4,634

Southold, NY Homes

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  • /2

    $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. A newly constructed residence where design, light, and landscape converge - set against sweeping, sunset 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
  • /26

    $12,500 Per Month

    • 4 Beds
    • 3.5 Baths
    • 2,500 Sq Ft
    • House for Rent

    16125 Soundview Ave, Southold, NY 11971

    Available 2026: September $12,500; October $12,500; November $8,500Experience the very best of the North Fork in this extraordinary soundfront retreat, where miles of pristine Long Island Sound beachfront become your backyard and sunsets RSVP nightly just for you. Wake each morning in the primary suite to panoramic water views that stretch to the horizon, framed by floor-to-ceiling glass that

    Sheri Winter Parker Corcoran

    16125 Soundview Ave, 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 $1,110,074

    Last Listing Agent Kelly Gatanas Daniel Gale Sothebys Intl Rlty

    70 Mockingbird Ln, Southold, NY 11971
  • /26

    $1,299,999

    $100K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,584 Sq Ft

    75 Birch Rd, Southold, NY 11971

    Tucked away on a beautifully landscaped property, this 2022 built 4 bedroom, 3.5 bath residence offers the perfect blend of modern construction, thoughtful design, and effortless North Fork charm. From the moment you arrive, the inviting front porch, complete with a classic swing, sets the tone for relaxed living. Inside, the home is thoughtfully designed with a seamless flow, anchored by a

    Susan Orioli Engel & Volkers North Fork

    75 Birch Rd, Southold, NY 11971
  • /25

    $6,000 Per Month

    • 3 Beds
    • 1 Bath
    • House for Rent

    400 Diamond Ln, Peconic, NY 11958

    June: $6,000.00 Enjoy stunning water views and all-season access to the Sound from this charming 3-bedroom, 1-bathroom waterfront home. This cozy home channels happy, mid-century vibes. Large living room with fireplace, dining nook, and sunroom, all with breathtaking views of the water. The patio with BBQ is the perfect spot to relax and enjoy the outdoors, and the path to the Sound makes it easy

    Sheri Winter Parker Corcoran

    400 Diamond Ln, Peconic, NY 11958
  • 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 $1,678,999

    Last Listing Agent Tom Uhlinger Douglas Elliman Real Estate

    630 Tarpon Dr, Southold, NY 11971
  • /44

    $3,450,000

    • 5 Beds
    • 3.5 Baths
    • 4,500 Sq Ft

    790 N Sea Dr, Southold, NY 11971

    Quintessential North Fork Beach House!! Perched high above with breathtaking views of the Long Island Sound, this stunning custom-built home offers the perfect blend of luxury, comfort, and location. Just across the street from the shores of Kenney’s Beach, this 2009-built residence features 5 spacious bedrooms and 3.5 beautifully appointed baths, including a serene first-floor primary suite. Set

    Kristy Naddell Douglas Elliman Real Estate

    790 N Sea Dr, Southold, NY 11971
  • /27

    $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 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
  • 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 $1,485,626

    Last Listing Agent Kristy Naddell Douglas Elliman Real Estate

    3635 Old North Rd, Southold, NY 11971
  • /14

    $999,999

    Pending
    • 2 Beds
    • 1 Bath
    • 1,954 Sq Ft

    600 Highwood Rd, Southold, NY 11971

    Unique opportunity in Southold to create your dream home on the North Fork. This A-frame-style house, reminiscent of a chalet, features a striking wall of windows that leads to open rafter ceilings. The main floor is perfect for entertaining, with a quaint kitchen, two bedrooms, a full bathroom, and the sunken A-frame living room that captures the essence of the home. Adjacent to the living room,

    Alexis Meadows Compass Greater NY LLC

    600 Highwood Rd, Southold, NY 11971
  • /47

    $45,000 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
  • 55075 Main Rd Unit 1, Southold, NY 11971

    $365,000

    Sold Jun 17, 2025

    55075 Main Rd Unit 1, Southold, NY 11971

    • 2 Beds
    • 1 Bath
    • 805 Sq Ft
    • Built 1968

    Last Sold Summary

    • 9% Below List Price
    • $453/SF
    • 72 Days On Market

    Last Listing Agent Scott Bennett Douglas Elliman Real Estate

    55075 Main Rd Unit 1, Southold, NY 11971
  • /40

    $1,295,000

    • 2 Beds
    • 1 Bath
    • 2,000 Sq Ft

    1220 Youngs Ave, Southold, NY 11971

    Wonderful 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 coming from widows on all sides of the house. In addition, there is a beautiful two-story, 1,100 square foot,

    Lee Beninati Beninati Associates

    1220 Youngs Ave, Southold, NY 11971
  • /20

    $10,000 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
  • 6980 N Bayview Rd, Southold, NY 11971

    $785,000

    Sold Sep 12, 2025

    6980 N Bayview Rd, Southold, NY 11971

    • 3 Beds
    • 2 Baths
    • 1,650 Sq Ft
    • Built 1989

    Last Sold Summary

    • 6% Below List Price
    • $476/SF
    • 96 Days On Market

    Current Estimated Value $832,377

    Last Listing Agent Nicholas Planamento William Raveis New York LLC

    6980 N Bayview Rd, Southold, NY 11971
  • /20

    $975,000

    • 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
  • /14

    $4,500 Per Month

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

    51970 New York 25, Southold, NY 11971

    Pack your bags and relax this summer in this beautifully renovated farmhouse in the heart of the North Fork! Enjoy a delightful retreat in this irresistible and stylishly appointed cottage with charm and comfort throughout! The recently updated eat-in kitchen features brand new stainless steel appliances, and all of the rooms throughout are fresh clean awaiting your arrival. This home is right in

