4,621

Southold, NY Homes

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  • /22

    $2,195,000

    • 4 Beds
    • 5.5 Baths
    • 3,000 Sq Ft

    600 Glenn Rd, Southold, NY 11971

    Modern Luxury Waterfront Tree House - Nature Lovers’ Paradise on West Creek!Discover this stunning 4-bedroom, 5.5-bath waterfront featuring a Black Onyx saltwater pool and private dock on the highly sought-after West Creek.Step into the upper-level living area, where floor-to-ceiling views create a serene bird’s-eye perspective of lush trees and sparkling water—a true sanctuary for birds

    Cathleen Dolson Corcoran

    600 Glenn Rd, Southold, NY 11971
  • /32

    $19,500 per month

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • House for Rent

    1355 Watersedge Way, Southold, NY 11971

    Welcome to 1355 Watersedge Way, a delightful Bayfront home offering breathtaking water and sunset views in Southold. Nestled next to a nature preserve with 300 feet of private beach, this home provides both serenity and direct water access.Inside, the spacious living room features a smart TV and a wall of sliding glass doors that open to a waterside deck, perfect for enjoying the bay breeze.

    Jeanmarie Bay William Raveis New York LLC

    1355 Watersedge Way, Southold, NY 11971
  • 800 Goose Creek Ln, Southold, NY 11971

    $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

    Current Estimated Value $1,244,392

    Last Listing Agent Nancy Cervelli Daniel Gale Sothebys Intl Rlty

    800 Goose Creek Ln, Southold, NY 11971
    • 400 Ships Dr, Southold, NY 11971

      Est $1,188,497 Not Listed For Sale

      400 Ships Dr, Southold, NY 11971

      • 3 Beds
      • 2 Baths
      • 2,100 Sq Ft
      • Built 2001
      400 Ships Dr, Southold, NY 11971

      Last Sold Summary

      • 13% Above List Price
      • $500/SF
      • 21 Days On Market

      Last Sold Price $1,050,000

      Last Listing Agent Regan Battuello The Agency Northshore NY

  • /2

    $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
  • /25

    $7,500 per month

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

    3400 Youngs Ave, Southold, NY 11971

    Permit #493 Newly Renovated Farmhouse Centrally Located In Southold With Easy Access By Bus, Train or Car. Enjoy Your Morning Coffee As The Sun Rises Over The Farm Field. Spend An Afternoon Exploring The Beauty of the North Fork, Soak in the Sun at one of the Beautiful Peconic Bay or Long Island Sound Beaches, Enjoy Live Music at Numerous Wineries and/or Breweries, Browse unique local finds at

    Thomas McCarthy Thomas J McCarthy Real Estate

    3400 Youngs Ave, Southold, NY 11971
  • 2555 Youngs Ave Unit 12E, Southold, NY 11971

    $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
    • 210 Northfield Ln, Southold, NY 11971

      Est $1,935,878 Not Listed For Sale

      210 Northfield Ln, Southold, NY 11971

      • 4 Beds
      • 4 Baths
      • 3,200 Sq Ft
      • Built 1990
      210 Northfield Ln, Southold, NY 11971

      Last Sold Summary

      • 12% Above List Price
      • $542/SF
      • 208 Days On Market

      Last Sold Price $1,735,000

      Last Listing Agent Jeanmarie Bay William Raveis New York LLC

  • /10

    $399,000 Pending

    • 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
  • /29

    $12,000 per month

    • 2 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • House for Rent

    250 Wesland Rd, Southold, NY 11971

    NEW TO THE RENTAL MARKET! JUST A DREAM BOAT! NEWLY RENOVATED, LIGHT AND BRIGHT, BEAUTIFULLY APPOINTED, EVERY CONVENIENCE - 2 BEDROOMS, 2 BATHS. PLUS - CONVERTIBLE QUEEN SOFABED! BEAUTIFUL OUTDOOR DINING, FIRE PIT, PORCH, ENCLOSED SHOWER! PRICED RIGHT! STEPS TO POPULAR KENNEY'S BEACH - JUST BRING YOUR LITTLE RED WAGON AND STROLL TO THE BEACH AND ENJOY! Additional information: Appearance excellent!

