Southold NY Real Estate & Homes for Sale

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Open House:

Saturday, 7/18

More Open House Info >

Beds:
4
Baths:
3.00
Sq.Ft.:
2,200
Status:
NEW LISTING
MLS#:
1023884
Type:
Single Family
Lot size:
2 Acres
Year built:
2003
A broker reciprocity listing Courtesy: Douglas Elliman Real Estate 631-354-8100
View additional info

ADDITIONAL INFORMATION

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 bath, and a first-floor bedroom currently used as a home office. Andersen windows and ceiling fans throughout provide comfort and abundant natural light. Upstairs, you’ll find a spacious primary suite with a private deck, walk-in shower, and Jacuzzi tub and additional two guest bedrooms which share an updated bath. The full unfinished basement has high ceilings and is perfect for future potential finishing and offers plenty of room for storage. Enjoy the peaceful outdoor setting from the inviting mahogany wraparound front porch or screened-in side porch. Plenty of room pool, garage, guest cottage and more! Close to Southold’s Kenneys, McCabe’s and Town Beach. A rare opportunity to own a private retreat with amazing grounds, perfect for year-round or part time living!

Beds:
3
Baths:
3.00
Sq.Ft.:
2,800
Status:
NEW LISTING
MLS#:
1015408
Type:
Single Family
Lot size:
0.5 Acres
Year built:
1930
A broker reciprocity listing Courtesy: Douglas Elliman Real Estate 631-354-8100
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ADDITIONAL INFORMATION

Nestled along picturesque Oregon Road, one of Cutchogue's most beloved country lanes, this beautifully restored farmhouse with a brand-new roof seamlessly blends timeless charm with modern comfort. Lovingly rebuilt in 2011 and thoughtfully maintained, this exceptional residence offers approximately 2,800 square feet of inviting living space on a half-acre parcel surrounded by the bucolic beauty of North Fork farmland. Rich in character, the home welcomes you with an original wood-beamed entry with a wood-burning stove that sets the tone for the warmth found throughout. Solid oak and country oak floors flow seamlessly from room to room. The three bedrooms, two and a half baths, along with the convenience of an elevator, whole-house generator, and three-zone heating system, are designed for effortless living and entertaining. The open-concept floor plan features a spacious living area with a wood-burning fireplace. and an expansive country kitchen, creating the perfect gathering place in every season. Step outside to your private backyard retreat, complete with a 14' x 26' heated saltwater swimming pool, ideal for relaxing summer afternoons or entertaining under the stars. Mature landscaping and miles of open farm views enhance the property's tranquil country setting. Located in the heart of Cutchogue's renowned wine country, surrounded by vineyards, farm stands, and some of the North Fork's most scenic landscapes, this special farmhouse offers a rare opportunity to enjoy the authentic charm and relaxed lifestyle that make Oregon Road such a treasured address.

Beds:
6
Baths:
3.00
Sq.Ft.:
3,093
Status:
NEW LISTING
MLS#:
1013610
Type:
Single Family
Lot size:
0.9 Acres
Year built:
1898
A broker reciprocity listing Courtesy: Corcoran 631-765-1300
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ADDITIONAL INFORMATION

Every once in a while, a home comes along that just makes you smile-and this is one of them. Set on just under an acre in Southold, this classic farmhouse is full of charm, character, and even its own secret garden. With 6 bedrooms and 3 bathrooms, there's plenty of room for everyone, plus multiple living spaces, cozy sitting rooms, a dining area made for gathering, an open kitchen, laundry room, and a covered porch you'll never want to leave. The backyard has room for the pool you've been dreaming about, while the gardens and outdoor space feel like your own private escape. Just minutes from Cedar Beach and Goose Creek Beach, this is the kind of home that feels like summer all year long. Whether you're looking for a forever home, a North Fork getaway, or a place to make memories for generations, this farmhouse is ready for its next chapter.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,850
Status:
Active
MLS#:
1018327
Type:
Single Family
Lot size:
0.93 Acres
Year built:
1979
A broker reciprocity listing Courtesy: Century 21 Albertson Realty 631-765-3800
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ADDITIONAL INFORMATION

