4,599

Southold, NY Homes

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  • /3

    $850,000

    Pre-Foreclosure
    • 3 Beds
    • 4 Baths
    • 2,100 Sq Ft

    150 Baywater Ave, Southold, NY 11971

    Steeped in history and set on a 1.05-acre parcel in the heart of the North Fork, this circa-1663 residence presents a rare opportunity to preserve and reimagine one of Southold’s oldest and most significant properties. Ideally positioned, it is just moments from one of the East End’s finest sandy bay beaches and Croteaux Vineyards, as well as a short drive to renowned wineries, farm stands, and

    Marco Maida Compass Greater NY LLC

    150 Baywater Ave, Southold, NY 11971
  • /30

    $10,000 Per Month

    • 3 Beds
    • 1.5 Baths
    • 1,578 Sq Ft
    • House for Rent

    425 Old Shipyard Ln, Southold, NY 11971

    Southold-Enjoy the North Fork in this adorable cottage. Located in Founder's Landing Southold beach community. Three bedrooms, living room, kitchen with dining area and sunroom overlooking yard and pool. This charming home has everything you need for a great summer getaway. Close to community beach and Park. Close to town, restaurants, shopping, The giving room yoga and juice bar, Southold fish

    Amy Kirincic The Agency Northshore NY

    425 Old Shipyard Ln, 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 $679,949

    Last Listing Agent Lisa Cerreta BERKSHIRE HATHAWAY

    900 Cedar Dr, 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 Realty Connect USA L I Inc

  • /35

    $1,750,000

    $249K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,000 Sq Ft

    3500 Pine Neck Rd, Southold, NY 11971

    Step into nearly three centuries of preserved history at 3500 Pine Neck Road, Southold—an extraordinary historic residence originally built in circa 1720 and impeccably maintained in pristine condition. This is not simply a home; it is a rare architectural heirloom, offering authenticity, craftsmanship, and legacy that cannot be replicated. Every historic element has been preserved to perfection,

    Trish Bergin Signature Premier Properties

    3500 Pine Neck Rd, Southold, NY 11971
  • /29

    $8,000 Per Month

    • 4 Beds
    • 3 Baths
    • 2,600 Sq Ft
    • House for Rent

    60 Water Terrace, Southold, NY 11971

    Settle into summer on the North Fork in this beautifully maintained and updated 4 bedroom, 3 full bath home located in the Angel Shores community of Southold. The layout is ideal for entertaining or just enjoying the lazy days of summer. This special home offers a 1st floor bedroom and full bath, along with a 2nd story spacious primary en-suite and 2 additional bedrooms to comfortably accommodate

    Natalie Hough Daniel Gale Sothebys Intl Rlty

    60 Water Terrace, 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
    • 605 Topsail Ln, Southold, NY 11971

      Est $1,054,423

      Not Listed For Sale

      605 Topsail Ln, Southold, NY 11971

      • 3 Beds
      • 2.5 Baths
      • Built 1992
      605 Topsail Ln, Southold, NY 11971

      Last Sold Summary

      • 55 Days On Market

      Last Listing Agent Bridget Elkin Compass Greater NY LLC

  • /42

    $3,695,000

    $155K PRICE DROP
    • 6 Beds
    • 4 Baths
    • 4,663 Sq Ft

    105 Waterview Dr, Southold, NY 11971

    Discover a rare waterfront property where privacy, space, and breathtaking views come together on 6.5 gated acres. Spanning two single-and-separate lots, this refreshed 6-bedroom, 4-bath colonial offers a den/office, bonus room, and sweeping water views from nearly every room. Thoughtfully designed for both comfort and future flexibility, the residence provides substantial expansion potential.

