Winchester Homes with Shingle Style

Welcome to Winchester, Massachusetts, a charming town nestled in Middlesex County that seamlessly blends rich history with modern living. Known for its picturesque landscapes and vibrant community, Winchester is a hidden gem just a short drive from the bustling city of Boston. With its tree-lined streets, top-rated schools, and an array of local parks, this town is perfect for families and professionals alike.

One of the standout features of Winchester is its stunning architectural landscape, particularly the enchanting Shingle Style homes that grace many neighborhoods. Characterized by their distinctive wooden shingles, these homes exude a timeless elegance and warmth that captivates both residents and visitors. The Shingle Style emerged in the late 19th century and has become synonymous with coastal New England charm, making Winchester an ideal location for those who appreciate unique architectural beauty.

Living in Winchester means enjoying a tight-knit community with a wealth of amenities at your fingertips. Explore the delightful shops and restaurants in the town center, or take advantage of the nearby recreational opportunities, including the scenic Fells Reservation and the tranquil shores of Horn Pond. With convenient access to public transportation, commuting to Boston is a breeze, allowing you to enjoy the best of both worlds.

Whether you're drawn to the historic allure of Shingle Style homes or the vibrant community spirit, Winchester, MA, is a place where you can truly feel at home. Experience the charm of this delightful town and discover the perfect blend of history, beauty, and modern convenience.

Newest Winchester Homes with Shingle Style

$18,000,000

6 Beds ⋅ 7 Baths ⋅ 73585235 MLS

A NEW BENCHMARK FOR LUXURY LIVING IN WINCHESTER. Introducing a truly one-of-a kind estate—an extraordinary new residence created without compromise on approximately one private acre at the end of a cul-de-sac. Encompassing nearly 10,000 SF, 21 rooms, 6 bedrooms and 7 baths, this remarkable property brings together architectural presence, exceptional craftsmanship, advanced technology and resort-caliber amenities rarely found in a single Greater Boston residence.Beyond its gated entrance and heated driveway, sophisticated interiors unfold through grand entertaining spaces, a statement chef’s kitchen, library/office with wet bar, glass-enclosed fitness studio, acoustically designed cinema, wine lounge and underground wine cellar. The exceptional primary suite features a luxurious dressing room and dramatic two-tier panoramic veranda overlooking the grounds.Outside, the estate transforms into a private resort: spectacular pool with waterfall, integrated spa, flame features and automatic cover; covered outdoor kitchen; sunken conversation lounge with central fire feature; covered dining terrace with fireplace; and beautifully designed grounds offering extraordinary privacy.Behind the elegance is equally impressive infrastructure: 18 heating zones, 9 cooling zones, 600-amp electrical service, approximately 2.5M BTU gas capacity, integrated AV/security, automated gated entry and a 3-car climate-conscious auto lounge with porcelain flooring and dual EV charging.Minutes from Winchester Center and convenient to Boston, this is far more than exceptional new construction. It is a meticulously conceived private estate where architecture, technology, wellness, entertainment and resort living converge—created for the buyer seeking something that simply cannot be replicated.

15 Vinson Circle, Winchester

Listing courtesy of Listing Agent: Anthony Marino from Listing Office: The Marino Group Collection.

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