Southold, NY Homes

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  /29

  $3,295,000

  • 4 Beds
  • 5.5 Baths
  • 7,341 Sq Ft

  80 Deer Run, Southold, NY 11971

  Southold Stunner- New ConstructionThis one's a North Fork knockout. Set at the end of a quiet cul de sac on over 2 private acres, minutes from the sand, the house was built to check every box. Inside you're met with all-day sunshine, four legit bedrooms, 4.5 spa-like baths (sanitary system in place for 7 bedrooms), and a true chef's kitchen-with a 48" Sub Zero, Wolf double range + wall oven,

  Sheri Winter Parker Corcoran

  80 Deer Run, Southold, NY 11971
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  /30

  $26,000 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
• 

  $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
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  /2

  Est $836,763 Not Listed For Sale

  • 3 Beds
  • 2 Baths

  1430 Bay Haven Ln, Southold, NY 11971

  1430 Bay Haven Ln, Southold, NY 11971
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  /28

  $4,495,000

  • 7 Beds
  • 7.5 Baths
  • 7,300 Sq Ft

  19620 Soundview Ave, Southold, NY 11971

  Experience the epitome of luxury living in this modern newly construction estate, a truly unique offering on the East End framed by breathtaking vineyard views. This newly constructed estate is move in ready with C/O in hand and spans an impressive 7,300 square feet, is a testament to meticulous craftsmanship and thoughtful design, where simplicity meets elegance. Upon arrival, you are greeted by

  Alexis Meadows Douglas Elliman Real Estate

  19620 Soundview Ave, Southold, NY 11971
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  /25

  $50,000 per month

  • 5 Beds
  • 3 Baths
  • 2,000 Sq Ft
  • House for Rent

  1160 Goose Creek Ln, Southold, NY 11971

  Available: July $50,000; Aug - LD: $50,000; July/Aug-LD $85,000Step back in time-without sacrificing comfort-in this beautifully preserved 5-bedroom, 3-bath home brimming with charm and nestled along the tranquil banks of Goose Creek. Surrounded by water on two sides and set on a private road, this unique property offers a rare blend of historic character and modern amenities. From the moment

  Sheri Winter Parker Corcoran

  1160 Goose Creek Ln, Southold, NY 11971
• 

  $599,000 Sold May 21, 2025

  45 Smith Dr N, Southold, NY 11971

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • Built 1959

  Last Sold Summary

  • $666/SF
  • 11 Days On Market

  Current Estimated Value $596,780

  Last Listing Agent Kristy Naddell Douglas Elliman Real Estate

  45 Smith Dr N, Southold, NY 11971
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  Est $3,400,333 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 4,051 Sq Ft

  9502 N Bayview Rd, Southold, NY 11971

  9502 N Bayview Rd, Southold, NY 11971
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  /2

  $795,000 Pending

  • Land
  • 0.67 Acre
  • $1,186,567 per Acre

  390 Wildberry Ln, Southold, NY 11971

  Luxury Builders Dream Lot and Ideal for a Land Buyer Who Wants to Build Their Dream Home in a World-Class Location. Building Permit Already Intact for 4,000+ Sq. Ft. Ultra-Luxury Residence. Seller Has Furnished Model of Identical Residence on Display at 2820 Stanley Road, Mattituck. A Shovel-Ready Building Lot, Perched Within a Waterview Cul-de-sac Development and Adjacent to Pastoral

  Robert Merolla Aurora Property Group

  390 Wildberry Ln, Southold, NY 11971
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  /18

  $3,500 per month

  • 3 Beds
  • 2 Baths
  • 1,100 Sq Ft
  • House for Rent

  315 Lake Dr, Southold, NY 11971

  Rental Permit # 0966 Fantastic home set directly on Great Pond and a block (975 feet) from Kenney's Beach with restaurant Little Fish just around the corner. This bright 3 bedroom and 2 full bathroom, with a 3 season room all window porch home has an expansive rear deck overlooking the fresh water pond. Watch osprey dive bomb for fresh water bass while geese, ducks and egrets meander across the

  Alexander Aquino Douglas Elliman Real Estate

  315 Lake Dr, Southold, NY 11971
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  $1,900,000 Sold Mar 18, 2025

  670 Kenneys Rd, Southold, NY 11971

  • 4 Beds
  • 2.5 Baths
  • 2,417 Sq Ft
  • Built 2025

  Last Sold Summary

  • 4% Below List Price
  • $786/SF
  • 4 Days On Market

  Current Estimated Value $1,805,607

  Last Listing Agent Robert Merolla Aurora Property Group

  670 Kenneys Rd, Southold, NY 11971
• 

  Est $895,119 Not Listed For Sale

  • 2 Beds
  • 1 Bath

  580 Jacobs Ln, Southold, NY 11971

  580 Jacobs Ln, Southold, NY 11971
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  /34

  $2,395,000

  • 4 Beds
  • 4.5 Baths
  • 3,238 Sq Ft

  1665 Glenn Rd, Southold, NY 11971

  Southold-West Creek Estates - Beautifully appointed, light-filled home. Recently completed with attention to every detail. A wood and glass front door and natural wood architectural accents set the tone at the front entrance. The large great room features a living area with a two-sided gas fireplace, dining area, and a generous chefs eat-in kitchen. The second side of the fireplace faces the

