Greenport West, NY Homes for Sale

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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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  /35

  $1,950,000

  $150K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,410 Sq Ft

  660 Sutton Place, Greenport, NY 11944

  Built in 2021 and offered in like-new condition, this stylish four-bedroom residence pairs clean contemporary design with the relaxed ease of North Fork living. A semi-open floor plan creates natural flow across the main level, connecting the living, dining, and kitchen spaces in a layout equally suited for everyday living and effortless entertaining. Four spacious bedrooms offer comfortable

  Bridget Elkin Compass Greater NY LLC

  660 Sutton Place, Greenport, NY 11944
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  /3

  $575,000

  • Land
  • 25,264 Sq Ft
  • $991,379 per Acre

  21 Tims Trail, Shelter Island, NY 11964

  This quiet community known as Long View acres is the perfect place to build your Shelter Island dream home. Located just minutes from Bootleggers Alley Beach which is known for their spectacular sunsets. This .58-acre vacant lot backs up to historic Westmoreland Farms creating a beautiful backyard views.

  Tina Marika Kaasik Daniel Gale Sothebys Intl Rlty

  21 Tims Trail, Shelter Island, NY 11964
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  /25

  $1,175,000

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

  130 Tasker Ln, Greenport, NY 11944

  Pool, private beach access and the North Fork lifestyle—all in one Greenport property. Set on approximately one-third acre, this spacious Cape offers 4 bedrooms, 2 full baths and approximately 2,400 square feet of above-grade living space, surrounded by mature landscaping and exceptional outdoor amenities.The private backyard is designed for summer living and entertaining, centered around

  Kristen Rishe Signature Premier Properties

  130 Tasker Ln, Greenport, NY 11944
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  /30

  $2,800,000

  $150K PRICE DROP

  • 5 Beds
  • 4.5 Baths
  • 4,200 Sq Ft

  12 Terry Dr, Shelter Island, NY 11964

  Located in the desirable Harborview area of Shelter Island, this modern farmhouse blends luxury, comfort, and coastal living. Just 0.2 miles from a private waterfront association, enjoy easy access to kayaking and the beach.Set on a beautifully landscaped half acre, the home is designed for seamless indoor-outdoor living. The open-concept interior is flooded with natural light, featuring a

  Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty

  12 Terry Dr, Shelter Island, NY 11964
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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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  /40

  $1,595,000

  • 6 Beds
  • 2 Baths
  • 1,920 Sq Ft

  430 1st St, Greenport, NY 11944

  Introducing an exceptional opportunity to own a truly turnkey, fully restored farmhouse-style two-family home in a prime Greenport Village location. 430 First Street features two meticulously updated residences, each offering three bedrooms, one full bathroom, and thoughtfully designed living spaces. The upper-level residence encompasses approximately 850 square feet and features soaring vaulted

  William Walters Daniel Gale Sothebys Intl Rlty

  430 1st St, Greenport, NY 11944
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  /44

  $4,995,000

  • 5 Beds
  • 6.5 Baths
  • 5,535 Sq Ft

  6 Great Circle Dr, Shelter Island, NY 11964

  Brand new in one of Shelter Island's premier enclaves along Gardiners Bay, this custom 5,535 +/- SF, south-facing residence developed by Juno Homes presents a refined blend of luxury, location, and design. Defined by soaring proportions, sleek attention to detail and bathed in natural light, the home features 5 ensuite bedrooms, 6 full baths and one half bathroom across two levels. Upon entry, a

  Kristy Naddell Douglas Elliman Real Estate

  6 Great Circle Dr, Shelter Island, NY 11964
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  /8

  $549,000

  $450K PRICE DROP

  • Land
  • 41,817 Sq Ft
  • $571,875 per Acre

  11100 Main Rd, East Marion, NY 11939

  Imagine creating your own North Fork retreat in East Marion, where peaceful country roads, beautiful beaches, farm stands, vineyards and the vibrant waterfront village of Greenport are all just moments away. Final subdivision approval is already in place for this exceptional 42,000-square-foot homesite, offering a rare opportunity to bring a thoughtfully designed coastal residence to life in one

  Nicholas Planamento William Raveis (Mattituck)

  11100 Main Rd, East Marion, NY 11939
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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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  /7

  $500,000

  • Land
  • 10,454 Sq Ft
  • $2,083,333 per Acre

  1400 Bay Shore Rd, Greenport, NY 11944

  Build your dream home near the beach! This .24 acre parcel offers a great opportunity to create your own retreat, just 3 miles from town. Enjoy deeded beach rights and the convenience of being close to local shops, dining and amenities, while still enjoying a private setting. A rare opportunity to own land with beach access—bring your vision and make it your own!

