. Ft. 4000.00:#
      Single Family For Sale ML# 3577500
      Located just a stone’s throw away from Kenney’s Beach, this 6 bedroom, 4 bath stately brick beauty was built in 2007 and sits on 2+ bucolic acres. This home is adorned with luxurious features including radiant heat throughout the kitchen and foyer, designer appliances, custom cabinetry and a lovely balcony located off of one of the bedrooms. There is a grand two-story entry, a spacious eat-in kitchen adjacent to the great room with a cozy wood-burning fireplace, plus a first floor bedroom. The paved rear yard, stone fire pit and new inground pool with built in sitting area and table are to name just a few attributes of this incredible home. Come and make it your own!
      Presented By: Compass Greater NY LLC  516-517-4751
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Prime location with great exposure! Excellent opportunity to own a profitable restaurant business and property with tremendous growth potential. Includes 1.5 acres of clear level land on Route 48, a well-traveled North Fork thoroughfare. The property has a successful fully functioning turnkey restaurant with plenty of parking and seating plus scenic rear view. Large open beautiful rear yard with view for catered outdoor events. A beautiful Wedding venue !, Additional information: Business Located At:447870 Cty Rd 48, Southold, NY, Dining seats:100, Building Size:2784 SQ FT 23
      44780 County Road 48 Southold, NY 11971
      $1,950,000
      Sq. Ft. 3000.00:#
      Retail Commercial ML# 3588916
      Prime location with great exposure! Excellent opportunity to own a profitable restaurant business and property with tremendous growth potential. Includes 1.5 acres of clear level land on Route 48, a well-traveled North Fork thoroughfare. The property has a successful fully functioning turnkey restaurant with plenty of parking and seating plus scenic rear view. Large open beautiful rear yard with view for catered outdoor events. A beautiful Wedding venue !, Additional information: Business Located At:447870 Cty Rd 48, Southold, NY, Dining seats:100, Building Size:2784 SQ FT
      Presented By: Thomas J McCarthy Real Estate  631-765-5815
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Designer Modern Farmhouse set on over 3.35 Acres with farm and scenic views, Renovated 2023, Open Concept LR/DR/KIT, Gorgeous KIT with quartz countertops, SS Appl., new, new, new, windows, interior and exterior doors, flooring throughout, baths, boiler, well pump and tank, hot water heater, spectacular 20x40 in ground pool with Cambridge paver patio, front porch. Close to McCabe beach or quick drive for incredible sunsets. Access to Resident only Town beaches, boat ramps and parks with town permit. Farm animals permitted. Marina, and airstrip nearby. 28
      3715 Hortons Lane Southold, NY 11971
      $1,850,000
      4 Bedrooms 4 Full Baths Sq. Ft. 3100.00:#
      Single Family For Sale ML# 3582082
      Designer Modern Farmhouse set on over 3.35 Acres with farm and scenic views, Renovated 2023, Open Concept LR/DR/KIT, Gorgeous KIT with quartz countertops, SS Appl., new, new, new, windows, interior and exterior doors, flooring throughout, baths, boiler, well pump and tank, hot water heater, spectacular 20x40 in ground pool with Cambridge paver patio, front porch. Close to McCabe beach or quick drive for incredible sunsets. Access to Resident only Town beaches, boat ramps and parks with town permit. Farm animals permitted. Marina, and airstrip nearby.
