Southold, NY Homes

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  /50

  $1,950,000

  • 4 Beds
  • 3.5 Baths
  • 4,173 Sq Ft

  295 Grange Rd, Southold, NY 11971

  Southold SanctuaryThere's a certain ease to life on the North Fork and knowing you are never far from the water - where summer stretches into fall, where neighbors still wave, and where the days' quiet rhythm becomes your soundtrack. Welcome to 4,173 square feet of newly built grace on just under a half-acre in Southold and one mile to Goose Creek Beach and two miles to Cedar Beach. This

  Sheri Winter Parker Corcoran

  295 Grange Rd, 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
• 

  $910,000 Sold Nov 03, 2025

  600 Parkway, Southold, NY 11971

  • 3 Beds
  • 1 Bath
  • 1,600 Sq Ft
  • Built 1969

  Last Sold Summary

  • 2% Above List Price
  • $569/SF
  • 12 Days On Market

  Current Estimated Value $884,533

  Last Listing Agent Alexis Meadows Douglas Elliman Real Estate

  600 Parkway, Southold, NY 11971
• 

  Est $1,525,061 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,934 Sq Ft

  2085 Bayview Ave, Southold, NY 11971

  2085 Bayview Ave, Southold, NY 11971
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  /15

  $1,699,000

  • 5 Beds
  • 2 Baths
  • 1,688 Sq Ft

  530 Sunset Way, Southold, NY 11971

  Wake up to breathtaking panoramic views of Peconic Bay from your own private waterfront retreat! With 160 feet of shoreline and a 6'x20' dock, this property is a dream for boaters, beach lovers, and anyone craving coastal serenity. Inside, there’s room for everyone with 5 bedrooms, 2 full baths, and a sunlit loft. The wraparound deck invites you to savor spectacular sunrises and sunsets,

  Thomas McCarthy Thomas J McCarthy Real Estate

  530 Sunset Way, 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
• 

  $287,500 Sold May 15, 2025

  1195 Ruch Ln, Southold, NY 11971

  • Land
  • 0.13 Acre
  • $2,211,538 per Acre

  Last Sold Summary

  • 27% Below List Price
  • 110 Days On Market

  Current Estimated Value $287,000

  Last Listing Agent Bridget Elkin Compass Greater NY LLC

  1195 Ruch Ln, Southold, NY 11971
• 

  Est $1,604,765 Not Listed For Sale

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

  265 Cedar Point Dr E, Southold, NY 11971

  265 Cedar Point Dr E, Southold, NY 11971
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  /40

  $2,499,000 Pending

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

  285 Blue Marlin Dr, Southold, NY 11971

  BONUS: Upon request builder will include a custom built 12x12 pool shed with the same materials and style identical to the house. Entire house completed and beautifully landscaped!!! 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

  Connie Liappas Compass

  285 Blue Marlin Dr, 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
• 

  $775,000 Sold Mar 14, 2025

  5535 Old Rd N, Southold, NY 11971

  • 3 Beds
  • 1 Bath
  • 1,760 Sq Ft
  • Built 1949

  Last Sold Summary

  • 7% Below List Price
  • $440/SF
  • 102 Days On Market

  Current Estimated Value $858,026

  Last Listing Agent Tom Scalia Century 21 Albertson Realty

  5535 Old Rd N, Southold, NY 11971
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  Est $2,809,333 Not Listed For Sale

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

  920 Cedar Point Dr E, Southold, NY 11971

  920 Cedar Point Dr E, Southold, NY 11971
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  /38

  $1,675,000

  • 4 Beds
  • 2.5 Baths
  • 3,110 Sq Ft

  1260 Water Terrace, Southold, NY 11971

  Welcome to your own slice of paradise in the coveted Angel Shores beach community. This beautifully crafted home offers deeded bay beach access at the end of the road, and a spectacular backyard retreat—complete with vibrant gardens, an inviting inground pool, hot tub, and tranquil waterfall. Whether you're entertaining guests or enjoying a quiet evening at home, this outdoor space delivers the

  Katie Schimpf Daniel Gale Sothebys Intl Rlty

  1260 Water Terrace, Southold, NY 11971
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  /28

  $3,800 per month

  • 3 Beds
  • 2 Baths
  • 1,450 Sq Ft
  • House for Rent

  5125 Main Bayview Rd, Southold, NY 11971

  Experience easy one-level living in this immaculate home in Southold! Clean and airy throughout along with a lovely yard with plenty of privacy. Set in the sought after Goose Neck Estates with its own sandy beach down the road. The welcoming front porch opens to an inviting and comfortable living room and spacious den with hardwood floors and a wood burning fireplace. The dining area leads to the