    Roric Tobin Compass Greater NY LLC

    105 Waterview Dr, Southold, NY 11971
  • /5

    $4,000 Per Month

    • 3 Beds
    • 1 Bath
    • 1,100 Sq Ft
    • House for Rent

    310 Old Shipyard Ln, Southold, NY 11971

    Southold Village Rental Charming and well-located, this 3-bedroom, 1-bath residence offers easy North Fork living just moments from the heart of Southold. A short distance to Southold Town, local shops, dining, and the waterfront, as well as close proximity to Founders Beach for swimming, sunsets, and seaside relaxation. The home features a comfortable layout with light-filled living spaces,

    Eric Frend Corcoran

    310 Old Shipyard Ln, 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 $736,547

    Last Listing Agent Rita Rooney Douglas Elliman Real Estate

    205 Grange Rd, Southold, NY 11971
    • 10995 N Bayview Rd, Southold, NY 11971

      Est $4,025,500

      Not Listed For Sale

      10995 N Bayview Rd, Southold, NY 11971

      • 5 Beds
      • 5.5 Baths
      • 6,162 Sq Ft
      • Built 2000
      10995 N Bayview Rd, Southold, NY 11971

      Last Sold Summary

      • 399 Days On Market

      Last Listing Agent Carol Szynaka Daniel Gale Sothebys Intl Rlty

  • /37

    $849,999

    $30K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,588 Sq Ft

    870 Crittens Ln, Southold, NY 11971

    Nestled in the Southwood Community on a beautifully landscaped 0.51-acre lot in Southold, this spacious ranch offers the perfect blend of comfort, charm, and North Fork living. Gleaming hardwood floors flow throughout the home, which features three generously sized bedrooms and two full bathrooms. The expansive formal living room is highlighted by a cozy wood-burning fireplace, while the large

    Stephen Zappalla Keller Williams Realty Elite

    870 Crittens Ln, Southold, NY 11971
  • /8

    $5,000 Per Month

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

    8415 Soundview Ave, Southold, NY 11971

    Step inside this charming 2 bedroom, 1 bath bungalow nestled on the serene shores of Great Pond in Southold. This cozy waterfront retreat offers tranquil water views and is just around the corner from Kenny's Beach and the popular Little Fish restaurant. Enjoy kayaking, paddle boarding, and fishing right from your backyard. Centrally located in the heart of the North Fork, you're perfectly

    Nicole Fitzgerald Signature Premier Properties

    8415 Soundview Ave, 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 $935,789

    Last Listing Agent Jeannine Kowaleski William Raveis New York LLC

    4100 Youngs Ave, Southold, NY 11971
    • 75 Reydon Dr, Southold, NY 11971

      Est $1,235,707

      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

      Last Listing Agent Nancy Cervelli Daniel Gale Sothebys Intl Rlty

  • /28

    $1,445,000

    $50K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft

    470 Windy Point Ln, Southold, NY 11971

    Boaters Dream! Located in Southold, this 3-bedroom, 2-bathroom canal-front home on Cory Creek offers a well-designed layout and direct access to the water. The creek leads out to the bay, and the property features a deep-water dock suitable for a variety of boating needs. Inside, the home offers an open-concept living, dining, and kitchen area with a comfortable, functional flow. The kitchen

    Katie Schimpf Daniel Gale Sothebys Intl Rlty

    470 Windy Point Ln, Southold, NY 11971
  • /29

    $27,000 Per Month

    • 4 Beds
    • 4.5 Baths
    • 3,100 Sq Ft
    • House for Rent

    590 Soundview Ave, Southold, NY 11971

    This Spacious Open Floor Plan Home Features Two Separate Living Areas, a Treetop Waterview Deck, A Chef's Kitchen with Pantry and a Large Stylish Dining Table. This Inviting Home's Layout Offers Comfortable Gathering Spaces. The Resort-Style Outdoor Living Area is Highlighted by an Inground Pool with a Built-In Hot Tub and Elegant Bluestone Pool Surround. Generous Seating Area Including Hammock,

