Southold, NY Homes for Sale with Garage

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  /10

  $605,000

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

  2555 Youngs Ave Unit 11A, Southold, NY 11971

  Welcome to this corner residence at Founders Village, where easy, low-maintenance living meets the North Fork lifestyle.This 1,200-square-foot home offers 2 bedrooms, 2 full baths and a full basement, giving you valuable storage and extra space that can be hard to find when downsizing to condominium living.The corner location provides added green space on multiple sides, along

  

  Timothy O'Keefe

  Signature Premier Properties

  2555 Youngs Ave Unit 11A, Southold, NY 11971
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  /48

  $2,899,000

  • 4 Beds
  • 3 Baths
  • 2,351 Sq Ft

  405 Williamsburgh Dr, Southold, NY 11971

  Scandinavian Chic Waterfront Masterpiece with Panoramic Water Views | Southold Built in 2022 with exceptional craftsmanship and professionally curated interiors, this breathtaking waterfront residence blends Scandinavian chic design with warm modern coastal luxury. Set on .35 acres with direct water access, the home features 4 bedrooms, 3 full baths, 2,351 square feet of beautifully designed

  

  Laura Cochran

  BERKSHIRE HATHAWAY

  405 Williamsburgh Dr, Southold, NY 11971
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  /44

  $1,999,999

  $150K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,367 Sq Ft

  2245 Little Peconic Bay Ln, Southold, NY 11971

  Rarely does a Southold waterfront property offer such a compellingcombination of privacy, direct bay access, and expansive water views.Set on a protected inlet with a permitted dock and kayak launch, thisthree-bedroom, three-bath home is designed around its extraordinarysetting. Sun-filled rooms open to a supersized waterfront deck, with achef's kitchen with soapstone

  Andrea Parks Douglas Elliman Real Estate

  2245 Little Peconic Bay Ln, Southold, NY 11971
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  /11

  $550,000

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

  2555 Youngs Ave Unit 3C, Southold, NY 11971

  Unit 3C offers a rare opportunity to create something truly your own. This 2-bedroom, 2-bath condo is ready for a new vision and offers the perfect blank canvas for buyers who would rather customize than compromise. There is tremendous potential to thoughtfully update the home to your style, selecting the finishes, fixtures, colors, and details you actually want along the way. The unfinished

  Thomas McCarthy Thomas J McCarthy Real Estate

  2555 Youngs Ave Unit 3C, Southold, NY 11971
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  /25

  $2,799,000

  New Construction $200K PRICE DROP

  • 8 Beds
  • 7 Baths
  • 5,600 Sq Ft

  1350 Hortons Ln, Southold, NY 11971

  2-Acre Private Oasis with Custom "To Be Built" Luxury Home - Excellent Location Near Town, Beaches & Vineyards! Discover the perfect blend of privacy, luxury and convenience with this exceptional vacant lot, tucked away in a serene, secluded setting --- Yet just minutes from downtown, pristine beaches, and world-class vineyards, shopping and dining. Plans are in-place for a "To Be Built" custom

  Thomas McCarthy Thomas J McCarthy Real Estate

  1350 Hortons Ln, Southold, NY 11971
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  /3

  $1,550,000

  New Construction $150K PRICE INCREASE

  • 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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  /26

  $799,000

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft

  650 Greenfields Ln, Southold, NY 11971

  Welcome to 650 Greenfields Lane, an inviting ranch-style home on just shy an acre of property, nestled in the heart of Southold, NY. This charming residence offers three bedrooms, and two full bathrooms, which includes a primary en suite that overlooks the back yard. The home's cozy living room features a traditional fireplace, perfect for creating a warm and welcoming atmosphere. The eat-in

  Barbara Poliwoda Douglas Elliman Real Estate

  650 Greenfields Ln, Southold, NY 11971
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  /37

  $574,999

  • 3 Beds
  • 1 Bath
  • 1,100 Sq Ft

  2600 Boisseau Ave, Southold, NY 11971

  Welcome to 2600 Boisseau Avenue, the best deal in all of Southold. This well-maintained 3-bedroom, 1-bath ranch situated on a spacious .39-acre property in the heart of the North Fork will not disappoint. Offering comfortable single-level living with plenty of potential, this home is a wonderful opportunity to enjoy everything the Southold lifestyle has to offer. Inside, you'll find a functional

  Zachary Scher Signature Premier Properties

  2600 Boisseau Ave, Southold, NY 11971
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  /33

  $2,695,000

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

  605 Cedar Dr, Southold, NY 11971

  This charming cedar shingle Cape has been expanded and completely renovated, resulting in a home that exudes a timeless sense of place across three full floors of living space. With five bedrooms and four bathrooms, the home expands comfortably for guests yet feels equally intimate for smaller gatherings, striking a perfect balance for those looking to host but also enjoy a refined and

