Southold, NY Homes

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  /7

  $1,499,000

  $201K PRICE DROP

  • 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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  /27

  $10,000 Per Month

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

  275 Maier Place, Southold, NY 11971

  Seasonal Rental in Scenic Southold, NY – 3 Bed, 3 Bath RetreatEscape to the heart of the North Fork with this beautifully appointed 3-bedroom, 2-bath seasonal rental in picturesque Southold, NY. Nestled among the region's famed vineyards, farm stands, and white sand beaches, this home offers the perfect blend of charm, comfort, and convenience.Inside, you'll find a spacious and

  Mary Terry MCKENNASHEA LLC

  275 Maier Place, Southold, NY 11971
• 

  $1,055,000

  Sold Nov 24, 2025

  610 Richmond Rd, Southold, NY 11971

  • 3 Beds
  • 2 Baths
  • 2,184 Sq Ft
  • Built 1930

  Last Sold Summary

  • 4% Below List Price
  • $483/SF
  • 41 Days On Market

  Current Estimated Value $1,048,352

  Last Listing Agent Bridget Elkin Compass Greater NY LLC

  610 Richmond Rd, Southold, NY 11971
• 

  Est $1,058,018

  Not Listed For Sale

  500 Glenn Rd, Southold, NY 11971

  • 3 Beds
  • 2 Baths
  • 1,550 Sq Ft
  • Built 1972

  500 Glenn Rd, Southold, NY 11971

  Last Sold Summary

  • 18 Days On Market
• 

  

  

  /25

  $2,295,000

  Pending

  • 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. Primary Ensuite and Two Additional Bedrooms and Hall Bath on Second Floor. Separate Fencing around Inground Heated Saltwater Pool with Easy Automatic Solar Cover and a Pool House. Large Stone

  Paul Loeb Douglas Elliman Real Estate

  450 Sterling Woods Ln, Southold, NY 11971
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  /38

  $35,000 Per Month

  • 6 Beds
  • 5.5 Baths
  • 5,155 Sq Ft
  • House for Rent

  610 Wildberry Ln, Southold, NY 11971

  Start your summer in pure luxury by securing this brand-new multi-level, beautifully decorated, modern farmhouse rental in Southold for the month of June, perfectly situated on the desirable North Fork of Long Island. This pristine property offers an exceptional outdoor oasis featuring an in-ground pool surrounded by a spacious patio for relaxation and entertaining; inside, the light-filled main

  Mackenzie Needham Daniel Gale Sothebys Intl Rlty

  610 Wildberry Ln, Southold, NY 11971
• 

  $2,100,000

  Sold May 29, 2026

  4745 N Bayview Rd, Southold, NY 11971

  • 4 Beds
  • 6 Baths
  • 5,500 Sq Ft
  • Built 1965

  Last Sold Summary

  • 5% Below List Price
  • $382/SF
  • 5 Days On Market

  Current Estimated Value $2,205,130

  Last Listing Agent Donielle Cardinale Daniel Gale Sothebys Intl Rlty

  4745 N Bayview Rd, Southold, NY 11971
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  Est $1,017,878

  Not Listed For Sale

  220 Glenn Rd, Southold, NY 11971

  • 3 Beds
  • 2 Baths
  • 1,610 Sq Ft
  • Built 1973

  220 Glenn Rd, Southold, NY 11971

  Last Sold Summary

  • 11 Days On Market
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  /15

  $699,000

  • 3 Beds
  • 1 Bath

  430 Grove Rd, Southold, NY 11971

  Enter the Season and enjoy North Fork Serenity with the creek across the street to launch into what Southold has to offer. Discover the perfect blend of coastal charm and country tranquility at 430 Grove Road, ideally located in the heart of Southold on the beautiful North Fork of Long Island—where vineyards, farms, and waterfront serenity define the lifestyle. This inviting 3-bedroom, 1-bath

