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 »
    • 675 Birch Avenue Southold, NY 11971
      $40,000
      5 Bedrooms 4 Full Baths Sq. Ft. 3100.00:# Square Feet
      Single Family For Rent ML# 3535739
      Immacualte 5 bedroom, 4 bath pool home only two houses away from Goose Creek. Lush landscaping and heated in-ground pool recently added. Three levels of living with bedrooms on each floor. Perfect home for entertaining. Fully finished lower level opens to pool. Main level has a screened porch and bbq porch that overlook the pool Enjoy the outdoors in the pool, on the newly built social area, or from the outdoor dining area. Truly a special jewel for the month of August-LD.
      Presented By: Compass Greater NY LLC  631-251-8644
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 3400 Youngs Avenue Southold, NY 11971
      $40,000
      4 Bedrooms 2 Full Baths
      Single Family For Rent ML# 3489027
      Permit #493 Newly Renovated Farmhouse Centrally Located In Southold With Easy Access By Bus, Train or Car. Enjoy Your Morning Coffee As The Sun Rises Over The Farmfield. Spend An Afternoon Exploring The Beauty of the North Fork, Soak in the Sun at one of the Beautiful Peconic Bay or Long Island Sound Beaches, Enjoy Live Music at Numerous Wineries and/or Breweries, Browse unique local finds at One of Many Antique and/or Quaint Shops, and Don’t Forget to Stop by Our Bountiful Farm Stands. Cool Off With a Dip in the Heated Saltwater Pool, Enjoy Dinner Under the Stars and Reminisce Around the Fire Pit. Utilities Included. 10% Security & Exit Clean. Enjoy Summer On The North Fork!
      Presented By: Thomas J McCarthy Real Estate  631-765-5815
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 910 Glenn Rd Southold, NY 11971
      $35,000
      4 Bedrooms 3 Full Baths 1 Half Bath
      Single Family For Rent NEW ML# 3546491
      Introducing your brand-new summer retreat! Available from July 2024, this stunning 4-bedroom, 3.5-bathroom waterfront oasis boasts the pinnacle of luxury living. Nestled on West Creek in Southold. Enjoy exclusive access to Peconic Bay via your private dock, perfect for soaking up the summer sun. Spanning approximately 3500 square feet of impeccable interior space, revel in the elegance of oak floors, a luxurious soaking tub, and high ceilings throughout. The first floor offers two primary ensuites, a spacious Great Room with a cozy fireplace, a convenient laundry room, and 2.5 baths. Plus, a two-car garage ensures ample parking for all your summer adventures. Ascend to the second floor to discover two additional bedrooms, a full bath, a second laundry area, and a sprawling bonus room-ideal for entertaining guests or unwinding after a day of exploration. Central air conditioning ensures comfort on even the hottest summer days, while a full basement provides plenty of storage space for your beach gear. Outside is your private paradise, complete with a refreshing 16 x 32 in-ground pool, currently being readied for the summer. Situated in the coveted Southold Park District, relish in access to Founder Landing and South Harbor Park, along with proximity to pristine bay beaches, renowned vineyards, charming farmstands, premier shopping destinations, and convenient public transportation. Don’t miss this unparalleled opportunity to experience the epitome of summer living and make memories to last a lifetime! Southold Town Rental Permit #1085.
      Presented By: Douglas Elliman Real Estate  631-354-8100
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 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
    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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