  Bridget Elkin Compass Greater NY LLC

  605 Cedar Dr, Southold, NY 11971
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  /50

  $1,249,000

  $350K PRICE DROP

  • 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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  /21

  $1,150,000

  • 2 Beds
  • 1 Bath
  • 1,500 Sq Ft

  380 Clark Rd, Southold, NY 11971

  Welcome to 380 Clark Road, a sun-filled North Fork escape perfectly located near the beautiful beaches of Southold. Blending comfort, charm, and endless backyard potential, this turn key home captures the easygoing lifestyle that makes the North Fork so desirable. Natural light pours throughout the home, creating bright, cheerful interiors and a warm, welcoming feel from the moment you arrive.

  Susan Orioli Engel & Volkers North Fork

  380 Clark Rd, Southold, NY 11971
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  /15

  $1,425,000

  $2M PRICE DROP

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

  535 Bay Home Rd, Southold, NY 11971

  Waterfront Opportunity on Bay Home Road. Welcome to 535 Bay Home Road, a rare and flexible offering on one of the North Fork’s most coveted canal-front streets, located in the prestigious Willow Point community. With panoramic water views, a private dock, and access to a secluded beach, this property combines timeless coastal charm with modern luxury. Buyers can choose from two exclusive paths to

  Kim Pirreca BERKSHIRE HATHAWAY

  535 Bay Home Rd, Southold, NY 11971
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  /29

  $2,995,000

  $300K PRICE DROP

  • 4 Beds
  • 5.5 Baths
  • 7,341 Sq Ft

  80 Deer Run, Southold, NY 11971

  Southold Stunner- New ConstructionThis one's a North Fork knockout. Set at the end of a quiet cul de sac on over 2 private acres, minutes from the sand, the house was built to check every box. Inside you're met with all-day sunshine, four legit bedrooms, 4.5 spa-like baths (sanitary system in place for 7 bedrooms), and a true chef's kitchen-with a 48" Sub Zero, Wolf double range + wall oven,

  Sheri Winter Parker Corcoran

  80 Deer Run, Southold, NY 11971
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  /25

  $1,549,999

  $50K PRICE DROP

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

  3715 Hortons Ln, Southold, NY 11971

  Designer Modern Farm 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, Custom Closets, New flooring, updated Designer Baths, New Boiler, New Well Pump, New Hot Water

  Arelis Olivieri RIN

  3715 Hortons Ln, Southold, NY 11971
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  /25

  $2,399,000

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

  470 Goose Creek Ln, Southold, NY 11971

  Waterfront living designed for effortless coastal comfort. Ideally located just moments from one of Southold’s premier beaches, this updated 3-bedroom, 2-bath contemporary home offers open water views, beautiful sunrises and sunsets, and a seamless indoor–outdoor flow. The light-filled main level features a newly built modern kitchen that opens directly to the outdoor entertaining area, along

  Thomas McCarthy Thomas J McCarthy Real Estate

  470 Goose Creek Ln, Southold, NY 11971
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  /45

  $3,675,000

  New Construction

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

  150 Deer Run, Southold, NY 11971

  Gorgeous estate-like Nantucket shingle home to be completed early August with time to enjoy summer of 2026 and the Fall Harvest Season on the North Fork! Seller will consider owner financing.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

  Jeffrey Mead Corcoran

  150 Deer Run, Southold, NY 11971
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  /44

  $2,695,000

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

  2850 Main Bayview Rd, Southold, NY 11971

  Set on five bucolic acres, this property perfectly captures the pastoral character that defines the region at its best. Mature trees frame the entrance, and split-rail fencing lines the property, offering a sense of privacy and openness rarely found so close to everything the North Fork has to offer. The three-bedroom, two-bathroom farmhouse is complemented by a large barn, currently outfitted

  Bridget Elkin Compass Greater NY LLC

  2850 Main Bayview Rd, Southold, NY 11971
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  /44

  $3,450,000

  • 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. Set

  Kristy Naddell Douglas Elliman Real Estate

  790 N Sea Dr, Southold, NY 11971
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  /19

  $2,950,000

  • 4 Beds
  • 3.5 Baths
  • 4,241 Sq Ft

  9305 Soundview Ave, Southold, NY 11971

  Wake up to the salt air at your new coastal compound, a rare waterfront opportunity for those seeking something truly different. Unapologetically distinctive, this mid-century modern residence offers an extraordinary combination of waterfront, privacy, architectural character, and artistic location.Held in the same family for more than 50 years, the over 4000-square-foot home is set on two

