Chestnut Hill Homes for Sale

Welcome to Chestnut Hill, Massachusetts, a picturesque suburb that perfectly blends the charm of New England with modern amenities. Nestled just six miles west of downtown Boston, Chestnut Hill is renowned for its lush greenery, elegant homes, and vibrant community spirit. The area boasts a rich history, with stunning architecture that ranges from stately Colonial homes to contemporary masterpieces, all set against the backdrop of scenic landscapes and well-manicured gardens.

Chestnut Hill is not just a beautiful place to live; it also offers an exceptional quality of life. Residents enjoy access to top-rated schools, boutique shopping, and a variety of dining options that cater to every palate. The nearby Chestnut Hill Reservoir provides ample opportunities for outdoor activities, including walking, jogging, and picnicking, making it a favorite spot for families and fitness enthusiasts alike.

For those looking to make Chestnut Hill their home, the real estate market is thriving. From charming single-family houses to luxurious estates, there’s a diverse range of homes for sale that cater to various lifestyles and budgets. Whether you’re a first-time buyer or seeking a spacious family home, Chestnut Hill has something for everyone.

With its welcoming community, excellent amenities, and stunning homes, Chestnut Hill is truly a hidden gem in Massachusetts. Explore the available listings today and discover why this enchanting suburb is the perfect place to call home!

Newest Chestnut Hill Homes for Sale

$1,995,000

5 Beds ⋅ 5 Baths ⋅ 73600221 MLS

A rare opportunity to own an architecturally significant Arts and Crafts residence in one of Brookline’s most sought-after neighborhoods. Set on three-quarters of an acre within the Chestnut Hill North Historic District, 91 Spooner Road is a distinctive five-bedroom, four-and-a-half-bath residence designed by the renowned architectural firm Putnam & Cox–built as William Putnam’s personal residence. The home was designed around a distinctive interior courtyard and was featured in American Country Houses of Today 1912, underscoring its architectural significance. Dramatically sited atop a high ledge, the property overlooks a wooded landscape to the east, with a rustic path descending toward the street to the north. Cherished by the same family for 60 years, the home showcases thoughtful design, generous proportions, abundant architectural detail, and three fireplaces. The interior courtyard, with screen doors and columns on three sides, brings natural light to the residence. Notable features include a gracious front-to-back entry gallery with brick floors and a sitting alcove; a formal living room with tall ceilings and a striking fireplace with a tiled surround; and a concealed, full-height built-in safe. Additional architectural highlights include a fireplace office or studio with loft, a tree-top sleeping porch with wraparound windows, expansive attic spaces, and separate guest quarters with a full bath. Two pantries, meandering walkways, copper gutters and downspouts, a private terrace, and a whole-house generator further distinguish this exceptional property. Offering an extraordinary opportunity for comprehensive renovation, this property combines architectural provenance, substantial grounds, privacy, and a remarkable natural setting. For those who appreciate historic architecture and envision restoring a residence of enduring character, the possibilities are exceptional. Conveniently located near the Green Line, Route 9, the shops and restaurants at The Street at Chestnut Hill, Roland Hayes Elementary, Brimmer and May, and the Chestnut Hill Schools.

91 Spooner Road, Brookline

Listing courtesy of Listing Agent: Todd Movsessian from Listing Office: Barrett Sotheby's International Realty.

$3,200,000

6 Beds ⋅ 6 Baths ⋅ 73599514 MLS

Looking for the perfect place to call home this holiday season? You've just found it! Welcome to an exceptional new construction residence in the heart of Chestnut Hill, where timeless elegance meets modern luxury. Thoughtfully designed with nearly 5,000 sq. ft. of living space, this stunning home showcases exquisite millwork, soaring ceilings, white oak floors, and beautifully curated finishes throughout. An elegant dining room sets the stage for memorable gatherings, while the sun-filled living room features a striking fireplace and sophisticated architectural detailing. The chef's kitchen impresses with custom cabinetry, premium FORNO Espresso appliances, an oversized stone island, and seamless flow into an inviting family room with a contemporary fireplace. A private first-floor office with its own bathroom offers the perfect work-from-home retreat. Featuring 6 bedrooms, 5.5 baths, and a two-car garage, this residence offers exceptional versatility. Ideally situated just off Route 9, minutes from the Longwood Medical Area, with convenient access to the Route 60 bus and Longwood shuttle connections. Enjoy proximity to Life Time Fitness, Chestnut Hill Mall (0.4 mi), Newton Centre T Station (1.2 mi), Hammond Pond Reservation (1.3 mi), and Crystal Lake (1.8 mi). An exceptional combination of luxury, location, and lifestyle. Your next chapter begins here!

