4,633

Southold, NY Homes

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  • /6

    $4,000,000

    • 3 Beds
    • 4 Baths
    • 3,496 Sq Ft

    1480 Old Wood Path, Southold, NY 11971

    Set on nearly four acres along one of the North Fork’s most coveted stretches of sandy bay beach, this is a rare opportunity to secure an exceptional waterfront property with meaningful upside. The existing three-bedroom, four-bath home offers a solid foundation for renovation or expansion, allowing a new owner to tailor the property to their vision. The grounds are equally compelling. A tennis

    Bridget Elkin Compass Greater NY LLC

    1480 Old Wood Path, 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
  • 5950 N Bayview Rd, Southold, NY 11971

    $1,375,000

    Sold Jun 16, 2025

    5950 N Bayview Rd, Southold, NY 11971

    • 3 Beds
    • 2 Baths
    • 1,547 Sq Ft
    • Built 2016

    Last Sold Summary

    • 8% Below List Price
    • $889/SF
    • 107 Days On Market

    Current Estimated Value $1,404,406

    Last Listing Agent Lisa Gillooly Compass Greater NY LLC

    5950 N Bayview Rd, Southold, NY 11971
  • /7

    $499,000

    • Land
    • 16,552 Sq Ft
    • $1,313,158 per Acre

    11195 N Bayview Rd, Southold, NY 11971

    .38-acre wooded level lot in a private and natural setting. Ideally located near Paradise Point, Cedar Beach, Southold shops, vineyards, farmstands and Greenport Brewery. This is a triangle shape lot with 258ft of frontage on N Bayview Rd and 178ft/182ft deep on each side. A rare opportunity to create your own coastal retreat in one of the North Fork’s most desirable neighborhoods. No preliminary

    Mariah Mills Daniel Gale Sothebys Intl Rlty

    11195 N Bayview 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
  • 2865 S Harbor Rd, Southold, NY 11971

    $1,150,000

    Sold Jul 10, 2025

    2865 S Harbor Rd, Southold, NY 11971

    • 3 Beds
    • 3 Baths
    • 2,250 Sq Ft
    • Built 1984

    Last Sold Summary

    • $511/SF
    • 24 Days On Market

    Current Estimated Value $1,185,496

    Last Listing Agent Shane Hafer Compass Greater NY LLC

    2865 S Harbor Rd, Southold, NY 11971
  • /43

    $4,250,000

    • 3 Beds
    • 2 Baths
    • 1,800 Sq Ft

    56875 Route 48, Southold, NY 11971

    Exceptional soundfront offering combining a beautifully maintained waterfront residence with a rare, separately buildable adjacent lot—creating a unique opportunity for legacy ownership or future development. The existing home sits on .75 acres with direct, no-bluff access to the Sound and showcases sweeping 180-degree panoramic water views. This 3-bedroom, 2-bath residence features a waterside

    Kris Pilles East End Luxury Ltd

    56875 Route 48, 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
  • 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 $1,748,851

    Last Listing Agent Kristy Naddell Douglas Elliman Real Estate

    3075 Lighthouse Rd, Southold, NY 11971
  • /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
  • /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
  • 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 $1,249,072

    Last Listing Agent Nancy Cervelli Daniel Gale Sothebys Intl Rlty

    800 Goose Creek Ln, Southold, NY 11971
    • 750 Cedar Dr, Southold, NY 11971

      Est $975,431

      Not Listed For Sale

      750 Cedar Dr, Southold, NY 11971

      • 3 Beds
      • 2.5 Baths
      • 1,800 Sq Ft
      • Built 2001
      750 Cedar Dr, Southold, NY 11971

      Last Sold Summary

      • 9 Days On Market

  • /42

    $3,850,000

    • 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
  • /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
  • 2555 Youngs Ave Unit 12E, Southold, NY 11971

    $602,500

    Sold Jul 08, 2025

    2555 Youngs Ave Unit 12E, Southold, NY 11971

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Built 1986

    Last Sold Summary

    • $502/SF
    • 19 Days On Market

    Last Listing Agent Timothy O'Keefe Signature Premier Properties

    2555 Youngs Ave Unit 12E, Southold, NY 11971
  • /24

    $1,249,000

    $500K PRICE INCREASE
    • 3 Beds
    • 2.5 Baths
    • 2,300 Sq Ft

    650 the Esplanade, Southold, NY 11971

    Southold, North Fork - Private Bayfront Community Living Discover effortless, upscale living in the coveted Angel Shores bayfront community, complete with private association access to a pristine sugar-sand beach. Set on a beautifully landscaped, ultra-private lot backing to over 20 acres of protected preserve land-with only one immediate neighboring home-this exceptional 2,300 sq ft contemporary

    Nicholas Planamento William Raveis (Mattituck)

    650 the Esplanade, Southold, NY 11971
  • /46

    $25,000 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
  • 1755 Yennecott Dr, Southold, NY 11971

    $940,000

    Sold Dec 02, 2025

    1755 Yennecott Dr, Southold, NY 11971

    • 6 Beds
    • 2.5 Baths
    • 3,200 Sq Ft
    • Built 1972

    Last Sold Summary

    • 22% Below List Price
    • $294/SF
    • 721 Days On Market

    Current Estimated Value $1,033,145

    Last Listing Agent Isaac Israel Richmond Realty Corp

    1755 Yennecott Dr, Southold, NY 11971
    • 1305 Cedar Dr, Southold, NY 11971

      Est $1,154,258

      Not Listed For Sale

      1305 Cedar Dr, Southold, NY 11971

      • 4 Beds
      • 3.5 Baths
      • 3,233 Sq Ft
      • Built 1973
      1305 Cedar Dr, Southold, NY 11971

