4,571

Southold, NY Homes

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  • /36

    $4,900,000

    $1M PRICE DROP
    • Land
    • 51 Acres
    • $96,078 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

    Susan Orioli Engel & Volkers North Fork

    44075 Route 25, Peconic, NY 11958
  • /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
  • 230 Booth Rd, Southold, NY 11971

    $942,500

    Sold Sep 18, 2026

    230 Booth Rd, Southold, NY 11971

    • 5 Beds
    • 2 Baths
    • 2,238 Sq Ft
    • Built 1967

    Last Sold Summary

    • 4% Below List Price
    • $421/SF
    • 38 Days On Market

    Current Estimated Value $987,042

    Last Listing Agent Nancy Cervelli Daniel Gale Sothebys Intl Rlty

    230 Booth Rd, Southold, NY 11971
    • 65 Pleasant Place, Southold, NY 11971

      Est $1,160,567

      Not Listed For Sale

      65 Pleasant Place, Southold, NY 11971

      • 4 Beds
      • 2 Baths
      • Built 1987
      65 Pleasant Place, Southold, NY 11971

      Last Sold Summary

      • 69 Days On Market

      Last Listing Agent Katie Schimpf Daniel Gale Sothebys Intl Rlty

  • /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 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, along

    Thomas McCarthy Thomas J McCarthy Real Estate

    470 Goose Creek Ln, Southold, NY 11971
  • /25

    $4,200 Per Month

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

    5650 N Bayview Rd, Southold, NY 11971

    Step into a special piece of North Fork history. Originally the Main Bayview Schoolhouse, this distinctive, furnished, Southold property has been thoughtfully converted into a welcoming five-bedroom, two-bath country residence that retains the warmth, charm and character of its past.Offering approximately 2,000 square feet of furnished living space, the home comfortably accommodates up to

    Nicholas Planamento William Raveis New York LLC

    5650 N Bayview Rd, Southold, NY 11971
  • 250 Paradise Point Rd, Southold, NY 11971

    $1,350,000

    Sold Aug 14, 2026

    250 Paradise Point Rd, Southold, NY 11971

    • 4 Beds
    • 3 Baths
    • 2,200 Sq Ft
    • Built 1982

    Last Sold Summary

    • 4% Above List Price
    • $614/SF
    • 47 Days On Market

    Current Estimated Value $1,315,204

    Last Listing Agent Barbara Poliwoda Douglas Elliman Real Estate

    250 Paradise Point Rd, Southold, NY 11971
    • 1085 Gin Ln, Southold, NY 11971

      Est $1,330,008

      Not Listed For Sale

      1085 Gin Ln, Southold, NY 11971

      • 4 Beds
      • 4 Baths
      • 3,400 Sq Ft
      • Built 1975
      1085 Gin Ln, Southold, NY 11971

      Last Sold Summary

      • 72 Days On Market

      Last Listing Agent Nancy Cervelli Daniel Gale Sothebys Intl Rlty

  • /25

    $925,000

    Pending
    • 2 Beds
    • 1 Bath
    • 1,054 Sq Ft

    1320 Arshamomaque Ave, Southold, NY 11971

    If the perfect North Fork cottage exists, you have just found it. Timeless, elegant, and rich in character, this thoughtfully crafted home offers a rare opportunity to own a piece of Southold history. Set within Beixedon Estates, an exclusive private enclave and beautiful waterfront community discretely set between Greenport and Southold, the property enjoys an exceptional location close to

    Kieran Collings Douglas Elliman Real Estate

    1320 Arshamomaque Ave, Southold, NY 11971
  • /28

    $7,500 Per Month

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

    3400 Youngs Ave, Southold, NY 11971

    Nobody comes to the North Fork because they're looking for excitement, they come because they're looking for something they've been missing. Time slows here. Not dramatically, but quietly. You notice it on the first morning when you realize you've finished your coffee without checking your phone. The windows are open, the breeze carries the scent of nearby fields, and the only thing on the agenda