  Barry Novick Daniel Gale Sothebys Intl Rlty

  1665 Glenn Rd, Southold, NY 11971
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  /20

  $3,000 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
• 

  $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 $1,018,852

  Last Listing Agent Donielle Cardinale Daniel Gale Sothebys Intl Rlty

  6815 Soundview Ave, Southold, NY 11971
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  Est $1,860,333 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 3,286 Sq Ft

  425 Jacobs Ln, Southold, NY 11971

  425 Jacobs Ln, Southold, NY 11971
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  $6,299,000

  • Land
  • 51 Acres
  • $123,510 per Acre

  44075 Route 25, Peconic, NY 11958

  Step into the heart of North Fork wine country with the rare opportunity to own Osprey’s Dominion, an award-winning, fully operational winery and vineyard with a celebrated brand and loyal following. Perfectly positioned along the highly visible Main Road (Route 25) in Peconic, this landmark estate combines prime location, modern facilities, and limitless growth potential. Spanning over 50 acres,

  Susan Orioli Engel & Volkers North Fork

  44075 Route 25, Peconic, NY 11958
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  /39

  $40,000 per month

  • 6 Beds
  • 5.5 Baths
  • 6,600 Sq Ft
  • House for Rent

  57305 Route 48, Greenport, NY 11944

  Spectacular, contemporary seasonal rental home with pool and Jacuzzi on the Long Island Sound front. 150 feet of direct waterfront and beach, with incredible view. Meticulously renovated and professionally designed. 6 bedrooms, 5.5 bathrooms. Hamptons luxury in North Fork. Home situated on 1 acre, 6,600 square feet. One master bedroom has jacuzzi and steam room and two extra bedrooms with full

  Zepur Diktas Compass Greater NY LLC

  57305 Route 48, Greenport, NY 11944
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  $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

  Last Listing Agent Stephanie Ranghelli Coldwell Banker American Homes

  20845 Soundview Ave, Southold, NY 11971
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  Est $1,190,288 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths

  1715 Minnehaha Blvd, Southold, NY 11971

  1715 Minnehaha Blvd, Southold, NY 11971
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  /50

  $1,950,000

  • 4 Beds
  • 3.5 Baths
  • 4,173 Sq Ft

  295 Grange Rd, Southold, NY 11971

  Southold SanctuaryThere's a certain ease to life on the North Fork and knowing you are never far from the water - where summer stretches into fall, where neighbors still wave, and where the days' quiet rhythm becomes your soundtrack. Welcome to 4,173 square feet of newly built grace on just under a half-acre in Southold and one mile to Goose Creek Beach and two miles to Cedar Beach. This

  Sheri Winter Parker Corcoran

  295 Grange Rd, Southold, NY 11971
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  /42

  $3,500 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
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  $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
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  Est $3,370,333 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 3,300 Sq Ft

  1480 Old Wood Path, Southold, NY 11971

  1480 Old Wood Path, Southold, NY 11971
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  /2

  $399,000 Pending

  • 3 Beds
  • 1 Bath

  6825 Hortons Ln, Southold, NY 11971

  3 bedroom 2 1/2 baths in need of total gut renovation

  Yvette Sanchez NEW YORK REALTY GP LLC

  6825 Hortons Ln, Southold, NY 11971
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  /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
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  $685,000 Sold Nov 18, 2025

  2555 Youngs Ave Unit 14A, Southold, NY 11971

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 1988

  Last Sold Summary

  • 1% Above List Price
  • $571/SF
  • 12 Days On Market

  Last Listing Agent Diane Mollica Compass Greater NY LLC

  2555 Youngs Ave Unit 14A, Southold, NY 11971
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  Est $2,802,840 Not Listed For Sale

  • 6 Beds
  • 3.5 Baths
  • 2,400 Sq Ft

  100 W Shore Dr, Southold, NY 11971

  100 W Shore Dr, Southold, NY 11971
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  /16

  $599,000

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

  48920 Route 25, Southold, NY 11971

  Fantastic opportunity to get into the North Fork market offered via this "move in" condition 2 bedroom/2bathroom cottage on .17 acres w/ large detached 1.5 car garage. The interior features a large and inviting living room, primary ensuite bedroom, guest ensuite bedroom with attached home office, galley kitchen and intimate dining area. The location is fantastic as you can take a short walk or

