4,571

Southold, NY Homes

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  • /33

    $2,895,000

    • 5 Beds
    • 5.5 Baths
    • 3,240 Sq Ft

    1135 Wildberry Ln, Southold, NY 11971

    North Fork living, refined. Welcome to Wildberry. Your newly constructed dream home, where design, light, and landscape converge - set against sweeping, vineyard views and crafted for effortless indoor-outdoor living. From the moment you enter, the home reveals a quiet sophistication, with natural light pouring through thoughtfully placed openings, creating a sense of calm and connection to its

    Melissa Principi Douglas Elliman Real Estate

    1135 Wildberry Ln, Southold, NY 11971
  • /28

    $9,500 Per Month

    • 3 Beds
    • 3 Baths
    • 2,280 Sq Ft
    • House for Rent

    205 Pine Ave, Southold, NY 11971

    A relaxed North Fork summer retreat with a private beaches, a pool for long afternoons, and easy access to vineyards, farmstands, and waterfront dining.Summer on the North Fork begins at 205 Pine Avenue!Located within the coveted Goose Bay Estates private beach community, this beautifully maintained Southold home offers access to two private beaches at the end of the street—perfect for

    Barbara Poliwoda Douglas Elliman Real Estate

    205 Pine Ave, Southold, NY 11971
  • 44600 County Road 48, Southold, NY 11971

    $740,000

    Sold Sep 16, 2026

    44600 County Road 48, Southold, NY 11971

    • 2 Beds
    • 1.5 Baths
    • 2,350 Sq Ft
    • Built 1968

    Last Sold Summary

    • 6% Below List Price
    • $315/SF
    • 46 Days On Market

    Current Estimated Value $875,651

    Last Listing Agent Gayle Marriner Smith Daniel Gale Sothebys Intl Rlty

    44600 County Road 48, Southold, NY 11971
    • 100 W Shore Dr, Southold, NY 11971

      Est $2,896,718

      Not Listed For Sale

      100 W Shore Dr, Southold, NY 11971

      • 6 Beds
      • 3.5 Baths
      • 2,400 Sq Ft
      • Built 1930
      100 W Shore Dr, Southold, NY 11971

      Last Sold Summary

      • 103 Days On Market

      Last Listing Agent Basil Boziotis Compass Greater NY LLC

  • /13

    $799,000

    Pending
    • Land
    • 41,817 Sq Ft
    • $832,292 per Acre

    13260 Soundview Ave, Southold, NY 11971

    Build your North Fork dream in the heart of Southold. This exceptional 0.96-acre parcel is nestled among mature trees and surrounded by the scenic beauty of farmland and nature. This peaceful setting with easy access to Long Island Sound beaches, with breathtaking sunsets, acclaimed wineries, farm stands, marinas, and charming village amenities. Buyer is responsible for verifying all zoning,

    Dennis Blachut Signature Premier Properties

    13260 Soundview Ave, Southold, NY 11971
  • /43

    $35,000 Per Month

    • 3 Beds
    • 3.5 Baths
    • 2,724 Sq Ft
    • House for Rent

    345 Colonial Rd, Southold, NY 11971

    Tucked away on a private setting in a peaceful North Fork neighborhood just minutes from Corey Creek, Croteaux Vineyards and Greenport Brewery, this exceptional colonial offers the perfect backdrop for an unforgettable summer. With approximately 2,700 sq. ft. of bright, inviting living space across two levels, there is ample room for family and friends to gather and create lasting memories. Step

    Gloria Scrocco STOEBE & CO

    345 Colonial Rd, Southold, NY 11971
  • 1040 Nakomis Rd, Southold, NY 11971

    $740,000

    Sold Nov 04, 2025

    1040 Nakomis Rd, Southold, NY 11971

    • 3 Beds
    • 1 Bath
    • 1,100 Sq Ft
    • Built 1971

    Last Sold Summary

    • 4% Below List Price
    • $673/SF
    • 12 Days On Market

    Current Estimated Value $765,573

    Last Listing Agent Maryse Bransfield William Raveis New York LLC

    1040 Nakomis Rd, Southold, NY 11971
    • 150 W Shore Dr, Southold, NY 11971

      Est $2,678,000

      Not Listed For Sale

      150 W Shore Dr, Southold, NY 11971

      • 4 Beds
      • 4 Baths
      • Built 1930
      150 W Shore Dr, Southold, NY 11971

