Southold, NY Homes

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  $6,299,000

  • Land
  • 51 Acres
  • $123,510 per Acre

  44075 Route 25, Peconic, NY 11958

  Step into the heart of North Fork wine country with the rare opportunity to own Osprey’s Dominion, an award-winning, fully operational winery and vineyard with a celebrated brand and loyal following. Perfectly positioned along the highly visible Main Road (Route 25) in Peconic, this landmark estate combines prime location, modern facilities, and limitless growth potential. Spanning over 50 acres,

  Susan Orioli Engel & Volkers North Fork

  44075 Route 25, Peconic, NY 11958
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  /20

  $3,000 per month

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • Apartment for Rent

  475 Youngs Ave Unit c, Southold, NY 11971

  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

  Nicholas Planamento William Raveis New York LLC

  475 Youngs Ave Unit c, Southold, NY 11971
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  $760,000 Sold Apr 03, 2025

  805 Oak Ave, Southold, NY 11971

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Built 1938

  Last Sold Summary

  • 1% Above List Price
  • $760/SF
  • 16 Days On Market

  Current Estimated Value $796,581

  Last Listing Agent Rita Rooney Douglas Elliman Real Estate

  805 Oak Ave, Southold, NY 11971
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  Est $1,103,721 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,850 Sq Ft

  1520 Paradise Shores Rd, Southold, NY 11971

  1520 Paradise Shores Rd, Southold, NY 11971
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  /40

  $624,900

  • 3 Beds
  • 2 Baths
  • 975 Sq Ft

  350 Brigantine Dr, Southold, NY 11971

  Welcome to 350 Brigantine Drive, a charming Southold retreat set in the peaceful waterfront-community of Harbor Lights where you can enjoy a private beach that overlooks the Peconic bay and Shelter Island. This home offers comfortable living, an inviting layout, and access to all the natural beauty and coastal lifestyle that make Southold so desirable. The main level features a bright and open

  Nicole Petersen Century 21 Icon

  350 Brigantine Dr, Southold, NY 11971
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  /47

  $40,000 per month

  • 6 Beds
  • 5.5 Baths
  • 6,600 Sq Ft
  • House for Rent

  57305 Route 48, Greenport, NY 11944

  Spectacular, contemporary seasonal rental home with pool and Jacuzzi on the Long Island Sound front. 150 feet of direct waterfront and beach, with incredible view. Meticulously renovated and professionally designed. 6 bedrooms, 5.5 bathrooms. Hamptons luxury in North Fork. Home situated on 1 acre, 6,600 square feet. One master bedroom has jacuzzi and steam room and two extra bedrooms with full

  Zepur Diktas Compass Greater NY LLC

  57305 Route 48, Greenport, NY 11944
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  $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 $1,002,435

  Last Listing Agent Tom Uhlinger Douglas Elliman Real Estate

  555 Oakwood Dr, Southold, NY 11971
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  Est $1,576,640 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

  $2,399,000

  • 3 Beds
  • 2 Baths
  • 2,000 Sq Ft

  470 Goose Creek Ln, Southold, NY 11971

  Waterfront living designed for effortless coastal comfort. Ideally located just moments from one of Southold’s premier beaches, this updated 3-bedroom, 2-bath contemporary home offers wide-open water views, beautiful sunrises and sunsets, and a seamless indoor–outdoor flow. The light-filled main level features a newly built modern kitchen that opens directly to the outdoor entertaining area,

  Thomas McCarthy Thomas J McCarthy Real Estate

  470 Goose Creek Ln, Southold, NY 11971
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  $3,500 per month

  • 4 Beds
  • 2 Baths
  • 2,000 Sq Ft
  • House for Rent

  6710 Soundview Ave, Southold, NY 11971

  Enjoy Southold this Summer at a Sleek Scandinavian Style Farm Ranch. Available for Bi-Weekly Rental Only. The Rate is Weekly at a Bi-Weekly Minimum. Nestled on Shy 2.5 Acres of Private Wooded Property You Can Truly Get Away from It All. Constructed in 2022 for Elegance and Comfort. Complete One Level Living at Its Finest. The Home Boasts a Grand Open Layout with Vaulted Ceilings Throughout.

