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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    103  properties match your search;

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    Showing 1 - 10 of 103 results| view:  results per page« 1|2|3|4|5|...|last »
    • 10995 N Bayview Rd Southold, NY 11971
      $7,750,000
      5 Bedrooms 5 Full Baths 1 Half Bath Sq. Ft. 6162.00:# Square Feet
      Single Family For Sale ML# 3482756
      Discover the charm of waterfront living on this 8-acre estate along Southold Bay, boasting 157 feet of pristine shoreline and a private beach for tranquil retreats. The welcoming gates open to a driveway lined with pear trees, leading to a home that celebrates the beauty of its natural surroundings. The foyer unfolds into a living room illuminated by 24-foot windows, offering panoramic views of the bay and easy access to your secluded beach. The heart of the home, the kitchen, is ready for any culinary endeavor and seamlessly connects to the dining and living areas, ideal for casual entertaining. A guest suite on the ground floor provides a quiet escape for visitors. Upstairs holds four ensuite bedrooms, with two featuring balconies that invite the outside in, each morning graced by waterfront vistas. With over 6, 000 square feet, the home offers ample space while maintaining a cozy ambiance. Outdoor life is a breeze with a deck designed for relaxation and gatherings, against the backdrop of your own beachfront. Beyond the tranquility of your estate, downtown Southold beckons with its lively dining scene, shops, and wineries, blending coastal serenity with community vibrancy in this unique Southold bayfront home.
      Presented By: Daniel Gale Sothebys Intl Rlty  631-734-5439
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 750 Paradise Point Rd Southold, NY 11971
      $7,395,000
      5 Bedrooms 6 Full Baths
      Single Family For Sale NEW ML# 3535372
      Paradise Point Road is one of the most prestigious addresses on the North Fork. This stunning home sits on 3.28 acres, has 252 ft of waterfront on the bay with its own sandy beach, newly built dock, and more! Privacy abounds with an electric entrance gate with telecom followed by a long tree lined driveway to this 5 bedroom, 6 bath home. All 5 bedrooms have ensuite baths, the primary bedroom overlooks the water with doors leading out to an expansive backyard. When you enter the home, the first thing you see is the bay! The foyer opens into a serene sitting room with floor to ceiling glass doors and panoramic water views. The great room includes an impressive stone fireplace which is easily controlled by remote for an instant gas flame. Also included in the great room is a new wet bar with ice maker, wine-fridge, sink and wine rack perfect for entertaining! The kitchen and dining areas both overlook the water with doors to the outdoor space and to a magnificent screened-in porch that has ample space for large gatherings. The outdoor space is an entertainer’s paradise, with outdoor speakers, a spacious bluestone patio equipped for a large dining table, a heated saltwater pool with an automatic pool cover, separate hot tub, pool house with wet bar, outdoor shower, gas firepit and beach cabana/boat house equipped electric and water. Smart technology throughout the home. Generac generator with cellular monitoring device. This home has been fully upgraded over the last 10 years including electric, insulation, etc. Too many upgrades to list. Must be seen in person to truly appreciate!
      Presented By: Douglas Elliman Real Estate  631-354-8100
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 50100 County Road 48 Southold, NY 11971
      $4,495,000
      Unimproved Land For Sale ML# 3520399
      Attention Developers and Discerning Investors! Opportunity knocks with this 36-acre parcel, Development Rights in Tact, nestled in the heart of the North Fork. Ideally positioned along Arshamomack Creek with access to both County and Municipal roadways, this property offers a perfect setting for the development of either workforce housing, an exclusive residential enclave or a private estate. A generous tract of land within the R80 zone, allowing for 2-acre zoning. Close proximity to pristine beaches, renowned farmstands, and esteemed wineries. Bring your vision. (see attachments for more info.)
      Presented By: Compass Greater NY LLC  631-251-8644
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 11535 N Bayview Rd Southold, NY 11971
      $4,300,000
      Unimproved Land For Sale ML# 3514107
      Rare opportunity to own this stunning 13.85 acres bay front parcel with over 450ft of secluded beach. This property boasts a depth of over 1000ft, creating a huge blank canvas to design your legacy estate. Offering scenic trails, serene ponds, and glorious sunrises. The perfect place to build your dream home and weave your everlasting story.
      Presented By: Daniel Gale Sothebys Intl Rlty  631-477-0013
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 17665 Soundview Avenue Southold, NY 11971
      $3,950,000
      4 Bedrooms 4 Full Baths 1 Half Bath
      Single Family For Sale NEW ML# 3536265
      Welcome to Everward Bluff, an exquisite waterfront residence nestled on the former site of the Alfred H. Cosden Eastward Estate, boasting unparalleled privacy and stunning, unobstructed vistas of the Long Island Sound. With 150’ +/- ft of private beach front, there are breath-taking water views from every room. Crafted with meticulous attention to detail by a reputable builder, this custom 4/5 bedrooms, 4.5 bathroom, Nantucket-style home offers modern elegance and expansive living spaces across over two acres of secluded grounds. Upon entry, a grand 2-story foyer welcomes you with a sweeping staircase and oversized windows framing picturesque park-like views. Designed for seamless entertaining, the first floor features an open-plan layout blending living, dining, and kitchen areas. The chef’s kitchen boasts top-of-the-line Viking appliances, custom cabinetry, and granite countertops, while a separate butler’s pantry offers additional storage and prep space. French doors in the living and dining areas seamlessly integrate indoor and outdoor living, opening to a wrap-around porch overlooking a pristine gunite pool, sunlit gardens, and glorious water views with spectacular sunsets. Upstairs, the primary suite offers a private deck with panoramic water views, complemented by a luxurious Italian-tiled shower in the ensuite bathroom. Off the primary bedroom is a wonderful room that could be used as a gym, laundry room, or easily converted to an additional bedroom. Two additional bedrooms, each with ensuite bathrooms and scenic water views, provide comfort and serenity. The larger of these bedrooms has a wood-burning fireplace and its own private deck. Additional amenities include a wood-burning fireplace, natural gas, 3-zone central air, a security system, central vacuum system, 2nd floor laundry room, and a bright third-floor attic space with a staircase leading to a widow’s walk offering breathtaking 360-degree vistas. Everward Bluff epitomizes coastal luxury living, combining timeless design with unmatched tranquility and natural beauty.