    Marie Beninati Beninati Associates

    250 Wesland Rd, Southold, NY 11971
  • 1755 Yennecott Dr, 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 $1,002,318

    Last Listing Agent Isaac Israel Richmond Realty Corp

    1755 Yennecott Dr, Southold, NY 11971
    • 8355 Main Bayview Rd, Southold, NY 11971

      Est $1,839,547 Not Listed For Sale

      8355 Main Bayview Rd, Southold, NY 11971

      • 4 Beds
      • 3 Baths
      • 2,662 Sq Ft
      • Built 1867
      8355 Main Bayview Rd, Southold, NY 11971

      Last Sold Summary

      • 2% Above List Price
      • $676/SF

      Last Sold Price $1,800,000

      Last Listing Agent Janet Markarian Daniel Gale Sotheby's

  • /34

    $30,000 per month

    • 8 Beds
    • 7 Baths
    • 5,400 Sq Ft
    • House for Rent

    650 Pine Ave, Southold, NY 11971

    A masterfully crafted resort style property, where coastal luxury meets effortless living. Tucked within a coveted private beach community with beach access, this resort-style property was designed for gathering, entertaining, and unwinding in total privacy. The home features a show-stopping 20’ x 40’ heated saltwater pool, framed by lush, manicured grounds that feel both serene and indulgent.

    Colin McCarthy Thomas J McCarthy Real Estate

    650 Pine Ave, Southold, NY 11971
  • 385 Cottage 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 $891,100

    Last Listing Agent Janet Markarian Daniel Gale Sothebys Intl Rlty

    385 Cottage Place, Southold, NY 11971
    • 275 Victoria Dr, Southold, NY 11971

      Est $736,460 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

      • 28% Above List Price
      • 22 Days On Market

      Last Sold Price $576,000

      Last Listing Agent Kevin Collins Signature Premier Properties

  • /15

    $3,500 per month

    • 2 Beds
    • 1 Bath
    • House for Rent

    3825 S Harbor Rd, Southold, NY 11971

    Classic North Fork Beach home located just 10 homes away from South Harbor Beach and Park, Amazing comfort and privacy on this acre plus setting. Home is crisp, clean, and fully furnished ready for you to enjoy. South Harbors expansive beach offers an inlet to paddle board, kayak, fish, and relax on the water. Please call for availability; 2025 Rates: January- April $3500, May $5000, June $7000,

    Barbara Poliwoda Douglas Elliman Real Estate

    3825 S Harbor Rd, Southold, NY 11971
  • 3680 Main Bayview Rd, 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 $626,739

    Last Listing Agent Barry Novick Daniel Gale Sothebys Intl Rlty

    3680 Main Bayview Rd, Southold, NY 11971
    • 750 Cedar Dr, Southold, NY 11971

      Est $906,749 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

      • 13% Above List Price
      • $444/SF
      • 9 Days On Market

      Last Sold Price $799,000

      Last Listing Agent Donna Bekisz Century 21 Sewanhaka Realty

  • /24

    $18,000 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
  • 9875 Main Bayview 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 $994,018

    Last Listing Agent Kristy Naddell Douglas Elliman Real Estate

    9875 Main Bayview Rd, Southold, NY 11971
    • 430 Highwood Rd, Southold, NY 11971

      Est $909,494 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

      • 10% Above List Price
      • 30 Days On Market

      Last Sold Price $825,000

      Last Listing Agent Jennifer Benton Compass Greater NY LLC

  • /34

    $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
  • 3700 Minnehaha Blvd, Southold, NY 11971

