Chestnut Hill Homes for Sale

Welcome to Chestnut Hill, Massachusetts, a picturesque community that seamlessly blends 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, stunning parks, and a rich tapestry of history, this region offers a perfect backdrop for families, professionals, and retirees alike.

One of the hallmarks of Chestnut Hill is its diverse range of homes for sale. From stately colonial mansions to modern townhouses and cozy bungalows, the real estate options here cater to a variety of tastes and lifestyles. Many properties boast expansive yards, elegant architectural details, and proximity to top-rated schools, making it an ideal choice for families seeking both comfort and community. The local market is competitive, reflecting the high demand for this desirable area, but there are always hidden gems waiting to be discovered.

Beyond the homes, Chestnut Hill offers an array of amenities that enhance the quality of life for its residents. Enjoy leisurely strolls through the scenic Chestnut Hill Reservoir, indulge in shopping at the upscale boutiques in the Chestnut Hill Square, or savor a meal at one of the many charming eateries. With easy access to public transportation and major highways, commuting to Boston or exploring the surrounding areas is a breeze.

Whether you’re looking to buy your first home, downsize, or invest in a property, Chestnut Hill is a community that promises not just a house, but a place to call home. Explore the homes for sale today and discover the enchanting lifestyle that awaits you in this delightful Massachusetts enclave!

Newest Chestnut Hill Homes for Sale

$2,850,000

6 Beds ⋅ 4 Baths ⋅ 73558881 MLS

Discover timeless elegance and exceptional versatility in this beautifully updated 1938 Cape, thoughtfully designed for today's discerning family. Offering 6 bedrooms and 3.5 baths, the home features two primary bedrooms with private ensuite baths, including a sought-after first-floor retreat ideal for multigenerational living, guests, or an au pair. The chef's kitchen is appointed with stainless steel appliances, a gas range, wall oven, stone countertops, and a center island with seating for three. A welcoming den, formal dining room, and sun-filled breakfast area provide inviting settings for both everyday life and elegant entertaining. The finished lower level offers a versatile recreation room with a dedicated laundry area. Completing the home are an attached two-car garage and two additional off-street parking spaces, blending classic New England charm with modern comfort and convenience. Close to Roland Hayes School & Brookline High School, Route 9, Chestnut Hill Reservoir, Golf Courses, Green Line (MBTA) and The Mall at Chestnut Hill. Quick drives to Newton Centre or Brookline hubs for everyday groceries and dining.

44 Valley Rd, Brookline

Listing courtesy of Listing Agent: The Kelleher Spalding Team from Listing Office: Gibson Sotheby's International Realty.

$1,999,000

4 Beds ⋅ 3 Baths ⋅ 73552349 MLS

Chestnut Hill - Baker School neighborhood. This 9-room brick Tudor pairs classic architectural charm with 3,123 square feet of updated living space, offering 4 bedrooms, 2.5 bathrooms on three levels. A beautifully updated eat-in kitchen, gracious living room with ornate fireplace and dining room set the stage for elegant entertaining. A first floor great room with vaulted ceiling opens to a 31'x19' patio and private backyard. Handsome masonry work throughout the beautifully landscaped outdoor spaces. The finished lower level features a family room with fireplace and stone surround. Direct access garage parking. A prime location near Chestnut Hill shopping and dining. Easy access to Cambridge, Boston, area hospitals and universities.

142 Beverly Rd., Brookline

Listing courtesy of Listing Agent: Friedler / Marchant Living Group from Listing Office: Hammond Residential Real Estate.

$1,995,000

4 Beds ⋅ 3 Baths ⋅ 73549795 MLS

Fantastic move-in-ready 4 bedroom, 2.5 bathroom in Chestnut Hill. Set on a 15,000+ level private lot, 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 hardwood floors throughout, a fireplaced living room, lovely dining room, stainless and granite 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.

$2,399,000

4 Beds ⋅ 3 Baths ⋅ 73547641 MLS

Prepare to be impressed by this beautifully renovated 4 Bed 3 Bath mid-century modern ranch in Chestnut Hill Brookline on the edge of the golf course! Set on over a half acre of beautiful landscaping surrounding the flat back yard lead to the golf course. Breathtaking renovations highlight modern living with soaring exposed beam ceilings, a dramatic living room with a wood-burning fireplace, and a wall of windows overlooking the screened porch, deck, and tranquil Japanese rock garden. The renovated kitchen features sleek cabinetry, updated countertops, appliances, a peninsula, pantry, and eat-in area. The main level offers three spacious bedrooms, including a large primary suite, while the finished walkout lower level includes a great room with kitchenette, fourth bedroom, full bath, studio, bonus room, patio access, and abundant storage. Perfect location with quick access to 9 & I-93 and a quick hop to local restaurants, shopping, Wegman's, and much more!

365 Newton St, Brookline

Listing courtesy of Listing Agent: Rose Hall from Listing Office: Blue Ocean Realty, LLC.

