#1: Spectacular Southampton Village Victorian
Located at 75 First Neck Lane, this spectacular 10-bedroom, 10-and-a-half-bath estate—originally built in 1895—sits on a lush two-acre lot and offers 9,500 square feet of living space. Now asking $14.25 million, this gorgeous, shingle-style home features oversized principal rooms adorned with detailed moldings and trim, including a large foyer that opens to the formal living room with a fireplace; a sunroom that leads into awning-covered patios; and a paneled dining area. Other spaces include a large eat-in kitchen, a butler’s pantry, a library, and a conservatory overlooking the expansive grounds. Outside lies a pool house with its own full bath, while a playroom and gym, wine cellar, and staff’s quarters can be found on the lower level. Extra amenities include a lap pool, putting green, tennis court, and a natural gas generator that power the whole estate. The listing agent is Michaela Keszler of Douglas Elliman.
For more information on this $14,250,000 listing, visit here.
#2: Marvelous Mansion on the Bay
Comprised of seven bedrooms and nine baths, this stunning residence overlooking Peconic Bay—now asking $8.45 million—opens to a 32-foot foyer, and showcases a living room/library, a bayfront dining room (both with fireplaces), and a gourmet kitchen with a pizza oven and breakfast nook. Situated on a wing of its own, the master suite has a fireplace, separate baths with steam showers, and a dressing room, plus a private deck with 200-degree views of the Bay. The 2,800-square-foot lower level boasts radiant-heated flooring, two bedrooms, a wine cellar, a game room with a fireplace, and a gym, while outside lies an attached, two-car garage, an infinity pool with a brick fireplace, and a large deck that leads to the beach and sea below. The listing agent is Michaela Keszler of Douglas Elliman.
For more information on this $8,450,000 listing, visit here.
#3: Opulence on Ox Pasture Road
This massive, amenity-rich estate rests on a 10-acre swath in the Estate Section of Southampton Village. The traditional-style home—now listed at $45 million—offers 18,000 square feet of living space, including a dozen bedrooms and 15 baths, a cutting-edge kitchen, an in-house gym, and a carriage house. Built in 1915, the fireplace-dotted residence features elegantly-decorated interiors. Leaded glass doors in the living room overlook its wonderfully-landscaped grounds, which house a four-car garage, a grass tennis court, a paddle court, and an outdoor pool with a pavilion and large waterslide. The listing agent is Michaela Keszler of Douglas Elliman.
For more information on this $45,000,000 listing, visit here.
#4: Awe-Inspiring Bayfront Traditional
With 7,000 square feet spanning eight bedrooms and 10 baths, this remarkable estate—now on the market for an undisclosed figure—features 435 feet of waterfront. Apart from its main structure and guesthouse, the property includes a heated infinity pool and tennis court—both overlooking the bay—and a dock, creating a residence ideal for watersports and relaxation. The listing agent is Michaela Keszler of Douglas Elliman.
For more information on this listing, visit here.
#5: Elegant Water Mill Estate
This 20,000-square-foot residential masterpiece—showcasing eight bedrooms and 11 baths—sits on four acres on Mecox Bay. Blending Old World elegance with modern convenience, the estate—now asking $45 million—features eight fireplaces with early 19th-Century mantles, coffered ceilings, and gracious balconies, while its grand foyer opens to a cast bronze double staircase and an antique stained-glass skylight. Other spaces in the posh abode include a wine cellar, gym, sauna, theater, and two kitchens. Outside lies an infinity-edged pool, Jacuzzi, tennis court, dock, and Koi pond, making the estate perfect for grand-scale entertaining. The listing agent is Michaela Keszler of Douglas Elliman.
For more information on this $39,000,000 listing, visit here.