Southold, NY Homes for Sale

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  /3

  $850,000

  Pre-Foreclosure

  • 3 Beds
  • 4 Baths
  • 2,100 Sq Ft

  150 Baywater Ave, Southold, NY 11971

  Steeped in history and set on a 1.05-acre parcel in the heart of the North Fork, this circa-1663 residence presents a rare opportunity to preserve and reimagine one of Southold’s oldest and most significant properties. Ideally positioned, it is just moments from one of the East End’s finest sandy bay beaches and Croteaux Vineyards, as well as a short drive to renowned wineries, farm stands, and

  Marco Maida Compass Greater NY LLC

  150 Baywater Ave, Southold, NY 11971
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  /30

  $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 circa 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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  /42

  $3,850,000

  Open Sat 11AM - 12:30PM

  • 6 Beds
  • 4 Baths
  • 4,663 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 6-bedroom, 4-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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  /24

  $1,249,000

  $500K PRICE INCREASE

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

  650 the Esplanade, Southold, NY 11971

  Southold, North Fork - Private Bayfront Community Living Discover effortless, upscale living in the coveted Angel Shores bayfront community, complete with private association access to a pristine sugar-sand beach. Set on a beautifully landscaped, ultra-private lot backing to over 20 acres of protected preserve land-with only one immediate neighboring home-this exceptional 2,300 sq ft contemporary

  Nicholas Planamento William Raveis (Mattituck)

  650 the Esplanade, Southold, NY 11971
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  /28

  $1,445,000

  Open Sat 10:30AM - 12PM $50K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,600 Sq Ft

  470 Windy Point Ln, Southold, NY 11971

  Boaters Dream! Located in Southold, this 3-bedroom, 3-bathroom canal-front home on Cory Creek offers a well-designed layout and direct access to the water. The creek leads out to the bay, and the property features a deep-water dock suitable for a variety of boating needs. Inside, the home offers an open-concept living, dining, and kitchen area with a comfortable, functional flow. The kitchen

  Katie Schimpf Daniel Gale Sothebys Intl Rlty

  470 Windy Point Ln, Southold, NY 11971
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  /22

  $970,000

  Open Sun 11:30AM - 1:30PM $80K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,989 Sq Ft

  5845 N Bayview Rd, Southold, NY 11971

  Tucked away in a peaceful enclave of Southold, this classic Cape Cod offers a private escape that backs directly onto protected woodlands. One of the home’s standout features is an expansive four-season sunroom, which serves as a light-filled bridge between the indoors and your own quiet backyard sanctuary. Whether you are hosting a summer brunch or enjoying a morning coffee, the surrounding

  Stephanie Visek Engel & Volkers North Fork

  5845 N Bayview Rd, Southold, NY 11971
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  /7

  $1,499,000

  $201K PRICE DROP

  • Land
  • 5.25 Acres
  • $285,524 per Acre

  11200 N Bayview Rd, Southold, NY 11971

  Extremely rare offering of 5.25 acres of undeveloped, wooded land in bucolic Paradise Point - the crown jewel of the charming hamlet of Southold. Once an scenic equestrian grazing meadow to an adjoining 33 acre estate, this land offers a tranquil, secluded location close to gorgeous Bay beaches. Borders preserved land. Just a few scenic miles to fine dining and cafes, tasting rooms & vineyards,

  Kathleen Travers Douglas Elliman Real Estate

  11200 N Bayview Rd, Southold, NY 11971
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  /31

  $1,950,000

  • 2 Beds
  • 2 Baths
  • 3,603 Sq Ft

  4630 Youngs Ave, Southold, NY 11971

  Calling all artists or collectors of any kind! This is what you have been waiting for. Welcome to Homeport, loft-like living on the North Fork. A fully sustainable, net-zero home with non-toxic, recyclable and eco-friendly materials including solar and an EV charging station. A 30' x 60' studio with a garage door and 12' ceilings. Space for at least 10+ cars. An ensuite office with an additional

  Sheri Winter Parker Corcoran

  4630 Youngs Ave, Southold, NY 11971
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  /41

  $1,925,000

  Coming Soon

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

  2100 Glenn Rd, Southold, NY 11971

  This turnkey opportunity in Southold, bordering beautiful Goose Creek, offers a private dock and is perfect for those seeking a North Fork beach house with a boater's lifestyle. Situated on more than two-thirds of an acre, this contemporary home features modern lines, abundant natural light, and a stunning yard ideal for outdoor entertaining. Upon arrival, you are welcomed by a spacious driveway

  Alexis Meadows Compass Greater NY LLC

  2100 Glenn Rd, Southold, NY 11971
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  /15

  $699,000

  Open Sat 11AM - 12:30PM

  • 3 Beds
  • 1 Bath

  430 Grove Rd, Southold, NY 11971

  Enter the Season and enjoy North Fork Serenity with the creek across the street to launch into what Southold has to offer. Discover the perfect blend of coastal charm and country tranquility at 430 Grove Road, ideally located in the heart of Southold on the beautiful North Fork of Long Island—where vineyards, farms, and waterfront serenity define the lifestyle. This inviting 3-bedroom, 1-bath

  Karyn Flores Compass Greater NY LLC

  430 Grove Rd, Southold, NY 11971
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  /27

  $4,300,000

  • Land
  • 45.77 Acres
  • $93,948 per Acre

  46975 Main Rd, Southold, NY 11971

  Some estates are acquired. The exceptional are entrusted to the next chapter. Set within the North Fork’s most storied agricultural landscape, this extraordinary lifestyle farm unfolds across protected vineyard acreage and open sky - a private world defined by refinement, scale, and possibility. Being offered together are two parcels: 43.7 preserved acres, where development rights have been sold

