4,599

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
  • /28

    $7,500 Per Month

    • 4 Beds
    • 2 Baths
    • 2,000 Sq Ft
    • House for Rent

    3400 Youngs Ave, Southold, NY 11971

    Nobody comes to the North Fork because they're looking for excitement, they come because they're looking for something they've been missing. Time slows here. Not dramatically, but quietly. You notice it on the first morning when you realize you've finished your coffee without checking your phone. The windows are open, the breeze carries the scent of nearby fields, and the only thing on the agenda

    Thomas McCarthy Thomas J McCarthy Real Estate

    3400 Youngs Ave, Southold, NY 11971
  • 2555 Youngs Ave Unit 7D, Southold, NY 11971

    $500,000

    Sold Oct 21, 2025

    2555 Youngs Ave Unit 7D, Southold, NY 11971

    • 2 Beds
    • 2 Baths
    • 1,100 Sq Ft
    • Built 1987

    Last Sold Summary

    • 13% Below List Price
    • $455/SF
    • 250 Days On Market

    Last Listing Agent Timothy O'Keefe Signature Premier Properties

    2555 Youngs Ave Unit 7D, Southold, NY 11971
    • 1100 Rambler Rd, Southold, NY 11971

      Est $901,858

      Not Listed For Sale

      1100 Rambler Rd, Southold, NY 11971

      • 4 Beds
      • 2 Baths
      • Built 1961
      1100 Rambler Rd, Southold, NY 11971

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Susan Orioli Engel & Volkers North Fork

  • /20

    $1,375,000

    • 3 Beds
    • 2 Baths
    • 1,841 Sq Ft

    1050 Bayview Ave, Southold, NY 11971

    Perfectly positioned between Greenport and Southold, this classic cedar-shingled Cape offers an easygoing North Fork lifestyle with beaches, restaurants, and village amenities just minutes away. Inside, the first-floor open plan is anchored by a fireplace and a large kitchen flooded with natural light. Multiple sliding doors lead to a generous wraparound deck, outfitted for dining, lounging, and

    Eric Elkin Compass Greater NY LLC

    1050 Bayview Ave, Southold, NY 11971
  • /42

    $4,900 Per Month

    • 4 Beds
    • 2 Baths
    • 2,000 Sq Ft
    • House for Rent

    6710 Soundview Ave, Southold, NY 11971

    Enjoy Southold this Summer at a Sleek Scandinavian Style Farm Ranch. Available for Bi-Weekly Rental Only. The Rate is Weekly at a Bi-Weekly Minimum. Nestled on Shy 2.5 Acres of Private Wooded Property You Can Truly Get Away from It All. Constructed in 2022 for Elegance and Comfort. Complete One Level Living at Its Finest. The Home Boasts a Grand Open Layout with Vaulted Ceilings Throughout.

    Rene Giacobbe Douglas Elliman Real Estate

    6710 Soundview Ave, Southold, NY 11971
  • 6815 Soundview Ave, Southold, NY 11971

    $975,000

    Sold Aug 28, 2025

    6815 Soundview Ave, Southold, NY 11971

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Built 1938

    Last Sold Summary

    • 3% Above List Price
    • $812/SF
    • 9 Days On Market

    Current Estimated Value $1,022,307

    Last Listing Agent Donielle Cardinale Daniel Gale Sothebys Intl Rlty

    6815 Soundview Ave, Southold, NY 11971
    • 65 Pleasant Place, Southold, NY 11971

      Est $1,160,567

      Not Listed For Sale

      65 Pleasant Place, Southold, NY 11971

      • 4 Beds
      • 2 Baths
      • Built 1987
      65 Pleasant Place, Southold, NY 11971

      Last Sold Summary

      • 69 Days On Market

      Last Listing Agent Katie Schimpf Daniel Gale Sothebys Intl Rlty

  • /26

    $1,239,999

    $160K PRICE DROP Pending
    • 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
  • /24

    $15,000 Per Month

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

    935 Corey Creek Ln, Southold, NY 11971

    Experience the ultimate North Fork summer in this stunning new construction home, designed for effortless entertaining and elevated coastal living. Professionally decorated and impeccably finished, this residence offers three bedrooms, four full bathrooms, a bonus room, and a beautifully finished lower level with an additional private half bath. Step outside to your own private retreat featuring