Nestled in the heart of the North Fork, this beautiful 4-bedroom, 2 1/2-bath Colonial offers the perfect blend of coastal charm and everyday convenience. Ideally situated near golf courses, pristine sandy beach, acclaimed restaurants, wineries, and the vibrant downtown area, this home provides an exceptional North Fork lifestyle. Inside, you'll find spacious living areas filled with natural light, generously sized bedrooms, and a thoughtfully designed layout perfect for both entertaining and comfortable family living. Step outside to your own private retreat featuring a large patio overlooking a beautifully landscaped backyard. The tranquil koi pond, elegant arbor, and lush gardens create a peaceful setting for outdoor dining, gatherings, or simply relaxing after a day at the beach or golf course. Whether you're seeking a year-round residence or a seasonal getaway, this charming Colonial offers the best of North Fork living in a highly desirable location.

Beds:
6
Baths:
4.00
Sq.Ft.:
3,000
Status:
Active
MLS#:
1019513
Type:
Single Family
Lot size:
1.37 Acres
Year built:
1920
A broker reciprocity listing Courtesy: Daniel Gale Sothebys Intl Rlty 631-477-0013
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ADDITIONAL INFORMATION

Tucked away along Terry Path, a rustic country lane within, an offshoot of the Camp Mineola Beach Association, this exceptional waterfront property is nestled in a quiet seaside enclave along the Great Peconic Bay. Opportunities to purchase within this historic neighborhood are exceptionally rare, making this a truly special offering. Set on approximately 1.4 acres with more than 110 feet of unobstructed frontage on the Great Peconic Bay, the classic Cape Cod-style residence offers timeless charm and tremendous potential. The spacious interior is centered around a striking stacked red brick wood-burning fireplace, while outside, a private sugar sand beach and full bulkhead provide an ideal setting for enjoying the waterfront. A substantial original boathouse, complemented by a newer three-car garage and expansive bonus space above, offers endless possibilities for storage, recreation, or future customization. The level, cleared grounds enjoy abundant sunlight throughout the day and provide ample space for expansion from the house, an in-ground pool as part of a remarkable waterfront compound. Combining a coveted Bayfront setting, generous acreage, and the enduring character of one of the North Fork's most treasured beach communities, this is a rare opportunity to create an exceptional coastal retreat.

Beds:
5
Baths:
2.00
Sq.Ft.:
2,238
Status:
Active
MLS#:
1017107
Type:
Single Family
Lot size:
0.43 Acres
Year built:
1967
A broker reciprocity listing Courtesy: Daniel Gale Sothebys Intl Rlty 631-734-5439
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ADDITIONAL INFORMATION

Welcome to 230 Booth Road, a prime Southold location offering effortless access to both Kenneys Beach and McCabe’s Beach-two of the North Fork’s most beloved Sound front destinations known for swimming, long shoreline walks, and unforgettable sunsets. This expanded cape provides exceptional flexibility for living and entertaining. The entry opens to a spacious living room with a cozy wood-burning fireplace, flowing into a dining room, both featuring oak floors currently protected by carpeting. The large eat-in kitchen offers abundant space for gatherings, with an adjacent laundry room and storage area that includes plumbing for an easy conversion to a powder room. Two bedrooms and a full bath complete the first floor. Upstairs, you’ll find three additional generous guest rooms and a full bath. An oversized walk-in attic presents potential for future expansion. The full basement offers ample storage, and Bilco doors make it simple to store outdoor furniture and seasonal items. Other features include a generator and new central air conditioning. The tranquil backyard provides plenty of room for summer entertaining. Whether you’re seeking a year-round residence or a seasonal escape, this home places you at the heart of the North Fork lifestyle—beautiful beaches, vineyards, farm stands, boutique shopping, and farm-to-table restaurants. This is the North Fork retreat you have been looking for.

