$5,750,000

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… Read More 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. Read Less

Listing Courtesy of Daniel Gale Sothebys Intl Rlty.

Listing Snapshot

Days Online

Last Updated

Nov 8, 2026

Property Type

Single Family Residence

Beds

Full Baths

Partial Baths

Square Ft.

5,080

Lot Size

1.61 Acres

Year Built

2011

Property Tax

$44,983

MLS Number

1048493

Additional Details

Property Access

Frontage Type: Private Road, Road Responsibility: Private Maintained Road

Appliances & Equipment

Dishwasher, Dryer, Gas Oven, Gas Range, Microwave, Refrigerator, Stainless Steel Appliance(s), Washer, Gas Water Heater, Other equipment: Generator, Pool Equip/Cover

Basement

Full, Storage Space, Unfinished, Walk-Out Access

Building

Built in 2011, Built in 2011 (effective), Living area: 5080, Levels: Three Or More, Construction Materials: HardiPlank Type, Shingle Siding, Frame

Cooling

Central Air

Exterior Features

Patio/Porch Features: Deck, Patio, Porch, Dock, Awning(s), Balcony

Fence

Partial

Fireplaces

2 fireplaces, Family Room, Gas, Living Room, Wood Burning

Floors

Hardwood

Garage

2 spaces

Heating

Forced Air, Natural Gas

Home Owner's Association

Association Fee: $750, Fee Frequency: Annually

Interior Features

First Floor Bedroom, First Floor Full Bath, Cathedral Ceiling(s), Eat-in Kitchen, Elevator, Entrance Foyer, Formal Dining, Granite Counters, High Ceilings, Kitchen Island, Primary Bathroom, Master Downstairs, Open Floorplan, Open Kitchen

Laundry

Laundry Room

Lot

1.6 acres, Level, Part Wooded, Sprinklers In Front, Sprinklers In Rear, Cul-De-Sac

Parking

Attached, Driveway, Garage, Garage Door Opener, Private, Underground

Pool

Fenced, In Ground

Property

Other structures: Outbuilding, Shed(s), Panoramic, Open

Security Features

Security System

Sewer

Septic Tank

Taxes

Additional parcels description:, Parcel Number: 1000-081-00-01-00-016-007, Annual Amount: $44,983, Tax Block: 1, Lot: 16, Year: 2026

Utilities

Natural Gas Connected, Water Connected, Water Source: Public

Water Features

Water Access, Waterfront, Bayfront, Bulkhead

Windows

Insulated Windows, Blinds, Screens

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