    Melissa Principi Douglas Elliman Real Estate

    935 Corey Creek Ln, Southold, NY 11971
  • 20845 Soundview Ave, Southold, NY 11971

    $1,730,000

    Sold Nov 12, 2025

    20845 Soundview Ave, Southold, NY 11971

    • 3 Beds
    • 2 Baths
    • 1,408 Sq Ft
    • Built 1951

    Last Sold Summary

    • 4% Below List Price
    • $1,229/SF
    • 39 Days On Market

    Current Estimated Value $1,778,067

    Last Listing Agent Stephanie Ranghelli Realty Connect USA L I Inc

    20845 Soundview Ave, Southold, NY 11971
    • 1085 Gin Ln, Southold, NY 11971

      Est $1,330,008

      Not Listed For Sale

      1085 Gin Ln, Southold, NY 11971

      • 4 Beds
      • 4 Baths
      • 3,400 Sq Ft
      • Built 1975
      1085 Gin Ln, Southold, NY 11971

      Last Sold Summary

      • 72 Days On Market

      Last Listing Agent Nancy Cervelli Daniel Gale Sothebys Intl Rlty

  • /35

    $785,000

    Pending
    • 2 Beds
    • 1.5 Baths
    • 2,350 Sq Ft

    44600 County Road 48, Southold, NY 11971

    A great business and/or investment opportunity awaits! Once a popular Southold holistic/chiropractic office with separate living quarters and then a childcare facility and apartment, this adaptable split-level property is awaiting its next creativite live-in business venture! Located on a beautiful .83 acre, this property fronts the high visibility County Road 48/North Road and backs up to scenic

    Gayle Marriner Smith Daniel Gale Sothebys Intl Rlty

    44600 County Road 48, 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
  • 105 Mailer Ct, Southold, NY 11971

    $600,000

    Sold Jul 21, 2026

    105 Mailer Ct, Southold, NY 11971

    • Land
    • 23,958 Sq Ft
    • $1,090,909 per Acre

    Last Sold Summary

    • 9% Above List Price
    • 7 Days On Market

    Current Estimated Value $550,653

    Last Listing Agent Maryse Bransfield William Raveis New York LLC

    105 Mailer Ct, Southold, NY 11971
    • 945 Gin Ln, Southold, NY 11971

      Est $1,140,980

      Not Listed For Sale

      945 Gin Ln, Southold, NY 11971

      • 4 Beds
      • 3 Baths
      • Built 1972
      945 Gin Ln, Southold, NY 11971

      Last Sold Summary

      • 51 Days On Market

      Last Listing Agent Tom Scalia Century 21 Albertson Realty

  • /45

    $3,675,000

    New Construction
    • 5 Beds
    • 6 Baths
    • 5,285 Sq Ft

    150 Deer Run, Southold, NY 11971

    Gorgeous estate-like Nantucket shingle home to be completed early August with time to enjoy summer of 2026 and the Fall Harvest Season on the North Fork! Seller will consider owner financing. Designed by the renowned firm of Nelson and Pope utilizing steel beam construction throughout and Benjamin Obdyke Hydrogap house wrap, the home features solid white oak hardwood floors, as well as many

    Jeffrey Mead Corcoran

    150 Deer Run, 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- A 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 $13,000,

    Mitch Pickman Thomas J McCarthy Real Estate

    215 Northfield Ln, Southold, NY 11971
  • 350 Brigantine Dr, Southold, NY 11971

    $750,750

    Sold Mar 27, 2026

    350 Brigantine Dr, Southold, NY 11971

    • 3 Beds
    • 2 Baths
    • 975 Sq Ft
    • Built 1986

    Last Sold Summary

    • 20% Above List Price
    • $770/SF
    • 31 Days On Market

    Current Estimated Value $752,140

    Last Listing Agent Nicole Petersen Century 21 Icon

    350 Brigantine Dr, Southold, NY 11971
    • 685 Bay Haven Ln, Southold, NY 11971

      Est $899,999

      Not Listed For Sale

      685 Bay Haven Ln, Southold, NY 11971

      • 3 Beds
      • 2 Baths
      • Built 1959
      685 Bay Haven Ln, Southold, NY 11971

