Southold, NY Homes

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  $2,895,000

  • 3 Beds
  • 2 Baths
  • 1,840 Sq Ft

  21515 Soundview Ave, Southold, NY 11971

  Life on the North Fork doesn't get better than this! Set along the Long Island Sound in one of Southold's most desirable locations, this chic waterfront escape offers sweeping water views, sensational sunsets, and effortless coastal living. Renovated in 2016 and completely move-in ready, the home blends sophisticated style with relaxed comfort, creating the perfect setting for both entertaining

  Kristy Naddell Douglas Elliman Real Estate

  21515 Soundview Ave, Southold, NY 11971
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  /26

  $30,000 Per Month

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

  485 Hickory Ave, Southold, NY 11971

  Impressive Goose Creek home with water views and large heated in-ground pool! This four bedroom, three bath house features a first floor primary bedroom with en-suite, a gourmet kitchen and open living space. The newly designed landscape with outdoor kitchen (not pictured) is ideal for entertaining or relaxing. Enjoy its large fire pit and BBQ grill after an afternoon of Kayaking. Close to

  Mackenzie Needham Daniel Gale Sothebys Intl Rlty

  485 Hickory Ave, Southold, NY 11971
• 

  $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

  Current Estimated Value $1,012,222

  Last Listing Agent Isaac Israel Richmond Realty Corp

  1755 Yennecott Dr, Southold, NY 11971
• 

  Est $775,178

  Not Listed For Sale

  275 Victoria Dr, Southold, NY 11971

  • 3 Beds
  • 1 Bath
  • Built 1970

  275 Victoria Dr, Southold, NY 11971

  Last Sold Summary

  • 22 Days On Market

  Last Listing Agent Kevin Collins Signature Premier Properties
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  /36

  $1,385,000

  • 4 Beds
  • 2.5 Baths
  • 2,200 Sq Ft

  4408 Old North Rd, Southold, NY 11971

  Located in one of the most sought-after locations on the North Fork sits this quintessential cedar shake farmhouse situated on 2 private acres! This home combines timeless charm with modern comforts. The main level features hardwood floors throughout, a spacious living room with a wood-burning fireplace, formal dining room, eat-in kitchen with granite countertops and pantry, a convenient half

  Kristy Naddell Douglas Elliman Real Estate

  4408 Old North Rd, Southold, NY 11971
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  /27

  $10,000 Per Month

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

  275 Maier Place, Southold, NY 11971

  Seasonal Rental in Scenic Southold, NY – 3 Bed, 3 Bath RetreatEscape to the heart of the North Fork with this beautifully appointed 3-bedroom, 2-bath seasonal rental in picturesque Southold, NY. Nestled among the region's famed vineyards, farm stands, and white sand beaches, this home offers the perfect blend of charm, comfort, and convenience.Inside, you'll find a spacious and

  Mary Terry MCKENNASHEA LLC

  275 Maier Place, Southold, NY 11971
• 

  $899,000

  Sold Mar 05, 2026

  385 Cottage Place, Southold, NY 11971

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft
  • Built 1900

  Last Sold Summary

  • 8% Below List Price
  • $624/SF
  • 131 Days On Market

  Current Estimated Value $899,975

  Last Listing Agent Janet Markarian Daniel Gale Sothebys Intl Rlty

  385 Cottage Place, Southold, NY 11971
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  Est $1,010,234

  Not Listed For Sale

  750 Cedar Dr, Southold, NY 11971

  • 3 Beds
  • 2.5 Baths
  • 1,800 Sq Ft
  • Built 2001

  750 Cedar Dr, Southold, NY 11971

  Last Sold Summary

  • 9 Days On Market

  Last Listing Agent Donna Bekisz Century 21 Sewanhaka Realty
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  $1,299,000

