North Fork Homes

/35
$1,450,000
- 4 Beds
- 2.5 Baths
- 2,700 Sq Ft
1025 Long Creek Dr, Southold, NY 11971

In the last month there have been lots of updates made to this exquisite waterfront home with wrap around porches and breathtaking views. Don’t miss this opportunity to own a waterfront property on the North Fork. Perfectly situated on the protected and tranquil water way of Arshomomaque, where you can enjoy fishing, crabbing, clamming, boating, or just relax and listen to the birds. The first

Barbara Poliwoda Douglas Elliman Real Estate

1025 Long Creek Dr, Southold, NY 11971
/30
$26,000 per month
- 4 Beds
- 3.5 Baths
- 3,800 Sq Ft
- House for Rent
365 Chablis Path, Southold, NY 11971

Space, Luxury, and Privacy Await in This Stunning Contemporary Home! Experience the perfect blend of elegance and comfort in this beautiful home, offering an expansive backyard ideal for dining, lounging, and entertaining. Enjoy endless hours of relaxation in the inground pool, or gather with loved ones in the spacious yard. A charming gazebo provides a welcome retreat from the sun, weather, or

Diane Arpaia Signature Premier Properties

365 Chablis Path, Southold, NY 11971
$675,000 Sold Aug 20, 2025
- 1,040 Sq Ft
- $649/SF
- 66 Days On Market
- 2 Beds
- 2 Baths
- Built 1982
215 Bridge St, Greenport, NY 11944

This sun-drenched corner-lot cottage offers the perfect Greenport retreat. The vaulted, open-concept layout creates a bright and airy living space, complemented by two generously sized bedrooms and a cozy, heated sunroom—ideal for year-round relaxation. Step outside to enjoy a beautifully landscaped patio, outdoor shower, and fully irrigated grounds surrounded by mature plantings. Just across the

Bridget Elkin Compass Greater NY LLC

215 Bridge St, Greenport, NY 11944

Est $1,713,941 Not Listed For Sale
- 4 Beds
- 2 Baths
250 Midway Rd, Southold, NY 11971

250 Midway Rd, Southold, NY 11971

/50
$1,425,000
- 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
/24
$6,500 per month
- 4 Beds
- 3 Baths
- 2,800 Sq Ft
- House for Rent
64230 County Road 48, Greenport, NY 11944

Enjoy summer fun on the North Fork in this MINT farmhouse on beautiful sprawling property! There's plenty of room for family and friends in this spacious home with 4 large bedrooms, 3 full baths, aneat-in-kitchen perfect for gatherings, impressive primary ensuite, den/home office and laundry room. Additionally, the basement is fully finished with a large and fun recreation room, full bathroom

Donald Bracken Thomas J McCarthy Real Estate

64230 County Road 48, Greenport, NY 11944
$1,325,000 Sold Aug 19, 2025
- 1,100 Sq Ft
- $1,205/SF
- 133 Days On Market
- 2 Beds
- 2 Baths
- Built 1905
2400 Bay Ave, East Marion, NY 11939

Fully renovated in 2023, this turnkey stunning seaside retreat offers the ultimate escape from the everyday. Thoughtfully designed with modern coastal living in mind, the home underwent a complete transformation, including a new roof, HVAC system, plumbing, and electrical; ensuring both effortless comfort and peace of mind.Upon stepping inside you are greeted with panoramic, unobstructed

Bridget Elkin Compass Greater NY LLC

2400 Bay Ave, East Marion, NY 11939

Est $1,480,409 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,600 Sq Ft
60 Water Terrace, Southold, NY 11971

60 Water Terrace, Southold, NY 11971

/28
$1,395,000
- 3 Beds
- 3 Baths
- 1,500 Sq Ft
308 Wiggins St, Greenport, NY 11944

Incredible investment opportunity to own #1 grossing LEGAL short term Airbnb in Greenport Village. Legally permitted - $220k annually. FULLY TURNKEY from furnishings, bedding / linens, towels, to all kitchen ware, even the artwork Maintenance team including house cleaner, pool care and landscaper are at your disposal. 2 minute walk into town - best location in Greenport, across from LIRR

