4,571

Southold, NY Homes

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  • /3

    $824,000

    • Land
    • 26,571 Sq Ft
    • $1,350,820 per Acre

    705 Wildberry Ln, Southold, NY 11971

    A rare opportunity to create a custom North Fork residence in desirable Wildberry Fields. This .61-acre level, wooded parcel is situated on a private 9-lot country road and backed by picturesque vineyards, offering beautiful vineyard views and a peaceful, private setting.Protective covenants help preserve the character and value of the community, requiring residences of more than 3,000

    Kim Pirreca BERKSHIRE HATHAWAY

    705 Wildberry Ln, Southold, NY 11971
  • /26

    $15,000 Per Month

    • 4 Beds
    • 3 Baths
    • 2,700 Sq Ft
    • House for Rent

    1000 Rambler Rd, Southold, NY 11971

    Beautiful like new colonial just 500 feet from sandy bay beach. Four bedrooms plus a lovely sunroom. Fully Furnished. Enjoy your morning coffee on the bedroom balcony. Outside shower and gas grill off backyard deck. Bicycles and a kayak with trailer included. A perfect beach house. Available July $15,000, August-Labor Day $20,000, July-Labor Day $35,000, utilities included.

    Pamela Hunt Colony Realty

    1000 Rambler Rd, Southold, NY 11971
  • 58315 North Rd, Greenport, NY 11944

    $992,000

    Sold Dec 12, 2025

    58315 North Rd, Greenport, NY 11944

    • 2 Beds
    • 2 Baths
    • 900 Sq Ft
    • Built 1972

    Last Sold Summary

    • 6% Below List Price
    • $1,102/SF
    • 0 Days On Market

    Current Estimated Value $1,003,247

    Last Listing Agent Donna Fakiris Modern Age Realty Group LLC

    58315 North Rd, Greenport, NY 11944
    • 2375 Laurel Ave, Southold, NY 11971

      Not Listed For Sale

      2375 Laurel Ave, Southold, NY 11971

      • 4 Beds
      • 4.5 Baths
      • 3,960 Sq Ft
      • Built 2025
      2375 Laurel Ave, Southold, NY 11971

      Last Sold Summary

      • 11 Days On Market

      Last Listing Agent Kristy Naddell Douglas Elliman Real Estate

  • /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 - Excellent Location Near Town, Beaches & Vineyards! Discover the perfect blend of privacy, luxury and convenience with this exceptional 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" custom

    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

    July 2 Weeks $12,000!, Full Month $22,000! (details below)...Fabulous Lux Vacations on the coveted Esplanade in "Angel Shores". This Striking 4BR/2.5B Designer Style Home has just undergone an entire first floor renovation thru early 2025. Enjoy your private deeded sandy bay beach and heated freeform lagoon pool with a zen waterfall. Property is fully fenced and enclosed by lush mature specimen

    Kate Carpluk William Raveis New York LLC

    1275 the Esplanade, Southold, NY 11971
  • 155 Shepard Dr, Southold, NY 11971

    $791,000

    Sold Dec 02, 2025

    155 Shepard Dr, Southold, NY 11971

    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft
    • Built 1988

    Last Sold Summary

    • 21% Below List Price
    • $494/SF
    • 217 Days On Market

    Current Estimated Value $895,232

    Last Listing Agent Isaac Israel Richmond Realty Corp

    155 Shepard Dr, Southold, NY 11971
    • 2555 Youngs Ave Unit 5E, Southold, NY 11971

      Not Listed For Sale

      2555 Youngs Ave Unit 5E, Southold, NY 11971

      • 2 Beds
      • 2 Baths
      • 1,200 Sq Ft
      • Built 1985
      2555 Youngs Ave Unit 5E, Southold, NY 11971

      Last Sold Summary

      • 35 Days On Market

      Last Listing Agent Timothy O'Keefe Signature Premier Properties

  • /27

    $935,000

    $215K PRICE DROP Pending
    • 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

    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
  • 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 $1,349,237

    Last Listing Agent Roseann Prussen Signature Premier Properties

    3520 Old Rd N, Southold, NY 11971
    • 1150 Kenneys Rd, Southold, NY 11971

      Est $1,064,585

      Not Listed For Sale

      1150 Kenneys Rd, Southold, NY 11971

      1150 Kenneys Rd, Southold, NY 11971

      Last Sold Summary

      • 59 Days On Market

      Last Listing Agent Thomas McCarthy Thomas J McCarthy Real Estate

  • /3

    $1,550,000

    New Construction $150K PRICE INCREASE
    • 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
  • /17