      Last Sold Summary

      • 20 Days On Market

      Last Listing Agent Kristy Naddell Douglas Elliman Real Estate

  • /38

    $1,599,000

    New Construction $100K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,668 Sq Ft

    1700 Smith Dr S, Southold, NY 11971

    Experience the best of North Fork living in this stunning new construction home offering beautiful water views and deeded beach access. Thoughtfully designed with modern coastal elegance, this residence blends quality craftsmanship, open-concept living, and effortless indoor-outdoor flow. The main living area is filled with natural light and showcases spacious interiors, elevated finishes, and a

    Kristy Naddell Douglas Elliman Real Estate

    1700 Smith Dr S, Southold, NY 11971
  • /18

    $15,500 Per Month

    • 3 Beds
    • 1 Bath
    • 1,500 Sq Ft
    • House for Rent

    2380 S Harbor Rd, Southold, NY 11971

    Available: August $15.5K, Oct 1, 2026 to Sept 30, 2027 - Monthly Rate $3,700. The Yellow House sits on five secluded acres in Southold on the North Fork of Long Island, offering sweeping vineyard views and stunning sunsets. One of the North Fork's best bay beaches is just a five-minute stroll to the end of the road. The home has been newly painted and furnished and features central air

    Sheri Winter Parker Corcoran

    2380 S Harbor Rd, Southold, NY 11971
  • 600 Highwood Rd, Southold, NY 11971

    $882,000

    Sold Jul 13, 2026

    600 Highwood Rd, Southold, NY 11971

    • 2 Beds
    • 1 Bath
    • 1,954 Sq Ft
    • Built 1976

    Last Sold Summary

    • 12% Below List Price
    • $451/SF
    • 23 Days On Market

    Last Listing Agent Alexis Meadows Compass Greater NY LLC

    600 Highwood Rd, Southold, NY 11971
    • 295 Grove Dr, Southold, NY 11971

      Est $1,327,962

      Not Listed For Sale

      295 Grove Dr, Southold, NY 11971

      • 3 Beds
      • 2.5 Baths
      • 2,492 Sq Ft
      • Built 1945
      295 Grove Dr, Southold, NY 11971

      Last Sold Summary

      • 38 Days On Market

      Last Listing Agent Nancy Cervelli Daniel Gale Sothebys Intl Rlty

  • /40

    $1,249,000

    $46K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 2,000 Sq Ft

    1220 Youngs Ave, Southold, NY 11971

    It's time to put your money in Real Estate! Here's a property that is in prime condition and generates an income plus appreciation! Hamlet Business (HB) zoned property, in the heart of the Hamlet of Southold! Currently a Legal two-family home - each apartment has two bedrooms, wood floors, updated eat-in kitchen, spacious living room, bathroom, window air-conditioners, with lots of natural light

    Lee Beninati Beninati Associates

    1220 Youngs Ave, Southold, NY 11971
  • /27

    $14,500 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 a wall of sliding glass doors that open to a waterside deck, perfect for enjoying the bay breeze. The eat-in

    Jeanmarie Bay William Raveis New York LLC

    1355 Watersedge Way, Southold, NY 11971
  • 2215 Laurel Ave, Southold, NY 11971

    $2,400,000

    Sold Oct 09, 2025

    2215 Laurel Ave, Southold, NY 11971

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

    Last Sold Summary

    • 5% Above List Price
    • $748/SF
    • 128 Days On Market

    Current Estimated Value $2,312,845

    Last Listing Agent Kristy Naddell Douglas Elliman Real Estate

    2215 Laurel Ave, Southold, NY 11971
    • 950 Paradise Shores Rd, Southold, NY 11971

      Est $983,959

      Not Listed For Sale

      950 Paradise Shores Rd, Southold, NY 11971

      • 4 Beds
      • 2 Baths
      • 1,700 Sq Ft
      • Built 1983
      950 Paradise Shores Rd, Southold, NY 11971

