Chestnut Hill Homes with Colonial Style

Welcome to Chestnut Hill, a picturesque neighborhood nestled in the heart of Brookline, Massachusetts, within Norfolk County. Known for its enchanting blend of suburban tranquility and urban convenience, Chestnut Hill offers a unique lifestyle that appeals to families, professionals, and retirees alike. With its tree-lined streets, lush parks, and vibrant community spirit, this area is a true gem in the Greater Boston region.

One of the most captivating features of Chestnut Hill is its stunning array of Colonial-style homes. These architectural masterpieces exude timeless charm and elegance, showcasing symmetrical facades, classic brickwork, and inviting front porches that beckon you to enjoy a warm cup of coffee while soaking in the serene surroundings. Many of these homes boast spacious interiors with high ceilings, hardwood floors, and intricate moldings, providing a perfect canvas for both modern living and traditional aesthetics.

Living in Chestnut Hill means having access to top-rated schools, upscale shopping, and a variety of dining options that cater to every palate. Additionally, residents enjoy proximity to the scenic Chestnut Hill Reservoir and the lush grounds of the nearby Boston College, offering ample opportunities for outdoor recreation and cultural enrichment.

Whether you’re seeking a family-friendly neighborhood or a peaceful retreat just moments from the bustling city, Chestnut Hill stands out as a prime location. Experience the charm of Colonial-style homes and the vibrant community that makes this area a sought-after destination for homebuyers. Discover your dream home in Chestnut Hill today, where history meets modern living in perfect harmony.

Newest Chestnut Hill Homes with Colonial Style

$4,898,000

6 Beds ⋅ 7 Baths ⋅ 73532609 MLS

Set on a picturesque, tree-lined street, this exceptional 2016 brick Colonial offers an unparalleled combination of luxury and privacy in desirable Chestnut Hill. Built with uncompromising attention to detail and thoughtfully designed for both grand-scale entertaining and sophisticated everyday living. A gracious floor plan features soaring 10-ft ceilings, exquisite millwork, and beautifully proportioned rooms filled with natural light. The chef's kitchen with premium appliances and custom cabinetry flows seamlessly into a spectacular family room overlooking an expansive patio and professionally landscaped grounds. The residence offers 6 bedrooms, 6.5 baths, including a luxurious primary suite with a spa-inspired bath and custom walk-in closet. The lower level elevates the lifestyle experience with a home theater, fitness studio, private office, and full bath. Just moments from premier schools, fine dining, upscale shopping, and convenient to downtown Boston. Heated 3-car garage.

129 Rangeley Rd, Brookline

$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

$2,765,000

5 Beds ⋅ 4 Baths ⋅ 73516948 MLS

Come fall in love with this storybook 5-bed, 3.5-bath Colonial Revival set on 0.3AC in Brookline’s Chestnut Hill. Built in 1926, this charming 4,028SF residence offers a layout tailored for modern living. Streaming southern sunshine, timeless architecture, 3 fireplaces, and oversized windows define the home. Welcoming entry connects the main living spaces. Gracious living room w/ fireplace and built-ins flows into bright conversatory. Opposite is a family room with fireplace, which opens to a bright dining room. Classic butler’s pantry connects to the kitchen. With ample counter space and a cozy eat-in area, the kitchen serves as the heart of the home with direct access to deck and yard. Mudroom and half bath complete floor. Upstairs has bright en-suite primary, 4 additional bedrooms, office, and 2 full baths. Walkout lower level with playroom and laundry. Attached garage. Landscaped grounds create a true sense of privacy. Close to “The Street”, top schools, and Green D line train.

401 Heath Street, Brookline

$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

$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

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