Southold, NY Homes

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  /9

  $775,000 Pending

  • 1 Bed
  • 4 Baths
  • 2,890 Sq Ft

  Unlisted Address

  Great office space with apartment! The office has 5+ exam rooms, large waiting area and 2 half baths. The 1 bedroom, 1 bath apartment has a large kitchen, loft area and large deck. The property sits on one acre and has ample parking. The office and apartment must be owner occupied, or the entire structure could be converted to all living space as well as keeping the apartment. Many uses for this

  Andrew Stype Andrew Stype Realty Inc

  Unlisted Address
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  /20

  $13,000 per month

  • 4 Beds
  • 3 Baths
  • 2,300 Sq Ft
  • House for Rent

  215 Northfield Ln, Southold, NY 11971

  Permit 0681- Enjoy This Beautifully Renovated 4 Bedroom, 3 Bath Ranch Style Home With Heated Pool. Open Floor Plan Includes LR With Cathedral Ceilings, High End EIK, Dining Area & Outdoor Shower. Plenty of Room For The Whole Family & Guests. Beautiful Goose Creek Beach Just 0.2 Miles Down The Road. Minutes To Local Wineries, Shopping & Dining. BOOK NOW FOR SUMMER 2025. Terms: May $13,000, June

  Mitch Pickman Thomas J McCarthy Real Estate

  215 Northfield Ln, Southold, NY 11971
• 

  $3,850,000 Sold Aug 25, 2025

  1750 Mount Beulah Ave, Southold, NY 11971

  • 6 Beds
  • 5.5 Baths
  • 6,000 Sq Ft
  • Built 1915

  Last Sold Summary

  • 4% Below List Price
  • $642/SF
  • 17 Days On Market

  Current Estimated Value $3,826,333

  Last Listing Agent Kristy Naddell Douglas Elliman Real Estate

  1750 Mount Beulah Ave, Southold, NY 11971
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  Est $1,175,810 Not Listed For Sale

  1750 Water Terrace, Southold, NY 11971

  • 4 Beds
  • 2.5 Baths
  • 2,000 Sq Ft
  • Built 2002

  1750 Water Terrace, Southold, NY 11971

  Last Sold Summary

  • 9% Above List Price
  • $540/SF
  • 68 Days On Market

  Last Sold Price $1,080,000

  Last Listing Agent Connie Liappas Compass Greater NY LLC
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  /46

  $3,825,000 Open Sat 11AM - 2PM

  • 5 Beds
  • 6 Baths
  • 5,285 Sq Ft

  150 Deer Run, Southold, NY 11971

  Gorgeous estate-like Nantucket shingle home in the final stage of construction. Designed by the renowned firm of Nelson and Pope utilizing steel beam construction throughout and Benjamin Obdyke Hydrogap house wrap, the home features solid white oak hardwood floors, as well as many custom details including maple cabinetry and vanities, Marvin Elevate windows, sliding and French doors, mahogany

  Jeffrey Mead Corcoran

  150 Deer Run, Southold, NY 11971
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  /21

  $22,500 per month

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

  270 N Sea Dr, Southold, NY 11971

  Southold, North Fork: Endless sunsets await at this exceptional vacation rental, available year-round with flexible terms and rates. Ideally located in the sought-after Kenny’s Beach community, this sun-drenched home is surrounded by wide sandy dunes perfect for walking, birdwatching, swimming, and relaxing days by the shore.Immaculately maintained, the residence offers 4 bedrooms and 3 full

  Nicholas Planamento William Raveis New York LLC

  270 N Sea Dr, Southold, NY 11971
• 

  $1,350,000 Sold Sep 05, 2025

  4710 Old Rd N, Southold, NY 11971

  • 4 Beds
  • 2.5 Baths
  • 2,400 Sq Ft
  • Built 1978

  Last Sold Summary

  • 8% Above List Price
  • $562/SF
  • 24 Days On Market

  Current Estimated Value $1,357,230

  Last Listing Agent Zachary Scher Signature Premier Properties

  4710 Old Rd N, Southold, NY 11971
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  Est $1,080,359 Not Listed For Sale

  505 Longview Ln, Southold, NY 11971

  • 3 Beds
  • 2 Baths
  • Built 1984

  505 Longview Ln, Southold, NY 11971

  Last Sold Summary

  • 3% Above List Price
  • 11 Days On Market

  Last Sold Price $1,050,000

  Last Listing Agent Nicole Fitzgerald Signature Premier Properties
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  /5