      Last Sold Summary

      • 43 Days On Market

      Last Listing Agent JoAnn Wind Daniel Gale Sothebys Intl Rlty

  • /20

    $895,000

    $80K PRICE DROP Pending
    • 3 Beds
    • 2.5 Baths
    • 1,988 Sq Ft

    445 Budds Pond Rd, Southold, NY 11971

    This light and bright three-bedroom, three-bath home in Willow Point has been thoughtfully cared for by its original owner since being built in 2003. Located just a few hundred yards from a sandy bay beach and featuring a privately owned deeded boat slip, the property offers meaningful water access rarely found at this price point. With its comfort, convenience, and true North Fork lifestyle

    Bridget Elkin Compass Greater NY LLC

    445 Budds Pond Rd, Southold, NY 11971
  • /47

    $49,000 Per Month

    • 6 Beds
    • 5.5 Baths
    • 6,600 Sq Ft
    • House for Rent

    57305 Route 48, Greenport, NY 11944

    Spectacular, contemporary seasonal rental home with pool and Jacuzzi on the Long Island Sound front. 150 feet of direct waterfront and beach, with incredible view. Meticulously renovated and professionally designed. 6 bedrooms, 5.5 bathrooms. Hamptons luxury in North Fork. Home situated on 1 acre, 6,600 square feet. One master bedroom has jacuzzi and steam room and two extra bedrooms with full

    Zepur Diktas Compass Greater NY LLC

    57305 Route 48, Greenport, NY 11944
  • 500 Meadow Ct Unit 28, Southold, NY 11971

    $865,000

    Sold Dec 04, 2025

    500 Meadow Ct Unit 28, Southold, NY 11971

    • 3 Beds
    • 2.5 Baths
    • 3,735 Sq Ft
    • Built 1994

    Last Sold Summary

    • 21% Below List Price
    • $232/SF
    • 112 Days On Market

    Last Listing Agent Gayle Marriner Smith Daniel Gale Sothebys Intl Rlty

    500 Meadow Ct Unit 28, Southold, NY 11971
    • 2230 Paradise Shores Rd, Southold, NY 11971

      Est $1,388,613

      Not Listed For Sale

      2230 Paradise Shores Rd, Southold, NY 11971

      • 3 Beds
      • 3 Baths
      • 2,800 Sq Ft
      • Built 2000
      2230 Paradise Shores Rd, Southold, NY 11971

      Last Sold Summary

      • 35 Days On Market

      Last Listing Agent Kenneth Poliwoda Douglas Elliman Real Estate

  • /6

    $1,649,000

    $150K PRICE DROP
    • Land
    • 8.65 Acres
    • $190,636 per Acre

    420 Leon Rd, Southold, NY 11971

    Calling all builders and investors! Beautiful 8.65 acres of cleared, leveled land in Southold Town. This parcel is zoned R-80, (2 Acre zoning) and has 250' of frontage on Sound Avenue (North Road) and access from adjacent Leon Road. Sellers will not consider offers "subject to" any permits or approvals.

    Melissa Principi Douglas Elliman Real Estate

    420 Leon Rd, Southold, NY 11971
  • /20

    $8,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,000 Sq Ft
    • House for Rent

    1050 Pine Ave, Southold, NY 11971

    North Fork summers are defined by sun-soaked beach days, vineyard hopping, and slow evenings spent cooking under the open sky—and this charming 3-bedroom, 2-bath cottage captures it all. Tucked away in Southold, this inviting rental places you right in the heart of the North Fork, perfectly positioned to experience everything the area has to offer. Spend your mornings browsing Southold’s curated

    Kieran Collings Douglas Elliman Real Estate

    1050 Pine Ave, Southold, NY 11971
  • 48920 Route 25, Southold, NY 11971

    $535,000

    Sold Apr 06, 2026

    48920 Route 25, Southold, NY 11971

    • 2 Beds
    • 2 Baths
    • 1,100 Sq Ft
    • Built 1955

    Last Sold Summary

    • 11% Below List Price
    • $486/SF
    • 102 Days On Market

    Current Estimated Value $588,665

    Last Listing Agent William Walters Daniel Gale Sothebys Intl Rlty

    48920 Route 25, Southold, NY 11971
    • 9390 N Bayview Rd, Southold, NY 11971

      Est $1,800,335

      Not Listed For Sale

      9390 N Bayview Rd, Southold, NY 11971

      • 3 Beds
      • 2.5 Baths
      • 3,700 Sq Ft
      • Built 2002
      9390 N Bayview Rd, Southold, NY 11971