  Thomas McCarthy Thomas J McCarthy Real Estate

  9305 Soundview Ave, Southold, NY 11971
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  /33

  $2,895,000

  • 5 Beds
  • 5.5 Baths
  • 3,240 Sq Ft

  1135 Wildberry Ln, Southold, NY 11971

  North Fork living, refined. Welcome to Wildberry. Your newly constructed dream home, where design, light, and landscape converge - set against sweeping, vineyard views and crafted for effortless indoor-outdoor living. From the moment you enter, the home reveals a quiet sophistication, with natural light pouring through thoughtfully placed openings, creating a sense of calm and connection to its

  Melissa Principi Douglas Elliman Real Estate

  1135 Wildberry Ln, Southold, NY 11971
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  /38

  $1,599,000

  New Construction $100K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,668 Sq Ft

  1700 Smith Dr S, Southold, NY 11971

  Experience the best of North Fork living in this stunning new construction home offering beautiful water views and deeded beach access. Thoughtfully designed with modern coastal elegance, this residence blends quality craftsmanship, open-concept living, and effortless indoor-outdoor flow. The main living area is filled with natural light and showcases spacious interiors, elevated finishes, and a

  Kristy Naddell Douglas Elliman Real Estate

  1700 Smith Dr S, Southold, NY 11971
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  /40

  $1,249,000

  $46K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 2,000 Sq Ft

  1220 Youngs Ave, Southold, NY 11971

  It's time to put your money in Real Estate! Here's a property that is in prime condition and generates an income plus appreciation! Hamlet Business (HB) zoned property, in the heart of the Hamlet of Southold! Currently a Legal two-family home - each apartment has two bedrooms, wood floors, updated eat-in kitchen, spacious living room, bathroom, window air-conditioners, with lots of natural light

  Lee Beninati Beninati Associates

  1220 Youngs Ave, Southold, NY 11971
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  /9

  $3,695,000

  $305K PRICE DROP

  • 3 Beds
  • 4 Baths
  • 3,496 Sq Ft

  1480 Old Wood Path, Southold, NY 11971

  Set on nearly four acres along one of the North Fork’s most coveted stretches of sandy bay beach, this is a rare opportunity to secure an exceptional waterfront property with meaningful upside. The existing three-bedroom, four-bath home offers a solid foundation for renovation or expansion, allowing a new owner to tailor the property to their vision.The grounds are equally compelling. A

  Bridget Elkin Compass Greater NY LLC

  1480 Old Wood Path, Southold, NY 11971
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  /28

  $2,200,000

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

  225 Lakeside Dr S, Southold, NY 11971

  Fully renovated and exceptionally private, this sophisticated waterfront contemporary is a true North Fork retreat, pairing stylish interiors with a serene setting and an effortless outdoor lifestyle. Hardwood floors and walls of glass define the open-concept, where a beautifully appointed kitchen flows into the living and dining spaces and an inviting sunroom, all oriented toward the water. Two

  Mariah Mills Daniel Gale Sothebys Intl Rlty

  225 Lakeside Dr S, Southold, NY 11971
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  /43

  $4,250,000

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

  56875 Route 48, Southold, NY 11971

  Exceptional soundfront offering combining a beautifully maintained waterfront residence with a rare, separately buildable adjacent lot—creating a unique opportunity for legacy ownership or future development. The existing home sits on .75 acres with direct, no-bluff access to the Sound and showcases sweeping 180-degree panoramic water views. This 3-bedroom, 2-bath residence features a waterside

  Kris Pilles East End Luxury Ltd

  56875 Route 48, Southold, NY 11971
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  /42

  $4,299,000

  • 4 Beds
  • 3 Baths
  • 3,500 Sq Ft

  3525 Paradise Point Rd, Southold, NY 11971

  WELCOME TO PARADISE. Commanding 2.38 private acres on the bay in Southold’s coveted Paradise Point, this remarkable waterfront estate possesses the cinematic North Fork presence of a setting from Nelson DeMille’s Plum Island—dramatic, intriguing and entirely unforgettable. With approximately 97 feet of private beach, panoramic views toward Shelter Island and the estate-lined shoreline beyond,

  Nicholas Planamento William Raveis New York LLC

  3525 Paradise Point Rd, Southold, NY 11971
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  /35

  $1,750,000

  $249K PRICE DROP

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

  3500 Pine Neck Rd, Southold, NY 11971

  Step into nearly three centuries of preserved history at 3500 Pine Neck Road, Southold—an extraordinary historic residence originally built in circa 1720 and impeccably maintained in pristine condition. This is not simply a home; it is a rare architectural heirloom, offering authenticity, craftsmanship, and legacy that cannot be replicated. Every historic element has been preserved to perfection,

  Trish Bergin Signature Premier Properties

  3500 Pine Neck Rd, Southold, NY 11971
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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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  /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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  /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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  /39

  $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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  /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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  /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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  /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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