Homes with Basements for Sale in Chestnut Hill, MA

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ABOUT THIS HOME
Home with Basement for sale in Chestnut Hill, MA:
SPACIOUS AND BRIGHT CONDO WITH TERRIFIC LOCATION!! This home offers a welcoming entrance into a spacious living room with a bank of windows and gleaming hardwood floors. The living room leads to a well equipped kitchen with ample counterspace and cabintry, built-in micro and outdoor access. A spacious bonus room off of the kitchen can be a dining room, office or (add a door) a second bedroom! The primary bedroom is well-proportioned with hardwood floors and offers a comfortable and private retreat. The art deco bathroom features original black and white tile work. The covered porch off the kitchen provides an inviting outdoor space, allowing you to enjoy the beautifully landscaped grounds.

$449,000

1 bed1 bath710 sq ft

33 Hammond Pond Pkwy #2, Chestnut Hill, MA 02467

Covered porch • Welcoming entrance • Ample counterspace

ABOUT THIS HOME
Home with Basement for sale in Chestnut Hill, MA:
Introducing Paine Estate, a grand Georgian Revival architectural treasure located in the highly coveted Chestnut Hill neighborhood of Brookline. This outstanding property has been extensively renovated, now combining traditional style and modern amenities with a thoughtful floor plan ideal for comfortable family living and grand entertaining. Exceptional features include a grand entry hall, elegant formal sunken living room overlooking the picturesque gardens, fireplaced dining room, gourmet chef's kitchen, family room, handsome wood paneled library and an expansive great room. 6 bedrooms include the luxurious primary suite complete with separate bathrooms and dressing rooms and balcony. Ad

$19,000,000

7 beds9.5 baths13,343 sq ft

1014 Boylston St, Chestnut Hill, MA 02467

Grand entry hall • Sunken living room • Expansive great room

ABOUT THIS HOME
Home with Basement for sale in Chestnut Hill, MA:
Beautifully restored 1900s French-style residence on an acre of land in Brookline’s coveted Fisher Hill. Over 6,000 sq ft of living space featuring five bedrooms and 4.5 bathrooms. Inviting foyer with fireplace & custom bookshelves, an impressive great room with 15’ ceilings & fireplace, an elegant living room with period details including a fireplace, and a dining room with French doors to a stone terrace. House features a chef’s kitchen with high-end appliances and two spacious first-floor primary suites offering serene terrace views. The second floor has two bedrooms and a full bathroom. There is also a fifth bedroom with private entrance, perfect for au pai

$5,000,000

5 beds4.5 baths6,419 sq ft

540 Chestnut Hill Ave, Brookline, MA 02445

Inviting foyer • Acre of land • Serene terrace views

ABOUT THIS HOME
Home with Basement for sale in Chestnut Hill, MA:
Renovate or build new, on one of Brookline’s most desirable and picturesque streets and sought after neighborhoods. Existing GLA of nearly 5k sqft (988 finished basement), or build 4396 sqft by right on upper floors. Survey and existing conditions plans are available. Demo hold expires October 2025

$2,295,000

4 beds4 baths4,855 sq ft

3 Glenoe Rd, Chestnut Hill, MA 02467

0.4 acre lot • 2 garage spots • Built 1939

ABOUT THIS HOME
Home with Basement for sale in Chestnut Hill, MA:
Fully Renovated 2 bed/ 1 bath in the heart of Chestnut Hill! In unit washer/dryer, Split System A/C two units with deeded parking spot, and ample guest parking. Master bedroom suite plus loft space perfectly as a second bedroom and/or office. Custom kitchen with stainless steel appliances and gorgeous bathroom with porcelain tile. The association is professionally managed and pet-friendly. Within seconds from Wegman's, Chestnut Hill Mall, and The Street shopping center. 15 min walk to Chestnut Hill train station and bus stops. Heat, hot water, and snow removal included.

