Southold, NY Homes

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  $699,990 Pending

  • Land
  • 2.11 Acres
  • $331,749 per Acre

  80 Deer Run, Southold, NY 11971

  Stephen Lee Realty Connect USA L I Inc

  80 Deer Run, Southold, NY 11971
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  $20,000 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
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  $665,000 Sold Dec 03, 2025

  205 Grange Rd, Southold, NY 11971

  • 3 Beds
  • 1 Bath
  • 1,300 Sq Ft
  • Built 1971

  Last Sold Summary

  • 11% Above List Price
  • $512/SF
  • 15 Days On Market

  Last Listing Agent Rita Rooney Douglas Elliman Real Estate

  205 Grange Rd, Southold, NY 11971
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  Est $980,731 Not Listed For Sale

  • 3 Beds
  • 2 Baths

  430 Highwood Rd, Southold, NY 11971

  430 Highwood Rd, Southold, NY 11971
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  $399,000

  • Land
  • 7.13 Acres
  • $55,961 per Acre

  1135 Boisseau Ave, Southold, NY 11971

  Turn-key 7-acre vineyard that you've been dreaming of in Southold! Perfectly situated near the village and shops. The vines are in their prime and have been meticulously maintained. Planted in 2006 is 2.2 Acres of Chardonnay and 2.5 Acres of Merlot and 1/2 acre Muscat Ottonel was planted in 2019. Producing approximately 2-3 tons per acre of grapes annually. Fully deer fenced, irrigated by well

  Melissa Principi Douglas Elliman Real Estate

  1135 Boisseau Ave, Southold, NY 11971
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  $20,000 per month

  • 4 Beds
  • 4 Baths
  • 3,200 Sq Ft
  • House for Rent

  950 Blue Marlin Dr, Southold, NY 11971

  Beachfront, located in Southold Shores, this architect's own home is built with all the beautiful appointments you can imagine. Embracing the purity of architectural detail, together with a refined simplicity, this waterfront home offers a timeless elegance. Sweeping sunsets eye-catching angles and thoughtful details provide constant visual interest. A large 4 bedrooms with 4 baths ensuite,

  Lori Feilen William Raveis New York LLC

  950 Blue Marlin Dr, Southold, NY 11971
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  $1,175,000 Sold Feb 04, 2026

  1475 Oaklawn Ave, Southold, NY 11971

  • 4 Beds
  • 2.5 Baths
  • 2,400 Sq Ft
  • Built 1966

  Last Sold Summary

  • $490/SF
  • 33 Days On Market

  Last Listing Agent William Walters Daniel Gale Sothebys Intl Rlty

  1475 Oaklawn Ave, Southold, NY 11971
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  Est $1,147,139 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,233 Sq Ft

  1305 Cedar Dr, Southold, NY 11971

  1305 Cedar Dr, Southold, NY 11971
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  $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
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  $1,375,000 Sold Jun 16, 2025

  5950 N Bayview Rd, Southold, NY 11971

  • 3 Beds
  • 2 Baths
  • 1,547 Sq Ft
  • Built 2016

  Last Sold Summary

  • 8% Below List Price
  • $889/SF
  • 107 Days On Market

  Current Estimated Value $1,403,324

  Last Listing Agent Lisa Gillooly Compass Greater NY LLC

  5950 N Bayview Rd, Southold, NY 11971
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  Est $1,747,356 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft

  1205 Waterview Dr, Southold, NY 11971

  1205 Waterview Dr, Southold, NY 11971
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  $10,000 per month

  • 4 Beds
  • 2.5 Baths
  • House for Rent

  1275 the Esplanade, Southold, NY 11971

  STUNNER 4BR DESIGNER HOME ~ PET FRIENDLY, HEATED POOL & BEACH!Fabulous Lux Vacations on the coveted Esplanade in "Angel Shores", with a deeded sandy bay beach and heated freeform lagoon pool with a waterfall. Property is fully fenced and private, with many lounge areas for sunning, a shady pergola when needed, and a great new outdoor shower. We offer a pet friendly policy, rare for an

  Kate Carpluk William Raveis New York LLC

  1275 the Esplanade, Southold, NY 11971
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  $1,150,000 Sold Jul 10, 2025