    Thomas McCarthy Thomas J McCarthy Real Estate

    3400 Youngs Ave, Southold, NY 11971
  • 265 Hummel Ave, Southold, NY 11971

    $620,000

    Sold Aug 11, 2026

    265 Hummel Ave, Southold, NY 11971

    • 2 Beds
    • 1 Bath
    • 1,114 Sq Ft
    • Built 1940

    Last Sold Summary

    • 17% Below List Price
    • $557/SF
    • 149 Days On Market

    Current Estimated Value $660,194

    Last Listing Agent Amanda Lin Douglas Elliman Real Estate

    265 Hummel Ave, Southold, NY 11971
    • 945 Gin Ln, Southold, NY 11971

      Est $1,140,980

      Not Listed For Sale

      945 Gin Ln, Southold, NY 11971

      • 4 Beds
      • 3 Baths
      • Built 1972
      945 Gin Ln, Southold, NY 11971

      Last Sold Summary

      • 51 Days On Market

      Last Listing Agent Tom Scalia Century 21 Albertson Realty

  • /20

    $1,375,000

    Pending
    • 3 Beds
    • 2 Baths
    • 1,841 Sq Ft

    1050 Bayview Ave, Southold, NY 11971

    Perfectly positioned between Greenport and Southold, this classic cedar-shingled Cape offers an easygoing North Fork lifestyle with beaches, restaurants, and village amenities just minutes away. Inside, the first-floor open plan is anchored by a fireplace and a large kitchen flooded with natural light. Multiple sliding doors lead to a generous wraparound deck, outfitted for dining, lounging, and

    Eric Elkin Compass Greater NY LLC

    1050 Bayview Ave, Southold, NY 11971
  • /42

    $8,000 Per Month

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

    6710 Soundview Ave, Southold, NY 11971

    Enjoy Southold this Thanksgiving or June 2027 at a Sleek Scandinavian Style Farm Ranch. Available November 15-30 for $8000 and June 7-30 for $20,000 or $6000 Weekly, at a Bi-Weekly Minimum, Starting June 7th. 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

    Rene Giacobbe Douglas Elliman Real Estate

    6710 Soundview Ave, Southold, NY 11971
  • 20845 Soundview Ave, Southold, NY 11971

    $1,730,000

    Sold Nov 12, 2025

    20845 Soundview Ave, Southold, NY 11971

    • 3 Beds
    • 2 Baths
    • 1,408 Sq Ft
    • Built 1951

    Last Sold Summary

    • 4% Below List Price
    • $1,229/SF
    • 39 Days On Market

    Current Estimated Value $1,778,067

    Last Listing Agent Stephanie Ranghelli BH&G R E Realty Connect

    20845 Soundview Ave, Southold, NY 11971
    • 685 Bay Haven Ln, Southold, NY 11971

      Est $899,999

      Not Listed For Sale

      685 Bay Haven Ln, Southold, NY 11971

      • 3 Beds
      • 2 Baths
      • Built 1959
      685 Bay Haven Ln, Southold, NY 11971

      Last Sold Summary

      • 27 Days On Market

      Last Listing Agent Eleanor Dunne Andron Realty Group Tulip R E

  • /26

    $1,239,999

    $160K PRICE DROP Pending
    • 4 Beds
    • 3.5 Baths
    • 2,584 Sq Ft

    75 Birch Rd, Southold, NY 11971

    Tucked away on a beautifully landscaped property, this 2022 built 4 bedroom, 3.5 bath residence offers the perfect blend of modern construction, thoughtful design, and effortless North Fork charm. From the moment you arrive, the inviting front porch, complete with a classic swing, sets the tone for relaxed living. Inside, the home is thoughtfully designed with a seamless flow, anchored by a