      Presented By: Coldwell Banker American Homes  516-302-8500
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Spanning 3.82 acres, this generous home seamlessly blends luxury with comfort. The formal entry opens to an oversized great room, where a soaring ceiling and a striking stone fireplace are complemented by a wet bar-perfect for entertaining. The kitchen, updated in 2023 with sleek stainless-steel appliances, counters, and backsplash, is a chef’s dream. Two well-sized bedrooms share a large full bath on the main floor, offering flexibility and convenience. Ascend to the second floor to discover a sprawling 1, 300 sq. ft. master suite, complete with walk-in closets, an office, and a luxurious master bath. Designed for an indoor-outdoor living experience, this home features a screened room leading to over 750 sq. ft. of IPE decking. The outdoor space is a true retreat, featuring a heated inground pool with a striking stone surround ideal for lounging and dining, all beautifully fenced and surrounded by meticulous landscaping. All systems in the home are regularly maintained, providing peace of mind. Additional highlights include radiant heated tile floors, ensuring year-round comfort and reliability. 31
      9390 N Bayview Rd Southold, NY 11971
      $1,850,000
      3 Bedrooms 2 Full Baths 1 Half Bath Sq. Ft. 3700.00:#
      Single Family For Sale ML# 3576752
      Spanning 3.82 acres, this generous home seamlessly blends luxury with comfort. The formal entry opens to an oversized great room, where a soaring ceiling and a striking stone fireplace are complemented by a wet bar-perfect for entertaining. The kitchen, updated in 2023 with sleek stainless-steel appliances, counters, and backsplash, is a chef’s dream. Two well-sized bedrooms share a large full bath on the main floor, offering flexibility and convenience. Ascend to the second floor to discover a sprawling 1, 300 sq. ft. master suite, complete with walk-in closets, an office, and a luxurious master bath. Designed for an indoor-outdoor living experience, this home features a screened room leading to over 750 sq. ft. of IPE decking. The outdoor space is a true retreat, featuring a heated inground pool with a striking stone surround ideal for lounging and dining, all beautifully fenced and surrounded by meticulous landscaping. All systems in the home are regularly maintained, providing peace of mind. Additional highlights include radiant heated tile floors, ensuring year-round comfort and reliability.
      Presented By: Daniel Gale Sothebys Intl Rlty  631-734-5439
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 2 Acres Of Highly Desirable Hamlet Business Zoning. Subdividable Into Half Acre Lots Or Build Multiple Structures. Multiple Residential Units Possible Or Residential/Commercial Mix. 4 Buildings Possible As Of Right. Great Route 25 Exposure & Great Location In Center Of Hamlet! Commercial Listing MLS# 3530579 4
      55975 Route 25 Southold, NY 11971
      $1,600,000
      Unimproved Land For Sale ML# 3530714
      2 Acres Of Highly Desirable Hamlet Business Zoning. Subdividable Into Half Acre Lots Or Build Multiple Structures. Multiple Residential Units Possible Or Residential/Commercial Mix. 4 Buildings Possible As Of Right. Great Route 25 Exposure & Great Location In Center Of Hamlet! Commercial Listing MLS# 3530579
      Presented By: Thomas J McCarthy Real Estate  631-765-5815
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 2 Acres Of Highly Desirable Hamlet Business Zoning. Subdividable Into Half Acre Lots Or Build Multiple Structures. Multiple Residential Units Possible Or Residential/Commercial Mix. 4 Buildings Possible As Of Right. Great Route 25 Exposure & Great Location In Center of Hamlet! Land Listing MLS# 3530714 5
      55975 Route 25 Southold, NY 11971
      $1,600,000
      Misc Commercial ML# 3530579
      2 Acres Of Highly Desirable Hamlet Business Zoning. Subdividable Into Half Acre Lots Or Build Multiple Structures. Multiple Residential Units Possible Or Residential/Commercial Mix. 4 Buildings Possible As Of Right. Great Route 25 Exposure & Great Location In Center of Hamlet! Land Listing MLS# 3530714
      Presented By: Thomas J McCarthy Real Estate  631-765-5815
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 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!, Additional information: Appearance:immaculate, Interior Features:Lr/Dr 36
      2055 Boisseau Avenue Southold, NY 11971
      $1,599,000
      3 Bedrooms 1 Full Bath 1 Half Bath Sq. Ft. 2000.00:#
      Single Family For Sale ML# 3590177
      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!, Additional information: Appearance:immaculate, Interior Features:Lr/Dr
      Presented By: Town And Country Real Estate  631-298-0600
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Great Opportunity To Own 3500 Sq Ft. On 1/2 Acre In High Exposure Location! Numerous Possibilities-- Convenience Store, Retail or Wholesale Business, Storage/Warehouse Facility, Automotive Services, Garden Sales And The List Goes On! Property Includes Overhead Doors, Waiting Room, Full Bath And Plenty Of Parking. A Profitable Auto Repair Business Also Available --- Not Included In The Asking Price. Zoning allows for Retail/service/professional etc, Additional information: Building Size:3500, Office Pct.:10 23
