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 98 results| view:  results per page« first|...|6|7|8|9|10 »
    • 215 Northfield Lane Southold, NY 11971
      $13,000
      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. BOOK NOW FOR SUMMER 2025. Terms: May $13K, June $14K, August-LD $28K, Sept, $14K, Oct 414K
      Presented By: Thomas J McCarthy Real Estate  631-765-5815
      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 #0834) Available for 2 weeks @ $3000 per week.
      Presented By: Town And Country Real Estate  631-477-5990
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 170 Laurel Avenue Southold, NY 11971
      $12,000
      4 Bedrooms 2 Full Baths
      Misc For Rent ML# 3539926
      Beautifully decorated, charming 4 bedroom, 2 bath home with custom details throughout. Complete with an outdoor shower, enjoy the tranquil setting relaxing on the patio or in the luxurious sauna. Revel in the great location conveniently located near sandy beaches, wineries, restaurants, and public transportation. Available for August. Rental Permit #0639.
      Presented By: Town And Country Real Estate  631-477-5990
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 250 Wesland Rd Southold, NY 11971
      $10,500
      2 Bedrooms 2 Full Baths Sq. Ft. 1400.00:#
      Single Family For Rent ML# 3478213
      NEW TO THE RENTAL MARKET! JUST A DREAM BOAT! NEWLY RENOVATED, LIGHT AND BRIGHT, BEAUTIFULLY APPOINTED, EVERY CONVENIENCE - 2 BEDROOMS, 2 BATHS. PLUS - CONVERTIBLE QUEEN SOFABED! BEAUTIFUL OUTDOOR DINING, FIRE PIT, PORCH, ENCLOSED SHOWER! PRICED RIGHT! STEPS TO POPULAR KENNEY’S BEACH - JUST BRING YOUR LITTLE RED WAGON AND STROLL TO THE BEACH AND ENJOY!, Additional information: Appearance:excellent!, Lease Term:August-Labor Day, July, July-August, June, Memorial-Labor, Off Season, Weekly, Weekly Rent Amt:3000
      Presented By: Beninati Associates  631-765-5333
      Call Today: 631-765-5333, 631-235-8980, or  Email: Marie Beninati
      Call Today: 631-765-5333, or  Email: Lee Beninati
    • Southold, NY 11971
      $10,000
      4 Bedrooms 2 Full Baths 1 Half Bath
      Single Family For Rent ML# 3289709
      Welcome to this fabulous vacation home located at 1275 The Esplanade, in Southold’s coveted Angel Shores private bay beach community. The private bay beach is so close you can hear the waves and feel the bay breeze from your porch. There is a glorious free form, heated pool, with a sparkling fountain and waterfall. Outdoor shower, patio fire pit, BBQ and plenty of outdoor lounge areas complete the private backyard. The interior is stunning! Stylish decor and furnishings, central air and a house generator, a huge sun room that overlooks the pool. Sleek and spacious rooms, with hardwood floors throughout. The first floor was totally renovated , completed in 2024. The large kitchen has quartz countertops and high-end appliances, open concept living room, spacious dining area, and a brand-new powder room. The second floor was renovated in 2023 with upscale spa like bathrooms and a second-floor laundry room for your convenience. The finished lower level has an entertainment area and game room with a pool table and arcade game. Also, there are 3 kayaks and 5 bicycles available for you to fully enjoy all the North Fork has to offer. Rental rates for 2025: Memorial Day Weekend Friday thru month of June $24, 500, month of July $29, 500, August thru Labor Day Tuesday Sept 2nd $39, 500. Full Season MD to LD $75, 000. Off season months of October thru April $10, 000 per with 2 month min. Your Best Summer Vacation Poolside and By the Sea Shore! RP#0439
      Presented By: Town And Country Real Estate  631-298-0600
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 13595 Soundview Avenue Southold, NY 11971
      $9,000
      3 Bedrooms 2 Full Baths 1 Half Bath
      Single Family For Rent ML# 3587451
      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
    • 935 Corey Creek Lane Southold, NY 11971
      $8,000
      3 Bedrooms 2 Full Baths 2 Half Baths
      Single Family For Rent ML# 3576925
