Extraordinary North Fork Bayfront Estate on a Private Peninsula on Paradise Point, Southold- Welcome to one of Southold's most exceptional waterfront offerings, a spectacular bayfront estate set on a private 1.6-acre peninsula within the coveted Paradise Point community. Surrounded by water on three sides and boasting an extraordinary 335 feet of Bayfront shoreline and private dock in a protected boat basin, this remarkable property captures sweeping panoramic views across Southold Bay to Shelter Island and beyond. Approached by a circular drive framed by mature specimen plantings and meticulously landscaped grounds, the residence immediately impresses with its timeless Nantucket-inspired architecture and commanding waterfront presence. Encompassing approximately 5,100 square feet, the home offers 4 bedrooms and 3.5 baths thoughtfully designed to maximize light, space, and breathtaking water vistas from nearly every room. A grand two-story foyer welcomes you with a dramatic sightline through the home to the open bay beyond. Soaring ceilings, expansive living spaces, and walls of windows create an atmosphere of elegance and tranquility. The open-concept main level features a gracious living room with a wood-burning fireplace, a waterfront sitting room with a gas fireplace, and an office alcove. The expansive chef's kitchen is designed for both entertaining and daily living, featuring stainless steel appliances, granite countertops, and captivating views of the bay and heated waterside pool. Casual dining overlooks the water, while the formal dining room enjoys picturesque views of the protected boat basin. The first floor also includes a bayside en-suite primary bedroom, laundry room, and powder room. Upstairs, the luxurious primary suite and private sitting room offer unrivaled views over the boat basin and open bay. Two additional oversized guest bedrooms, each with water views, share a full bath, while the open landing provides yet another spectacular vantage point. Additional amenities include an elevator to all three level, whole house generator, spacious walkout basement ready for customization, 2-car garage and a heated waterfront pool. Rarely does a property combine such privacy, waterfront frontage, boating access, and panoramic views in one extraordinary setting. This is a once-in-a-generation opportunity to own a signature North Fork estate with dock and waterside pool. A truly exceptional waterfront retreat unlike any other.

Last Updated	9/10/2026	Tract	Paradise Point HOA
Year Built	2011	Garage Spaces	2.0
County	Suffolk

SCHOOLS

Elementary School	Southold Elementary School
Jr. High School	Southold Junior-Senior High School
High School	Southold Junior-Senior High School

Additional Details

AIR	Central Air
AIR CONDITIONING	Yes
APPLIANCES	Dishwasher, Dryer, Gas Oven, Gas Range, Gas Water Heater, Microwave, Refrigerator, Stainless Steel Appliance(s), Washer
BASEMENT	Full, Storage Space, Unfinished, Walk-Out Access
CONSTRUCTION	Frame, HardiPlank Type, Shingle Siding
EXTERIOR	Awning(s), Balcony, Dock
FIREPLACE	Yes
GARAGE	Attached Garage, Yes
HEAT	Forced Air, Natural Gas
HOA DUES	750
INTERIOR	Cathedral Ceiling(s), Eat-in Kitchen, Elevator, Entrance Foyer, Granite Counters, High Ceilings, Kitchen Island, Master Downstairs, Open Floorplan
LOT	1.6 acre(s)
LOT DESCRIPTION	Cul-De-Sac, Level, Sprinklers In Front, Sprinklers In Rear, Waterfront
PARKING	Attached, Driveway, Garage, Garage Door Opener, Private, Underground
POOL	Yes
POOL DESCRIPTION	Fenced, In Ground, Private
SEWER	Septic Tank
STORIES	3+
STYLE	Traditional
SUBDIVISION	Paradise Point HOA
TAXES	44983
UTILITIES	Natural Gas Available, Natural Gas Connected, Water Connected
VIEW	Yes
VIEW DESCRIPTION	Panoramic
WATER	Public
WATERFRONT DESCRIPTION	Waterfront, Waterfront Access

Location

 

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