Chestnut Hill Homes with Colonial Style

Welcome to Chestnut Hill, Massachusetts—a picturesque community that perfectly blends suburban charm with urban convenience. Nestled just a stone's throw from Boston, this enchanting neighborhood is renowned for its lush green landscapes, historic architecture, and vibrant local culture. Whether you’re strolling along tree-lined streets or enjoying a day at the Chestnut Hill Reservation, you’ll quickly discover why this area is a coveted destination for families and professionals alike.

One of the standout features of Chestnut Hill is its stunning array of homes, particularly the timeless Colonial-style residences that grace the neighborhood. These homes, characterized by their symmetrical facades, classic brick exteriors, and inviting front porches, exude a sense of warmth and history. Many of these Colonial gems have been meticulously maintained or thoughtfully updated, blending modern comforts with traditional elegance. Inside, you’ll find spacious layouts, grand fireplaces, and beautiful hardwood floors, making them perfect for both entertaining and everyday living.

Living in Chestnut Hill means enjoying a strong sense of community, with top-rated schools, boutique shopping, and delectable dining options just minutes away. The area is also conveniently located near public transportation, providing easy access to downtown Boston and beyond. Whether you’re looking for a serene retreat or a vibrant lifestyle, Chestnut Hill offers the best of both worlds. Explore the charm of this remarkable neighborhood and discover your dream Colonial home today!

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

Listing courtesy of Listing Agent: Ingvild Brown from Listing Office: Keller Williams Realty.

$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.

$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

Listing courtesy of Listing Agent: Hilary Maddox Team from Listing Office: Compass.

$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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