Southold, NY Homes

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  $1,495,000 Pending

  • Land
  • 9.5 Acres
  • $157,368 per Acre

  3635 Old North Rd, Southold, NY 11971

  Prime opportunity in the heart of Southold. This exceptional 9.5 acres (approx) parcel with development rights in tact, offers endless potential, including the possibility for future subdivision. Perfectly situated among preserved farmland and surrounded by distinguished estate properties, the setting provides both privacy and prestige. Moments from Southold’s beautiful beaches, vineyards, and

  Kristy Naddell Douglas Elliman Real Estate

  3635 Old North Rd, Southold, NY 11971
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  /39

  $10,000 per month

  • 3 Beds
  • 2.5 Baths
  • 2,000 Sq Ft
  • House for Rent

  485 Pine Rd, Southold, NY 11971

  2026 Rates: MDW- June $12,000; July 23,500 A1-LD $25,000; September $12,000; October $10,000: Discover your perfect getaway in this expansive and meticulously updated ranch home, designed for relaxation and rejuvenation. Experience a resort-like atmosphere with the stunning gunite, heated saltwater pool, complemented by a beautiful stone surround and convenient outdoor shower. Step inside to find

  William Walters Daniel Gale Sothebys Intl Rlty

  485 Pine Rd, Southold, NY 11971
• 

  $899,000 Sold Jul 25, 2025

  555 Oakwood Dr, Southold, NY 11971

  • 4 Beds
  • 2.5 Baths
  • 2,300 Sq Ft
  • Built 1967

  Last Sold Summary

  • 10% Below List Price
  • $391/SF
  • 42 Days On Market

  Current Estimated Value $981,493

  Last Listing Agent Tom Uhlinger Douglas Elliman Real Estate

  555 Oakwood Dr, Southold, NY 11971
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  Est $1,546,638 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,800 Sq Ft

  2230 Paradise Shores Rd, Southold, NY 11971

  2230 Paradise Shores Rd, Southold, NY 11971
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  /25

  $2,750,000

  • 3 Beds
  • 2 Baths
  • 1,250 Sq Ft

  1455 Cedar Point Dr E, Southold, NY 11971

  Wake up to endless views of the Peconic Bay — sunlight glimmering off the water, birds gliding over the nearby nature preserve, and the calm rhythm of the deep-water inlet just beyond your deck. This sweet beach cottage captures everything that makes summer on the North Fork unforgettable. With 3 comfortable bedrooms, 2 baths, and an open, easy-flow layout connecting the living, dining, kitchen,

  Maureen Sullivan Daniel Gale Sothebys Intl Rlty

  1455 Cedar Point Dr E, Southold, NY 11971
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  /27

  $35,000 per month

  • 4 Beds
  • 3 Baths
  • 2,350 Sq Ft
  • House for Rent

  485 Hickory Ave, Southold, NY 11971

  Beautiful Goose Creek view home with large heated in-ground pool! This 4 bedroom, 3 bath house features a 1st floor primary with en-suite, a gourmet kitchen and open living space. The outdoor living space has newly designed landscape and is ideal for entertaining or relaxing. Fire pit and grill. Lawn is sprayed for ticks. Close to Southold town and Corey Creek Beach.

  Mackenzie Needham Daniel Gale Sothebys Intl Rlty

  485 Hickory Ave, Southold, NY 11971
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  $690,000 Sold Jan 02, 2025

  190 Richmond Rd E, Southold, NY 11971

  • 3 Beds
  • 1 Bath
  • 1,028 Sq Ft
  • Built 1950

  Last Sold Summary

  • 5% Below List Price
  • $671/SF
  • 58 Days On Market

  Current Estimated Value $716,940

  Last Listing Agent Edward Taraskewich Howard Hanna Rand Realty

  190 Richmond Rd E, Southold, NY 11971
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  Est $1,273,055 Not Listed For Sale

  • 3 Beds
  • 3 Baths

  670 Seawood Dr, Southold, NY 11971

  670 Seawood Dr, Southold, NY 11971
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  /15

  $1,699,000

  • 5 Beds
  • 2 Baths
  • 1,688 Sq Ft

  530 Sunset Way, Southold, NY 11971

  Wake up to breathtaking panoramic views of Peconic Bay from your own private waterfront retreat! With 160 feet of shoreline and a 6'x20' dock, this property is a dream for boaters, beach lovers, and anyone craving coastal serenity. Inside, there’s room for everyone with 5 bedrooms, 2 full baths, and a sunlit loft. The wraparound deck invites you to savor spectacular sunrises and sunsets,