      Presented By: Compass Greater NY LLC  917-499-2824
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 1400 Youngs Avenue Southold, NY 11971
      $3,800,000
      Mixed Use Commercial ML# 3432230
      Invest In The North Fork. Approximately 19, 000 Sq. Ft. Office Space. Solid Brick Build. Full Basement With Tall Ceiling Height. Meticulously Maintained. Located In The Heart Of The Town Of Southold And Across The Street From the LIRR Train Station. Widows Surround For Ample Natural Light. Several Private Office Spaces On Each Floor. Basement Has Cafeteria And Meeting Space. Ample Parking. 3 Bay Storage Garage
      Presented By: Daniel Gale Sothebys Intl Rlty  631-477-0013
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 150 Deer Run Southold, NY 11971
      $3,695,000
      5 Bedrooms 4 Full Baths 2 Half Baths Sq. Ft. 5285.00:# Square Feet
      Single Family For Sale ML# 3467781
      Gorgeous estate-like Nantucket shingle home currently under construction. Designed by the renowned firm of Nelson and Pope, this lovely home follows an entertainer’s dream layout: open Great Room concept with fireplace, Chef’s gourmet kitchen with Bertazzoni appliances, large island and breakfast nook, formal dining room with Butler’s pantry, a first floor junior master ensuite, and library. White oak hardwood floors throughout. Upstairs is a spacious mater ensuite with two walk in closets, 3 more bedrooms, 2 full baths, a laundry room, and a bonus family room. The walk out basement is ready for you to finish as you wish, with room for home theatre, wine cellar, gym or other uses. Outside enjoy multiple covered porches and your lovely pool, all surrounded by the peace and quiet of this serene and private setting. This is truly a Hampton-style masterpiece on the North Fork. Still time to customize. Projected completion June 2024
      Presented By: Corcoran  978-201-9282
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 630 Calves Neck Rd Southold, NY 11971
      $3,149,000
      4 Bedrooms 5 Full Baths 1 Half Bath Sq. Ft. 4400.00:# Square Feet
      Single Family For Sale NEW ML# 3537102
      Welcome to 630 Calves Neck Road! This new construction North Fork diamond boasts 4, 400 square feet of luxury with 4 en-suite bedrooms, 5.5 baths and a huge bonus room with skylights. Set on .75 acres and offering seamless architectural details, the meticulous craftsmanship is evident in a gorgeous EIK with center island, high end finishes including Wolf and Sub-zero appliances, marble and porcelain baths, radiant heat, and double washer/dryers. One sun-filled room flows into the next for the ultimate in comfort, convenience and modern day living. Each detail has been thoughtfully designed from the vaulted ceilings, built-ins, cabled railings and pantry, to a fully fenced heated salt water in-ground pool, first floor primary bedroom, gas fireplace, and gleaming hardwood floors. Close to marinas, beaches, boating, golf, shopping and world class restaurants, farms and vineyards. Don’t miss out on the opportunity to make it all yours!
      Presented By: Compass Greater NY LLC  516-319-3274
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 9502 N Bayview Rd Southold, NY 11971
      $3,100,000
      5 Bedrooms 4 Full Baths 1 Half Bath Sq. Ft. 4051.00:# Square Feet
      Single Family For Sale ML# 3515679
      The Intelligent Choice For Those Who Value A Home Which Embodies Privacy, Luxury And Time Well Spent . Welcome Your Family And Friends Into This Very Tasteful Turnkey Oasis With Amenities Galore Including Professional Kitchen With Patio Service Window, Butler’s Pantry For Proper Wine And Coffee Service, And A Sumptuous Yard. They May Never Want To Leave! No Detail Has Been Spared In This Estate Setting Including A Huge Bunk Room For The Kids And Overflow Guests, Library, Pool, Hot Tub And Expansive Yard. Please Call To Schedule A Private Viewing.
      Presented By: Thomas J McCarthy Real Estate  631-765-5815
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 70 Wildberry Lane Southold, NY 11971
      $2,995,000
      5 Bedrooms 4 Full Baths 1 Half Bath
      Single Family For Sale NEW ML# 3538082
      Beautiful custom home located in the hamlet of Southold captures amazing views of the LI Sound. Architectural details include an open floor plan, floating staircase, private roof-top, mahogany decks with horizontal cable railings, and all custom European windows and doors. An expansive luxury kitchen, a chic water-view lounge, and a first-floor ensuite bedroom provide a sophisticated North Fork retreat. The exterior is board and baton mixed with cedar. The pool is 20 x 40 with room for a pool house or cabana. The full basement provides an additional 1500 sq ft that can be finished. Southold Town Beach is less than 0.5 miles, approximately 10 min walk. Close to all that the East End has to offer. Professional photos will be coming soon.
      Presented By: Douglas Elliman Real Estate  631-288-6244
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    Showing 1 - 10 of 103 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.

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