  Karyn Flores Compass Greater NY LLC

  430 Grove Rd, Southold, NY 11971
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  /17

  $4,800 Per Month

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

  13595 Soundview Ave, Southold, NY 11971

  Built in 2019, this beautifully designed home offers a bright, open floor plan with clean, modern finishes throughout. Set on over an acre of private property, the setting provides both space and serenity just moments from the water. Located only one-third mile from McCabe’s Beach—a stunning sandy Sound beach—this home combines coastal living with contemporary comfort. Exterior boasts an outdoor

  Lisa Gillooly Compass Greater NY LLC

  13595 Soundview Ave, Southold, NY 11971
• 

  $678,000

  Sold Jun 24, 2025

  1745 Nokomis Rd, Southold, NY 11971

  • 2 Beds
  • 1 Bath
  • Built 1972

  Last Sold Summary

  • 7 Days On Market

  Current Estimated Value $698,446

  Last Listing Agent Maryse Bransfield William Raveis New York LLC

  1745 Nokomis Rd, Southold, NY 11971
• 

  Est $1,888,226

  Not Listed For Sale

  4015 Main Bayview Rd, Southold, NY 11971

  • 3 Beds
  • 3.5 Baths
  • 3,377 Sq Ft
  • Built 1930

  4015 Main Bayview Rd, Southold, NY 11971

  Last Sold Summary

  • 75 Days On Market
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  /26

  $4,300,000

  • Land
  • 45.77 Acres
  • $93,948 per Acre

  46975 Main Rd, Southold, NY 11971

  Some estates are acquired. The exceptional are entrusted to the next chapter. Set within the North Fork’s most storied agricultural landscape, this extraordinary lifestyle farm unfolds across protected vineyard acreage and open sky - a private world defined by refinement, scale, and possibility. Being offered together are two parcels: 43.7 preserved acres, where development rights have been sold

  Andrea Parks Douglas Elliman Real Estate

  46975 Main Rd, Southold, NY 11971
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  $950,000

  Sold Jul 11, 2025

  1575 Founders Path, Southold, NY 11971

  • 3 Beds
  • 2 Baths
  • 1,632 Sq Ft
  • Built 1927

  Last Sold Summary

  • 1% Below List Price
  • $582/SF
  • 13 Days On Market

  Current Estimated Value $932,659

  Last Listing Agent Timothy O'Keefe Signature Premier Properties

  1575 Founders Path, Southold, NY 11971
• 

  Est $890,457

  Not Listed For Sale

  3715 Main Bayview Rd, Southold, NY 11971

  • 3 Beds
  • 2.5 Baths
  • 1,400 Sq Ft
  • Built 1942

  3715 Main Bayview Rd, Southold, NY 11971

  Last Sold Summary

  • 58 Days On Market
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  /26

  $950,000

  • 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
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  $750,000

  Sold Dec 17, 2025

  57020 Route 25, Southold, NY 11971

  • 3 Beds
  • 3 Baths
  • 2,100 Sq Ft
  • Built 1783

  Last Sold Summary

  • 23% Below List Price
  • $357/SF
  • 169 Days On Market

  Current Estimated Value $803,597

  Last Listing Agent Eugene Rindfuss Coldwell Banker Reliable R E

  57020 Route 25, Southold, NY 11971
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  Est $1,368,404

  Not Listed For Sale

  2305 Glenn Rd, Southold, NY 11971

  • 4 Beds
  • 2.5 Baths
  • 2,020 Sq Ft
  • Built 1992

  2305 Glenn Rd, Southold, NY 11971

  Last Sold Summary

  • 8 Days On Market
• 

  

  /10

  $899,000

  $26K PRICE DROP Pending

  • 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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  $525,000

  Sold Nov 13, 2025

  2555 Youngs Ave Unit 11D, Southold, NY 11971

  • 2 Beds
  • 2 Baths
  • 1,100 Sq Ft
  • Built 1987

  Last Sold Summary

  • $477/SF
  • 54 Days On Market

  Last Listing Agent Patrick Carpenter Signature Premier Properties

  2555 Youngs Ave Unit 11D, Southold, NY 11971
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  Est $782,752

  Not Listed For Sale

  645 Shepard Dr, Southold, NY 11971

  • 2 Beds
  • 2 Baths
  • 1,150 Sq Ft
  • Built 1985

  645 Shepard Dr, Southold, NY 11971

  Last Sold Summary

  • 12 Days On Market
• 

  