  2865 S Harbor Rd, Southold, NY 11971

  • 3 Beds
  • 3 Baths
  • 2,250 Sq Ft
  • Built 1984

  Last Sold Summary

  • $511/SF
  • 24 Days On Market

  Current Estimated Value $1,172,351

  Last Listing Agent Shane Hafer Compass Greater NY LLC

  2865 S Harbor Rd, Southold, NY 11971
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  Est $989,392 Not Listed For Sale

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

  60 Koke Dr, Southold, NY 11971

  60 Koke Dr, Southold, NY 11971
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  $30,000 per month

  • 6 Beds
  • 4 Baths
  • 3,000 Sq Ft
  • House for Rent

  1695 Old Woods Path, Southold, NY 11971

  Southold, North Fork: This beautiful estate, bayfront home offers complete privacy in a peaceful woodland setting with a historic provenance and featuring a sugar sand beach. Despite its private location, it is conveniently close to the village and North Fork amenities. Croteaux is just up the lane, and NoFo table is a short bike ride away. The estate house has a broad porch, a living room with a

  Nicholas Planamento William Raveis New York LLC

  1695 Old Woods Path, Southold, NY 11971
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  $849,000 Sold Mar 19, 2025

  950 Paradise Shores Rd, Southold, NY 11971

  • 4 Beds
  • 2 Baths
  • 1,700 Sq Ft
  • Built 1983

  Last Sold Summary

  • $499/SF
  • 7 Days On Market

  Current Estimated Value $911,074

  Last Listing Agent Diane Mollica Compass Greater NY LLC

  950 Paradise Shores Rd, Southold, NY 11971
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  Est $1,562,027 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 2,232 Sq Ft

  6320 Main Bayview Rd, Southold, NY 11971

  6320 Main Bayview Rd, Southold, NY 11971
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  $1,250,000 Sold Nov 25, 2025

  800 Goose Creek Ln, Southold, NY 11971

  • 3 Beds
  • 3 Baths
  • 2,032 Sq Ft
  • Built 1997

  Last Sold Summary

  • $615/SF
  • 21 Days On Market

  Last Listing Agent Nancy Cervelli Daniel Gale Sothebys Intl Rlty

  800 Goose Creek Ln, Southold, NY 11971
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  Est $939,224 Not Listed For Sale

  • 3 Beds
  • 2 Baths

  600 Corey Creek Ln, Southold, NY 11971

  600 Corey Creek Ln, Southold, NY 11971
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  $602,500 Sold Jul 08, 2025

  2555 Youngs Ave Unit 12E, Southold, NY 11971

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 1986

  Last Sold Summary

  • $502/SF
  • 19 Days On Market

  Last Listing Agent Timothy O'Keefe Signature Premier Properties

  2555 Youngs Ave Unit 12E, Southold, NY 11971
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  Est $953,219 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  50 Wabasso St, Southold, NY 11971

  50 Wabasso St, Southold, NY 11971
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  $690,000 Sold Mar 03, 2025

  500 Gagens Landing Rd, Southold, NY 11971

  • 3 Beds
  • 1.5 Baths
  • Built 1964

  Last Sold Summary

  • 9% Below List Price
  • 167 Days On Market

  Current Estimated Value $748,326

  Last Listing Agent Katie Schimpf Daniel Gale Sothebys Intl Rlty

  500 Gagens Landing Rd, Southold, NY 11971
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  Est $1,062,928 Not Listed For Sale

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

  150 Baywater Ave, Southold, NY 11971

  150 Baywater Ave, Southold, NY 11971
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  $940,000 Sold Dec 02, 2025

  1755 Yennecott Dr, Southold, NY 11971

  • 6 Beds
  • 2.5 Baths
  • 3,200 Sq Ft
  • Built 1972

  Last Sold Summary

  • 22% Below List Price
  • $294/SF
  • 721 Days On Market

  Last Listing Agent Isaac Israel Richmond Realty Corp

  1755 Yennecott Dr, Southold, NY 11971
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  Est $1,215,667 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,550 Sq Ft

  500 Glenn Rd, Southold, NY 11971

  500 Glenn Rd, Southold, NY 11971
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  $551,000 Sold Mar 13, 2025

  11212 Soundview Ave, Southold, NY 11971

  • Land
  • 1.03 Acres
  • $534,951 per Acre

  Last Sold Summary

  • 10% Above List Price
  • 18 Days On Market

  Current Estimated Value $573,864

  Last Listing Agent Thomas McCarthy Thomas J McCarthy Real Estate

  11212 Soundview Ave, Southold, NY 11971
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  Est $1,174,432 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,610 Sq Ft

