4,634

Southold, NY Homes

Section Image
  • /22

    $939,000

    $150K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft

    6625 Hortons Ln, Southold, NY 11971

    A beautiful and lovingly-maintained ranch with a front porch, set on a corner lot, offers a serene, country setting. Home features a primary bedroom ensuite, plus 2 comfortably-sized bedrooms, 2 full bathrooms and a bright, newly-renovated eat-in kitchen with French doors leading to a picturesque, level backyard with a patio. A spacious living room and family room with a brick, wood burning

    Detra Sarris Signature Premier Properties

    6625 Hortons Ln, Southold, NY 11971
  • /21

    $22,500 Per Month

    • 4 Beds
    • 3 Baths
    • 1,800 Sq Ft
    • House for Rent

    270 N Sea Dr, Southold, NY 11971

    Southold, North Fork: Endless sunsets await at this exceptional vacation rental, available year-round with flexible terms and rates. Ideally located in the sought-after Kenny’s Beach community, this sun-drenched home is surrounded by wide sandy dunes perfect for walking, birdwatching, swimming, and relaxing days by the shore.Immaculately maintained, the residence offers 4 bedrooms and 3 full

    Nicholas Planamento William Raveis New York LLC

    270 N Sea Dr, Southold, NY 11971
  • 2555 Youngs Ave Unit 14A, Southold, NY 11971

    $685,000

    Sold Nov 18, 2025

    2555 Youngs Ave Unit 14A, Southold, NY 11971

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Built 1988

    Last Sold Summary

    • 1% Above List Price
    • $571/SF
    • 12 Days On Market

    Last Listing Agent Diane Mollica Compass Greater NY LLC

    2555 Youngs Ave Unit 14A, Southold, NY 11971
  • /30

    $1,099,000

    $76K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 3,000 Sq Ft

    5045 Main Bayview Rd, Southold, NY 11971

    Welcome to this charming residence nestled in the heart of Southold. This gem boasts 4 spacious bedrooms, 2 full bathrooms, along with an additional half bath for your convenience. Step inside to be greeted by a formal dining room, perfect for hosting memorable gatherings. The primary bathroom offers a private sanctuary, while the walk-through kitchen is equipped with stainless steel appliances

    Peter Halpin Douglas Elliman Real Estate

    5045 Main Bayview Rd, Southold, NY 11971
  • /20

    $13,000 Per Month

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

    215 Northfield Ln, Southold, NY 11971

    Permit 0681- Enjoy This Beautifully Renovated 4 Bedroom, 3 Bath Ranch Style Home With Heated Pool. Open Floor Plan Includes LR With Cathedral Ceilings, High End EIK, Dining Area & Outdoor Shower. Plenty of Room For The Whole Family & Guests. Beautiful Goose Creek Beach Just 0.2 Miles Down The Road. Minutes To Local Wineries, Shopping & Dining. BOOK NOW FOR SUMMER 2026. Terms & Availability: May

    Mitch Pickman Thomas J McCarthy Real Estate

    215 Northfield Ln, Southold, NY 11971
  • 555 Oakwood Dr, Southold, NY 11971

    $899,000

    Sold Jul 25, 2025

    555 Oakwood Dr, Southold, NY 11971

    • 4 Beds
    • 2.5 Baths
    • 2,300 Sq Ft
    • Built 1967

    Last Sold Summary

    • 10% Below List Price
    • $391/SF
    • 42 Days On Market

    Current Estimated Value $953,789

    Last Listing Agent Tom Uhlinger Douglas Elliman Real Estate

    555 Oakwood Dr, Southold, NY 11971
  • /21

    $1,150,000

    • 2 Beds
    • 1 Bath
    • 1,500 Sq Ft

    380 Clark Rd, Southold, NY 11971

    Welcome to 380 Clark Road, a sun-filled North Fork escape perfectly located near the beautiful beaches of Southold. Blending comfort, charm, and endless backyard potential, this turn key home captures the easygoing lifestyle that makes the North Fork so desirable. Natural light pours throughout the home, creating bright, cheerful interiors and a warm, welcoming feel from the moment you arrive.

