4,599

Southold, NY Homes

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  • /44

    $6,850,000

    $1M PRICE DROP
    • 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

    $11,213

    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 $11,213/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

    810 Waterview Dr Unit SI ID1261529P, 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 $476,000

    Last Listing Agent Mary Ellen Ellwood Douglas Elliman Real Estate

    4077 Main Bayview Rd, Southold, NY 11971
    • 620 Rogers Rd, Southold, NY 11971

      Est $1,511,631

      Not Listed For Sale

      620 Rogers Rd, Southold, NY 11971

      • 4 Beds
      • 3 Baths
      • Built 1938
      620 Rogers Rd, Southold, NY 11971

      Last Sold Summary

      • 34 Days On Market

      Last Listing Agent Eric Elkin Compass Greater NY LLC

  • /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. This private community on Hashamomuck Pond offers 2 bedrooms, warm oak floors, spacious living room, and waterfront views galore. Enjoy kayaking, paddleboarding, fishing, and swimming right out your back door. This is the

    Agent Photo

    Joseph Nina

    Douglas Elliman Real Estate

    136 Bayview Ave, 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
  • 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
    • 55075 Route 25 Unit 1, Southold, NY 11971

      Est $378,000

      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

  • /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
  • /29

    $15,019

    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 $15,019/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 29, 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

    1345 Long Creek Dr Unit SI ID1512339P, 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
    • 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

  • /21

    $989,000

    Pending
    • 2 Beds
    • 1 Bath
    • 1,200 Sq Ft

    2070 Cedar Dr, Southold, NY 11971

    2070 Cedar Drive offers the kind of North Fork lifestyle buyers search for but rarely find — a welcoming home in a peaceful setting. There’s a sandy neighborhood beach right across the street and it’s positioned near other beaches, marinas, and North Fork vineyards. Located in a highly desirable Southold waterfront enclave, the property presents a compelling opportunity for both lifestyle buyers

    Agent Photo

    Dawn Watson

    Serhant East End LLC

    2070 Cedar Dr, 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
  • 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 $1,716,000

    Last Listing Agent Connie Liappas Compass Greater NY LLC

    285 Blue Marlin Dr, 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

  • /49

    $1,899,000

    • 4 Beds
    • 2.5 Baths
    • 3,800 Sq Ft

    25 Lighthouse Rd, Southold, NY 11971

    Tucked at the end of a long, private drive on one of Southold’s historic streets, this custom-built, designer's own Nantucket-style home delivers 3,800 square feet of luxury on just under an acre of manicured gardens. Minutes from both the Sound and Peconic Bay, plus the restaurants, wineries, and village charm that make North Fork living feel like a permanent vacation. Step onto the mahogany

    Agent Photo

    Janet Bidwell

    Douglas Elliman Real Estate

    25 Lighthouse Rd, 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
  • 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
    • 200 Deer Run, Southold, NY 11971

      Est $3,800,667

      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

  • /44

    $2,150,000

    • 3 Beds
    • 2.5 Baths
    • 2,367 Sq Ft

    2245 Little Peconic Bay Ln, Southold, NY 11971

    Perfectly sited on a protected inlet on West Lake, with direct access to the pristine waters of the Little Peconic Bay, this exceptional waterfront retreat embodies the effortless elegance of North Fork living. Thoughtfully designed to embrace its spectacular setting, the home is filled with natural light and showcases captivating water views from its principal living spaces. The main level

    Andrea Parks Douglas Elliman Real Estate

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

  • /30

    $1,249,000

    Pending
    • 3 Beds
    • 2.5 Baths
    • 2,300 Sq Ft

    650 the Esplanade, Southold, NY 11971

    Southold, North Fork – Private Bayfront Community LivingDiscover effortless, upscale living in the coveted Angel Shores bayfront community, complete with private association access to a pristine sugar-sand beach. Set on a beautifully landscaped, ultra-private lot backing to over 20 acres of protected preserve land—with only one immediate neighboring home—this exceptional 2,300 sq ft