      45845 County Road 48 Southold, NY 11971
      $1,599,000
      Sq. Ft. 3500.00:#
      Retail Commercial ML# 3586688
      Great Opportunity To Own 3500 Sq Ft. On 1/2 Acre In High Exposure Location! Numerous Possibilities-- Convenience Store, Retail or Wholesale Business, Storage/Warehouse Facility, Automotive Services, Garden Sales And The List Goes On! Property Includes Overhead Doors, Waiting Room, Full Bath And Plenty Of Parking. A Profitable Auto Repair Business Also Available --- Not Included In The Asking Price. Zoning allows for Retail/service/professional etc, Additional information: Building Size:3500, Office Pct.:10
      Presented By: Thomas J McCarthy Real Estate  631-765-5815
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Enter a sanctuary of light and space in this beautifully designed home, where the grandeur of the Long Island Sound meets serene beachside living. As you enter, you’re greeted by a stunning wall of windows that invites the outside in, setting a tranquil tone throughout the residence. The first floor offers three well-appointed bedrooms, including a master with en-suite bathroom with its own private deck accessed through sliding glass doors-an ideal retreat for morning coffees or evening relaxation. Two additional bedrooms have a full bathroom across the hall. Additionally, a separate laundry room provides practical utility without compromising on style. Ascend to the second floor and discover the heart of the home: an open concept living area that combines the living room, dining room, and a modern kitchen equipped with granite countertops and new stainless steel appliances. Cathedral ceilings with exposed wooden beams accentuate the feeling of openness, further enhanced by plentiful natural light and two sliding glass doors that lead out to an impressive 1, 400 square foot wrap-around deck. Here, panoramic views of the Long Island Sound unfold in every direction, offering a breathtaking backdrop for entertaining or quiet reflection. Outside, the property is bordered by preserved land, ensuring unspoiled vistas and privacy. Just a direct half-mile down the street lies Kenney’s Beach, a sandy beach, rare for the Long Island Sound that stretches for miles. Whether you are meandering east towards Horton’s Point Lighthouse or west towards Goldsmith’s Inlet, the journey is as captivating as the destination. The nearby 60-acre nature trail just down the beach invites leisurely exploration, enhancing the natural allure of the area. Perfect for those who cherish peace, privacy, and the unique beauty of coastal living, this home offers promising unforgettable sunsets and a tranquil lifestyle nestled in a coveted private beach community. 35
      350 West Drive Southold, NY 11971
      $1,395,000
      3 Bedrooms 2 Full Baths 1 Half Bath Sq. Ft. 1900.00:#
      Single Family For Sale ML# 3554407
      Enter a sanctuary of light and space in this beautifully designed home, where the grandeur of the Long Island Sound meets serene beachside living. As you enter, you’re greeted by a stunning wall of windows that invites the outside in, setting a tranquil tone throughout the residence. The first floor offers three well-appointed bedrooms, including a master with en-suite bathroom with its own private deck accessed through sliding glass doors-an ideal retreat for morning coffees or evening relaxation. Two additional bedrooms have a full bathroom across the hall. Additionally, a separate laundry room provides practical utility without compromising on style. Ascend to the second floor and discover the heart of the home: an open concept living area that combines the living room, dining room, and a modern kitchen equipped with granite countertops and new stainless steel appliances. Cathedral ceilings with exposed wooden beams accentuate the feeling of openness, further enhanced by plentiful natural light and two sliding glass doors that lead out to an impressive 1, 400 square foot wrap-around deck. Here, panoramic views of the Long Island Sound unfold in every direction, offering a breathtaking backdrop for entertaining or quiet reflection. Outside, the property is bordered by preserved land, ensuring unspoiled vistas and privacy. Just a direct half-mile down the street lies Kenney’s Beach, a sandy beach, rare for the Long Island Sound that stretches for miles. Whether you are meandering east towards Horton’s Point Lighthouse or west towards Goldsmith’s Inlet, the journey is as captivating as the destination. The nearby 60-acre nature trail just down the beach invites leisurely exploration, enhancing the natural allure of the area. Perfect for those who cherish peace, privacy, and the unique beauty of coastal living, this home offers promising unforgettable sunsets and a tranquil lifestyle nestled in a coveted private beach community.
      Presented By: Douglas Elliman Real Estate  631-477-2220
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
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    Office: 52875 Main Road, Southold NY 11971
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