67 Moody St, Newton

Listing courtesy of Listing Agent: Katya Malakhova from Listing Office: William Raveis R. E. & Home Services.

$1,379,000

3 Beds ⋅ 2 Baths ⋅ 73597241 MLS

Location, lifestyle & versatility await in Brookline's coveted Fisher Hill neighborhood! This charming 3-bed, 2-bath multi-level home offers the perfect blend of comfort, convenience & endless possibilities! Featuring a thoughtful layout, gleaming hardwood floors, an abundance of natural light & flexible living spaces, this home is designed to accommodate a variety of lifestyles. Recent updates include fresh interior & exterior paint, upgraded light fixtures, a brand-new induction range & more! Enjoy the privacy of a fenced-in backyard, perfect for outdoor entertaining, gardening or simply unwinding, plus the convenience of an attached one-car garage. Nestled in one of Greater Boston's most desirable communities, this home is just minutes from Boston College, The Shops at Chestnut Hill, Brookline Reservoir & the Green Line at Cleveland Circle, offering unparalleled access to shopping, dining, recreation & Boston. With Brookline's highly rated schools and an unbeatable location, this move-in-ready gem is ready for its next chapter. Bring your vision and make this special property your own!

622 Chestnut Hill Ave, Brookline

Listing courtesy of Listing Agent: The Dovetail Group from Listing Office: eXp Realty LLC - Corporate Office.

$849,900

3 Beds ⋅ 1 Baths ⋅ 73594577 MLS

Entering Brookline! Welcome home! Lovely entryway with closet welcomes you into fire placed, sunlit living room with mellow hardwood floors that opens to ample dining room perfect for holiday entertaining. Three season sunroom and fully applianced kitchen round out the first floor. Direct entry garage is a bonus! Second level offers 2 generous bedrooms and a smaller nursery or office and full bath. Basement is partially finished for bonus space! Situated on a lovely fenced lot. Bring your ideas and pack your bags. There is so much potential with this property. Excellent location, Baker school district. Best value in Chestnut Hill! Don't miss! Offers, if any, due Tuesday at noon!

77 Payson Rd, Brookline

Listing courtesy of Listing Agent: Patsy Brennan from Listing Office: Vogt Realty Group, LLC.

$2,799,999

4 Beds ⋅ 4 Baths ⋅ 73592951 MLS

Tucked away on a quiet Chestnut Hill street, this 1927 classic Tudor is filled with warmth, character, and thoughtful modern updates. With 4 bedrooms, 3.5 bathrooms, central air conditioning, a dedicated playroom, and an attached two-car garage, the home offers plenty of space and everyday practicality without sacrificing personality. A welcoming foyer leads to the formal open living and dining room, while the updated chef’s kitchen connects seamlessly to the family room, creating an easy layout for modern living. A sunny breakfast room provides the perfect spot for casual meals, and just beyond the family room, a deck overlooks the beautifully landscaped backyard, extending the living space outdoors. Upstairs, the primary bedroom is joined by two additional bedrooms, two full bathrooms, and generous storage. The lower level includes a fourth bedroom, laundry room, additional storage, another full bathroom, and direct access to the two-car garage. Fabulous Chestnut Hill location close to the shops and restaurants at The Street at Chestnut Hill, convenient access to Route 9 and just half a mile from the Green Line "T".

79 Randolph Road, Brookline

Listing courtesy of Listing Agent: Jeffrey Hamilton from Listing Office: Columbus and Over Group, LLC.

$925,000

3 Beds ⋅ 2 Baths ⋅ 73590431 MLS

Charming Colonial in a Coveted Brookline Location! Situated in an excellent neighborhood just a stone’s throw from Allandale Farm, Larz Anderson Park and Brookline's top-rated schools, this 3-bedroom, 1.5-bath Garrison Colonial presents a wonderful opportunity to create your dream home. The property features hardwood floors throughout, garage parking with direct access to the home and a generous lot of over 7,500 square feet. In need of updating, this home offers tremendous potential for renovation, personalization and long-term value in a highly desirable location. A rare opportunity to bring your vision to life in one of Brookline’s sought-after neighborhoods, close to parks, local amenities, hospitals and excellent educational opportunities.

30 Hackensack Road, Brookline

Listing courtesy of Listing Agent: DelRose McShane Team from Listing Office: Coldwell Banker Realty - Belmont.