  Thomas McCarthy Thomas J McCarthy Real Estate

  530 Sunset Way, Southold, NY 11971
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  /36

  $26,900 per month

  • 4 Beds
  • 4 Baths
  • 4,000 Sq Ft
  • House for Rent

  1205 Lake Dr, Southold, NY 11971

  Looking to create a beautiful memory of true summer experience on the beautiful North Fork of Long Island? look no further. This Spacious home has the full spectrum of mother nature right on your own huge back yard on the great lake with 2 fire pits. Featuring 4 Bedrooms, 4 Bath, An Oversize Patio, Large Heated In ground pool. Your own fully equipped gym to help keep you in the best of shape! You

  Chrisand Castella Douglas Elliman Real Estate

  1205 Lake Dr, Southold, NY 11971
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  $660,000 Sold Apr 07, 2025

  700 Bayview Ave, Southold, NY 11971

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • Built 1960

  Last Sold Summary

  • 24% Below List Price
  • $412/SF
  • 286 Days On Market

  Current Estimated Value $751,156

  Last Listing Agent Cynthia Dgheim Century 21 Albertson Realty

  700 Bayview Ave, Southold, NY 11971
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  Est $949,938 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,420 Sq Ft

  1750 Seawood Dr, Southold, NY 11971

  1750 Seawood Dr, Southold, NY 11971
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  /6

  $500,000 Pending

  • Land
  • 0.6 Acre
  • $833,333 per Acre

  265 Arshamomaque Ave, Southold, NY 11971

  Building Lot in Beixedon Estates private community. Private road, deeded access to private community beach. Broker/Owner.

  John J. Nickles, Jr. Lewis & Nickles LTD

  265 Arshamomaque Ave, Southold, NY 11971
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  /29

  $38,000 per month

  • 4 Beds
  • 4.5 Baths
  • 3,100 Sq Ft
  • House for Rent

  590 Soundview Ave, Southold, NY 11971

  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. Winter Rental (November 2025 to April 2026) $9,000 Per Month for Single or Multiple Months; Summer 2026 - Memorial Day to Labor

  Paul Loeb Douglas Elliman Real Estate

  590 Soundview Ave, Southold, NY 11971
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  $1,870,000 Sold Feb 28, 2025

  1820 Kenneys Rd, Southold, NY 11971

  • 6 Beds
  • 4 Baths
  • 4,000 Sq Ft
  • Built 2007

  Last Sold Summary

  • 6% Below List Price
  • $468/SF
  • 127 Days On Market

  Current Estimated Value $1,967,000

  Last Listing Agent Kristen Vlahopoulos Compass Greater NY LLC

  1820 Kenneys Rd, Southold, NY 11971
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  Est $892,467 Not Listed For Sale

  • 3 Beds
  • 2 Baths

  1785 Seawood Dr, Southold, NY 11971

  1785 Seawood Dr, Southold, NY 11971
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  /15

  $2,600,000 Pending

  • 4 Beds
  • 4.5 Baths
  • 3,960 Sq Ft

  1635 Laurel Ave, Southold, NY 11971

  TO BE COMPLETED FALL 2025. The Laurel Collection by Marrcon. New Luxury Construction located in the heart of the North Fork's Town of Southold. The Laurel model is situated on .80 acres & boasts 3,960SF of living space with 4 bedrooms and 4.5 baths.. The Laurel combines clean lines of modern design with the allure of the Hamptons. This home comes with Authentic Western Red Cedar Shingle siding

  Kristy Naddell Douglas Elliman Real Estate

  1635 Laurel Ave, Southold, NY 11971
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  /17

  $9,000 per month

  • 3 Beds
  • 2 Baths
  • 1,750 Sq Ft
  • House for Rent

  1265 Brigantine Dr, Southold, NY 11971

  Impeccable, like new ranch for rent with quality features throughout in Harbor Lights with a deeded beach and park at the end of the street. There are three bedrooms, two full bathrooms, open floor plan from kitchen through the dining area into the vaulted ceiling living room, Enjoy the beautiful screened in porch which overlooks the private back yard with slate patio, grass lawn, and outdoor

  Barbara Poliwoda Douglas Elliman Real Estate

  1265 Brigantine Dr, Southold, NY 11971
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  $675,000 Sold Mar 31, 2025

  155 Seawood Dr, Southold, NY 11971

  • 2 Beds
  • 1 Bath
  • Built 1958

  Last Sold Summary

  • 2% Above List Price
  • 33 Days On Market

  Current Estimated Value $723,119

  Last Listing Agent Scott Bennett Douglas Elliman Real Estate

  155 Seawood Dr, Southold, NY 11971
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  Est $1,134,597 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths

