4,571

Southold, NY Homes

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  • /14

    $999,000

    $101K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 800 Sq Ft

    136 Bayview Ave, Southold, NY 11971

    The Summer has never been sweeter in this coastal cottage right on the water. Peaceful breezes blow while you sit on the covered deck and watch the paddle boarders go by. Located on a dead-end street on Hashamomuck Pond, this home offers a private dock, 2 bedrooms, warm oak floors, spacious living room, and waterfront views galore. Enjoy boating, kayaking, paddleboarding, fishing, and swimming

    Agent Photo

    Joseph Nina

    Douglas Elliman Real Estate

    136 Bayview Ave, Southold, NY 11971
  • /29

    $19,730

    Total Monthly Price

    • 4 Beds
    • 2 Baths
    • 3,196 Sq Ft
    • Condo for Rent

    1345 Long Creek Dr Unit SI ID1512339P, Southold, NY 11971

    The advertised rate of $19,730/month is the lowest available price, based on a 30 day(s) stay with a move-in date of May 8, 2027. Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    1345 Long Creek Dr Unit SI ID1512339P, Southold, NY 11971
  • 4077 Main Bayview Rd, Southold, NY 11971

    $475,000

    Sold Mar 30, 2026

    4077 Main Bayview Rd, Southold, NY 11971

    • Land
    • 40,075 Sq Ft
    • $516,304 per Acre

    Last Sold Summary

    • 21% Below List Price
    • 143 Days On Market

    Current Estimated Value $478,667

    Last Listing Agent Mary Ellen Ellwood Douglas Elliman Real Estate

    4077 Main Bayview Rd, Southold, NY 11971
    • 55075 Route 25 Unit 1, Southold, NY 11971

      Est $399,000

      Not Listed For Sale

      55075 Route 25 Unit 1, Southold, NY 11971

      • 2 Beds
      • 1 Bath
      • 1,000 Sq Ft
      • Built 1968
      55075 Route 25 Unit 1, Southold, NY 11971

      Last Sold Summary

      • 28 Days On Market

      Last Listing Agent Kenneth Poliwoda Douglas Elliman Real Estate

  • /44

    $6,850,000

    $1M PRICE DROP Pending
    • 5 Beds
    • 4.5 Baths
    • 4,627 Sq Ft

    1750 Hobart Rd, Southold, NY 11971

    Welcome to a stunning, one-of-a-kind, luxury modern waterfront home in the highly sought-after hamlet of Southold. This custom, newly constructed, residence is perfectly oriented West on Town Creek. Featuring 160’ of waterfront and expansive views of Peconic Bay, it includes a private 6 x 20' dock and an 82’ Trex catwalk. Constructed with every attention to detail, the home includes maximum

    Agent Photo

    Deborah Pirro

    Daniel Gale Sothebys Intl Rlty

    1750 Hobart Rd, Southold, NY 11971
  • /19

    $9,879

    Total Monthly Price

    • 3 Beds
    • 1 Bath
    • 1,097 Sq Ft
    • Condo for Rent

    810 Waterview Dr Unit SI ID1261529P, Southold, NY 11971

    The advertised rate of $9,879/month is the lowest available price, based on a 1 month(s) stay with a move-in date of November 22, 2026. Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    810 Waterview Dr Unit SI ID1261529P, Southold, NY 11971
  • 5805 Main Bayview Rd, Southold, NY 11971

    $2,700,000

    Sold Jan 12, 2026

    5805 Main Bayview Rd, Southold, NY 11971

    • 4 Beds
    • 3 Baths
    • 3,253 Sq Ft
    • Built 1989

    Last Sold Summary

    • 17% Below List Price
    • $830/SF
    • 65 Days On Market

    Current Estimated Value $2,531,963

    Last Listing Agent Kristy Naddell Douglas Elliman Real Estate

    5805 Main Bayview Rd, Southold, NY 11971
    • 245 Clearview Ave W, Southold, NY 11971

      Est $1,443,008

      Not Listed For Sale

      245 Clearview Ave W, Southold, NY 11971

      • 3 Beds
      • 3 Baths
      • 2,450 Sq Ft
      • Built 2018
      245 Clearview Ave W, Southold, NY 11971