    Paul Loeb Douglas Elliman Real Estate

    590 Soundview 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 $1,166,960

    Last Listing Agent William Walters Daniel Gale Sothebys Intl Rlty

    1475 Oaklawn Ave, Southold, NY 11971
    • 400 Windjammer Dr, Southold, NY 11971

      Est $2,296,667

      Not Listed For Sale

      400 Windjammer Dr, Southold, NY 11971

      • 4 Beds
      • 4 Baths
      • 3,373 Sq Ft
      • Built 1985
      400 Windjammer Dr, Southold, NY 11971

      Last Sold Summary

      • 122 Days On Market

      Last Listing Agent Mariah Mills Daniel Gale Sothebys Intl Rlty

  • /26

    $950,000

    $100K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,989 Sq Ft

    5845 N Bayview Rd, Southold, NY 11971

    Tucked away in a peaceful enclave of Southold, this classic Cape Cod offers a private escape that backs directly onto protected woodlands. One of the home’s standout features is an expansive four-season sunroom, which serves as a light-filled bridge between the indoors and your own quiet backyard sanctuary. Whether you are hosting a summer brunch or enjoying a morning coffee, the surrounding

    Stephanie Visek Engel & Volkers North Fork

    5845 N Bayview Rd, Southold, NY 11971
  • /43

    $14,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,693 Sq Ft
    • House for Rent

    4525 S Harbor Rd, Southold, NY 11971

    2026 Availability: July $12,000; August $14,000. Newly renovated Southold home offering 3 bedrooms and 2 full baths, ideally located just 0.2 miles from South Harbor beach. An open concept kitchen and living room, anchored by a fireplace and filled with natural light offers the perfect place to unwind after a day of exploring the North Fork. Outdoors, a patio with dining area, built in barbecue,

    Bridget Elkin Compass Greater NY LLC

    4525 S Harbor Rd, Southold, NY 11971
  • 800 Corey Creek Ln, Southold, NY 11971

    $2,050,000

    Sold Jul 01, 2026

    800 Corey Creek Ln, Southold, NY 11971

    • 4 Beds
    • 5 Baths
    • 3,025 Sq Ft
    • Built 2026

    Last Sold Summary

    • 5% Above List Price
    • $678/SF
    • 19 Days On Market

    Current Estimated Value $1,980,333

    Last Listing Agent Lisa Davey LI Probate Realty Inc

    800 Corey Creek Ln, Southold, NY 11971
    • 1565 Brigantine Dr, Southold, NY 11971

      Est $1,039,963

      Not Listed For Sale

      1565 Brigantine Dr, Southold, NY 11971

      • 3 Beds
      • 2.5 Baths
      1565 Brigantine Dr, Southold, NY 11971

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Trish English Signature Premier Properties

  • /7

    $1,499,000

    $201K PRICE DROP
    • Land
    • 5.25 Acres
    • $285,524 per Acre

    11200 N Bayview Rd, Southold, NY 11971

    Extremely rare offering of 5.25 acres of undeveloped, wooded land in bucolic Paradise Point - the crown jewel of the charming hamlet of Southold. Once an scenic equestrian grazing meadow to an adjoining 33 acre estate, this land offers a tranquil, secluded location close to gorgeous Bay beaches. Borders preserved land. Just a few scenic miles to fine dining and cafes, tasting rooms & vineyards,

    Kathleen Travers Douglas Elliman Real Estate

    11200 N Bayview Rd, Southold, NY 11971
  • /46

    $12,000 Per Month

    • 4 Beds
    • 3 Baths
    • 2,900 Sq Ft
    • House for Rent

    110 Sleepy Hollow Ln, Southold, NY 11971

    Discover this stunningly renovated 4-bedroom, 3-bath home, offering an expansive open floor plan, a cozy den, and a versatile bonus room. Designed for both comfort and style, the chef’s kitchen includes a massive eat-in-quartz island and boasts top-of-the-line Fisher & Paykel appliances, including a double-drawer dishwasher, induction cooktop, and convection oven. Perfect for entertaining and

