Southold

Southold

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$12,500,000
 

1430 The Esplanade, Southold

5 Beds, 8 Baths, 7,000 SqFt
"The Esplanade", a spectacular Nantucket Style 5-bedroom Bayfront Estate located on the west side of the Bayview Peninsula in Southold, a desirable North Fork location. Surrounded by water and preserved land, this home is custom designed. Recognizing the rarity of this special location the owners of the property accumulated adjoining Bayfront lots over twenty years, creating this private estate and, simultaneously, an exceptional
Status: Active
New
$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
New
$5,995,000
 

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
New
$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
New
$3,500,000
 

5615 Soundview Avenue, Southold

3 Beds, 1 Bath,
Ten Beautiful Private Acres Overlooking Long Island Sound! Surrounded By Large Nature Preserve And Peconic Dunes As Neighbors. 6.3 Acres Of Residential Acreage, & A Home Currently Sits On 2.9 Acres. Both Parcels (1000-52-1-2.1 & 2.2) Are Being Sold Together. Great Opportunities Await! MLS #s 3244537 & 3244517
Status: Active
New
$3,500,000
 

5615 Soundview Avenue, Southold

Ten Beautiful Private Acres Overlooking Long Island Sound! Surrounded By Nature With A Large Preserve And Peconic Dunes As Neighbors. 6.3 Acres Of Residential Acreage & A Home Currently Sits On 2.9 Acres. Both Parcels (1000-52-1-2.1 & 2.2) Being Sold Together. Great Opportunities Await! MLS# 3244537 & 3244517
Status: Active
New
$3,395,000
 

53930 Route 25, Southold

3 Beds, 9 Baths, 6,700 SqFt
Two properties one: a stunning church/community building of 320 people capacity and the other, a beautiful 10 rooms home in the heart of the village of Southold on the North Fork on Long Island. An abundance of business, artistic or fitness potential with its 30 car parking. Set on a 1.15-acre lot in the heart of the Business Hamlet of Southold, this rare property offers the chance to blend business with pleasure thanks to being zoned commercial
Status: Pending
$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: Active
New
$2,750,000
 

18915 Soundview Avenue, Southold

4 Beds, 4 Baths,
Located along the North Fork's northern coastline rests this pristine newly constructed Modern water-front home. This unique home rests atop a Sound side bluff and offers elevated forever water-views w/ breath taking sunsets, and truly captures the embodiment of what it means to live the North Fork lifestyle. The interior offers 4 bedrooms, 4 bathrooms, floor to ceiling windows and chef's kitchen with open in-door/out-door living. Transition
Status: Pending
$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: Active
New
$1,990,000
 

57856 (private) Main Road, Southold

5 Beds, 6 Baths, 5,080 SqFt
Escape The City Life In This Distinguished Home Featuring 1st Flr. Mstr Ste W/Full Bath And Frplc W/Add'l 4 Ensuite Bdrms & Frplcs. Professional Kit W/Granite Countertops, Open Floor Plan, 10 Ft. Ceilings & 3Car Gar. Great Home For Entertaining The Extended Family!
Status: Pending
$1,649,000
 

N/A, Southold

2 Beds, 2 Baths, 1,786 SqFt
Southold, North Fork expanded 'farm' ranch located on Town Harbor with dock in X zone! Sublime upscale setting nestled behind the historical society on private road hidden, but easily accessible to all. Home features wonderful views from almost every room. Living room with wood burning fireplace leads to waterside deck, Dining room, eat-in-kitchen, laundry, den with second fireplace, plus master suite w/full bath & terrace access, second
Status: Pending
$1,569,000
 

2060 Clearview Avenue, Southold

3 Beds, 2 Baths, 2,300 SqFt
New to the market! Enjoy the best of everything! 134 feet of wide waterfront views of nature at it's best on Goose Creek; private dock, expansive lawn with plenty of room to run and play, wide, deep waterside deck. The home is in excellent condition, superbly maintained with an open plan, family room with fireplace, updated kitchen, large LR/DR combo, master suite and 2 additional bedrooms and bath. 2-car garage. Beautiful gardens. Close to
Status: Active
New
$1,550,000
 

530 Sunset Way, Southold

5 Beds, 2 Baths, 1,620 SqFt
Turn this into your waterfront escape! 160' of waterfront, a 6x20 dock, 2.5 at MLT, 5 Bedrooms, 2 balconies, 2 Bathrooms and a loft area. Wraparound deck providing spectacular Bay views. Enjoy beautiful sunrises and sunsets. Steps from Cedar Beach! Surrounded by award winning North Fork vineyards, restaurants, farm stands, beaches, boating & great shopping. This won't last!
Status: Active
New
$1,495,000
 

50 N Sea Drive, Southold

Southold, well established restaurant in business 33 years, popular destination for tourists and locals. Close to Long Island Sound Beach. A great location to make your mark in the restaurant business on the North Fork .
Status: Active
New
$1,495,000
 

20675 Soundview Avenue, Southold

3 Beds, 2 Baths,
Light Bright and Airy Summer Cottage Designed for Ample Outdoor Activities. Spacious Backyard w/ an Oversized Deck and Pergola Shade. Plenty of Lounge Space for sunny days, a Fire Pit, and Outdoor Shower. Including a Walkout Balcony Over looking the Sound Horizon. You'll Have Your Own Private Beach w/ a Bulkhead. These Waterfront Luxuries Make This Property Unique In it's Own Special Way. All Furnishings are Included with Sale.
Status: Pending

 


 

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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