  • 4 Beds
  • 3 Baths
  • 2,240 Sq Ft

  1075 Ships Dr, Southold, NY 11971

  Classic Americana meets the North Fork lifestyle on Southold's Bayview Peninsula. Set on a level half acre backing to protected town owned land, this four bedroom, three bath Center Hall Colonial combines timeless design, thoughtful updates, and an exceptional location near Southold's most sought-after waterfront destinations. A welcoming portico leads into a home with wood floors throughout. The

  Joshua Whalley Douglas Elliman Real Estate

  1075 Ships Dr, 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

  Current Estimated Value $686,318

  Last Listing Agent Barry Novick Daniel Gale Sothebys Intl Rlty

  3680 Main Bayview Rd, Southold, NY 11971
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  Est $930,922

  Not Listed For Sale

  430 Highwood Rd, Southold, NY 11971

  • 3 Beds
  • 2 Baths
  • Built 1983

  430 Highwood Rd, Southold, NY 11971

  Last Sold Summary

  • 30 Days On Market

  Last Listing Agent Jennifer Benton Compass Greater NY LLC
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  /15

  $699,000

  • 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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  $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

  Current Estimated Value $990,182

  Last Listing Agent Kristy Naddell Douglas Elliman Real Estate

  9875 Main Bayview Rd, Southold, NY 11971
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  Est $1,334,986

  Not Listed For Sale

  1305 Cedar Dr, Southold, NY 11971

  • 4 Beds
  • 3.5 Baths
  • 3,233 Sq Ft
  • Built 1973

  1305 Cedar Dr, Southold, NY 11971

  Last Sold Summary

  • 105 Days On Market

  Last Listing Agent Alexis Meadows Compass Greater NY LLC
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  /41

  $969,000

  Open Sun 12:30PM - 2PM

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

  270 Opechee Ave, Southold, NY 11971

  Welcome to North Fork living! Nestled in the desirable, private beach community of Laughing Water, this charming 3-bedroom, 2-bath Ranch sits on a 0.38-acre lot. Inside, enjoy hardwood floors throughout the living and dining areas, along with a newly updated kitchen featuring new appliances, a center island, and generous storage. A 10’ x 13’ screened-in porch provides the perfect three-season

  Patricia Shackel Douglas Elliman Real Estate

  270 Opechee Ave, Southold, NY 11971
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  $1,025,000

  Sold Feb 13, 2026

  3700 Minnehaha Blvd, Southold, NY 11971

  • 3 Beds
  • 1.5 Baths
  • 1,144 Sq Ft
  • Built 2003

  Last Sold Summary

  • 11% Below List Price
  • $896/SF
  • 53 Days On Market

  Current Estimated Value $1,025,233

  Last Listing Agent Rita Rooney Douglas Elliman Real Estate

  3700 Minnehaha Blvd, Southold, NY 11971
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  Est $1,496,404

  Not Listed For Sale

  1205 Waterview Dr, Southold, NY 11971

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft
  • Built 1971

  1205 Waterview Dr, Southold, NY 11971

  Last Sold Summary

  • 43 Days On Market

  Last Listing Agent Alexis Meadows Compass Greater NY LLC
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  /25

  $2,500,000

  $500K PRICE INCREASE

  • 5 Beds
  • 4.5 Baths
  • 3,800 Sq Ft

  3470 N Bayview Rd, Southold, NY 11971

  Welcome to the epitome of elegance and comfort at 3470 N Bayview Rd, Southold NY. This high-quality 5-bedroom, 5-bathroom home is located just a stone's throw away from the popular Goose Creek Beach. The spacious horseshoe driveway and 2-car garage ensure ample parking and easy access. Step inside to be greeted by high ceilings and an open floor plan, allowing for a seamless flow throughout the

  Barbara Poliwoda Douglas Elliman Real Estate

  3470 N Bayview 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

  Current Estimated Value $1,079,533

  Last Listing Agent Bridget Elkin Compass Greater NY LLC

  610 Richmond Rd, Southold, NY 11971
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  Est $910,803

  Not Listed For Sale

  60 Koke Dr, Southold, NY 11971

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • Built 1960

  60 Koke Dr, Southold, NY 11971

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Scott Bennett Douglas Elliman Real Estate
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  /38