    Susan Orioli Engel & Volkers North Fork

    380 Clark Rd, Southold, NY 11971
  • /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
  • 295 Grange Rd, Southold, NY 11971

    $1,900,000

    Sold Apr 14, 2026

    295 Grange Rd, Southold, NY 11971

    • 4 Beds
    • 3.5 Baths
    • 4,173 Sq Ft
    • Built 2025

    Last Sold Summary

    • 3% Below List Price
    • $455/SF
    • 124 Days On Market

    Current Estimated Value $1,802,000

    Last Listing Agent Sheri Winter Parker Corcoran

    295 Grange Rd, Southold, NY 11971
    • 425 Jacobs Ln, Southold, NY 11971

      Est $1,777,333

      Not Listed For Sale

      425 Jacobs Ln, Southold, NY 11971

      • 5 Beds
      • 3.5 Baths
      • 3,286 Sq Ft
      • Built 2001
      425 Jacobs Ln, Southold, NY 11971

      Last Sold Summary

      • 86 Days On Market

  • /39

    $1,200,000

    • 3 Beds
    • 1.5 Baths
    • 2,000 Sq Ft

    3475 Oaklawn Ave, Southold, NY 11971

    Circa-1909 Cozy Farmhouse Near the Water & Southold Village Welcome to 3475 Oaklawn Road, Southold, a circa-1909 farmhouse rich in warmth, character, and North Fork authenticity. This charming home, situated on a 1/2 acre, captures the essence of early-20th-century farmhouse living, offering a cozy, inviting atmosphere paired with thoughtful functionality and future potential. The residence

    Trish Bergin Signature Premier Properties

    3475 Oaklawn Ave, Southold, NY 11971
  • /24

    $8,000 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
  • 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 $702,503

    Last Listing Agent Maryse Bransfield William Raveis New York LLC

    1040 Nakomis Rd, Southold, NY 11971
  • /24

    $1,299,000

    Open Sat 11AM - 1PM
    • 4 Beds
    • 3 Baths
    • 2,200 Sq Ft

    250 Paradise Point Rd, Southold, NY 11971

    Welcome to 250 Paradise Point Rd, Southold NY, a beautiful ranch-style home complete with an in-ground pool is nestled in a serene location, just a stone's throw away from Cedar Beach. This spacious home boasts four bedrooms, two of which are en suites with full bathrooms, ensuring ample space and privacy for everyone. The heart of the home is the cozy family room, complete with a fireplace and

    Barbara Poliwoda Douglas Elliman Real Estate

    250 Paradise Point Rd, Southold, NY 11971
  • /32

    $44,000 Per Month

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

    70 Arshamomaque Ave, Southold, NY 11971

    Southold, North Fork AUGUST 1-14, 2026 Rental: Heaven Off Main. Chic new retreat with ultra vacation vibe. 4 en suite bedrooms, each with a different theme and a full bath, complement the 'public' rooms designed for entertaining. Home opens up to poolside terrace and gorgeous sun! Located in the private bayfront beach community of Beixedon. Book your stay today. Pets on an individual basis.

    Nicholas Planamento William Raveis New York LLC

    70 Arshamomaque Ave, 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 $2,298,509

    Last Listing Agent Kristy Naddell Douglas Elliman Real Estate

    2215 Laurel Ave, Southold, NY 11971
  • /7

    $150,000

    • 1 Bath
    • 230 Sq Ft

    52325 County Road 48 Unit 8, Southold, NY 11971

    Waterfront Studio Condo in Southold property features living room / kitchen combo with 1 Queen Size bed and 2 pull out trundle beds which can become 1 full size bed. outdoor area includes boat storage for small fee BBQ area on grounds free laundry room. Rentals are permitted can be rented seasonally if desired.Low property taxes and low common charges which include all utilities.Seasonal

    Peter Vekiarellis ERealty Advisors Inc

    52325 County Road 48 Unit 8, Southold, NY 11971
  • /16

    $2,600 Per Month

    • 1 Bed
    • 1 Bath
    • 530 Sq Ft
    • Apartment for Rent

    55075 Main Rd Unit Youngs Bldg 3, Southold, NY 11971

    Newly renovated and pristine year-round rental in the heart of Southold's beautiful Colonial Village, an exclusive 55 an over adult community. This inviting ground level 1 bedroom, 1 bath apartment offers comfort and convenience boasting a modern eat-in kitchen with granite countertops, all new stainless steel appliances and cabinetry; spacious living room & bedroom; ample storage; hardwood

    Thomas McCarthy Thomas J McCarthy Real Estate

    55075 Main Rd Unit Youngs Bldg 3, Southold, NY 11971
  • 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
    • 295 Grove Dr, Southold, NY 11971

      Est $1,315,704

      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

  • /15

    $649,000

    $100K PRICE DROP Pending
    • 2 Beds
    • 1 Bath
    • 1,114 Sq Ft

    265 Hummel Ave, Southold, NY 11971

    Welcome to 265 Hummel Ave in Southold, a charming two-bedroom, one-bathroom gem that embodies the perfect balance of comfort and potential. This property is a blank canvas for your imagination, boasting a full attic that presents an exciting opportunity for expansion, allowing you to customize the loft space to your unique needs and taste. The home is situated in a vibrant community that thrives

