4,571

Southold, NY Homes

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  • /33

    $2,695,000

    • 5 Beds
    • 3.5 Baths
    • 3,500 Sq Ft

    605 Cedar Dr, Southold, NY 11971

    This charming cedar shingle Cape has been expanded and completely renovated, resulting in a home that exudes a timeless sense of place across three full floors of living space. With five bedrooms and four bathrooms, the home expands comfortably for guests yet feels equally intimate for smaller gatherings, striking a perfect balance for those looking to host but also enjoy a refined and

    Bridget Elkin Compass Greater NY LLC

    605 Cedar Dr, Southold, NY 11971
  • /20

    $3,000 Per Month

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft
    • Apartment for Rent

    475 Youngs Ave Unit c, Southold, NY 11971

    Southold, North Fork: Discover the epitome of easy living at Unit C "Baldwin T. Payne" in Southold, North Fork. This condo-like residence, part of the North Fork Resident's Inn, offers a one-of-a-kind opportunity to embrace a modern lifestyle in a historic setting. The unit boasts a spacious layout with direct garden access, abundant natural light, and contemporary furnishings. With upscale

    Nicholas Planamento William Raveis New York LLC

    475 Youngs Ave Unit c, Southold, NY 11971
  • 265 Arshamomaque Ave, Southold, NY 11971

    $1,700,000

    Sold May 29, 2026

    265 Arshamomaque Ave, Southold, NY 11971

    • 4 Beds
    • 3.5 Baths
    • 3,245 Sq Ft
    • Built 2025

    Last Sold Summary

    • 19% Below List Price
    • $524/SF
    • 235 Days On Market

    Current Estimated Value $1,761,667

    Last Listing Agent Cathleen Dolson Corcoran

    265 Arshamomaque Ave, Southold, NY 11971
    • 475 Jernick Ln, Southold, NY 11971

      Est $866,108

      Not Listed For Sale

      475 Jernick Ln, Southold, NY 11971

      • 2 Beds
      • 2 Baths
      • Built 1978
      475 Jernick Ln, Southold, NY 11971

      Last Sold Summary

      • 265 Days On Market

      Last Listing Agent Marilyn Sandroni Baldwin Realty

  • /50

    $1,249,000

    $350K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 2,000 Sq Ft

    2055 Boisseau Ave, Southold, NY 11971

    Southold, North Fork: The historic Boisseau farmhouse, built around 1890, is situated on 1.75 acres (76,230 square feet) with R40 residential zoning, in a picturesque setting featuring mature trees and a sprawling lawn. The property is adjacent to fallow, and partially wooded acreage owned by the Town of Southold. The traditional home boasts a charming covered front porch, an entry foyer, and a

    Nicholas Planamento William Raveis New York LLC

    2055 Boisseau Ave, Southold, NY 11971
  • /19

    $4,000 Per Month

    • 3 Beds
    • 2 Baths
    • House for Rent

    1975 Youngs Ave, Southold, NY 11971

    This beautifully furnished farmhouse offers you a warm welcome home on the North Fork. Amazing decor throughout every room for you to enjoy your stay. There are three bedrooms and two full bathrooms, hardwood floors, central air conditioning, and a back deck overlooking a fenced in yard. Great location just one block from the town restaurants, shops, and all transportation. Numerous beaches to

    Barbara Poliwoda Douglas Elliman Real Estate

    1975 Youngs Ave, Southold, NY 11971
  • 1400 Calves Neck Rd, Southold, NY 11971

    $1,125,000

    Sold May 15, 2026

    1400 Calves Neck Rd, Southold, NY 11971

    • 4 Beds
    • 3 Baths
    • 2,900 Sq Ft
    • Built 1966

    Last Sold Summary

    • 25% Above List Price
    • $388/SF
    • 10 Days On Market

    Current Estimated Value $1,254,201

    Last Listing Agent Mariah Mills Daniel Gale Sothebys Intl Rlty

    1400 Calves Neck Rd, Southold, NY 11971
    • 1345 Long Creek Dr, Southold, NY 11971

      Est $1,310,297

      Not Listed For Sale

      1345 Long Creek Dr, Southold, NY 11971

      • 4 Beds
      • 2 Baths
      • Built 1969
      1345 Long Creek Dr, Southold, NY 11971

      Last Sold Summary

      • 25 Days On Market

      Last Listing Agent Scott Bennett Douglas Elliman Real Estate

  • /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
  • /31

    $16,000 Per Month

    • 4 Beds
    • 3.5 Baths
    • House for Rent

    75 Clearview Ave, Southold, NY 11971

    2026 Rates: NO AVAILABILITY New Modern Farmhouse Completed in 2021 and located in the heart Hog's Neck in Southold Hamlet. This home features an impressive 20 x 50 heated pool with electric cover, out door shower and sprawling paver patio. The interior is open and airy with Chef's Kitchen outfitted with Thermador appliances, large living room with built in shelving, gas fireplace and formal

