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 51 - 60 of 86 results| view:  results per page« first|...|5|6|7|8|9 »
    • 950 Blue Marlin Drive Southold, NY 11971
      $20,000
      4 Bedrooms 4 Full Baths Sq. Ft. 3200.00:#
      Single Family For Rent ML# 3376195
      Beachfront, located in Southold Shores, this architect’s own home is built with all the beautiful appointments you can imagine. Embracing the purity of architectural detail, together with a refined simplicity, this waterfront home offers a timeless elegance. Sweeping sunsets eye-catching angles and thoughtful details provide constant visual interest. A large 4 bedrooms with 4 baths ensuite, seaside floor to ceiling windows overlooking the Bayfront, Chefs kitchen leading to large outdoor deck and lovely garden. It is truly stunning. A special summer oasis. Available August $40K, Sept $20K RP# 0857
      Presented By: Town And Country Real Estate  631-477-5990
      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:#
      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 RATES: MD-LD $19, 000 ; June $3500; July $7, 000’ Aug-LD $8, 000 July/Aug-LD $15, 000 - off season/Fall 2025 available.
      Presented By: Town And Country Real Estate  631-298-0600
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 50 Wabasso Street Southold, NY 11971
      $18,000
      3 Bedrooms 2 Full Baths Sq. Ft. 1200.00:#
      Single Family For Rent ML# 3559692
      Planning a staycation? this Laughing Waters Association ranch is the perfect destination for a resort-style stay this year. Come experience the private bay beach, smell the salt air, and enjoy time boating/SUP/kayaking in the creek or try your luck clamming. The home is an easy and comfortable springboard to the North Fork lifestyle and features an open plan ideal for entertaining. Living room, Dining room, large kitchen to make the most serious cooks feel at home - plus an en suite bedroom with full bath and two additional bedrooms and full bath. Beyond the covered porch is a verdant and fully fenced in lawn area ideal for play, a bbq area, multiple sitting areas, a game room adjacent to the garage, a pool house with ’bar’ area and the most amazing outdoor, poolside shower. No detail for enjoyment has been overlooked - there is even a firepit for idle-hour! Available monthly, or weekly - inquire. Pets permited - fully fenced in property! Southold RP# 1149 expires 6/10/26
      Presented By: Town And Country Real Estate  631-298-0600
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 350 West Drive Southold, NY 11971
      $16,000
      3 Bedrooms 2 Full Baths 1 Half Bath Sq. Ft. 1900.00:# Square Feet
      Single Family For Rent NEW ML# 809819
      Rental Permit #0609 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 heading east to Horton’s Point Lighthouse or west to Goldsmith’s Inlet, the journey is as stunning as the destination. The nearby 60-acre nature trail invites exploration, while this home offers peace, privacy, and breathtaking sunsets 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
    • 425 Cedar Point Drive E Southold, NY 11971
      $15,000
      5 Bedrooms 3 Full Baths 1 Half Bath Sq. Ft. 3700.00:#
      Single Family For Rent ML# 3573270
      Now Available for Off Season Rental Until March 31, 2025 and Post Labor Day 2025. Rented June 1 - September 30th. Set Creekfront with Private Dock and Associated Bay Beach Access in Community. The Extensive Rear Patio Area is Impressive with an Inground Pool and Jacuzzi. All Creekfront with a Beautiful View. The Home is Grand and Designed to Entertain. Boasting 5 Bedrooms and 4 Baths. 2 Large Living Rooms, Well Appointed Kitchen with All High-End Appliances. 6 Burner Wolf Stove for Cooking. All Overlooking Dining, Living and Bar Area. All Utilities (Except Electric), Cleaning, Pool, Jacuzzi and Exterior Maintenance Provided by Landlord. Ample Parking. The Home Also Includes a Bocce Court, Ping-Pong and Shuffleboard Tables. All Prospective Tenants to Provide a Completed Application Via RentSpree. Link to be Provided. Rental Permit # 1180, Additional information: Appearance: Beautiful, Interiorr Features: Efficiency Kitchen, Guest Quarters, Interior Features: Separate Thermostat
      Presented By: Douglas Elliman Real Estate  631-298-8000
      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:#
      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 Southold’s Park District, includes access to Founders’ Landing treasured sandy Bay beach park & playground. Everything you need for a fantastic North Fork vacation. Rental permit #0392; Expiration date 4/18/2025, Additional information: Appearance:Excellent, Weekly Rent Amt:2500
      Presented By: Douglas Elliman Real Estate  631-477-2220
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 1175 Waterview Drive Southold, NY 11971
      $14,000
      3 Bedrooms 3 Full Baths Sq. Ft. 1800.00:#
      Single Family For Rent ML# 3519239
      Southold Goose Creek Waterfront Home. Immaculate sun-filled home with all you will need to relax and enjoy summer. Large living room, and dining room. Well equipped Kitchen with sliders to deck, Den with amazing water views. Ensuite bedroom with water views, 2 additional bedrooms and bathrooms. Furnished deck and large yard. There is a dock to fish, boat, paddle board or kayak (2 included) from your own dock. A perfect retreat close to all the best of the North Fork. Rental Permit 0691. Available Rental Dates 2025:Memorial-Labor Day $34, 000, June $12, 000, July $14, 000, July-August $30, 000, August-LD: $17, 000. Rental Permit #0691.
