4,571

Southold, NY Homes

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  • /28

    $2,200,000

    • 3 Beds
    • 3 Baths
    • 2,600 Sq Ft

    225 Lakeside Dr S, Southold, NY 11971

    Fully renovated and exceptionally private, this sophisticated waterfront contemporary is a true North Fork retreat, pairing stylish interiors with a serene setting and an effortless outdoor lifestyle. Hardwood floors and walls of glass define the open-concept, where a beautifully appointed kitchen flows into the living and dining spaces and an inviting sunroom, all oriented toward the water. Two

    Mariah Mills Daniel Gale Sothebys Intl Rlty

    225 Lakeside Dr S, 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
  • 530 Sunset Way, Southold, NY 11971

    $1,550,000

    Sold Sep 22, 2026

    530 Sunset Way, Southold, NY 11971

    • 5 Beds
    • 2 Baths
    • 1,688 Sq Ft
    • Built 1975

    Last Sold Summary

    • 9% Below List Price
    • $918/SF
    • 257 Days On Market

    Current Estimated Value $1,585,709

    Last Listing Agent Thomas McCarthy Thomas J McCarthy Real Estate

    530 Sunset Way, Southold, NY 11971
    • 50 Summit Dr, Southold, NY 11971

      Est $931,164

      Not Listed For Sale

      50 Summit Dr, Southold, NY 11971

      • 3 Beds
      • 2.5 Baths
      • 1,651 Sq Ft
      • Built 1966
      50 Summit Dr, Southold, NY 11971

      Last Sold Summary

      • 28 Days On Market

      Last Listing Agent Jerry Cibulski Century 21 Albertson Realty

  • /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
  • /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
  • 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
    • 10995 N Bayview Rd, Southold, NY 11971

      Est $3,710,500

      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

  • /42

    $2,650,000

    Open Sun 1PM - 3PM
    • 6 Beds
    • 5.5 Baths
    • 5,111 Sq Ft

    47100 Route 25, Southold, NY 11971

    A striking blend of authentic farmhouse architecture and modern design as realized by FHS Interiors, this beautifully renovated Southold home with gunite pool and spa offers exceptional style and comfort on a half-acre parcel in the heart of the North Fork. Wrapped in a dramatic charcoal exterior and welcoming covered porch, the home immediately sets itself apart with timeless curb appeal and

    Edmond Zenuni Saunders & Associates

    47100 Route 25, 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
  • 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
    • 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

  • /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
  • 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
    • 400 Windjammer Dr, Southold, NY 11971

      Est $2,185,333

      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

  • /42

    $4,299,000

    • 4 Beds
    • 3 Baths
    • 3,500 Sq Ft

    3525 Paradise Point Rd, Southold, NY 11971

    WELCOME TO PARADISE. Commanding 2.38 private acres on the bay in Southold’s coveted Paradise Point, this remarkable waterfront estate possesses the cinematic North Fork presence of a setting from Nelson DeMille’s Plum Island—dramatic, intriguing and entirely unforgettable. With approximately 97 feet of private beach, panoramic views toward Shelter Island and the estate-lined shoreline beyond,

    Nicholas Planamento William Raveis New York LLC

    3525 Paradise Point Rd, 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
  • 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
    • 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

  • /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
  • /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
  • 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
    • 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

  • /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

    Roric Tobin Compass Greater NY LLC

    105 Waterview Dr, Southold, NY 11971
  • /9

    $3,300 Per Month

    • 1 Bed
    • 1 Bath
    • 900 Sq Ft
    • House for Rent

    475 Clark Rd, Southold, NY 11971

    This cozy 1 bedroom with bonus rooms is ready for its next tenant! 2019 gut renovation. Brand name appliances, hardwood floors and a sun-filled kitchen. The front room can be used as a formal dining room or perhaps a nice bright office space! Large living room with tons of light from expansive front facing window and flanking side windows. Multiple entry points - through the front door or

    Brenna Shields Corcoran

    475 Clark 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 $2,006,667

    Last Listing Agent Lisa Davey LI Probate Realty Inc

    800 Corey Creek 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

  • /37

    $849,999

    $30K PRICE DROP Pending
    • 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
  • /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

    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
    • 275 Victoria Dr, Southold, NY 11971

      Est $775,178

      Not Listed For Sale

      275 Victoria Dr, Southold, NY 11971

      • 3 Beds
      • 1 Bath
      • Built 1970
      275 Victoria Dr, Southold, NY 11971

      Last Sold Summary

      • 22 Days On Market

      Last Listing Agent Kevin Collins Signature Premier Properties

  • /26

    $895,000

    $155K PRICE DROP Pending
    • 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
  • /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
  • 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
    • 750 Cedar Dr, Southold, NY 11971

      Est $1,010,234

      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

      Last Listing Agent Donna Bekisz Century 21 Sewanhaka Realty

  • /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 &

    Kathleen Travers Douglas Elliman Real Estate

    11200 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
  • 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
    • 430 Highwood Rd, Southold, NY 11971

      Est $930,922

      Not Listed For Sale

      430 Highwood Rd, Southold, NY 11971

      • 3 Beds
      • 2 Baths
      • Built 1983
      430 Highwood Rd, Southold, NY 11971

      Last Sold Summary

      • 30 Days On Market

      Last Listing Agent Jennifer Benton Compass Greater NY LLC

Showing Results 201 - 240, Page 6 of 18

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