Chestnut Hill Real Estate

Welcome to Chestnut Hill, Massachusetts – a charming and 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 architecture, and vibrant community spirit.

This idyllic neighborhood is characterized by its stunning tree-lined streets, offering a serene environment that appeals to families, professionals, and retirees alike. With a rich history dating back to the 19th century, Chestnut Hill boasts a collection of beautiful homes, from stately mansions to cozy bungalows, each with its own unique charm.

One of the area's standout features is its commitment to green spaces. The Chestnut Hill Reservation, a part of the Metropolitan Park System, provides residents with ample opportunities for outdoor recreation. Enjoy a leisurely stroll, a vigorous hike, or a picnic with friends while surrounded by nature’s beauty. For golf enthusiasts, the historic Chestnut Hill Golf Club offers a challenging course with breathtaking views.

Education is a cornerstone of this community, with access to some of the top schools in the state, including the prestigious Boston College. The area is also well-connected by public transportation, making it easy to commute to Boston for work or leisure.

Chestnut Hill is not only a place to live but a place to thrive. With a delightful mix of local shops, fine dining, and cultural attractions, residents can indulge in a vibrant lifestyle. Experience the best of both worlds in Chestnut Hill – a serene suburban oasis with the excitement of city living just a stone's throw away. Welcome home!

Newest Listings in Chestnut Hill

$1,900,000

2 Beds ⋅ 3 Baths ⋅ 73591946 MLS ⋅ ['The Farm'] BLDG.

Sunlight fills this distinctive penthouse crowning The Farm, with sweeping views of the pond, waterfall, and beautifully landscaped grounds. The spacious living room features a fireplace, built-in bookshelves, and a concealed wet bar, with access to a private balcony overlooking the tranquil setting. The sunny eat-in kitchen is a welcoming space for everyday meals and easy entertaining. Two thoughtfully separated bedrooms provide privacy, and the generous primary suite is a true retreat, with skylights, a dressing area, a full bath, and a separate office. With three full baths in all, the home is comfortable for residents and guests alike. Parking is a luxury in itself: two deeded spaces in the building, plus a separate garage for a third car with room for additional storage. A rare opportunity for carefree living at one of Chestnut Hill’s most sought-after addresses.

99 Florence St Unit 10-5B, Newton

Listing courtesy of Listing Agent: Suburban Boston Team from Listing Office: Compass.

250 Hammond Pond Parkway Unit 812 N, Newton

$529,000

1 Beds ⋅ 2 Baths ⋅ 73591578 MLS ⋅ ['The Towers Of Chestnut Hill'] BLDG.

Eighth Floor Beauty! Rarely available one bedroom, one- and one-half bath, light and bright unit in the North Building of The Towers of Chestnut Hill. with 24-hour concierge, a deeded parking spot just outside the door, heated swimming pool, recently renovated workout room and more! Set on over 17 lush acres with walking trails galore and just minutes to shopping (Wegman’s, The Street, Chestnut Hill Mall) and medical offices (Longwood, NE Baptist). Move right in or bring your decorating ideas. Thoughtful renovations include granite countertops, generous cabinet space in the kitchen and marble countertop in the half bath. Newer SS refrigerator and in-unit washer/dryer. Amenities include gated entrance, library, game room, pickleball and tennis courts, garden area and two beautiful residence lounges. The ultimate in luxury and convenience, make the Towers of Chestnut Hill your new home!

250 Hammond Pond Parkway Unit 812 N, Newton

Listing courtesy of Listing Agent: Maureen Murphy Olsen from Listing Office: Louise Condon Realty.

$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.

$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.

$4,200,000

4 Beds ⋅ 5 Baths ⋅ 73588000 MLS

Welcome to the Golden Triangle of Chestnut Hill! Ideally situated between Newton Centre, The Street and Chestnut Hill Square, with convenient access to Rt.9 and the Mass Pike, this exceptional home offers a rare combination of privacy, mature landscape, and character of an established Chestnut Hill setting with the scale, ceiling heights, infrastructure, and quality of a custom-built home. From the dramatic marble foyer and sweeping staircase, the home's defining sense of volume is immediately apparent. High ceilings extend throughout all levels of the home, while oversized windows fill the interiors with natural light. Generous proportions and airy living spaces create a sense of scale rarely found in established homes. The heart of the home features a spacious kitchen and informal dining area overlooking the grounds and pool, while formal living and dining rooms provide elegant spaces for entertaining. A front-to-back family room and extensive floor-to-ceiling windows create a seamless connection between indoor and outdoor living. Upstairs, the oversized primary suite offers remarkable scale and flexibility, with a large walk-in closet and luxurious bath with jacuzzi tub and steam shower. The bedroom could potentially be reconfigured into two generously proportioned bedrooms. The additional bedrooms are equally spacious, with private bathroom access. Mature landscaping surrounds the property with exceptional privacy, creating a secluded oasis. A large heated saltwater pool and expansive patio provide the perfect setting for summer entertaining, outdoor dining, and relaxed afternoons at home. A three-car garage adds exceptional convenience and storage.

7 Monadnock Rd, Newton

Listing courtesy of Listing Agent: Esin Susol Team from Listing Office: William Raveis R. E. & Home Services.