$7,995,000

8 Beds ⋅ 9 Baths ⋅ 73590108 MLS

334 Hammond Street presents a rare opportunity to own a distinguished Georgian Revival residence, lovingly maintained and thoughtfully evolved by the same family for the past 25 YEARS. Set back from the road behind its classic brick façade, this circa-1900 home is remarkably understated from the street, revealing an unexpected sense of scale and versatility within. Generously proportioned rooms, beautifully preserved architectural character, and restored Palladian windows speak to the home’s history, while thoughtful updates and a more contemporary rear addition reflect the way it has evolved for modern living. With 8 bedrooms, expansive gathering spaces, and a finished lower level complete with an in-law suite, the floor plan offers exceptional flexibility for family, guests, work, and entertaining. One of the property’s most distinctive features is the detached indoor swimming pool, creating a private retreat that can be enjoyed in every season. Carefully cared for through the years, 334 Hammond Street offers the character and presence of a historic Newton home together with the space and adaptability to serve its next generation for years to come!

334 Hammond St, Newton

Listing courtesy of Listing Agent: The Sarkis Team from Listing Office: Douglas Elliman Real Estate - The Sarkis Team.

$2,990,000

5 Beds ⋅ 7 Baths ⋅ 73581626 MLS

Exceptional in scale, craftsmanship & setting, this beautifully constructed 2013 Chestnut Hill home offers 3 gracious levels of living on a substantial lot in a coveted, tranquil cul-de-sac location, combining classic architectural details with sophisticated modern amenities. High ceilings (tray & coffered), wainscoting, crown molding, hardwood floors with distinctive inlay, custom built-ins+ and 3 fireplaces underscore the home’s refined character. Generously proportioned custom windows throughout all 3 levels fill the home with abundant natural light. A dramatic foyer entrance sets the tone with its grand staircase & statement chandelier that opens to the 2nd floor, while French doors introduce the elegant open living & dining room space with gas fireplace. The chef’s kitchen features high-end stainless steel appliances, sleek counters, tile backsplash & generous island with prep sink, wine fridge & microwave. A window-lined dining area flows seamlessly to generous family room with coffered ceiling, cozy fireplace, wainscoting & oversized doors to deck & beautiful rear grounds. A 1st-floor en suite bedroom offers flexibility for guests, office or multi-generational living. Upstairs, the primary suite is a welcome retreat with its gas fireplace, oversized walk-in closet & spa-like bath with soaking tub, large tiled shower, dual vanity & private water closet. The 3 additional bedrooms are each en suite, complemented by a convenient 2nd-floor laundry. The lower level is a destination of its own, with an oversized game room with fully equipped wet bar & golf simulator. Plus, you’ll also enjoy a gym, bonus room & full bath on this level. Golf enthusiasts can take their game outdoors to the private putting green in the generous backyard that also offers its nicely-sized deck, covered patio area & added space to relax & enjoy the serenity of your surroundings. A heated 2-car garage & semicircular paver drive complete this remarkable property, offering exceptional living inside & out in one of Chestnut Hill’s most sought-after locations.

80 High Rock Ter, Newton

Listing courtesy of Listing Agent: Sissi Zhang from Listing Office: REMAX Andrew Realty Services.

$4,980,000

5 Beds ⋅ 7 Baths ⋅ 73579970 MLS

Welcome to 90 Suffolk Road, a truly special Chestnut Hill residence where classic architecture, beautiful proportions, and a warm, welcoming feel come together on approximately one private acre. From the moment you arrive, there is a sense of space, privacy, and timeless elegance that makes this house feel like home. Sunlight fills the gracious main level, where generously sized rooms flow naturally from one to the next. The spacious cooks kitchen is made for gathering, while the elegant living and dining rooms provide the perfect setting for entertaining. A fireplaced den or office offers a cozy retreat, and the living room fireplace adds warmth and character. A beautifully appointed in-law suite with full bath provides exceptional flexibility for guests or extended family visits. A wraparound deck overlooks the expansive grounds. Upstairs, the primary suite is a peaceful retreat, with a spa-like bath, two custom walk-in closets, and beautiful views across the property. Three additional spacious bedrooms and 2 bathrooms complete the second level. The walk-out lower level adds another dimension to the home, with a comfortable family room, playroom, and bonus office space. The grounds are magical—private and lush, and offering a rare sense of space in one of Chestnut Hill's most sought-after neighborhoods. Close proximity to Boston, public transportation, major hospitals, schools, and shopping.

