Southold, NY Homes for Sale

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  /42

  $3,695,000

  $155K PRICE DROP

  • 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

  Roric Tobin Compass Greater NY LLC

  105 Waterview Dr, Southold, NY 11971
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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 &

  Kathleen Travers Douglas Elliman Real Estate

  11200 N Bayview Rd, Southold, NY 11971
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  /44

  $939,000

  • 3 Beds
  • 3.5 Baths
  • 2,950 Sq Ft

  595 Greenfields Ln, Southold, NY 11971

  Location!Location!Location! Some homes are beautiful, others are truly one of a kind. 595 Greenfields Lane is both! Set on nearly 1 acre of meticulously landscaped property on a quiet dead end street, this exceptional custom built home is located just moments away from the historic village of Southold and the very best of the North Fork! Just a mile from the beach and steps away from Long

  Giuseppe Pinello Exit Realty Achieve

  595 Greenfields Ln, Southold, NY 11971
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  /43

  $1,849,000

  $76K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 2,850 Sq Ft

  2100 Glenn Rd, Southold, NY 11971

  This turnkey opportunity in Southold, bordering beautiful Goose Creek, offers a private dock and is perfect for those seeking a North Fork beach house with a boater's lifestyle. Situated on more than two-thirds of an acre, this contemporary home features modern lines, abundant natural light, and a stunning yard ideal for outdoor entertaining. Upon arrival, you are welcomed by a spacious driveway

  Alexis Meadows Compass Greater NY LLC

  2100 Glenn Rd, Southold, NY 11971
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  /34

  $3,100,000

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

  3651 Soundview Ave, Peconic, NY 11958

  Charming updated Soundfront beach house! This home is what dreams are made of. Steps away is a plush, powder white sandy path leading to a serene private beach where panoramic vistas and mesmerizing sunsets will sweep you off your feet. Offering approximately 1,600 sq. ft. of living space, the first level boasts an eat-in-kitchen, living room with fireplace to cozy up to during those brisk fall

  Nicholas Liappas Compass Greater NY LLC

  3651 Soundview Ave, Peconic, NY 11958
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  /48

  $2,595,000

  $300K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,840 Sq Ft

  21515 Soundview Ave, Southold, NY 11971

  Life on the North Fork doesn't get better than this! Set along the Long Island Sound in one of Southold's most desirable locations, this chic waterfront escape offers sweeping water views, sensational sunsets, and effortless coastal living. Renovated in 2016 and completely move-in ready, the home blends sophisticated style with relaxed comfort, creating the perfect setting for both entertaining

  Kristy Naddell Douglas Elliman Real Estate

  21515 Soundview Ave, Southold, NY 11971
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  $1,299,000

  $86K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,200 Sq Ft

  4408 Old North Rd, Southold, NY 11971

  Located in one of the most sought-after locations on the North Fork sits this quintessential cedar shake farmhouse situated on 2 private acres! This home combines timeless charm with modern comforts. The main level features hardwood floors throughout, a spacious living room with a wood-burning fireplace, formal dining room, eat-in kitchen with granite countertops and pantry, a convenient half

  Kristy Naddell Douglas Elliman Real Estate

  4408 Old North Rd, Southold, NY 11971
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  /42

  $1,299,000

  • 4 Beds
  • 3 Baths
  • 2,240 Sq Ft

  1075 Ships Dr, Southold, NY 11971

  Classic Americana meets the North Fork lifestyle on Southold's Bayview Peninsula. Set on a level half acre backing to protected town owned land, this four bedroom, three bath Center Hall Colonial combines timeless design, thoughtful updates, and an exceptional location near Southold's most sought-after waterfront destinations. A welcoming portico leads into a home with wood floors throughout. The

  Joshua Whalley Douglas Elliman Real Estate

  1075 Ships Dr, Southold, NY 11971
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  /40

  $3,300,000

  • 4 Beds
  • 2.5 Baths
  • 3,028 Sq Ft

  3645 Soundview Ave, Peconic, NY 11958

  North Fork retreat! A powder white sandy path leads to a gorgeous private beach offering 116 ft. of waterfrontage while incredible sparkling Sound views, sunsets, and lush greenery set this property apart. Enjoy water views from the open concept main level and the expansive 800+ sq. ft. rear deck - perfect for lounging, al fresco dining and taking in the fresh sea air. With over 3,000 sq. ft. of

  Nicholas Liappas Compass Greater NY LLC

  3645 Soundview Ave, Peconic, NY 11958
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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

  Karyn Flores Compass Greater NY LLC

  430 Grove Rd, Southold, NY 11971
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  /41

  $969,000

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

  270 Opechee Ave, Southold, NY 11971

  Welcome to North Fork living! Nestled in the desirable, private beach community of Laughing Water, this charming 3-bedroom, 2-bath Ranch sits on a 0.38-acre lot.Inside, enjoy hardwood floors throughout the living and dining areas, along with a newly updated kitchen featuring new appliances, a center island, and generous storage. A 10’ x 13’ screened-in porch provides the perfect

  Patricia Shackel Douglas Elliman Real Estate

  270 Opechee Ave, Southold, NY 11971
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  /38

  $3,899,000

  $401K PRICE DROP

  • Land
  • 45.77 Acres
  • $85,187 per Acre

  46975 Main Rd, Southold, NY 11971

  A rare opportunity to create a truly bespoke North Fork lifestyle or equestrian estate in the heart of Southold’s celebrated agricultural landscape. Privately set across 45.54 acres, the offering includes 43.7 acres of preserved agricultural land and a separate 1.84-acre residential parcel with development rights intact-an exceptional setting to create a distinctive residence overlooking your own

