Southold, NY Homes

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  $13,000,000 Pending

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

  59600 Main Rd, Southold, NY 11971

  A singular opportunity to acquire 21.41 contiguous acres on the Peconic Bay, offering 470 feet of premier bayfront and a private sandy beach. More than 10 acres are planted with mature vines producing an impressive range of grape varietals. Development rights are intact, allowing for future potential.At the southern edge, a 3,500 sq. ft. waterfront residence captures sweeping bay views,

  Bridget Elkin Compass Greater NY LLC

  59600 Main 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: May $5000, June $7000, October $4500,

  Kenneth Poliwoda Douglas Elliman Real Estate

  3825 S Harbor 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 $1,726,674 Not Listed For Sale

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

  1205 Waterview Dr, Southold, NY 11971

  1205 Waterview Dr, Southold, NY 11971
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  /2

  $549,000 Pending

  • Land
  • 3.03 Acres
  • $181,188 per Acre

  Unlisted Address

  Calling all privacy seekers! Located in the heart of Long Island's North Fork, this 3 acre flag lot is close to all that this area has to offer. Goldsmiths Inlet Park is just .5 mile down the road while Kennys sandy LI Sound beach is just 1.3 miles away. Close to vineyards, award winning dining, golf and so much more!

  Erica McKenzie Andrew Stype Realty Inc

  Unlisted Address
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  /24

  $20,000 per month

  • 3 Beds
  • 3 Baths
  • House for Rent

  355 Midway Rd, Southold, NY 11971

  Available seasonally, this impeccable modern 3 bedroom 3 bath home in Southold's coveted Cedar Beach district offers privacy, water views and a private neighborhood beach. The open plan includes kitchen, dining area, den/office, and living room with fireplace. Sliding doors open to the bluestone patio with gas grill and plenty of room for entertaining and sunning. The three bedrooms, including a

  Marianne Collins Brown Harris Stevens N Fork

  355 Midway Rd, 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 $702,861

  Last Listing Agent Janet Markarian Daniel Gale Sothebys Intl Rlty

  280 Lakeside Dr N, Southold, NY 11971
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  Est $991,950 Not Listed For Sale

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

  60 Koke Dr, Southold, NY 11971

  60 Koke Dr, Southold, NY 11971
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  $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.

  Kristy Naddell Douglas Elliman Real Estate

  790 N Sea Dr, Southold, NY 11971
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  $20,000 per month

  • 4 Beds
  • 4 Baths
  • 3,200 Sq Ft
  • House for Rent

  950 Blue Marlin Dr, Southold, NY 11971

  Beachfront, located in Southold Shores, this architect's own home is built with all the beautiful appointments you can imagine. Embracing the purity of architectural detail, together with a refined simplicity, this waterfront home offers a timeless elegance. Sweeping sunsets eye-catching angles and thoughtful details provide constant visual interest. A large 4 bedrooms with 4 baths ensuite,

  Lori Feilen William Raveis New York LLC

  950 Blue Marlin Dr, Southold, NY 11971
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  $1,573,500 Sold Jan 10, 2025

  500 Arshamomaque Ave, Southold, NY 11971

  • 4 Beds
  • 5 Baths
  • 2,334 Sq Ft
  • Built 2024

  Last Sold Summary

  • 5% Below List Price
  • $674/SF
  • 50 Days On Market

  Current Estimated Value $1,581,678

  Last Listing Agent Lisa Davey LI Probate Realty Inc

  500 Arshamomaque Ave, Southold, NY 11971
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  Est $1,509,810 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 2,232 Sq Ft

  6320 Main Bayview Rd, Southold, NY 11971

  6320 Main Bayview Rd, Southold, NY 11971
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  $925,000

  • Land
  • 2 Acres
  • $462,500 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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  /21

  $6,000 per month

  • 4 Beds
  • 3 Baths
  • House for Rent

  1155 Old Harbor Rd, Southold, NY 11971

  Quintessential North Fork sandy bay beachfront rental. Stunning views across Cutchogue Harbor and Peconic Bay will be yours at this spacious waterfront home, whether from the airy great room, the brick patio, or from the beachside deck. Tucked away down a quiet drive, this home offers peace and privacy in historic New Suffolk. There are 3 bedrooms and 2 baths upstairs, one bedroom and one bath

  Marianne Collins Brown Harris Stevens N Fork

  1155 Old Harbor Rd, Southold, NY 11971
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  $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

  Last Listing Agent Rita Rooney Douglas Elliman Real Estate

  205 Grange Rd, Southold, NY 11971
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  Est $940,114 Not Listed For Sale

  • 3 Beds
  • 2 Baths

  600 Corey Creek Ln, Southold, NY 11971

  600 Corey Creek Ln, Southold, NY 11971
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  /18

  $799,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,300 Sq Ft

  150 Hobart Rd, Southold, NY 11971

  Welcome to your dream North Fork escape! A storybook coastal cottage tucked away on a quiet street, just a few blocks from Founder’s Landing Park, the beach, and the Wharf House, This 2-bedroom, 2-bathroom cedar shake home is full of charm, comfort, and convenience. Whether you're looking for a full-time home, a weekend getaway, or a stylish rental property, this one has it all—and then some.