Beds:
2
Baths:
1.00
Sq.Ft.:
850
Status:
Active
MLS#:
1015770
Type:
Single Family
Lot size:
0.25 Acres
Year built:
1920
A broker reciprocity listing Courtesy: Daniel Gale Sothebys Intl Rlty 631-477-0013
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ADDITIONAL INFORMATION

Grab your beach chair and your towel and get ready for summer! This quintessential Long Island Sound beachfront cottage offers water views from every room plus spectacular, and unobstructed western sunsets. Turn-key and move-in ready, this 2-bedroom, 1-bath gem perfectly blends classic seaside charm with modern comfort, featuring a renovated kitchen, and bath. Situated on .25-acre, this waterfront property has plenty of room for enjoying outdoor entertaining. Just step outside, breathe in the salt air, and start living the North Fork beach life.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,782
Status:
Active
MLS#:
1017642
Type:
Single Family
Lot size:
0.92 Acres
Year built:
1969
A broker reciprocity listing Courtesy: Compass Greater NY LLC 631-251-8644
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ADDITIONAL INFORMATION

Charming, private, and uniquely connected to the water, this cedar-shingled three-bedroom cottage offers a compelling combination of immediate enjoyment and future potential. Set on nearly an acre, the property includes a 50' wide section that extends to the bay, where a beachside double deck and stairs provide direct access to your private stretch of sandy beach. Inside, the living room is anchored by a beautiful fireplace and opens to a brick patio, creating an easy flow between indoor and outdoor living. Wrapped in glass, the sunroom addition serves as a cozy retreat, immersing you in the property's natural surroundings. Multiple en-suite bedrooms round out the offering. Whether enjoyed as a quintessential North Fork getaway or expanded to create a larger coastal residence, the setting is exceptional. True private bayfront at a price point that rarely exists.

Beds:
3
Baths:
2.00
Sq.Ft.:
3,453
Status:
Active
MLS#:
1016402
Type:
Single Family
Lot size:
0.51 Acres
Year built:
1954
A broker reciprocity listing Courtesy: Keller Williams Realty Elite 516-795-6900
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ADDITIONAL INFORMATION

Nestled in the Southwood Community on a beautifully landscaped 0.51-acre lot in Southold, this spacious ranch offers the perfect blend of comfort, charm, and North Fork living. Gleaming hardwood floors flow throughout the home, which features three generously sized bedrooms and two full bathrooms. The expansive formal living room is highlighted by a cozy wood-burning fireplace, while the large eat-in kitchen and versatile dining/flex room provide ample space for everyday living and entertaining. A heated 200-square-foot sunroom provides the perfect setting to enjoy your morning coffee or unwind with an evening cocktail. Additional features include an attached two-car garage, abundant off-street parking, and ample rear parking ideal for storing a boat, RV, trailer, or additional vehicles. The home also offers 150-amp electric service, a newer boiler and hot water heater, and was recently connected to municipal water. A massive unfinished basement complete with a cedar closet provides exceptional storage and endless possibilities for future expansion. Located just moments from sought-after beaches including Town Beach and Goose Creek Beach, and surrounded by renowned farms, vineyards, and the historic towns of Mattituck, Jamesport, and Greenport, this turnkey property presents an exceptional opportunity for those seeking a year-round residence, weekend getaway, or investment property in the heart of the North Fork.

Open House:

Saturday, 7/18

More Open House Info >

Beds:
2
Baths:
2.00
Sq.Ft.:
2,350
Status:
Active
MLS#:
1015353
Type:
Single Family
Lot size:
0.83 Acres
Year built:
1968
A broker reciprocity listing Courtesy: Daniel Gale Sothebys Intl Rlty 631-734-5439
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ADDITIONAL INFORMATION

A great business and/or investment opportunity awaits! Once a popular Southold holistic/chiropractic office with separate living quarters and then a childcare facility and apartment, this adaptable split-level property is awaiting its next creativite live-in business venture! Located on a beautiful .83 acre, this property fronts the high visibility County Road 48/North Road and backs up to scenic preserved farmland. The ground floor has a large waiting room, offices with sinks, and a half bath. The 2nd floor is a spacious 2-bedroom 1 bath rental apartment that could also be used as the business owner's home. Its Limited Business Zoning offers many opportunities including professional office, retail operation, custom workshop, garden shop/nursery, restaurant, dog and cat care facility, repair shop, etc.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,200
Status:
Active
MLS#:
1016493
Type:
Single Family
Lot size:
2.1 Acres
Year built:
1992
A broker reciprocity listing Courtesy: Daniel Gale Sothebys Intl Rlty 631-477-0013
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ADDITIONAL INFORMATION

