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 81 - 90 of 130 results| view:  results per page« first|...|7|8|9|10|...|last »
    • 18805 Soundview Avenue Southold, NY 11971
      $23,000
      4 Bedrooms 3 Full Baths 1 Half Bath Sq. Ft. 3800.00:# Square Feet
      Single Family For Rent ML# 3529983
      Magnificent Waterfront with Pool! Enjoy the luxury of coastal living in this beautifully constructed home with its own private beach. Open and airy spaces with all the amenities for comfort and relaxation. Spacious kitchen, Dining Rm, Living Rm w/fp, Four generous sized bedrooms & 3.5 baths. The upstairs loft boasts an amazing recreational area with soaring ceilings & walls of glass overlooking spectacular views of the sound & sunsets. Close to shopping, vineyards, boating, world-class dining and more! Last two weeks of June (6/15-6/30): $23, 000. Full Month of July: $50, 000. First two weeks of August (8/1-8/15): $25, 000.
      Presented By: Compass Greater NY LLC  516-517-4751
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 3675 Wells Avenue Southold, NY 11971
      $22,000
      4 Bedrooms 2 Full Baths
      Single Family For Rent ML# 3467464
      Enjoy an experience on the North Fork of LI this summer. Whether a couple of weeks, a month, or the whole season, spend it nestled in a quiet spot that is near downtown Southold. Feel embraced by all the NOFO has to offer in this meticulously renovated, waterfront Cape, while enjoying the utmost in privacy and waterfront access. Step down into your own private swimming spot in clear Jockey Creek or enjoy your own private deep-water dock (bring your boat!). Kayak, canoe or paddle directly to Southold Bay, Shelter Island Sound and the extended fishing grounds of Greenport, Bug Light, Orient and beyond. Enjoy a quick ride into the charming downtown of Southold for elegant dining, shopping and easy access to LIRR/Jitney into NYC. Make lasting summer memories on this expansive idyllic, half acre, creekfront property which is perfect for quiet time, entertaining on the deck or play.
      Presented By: Signature Premier Properties  631-765-6000
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 4200 Youngs Avenue Southold, NY 11971
      $21,500
      4 Bedrooms 2 Full Baths Sq. Ft. 2400.00:# Square Feet
      Single Family For Rent ML# 3534791
      Tranquil farm setting in the heart of North Fork, close to all. Centrally located to all the North Fork has to offer, but tucked away on quiet block surrounded by farms. Enjoy our newly furnished home with 5 beds, 2 baths, and an in-ground saltwater pool. Wake up and sip coffee on your front porch & enjoy the serene views with farm animals roaming in the background. 2 mins drive to Southold town. 4 mins drive to Horton Point lighthouse or Mcbain beach. 10 mins to Greenport Village.
      Presented By: Century 21 Albertson Realty  631-765-3800
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Southold, NY 11971
      $19,000
      1 Bedroom 1 Full Bath Sq. Ft. 750.00:# Square Feet
      Single Family For Rent ML# 3525718
      Southold, North Fork - artful cottage located in Southold by Founder’s Landing Park/Wharf House. Opposite a fabulous bay beach sits this unique, furnished, one bedroom residence. Full kitchen with dishwasher, bright and sunny living room, comfortable bedroom... home is heated by natural gas. Park like property with outside sitting area. Privacy and pet friendly. Enjoy life on the east end in this furnished home ready for you and convenient to area restaurants, wineries, and all the North Fork has to offer. Permit #0107
      Presented By: Town And Country Real Estate  631-298-0600
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 50 Oak Avenue Southold, NY 11971
      $18,000
      3 Bedrooms 3 Full Baths Sq. Ft. 2328.00:# Square Feet
      Single Family For Rent ML# 3536769
      Escape to this idyllic waterfront haven. This summer retreat includes 3-bedrooms and 3-bathrooms, blending luxury and comfort seamlessly. Enjoy modern amenities including a fully equipped Chefs kitchen, and an open concept living space with floor to ceiling windows. Kayak, or Paddle Board from your private dock to the local sandy beach. The property also features a generous outdoor space, perfect for relaxation and entertaining and a Tesla charging station adding additional convenience. Don’t miss the opportunity to make this waterfront sanctuary your summer getaway!