      Last Sold Summary

      • 9 Days On Market

      Last Listing Agent Mariah Mills Daniel Gale Sothebys Intl Rlty

  • /10

    $605,000

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

    2555 Youngs Ave Unit 11A, Southold, NY 11971

    Welcome to this corner residence at Founders Village, where easy, low-maintenance living meets the North Fork lifestyle.This 1,200-square-foot home offers 2 bedrooms, 2 full baths and a full basement, giving you valuable storage and extra space that can be hard to find when downsizing to condominium living.The corner location provides added green space on multiple sides, along

    Agent Photo

    Timothy O'Keefe

    Signature Premier Properties

    2555 Youngs Ave Unit 11A, Southold, NY 11971
  • /20

    $6,000 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,750 Sq Ft
    • House for Rent

    1854 N Bayview Rd, Southold, NY 11971

    Year round lease. Amazing location with private beach, amazing waterviews and a private dock! Home is fully furnished and has 2 bedrooms, 2 full bathrooms and a 1/2 bathroom. Bring your boat or kayaks!

    Isaac Israel Richmond Realty Corp

    1854 N Bayview Rd, Southold, NY 11971
  • 650 the Esplanade, Southold, NY 11971

    $1,249,000

    Sold Aug 14, 2026

    650 the Esplanade, Southold, NY 11971

    • 3 Beds
    • 2.5 Baths
    • 2,300 Sq Ft
    • Built 1998

    Last Sold Summary

    • $543/SF
    • 24 Days On Market

    Current Estimated Value $1,258,730

    Last Listing Agent Nicholas Planamento William Raveis New York LLC

    650 the Esplanade, Southold, NY 11971
    • 43475 Route 25, Peconic, NY 11958

      Est $915,674

      Not Listed For Sale

      43475 Route 25, Peconic, NY 11958

      • 4 Beds
      • 1.5 Baths
      • 2,400 Sq Ft
      • Built 1890
      43475 Route 25, Peconic, NY 11958

      Last Sold Summary

      • 29 Days On Market

      Last Listing Agent Paul Loeb Douglas Elliman Real Estate

  • /34

    $1,799,000

    $100K PRICE DROP Pending
    • 4 Beds
    • 2.5 Baths
    • 3,800 Sq Ft

    25 Lighthouse Rd, Southold, NY 11971

    Private, polished, and distinctly North Fork, this designer's own Nantucket-style home offers generous spaces and exceptional privacy at the end of a long drive near historic Horton’s Point Lighthouse. Set on nearly an acre of mature landscaping, a wide mahogany porch opens to a dramatic foyer and expansive, light-filled living area with custom moldings, French doors to patio and plantation

    Agent Photo

    Janet Bidwell

    Douglas Elliman Real Estate

    25 Lighthouse Rd, Southold, NY 11971
  • /18

    $22,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,300 Sq Ft
    • House for Rent

    2845 Hobart Rd, Southold, NY 11971

    Mint mid-century modern cottage offering 3 bedrooms and 2 baths, ideally located just 100 yards from sandy Founders Landing beach. The interior features clean, modern lines, anchored by a fireplace and expansive picture windows that fill the space with natural light and capture beautiful water views. Outdoors, your backyard with fire pit and outdoor shower creates an ideal setting for summer

    Eric Elkin Compass Greater NY LLC

    2845 Hobart Rd, Southold, NY 11971
  • 2120 Brigantine Dr, Southold, NY 11971

    $1,150,000

    Sold Jan 27, 2026

    2120 Brigantine Dr, Southold, NY 11971

    • 4 Beds
    • 4 Baths
    • 2,000 Sq Ft
    • Built 1972

    Last Sold Summary

    • 8% Below List Price
    • $575/SF
    • 76 Days On Market

    Current Estimated Value $1,173,616

    Last Listing Agent Barbara Poliwoda Douglas Elliman Real Estate

    2120 Brigantine Dr, Southold, NY 11971
    • 200 Deer Run, Southold, NY 11971

      Est $4,034,000

      Not Listed For Sale

      200 Deer Run, Southold, NY 11971

      • 5 Beds
      • 9 Baths
      • 6,000 Sq Ft
      • Built 2015
      200 Deer Run, Southold, NY 11971

      Last Sold Summary

      • 88 Days On Market

      Last Listing Agent Carol Szynaka Daniel Gale Sothebys Intl Rlty

  • /48

    $2,899,000

    • 4 Beds
    • 3 Baths
    • 2,351 Sq Ft

    405 Williamsburgh Dr, Southold, NY 11971

    Scandinavian Chic Waterfront Masterpiece with Panoramic Water Views | Southold Built in 2022 with exceptional craftsmanship and professionally curated interiors, this breathtaking waterfront residence blends Scandinavian chic design with warm modern coastal luxury. Set on .35 acres with direct water access, the home features 4 bedrooms, 3 full baths, 2,351 square feet of beautifully designed