  $799,000

  • Land
  • 2.29 Acres
  • $348,908 per Acre

  1350 Hortons Ln, Southold, NY 11971

  Discover The Perfect Canvas For Your Dream Estate On This Expansive 2+ Acre Lot, Offering The Ideal Balance Of Privacy And Convenience. Nestled In A Serene Setting, Yet Just Moments Away From The Vibrant Town Life, You’ll Be Close To Fine Dining, Shopping, And Everything The North Fork Has To Offer. This Unique Parcel Comes With Suffolk County Health Department Approval For An 8-Bedroom

  Thomas McCarthy Thomas J McCarthy Real Estate

  1350 Hortons Ln, Southold, NY 11971
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  /31

  $35,000 per month

  • 3 Beds
  • 3.5 Baths
  • 2,085 Sq Ft
  • House for Rent

  Unlisted Address

  This beautiful home with in-ground pool and ample private open space exudes beach resort ease and is rarely available for rent. Located in a quiet enclave off the vineyards mile of Southold on the north fork, it is within proximity to farms, town, beaches and restaurants. The home which entered via a tree lined drive, is comprised of two stories, plus a lower level. The first floor features a

  Scott Bortzner Compass Greater NY LLC

  Unlisted Address
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  $762,000 Sold Sep 12, 2025

  Unlisted Address

  • 3 Beds
  • 2.5 Baths
  • 1,572 Sq Ft
  • Built 1982

  Last Sold Summary

  • 20% Below List Price
  • $485/SF
  • 320 Days On Market

  Current Estimated Value $804,429

  Last Listing Agent Nicholas Planamento William Raveis New York LLC

  Unlisted Address
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  Est $996,953 Not Listed For Sale

  1100 Rambler Rd, Southold, NY 11971

  • 4 Beds
  • 2 Baths
  • Built 1961

  1100 Rambler Rd, Southold, NY 11971

  Last Sold Summary

  • 25% Above List Price
  • 6 Days On Market

  Last Sold Price $800,000

  Last Listing Agent Susan Orioli Engel & Volkers North Fork
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  /18

  $899,000 Pending

  • 4 Beds
  • 3 Baths
  • 2,900 Sq Ft

  1400 Calves Neck Rd, Southold, NY 11971

  Located on a half-acre corner lot in one of Southold’s most sought-after neighborhoods, this 4-bed, 3-bath Cape offers ~2,900sqft of living space and the potential for a pool, subject to variance approval. There’s a spacious eat-in kitchen with stainless steel appliances and a center island, opening to a back patio creating a seamless space for indoor-outdoor entertaining. Additionally, the main

  Mariah Mills Daniel Gale Sothebys Intl Rlty

  1400 Calves Neck Rd, Southold, NY 11971
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  /5

  $4,000 per month

  • 3 Beds
  • 1 Bath
  • 1,100 Sq Ft
  • House for Rent

  310 Old Shipyard Ln, Southold, NY 11971

  Southold Village Rental Charming and well-located, this 3-bedroom, 1-bath residence offers easy North Fork living just moments from the heart of Southold. A short distance to Southold Town, local shops, dining, and the waterfront, as well as close proximity to Founders Beach for swimming, sunsets, and seaside relaxation. The home features a comfortable layout with light-filled living spaces,

  Eric Frend Corcoran

  310 Old Shipyard Ln, Southold, NY 11971
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  $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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  Est $1,172,017 Not Listed For Sale

  65 Pleasant Place, Southold, NY 11971

  • 4 Beds
  • 2 Baths
  • Built 1987

  65 Pleasant Place, Southold, NY 11971

  Last Sold Summary

  • 7% Above List Price
  • 69 Days On Market

  Last Sold Price $1,100,000

  Last Listing Agent Katie Schimpf Daniel Gale Sotheby's
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  /23

  $725,000 Pending

  • 2 Beds
  • 1 Bath
  • 840 Sq Ft

  340 Pine Rd, Southold, NY 11971

  Southold- Get ready to kick off your shoes this summer... Kenneys Beach is waiting for you. This two bedroom, one bath ranch home has been lovingly maintained. An easy, open floor plan consists of a living room, eat-in-kitchen, and separate dining room/den. Slider to a large patio perfect for entertaining and family get-togethers. Two comfortable bedrooms. One bath with a tub/shower combo. Wood