  /10

  $560,000

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

  2555 Youngs Ave Unit 1D, Southold, NY 11971

  Gorgeous, light, bright, and airy, this immaculate 2-bedroom, 2-bath condominium is located in the highly desirable Founders Village 55+ community. Featuring soaring vaulted ceilings, an eat-in kitchen, spacious living and dining areas, and an inviting open layout, this home is designed for comfortable, low-maintenance living. The primary suite offers a private bath and generous closet space,

  Thomas McCarthy Thomas J McCarthy Real Estate

  2555 Youngs Ave Unit 1D, Southold, NY 11971
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  $2,495,000

  Sold Jun 27, 2025

  2375 Laurel Ave, Southold, NY 11971

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

  Last Sold Summary

  • $630/SF
  • 11 Days On Market

  Last Listing Agent Kristy Naddell Douglas Elliman Real Estate

  2375 Laurel Ave, Southold, NY 11971
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  Est $1,379,306

  Not Listed For Sale

  480 Grissom Ln, Southold, NY 11971

  • 4 Beds
  • 3 Baths
  • 3,200 Sq Ft
  • Built 1985

  480 Grissom Ln, Southold, NY 11971

  Last Sold Summary

  • 22 Days On Market
• 

  

  /30

  $2,995,000

  • 2 Beds
  • 1 Bath
  • 837 Sq Ft

  825 N Sea Dr, Southold, NY 11971

  It’s All About the Location! Perfectly situated along the Long Island Sound in the coveted hamlet of Southold. This quintessential North Fork beach cottage captures the very essence of coastal living, offering 100 feet of prime, sandy beachfront—a rare and exceptional find. While intimate in scale, the property delivers a lifestyle that’s nothing short of extraordinary. Spend your days seaside,

  William Walters Daniel Gale Sothebys Intl Rlty

  825 N Sea Dr, Southold, NY 11971
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  $815,000

  Sold Nov 14, 2025

  2575 Oaklawn Ave, Southold, NY 11971

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1960

  Last Sold Summary

  • $582/SF
  • 19 Days On Market

  Current Estimated Value $812,148

  Last Listing Agent Bridget Elkin Compass Greater NY LLC

  2575 Oaklawn Ave, Southold, NY 11971
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  Est $564,962

  Not Listed For Sale

  900 Pine Ave, Southold, NY 11971

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

  900 Pine Ave, Southold, NY 11971

  Last Sold Summary

  • 35 Days On Market
• 

  

  /46

  $2,350,000

  • 4 Beds
  • 4.5 Baths
  • 3,248 Sq Ft

  1665 Glenn Rd, Southold, NY 11971

  Newly built and beautifully enhanced with approx. $300K in upgrades since purchase, 1665 Glenn Road offers a turnkey North Fork retreat with thoughtful upgrades, elevated finishes, and exceptional indoor-outdoor living. Set on a .52-acre lot in Southold, this 4-bedroom, 4.5-bath home spans approximately 3,248 square feet and features a desirable layout with a first-floor ensuite primary bedroom

  Kristy Naddell Douglas Elliman Real Estate

  1665 Glenn Rd, Southold, NY 11971
• 

  $800,000

  Sold Oct 03, 2025

  265 Custer Ave, Southold, NY 11971

  • 3 Beds
  • 1.5 Baths
  • 1,800 Sq Ft
  • Built 1965

  Last Sold Summary

  • 9% Below List Price
  • $444/SF
  • 118 Days On Market

  Current Estimated Value $836,108

  Last Listing Agent Kenneth Poliwoda Douglas Elliman Real Estate

  265 Custer Ave, Southold, NY 11971
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  Est $1,033,710

  Not Listed For Sale

  2230 Cedar Dr, Southold, NY 11971

  • 3 Beds
  • 2 Baths
  • 2,000 Sq Ft
  • Built 1986

  2230 Cedar Dr, Southold, NY 11971

  Last Sold Summary

  • 3 Days On Market
• 

  