  Kim Parshley Compass Greater NY LLC

  150 Hobart Rd, Southold, NY 11971
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  /40

  $10,000 per month

  • 4 Beds
  • 2.5 Baths
  • House for Rent

  1275 the Esplanade, Southold, NY 11971

  STUNNER 4BR DESIGNER HOME ~ PET FRIENDLY, HEATED POOL & BEACH!August 2 Weeks Only $15,000 and $18,000! First Time Offered! (see below) Fabulous vacations on the coveted Esplanade in "Angel Shores", with a deeded sandy bay beach and heated freeform lagoon pool with a waterfall. Property is fully fenced and private, with many lounge areas for sunning, a shady pergola when needed, and a great

  Kate Carpluk William Raveis New York LLC

  1275 the Esplanade, Southold, NY 11971
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  $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 $1,350,263

  Last Listing Agent Lisa Gillooly Compass Greater NY LLC

  5950 N Bayview Rd, Southold, NY 11971
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  Est $974,022 Not Listed For Sale

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

  50 Wabasso St, Southold, NY 11971

  50 Wabasso St, 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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  /11

  $7,000 per month

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

  470 Goose Creek Ln, Southold, NY 11971

  Rental permit 405. Dine Al Fresco! Enjoy The Spectacular Sunsets At This Waterfront Paradise. 3 Bedroom 2 bath Contemporary Home With 1st Floor Waterside Master Suite. New Soft padded Heated/Lighted Salt Water IG Pool W/Automatic Cover, Unobstructed Spectacular Waterviews, Enclosed Outdoor Shower, Hi End Newly Built Kitchen. Enjoy Kayaking, Paddle Boarding and Fishing From Your Own Dock. Easy

  Thomas McCarthy Thomas J McCarthy Real Estate

  470 Goose Creek Ln, Southold, NY 11971
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  $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 $1,144,341

  Last Listing Agent Shane Hafer Compass Greater NY LLC

  2865 S Harbor Rd, Southold, NY 11971
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  Est $1,068,735 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,100 Sq Ft

  150 Baywater Ave, Southold, NY 11971

  150 Baywater Ave, Southold, NY 11971
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  $839,000

  • 4 Beds
  • 2 Baths
  • 1,600 Sq Ft

  280 Clearview Ave, Southold, NY 11971

  A charming four-bedroom, two-bath, one-level home with a touch of nostalgic appeal. This home boasts wood flooring and an attached two-car garage, nestled on a level corner lot. The primary bedroom offers the convenience of an attached full bathroom. The house, while in need of a little TLC, presents an exciting opportunity - a blank canvas ready for your personal touch. The full basement adds to

  Rita Rooney Douglas Elliman Real Estate

  280 Clearview Ave, Southold, NY 11971
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  /32

  $30,000 per month

  • 6 Beds
  • 4 Baths
  • 3,000 Sq Ft
  • House for Rent

  1695 Old Woods Path, Southold, NY 11971

  Southold, North Fork: This beautiful estate, bayfront home offers complete privacy in a peaceful woodland setting with a historic provenance and featuring a sugar sand beach. Despite its private location, it is conveniently close to the village and North Fork amenities. Croteaux is just up the lane, and NoFo table is a short bike ride away. The estate house has a broad porch, a living room with a

  Nicholas Planamento William Raveis New York LLC

  1695 Old Woods Path, Southold, NY 11971
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  $849,000 Sold Mar 19, 2025

  950 Paradise Shores Rd, Southold, NY 11971

  • 4 Beds
  • 2 Baths
  • 1,700 Sq Ft
  • Built 1983

  Last Sold Summary

  • $499/SF
  • 7 Days On Market

  Current Estimated Value $895,487

  Last Listing Agent Diane Mollica Compass Greater NY LLC

  950 Paradise Shores Rd, Southold, NY 11971
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  Est $1,152,129 Not Listed For Sale

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

  500 Glenn Rd, Southold, NY 11971

  500 Glenn Rd, Southold, NY 11971
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  $1,649,999

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

  3715 Hortons Ln, Southold, NY 11971

  Designer Modern Farmhouse ranch set on over 3.35 Acres with farm and scenic views. Renovated 2023. Open concept Living room, Dining room and Kitchen, Gorgeous kitchen with quartz countertops, Stainless Steel Appliances, built in wine cooler, new windows throughout, new interior doors, new exterior doors, new flooring, updated designer baths, new boiler, new well pump, new hot water heater.

