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In storied locations from San Francisco to Sag Harbor, these irreplaceable homes afford the opportunity to own a piece of American history.
Sag Harbor, New York | Dana Trotter, Sotheby’s International Realty – Bridgehampton Brokerage
Capturing the rustic charm of Sag Harbor, this four-bedroom home was once the manse of the Old Whaler’s Church. Dating to circa 1765 and sensitively updated in 2012, it is filled with period character and beautifully preserved details, including walls constructed from ship ballasts, floors of brick and pumpkin pine, waxed Venetian plaster walls, and classic dentil moldings. It is equally inviting in winter and summer, with four warming fireplaces, a wine cellar, and a deck overlooking a heated pool and lush landscaped grounds.
San Francisco, California | Janet Feinberg Schindler, Sotheby’s International Realty – San Francisco Brokerage
In a coveted location with bay views, this light-filled residence once hosted former president Theodore Roosevelt and his wife. It offers four bedrooms, living and dining rooms, an eat-in kitchen, a deck, and a family room—all detailed with such classical elements as rich hardwood floors, warming fireplaces, and leaded-glass windows. A delightful two-bedroom garden apartment is located on the lower level. Up to five cars can be accommodated here, but the home is also an easy walk from nearly every amenity, attraction, and convenience.
This historically significant property near the Taos Plaza is a peaceful gated tree-covered compound comprising two homes on eight acres. Built in the late 1800s, the 5,600-square-foot four-bedroom adobe main residence was designed for entertaining, offering numerous gathering spaces, two master suites, patios, six indoor fireplaces, and countless custom features. The 2,816-square-foot Pueblo-style guesthouse has an open floor plan with three bedrooms. Boasting lush pastures, two wells, and a natural spring, the property would be ideal as an equestrian estate or private getaway.
Centerville, Massachusetts | Colleen Riley & Natalia Dukhovich, Sotheby’s International Realty – Osterville Brokerage
A delightful wraparound porch introduces this landmark home, which was built by sea captain Eli Phinney in the 1800s. Located in a national historic district of Centerville, the five-bedroom residence is filled with vintage charm, from southern pine floors to classic moldings and built-ins. Day-to-day living is easy thanks to formal living and dining rooms with fireplaces, a sunny casual family living area adjoining the kitchen, a mahogany-clad office, and five restful bedrooms. The lush backyard offers a refreshing swimming pool.
Los Alamos, California | Patty Murphy, Sotheby’s International Realty – Santa Ynez Valley Brokerage
Comprising 574 acres of rolling green hills and stalwart oaks in a picturesque valley, this idyllic ranch is part of California wine country history, owned by the renowned Jackson vintner family. The early-20th-century main residence features richly hued hardwood floors, French doors, high ceilings, abundant natural light, and plentiful authentic California farmland character. Completing the pastoral retreat are a detached two-bedroom guesthouse, a pair of two-car garages, and a newer three-bedroom manager’s residence—all with views of sweeping grasslands and the San Rafael Mountains.
Bridgehampton, New York | Eve Combemale, Sotheby’s International Realty – Bridgehampton Brokerage
Combining Old World accents with modern amenities, this lovingly restored and expanded 1840 residence is minutes from Bridgehampton Village and ocean beaches. It offers an open-plan living, dining, and kitchen area; four bedrooms that include a second-level master suite with an office, a spa-like bath, and a terrace; and a host of vintage elements, such as wide-plank wood floors and French doors. A dining patio and a breezy screened porch overlook the captivating modern pool. The grounds also include a freestanding 486-square-foot studio.
Discover more homes with incredible heritage in 5 Homes That Tell A Story