    William Walters Daniel Gale Sothebys Intl Rlty

    75 Clearview Ave, Southold, NY 11971
  • 340 Pine Rd, Southold, NY 11971

    $720,000

    Sold Apr 27, 2026

    340 Pine Rd, Southold, NY 11971

    • 2 Beds
    • 1 Bath
    • 840 Sq Ft
    • Built 1955

    Last Sold Summary

    • 1% Below List Price
    • $857/SF
    • 40 Days On Market

    Current Estimated Value $731,106

    Last Listing Agent Nancy Cervelli Daniel Gale Sothebys Intl Rlty

    340 Pine Rd, Southold, NY 11971
    • 2085 Bayview Ave, Southold, NY 11971

      Est $1,433,556

      Not Listed For Sale

      2085 Bayview Ave, Southold, NY 11971

      • 4 Beds
      • 1.5 Baths
      • 1,934 Sq Ft
      • Built 1955
      2085 Bayview Ave, Southold, NY 11971

      Last Sold Summary

      • 45 Days On Market

      Last Listing Agent Janet Markarian Daniel Gale Sothebys Intl Rlty

  • /15

    $1,425,000

    $2M PRICE DROP
    • 3 Beds
    • 4 Baths
    • 2,900 Sq Ft

    535 Bay Home Rd, Southold, NY 11971

    Waterfront Opportunity on Bay Home Road. Welcome to 535 Bay Home Road, a rare and flexible offering on one of the North Fork’s most coveted canal-front streets, located in the prestigious Willow Point community. With panoramic water views, a private dock, and access to a secluded beach, this property combines timeless coastal charm with modern luxury. Buyers can choose from two exclusive paths to

    Kim Pirreca BERKSHIRE HATHAWAY

    535 Bay Home Rd, Southold, NY 11971
  • /29

    $7,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • House for Rent

    250 Wesland Rd, Southold, NY 11971

    JUST A DREAM BOAT! NEWLY RENOVATED, LIGHT AND BRIGHT, BEAUTIFULLY APPOINTED, EVERY CONVENIENCE - 2 BEDROOMS, 2 BATHS. PLUS -SUPER COMFORTABLE CONVERTIBLE QUEEN SOFABED! BEAUTIFUL OUTDOOR DINING, FIRE PIT, PORCH, ENCLOSED SHOWER! PRICED RIGHT! STEPS TO POPULAR KENNEY'S BEACH - JUST BRING OUR LITTLE RED WAGON AND STROLL TO THE BEACH AND ENJOY! Additional information: Appearance excellent! Lease

    Marie Beninati Beninati Associates

    250 Wesland Rd, Southold, NY 11971
  • 340 Rambler Rd, Southold, NY 11971

    $961,000

    Sold Aug 06, 2026

    340 Rambler Rd, Southold, NY 11971

    • 3 Beds
    • 2 Baths
    • 1,700 Sq Ft
    • Built 1976

    Last Sold Summary

    • $565/SF
    • 22 Days On Market

    Current Estimated Value $971,826

    Last Listing Agent Diane Mollica Compass Greater NY LLC

    340 Rambler Rd, Southold, NY 11971
    • 1275 Ruch Ln, Southold, NY 11971

      Est $2,106,667

      Not Listed For Sale

      1275 Ruch Ln, Southold, NY 11971

      • 5 Beds
      • 6 Baths
      • 4,780 Sq Ft
      • Built 1972
      1275 Ruch Ln, Southold, NY 11971

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Bridget Elkin Compass Greater NY LLC

  • /29

    $2,995,000

    $300K PRICE DROP
    • 4 Beds
    • 5.5 Baths
    • 7,341 Sq Ft

    80 Deer Run, Southold, NY 11971

    Southold Stunner- New ConstructionThis one's a North Fork knockout. Set at the end of a quiet cul de sac on over 2 private acres, minutes from the sand, the house was built to check every box. Inside you're met with all-day sunshine, four legit bedrooms, 4.5 spa-like baths (sanitary system in place for 7 bedrooms), and a true chef's kitchen-with a 48" Sub Zero, Wolf double range + wall oven,

    Sheri Winter Parker Corcoran

    80 Deer Run, 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 - Available 2027: May $12,500; July $22,500; Aug-LD $28,000; 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

    Sheri Winter Parker Corcoran

    16125 Soundview Ave, Southold, NY 11971
  • /36

    $2,700,000

    Sold Sep 25, 2025

    54985 County Road 48, Southold, NY 11971

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

    Last Sold Summary

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

    Current Estimated Value $2,488,689

    Last Listing Agent Nicholas Planamento William Raveis (Mattituck)