  Nancy Cervelli Daniel Gale Sothebys Intl Rlty

  340 Pine Rd, 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
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  $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

  Last Listing Agent Kristy Naddell Douglas Elliman Real Estate

  45 Smith Dr N, Southold, NY 11971
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  Est $1,132,337 Not Listed For Sale

  945 Gin Ln, Southold, NY 11971

  • 4 Beds
  • 3 Baths
  • Built 1972

  945 Gin Ln, Southold, NY 11971

  Last Sold Summary

  • 9% Above List Price
  • 51 Days On Market

  Last Sold Price $1,040,000

  Last Listing Agent Tom Scalia Century 21 Albertson Realty
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  /5

  $1,499,000

  • Land
  • 4.24 Acres
  • $353,538 per Acre

  18365 County Road 48, Southold, NY 11935

  Motivated Seller! Opportunity to own 4+ acres of buildable vacant land in the heart of Cutchogue on Long Island’s scenic North Fork. Water, electric, and natural gas connections are available at the street, making this an ideal site to build your dream home, private retreat, or investment property. Enjoy a peaceful setting surrounded by vineyards, farm stands, and open farmland, while being just

  Michael Graziose Redfin Real Estate

  18365 County Road 48, Southold, NY 11935
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  /15

  $30,000 per month

  • 5 Beds
  • 4.5 Baths
  • 3,600 Sq Ft
  • House for Rent

  11925 Soundview Ave, Southold, NY 11971

  .Enjoy water views and Long Island Sound sunsets from this magnificent new construction home for rent! Perfectly situated on 1.5 scenic acres, this home offers exclusivity and privacy. The beautiful eat-in-kitchen features high-end amenities including a Viking refrigerator and 8 burner range, double ovens, dual Bosch dishwashers plus two wine coolers. The airy and spacious living room is accented

  Nicholas Liappas Compass Greater NY LLC

  11925 Soundview Ave, Southold, NY 11971
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  $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 $999,560

  Last Listing Agent Donielle Cardinale Daniel Gale Sothebys Intl Rlty

  6815 Soundview Ave, Southold, NY 11971
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  Est $867,024 Not Listed For Sale

  685 Bay Haven Ln, Southold, NY 11971

  • 3 Beds
  • 2 Baths
  • Built 1959

  685 Bay Haven Ln, Southold, NY 11971

  Last Sold Summary

  • 6% Above List Price
  • 27 Days On Market

  Last Sold Price $815,000

  Last Listing Agent Eleanor Dunne Andron Realty Group Tulip R E
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  /50

  $1,350,000 Open Sat 11AM - 1PM

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

  2055 Boisseau Ave, Southold, NY 11971

  Southold, North Fork: The historic Boisseau farmhouse, built around 1890, is situated on 1.75 acres (76,230 square feet) with R40 residential zoning, in a picturesque setting featuring mature trees and a sprawling lawn. The property is adjacent to fallow, and partially wooded acreage owned by the Town of Southold. The traditional home boasts a charming covered front porch, an entry foyer, and a

  Nicholas Planamento William Raveis New York LLC

  2055 Boisseau Ave, Southold, NY 11971
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  /46

  $40,000 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 and

  Paul Loeb Douglas Elliman Real Estate

  110 Sleepy Hollow Ln, Southold, NY 11971
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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

  Current Estimated Value $1,758,622

  Last Listing Agent Stephanie Ranghelli Realty Connect USA LI Inc

  20845 Soundview Ave, Southold, NY 11971
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  /2

  Est $713,177 Not Listed For Sale

  1430 Bay Haven Ln, Southold, NY 11971

  • 3 Beds
  • 2 Baths
  • Built 1973

  1430 Bay Haven Ln, Southold, NY 11971

  Last Sold Summary

  • 5% Below List Price

  Last Sold Price $677,000

  Last Listing Agent Diane Mollica Compass Greater NY LLC
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  /39

  $1,200,000

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

  3475 Oaklawn Ave, Southold, NY 11971

  Circa-1909 Cozy Farmhouse Near the Water & Southold Village Welcome to 3475 Oaklawn Road, Southold, a circa-1909 farmhouse rich in warmth, character, and North Fork authenticity. This charming home, situated on a 1/2 acre, captures the essence of early-20th-century farmhouse living, offering a cozy, inviting atmosphere paired with thoughtful functionality and future potential. The residence