    Susan Orioli Engel & Volkers North Fork

    75 Birch Rd, Southold, NY 11971
  • /24

    $15,000 Per Month

    • 3 Beds
    • 4 Baths
    • 1,800 Sq Ft
    • House for Rent

    935 Corey Creek Ln, Southold, NY 11971

    Experience the ultimate North Fork summer in this stunning new construction home, designed for effortless entertaining and elevated coastal living. Professionally decorated and impeccably finished, this residence offers three bedrooms, four full bathrooms, a bonus room, and a beautifully finished lower level with an additional private half bath. Step outside to your own private retreat featuring

    Melissa Principi Douglas Elliman Real Estate

    935 Corey Creek Ln, Southold, NY 11971
  • 105 Mailer Ct, Southold, NY 11971

    $600,000

    Sold Jul 21, 2026

    105 Mailer Ct, Southold, NY 11971

    • Land
    • 23,958 Sq Ft
    • $1,090,909 per Acre

    Last Sold Summary

    • 9% Above List Price
    • 7 Days On Market

    Current Estimated Value $550,653

    Last Listing Agent Maryse Bransfield William Raveis New York LLC

    105 Mailer Ct, Southold, NY 11971
    • /2

      Est $816,134

      Not Listed For Sale

      1430 Bay Haven Ln, Southold, NY 11971

      • 3 Beds
      • 2 Baths
      • Built 1973
      1430 Bay Haven Ln, Southold, NY 11971

  • /45

    $3,675,000

    New Construction
    • 5 Beds
    • 6 Baths
    • 5,285 Sq Ft

    150 Deer Run, Southold, NY 11971

    Gorgeous estate-like Nantucket shingle home to be completed early August with time to enjoy summer of 2026 and the Fall Harvest Season on the North Fork! Seller will consider owner financing.Designed by the renowned firm of Nelson and Pope utilizing steel beam construction throughout and Benjamin Obdyke Hydrogap house wrap, the home features solid white oak hardwood floors, as well as

    Jeffrey Mead Corcoran

    150 Deer Run, Southold, NY 11971
  • /21

    $22,500 Per Month

    • 4 Beds
    • 3 Baths
    • 1,800 Sq Ft
    • House for Rent

    270 N Sea Dr, Southold, NY 11971

    Southold, North Fork: Endless sunsets await at this exceptional vacation rental, available year-round with flexible terms and rates. Ideally located in the sought-after Kenny’s Beach community, this sun-drenched home is surrounded by wide sandy dunes perfect for walking, birdwatching, swimming, and relaxing days by the shore.Immaculately maintained, the residence offers 4 bedrooms and 3 full

    Nicholas Planamento William Raveis New York LLC

    270 N Sea Dr, Southold, NY 11971
  • 350 Brigantine Dr, Southold, NY 11971

    $750,750

    Sold Mar 27, 2026

    350 Brigantine Dr, Southold, NY 11971

    • 3 Beds
    • 2 Baths
    • 975 Sq Ft
    • Built 1986

    Last Sold Summary

    • 20% Above List Price
    • $770/SF
    • 31 Days On Market

    Current Estimated Value $752,140

    Last Listing Agent Nicole Petersen Century 21 Icon

    350 Brigantine Dr, Southold, NY 11971
    • 380 Gin Ln, Southold, NY 11971

      Est $1,050,911

      Not Listed For Sale

      380 Gin Ln, Southold, NY 11971

      • 6 Beds
      • 3 Baths
      • 3,784 Sq Ft
      • Built 1960
      380 Gin Ln, Southold, NY 11971

      Last Sold Summary

      • 88 Days On Market

      Last Listing Agent Ryan Springer Corcoran

  • /44

    $2,695,000

    • 3 Beds
    • 2 Baths
    • 1,650 Sq Ft

    2850 Main Bayview Rd, Southold, NY 11971

    Set on five bucolic acres, this property perfectly captures the pastoral character that defines the region at its best. Mature trees frame the entrance, and split-rail fencing lines the property, offering a sense of privacy and openness rarely found so close to everything the North Fork has to offer. The three-bedroom, two-bathroom farmhouse is complemented by a large barn, currently outfitted

