Southold, NY Homes

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  $4,495,000

  • Land
  • 36 Acres
  • $124,861 per Acre

  50100 County Road 48, Southold, NY 11971

  Attention Developers and Discerning Investors! Opportunity knocks with this 36-acre parcel, Development Rights in Tact, nestled in the heart of the North Fork. Ideally positioned along Arshamomack Creek with access to both County and Municipal roadways, this property offers a perfect setting for the development of either workforce housing, an exclusive residential enclave or a private estate. A

  Lisa Gillooly Compass Greater NY LLC

  50100 County Road 48, Southold, NY 11971
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  /19

  $28,000 per month

  • 3 Beds
  • 2 Baths
  • House for Rent

  1100 Pine Ave, Southold, NY 11971

  Permit #: 0160. This Superb 3-Bedroom, 2-Bathroom Ranch Home Showcases Gorgeous Water Views And Is Strategically Located Near Goose Creek Beach And The Pulsating Heart Of Southold, Allowing You To Enjoy The Best Of Both Worlds. The Interior Is Beautifully Designed With A Minimalist Aesthetic, Offering A Serene Retreat From The Every Day Hustle And Bustle. The Open Layout Allows For Easy Movement

  Colin McCarthy Thomas J McCarthy Real Estate

  1100 Pine Ave, Southold, NY 11971
• 

  $998,500 Sold Mar 21, 2025

  1150 Kenneys Rd, Southold, NY 11971

  • Land
  • 6.96 Acres
  • $143,463 per Acre

  Last Sold Summary

  • 9% Below List Price
  • 59 Days On Market

  Current Estimated Value $1,044,254

  Last Listing Agent Thomas McCarthy Thomas J McCarthy Real Estate

  1150 Kenneys Rd, Southold, NY 11971
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  Est $1,034,242 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,167 Sq Ft

  465 Windjammer Dr, Southold, NY 11971

  465 Windjammer Dr, Southold, NY 11971
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  /7

  $1,499,000

  • 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 & vineyards,

  Kathleen Travers Douglas Elliman Real Estate

  11200 N Bayview Rd, Southold, NY 11971
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  /13

  $7,000 per month

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

  Unlisted Address

  Experience the charm of this delightful rental cottage nestled in Southold, North Fork, just a stone’s throw from Founder's Landing Park and Wharf House, with one of the most amazing sugar sand beaches in our community. This unique, fully furnished one-bedroom retreat features flexible rental periods and competitive rates throughout the year.Imagine waking up to the serene views of a

  Nicholas Planamento William Raveis New York LLC

  Unlisted Address
• 

  $1,020,000 Sold Jan 16, 2025

  375 Kenneys Rd, Southold, NY 11971

  • 4 Beds
  • 2.5 Baths
  • 2,700 Sq Ft
  • Built 2004

  Last Sold Summary

  • 2% Above List Price
  • $378/SF
  • 29 Days On Market

  Current Estimated Value $1,137,605

  Last Listing Agent Regan Battuello The Agency Northshore NY

  375 Kenneys Rd, Southold, NY 11971
• 

  Est $2,878,000 Not Listed For Sale

  • 5 Beds
  • 6 Baths
  • 5,000 Sq Ft

  165 Deer Run, Southold, NY 11971

  165 Deer Run, Southold, NY 11971
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  /29

  $899,000

  • 3 Beds
  • 2 Baths
  • 1,550 Sq Ft

  515 Corey Creek Ln, Southold, NY 11971

  Welcome to this beautifully maintained 3-bedroom, 2-bath ranch set on a pristine half-acre. Enjoy the best of indoor and outdoor living with a spacious living room w/FP, bright den and primary BR ensuite. Step outside to your own private oasis - an expansive 16'x32' inground pool surrounded by manicured landscaping and plenty of room for entertaining. Private cul de sac and association with its

  Thomas McCarthy Thomas J McCarthy Real Estate

  515 Corey Creek Ln, Southold, NY 11971
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  /26

  $17,000 per month

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

  1175 Waterview Dr, Southold, NY 11971

  Southold Goose Creek Waterfront Home. Immaculate sun-filled home with all you will need to relax and enjoy summer. Large living room, and dining room. Well equipped Kitchen with sliders to deck, Den with amazing water views. Ensuite bedroom with water views, 2 additional bedrooms and bathrooms. Furnished deck and large yard. There is a dock to fish, boat, paddle board or kayak (2 included) from

