Southold, NY Homes

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  /43

  $3,995,000

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

  1750 Mount Beulah Ave, Southold, NY 11971

  Welcome to one of the North Fork's most iconic and impeccably restored estates, where timeless grandeur blends seamlessly with refined modern living. Originally built circa 1915, this Georgian estate, formally known as the Cosden Estate, has been lovingly restored for today's modern luxuries while maintaining its historic vibe. Set on a professionally landscaped acre in one of Southold's most

  Kristy Naddell Douglas Elliman Real Estate

  1750 Mount Beulah Ave, Southold, NY 11971
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  /23

  $25,000 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 moments

  Nicholas Planamento William Raveis New York LLC

  495 N Parish Dr, Southold, NY 11971
• 

  $998,500 Sold Mar 21, 2025

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

  • 59 Days On Market

  1150 Kenneys Rd, Southold, NY 11971

  This property is a rare gem, offering the flexibility to bring your vision to life. Whether you're cultivating the land, caring for horses, or simply savoring the peaceful surroundings, this estate promises a lifestyle of unparalleled beauty and possibility.

  Thomas McCarthy Thomas J McCarthy Real Estate

  1150 Kenneys Rd, Southold, NY 11971
• 

  Est $1,411,128 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,800 Sq Ft

  2230 Paradise Shores Rd, Southold, NY 11971

  2230 Paradise Shores Rd, Southold, NY 11971
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  /39

  $1,249,999

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

  4710 Old Rd N, Southold, NY 11971

  Welcome to 4710 Old North Rd, a private Southold retreat. This beautifully maintained 2,400 sqft Expanded Cape offers the perfect blend of comfort, space, and privacy in the heart of Southold. Situated on over 3 scenic acres, with potential for subdivision, this home is a rare North Fork find featuring 4 spacious bedrooms, 2.5 bathrooms, a full basement, a 2-car garage and a heated in-ground

  Zachary Scher Signature Premier Properties

  4710 Old Rd N, Southold, NY 11971
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  /32

  $15,000 per month

  • 4 Beds
  • 4 Baths
  • 3,585 Sq Ft
  • House for Rent

  580 Gin Ln, Southold, NY 11971

  Wonderful opportunity to spend part of the summer in the wonderful Southold community of Bay Haven. Choose to spend the sunny days by your own pool, or head down the block to the community's private bay beach. There is more than ample space to host in this brightly renovated cape with room for everyone. The main level is comprised of a lounge area with fireplace and dry bar, an open kitchen

  Scott Bortzner Compass Greater NY LLC

  580 Gin Ln, Southold, NY 11971
• 

  $1,900,000 Sold Mar 18, 2025

  • 2,417 Sq Ft
  • $786/SF
  • 4 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2025

  670 Kenneys Rd, Southold, NY 11971

  Fully Finished and Furnished Outstanding Brand New Construction by Esteemed Builder. Perfectly Situated On Expansive 1 Acre Property Down The Block From Spectacular Kenney's Beach and Little Fish Restaurant. Modern Concept Colonial Bursting With Luxury Designer Selected Finishes Throughout, Including Double Cabinetry Imported from England, Waterfall Silestone Countertops, 9-Inch-Wide Plank Oak

  Robert Merolla Aurora Property Group

  670 Kenneys Rd, Southold, NY 11971
• 

  Est $1,198,885 Not Listed For Sale

  • 3 Beds
  • 3 Baths

  670 Seawood Dr, Southold, NY 11971

  670 Seawood Dr, Southold, NY 11971
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  /9

  $699,000

  • Land
  • 7 Acres
  • $98,036 per Acre

  1135 Boisseau Ave, Southold, NY 11971

  Turn-key 7-acre vineyard that you've been dreaming of in Southold! Perfectly situated near the village and shops. The vines are in their prime and have been meticulously maintained. Planted in 2006 is 2.2 Acres of Chardonnay and 2.5 Acres of Merlot and 1/2 acre Muscat Ottonel was planted in 2019. Producing approximately 2-3 tons per acre of grapes annually, which could average about 600 cases of

  Melissa Principi Douglas Elliman Real Estate

  1135 Boisseau Ave, Southold, NY 11971
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  /49

  $35,000 per month

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

  56765 Route 48, Southold, NY 11971

  Beautiful 3bd 2bath spacious home with pool on the Sound. Modern finishes and open floor plan help make this a special place to spend the summer months. Close proximity to local beaches, shops, and restaurants.