    Agent Photo

    Laura Cochran

    BERKSHIRE HATHAWAY

    405 Williamsburgh Dr, Southold, NY 11971
  • /20

    $20,000 Per Month

    • 3 Beds
    • 4 Baths
    • 2,600 Sq Ft
    • House for Rent

    2045 Lake Dr, Southold, NY 11971

    Offered June $10,000 ($2,500/wk); July $20,000 ($5,000/wk); Aug $25,000 ($6,250/wk); Sept $12,000 ($3,000/wk); Oct $10,000 ($2,500/wk). Two-week minimum. This contemporary waterfront home on Great Pond enjoys sunrise over the water and spectacular sunsets over Long Island Sound from its hilltop setting in one of the North Fork’s most distinctive beach communities. Surrounded by native plantings

    Janet Markarian Daniel Gale Sothebys Intl Rlty

    2045 Lake Dr, Southold, NY 11971
  • 52325 County Road 48 Unit 31, Southold, NY 11971

    $230,000

    Sold Aug 19, 2026

    52325 County Road 48 Unit 31, Southold, NY 11971

    • 1 Bath
    • 250 Sq Ft
    • Built 1960

    Last Sold Summary

    • 4% Below List Price
    • $920/SF
    • 213 Days On Market

    Last Listing Agent Paul Loeb Douglas Elliman Real Estate

    52325 County Road 48 Unit 31, Southold, NY 11971
    • 4710 Old Rd N, Southold, NY 11971

      Est $1,374,474

      Not Listed For Sale

      4710 Old Rd N, Southold, NY 11971

      • 4 Beds
      • 2.5 Baths
      • 2,400 Sq Ft
      • Built 1978
      4710 Old Rd N, Southold, NY 11971

      Last Sold Summary

      • 24 Days On Market

      Last Listing Agent Zachary Scher Signature Premier Properties

  • /2

    $700,000

    Pending
    • Land
    • 22,215 Sq Ft
    • $1,372,549 per Acre

    875 The Strand, Southold, NY 11939

    Set along one of East Marion's most coveted waterfront stretches, 875 The Strand presents a rare opportunity to create a custom North Fork retreat on .51 acres within the desirable Pebble Beach community. The property enjoys an exceptional sense of privacy, abutting a non-buildable parcel to the south and buffered by mature landscaping to the east and west-a combination that provides unusual

    Agent Photo

    Dawn Watson

    Serhant East End LLC

    875 The Strand, Southold, NY 11939
  • /20

    $55,000 Per Month

    • 5 Beds
    • 3.5 Baths
    • 2,750 Sq Ft
    • House for Rent

    7635 Main Bayview Rd, Southold, NY 11971

    Elegant Historic Home in Southold – Coastal Charm Meets Modern Luxury Escape to the North Fork and enjoy this beautifully restored historic Southold home, perfectly blending timeless elegance with every modern comfort. This spacious retreat features 5 bedrooms and 3.5 baths, ideal for families or groups seeking a serene getaway. Enjoy central air conditioning, high-speed internet, and five smart

    Mary Terry MCKENNASHEA LLC

    7635 Main Bayview Rd, Southold, NY 11971
  • 285 Blue Marlin Dr, Southold, NY 11971

    $2,225,000

    Sold Mar 20, 2026

    285 Blue Marlin Dr, Southold, NY 11971

    • 4 Beds
    • 4.5 Baths
    • 2,842 Sq Ft
    • Built 2025

    Last Sold Summary

    • 18% Below List Price
    • $783/SF
    • 248 Days On Market

    Current Estimated Value $3,319,667

    Last Listing Agent Connie Liappas Compass Greater NY LLC

    285 Blue Marlin Dr, Southold, NY 11971
    • 1745 Nokomis Rd, Southold, NY 11971

      Est $738,893

      Not Listed For Sale

      1745 Nokomis Rd, Southold, NY 11971

      • 2 Beds
      • 1 Bath
      • Built 1972
      1745 Nokomis Rd, Southold, NY 11971

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Maryse Bransfield William Raveis New York LLC