    $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 $1,124,794

    Last Listing Agent Rita Rooney Douglas Elliman Real Estate

    3700 Minnehaha Blvd, Southold, NY 11971
    • 1305 Cedar Dr, Southold, NY 11971

      Est $1,101,391 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

      • 10% Above List Price
      • $309/SF
      • 105 Days On Market

      Last Sold Price $999,999

      Last Listing Agent Alexis Meadows Douglas Elliman Real Estate

  • /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
  • 610 Richmond Rd, Southold, NY 11971

    $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 $1,062,808

    Last Listing Agent Bridget Elkin Compass Greater NY LLC

    610 Richmond Rd, Southold, NY 11971
    • 1205 Waterview Dr, Southold, NY 11971

      Est $1,463,647 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

      • 9% Below List Price
      • $889/SF
      • 43 Days On Market

      Last Sold Price $1,600,000

      Last Listing Agent Alexis Meadows Douglas Elliman Real Estate

  • /39

    $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
  • 1745 Nokomis Rd, Southold, NY 11971

    $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 $712,357

    Last Listing Agent Maryse Bransfield William Raveis New York LLC

    1745 Nokomis Rd, Southold, NY 11971
    • 60 Koke Dr, Southold, NY 11971

      Est $840,459 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

      • 8% Above List Price
      • $520/SF
      • 5 Days On Market

      Last Sold Price $780,000

      Last Listing Agent Scott Bennett Douglas Elliman Real Estate

  • /32

    $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
  • 1575 Founders Path, Southold, NY 11971

    $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 $951,872

    Last Listing Agent Timothy O'Keefe Signature Premier Properties

    1575 Founders Path, Southold, NY 11971
    • 600 Corey Creek Ln, Southold, NY 11971

      Est $867,125 Not Listed For Sale

      600 Corey Creek Ln, Southold, NY 11971

      • 3 Beds
      • 2 Baths
      • Built 1973
      600 Corey Creek Ln, Southold, NY 11971

      Last Sold Summary

      • 15% Above List Price
      • 60 Days On Market

      Last Sold Price $756,000

      Last Listing Agent Marcia Sheldon William Raveis New York LLC

  • 57020 Route 25, 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 $823,214

    Last Listing Agent Eugene Rindfuss Coldwell Banker Reliable R E

    57020 Route 25, Southold, NY 11971
    • 50 Wabasso St, Southold, NY 11971

      Est $861,737 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

      • 1% Above List Price
      • $607/SF
      • 182 Days On Market

      Last Sold Price $850,000

      Last Listing Agent William Walters Daniel Gale Sotheby's

  • 2555 Youngs Ave Unit 11D, 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
    • 150 Baywater Ave, Southold, NY 11971

      Est $1,003,901 Not Listed For Sale

      150 Baywater Ave, Southold, NY 11971

      • 3 Beds
      • 2.5 Baths
      • 2,100 Sq Ft
      • Built 1663
      150 Baywater Ave, Southold, NY 11971

      Last Sold Summary

      • 43% Above List Price
      • $333/SF
      • 46 Days On Market

      Last Sold Price $700,000

      Last Listing Agent Paul Loeb Douglas Elliman Real Estate

  • 2375 Laurel Ave, Southold, NY 11971

    $2,495,000 Sold Jun 27, 2025

    2375 Laurel Ave, Southold, NY 11971

    • 4 Beds
    • 4.5 Baths
    • 3,960 Sq Ft
    • Built 2025

    Last Sold Summary

    • $630/SF
    • 11 Days On Market

    Last Listing Agent Kristy Naddell Douglas Elliman Real Estate

    2375 Laurel Ave, Southold, NY 11971
    • 500 Glenn Rd, Southold, NY 11971

      Est $1,059,396 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

      • 19% Below List Price
      • $839/SF
      • 18 Days On Market

      Last Sold Price $1,300,000

      Last Listing Agent Lee Beninati Beninati Associates

  • 2575 Oaklawn Ave, 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 $803,852

    Last Listing Agent Bridget Elkin Compass Greater NY LLC

    2575 Oaklawn Ave, Southold, NY 11971

Showing Results 201 - 240, Page 6 of 18

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