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.

    Learn more about Southold

    to
     
     
     
    Search Search
    •  
    Search

    85  properties match your search;

    Save Search
    Showing 21 - 30 of 85 results| view:  results per page« 1|2|3|4|5|...|last »
    • 1150 Kenneys Rd Southold, NY 11971
      $1,100,000
      Misc For Sale ML# 804225
      This property is a rare gem, offering the flexibility to bring your vision to life. Whether you’re cultivating the land, caring for horses, or simply savoring the peaceful surroundings, this estate promises a lifestyle of unparalleled beauty and possibility.
      Presented By: Thomas J McCarthy Real Estate  631-765-5815
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 1755 Yennecott Drive Southold, NY 11971
      $1,100,000
      6 Bedrooms 2 Full Baths 1 Half Bath Sq. Ft. 3200.00:#
      Single Family For Sale ML# 3509055
      Nestled on a wooded lot, this location feels private while only short distance to downtown Southold and 10 Minutes East to the Village of Greenport. With spacious, airy rooms and hardwood floors, this inviting residence promises a cozy and warm ambiance from the moment you step inside, hand painted wall mosaic, 2 fire places, Spacious Eat In Kitchen, Formal Dining room, Family room and when its time to relax step outside onto the Patio or front porch for a perfect spot to sit with a cup of coffee to observe the serene nature filled yard or the pool. HOA Fee of $150., Additional information: Interior Features:Lr/Dr
      Presented By: Richmond Realty Corp  631-727-5500
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 1475 Oaklawn Avenue Southold, NY 11971
      $1,024,000
      $999,000
      4 Bedrooms 2 Full Baths 1 Half Bath
      Single Family For Sale PRICE REDUCED ML# 3573918
      Welcome to this beautiful, fully renovated home, where classic charm meets modern luxury. Nestled in a serene neighborhood, this exceptional property offers an inviting open floor plan, highlighted by elegant finishes and thoughtful updates throughout. The main level features a spacious living room with a cozy fireplace, seamlessly flowing into a brand new beautiful kitchen equipped with top-of-the-line stainless steel appliances, sleek countertops, and custom cabinetry. Adjacent to the kitchen, the dining area is perfect for both everyday meals and entertaining guests. The main level also includes a luxurious bedroom and a spa-like en-suite bathroom, as well as an additional family room and half bathroom. Upstairs, you’ll find three generously sized bedrooms with ample closet space, as well as a beautiful brand new full bathroom. Outside, the expansive backyard provides a private oasis with a patio area, perfect for outdoor gatherings and summer barbecues. Additional Highlights include New siding, New roof, New doors, New floors, New electrical and plumbing systems, New kitchen, New bathrooms, New Anderson windows and a Two Car Garage. Don’t miss the opportunity to make this beautifully renovated home yours!
      Presented By: Keller Williams Points North  516-865-1800
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 57020 Route 25 Southold, NY 11971
      $995,000
      3 Bedrooms 3 Full Baths Sq. Ft. 2100.00:#
      Single Family For Sale ML# 3574281
      Beautifully restored and updated Colonial Path House. The front facade of the house has been restored to clapboard siding and cedar shake. The original rooms on the first floor include a cozy parlor with wood burning fireplace, an adjacent dining room, farm kitchen and full bath/laundry room. All with antique wide plank floors. The second floor has 2 bedrooms and large storage closet, as well as a full bath with an antique soaker tub. A new addition doubled the living area. The design of the addition compliments the old part of the house while modernizing the space with an ensuite bedroom, living room, a year-round sunroom, wide plank hardwood floors and working fireplace with a hand carved mantle from a Victorian Mansion. The kitchen has been updated with built in cabinets, a farm sink, a Bosch dishwasher and Viking stove. A bluestone patio is directly off the Primary bedroom. A successful and popular bed and breakfast was operated in this new addition. An accessory cottage is perfect for your studio or office. House in the heart of wine country. Top Southold Restaurants: John Fraser’s North Fork Table and Chef Panyard’s Southold Social. Note: Access to Founders Landing Beach., Additional information: Interior Features:Lr/Dr, Separate Hotwater Heater:1
      Presented By: Coldwell Banker Reliable R E  631-728-8070
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 345 Private Rd Unit 21 Southold, NY 11971
      $899,000
      4 Bedrooms 2 Full Baths 1 Half Bath Sq. Ft. 1800.00:#
      Single Family For Sale ML# 3590576
      Nestled on a serene and private road, this beautifully maintained Cape Cod-style home offers the perfect blend of classic charm and modern convenience. Boasting 4 spacious bedrooms and 2 1/2 well-appointed bathrooms, this home is ideal for anyone seeking both comfort and privacy. The inviting features of Cape Cod design, complemented by a lush, green landscape and a peaceful, wooded backdrop. Inside, you’ll find an open and airy floor plan with hardwood floors, and a warm, welcoming atmosphere. The spacious living room serves as the heart of the home, the eat-in kitchen is both functional and charming, with ample counter space, modern appliances, and a cozy dining nook overlooking the backyard, off the kitchen the family room offers easy access to the deck and yard. The first floor includes two bedrooms with easy access to a full bath, while the upper level offers two additional bedrooms. The second full bath is tastefully updated and easily accessible from all bedrooms. Enjoy the peaceful surroundings from the large backyard, ideal for entertaining or simply relaxing in nature. The private road ensures minimal traffic and adds to the home’s sense of seclusion while still being conveniently located near the pristine bay beaches and short distance to town. With its timeless appeal, functional layout, and tranquil location, this Cape Cod-style home is a true gem. Come explore the perfect North Fork retreat.