  Shannon Oshea East End Luxury Ltd

  56765 Route 48, Southold, NY 11971
• 

  $775,000 Sold Mar 14, 2025

  • 1,760 Sq Ft
  • $440/SF
  • 102 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1949

  5535 Old Rd N, Southold, NY 11971

  A classic North Fork farmhouse nestled in the heart of wine country, a winery adjacent to the property provides breathtaking vineyard views . This home features traditional design and layout, wood floors, upgraded heat and AC systems, one car detached garage and a welcoming sunroom perfect for relaxing and taking in the scenery. The lush landscaping is abundant with vibrant greenery, gardens,

  Tom Scalia Century 21 Albertson Realty

  5535 Old Rd N, Southold, NY 11971
• 

  Est $809,643 Not Listed For Sale

  • 3 Beds
  • 2 Baths

  1785 Seawood Dr, Southold, NY 11971

  1785 Seawood 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

  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 featuring Belgian block pathways, crushed pea gravel,

  Jerry Cibulski Century 21 Albertson Realty

  465 Ripple Water Ln, Southold, NY 11971
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  /30

  $15,000 per month

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

  295 Beckwith Ave, Southold, NY 11971

  Experience the perfect North Fork summer in this stunning designer-curated home, where historic charm blends seamlessly with modern convenience. Thoughtfully restored with nods to its rich past, this home offers a stylish and comfortable retreat with every contemporary amenity you need.Ideally located near Southold’s charming Main Road, you’ll have effortless access to boutique shops,

  Andrea Parks Douglas Elliman Real Estate

  295 Beckwith Ave, Southold, NY 11971
• 

  $551,000 Sold Mar 13, 2025

  • Land
  • 1.03 Acres
  • $534,951 per Acre

  • 18 Days On Market

  11212 Soundview Ave, Southold, NY 11971

  Opportunity Knocks!!! Build Your Ideal Vacation Home Or Year Round Residence On This 1 Plus Acre Private Residential Lot Located In The Beautiful Soundview Section Of Southold. Perfect North Fork Location --- Just Minutes To Kenney's And Mccabes Beaches Where You Can Enjoy Breathtaking Sunsets And The Village With Its Fine Restaurants And Quaint Shops Along With Nearby Wineries And Farm-stands.

  Thomas McCarthy Thomas J McCarthy Real Estate

  11212 Soundview Ave, Southold, NY 11971
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  Est $1,019,638 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths

  605 Topsail Ln, Southold, NY 11971

  605 Topsail Ln, Southold, NY 11971
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  /35

  $2,750,000

  • 4 Beds
  • 2.5 Baths
  • 2,800 Sq Ft

  2335 Minnehaha Blvd, Southold, NY 11971

  Step into a world of endless summer at this quintessential Nantucket-style cedar shake home, perfectly sited with expansive views of the Peconic bay and Corey creek. With its charming Dutch doors and expansive upper and lower decks, you’ll be invited to soak in the refreshing sea breezes and panoramic waterside vistas along with views of your private dock across the street, deep enough for a 66’

  Mariah Mills Daniel Gale Sothebys Intl Rlty

  2335 Minnehaha Blvd, Southold, NY 11971
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  /30

  $22,500 per month

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

  270 N Sea Dr, Southold, NY 11971

  Indulge in a sun-drenched Southold summer at this immaculate 4-bedroom, 3-bath retreat, where Kenny's Beach views paint a picturesque backdrop from the primary suite's private porch. A bright, comfortable atmosphere permeates the home, featuring seamless indoor/outdoor dining, a sprawling porch/decking, and a luxurious saltwater pool. Enjoy the added perks of "toys" provided by the owner,

  Mackenzie Needham Daniel Gale Sothebys Intl Rlty

  270 N Sea Dr, Southold, NY 11971
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  $2,250,000 Sold Mar 03, 2025

  • 4,780 Sq Ft
  • $471/SF
  • 7 Days On Market

  • 5 Beds
  • 6 Baths
  • Built 1972

  1275 Ruch Ln, Southold, NY 11971

  This stunning newly constructed home offers a picturesque setting at the end of Ruch Lane, boasting water views of Hashamomuck Pond and private community beach access. The home features five bedrooms, 5 baths, a luxurious primary suite and two additional ensuite guest rooms, a high-end kitchen, a double-sided fireplace, vaulted ceilings, both living room and family room, a lovely screened-in

  Bridget Elkin Compass Greater NY LLC

  1275 Ruch Ln, Southold, NY 11971
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  Est $1,053,378 Not Listed For Sale