$565,000

2 beds1 bath810 sq ft

11 Hammond Pond Pkwy #3, Chestnut Hill, MA 02467

Guest parking • Custom kitchen • In unit washer dryer

Property at 15 Glenland, Chestnut Hill, MA 02467, 5 beds, 4.5 baths

$3,749,000

5 beds4.5 baths4,711 sq ft

15 Glenland, Chestnut Hill, MA 02467

Property at 59 Ackers Ave #1, Brookline, MA 02445, 2 beds, 1 bath

$825,000

2 beds1 bath1,128 sq ft

59 Ackers Ave #1, Brookline, MA 02445

Property at 88 Essex Rd, Chestnut Hill, MA 02467, 5 beds, 6.5 baths

$9,700,000

5 beds6.5 baths8,750 sq ft

88 Essex Rd, Chestnut Hill, MA 02467

Property at 120 Cabot St, Chestnut Hill, MA 02467, 6 beds, 7.5 baths

$6,995,000

6 beds7.5 baths8,849 sq ft

120 Cabot St, Chestnut Hill, MA 02467

Property at 27-29 Commonwealth Ave #9, Chestnut Hill, MA 02467, 1 bed, 1 bath

$595,000

1 bed1 bath756 sq ft

27-29 Commonwealth Ave #9, Chestnut Hill, MA 02467

Property at 130 Cabot St, Chestnut Hill, MA 02467, 6 beds, 8 baths

$6,995,000

6 beds8 baths9,755 sq ft

130 Cabot St, Chestnut Hill, MA 02467

Property at 321 Hammond Pond Pkwy #106, Chestnut Hill, MA 02467, 2 beds, 2 baths

$949,000

2 beds2 baths1,188 sq ft

321 Hammond Pond Pkwy #106, Chestnut Hill, MA 02467

Property at 85 Gate House Rd, Chestnut Hill, MA 02467, 5 beds, 5.5 baths

$4,375,000

5 beds5.5 baths8,000 sq ft

85 Gate House Rd, Chestnut Hill, MA 02467

Property at 460 Heath St, Chestnut Hill, MA 02467, 5 beds, 3.5 baths

$3,699,000

5 beds3.5 baths6,196 sq ft

460 Heath St, Chestnut Hill, MA 02467

Property at 27-29 Commonwealth Ave #5, Chestnut Hill, MA 02467, 1 bed, 1 bath

$580,000

1 bed1 bath724 sq ft

27-29 Commonwealth Ave #5, Chestnut Hill, MA 02467

Property at 321 Hammond Pond Pkwy Unit U301, Chestnut Hill, MA 02467, 2 beds, 2.5 baths

$1,225,000

2 beds2.5 baths1,527 sq ft

321 Hammond Pond Pkwy Unit U301, Chestnut Hill, MA 02467

Property at 321 Hammond Pond Pkwy #103, Chestnut Hill, MA 02467, 2 beds, 2 baths

$1,099,000

2 beds2 baths1,350 sq ft

321 Hammond Pond Pkwy #103, Chestnut Hill, MA 02467

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NEW 4 HRS AGO

ABOUT THIS HOME
Home with Basement for sale in Chestnut Hill, MA:
This sprawling condominium with 16th floor awe-inspiring views is truly a rare find at the Towers of Chestnut Hill. This corner unit showcases wonderful space, light and well-proportioned rooms and expands nearly 1000 sq. ft. and feels even larger. Truly panoramic unobstructed views from every room allow the perfect backdrop for entertaining. From the moment you drive up to the circular drive, the Towers offers the ultimate in privacy, service and luxury. The Towers of Chestnut Hill sits on 17 beautiful acres in the finest area in Chestnut Hill. 24-hour doorman underscores it all. strong, healthy HOA. Solid investment.

