Southold, NY Homes

• 

  

  

  /43

  $4,250,000

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

  56875 Route 48, Southold, NY 11971

  Exceptional soundfront offering combining a beautifully maintained waterfront residence with a rare, separately buildable adjacent lot—creating a unique opportunity for legacy ownership or future development. The existing home sits on .75 acres with direct, no-bluff access to the Sound and showcases sweeping 180-degree panoramic water views. This 3-bedroom, 2-bath residence features a waterside

  Kris Pilles East End Luxury Ltd

  56875 Route 48, Southold, NY 11971
• 

  

  

  /39

  $10,000 per month

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

  485 Pine Rd, Southold, NY 11971

  2026 Rates: MDW- June $12,000; July 23,500; September $12,000; October $10,000: Discover your perfect getaway in this expansive and meticulously updated ranch home, designed for relaxation and rejuvenation. Experience a resort-like atmosphere with the stunning gunite, heated saltwater pool, complemented by a beautiful stone surround and convenient outdoor shower. Step inside to find high vaulted

  William Walters Daniel Gale Sothebys Intl Rlty

  485 Pine Rd, Southold, NY 11971
• 

  $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

  Current Estimated Value $1,445,500

  Last Listing Agent Kristy Naddell Douglas Elliman Real Estate

  3635 Old North Rd, Southold, NY 11971
• 

  Est $890,265 Not Listed For Sale

  1750 Seawood Dr, Southold, NY 11971

  • 3 Beds
  • 2 Baths
  • 1,420 Sq Ft
  • Built 1989

  1750 Seawood Dr, Southold, NY 11971

  Last Sold Summary

  • 17% Above List Price
  • $535/SF
  • 31 Days On Market

  Last Sold Price $759,000

  Last Listing Agent Stacy Zigman RE/MAX
• 

  

  

  /28

  $1,999,000

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

  3500 Pine Neck Rd, Southold, NY 11971

  Step into nearly three centuries of preserved history at 3500 Pine Neck Road, Southold—an extraordinary historic residence originally built in 1720 and impeccably maintained in pristine condition. This is not simply a home; it is a rare architectural heirloom, offering authenticity, craftsmanship, and legacy that cannot be replicated. Every historic element has been preserved to perfection,

  Trish Bergin Signature Premier Properties

  3500 Pine Neck Rd, 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
• 

  $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
• 

  Est $817,556 Not Listed For Sale

  1785 Seawood Dr, Southold, NY 11971

  • 3 Beds
  • 2 Baths
  • Built 1976

  1785 Seawood Dr, Southold, NY 11971

  Last Sold Summary

  • 14% Above List Price
  • 25 Days On Market

  Last Sold Price $715,000

  Last Listing Agent Laura Freudenberg Realty Connect USA L I Inc
• 

  

  /42

  $3,850,000

  • 6 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 6-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
• 

  

  /31

  $32,000 per month

  • 4 Beds
  • 3.5 Baths
  • House for Rent

  75 Clearview Ave, Southold, NY 11971

  2026 Rates: August 1-LD $39,500 or $32K for August 1-31: 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,

  William Walters Daniel Gale Sothebys Intl Rlty

  75 Clearview Ave, Southold, NY 11971
• 

  $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 $555,864

  Last Listing Agent Diana Mellone Daniel Gale Sothebys Intl Rlty

  900 Pine Ave, Southold, NY 11971
• 

  Est $1,042,799 Not Listed For Sale

  605 Topsail Ln, Southold, NY 11971

  • 3 Beds
  • 2.5 Baths
  • Built 1992

  605 Topsail Ln, Southold, NY 11971

  Last Sold Summary

  • 13% Above List Price
  • 55 Days On Market

  Last Sold Price $920,000

  Last Listing Agent Bridget Elkin Compass Greater NY LLC
• 

  

  /50

  $4,395,000

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

  19620 Soundview Ave, Southold, NY 11971

  Soundview on the Vines presents a rare opportunity to own a new construction vineyard-side estate where modern architecture, refined craftsmanship, and the natural beauty of the North Fork converge. Spanning approximately 7,300SF and situated on nearly 2 acres, this exceptional residence has been thoughtfully designed to balance grand-scale entertaining with relaxed, everyday luxury. Upon