Location is everything. Privately set on 2.1 secluded acres, this stylish and charming farmhouse style home is approached by a long winding drive that reveals a striking 1,000-square-foot post-and-beam barn before opening to sweeping views of the property's picturesque grounds. Thoughtfully maintained and rich in character, the home offers a traditional floor plan complemented by hardwood flooring throughout and a substantial wood-burning fireplace that anchors the main living space. The kitchen has been tastefully updated with a gas range and generous peninsula seating, flowing seamlessly into a dining area overlooking the manicured landscape and seasonal water views beyond. Upstairs, four well-proportioned bedrooms include three guest bedrooms served by a full hall bath, while the sun-filled primary suite offers a private retreat overlooking the property, also offering those peek-a-boo winter water-views. A rare opportunity to enjoy privacy, acreage, and timeless North Fork charm in an exceptional setting w/ ample room an in-ground pool or equestrian activities. This is the country house on the North Fork you've searching for!

Beds:
4
Baths:
3.00
Sq.Ft.:
2,240
Status:
Active
MLS#:
1016785
Type:
Single Family
Lot size:
0.5 Acres
Year built:
2000
A broker reciprocity listing Courtesy: Douglas Elliman Real Estate 631-422-7510
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ADDITIONAL INFORMATION

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 living room features a wood burning fireplace, while the formal dining room overlooks the rear yard through a bay window. A butler's passthrough connects to the kitchen, complete with stone countertops, a massive center island, stainless steel appliances, and a stainless-steel range hood. The first floor includes a full bath and adjacent family room that could easily become a first-floor primary suite or private guest space. Upstairs, the primary suite offers a private bath and second floor laundry. Three additional bedrooms share a hall bath. Additional features include an attached two car garage with mudroom access, a full basement with outside entrance, and recently updated roof, heating system, and central air. Life on Bayview Peninsula is all about the water. Pine Neck Boat Ramp, Goose Creek Beach, and Cedar Beach are all nearby. Enjoy award winning wineries, farm stands, and restaurants throughout the North Fork, with the Orient Point Ferry just a short drive away for easy access to New England. Whether you are looking for a year-round residence or a North Fork getaway, 1075 Ships Drive offers an outstanding opportunity to enjoy coastal living in one of Southold's most desirable neighborhoods.

Beds:
3
Baths:
3.00
Sq.Ft.:
3,000
Status:
Active
MLS#:
1016523
Type:
Single Family
Lot size:
0.42 Acres
Year built:
1957
A broker reciprocity listing Courtesy: Daniel Gale Sothebys Intl Rlty 631-734-5439
View additional info

ADDITIONAL INFORMATION

Southold – Goose Creek- Located along a quiet private lane leading to Goose Creek Beach, this beautifully crafted and completely renovated cedar shingled two story home offers the perfect blend of charm, privacy, and North Fork living. The first floor features an open, sun filled layout highlighted by a spacious living room with a wood burning stove, a bright and airy kitchen with an expansive dining area framed by walls of windows, and a dining area with doors opening to the pool and patio. A first floor sitting room with an adjacent full bath provides a flexible space that can be easily converted into a first floor primary en-suite. Upstairs, the generous primary en-suite offers creek views, accompanied by two additional guest bedrooms and a full guest bath. Privacy surrounds the heated saltwater in ground pool and patio, creating a peaceful retreat for relaxation or entertaining. This exceptional property captures the essence of the North Fork lifestyle — a short stroll to beautiful Goose Creek Bay beach, yet tucked away in a quiet, coveted location. With creek access you can launch a kayak or paddleboard and enjoy the serene waters of Goose Creek. f you are interested in a "real" North Fork experience, this house checks off all the boxes. Restaurants, shopping, farm stands, wineries, breweries, boating... you name it. It's all right there.

Beds:
7
Baths:
7.00
Sq.Ft.:
4,544
Status:
Active
MLS#:
1016379
Type:
Single Family
Subdivision:
Eastern Shores
Lot size:
0.42 Acres
Year built:
2026
A broker reciprocity listing Courtesy: Realty Connect USA L I Inc 631-881-5160
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ADDITIONAL INFORMATION