  Rene Giacobbe Douglas Elliman Real Estate

  6710 Soundview Ave, 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 $770,478

  Last Listing Agent Cynthia Dgheim Century 21 Albertson Realty

  700 Bayview Ave, Southold, NY 11971
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  Est $1,318,628 Not Listed For Sale

  • 3 Beds
  • 3 Baths

  670 Seawood Dr, Southold, NY 11971

  670 Seawood Dr, Southold, NY 11971
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  /2

  $399,000 Pending

  • 3 Beds
  • 1 Bath

  6825 Hortons Ln, Southold, NY 11971

  3 bedroom 2 1/2 baths in need of total gut renovation

  Yvette Sanchez NEW YORK REALTY GP LLC

  6825 Hortons Ln, Southold, NY 11971
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  /30

  $10,000 per month

  • 3 Beds
  • 1.5 Baths
  • 1,578 Sq Ft
  • House for Rent

  425 Old Shipyard Ln, Southold, NY 11971

  Southold-Enjoy the North Fork in this adorable cottage. Located in Founder's Landing Southold beach community. Three bedrooms, living room, kitchen with dining area and sunroom overlooking yard and pool. This charming home has everything you need for a great summer getaway. Close to community beach and Park. Close to town, restaurants, shopping, The giving room yoga and juice bar, Southold fish

  Amy Kirincic The Agency Northshore NY

  425 Old Shipyard Ln, 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 $2,067,333

  Last Listing Agent Kristen Vlahopoulos Compass Greater NY LLC

  1820 Kenneys Rd, Southold, NY 11971
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  Est $947,849 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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  /16

  $565,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,100 Sq Ft

  48920 Route 25, Southold, NY 11971

  Fantastic opportunity to get into the North Fork market offered via this "move in" condition 2 bedroom/2bathroom cottage on .17 acres w/ large detached 1.5 car garage. The interior features a large and inviting living room, primary ensuite bedroom, guest ensuite bedroom with attached home office, galley kitchen and intimate dining area. The location is fantastic as you can take a short walk or

  William Walters Daniel Gale Sothebys Intl Rlty

  48920 Route 25, Southold, NY 11971
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  /21

  $10,000 per month

  • 5 Beds
  • 7 Baths
  • 3,500 Sq Ft
  • House for Rent

  495 N Parish Dr, Southold, NY 11971

  Southold, North Fork.Experience the beauty of seasonal living on Southold Bay. This newly renovated contemporary bayfront estate home invites you to bask in its light and bright ambiance, perfect for relaxation and rejuvenation. With its Zen-inspired organic design, you’ll find comfort and privacy combined with the conveniences of modern life.Nestled near the Southold Yacht Club, just

  Nicholas Planamento William Raveis New York LLC

  495 N Parish 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 $738,529

  Last Listing Agent Scott Bennett Douglas Elliman Real Estate

  155 Seawood Dr, Southold, NY 11971
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  Est $895,029 Not Listed For Sale

  • 3 Beds
  • 2 Baths

  1785 Seawood Dr, Southold, NY 11971

  1785 Seawood Dr, 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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  /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
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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

  Current Estimated Value $736,403

  Last Listing Agent Maryse Bransfield William Raveis New York LLC

  1040 Nakomis Rd, Southold, NY 11971
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  Est $1,169,202 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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  /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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  $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 $1,309,333 Not Listed For Sale

  • 5 Beds
  • 4 Baths

  1525 Leeward Dr, Southold, NY 11971

  1525 Leeward Dr, 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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  /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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  $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 $3,211,500 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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  /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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  $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 $1,792,327

  Last Listing Agent Kristy Naddell Douglas Elliman Real Estate

  17240 Soundview Ave, Southold, NY 11971
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  Est $1,346,423 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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  /28

  $1,999,000

  • 3 Beds
  • 2.5 Baths
  • 2,000 Sq Ft

  3500 Pine Neck Rd, Southold, NY 11971

  Step into nearly three centuries of preserved history at 3500 Pine Neck Road, Southold—an extraordinary historic residence originally built in 1720 and impeccably maintained in pristine condition. This is not simply a home; it is a rare architectural heirloom, offering authenticity, craftsmanship, and legacy that cannot be replicated. Every historic element has been preserved to perfection,

  Trish Bergin Signature Premier Properties

  3500 Pine Neck Rd, 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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  $998,500 Sold Mar 21, 2025

  1150 Kenneys Rd, Southold, NY 11971

  • Land
  • 6.96 Acres
  • $143,463 per Acre

  Last Sold Summary

  • 9% Below List Price
  • 59 Days On Market

  Current Estimated Value $1,041,500

  Last Listing Agent Thomas McCarthy Thomas J McCarthy Real Estate

  1150 Kenneys Rd, Southold, NY 11971
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  Est $3,036,667 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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