  William Walters Daniel Gale Sothebys Intl Rlty

  48920 Route 25, Southold, NY 11971
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  /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
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  $370,000 Sold May 23, 2025

  55075 Route 25 Unit 1, Southold, NY 11971

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Built 1968

  Last Sold Summary

  • 3% Below List Price
  • $370/SF
  • 28 Days On Market

  Current Estimated Value $337,000

  Last Listing Agent Kenneth Poliwoda Douglas Elliman Real Estate

  55075 Route 25 Unit 1, Southold, NY 11971
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  Est $3,223,667 Not Listed For Sale

  • 4 Beds
  • 4 Baths

  150 W Shore Dr, Southold, NY 11971

  150 W Shore Dr, Southold, NY 11971
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  /50

  $3,649,999

  • 4 Beds
  • 5.5 Baths
  • 6,366 Sq Ft

  465 Ripple Water Ln, Southold, NY 11971

  COME and see this floor plan before it is gone!!!! Welcome to your bespoke farmhouse retreat nestled in the serene beauty of the North Fork of Long Island. This custom crafted home offers an unparalleled blend of luxury, comfort, and tranquility, enveloped by a meticulously designed landscape that creates a secluded oasis. Approaching the property, you're greeted by a custom landscape package

  Jerry Cibulski Century 21 Albertson Realty

  465 Ripple Water Ln, Southold, NY 11971
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  /23

  $10,000 per month

  • 4 Beds
  • 4 Baths
  • 2,082 Sq Ft
  • House for Rent

  780 Minnehaha Blvd, Southold, NY 11971

  Welcome to this high-quality beach home to stay for a couple of weeks in the summer or for a few months in the offseason. This custom designed impeccable home contains four bedrooms and four full bathrooms. There is an open floor plan with vaulted ceilings, from the chef's kitchen to the dining and living room. Enjoy a barbecue in the enclosed porch. Beautiful tranquil setting with views of

  Kenneth Poliwoda Douglas Elliman Real Estate

  780 Minnehaha Blvd, Southold, NY 11971
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  $1,940,000 Sold Feb 15, 2025

  650 Old Harbor Rd, Southold, NY 11971

  • 2 Beds
  • 3 Baths
  • 2,025 Sq Ft
  • Built 1971

  Last Sold Summary

  • 8% Above List Price
  • $958/SF
  • 27 Days On Market

  Current Estimated Value $1,980,591

  Last Listing Agent Bridget Elkin Compass Greater NY LLC

  650 Old Harbor Rd, Southold, NY 11971
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  Est $1,365,194 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,492 Sq Ft

  295 Grove Dr, Southold, NY 11971

  295 Grove Dr, Southold, NY 11971
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  /44

  $1,899,000

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

  630 Tarpon Dr, Southold, NY 11971

  Waterfront dream! This 3-bed, 2.5-bath home boasts safe deep-water docking on 50' wide canal. Open floor plan on both levels features two stone fireplaces, primary en-suite, ample storage, and a large open kitchen with breakfast and dining areas. Enjoy large sliders accessing two decks overlooking the waterfront, plus a spacious waterside boat house. Benefit from a brand new bulkhead ramp,

  Tom Uhlinger Douglas Elliman Real Estate

  630 Tarpon Dr, Southold, NY 11971
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  /28

  $10,000 per month

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

  9325 Main Bayview Rd, Southold, NY 11971

  2025 Rates: Last two weeks of June: $10,000.00, September 2-30 $15,000.00, October $12,500.00, Off season $6,000.00/month: Stunning New Construction in Southold's Hog Neck community. Enjoy open living w/ high vaulted ceilings in this sprawling modern farm house. Grand room features a combination of living room w/ gas fireplace, dining room, sun-soaked eat-in-kitchen w/ center island and shaker

  William Walters Daniel Gale Sothebys Intl Rlty

  9325 Main Bayview Rd, Southold, NY 11971
• 

  $760,000 Sold Apr 03, 2025

  805 Oak Ave, Southold, NY 11971

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Built 1938

  Last Sold Summary

  • 1% Above List Price
  • $760/SF
  • 16 Days On Market

  Current Estimated Value $777,335

  Last Listing Agent Rita Rooney Douglas Elliman Real Estate

  805 Oak Ave, Southold, NY 11971
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  Est $1,076,198 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,850 Sq Ft

  1520 Paradise Shores Rd, Southold, NY 11971

  1520 Paradise Shores Rd, Southold, NY 11971

Showing Results 81 - 120, Page 3 of 18