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(Photo courtesy of Douglas Elliman)

This home is all about the water lifestyle, whether you’re looking at the bay through the oversized windows, swimming in the backyard pool or getting up close and personal via your own 252 feet of waterfront and private dock on Shelter Island Sound.

The nuts and bolts

3.28 acres, with 252 feet of waterfront

4,362 square feet

5 bedrooms

6 bathrooms

Built 1970

House proud

Set back from Paradise Point Road by a long, gated tree-lined driveway and on more than three acres, this home offers seclusion, numerous exterior assets and entertainment amenities, making this a compound by the water that can rival an all-inclusive resort. 

“The sellers are meticulous homeowners and everything has been perfectly done, maintained and serviced, the home is turn key in every aspect,” says Kristy Naddell, the Douglas Elliman agent who is co-listing the home with Thomas Uhlinger. “It’s completely set up for indoor and outdoor entertaining – it really doesn’t get any better.”

What’s the plan?

The main entry into the home is through a covered porch that leads into a 271-square-foot foyer, which serves as a hub to the main living areas and two wings that house the five ensuite bedrooms. An oversized floor-to-ceiling stone fireplace and chimney anchors the open format living /dining room—a show-stopping feature made of variously sized stacked stone, a reclaimed timber mantle, a stone sitting hearth and integrated wood box (though the fireplace itself is gas powered). It provides separation between the 506-square-foot great room and the 233-square-foot dining room. Adjacent to the kitchen is a large family room, breakfast nook and a bathroom. The three bedrooms on this side of the house average around 165 square feet. On the other wing, the two bedrooms include the 267-square foot primary suite and a fifth bedroom comparable in size to the others.

What’s cooking?

(Photo courtesy of Douglas Elliman)

The 220-square-foot is equipped with a Viking oven and hood, GE Monogram fridge and Miele dishwasher, and an integrated microwave in the center island. Quartz counters top the custom cabinetry and island, which offer ample storage and work space. The custom-tiled backsplash is reminiscent of an Italian terrazzo floor. Sliding doors just beyond the L-shaped counter lead to the 760-square-foot grill-ready patio, expanding the dining and entertainment space. 

What else?

(Photo courtesy of Douglas Elliman)

Adjacent to the fireplace is a custom-built wet bar and entertainment area with an undercounter mini fridge and wine cooler. Throughout the home, the owners converted tile floors to hardwood, refinished the wood floors they kept and installed new marble as necessary. 

Starting with an anteroom and continuing through the great room, dining area and sun room, the back of the house is virtually a continuous wall of windows overlooking the water. The 580-square-foot sunroom offers expansive water views and seasonal dining and entertainment.

Amenities and more

Naddell calls the outdoor space “an entertainer’s paradise” with an outdoor sound system, gas firepit, a heated saltwater pool with an automatic pool cover, separate hot tub, and a pool house fully equipped with a wet bar and seating, media screen and an outdoor shower. The waterside cabana/boat house is equipped with electric and plumbing and is reached by private stairs. 

One cool thing (or two)

  • The meticulously landscaped grounds include a mature vegetable garden that can supplement shopping trips to the farmer’s market. 
  • With generous and expansive lawns, there’s ample room to add a pickleball or tennis court, making this a truly all-inclusive resort experience.   

Agent’s callout 

(Photo courtesy of Douglas Elliman)

“It’s hard to find something like this. A lot of homes on the bay are not so private, but, here, you really don’t see your neighbors on either side,” Naddell says. “It’s only those homeowners there—no public access or through traffic —so it’s very private.”

Location, location, location

Paradise Point Road is on a peninsula jutting out into Shelter Island Sound leading into Noyack and Little Peconic bays. The home at 750 is about 4.5 miles from the 10-and-a-half-square-mile hamlet of Southold, and in the other direction, seven miles from Cutchogue. It’s also at the gateway of North Fork wine country, with some of the area’s most pioneering wineries within five miles. Founders Landing Park is five miles from the home and Emerson Park is 3.4 miles. 



The home at 750 Paradise Point Road in Southold lists for $7,395,000 and the details can be seen here