UNDER CONSTRUCTION - IN PHASE 3 - PROPERTY IS CLOSED IN, ROUGHED IN AND CLOSING IN WALLS - NOW AVAILABLE FOR PRIVATE IN PERSON VIEWINGS - Introducing an exceptional opportunity to own a brand new construction home in Greenport’s coveted Eastern Shores where North Fork charm meets modern luxury living. Don't miss this opportunity to claim for yourself this thoughtfully designed, currently under construction and anticipated to be completed summer 2026 in time for your East End getaway. This stunning seven bedroom six and half bath residence offers 4,544 sqft of refined living space designed with no desire left unrecognized. From the moment you arrive, you’ll appreciate the timeless architectural detail, modern farmhouse feel with a blend of contemporary finishes throughout. The open concept is ideal for entertaining featuring a chefs kitchen with oversized island, premium appliances, abundant cabinet space and butler pantry all flowing effortlessly into the spacious living room, formal dining room or out to the rear covered porch. Seven generously sized bedrooms include an expansive primary suite with oversized bathroom, walk in closet and private second story deck overlooking the backyard. Four of the bedrooms including the primary are on the second level, one bedroom on the main level and two bedrooms are located in the lower level all situated with their own respective bathrooms with the mindfulness around a main level bedroom with en suite full bath. Additional features in the build include a finished walk out lower level with recreational room, in ground vinyl pool and a detached two car garage. This beautifully crafter modern farmhouse is situated between the tranquil Inlet Pond and the beloved Kontokosta Winery also just minutes from the vibrant downtown of Greenport Village. This property is located on the north end of Tasker lane alongside a cleared public pathway with just a 2 minute walk to the famed 67 Step Beach of Greenport. Whether you’re seeking a year round residence, a second home or a vacation rental investment, 1050 Tasker Lane delivers a rare combination of location, luxury, and lifestyle on the North Fork.

Beds:
4
Baths:
4.00
Sq.Ft.:
4,100
Status:
Active
MLS#:
995201
Type:
Single Family
Lot size:
2 Acres
Year built:
2020
A broker reciprocity listing Courtesy: Corcoran 631-765-1300
View additional info

ADDITIONAL INFORMATION

Bucolic Cutchogue Compound. Set on iconic Oregon Road in Cutchogue, amongst farmstands and vineyards, this incredible 2 acre compound offers exactly the North Fork vibe everyone is looking for. The main house features 4 bedrooms and 3.5 bathrooms, opening out to a 20x44 in ground saltwater pool that quietly becomes the center of summer. Great flexible space throughout, generator ready, full basement, a 3 car garage and a separate studio with its own 4 car garage, giving you all the flexible space you need for guests, work, cars, or a full on creative or wellness setup. Minutes to beaches, restaurants, nature preserves, shopping, boating, and North Fork Country Club. Could be you!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,735
Status:
Active
MLS#:
1015877
Type:
Single Family
Subdivision:
August Acres
Lot size:
0.92 Acres
Year built:
1997
A broker reciprocity listing Courtesy: Daniel Gale Sothebys Intl Rlty 631-734-5439
View additional info

ADDITIONAL INFORMATION

Enjoy the best of North Fork living in Greenport’s sought-after August Acres community. This meticulously maintained 3-bedroom, 2-bath ranch sits on a shy acre, offering exceptional privacy and ample room to create your own backyard retreat — including space for a pool. Thoughtful updates enhance the home’s comfort and appeal, including fresh interior paint (2026), a new deck, an updated kitchen, and a new heating system. The spacious den, featuring a wood-burning fireplace and sliding doors to the deck, provides an inviting setting for relaxing or entertaining. Additional highlights include a primary en-suite with a generous bath and walk-in closet, a bright living room, dining area, convenient laundry room, full basement and a 2-car garage. Residents also enjoy access to the association’s deeded bay beach — the perfect spot to experience the beauty of North Fork living. This house checks off all the boxes. Restaurants, shopping, farm stands, wineries, breweries, boating... you name it. It's all right there.

Beds:
10
Baths:
11.00
Sq.Ft.:
11,000
Status:
Active
MLS#:
1015559
Type:
Single Family
Lot size:
4.25 Acres
Year built:
2006
A broker reciprocity listing Courtesy: Corcoran 631-765-1300
View additional info

