Southold

Southold

All Listings Under $100,000 $100,000 - $200,000
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$12,500,000
 

- The Esplanade, Southold

5 Beds, 8 Baths, 6,475 SqFt
"The Esplanade", A private estate surrounded by water & preserved land comprised of 3 separate Bayfront lots totaling shy 5 acres & 400' of sandy beach, fronting Peconic Bay. Nantucket style 6475sf home, crafted with crown moldings, NF Stone, cedar shake, and marble. Cooks are delighted by the two tone Clive Christian Kitchen outfitted with La Cornue Gas Stove, Sub Zero & Miele appliances. The kitchen blends into the
Status: Active
$10,000,000
 

10995 N Bayview Road, Southold

5 Beds, 6 Baths, 9,600 SqFt
For the discerning buyer. Down a long gated driveway, lined with spectacular white pear trees, lies this 8 acre compound on Southold Bay. Incredible privacy, 157 feet of private beach and over 9600 SF of living space. Meticulously maintained and incredible attention to detail. 5 bedrooms all ensuite, Chefs kitchen including double convection ovens, full subzero refrigerator and freezer, True Butler pantry including a dishwasher, outdoor Viking
Status: Active
$8,000,000
 

1430 Esplanade, Southold

5 Beds, 8 Baths, 6,475 SqFt
"The Esplanade", A private estate surrounded by water & preserved land with 170' of sandy beach, fronting Peconic Bay. Nantucket style 6475sf home, crafted with crown moldings, NF Stone, cedar shake, and marble. Cooks are delighted by the two tone Clive Christian Kitchen outfitted with La Cornue Gas Stove, Sub Zero & Miele appliances. The kitchen blends into the dining/living room enclosed by glass overlooking sprawling lawn
Status: Active
$4,995,000
 

1645 Boisseau Avenue, Southold

Amazing opportunity to acquire development rights intact R-80 parcel within the HALO zone. This one in a lifetime parcel offers frontage on 3 roads and is situated in the heart of Southold. Call for details.
Status: Active
$4,599,999
 

1400 Youngs Avenue, Southold

Investment Opportunity. Approximately 19,0000 Square Foot Brick Office Building With Room To Social Distance. Meticulosity Maintained Over The Years. Located In The Heart Of The Town Of Southold And Across The Street From Southold's LIRR Train Station. Generous Windows For Natural Light, Separate Private Office Spaces On Both Floors Including The Basement Where There Is Also A Cafeteria And Meeting Space. Abundant Parking. A Three Bay Storage
Status: Active
$3,500,000
 

17877 Soundview Avenue, Southold

5 Beds, 5 Baths, 5,000 SqFt
Stunning new construction Sound front, this is the one you have been waiting for! 110' of Long Island Sound front and private stairs to your beach. 10ft ceilings throughout the first floor, open floorplan with panoramic views. The living room has an oversized fireplace, built in cabinets and coffered ceilings, glass doors that open directly to the patio. Viking full stainless steel appliance package, double dishwashers, gas stove with custom
Status: Active
$3,400,000
 

425 Jacobs Ln, Southold

5 Beds, 4 Baths, 3,286 SqFt
This sustainable sanctuary is meticulously maintained and turnkey! Using solar energy and featuring a true chef's kitchen with an AGA stove, great room with wood burning fireplace, den, formal dining room, first floor office/ study, butler's pantry with a commercial dishwasher, ice maker, LavAzza espresso point machine, 5 bedrooms including a large primary bedroom with a killer walk in closet and en suite bathroom, a second primary/ B&B
Status: Active
$3,365,000
 

751 Laurel Avenue, Southold

Calling all builders & Investors! Southold, North Fork RARE 50 acre (approx) offering includes 3 lots (705,751, and 2425 Laurel Avenue) made up of 3 SCTM parcels: 1000-55-6-35 (23 acres) & 36 (11.5 acres) and 1000-56-1-1(10.68 acres). Wooded, sub-dividable LAND with development rights in place - Expired 18 lot subdivision "Bayberry" can be re-activated per Town of Southold Planning Dept. an ideal investment for builders OR
Status: Pending
$3,250,000
 

5615 Soundview Avenue, Southold

3 Beds, 1 Bath, 1,500 SqFt
Spectacular Waterfront Oasis Located In Peconic Dunes. Features 9+ Acres Of Luch Woodland. Overlooking LI Sound, With 250 Feet Of Sandy Beach For Swimming And Fishing. Incredible Sunset, Nature Trail Amongst Blueberry, Cranberry & Beach Plums. Osprey Platform In Dunes, Achery Hunting, And Much More. Existing Structure On Property Is Sold As Is And The Perfect Spot To Build Your Dream Home.
Status: Active
$3,222,000
 