  605 Topsail Ln, Southold, NY 11971

  605 Topsail Ln, Southold, NY 11971
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  /7

  $499,000

  • Land
  • 0.38 Acre
  • $1,313,158 per Acre

  11195 N Bayview Rd, Southold, NY 11971

  .38-acre wooded level lot in a private and natural setting. Ideally located near Paradise Point, Cedar Beach, Southold shops, vineyards, farmstands and Greenport Brewery. This is a triangle shape lot with 258ft of frontage on N Bayview Rd and 178ft/182ft deep on each side. A rare opportunity to create your own coastal retreat in one of the North Fork’s most desirable neighborhoods. No preliminary

  Mariah Mills Daniel Gale Sothebys Intl Rlty

  11195 N Bayview Rd, Southold, NY 11971
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  /16

  $10,000 per month

  • 4 Beds
  • 2.5 Baths
  • 1,625 Sq Ft
  • House for Rent

  455 W Shore Dr, Southold, NY 11971

  Welcome to 455 West Shore Road, Southold, NY. This charming 4-bedroom, 2. 5-bathroom rental property offers 1,600 square feet of comfortable living space. Nestled in a serene location, the home provides exclusive beach rights, perfect for summer enjoyment. The spacious layout includes a well-appointed kitchen, inviting living areas, and ample storage. The property is ideal for those seeking a

  Eric Frend Corcoran

  455 W Shore Dr, Southold, NY 11971
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  $1,925,000 Sold Jan 23, 2025

  4015 Main Bayview Rd, Southold, NY 11971

  • 3 Beds
  • 3.5 Baths
  • 3,377 Sq Ft
  • Built 1930

  Last Sold Summary

  • 4% Below List Price
  • $570/SF
  • 75 Days On Market

  Current Estimated Value $1,966,682

  Last Listing Agent Susan Orioli Engel & Volkers North Fork

  4015 Main Bayview Rd, Southold, NY 11971
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  Est $1,255,000 Not Listed For Sale

  • 5 Beds
  • 4 Baths

  1525 Leeward Dr, Southold, NY 11971

  1525 Leeward Dr, Southold, NY 11971
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  /34

  $899,000 Pending

  • 5 Beds
  • 3 Baths
  • 2,300 Sq Ft

  4100 Youngs Ave, Southold, NY 11971

  ***NEW IMPROVED PRICE**Ideal for the Self-Employed Buyer or Multigenerational family: Flexibility, and Income Potential in Southold’s Wine Country.This beautifully renovated farmhouse blends timeless charm with modern comfort—perfectly suited for self-employed professionals. With 5 spacious bedrooms and 3 elegantly updated bathrooms across 2 floors, this home offers flexibility.A

  Jeannine Kowaleski William Raveis New York LLC

  4100 Youngs Ave, Southold, NY 11971
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  /31

  $34,500 per month

  • 4 Beds
  • 3.5 Baths
  • House for Rent

  75 Clearview Ave, Southold, NY 11971

  2026 Rates: July $34,500; August 1-LD $44,500: New Modern Farmhouse Completed in 2021 and located in the heart Hog's Neck in Southold Hamlet. This home features an impressive 20 x 50 heated pool with electric cover, out door shower and sprawling paver patio. The interior is open and airy with Chef's Kitchen outfitted with Thermador appliances, large living room with built in shelving, gas

  William Walters Daniel Gale Sothebys Intl Rlty

  75 Clearview Ave, Southold, NY 11971
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  $740,000 Sold Nov 04, 2025

  1040 Nakomis Rd, Southold, NY 11971

  • 3 Beds
  • 1 Bath
  • 1,100 Sq Ft
  • Built 1971

  Last Sold Summary

  • 4% Below List Price
  • $673/SF
  • 12 Days On Market

  Last Listing Agent Maryse Bransfield William Raveis New York LLC

  1040 Nakomis Rd, Southold, NY 11971
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  Est $3,433,500 Not Listed For Sale

  • 5 Beds
  • 5.5 Baths
  • 6,162 Sq Ft

  10995 N Bayview Rd, Southold, NY 11971

  10995 N Bayview Rd, Southold, NY 11971
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  /26

  $1,175,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,400 Sq Ft

  1475 Oaklawn Ave, Southold, NY 11971

  Welcome to this stunning Cape Cod-style home, completely updated in 2025 and thoughtfully designed for modern living with timeless charm. Nestled on a generous half-acre lot, this 4-bedroom, 2.5-bathroom home offers an ideal combination of style, space, and resort-style amenities. Step inside to discover a bright, open floor plan that seamlessly connects the main living areas—perfect for

  William Walters Daniel Gale Sothebys Intl Rlty

  1475 Oaklawn Ave, Southold, NY 11971
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  /30

  $24,000 per month

  • 4 Beds
  • 3.5 Baths
  • House for Rent

  6430 Hortons Ln, Southold, NY 11971

  Lovely spacious newly built Colonial just down the lane from 4 gorgeous LI Sound Beaches. Main Floor Primary Bedroom En-suite with private side entrance and it's own deck. Second Primary Bedroom En-Suite on level 2 (has radiant heat floor and heat lamp). Two additional Bedrooms, a full Bath in the hall, and Laundry Room. Kitchen has huge island with seating, 6 burner or griddle dual fuel oven.