      Last Sold Summary

      • 155 Days On Market

      Last Listing Agent Mariah Mills Daniel Gale Sothebys Intl Rlty

  • /13

    $4,300,000

    Pending
    • Land
    • 13.85 Acres
    • $310,469 per Acre

    11535 N Bayview Rd, Southold, NY 11971

    Rare opportunity to own this stunning 13.85 acres bay front parcel with over 450ft of secluded beach. This property boasts a depth of over 1000ft, creating a huge blank canvas to design your legacy estate. Offering scenic trails, serene ponds, and glorious sunrises. The perfect place to build your dream home and weave your everlasting story.

    Peggy VanGorden Daniel Gale Sothebys Intl Rlty

    11535 N Bayview Rd, Southold, NY 11971
  • /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
  • 58425 Route 48, Greenport, NY 11944

    $1,240,000

    Sold Dec 23, 2025

    58425 Route 48, Greenport, NY 11944

    • 3 Beds
    • 2 Baths
    • 1,300 Sq Ft
    • Built 1982

    Last Sold Summary

    • 11% Below List Price
    • $954/SF
    • 356 Days On Market

    Current Estimated Value $1,311,401

    Last Listing Agent William Walters Daniel Gale Sothebys Intl Rlty

    58425 Route 48, Greenport, NY 11944
    • 670 Seawood Dr, Southold, NY 11971

      Est $1,228,788

      Not Listed For Sale

      670 Seawood Dr, Southold, NY 11971

      • 3 Beds
      • 3 Baths
      • Built 1961
      670 Seawood Dr, Southold, NY 11971

      Last Sold Summary

      • 31 Days On Market

      Last Listing Agent Nicole Galluccio Compass Greater NY LLC

  • /43

    $1,395,000

    $150K PRICE DROP Pending
    • 4 Beds
    • 3.5 Baths
    • 2,600 Sq Ft

    425 Maple Ln, Southold, NY 11971

    Coveted Maple Lane setting in the heart of Southold Village with easy access to all Southold Village amenities and LIRR ~ This recently transformed shingled Craftsman Style residence offers 4 bedrooms, 3.5 baths, timeless architectural character, exceptional private outdoor living, and a truly special North Fork lifestyle. Beautifully landscaped with specimen plantings, the property is designed

    Nancy Cervelli Daniel Gale Sothebys Intl Rlty

    425 Maple Ln, Southold, NY 11971
  • /33

    $25,000 Per Month

    • 4 Beds
    • 3.5 Baths
    • House for Rent

    910 Glenn Rd, Southold, NY 11971

    Introducing your perfect retreat! This stunning 4-bed, 3.5-bath waterfront oasis nestled on West Creek in Southold. Enjoy access to Peconic Bay via your private dock. Spanning approx 3500 sq ft, revel in the elegance of oak floors, a luxurious soaking tub, and high ceilings throughout. The 1st floor has 2 primary ensuites, a spacious Great Room with cozy fireplace, laundry, and 2.5 baths +2-car

    Andrea Parks Douglas Elliman Real Estate

    910 Glenn Rd, Southold, NY 11971
  • 70 Mockingbird Ln, Southold, NY 11971

    $1,130,000

    Sold Sep 30, 2025

    70 Mockingbird Ln, Southold, NY 11971

    • 4 Beds
    • 3 Baths
    • Built 2001

    Last Sold Summary

    • 16% Below List Price
    • 143 Days On Market

    Current Estimated Value $1,102,078

    Last Listing Agent Kelly Gatanas Daniel Gale Sothebys Intl Rlty

    70 Mockingbird Ln, Southold, NY 11971
    • 1750 Seawood Dr, Southold, NY 11971

      Est $932,041

      Not Listed For Sale

      1750 Seawood Dr, Southold, NY 11971

      • 3 Beds
      • 2 Baths
      • 1,420 Sq Ft
      • Built 1989
      1750 Seawood Dr, Southold, NY 11971

