4,633

Southold, NY Homes

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  • /25

    $2,799,000

    New Construction $200K PRICE DROP
    • 8 Beds
    • 7 Baths
    • 5,600 Sq Ft

    1350 Hortons Ln, Southold, NY 11971

    2-Acre Private Oasis with Custom "To Be Built" Luxury Home - Prime Location Near Town, Beaches & Vineyards! Discover the perfect blend of privacy, luxury and convenience with this exceptional 2-acre vacant lot, tucked away in a serene, secluded setting --- Yet just minutes from downtown, pristine beaches, and world-class vineyards, shopping and dining. Plans are in-place for a "To Be Built"

    Thomas McCarthy Thomas J McCarthy Real Estate

    1350 Hortons Ln, Southold, NY 11971
  • /45

    $10,000 Per Month

    • 4 Beds
    • 2.5 Baths
    • House for Rent

    1275 the Esplanade, Southold, NY 11971

    STUNNER 4BR DESIGNER HOME ~ PET FRIENDLY, HEATED POOL & BEACH!Fabulous Lux Vacations on the coveted Esplanade in "Angel Shores", with a deeded sandy bay beach and heated freeform lagoon pool with a waterfall. Property is fully fenced and private, with many lounge areas for sunning, a shady pergola when needed, and a great new outdoor shower. We offer a pet friendly policy, rare for an

    Kate Carpluk William Raveis New York LLC

    1275 the Esplanade, Southold, NY 11971
  • 3520 Old Rd N, Southold, NY 11971

    $1,307,000

    Sold Nov 14, 2025

    3520 Old Rd N, Southold, NY 11971

    • 3 Beds
    • 3 Baths
    • 3,000 Sq Ft
    • Built 1989

    Last Sold Summary

    • 98,990% Above List Price
    • $436/SF
    • 16 Days On Market

    Current Estimated Value $1,320,244

    Last Listing Agent Roseann Prussen Signature Premier Properties

    3520 Old Rd N, Southold, NY 11971
  • /20

    $1,150,000

    Open Fri 2PM - 4PM Coming Soon
    • 3 Beds
    • 2 Baths
    • 1,800 Sq Ft

    100 Bayberry Ln, Southold, NY 11971

    Just a stone's throw from the sands of Town Sound Beach, this bright and airy retreat offers the perfect blend of coastal proximity and quiet privacy. Freshly painted inside and out, the home feels crisp and modern, anchored by a stunning living room featuring cathedral ceilings, a cozy wood-burning fireplace, and oversized windows that flood the space with natural light. The layout is designed

    Diane Mollica Compass Greater NY LLC

    100 Bayberry Ln, Southold, NY 11971
  • /22

    $3,900 Per Month

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft
    • House for Rent

    440 Longview Ln, Southold, NY 11971

    Experience effortless one-level living in this immaculate Southold retreat. Set in the coveted Terry Waters community with its own sandy beach just down the road, this clean, airy home offers comfort, privacy, and classic North Fork charm. A welcoming front porch opens to an inviting living room and a spacious den featuring hardwood floors and a wood-burning fireplace. The dining area flows into

    Ryan McQueeney True North Realty Luxury Homes

    440 Longview Ln, Southold, NY 11971
  • Unlisted Address

    $733,000

    Sold May 22, 2026

    Unlisted Address

    • 1 Bed
    • 4 Baths
    • 2,890 Sq Ft
    • Built 1985

    Last Sold Summary

    • 5% Below List Price
    • $254/SF
    • 154 Days On Market

    Last Listing Agent Andrew Stype Andrew Stype Realty Inc

    Unlisted Address
  • /3

    $1,400,000

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 2,215 Sq Ft

    500 Summer Ln, Southold, NY 11971

    The classic North Fork lifestyle you have been waiting for has finally arrived. Nestled in a quiet Southold neighborhood, 500 Summer Lane offers the rare opportunity to create a retreat just moments from the beaches, vineyards, and beloved local destinations that define the North Fork. Here, tranquility meets convenience—you’re never far from the shoreline or the vibrant heartbeat of the

    Catherine Flood Compass Greater NY LLC

    500 Summer Ln, Southold, NY 11971
  • /20

    $25,000 Per Month

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

    2045 Lake Dr, Southold, NY 11971

    Offered June $15,000; July $25,000; August $30,000; September $20,000; October $15,000. This contemporary waterfront home on Great Pond enjoys sunrise over the water and spectacular sunsets over Long Island Sound from its hilltop setting in one of the North Fork’s most distinctive beach communities. Surrounded by native plantings and filled with natural light and cooling breezes, the home is

    Janet Markarian Daniel Gale Sothebys Intl Rlty

    2045 Lake Dr, Southold, NY 11971
  • 920 Pine Neck Rd Unit 2D1, Southold, NY 11971

    $877,500

    Sold Mar 17, 2026

    920 Pine Neck Rd Unit 2D1, Southold, NY 11971

    • 2 Beds
    • 1 Bath
    • 1,300 Sq Ft
    • Built 1967

    Last Sold Summary

    • 4% Below List Price
    • $675/SF
    • 76 Days On Market

    Current Estimated Value $883,346

    Last Listing Agent Erica Kelly Daniel Gale Sothebys Intl Rlty

    920 Pine Neck Rd Unit 2D1, Southold, NY 11971
    • 355 Cedar Dr, Southold, NY 11971

      Est $1,026,765

      Not Listed For Sale

      355 Cedar Dr, Southold, NY 11971

      • 3 Beds
      • 2 Baths
      • 2,230 Sq Ft
      • Built 1960
      355 Cedar Dr, Southold, NY 11971

