Southold

All Listings Under $100,000 $100,000 - $200,000
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$800,000 - $900,000 $900,000 - $1,000,000 Over $1,000,000
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$1,899,000
 

3525 Paradise Point Road, Southold

4 Beds, 3 Baths, 3,500 SqFt
Welcome To Paradise. Rare Southold Bayfront Situated On 2.3 Acres With 97 Feet Of Private Beach And Community Boating Rights. Take In Magnificent Water Views From The Custom Built 4 Bd., 3 Ba. Residence With 3 Levels Of Luxurious Living Featuring A Double-Height Great Room With Natural Coral Hearth, Large Eat-In Kitchen, And Waterfront Master Suite. Spacious 1st Floor Office Makes It Easy To Work From Home. Privacy Abounds On The Park-Like
New
$1,800,000
 

1515 Calves Neck Road, Southold

2 Beds, 2 Baths, 2,350 SqFt
Cape Cod Waterfront located on one of Southold's most coveted streets, combines the best of elegance, style, & craftsmanship. Vaulted ceilings, 2 wb frplcs & a long stretch of windows w/ spectacular views of Town Creek & Southold Bay connect the open chef's EIK-living-dining. Enjoy the large waterside deck, or meander down to the shoreline, protected by rip rap, to a long gracious dock w/ 3ft.8in of depth at low tide. Room for
New
$1,800,000
 

8360 N Bayview Road, Southold

28 Acres On North Bayview. Development Rights Entact. Possible Sub-Division With Approval. All Or Part Of Development Rights May Be Sold To A Variety Of Local Municipalities. Development Potential : Possible Use As An Estate, Horse Farm. Agricultural Friendly Land Use, As Well. Possible Winery.
$1,800,000
 

44780 County Road 48, Southold

Southold North Fork: Turnkey restaurant with substantial land overlooking preserved farmland on well traveled Route 48 between 2 lights. Make your mark in the food and beverage industry on the North Fork! Ideal site for a brew pub, beer or wine garden. Well regarded destination restaurant since 1967 serving locals and tourists alike.
New
$1,799,999
 

50 Goose Creek Lane, Southold

5 Beds, 2 Baths, 2,062 SqFt
Incredible opportunity to own an expansive, 1 1/2 acre waterfront estate just 150 yards from Goose Creek Beach. 270' of total water frontage with 55' feet of bulkheading and private dock. House with five total bedrooms (three with water views), formal living room with fireplace and water views, plus two car detached garage, waterside patio and firepit, and outdoor shower. Plenty of room for expansion so bring your vision and your architect.
New
$1,799,000
 

565 South Harbor Road, Southold

5 Beds, 6 Baths, 4,100 SqFt
Classic 1897 Cross Gable North Fork Farmhouse completely renovated, expanded, and transformed in 2019 to offer the perfect blend of locale and luxury. This home includes five luxurious impeccable ensuite baths, four fireplaces, wrap around porch and a gourmet kitchen. With its exacting attention to comfort, every detail has been thoughtfully executed to allow you to create a memorable celebration or intimate gatherings. A true world class
$1,699,000
 

1195 Watersedge Way, Southold

3 Beds, 3 Baths, 2,400 SqFt
The One You Have Been Waiting For! Light and Bright, Open Floor Plan Bay Front Home with Gourmet Kitchen, Living Room with Fireplace, 1st Floor Master Suite, Open Loft Sitting Area on 2nd Floor and Bay Views from All Rooms. Waterside Patio with Pergola. 2 Car Garage Plus Storage Shed. Generator. Hurricane Shutters.
$1,650,000
 

625 N Sea Drive, Southold

4 Beds, 2 Baths, 1,578 SqFt
Best deep(100' from deck to high water mark) and level sandy beach on the North Fork awaits your presence. Situated on the beautiful North Fork, your pristine setting and spectacular sunsets includes a seasonal 1578 sqft beach cottage with 7 rooms, 2 baths plus a 2nd floor loft and water view covered deck.
Reduced
$1,650,000
 

62375 Route 25, Southold

Established restaurant building. Marine 2 Zoning. 300 feet of high visibility route 25 road frontage. Water view patios with marinas and hotel across the street. Prime Location just west of Greenport!
New
$1,649,000
 

17975 Soundview Avenue, Southold

3 Beds, 2 Baths, 1,500 SqFt
Breathtaking views of the Sound all the way to Connecticut are yours in this light filled home. Very private setting on beautifully landscaped 1.2 acres. 115' of beachfront. Beautifully renovated with open floor plan ideal for summer entertaining. New kitchen is the perfect place to prepare gourmet meals. Dine al fresco on your deck as you watch the sun set into the shimmering sound. Nestled between the sound & bucolic vineyards this superb
$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
$1,575,000
 

1175 Hill Road W, Southold

3 Beds, 3 Baths,
Uniquely beautiful waterfront home located in Calves Neck area on 1.15 acres of land. Although 1 parcel of land, it contains 2 lots w/ 2 properties! Main house: open concept 3-bed, 3-bath home w/ a large waterfront, wraparound porch ideal for warm summer days. Property overlooks lush waterfall & private boat dock w/ 2-20+ bulkheads & direct access to Peconic Bay. Cold winter nights, gather around either of 2 wood burning fireplaces on
New
$1,495,000
 

50 N Sea Drive, Southold

Southold, well established restaurant in business 32 years, popular destination for tourists and locals. Close to Long Island Sound Beach. A great location to make your mark in the restaurant business on the North Fork .
New
$1,495,000
 

2000 Glenn Road, Southold

3 Beds, 3 Baths, 3,000 SqFt
North Fork Waterfront Escape. This Custom Built Post Modern home on Goose Creek has an open floor plan & features a gourmet chef's kitchen w/double drawer Fisher & Paykel dishwasher, Wolf appliances, sub-zero wine fridge & granite counter tops, dining area & great room w/ gas fpl, all with access to the deck overlooking lush grounds &direct water access. A generous light filled sunroom leading to a screened in porch, full
$1,489,000
 

3370 Paradise Point Road, Southold

5 Beds, 4 Baths, 5,300 SqFt
Move in ready double diamond Home With 5300 Sq.Ft. Of Living Area.Located On Shy 3 Aces Of Wooded Paradise, Entire exterior freshly painted. 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 with new Bosch appliances being installed, Walkout Full Finished Basement. Beach And Boating Rights. Work-from-home, have your own garden,
Reduced
$1,475,000
 

622 Lighthouse Road, Southold

3 Beds, 2 Baths, 2,800 SqFt
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

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