    Bridget Elkin Compass Greater NY LLC

    2850 Main Bayview Rd, Southold, NY 11971
  • /20

    $13,000 Per Month

    • 4 Beds
    • 3 Baths
    • 2,300 Sq Ft
    • House for Rent

    215 Northfield Ln, Southold, NY 11971

    Permit 0681- A 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 2026. Terms & Availability: May $13,000,

    Mitch Pickman Thomas J McCarthy Real Estate

    215 Northfield Ln, Southold, NY 11971
  • 6900 Main Bayview Rd, Southold, NY 11971

    $600,000

    Sold Jul 31, 2026

    6900 Main Bayview Rd, Southold, NY 11971

    • 2 Beds
    • 1 Bath
    • 1,200 Sq Ft
    • Built 1955

    Last Sold Summary

    • $500/SF
    • 40 Days On Market

    Current Estimated Value $618,460

    Last Listing Agent Todd Yovino Island Advantage Realty LLC

    6900 Main Bayview Rd, Southold, NY 11971
    • 155 Seawood Dr, Southold, NY 11971

      Est $708,089

      Not Listed For Sale

      155 Seawood Dr, Southold, NY 11971

      • 2 Beds
      • 1 Bath
      • Built 1958
      155 Seawood Dr, Southold, NY 11971

      Last Sold Summary

      • 33 Days On Market

      Last Listing Agent Scott Bennett Douglas Elliman Real Estate

  • /44

    $3,450,000

    • 5 Beds
    • 3.5 Baths
    • 4,500 Sq Ft

    790 N Sea Dr, Southold, NY 11971

    Quintessential North Fork Beach House!! Perched high above with breathtaking views of the Long Island Sound, this stunning custom-built home offers the perfect blend of luxury, comfort, and location. Just across the street from the shores of Kenney’s Beach, this 2009-built residence features 5 spacious bedrooms and 3.5 beautifully appointed baths, including a serene first-floor primary suite. Set

    Kristy Naddell Douglas Elliman Real Estate

    790 N Sea Dr, Southold, NY 11971
  • /21

    $6,000 Per Month

    • 4 Beds
    • 3 Baths
    • House for Rent

    1155 Old Harbor Rd, Southold, NY 11971

    Quintessential North Fork sandy bay beachfront rental. Stunning views across Cutchogue Harbor and Peconic Bay will be yours at this spacious waterfront home, whether from the airy great room, the brick patio, or from the beachside deck. Tucked away down a quiet drive, this home offers peace and privacy in historic New Suffolk. There are 3 bedrooms and 2 baths upstairs, one bedroom and one bath

    Marianne Collins Brown Harris Stevens N Fork

    1155 Old Harbor Rd, Southold, NY 11971
  • 54985 Middle Rd, Southold, NY 11971

    $2,700,000

    Sold Sep 25, 2025

    54985 Middle Rd, Southold, NY 11971

    • 4 Beds
    • 5 Baths
    • 3,500 Sq Ft
    • Built 2010

    Last Sold Summary

    • 16% Below List Price
    • $771/SF
    • 133 Days On Market

    Last Listing Agent Nicholas Planamento William Raveis New York LLC

    54985 Middle Rd, Southold, NY 11971
    • 9502 N Bayview Rd, Southold, NY 11971

      Est $3,310,667

      Not Listed For Sale

      9502 N Bayview Rd, Southold, NY 11971

      • 5 Beds
      • 4.5 Baths
      • 4,051 Sq Ft
      • Built 2019
      9502 N Bayview Rd, Southold, NY 11971

      Last Sold Summary

      • 187 Days On Market

      Last Listing Agent Thomas McCarthy Thomas J McCarthy Real Estate

  • /27

    $2,650,000

    • 4 Beds
    • 3.5 Baths
    • 2,600 Sq Ft

    195 Williamsburgh Dr, Southold, NY 11971

    This breezy, open-concept home was made for hosting, with seamless flow and water views at every turn. Set on 101 feet of Corey Creek frontage, you get a brand-new bulkhead, your own boat ramp, and instant access to the bay. With 4 bedrooms and 3.5 baths, including both a first-floor primary ensuite and a second-floor primary suite, there's room for everyone to spread out in style. Two mahogany