    Paul Loeb Douglas Elliman Real Estate

    110 Sleepy Hollow Ln, Southold, NY 11971
  • 3075 Lighthouse Rd, Southold, NY 11971

    $1,655,000

    Sold Apr 28, 2026

    3075 Lighthouse Rd, Southold, NY 11971

    • 3 Beds
    • 2 Baths
    • 1,446 Sq Ft
    • Built 1927

    Last Sold Summary

    • 4% Below List Price
    • $1,145/SF
    • 59 Days On Market

    Current Estimated Value $1,721,124

    Last Listing Agent Kristy Naddell Douglas Elliman Real Estate

    3075 Lighthouse Rd, Southold, NY 11971
    • 465 Windjammer Dr, Southold, NY 11971

      Est $947,153

      Not Listed For Sale

      465 Windjammer Dr, Southold, NY 11971

      • 3 Beds
      • 2 Baths
      • 1,167 Sq Ft
      • Built 1923
      465 Windjammer Dr, Southold, NY 11971

      Last Sold Summary

      • 46 Days On Market

      Last Listing Agent Nancy Cervelli Daniel Gale Sothebys Intl Rlty

  • /31

    $1,950,000

    Pending
    • 2 Beds
    • 2 Baths
    • 3,603 Sq Ft

    4630 Youngs Ave, Southold, NY 11971

    Calling all artists or collectors of any kind! This is what you have been waiting for. Welcome to Homeport, loft-like living on the North Fork. A fully sustainable, net-zero home with non-toxic, recyclable and eco-friendly materials including solar and an EV charging station. A 30' x 60' studio with a garage door and 12' ceilings. Space for at least 10+ cars. An ensuite office with an additional

    Sheri Winter Parker Corcoran

    4630 Youngs Ave, Southold, NY 11971
  • /20

    $5,000 Per Month

    • 3 Beds
    • 1 Bath
    • 1,200 Sq Ft
    • House for Rent

    145 Founders Path, Southold, NY 11971

    Beautiful Charming Cottage Located in the Coveted Community of Founders. Close to a gorgeous sandy beach, grocery shopping, coffee shop, restaurants, jitney stop, and all things North Fork. Three bedrooms, one bath, LR, kitchen, outdoor deck, fire pit, outdoor shower. Available Sept. $5000, Oct & Nov $4000, Dec through March $3,000, April $3,500. May $5,000, June $6,000 and August $12,000.

    Diane Mollica Compass Greater NY LLC

    145 Founders Path, Southold, NY 11971
  • 19620 Soundview Ave, Southold, NY 11971

    $4,000,000

    Sold Jun 23, 2026

    19620 Soundview Ave, Southold, NY 11971

    • 7 Beds
    • 7.5 Baths
    • 7,300 Sq Ft
    • Built 2025

    Last Sold Summary

    • 9% Below List Price
    • $548/SF
    • 69 Days On Market

    Current Estimated Value $3,923,454

    Last Listing Agent Kristy Naddell Douglas Elliman Real Estate

    19620 Soundview Ave, Southold, NY 11971
    • 165 Deer Run, Southold, NY 11971

      Est $3,075,333

      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

      Last Listing Agent Connie Liappas Compass Greater NY LLC

  • /25

    $2,295,000

    Pending
    • 4 Beds
    • 3 Baths
    • 3,769 Sq Ft

    450 Sterling Woods Ln, Southold, NY 11971

    Spacious Open Plan Home with So Much to Offer near Several Great Beaches. Open Livingroom, Dining Room, Kitchen, a Separate Den and a Separate Office as well as a Good Size Bedroom and Bath on First Floor. Primary Ensuite and Two Additional Bedrooms and Hall Bath on Second Floor. Separate Fencing around Inground Heated Saltwater Pool with Easy Automatic Solar Cover and a Pool House. Large Stone

