4,634

Southold, NY Homes

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  • /41

    $1,399,000

    Pending
    • 4 Beds
    • 2.5 Baths
    • 2,690 Sq Ft

    1025 Long Creek Dr, Southold, NY 11971

    Welcome to your North Fork waterfront oasis in highly desirable Yennecott Park, offering the rare combination of privacy, natural beauty, and effortless access to all. Perfectly positioned along scenic Long Creek with views toward Hashamomuck Preserve, this 4-bedroom waterfront home delivers a relaxed coastal lifestyle. Set on .75 acres with lush mature landscaping and generous water frontage,

    Susan Orioli Engel & Volkers North Fork

    1025 Long Creek Dr, 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
  • 1710 N Bayview Road Extension, Southold, NY 11971

    $2,250,000

    Sold Oct 24, 2025

    1710 N Bayview Road Extension, Southold, NY 11971

    • 4 Beds
    • 4.5 Baths
    • 3,700 Sq Ft
    • Built 2005

    Last Sold Summary

    • 2% Below List Price
    • $608/SF
    • 13 Days On Market

    Current Estimated Value $2,186,491

    Last Listing Agent Eric Elkin Compass Greater NY LLC

    1710 N Bayview Road Extension, Southold, NY 11971
  • /4

    $1,600,000

    • Land
    • 2 Acres
    • $800,000 per Acre

    55975 Route 25, Southold, NY 11971

    2 Acres Of Highly Desirable Hamlet Business Zoning. Subdividable Into Half Acre Lots Or Build Multiple Structures. Multiple Residential Units Possible Or Residential/Commercial Mix. 4 Buildings Possible As Of Right. Great Route 25 Exposure & Great Location In Center Of Hamlet! Commercial Listing MLS# 3530579

    Colin McCarthy Thomas J McCarthy Real Estate

    55975 Route 25, Southold, NY 11971
  • /30

    $30,000 Per Month

    • 4 Beds
    • 3.5 Baths
    • 3,800 Sq Ft
    • House for Rent

    365 Chablis Path, Southold, NY 11971

    Space, Luxury, and Privacy Await in This Stunning Contemporary Home! Experience the perfect blend of elegance and comfort in this beautiful home, offering an expansive backyard ideal for dining, lounging, and entertaining. Enjoy endless hours of relaxation in the inground pool, or gather with loved ones in the spacious yard. A charming gazebo provides a welcome retreat from the sun, weather, or

    Diane Arpaia Signature Premier Properties

    365 Chablis Path, Southold, NY 11971
  • 55 Cedar Point Dr W, Southold, NY 11971

    $1,035,000

    Sold Jun 20, 2025

    55 Cedar Point Dr W, Southold, NY 11971

    • 3 Beds
    • 2 Baths
    • 1,650 Sq Ft
    • Built 1973

    Last Sold Summary

    • 5% Below List Price
    • $627/SF
    • 62 Days On Market

    Current Estimated Value $1,114,414

    Last Listing Agent Kristy Naddell Douglas Elliman Real Estate

    55 Cedar Point Dr W, Southold, NY 11971
  • /20

    $1,150,000

    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
  • /31

    $16,000 Per Month

    • 4 Beds
    • 3.5 Baths
    • House for Rent

    75 Clearview Ave, Southold, NY 11971

    2026 Rates: NO AVAILABILITY New Modern Farmhouse Completed in 2021 and located in the heart Hog's Neck in Southold Hamlet. This home features an impressive 20 x 50 heated pool with electric cover, out door shower and sprawling paver patio. The interior is open and airy with Chef's Kitchen outfitted with Thermador appliances, large living room with built in shelving, gas fireplace and formal

    William Walters Daniel Gale Sothebys Intl Rlty

    75 Clearview Ave, Southold, NY 11971
  • 390 Wildberry Ln, Southold, NY 11971

    $780,000

    Sold Jan 06, 2026

    390 Wildberry Ln, Southold, NY 11971

    • Land
    • 29,185 Sq Ft
    • $1,164,179 per Acre

    Last Sold Summary

    • 2% Below List Price
    • 18 Days On Market

    Current Estimated Value $799,333

    Last Listing Agent Robert Merolla Aurora Property Group

    390 Wildberry Ln, Southold, NY 11971
  • /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
  • /29

    $12,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • House for Rent

    250 Wesland Rd, Southold, NY 11971

    JUST A DREAM BOAT! NEWLY RENOVATED, LIGHT AND BRIGHT, BEAUTIFULLY APPOINTED, EVERY CONVENIENCE - 2 BEDROOMS, 2 BATHS. PLUS -SUPER COMFORTABLE CONVERTIBLE QUEEN SOFABED! BEAUTIFUL OUTDOOR DINING, FIRE PIT, PORCH, ENCLOSED SHOWER! PRICED RIGHT! STEPS TO POPULAR KENNEY'S BEACH - JUST BRING OUR LITTLE RED WAGON AND STROLL TO THE BEACH AND ENJOY! Additional information: Appearance excellent! Lease