$599,000

1 bed1.5 baths899 sq ft

250 Hammond Pond Pkwy Unit 1604N, Chestnut Hill, MA 02467

17.48 acre lot • $693 HOA • Garage

NEW 12 HRS AGO

ABOUT THIS HOME
Home with Basement for sale in Chestnut Hill, MA:
Welcome to 799 Heath Street, Unit 2 - an inviting and elegant 4-bedroom, 2.5-bathroom townhouse nestled in the prestigious Chestnut Hill neighborhood of Brookline. This exquisite residence offers 2,366 square feet of modern luxury and comfort, designed with discerning tastes in mind. Step into the main level, where a gourmet kitchen and dining area set the stage for culinary delights and entertaining. The spacious living room, featuring custom woodwork and newly installed blinds, provides a perfect setting for relaxation and gatherings. Upstairs, a serene master suite awaits, alongside two additional bedrooms that offer ample space and privacy. The first level showcases a versatile bonus ro

$1,749,000

4 beds2.5 baths2,366 sq ft

799 Heath St #2, Chestnut Hill, MA 02467

2 garage spots • Very walkable

ABOUT THIS HOME
Home with Basement for sale in Chestnut Hill, MA:
Located at 173-175 Warren St, in the charming city of Newton, Massachusetts, this multi-family residence presents itself as an inviting home, ready to welcome its residents. Imagine evenings spent in the living room, the fireplace casting a warm glow across the space, while the detailed crown molding adds a touch of architectural sophistication. Picture yourself crafting culinary masterpieces in the kitchen, where the stone countertops provide a beautiful and functional workspace. The property offers several spaces designed to enhance your lifestyle, including a porch ideal for relaxing, a sunroom promising light-filled mornings, a deck perfect for entertaining, and a balcony offering a pri

$1,800,000

7 beds2 baths2,476 sq ft

173-175 Warren St, Newton Center, MA 02459

9,418 sq ft lot • 2 garage spots • Very walkable

OPEN WED, 12PM TO 1PM

ABOUT THIS HOME
Home with Basement for sale in Chestnut Hill, MA:
Located on Aspinwall Hill just across from across from Schick park is this total gut renovated 5 bed, 3.5 bath 3,250 sq. ft. duplex that artfully blends luxury with comfort. The expansive foyer leads you to a state-of-the-art chef's kitchen, complete with stone countertops, high-end Thermador appliances & island leading to a breakfast area. There is a generous deck great for entertaining as well as a formal dining area & spacious living room. An office space with its own private deck, 2 bedrooms, a full bath & 1/2 bath complete this level. The upper level boasts a primary suite with a walk-in closet & stunning bath flanked by 2 add'l bedrooms, full bath & laun

$3,200,000

5 beds3.5 baths3,250 sq ft

90 Addington #2, Brookline, MA 02445

Somewhat walkable

ABOUT THIS HOME
Home with Basement for sale in Chestnut Hill, MA:
Ideally located on Strathmore Road next to Dean Park, this beautifully updated two-bedroom, two-bath garden-level home offers comfort, convenience, and charm. Features include high ceilings, hardwood floors, and a spacious living area with a fireplace. The modern kitchen and baths have been tastefully renovated, blending style with functionality. Enjoy central air, in-unit laundry, and the rare benefit of parking. Step outside to a private patio—perfect for relaxing or entertaining. Just steps to the C and D trolley lines, shops, and restaurants, this home offers easy access to the Longwood Medical Area and downtown Boston. A wonderful opportunity to enjoy Brookline living at its best

$740,000

2 beds2 baths1,375 sq ft

8 Strathmore Rd Unit G, Brookline, MA 02445

$267 HOA • Very walkable

ABOUT THIS HOME
Home with Basement for sale in Chestnut Hill, MA:
Sunny and convenient 3-story, 3-bedroom townhouse perfect for investors or owner-occupants. Features a spacious high-ceiling living/dining area with large bay windows, and an extra office space on the second floor. All bedrooms are bright with walk-in closets. The kitchen includes a gas stove, dishwasher, and refrigerator, plus in-unit washer/dryer, central AC, updated heating (2020), and a new gas water heater (2024). Hardwood floors throughout the unit. Walking distance to Green B Line, bus stops, shops, and restaurants. Includes one assigned parking space. Currently leased through 7/31/2026 for $5,225/month.

