Chestnut Hill Homes for Sale

Chestnut Hill Homes for Sale

Welcome to Chestnut Hill, a picturesque and vibrant region located in Massachusetts. Known for its leafy streets, upscale shopping, and beautiful homes, Chestnut Hill offers a perfect blend of urban convenience and suburban tranquility.

If you are looking for homes for sale in Chestnut Hill, you are in for a treat. This charming neighborhood boasts a variety of real estate options, from cozy single-family homes to luxurious estates. Whether you are a first-time homebuyer or looking to upgrade to your dream home, Chestnut Hill has something for everyone.

With its top-rated schools, proximity to Boston, and abundance of green spaces, Chestnut Hill is a popular choice for families and professionals alike. Imagine starting your day with a peaceful stroll through the Chestnut Hill Reservoir or enjoying a leisurely afternoon shopping at The Street, Chestnut Hill's premier shopping destination.

Don't miss the opportunity to make Chestnut Hill your home. Explore the homes for sale in this desirable region and discover why so many people are proud to call Chestnut Hill their home.

Newest Chestnut Hill Homes for Sale

101 Hackensack Road, Brookline
$1,549,000
4 Beds ⋅ 4 Baths ⋅ 73595643 MLS
Situated in prestigious Chestnut Hill along the Brookline line, this exceptional location offers convenient access to some of the area’s most sought-after private schools, including Dexter Southfield, The Park School, The British International School of Boston, Beaver Country Day, and Brimmer & May. Enjoy the advantages of this coveted neighborhood, including Boston’s comparatively favorable property taxes, proximity to the renowned Longwood Medical Area, Brigham and Women’s Faulkner Hospital just down the street, and easy access to some of the country’s most prestigious universities. This fully renovated, sprawling ranch-style home lives like new construction, blending modern luxury with a super contemporary flare. Perfect for families looking for proximity to the Dexter School, Park School, The British School, Beaver Country Day and Brimmer & May School. The home features four bedrooms, plus a dedicated gym and sauna. The stylish kitchen showcases stainless steel appliances, sleek finishes, and an open-concept layout flowing seamlessly into the living room, anchored by a striking Frank Lloyd Wright-inspired fireplace.Three generously sized bedrooms feature custom built-ins, complemented by an expansive laundry room and a beautifully appointed bathroom with a double vanity. The private primary suite offers a luxurious retreat with a private bathroom including solid stone surround, glass enclosed shower with jets and soaking tub complimented by contemporary style fixtures with a custom walk-in closet.The finished lower level adds exceptional versatility, with heated floors throughout, a full bathroom & bedroom, additional space for recreation, fitness, spa like treatment in your indoor built-in sauna and a massive addtional living space perfect for an entertainment area. Outside, enjoy a private patio and abundant green space on a desirable corner lot, along with a spacious two-car garage and an irrigation system. A rare opportunity to enjoy the feel of new construction in one of Boston’s most sought after, highly desirable neighborhoods.

101 Hackensack Road, Brookline

Listing courtesy of Listing Agent: Steven Musto from Listing Office: Insight Realty Group, Inc..
77 Payson Rd, Brookline
$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.
79 Randolph Road, Brookline
$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.
30 Hackensack Road, Brookline
$995,000
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. Offers, if any, to be reviewed on Monday, 10/19 by 2pm.

30 Hackensack Road, Brookline

Listing courtesy of Listing Agent: DelRose McShane Team from Listing Office: Coldwell Banker Realty - Belmont.
334 Hammond St, Newton
$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.
80 High Rock Ter, Newton
$3,150,000
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.
90 Suffolk Rd, Newton
$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.
79 Woodchester Dr, Newton
$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.
344 Boylston Street Unit A, Newton
$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.
17 Glenoe Rd, Brookline
$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.
284 Woodland Road, Brookline
$2,595,000
5 Beds ⋅ 5 Baths ⋅ 73573502 MLS
ABSOLUTELY INCREDIBLE OPPORTUNITY AT THIS PRICE!!!!!! A rare combination of character, space, and setting in Chestnut Hill, this beautifully maintained Cape sits on a scenic half-acre with approximately 3,900 SF, 5 bedrooms, and 4.5 baths. Enter into a home filled with classic period details, wide-plank floors, and abundant south-facing light. The gracious living room welcomes with a fireplace and French doors opening to the patio, while the spacious family room features custom built-ins. At the heart of the home, an updated eat-in kitchen flows into a comfortable sitting area and opens directly to the backyard. A convenient mudroom leads to the driveway and two-car garage.Upstairs, the sun-filled primary suite offers an en-suite bath and private balcony, joined by four additional bedrooms, including a second primary, a study, and three full baths. Private guest quarters with separate stair access add flexibility. The lower level offers laundry, recreation space, and storage. Step outside to discover a pool surrounded by mature landscaping, a spacious patio, and peaceful grounds that create a private oasis.Set along beautiful Woodland Road, a leafy, tree-lined neighborhood with a welcoming community atmosphere, the setting is ideal for walking and running beneath towering oaks and mature trees. Dane Park, a wooded town park with trails, is within walking distance, while Wegmans, The Shoppes at Chestnut Hill, SuperLux, and an array of shops and restaurants are just minutes away. Convenient access to major routes also makes commuting easy, including a direct surface-road connection to Cambridge. With its distinctive character, generous scale, flexible layout, and exceptional outdoor setting, this is a property that truly needs to be experienced in person.

284 Woodland Road, Brookline

Listing courtesy of Listing Agent: The Denman Group from Listing Office: eXp Realty LLC.
401 Heath Street, Brookline
$2,765,000
5 Beds ⋅ 4 Baths ⋅ 73572599 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.
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