Josh Shenkle EAST END ALLIANCE REAL ESTATE AND DEVELOPMENT LLC

308 Wiggins St, Greenport, NY 11944
/17
$9,000 per month
- 4 Beds
- 5.5 Baths
- 102,802 Sq Ft
- House for Rent
525 S Harbor Rd, Southold, NY 11971

NORTH FORK FALL RENTAL! Enjoy this Privately Situated Home in the Heart of Southold Yet Close to All that the North Fork Has to Offer- Visit the Farms, Vineyards and Shopping. Open Concept Liv Rm, Din Rm, Updated Kit, Renovated 4 Bed/5.5 Bath Home With Family and Guests in Mind. Windowed Doors Lead Out to a Fabulous Resort Style Yard. Enjoy The North Fork At This Unforgettable Poolside Paradise.

Teresa Rogers Douglas Elliman Real Estate

525 S Harbor Rd, Southold, NY 11971
$2,200,000 Sold Aug 18, 2025
- 2,650 Sq Ft
- $830/SF
- 33 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1701
675 Champlin Place, Greenport, NY 11944

This captivating property is the perfect canvas for a quintessential Greenport farmhouse dating back to the 17th century. Meticulously renovated to fuse contemporary comfort with timeless North Fork charm, the smart, flowing layout offers a seamless balance of style and function. Set on a beautifully landscaped lot, the outdoor spaces are designed for effortless entertaining, featuring an 18x40'

Bridget Elkin Compass Greater NY LLC

675 Champlin Place, Greenport, NY 11944

Est $1,249,657 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

/40
$1,319,000 Pending
- 3 Beds
- 3 Baths
- 3,000 Sq Ft
3520 Old Rd N, Southold, NY 11971

Cape Cod Style Retreat in the Heart of SoutholdThis Southold gem delivers the perfect blend of peace, privacy, and proximity to all the North Fork has to offer. Enjoy Blocks to McCabes Beach, Kenny’s Beach, Horton Point Lighthouse, vineyards, farm stands, and charming local shops—all just minutes away.Originally built in 1989, this home has been thoughtfully updated and expanded

Roseann Prussen Signature Premier Properties

3520 Old Rd N, Southold, NY 11971
/20
$5,600 per month
- 4 Beds
- 2 Baths
- 1,800 Sq Ft
- House for Rent
3175 Kenneys Rd, Southold, NY 11971

Lakefront vacation property with a fantastic view, central air and hot tub. This space is open and updated with 3 bedrooms, and bonus room. Walk to Kenney's Beach with all beach gear included. This Neighborhood is close to restaurants, wineries, farm stands and music.

Jason Romaniello Blue Shark Realty Group Inc

3175 Kenneys Rd, Southold, NY 11971
$1,100,000 Sold Aug 18, 2025
- 2,200 Sq Ft
- $500/SF
- 89 Days On Market
- 3 Beds
- 1.5 Baths
- Built 1840
529 2nd St, Greenport, NY 11944

This Beautifully Updated 3 Bedroom Blends 19th-century Charm with Modern Comfort. The Picturesque Facade Welcomes You Into a Residence that Exudes Timeless Elegance, Thoughtfully Renovated to Preserve its Historical Character While Offering Contemporary Amenities.The Tranquil Yard is a True Oasis, featuring Mature Trees and a Array of Vibrant Plantings. Ideally Located, This

Paul Loeb Douglas Elliman Real Estate

529 2nd St, Greenport, NY 11944

Est $1,211,675 Not Listed For Sale
- 3 Beds
- 2 Baths
505 Longview Ln, Southold, NY 11971

505 Longview Ln, Southold, NY 11971

/47
$1,399,000 Pending
- 4 Beds
- 2.5 Baths
- 3,226 Sq Ft
1465 Ackerly Pond Ln, Southold, NY 11971

Nestled in the heart of Southold’s coveted North Fork, 1465 Ackerly Pond Lane offers a rare opportunity to own a custom home on over 2.5 acres of serene, private land. This single-family property is surrounded by natural beauty and tucked away on a quiet lane, making it ideal for those seeking peace and space just minutes from the village, vineyards, and beaches. Home features a large gourmet

