Chestnut Hill Real Estate

Chestnut Hill Real Estate

Welcome to Chestnut Hill, Massachusetts, a picturesque community that beautifully blends suburban charm with urban convenience. Nestled just six miles from downtown Boston, Chestnut Hill is renowned for its stunning landscapes, historic architecture, and vibrant lifestyle. This idyllic neighborhood is characterized by its tree-lined streets, elegant homes, and a strong sense of community that makes it a sought-after destination for families and professionals alike.

One of the standout features of Chestnut Hill is its rich cultural heritage, reflected in its historic landmarks and well-preserved buildings. The area is home to the prestigious Boston College, which not only adds a youthful energy to the community but also offers a variety of cultural and sporting events throughout the year. Local parks, such as the beautiful Chestnut Hill Reservation, provide ample opportunities for outdoor recreation, from hiking and biking to leisurely picnics.

Shopping enthusiasts will delight in the diverse array of boutiques and specialty shops at The Chestnut Hill Mall and The Street Chestnut Hill, where you can find everything from high-end fashion to gourmet dining. The local dining scene is equally impressive, featuring a mix of cozy cafes and upscale restaurants that cater to every palate.

With excellent public transportation options and top-rated schools, Chestnut Hill is perfect for those seeking both tranquility and accessibility. Whether you’re looking for a serene place to raise a family or a vibrant community to call home, Chestnut Hill, MA, offers a unique blend of comfort and sophistication that is hard to resist. Experience the charm of this exceptional neighborhood and discover why so many choose to call Chestnut Hill home!

Newest Listings in Chestnut Hill

63-65 Commonwealth Avenue, Newton
$7,350,000
8 Beds ⋅ 10 Baths ⋅ 73599780 MLS
Presenting The Lennox Chestnut Hill, a rare opportunity to acquire two newly constructed, Scandinavian-inspired luxury residences at 63–65 Commonwealth Avenue, designed and built by award-winning developer Excelsior Development Partners. A 2026 PRISM Gold Award Winner for Best Kitchen, The Lennox offers approximately 9,000 SF of combined living space with eight bedrooms, eight full and two half baths, and four garage parking spaces. Each four-level residence features a private elevator, chef's kitchen with natural quartzite, Scavolini Italian cabinetry, Gaggenau appliances, Thermador refrigeration, and a hidden pantry. Additional highlights include private outdoor spaces, spa-inspired primary suites, custom walk-in closets, finished lower levels, top-floor bonus rooms with fireplaces, oak flooring, and Control4 home automation. Ideally situated in Chestnut Hill, just minutes from Boston College, the Green Line, Newton schools, The Street at Chestnut Hill, and downtown Boston, offering exceptional convenience and accessibility. With an estimated combined rental potential of $50,000 per month, this two-residence offering presents a compelling investment opportunity, with flexibility for multigenerational living, owner occupancy, or rental income. A unique opportunity to own two exceptional new-construction homes in one of Greater Boston's most desirable locations.

63-65 Commonwealth Avenue, Newton

Listing courtesy of Listing Agent: Khoury Group from Listing Office: Serhant.
67 Moody St, Newton
$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.
250 Hammond Pond Parkway Unit 310N, Newton
$550,000
1 Beds ⋅ 2 Baths ⋅ 73597326 MLS ⋅ ['Towers Of Chestnut Hill'] BLDG.
A rare opportunity to experience the very best of luxury living at The Towers of Chestnut Hill, Hammond Pond Parkway’s most distinguished condominium residence. A premier, five-star community, The Towers embodies the essence of sophisticated, maintenance-free Chestnut Hill living. On rare occasions, a one-bedroom residence with 1½ baths becomes available, making this third-floor offering particularly special. Spanning nearly 1,000 square feet, this gracious home showcases exceptional space, abundant natural light, and generously proportioned rooms that create an impressive sense of openness. Residents enjoy an extraordinary collection of amenities designed to complement an effortless lifestyle, including 24-hour concierge service, an indoor heated swimming pool, a newly installed fitness center, clubhouse, two resident lounges, library, pickleball and tennis courts, basketball court, landscaped gardens, gardening club, outdoor fire pit and grilling areas. Additional amenities include a children’s play area, game room featuring ping-pong and foosball, secure package room, bicycle storage, and two elevators. Ideally situated just steps from the Longwood Medical Area shuttle and minutes from Longwood Medical, premier shopping, dining, and everything Chestnut Hill has to offer. A truly rare offering in one of Chestnut Hill’s most iconic luxury condominium communities. 1 deeded garage space included in the sale. Solid investment.

250 Hammond Pond Parkway Unit 310N, Newton

Listing courtesy of Listing Agent: Richard C. Dore from Listing Office: Hammond Residential Real Estate.
622 Chestnut Hill Ave, Brookline
$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.
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.
99 Florence St Unit 10-5B, Newton
$1,799,000
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.
30 Hackensack Road, Brookline
$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.
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.
57 Broadlawn Park Unit 3A, Boston
$389,000
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.
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