Southold, NY Homes

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  /42

  $3,850,000

  • 5 Beds
  • 4 Baths
  • 4,663 Sq Ft

  105 Waterview Dr, Southold, NY 11971

  Discover a rare waterfront property where privacy, space, and breathtaking views come together on 6.5 gated acres. Spanning two single-and-separate lots, this refreshed 5-bedroom, 4-bath colonial offers a den/office, bonus room, and sweeping water views from nearly every room. Thoughtfully designed for both comfort and future flexibility, the residence provides substantial expansion potential.

  Roric Tobin Compass Greater NY LLC

  105 Waterview Dr, Southold, NY 11971
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  /33

  $25,000 per month

  • 4 Beds
  • 3.5 Baths
  • House for Rent

  910 Glenn Rd, Southold, NY 11971

  Introducing your perfect retreat! This stunning 4-bed, 3.5-bath waterfront oasis nestled on West Creek in Southold. Enjoy access to Peconic Bay via your private dock. Spanning approx 3500 sq ft, revel in the elegance of oak floors, a luxurious soaking tub, and high ceilings throughout. The 1st floor has 2 primary ensuites, a spacious Great Room with cozy fireplace, laundry, and 2.5 baths +2-car

  Andrea Parks Douglas Elliman Real Estate

  910 Glenn Rd, Southold, NY 11971
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  $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 $811,252

  Last Listing Agent Mariah Mills Daniel Gale Sothebys Intl Rlty

  50605 Route 25, Southold, NY 11971
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  Est $1,005,159 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths

  1565 Brigantine Dr, Southold, NY 11971

  1565 Brigantine Dr, Southold, NY 11971
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  /47

  $3,598,999

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

  465 Ripple Water Ln, Southold, NY 11971

  You know we have been looking at new homes for a while. This one is the first that felt like, "okay, this checks the boxes"The granite front porch sold me right away. wine and cheese with everyone and with the larger width and depth, you can see they built the home with this in mind. And the kitchen is exactly what I wanted because this is where we all hang out and this has the built in

  Jerry Cibulski Century 21 Albertson Realty

  465 Ripple Water Ln, 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
• 

  $1,240,000 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 $1,030,481 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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  /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
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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

  Current Estimated Value $1,129,638

  Last Listing Agent Kelly Gatanas Daniel Gale Sothebys Intl Rlty

  70 Mockingbird Ln, Southold, NY 11971
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  Est $3,362,000 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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  /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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  $1,500,000 Sold Jan 08, 2026

  3635 Old North Rd, Southold, NY 11971

  • Land
  • 9.5 Acres
  • $157,895 per Acre

  Last Sold Summary

  • 8 Days On Market

  Last Listing Agent Kristy Naddell Douglas Elliman Real Estate

  3635 Old North Rd, Southold, NY 11971
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  Est $1,059,251 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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  /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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  $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 $1,360,047 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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  /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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  $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 $580,326

  Last Listing Agent Diana Mellone Daniel Gale Sothebys Intl Rlty

  900 Pine Ave, Southold, NY 11971
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  Est $2,026,831 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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  /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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  /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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  $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 $810,908

  Last Listing Agent Nicholas Planamento William Raveis New York LLC

  6980 N Bayview Rd, Southold, NY 11971
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  Est $801,245 Not Listed For Sale

  • 3 Beds
  • 1 Bath

  275 Victoria Dr, Southold, NY 11971

  275 Victoria Dr, Southold, NY 11971
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  /44

  $3,950,000

  • 5 Beds
  • 3.5 Baths
  • 4,500 Sq Ft

  790 N Sea Dr, Southold, NY 11971

  Quintessential North Fork Beach House!! Perched high above with breathtaking views of the Long Island Sound, this stunning custom-built home offers the perfect blend of luxury, comfort, and location. Just across the street from the shores of Kenney’s Beach, this 2009-built residence features 5 spacious bedrooms and 3.5 beautifully appointed baths, including a serene first-floor primary suite. Set

  Kristy Naddell Douglas Elliman Real Estate

  790 N Sea Dr, Southold, NY 11971
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  /29

  $12,000 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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  $650,000 Sold Nov 21, 2025

  900 Cedar Dr, Southold, NY 11971

  • 3 Beds
  • 1 Bath
  • 1,100 Sq Ft
  • Built 1967

  Last Sold Summary

  • 11% Below List Price
  • $591/SF
  • 144 Days On Market

  Last Listing Agent Lisa Cerreta BERKSHIRE HATHAWAY

  900 Cedar Dr, Southold, NY 11971
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  Est $963,327 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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  /10

  $899,000

  • Land
  • 2 Acres
  • $449,500 per Acre

  195 Mount Beulah Ave, Southold, NY 11971

  Build Your Dream Estate in Southold. Prime 2 Acre Corner Lot Near the BeachAn exceptional opportunity awaits in one of Southold’s most desirable neighborhoods. This premium 2-acre corner parcel provides the ideal setting to design and build a custom luxury residence with plenty of room for a pool, pool house, guest cottage, tennis or pickleball courts, lush gardens, and expansive outdoor

  Kristy Naddell Douglas Elliman Real Estate

  195 Mount Beulah Ave, 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

  A masterfully crafted resort style property, where coastal luxury meets effortless living. Tucked within a coveted private beach community with beach access, this resort-style property was designed for gathering, entertaining, and unwinding in total privacy. The home features a show-stopping 20’ x 40’ heated saltwater pool, framed by lush, manicured grounds that feel both serene and indulgent.

  Colin McCarthy Thomas J McCarthy Real Estate

  650 Pine Ave, Southold, NY 11971
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  $625,000 Sold Feb 28, 2025

  280 Lakeside Dr N, Southold, NY 11971

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

  Last Sold Summary

  • 14% Below List Price
  • 271 Days On Market

  Current Estimated Value $787,150

  Last Listing Agent Janet Markarian Daniel Gale Sothebys Intl Rlty

  280 Lakeside Dr N, Southold, NY 11971
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  Est $1,096,253 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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  /22

  $2,195,000

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

  600 Glenn Rd, Southold, NY 11971

  Modern Luxury Waterfront Tree House - Nature Lovers’ Paradise on West Creek!Discover this stunning 4-bedroom, 5.5-bath waterfront featuring a Black Onyx saltwater pool and private dock on the highly sought-after West Creek.Step into the upper-level living area, where floor-to-ceiling views create a serene bird’s-eye perspective of lush trees and sparkling water—a true sanctuary for birds

  Cathleen Dolson Corcoran

  600 Glenn Rd, Southold, NY 11971
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  /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; 2025 Rates: January- April $3500, May $5000, June $7000,

  Barbara Poliwoda Douglas Elliman Real Estate

  3825 S Harbor Rd, Southold, NY 11971
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  $2,600,000 Sold Feb 02, 2026

  1635 Laurel Ave, Southold, NY 11971

  • 4 Beds
  • 4.5 Baths
  • 3,960 Sq Ft
  • Built 2025

  Last Sold Summary

  • $657/SF
  • 7 Days On Market

  Last Listing Agent Kristy Naddell Douglas Elliman Real Estate

  1635 Laurel Ave, Southold, NY 11971
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  Est $1,494,017 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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