Southold

Southold

All Listings Under $100,000 $100,000 - $200,000
$200,000 - $300,000 $300,000 - $400,000 $400,000 - $500,000
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$800,000 - $900,000 $900,000 - $1,000,000 Over $1,000,000
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$1,619,000
 

3370 Paradise Point Rd, Southold

5 Beds, 4 Baths, 5,300 SqFt
Double diamond move in ready Home With 5300Sq.Ft. Of Living Area.Located On Shy 3 Aces Of Wooded Paradise. Soaring Marble Floored Foyer, 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
New
$299,000
 

6297 Hortons Ln, Southold

Lovely Private Treed 1.45 Acre Property Located A Short Distance To Popular McCabe's Sound Beach. This Property Abuts 22 Acres Of Southold Town Preserved Land.
New
$189,000
 

9450 Main Bayview Rd, Southold

Wooded 1.20 acre building lot,located near to many million dollar plus homes, easy access to water and Town.
New
$1,995,000
 

1395 Sleepy Hollow Ln, Southold

4 Beds, 5 Baths, 3,900 SqFt
Southold, North Fork: Authentic barn relocated to Goose Creek waterfront. Private setting. Sublime views. Flexible floorplan lends itself to owner occupied B&B (w/Town permit req'd). Large, open rooms include vaulted ceiling in the main living spaces and loft plus 3 en suite bedrooms with exquisite baths, additional bedroom and 1.5 baths. 2 fireplaces - feature incredible stonework. Study. Office. Dayroom and more. Large porches
New
$3,465
 

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
New
$825,000
 

215 Garden Ct, Southold

4 Beds, 3 Baths,
This is the best of the North Fork! Come home to this lovely Dutch Colonial located on a quiet cul-de-sac. Wonderful private garden w/ privets around your 20x40 ig heated swimming pool. This home welcomes you and your guests w/ 4 brs, 3 full baths, formal dr, lr, e-i k, family room w/ fp, sunroom, and finished basement! Wood floors throughout, new windows, heater, furnace, new cac, and more! Founders landing district w/ potential for boat dock
New
$17,000
 

17915 Soundview Ave, Southold

4 Beds, 4 Baths,
More pictures to come. Enter this home and you will be greeted by spectacular views of the Sound and soothed by the calming, open and luxurious design. Enjoy lounging on the private beach, at the heated pool or in the hot-tub... the choice is yours!
$40,000
 

920 E Cedar Point Driv, Southold

5 Beds, 5 Baths,
1st Time Offered. Gorgeous Nantucket Style Home. Gut Renovated. 200' Direct Waterfront And Beach With Incredible Views From All Principal Rooms. Slate Patios, Beach Decks And Al Fresco Dining - All With Direct Water Access. Outdoor Shower And Yards Complete The Best In Coastal Living. 5 Bedrooms(King, Queen & 3 Fulls)
$449,000
 

50705 Main Rd, Southold

4 Beds, 1 Bath, 1,400 SqFt
Southold, North Fork - Own a piece of local history: Bayles-Tuthill-Corey farmhouse circa 1656-67. This home is as old as Southold/North Fork history! Virtually intact and undisturbed, includes private, park-like property close to all Village amenities & beach. Charming cottage in Residential Office zone - allows adaptive repurpose w/permits or beckons the 'real' North Fork lifestyle for weekend or year-round enjoyment. Beautiful and
$8,000
 

58235 Route 48, Southold

3 Beds, 2 Baths,
Water Front Living on the North Fork of Long Islands wine country awaits you with your very own private beach. Contemporary spacious 3 bedroom, 2 full bath home with breathtaking views of the Long Island Sound. Balconies on both floors with parking for up to 5 cars. Home located walking distance to the Sound View Hotel with great restaurant and piano bar. All Utilities are included with rental price.
$33,000
 

4405 S. Harbor Rd, Southold

4 Beds, 3 Baths,
Make This A Vacation To Remember In Your Summer Dream Home By The Bay. Completely New And Totally Renovated - Immaculate & Stylish, Roomy & Comfortable, This Home Sleeps 8 Or More, Has Large Open Concept First Floor Living And Entertaining, Master Ensuite, Plus 3 More Bedrooms, Family Room, Lr W/ Fireplace, Formal Dining Room. Roll Out Of Bed And Onto The Beach 200 Ft Away. Enjoy Kayaking, Biking, Swimming, Wine, Shopping. This Home
$753,690
 

2705 Lighthouse Rd, Southold

4 Beds, 2 Baths, 2,377 SqFt
4-5 Br, 2 Ba Craftsman Cape Style Home Close To Horton's Pt Lighthouse And Stairs To L.I. Sound Beach; Includes 256 Sqft Horse Barn, Chicken Coop, Large Peacock Coop And 800 Sqft 2 Story Detached Caretaker's Cottage With Bath And Oil Heat.
$8,000
 

3050 Kenneys Rd, Southold

2 Beds, 2 Baths,
Make The Most Out Of Your Summer At This Charming Cottage! This Charming Beach Home Offers 2 Bedrooms, 1.5 Baths, Kitchen, & A Livingroom/Dining Room. Enjoy Relaxing By The In-Ground Pool Or Take A Stroll To Kennys Beach.
$9,900
 

12, Southold

3 Beds, 3 Baths,
Be Prepared To Be Enchanted From This Waterfront End Unit In The Private Community Of The Cove. Views From All Rooms. 2 Waterfront Private Decks. Newly Renovated Tennis Courts. Ig Pool Is Heated. Launch Area For Paddle Boards, Kayaks. Minutes To Bay. Spacious 3 Bedroom, 2.5 Bath Located Smack In The Middle Of Foodie And Winey Heaven, Surrounded By Sandy Beaches. Paradise.
$24,000
 

1975 Youngs Ave, Southold

3 Beds, 2 Baths,
This Charming Cottage Is Delightfully & Stylishly Decorated Located In The Heart Of Town. Enjoy Local Restaurants, Library, Opera House, Convenience Of Grocery & Pharmacy Nearby. Beautiful Founders Beach A Short Distance Away. Plenty Of Room For Guests - 3 Bedrooms - Sleeps 10. Formal Dining Room, Eik, Lr W/ Fireplace, Deck Off Kitchen, Sitting Room/Den. Fabulous Backyard For Entertaining.
$564,900
 

7480 N Bayview Rd, Southold

5 Beds, 2 Baths, 2,500 SqFt
This Is A Fannie Mae Homepath Property! Unique 2500 Sq Ft 5 Bedroom 2 Story Home On Shy Acre. Lr, Dr, Large Eik, Family Room And 2 Full Baths. Full Unfinished Basement For Storage. Front Porch And Rear Deck For Entertaining. Close To North Fork Beaches And Wineries.

 


 

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.

The source of the displayed data is either the property owner or public record provided by non-governmental third parties. It is believed to be reliable but not guaranteed. This information is provided exclusively for consumers' personal, non-commercial use.

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