      Last Sold Summary

      • 65 Days On Market

  • /41

    $2,795,000

    Pending
    • 4 Beds
    • 4.5 Baths
    • 4,327 Sq Ft

    1815 Laurel Ave, Southold, NY 11971

    Welcome to the Laurel Collection by Marrcon. New Luxury Construction located in the heart of the North Fork's Town of Southold. This home is situated on .80 acres & boasts 4,327 SF of living space with 4 bedrooms and 4.5 baths and combines clean lines of modern design with the allure of North Fork chic. This home comes with Authentic Western Red Cedar Shingle siding and a stucco accented stair

    Kristy Naddell Douglas Elliman Real Estate

    1815 Laurel Ave, Southold, NY 11971
  • /17

    $6,000 Per Month

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

    215 Leon Rd, Southold, NY 11971

    Enjoy this spacious vacation rental located just a short distance from Southold Town Beach. With room for the whole family, this home features three en-suite bedrooms plus an additional bedroom and full bath. The well-equipped kitchen opens to the dining and living rooms, where a cozy fireplace adds charm and warmth. Sliding glass doors lead to a deck overlooking a large backyard, perfect for

    Jeanmarie Bay William Raveis New York LLC

    215 Leon Rd, Southold, NY 11971
  • 875 Oak Ave, Southold, NY 11971

    $535,000

    Sold Jul 28, 2025

    875 Oak Ave, Southold, NY 11971

    • 2 Beds
    • 1 Bath
    • Built 1966

    Last Sold Summary

    • 26% Below List Price
    • 255 Days On Market

    Current Estimated Value $604,470

    Last Listing Agent Alexis Veryzer Engel & Volkers North Fork

    875 Oak Ave, Southold, NY 11971
  • /46

    $3,799,999

    New Construction $25K PRICE DROP
    • 5 Beds
    • 6 Baths
    • 5,285 Sq Ft

    150 Deer Run, Southold, NY 11971

    Gorgeous estate-like Nantucket shingle home in the final stage of construction. 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 custom details including maple cabinetry and vanities, Marvin Elevate windows, sliding and French doors, mahogany

    Jeffrey Mead Corcoran

    150 Deer Run, Southold, NY 11971
  • /32

    $30,000 Per Month

    • 6 Beds
    • 4 Baths
    • 3,000 Sq Ft
    • House for Rent

    1695 Old Woods Path, Southold, NY 11971

    Southold, North Fork: This beautiful estate, bayfront home offers complete privacy in a peaceful woodland setting with a historic provenance and featuring a sugar sand beach. Despite its private location, it is conveniently close to the village and North Fork amenities. Croteaux is just up the lane, and NoFo table is a short bike ride away. The estate house has a broad porch, a living room with a

    Nicholas Planamento William Raveis New York LLC

    1695 Old Woods Path, Southold, NY 11971
  • 1465 Ackerly Pond Ln, Southold, NY 11971

    $1,250,000

    Sold Feb 09, 2026

    1465 Ackerly Pond Ln, Southold, NY 11971

    • 4 Beds
    • 2.5 Baths
    • 3,226 Sq Ft
    • Built 2005

    Last Sold Summary

    • 11% Below List Price
    • $387/SF
    • 77 Days On Market

    Last Listing Agent Scott Bennett Douglas Elliman Real Estate

    1465 Ackerly Pond Ln, Southold, NY 11971
  • /5

    $799,000

    • Land
    • 2.29 Acres
    • $348,908 per Acre

    1350 Hortons Ln, Southold, NY 11971

    Discover The Perfect Canvas For Your Dream Estate On This Expansive 2+ Acre Lot, Offering The Ideal Balance Of Privacy And Convenience. Nestled In A Serene Setting, Yet Just Moments Away From The Vibrant Town Life, You’ll Be Close To Fine Dining, Shopping, And Everything The North Fork Has To Offer. This Unique Parcel Comes With Suffolk County Health Department Approval For An 8-Bedroom

    Thomas McCarthy Thomas J McCarthy Real Estate

    1350 Hortons Ln, Southold, NY 11971
  • /10

    $4,000 Per Month

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

    8515 Soundview Ave, Southold, NY 11971

    Tucked away on the peaceful edge of freshwater Great Pond in Southold, this delightful 2-bedroom, 1-bath cottage offers the perfect blend of comfort and charm. Enjoy quiet mornings with water views and spend your days kayaking, paddle boarding, or fishing right from your backyard. Barbecue and dine on the spacious deck with a sunset view of the lake. Ideally situated just moments from Kenny's

