54 exquisite homes on one of Milton's historic private estates

A view of a livingroom at Wolcott Woods, a luxury home for sale in Milton, MA.

Welcome to Wolcott Woods

Nestled on 47 hillside acres neighboring the Blue Hills Reservation, Wolcott Woods is a new 55+ community from an award-winning team offering 54 exquisite homes on one of Milton's historic private estates.

Start your next chapter…open the door to find a new place to call home

Wolcott Woods is comprised of 54 homes, offering free-standing and duplex style properties and three original homes dating back to the 1800s that are being meticulously remodeled. The estate-feel to the property is being maintained by using architectural elements found in the existing historic homes on the site and estate homes in the area.

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A new 55+ neighborhood with prime location, thoughtful design and compelling history

Integrating design elements of the past into modern architecture was a key goal of the Wolcott Woods design team. Everything from materials used to the plants in the landscaping has been chosen to honor the past and the local environment. The 54 stately homes that make up this new 55+ community feature a diverse collection of architectural styles and materials, including stucco, shingle, and brick exteriors. Inspiration for the new residences has been drawn from the estate’s three historic homes and estate homes in the area, all of which will be preserved and updated.

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A view of the kitchen in the Cushing home model in Wolcott Woods, a luxury home for sale in Milton, MA

“It’s just beautiful. I think it’s one of the most beautiful communities in Suburban Boston. I saw value there: the historic nature of the setting, the charm of the house I’m buying…I’m looking forward to living there.”

— Denise & Kevin

“As soon as I set foot on the property, I knew I was home. Wolcott Woods offered everything I loved about Metrowest living, and it was hard to believe I was only 15 minutes from Boston. It's convenient to everything and still feels close to nature in such a beautiful setting.

— Anne Marie

“I love the way the light comes in — it just absolutely pours in. Everybody responds to the light when they come in, and they say it feels like I'm outdoors here. So, it's almost like a tree house, and I would say that’s my favorite thing about this build.”

— Mallory