  Amy Kirincic The Agency Northshore NY

  1175 Waterview Dr, Southold, NY 11971
• 

  $810,000 Sold Sep 10, 2025

  50605 Route 25, Southold, NY 11971

  • 2 Beds
  • 1.5 Baths
  • Built 1701

  Last Sold Summary

  • 9% Below List Price
  • 67 Days On Market

  Current Estimated Value $821,603

  Last Listing Agent Mariah Mills Daniel Gale Sothebys Intl Rlty

  50605 Route 25, Southold, NY 11971
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  Est $1,051,169 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,000 Sq Ft

  5845 N Bayview Rd, Southold, NY 11971

  5845 N Bayview Rd, Southold, NY 11971
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  /14

  $899,000

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

  385 Cottage Place, Southold, NY 11971

  Stately and classic vintage farmhouse with wrap-around porch, original in-tact architectural details and hardwood floors throughout. Built in 1900 as part of the Southold Hotel on Main Road. Moved to current location in 1920. Beautifully maintained with lots of natural light, eat-in kitchen, large private back yard, walking/biking distance to Southold Village and Founders Landing Park with

  Janet Markarian Daniel Gale Sothebys Intl Rlty

  385 Cottage Place, Southold, NY 11971
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  /19

  $6,500 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

  Kenneth Poliwoda Douglas Elliman Real Estate

  1975 Youngs Ave, Southold, NY 11971
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  $1,240,000 Sold Dec 23, 2025

  58425 Route 48, Greenport, NY 11944

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft
  • Built 1982

  Last Sold Summary

  • 11% Below List Price
  • $954/SF
  • 356 Days On Market

  Last Listing Agent William Walters Daniel Gale Sothebys Intl Rlty

  58425 Route 48, Greenport, NY 11944
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  Est $1,288,710 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,100 Sq Ft

  400 Ships Dr, Southold, NY 11971

  400 Ships Dr, Southold, NY 11971
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  /25

  $635,000 Pending

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

  3680 Main Bayview Rd, Southold, NY 11971

  Southold - Jonathan Jennings House circa 1761- Moved to its current location in 1761, this clapboard home has historical and architectural significance. The original wood frame house was built with interlocking joists and carelessly dressed ceiling beams. The house has a baker's brick oven with an ash pit, two fireplaces, and a brick foundation. Reportedly the first owner, Jonathan Jennings,

  Barry Novick Daniel Gale Sothebys Intl Rlty

  3680 Main Bayview Rd, Southold, NY 11971
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  /25

  $24,000 per month

  • 3 Beds
  • 1 Bath
  • House for Rent

  400 Diamond Ln, Peconic, NY 11958

  Memorial Day – Labor Day: $24,000.00 // June: $6,000.00 // July: $10,000.00 // August: $12,000.00 Enjoy stunning water views and all-season access to the Sound from this charming 3-bedroom, 1-bathroom waterfront home. This cozy home channels happy, mid-century vibes. Large living room with fireplace, dining nook, and sunroom, all with breathtaking views of the water. The patio with BBQ is the

  Sheri Winter Parker Corcoran

  400 Diamond Ln, Peconic, NY 11958
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  $1,130,000 Sold Sep 30, 2025

  70 Mockingbird Ln, Southold, NY 11971

  • 4 Beds
  • 3 Baths
  • Built 2001

  Last Sold Summary

  • 16% Below List Price
  • 143 Days On Market

  Last Listing Agent Kelly Gatanas Daniel Gale Sothebys Intl Rlty

  70 Mockingbird Ln, Southold, NY 11971
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  Est $1,977,874 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 3,200 Sq Ft

  210 Northfield Ln, Southold, NY 11971

  210 Northfield Ln, Southold, NY 11971
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  /38

  $2,295,000

  • 4 Beds
  • 3 Baths
  • 3,769 Sq Ft

  450 Sterling Woods Ln, Southold, NY 11971

  Spacious Open Plan Home with So Much to Offer near Several Great Beaches. Open Livingroom, Dining Room, Kitchen, a Separate Den and a Separate Office as well as a Good Size Bedroom and Bath on First Floor. The Spacious Kitchen Offers Sub Zero Refrigerator, a Wine Fridge and a Separate Fridge Dedicated to Drinks You Grab on Way to Pool. Primary Ensuite and Two Additional Bedrooms and Hall Bath on