    54985 County Road 48, Southold, NY 11971
    • 265 Cedar Point Dr E, Southold, NY 11971

      Est $1,487,075

      Not Listed For Sale

      265 Cedar Point Dr E, Southold, NY 11971

      • 3 Beds
      • 2.5 Baths
      • 2,000 Sq Ft
      • Built 2000
      265 Cedar Point Dr E, Southold, NY 11971

      Last Sold Summary

      • 113 Days On Market

      Last Listing Agent Rene Giacobbe Douglas Elliman Real Estate

  • /35

    $999,000

    $201K PRICE DROP Pending
    • 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
  • /20

    $6,000 Per Month

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

    345 Old Cove Blvd, Southold, NY 11971

    Seasonal Rental. Set directly across from Town Beach in Southold, this beautifully maintained seasonal rental captures the best of North Fork coastal living with unobstructed water views, direct beach access, and a relaxed indoor-outdoor lifestyle. Located within a private home built approximately six years ago, the apartment offers its own private side entrance from the patio area, complete with

    Basil Boziotis Compass Greater NY LLC

    345 Old Cove Blvd, Southold, NY 11971
  • 700 Gin Ln, Southold, NY 11971

    $1,785,000

    Sold Jul 07, 2026

    700 Gin Ln, Southold, NY 11971

    • 4 Beds
    • 3.5 Baths
    • 2,627 Sq Ft
    • Built 2018

    Last Sold Summary

    • 1% Below List Price
    • $679/SF
    • 30 Days On Market

    Current Estimated Value $1,778,021

    Last Listing Agent Dawn Watson Serhant East End LLC

    700 Gin Ln, Southold, NY 11971
    • 55 Cedar Point Dr W, Southold, NY 11971

      Est $1,094,058

      Not Listed For Sale

      55 Cedar Point Dr W, Southold, NY 11971

      • 3 Beds
      • 2 Baths
      • 1,650 Sq Ft
      • Built 1973
      55 Cedar Point Dr W, Southold, NY 11971

      Last Sold Summary

      • 62 Days On Market

      Last Listing Agent Kristy Naddell Douglas Elliman Real Estate

  • /36

    $1,100,000

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

    61341 Route 25, Southold, NY 11971

    Private Southold Retreat on 2.18 Acres- Tucked away at the end of a private lane in desirable North Fork location, this special property offers the perfect balance of privacy and convenience. Surrounded by preserved land, large properties and a horse property, the picturesque 2.18-acre setting provides a peaceful retreat while remaining just minutes from restaurants, marinas, shops, wineries,

    Nancy Cervelli Daniel Gale Sothebys Intl Rlty

    61341 Route 25, Southold, NY 11971
  • /29

    $10,000 Per Month

    • 2 Beds
    • 1.5 Baths
    • 940 Sq Ft
    • House for Rent

    1825 Main Bayview Rd, Southold, NY 11971

    Clean and Tidy 2 Bedroom/1.5 Bath Cottage with North Fork Character and Charm, Located Near Bay Beach and Farmstand. Nice Yard and Deck for Enjoyable Outdoor Living. July $8,000 (or $2,000 per week with two week minimum); August to Labor Day $10,000 (or $2,000 per week with two week minimum); Labor Day thru September $6,000 (or $2,000 per week with two week minimum); October $6,000. Rental Permit

    Paul Loeb Douglas Elliman Real Estate

    1825 Main Bayview Rd, Southold, NY 11971
  • 1710 N Bayview Road Extension, Southold, NY 11971

    $2,250,000

    Sold Oct 24, 2025

    1710 N Bayview Road Extension, Southold, NY 11971

    • 4 Beds
    • 4.5 Baths
    • 3,700 Sq Ft
    • Built 2005

    Last Sold Summary

    • 2% Below List Price
    • $608/SF
    • 13 Days On Market

    Current Estimated Value $2,236,550

    Last Listing Agent Eric Elkin Compass Greater NY LLC

    1710 N Bayview Road Extension, Southold, NY 11971
    • 250 Midway Rd, Southold, NY 11971

      Est $2,380,000

      Not Listed For Sale

      250 Midway Rd, Southold, NY 11971

      • 4 Beds
      • 2 Baths
      • Built 1950
      250 Midway Rd, Southold, NY 11971

      Last Sold Summary

      • 27 Days On Market

      Last Listing Agent Katie Schimpf Daniel Gale Sothebys Intl Rlty

  • /21

    $1,995,000

    Pending
    • 3 Beds
    • 3 Baths
    • 1,782 Sq Ft

    680 Private Rd Unit 17, Southold, NY 11971

    Charming, private, and uniquely connected to the water, this cedar-shingled three-bedroom cottage offers a compelling combination of immediate enjoyment and future potential. Set on nearly an acre, the property includes a 50' wide section that extends to the bay, where a beachside double deck and stairs provide direct access to your private stretch of sandy beach. Inside, the living room is

    Bridget Elkin Compass Greater NY LLC

    680 Private Rd Unit 17, Southold, NY 11971
  • /6

    $15,000 Per Month

    • 1 Bath
    • 230 Sq Ft
    • Condo for Rent

    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 BBQ area on grounds free laundry room.Seasonal Condo Use Only Open from April - November then the condo closes for season.