    Sheri Winter Parker Corcoran

    195 Williamsburgh Dr, Southold, NY 11971
  • /24

    $8,000 Per Month

    • 3 Beds
    • 3 Baths
    • House for Rent

    355 Midway Rd, Southold, NY 11971

    Available seasonally, this impeccable modern 3 bedroom 3 bath home in Southold's coveted Cedar Beach district offers privacy, water views and a private neighborhood beach. The open plan includes kitchen, dining area, den/office, and living room with fireplace. Sliding doors open to the bluestone patio with gas grill and plenty of room for entertaining and sunning. The three bedrooms, including a

    Marianne Collins Brown Harris Stevens N Fork

    355 Midway Rd, Southold, NY 11971
  • 2555 Youngs Ave Unit 14A, Southold, NY 11971

    $685,000

    Sold Nov 18, 2025

    2555 Youngs Ave Unit 14A, Southold, NY 11971

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Built 1988

    Last Sold Summary

    • 1% Above List Price
    • $571/SF
    • 12 Days On Market

    Last Listing Agent Diane Mollica Compass Greater NY LLC

    2555 Youngs Ave Unit 14A, Southold, NY 11971
    • 580 Jacobs Ln, Southold, NY 11971

      Est $749,377

      Not Listed For Sale

      580 Jacobs Ln, Southold, NY 11971

      • 2 Beds
      • 1 Bath
      580 Jacobs Ln, Southold, NY 11971

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Sheri Winter Parker Corcoran

  • /19

    $2,950,000

    • 4 Beds
    • 3.5 Baths
    • 4,241 Sq Ft

    9305 Soundview Ave, Southold, NY 11971

    Wake up to the salt air at your new coastal compound, a rare waterfront opportunity for those seeking something truly different. Unapologetically distinctive, this mid-century modern residence offers an extraordinary combination of waterfront, privacy, architectural character, and artistic location.Held in the same family for more than 50 years, the over 4000-square-foot home is set on two

    Thomas McCarthy Thomas J McCarthy Real Estate

    9305 Soundview Ave, Southold, NY 11971
  • /16

    $2,450 Per Month

    • 1 Bed
    • 1 Bath
    • 530 Sq Ft
    • Apartment for Rent

    55075 Main Rd Unit Youngs Bldg 3, Southold, NY 11971

    Newly renovated and pristine year-round rental in the heart of Southold's beautiful Colonial Village, an exclusive 55 an over adult community. This fantastic home has heat and water included in rent for tremendous savings to the tenant ! This inviting ground level one bedroom, one bath apartment offers comfort and convenience boasting a modern eat-in kitchen with granite countertops, all new

    Thomas McCarthy Thomas J McCarthy Real Estate

    55075 Main Rd Unit Youngs Bldg 3, Southold, NY 11971
  • 295 Grange Rd, Southold, NY 11971

    $1,900,000

    Sold Apr 14, 2026

    295 Grange Rd, Southold, NY 11971

    • 4 Beds
    • 3.5 Baths
    • 4,173 Sq Ft
    • Built 2025

    Last Sold Summary

    • 3% Below List Price
    • $455/SF
    • 124 Days On Market

    Current Estimated Value $1,929,333

    Last Listing Agent Sheri Winter Parker Corcoran

    295 Grange Rd, Southold, NY 11971
    • 425 Jacobs Ln, Southold, NY 11971

      Est $1,987,667

      Not Listed For Sale

      425 Jacobs Ln, Southold, NY 11971

      • 5 Beds
      • 3.5 Baths
      • 3,286 Sq Ft
      • Built 2001
      425 Jacobs Ln, Southold, NY 11971

      Last Sold Summary

      • 86 Days On Market

      Last Listing Agent Lisa Gillooly Compass Greater NY LLC

Showing Results 121 - 160, Page 4 of 18

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