835 Tarpon Drive, Southold

4 Beds, 3 Baths, 3,400 SqFt
Your own private fisherman's cove tucked away, with a deep-water dock that accommodates substantial boats and offers quick access to serious fishing - an aspiration for every angler! Situated on 1.4 acres, this home is surrounded by panoramic water views from every room. Updated and modern, each room is filled with light. Enjoy the eat-in kitchen-family room combination with its cozy fireplace, the separate dining room and the living room also
Status: Active
$2,799,999
 

1165 Calves Neck Road, Southold

4 Beds, 5 Baths,
Waterfront gem located in one of Southold's prime coveted neighborhoods with open panoramic water views of the creek and bay. This meticulously landscaped property provides lush privacy with gorgeous blooms, along with a deeded dock and direct access to the bay. Hostessing made easy with guests taking quarters on the east side suite located on the main floor, along with the home's open floor plan. A great room with a wood-burning fireplace,
Status: Pending
$2,500,000
 

47420 Route 25, Southold

Incredible location! Over 10 acres with more than 800 feet of frontage on the Main Road at the head of Southold Hamlet. Established plant and vegetable farm with existing farm stand, 12 greenhouses, outbuildings and many temporary greenhouses. Property being sold ''as is" with everything you need to continue the legacy or reinvent it with your own agricultural dream. Large enough for a vineyard, livestock, fruit trees, vegetables, or all
Status: Active
$2,500,000
 

47420 Route 25, Southold

Incredible location! Over 10 acres with more than 800 feet of frontage on the Main Road at the head of Southold Hamlet. Established plant and vegetable farm with existing farm stand, 12 greenhouses, outbuildings and many temporary greenhouses. Property being sold ''as is" with everything you need to continue the legacy or reinvent it with your own agricultural dream. Large enough for a vineyard, livestock, fruit trees, vegetables, or all
Status: Active
$2,350,000
 

380 Midway Road, Southold

4 Beds, 4 Baths, 3,400 SqFt
Spectacular Renovated Bayfront, embracing the prevailing southwesterly breezes & sweeping views over the Peconic Bay to the South Fork. Expansive waterside deck destined for entertaining & cocktails at sunset. Updated kitchen, formal DR, LR w/flp, sunroom, all with waterview's. 2nd flr guest wing includes a guest ensuite with updated bath, 2 additional BRs w/ full updated bth. On the East side of the house is a private master wing, LR
Status: Pending
$1,779,000
 

130 West Lake Drive, Southold

3 Beds, 2 Baths, 1,500 SqFt
Enjoy the breathtaking views in this exclusive Bayfront home, 1 of 6 homes in a private entity on Little Peconic Bay. Come enjoy the spectacular panoramic water views of the bay and a gentle breeze in your own gated compound. The 1930's Nantucket style home is part of the West Lake Association with its own private beach and deeded access to the pond which you can navigate your way out to the bay. Enjoy the magnificent eastern sunrises and
Status: Pending
$1,775,000
 

1725 Oak Drive, Southold

3 Beds, 2 Baths,
Rare opportunity to own a perfect North Fork bay front home in the highly sought after Reydon Shores community featuring a private community beach and marina only steps away. This move in condition 3 bedroom, 2 full bath water front home offers breathtaking panoramic views of Shelter Island, 2 floors of decks, manicured landscaping, CAC, new plastic navy style bulkhead and a whole house generator. Renovate or expand to make your dreams come
Status: Active
New

 


 

Nowhere in Southold Town is there a more rich history than in its namesake hamlet of Southold.

Southold was the first English settlement in the future New York State, founded by Puritans from New Haven, Connecticut, in the summer of 1640, on land purchased from the Corchaug Indians. The Indian name for the land that would become Southold was Yenicott. Southold remained under the jurisdiction of Connecticut until 1674.

The name Southold is believed by some to be a misspelling of Southwold, which is a coastal town in the corresponding English county of Suffolk. This claim is debatable, but John Youngs, one of the town’s founding fathers, was born and raised in Southwold.

A portion of this historic hamlet is a federally recognized historic district and there are many homes and structures dating back to the 17th Century.

Southold has long been a vibrant community which continues to evolve with each passing year. The hamlet of Southold features miles of both bay and sound front beaches, sprawling vineyards, boutique wineries, farm stands, museums, an observatory, and unlimited recreational activities. There are a number of quaint home décor shops in Southold’s downtown, as well as a good number of casual eateries and coffee shops. Most of Southold Town's government buildings are also located in the hamlet of Southold.

Southold students attend the elementary, middle and senior high school centrally located on a single sprawling campus on Oaklawn Avenue.

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