  Arelis Olivieri RIN

  3715 Hortons Ln, Southold, NY 11971
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  $1,250,000 Sold Nov 25, 2025

  800 Goose Creek Ln, Southold, NY 11971

  • 3 Beds
  • 3 Baths
  • 2,032 Sq Ft
  • Built 1997

  Last Sold Summary

  • $615/SF
  • 21 Days On Market

  Last Listing Agent Nancy Cervelli Daniel Gale Sothebys Intl Rlty

  800 Goose Creek Ln, Southold, NY 11971
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  Est $1,136,890 Not Listed For Sale

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

  220 Glenn Rd, Southold, NY 11971

  220 Glenn Rd, Southold, NY 11971
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  $1,799,000

  • 5 Beds
  • 5.5 Baths
  • 3,350 Sq Ft

  480 Ackerly Pond Ln, Southold, NY 11971

  Step into this custom home where luxury craftsmanship provides everyday tranquility. Experience the pinnacle of North Fork living in this bespoke custom-built residence, thoughtfully constructed with modern elegance and a timeless design. Nestled on a quiet property and offering seamless access to Southold Town beaches, vineyards, breweries, marinas, and North Fork restaurants, this exceptional

  Catherine Flood Compass Greater NY LLC

  480 Ackerly Pond Ln, Southold, NY 11971
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  $602,500 Sold Jul 08, 2025

  2555 Youngs Ave Unit 12E, Southold, NY 11971

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 1986

  Last Sold Summary

  • $502/SF
  • 19 Days On Market

  Last Listing Agent Timothy O'Keefe Signature Premier Properties

  2555 Youngs Ave Unit 12E, Southold, NY 11971
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  Est $951,223 Not Listed For Sale

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

  3715 Main Bayview Rd, Southold, NY 11971

  3715 Main Bayview Rd, Southold, NY 11971
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  $824,000 Pending

  • 2 Beds
  • 1 Bath
  • 1,472 Sq Ft

  80 Clearview Ave W, Southold, NY 11971

  Nestled on .49 acre corner lot, this 2-bedroom, 1-bath home offers a thoughtful blend of comfort, charm, and modern updates. The heart of the home is the large kitchen, beautifully redone in 2018 with granite countertops, stainless steel appliances, a pantry, coffee bar, wine fridge, and a peninsula with seating that makes entertaining effortless. An open dining area flows naturally into the

  Erica Kelly Daniel Gale Sothebys Intl Rlty

  80 Clearview Ave W, Southold, NY 11971
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  $690,000 Sold Mar 03, 2025

  500 Gagens Landing Rd, Southold, NY 11971

  • 3 Beds
  • 1.5 Baths
  • Built 1964

  Last Sold Summary

  • 9% Below List Price
  • 167 Days On Market

  Current Estimated Value $730,590

  Last Listing Agent Katie Schimpf Daniel Gale Sothebys Intl Rlty

  500 Gagens Landing Rd, Southold, NY 11971
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  Est $1,510,833 Not Listed For Sale

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

  2305 Glenn Rd, Southold, NY 11971

  2305 Glenn Rd, Southold, NY 11971
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  /2

  $699,990 Pending

  • Land
  • 2.11 Acres
  • $331,749 per Acre

  80 Deer Run, Southold, NY 11971

  Stephen Lee Realty Connect USA L I Inc

  80 Deer Run, Southold, NY 11971
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  $2,900,000 Sold Dec 26, 2024

  215 Colony Rd, Southold, NY 11971

  • 5 Beds
  • 4.5 Baths
  • 4,240 Sq Ft
  • Built 1996

  Last Sold Summary

  • 19% Below List Price
  • $684/SF
  • 50 Days On Market

  Current Estimated Value $3,478,500

  Last Listing Agent Sheri Winter Parker Corcoran

  215 Colony Rd, Southold, NY 11971
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  Est $859,204 Not Listed For Sale

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

  645 Shepard Dr, Southold, NY 11971

  645 Shepard Dr, Southold, NY 11971

Showing Results 201 - 240, Page 6 of 18