151 Oakland Street, Wellesley 02481
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Set on a serene 1.15-acre knoll overlooking the fairways of the Wellesley Country Club, this remarkable historic residence offers breathtaking sunrise and sunset views in one of Wellesley’s most coveted settings. Abutting Centennial Reservation with direct access to walking trails, the property blends privacy, pastoral beauty, and timeless New England character.
Originally built in 1790 and thoughtfully relocated to this site in 1970, the home has been lovingly expanded and extensively renovated, with the majority of updates completed in 2022. Today, it offers three gracious levels of living with 16 rooms, wide pine floors, six fireplaces, and walls of windows framing the surrounding landscape.
The main level features an inviting great room with vaulted ceilings added in 2000, a paneled library or office, a gracious dining room, a cozy den, and a separate home office with private entrance. Upstairs, a vaulted-ceiling primary suite anchors the second floor alongside five plus additional bedrooms, an office or computer room, and a walk-up attic ideal for play or creative space. The newly built top-floor family and game room, connected to a bedroom, creates a flexible retreat perfect for entertaining or multi-generational living.
The finished lower level includes a spacious bonus room, gym, pool room, workshop, and abundant storage. Central air ensures modern comfort throughout.
Outdoor living is equally compelling. A bluestone patio with firepit, wraparound deck, mature gardens, fruit trees, and sweeping golf course views invite year-round enjoyment. A classic 19th-century barn, relocated from Maine, features two horse stalls and a fenced paddock, complemented by a new shed for a golf cart or equipment. Parking includes a two-car garage plus additional driveway spaces.
This is a rare opportunity to own a true piece of Wellesley history, perfectly updated for modern living, in a setting that feels both expansive and intimate. A property of this caliber, location, and provenance comes along once in a lifetime.
I would love to help you see this beautiful home! As a full-service brokerage, I can help you tour. Please submit an offer, and answer questions about the buying process.