  Kristy Naddell Douglas Elliman Real Estate

  19620 Soundview Ave, Southold, NY 11971
• 

  

  /27

  $8,000 per month

  • 3 Beds
  • 2 Baths
  • 1,620 Sq Ft
  • House for Rent

  400 Hill Rd, Southold, NY 11971

  Welcome to your perfect summer getaway located in the desirable Claves Neck neighborhood of Southold. This comfortable Ranch has ample space for the whole family to unwind and recharge after a day of exploring the North Fork. The home offers a fully equipped kitchen, spacious living, and dining rooms, three pleasant bedrooms, two pristine bathrooms. Outside, a savor al fresco dining amid the lush

  Jeanmarie Bay William Raveis New York LLC

  400 Hill Rd, Southold, NY 11971
• 

  $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 $836,531

  Last Listing Agent Nicholas Planamento William Raveis New York LLC

  6980 N Bayview Rd, Southold, NY 11971
• 

  Est $1,327,667 Not Listed For Sale

  1525 Leeward Dr, Southold, NY 11971

  • 5 Beds
  • 4 Baths
  • Built 2003

  1525 Leeward Dr, Southold, NY 11971

  Last Sold Summary

  • 33% Above List Price
  • 117 Days On Market

  Last Sold Price $997,499

  Last Listing Agent Connie Liappas Compass Greater NY LLC
• 

  

  /24

  $1,050,000 Open Sat 12PM - 1:30PM

  • 3 Beds
  • 2 Baths
  • 1,989 Sq Ft

  5845 N Bayview Rd, Southold, NY 11971

  Tucked away in a peaceful enclave of Southold, this classic Cape Cod offers a private escape that backs directly onto protected woodlands. One of the home’s standout features is an expansive three-season sunroom, which serves as a light-filled bridge between the indoors and your own quiet backyard sanctuary. Whether you are hosting a summer brunch or enjoying a morning coffee, the surrounding

  Stephanie Visek Engel & Volkers North Fork

  5845 N Bayview Rd, Southold, NY 11971
• 

  

  /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
• 

  $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

  Current Estimated Value $659,203

  Last Listing Agent Lisa Cerreta BERKSHIRE HATHAWAY

  900 Cedar Dr, Southold, NY 11971
• 

  Est $3,330,344 Not Listed For Sale

  10995 N Bayview Rd, Southold, NY 11971

  • 5 Beds
  • 5.5 Baths
  • 6,162 Sq Ft
  • Built 2000

  10995 N Bayview Rd, Southold, NY 11971

  Last Sold Summary

  • 54% Below List Price
  • $1,177/SF
  • 399 Days On Market

  Last Sold Price $7,250,000

  Last Listing Agent Carol Szynaka Daniel Gale Sotheby's
• 

  

  /45

  $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
• 

  

  /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
• 

  $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
• 

  Est $1,232,712 Not Listed For Sale

  75 Reydon Dr, Southold, NY 11971

  • 3 Beds
  • 3 Baths
  • 2,492 Sq Ft
  • Built 1991

  75 Reydon Dr, Southold, NY 11971

  Last Sold Summary

  • 23% Above List Price
  • $401/SF
  • 62 Days On Market

  Last Sold Price $999,999

  Last Listing Agent Nancy Cervelli Daniel Gale Sotheby's
• 

  

  /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
• 

  

  /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
• 

  $665,000 Sold Dec 03, 2025

  205 Grange Rd, Southold, NY 11971

  • 3 Beds
  • 1 Bath
  • 1,300 Sq Ft
  • Built 1971

  Last Sold Summary

  • 11% Above List Price
  • $512/SF
  • 15 Days On Market

  Current Estimated Value $671,582

  Last Listing Agent Rita Rooney Douglas Elliman Real Estate

  205 Grange Rd, Southold, NY 11971
• 

  Est $2,485,667 Not Listed For Sale

  400 Windjammer Dr, Southold, NY 11971

  • 4 Beds
  • 4 Baths
  • 3,373 Sq Ft
  • Built 1985

  400 Windjammer Dr, Southold, NY 11971

  Last Sold Summary

  • 9% Below List Price
  • $808/SF
  • 122 Days On Market

  Last Sold Price $2,725,000

  Last Listing Agent Mariah Mills Daniel Gale Sotheby's
• 

  /2

  $950,000 Coming Soon

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

  36595 County Road 48, Peconic, NY 11958

  Welcome to your opportunity to own a piece of the North Fork lifestyle. Situated on over half an acre in the heart of Peconic, this expanded ranch offers the perfect blend of comfort, space, and potential just minutes from everything that makes the North Fork one of Long Island’s most sought-after destinations. This well-maintained home features a functional single-level layout with an updated