      Last Sold Summary

      • 105 Days On Market

  • /50

    $4,395,000

    Pending
    • 7 Beds
    • 7.5 Baths
    • 7,300 Sq Ft

    19620 Soundview Ave, Southold, NY 11971

    Soundview on the Vines presents a rare opportunity to own a new construction vineyard-side estate where modern architecture, refined craftsmanship, and the natural beauty of the North Fork converge. Spanning approximately 7,300SF and situated on nearly 2 acres, this exceptional residence has been thoughtfully designed to balance grand-scale entertaining with relaxed, everyday luxury. Upon

    Kristy Naddell Douglas Elliman Real Estate

    19620 Soundview 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
  • 385 Cottage Place, Southold, NY 11971

    $899,000

    Sold Mar 05, 2026

    385 Cottage Place, Southold, NY 11971

    • 3 Beds
    • 2 Baths
    • 1,440 Sq Ft
    • Built 1900

    Last Sold Summary

    • 8% Below List Price
    • $624/SF
    • 131 Days On Market

    Current Estimated Value $892,590

    Last Listing Agent Janet Markarian Daniel Gale Sothebys Intl Rlty

    385 Cottage Place, Southold, NY 11971
  • /28

    $1,445,000

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

    470 Windy Point Ln, Southold, NY 11971

    Boaters Dream! Located in Southold, this 3-bedroom, 3-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
  • /39

    $12,000 Per Month

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

    485 Pine Rd, Southold, NY 11971

    2026 Rates: MDW- June 30 $12,000; September $12,000; 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

    William Walters Daniel Gale Sothebys Intl Rlty

    485 Pine Rd, Southold, NY 11971
  • 3680 Main Bayview Rd, Southold, NY 11971

    $590,000

    Sold Jan 08, 2026

    3680 Main Bayview Rd, Southold, NY 11971

    • 3 Beds
    • 2 Baths
    • 1,442 Sq Ft
    • Built 1761

    Last Sold Summary

    • 7% Below List Price
    • $409/SF
    • 14 Days On Market

    Current Estimated Value $651,804

    Last Listing Agent Barry Novick Daniel Gale Sothebys Intl Rlty

    3680 Main Bayview Rd, Southold, NY 11971
    • 60 Koke Dr, Southold, NY 11971

      Est $897,877

      Not Listed For Sale

      60 Koke Dr, Southold, NY 11971

      • 3 Beds
      • 2 Baths
      • 1,500 Sq Ft
      • Built 1960
      60 Koke Dr, Southold, NY 11971

      Last Sold Summary

      • 5 Days On Market

  • /22

    $970,000

    Open Sun 11AM - 1PM $80K 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
  • /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
  • 9875 Main Bayview Rd, Southold, NY 11971

    $950,000

    Sold Nov 18, 2025

    9875 Main Bayview Rd, Southold, NY 11971

    • 4 Beds
    • 3 Baths
    • 2,000 Sq Ft
    • Built 1838

    Last Sold Summary

    • 27% Below List Price
    • $475/SF
    • 231 Days On Market

    Current Estimated Value $970,740

    Last Listing Agent Kristy Naddell Douglas Elliman Real Estate

    9875 Main Bayview Rd, Southold, NY 11971
  • /46

    $3,598,999

    New Construction Pending
    • 4 Beds
    • 5.5 Baths
    • 6,366 Sq Ft

    465 Ripple Water Ln, Southold, NY 11971

    You know we have been looking at new homes for a while. This one is the first that felt like, "okay, this checks the boxes"The granite front porch sold me right away. wine and cheese with everyone and with the larger width and depth, you can see they built the home with this in mind. And the kitchen is exactly what I wanted because this is where we all hang out and this has the built in

    Jerry Cibulski Century 21 Albertson Realty

    465 Ripple Water Ln, Southold, NY 11971
  • /26

    $30,000 Per Month

    • 4 Beds
    • 3 Baths
    • 2,350 Sq Ft
    • House for Rent

    485 Hickory Ave, Southold, NY 11971

    Impressive Goose Creek home with water views and large heated in-ground pool! This four bedroom, three bath house features a first floor primary bedroom with en-suite, a gourmet kitchen and open living space. The newly designed landscape with outdoor kitchen (not pictured) is ideal for entertaining or relaxing. Enjoy its large fire pit and BBQ grill after an afternoon of Kayaking. Close to

    Mackenzie Needham Daniel Gale Sothebys Intl Rlty

    485 Hickory Ave, Southold, NY 11971
  • 3700 Minnehaha Blvd, Southold, NY 11971

    $1,025,000

    Sold Feb 13, 2026

    3700 Minnehaha Blvd, Southold, NY 11971

    • 3 Beds
    • 1.5 Baths
    • 1,144 Sq Ft
    • Built 2003

    Last Sold Summary

    • 11% Below List Price
    • $896/SF
    • 53 Days On Market

    Current Estimated Value $1,025,146

    Last Listing Agent Rita Rooney Douglas Elliman Real Estate

    3700 Minnehaha Blvd, Southold, NY 11971

Showing Results 201 - 240, Page 6 of 18

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