90 Suffolk Rd, Newton

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

$2,495,000

4 Beds ⋅ 5 Baths ⋅ 73578296 MLS

Majestic Tudor style home in Newton’s highly desirable Chestnut Hill neighborhood! This property boasts architectural details, an abundance of character & timeless charm through its high ceilings, hardwood floors, beautiful moldings and built ins. Enter into an open & airy front foyer with a dramatic center staircase. Resume the tour through a sunken living room boasting coffered ceilings & a gorgeous fireplace, then to the family room w/custom cabinets, dining room with built in window seating & large picturesque windows, a large remodeled EIK with a generous amount of cabinets/counter space and a full bath. The second floor flaunts an open office space, laundry, 2 full bathrooms & 4 generous size bedrooms(one primary suite). The walk up third floor has a gigantic rec room w/ gas fireplace & full bathroom. Basement includes 3 more finished rooms, a half bath & direct access to the garage. Enjoy the outdoors on a large back deck, with great yard space and mature landscaping.

79 Woodchester Dr, Newton

Listing courtesy of Listing Agent: Jarrod L. Pescosolido from Listing Office: Romo Realty Group.

$2,250,000

3 Beds ⋅ 4 Baths ⋅ 73574038 MLS

Rarely available fully renovated end-unit 3 bed+office / 3.5 bath townhouse at The Residences at Chestnut Hill offers an enviable combination of privacy, space and convenience. Set back from Boylston Street and abutting a tranquil conservation area, this beautifully appointed residence has been thoughtfully renovated offering an abundance of natural light and features generous proportions, including a magnificently renovated kitchen and beautifully updated bathrooms. The main living level boasts 9’ ceilings, a convenient powder room and a chef’s dream kitchen with a center island, custom cabinetry and a charming bay-windowed eat-in area. The kitchen flows seamlessly into a spacious living room anchored by a gas fireplace and custom built-ins, a dining area and a sliding door opening to a private deck overlooking the landscaped side yard. The second floor is comprised of a spacious primary suite with two walk-in closets, in-unit washer/dryer and a luxurious en-suite bath featuring a double vanity, walk-in shower and separate soaking tub with skylight overhead. An oversized guest bedroom with an adjacent full bathroom completes the second floor. The finished lower level offers flexibility with an additional bedroom, full bathroom and a separate office/den area. Additional highlights include a 2-car attached garage, mudroom area, 20’ grand foyer entry, central air, recessed lighting throughout and access to the association's fitness center. Ideally located near an abundance of shopping/restaurants at Chestnut Hill Square/Wegmans, The Shops at Chestnut Hill, The Street and just steps from Lifetime Fitness and the trails of Lost Pond Reservation, this exceptional residence offers effortless suburban living just minutes from Boston. **** Set back from Route 9 at the end of a private cul-de-sac and abutting conservation land. Don't be fooled by the address! ****

344 Boylston Street Unit A, Newton

Listing courtesy of Listing Agent: Neda Vander Stoep from Listing Office: Coldwell Banker Realty - Boston.

$3,695,000

4 Beds ⋅ 5 Baths ⋅ 73573585 MLS

Welcome to this stunning center-entrance Colonial in Brookline's Chestnut Hill estate area, set on a level half-acre lot. This expansive home features 4+ bedrooms, 4 full and 1 half baths & offers over 4,895 square feet across three finished levels. The foyer opens to a fireplaced living room and a formal dining room that seats 12. The Chef’s kitchen features a Wolf range, Sub-Zero refrigerator, double wall ovens including steam, Cove dishwashers, two sinks, custom cabinetry & granite counters. A library with built-ins cabinetry sits off the dining room & kithcen. The family room, with gas fireplace opens through French doors to a bluestone patio and a broad, fenced, level yard. Upstairs, the primary suite includes a private balcony, Carrara marble bath, dressing area, and two walk-in closets. Three additional bedrooms and two full baths & laundry complete the floor. The lower level consists of a media/playroom, gym, wet bar, beautiful full bath with glass enclosed shower + another set of laundry. Central air & Sonos throughout, EV charging & 2-car garage. Close proximity to the D Line at Chestnut Hill, shops and restaurants at The Street at Chestnut Hill, Soule Playground, and Dane Park.

17 Glenoe Rd, Brookline

Listing courtesy of Listing Agent: Jamie Genser from Listing Office: Coldwell Banker Realty - Brookline.

Start Your Search

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

Chestnut Hill Homes for Sale

Newest Chestnut Hill Homes for Sale

How much is your home worth?

How much is your home worth?