ADDITIONAL INFORMATION

Nassau Point Waterfront Estate. Along the shores of the Peconic Bay, where boats drift past the coveted coastline of Nassau Point, an exceptional sunset side waterfront estate quietly commands attention. Spanning 4.25 acres with more than 300 feet of private beach, this remarkable property offers a rare blend of privacy, presence, and North Fork coastal beauty. The nearly 10,000-square-foot main residence sits gracefully within the landscape, designed to celebrate both the surrounding water and the art of refined living. Sunlight pours through expansive windows, illuminating generous entertaining spaces and framing panoramic bay views that shift beautifully throughout the day into the evening. The home features eight bedrooms and eight and a half bathrooms, thoughtfully arranged to create both comfort and space. A private screening room, gym, and sauna offers relaxation and recreation. A separate guest cottage with two bedrooms and two bathrooms provides a welcoming retreat for your guests, creating the perfect balance of independence and hospitality. Outside encompasses every aspect of waterfront resort living, boating from your deep water dock, swimming in the Gunite pool to playing tennis or catching shade in the pool house and dining seaside while watching the sunset. Combining extraordinary scale, exceptional waterfront frontage, and a setting that captures the spirit of the North Fork, this Nassau Point estate offers a rare opportunity to own a truly distinguished coastal retreat - ideal as a legacy property or an unforgettable seasonal escape.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,600
Status:
Active
MLS#:
1007703
Type:
Single Family
Lot size:
0.97 Acres
Year built:
1985
A broker reciprocity listing Courtesy: Corcoran 631-765-1300
View additional info

ADDITIONAL INFORMATION

This East Marion gem is on the perfect sunlit corner lot! Set on a shy acre, in a park like setting with room for a pool and waiting for you to take to the next level. Minutes to all the best beaches, including 67 Steps Beach, located within the community. Cozy front porch and spacious backyard deck. An open layout, living room with fireplace, 3 beds, 2 baths and a full basement. You can keep it simple or get as bougie as you wish! Create memories that are built to last. Surrounded by North Fork farm stands, marinas, boating, award winning wineries, great shopping, and Duryea's in Orient Point! This one will go fast!

Beds:
4
Baths:
5.00
Sq.Ft.:
4,500
Status:
Active
MLS#:
1012436
Type:
Single Family
Lot size:
1.75 Acres
Year built:
2001
A broker reciprocity listing Courtesy: Compass Greater NY LLC 631-629-7675
View additional info

ADDITIONAL INFORMATION

Introducing a stunning waterfront estate on the Long Island Sound, now available for the first time from its original owners. This coastal gem, located in the North Fork, is situated in one of the most sought-after and picturesque areas on the East End. Nestled on nearly 2 acres, this 4,500 sq. ft. residence offers exceptional views and over 200 feet of private waterfront. The spacious open floor plan includes a junior primary ensuite on the first floor, featuring a separate entrance, a wrap-around covered porch, and direct access to the backyard. The gourmet kitchen is designed to capture breathtaking coastal views, boasting custom cabinetry, high-end appliances, beautiful granite countertops, and a spacious island with seating. Al fresco dining is made easy through the breezeway, which leads to the inviting patio and outdoor decks. The living room and dining room, enhanced by a central fireplace, are filled with natural light and feature beautiful wood floors. Tucked behind the fireplace and accessed through sliding barn doors, the home office offers water views and separate access to the yard. Upstairs, the primary bedroom features a balcony and an ensuite bathroom, showcasing stunning views. Additional bedrooms with balconies, a full bathroom, and a bonus space ensure privacy and comfort for guests. An oversized lounge, also with a waterside balcony and fireplace, connects to the kitchen below via a private staircase, creating an ideal space for a quiet retreat. The spacious art studio, built as part of the expansion, has cork flooring and a wall of windows overlooking the outdoor entertaining space, which includes a fully equipped custom kitchen, dining area, stunning pool, and spa amenities. The yard's mature landscaping and expansive lawn create a welcoming atmosphere for gatherings, with curated spaces for relaxation, including Adirondack chairs nestled along the coastline to enjoy the breathtaking sunsets. Additional amenities include an attached garage, greenhouse, a full unfinished basement with side yard access, and a generator. This property is conveniently located near Greenport Village, wineries, farms, and the bucolic landscape that exemplifies the essence of the North Fork region.