  Suzette Reiss Douglas Elliman Real Estate

  5125 Main Bayview Rd, Southold, NY 11971
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  /36

  $2,700,000 Sold Sep 25, 2025

  54985 County Road 48, Southold, NY 11971

  • 4 Beds
  • 5 Baths
  • 3,500 Sq Ft
  • Built 2010

  Last Sold Summary

  • 16% Below List Price
  • $771/SF
  • 134 Days On Market

  Current Estimated Value $1,952,655

  Last Listing Agent Nicholas Planamento William Raveis (Mattituck)

  54985 County Road 48, Southold, NY 11971
• 

  Est $2,902,712 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths

  750 Cedar Point Dr E, Southold, NY 11971

  750 Cedar Point Dr E, Southold, NY 11971
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  /20

  $554,000 Pending

  • Land
  • 0.92 Acre
  • $602,174 per Acre

  4077 Main Bayview Rd, Southold, NY 11971

  Here is a wonderful opportunity to build your dream home on this private shy waterfront acre on West Creek. Building plans approved for 2,900 sq ft home with 3BRs/2.5Baths with 2 car garage. This is a flag lot. Property is close to town, beaches and the North Fork has to offer. Seller has the following approvals: Zoning Board of Appeals, Southold Town Trustees wetland permit; health department

  Mary Ellen Ellwood Douglas Elliman Real Estate

  4077 Main Bayview Rd, Southold, NY 11971
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  $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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  $2,250,000 Sold Oct 24, 2025

  1710 N Bayview Road Extension, Southold, NY 11971

  • 4 Beds
  • 4.5 Baths
  • 3,700 Sq Ft
  • Built 2005

  Last Sold Summary

  • 2% Below List Price
  • $608/SF
  • 13 Days On Market

  Current Estimated Value $2,256,105

  Last Listing Agent Eric Elkin Compass Greater NY LLC

  1710 N Bayview Road Extension, Southold, NY 11971
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  Est $2,201,333 Not Listed For Sale

  • 4 Beds
  • 2 Baths

  250 Midway Rd, Southold, NY 11971

  250 Midway Rd, Southold, NY 11971
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  /19

  $239,000

  • 1 Bath
  • 250 Sq Ft

  52325 County Road 48 Unit 31, Southold, NY 11971

  Seasonal Condo Near a Memorable Long Island Sound Beach (Town Beach). Studio Apartment with Efficiency Kitchen and is Located on the 2nd Floor. The Condo Offers a Community Room, Lawn with BBQ Area, Laundry, Off Street Parking, Boat Storage, Beach Storage. Electric, Water, Cable and Sewer/Cesspool included in Common Charge of $253 Monthly. SEASONAL CONDO OPEN APRIL TO NOVEMBER. NOT YEAR ROUND.

  Paul Loeb Douglas Elliman Real Estate

  52325 County Road 48 Unit 31, Southold, NY 11971
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  /17

  $3,200 per month

  • 2 Beds
  • 1 Bath
  • 1,155 Sq Ft
  • Apartment for Rent

  49925 Main Rd, Southold, NY 11971

  Southold Town Rental Permit #0787. NEWLY RENOVATED Light, Bright And Airy 2nd Floor YEAR ROUND Apartment With 2 Bedrooms And A Full Bath In Southold's Historic Corridor, Gorgeous Grounds And Landscaping, Close To All!, Additional information: Appearance:Excellent

  Thomas McCarthy Thomas J McCarthy Real Estate

  49925 Main Rd, Southold, NY 11971
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  $650,000 Sold Apr 30, 2025

  2340 Ackerly Pond Ln, Southold, NY 11971

  • Land
  • 15.96 Acres
  • $40,727 per Acre

  Last Sold Summary

  • 9% Above List Price
  • 16 Days On Market

  Last Listing Agent Joseph Divello Century 21 Albertson Realty

  2340 Ackerly Pond Ln, Southold, NY 11971
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  Est $1,351,556 Not Listed For Sale

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

  1750 Water Terrace, Southold, NY 11971

  1750 Water Terrace, Southold, NY 11971
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  /9

  $450,000 Pending

  • Land
  • 0.3 Acre
  • $1,500,000 per Acre

  140 Arshamomaque Ave, Southold, NY 11971

  Building Lot in Beixedon Estates private community. Private road, deeded access to private community beach. Broker/Owner.