  Kristy Naddell Douglas Elliman Real Estate

  1400 Bay Shore Rd, Greenport, NY 11944
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  /12

  $3,499,000

  • 4 Beds
  • 3.5 Baths
  • 3,856 Sq Ft

  9 Locust Woods Dr, Shelter Island, NY 11964

  Welcome to Shelter Island — a place where time slows down and nature takes center stage.Accessible only by ferry, this rare island community offers a level of peace, privacy, and authenticity that is nearly impossible to find in today’s world. Set on over 2 acres of beautifully engineered rolling landscape, this property has been thoughtfully designed to enhance natural beauty while

  Ron Moschetta Keller Williams Realty Greater

  9 Locust Woods Dr, Shelter Island, NY 11964
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  /27

  $1,895,000

  Open Sun 10:30AM - 12PM $455K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,484 Sq Ft

  23 Osprey Rd, Shelter Island, NY 11964

  Situated in the desirable Shorewood Farms neighborhood, just moments from the private beach and tennis court, this charming shingled home has been fully refreshed and is move in ready. Built in 2005 by renowned Shelter Island builder, George Phriender, it is convenient to the South Ferry as well as south shore restaurants and marinas. Enjoy the peace and quiet of Shelter Island only a few minutes

  Kieran Brew SERHANT.

  23 Osprey Rd, Shelter Island, NY 11964
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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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  /26

  $2,700,000

  • 6 Beds
  • 3 Baths
  • 5,900 Sq Ft

  2 Prospect Ave, Shelter Island, NY 11964

  A rare opportunity to own a legacy compound on Shelter Island, this offering brings together three income-producing historic cottages and a separate buildable lot, all just moments from the water. Positioned at 2 Prospect Avenue and 38 Rock Point Road, the properties are offered as one cohesive investment, blending immediate revenue with exceptional future potential. Each of the three cottages

  Marco Maida Compass Greater NY LLC

  2 Prospect Ave, Shelter Island, NY 11964
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  /12

  $864,200

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

  410 6th St, Greenport, NY 11944

  Built in 1910, this classic Greenport Village farmhouse offers something that is becoming increasingly hard to find in the Village by having an extra wide, extra deep lot with the space to truly create the backyard lifestyle you have been wanting. With an outdoor fireplace under the stars, long summer dinners, gardens, entertaining space, and afternoons spent soaking up the sun before heading

  Jerry Cibulski Century 21 Albertson Realty

  410 6th St, Greenport, NY 11944
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  /36

  $1,100,000

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

  61341 Route 25, Southold, NY 11971

  Private Southold Retreat on 2.18 Acres- Tucked away at the end of a private lane in desirable North Fork location, this special property offers the perfect balance of privacy and convenience. Surrounded by preserved land, large properties and a horse property, the picturesque 2.18-acre setting provides a peaceful retreat while remaining just minutes from restaurants, marinas, shops, wineries,

  Nancy Cervelli Daniel Gale Sothebys Intl Rlty

  61341 Route 25, Southold, NY 11971
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  /17

  $795,000

  • Land
  • 5,227 Sq Ft
  • $6,625,000 per Acre

  55915 County Road 48, Greenport, NY 11944

  Life's better on the sound! This sound-front lot boasts 50’ of waterfront and approved plans for a 3-bedroom, 2-bath home. Imagine mornings on the porch, afternoons on the water, and evenings with a front-row seat to the most spectacular sunsets around. Whether you're building your forever home, a weekend retreat, or an investment property, this lot is ready when you are and offers the best of

  Sheri Winter Parker Corcoran

  55915 County Road 48, Greenport, NY 11944
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  /34

  $2,250,000

  • 3 Beds
  • 2 Baths
  • 2,352 Sq Ft

  1945 Village Ln, Orient, NY 11957

  Located in the heart of Orient Village, across the street from the Yacht Club and near all Village amenities, this fully updated nineteenth-century home features a wrap-around front porch, original hardwood floors, three bedrooms, first & second floor full baths, and a large eat-in kitchen with original pantry. The home has a front and rear staircase and a glass pocket door between the living