  /22

  $2,195,000

  New Construction $300K PRICE DROP Pending

  • 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
• 

  $864,000

  Sold Nov 12, 2025

  440 Jernick Ln, Southold, NY 11971

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • Built 1972

  Last Sold Summary

  • 1% Below List Price
  • $540/SF
  • 17 Days On Market

  Current Estimated Value $879,610

  Last Listing Agent Thomas McCarthy Thomas J McCarthy Real Estate

  440 Jernick Ln, Southold, NY 11971
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  Est $595,435

  Not Listed For Sale

  375 Oak Ave, Southold, NY 11971

  • 2 Beds
  • 1.5 Baths
  • Built 1930

  375 Oak Ave, Southold, NY 11971

  Last Sold Summary

  • 26 Days On Market
• 

  

  /20

  $949,000

  $50K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 1,862 Sq Ft

  240 Lisa Dr, Southold, NY 11971

  Welcome to this spacious 4-bedroom, 2.5-bath two-story home located in the desirable Highpoint Meadows community of Southold. Set on a corner lot, this property offers a welcoming front yard and a generously sized backyard with ample room for a pool and outdoor entertaining. Inside, the home features an open-concept kitchen and dining area ideal for everyday living and gatherings, complemented by

  Scott Bennett Douglas Elliman Real Estate

  240 Lisa Dr, Southold, NY 11971
• 

  $1,049,000

  Sold Mar 26, 2026

  633 Pine Neck Rd, Southold, NY 11971

  • 3 Beds
  • 1.5 Baths
  • 1,068 Sq Ft
  • Built 1920

  Last Sold Summary

  • 30% Below List Price
  • $982/SF
  • 882 Days On Market

  Current Estimated Value $1,068,235

  Last Listing Agent Tom Uhlinger Douglas Elliman Real Estate

  633 Pine Neck Rd, Southold, NY 11971
• 

  Est $804,895

  Not Listed For Sale

  980 Oak Ave, Southold, NY 11971

  • 2 Beds
  • 1 Bath
  • Built 1940

  980 Oak Ave, Southold, NY 11971

  Last Sold Summary

  • 177 Days On Market
• 

  

  /30

  $6,550,000

  • 5 Beds
  • 4.5 Baths
  • 3,500 Sq Ft

  920 Cedar Point Dr E, Southold, NY 11971

  An extraordinary offering on the Peconic Bay, this refined Cedar Beach waterfront estate presents over 200 feet of direct, sun drenched, south facing shoreline and beach with a protected, private dock deep enough for a mid-twenty-foot boat, a truly rare combination of attributes to find on the North Fork. Thoughtfully designed to embrace its breathtaking setting, the house is set on a double lot

  Patricia Cosmadelis Daniel Gale Sothebys Intl Rlty

  920 Cedar Point Dr E, Southold, NY 11971
• 

  $12,350,000

  Sold Jan 28, 2026

  59600 Main Rd, Southold, NY 11971

  • 4 Beds
  • 5 Baths
  • 5,500 Sq Ft
  • Built 1880

  Last Sold Summary

  • 5% Below List Price
  • $2,245/SF
  • 48 Days On Market

  Current Estimated Value $2,105,000

  Last Listing Agent Bridget Elkin Compass Greater NY LLC

  59600 Main Rd, Southold, NY 11971
• 

  Est $782,439

  Not Listed For Sale

  805 Oak Ave, Southold, NY 11971

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

  805 Oak Ave, Southold, NY 11971

  Last Sold Summary

  • 16 Days On Market
• 

  $400,000

  Sold Jan 22, 2026

  Unlisted Address

  • Land
  • 3.03 Acres
  • $132,013 per Acre

  Last Sold Summary

  • 33% Below List Price
  • 615 Days On Market

  Current Estimated Value $887,380

  Last Listing Agent Erica McKenzie Andrew Stype Realty Inc

  Unlisted Address

Showing Results 241 - 280, Page 7 of 18