  • 5 Beds
  • 2 Baths
  • 2,050 Sq Ft

  85 Leeward Dr, Southold, NY 11971

  85 Leeward Dr, Southold, NY 11971
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  /44

  $2,649,000

  • 4 Beds
  • 4.5 Baths
  • 2,842 Sq Ft

  285 Blue Marlin Dr, Southold, NY 11971

  Interior Completed! The pool and landscaping are slated for completion the end of August. With incredible water views and access to a picturesque private beach, 285 Blue Marlin exemplifies luxury coastal living at its finest. Constructed by the North Fork’s most revered builders, no expense has been spared and the utmost attention to detail is evident with attributes such as designer fixtures,

  Connie Liappas Compass Greater NY LLC

  285 Blue Marlin Dr, 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
• 

  $690,000 Sold Mar 03, 2025

  • 167 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1964

  500 Gagens Landing Rd, Southold, NY 11971

  Gagen's Landing Retreat awaits your arrival, ready to be your summer home or year-round retreat with the perfect blend of relaxation and adventure. With ample space for a pool and potential for expansion, this 3-bedroom home offers all the amenities of a beach community. A short stroll takes you to the water, perfect for escaping with your paddle board or kayak, leading out to Goose Creek Beach

  Katie Schimpf Daniel Gale Sothebys Intl Rlty

  500 Gagens Landing Rd, Southold, NY 11971
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  Est $911,296 Not Listed For Sale

  • 5 Beds
  • 4 Baths

  1525 Leeward Dr, Southold, NY 11971

  1525 Leeward Dr, Southold, NY 11971
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  /27

  $799,000

  • 2 Beds
  • 1.5 Baths

  50605 Route 25, Southold, NY 11971

  A Hidden Gem of Serenity and Style. Tucked away in a private, storybook setting, this stunningly charming and meticulously crafted 1600s home is a true sanctuary. Surrounded by mature specimen trees and lush, professionally landscaped gardens, every inch of this light-filled retreat exudes warmth and character. Rich wood floors flow throughout the thoughtfully designed interior, which offers an

  Mariah Mills Daniel Gale Sothebys Intl Rlty

  50605 Route 25, Southold, NY 11971
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  /46

  $12,000 per month

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

  110 Sleepy Hollow Ln, Southold, NY 11971

  Discover this stunningly renovated 4-bedroom, 3-bath home, offering an expansive open floor plan, a cozy den, and a versatile bonus room. Designed for both comfort and style, the chef’s kitchen includes a massive eat-in-quartz island and boasts top-of-the-line Fisher & Paykel appliances, including a double-drawer dishwasher, induction cooktop, and convection oven.Perfect for entertaining

  Paul Loeb Douglas Elliman Real Estate

  110 Sleepy Hollow Ln, Southold, NY 11971
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  $625,000 Sold Feb 28, 2025

  • Land
  • 0.55 Acre
  • $1,136,364 per Acre

  • 271 Days On Market

  280 Lakeside Dr N, Southold, NY 11971

  Beautiful .55-acre waterfront building lot with 178 ft on Stillwater Lake and access by water to Cedar Beach Creek and Peconic Bay. Member of Cedar Beach Park Association with community bay beach. Suffolk County Department of Health Services Permit approval has been obtained for construction of a 2-story single-family residence with a maximum of 4 bedrooms. Lot is partially cleared with many

  Janet Markarian Daniel Gale Sothebys Intl Rlty

  280 Lakeside Dr N, Southold, NY 11971
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  Est $2,427,154 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 3,373 Sq Ft

  400 Windjammer Dr, Southold, NY 11971

  400 Windjammer Dr, Southold, NY 11971
• 

  

  /20

  $3,900,000

  • 3 Beds
  • 1 Bath
  • 1,500 Sq Ft

  5615 Soundview Ave, Southold, NY 11971

  Includes TWO lots totaling one residential waterfront lot with a preexisting two story house on 7 acres. The other is an additional vacant buildable lot available with nearly 2 acres. With 250 feet of private sandy beach, you'll have endless opportunities. Explore a rich natural landscape with a dedicated nature trail, home to wild blueberries, cranberries, and beach plums, plus an osprey

  Donielle Cardinale Daniel Gale Sothebys Intl Rlty

  5615 Soundview Ave, 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
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  $1,870,000 Sold Feb 28, 2025

  • 4,000 Sq Ft
  • $468/SF
  • 127 Days On Market

  • 6 Beds
  • 4 Baths
  • Built 2007

  1820 Kenneys Rd, Southold, NY 11971

  Located just a stone's throw away from Kenney's Beach, this 6 bedroom, 4 bath stately brick beauty was built in 2007 and sits on 2+ bucolic acres. This home is adorned with luxurious features including radiant heat throughout the kitchen and foyer, designer appliances, custom cabinetry and a lovely balcony located off of one of the bedrooms. There is a grand two-story entry, a spacious eat-in

