Southold, NY Homes

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  $939,000

  • 3 Beds
  • 3.5 Baths
  • 2,950 Sq Ft

  595 Greenfields Ln, Southold, NY 11971

  Location!Location!Location! Some homes are beautiful, others are truly one of a kind. 595 Greenfields Lane is both! Set on nearly 1 acre of meticulously landscaped property on a quiet dead end street, this exceptional custom built home is located just moments away from the historic village of Southold and the very best of the North Fork! Just a mile from the beach and steps away from Long

  Giuseppe Pinello Exit Realty Achieve

  595 Greenfields Ln, 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
• 

  $3,400,000

  Sold Jun 26, 2026

  465 Ripple Water Ln, Southold, NY 11971

  • 4 Beds
  • 5.5 Baths
  • 6,366 Sq Ft
  • Built 2025

  Last Sold Summary

  • 6% Below List Price
  • $534/SF
  • 139 Days On Market

  Last Listing Agent Jerry Cibulski Century 21 Albertson Realty

  465 Ripple Water Ln, Southold, NY 11971
• 

  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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  /43

  $1,849,000

  $76K PRICE DROP

  • 4 Beds
  • 4 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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  /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
• 

  $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 $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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  $3,100,000

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

  3651 Soundview Ave, Peconic, NY 11958

  Charming updated Soundfront beach house! This home is what dreams are made of. Steps away is a plush, powder white sandy path leading to a serene private beach where panoramic vistas and mesmerizing sunsets will sweep you off your feet. Offering approximately 1,600 sq. ft. of living space, the first level boasts an eat-in-kitchen, living room with fireplace to cozy up to during those brisk fall

  Nicholas Liappas Compass Greater NY LLC

  3651 Soundview Ave, Peconic, NY 11958
• 

  $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
• 

  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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  $2,595,000

  $300K PRICE DROP

  • 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
• 

  $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 $1,409,851

  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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  /36

  $1,299,000

  $86K PRICE DROP

  • 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
• 

  $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 $929,469

  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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  $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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  $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 $1,185,140

  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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  /40

  $3,300,000

  • 4 Beds
  • 2.5 Baths
  • 3,028 Sq Ft

  3645 Soundview Ave, Peconic, NY 11958

  North Fork retreat! A powder white sandy path leads to a gorgeous private beach offering 116 ft. of waterfrontage while incredible sparkling Sound views, sunsets, and lush greenery set this property apart. Enjoy water views from the open concept main level and the expansive 800+ sq. ft. rear deck - perfect for lounging, al fresco dining and taking in the fresh sea air. With over 3,000 sq. ft. of

  Nicholas Liappas Compass Greater NY LLC

  3645 Soundview Ave, Peconic, NY 11958
• 

  $1,800,000

  Sold Sep 01, 2026

  4630 Youngs Ave, Southold, NY 11971

  • 2 Beds
  • 2 Baths
  • 3,603 Sq Ft
  • Built 2020

  Last Sold Summary

  • 8% Below List Price
  • $500/SF
  • 33 Days On Market

  Current Estimated Value $1,931,753

  Last Listing Agent Sheri Winter Parker Corcoran

  4630 Youngs 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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  /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

  Karyn Flores Compass Greater NY LLC

  430 Grove 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 $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
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  /41

  $969,000

  • 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

  Patricia Shackel Douglas Elliman Real Estate

  270 Opechee Ave, Southold, NY 11971
• 

  $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
• 

  Est $931,434

  Not Listed For Sale

  3715 Main Bayview Rd, Southold, NY 11971

  • 3 Beds
  • 2.5 Baths
  • 1,400 Sq Ft
  • Built 1942

  3715 Main Bayview Rd, Southold, NY 11971

  Last Sold Summary

  • 58 Days On Market

  Last Listing Agent Jennifer Benton Compass Greater NY LLC
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  /25

  $2,500,000

  $500K PRICE INCREASE Pending

  • 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

  Barbara Poliwoda Douglas Elliman Real Estate

  3470 N Bayview Rd, Southold, NY 11971
• 

  $915,000

  Sold Sep 02, 2026

  2070 Cedar Dr, Southold, NY 11971

  • 2 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • Built 1938

  Last Sold Summary

  • 7% Below List Price
  • $762/SF
  • 231 Days On Market

  Current Estimated Value $963,625

  Last Listing Agent Dawn Watson Serhant East End LLC

  2070 Cedar Dr, Southold, NY 11971
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  Est $1,386,526

  Not Listed For Sale

  2305 Glenn Rd, Southold, NY 11971

  • 4 Beds
  • 2.5 Baths
  • 2,020 Sq Ft
  • Built 1992

  2305 Glenn Rd, Southold, NY 11971

  Last Sold Summary

  • 8 Days On Market

  Last Listing Agent Erin Kaelin Signature Premier Properties
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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

  A rare opportunity to create a truly bespoke North Fork lifestyle or equestrian estate in the heart of Southold’s celebrated agricultural landscape. Privately set across 45.54 acres, the offering includes 43.7 acres of preserved agricultural land and a separate 1.84-acre residential parcel with development rights intact-an exceptional setting to create a distinctive residence overlooking your own

  Andrea Parks Douglas Elliman Real Estate

  46975 Main Rd, Southold, NY 11971
• 

  $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 $827,414

  Last Listing Agent Eugene Rindfuss Coldwell Banker Reliable R E

  57020 Route 25, Southold, NY 11971
• 

  Est $807,473

  Not Listed For Sale

  645 Shepard Dr, Southold, NY 11971

  • 2 Beds
  • 2 Baths
  • 1,150 Sq Ft
  • Built 1985

  645 Shepard Dr, Southold, NY 11971

  Last Sold Summary

  • 12 Days On Market

  Last Listing Agent Barry Novick 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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  $2,252,500

  Sold Aug 19, 2026

  450 Sterling Woods Ln, Southold, NY 11971

  • 4 Beds
  • 3 Baths
  • 3,769 Sq Ft
  • Built 2010

  Last Sold Summary

  • 2% Below List Price
  • $598/SF
  • 44 Days On Market

  Current Estimated Value $2,280,177

  Last Listing Agent Paul Loeb Douglas Elliman Real Estate

  450 Sterling Woods Ln, Southold, NY 11971
• 

  Est $1,528,145

  Not Listed For Sale

  480 Grissom Ln, Southold, NY 11971

  • 4 Beds
  • 3 Baths
  • 3,200 Sq Ft
  • Built 1985

  480 Grissom Ln, Southold, NY 11971

  Last Sold Summary

  • 22 Days On Market

  Last Listing Agent Kenneth Poliwoda Douglas Elliman Real Estate
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  /46

  $2,250,000

  $100K PRICE DROP Pending

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

  1665 Glenn Rd, Southold, NY 11971

  Newly built and beautifully enhanced with many expensive 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 and

  Kristy Naddell Douglas Elliman Real Estate

  1665 Glenn Rd, Southold, NY 11971
• 

  $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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