  • /44

    $1,999,999

    $150K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,367 Sq Ft

    2245 Little Peconic Bay Ln, Southold, NY 11971

    Rarely does a Southold waterfront property offer such a compellingcombination of privacy, direct bay access, and expansive water views.Set on a protected inlet with a permitted dock and kayak launch, thisthree-bedroom, three-bath home is designed around its extraordinarysetting. Sun-filled rooms open to a supersized waterfront deck, with achef's kitchen with soapstone

    Andrea Parks Douglas Elliman Real Estate

    2245 Little Peconic Bay Ln, Southold, NY 11971
  • /20

    $14,500 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,572 Sq Ft
    • House for Rent

    465 Tarpon Dr, Southold, NY 11971

    August Rental $14,500: This elegant mid-century coastal charming North Fork rental is nestled in Southold Shore Community with a bayfront beach, marina and water access for launching a kayak. This chic and sophisticated modern home has been completely renovated and sits on a private road with a manicured front lawn and a two car garage. Enjoy your cup of coffee or lunch on the beautiful large

    Maryse Bransfield William Raveis New York LLC

    465 Tarpon Dr, Southold, NY 11971
  • 12250 Soundview Ave, Southold, NY 11971

    $1,300,000

    Sold May 04, 2026

    12250 Soundview Ave, Southold, NY 11971

    • 3 Beds
    • 3.5 Baths
    • 2,400 Sq Ft
    • Built 1985

    Last Sold Summary

    • 18% Below List Price
    • $542/SF
    • 144 Days On Market

    Current Estimated Value $1,223,608

    Last Listing Agent Scott Bennett Douglas Elliman Real Estate

    12250 Soundview Ave, Southold, NY 11971
  • /11

    $550,000

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

    2555 Youngs Ave Unit 3C, Southold, NY 11971

    Unit 3C offers a rare opportunity to create something truly your own. This 2-bedroom, 2-bath condo is ready for a new vision and offers the perfect blank canvas for buyers who would rather customize than compromise. There is tremendous potential to thoughtfully update the home to your style, selecting the finishes, fixtures, colors, and details you actually want along the way. The unfinished

    Thomas McCarthy Thomas J McCarthy Real Estate

    2555 Youngs Ave Unit 3C, Southold, NY 11971
  • /19

    $28,000 Per Month

    • 3 Beds
    • 2 Baths
    • House for Rent

    1100 Pine Ave, Southold, NY 11971

    Permit #: 0160. Superb 3-Bedroom, 2-Bathroom Ranch Home Showcases Gorgeous Water Views And Is Perfectly Located Near Goose Creek Beach And The Pulsating Heart Of Southold. The Interior Is Beautifully Designed With A Minimalist Aesthetic, Offering A Serene Retreat From The Every Day Hustle And Bustle. The Open Layout Allows For Easy Movement And A Seamless Blend Of Indoor And Outdoor Living

    Colin McCarthy Thomas J McCarthy Real Estate

    1100 Pine Ave, Southold, NY 11971
  • 1955 Laurel Ave, Southold, NY 11971

    $2,400,000

    Sold Mar 03, 2026

    1955 Laurel Ave, Southold, NY 11971

    • 3 Beds
    • 3.5 Baths
    • 3,210 Sq Ft
    • Built 2025

    Last Sold Summary

    • $748/SF
    • 104 Days On Market

    Last Listing Agent Kristy Naddell Douglas Elliman Real Estate

    1955 Laurel Ave, Southold, NY 11971
    • 2555 Youngs Ave Unit 12E, Southold, NY 11971

      Not Listed For Sale

      2555 Youngs Ave Unit 12E, Southold, NY 11971

      • 2 Beds
      • 2 Baths
      • 1,200 Sq Ft
      • Built 1986
      2555 Youngs Ave Unit 12E, Southold, NY 11971

      Last Sold Summary

      • 19 Days On Market

      Last Listing Agent Timothy O'Keefe Signature Premier Properties

  • /8

    $629,000

    • Land
    • 16,117 Sq Ft
    • $1,700,000 per Acre

    2560 Hyatt Rd, Southold, NY 11971

    Ideally Located Vacant Land. A Rare Opportunity to Create Your Own North Fork Retreat or Year-Round Home on Desirable Hyatt Road, a Quiet Setting Just Off Soundview Avenue in Southold. This Ideally Located Vacant Parcel is Just a Short Distance from Memorable McCabe’s Town Beach. The Lot is Reported to Include Coveted Deeded Rights to a Private Long Island Sound Beach. Enjoy the Tranquility of a