    $5,000 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
  • 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
    • 200 Crittenden Ln, Southold, NY 11971

      Not Listed For Sale

      200 Crittenden Ln, Southold, NY 11971

      • 3 Beds
      • 2 Baths
      • 1,560 Sq Ft
      • Built 1964
      200 Crittenden Ln, Southold, NY 11971

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Katie DiGregorio Corcoran

  • /26

    $799,000

    Pending
    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft

    650 Greenfields Ln, Southold, NY 11971

    Welcome to 650 Greenfields Lane, an inviting ranch-style home on just shy an acre of property, nestled in the heart of Southold, NY. This charming residence offers three bedrooms, and two full bathrooms, which includes a primary en suite that overlooks the back yard. The home's cozy living room features a traditional fireplace, perfect for creating a warm and welcoming atmosphere. The eat-in

    Barbara Poliwoda Douglas Elliman Real Estate

    650 Greenfields Ln, 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
  • 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 $903,175

    Last Listing Agent Erica Kelly Daniel Gale Sothebys Intl Rlty

    920 Pine Neck Rd Unit 2D1, Southold, NY 11971
    • 650 Old Harbor Rd, Southold, NY 11971

      Est $1,798,590

      Not Listed For Sale

      650 Old Harbor Rd, Southold, NY 11971

      • 2 Beds
      • 3 Baths
      • 2,025 Sq Ft
      • Built 1971
      650 Old Harbor Rd, Southold, NY 11971

      Last Sold Summary

      • 27 Days On Market

      Last Listing Agent Bridget Elkin Compass Greater NY LLC

  • /37

    $574,999

    • 3 Beds
    • 1 Bath
    • 1,100 Sq Ft

    2600 Boisseau Ave, Southold, NY 11971

    Welcome to 2600 Boisseau Avenue, the best deal in all of Southold. This well-maintained 3-bedroom, 1-bath ranch situated on a spacious .39-acre property in the heart of the North Fork will not disappoint. Offering comfortable single-level living with plenty of potential, this home is a wonderful opportunity to enjoy everything the Southold lifestyle has to offer. Inside, you'll find a functional

    Zachary Scher Signature Premier Properties

    2600 Boisseau Ave, Southold, NY 11971
  • /22

    $15,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,280 Sq Ft
    • House for Rent

    570 Hippodrome Dr, Southold, NY 11971

    A quintessential North Fork retreat in Beixedon Estates in an extraordinary waterfront setting. Tucked beside the winding Hippodome Creek and surrounded by lush coastal landscape, this charming month-to-month rental offers privacy, tranquility, and beautiful water views just moments from the Bay. The property’s peaceful natural surroundings create the perfect backdrop for relaxed morning coffee

    Andrea Parks Douglas Elliman Real Estate

    570 Hippodrome Dr, Southold, NY 11971
  • 1815 Laurel Ave, Southold, NY 11971

    $2,725,000

    Sold Jun 15, 2026

    1815 Laurel Ave, Southold, NY 11971

    • 4 Beds
    • 4.5 Baths
    • 4,327 Sq Ft
    • Built 2025

    Last Sold Summary

    • 3% Below List Price
    • $630/SF
    • 127 Days On Market

    Current Estimated Value $2,724,818

    Last Listing Agent Kristy Naddell Douglas Elliman Real Estate

    1815 Laurel Ave, Southold, NY 11971
    • 1720 Carroll Ave, Peconic, NY 11958

      Est $729,196

      Not Listed For Sale

      1720 Carroll Ave, Peconic, NY 11958

      • 3 Beds
      • 2 Baths
      • 1,575 Sq Ft
      • Built 1957
      1720 Carroll Ave, Peconic, NY 11958

      Last Sold Summary

      • 18 Days On Market

      Last Listing Agent Bridget Elkin Compass Greater NY LLC

  • /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
  • 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
    • 500 Arshamomaque Ave, Southold, NY 11971

      Est $1,616,576

      Not Listed For Sale

      500 Arshamomaque Ave, Southold, NY 11971

      • 4 Beds
      • 5 Baths
      • 2,334 Sq Ft
      • Built 2024
      500 Arshamomaque Ave, Southold, NY 11971

      Last Sold Summary

      • 50 Days On Market

      Last Listing Agent Lisa Davey LI Probate Realty Inc

  • /25

    $1,149,999

    $150K PRICE DROP Pending
    • 3 Beds
    • 2 Baths
    • 1,576 Sq Ft

    52755 Soundview Ave, Southold, NY 11971

    Welcome to this One-of-a-Kind 3-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
  • /31