Beds:
2
Baths:
1.00
Sq.Ft.:
1,300
Status:
Active
MLS#:
986841
Type:
Single Family
Lot size:
0.41 Acres
Year built:
1963
A broker reciprocity listing Courtesy: Corcoran 631-765-1300
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ADDITIONAL INFORMATION

Some things are worth holding onto and this one is no exception. Nestled in one of the North Fork's most coveted beachside enclaves, this authentic mid-century modern gem offers the rare combination of style, privacy and beach access to one of the best bay beaches in the region! The detached 2-car garage handles the practical side of life beautifully with owned solar panels, including backup battery, while the working vegetable garden reminds you that the good life really is grown here. There's room for a pool, room to expand, and plenty of room to exhale. Optional membership in the Fleets Neck Property Owners Association gets you access to a private bay beach on the east end of Dave Allison Beach - plus storage for two kayaks. This is the kind of property that smart buyers recognize immediately - and move on quickly. The bones are right. The location is right. The potential? Even better.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,200
Status:
Active
MLS#:
1014052
Type:
Single Family
Lot size:
0.58 Acres
Year built:
1998
A broker reciprocity listing Courtesy: Keller Williams Realty Elite 516-795-6900
View additional info

ADDITIONAL INFORMATION

Welcome to 3755 Grand Avenue in Mattituck, a rare opportunity to own a meticulously maintained home in one of the North Fork’s most coveted locations. Situated on an expansive .58-acre property, this 1998-built residence offers the perfect blend of privacy, modern mechanical updates, and the laid-back coastal lifestyle that has made Mattituck one of Long Island’s most desirable destinations. Constructed on a poured concrete foundation, the home has been thoughtfully improved with numerous major updates, including recently installed municipal water service, 200-amp electric, replacement windows, and a roof less than ten years old. Over the last five years, the boiler, hot water heater, and central air conditioning system have all been replaced, providing peace of mind for years to come. An attached garage offers convenience and additional storage. Enjoy the tranquility and spaciousness of North Fork living while remaining just minutes from vineyards, farm stands, Love Lane shops and restaurants, marinas, beaches, and all that makes Mattituck such a sought-after destination. With taxes under $7,100, this property presents an exceptional opportunity to enjoy year-round living or the perfect weekend retreat.

Beds:
2
Baths:
1.00
Sq.Ft.:
1,014
Status:
Active
MLS#:
1011722
Type:
Single Family
Lot size:
0.32 Acres
Year built:
1950
A broker reciprocity listing Courtesy: Engel & Volkers North Fork 631-298-7953
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ADDITIONAL INFORMATION

Nestled in the desirable Sigsbee community of Mattituck, this delightful two-bedroom, one-bathroom cottage offers the perfect blend of privacy, convenience, and coastal living. Set on a spacious lot with a large backyard, the property provides a peaceful setting for relaxing, entertaining, or enjoying summer evenings outdoors. Inside, the home features a bright and inviting layout with comfortable living spaces and timeless cottage charm. Whether you’re looking for a year-round residence, weekend getaway, or investment opportunity, this home offers endless potential. Enjoy exclusive access to the community’s private association beach nearby, perfect for swimming, kayaking, paddleboarding, or simply taking in the stunning expansive white sandy beach. Conveniently located near Mattituck’s shops, restaurants, wineries, farm stands, and transportation, this property allows you to experience the best of North Fork living while maintaining a tranquil retreat-like atmosphere. A rare opportunity to own a charming beach-community home with a generous backyard and private beach rights in one of Mattituck’s most sought-after neighborhoods.

Beds:
4
Baths:
4.00
Sq.Ft.:
2,668
Status:
Active
MLS#:
1011372
Type:
Single Family
Lot size:
0.4 Acres
Year built:
2026
A broker reciprocity listing Courtesy: Douglas Elliman Real Estate 631-354-8100
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ADDITIONAL INFORMATION

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 seamless connection to the surrounding landscape. A beautifully appointed kitchen, generous entertaining spaces, and well-designed bedroom suites create the perfect balance of comfort and sophistication. The home also includes a full basement with egress, offering excellent potential to be finished to suit your needs such as additional living space, recreation, fitness, media, or storage. The property includes full landscaping and offers room for a pool, creating the opportunity to design your ideal outdoor retreat. Enjoy peaceful water views, coastal breezes, and direct access to a private deeded beach which is ideal for kayaking, paddleboarding, swimming, or simply relaxing by the shore. Perfectly situated near North Fork vineyards, farm stands, restaurants, marinas, and village amenities, this home offers a rare opportunity to enjoy new construction with true coastal lifestyle appeal. A refined North Fork retreat designed for year-round living, weekend escapes, and effortless entertainment.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,100
Status:
Active
MLS#:
1010914
Type:
Single Family
Lot size:
0.12 Acres
Year built:
1910
A broker reciprocity listing Courtesy: Century 21 Cor Ace Realty Inc 631-878-3400
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ADDITIONAL INFORMATION

