Chestnut Hill Homes with Colonial Style

Welcome to Chestnut Hill, Massachusetts – a picturesque community that seamlessly blends suburban tranquility with urban convenience. Nestled just a stone’s throw from Boston, Chestnut Hill is renowned for its lush landscapes, historic charm, and vibrant cultural scene. With its tree-lined streets and beautifully manicured gardens, this neighborhood is a sanctuary for those seeking a peaceful retreat without sacrificing proximity to city amenities.

One of the standout features of Chestnut Hill is its stunning selection of homes, particularly those showcasing the timeless elegance of Colonial architecture. These homes, characterized by their symmetrical facades, grand columns, and classic brick exteriors, exude a sense of history and sophistication. Many Colonial-style homes in the area feature spacious interiors, with high ceilings, intricate moldings, and inviting fireplaces, making them perfect for both entertaining and cozy family gatherings.

Living in Chestnut Hill means enjoying a wealth of local amenities, including boutique shops, gourmet dining, and access to top-rated schools. The area is also home to beautiful parks and recreational facilities, perfect for outdoor enthusiasts. Whether you’re taking a leisurely stroll through the scenic paths of the Chestnut Hill Reservoir or enjoying a round of golf at one of the nearby country clubs, there’s no shortage of activities to keep you engaged.

In Chestnut Hill, you’ll find not just a home, but a lifestyle steeped in history and community spirit. Explore the charm of Colonial-style homes and discover why this enchanting neighborhood is the perfect place to call home!

Newest Chestnut Hill Homes with Colonial Style

$3,999,999

6 Beds ⋅ 6 Baths ⋅ 73568425 MLS

Tucked at the end of a desirable cul-de-sac in Chestnut Hill, this classic shingle-style residence offers four beautifully finished levels of living with a timeless traditional design. Hardwood floors, gracious room proportions, and a warm, inviting floor plan create a home equally suited for everyday living and entertaining.Featuring 6 bedrooms and 6 full bathrooms, the residence offers exceptional flexibility for family, guests, home offices, and additional living spaces. The finished walk-out lower level adds another dimension of usable space with direct access outdoors, while the three-car garage provides both convenience and ample storage.Beautifully landscaped grounds enhance the home’s curb appeal and sense of privacy, with the property set on approximately 25,000 square feet of land. Combining substantial living space, classic New England architecture, and a sought-after Chestnut Hill cul-de-sac location, this is a special opportunity to enjoy comfort, scale, and timeless character.

31 Kesseler Way, Newton

Listing courtesy of Listing Agent: Samantha Stumpo from Listing Office: Serhant.

$8,200,000

6 Beds ⋅ 9 Baths ⋅ 73526856 MLS

Set on over 1.2 acres with a 1.62-acre experience via a neighboring easement, this exceptional Chestnut Hill estate offers a tranquil oasis on one of the area’s most coveted and secluded streets. Originally built in 1900 and thoughtfully renovated over time, the residence spans more than 9,300 square feet with six bedrooms, six full bathrooms, and three half bathrooms. Its richly detailed living spaces were designed for both elegant entertaining and everyday comfort. Gracious formal rooms, soaring ceilings, and exquisite millwork overlook beautifully landscaped grounds featuring a heated, in-ground pool, a basketball court, and ample parking. Once home to Alvan T. Fuller, the 50th Governor of Massachusetts, the property carries remarkable historic provenance. The grounds were originally designed by Frederick Law Olmsted, further contributing to the property’s timeless character. This is a rare opportunity to own a historic estate of this scale in an unbeatable location.

40 Singletree Rd, Brookline

Listing courtesy of Listing Agent: Maggie Gold Seelig from Listing Office: MGS Group Real Estate LTD.

$3,450,000

7 Beds ⋅ 7 Baths ⋅ 73494324 MLS

Location ! Location! Location! This stunning Colonial effortlessly blends timeless architecture w/ modern luxury, offering exceptional living space.Main level showcases a gracious family room w/ beamed ceilings & a fireplace, a chef’s kitchen w/ a butler’s pantry & a sun-drenched breakfast area that opens to a patio & a professionally landscaped, fenced-in backyard ideal for indoor-outdoor entertaining. A formal living room, dining room, ensuite bedroom, powder room & a mudroom w/ direct access to a 2 car garage complete this level. 2nd floor the expansive primary suite features a spa-like bathroom, a walk-in closet & a serene sitting area/ office. Spacious bedrooms w/ en suite baths & a well-designed Jack& Jill bath. Lower level adds exceptional versatility with a gym, wet bar, playroom, bedroom suite, & abundant storage ideal for multigenerational living. New 2026 Boiler installed. Bonus attic offers additional space potential for expansion/customization. A true gem in desirable area

22 Scotney Road, Newton

Listing courtesy of Listing Agent: Esin Susol Team from Listing Office: William Raveis R. E. & Home Services.

$9,985,000

5 Beds ⋅ 8 Baths ⋅ 73478330 MLS

Set on .74 acres in one of Brookline’s most coveted neighborhoods, this newly constructed estate blends timeless architecture with exceptional modern design. With impeccably finished living spaces and full AV wiring, it offers 5 bedrooms, 6 full and 2 half baths, and a layout ideal for today’s lifestyle. The heart of the home is a showstopping chef’s kitchen with top-tier appliances, custom cabinetry, and a large island opening to sun-filled living and dining areas. A seamless indoor-outdoor flow connects to the private, flat tree-lined lot—perfect for entertaining or relaxation. Highlights include a luxurious primary suite with spa bath, generous secondary bedrooms, family room and a versatile finished lower level, attached 3-car garage with heated driveway, permitting for a pool. Built by a renowned local builder, this move-in-ready residence offers unmatched style, craftsmanship, and comfort in one of Brookline’s most desirable settings. Just bring your toothbrush!

68 Clyde Street, Brookline

Listing courtesy of Listing Agent: Maggie Gold Seelig from Listing Office: MGS Group Real Estate LTD.

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