$1,190,000

3 beds2.5 baths1,985 sq ft

1304 Commonwealth Ave #5, Boston, MA 02134

$567 HOA • Walker's paradise

Property at 40 Orkney Rd #1, Brighton, MA 02135, 2 beds, 1 bath

$545,000

2 beds1 bath800 sq ft

40 Orkney Rd #1, Brighton, MA 02135

Property at 85 Brainerd Rd Unit TH7, Allston, MA 02134, 3 beds, 2.5 baths

$1,199,900

3 beds2.5 baths1,900 sq ft

85 Brainerd Rd Unit TH7, Allston, MA 02134

Property at 1731 Beacon St #717, Brookline, MA 02445, 2 beds, 2 baths

$873,000

2 beds2 baths1,218 sq ft

1731 Beacon St #717, Brookline, MA 02445

Property at 33 Shannon St #3, Brighton, MA 02135, 3 beds, 2.5 baths

$749,999

3 beds2.5 baths1,371 sq ft

33 Shannon St #3, Brighton, MA 02135

Property at 771 Heath St #771, Chestnut Hill, MA 02467, 3 beds, 3.5 baths

$1,750,000

3 beds3.5 baths3,070 sq ft

771 Heath St #771, Chestnut Hill, MA 02467

Property at 45 Bartlett Cres #305, Brookline, MA 02446, 2 beds, 2 baths

$1,233,850

2 beds2 baths946 sq ft

45 Bartlett Cres #305, Brookline, MA 02446

Property at 39 South St Unit B, Brighton, MA 02135, 2 beds, 1 bath

$569,000

2 beds1 bath1,040 sq ft

39 South St Unit B, Brighton, MA 02135

Property at 38 Tanglewood Rd #38, Newton Center, MA 02459, 3 beds, 3 baths

$1,649,000

3 beds3 baths3,096 sq ft

38 Tanglewood Rd #38, Newton Center, MA 02459

Property at 2400 Beacon St #112, Chestnut Hill, MA 02467, 2 beds, 2 baths

$1,349,000

2 beds2 baths1,347 sq ft

2400 Beacon St #112, Chestnut Hill, MA 02467

Property at 15 Nantasket Ave, Brighton, MA 02135, 5 beds, 3 baths

$1,225,000

5 beds3 baths2,750 sq ft

15 Nantasket Ave, Brighton, MA 02135

Property at 1856 Beacon St Unit 2C, Brookline, MA 02445, 2 beds, 1.5 baths

$740,000

2 beds1.5 baths913 sq ft

1856 Beacon St Unit 2C, Brookline, MA 02445

Property at 1515 Commonwealth Ave #311, Boston, MA 02135, 2 beds, 2 baths

$1,349,000

2 beds2 baths1,246 sq ft

1515 Commonwealth Ave #311, Boston, MA 02135

Property at 65 Strathmore Rd #49, Brighton, MA 02135, 1 bed, 1 bath

$530,000

1 bed1 bath764 sq ft

65 Strathmore Rd #49, Brighton, MA 02135

Property at 100 Lanark Rd Unit A, Brighton, MA 02135, 2 beds, 1 bath

$399,000

2 beds1 bath730 sq ft

100 Lanark Rd Unit A, Brighton, MA 02135

Homes with Basements for Sale in Chestnut Hill

There are currently 17 homes with basements for sale in Chestnut Hill at a median listing price of $1.39M. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Chestnut Hill stay on the market for 83 days and receive 1 offers. Popular neighborhoods include Jamaica Plain, Roslindale, Brighton, Allston, and West Roxbury. This map is refreshed with the newest listings in Chestnut Hill every 15 minutes.

In the past month, 4 homes have been sold in Chestnut Hill. In addition to houses in Chestnut Hill, there were also 13 condos, 1 townhouse, and 1 multi-family unit for sale in Chestnut Hill last month. Chestnut Hill is a moderately walkable neighborhood in Middlesex County with a Walk Score of 52. Chestnut Hill is home to approximately 9,146 people. Find your dream home in Chestnut Hill using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Chestnut Hill are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Chestnut Hill. If you're looking to sell your home in the Chestnut Hill area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Chestnut Hill with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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