  Kristen Vlahopoulos Compass Greater NY LLC

  1820 Kenneys Rd, Southold, NY 11971
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  Est $994,403 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths

  1565 Brigantine Dr, Southold, NY 11971

  1565 Brigantine Dr, Southold, NY 11971
• 

  

  /20

  $3,200,000

  • 3 Beds
  • 1 Bath
  • 1,500 Sq Ft

  5615 Soundview Ave, Southold, NY 11971

  Residential waterfront lot with a preexisting two story house. Imagine owning over 7 acres of pristine woodland in Peconic Dunes, your very own waterfront haven on the Long Island Sound. With 250 feet of private sandy beach, you'll have endless opportunities for swimming, fishing, and soaking in incredible sunsets. Explore a rich natural landscape with a dedicated nature trail, home to wild

  Donielle Cardinale Daniel Gale Sothebys Intl Rlty

  5615 Soundview Ave, Southold, NY 11971
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  /10

  $4,000 per month

  • 4 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • House for Rent

  380 Eds Rd, Southold, NY 11971

  Discover a wonderful opportunity for year-round rental in the heart of Southold. This beautifully renovated home exudes style and comfort, featuring exquisite hardwood floors and a seamless flow from the kitchen/dining room to an inviting deck—perfect for entertaining or relaxing. With two newly updated bathrooms, this home is fresh, clean, and ready for move-in.Enjoy the convenience of a fully

  Diane Mollica Compass Greater NY LLC

  380 Eds Rd, Southold, NY 11971
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  $1,800,000 Sold Feb 27, 2025

  • 2,662 Sq Ft
  • $676/SF

  • 4 Beds
  • 3 Baths
  • Built 1867

  8355 Main Bayview Rd, Southold, NY 11971

  Meticulously restored and maintained 19th C Italianate style residence, beautifully set on elevated 1.25-acre lot. Built around 1850 by Silas Horton and occupied by his descendants until the 1960's. original wrap around porch, floor to ceiling windows, ornate Cupula, marble fireplace mantles, original wide floorboards, in-tact period moldings, trims, banisters, and doors. Large, updated kitchen

  Janet Markarian Daniel Gale Sothebys Intl Rlty

  8355 Main Bayview Rd, Southold, NY 11971
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  Est $941,769 Not Listed For Sale

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

  465 Windjammer Dr, Southold, NY 11971

  465 Windjammer Dr, Southold, NY 11971
• 

  

  /22

  $850,000

  • 3 Beds
  • 2 Baths
  • 1,425 Sq Ft

  2955 Hyatt Rd, Southold, NY 11971

  This bright and airy 3-bedroom, 2-bathroom home on Southold's charming Hyatt Road offers a perfect blend of open and closed living spaces. With numerous windows and skylights, the home seamlessly integrates with the surrounding mature landscaping. Each bedroom boasts vaulted ceilings and picturesque views of the park-like setting. The Primary has a large ensuite bath. Conveniently located just

  Bridget Elkin Compass Greater NY LLC

  2955 Hyatt Rd, Southold, NY 11971
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  /36

  $12,000 per month

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

  54505 County Road 48 Aka Rd N, Southold, NY 11971

  **Southold, North Fork:** Picture yourself enjoying the most enchanting summer in this exquisite beach house situated on the sparkling Long Island Sound. With 100 feet of private waterfront beach and stunning sunset views, this home promises an unforgettable summer or vacation escape. Experience affordable luxury and peace as you relax in this tranquil setting, conveniently located near the

  Nicholas Planamento William Raveis New York LLC

  54505 County Road 48 Aka Rd N, Southold, NY 11971
• 

  $1,575,000 Sold Feb 25, 2025

  • 2,000 Sq Ft
  • $788/SF
  • 86 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1977

  2505 Wells Ave, Southold, NY 11971

  Charming, Sleek, and Sexy waterfront cape-style home with exceptional water views located on Jockey Creek! This private retreat boasts 3 bedrooms, and 2 baths and is situated on .66 acres with a dock, and room for a pool. Enjoy an updated kitchen and beautiful baths, a bright and open floor plan, a living room with wood-burning stove, and sliders to the waterfront deck. Other features include

  Kristy Naddell Douglas Elliman Real Estate

  2505 Wells Ave, Southold, NY 11971
• 

  Est $2,644,211 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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