      Presented By: Compass Greater NY LLC  917-848-5102
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 1205 Lake Drive Southold, NY 11971
      $17,500 - $25,000
      4 Bedrooms 4 Full Baths
      Single Family For Rent ML# 3528933
      Public Remarks:If you are looking for a true summer experience on the beautiful North Fork of Long Island, look no further. This Spacious home has the full spectrum of mother nature right on your own huge back yard on the great lake with 2 fire pits. Featuring 4 Bedrooms, 4 Bath, An Oversize Patio, Large Heated In ground pool. Your own fully equipped gym to help keep you in the best of shape! You may enjoy fishing in a lake only a few steps away, as well as close distance to Kenny’s Beach on the Sound. Ample of Marinas around the corners, as well as endless Vegetable & Fruit Farms & Stands, Wineries, Restaurants & Shopping. Enjoy this rare find for a memorable summer experience! Permit no: 0080 Expire: 06/07/2025 - JULY & AUGUST ARE NO LONGER AVAILABLE .
      Presented By: Douglas Elliman Real Estate  631-298-8000
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 1820 Kenneys Rd Southold, NY 11971
      $15,000
      6 Bedrooms 4 Full Baths Sq. Ft. 5028.00:# Square Feet
      Single Family For Rent ML# 3505469
      Room for All in this Spacious 6 Bedroom Luxurious Home with Gourmet Kitchen with 6 Burner Wolf Stove, Formal Dining Room. Large Living Room with Fireplace, a Separate Den and Large Bedrooms. Rainy Day Game Room and More in Lower Level. All set on 2.3 Acres with In Ground Pool, Nicely Finished Outdoor Space and Yard Area and Just a Short Distance to Kenneys and McCabes Beaches. Summer 2024 - June 1 to June 28 - $30, 000 or $8, 500 Per Week With Two Week Minimum. August 25 to September 8 (Two Weeks) $18, 500; September $30, 000 or $8, 500 per Week With Two Week Minimum. Off Season - October through April at $15, 000 Per month for Single or Multiple Month Rentals. Permit #0233.
      Presented By: Douglas Elliman Real Estate  631-477-2220
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 695 Rogers Rd Southold, NY 11971
      $15,000
      5 Bedrooms 2 Full Baths Sq. Ft. 1800.00:# Square Feet
      Single Family For Rent ML# 3470466
      Located in a gorgeous Bay beach private community, just a stone’s throw from Southold Bay. Waterviews from many rooms and the sprawling backyard. Immaculate, light filled, 5 bedroom/2 bath charmer with room for all. Features include walkout deck, a library, sunroom w/gorgeous Bay views, outdoor showerhouse. Super convenient to fine dining, shopping & wineries - just 5 minutes to either Southold or Greenport....even 3 stellar farm stands just up the road including a CSA. Farm to table heaven! Located within the Park District with access to Founders’ Landing Park’s treasured sandy Bay beach. Everything you need to enjoy your summer on the amazing North Fork! Rental permit #0392; Expiration date 4/7/25.
      Presented By: Douglas Elliman Real Estate  631-477-2220
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 1695 Old Woods Path Southold, NY 11971
      $15,000 - $30,000
      6 Bedrooms 4 Full Baths
      Single Family For Rent ML# 3212687
      Southold, North Fork: This beautiful estate, bayfront home offers complete privacy in a peaceful woodland setting with a historic provenance and featuring a sugar sand beach. Despite its private location, it is conveniently close to the village and North Fork amenities. Croteaux is just up the lane, and NoFo table is a short bike ride away. The estate house has a broad porch, a living room with a fireplace, a formal dining room, a den, a large kitchen, and a pantry. Upstairs, there are five bedrooms, three baths, PLUS, an outdoor shower convenient for all to enjoy. The outbuilding, known as The Birdhouse, offers dormitory space for overflow guests with a private bathroom. The estate has a direct beachfront setting, with sugar sand and carefree days awaiting visitors in an old-fashioned East End seaside cottage. Permit# 0996
      Presented By: Town And Country Real Estate  631-298-0600
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 2445 Minnehaha Boulevard Southold, NY 11971
      $14,000
      3 Bedrooms 2 Full Baths
      Single Family For Rent ML# 3526587
      Bring your swim suit, flip flops, and summer vibe! This amazing property located in a private beachfront community across the street from a beautiful sandy bay beach. The community is set far off the main rd providing a great ambience of being away from it all! Great place to relax, boat, entertain, dine al fresco, and all things fun in the sun. Lovely updated, immaculate home with 3beds and 2 full baths, office space, living room, dining room, outdoor deck with bay views! Pack some extra clothes, you will not want to go home!
      Presented By: Compass Greater NY LLC  631-251-8644
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    Showing 81 - 90 of 130 results| view:  results per page« first|...|7|8|9|10|...|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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