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 71 - 80 of 132 results| view:  results per page« first|...|6|7|8|9|...|last »
    • 630 Calves Neck Rd Southold, NY 11971
      $35,000 - $65,000
      4 Bedrooms 5 Full Baths 1 Half Bath Sq. Ft. 4400.00:# Square Feet
      Single Family For Rent ML# 3542038
      New Construction with all high end finishes. First Floor Primary Suite. Three additional oversized bedrooms - all ensuite. 2 King beds, 2 Queen beds. Den/Office facing inground pool, Huge 2nd Fl Bonus Room, 5.5 Luxurious Baths. Every detail has been carefully considered and designed to accommodate multiple guests. Close to shopping, multiple parks, beaches, golf and fine dining. This is Truly an Entertainer’s Delight! Dogs allowed up to 10 lbs. Tenant pays utilities and pool care.
      Presented By: Compass Greater NY LLC  516-319-3274
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 45805 Main Rd Southold, NY 11971
      $35,000
      5 Bedrooms 4 Full Baths 1 Half Bath Sq. Ft. 3600.00:# Square Feet
      Single Family For Rent ML# 3532208
      Ideal summer getaway in the heart of the North Fork with 5 bed and 4.5 baths. The home sits on a shy half acre complete with accessory office/gym structure, inground gunite pool and has incredible views of the neighboring North Fork vineyard. The first floor features an open floor plan with a large eat-in kitchen, dining area, living room and family room. There are four bedrooms in the main portion of home and an accessory attached apartment with an additional bedroom, family room and kitchenette. Enjoy close proximity to downtown Southold, beaches and wineries. Renovated top to bottom in 2021. June- 25K, July 35K.
      Presented By: Compass Greater NY LLC  516-330-6086
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 292 Waterview Drive Southold, NY 11971
      $33,000
      4 Bedrooms 3 Full Baths
      Single Family For Rent ML# 3528449
      This updated and well maintained home and pool is poised on a sprawling three private acres and a true getaway! Boasting four large bedrooms, 3 full recently renovated bathrooms. Backyard oasis with playset and lush lawn. Located less than two miles to Southold’s favorite Cedar Beach and Goose Creek Beach, just over one mile to Croteaux Vineyards- plenty of other wineries, organic farms and restaurants nearby! The space features a first floor living room area with high ceilings and access to an outside wrap around deck which overlooks pool area. Modern Chef’s Kitchen, Dining Area, Bedroom 1, Master Bedroom with a CAL king bed and Bath and access to the Garage. Downstairs has a fun Bar Room with direct access to the Pool, Bedroom 2 has a king bed, Bathroom down the hall, the Laundry Room with Washer/Dryer and another Living Room area with a piano, TV and games. Upstairs, Bedroom 3 has a full over full bunk bed with trundle, daybed and crib if needed. Bedroom 4 has a king bed. You will make wonderful summer memories in this home! Rental Permit #0362
      Presented By: Douglas Elliman Real Estate  631-354-8100
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 315 Maple Lane Southold, NY 11971
      $30,000
      4 Bedrooms 4 Full Baths Sq. Ft. 3500.00:# Square Feet
      Single Family For Rent ML# 3528088
      Ideal North Fork Dream Home for Spring and Summer Living! Embrace the vibrant spirit of Southold with this spacious and inviting home. Boasting four generously sized bedrooms, three equipped with ensuite bathrooms and the first-floor bedroom conveniently offering access to a full bath across the hall, this residence ensures comfort and convenience. The heart of the home, the great room, showcases the second fireplace and opens up to the rear masonry deck, which overlooks the large, heated pool and the backyard. Just a few blocks away is an array of charming shops, cafes, and restaurants, adding to the allure of this perfect home base for your North Fork experience. Available Year Round at 10k per month. June: 30K July: 38k August: 45k. Memorial Day- Labor Day: 100k. Also available off season.