      Presented By: The Agency Northshore NY  631-870-0753
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 215 Northfield Lane Southold, NY 11971
      $14,000
      4 Bedrooms 3 Full Baths Sq. Ft. 2300.00:#
      Single Family For Rent ML# 3386926
      Permit 681 .Enjoy This Beautifully Renovated 4 Bedroom, 3 Bath Ranch Style Home With Heated Pool. Open Floor Plan Includes LR With Cathedral Ceilings, High End EIK, Dining Area & Outdoor Shower. Plenty of Room For The Whole Family & Guests. Beautiful Goose Creek Beach Just 0.2 Miles Down The Road. Minutes To Local Wineries, Shopping & Dining. Make Memories In This Wonderful Summer Rental!
      Presented By: Thomas J McCarthy Real Estate  631-765-5815
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 11925 Soundview Avenue Southold, NY 11971
      $12,500
      5 Bedrooms 4 Full Baths 1 Half Bath Sq. Ft. 3600.00:#
      Single Family For Rent ML# 3571029
      Enjoy water views and Long Island Sound sunsets from this magnificent new construction home for rent! Perfectly situated on 1.5 scenic acres, this home offers exclusivity and privacy. The beautiful eat-in-kitchen features high-end amenities including a Viking refrigerator and 8 burner range, double ovens, dual Bosch dishwashers plus two wine coolers. The airy and spacious living room is accented with dramatic vaulted ceilings, fireplace and wet bar. A wall of oversized sliding glass doors allow for plenty of natural light and lead to a 2, 000 sq. ft mahogany deck and heated gunite pool - ideal for comfort and relaxation. Two generously sized bedrooms and 1.5 baths complete the first floor. The second floor boasts an expansive primary suite with two walk-in closets and a luxurious bath including radiant heated floors, soaking tub, water closet, rain shower & body jets. Enjoy an early morning cup of coffee or star gaze in the evenings from your private water view balcony, making this room the perfect retreat. You will also find two additional bedrooms and two full baths on this floor. Enjoy all the North Fork has to offer and more with the deeded right of way that comes with this home which provides convenient access to sought-after McCabe’s Beach! Kenney’s Beach is also just a stone’s throw away! Don’t miss the opportunity to create a vacation to remember with this special home! Two-week terms are also available. Appearance: Mint
      Presented By: Compass Greater NY LLC  516-517-4751
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 400 Hill Rd Southold, NY 11971
      $12,000
      3 Bedrooms 2 Full Baths Sq. Ft. 1620.00:#
      Single Family For Rent ML# 3549421
      Welcome to your perfect summer getaway located in the desirable Claves Neck neighborhood of Southold. This comfortable Ranch has ample space for the whole family to unwind and recharge after a day of exploring the North Fork. The home offers a fully equipped kitchen, spacious living, and dining rooms, three pleasant bedrooms, two pristine bathrooms. Outside, a savor al fresco dining amid the lush greenery surrounding the screened in porch and brick patio with outdoor dining area and gas BBQ. Whether you are hosting a barbecue with loved ones or simply enjoying a quiet moment, this outdoor oasis provides the perfect backdrop for making memories. Popular beaches, restaurants, and wineries are all close by. Do not miss your chance to experience the best of Southold living (Southold Town rental permit #49090) Available for 2 weeks @ $3000 per week., Additional information: Appearance:Rxcellent, Weekly Renta Amt:3000
      Presented By: Town And Country Real Estate  631-477-5990
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    Showing 51 - 60 of 86 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.

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