    Nicole Fitzgerald Signature Premier Properties

    8515 Soundview Ave, Southold, NY 11971
  • 150 Goldin Ln, Southold, NY 11971

    $756,000

    Sold Jan 30, 2026

    150 Goldin Ln, Southold, NY 11971

    • 3 Beds
    • 1 Bath
    • 900 Sq Ft
    • Built 2006

    Last Sold Summary

    • 4% Below List Price
    • $840/SF
    • 80 Days On Market

    Current Estimated Value $759,126

    Last Listing Agent Scott Bennett Douglas Elliman Real Estate

    150 Goldin Ln, Southold, NY 11971
  • /25

    $1,299,999

    • 4 Beds
    • 2 Baths
    • 1,576 Sq Ft

    52755 Soundview Ave, Southold, NY 11971

    Welcome to this One-of-a-Kind 4-Bedroom, Custom Built Colonial, Beachfront Property, ideally located on the North Fork of Long Island along the Beautiful LONG ISLAND SOUND! True Meaning of LOCATION! This Spectacular Waterfront Home offers Breathtaking Panoramic Views, Direct Beach Access (Southold Beach), and the Perfect Blend of Privacy and Coastal Charm. Wake up to Stunning Sunrises and the

    Argie Karavas BERKSHIRE HATHAWAY

    52755 Soundview Ave, Southold, NY 11971
  • /14

    $25,000 Per Month

    • 3 Beds
    • 1.5 Baths
    • 1,300 Sq Ft
    • House for Rent

    2662 Paradise Shores Rd, Southold, NY 11971

    Your quintessential North Fork summer starts here. Tucked away in the quiet beach community of Paradise Shores, this Bayfront cottage is the summer retreat you’ve been dreaming of. Positioned directly on Southold Bay with unobstructed views of Shelter Island, this charming cottage offers the best scenery on the North Fork. Whether you're hosting a sunset dinner or just enjoying a quiet morning,

    JoAnn Wind Daniel Gale Sothebys Intl Rlty

    2662 Paradise Shores Rd, Southold, NY 11971
  • 600 Parkway, Southold, NY 11971

    $910,000

    Sold Nov 03, 2025

    600 Parkway, Southold, NY 11971

    • 3 Beds
    • 1 Bath
    • 1,600 Sq Ft
    • Built 1969

    Last Sold Summary

    • 2% Above List Price
    • $569/SF
    • 12 Days On Market

    Current Estimated Value $901,522

    Last Listing Agent Alexis Meadows Compass Greater NY LLC

    600 Parkway, Southold, NY 11971
  • /18

    $960,000

    Pending
    • 3 Beds
    • 2 Baths
    • 1,700 Sq Ft

    340 Rambler Rd, Southold, NY 11971

    Set within the coveted private Terry Waters beach community in Southold, this beautiful three-bedroom, two-bath extended ranch offers relaxed coastal living in an enchanting, private setting. A welcoming entry opens to a spacious living room anchored by a classic brick fireplace, while the thoughtfully designed layout includes a primary bedroom with an ensuite bath, an additional bonus family

    Diane Mollica Compass Greater NY LLC

    340 Rambler Rd, Southold, NY 11971
  • /15

    $3,500 Per Month

    • 2 Beds
    • 1 Bath
    • House for Rent

    3825 S Harbor Rd, Southold, NY 11971

    Classic North Fork Beach home located just 10 homes away from South Harbor Beach and Park, Amazing comfort and privacy on this acre plus setting. Home is crisp, clean, and fully furnished ready for you to enjoy. South Harbors expansive beach offers an inlet to paddle board, kayak, fish, and relax on the water. Please call for availability; 2025 Rates: January- April $3500, May $5000, June $7000,

    Barbara Poliwoda Douglas Elliman Real Estate

    3825 S Harbor Rd, 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 $1,033,644

    Last Listing Agent Mariah Mills Daniel Gale Sothebys Intl Rlty

    1400 Calves Neck Rd, Southold, NY 11971
    • 1275 Ruch Ln, Southold, NY 11971

      Est $1,987,968

      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

  • /5

    $1,399,000

    $100K PRICE DROP
    • Land
    • 4.24 Acres
    • $329,953 per Acre

    18365 County Road 48, Southold, NY 11935

    Motivated Seller! Opportunity to own 4+ acres of buildable vacant land in the heart of Cutchogue on Long Island’s scenic North Fork. Water, electric, and natural gas connections are available at the street, making this an ideal site to build your dream home, private retreat, or investment property. Enjoy a peaceful setting surrounded by vineyards, farm stands, and open farmland, while being just

    Michael Graziose Redfin Real Estate

    18365 County Road 48, Southold, NY 11935
  • /20

    $19,000 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
  • 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 $724,536

    Last Listing Agent Nancy Cervelli Daniel Gale Sothebys Intl Rlty

    340 Pine Rd, Southold, NY 11971
  • /50

    $1,249,000

    Open Sat 11AM - 1PM $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
  • 54985 County Road 48, Southold, NY 11971

    $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 $2,479,458

    Last Listing Agent Nicholas Planamento William Raveis (Mattituck)

    54985 County Road 48, Southold, NY 11971

Showing Results 41 - 80, Page 2 of 18

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