Scott Bennett Douglas Elliman Real Estate

1465 Ackerly Pond Ln, Southold, NY 11971
/25
$40,000 per month
- 5 Beds
- 3 Baths
- 2,000 Sq Ft
- House for Rent
1160 Goose Creek Ln, Southold, NY 11971

Step back in time-without sacrificing comfort-in this beautifully preserved 5-bedroom, 3-bath home brimming with charm and nestled along the tranquil banks of Goose Creek. Surrounded by water on two sides and set on a private road, this unique property offers a rare blend of historic character and modern amenities. From the moment you arrive, you'll be captivated by the timeless architecture,

Sheri Winter Parker Corcoran

1160 Goose Creek Ln, Southold, NY 11971
$1,100,000 Sold Aug 14, 2025
- 1,750 Sq Ft
- $629/SF
- 33 Days On Market
- 2 Beds
- 2 Baths
- Built 1850
162 Central Ave, Greenport, NY 11944

Charming Legal 2-Family Home in the Heart of Historic Greenport Village. Step back in time with this well-maintained late 1800s home, ideally located on a picturesque, tree-lined street surrounded by other beautifully preserved historic homes. Currently configured as a legal two-family residence, the property features a spacious 1+ bedroom apartment on the first floor and a cozy 1-bedroom

Paul Loeb Douglas Elliman Real Estate

162 Central Ave, Greenport, NY 11944

Est $954,343 Not Listed For Sale
- 4 Beds
- 2 Baths
1100 Rambler Rd, Southold, NY 11971

1100 Rambler Rd, Southold, NY 11971

/41
$1,350,000 Pending
- 3 Beds
- 3 Baths
- 2,700 Sq Ft
180 Pine Terrace, East Marion, NY 11939

Custom-built Ranch Situated on an Expansive 40,152 sq ft lot Just Blocks from the Beach! In One of East Marion’s Most Beautiful and Sought-After Neighborhoods. This Meticulously Crafted, Never Lived In Home, Offers A Primary Bedroom w/ Huge Walk In Closet and Private Full Bath w/Jacuzzi and Stall Shower. Plus, 2 Additional Bedrooms and 2 Full Bathrooms, Featuring Rich Hardwood Floors Throughout

Tracy Ascani Century 21 Sewanhaka Realty

180 Pine Terrace, East Marion, NY 11939
/18
$3,800 per month
- 3 Beds
- 2 Baths
- 1,100 Sq Ft
- House for Rent
315 Lake Dr, Southold, NY 11971

Rental Permit # 0966 Fantastic home set directly on Great Pond and a block (975 feet) from Kenney's Beach with restaurant Little Fish just around the corner. This bright 3 bedroom and 2 full bathroom, with a 3 season room all window porch home has an expansive rear deck overlooking the fresh water pond. Watch osprey dive bomb for fresh water bass while geese, ducks and egrets meander across the

Alexander Aquino Douglas Elliman Real Estate

315 Lake Dr, Southold, NY 11971
$1,050,000 Sold Aug 13, 2025
- 1,655 Sq Ft
- $634/SF
- 13 Days On Market
- 3 Beds
- 2 Baths
- Built 1976
75 Gull Pond Ln, Greenport, NY 11944

This stunning designer Cape has spacious open-concept living and dining areas, highlighted by soaring cathedral ceilings and an inviting gas fireplace.The chef’s kitchen is a showstopper—generously sized and thoughtfully laid out for seamless entertaining. A private back patio is perfect for al fresco dining or morning coffee.On the first floor, you’ll find two inviting guest bedrooms and

Allison Sirico Daniel Gale Sothebys Intl Rlty

75 Gull Pond Ln, Greenport, NY 11944

Est $1,217,985 Not Listed For Sale
- 4 Beds
- 2 Baths
65 Pleasant Place, Southold, NY 11971

65 Pleasant Place, Southold, NY 11971

/32
$1,695,000 Pending
- 3 Beds
- 1.5 Baths
- 2,290 Sq Ft
2515 Sound Dr, Greenport, NY 11944

This one-of-a-kind, mid-century modern was designed by renowned architect Claude Samton. Named "Winged Weekend Flight", a wood hewn escape from city ways. When you enter, you will leave your worries behind. Incredible light and gorgeous landscape envelop this 3 bedroom, 1.5 bath sanctuary. Gunite pool with an automatic cover, Ipe decking and beach rights to a gorgeous sound front beach

