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44075 Route 25, Southold

18k SqFt
Successful, 90 Acre Vineyard For Sale. 20 Of The 90 Acres Still Have Their Development Rights Intact. 74 Of The 90 Acres Are Vines. The Vineyard Currently Has 28000 Cases Of Wine. This Is Your Chance To Own The Prestigious Osprey Dominion Vineyards. Sale Includes 3 Properties On Route 25 On 5 Deeds, $2,729,025 Of Inventory, $1,418,686 Equip. & 16+ Acre Corner Property!

N/A, Southold

Brick Cove Was Originally A Brickyard Built In 1887. Today, It Is Home To A Thriving Marina With 138 Slips And A Single-Family Residence. Other Buildings On The Property Include Workshops, A Steel Barn, An Office/Marina Store, Pool House And Sheds. Guests Can Enjoy A Private Picnic Area, 25X50' In-Ground Pool, Three Tennis Courts And A 680' Private Bayfront Beach.

61600 S Main Road, Southold

A One Of A Kind Waterfront Property. 2-Acres On The Bay. 20 Motel Keys, Several With Kitchens. A Commercial Kitchen For A 16 Caf? And Take Out Entity In A Waterfront Building That Accommodates Catering And Events. Road Front Retail Building That Can House A Gym And Marine Related Retail Units. The Potential Is Endless!

19965 Soundview Ave, Southold

3 Beds, 4 Baths, 3,064 SqFt
Simply Exquisite Pristine Nantucket Style Waterfront Compound Adorns Bluffs Sitting High Above Li Sound. The Chic Main House With Gourmet Kitchen And Double Sided Fireplace And Separate Pool House Are Built Around The Common Outdoor Recreational Areas, Gunite Heated Pool, Blue Stone Patio,, Bar-B-Que, And Staircase Leading To 148" Of Beachfront.

8360 N Bayview Rd, Southold

28 Acres On North Bayview. Development Rights Entact. Possible Sub-Division With Approval. All Or Part Of Development Rights May Be Sold To A Variety Of Local Municipalities. Development Potential : Possible Use As An Estate, Horse Farm. Agricultural Friendly Land Use, As Well. Possible Winery.

1700 N Hyatt Rd, Southold

5 Beds, 6 Baths, 6,365 SqFt
Majestic 6300Sf +, 5 Bed En-Suite Looming High On The Bluffs Of The Sound. Over 1 Acre In A Rare Nfork Location Where Value Far Exceeds Asking Price. Ride In The 3-Story Elevator To Enjoy Sea Side Living; Cozy And Charming With 3 Fireplaces, Private Road, 100' Of Sandy Beach Out The Back Door For Breathtaking North Fork Views.

57225 Route 25, Southold

Iconic Restaurant & Inn - Renovated Historic Building. 1.076 Acres On Main Rd Offering Great Exposure. 6500 Sq Ft, 103 Seats, 4 Guest Rooms On Second Floor And 4 Rooms On Third Floor For Business Use. Turn Key Operation With 30 Employees And Owners Available For Transition. Comes With Infamous Nft Food Truck And Dedicated Parking Lot.

2707 Long Creek Dr, Southold

18+ Waterfront Acres Made Up Of 3 Sctm Lots - 18 Acre Lot Already Developed W/House, Pool & Tennis Plus Old Boat House.. Wooded And Natural Setting - Ideal For Deveopment Potential Or Use As Estate, Etc.

2704 Long Creek Dr, Southold

4 Beds, 3 Baths, 3,500 SqFt
Spectacular North Fork Setting Of Over 18 Waterfront Acres! 3,000 Linear Feet Of Waterfront With Incredible Views. Lodge Style Home Designed For Entertaining Offers Pool And Tennis Plus Abandoned 'Boat House' - An Ideal Family Compound - Private Yet Convenient To All.

1455 Cedar Point Dr, Southold

3 Beds, 2 Baths,
Featured In Coastal Living Magazine, This Contemporary Beach Cottage Overlooks The Peconic Bay, A Nature Preserve, And A Deep Water Inlet. 3 Bedrooms, 2 Baths, Open Concept, Including Living, Dining, Kitchen And An Entertainment Nook, Wood Burning Fireplace And Large Surrounding Deck. 120 Ft Of Beach Front As Well As Steps Away From The Private Association Beach. Secluded.

20575 Aka Soundview Ave, Southold

4 Beds, 3 Baths, 2,200 SqFt
Move In Ready, Immaculate Soundfront Residence W/Private Beach And Fully Bulkheaded. Room For Pool. Spectacular Sunsets All Year Long... Large Living Room / Dinning Room W/Waterside Terrace, Eik, Bath, Laundry And Master Suite W/Bath Plus Bedroom On Primary - Upstairs Waterside Lounge, 2 Bedrooms, Full Bath And Large Storage Room... Easily Expanded. Room For Pool.

3370 Paradise Point Rd, Southold

5 Beds, 4 Baths, 5,300 SqFt
Stunning Custom Home Located On Shy 3 Aces Of Wooded Paradise. Soaring Marble Floored Foyer, 5300Sq.Ft. Of Living Area. Ensuite Mbr, Jr. Master Ensuite 3 Additional Br, Bath, .5Ba, 3 F/P. Custom Built 3200 Bottle Wine Cellar W/Tasting Room, Gourmet Kitchen, Walkout Full Finished Basement. Beach And Boating Rights. Many More Amenities And Features

1175 W Hill Rd, Southold

3 Beds, 3 Baths, 2,100 SqFt
Spacious 3Bd Waterfront Home In Calves Neck Area Of Southold. 30' Of Bulkheading & Dock (3' Mlt) W/Direct Access To Peconic Bay. Large Waterfront Deck, Lush Grounds W/Waterfall, Gourmet Kitchen W/Granite, Finished Lower Level, And 2 Fireplaces. Separate Utilitly Building With Additional 2 Car Garage And Full Bath.

1375 Ackerly Pond Ln, Southold

4 Beds, 3 Baths,
Enjoy Forever Vineyard Views And Sunsets From This Serene 10-Acre Horse Farm In Bucolic Southold. The Property Boasts A 4 Bedroom, 3 Bath Updated Farmhouse, 2 Barns With 8 Stalls And 2 Tack Rooms, 100' By 200' Irrigated Riding Arena, And 5 Irrigated Paddocks. Attached To The Barn Is A Fully Enclosed Garage Space. The Farm Could Be Expanded To Include An Indoor Arena.

1230 Kimberly Ln, Southold

5 Beds, 3 Baths, 4,477 SqFt
Relaxation And Gracious Living Await At This Perfectly Sited Home Set On 1.08 Acres. Enjoy Tranquil Bay Views And Breezes From Your Covered Front Porch. With Plenty Of Room For A Pool And A Large Deck For Entertaining, This Spacious Home Accommodates All. Private Deeded Beach, Plus A Short Stroll To Renown Goose Creek Beach. Close To Wineries, Restaurants, & Farm Stands.

3735 Paradise Point Rd, Southold

4 Beds, 4 Baths, 2,500 SqFt
Location, Style, Privacy, Beach, Boating...This Property Has It All! Open Floor Plan With Plenty Of Natural Light To Highlight The Hardwood Floors And High Ceilings. Sprawling Entertaining Spaces Flow Outside To The Wood Deck Where You'll Enjoy Pond And Bay Views. Discover Your North Fork Dream Home Today In This Beautiful Section Of Southold.



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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