    Paul Loeb Douglas Elliman Real Estate

    450 Sterling Woods Ln, Southold, NY 11971
  • /39

    $7,500 Per Month

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

    485 Pine Rd, Southold, NY 11971

    2026 Rates: September $7500; October $10,000: Discover your perfect getaway in this expansive and meticulously updated ranch home, designed for relaxation and rejuvenation. Experience a resort-like atmosphere with the stunning gunite, heated saltwater pool, complemented by a beautiful stone surround and convenient outdoor shower. Step inside to find high vaulted ceilings that create an airy

    William Walters Daniel Gale Sothebys Intl Rlty

    485 Pine Rd, Southold, NY 11971
  • 800 Goose Creek Ln, Southold, NY 11971

    $1,250,000

    Sold Nov 25, 2025

    800 Goose Creek Ln, Southold, NY 11971

    • 3 Beds
    • 3 Baths
    • 2,032 Sq Ft
    • Built 1997

    Last Sold Summary

    • $615/SF
    • 21 Days On Market

    Current Estimated Value $1,276,140

    Last Listing Agent Nancy Cervelli Daniel Gale Sothebys Intl Rlty

    800 Goose Creek Ln, Southold, NY 11971
    • 210 Northfield Ln, Southold, NY 11971

      Est $1,854,158

      Not Listed For Sale

      210 Northfield Ln, Southold, NY 11971

      • 4 Beds
      • 4 Baths
      • 3,200 Sq Ft
      • Built 1990
      210 Northfield Ln, Southold, NY 11971

      Last Sold Summary

      • 208 Days On Market

      Last Listing Agent Jeanmarie Bay William Raveis New York LLC

  • /41

    $1,849,000

    $76K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 2,850 Sq Ft

    2100 Glenn Rd, Southold, NY 11971

    This turnkey opportunity in Southold, bordering beautiful Goose Creek, offers a private dock and is perfect for those seeking a North Fork beach house with a boater's lifestyle. Situated on more than two-thirds of an acre, this contemporary home features modern lines, abundant natural light, and a stunning yard ideal for outdoor entertaining. Upon arrival, you are welcomed by a spacious driveway

    Alexis Meadows Compass Greater NY LLC

    2100 Glenn Rd, Southold, NY 11971
  • /21

    $10,000 Per Month

    • 5 Beds
    • 7 Baths
    • 3,500 Sq Ft
    • House for Rent

    495 N Parish Dr, Southold, NY 11971

    Southold, North Fork.Experience the beauty of seasonal living on Southold Bay. This newly renovated contemporary bayfront estate home invites you to bask in its light and bright ambiance, perfect for relaxation and rejuvenation. With its Zen-inspired organic design, you’ll find comfort and privacy combined with the conveniences of modern life.Nestled near the Southold Yacht Club, just

    Nicholas Planamento William Raveis New York LLC

    495 N Parish Dr, Southold, NY 11971
  • 465 Ripple Water Ln, Southold, NY 11971

    $3,400,000

    Sold Jun 26, 2026

    465 Ripple Water Ln, Southold, NY 11971

    • 4 Beds
    • 5.5 Baths
    • 6,366 Sq Ft
    • Built 2025

    Last Sold Summary

    • 6% Below List Price
    • $534/SF
    • 139 Days On Market

    Last Listing Agent Jerry Cibulski Century 21 Albertson Realty

    465 Ripple Water Ln, Southold, NY 11971
    • 8355 Main Bayview Rd, Southold, NY 11971

      Est $1,764,026

      Not Listed For Sale

      8355 Main Bayview Rd, Southold, NY 11971

      • 4 Beds
      • 3 Baths
      • 2,662 Sq Ft
      • Built 1867
      8355 Main Bayview Rd, Southold, NY 11971

      Last Sold Summary

      Last Listing Agent Janet Markarian Daniel Gale Sothebys Intl Rlty

Showing Results 201 - 240, Page 6 of 18

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