  Kate Carpluk William Raveis New York LLC

  6430 Hortons Ln, Southold, NY 11971
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  $2,400,000 Sold Oct 09, 2025

  2215 Laurel Ave, Southold, NY 11971

  • 3 Beds
  • 3.5 Baths
  • 3,210 Sq Ft
  • Built 2025

  Last Sold Summary

  • 5% Above List Price
  • $748/SF
  • 128 Days On Market

  Last Listing Agent Kristy Naddell Douglas Elliman Real Estate

  2215 Laurel Ave, Southold, NY 11971
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  Est $1,311,386 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,492 Sq Ft

  75 Reydon Dr, Southold, NY 11971

  75 Reydon Dr, Southold, NY 11971
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  /42

  $3,850,000

  • 4 Beds
  • 3 Baths
  • 4,103 Sq Ft

  105 Waterview Dr, Southold, NY 11971

  Discover a rare waterfront property where privacy, space, and breathtaking views come together on 6.5 gated acres. Spanning two single-and-separate lots, this refreshed 4-bedroom, 3-bath colonial offers a den/office, bonus room, and sweeping water views from nearly every room. Thoughtfully designed for both comfort and future flexibility, the residence provides substantial expansion potential.

  Roric Tobin Compass Greater NY LLC

  105 Waterview Dr, Southold, NY 11971
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  /27

  $8,000 per month

  • 3 Beds
  • 2 Baths
  • 1,620 Sq Ft
  • House for Rent

  400 Hill Rd, Southold, NY 11971

  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

  Jeanmarie Bay William Raveis New York LLC

  400 Hill Rd, Southold, NY 11971
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  $865,000 Sold Dec 04, 2025

  500 Meadow Ct Unit 28, Southold, NY 11971

  • 3 Beds
  • 2.5 Baths
  • 3,735 Sq Ft
  • Built 1994

  Last Sold Summary

  • 21% Below List Price
  • $232/SF
  • 112 Days On Market

  Last Listing Agent Gayle Marriner Smith Daniel Gale Sothebys Intl Rlty

  500 Meadow Ct Unit 28, Southold, NY 11971
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  Est $2,758,667 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 3,373 Sq Ft

  400 Windjammer Dr, Southold, NY 11971

  400 Windjammer Dr, Southold, NY 11971
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  /36

  $2,499,000

  • 4 Beds
  • 4.5 Baths
  • 2,842 Sq Ft

  285 Blue Marlin Dr, Southold, NY 11971

  BONUS: Upon request builder will include a custom built 12x12 pool shed with the same materials and style identical to the house. Entire house completed and beautifully landscaped!!! With incredible water views and access to a picturesque private beach, 285 Blue Marlin exemplifies luxury coastal living at its finest. Constructed by the North Fork's most revered builders, no expense has been

  Connie Liappas Compass

  285 Blue Marlin Dr, Southold, NY 11971
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  /33

  $25,000 per month

  • 4 Beds
  • 3.5 Baths
  • House for Rent

  910 Glenn Rd, Southold, NY 11971

  Introducing your perfect retreat! This stunning 4-bed, 3.5-bath waterfront oasis nestled on West Creek in Southold. Enjoy access to Peconic Bay via your private dock. Spanning approx 3500 sq ft, revel in the elegance of oak floors, a luxurious soaking tub, and high ceilings throughout. The 1st floor has 2 primary ensuites, a spacious Great Room with cozy fireplace, laundry, and 2.5 baths +2-car

  Andrea Parks Douglas Elliman Real Estate

  910 Glenn Rd, Southold, NY 11971
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  $1,780,000 Sold Jul 11, 2025

  17240 Soundview Ave, Southold, NY 11971

  • Land
  • 25 Acres
  • $71,200 per Acre

  Last Sold Summary

  • 1% Below List Price
  • 40 Days On Market

  Current Estimated Value $1,799,760

  Last Listing Agent Kristy Naddell Douglas Elliman Real Estate

  17240 Soundview Ave, Southold, NY 11971
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  Est $1,059,068 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths

  1565 Brigantine Dr, Southold, NY 11971

  1565 Brigantine Dr, Southold, NY 11971

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