    Marie Beninati Beninati Associates

    250 Wesland Rd, Southold, NY 11971
  • 1750 Mount Beulah Ave, Southold, NY 11971

    $3,850,000

    Sold Aug 25, 2025

    1750 Mount Beulah Ave, Southold, NY 11971

    • 6 Beds
    • 5.5 Baths
    • 6,000 Sq Ft
    • Built 1915

    Last Sold Summary

    • 4% Below List Price
    • $642/SF
    • 17 Days On Market

    Current Estimated Value $3,510,000

    Last Listing Agent Kristy Naddell Douglas Elliman Real Estate

    1750 Mount Beulah 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
  • /20

    $8,000 Per Month

    • 2 Beds
    • 3 Baths
    • 1,000 Sq Ft
    • Apartment for Rent

    345 Old Cove Blvd, Southold, NY 11971

    Seasonal Rental | 345 Old Cove Blvd, Southold Set directly across from Town Beach in Southold, this beautifully maintained seasonal rental captures the best of North Fork coastal living with unobstructed water views, direct beach access, and a relaxed indoor-outdoor lifestyle. Located within a private home built approximately six years ago, the apartment offers its own private side entrance from

    Basil Boziotis Compass Greater NY LLC

    345 Old Cove Blvd, Southold, NY 11971
  • 4710 Old Rd N, Southold, NY 11971

    $1,350,000

    Sold Sep 05, 2025

    4710 Old Rd N, Southold, NY 11971

    • 4 Beds
    • 2.5 Baths
    • 2,400 Sq Ft
    • Built 1978

    Last Sold Summary

    • 8% Above List Price
    • $562/SF
    • 24 Days On Market

    Current Estimated Value $1,344,179

    Last Listing Agent Zachary Scher Signature Premier Properties

    4710 Old Rd N, 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
  • /22

    $30,000 Per Month

    • 5 Beds
    • 4.5 Baths
    • 3,233 Sq Ft
    • House for Rent

    1700 Cedar Dr, Southold, NY 11971

    2026 Availability: June $30,000. July RENTED. Perfect summer getaway with 5 bed, 4.5 bath in the heart of the North Fork. The home sits on 1.24 acres and features an open floor plan, large screened-in porch, full finished basement, wood burning fireplace, outdoor shower, and a saltwater, gunite pool. The primary bedroom has a large roof deck overlooking the pool and rear yard. Bedrooms and full

    Shane Hafer Compass Greater NY LLC

    1700 Cedar Dr, Southold, NY 11971
  • 2555 Youngs Ave Unit 7D, Southold, NY 11971

    $500,000

    Sold Oct 21, 2025

    2555 Youngs Ave Unit 7D, Southold, NY 11971

    • 2 Beds
    • 2 Baths
    • 1,100 Sq Ft
    • Built 1987

    Last Sold Summary

    • 13% Below List Price
    • $455/SF
    • 250 Days On Market

    Last Listing Agent Timothy O'Keefe Signature Premier Properties

    2555 Youngs Ave Unit 7D, 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
  • /17

    $9,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,750 Sq Ft
    • House for Rent

    1265 Brigantine Dr, Southold, NY 11971

    Impeccable, like new ranch for rent with quality features throughout in Harbor Lights with a deeded beach and park at the end of the street. There are three bedrooms, two full bathrooms, open floor plan from kitchen through the dining area into the vaulted ceiling living room, Enjoy the beautiful screened in porch which overlooks the private back yard with slate patio, grass lawn, and outdoor