      Last Sold Summary

      • 27 Days On Market

      Last Listing Agent Eleanor Dunne Andron Realty Group Tulip R E

  • /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
  • /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
  • 6900 Main Bayview Rd, Southold, NY 11971

    $600,000

    Sold Jul 31, 2026

    6900 Main Bayview Rd, Southold, NY 11971

    • 2 Beds
    • 1 Bath
    • 1,200 Sq Ft
    • Built 1955

    Last Sold Summary

    • $500/SF
    • 40 Days On Market

    Current Estimated Value $631,275

    Last Listing Agent Todd Yovino Island Advantage Realty LLC

    6900 Main Bayview Rd, Southold, NY 11971
    • /2

      Est $816,134

      Not Listed For Sale

      1430 Bay Haven Ln, Southold, NY 11971

      • 3 Beds
      • 2 Baths
      • Built 1973
      1430 Bay Haven Ln, Southold, NY 11971

  • /27

    $2,650,000

    • 4 Beds
    • 3.5 Baths
    • 2,600 Sq Ft

    195 Williamsburgh Dr, Southold, NY 11971

    This breezy, open-concept home was made for hosting, with seamless flow and water views at every turn. Set on 101 feet of Corey Creek frontage, you get a brand-new bulkhead, your own boat ramp, and instant access to the bay. With 4 bedrooms and 3.5 baths, including both a first-floor primary ensuite and a second-floor primary suite, there's room for everyone to spread out in style. Two mahogany

    Sheri Winter Parker Corcoran

    195 Williamsburgh Dr, 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
  • 54985 Middle Rd, Southold, NY 11971

    $2,700,000

    Sold Sep 25, 2025

    54985 Middle Rd, Southold, NY 11971

    • 4 Beds
    • 5 Baths
    • 3,500 Sq Ft
    • Built 2010

    Last Sold Summary

    • 16% Below List Price
    • $771/SF
    • 133 Days On Market

    Last Listing Agent Nicholas Planamento William Raveis New York LLC

    54985 Middle Rd, Southold, NY 11971
    • 380 Gin Ln, Southold, NY 11971

      Est $1,050,911

      Not Listed For Sale

      380 Gin Ln, Southold, NY 11971

      • 6 Beds
      • 3 Baths
      • 3,784 Sq Ft
      • Built 1960
      380 Gin Ln, Southold, NY 11971

      Last Sold Summary

      • 88 Days On Market

      Last Listing Agent Ryan Springer Corcoran

  • /13

    $799,000

    • 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
  • /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
  • 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
    • 155 Seawood Dr, Southold, NY 11971

      Est $708,089

      Not Listed For Sale

      155 Seawood Dr, Southold, NY 11971

      • 2 Beds
      • 1 Bath
      • Built 1958
      155 Seawood Dr, Southold, NY 11971

      Last Sold Summary

      • 33 Days On Market

      Last Listing Agent Scott Bennett Douglas Elliman Real Estate

  • /38

    $1,625,000

    New Construction $74K 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
  • /16

    $2,500 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 fantastic home has heat and water included in rent for tremendous savings to the tenant ! This inviting ground level one bedroom, one bath apartment offers comfort and convenience boasting a modern eat-in kitchen with granite countertops, all new

    Thomas McCarthy Thomas J McCarthy Real Estate

    55075 Main Rd Unit Youngs Bldg 3, 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 $1,930,333

    Last Listing Agent Sheri Winter Parker Corcoran

    295 Grange Rd, Southold, NY 11971
    • 9502 N Bayview Rd, Southold, NY 11971

      Est $3,176,000

      Not Listed For Sale

      9502 N Bayview Rd, Southold, NY 11971

      • 5 Beds
      • 4.5 Baths
      • 4,051 Sq Ft
      • Built 2019
      9502 N Bayview Rd, Southold, NY 11971

      Last Sold Summary

      • 187 Days On Market

      Last Listing Agent Thomas McCarthy Thomas J McCarthy Real Estate

  • /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
  • /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
  • 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
    • 580 Jacobs Ln, Southold, NY 11971

      Est $749,377

      Not Listed For Sale

      580 Jacobs Ln, Southold, NY 11971

      • 2 Beds
      • 1 Bath
      580 Jacobs Ln, Southold, NY 11971

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Sheri Winter Parker Corcoran

Showing Results 121 - 160, Page 4 of 18

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