  Trish Bergin Signature Premier Properties

  3475 Oaklawn Ave, Southold, NY 11971
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  /26

  $20,000 per month

  • 4 Beds
  • 3 Baths
  • 2,700 Sq Ft
  • House for Rent

  1000 Rambler Rd, Southold, NY 11971

  Beautiful like new colonial just 500 feet from sandy bay beach. Four bedrooms plus a lovely sunroom. Fully Furnished. Enjoy your morning coffee on the bedroom balcony. Outside shower and gas grill off backyard deck. Bicycles and a kayak with trailer included. A perfect beach house. Available July $20,000, July and August $45,000, August-Labor Day $25,000 utilities included.

  Pamela Hunt Colony Realty

  1000 Rambler Rd, 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 $1,042,311 Not Listed For Sale

  380 Gin Ln, Southold, NY 11971

  • 6 Beds
  • 3 Baths
  • 3,784 Sq Ft
  • Built 1960

  380 Gin Ln, Southold, NY 11971

  Last Sold Summary

  • 4% Above List Price
  • $264/SF
  • 88 Days On Market

  Last Sold Price $999,000

  Last Listing Agent Ryan Springer Corcoran
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  /15

  $699,000

  • 2 Beds
  • 1 Bath
  • 1,114 Sq Ft

  265 Hummel Ave, Southold, NY 11971

  Welcome to 265 Hummel Ave in Southold, a charming two-bedroom, one-bathroom gem that embodies the perfect balance of comfort and potential. This property is a blank canvas for your imagination, boasting a full attic that presents an exciting opportunity for expansion, allowing you to customize the loft space to your unique needs and taste. The home is situated in a vibrant community that thrives

  Amanda Lin Douglas Elliman Real Estate

  265 Hummel Ave, Southold, NY 11971
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  /47

  $20,000 per month

  • 5 Beds
  • 3.5 Baths
  • 3,700 Sq Ft
  • House for Rent

  425 Cedar Point Dr E, Southold, NY 11971

  Now Available for June, July or August 2026. June for $20,000, July for $27,500 or August for $32,500. This Impressive Home is Set Creekfront with Private Dock with Peconic Bay Access and Associated Bay Beach within the Community. The Extensive Rear Patio Area is Impressive with an Inground Pool and Jacuzzi. All Creekfront with a Beautiful View. The Home is Grand and Designed to Entertain.

  Rene Giacobbe Douglas Elliman Real Estate

  425 Cedar Point Dr E, Southold, NY 11971
• 

  $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 $692,222 Not Listed For Sale

  155 Seawood Dr, Southold, NY 11971

  • 2 Beds
  • 1 Bath
  • Built 1958

  155 Seawood Dr, Southold, NY 11971

  Last Sold Summary

  • 3% Above List Price
  • 33 Days On Market

  Last Sold Price $675,000

  Last Listing Agent Scott Bennett Douglas Elliman Real Estate
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  /36

  $4,900,000

  • Land
  • 51 Acres
  • $96,078 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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  /20

  $55,000 per month

  • 5 Beds
  • 3.5 Baths
  • 2,750 Sq Ft
  • House for Rent

  7635 Main Bayview Rd, Southold, NY 11971

  Elegant Historic Home in Southold – Coastal Charm Meets Modern Luxury Escape to the North Fork and enjoy this beautifully restored historic Southold home, perfectly blending timeless elegance with every modern comfort. This spacious retreat features 5 bedrooms and 3.5 baths, ideal for families or groups seeking a serene getaway. Enjoy central air conditioning, high-speed internet, and five smart

  Mary Terry MCKENNASHEA LLC

  7635 Main Bayview Rd, Southold, NY 11971
• 

  $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 $414,000

  Last Listing Agent Kenneth Poliwoda Douglas Elliman Real Estate

  55075 Route 25 Unit 1, Southold, NY 11971
• 

  Est $3,014,000 Not Listed For Sale

  9502 N Bayview Rd, Southold, NY 11971

  • 5 Beds
  • 4.5 Baths
  • 4,051 Sq Ft
  • Built 2019

  9502 N Bayview Rd, Southold, NY 11971

  Last Sold Summary

  • 3% Below List Price
  • $765/SF
  • 187 Days On Market

  Last Sold Price $3,100,000

  Last Listing Agent Thomas McCarthy Thomas J McCarthy Real Estate

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