    Suzette Reiss Douglas Elliman Real Estate

    51970 New York 25, Southold, NY 11971
  • 900 Cedar Dr, Southold, NY 11971

    $650,000

    Sold Nov 21, 2025

    900 Cedar Dr, Southold, NY 11971

    • 3 Beds
    • 1 Bath
    • 1,100 Sq Ft
    • Built 1967

    Last Sold Summary

    • 11% Below List Price
    • $591/SF
    • 144 Days On Market

    Current Estimated Value $671,449

    Last Listing Agent Lisa Cerreta BERKSHIRE HATHAWAY

    900 Cedar Dr, Southold, NY 11971
    • 75 Reydon Dr, Southold, NY 11971

      Est $1,241,899

      Not Listed For Sale

      75 Reydon Dr, Southold, NY 11971

      • 3 Beds
      • 3 Baths
      • 2,492 Sq Ft
      • Built 1991
      75 Reydon Dr, Southold, NY 11971

      Last Sold Summary

      • 62 Days On Market

  • /6

    $1,799,000

    • Land
    • 8.65 Acres
    • $207,977 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
  • /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
  • 1635 Laurel Ave, Southold, NY 11971

    $2,600,000

    Sold Feb 02, 2026

    1635 Laurel Ave, Southold, NY 11971

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

    Last Sold Summary

    • $657/SF
    • 7 Days On Market

    Last Listing Agent Kristy Naddell Douglas Elliman Real Estate

    1635 Laurel Ave, Southold, NY 11971
  • /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
  • /41

    $14,950 Per Month

    • 6 Beds
    • 3.5 Baths
    • 3,500 Sq Ft
    • House for Rent

    100 W Shore Dr, Southold, NY 11971

    Set in the highly sought-after Reydon Shores community, 100 W Shore Dr, Southold is a rare dog-friendly North Fork waterfront seasonal rental with your own private, sandy beach and sweeping bay views to Shelter Island. This renovated classic offers three levels of living with a great room and sunroom, 6 bedrooms, 3.5 baths, two wood-burning fireplaces, and a huge Trex deck built for sunset

    Basil Boziotis Compass Greater NY LLC

    100 W Shore Dr, Southold, NY 11971
  • 205 Grange Rd, Southold, NY 11971

    $665,000

    Sold Dec 03, 2025

    205 Grange Rd, Southold, NY 11971

    • 3 Beds
    • 1 Bath
    • 1,300 Sq Ft
    • Built 1971

    Last Sold Summary

    • 11% Above List Price
    • $512/SF
    • 15 Days On Market

    Current Estimated Value $688,371

    Last Listing Agent Rita Rooney Douglas Elliman Real Estate

    205 Grange Rd, Southold, NY 11971
  • /25

    $2,495,000

    $255K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,250 Sq Ft

    1455 Cedar Point Dr E, Southold, NY 11971

    Wake up to endless views of the Peconic Bay — sunlight glimmering off the water, birds gliding over the nearby nature preserve, and the calm rhythm of the deep-water inlet just beyond your deck. This sweet beach cottage captures everything that makes summer on the North Fork unforgettable. With 3 comfortable bedrooms, 2 baths, and an open, easy-flow layout connecting the living, dining, kitchen,

    Maureen Sullivan Daniel Gale Sothebys Intl Rlty

    1455 Cedar Point Dr E, 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
  • 4100 Youngs Ave, Southold, NY 11971

    $890,000

    Sold Apr 17, 2026

    4100 Youngs Ave, Southold, NY 11971

    • 5 Beds
    • 3 Baths
    • 2,300 Sq Ft
    • Built 1970

    Last Sold Summary

    • 9% Below List Price
    • $387/SF
    • 174 Days On Market

    Current Estimated Value $925,673

    Last Listing Agent Jeannine Kowaleski William Raveis New York LLC

    4100 Youngs Ave, Southold, NY 11971
  • /6

    $500,000

    Pending
    • Land
    • 26,136 Sq Ft
    • $833,333 per Acre

    265 Arshamomaque Ave, Southold, NY 11971

    Building Lot in Beixedon Estates private community. Private road, deeded access to private community beach. Broker/Owner.

    John J. Nickles, Jr. Lewis & Nickles LTD

    265 Arshamomaque Ave, 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

    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
  • 1475 Oaklawn Ave, Southold, NY 11971

    $1,175,000

    Sold Feb 04, 2026

    1475 Oaklawn Ave, Southold, NY 11971

    • 4 Beds
    • 2.5 Baths
    • 2,400 Sq Ft
    • Built 1966

    Last Sold Summary

    • $490/SF
    • 33 Days On Market

    Current Estimated Value $1,154,396

    Last Listing Agent William Walters Daniel Gale Sothebys Intl Rlty

    1475 Oaklawn Ave, Southold, NY 11971
    • 165 Deer Run, Southold, NY 11971

      Est $3,056,667

      Not Listed For Sale

      165 Deer Run, Southold, NY 11971

      • 5 Beds
      • 6 Baths
      • 5,000 Sq Ft
      • Built 2006
      165 Deer Run, Southold, NY 11971

      Last Sold Summary

      • 20 Days On Market

Showing Results 161 - 200, Page 5 of 18

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