  Andrea Parks Douglas Elliman Real Estate

  46975 Main Rd, Southold, NY 11971
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  $950,000

  • 4 Beds
  • 3 Baths
  • 1,500 Sq Ft

  36595 County Road 48, Peconic, NY 11958

  Welcome to your opportunity to own a piece of the North Fork lifestyle. Situated on over half an acre in the heart of Peconic, this expanded ranch offers the perfect blend of comfort, space, and potential just minutes from everything that makes the North Fork one of Long Island’s most sought-after destinations. This well-maintained home features a functional single-level layout with an updated

  Anthony Gutierrez Signature Premier Properties

  36595 County Road 48, Peconic, NY 11958
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  /10

  $560,000

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

  2555 Youngs Ave Unit 1D, Southold, NY 11971

  Gorgeous, light, bright, and airy, this immaculate 2-bedroom, 2-bath condominium is located in the highly desirable Founders Village 55+ community. Featuring soaring vaulted ceilings, an eat-in kitchen, spacious living and dining areas, and an inviting open layout, this home is designed for comfortable, low-maintenance living. The primary suite offers a private bath and generous closet space,

  Thomas McCarthy Thomas J McCarthy Real Estate

  2555 Youngs Ave Unit 1D, Southold, NY 11971
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  /30

  $2,995,000

  • 2 Beds
  • 1 Bath
  • 837 Sq Ft

  825 N Sea Dr, Southold, NY 11971

  It’s All About the Location! Perfectly situated along the Long Island Sound in the coveted hamlet of Southold. This quintessential North Fork beach cottage captures the very essence of coastal living, offering 100 feet of prime, sandy beachfront—a rare and exceptional find. While intimate in scale, the property delivers a lifestyle that’s nothing short of extraordinary. Spend your days seaside,

  William Walters Daniel Gale Sothebys Intl Rlty

  825 N Sea Dr, Southold, NY 11971
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  /46

  $2,350,000

  • 4 Beds
  • 4.5 Baths
  • 3,248 Sq Ft

  1665 Glenn Rd, Southold, NY 11971

  Newly built and beautifully enhanced with approx. $300K in upgrades since purchase, 1665 Glenn Road offers a turnkey North Fork retreat with thoughtful upgrades, elevated finishes, and exceptional indoor-outdoor living. Set on a .52-acre lot in Southold, this 4-bedroom, 4.5-bath home spans approximately 3,248 square feet and features a desirable layout with a first-floor ensuite primary bedroom

  Kristy Naddell Douglas Elliman Real Estate

  1665 Glenn Rd, Southold, NY 11971
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  /20

  $949,000

  $50K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 1,862 Sq Ft

  240 Lisa Dr, Southold, NY 11971

  Welcome to this spacious 4-bedroom, 2.5-bath two-story home located in the desirable Highpoint Meadows community of Southold. Set on a corner lot, this property offers a welcoming front yard and a generously sized backyard with ample room for a pool and outdoor entertaining. Inside, the home features an open-concept kitchen and dining area ideal for everyday living and gatherings, complemented by

  Scott Bennett Douglas Elliman Real Estate

  240 Lisa Dr, Southold, NY 11971
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  /30

  $6,550,000

  • 5 Beds
  • 4.5 Baths
  • 3,500 Sq Ft

  920 Cedar Point Dr E, Southold, NY 11971

  An extraordinary offering on the Peconic Bay, this refined Cedar Beach waterfront estate presents over 200 feet of direct, sun drenched, south facing shoreline and beach with a protected dock deep enough for a mid-twenty-foot boat, a truly rare combination of attributes to find on the North Fork. Thoughtfully designed to embrace its breathtaking setting, the house is set on a double lot whose

  Patricia Cosmadelis Daniel Gale Sothebys Intl Rlty

  920 Cedar Point Dr E, Southold, NY 11971
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  /26

  $999,000

  • 3 Beds
  • 1.5 Baths
  • 2,350 Sq Ft

  155 2nd Ave, Peconic, NY 11958

  North Fork Coastal Living by the Sound. Located in Peconic near Goldsmith Inlet and the Long Island Sound, this house was personally built by the owner, an experienced home builder, with a focus on superior materials, meticulous construction and pride of ownership. An open living, dining, and kitchen areas extend to a balcony that showcases beautiful sunsets and water views, creating a seamless

  Scott Bennett Douglas Elliman Real Estate

  155 2nd Ave, Peconic, NY 11958
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  /46

  $1,499,000

  Open Sun 1PM - 2:30PM

  • 4 Beds
  • 1.5 Baths
  • 1,880 Sq Ft

  1760 Albertson Ln, Greenport, NY 11944

  Scenic and bucolic, this 3+ acre country farm is steeped in classic North Fork charm. The property features an authentic 1800s four-bedroom, one and a half bath, farmhouse, a 2+ car garage (1976) with a workshop, office and mechanics pit, and a 1985 barn equipped with three horse stalls and ample space for tractors. Additional structures include a cinderblock chicken coop and a pig sty, offering

  Paul Loeb Douglas Elliman Real Estate

  1760 Albertson Ln, Greenport, NY 11944

Showing Results 41 - 59, Page 2 of 2