  $3,899,000

  $401K PRICE DROP

  • Land
  • 45.77 Acres
  • $85,187 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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  $2,100,000

  Sold May 29, 2026

  4745 N Bayview Rd, Southold, NY 11971

  • 4 Beds
  • 6 Baths
  • 5,500 Sq Ft
  • Built 1965

  Last Sold Summary

  • 5% Below List Price
  • $382/SF
  • 5 Days On Market

  Current Estimated Value $2,180,776

  Last Listing Agent Donielle Cardinale Daniel Gale Sothebys Intl Rlty

  4745 N Bayview Rd, Southold, NY 11971
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  Est $1,429,779

  Not Listed For Sale

  6060 Main Bayview Rd, Southold, NY 11971

  • 3 Beds
  • 2 Baths
  • 1,694 Sq Ft
  • Built 1975

  6060 Main Bayview Rd, Southold, NY 11971

  Last Sold Summary

  • 56 Days On Market

  Last Listing Agent Joanne Calandra Douglas Elliman Real Estate
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  /33

  $1,975,000

  Pending

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

  2300 Glenn Rd, Southold, NY 11971

  Located in one of Southold’s most coveted locations, this waterfront oasis offers peace, privacy, and stunning views of Goose Creek. Surrounded by professionally designed and meticulously maintained landscaping, this property exudes tranquility and natural beauty. The home features a spacious and thoughtfully designed layout with wood floors throughout. The updated kitchen is a chef’s

  Kristy Naddell Douglas Elliman Real Estate

  2300 Glenn Rd, 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

  Current Estimated Value $785,215

  Last Listing Agent Eugene Rindfuss Coldwell Banker Reliable R E

  57020 Route 25, Southold, NY 11971
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  Est $852,752

  Not Listed For Sale

  50 Wabasso St, Southold, NY 11971

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1950

  50 Wabasso St, Southold, NY 11971

  Last Sold Summary

  • 182 Days On Market

  Last Listing Agent William Walters Daniel Gale Sothebys Intl Rlty
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  /32

  $798,500

  Pending

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft

  723 Private Rd Unit 12, Southold, NY 11971

  Tucked away in a secluded waterfront setting, this charming bayside cottage offers a rare opportunity to enjoy peaceful North Fork living surrounded by natural beauty and captivating water views. Designed to embrace its exceptional location, the home features an open-concept living, dining, and kitchen area where abundant windows frame the water and fill the interior with natural light throughout

  Scott Bennett Douglas Elliman Real Estate

  723 Private Rd Unit 12, Southold, NY 11971
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  $525,000

  Sold Nov 13, 2025

  2555 Youngs Ave Unit 11D, Southold, NY 11971

  • 2 Beds
  • 2 Baths
  • 1,100 Sq Ft
  • Built 1987

  Last Sold Summary

  • $477/SF
  • 54 Days On Market

  Last Listing Agent Patrick Carpenter Signature Premier Properties

  2555 Youngs Ave Unit 11D, Southold, NY 11971
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  Est $1,185,140

  Not Listed For Sale

  2865 S Harbor Rd, Southold, NY 11971

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

  2865 S Harbor Rd, Southold, NY 11971

  Last Sold Summary

  • 24 Days On Market

  Last Listing Agent Shane Hafer Compass Greater NY LLC
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  /46