    Peter Vekiarellis ERealty Advisors Inc

    52325 County Road 48 Unit 8, Southold, NY 11971
  • 6625 Hortons Ln, Southold, NY 11971

    $910,000

    Sold Jul 28, 2026

    6625 Hortons Ln, Southold, NY 11971

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft
    • Built 1966

    Last Sold Summary

    • 16% Below List Price
    • $607/SF
    • 75 Days On Market

    Current Estimated Value $945,055

    Last Listing Agent Detra Sarris Signature Premier Properties

    6625 Hortons Ln, Southold, NY 11971
    • 1750 Water Terrace, Southold, NY 11971

      Est $1,231,001

      Not Listed For Sale

      1750 Water Terrace, Southold, NY 11971

      • 4 Beds
      • 2.5 Baths
      • 2,000 Sq Ft
      • Built 2002
      1750 Water Terrace, Southold, NY 11971

      Last Sold Summary

      • 68 Days On Market

      Last Listing Agent Connie Liappas Compass Greater NY LLC

  • /17

    $795,000

    • Land
    • 5,227 Sq Ft
    • $6,625,000 per Acre

    55915 County Road 48, Greenport, NY 11944

    Life's better on the sound! This sound-front lot boasts 50’ of waterfront and approved plans for a 3-bedroom, 2-bath home. Imagine mornings on the porch, afternoons on the water, and evenings with a front-row seat to the most spectacular sunsets around. Whether you're building your forever home, a weekend retreat, or an investment property, this lot is ready when you are and offers the best of

    Sheri Winter Parker Corcoran

    55915 County Road 48, Greenport, NY 11944
  • /22

    $30,000 Per Month

    • 5 Beds
    • 4.5 Baths
    • 3,233 Sq Ft
    • House for Rent

    1700 Cedar Dr, Southold, NY 11971

    2026 Availability: June $30,000. July RENTED. Perfect summer getaway with 5 bed, 4.5 bath in the heart of the North Fork. The home sits on 1.24 acres and features an open floor plan, large screened-in porch, full finished basement, wood burning fireplace, outdoor shower, and a saltwater, gunite pool. The primary bedroom has a large roof deck overlooking the pool and rear yard. Bedrooms and full

    Shane Hafer Compass Greater NY LLC

    1700 Cedar Dr, Southold, NY 11971
  • 875 Oak Ave, Southold, NY 11971

    $590,000

    Sold May 07, 2026

    875 Oak Ave, Southold, NY 11971

    • 2 Beds
    • 1 Bath
    • 973 Sq Ft
    • Built 1938

    Last Sold Summary

    • 6% Below List Price
    • $606/SF
    • 41 Days On Market

    Current Estimated Value $600,384

    Last Listing Agent Cheryl Schneider The Agency Northshore NY

    875 Oak Ave, Southold, NY 11971
    • 505 Longview Ln, Southold, NY 11971

      Est $1,093,396

      Not Listed For Sale

      505 Longview Ln, Southold, NY 11971

      • 3 Beds
      • 2 Baths
      • Built 1984
      505 Longview Ln, Southold, NY 11971

      Last Sold Summary

      • 11 Days On Market

      Last Listing Agent Nicole Fitzgerald Signature Premier Properties

  • /25

    $1,549,999

    $50K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 2,200 Sq Ft

    3715 Hortons Ln, Southold, NY 11971

    Designer Modern Farm Ranch set on over 3.35 Acres with farm and scenic views. Renovated 2023. Open concept Living Room, Dining Room and Kitchen, Gorgeous Kitchen with quartz countertops, Stainless Steel Appliances, built in Wine Cooler, New Windows throughout, New Interior Doors, New Exterior Doors, Custom Closets, New flooring, updated Designer Baths, New Boiler, New Well Pump, New Hot Water

    Arelis Olivieri RIN

    3715 Hortons Ln, Southold, NY 11971
  • /20

    $3,995 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,600 Sq Ft
    • House for Rent

    13595 Soundview Ave, Southold, NY 11971

    Tucked away among the trees, this charming home offers the perfect blend of privacy and natural light. Thoughtfully furnished and move-in ready, it features inviting living spaces, including both a comfortable living room and a separate TV/family room. The fully equipped kitchen has everything you need, while three cozy bedrooms—including a private en-suite primary bedroom—provide a welcoming

    Diane Arpaia Signature Premier Properties

    13595 Soundview 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

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