Southold

Southold

All Listings Under $100,000 $100,000 - $200,000
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$1,645,000
 

1395 Sleepy Hollow Lane, Southold

4 Beds, 5 Baths, 4,500 SqFt
Southold, North Fork: Authentic barn house on Goose Creek waterfront. Private setting. Sublime views. Flexible floorplan lends itself to 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 - incredible stonework. Study. Office. Dayroom and more. Large porches & great light. Convenient
Reduced
$840,000
 

590 Budds Pond Road, Southold

2 Beds, 2 Baths, 1,560 SqFt
Waterfront Ranch with dock .Enter from the delightful covered front porch & you are immediately drawn to the lovely waterview through big picture windows. The interior has a open floor plan. The kitchen, dining area, & living rm w/ gas flp all have a waterview. There is a master BR with a full bth,1 guest BR, guest full bth, a den that converts to a 3rd bedroom, laundry rm, & 2 car garage. The exterior has a waterside deck ,
New
$6,750,000
 

845 Maple Ln, Southold

5 Beds, 6 Baths, 4,565 SqFt
This magical waterfront compound encompasses over 5 acres, 421' of waterfront, a deep water dock with access to the Bay. 5+ bedrooms, 5.5 bathrooms, grand eat-in-kitchen with a fireplace, enclosed porch, sun-room, living room with fireplace and a partially finished basement. Heated salt water pool and spa, pool house with a bathroom and cabana changing area, 2 large barns, fire pits and outdoor seating throughout. Further details upon request.
New
$1,290,000
 

2100 Glenn Road, Southold

3 Beds, 3 Baths,
Newly renovated Contemporary, waterfront home! Dock your boat in your own backyard. Easy living in this updated, private home in an ideal North Fork neighborhood. Be in before summer!
New
$299,000
 

55075 Route 25 # 2w, Southold

2 Beds, 1 Bath, 1,000 SqFt
This beautiful 55 plus Co-op is located in the center of the Town of Southold to enjoy easy access to shopping & transportation. Common charges include heat, water, sewer, taxes, ground maintenance, management and more. There are two bedrooms, full bathroom, large kitchen, and living/dining room with sliding door to terraced balcony. Clean oak hardwood flooring throughout. Founders Park and Beach district access too!
New
$2,295,000
 

19625 Soundview Avenue, Southold

4 Beds, 4 Baths, 3,500 SqFt
Expansive water views of Long Island Sound awaits at the gracious entry to this 3500 sf custom built contemporary home in move-in condition. The open floor plan skillfully draws One's eye from the wood floors to high ceilings with architecturally inspired doors & windows that showcase the big open space and fuse the water views to the interior. Nestled between the Sound and vineyard, all rooms enjoy breathtaking views. Spacious bedrooms
New
$20,000
 

405 Cedar Point Dr.w, Southold

4 Beds, 4 Baths, 2,400 SqFt
Impeccable home with numerous upgrades. Tastefully decorated. 4 Beds, 3.5 Baths with watervviews. New in-ground pool, Hot Tub. Private community bay beach. Ready For Summer Fun? Come To The North Fork... Everybody's Doing It!!
New
$40,000
 

200 Gin Lane, Southold

3 Beds, 3 Baths,
Beautifully Appointed Beach House. Bay Haven Homeowners Association Private Beach At End Of Street. Spacious Home Featuring State Of The Art Sound System Throughout, Master-En-Suite, Lr W/ 50" Flat Screen TV, Dr And Gourmet Kitchen. Two Large 2nd Floor Br, One Includes A Deck Overlooking Private Yard. Second Floor Has Inviting Loft Seating Area. Entertain In A Charming Screened In Porch Or Fully Equipped Outdoor Deck. Close Proximity To
New
$20,000
 

845 Budds Pond Road, Southold

3 Beds, 3 Baths,
Turn Key Bayfront Beauty! Located On A Quiet Cul-De-Sac In Willow Point Estates And Close To Bay Beaches And Southold Village, This Elegant North Fork Contemporary Is The Perfect Year Round Escape. Private And Beautifully Landscaped, The House's Open Layout Makes It Ideal For Entertaining. This Fully Renovated Lovingly Furnished Home Features A Master Suite, 2 Bedrooms, 2.5 Baths, Spacious Living Room, Dining Room And Kitchen.The Outdoor Area
New
$35,000
 

1205 Lake Drive, Southold

4 Beds, 4 Baths, 4,000 SqFt
Rented June, July and August through Labor Day. Fabulous Lakefront Home With All The Amenities For A Wonderful Summer Vacation! Great Views Of Li Sound And Lake. 4 Bedrooms, 4 Baths, Panoramic Vies Of Long Island Sound, 20X60 In-Ground Heated Pool, Central Air. Perfect For Large Family Vacation. Tiptop Shape.
New
$10,000
 

400 Windjammer Drive, Southold

4 Beds, 4 Baths,
Beautiful bayside retreat in Harbor Lights. Open concept with expansive views out to the creek and bay through almost every window. Completely updated, comfortable, spacious, super clean and meticulously landscaped. Relax around one of the three fireplaces, with a book next to the koi pond, or on the wrap around fully furnished back deck with a gas- grill and fire pit. Kayak off the new 60 ft bulkhead with two new docks. Around the corner from
New
$10,000
 

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 concepts complimented by a 360 degree deck surrounding it. There is a dock, outdoor shower and a large garage with water toys and equipment.
New
$10,500
 

1325 Old Shipyard Lane, Southold

3 Beds, 3 Baths, 1,792 SqFt
Founders Landing Southold Neighborhood Contemporary Home with vaulted livingroom ceiling. All new expansive rear deck. Designed for one level living with first floor bedroom suite, and laundry. Additional 2 bedrooms, and full bath upstairs. Sliders to rear deck and yard. Central air. Moments to Founders Landing Park/Beach and Southold Village.
New
$22,500
 

485 Hickory Avenue, Southold

4 Beds, 3 Baths, 2,350 SqFt
Rented through Labor Day. Turnkey water view home with pool. Beautifully appointed 4 bedroom, 3 bath, walking distance to Goose Creek. Gourmet Kitchen, Open Living Space, First Floor Master Suite. Outdoor space ideal for entertaining. Heated deep pool up to 8 Ft. Kayaks available with waiver. Owner will consider dog with additional $500 Security deposit. Close to Southold town and beaches.
New
$14,500
 

355 Terry Lane, Southold

4 Beds, 4 Baths, 4,000 SqFt
Sugar sand beach and spectacular water views from this modern Southold Bay stunner. Design and decor is "House Beautiful" on all 3 levels. Exterior living includes 2 waterside patios, deck and master bedroom balcony. House has 4 bedrooms and 4 baths. Perfect vacation home on the North Fork! August 26-Sept 9 $14.5k/wk, Sept 11-30 $8k/wk, Oct $7k/wk, Nov-May $5k/wk.
New
$4,750
 

430 Terry Lane, Southold

2 Beds, 1 Bath, 800 SqFt
Picture Perfect 2-bed, 1-Ba Cottage in Founders Landing. 2 Pristine Beaches Nearby. Chic & Simple Beach House, Completely Renovated. Private Backyard. A Great Place From Which to Explore All the North Fork has to Offer.
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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