42 Highfields Road

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About this home

MANY More photos (and video) coming Friday 9/11/26 in the am. Rare true post-and-beam Cape tucked away on a quiet dead-end road in one of Wilton’s most inviting country settings. Warm, natural, and full of character, this home offers exposed beams, rich wood details, over 2400 square feet of living space, a wood stove insert as well as a free standing wood stove in the finished lower level, quality cherry cabinetry with soapstone counters, and comfortable gathering spaces that feel timeless and welcoming inside and out. The current owners have completed an impressive list of major improvements, including new appliances, a new roof, new siding, new heating system, mini-split AC/heat pumps, almost all new triple-pane Pella windows, a rebuilt deck and an all new wood-burning sauna. The main living areas offer a wonderful blend of craftsmanship and comfort, while the large (24 X 16) deck overlooks the backyard and creates a beautiful place to relax, entertain, or enjoy the peaceful surroundings. The walk-out daylight lower level adds valuable finished living space with a beautifully finished walk-out lower level offering flexible guest, office, media, or extended-family space, complete with a three-quarter bath, third “bedroom” and bar area with a free standing wood stove offering excellent flexibility for guests, office space, media room, hobbies, extended family, or a private retreat. Set on approximately 2 acres, this property offers a private natural feel while still being just moments from Hilltop Café, the Waldorf school community, Wilton Center, local farms, trails, and the charm that makes Wilton so special. A distinctive home for buyers seeking craftsmanship, comfort, privacy, and a lifestyle that is hard to duplicate. All barely an hour from the Boston City Limits and under 90 minutes from the Coast or the Mountains. Showings to begin Saturday 9/12 at ten am at the Open House. Sale subject to sellers securing housing, and they're actively making offers!

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Explore costs at the $639,900 asking price. Adjust the assumptions to your situation.

Partial estimate: add insurance, monthly HOA to include those costs. Blank amounts are unknown.

The initial 6.5% rate is illustrative, not a current rate or lender quote. Excludes utilities, maintenance, closing costs and mortgage insurance, which may apply with a down payment below 20%. Taxes and insurance can change.

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Active city listing statistics from PrimeMLS as of September 11, 2026. Asking prices are not completed-sale values.

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