      Stunning Southold Luxe New Construction Rental with Dreamy Backyard. Make memories and have fun in this three bedroom, four bathroom home with finished basement, huge pool house, outdoor kitchen, in-ground pool. Meticulously landscaped outside and luxury decor and amenities throughout. Rental Permit #0515, Additional information: Weekly Renta Amt:5000
      Presented By: Douglas Elliman Real Estate  631-354-8100
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 450 Sterling Woods Lane Southold, NY 11971
      $8,000
      4 Bedrooms 3 Full Baths Sq. Ft. 3400.00:#
      Single Family For Rent ML# 3559564
      Spacious Open Plan Home with So Much to Offer near Several Great Beaches. Open Livingroom, Dining Room, Kitchen, a Separate Den and a Separate Office as well as a Good Size Bedroom and Bath on First Floor. The Spacious Kitchen Offers Sub Zero Refrigerator, a Wine Fridge and a Separate Fridge Dedicated to Drinks You Grab on Way to Pool. Primary Ensuite and Two Bedrooms and Hall Bath on Second Floor. Finished Lower Level Family Room offers TV with Gaming Hookup and a Closet Full of Games to Enjoy. Fully Fenced Large Back Yard. Additional Separate Fencing around Inground Heated Pool with Easy Automatic Solar Cover and Pool House. Large Stone Patio for BBQing, Dining and Lounging and Lots of Open Backyard Grass Area to Play the Yard Games Provided or to Simply Star Gaze at Night. Room for All. Available Single or Multiple Months 10/13/24 to 4/30/25 at $8, 000 Per Month and Summer 2025 - Memorial Day to Labor Day $90, 000; June $28, 000; July $32, 000; August to Labor Day $40, 000; Labor Day to end of September $10, 000. Pets Considered on Case-by-Case Basis. Permit #0913.
      Presented By: Douglas Elliman Real Estate  631-477-2220
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 475 Youngs Avenue Unit #c Southold, NY 11971
      $8,000
      2 Bedrooms 1 Full Bath Sq. Ft. 900.00:#
      Apartment For Rent ML# 3552884
      Southold, North Fork: Discover the epitome of easy living at Unit C Baldwin T. Payne in Southold, North Fork. This condo-like residence, part of the North Fork Resident’s Inn, offers a one-of-a-kind opportunity to embrace a modern lifestyle in a historic setting. The unit boasts a spacious layout with direct garden access, abundant natural light, and contemporary furnishings. With upscale appliances (including gas range, refrigerator/freezer with ice maker, dishwasher, on-site laundry, and more), wide plank floors, and elegant marble touches, every detail has been carefully considered. The property is conveniently located near public transportation, quality shopping, parks, and beaches, making it an ideal choice for anyone seeking a convenient and comfortable living space. With flexible rates throughout the year (MD-LD $21k; June $6500k; July $7.5k, Aug-LD $8.5k, Bal of Sept or October $5k; November through April $3.5k or year-round $4.5k per mo) and the possibility of bringing pets with landlord approval, this property is a standout option for those looking to vacation or settle into the North Fork lifestyle. Broker/Owner. Rental Permit #0171.
      Presented By: Town And Country Real Estate  631-298-0600
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 475 Youngs Avenue Unit B Southold, NY 11971
      $7,000
      1 Bedroom 1 Full Bath Sq. Ft. 800.00:#
      Single Family For Rent ML# 3589448
      Southold, North Fork - centrally located (no car needed) 1 bedroom apartment in legal 3-family building. Unit is completely separate and independent of other units. Fully furnished. Tenant responsible for utilities, security, etc and is to carry insurance. Pets on individual basis. A perfect pied-a-terre in wine country whether short stay, vacation, or possibly year-round...comfortably furnished and convenient to all. Rental Permit# 170.
      Presented By: Town And Country Real Estate  631-298-0600
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    Showing 71 - 80 of 98 results| view:  results per page« first|...|6|7|8|9|10 »
    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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