  Janet Markarian Daniel Gale Sothebys Intl Rlty

  1945 Village Ln, Orient, NY 11957
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  /28

  $3,850,000

  New Construction

  • 4 Beds
  • 5.5 Baths
  • 3,985 Sq Ft

  8 Hilo Dr, Shelter Island, NY 11964

  This newly constructed modern residence offers stunning south-facing water views over West Neck Bay in Shelter Island. Thoughtfully designed to maximize its prime setting, the home spans approximately 3,985 square feet and features 4 ensuite bedrooms and 5.5 bathrooms, providing exceptional comfort and privacy. The interiors showcase a high level of craftsmanship and attention to detail,

  Enzo Morabito Douglas Elliman Real Estate

  8 Hilo Dr, Shelter Island, NY 11964
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  /2

  $2,399,000

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,250 Sq Ft

  1760 Mccann Ln, Greenport West, NY 11944

  Welcome to your luxury retreat on the North Fork, ideally located in the hamlet of Greenport. This brand new residence offers the perfect blend of sophisticated design, modern comfort and effortless indoor-outdoor living - all just moments from the Long Island Sound with deeded beach rights to a private community beach. Your days can begin with morning walks along the shoreline and end with

  John Quinn John Quinn Inc

  1760 Mccann Ln, Greenport West, NY 11944
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  /7

  $6,395,000

  • 5 Beds
  • 6.5 Baths
  • 4,250 Sq Ft

  8 Margaret's Dr, Shelter Island, NY 11964

  Set on 1.05± acres along the shores of West Neck Creek, 8 Margaret's Drive presents a newly constructed waterfront residence designed to embrace the natural beauty and relaxed character of Shelter Island. With direct frontage along the creek and a thoughtful orientation toward the water, the property brings together refined new construction, generous outdoor living, and a private waterfront

  Hedgerow Exclusive Team Hedgerow Exclusive Properties

  8 Margaret's Dr, Shelter Island, NY 11964
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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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  /49

  $2,995,000

  • 3 Beds
  • 2.5 Baths
  • 2,300 Sq Ft

  13 Spring Garden Ave, Shelter Island Heights, NY 11965

  Own a distinctive piece of Shelter Island Heights history in this beautifully restored circa-1875 residence, thoughtfully updated for today’s lifestyle while retaining the character and architectural details that make a historic home so special. Set on approximately 0.40 acres, the property offers second-level water views, inviting private gardens, and a classic wraparound porch ideal for

  Douglas Cabral Century 21 Excelsior Realty

  13 Spring Garden Ave, Shelter Island Heights, NY 11965
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  /7

  $549,000

  $101K PRICE DROP

  • Land
  • 41,991 Sq Ft
  • $569,502 per Acre

  11100 Main Rd, East Marion, NY 11939

  Imagine creating your own North Fork retreat in East Marion, where peaceful country roads, beautiful beaches, farm stands, vineyards and the vibrant waterfront village of Greenport are all just moments away. Final subdivision approval is already in place for this exceptional 42,000-square-foot homesite, offering a rare opportunity to bring a thoughtfully designed coastal residence to life in one

  Nicholas Planamento William Raveis New York LLC

  11100 Main Rd, East Marion, NY 11939
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  /21

  $859,000

  $36K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 990 Sq Ft

  307 Champlin Place, Greenport, NY 11944

  GREENPORT, NY: Recently renovated farmhouse in a quiet neighborhood. 2 bedrooms 1 bath. Open concept, eat in kitchen, central air conditioning, washer/dryer, Gas grill, fire pit, dining /seating area, WiFi/cable. Close to downtown Greenport, beaches, wineries, and major North Fork attractions. Ready for Summer 2026! Exclusive: $895K.

  Angelo Piccozzi DERING HARBOR REAL ESTATE LLC

  307 Champlin Place, Greenport, NY 11944
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  /25

  $2,595,000

  • 4 Beds
  • 2.5 Baths
  • 1,994 Sq Ft

  11 Prospect Ave, Shelter Island, NY 11964

  Shelter Island Heights IconGracefully positioned in the heart of Shelter Island Heights, this timeless residence has been thoughtfully renovated and restored to honor its original character while seamlessly incorporating today's modern comforts. Rich in architectural charm and classic detail, the home offers an elegant blend of historic beauty and refined living. A gracious, oversized covered

  Donna Walker Douglas Elliman Real Estate

  11 Prospect Ave, Shelter Island, NY 11964
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  /22

  $799,000

  • 2 Beds
  • 1 Bath
  • 1,090 Sq Ft

  44 (1180) Sound Rd, Greenport, NY 11944

  A rare opportunity to own an early 20th-century Adirondack-style cottage in Greenport, ideally situated just 0.12 miles from a beautiful Sound beach and only one mile from the heart of Greenport Village. This charming cottage showcases many of the home’s original details starting with a screened-in front porch spanning the full width of the façade, creating a welcoming indoor/outdoor retreat.

