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61 Houses For Sale in Southold, NY

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$816,500Est. Payment
3 Beds | 2 Baths | 1,225 Sqft
350 Richmond E Road, Southold, NY 11971
House For Sale

Architect owned & designed, fully renovated contemporary home on private road, just a short walk to association beach on Hashamomuck Pond in Southold. 3 bedrooms, 2 full baths, eat-in-kitchen with open common area. New mechanicals, appliances, upgraded electric, CAC, large deck and room for a pool. The perfect getaway with excellent rental potential.

$1,400,000Est. Payment
4 Beds | 4 Baths | 3,181 Sqft
40135 North Road, Southold, NY 11971
House For Sale

Vineyard Overlook combines North Fork character with a modern take on farmhouse style which melds perfectly with the tree lined entrance and vistas over sweeping scenic vineyards. Nestled in on three sides with evergreen plantings that capture the snow and seclusion, picturesque sunsets from the pool and property showcase the rolling vineyards. 2 fireplaces, wrap around porch, finished basement with den, laundry room, home office complete interior/exterior refresh in 2020. Highlights the best elements of a North Fork retreat. Moments from Kenney's Beach, Southold Village shops and adjacent to Sparkling Pointe Vineyard.

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Thomas McCarthy

(631) 765-7734
$1,400,000Est. Payment
4 Beds | 4 Baths | 3,181 Sqft
40135 North Rd, Southold, NY 11971
House For Sale

Vineyard Overlook combines the North Fork character with a modern take on the farmhouse that delves perfectly into the tree lined entrance and vistas over the scenic vineyards. Nestled in on three sides with evergreen plantings that capture the snow and seclusion, the sunsets from the pool and property showcase the rolling vineyards. 2 fireplaces, wrap around porch, finished basement with den, laundry room, home office and complete interior/exterior refresh in 2020 highlights the best elements of a North Fork retreat. Moments from Kenneys Beach, Southold Village shops and adjacent to Sparkling Point Vineyard.

$1,349,000Est. Payment
4 Beds | 4 Baths | 2,872 Sqft
675 Glenn Road, Southold, NY 11971
House For Sale

NEW CONSTRUCTION! SALT BOX COLONIAL. A place all your own with an open floor plan, 4 bedrooms, 4 baths, living room with fireplace and 9ft ceilings on both floors. Fabulous kitchen featuring an island, high end Wolf stove, 36" Bosch refrigerator, Bosch microwave and dishwasher. Lovely screened in porch with access from the Great Room. Beautiful 5" white oak floors throughout. Upstairs is an additional 330 sq ft finished bonus room you can use for a theater, office or gym. Enjoy lazy afternoons in the heated 20 x 40 salt water pool and endless possibilities with full basement w/8ft ceiling. The best lifestyle with South Harbor Beach less than 1 mile away, vineyards, restaurants, shopping. The photo is a rendering of home that is currently under construction.

$1,075,000Est. Payment
3 Beds | 3 Baths | 2,500 Sqft
695 Town Harbor Lane, Southold, NY 11971
House For Sale

Step behind the hedges. Founders Landing, Southold. Private park-like .63 acre. Custom Arts & Crafts influenced home. Bay beaches, marina, restaurants, shopping & transportation all just a stone's throw away. Exquisitely landscaped. Gracious front porch. Large foyer with a one-of-a-kind staircase with crafted newel posts. Vaulted ceilings, large windows w/ transoms and an openness that invites nature inside. Imposing brick wood-burning fireplace. Custom kitchen, dining room w/ tray ceiling. French doors lead to sunroom w/ west, south & north exposures. 1st fl master suite.. Beautiful fenced backyard w/ brick patio & specimen plantings. Plenty of room for the pool of your dreams. Whole house generator. Meticulously maintained and move-in ready. Adjacent .64 acre property also available. Call for details. Your family compound might just be in sight.

$595,000Est. Payment
3 Beds | 2 Baths | 885 Sqft
142d Orchard Road, Shelter Island, NY 11971
House For Sale

Adorable Craftsman style 3BR/1.5Ba Cottage centrally located. Access to Gardiner's Creek at the end of the private road for your kayak. LR w/FP & built-in book shelves opens to the formal DR. The first floor also hosts 2 BRs, Full BA, 3 season porch, Kitchen w/door to back yard & stairs up. The second floor has a large bedroom with half bath and lots of storage. Covered patio, shed for storage & spacious grounds all add to this Island charmer.

$1,195,000Est. Payment
4 Beds | 4 Baths | 3,000 Sqft
497 Ripplewater Lane, Southold, NY 11971
House For Sale

This beautiful home located at the end of a private road was completed in 2011, and designed to enjoy water views from all main living areas in the home. Enjoy morning coffee as swans swim by just outside the oversized windows. Sliding doors lead to maintenance free decking and new heated pool. Private dock is perfect for launching kayaks and small crafts. 1st floor boasts oversized rooms & high ceilings. Family room with fireplace, gourmet eat in kitchen with high end appliances, Bosch dishwasher and latest technology induction stove & convection oven. Master Bedroom ensuite has two walk in closets fitted with closet systems, large master bath with separate tub and shower, balcony overlooks pool and Goose Creek. A Jr. master suite with walk-in closet and ensuite bathroom. 2 additional large bedrooms, full-bath, laundry. Full dry basement with high ceilings,great for storage or can be finished. This house has it all-a must see for any family looking for the perfect North Fork Home.

