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54180 Route 25, Southold

4,400 SqFt
4400 Sq.Ft Of Newly Renovated Commercial Space In Prime Retail Shopping District. Ideal For Upscale Retail, Farm To Table, Take-Out, And Other Retail. Amazing Outdoor Square And New 2200 Sq Ft Basement Included.

49200 Route 25, Southold

422 SqFt
422 Sq.Ft. Of Storage/Garage Space

55000 Main Rd, Southold

Prominent And Picturesque Office Building With Various Configurations/Costs Ranging From $500 To $1,500 Or More. Off Street Parking. See Attachment For Various Office Configurations And Their Costs.

53345 Rt 25 / Main Rd, Southold

Great Opportunity To Be A Part Of Feather Hill Village In The Heart Of Southold. Beautiful And Cozy Office Space With Rustic Beams, Wide Plank Floors And Cathedral Ceiling. Perfect For Attorney, Architect, Accountant, Consulting Etc...

53740 Route 25, Southold

1 Bath,
Second Floor - Updated Office Space Ideal For Professional. This Is Not Residential Space.

1100 Pine Ave, Southold

3 Beds, 2 Baths,
Available Through May 31,2019 Only (Fall/Winter/Spring). Beautifully Renovated,Recent Kitchen And Spacious Open Floor Plan. Sprawling Waterfront In A Sequestered Beach Community. This Is A Winter Rental.

1875 Bayview Ave, Southold

3 Beds, 2 Baths,
Enjoy The Tranquility Of The Nf While Sitting On Your Waterfront Deck Or In Front Of The Fireplace Overlooking Hashomomuk Pond. Charming 3 Bed/2 Bath Has A Bonus Sunroom & Loft.

49200 Route 25, Southold

1,931 SqFt
900 Sqft. Office/Retail + 1031 Sqft. 2+ Garage

48555 County Rd 48, Southold

3 Beds, 2 Baths,
Farmhouse Year Round Rental. Many Updates. Convenient Location.

975 Tuckers Ln, Southold

3 Beds, 2 Baths,
Cottage Style Ranch W/Hardwood Floors, Charming Kitchen And Dining Area. Good Size Bedrooms And Den. Rear Deck Overlooks Large, Fully Fenced Back Yard With Beautiful Vineyard Views. Available 4/1/19.

N/A, Southold

4 Beds, 2 Baths,
Book Your North Fork Vacation Now! Sleeps 8, Fully Equipped With All Your Vacation Needs. Moments To Finest Wineries, Breweries, Farms,Beaches,Shops. A Short Drive To Greenport/Harbor/Ferry To Shelter Island.Includes Gas Grill, Bikes, Beach Chairs, Fully Equipped Kitchen, Cable, And Central Air. Hot Nightlife, Sunsets On The Breathtaking Long Island Sound,The Laid Back Yet Very Cool North Fork Is Calling. *2 Week Minimum Rental Required*

170 Lake Dr, Southold

3 Beds, 2 Baths,
A Great Front Beach Cottage A Short Distance To Kenny's Beach. 3 Beds, 2 Baths, Dining Room, Living Room With Sliders To Back Deck Facing Long Island Sound. 1 Queen Bed, 1 Full Bed And 2 Twin Beds .Near Vineyards, Shopping And Restaurants.

2155 Long Creek Dr, Southold

4 Beds, 3 Baths,
Enchanting North Fork Waterfront Rental~Set on a magical one-acre promontory, jutting into beautiful Long Creek with spectacular water views from every room, this light and airy 4 bedroom, 2.5 bath property is the perfect retreat! Furnished a la Coastal Living, with a large deck and grounds, enjoy kayaking and swimming right from your own beach. Or take a bike ride or short drive to shopping, restaurants, transportation, wineries and Bay or

575 Hill Rd, Southold

4 Beds, 3 Baths,
Desirable Calves Neck Creekfront Furnished Winter Rental W/ Dock. Idyllic Fall And Winter Entertaining On Spacious Outdoor Deck And Grill. Kayaks Provided. Outdoor Shower. Walk To Southold Town, Hampton Jitney And Lirr. 4/5 Bedrooms, 3 Baths, Open Living/Dining Room, Sun Room, Mud Room And Laundry Room.

560 Wampum Way, Southold

5 Beds, 3 Baths,
Sitting Three Stories High, This Beautiful Waterfront Property Is Located In The Community Of Nunnakoma Waters In Southold, Ny! The Voluminous Home Has An Open Floor Concept Complimented By A 360 Degree Deck Surrounding It. A Dock, Outdoor Shower, And Large Garage With Water Toys And Equipment.

340 Locust Ln, Southold

3 Beds, 2 Baths,
Have The Total North Fork Experience. Founders Landing Home With Farmhouse Feel And Modern Amenities. Perfect Location, Walk To Town And Beach. Open Floor Plan With Lots Of Light. Wood Floors, Gourmet Kitchen. A Relaxed Comfortable Home. Private Fenced Back Yard, Herb Garden, Grill, Fishing Poles, Bikes And Paddle Board For Your Use. Pets Allowed With Additional Security.



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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