$3,299,999

4 Beds ⋅ 4 Baths ⋅ 73543931 MLS

An architectural masterpiece, this stunning custom-built contemporary home showcases modern design at its finest. Featuring soaring ceilings, an open-concept layout, and gallery-style lighting, the home is filled with natural light from expansive walls of windows offering breathtaking views. The gourmet kitchen is equipped with Miele appliances, perfect for both everyday living and entertaining. A fireplaced library on the main level provides a warm and inviting retreat. Enjoy spectacular sunsets from the sunroom or the private second-story balcony off the luxurious primary suite. The finished walk-out lower level offers exceptional additional space, featuring a dedicated gym area, a spacious game room, multiple bonus rooms that can be used as guest rooms, or office spaces, and abundant storage throughout. Step outside to a beautifully landscaped outdoor retreat with exterior stairs leading to a serene, courtyard garden, creating a peaceful setting for relaxation or entertaining.

28 Kesseler Way, Newton

Listing courtesy of Listing Agent: Xianbin Yin from Listing Office: Harmony Hill Realty LLC.

$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.

$3,399,000

9 Beds ⋅ 7 Baths ⋅ 73527701 MLS

Brookline’s prestigious Chestnut Hill neighborhood and within one of the town’s top-rated school districts, this 1899 estate seamlessly combines timeless architecture with a full modern renovation. The home offers 6,292 square feet of refined living space across three finished levels, featuring nine bedrooms, four full and three half baths, and two well-appointed kitchens ideal for entertaining or multi-generational living. Newly updated interiors blend classic charm with contemporary finishes, while balconies overlook beautifully landscaped grounds that provide exceptional privacy. A rare opportunity to own a historic Brookline residence perfectly renewed for today’s lifestyle.

476 Heath Street, Brookline

Listing courtesy of Listing Agent: Andrew Haddad from Listing Office: Northeast Development & Investment, Inc..

$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.

$2,749,999

5 Beds ⋅ 6 Baths ⋅ 73523918 MLS

Luxury Living in Chestnut Hill, Brookline. Spacious 5-bedroom home designed for extended families, aging parents, or long-term guests. Four bedrooms feature private en suite bathrooms, offering comfort and privacy throughout. Two bedrooms are conveniently located on the main level, while two upstairs bedrooms feature skylights filled with natural light. An additional lower-level bedroom creates flexible living options. Enjoy a warm family room with a fireplace, plus a finished lower level complete with a second fireplace, a kitchenette, and flexible space perfect for a family room, theater room, game room, or private guest retreat. Step outside to your private inground pool and enjoy peaceful surroundings near the renowned Brookline Golf Course. Complete with a 2-car garage and close proximity to Boston, medical centers, shopping, dining, and major routes, this home blends luxury, flexibility, convenience, and multigenerational living in the heart of Chestnut Hill.

171 Shaw Rd, Brookline

Listing courtesy of Listing Agent: Melvin A. Vieira Jr. from Listing Office: RE/MAX Real Estate Center.

$4,998,500

4 Beds ⋅ 5 Baths ⋅ 73520842 MLS

Nestled on a private 0.92-acre lot in the prestigious Chestnut Hill neighborhood, this exceptional custom-designed Mid-Century Modern ranch, inspired by the timeless architecture of Frank Lloyd Wright, offers a rare blend of sophistication, privacy, and seamless indoor-outdoor living. Thoughtfully designed with gracious proportions and walls of glass, the home is filled with natural light and overlooks beautifully landscaped grounds. A spectacular four-season breakfast room with four skylights complements the chef’s kitchen featuring top-of-the-line appliances, three ovens, two dishwashers, and custom cabinetry. The luxurious primary suite serves as a private sanctuary with dual showers and vanities, smart toilets, separate dressing areas, a soaking tub, and an attached office/library. The versatile lower level offers excellent potential for an in-law suite. Sliding glass doors line the rear of the home, opening to a serene outdoor retreat with an elegant patio and heated pool. Superb

9 Singletree Rd, Brookline

Listing courtesy of Listing Agent: Deborah M. Gordon from Listing Office: Coldwell Banker Realty - 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

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

$6,400,000

4 Beds ⋅ 5 Baths ⋅ 73500458 MLS

A magnificent home located in the highly coveted estate section of Brookline directly across from the famed Country Club. 198 Clyde Street is a wonderful cape style estate perfectly adapted to modern living. The property offers 6,521 square feet of living space located on just under 1 acre of impeccably landscaped grounds. Beautifully appointed interiors include grand formal living and dining rooms overlooking the outdoor space, a gourmet kitchen, and a spectacular family room with double-height ceilings. The luxurious primary suite is complete with separate dressing rooms and bathrooms and direct access to an outdoor sitting area. The exterior is as wonderful as the interior with multiple outdoor patios, a sprawling lawn and a pergola. Additional features include a 2-car garage, laundry room, home office, wine cellar, wood paneled den and a custom hockey training area. This outstanding home is minutes from Larz Anderson, Dexter/Southfield, Park School, and The Street at Chestnut Hill.

198 Clyde Street, Brookline

Listing courtesy of Listing Agent: Tracy Campion from Listing Office: Campion & Company Fine Homes Real Estate.

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