    $4,500 Per Month

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

    65 Lake Dr, Southold, NY 11971

    Two week minimum rental. Available in July and August, $4,500 / week. August 16 through Labor Day, $5,500/week. 3% discount for rentals longer than 3 weeks. Perfectly situated in one of the North Fork's most desirable beach communities, this welcoming 4-bedroom, 2-bath, 2-story beach bungalow is just a 3 minute stroll to the sandy shoreline of Kenney's Beach, 7 minutes to the Great Pond, a 10

    Jon Tomlinson Daniel Gale Sothebys Intl Rlty

    65 Lake Dr, Southold, NY 11971
  • 56055 County Road 48, Southold, NY 11971

    $1,250,000

    Sold Aug 19, 2026

    56055 County Road 48, Southold, NY 11971

    • 2 Beds
    • 1 Bath
    • 850 Sq Ft
    • Built 1920

    Last Sold Summary

    • 26% Above List Price
    • $1,471/SF
    • 28 Days On Market

    Last Listing Agent JoAnn Wind Daniel Gale Sothebys Intl Rlty

    56055 County Road 48, Southold, NY 11971
    • 5535 Old Rd N, Southold, NY 11971

      Est $934,588

      Not Listed For Sale

      5535 Old Rd N, Southold, NY 11971

      • 3 Beds
      • 1 Bath
      • 1,760 Sq Ft
      • Built 1949
      5535 Old Rd N, Southold, NY 11971

      Last Sold Summary

      • 102 Days On Market

      Last Listing Agent Tom Scalia Century 21 Albertson Realty

  • /33

    $1,277,000

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

    1025 Seawood Dr, Southold, NY 11971

    Welcome to 1025 Seawood Drive, where space, comfort, and the North Fork lifestyle come together beautifully!Experience the relaxed sophistication of North Fork living in this beautifully, maintained, move-in-ready 4 bedroom, 3.5 bath Colonial in the heart of Southold. Filled with natural light and designed for modern living this home features 9' ceilings, hardwood floors and an easy-flowing

    Clorinda Tagios Douglas Elliman Real Estate

    1025 Seawood Dr, Southold, NY 11971
  • /21

    $30,000 Per Month

    • 4 Beds
    • 2 Baths
    • 1,900 Sq Ft
    • House for Rent

    1225 Leeton Dr, Southold, NY 11971

    Summer is here, and this home has vacation written all over it. Enjoy spectacular sunset water views of the Long Island Sound from the spacious wrap-around deck or from the bright, open-concept living spaces inside. Perfect for entertaining, the layout features 4 bedrooms and 2 full bathrooms, offering a beautiful oasis for relaxation and togetherness. The lifestyle here is effortless: Kenny's

    Mackenzie Needham Daniel Gale Sothebys Intl Rlty

    1225 Leeton Dr, 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 $762,643

    Last Listing Agent Scott Bennett Douglas Elliman Real Estate

    150 Goldin Ln, Southold, NY 11971
    • 355 Cedar Dr, Southold, NY 11971

      Est $1,080,076

      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

      Last Listing Agent Carol Szynaka Daniel Gale Sothebys Intl Rlty

  • /3

    $699,000

    • Land
    • 32,670 Sq Ft
    • $932,000 per Acre

    49295 Route 25, Southold, NY 11971

    High-Visibility Commercial Land in Southold. Rare opportunity to acquire a highly visible vacant parcel along main road in Southold Town. Zoned "General Business", the property offers a wide range of potential uses and flexibility for an owner-user, investor, or contractor. Permitted uses include retail and wholesale businesses, convenience store, contractor-related uses, storage, and residential

    Melissa Principi Douglas Elliman Real Estate

    49295 Route 25, 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; 2027 Rates: January- April $3500, May $5000, June $7000,

    Barbara Poliwoda Douglas Elliman Real Estate

    3825 S Harbor 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 $913,898

    Last Listing Agent Alexis Meadows Compass Greater NY LLC

    600 Parkway, Southold, NY 11971
    • 1095 Oak Ave, Southold, NY 11971

      Est $802,782

      Not Listed For Sale

      1095 Oak Ave, Southold, NY 11971

      • 3 Beds
      • 1 Bath
      • Built 1939
      1095 Oak Ave, Southold, NY 11971

      Last Sold Summary

      • 19 Days On Market

      Last Listing Agent Gayle Marriner Smith Daniel Gale Sothebys Intl Rlty

Showing Results 41 - 80, Page 2 of 18

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