      Presented By: Compass Greater NY LLC  516-330-6086
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 590 Soundview Av Ext Southold, NY 11971
      $30,000
      4 Bedrooms 4 Full Baths 1 Half Bath
      Single Family For Rent ML# 3524504
      Spacious Open Floor Plan Newer Home. Inground Pool with Built in Hot Tub and Blue Stone Pool Surround. Screened Porch Overlooking Pool Area. Nice Yard. Wood Burning Fireplace. Good Wifi. Long Island Sound Beach and Historic Lighthouse Museum and Park Several Doors Away. Summer 2024 - Memorial Day through June $30, 000. Off Season Until End of April 2024 at $10, 000 Per Month (Single or Multiple Months Rental Considered). Permit #0537.
      Presented By: Douglas Elliman Real Estate  631-477-2220
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 470 Goose Creek Lane Southold, NY 11971
      $30,000
      3 Bedrooms 2 Full Baths Sq. Ft. 2000.00:# Square Feet
      Single Family For Rent ML# 3236473
      Rental permit 405. Dine Al Fresco! Enjoy The Spectacular Sunsets At This Waterfront Paradise. 3 Bedroom 2 bath Contemporary Home With 1st Floor Waterside Master Suite. New Soft padded Heated/Lighted Salt Water IG Pool W/Automatic Cover, Unobstructed Waterviews, Enclosed Outdoor Shower, Hi End Newly Built Kitchen. Enjoy Kayaking, Paddle Boarding and Fishing From Your Own Dock. Easy Direct Bay Access. Beautiful Goose Creek Beach Practically at Your Doorstep. Available October 24 - April 2025 Or July 2025. Exit Clean, Utility & Security Deposit Required. Leased For July 24
      Presented By: Thomas J McCarthy Real Estate  631-765-5815
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 75 Clearview Avenue Southold, NY 11971
      $32,500
      $27,000
      4 Bedrooms 3 Full Baths 1 Half Bath
      Single Family For Rent PRICE REDUCED ML# 3513782
      2024 Rates July $6, 750.00/week (two week minimum) or $27, 000.00 for the month: Brand New Modern Farmhouse Completed in 2021 and located in the heart Hog’s Neck in Southold Hamlet. This home features an impressive 20x50 heated pool w/ electric cover, out door shower and sprawling paver patio. The interior is open and airy w/ Chef’s Kitchen outfitted with Thermador appliances, large living room with built in shelving, gas fireplace and formal dining room. All four bedrooms are located on the second level: 1 Primary En-suite, 1 Junior Suite, 2 Guest Bedrooms and Full Hallway Bathroom. You will enjoy being within close proximity to Goose Creek, South Harbor Park Beach and Southold’s vibrant business district!
      Presented By: Daniel Gale Sothebys Intl Rlty  631-477-0013
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 950 Blue Marlin Drive Southold, NY 11971
      $24,000
      4 Bedrooms 4 Full Baths Sq. Ft. 3200.00:# Square Feet
      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 June $24K, August $45K, Sept $25K RP# 0857
      Presented By: Town And Country Real Estate  631-477-5990
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 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
    • 2740 Main Bayview Rd Southold, NY 11971
      $22,000
      3 Bedrooms 3 Full Baths
      Single Family For Rent ML# 3531922
      Incredibly charming North Fork rental complete with farm field views, in-ground pool, pool house, gas fire pit and more. Stylish and updated, this 3 bedroom home is flooded with natural light, has both interior and exterior fire places, farmhouse kitchen and charming period details. Enjoy the resort-like pool area with family and guests, taking in the beautiful views of the vineyards and farms on the neighboring lots. Plenty of extra guest space. Also available off season, please inquire. June- 22k July-28k August-35k Mem-LD- 80K
      Presented By: Compass Greater NY LLC  516-330-6086
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    Showing 71 - 80 of 132 results| view:  results per page« first|...|6|7|8|9|...|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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