Sheri Winter Parker Corcoran

2515 Sound Dr, Greenport, NY 11944
/31
$10,000 per month
- 3 Beds
- 3 Baths
- 2,400 Sq Ft
- House for Rent
3650 Bay Shore Rd, Greenport, NY 11944

Your Fabulous Beach House Vacation! 2 Week Rentals or Monthly! Spacious summer house in the coveted Peconic Bay Estates private beach community on the Bay. A darling hidden path brings you to the sweetest surprise little wooden bridge to cross over to arrive on the sandy beach. Fun! No shirt, no shoes, lazy day, Yes! Very quiet water front cove, lots of area biking, kayaking, taking beach

Kate Carpluk William Raveis New York LLC

3650 Bay Shore Rd, Greenport, NY 11944
$740,000 Sold Aug 11, 2025
- 1,629 Sq Ft
- $454/SF
- 77 Days On Market
- 4 Beds
- 2 Baths
- Built 1963
950 Main Bayview Rd, Southold, NY 11971

DON'T LET THE ROAD FOOL YOU! Step inside this move-in ready Southold classic and you'll find vintage charm, a huge lot, and major potential- including possible AirBNB with proper permits! This vintage 4-bedroom, 2-bath Cape on almost a half-acre features newly refinished oak floors, updated roof (10 years) and windows throughout, a vintage eat-in kitchen with new LVT flooring, flexible layout-

JoAnn Spatola Realty Connect USA L I Inc

950 Main Bayview Rd, Southold, NY 11971

Est $979,440 Not Listed For Sale
- 4 Beds
- 3 Baths
945 Gin Ln, Southold, NY 11971

945 Gin Ln, Southold, NY 11971

/23
$1,675,000 Pending
- 3 Beds
- 2 Baths
- 1,924 Sq Ft
1620 Village Ln, Orient, NY 11957

Beautifully restored & maintained 18th C Village classic home located on coveted Village Lane in the heart of Orient Village. Private access to abutting open space of Poquatuck Field Park provides pastoral field and bay views in perpetuity. The home offers 3 bedrooms, 2 full baths, 2 fireplaces, and a gourmet kitchen that opens onto the dining/family room and 3-season screened sunroom. The 1,924

Janet Markarian Daniel Gale Sothebys Intl Rlty

1620 Village Ln, Orient, NY 11957
/15
$12,000 per month
- 4 Beds
- 2.5 Baths
- 2,400 Sq Ft
- House for Rent
39595 Main Rd, Orient, NY 11957

Spacious Traditional Home with 4 bedrooms, 2.5 baths near Orient State Park and Cross Sound Ferry.The private landscaped backyard features a pool with patio and lounge chairs and a large deck with glass doors to the kitchen. The first floor has a private living room space and a kitchen/family room open plan for entertainment. The second floor has a master ensuite with full bath overlooking the

Janet Markarian Daniel Gale Sothebys Intl Rlty

39595 Main Rd, Orient, NY 11957
$1,885,000 Sold Aug 01, 2025
- 3,500 Sq Ft
- $539/SF
- 33 Days On Market
- 4 Beds
- 3.5 Baths
- Built 2005
155 Caiola Ct, Greenport, NY 11944

Discover an exceptional opportunity to own in Rock Cove Estates, one of the North Fork’s most sought-after communities. This 4-bedroom, 3.5-bathroom home is surrounded by similarly elegant, high-caliber residences—each reflecting a shared standard of luxury and pride of ownership that defines this prestigious enclave. Perfectly positioned at the end of a cul-de-sac on a lush .63-acre lot, this

William Walters Daniel Gale Sothebys Intl Rlty

155 Caiola Ct, Greenport, NY 11944

/2
Est $846,242 Not Listed For Sale
- 3 Beds
- 2 Baths
1430 Bay Haven Ln, Southold, NY 11971

1430 Bay Haven Ln, Southold, NY 11971

/14
$1,563,000 Pending
- 4 Beds
- 3.5 Baths
- 2,700 Sq Ft
410 Aquaview Ave, East Marion, NY 11939