$398,000

1 Beds ⋅ 1 Baths ⋅ 73582234 MLS ⋅ ['Broadlawn Park Condominium'] BLDG.

Discover the easy living lifestyle at Broadlawn Park Condominiums in Chestnut Hill. This one-bedroom 2nd floor unit offers a comfortable place to relax, work, and entertain, with the convenience of a Chestnut Hill address, with wonderful shopping and dining amenities at The Street in Chestnut Hill, which is across the street from Wegman's for groceries. There is excellent closet space within the unit, as well as an oversized, locked private storage bin in the lower level for spillover belongings. Whether you’re looking for your first home, a place to downsize, or a Boston-area retreat, this well maintained condominium is an inviting opportunity to make the space your own. Spacious open living/dining great room with sliders to your private balcony for morning coffee and end of day sunsets. The building features landscaped grounds, professional management, clean laundry room, elevator, storage and a terrific, clean & modern clubhouse and outdoor pool for resident use! The clubhouse has excellent amenities like kitchen facilities, ping pong table, a library of books, and is almost an extension of your unit for a quiet place to sit and read, work from home, compose your next novel or entertain friends and family in a huge room with walk out access to the pool and large patio areas. Your parking space is just beyond your balcony, and there are typically rental spaces available for a 2nd car. There is a lot of appeal in this established condominium setting. Priced to sell and easy to show.

57 Broadlawn Park Unit 3A, Boston

Listing courtesy of Listing Agent: Ed Lyon from Listing Office: Preservation Properties.

250 Hammond Pond Parkway Unit 1611N, Newton

$1,349,000

3 Beds ⋅ 2 Baths ⋅ 73581961 MLS ⋅ ['The Towers Of Chestnut Hill'] BLDG.

Rare opportunity to own this distinctive three-bedroom luxury residence in one of Chestnut Hill’s most prominent buildings, ideally located on Hammond Pond Parkway and just minutes from Longwood, Back Bay, Beacon Hill, the South End and Coolidge Corner. Framed with over-sized windows throughout, this 16th-floor residence in the North Tower offers breathtaking southwest-facing views, spectacular sunsets and nearly 1,700 square feet of spacious, comfortable living with a thoughtfully designed open floor plan is ideal for both everyday living and entertaining. The modern kitchen features custom cabinetry, quartz countertops and stainless steel appliances, while the adjacent dining area provides a perfect setting for casual meals or hosting guests. The spacious primary suite offers an en-suite bath with an expansive closet and a dedicated dressing area. Two additional generously sized bedrooms another full bath, in-unit laundry, generous closet space and numerous thoughtful details create an exceptional sense of comfort and scale. The residence includes two deeded parking spaces: one garage space (#337) and one outdoor space (#1). Residents enjoy full-service living with professional on-site management, maintenance staff and a 24-hour doorman, along with an impressive array of amenities. These include an indoor heated swimming pool, recently upgraded fitness center, brand-new pickleball court, tennis courts, outdoor playground and indoor children's playroom--all set on 17 professionally landscaped acres. The Towers is ideally situated in a prime Chestnut Hill location, close to Chestnut Hill Mall, The Street, Wegman's, Movie Theatre, the MBTA and Longwood Medical Center shuttle services. With convenient access to public transportation, shopping, dining, and nature, this exceptional residence offers a combination of space, luxury, convenience, and resort-style living.

250 Hammond Pond Parkway Unit 1611N, Newton

Listing courtesy of Listing Agent: Ilene Solomon from Listing Office: Coldwell Banker Realty - Newton.

$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.

250 Hammond Pond Pkwy Unit 1006N, Newton

$849,000

2 Beds ⋅ 2 Baths ⋅ 73578905 MLS ⋅ ['Chestnut Hill Condominium'] BLDG.

Experience luxury high-rise living at the sought-after Chestnut Hill Condominium! Positioned on the 10th floor, this expansive single-level residence offers 2 spacious bedrooms and 2 full bathrooms. The light-filled layout features rich hardwood floors, an inviting open living room, a distinct dining area, with central air. The fully equipped kitchen. The spacious primary suite highlights plush wall-to-wall carpeting, a large walk-in closet, and a private en-suite bathroom. A second bright bedroom with hardwood floors is paired with a second full bathroom. This unit includes 2 assigned parking spaces, including 1 garage space under the building. Set on 17+ landscaped acres directly behind The Shops at Chestnut Hill, enjoys 24-hour concierge service, security gate access, an indoor heated pool, fitness center, tennis courts, and clubroom. Live close to luxury shopping at The Street, fine dining, Hammond Pond Reservation, and direct Boston transit via Route 9 and the MBTA Green Line. A true turn-key retreat!

250 Hammond Pond Pkwy Unit 1006N, Newton

Listing courtesy of Listing Agent: Delince P. Louis from Listing Office: Redfin Corp..

$549,000

1 Beds ⋅ 2 Baths ⋅ 73578825 MLS ⋅ ['Imperial Towers'] BLDG.

Fabulous Imperial Towers Chestnut Hill, totally updated One bedroom unit. Worry free lifestyle with the ease of full-service condominium living. Featuring an abundance of natural light, open floor plan, sweeping skyline city and tree top views, generous closets/storage space, Renovated bathrooms and kitchen. Enjoy the many amenities—heated seasonal pool, a new fitness center, a clubroom, library, EV Charging Station, bicycle storage & extra storage.1 car deeded carport space #53. The 24 Hour concierge, on-site management and live-in superintendent ensure effortless living, 100% owner occupied, move in/out fee $400. Prime location near Chestnut Hill Square,The Street, The Shops at Chestnut Hill , Wegman's & many wonderful restaurants. Easy access to Boston & Longwood Medical area. A very well maintained building with many updates. Unit 908 at the Imperial Towers is Chestnut Hill living at its finest!

280 Boylston Street Unit 908, Newton

Listing courtesy of Listing Agent: Cary Berger from Listing Office: Coldwell Banker Realty - 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.

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