    Amanda Lin Douglas Elliman Real Estate

    265 Hummel Ave, 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
  • 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 $559,812

    Last Listing Agent William Walters Daniel Gale Sothebys Intl Rlty

    48920 Route 25, Southold, NY 11971
  • /14

    $250,000

    Pending
    • 1 Bath

    52325 County Road 48 Unit 5, Southold, NY 11971

    Cozy, Renovated Condo Near Town Beach - Southold, NY- 7 Minute Drive to Greenport Town Don't miss this beautifully renovated first-floor condo just steps from Town Beach in Southold! (You also get your own private beach across the street behind the condo) Enjoy the perfect North Fork lifestyle with stunning water views right across the street, or take a quick 2-minute walk to the beach for

    Christos Lolis EAST COAST NEW YORK

    52325 County Road 48 Unit 5, Southold, NY 11971
  • /31

    $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
  • 17240 Soundview Ave, Southold, NY 11971

    $1,780,000

    Sold Jul 11, 2025

    17240 Soundview Ave, Southold, NY 11971

    • Land
    • 25 Acres
    • $71,200 per Acre

    Last Sold Summary

    • 1% Below List Price
    • 40 Days On Market

    Current Estimated Value $1,807,243

    Last Listing Agent Kristy Naddell Douglas Elliman Real Estate

    17240 Soundview Ave, Southold, NY 11971
  • /36

    $4,900,000

    $1M PRICE DROP
    • Land
    • 51 Acres
    • $96,078 per Acre

    44075 Route 25, Peconic, NY 11958

    Step into the heart of North Fork wine country with the rare opportunity to own Osprey’s Dominion, an award-winning, fully operational winery and vineyard with a celebrated brand and loyal following. Perfectly positioned along the highly visible Main Road (Route 25) in Peconic, this landmark estate combines prime location, modern facilities, and limitless growth potential. Spanning over 50 acres,

    Susan Orioli Engel & Volkers North Fork

    44075 Route 25, Peconic, NY 11958
  • /17

    $3,200 Per Month

    • 2 Beds
    • 1 Bath
    • 606 Sq Ft
    • House for Rent

    1385 Old Shipyard Ln, Southold, NY 11971

    Charming year-round rental in coveted Founders Landing! Just moments from a sugar sand Bay beach and a marina with deep water access. Nestled on a spacious 1/4 acre parcel perfect for outdoor activities. Featuring two cozy bedrooms and a well-appointed bath, this home offers plenty of room for entertaining while being easy to maintain. Conveniently close to shops, beaches, and dining. Don't miss

    Andrea Parks Douglas Elliman Real Estate

    1385 Old Shipyard Ln, Southold, NY 11971
  • 50605 Route 25, Southold, NY 11971

    $810,000

    Sold Sep 10, 2025

    50605 Route 25, Southold, NY 11971

    • 2 Beds
    • 1.5 Baths
    • Built 1701

    Last Sold Summary

    • 9% Below List Price
    • 67 Days On Market

    Current Estimated Value $812,350

    Last Listing Agent Mariah Mills Daniel Gale Sothebys Intl Rlty

    50605 Route 25, Southold, NY 11971
  • /12

    $550,000

    Pending
    • Land
    • 23,958 Sq Ft
    • $1,000,000 per Acre

    105 Mailer Ct, Southold, NY 11971

    Wonderful opportunity in prime location to build your dream home on this bright and private corner lot of 0.55 acre in the desirable community of Southold. This land has partial water view and access to ramp at the end of the road to Goose Creek for boating, kayaking, and fishing. And yes, it is only a few minutes from town, restaurants, farmstands, wineries, antique shops, and more.

    Maryse Bransfield William Raveis New York LLC

    105 Mailer Ct, Southold, NY 11971
  • /47

    $20,000 Per Month

    • 5 Beds
    • 3.5 Baths
    • 3,700 Sq Ft
    • House for Rent

    425 Cedar Point Dr E, Southold, NY 11971

    Now Available for June, July or August 2027. Rented July and August 2026. This Impressive Home is Set Creekfront with Private Dock with Peconic Bay Access and Associated Bay Beach within the Community. The Extensive Rear Patio Area is Impressive with an Inground Pool and Jacuzzi. All Creekfront with a Beautiful View. The Home is Grand and Designed to Entertain. Boasting 5 Bedrooms and 4 Baths. 2

    Rene Giacobbe Douglas Elliman Real Estate

    425 Cedar Point Dr E, 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 $1,278,104

    Last Listing Agent William Walters Daniel Gale Sothebys Intl Rlty

    58425 Route 48, Greenport, NY 11944

Showing Results 121 - 160, Page 4 of 18

How to Buy a Home How to Finance a Home How to Sell a Home