  Andrea Parks Douglas Elliman Real Estate

  46975 Main Rd, Southold, NY 11971
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  /17

  $895,000

  $104K 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 with new refrigerator, and dining area ideal for everyday living

  Scott Bennett Douglas Elliman Real Estate

  240 Lisa Dr, Southold, NY 11971
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  /23

  $1,445,000

  $150K PRICE DROP

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

  2015 Kenneys Rd, Southold, NY 11971

  Explore a prime location in Southold, perfect for a beach getaway, featuring the highly sought-after Kenneys Beach—one of the most picturesque beaches on the North Fork. This traditional-style home is built with meticulous attention to detail and quality craftsmanship. Upon entering, you are greeted by a cathedral ceiling that highlights a stunning stone staircase with iron railings. The spacious

  Alexis Meadows Compass Greater NY LLC

  2015 Kenneys Rd, Southold, NY 11971
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  /18

  $650,000

  • Land
  • 40,162 Sq Ft
  • $704,989 per Acre

  420 Lake Dr, Southold, NY 11971

  The Dune Road of the North Fork. Do you love the beach? You know that feeling, tranquility and the sound of the waves off in the distance. Well, this is your chance to capture it and create your safe haven, your wellness retreat. This is what the doctor ordered! Steps from Little Fish and Kenney's and McCabe Beaches. Hurry up, this one is going to go fast!

  Sheri Winter Parker Corcoran

  420 Lake Dr, Southold, NY 11971
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  /3

  $1,495,000

  • 4 Beds
  • 4 Baths
  • 4,300 Sq Ft

  3995 Wells Ave, Southold, NY 11971

  Bring your vision to the waterfront in Southold. Set along a peaceful creek with direct water access, this fully gutted home offers a rare opportunity to create a custom North Fork retreat. A newly installed bulkhead and existing private dock provide the perfect setting for boating, fishing, kayaking and unforgettable days on the water. Renovate, redesign and make it your own—all just minutes

  James Bissett Hedgestone Commercial Rlty LLC

  3995 Wells Ave, Southold, NY 11971
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  /39

  $5,995,000

  $555K PRICE DROP

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

  920 Cedar Point Dr E, Southold, NY 11971

  Welcome to 920 Cedar Point E in Southold, a spectacular 1.4-acre waterfront estate overlooking one of the most breathtaking stretches of the Peconic Bay, complete with a private deeded dock slip just steps from the property. Featuring 200 feet of pristine sugar-sand beachfront, this exceptional setting offers privacy, serenity, all-day sunshine, and the gentle prevailing southwest breezes for

  William Mcintosh Daniel Gale Sothebys Intl Rlty

  920 Cedar Point Dr E, Southold, NY 11971
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  /11

  $3,295,000

  New Construction Open House 10/03

  • 4 Beds
  • 4.5 Baths
  • 5,100 Sq Ft

  390 Wildberry Ln, Southold, NY 11971

  New Construction Luxury Southold Home underway set to be complete September 2026. Nestled in the prestigious Wildberry Fields, this new home blends coastal elegance with peaceful North Fork country living. Features 5,100 SF of living space on 3 levels with 4 Bedrooms and 4.5 Bathrooms plus a bonus room/office over your attached 3 car garage. This stunning home has everything including a Giant

  Shaun McQuilkin Migrate Realty LLC

  390 Wildberry Ln, Southold, NY 11971
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  /2

  $799,000

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

  36595 County Road 48, Peconic, NY 11958

  Lovely 4 bedroom, 2bath Ranch homelg living room, dining rm and new kitchen 2years ago.Excellent investment property. Surrounded by quite farm field.

  Donna Fakiris Modern Age Realty Group LLC

  36595 County Road 48, Peconic, NY 11958
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  /22

  $949,000

  • 3 Beds
  • 1.5 Baths
  • 2,350 Sq Ft

  155 2nd Ave, Peconic, NY 11958

  North Fork Coastal Living by the Sound. Welcome to 155 Second Avenue, located in the charming hamlet of Peconic. The beach retreat you've been looking for, just 500 feet from both private and town beach access at Goldsmiths Inlet Beach. Custom built in 2005 by the current owner, this thoughtfully constructed beach home reflects true pride of ownership. Featuring open-concept living, dining, and

  Melissa Principi Douglas Elliman Real Estate

  155 2nd Ave, Peconic, NY 11958
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  /17

  $789,900

  Open Sat 11AM - 1PM $29K PRICE DROP

  • 3 Beds
  • 1 Bath

  725 Peconic Ln, Peconic, NY 11958

  Fall is just around the corner!Don’t miss your chance to own a home in the heart of Wine Country and experience the beauty and fun of farm country right outside your door!Imagine apple picking, pumpkin picking, fresh pies, local fruit stands, beautiful farms, vineyards, and so much more.**People drive for miles to visit this beautiful destination—you could have the opportunity to live

  Savita Ramphal Island Group Realty Inc

  725 Peconic Ln, Peconic, NY 11958

Showing Results 41 - 61, Page 2 of 2