  Anthony Gutierrez Signature Premier Properties

  36595 County Road 48, Peconic, NY 11958
• 

  

  /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
• 

  $1,175,000 Sold Feb 04, 2026

  1475 Oaklawn Ave, Southold, NY 11971

  • 4 Beds
  • 2.5 Baths
  • 2,400 Sq Ft
  • Built 1966

  Last Sold Summary

  • $490/SF
  • 33 Days On Market

  Current Estimated Value $1,104,238

  Last Listing Agent William Walters Daniel Gale Sothebys Intl Rlty

  1475 Oaklawn Ave, Southold, NY 11971
• 

  Est $992,240 Not Listed For Sale

  1565 Brigantine Dr, Southold, NY 11971

  • 3 Beds
  • 2.5 Baths

  1565 Brigantine Dr, Southold, NY 11971

  Last Sold Summary

  • 29% Above List Price
  • 7 Days On Market

  Last Sold Price $770,000

  Last Listing Agent Tricia English Signature Premier Properties
• 

  

  /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
• 

  

  /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
• 

  $1,375,000 Sold Jun 16, 2025

  5950 N Bayview Rd, Southold, NY 11971

  • 3 Beds
  • 2 Baths
  • 1,547 Sq Ft
  • Built 2016

  Last Sold Summary

  • 8% Below List Price
  • $889/SF
  • 107 Days On Market

  Current Estimated Value $1,354,640

  Last Listing Agent Lisa Gillooly Compass Greater NY LLC

  5950 N Bayview Rd, Southold, NY 11971
• 

  Est $1,021,006 Not Listed For Sale

  465 Windjammer Dr, Southold, NY 11971

  • 3 Beds
  • 2 Baths
  • 1,167 Sq Ft
  • Built 1923

  465 Windjammer Dr, Southold, NY 11971

  Last Sold Summary

  • 29% Above List Price
  • $677/SF
  • 46 Days On Market

  Last Sold Price $790,000

  Last Listing Agent Nancy Cervelli Daniel Gale Sotheby's
• 

  

  /10

  $699,000 Pending

  • 2 Beds
  • 1 Bath
  • 1,189 Sq Ft

  1000 Gin Ln, Southold, NY 11971

  Picture this: you’ve been walking through homes that are either way too much house... or feel like a shoebox with a mortgage. Then you walk into this one and it just clicks, not too big, not too small, and it actually makes sense for real life. It’s a two-bedroom layout that works, and the bathroom is basically begging for a remodel. The pink tile had its moment, but I’d happily retire it and put

  Jerry Cibulski Century 21 Albertson Realty

  1000 Gin Ln, Southold, NY 11971
• 

  

  /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
• 

  $1,150,000 Sold Jul 10, 2025

  2865 S Harbor Rd, Southold, NY 11971

  • 3 Beds
  • 3 Baths
  • 2,250 Sq Ft
  • Built 1984

  Last Sold Summary

  • $511/SF
  • 24 Days On Market

  Current Estimated Value $1,141,451

  Last Listing Agent Shane Hafer Compass Greater NY LLC

  2865 S Harbor Rd, Southold, NY 11971
• 

  Est $2,958,500 Not Listed For Sale

  165 Deer Run, Southold, NY 11971

  • 5 Beds
  • 6 Baths
  • 5,000 Sq Ft
  • Built 2006

  165 Deer Run, Southold, NY 11971

  Last Sold Summary

  • 12% Above List Price
  • $530/SF
  • 20 Days On Market

  Last Sold Price $2,650,000

  Last Listing Agent Connie Liappas Compass Greater NY LLC

Showing Results 161 - 200, Page 5 of 18