  Paul Loeb Douglas Elliman Real Estate

  450 Sterling Woods Ln, Southold, NY 11971
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  /21

  $60,000 per month

  • 3 Beds
  • 2 Baths
  • House for Rent

  355 Windjammer Dr, Southold, NY 11971

  This soothing beach house is so Zen, you will feel like you are at a spa retreat! Peaceful and perfectly appointed, the backyard features a fabulous lagoon style pool, with a waterfall and hot tub, an amazing outdoor kitchen and bar, bathroom and outdoor shower! 3 bedrooms, 2 baths, including a spacious primary suite with a gorgeous spa like bathroom. All this and steps to the association beach!

  Sheri Winter Parker Corcoran

  355 Windjammer Dr, Southold, NY 11971
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  $407,000 Sold Nov 12, 2025

  500 Summer Ln, Southold, NY 11971

  • 2 Beds
  • 1.5 Baths
  • 880 Sq Ft
  • Built 1971

  Last Sold Summary

  • 17% Below List Price
  • $462/SF
  • 116 Days On Market

  Last Listing Agent Tom Scalia Century 21 Albertson Realty

  500 Summer Ln, Southold, NY 11971
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  Est $757,071 Not Listed For Sale

  • 3 Beds
  • 1 Bath

  275 Victoria Dr, Southold, NY 11971

  275 Victoria Dr, Southold, NY 11971
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  /40

  $1,150,000 Pending

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

  3700 Minnehaha Blvd, Southold, NY 11971

  3700 Minnehaha Blvd., Southold, a darling waterfront home nestled in Laughing Waters private beach community. This home is NOT in a flood zone!!! NO flood insurance is required! This house has something for everyone! For boaters, this home is so convenient, with its very own bulkhead and easy access to the Great Peconic Bay, just untie your boat and go! For nature lovers, the views and

  Rita Rooney Douglas Elliman Real Estate

  3700 Minnehaha Blvd, Southold, NY 11971
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  /32

  $19,500 per month

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • House for Rent

  1355 Watersedge Way, Southold, NY 11971

  Welcome to 1355 Watersedge Way, a delightful Bayfront home offering breathtaking water and sunset views in Southold. Nestled next to a nature preserve with 300 feet of private beach, this home provides both serenity and direct water access.Inside, the spacious living room features a smart TV and a wall of sliding glass doors that open to a waterside deck, perfect for enjoying the bay breeze.

  Jeanmarie Bay William Raveis New York LLC

  1355 Watersedge Way, Southold, NY 11971
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  $365,000 Sold Jun 17, 2025

  55075 Main Rd Unit 1, Southold, NY 11971

  • 2 Beds
  • 1 Bath
  • 805 Sq Ft
  • Built 1968

  Last Sold Summary

  • 9% Below List Price
  • $453/SF
  • 72 Days On Market

  Last Listing Agent Scott Bennett Douglas Elliman Real Estate

  55075 Main Rd Unit 1, Southold, NY 11971
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  Est $973,555 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft

  1075 Victoria Dr, Southold, NY 11971

  1075 Victoria Dr, Southold, NY 11971
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  /44

  $1,695,000

  • 3 Beds
  • 3 Baths
  • 1,850 Sq Ft

  3630 Soundview Ave, Peconic, NY 11958

  3630 Soundview Avenue in Peconic offers the perfect balance of modern living and coastal charm- a nature lovers paradise Tucked along Southold’s Sound-front corridor, this newly renovated contemporary is just across the street from a dune trail leading directly to a sandy beach. Goldsmith's Inlet, Kenney's Beach and McCabe's Beach are also close by, giving you endless opportunities to enjoy the

  Scott Bennett Douglas Elliman Real Estate

  3630 Soundview Ave, Peconic, NY 11958
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  /25

  $7,500 per month

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

  3400 Youngs Ave, Southold, NY 11971

  Permit #493 Newly Renovated Farmhouse Centrally Located In Southold With Easy Access By Bus, Train or Car. Enjoy Your Morning Coffee As The Sun Rises Over The Farm Field. Spend An Afternoon Exploring The Beauty of the North Fork, Soak in the Sun at one of the Beautiful Peconic Bay or Long Island Sound Beaches, Enjoy Live Music at Numerous Wineries and/or Breweries, Browse unique local finds at

