Chestnut Hill Homes for Sale

Chestnut Hill Homes for Sale

Welcome to Chestnut Hill, Massachusetts—a picturesque neighborhood that perfectly blends suburban charm with urban convenience. Nestled just six miles west of downtown Boston, Chestnut Hill is renowned for its lush landscapes, historic architecture, and vibrant community spirit. This idyllic area is characterized by its tree-lined streets, stunning parks, and a rich cultural heritage that makes it a sought-after destination for families, professionals, and retirees alike.

Chestnut Hill boasts a unique array of homes for sale, each with its own character and charm. From elegant single-family residences to modern townhomes, there’s something to suit every taste and lifestyle. Many properties feature spacious yards, perfect for outdoor gatherings, while others offer breathtaking views of the surrounding hills and gardens. The architectural styles range from classic colonial to contemporary designs, ensuring that you’ll find a home that resonates with your personal aesthetic.

In addition to its beautiful homes, Chestnut Hill is conveniently located near top-rated schools, shopping centers, and recreational facilities. Residents enjoy easy access to the Chestnut Hill Reservoir, a popular spot for walking, jogging, and enjoying nature. The nearby Mall at Chestnut Hill offers a variety of shopping and dining options, while the local farmers' market provides fresh produce and artisanal goods.

Whether you’re looking to settle down or invest, Chestnut Hill offers a vibrant community with a welcoming atmosphere. Explore the homes for sale in this enchanting neighborhood and discover the perfect place to call home!

Newest Chestnut Hill Homes for Sale

$3,349,000
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.
$3,995,000
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.
$3,100,000
5 Beds ⋅ 5 Baths ⋅ 73573502 MLS
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.
$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.
$1,790,000
4 Beds ⋅ 3 Baths ⋅ 73572511 MLS
Captivating colonial tastefully designed for elegant entertaining and comfort in mind. Privacy + nature abound in this 4 bedrooms, 3 bathrooms + 2450 square feet of refined living space in a premier Chestnut Hill location. Near Baker Elementary school (grades K-8) + close proximity to Putterham Shops, tennis, golf, wildlife sanctuary, Longwood Medical Area, Arnold Arboretum + Jamaica Pond. First floor has living room with wood burning fireplace, family room, bedroom with full bath + access to expansive outdoor deck. In the heart of the residence is a beautifully renovated kitchen with custom white shaker cabinets, sleek black granite countertops, stainless steel appliances + generous center island. Upper level has a sprawling primary bedroom suite complimented by majestic sunset views + an abundance of attributes such as walk-in closet, separate sitting area + spa-like bath with dual sink vanity, glass enclosed shower + soaking tub/jacuzzi. Additional finished lower level provides versatile space for a fitness gym, home theatre or home office to meet today's evolving lifestyle needs. One car garage, one carport + plenty of additional driveway parking make this an ideal residence to call home.

133 Wolcott Road, Brookline

Listing courtesy of Listing Agent: Mary Lochner from Listing Office: Coldwell Banker Realty - Brookline.
$2,395,000
4 Beds ⋅ 5 Baths ⋅ 73569446 MLS
Set along one of Chestnut Hill’s picturesque tree-lined streets, this handsome brick Tudor offers a thoughtful blend of classic architecture, generous proportions & comfortable everyday living. A welcoming foyer introduces elegant living & dining rooms with hardwood floors & distinctive period details, while the spacious eat-in kitchen, with abundant cabinetry, updated appliances & wet bar, opens naturally to a relaxed family room with direct access to the backyard. Upstairs, four well-proportioned bedrooms include a generous primary suite overlooking the backyard, complete with a sizable walk-in closet & ensuite bath. A second ensuite bedroom, along with two additional bedrooms, provides flexibility for family, guests or a home office. The lower level offers versatile space for recreation, hobbies, storage or future expansion, with convenient access to the garage. Outdoors, a tiered backyard creates a private setting with a pool, deck & lawn, offering multiple spaces for entertaining, relaxing & enjoying the warmer months. Fresh paint, new and refreshed flooring & an updated back deck enhance the home’s appeal while preserving its distinctive character. Ideally situated in the Baker School District, with easy access to Route 9, shopping, dining & the amenities of Chestnut Hill, this is a home with both an inviting sense of place & room to make it your own.

72 Beverly Rd, Brookline

Listing courtesy of Listing Agent: Ovesen Group from Listing Office: Coldwell Banker Realty - Brookline.
$3,999,999
6 Beds ⋅ 6 Baths ⋅ 73568425 MLS
Tucked at the end of a desirable cul-de-sac in Chestnut Hill, this classic shingle-style residence offers four beautifully finished levels of living with a timeless traditional design. Hardwood floors, gracious room proportions, and a warm, inviting floor plan create a home equally suited for everyday living and entertaining.Featuring 6 bedrooms and 6 full bathrooms, the residence offers exceptional flexibility for family, guests, home offices, and additional living spaces. The finished walk-out lower level adds another dimension of usable space with direct access outdoors, while the three-car garage provides both convenience and ample storage.Beautifully landscaped grounds enhance the home’s curb appeal and sense of privacy, with the property set on approximately 25,000 square feet of land. Combining substantial living space, classic New England architecture, and a sought-after Chestnut Hill cul-de-sac location, this is a special opportunity to enjoy comfort, scale, and timeless character.

31 Kesseler Way, Newton

Listing courtesy of Listing Agent: Samantha Stumpo from Listing Office: Serhant.
$1,790,000
4 Beds ⋅ 3 Baths ⋅ 73549795 MLS
$200,000 PRICE REDUCTION!! Fantastic move-in-ready 4 bedroom, 2.5 bathroom in BROOKLINE. Set on a 15,000+ level private lot, LEAD FREE, perfect for INVESTOR or END USER, 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 hardwoods, a fireplaced living room, lovely dining room, 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.
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