Southold

Southold

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$200,000 - $300,000 $300,000 - $400,000 $400,000 - $500,000
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$1,695,000
 

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
New
$685,000
 

2865 South Harbor Road, Southold

3 Beds, 2 Baths, 1,130 SqFt
Southold - South Harbor Road. Be the first to enjoy this renovated 3 bedroom, 2 bath home. New central air and electric. SS kitchen with quartz counters. Brand new tile baths. Lovely 1/3 acre level lot, mature trees and new plantings. Fireplace, wood floors throughout. Laughing Waters Beach and Boating Assoc. Emerson Park and Beach at your doorstep.
New
$2,550,000
 

1605 N Parish Drive, Southold

6 Beds, 4 Baths, 4,000 SqFt
North Fork Coastal Living! Stunning Six Bedroom Bayfront Home With Panoramic Views Of Peconic Bay, Shelter Island And Beyond! The Most Desired Beach And Sailing Location In All Of Southold. Includes An Expansive Deck For Entertaining And Dock Your Own Boat. A Spectacular Seaside Retreat! Room for bayside view pool with fabulous view ! Check Out Our Virtual 3D Tour Now Available For Your Viewing Convenience
New
$1,645,000
 

1380 Oakwood Drive, Southold

4 Beds, 5 Baths, 3,800 SqFt
Welcome to this impeccably maintained Post Modern home. With over 3800 sq.ft. of living space and 92' water front w/dock & direct bay access. Contained within are 4 BRs, 4.5 baths including 2 master suites, office, EIK, den w/fireplace & wet bar. Formal LR, Formal DR, three season water view sun room. Expansive upper & lower water view decks. Finished basement, 2 car garage. Professionally landscaped grounds w/mature plantings.
New
$869,000
 

3995 Wells Avenue, Southold

4 Beds, 2 Baths, 2,000 SqFt
Premium waterfront location off of the mouth of Jockey Creek in Southold w/ 160' of creek front . 8 year old deep water dock (4.5' at low tide) w/ straight shot views of Great Peconic Bay from dock. You can be steps away from your boat on the this creek front property and less than 5 minutes from boating on the Bay. Goose Creek beach is just a 3 minute drive away as well. Property is also conveniently located within biking distance of Southold
New
$1,299,000
 

535 Lighthouse Road, Southold

4 Beds, 3 Baths, 2,850 SqFt
A Long Tree Lined Drive To This Custom Built 4 Br, 2.5 Bath Post Modern. Sited On 5+ Private Acres. Perfect For Horses, Vineyard Or Many Other Ideas. The Choice Is Yours. Large Great Room With Stone F/P Opens Into A Gourmet Kitchen, Dbl Ovens, Granite Tops, Stainless Appliances, Fdr, Md Rm. Breakfast Nook Overlooking 45 Acres Of Drs Land And 8 Acres Of Farmland.
New
$695,000
 

625 Private Rd #2, Southold

3 Beds, 2 Baths, 1,700 SqFt
You'll find old world charm in this vintage renovated 1830 Farmhouse on 1.35 acres of natural wildlife habitat right in the heart of Southold Village. Large private property includes a 2 car garage and studio/barn. Both suitable for studios/offices or workshops. Take a 5 minute stroll down your country lane and you are in middle of downtown Southold Village. Zoned for Hamlet Business.
New
$180,000
 

55075 Route 25 # 5, Southold

1 Bed, 1 Bath, 529 SqFt
Southold Co-Op for sale as an investment with a long term tenant lease in place. Beautiful park like landscaped property. Renovated Kitchen, Bath, hardwood floors, etc... Located within the town close to shopping and all transportation. Monthly common charges include Heat, Water, Ground Care, Exterior Maintenance and much more.
New
$850,000
 

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 homestead encompasses over 5 acres, 421 ft of water w. a dock and channels vacation vibes. 5+ BRs, 5.5 BAs, grand EIK w/ fpl, encl. porch, sun-room, LR w. a fpl and a partially fin basement. Step outside and experience the magic w/a heated salt water pool and spa, pool house w. BA and cabana changing area, 2 large barns, fire pits & outdoor seating throughout and a private deep water dock with access to the Bay. 3
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
$899,000
 

7105 Main Bayview Road, Southold

4 Beds, 3 Baths, 2,300 SqFt
Southold Farmhouse With Private Lush Gardens, Pergola and In-Ground Pool. This 4 Bedroom 2.5 Bath Home Includes Formal Dining Room, Eat-in-Kitchen And Family Room With Fireplace. Enjoy Goose Creek Beach, Southold Village and All That The North Fork Has To Offer.Buy now and enjoy the best summer ever ! Ready for summer occupancy! Check Out 3D Tour
New
$624,900
 

810 Hiawathas Path, Southold

3 Beds, 2 Baths,
Located in the beautiful bay side beach community of Laughing Waters offering a private beach, picnic area & boat slips w/ launch ramp on Corey Creek. Easy access to Peconic Bay. South Harbor Park Beach is around the corner. Set on .67 acre lot. Relax on the front porch, back deck, patio, hot tub, outdoor shower & huge yard. Open concept living room and kitchen w/ a breakfast bar and wood burning stove. Master bedroom has a full bath.
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
$589,000
 

145 Budds Pond Road, Southold

3 Beds, 2 Baths, 1,250 SqFt
Boaters delight! Willow Point Estates Ranch with deeded beach and use of marina. This home offers an open floor plan with vaulted ceilings and sliding glass doors to the deck. There is a master bedroom with a full bath plus 2 additional bedrooms, central air conditioning, oak hard wood flooring, and many updates. There is a 2 car garage below plus a full height basement. Large deck looking over a great yard for entertainment. Wonderful
New
$825,000
 

450 E Richmond Road, Southold

3 Beds, 1 Bath,
Graciously updated water front cottage with spectacular water views. Beautiful yard with new bulkhead and stairs for water access. This home offers a chefs kitchen with wolf stove, three good size bedrooms, one full bath with marble tiles. There is a great room with vaulted ceiling for entertaining leading out through sliders to a paver patio. The Long Island Sound Beach is across the street. Come enjoy Hashamomaque Pond which leads out to
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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