      Last Sold Summary

      • 31 Days On Market

      Last Listing Agent Stacy Zigman RE/MAX City Square

  • /9

    $3,695,000

    $305K PRICE DROP
    • 3 Beds
    • 4 Baths
    • 3,496 Sq Ft

    1480 Old Wood Path, Southold, NY 11971

    Set on nearly four acres along one of the North Fork’s most coveted stretches of sandy bay beach, this is a rare opportunity to secure an exceptional waterfront property with meaningful upside. The existing three-bedroom, four-bath home offers a solid foundation for renovation or expansion, allowing a new owner to tailor the property to their vision.The grounds are equally compelling. A

    Bridget Elkin Compass Greater NY LLC

    1480 Old Wood Path, Southold, NY 11971
  • /34

    $30,000 Per Month

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

    650 Pine Ave, Southold, NY 11971

    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
  • 630 Tarpon Dr, Southold, NY 11971

    $1,943,000

    Sold Apr 17, 2026

    630 Tarpon Dr, Southold, NY 11971

    • 3 Beds
    • 2.5 Baths
    • 2,100 Sq Ft
    • Built 1980

    Last Sold Summary

    • 2% Above List Price
    • $925/SF
    • 64 Days On Market

    Current Estimated Value $1,678,945

    Last Listing Agent Tom Uhlinger Douglas Elliman Real Estate

    630 Tarpon Dr, Southold, NY 11971
    • 6980 N Bayview Rd, Southold, NY 11971

      Est $864,170

      Not Listed For Sale

      6980 N Bayview Rd, Southold, NY 11971

      • 3 Beds
      • 2 Baths
      • 1,650 Sq Ft
      • Built 1989
      6980 N Bayview Rd, Southold, NY 11971

      Last Sold Summary

      • 96 Days On Market

      Last Listing Agent Nicholas Planamento William Raveis New York LLC

  • /7

    $499,000

    • Land
    • 16,552 Sq Ft
    • $1,313,158 per Acre

    11195 N Bayview Rd, Southold, NY 11971

    .38-acre wooded level lot in a private and natural setting. Ideally located near Paradise Point, Cedar Beach, Southold shops, vineyards, farmstands and Greenport Brewery. This is a triangle shape lot with 258ft of frontage on N Bayview Rd and 178ft/182ft deep on each side. A rare opportunity to create your own coastal retreat in one of the North Fork’s most desirable neighborhoods. No preliminary

    Mariah Mills Daniel Gale Sothebys Intl Rlty

    11195 N Bayview Rd, Southold, NY 11971
  • /13

    $7,000 Per Month

    • 1 Bed
    • 1 Bath
    • 750 Sq Ft
    • House for Rent

    Unlisted Address

    Experience the charm of this delightful rental cottage nestled in Southold, North Fork, just a stone’s throw from Founder's Landing Park and Wharf House, with one of the most amazing sugar sand beaches in our community. This unique, fully furnished one-bedroom retreat features flexible rental periods and competitive rates throughout the year.Imagine waking up to the serene views of a

    Nicholas Planamento William Raveis New York LLC

    Unlisted Address
  • 3635 Old North Rd, Southold, NY 11971

    $1,500,000

    Sold Jan 08, 2026

    3635 Old North Rd, Southold, NY 11971

    • Land
    • 9.5 Acres
    • $157,895 per Acre

    Last Sold Summary

    • 8 Days On Market

    Current Estimated Value $1,495,268

    Last Listing Agent Kristy Naddell Douglas Elliman Real Estate

    3635 Old North Rd, Southold, NY 11971
    • 1785 Seawood Dr, Southold, NY 11971

      Est $822,191

      Not Listed For Sale

      1785 Seawood Dr, Southold, NY 11971

      • 3 Beds
      • 2 Baths
      • Built 1976
      1785 Seawood Dr, Southold, NY 11971

      Last Sold Summary

      • 25 Days On Market

      Last Listing Agent Laura Freudenberg BH&G R E Realty Connect

Showing Results 161 - 200, Page 5 of 18

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