    Barbara Poliwoda Douglas Elliman Real Estate

    1265 Brigantine Dr, Southold, NY 11971
  • 6815 Soundview Ave, Southold, NY 11971

    $975,000

    Sold Aug 28, 2025

    6815 Soundview Ave, Southold, NY 11971

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Built 1938

    Last Sold Summary

    • 3% Above List Price
    • $812/SF
    • 9 Days On Market

    Current Estimated Value $1,000,502

    Last Listing Agent Donielle Cardinale Daniel Gale Sothebys Intl Rlty

    6815 Soundview Ave, 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
  • /28

    $7,500 Per Month

    • 4 Beds
    • 2 Baths
    • 2,000 Sq Ft
    • House for Rent

    3400 Youngs Ave, Southold, NY 11971

    Beautifully renovated North Fork farmhouse retreat blending relaxed luxury with resort-style outdoor living. Set on a private, tree-lined property, the home features a heated saltwater pool, expansive lawn, dramatic landscape lighting, and multiple indoor/outdoor entertaining spaces designed for unforgettable summer living. Thoughtfully updated interiors, a detached pool house, and curated

    Thomas McCarthy Thomas J McCarthy Real Estate

    3400 Youngs Ave, Southold, NY 11971
  • 20845 Soundview Ave, Southold, NY 11971

    $1,730,000

    Sold Nov 12, 2025

    20845 Soundview Ave, Southold, NY 11971

    • 3 Beds
    • 2 Baths
    • 1,408 Sq Ft
    • Built 1951

    Last Sold Summary

    • 4% Below List Price
    • $1,229/SF
    • 39 Days On Market

    Current Estimated Value $1,789,701

    Last Listing Agent Stephanie Ranghelli Realty Connect USA LI Inc

    20845 Soundview Ave, Southold, NY 11971
    • /2

      Est $779,705

      Not Listed For Sale

      1430 Bay Haven Ln, Southold, NY 11971

      • 3 Beds
      • 2 Baths
      • Built 1973
      1430 Bay Haven Ln, Southold, NY 11971

      Last Sold Summary

  • /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
  • /42

    $4,900 Per Month

    • 4 Beds
    • 2 Baths
    • 2,000 Sq Ft
    • House for Rent

    6710 Soundview Ave, Southold, NY 11971

    Enjoy Southold this Summer at a Sleek Scandinavian Style Farm Ranch. Available for Bi-Weekly Rental Only. The Rate is Weekly at a Bi-Weekly Minimum. Nestled on Shy 2.5 Acres of Private Wooded Property You Can Truly Get Away from It All. Constructed in 2022 for Elegance and Comfort. Complete One Level Living at Its Finest. The Home Boasts a Grand Open Layout with Vaulted Ceilings Throughout.

    Rene Giacobbe Douglas Elliman Real Estate

    6710 Soundview Ave, Southold, NY 11971
  • 350 Brigantine Dr, Southold, NY 11971

    $750,750

    Sold Mar 27, 2026

    350 Brigantine Dr, Southold, NY 11971

    • 3 Beds
    • 2 Baths
    • 975 Sq Ft
    • Built 1986

    Last Sold Summary

    • 20% Above List Price
    • $770/SF
    • 31 Days On Market

    Current Estimated Value $677,661

    Last Listing Agent Nicole Petersen Century 21 Icon

    350 Brigantine Dr, Southold, NY 11971
    • 380 Gin Ln, Southold, NY 11971

      Est $1,025,765

      Not Listed For Sale

      380 Gin Ln, Southold, NY 11971

      • 6 Beds
      • 3 Baths
      • 3,784 Sq Ft
      • Built 1960
      380 Gin Ln, Southold, NY 11971

      Last Sold Summary

      • 88 Days On Market

  • /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
  • /24

    $15,000 Per Month

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

    935 Corey Creek Ln, Southold, NY 11971

    Experience the ultimate North Fork summer in this stunning new construction home, designed for effortless entertaining and elevated coastal living. Professionally decorated and impeccably finished, this residence offers three bedrooms, four full bathrooms, a bonus room, and a beautifully finished lower level with an additional private half bath. Step outside to your own private retreat featuring

    Melissa Principi Douglas Elliman Real Estate

    935 Corey Creek Ln, Southold, NY 11971
  • 54985 Middle Rd, Southold, NY 11971

    $2,700,000

    Sold Sep 25, 2025

    54985 Middle Rd, Southold, NY 11971

    • 4 Beds
    • 5 Baths
    • 3,500 Sq Ft
    • Built 2010

    Last Sold Summary

    • 16% Below List Price
    • $771/SF
    • 133 Days On Market

    Last Listing Agent Nicholas Planamento William Raveis New York LLC

    54985 Middle Rd, Southold, NY 11971

Showing Results 81 - 120, Page 3 of 18

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