Southold, NY homes for sale & real estate

Southold, NY Homes for Sale

Waterfront dream! This 3-bed, 2.5-bath home boasts deep-water docking. Open floor plan on both levels features two stone fireplaces, primary en-suite, ample storage, and a large open kitchen with breakfast and dining areas. Enjoy large sliders accessing two decks overlooking the waterfront, plus a spacious waterside boat house. Benefit from a brand new bulkhead & decking completed in 2025. Built by Deck Homes for guaranteed quality!

Southold, NY Homes for Sale

Gorgeous estate-like Nantucket shingle home in the final stage of construction. Designed by the renowned firm of Nelson and Pope, this lovely home follows an entertainer's dream layout: open Great Room concept with fireplace, Chef's gourmet kitchen with custom cabinetry and Bertazzoni appliances, large island and breakfast nook, formal dining room with Butler's pantry, a first floor junior primary ensuite, and library. White oak hardwood floors throughout. Upstairs is a spacious primary ensuite with two walk in closets, 3 more bedrooms, 2 full baths, a laundry room, and a bonus family room. The walk out basement is ready for you to finish as you wish, with room for home theatre, wine cellar

Southold, NY Homes for Sale

Scenic and bucolic, this 3+ acre country farm is steeped in classic North Fork charm. The property features an authentic 1800s four-bedroom, one and a half bath, farmhouse, a 2+ car garage (1976) with a workshop, office and mechanics pit, and a 1985 barn equipped with three horse stalls and ample space for tractors. Additional structures include a cinderblock chicken coop and a pig sty, offering true farmstead character. A large, established two thirds of an acre vegetable garden and an active farm stand highlight the property’s agricultural potential, while the watering hole rises and falls with the rains. Whether you choose to reimagine, repurpose, or preserve this unique homestead

Southold, NY Homes for Sale

A charming four-bedroom, two-bath, one-level home with a touch of nostalgic appeal. This home boasts wood flooring and an attached two-car garage, nestled on a level corner lot. The primary bedroom offers the convenience of an attached full bathroom. The house, while in need of a little TLC, presents an exciting opportunity - a blank canvas ready for your personal touch. The full basement adds to the potential of this home. The property is part of the Southold Park District, providing special beach privileges at Founders Landing Park and the Wharf House. Additionally, a chance to participate in the town lottery for a discounted boat slip is an enticing extra. Located just a stone's throw fr