Renovated 1910 Colonial with Open Floor Plan. Down the Road From Town Beach. Just a Short Bike Ride to Down Town Greenport and Wineries !! Possibility of Selling Fully Furnished !! Large Back Building Could Be Turned into a Pool House, Garage or Shed, Additional information: Appearance Diamond, Interior Features: Living Rm, Dining Area, Spacious Eat in Kitchen with Large Island, Breakfast Nook, 3 Bedrooms(Small one on First Floor, 2 On 2nd Floor), 1.5 Renovated Bathrooms. Separate Hotwater Heater, 2 Separate Driveways SELLER IS APPLYING FOR PERMIT AND VARIANCE FOR A INGROUND POOL, HE IS SELLING WITH PERMIT ONLY FOR IT NOT INSTALL.

Beds:
2
Baths:
1.00
Sq.Ft.:
800
Status:
Active
MLS#:
1017744
Type:
Single Family
Lot size:
0.21 Acres
Year built:
1948
A broker reciprocity listing Courtesy: Douglas Elliman Real Estate 516-621-3555
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ADDITIONAL INFORMATION

The Summer has never been sweeter in this coastal cottage right on the water. Peaceful breezes blow while you sit on the covered deck and watch the paddle boarders go by. This private community on Hashamomuck Pond offers 2 bedrooms, warm oak floors, spacious living room, and waterfront views galore. Enjoy kayaking, paddleboarding, fishing, and swimming right out your back door. This is the lifestyle you have thought about, why not make it happen now!

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Andrea D. Conner, License 10311208085, Xome Inc., License 10991227159, [email protected], 844-400-XOME (9663), 750 Highway 121 Bypass, Suite 100, Lewisville, Texas 75067

Listings courtesy of One Key MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of 11/13/2024. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Properties displayed may be listed or sold by various participants in the MLS. Per New York legal requirement, click here for the Standard Operating Procedures. Copyright 2026, OneKey MLS, Inc. All Rights Reserved.



Southold Real Estate

Southold is located in New York. Southold, New York has a population of 23,571. Southold is less family-centric than the surrounding county with 21.26% of the households containing married families with children. The county average for households married with children is 32.94%.

The median household income in Southold, New York is $92,229. The median household income for the surrounding county is $111,660 compared to the national median of $69,021. The median age of people living in Southold is 56.1 years.

Southold Weather

The average high temperature in July is 80.9 degrees, with an average low temperature in January of 23.6 degrees. The average rainfall is approximately 48 inches per year, with 27.3 inches of snow per year.

Southold Map

Southold Real Estate Market Conditions

  • Median sales price

    $1,477,500
    16.1%
    change since last quarter
  • # Active listings

    96
    30-day change

Southold Schools and Demographics

Education near Southold, NY

City County
High School Graduates 92.84 90.39
College Degree - 2 year 9.44 9.66
College Degree - 4 year 48.04 38.31
Graduate Degree 15.03 12.89
Expenditures per Student 30,219 30,219
Students per Teacher 12.3 12.3

Elementary Schools near Southold, NY

Grades Students P/T Ratio ZIP
Greenport Elementary School PK - 06 330 15 11944
Mattituck-Cutchogue Elementary School KG - 06 580 10.4 11935
New Suffolk School PK - 06 17 6.8 11956
Southold Elementary School KG - 06 403 11 11971

High Schools near Southold, NY

Grades Students P/T Ratio ZIP
Greenport High School 07 - 12 353 15.3 11944
Southold Junior-Senior High School 07 - 12 423 11.2 11971

Ungraded Schools near Southold, NY

Grades Students P/T Ratio ZIP
Shelter Island School PK - 12 221 6.8 11964

Demographics near Southold, NY

City County
Neighborhood Type Suburban
Population 23,571 1,522,998
Population Density 438 1,670
Median Age 56.1 41.7
People per Household 2.3 3
Median Household Income 92,229 111,660
Average Income per Capita 60,908 49,404

Real estate near Southold