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 71 - 80 of 85 results| view:  results per page« first|...|5|6|7|8|9 »
    • 455 W Shore Drive Southold, NY 11971
      $5,000
      4 Bedrooms 2 Full Baths 1 Half Bath Sq. Ft. 1625.00:#
      Single Family For Rent ML# 3591372
      Presented By: Corcoran  631-765-1300
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 53245 Main road Southold, NY 11971
      $4,800
      Retail Commercial NEW ML# 806620
      Location, location, location!! Great opportunity to lease an absolute gem right on main street in Southold Town. More pictures and interior blueprints coming. Available April 1st 2025.
      Presented By: Signature Premier Properties  631-765-6000
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 13595 Soundview Avenue Southold, NY 11971
      $4,800
      3 Bedrooms 2 Full Baths 1 Half Bath
      Single Family For Rent ML# 3586919
      Located on a private and serene 1.09 acre parcel of land and only 1/3 of a mile from McCabes Beach, with miles of Long Island Sound beach to traverse to the east and west, this charming and newly built two story home offers an open concept living space with plentiful natural light on the first floor with a half bathroom between the living and dining room, with a half bathroom off of the hallway leading to the eat-in-kitchen and den/tv room. The second floor provides a master bedroom with en-suite bathroom, two additional bedrooms and another full bathroom. There are large sliding glass doors in the kitchen that lead to a picturesque patio and outdoor sitting area with grill, tables and umbrella. Take in all the North Fork has to offer. Rental permit # 0343
      Presented By: Douglas Elliman Real Estate  631-477-2220
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 240 Wampum Way Southold, NY 11971
      $4,750
      5 Bedrooms 2 Full Baths 1 Half Bath Sq. Ft. 2400.00:#
      Single Family For Rent ML# 3455253
      LOWER RATES! Make meaningful memories in this soaring contemporary overlooking beautiful Hog Neck Bay and Corey Creek. Enjoy water views from nearly every room. Open floor living/dining area. CAC, W/D, Internet/WiFi, all utilities included. Large waterside deck, huge patio with nearly-new Weber gas grill, outdoor shower, private community beach. Permit #0520.Additional information: Appearance:dramatic Weekly Rent Amt: 4750
      Presented By: Douglas Elliman Real Estate  631-298-8000
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 8200 Soundview Avenue Southold, NY 11971
      $4,000
      3 Bedrooms 2 Full Baths
      Single Family For Rent ML# 3590047
      Contemporary Home with Heated Pool, Less then a 1/2 Mile from a Gorgeous Long Island Sound Beach. Come Enjoy the Great North Fork. The Perfect Getaway Does Exist! With 3 Bedrooms and 2 Full Baths, Close Proximity to the Beach, a Pool Integrated into the Deck, and a Separate Rooftop Deck, This Property Offers an Ideal Mix of Relaxation and Style. The Spacious Gourmet Kitchen (Sub-Zero Fridge, Meile Oven, Wolf Gas Range) and Multiple Living Areas Make it Great for Both Quiet Retreats and Entertaining Guests. The North Fork is Known for its Beautiful Landscapes, Beaches, Wineries, and Local Charm, So This Home is in a Prime Spot to Enjoy All it Has to Offer! Off Season $4, 000 Per Month; Year Round $4, 200 Per Month, Memorial Day to Labor Day $32, 000; June $8, 000; July $12, 000, August to Labor Day $15, 000; $3, 000 Weekly with 2 Week Minimum. Permit #1217.
      Presented By: Douglas Elliman Real Estate  631-477-2220
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 1425 Paradise Point Rd Southold, NY 11971
      $4,000
      3 Bedrooms 1 Full Bath 1 Half Bath Sq. Ft. 1650.00:#
      Single Family For Rent ML# 3575668
      Renovated North Fork getaway situated on a lush 5 acre property. The tranquil setting is perfect in all seasons. 3 beds, 2 baths, nursery/office, plenty of living space, chef’s kitchen and close to all the North Fork has to offer. Walking distance to coveted Cedar Beach. North fork with a New England vibe.
      Presented By: Compass Greater NY LLC  631-251-8644
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 480 N Bayview Road Southold, NY 11971
      $4,000
      3 Bedrooms 3 Full Baths
      Misc For Rent ML# 3529080
      Experience refined living in the exquisite 3 bedroom 3 bath home available to rent for the summer season. This charming residence is in the heart of Southold where beach and town access is most convenient. Delight in the spacious grounds surrounding this property tucked up on a meandering hill providing a serene, private retreat. The backyard is fenced and pets are welcome. Step inside to discover a modern chic interior, perfectly curated for comfort and style. The spacious grand primary en-suite bedroom is complete with a new spa-appointed bathroom, vaulted ceilings, and walls of windows. There is also another en-suite bedroom equally appointed with great light and plenty of closet space. The third bedroom is on the main level with easy access to the living quarters. The home is complete with a beautiful kitchen that leads out to a large deck for entertaining, a comfortable and spacious living space, and a formal dining room. The lower level has laundry and a small recreation space. Goose Creek Beach is within a mile. Come enjoy the East End!
      Presented By: Douglas Elliman Real Estate  631-288-6244
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 5650 North Bayview Rd Southold, NY 11971
      $3,900
      5 Bedrooms 2 Full Baths Sq. Ft. 2000.00:#
      Single Family For Rent ML# 3566958
      Historic Main Bayview schoolhouse converted to country residence located at 5650 N Bayview Road, Southold. Available for winter rental, September 3, 2024 - June 30, 2025 $3, 900 per mo plus utilities, etc Country residence features 5 bedrooms in historic Main Bayview Schoolhouse converted to residence - sleeps max 10 people. Pet friendly. Equidistant to Cedar Beach and Goose Creek Beach. Moments to village of Southold, North Fork wine trail, area shops and top tier restaurants. An ideal vacation destination OR winter residence. Private fenced yard. Living room features woodstove. Finished lower level offers playspace or make it a home office. Rental Permit #0336
      Presented By: Town And Country Real Estate  631-298-0600
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 53395 Route 25 Unit Apt 1 Southold, NY 11971
      $3,500
      1 Bedroom 1 Full Bath Sq. Ft. 750.00:# Square Feet
      Apartment For Rent ML# 805184
      Brand New Tastefully Renovated Furnished Apartment conveniently located in the heart of Southold. The apartment is Available to rent at flexible time-frame(s). Public transportation is in near proximity, along with everything else the North Fork has to offer.Price is $3, 500 for month to month, 6 month lease would be $2, 400 a month
      Presented By: Century 21 Albertson Realty  631-765-3800
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 45 Baywater Avenue Southold, NY 11971
      $3,500
      3 Bedrooms 2 Full Baths
      Single Family For Rent ML# 3581131
      Charming home, originally built in approximately 1905.Main Rd, South onto South Harbor Road, Left on to Baywater Ave. Close proximity all the North Fork has to offer. Down the road. to Croteaux Vinyards and South Harbor Park for swimming, kayaking and boating. Close to the best North Fork restaurants, marinas and farm stands.
      Presented By: Daniel Gale Sothebys Intl Rlty  631-734-5439
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    Showing 71 - 80 of 85 results| view:  results per page« first|...|5|6|7|8|9 »
    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