Southold, NY Homes for Sale with Acreage

2-Acre Private Oasis with Custom "To Be Built" Luxury Home - Excellent Location Near Town, Beaches & Vineyards! Discover the perfect blend of privacy, luxury and convenience with this exceptional vacant lot, tucked away in a serene, secluded setting --- Yet just minutes from downtown, pristine beaches, and world-class vineyards, shopping and dining. Plans are in-place for a "To Be Built" custom

Thomas McCarthy Thomas J McCarthy Real Estate

Southold, North Fork: The historic Boisseau farmhouse, built around 1890, is situated on 1.75 acres (76,230 square feet) with R40 residential zoning, in a picturesque setting featuring mature trees and a sprawling lawn. The property is adjacent to fallow, and partially wooded acreage owned by the Town of Southold. The traditional home boasts a charming covered front porch, an entry foyer, and a

Nicholas Planamento William Raveis New York LLC

Southold Stunner- New ConstructionThis one's a North Fork knockout. Set at the end of a quiet cul de sac on over 2 private acres, minutes from the sand, the house was built to check every box. Inside you're met with all-day sunshine, four legit bedrooms, 4.5 spa-like baths (sanitary system in place for 7 bedrooms), and a true chef's kitchen-with a 48" Sub Zero, Wolf double range + wall oven,

Sheri Winter Parker Corcoran

Private Southold Retreat on 2.18 Acres- Tucked away at the end of a private lane in desirable North Fork location, this special property offers the perfect balance of privacy and convenience. Surrounded by preserved land, large properties and a horse property, the picturesque 2.18-acre setting provides a peaceful retreat while remaining just minutes from restaurants, marinas, shops, wineries,

Nancy Cervelli Daniel Gale Sothebys Intl Rlty

Designer Modern Farm Ranch set on over 3.35 Acres with farm and scenic views. Renovated 2023. Open concept Living Room, Dining Room and Kitchen, Gorgeous Kitchen with quartz countertops, Stainless Steel Appliances, built in Wine Cooler, New Windows throughout, New Interior Doors, New Exterior Doors, Custom Closets, New flooring, updated Designer Baths, New Boiler, New Well Pump, New Hot Water

Arelis Olivieri RIN

Gorgeous estate-like Nantucket shingle home to be completed early August with time to enjoy summer of 2026 and the Fall Harvest Season on the North Fork! Seller will consider owner financing.Designed by the renowned firm of Nelson and Pope utilizing steel beam construction throughout and Benjamin Obdyke Hydrogap house wrap, the home features solid white oak hardwood floors, as well as

Jeffrey Mead Corcoran

Set on five bucolic acres, this property perfectly captures the pastoral character that defines the region at its best. Mature trees frame the entrance, and split-rail fencing lines the property, offering a sense of privacy and openness rarely found so close to everything the North Fork has to offer. The three-bedroom, two-bathroom farmhouse is complemented by a large barn, currently outfitted

Bridget Elkin Compass Greater NY LLC

Wake up to the salt air at your new coastal compound, a rare waterfront opportunity for those seeking something truly different. Unapologetically distinctive, this mid-century modern residence offers an extraordinary combination of waterfront, privacy, architectural character, and artistic location.Held in the same family for more than 50 years, the over 4000-square-foot home is set on two

Thomas McCarthy Thomas J McCarthy Real Estate

Set on nearly four acres along one of the North Fork’s most coveted stretches of sandy bay beach, this is a rare opportunity to secure an exceptional waterfront property with meaningful upside. The existing three-bedroom, four-bath home offers a solid foundation for renovation or expansion, allowing a new owner to tailor the property to their vision.The grounds are equally compelling. A

Bridget Elkin Compass Greater NY LLC

Steeped in history and set on a 1.05-acre parcel in the heart of the North Fork, this circa-1663 residence presents a rare opportunity to preserve and reimagine one of Southold’s oldest and most significant properties. Ideally positioned, it is just moments from one of the East End’s finest sandy bay beaches and Croteaux Vineyards, as well as a short drive to renowned wineries, farm stands, and

Marco Maida Compass Greater NY LLC

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,

Nicholas Planamento William Raveis New York LLC

Discover a rare waterfront property where privacy, space, and breathtaking views come together on 6.5 gated acres. Spanning two single-and-separate lots, this refreshed 6-bedroom, 4-bath colonial offers a den/office, bonus room, and sweeping water views from nearly every room.Thoughtfully designed for both comfort and future flexibility, the residence provides substantial expansion

Roric Tobin Compass Greater NY LLC

Charming updated Soundfront beach house! This home is what dreams are made of. Steps away is a plush, powder white sandy path leading to a serene private beach where panoramic vistas and mesmerizing sunsets will sweep you off your feet. Offering approximately 1,600 sq. ft. of living space, the first level boasts an eat-in-kitchen, living room with fireplace to cozy up to during those brisk fall

Nicholas Liappas Compass Greater NY LLC

Located in one of the most sought-after locations on the North Fork sits this quintessential cedar shake farmhouse situated on 2 private acres! This home combines timeless charm with modern comforts. The main level features hardwood floors throughout, a spacious living room with a wood-burning fireplace, formal dining room, eat-in kitchen with granite countertops and pantry, a convenient half

Kristy Naddell Douglas Elliman Real Estate

North Fork retreat! A powder white sandy path leads to a gorgeous private beach offering 116 ft. of waterfrontage while incredible sparkling Sound views, sunsets, and lush greenery set this property apart. Enjoy water views from the open concept main level and the expansive 800+ sq. ft. rear deck - perfect for lounging, al fresco dining and taking in the fresh sea air. With over 3,000 sq. ft. of

Nicholas Liappas Compass Greater NY LLC

Welcome to 920 Cedar Point E in Southold, a spectacular 1.4-acre waterfront estate overlooking one of the most breathtaking stretches of the Peconic Bay, complete with a private deeded dock slip just steps from the property. Featuring 200 feet of pristine sugar-sand beachfront, this exceptional setting offers privacy, serenity, all-day sunshine, and the gentle prevailing southwest breezes for

William Mcintosh Daniel Gale Sothebys Intl Rlty