  John J. Nickles, Jr. Lewis & Nickles LTD

  140 Arshamomaque Ave, Southold, NY 11971
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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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  $1,035,000 Sold Jun 20, 2025

  55 Cedar Point Dr W, Southold, NY 11971

  • 3 Beds
  • 2 Baths
  • 1,650 Sq Ft
  • Built 1973

  Last Sold Summary

  • 5% Below List Price
  • $627/SF
  • 62 Days On Market

  Current Estimated Value $1,103,519

  Last Listing Agent Kristy Naddell Douglas Elliman Real Estate

  55 Cedar Point Dr W, Southold, NY 11971
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  Est $1,256,028 Not Listed For Sale

  • 3 Beds
  • 2 Baths

  505 Longview Ln, Southold, NY 11971

  505 Longview Ln, Southold, NY 11971
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  /29

  $1,298,500

  • 3 Beds
  • 3.5 Baths
  • 2,400 Sq Ft

  12250 Soundview Ave, Southold, NY 11971

  North Fork Coastal Living With Sunset & Water ViewsEnjoy breathtaking sunsets and water views from any of the three private balconies of this beautiful North Fork retreat. Designed for comfort and relaxed elegance, this residence features a dynamic open floor plan that seamlessly connects the living room, dining, and kitchen areas leading to outdoor balconies. The granite kitchen is perfect

  Scott Bennett Douglas Elliman Real Estate

  12250 Soundview Ave, Southold, NY 11971
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  /46

  $30,000 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
• 

  $780,000 Sold Jan 06, 2026

  390 Wildberry Ln, Southold, NY 11971

  • Land
  • 0.67 Acre
  • $1,164,179 per Acre

  Last Sold Summary

  • 2% Below List Price
  • 18 Days On Market

  Last Listing Agent Robert Merolla Aurora Property Group

  390 Wildberry Ln, Southold, NY 11971
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  Est $1,037,114 Not Listed For Sale

  • 4 Beds
  • 2 Baths

  1100 Rambler Rd, Southold, NY 11971

  1100 Rambler Rd, Southold, NY 11971
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  /4

  $1,600,000

  • Land
  • 2 Acres
  • $800,000 per Acre

  55975 Route 25, Southold, NY 11971

  2 Acres Of Highly Desirable Hamlet Business Zoning. Subdividable Into Half Acre Lots Or Build Multiple Structures. Multiple Residential Units Possible Or Residential/Commercial Mix. 4 Buildings Possible As Of Right. Great Route 25 Exposure & Great Location In Center Of Hamlet! Commercial Listing MLS# 3530579

  Colin McCarthy Thomas J McCarthy Real Estate

  55975 Route 25, Southold, NY 11971
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  /26

  $5,000 per month

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

  1000 Rambler Rd, Southold, NY 11971

  Available Year-Round or Seasonal: Beautiful like new colonial just 500 feet from sandy bay beach. Four bedrooms plus a lovely sunroom. 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. Year-Round $5000/month plus utilities. Memorial Day-Labor Day $65,000, or July & August $50,000

  Pamela Hunt Colony Realty

  1000 Rambler Rd, Southold, NY 11971
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  $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 $3,825,000

  Last Listing Agent Kristy Naddell Douglas Elliman Real Estate

  1750 Mount Beulah Ave, Southold, NY 11971
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  Est $1,345,410 Not Listed For Sale

  • 4 Beds
  • 2 Baths

  65 Pleasant Place, Southold, NY 11971

  65 Pleasant Place, Southold, NY 11971
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  /3

  $1,400,000

  • 4 Beds
  • 3.5 Baths
  • 2,215 Sq Ft

  500 Summer Ln, Southold, NY 11971

  The classic North Fork lifestyle you have been waiting for has finally arrived. Nestled in a quiet Southold neighborhood, 500 Summer Lane offers the rare opportunity to create a retreat just moments from the beaches, vineyards, and beloved local destinations that define the North Fork. Here, tranquility meets convenience—you’re never far from the shoreline or the vibrant heartbeat of the

  Catherine Flood Compass Greater NY LLC

  500 Summer Ln, Southold, NY 11971
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  /47

  $25,000 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 2026. 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. Boasting 5 Bedrooms and 4 Baths. 2 Large Living Rooms, Well Appointed Kitchen

  Rene Giacobbe Douglas Elliman Real Estate

  425 Cedar Point Dr E, Southold, NY 11971
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  $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 $1,320,939

  Last Listing Agent Zachary Scher Signature Premier Properties

  4710 Old Rd N, Southold, NY 11971
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  Est $1,195,444 Not Listed For Sale

  • 4 Beds
  • 3 Baths

  945 Gin Ln, Southold, NY 11971

  945 Gin Ln, Southold, NY 11971

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