  Thomas McCarthy Thomas J McCarthy Real Estate

  3400 Youngs Ave, Southold, NY 11971
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  $525,000 Sold May 28, 2025

  900 Pine Ave, Southold, NY 11971

  • 3 Beds
  • 1 Bath
  • 900 Sq Ft
  • Built 1961

  Last Sold Summary

  • 5% Below List Price
  • $583/SF
  • 35 Days On Market

  Current Estimated Value $567,206

  Last Listing Agent Diana Mellone Daniel Gale Sothebys Intl Rlty

  900 Pine Ave, Southold, NY 11971
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  Est $1,069,801 Not Listed For Sale

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

  750 Cedar Dr, Southold, NY 11971

  750 Cedar Dr, Southold, NY 11971
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  /43

  $2,995,000

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

  10947 N Bayview Rd, Southold, NY 11971

  Set on over two secluded acres within the coveted Shellfisher Preserve association near Paradise Point, this extraordinary estate offers sweeping water views from the backyard, kitchen, and upstairs rooms. A private deeded beach and your own deep-water dock is just a short pathway away. The property is graced by a pristine tidal lagoon, preserved and maintained by the Peconic Land Trust. The

  Melissa Principi Douglas Elliman Real Estate

  10947 N Bayview Rd, Southold, NY 11971
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  /29

  $10,500 per month

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

  250 Wesland Rd, Southold, NY 11971

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

  Marie Beninati Beninati Associates

  250 Wesland Rd, Southold, NY 11971
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  $725,000 Sold Jan 31, 2025

  155 Glover St, Southold, NY 11971

  • 2 Beds
  • 2 Baths
  • 1,300 Sq Ft

  Last Sold Summary

  • 7% Above List Price
  • $558/SF
  • 15 Days On Market

  Current Estimated Value $793,813

  Last Listing Agent Kenneth Poliwoda Douglas Elliman Real Estate

  155 Glover St, Southold, NY 11971
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  Est $1,406,933 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,793 Sq Ft

  750 Highwood Rd, Southold, NY 11971

  750 Highwood Rd, Southold, NY 11971
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  /36

  $1,215,000 Pending

  • 3 Beds
  • 1.5 Baths
  • 1,068 Sq Ft

  633 Pine Neck Rd, Southold, NY 11971

  A must see secluded water front Compound. Rarely do you find two houses on a one acre lot. Main cottage is 3 BR, Eik, FDR,, LR with fireplace, hardwood floors, basement and inviting water side covered porch, second cottage has Primary ensuite and guest Br with second bath, Eik, LR w/Fireplace hardwood floors full basement. Small out building, Additional information: Appearance:Very good

  Tom Uhlinger Douglas Elliman Real Estate

  633 Pine Neck Rd, Southold, NY 11971
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  /34

  $30,000 per month

  • 8 Beds
  • 7 Baths
  • 5,400 Sq Ft
  • House for Rent

  650 Pine Ave, Southold, NY 11971

  Permit 816. Beautiful New Construction In Private Beach Community. Creekfront Beach Access Along With 20x40 Heated Saltwater Pool. Ideal For Large Groups & Perfect For Entertaining, This Property Has It All. 8 Bedrooms And 7 Bathrooms Set On Lush Manicured Grounds, Provides Spacious Accommodations For Up To 16 Guests. Spend Afternoons Lounging By The Pool & Evenings Gathering With Family And

  Colin McCarthy Thomas J McCarthy Real Estate

  650 Pine Ave, Southold, NY 11971
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  $785,000 Sold Sep 12, 2025

  6980 N Bayview Rd, Southold, NY 11971

  • 3 Beds
  • 2 Baths
  • 1,650 Sq Ft
  • Built 1989

  Last Sold Summary

  • 6% Below List Price
  • $476/SF
  • 96 Days On Market

  Current Estimated Value $815,566

  Last Listing Agent Nicholas Planamento William Raveis New York LLC

  6980 N Bayview Rd, Southold, NY 11971
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  Est $965,601 Not Listed For Sale

  • 3 Beds
  • 2 Baths

  430 Highwood Rd, Southold, NY 11971

  430 Highwood Rd, Southold, NY 11971

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