    Nicholas Planamento William Raveis New York LLC

    650 the Esplanade, 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
  • 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
    • 17240 Soundview Ave, Southold, NY 11971

      Est $1,807,243

      Not Listed For Sale

      17240 Soundview Ave, Southold, NY 11971

      17240 Soundview Ave, Southold, NY 11971

      Last Sold Summary

      • 40 Days On Market

      Last Listing Agent Kristy Naddell Douglas Elliman Real Estate

  • /12

    $239,000

    Pending
    • 1 Bath
    • 250 Sq Ft

    52325 County Road 48 Unit 31, Southold, NY 11971

    Seasonal Condo Near a Memorable Long Island Sound Beach (Town Beach). Studio Apartment is Located on the 2nd Floor. The Condo Offers a Community Room, Lawn with BBQ Area, Laundry, Off Street Parking, Boat Storage, Beach Storage. Electric, Water, Cable and Sewer/Cesspool included in Common Charge. SEASONAL CONDO OPEN APRIL TO NOVEMBER. NOT YEAR ROUND.

    Paul Loeb Douglas Elliman Real Estate

    52325 County Road 48 Unit 31, 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
  • 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 $1,383,756

    Last Listing Agent Susan Orioli Engel & Volkers North Fork

    1025 Long Creek Dr, 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

  • /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
  • 58315 North Rd, Greenport, NY 11944

    $992,000

    Sold Dec 12, 2025

    58315 North Rd, Greenport, NY 11944

    • 2 Beds
    • 2 Baths
    • 900 Sq Ft
    • Built 1972

    Last Sold Summary

    • 6% Below List Price
    • $1,102/SF
    • 0 Days On Market

    Current Estimated Value $1,003,247

    Last Listing Agent Donna Fakiris Modern Age Realty Group LLC

    58315 North Rd, Greenport, NY 11944
    • 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

  • /25

    $2,799,000

    New Construction $200K PRICE DROP
    • 8 Beds
    • 7 Baths
    • 5,600 Sq Ft

    1350 Hortons Ln, Southold, NY 11971

    2-Acre Private Oasis with Custom "To Be Built" Luxury Home - Excellent Location Near Town, Beaches & Vineyards! Discover the perfect blend of privacy, luxury and convenience with this exceptional vacant lot, tucked away in a serene, secluded setting --- Yet just minutes from downtown, pristine beaches, and world-class vineyards, shopping and dining. Plans are in-place for a "To Be Built" custom

    Thomas McCarthy Thomas J McCarthy Real Estate

    1350 Hortons Ln, Southold, NY 11971
  • /26

    $15,000 Per Month

    • 4 Beds
    • 3 Baths
    • 2,700 Sq Ft
    • House for Rent

    1000 Rambler Rd, Southold, NY 11971

    Beautiful like new colonial just 500 feet from sandy bay beach. Four bedrooms plus a lovely sunroom. Fully Furnished. Enjoy your morning coffee on the bedroom balcony. Outside shower and gas grill off backyard deck. Bicycles and a kayak with trailer included. A perfect beach house. Available July $15,000, August-Labor Day $20,000, July-Labor Day $35,000, utilities included.

    Pamela Hunt Colony Realty

    1000 Rambler Rd, Southold, NY 11971
  • 155 Shepard Dr, Southold, NY 11971

    $791,000

    Sold Dec 02, 2025

    155 Shepard Dr, Southold, NY 11971

    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft
    • Built 1988

    Last Sold Summary

    • 21% Below List Price
    • $494/SF
    • 217 Days On Market

    Current Estimated Value $895,232

    Last Listing Agent Isaac Israel Richmond Realty Corp

    155 Shepard 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
$672
Number of Homes for Sale
48
Last 12 months Home Sales
99
Months of Supply
5.80
Median List Price
$1,250,000
Median Change From 1st List Price
4%
Median Home Sale Price YoY Change
-7%
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