  Janet Markarian Daniel Gale Sothebys Intl Rlty

  44 (1180) Sound Rd, Greenport, NY 11944
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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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  /30

  $8,900,000

  Open Sat 12PM - 1:30PM

  • 6 Beds
  • 9 Baths
  • 7,300 Sq Ft

  22 Locust Point Rd, Shelter Island, NY 11964

  Rarely available in an enviable location directly across from the water with mooring rights, this new construction home in Dering Harbor delivers the best of Hamptons living on Shelter Island, ready for immediate enjoyment and for generations to come. Built in 2026 and sited on 2.4 acres, the new construction property has 7,300 +/- SF of interior living space (including the finished lower level)

  Romaine Gordon Saunders & Associates

  22 Locust Point Rd, Shelter Island, NY 11964
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  /15

  $283,950

  $35K PRICE INCREASE

  • 1 Bed
  • 1 Bath

  690 Queen St Unit 4 Coastal Cottage, Greenport, NY 11944

  North Fork Resort offers a private cottage resort experience in Greenport, in the heart of North Fork wine country. This fully furnished Park Model Vacation Cottage provides a place to return to - whether for a few days, a week, or extended time throughout the season - without the burden of traditional second-home ownership. Enjoy the comfort of your own cottage with access to a full resort

  Samantha Ripka RESOURCE REALTY GROUP

  690 Queen St Unit 4 Coastal Cottage, Greenport, NY 11944
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  /35

  $2,349,000

  • 3 Beds
  • 2.5 Baths
  • 3,312 Sq Ft

  5 + Part 3 Hagar Rd, Shelter Island, NY 11964

  Set on 1.06 acres with elevated sunrise vistas, this freshly renovated single-story cottage is fully turn-key. The entry foyer, featuring a powder room and separate laundry room, opens to a bright, vaulted main living space that seamlessly combines living and dining areas, featuring a wood-burning fireplace with raised hearth. Strategically placed windows, including a striking round accent window

  Penelope Moore SAUNDERS & ASSOCIATES

  5 + Part 3 Hagar Rd, Shelter Island, NY 11964
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  /35

  $1,675,000

  • 4 Beds
  • 3 Baths
  • 2,117 Sq Ft

  2737 Rocky Point Rd, East Marion, NY 11939

  Located in the quaint town of East Marion this beautifully appointed ranch offers effortless one level living. Set on an acre property, bordering preserved land, this renovated home has been thoughtfully designed with four bedrooms, two of which are ensuite and three full bathrooms.Step inside to an open, light-filled layout where the kitchen flows seamlessly into inviting living room with

  Amy Kirincic The Agency Northshore NY

  2737 Rocky Point Rd, East Marion, NY 11939
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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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  /27

  $2,650,000

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

  195 Williamsburgh Dr, Southold, NY 11971

  This breezy, open-concept home was made for hosting, with seamless flow and water views at every turn. Set on 101 feet of Corey Creek frontage, you get a brand-new bulkhead, your own boat ramp, and instant access to the bay. With 4 bedrooms and 3.5 baths, including both a first-floor primary ensuite and a second-floor primary suite, there's room for everyone to spread out in style. Two mahogany

  Sheri Winter Parker Corcoran

  195 Williamsburgh Dr, Southold, NY 11971
• 

  

  /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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  /17

  $1,250,000

  $500K PRICE DROP

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

  240 August Ln, Greenport, NY 11944

  Greenport - Historic Colonial Farmhouse in Peconic Bay Estates.Offered for the first time in decades is this rare slice of Long Island history. Step back in time without sacrificing modern comfort in this circa 1600s, Dutch Colonial farmhouse, gracefully set on .39 acres in the heart of the North Fork. With 4-5 bedrooms, 3 full baths, and over 400 years of character, this one-of-a-kind home

  Deirdre DeVita Sothebys Int'l Realty Hamptons

  240 August Ln, Greenport, NY 11944

Showing Results 41 - 80, Page 2 of 4