$965,000Est. Payment
3 Beds | 3 Baths | 2,400 Sqft
3330 N Bayview Road, Southold, NY 11971
House For Sale

This is the location you have been searching for! Steps to Goose Creek Beach and the Southold Yacht Club, this custom built residence is perfectly sited on a one acre parcel bordered by preserved land and set back for privacy with room for a pool. Features include 1st floor Master Bedroom with Master bath including separate tub and shower, spacious updated kitchen, light filled breakfast room, home office and Great room with brick fireplace with 20 ' ceilings and skylights to bring in natural light. Close to all North Fork amenities. A perfect location!

$769,000Est. Payment
3 Beds | 2 Baths | 1,600 Sqft
450 Bay Haven Lane, Southold, NY 11971
House For Sale

Newly Renovated, Mint Condition Beach Home Features One Level Open Floor Plan, Large Eat-In Kitchen, Living Room W/ Fireplace And Dining Area. Master Ensuite Bedroom, New Decking With Room For Fire Pit & Backyard Pool. Deeded Beach Rights. New Siding, Gutters, And Full, Dry Basement That Can Easily Be Finished.

$1,475,000Est. Payment
3 Beds | 2 Baths | 3,700 Sqft
622 Lighthouse Road, Southold, NY 11971
House For Sale

Southold Circa 1910 Converted Barn. This is your opportunity to own a truly special property on the North Fork. Set on 1.5 secluded acres. Brilliantly renovated combining original rustic barn details with modern amenities. Original exposed wood beams, and steel trusses, barn doors, wide plank floors, and vaulted ceilings. Designed to allow Indoor and outdoor spaces to flow seamlessly. Gunite pool and pool house/studio. A magical home and setting just 2 blocks to Hortons Pt. Lighthouse and beach.

$3,395,000Est. Payment
3 Beds | 9 Baths | 6,700 Sqft
53930 Route 25, Southold, NY 11971
House For Sale

Two properties one: a stunning church/community building of 320 people capacity and the other, a beautiful 10 rooms home in the heart of the village of Southold on the North Fork on Long Island. An abundance of business, artistic or fitness potential with its 30 car parking. Set on a 1.15-acre lot in the heart of the Business Hamlet of Southold, this rare property offers the chance to blend business with pleasure thanks to being zoned commercial and residential. The options are endless. Whether you want to transform this elegant property into a restaurant, wedding venue, an art gallery, a music hall, a coffee shop, bed and breakfast or solely residential the choice is all yours.

$400,000
$1,300,000Est. Payment
3 Beds | 3 Baths | -- Sqft
400 Lakeside Dr, Southold, NY 11971
House For Sale

Beautiful Ranch style home nestled away on Cedar Point with idyllic views of Cedar Beach Creek and 300ft+ of water frontage. This light filled, well maintained home offers 3 bedrooms, 2.5 baths, dining room, living room with fireplace, Den with wood burning stove and a walkout lower level. Great house for entertaining. Enjoy easy access to the bay from your own private dock and an adjacent single & separate buildable lot with potential for a guest home or compound setting. Just minutes to wineries, restaurants and beaches!

$1,275,000Est. Payment
4 Beds | 3 Baths | 3,100 Sqft
1160 N Bayview Rd, Southold, NY 11971
House For Sale

Southold Farmhouse. Meticulously maintained interior designer's own home with attention to detail throughout. Wrap around front covered porch with mahogany floor and covered back porch. A Chef's dream kitchen-granite countertops, Garland commercial 6 burner stove with griddle, Sub zero refrigerator, kitchen island with sub zero double drawer refrigerators and walk in pantry. Great room with fireplace and vaulted ceilings. Wine room with sink in basement. Set on 1.75 landscaped acres with flower and vegetable gardens. One mile to Goose Creek Beach.

$649,000Est. Payment
3 Beds | 2 Baths | 2,200 Sqft
3475 Oaklawn Avenue, Southold, NY 11971
House For Sale

Live the life you have always dreamed of in this easy to love, upgraded and quality built 1909 farmhouse with a four car detached garage. With its three bedrooms and one and a half baths, and located in the Southold Park District, this home outclasses newer homes with its higher ceilings and evermore charm. The true North Fork life awaits you with a boat launch at the end of the road, Goose Creek sandy bay beach close by as well as wineries, restaurants, shopping, public transportation and more. Take a refreshing break and see a classic.

$729,000Est. Payment
3 Beds | 2 Baths | 2,300 Sqft
1300 1300 Long Creek Drive Drive, Southold, NY 11971
House For Sale

Mint condition Cape includes a large back deck with outdoor fireplace. Owner's suite on second floor includes den/home office. Located in quiet area of Yennecott Park just one block from creek access for kayaking/paddle boarding.

$549,000Est. Payment
2 Beds | 1 Bath | -- Sqft
1385 Old Shipyard Lane, Southold, NY 11971
House For Sale

Adorable cape style home located in Founders Landing a only seconds from a sugar sand bay beach and deep water marina. Situated on a generous 1/4 acre prairie like parcel, this home offers plenty of room for expansion or a pool. Located close to fine dining and shopping experiences this home is an attractive offering for summer rentals or indulge and keep the North Fork getaway all to yourself. Offering two bedrooms and one bath, this home has space to entertain yet remains conservative to maintain. New to the market and sure to disappear quickly!

$925,000Est. Payment
4 Beds | 5 Baths | 3,500 Sqft
350 Jockey Creek Drive, Southold, NY 11971
House For Sale

Construction by Roberts Premier Development is underway for this immaculate 4-bedroom, 4.5-bath creek front Farmhouse. The first floor offers a master suite, great room, dining room, eat in kitchen with breakfast area and pantry, mud room, fireplace, covered rear porch and more. The second level boasts 2 en site bedrooms and a game room. There is a washer/dryer on both floors, attached 2-car garage, full basement awaiting your finishing touches, boat doc and a permit for a pool. This 3500sf beauty is energy efficient and offers high-end finishes throughout. Move in this fall.

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