Chestnut Hill Homes with Tudor Style

Welcome to Chestnut Hill, Massachusetts—a picturesque community that beautifully marries suburban tranquility with urban convenience. Nestled just six miles west of downtown Boston, Chestnut Hill is renowned for its lush landscapes, historic charm, and vibrant cultural scene. With its tree-lined streets, boutique shops, and top-rated schools, this area offers a perfect setting for families, professionals, and retirees alike.

One of the most enchanting aspects of Chestnut Hill is its stunning collection of Tudor-style homes. These architectural gems, characterized by their steeply pitched gable roofs, decorative half-timbering, and intricate masonry, evoke a sense of timeless elegance. Each Tudor home tells a story, boasting unique features such as leaded glass windows, grand fireplaces, and expansive gardens that create a warm and inviting atmosphere.

Living in a Tudor-style home in Chestnut Hill means embracing a lifestyle steeped in history and sophistication. The spacious interiors often include cozy nooks perfect for reading, entertaining, or simply enjoying a cup of tea. The expansive lots allow for outdoor gatherings, where you can soak in the beauty of the changing seasons—a true hallmark of New England living.

In addition to the architectural allure, Chestnut Hill offers a wealth of recreational opportunities. From the scenic paths of the Chestnut Hill Reservoir to the nearby shops and dining options, residents enjoy a blend of leisure and convenience. Whether you’re exploring the local parks or indulging in a culinary experience at one of the area’s acclaimed restaurants, Chestnut Hill is a community that invites you to live life to the fullest. Come discover your dream home in this charming enclave, where history and modern living coexist beautifully.

Newest Chestnut Hill Homes with Tudor Style

$2,395,000

4 Beds ⋅ 5 Baths ⋅ 73569446 MLS

Set along one of Chestnut Hill’s picturesque tree-lined streets, this handsome brick Tudor offers a thoughtful blend of classic architecture, generous proportions & comfortable everyday living. A welcoming foyer introduces elegant living & dining rooms with hardwood floors & distinctive period details, while the spacious eat-in kitchen, with abundant cabinetry, updated appliances & wet bar, opens naturally to a relaxed family room with direct access to the backyard. Upstairs, four well-proportioned bedrooms include a generous primary suite overlooking the backyard, complete with a sizable walk-in closet & ensuite bath. A second ensuite bedroom, along with two additional bedrooms, provides flexibility for family, guests or a home office. The lower level offers versatile space for recreation, hobbies, storage or future expansion, with convenient access to the garage. Outdoors, a tiered backyard creates a private setting with a pool, deck & lawn, offering multiple spaces for entertaining, relaxing & enjoying the warmer months. Fresh paint, new and refreshed flooring & an updated back deck enhance the home’s appeal while preserving its distinctive character. Ideally situated in the Baker School District, with easy access to Route 9, shopping, dining & the amenities of Chestnut Hill, this is a home with both an inviting sense of place & room to make it your own.

72 Beverly Rd, Brookline

Listing courtesy of Listing Agent: Ovesen Group from Listing Office: Coldwell Banker Realty - Brookline.

$1,790,000

4 Beds ⋅ 3 Baths ⋅ 73549795 MLS

$200,000 PRICE REDUCTION!! Fantastic move-in-ready 4 bedroom, 2.5 bathroom in BROOKLINE. Set on a 15,000+ level private lot, LEAD FREE, perfect for INVESTOR or END USER, close to schools, shops, restaurants, public transportation, golf & Skyline Park with its trails, playgrounds, fields and other amenities. Filled with natural light, the main level has beautiful hardwoods, a fireplaced living room, lovely dining room, eat-in kitchen, family room, home office and guest bathroom. Upstairs are 4 very generous bedrooms. and a full hallway bathroom.The primary bedroom has vaulted ceilings, sky lights and, in addition to the large ensuite bathroom, a second separate dressing room with its own sink and vanity. The home's lower level has high ceilings and unlimited potential to be used as a gym, movie theatre or what ever your needs maybe. There is central a/c.The backyard is level and private, with an expansive deck off the kitchen and family room for entertaining. A 2 car garage and large driveway complete this offering.

75 Hammond Pond Parkway, Brookline

Listing courtesy of Listing Agent: Amy Sassoon from Listing Office: Coldwell Banker Realty - Brookline.

$2,199,000

4 Beds ⋅ 4 Baths ⋅ 73529380 MLS

Welcome home to this impeccably maintained 4BR English Tudor offering the perfect blend of historic charm and modern updates. Set back on a lush 0.43-acre lot, enjoy panoramic views of the Brookline Golf Course directly across the street. This property is entirely turn-key for today’s active family, featuring an expansive 12-room layout with soaring ceilings, a sunlit family room, and central A/C. Outdoor living shines with a classic screened porch and a private brick patio nestled in an oversized, professionally landscaped yard. Situated in a premier neighborhood steps from the acclaimed Baker School (K-8), local shopping at Putterham Circle, and an effortless commute to Longwood Medical Center and downtown Boston. Move right in and enjoy the quintessential Brookline lifestyle!

518 Newton St, Brookline

Listing courtesy of Listing Agent: Shi Earls from Listing Office: Winterspring Real Estate, LLC.

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