  220 Glenn Rd, Southold, NY 11971

  220 Glenn Rd, Southold, NY 11971
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  $875,000 Sold Mar 31, 2025

  1490 Long Creek Dr, Southold, NY 11971

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • Built 1975

  Last Sold Summary

  • $547/SF
  • 24 Days On Market

  Current Estimated Value $961,460

  Last Listing Agent Kristy Naddell Douglas Elliman Real Estate

  1490 Long Creek Dr, Southold, NY 11971
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  Est $1,957,413 Not Listed For Sale

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

  4015 Main Bayview Rd, Southold, NY 11971

  4015 Main Bayview Rd, Southold, NY 11971
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  $590,000 Sold Jan 08, 2026

  3680 Main Bayview Rd, Southold, NY 11971

  • 3 Beds
  • 2 Baths
  • 1,442 Sq Ft
  • Built 1761

  Last Sold Summary

  • 7% Below List Price
  • $409/SF
  • 14 Days On Market

  Last Listing Agent Barry Novick Daniel Gale Sothebys Intl Rlty

  3680 Main Bayview Rd, Southold, NY 11971
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  Est $953,152 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,400 Sq Ft

  3715 Main Bayview Rd, Southold, NY 11971

  3715 Main Bayview Rd, Southold, NY 11971
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  $950,000 Sold Nov 18, 2025

  9875 Main Bayview Rd, Southold, NY 11971

  • 4 Beds
  • 3 Baths
  • 2,000 Sq Ft
  • Built 1838

  Last Sold Summary

  • 27% Below List Price
  • $475/SF
  • 231 Days On Market

  Last Listing Agent Kristy Naddell Douglas Elliman Real Estate

  9875 Main Bayview Rd, Southold, NY 11971
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  Est $1,543,412 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,020 Sq Ft

  2305 Glenn Rd, Southold, NY 11971

  2305 Glenn Rd, Southold, NY 11971
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  $1,055,000 Sold Nov 24, 2025

  610 Richmond Rd, Southold, NY 11971

  • 3 Beds
  • 2 Baths
  • 2,184 Sq Ft
  • Built 1930

  Last Sold Summary

  • 4% Below List Price
  • $483/SF
  • 41 Days On Market

  Last Listing Agent Bridget Elkin Compass Greater NY LLC

  610 Richmond Rd, Southold, NY 11971
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  Est $881,317 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,150 Sq Ft

  645 Shepard Dr, Southold, NY 11971

  645 Shepard Dr, Southold, NY 11971
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  $678,000 Sold Jun 24, 2025

  1745 Nokomis Rd, Southold, NY 11971

  • 2 Beds
  • 1 Bath
  • Built 1972

  Last Sold Summary

  • 7 Days On Market

  Current Estimated Value $728,934

  Last Listing Agent Maryse Bransfield William Raveis New York LLC

  1745 Nokomis Rd, Southold, NY 11971
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  Est $1,786,642 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,200 Sq Ft

  480 Grissom Ln, Southold, NY 11971

  480 Grissom Ln, Southold, NY 11971
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  $950,000 Sold Jul 11, 2025

  1575 Founders Path, Southold, NY 11971

  • 3 Beds
  • 2 Baths
  • 1,632 Sq Ft
  • Built 1927

  Last Sold Summary

  • 1% Below List Price
  • $582/SF
  • 13 Days On Market

  Current Estimated Value $958,050

  Last Listing Agent Timothy O'Keefe Signature Premier Properties

  1575 Founders Path, Southold, NY 11971
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  Est $1,081,552 Not Listed For Sale

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

  2230 Cedar Dr, Southold, NY 11971

  2230 Cedar Dr, Southold, NY 11971
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  $750,000 Sold Dec 17, 2025

  57020 Route 25, Southold, NY 11971

  • 3 Beds
  • 3 Baths
  • 2,100 Sq Ft
  • Built 1783

  Last Sold Summary

  • 23% Below List Price
  • $357/SF
  • 169 Days On Market

  Last Listing Agent Eugene Rindfuss Coldwell Banker Reliable R E

  57020 Route 25, Southold, NY 11971

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