    Paul Loeb Douglas Elliman Real Estate

    2560 Hyatt Rd, Southold, NY 11971
  • /32

    $12,500 Per Month

    • 4 Beds
    • 4 Baths
    • 3,585 Sq Ft
    • House for Rent

    580 Gin Ln, Southold, NY 11971

    Wonderful opportunity to spend time in the wonderful Southold community of Bay Haven. Choose to spend the sunny days by your own pool, or head down the block to the community's private bay beach. There is more than ample space to host in this brightly renovated cape with room for everyone. The main level is comprised of a lounge area with fireplace and dry bar, an open kitchen and a large great

    Scott Bortzner Compass Greater NY LLC

    580 Gin Ln, Southold, NY 11971
  • 20210 Soundview Ave, Southold, NY 11971

    $2,075,000

    Sold Oct 23, 2025

    20210 Soundview Ave, Southold, NY 11971

    • 4 Beds
    • 5.5 Baths
    • 4,671 Sq Ft
    • Built 1984

    Last Sold Summary

    • 15% Below List Price
    • $444/SF
    • 79 Days On Market

    Current Estimated Value $2,046,141

    Last Listing Agent Marco Maida Compass Greater NY LLC

    20210 Soundview Ave, Southold, NY 11971
    • 55075 Main Rd Unit 1, Southold, NY 11971

      Not Listed For Sale

      55075 Main Rd Unit 1, Southold, NY 11971

      • 2 Beds
      • 1 Bath
      • 805 Sq Ft
      • Built 1968
      55075 Main Rd Unit 1, Southold, NY 11971

      Last Sold Summary

      • 72 Days On Market

      Last Listing Agent Scott Bennett Douglas Elliman Real Estate

  • /4

    $1,600,000

    • Land
    • 2 Acres
    • $800,000 per Acre

    55975 Route 25, Southold, NY 11971

    2 Acres Of Highly Desirable Hamlet Business Zoning. Subdividable Into Half Acre Lots Or Build Multiple Structures. Multiple Residential Units Possible Or Residential/Commercial Mix. Four Buildings Possible As Of Right. Excellent Route 25 Exposure & Great Location In Center Of The Hamlet! Commercial Listing MLS# 3530579

    Colin McCarthy Thomas J McCarthy Real Estate

    55975 Route 25, Southold, NY 11971
  • /21

    $60,000 Per Month

    • 3 Beds
    • 2 Baths
    • House for Rent

    355 Windjammer Dr, Southold, NY 11971

    This soothing beach house is so Zen, you will feel like you are at a spa retreat! Peaceful and perfectly appointed, the backyard features a fabulous lagoon style pool, with a waterfall and hot tub, an amazing outdoor kitchen and bar, bathroom and outdoor shower! 3 bedrooms, 2 baths, including a spacious primary suite with a gorgeous spa like bathroom. All this and steps to the association beach!

    Sheri Winter Parker Corcoran

    355 Windjammer Dr, Southold, NY 11971
  • 1025 Long Creek Dr, Southold, NY 11971

    $1,375,000

    Sold Jun 18, 2026

    1025 Long Creek Dr, Southold, NY 11971

    • 4 Beds
    • 2.5 Baths
    • 2,690 Sq Ft
    • Built 1997

    Last Sold Summary

    • 2% Below List Price
    • $511/SF
    • 18 Days On Market

    Current Estimated Value $1,378,497

    Last Listing Agent Susan Orioli Engel & Volkers North Fork

    1025 Long Creek Dr, Southold, NY 11971
    • 670 Kenneys Rd, Southold, NY 11971

      Est $1,743,017

      Not Listed For Sale

      670 Kenneys Rd, Southold, NY 11971

      • 4 Beds
      • 2.5 Baths
      • 2,417 Sq Ft
      • Built 2025
      670 Kenneys Rd, Southold, NY 11971

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Robert Merolla Aurora Property Group

Showing Results 1 - 40, Page 1 of 18

Home Price Trends

Median Sale Price
$950,000
Median Single Family Sale Price
$1,249,000
Median Townhouse Sale Price
$865,000
Median 2 Bedroom Sale Price
$718,000
Median 1 Bedroom Sale Price
$733,000
Average Price Per Sq Ft
$673
Number of Homes for Sale
4,571
Last 12 months Home Sales
99
Months of Supply
5.50
Median List Price
$1,250,000
Median Change From 1st List Price
4%
Median Home Sale Price YoY Change
-5%
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