      Presented By: Signature Premier Properties  631-765-6000
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 57190 Route 25 Southold, NY 11971
      $899,000
      Misc Commercial ML# 3582488
      Prime real estate in the (HB) Hamlet Business District on the North Fork of Long Island. The property has ample parking and main road signage. Perfect for a real estate investor or entrepreneur looking to expand their business in Southold Town. Close to restaurants, shopping, wineries, and public transportation.
      Presented By: Century 21 Excelsior Realty  631-767-1069
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Southold, NY 11971
      $899,000
      3 Bedrooms 2 Full Baths 1 Half Bath Sq. Ft. 1572.00:#
      Single Family For Sale ML# 3572625
      Introducing 465 Tarpon Drive, a stunning property in the coveted Southold Shores Bayfront beach community on the North Fork. This contemporary and expanded cape is situated on a private, secluded road, surrounded by marinas, beaches, farms, and wineries. With an airy open floor plan, this home boasts a light-filled living space and a primary floor owner’s suite. The living room features soaring cathedral ceilings and a charming wood burning fireplace, while the bright and airy den offers vaulted ceilings and large windows to take in stunning woodlands behind the house and the winter water views of Brick Cove. The spacious eat-in kitchen is awaiting your personal touch. With 2-3 bedrooms and 2.5 baths, this home offers substantial decking providing an ideal setting for entertaining. Other features include basement laundry, utilities, and storage, as well as an attached 1++ car garage. Nestled on a peaceful lane in the Southold Shores bayfront beach community, this property offers a private yard, association beach access and is conveniently located between Southold Village and Greenport. Don’t miss this opportunity to enjoy the best of seaside living in the North Fork!, Additional information: Location Features:Protected Wetland
      Presented By: Town And Country Real Estate  631-298-0600
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 5535 Old North Rd Southold, NY 11971
      $835,000
      3 Bedrooms 1 Full Bath Sq. Ft. 1760.00:#
      Single Family For Sale ML# 3581696
      A classic North Fork farmhouse nestled in the heart of wine country, a winery adjacent to the property provides breathtaking vineyard views . This home features traditional design and layout, wood floors, upgraded heat and AC systems, one car detached garage and a welcoming sunroom perfect for relaxing and taking in the scenery. The lush landscaping is abundant with vibrant greenery, gardens, and flower beds with seasonal blooms, evoking a rustic yet elegant charm. Don’t miss this one!
      Presented By: Century 21 Albertson Realty  631-765-3800
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Southold, NY 11971
      $799,000
      3 Full Baths 1 Half Bath Sq. Ft. 1860.00:# Square Feet
      Single Family For Sale ML# 804042
      1-1/2 story medical office, with reception area, offices, exam rooms, 3-1/2 bathrooms, supply room, attic storage, 80% full, unfinished basement w/6-1/2 ft ceiling and outside entrance, 20 crawl space. Detached garage. Great location. Area is mixed use with single family residential homes, offices and light business. Zoned Residential/Office - Currently used as a dental office. Located in a flood zone.
      Presented By: Andrew Stype Realty Inc  631-298-8760
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 875 Oak Avenue Southold, NY 11971
      $699,000
      2 Bedrooms 1 Full Bath
      Single Family For Sale ML# 3577803
      Nestled in the serene Goose Bay Estates, this cozy Ranch, offers the perfect North Fork retreat. Featuring peaceful water views, this property comes with access to the beach, providing opportunities for boating, swimming and kayaking just moments from your doorstep. The home includes a sunroom and a cozy wood burning stove, adding warmth and character to the living space. Originally a 2 bedroom home, it has been converted to a spacious 1 bedroom layout but has plenty of potential for expansion or renovation. While it could use some TLC, this is a rare chance to customize your dream home in a beautiful coastal setting. Close to South Harbor beach, vineyards and farms. Don’t miss this chance to own a piece of paradise!, Additional information: Interior Features:Lr/Dr
      Presented By: Engel & Volkers North Fork  631-298-7953
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    Showing 21 - 30 of 85 results| view:  results per page« 1|2|3|4|5|...|last »
    OneKeyâ„¢ MLS The data relating to real estate for sale on this web site comes in part from the OneKeyâ„¢ MLS. Real Estate listings held by brokerage firms other than Beninati are marked with the Broker Reciprocity logo and detailed information about them includes the name of the listing brokers.

    Questions? Just Ask!

    Submit