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$2,999,000

Set on an extraordinary 11.31 private acres in one of Southold’s most prestigious enclaves, this expansive estate was built in 1997 yet thoughtfully designed to capture the timeless character and gracious proportions of a grand early-1900s country home. A stately approach, welcoming covered porches and impressive entry set the tone for generously scaled interiors designed for both everyday living and large-scale entertaining. The home features 4 spacious en suite bedrooms, grand living and dining spaces, a library, serving kitchen, 5 fireplaces and an abundance of room for family and guests. A separate apartment with its own entrance provides additional flexibility for extended family, guests, work-from-home needs or private accommodations. Once operated as a bed and breakfast, the residence offers a distinctive layout and exceptional versatility. Additional features include a 4-car garage, expansive basement with 10-foot ceilings, irrigation system and 2-stall barn. Of the 11.31 acres, approximately 9.31 acres are open space with an additional 2 acres of buildable land, creating a rare opportunity for a private compound, equestrian use, extensive gardens or future possibilities. A truly unique North Fork offering combining substantial acreage, grand proportions, architectural character and exceptional privacy.

4 Beds ⋅ 6 Baths ⋅ 1052436 MLS

9680 N Bayview Road, Southold

$4,299,000

WELCOME TO PARADISE. Commanding 2.38 private acres on the bay in Southold’s coveted Paradise Point, this remarkable waterfront estate possesses the cinematic North Fork presence of a setting from Nelson DeMille’s Plum Island—dramatic, intriguing and entirely unforgettable. With approximately 97 feet of private beach, panoramic views toward Shelter Island and the estate-lined shoreline beyond, plus community boating rights with access to the residents’ boat basin, the property offers exceptional privacy without sacrificing comfort or convenience. Custom built in 1993, the approximately 3,500-square-foot residence offers four bedrooms, three full baths and three levels designed for gracious year-round living. Bold proportions, soaring 20-foot ceilings, walls of glass and a sweeping staircase capture the confident glamour of grand-scale coastal architecture, while abundant natural light and extraordinary water views give the interiors a timeless quality. This is not a conventional beach house; it is a substantial bayfront residence designed to make an impression. The dramatic double-height great room is anchored by a rare natural coral-stone fireplace and opens to more than 1,500 square feet of exterior decking—an exceptional setting for entertaining, dining outdoors or simply watching the light move across the bay. A formal waterside dining room complements the spacious eat-in kitchen, which provides generous counter space and an inviting place for everyday gatherings. The main level also includes pantry and laundry areas, together with a flexible 4th bedroom or den and adjacent full bath—ideal for guests, a private home office or convenient first-floor living. Ascend the sweeping staircase to the waterfront primary suite, a private retreat featuring magnificent bay views, its own waterside terrace, a luxurious full bath and walk-in closet. Two additional bedrooms and another full bath complete the upper level. The finished lower level expands the home’s recreational possibilities with a game or media area, direct access to a waterside terrace and an attached multicar garage. Outside, the expansive, level grounds provide ample room for entertaining, recreation and quiet enjoyment amid beautiful natural surroundings. A private boardwalk leads directly to the sandy beach, where days can be spent swimming, fishing, kayaking, paddleboarding or launching a morning adventure on the bay. Although wonderfully private, the estate is only minutes from Southold Village and the restaurants, vineyards, farm stands, shops, beaches and boating destinations that define North Fork living. Additional amenities include public water, a supplemental well, oil-fired forced-air heat and central air conditioning. Rare acreage, substantial private beach frontage, community boating access and a dramatic waterfront residence come together in one extraordinary Southold offering. Paradise Found.

4 Beds ⋅ 3 Baths ⋅ 1053616 MLS

3525 Paradise Point Road, Southold