Waterview new construction contemporary home offering 4 bedrooms and 3.5 baths over three levels including the walk out lower level. Roof deck with water views. The clever design maximizes floor space and provides for exceptional living. Innovative finishes include rough sawn pine exterior lap siding from a Long Island sawmill, first and lower-level polished concrete flooring, white oak flooring

Paul Loeb Douglas Elliman Real Estate

410 Aquaview Ave, East Marion, NY 11939
/28
$7,375 per month
- 5 Beds
- 3 Baths
- 3,700 Sq Ft
- House for Rent
2700 Sound Dr, Greenport, NY 11944

2025 Rates: September 1-30 $29,500; October $25,000: Escape to this exceptional seasonal rental, perfectly situated on the shores of the Long Island Sound. This beautifully appointed waterfront home offers the ultimate coastal living experience, featuring private stairs leading directly to the beach, an in-ground heated gunite pool, and panoramic water views from nearly every room. With 4

William Walters Daniel Gale Sothebys Intl Rlty

2700 Sound Dr, Greenport, NY 11944
$2,770,000 Sold Jul 31, 2025
- 5,800 Sq Ft
- $478/SF
- 266 Days On Market
- 5 Beds
- 5.5 Baths
- Built 2024
2350 Shipyard Ln, East Marion, NY 11939

Another beautiful new construction home by one of Long Island's most coveted construction companies, Modern Age Home Builders! 2350 Shipyard Ln features a European style modern design home with the first and second floor totaling 4,000 sq ft. with a detached oversized 2 car garage (with an electric car charger), all sitting on over 1.5 acres of land. The property offers the possibility to join

Catherine Bukowski Modern Age Realty Group LLC

2350 Shipyard Ln, East Marion, NY 11939

Est $2,410,990 Not Listed For Sale
- 5 Beds
- 4.5 Baths
- 4,051 Sq Ft
9502 N Bayview Rd, Southold, NY 11971

9502 N Bayview Rd, Southold, NY 11971

/7
$1,499,000 Coming Soon
- 4 Beds
- 1.5 Baths
- 1,835 Sq Ft
609 1st St, Greenport, NY 11944

A true gem!!! Rare opportunity to own this charming 4 BR beautifully preserved home in the heart of the vibrant maritime village of Greenport. Ideal location just blocks to waterfront dining, quaint shops, transportation, beaches and everything that makes this village so special. This elegant home has a welcoming front porch, a warm inviting foyer/parlor, eat-in kitchen, formal dining room,

Thomas McCarthy Thomas J McCarthy Real Estate

609 1st St, Greenport, NY 11944
/35
$15,000 per month
- 3 Beds
- 4 Baths
- 3,500 Sq Ft
- House for Rent
63615 North Rd, Greenport, NY 11944

Rental Permit # 1304 Chalet-Style Retreat with Private Soundfront Beach – Summer Rental in Greenport, NYNestled on 2.52 secluded acres along the North Fork’s coveted Soundfront, this architectural chalet-style home offers the ultimate summer escape. Featuring 3 oversized bedrooms and 4 full bathrooms, this expansive and warm retreat blends rustic charm with modern luxury.Soaring

Marco Maida Compass Greater NY LLC

63615 North Rd, Greenport, NY 11944
$3,000,000 Sold Jul 28, 2025
- 3,756 Sq Ft
- $799/SF
- 47 Days On Market
- 4 Beds
- 3 Baths
- Built 2023
1740 Inlet Pond Rd, Greenport, NY 11944

Experience the allure of this stunning custom-built modern shore house, completed in 2023 and nestled in sought-after Rock Cove Estates, just moments from Greenport Village. This extraordinary property has been meticulously designed to showcase unique architectural elements and a phenomenal floor plan that flows seamlessly, perfect for entertaining. Upon entering, you are welcomed by an inviting

William Walters Daniel Gale Sothebys Intl Rlty

1740 Inlet Pond Rd, Greenport, NY 11944

Est $801,624 Not Listed For Sale
- 2 Beds
- 1 Bath
580 Jacobs Ln, Southold, NY 11971

580 Jacobs Ln, Southold, NY 11971

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