  $2,250,000

  $100K PRICE DROP

  • 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
• 

  $815,000

  Sold Nov 14, 2025

  2575 Oaklawn Ave, Southold, NY 11971

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1960

  Last Sold Summary

  • $582/SF
  • 19 Days On Market

  Current Estimated Value $815,516

  Last Listing Agent Bridget Elkin Compass Greater NY LLC

  2575 Oaklawn Ave, Southold, NY 11971
• 

  Est $1,205,667

  Not Listed For Sale

  500 Glenn Rd, Southold, NY 11971

  • 3 Beds
  • 2 Baths
  • 1,550 Sq Ft
  • Built 1972

  500 Glenn Rd, Southold, NY 11971

  Last Sold Summary

  • 18 Days On Market

  Last Listing Agent Lee Beninati Beninati Associates
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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 with new refrigerator, and dining area ideal for everyday living and

  Scott Bennett Douglas Elliman Real Estate

  240 Lisa Dr, Southold, NY 11971
• 

  $800,000

  Sold Oct 03, 2025

  265 Custer Ave, Southold, NY 11971

  • 3 Beds
  • 1.5 Baths
  • 1,800 Sq Ft
  • Built 1965

  Last Sold Summary

  • 9% Below List Price
  • $444/SF
  • 118 Days On Market

  Current Estimated Value $850,744

  Last Listing Agent Kenneth Poliwoda Douglas Elliman Real Estate

  265 Custer Ave, Southold, NY 11971
• 

  Est $1,020,084

  Not Listed For Sale

  220 Glenn Rd, Southold, NY 11971

  • 3 Beds
  • 2 Baths
  • 1,610 Sq Ft
  • Built 1973

  220 Glenn Rd, Southold, NY 11971

  Last Sold Summary

  • 11 Days On Market

  Last Listing Agent Scott Bennett Douglas Elliman Real Estate
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  /33

  $1,495,000

  $100K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,900 Sq Ft

  2015 Kenneys Rd, Southold, NY 11971

  Explore a prime location in Southold, perfect for a beach getaway, featuring the highly sought-after Kenneys Beach—one of the most picturesque beaches on the North Fork. This traditional-style home is built with meticulous attention to detail and quality craftsmanship. Upon entering, you are greeted by a cathedral ceiling that highlights a stunning stone staircase with iron railings. The spacious

  Alexis Meadows Compass Greater NY LLC

  2015 Kenneys Rd, Southold, NY 11971
• 

  $864,000

  Sold Nov 12, 2025

  440 Jernick Ln, Southold, NY 11971

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • Built 1972

  Last Sold Summary

  • 1% Below List Price
  • $540/SF
  • 17 Days On Market

  Current Estimated Value $914,649

  Last Listing Agent Thomas McCarthy Thomas J McCarthy Real Estate

  440 Jernick Ln, Southold, NY 11971
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  Est $1,945,878

  Not Listed For Sale

  4015 Main Bayview Rd, Southold, NY 11971

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

  4015 Main Bayview Rd, Southold, NY 11971

  Last Sold Summary

  • 75 Days On Market

  Last Listing Agent Susan Orioli Engel & Volkers North Fork
• 

  

  /23

  $1,250,000

  • 6 Beds
  • 3 Baths
  • 3,093 Sq Ft

  13675 Main Bayview Rd, Southold, NY 11971

  Every once in a while, a home comes along that just makes you smile-and this is one of them. Set on just under an acre in Southold, this classic farmhouse is full of charm, character, and even its own secret garden. With 6 bedrooms and 3 bathrooms, there's plenty of room for everyone, plus multiple living spaces, cozy sitting rooms, a dining area made for gathering, an open kitchen, laundry room,

  Sheri Winter Parker Corcoran

  13675 Main Bayview Rd, Southold, NY 11971
• 

  $1,049,000

  Sold Mar 26, 2026

  633 Pine Neck Rd, Southold, NY 11971

  • 3 Beds
  • 1.5 Baths
  • 1,068 Sq Ft
  • Built 1920

  Last Sold Summary

  • 30% Below List Price
  • $982/SF
  • 882 Days On Market

  Current Estimated Value $1,071,404

  Last Listing Agent Tom Uhlinger Douglas Elliman Real Estate

  633 Pine Neck Rd, Southold, NY 11971

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