Recently Sold Homes in Chestnut Hill, MA

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SOLD OCT 31, 2025

ABOUT THIS HOME
Recently Sold Home in Chestnut Hill, MA:
First floor, 2 bedroom condo in Brookline’s highly desirable Chestnut Hill neighborhood! Located right around corner from Heath School. Centrally located just 100 ft from bus, 1/2 mile from nearest Green Line stop, within mile of the street shopping, restaurants, close to Boston’s medical area, universities, parks/playgrounds! Daytime resident parking with permit available on street. Take advantage of this below market priced project and stellar location. Cash offers preferred.

$416,000 Last sold price

2 beds1 bath1,028 sq ft

765 Boylston St #1, Chestnut Hill, MA 02467

SOLD AUG 26, 2025VIDEO TOUR

ABOUT THIS HOME
Recently Sold Home in Chestnut Hill, MA:
This beautifully renovated single-family home in Chestnut Hill combines timeless elegance with modern amenities. Spanning four levels, it features five spacious bedrooms and three full bathrooms with custom finishes, plus two well appointed half baths. The open-concept living areas include a formal living room and a den, both with oversized windows. The chef's kitchen includes stainless steel appliances, a large island, and ample counter space. Located off the kitchen is a cozy breakfast nook that flows into the formal dining room opening onto an expansive deck. The private deck overlooks a fenced in yard, perfect for outdoor entertainment and enjoyment. The primary suite offers a spacious

$2,485,000 Last sold price

5 beds4 baths4,119 sq ft

254 Commonwealth Ave, Chestnut Hill, MA 02467

SOLD NOV 10, 2025

ABOUT THIS HOME
Recently Sold Home in Chestnut Hill, MA:
Timeless elegance in Chestnut Hill’s most coveted location! This stunning Georgian-style brick mansion, complete with a separate carriage house, is set on nearly an acre of beautifully landscaped grounds with rolling lawns, mature trees, and lush gardens. Inside, high ceilings, abundant natural light, and a fantastic floor plan enhance its graceful character. A porte-cochère leads to a lovely entry hall and magnificent first-floor rooms, including grand living and dining, expansive kitchen with access to the impressive breakfast room, family room with walls of glass, library, and great room. The second level offers five bedrooms, while the finished third floor includes three bo

$3,700,000 Last sold price

6 beds4.5 baths6,943 sq ft

87 Hammond St, Chestnut Hill, MA 02467

SOLD SEP 5, 2025

ABOUT THIS HOME
Recently Sold Home in Chestnut Hill, MA:
Nestled on a beautiful tree-lined street in Olde Chestnut Hill, this spectacular home offers an open and elegant floor-plan perfect for living and entertaining. Thoughtfully renovated in 2012, this home masterfully blends timeless architectural charm with modern amenities. High ceilings, abundant natural light, and beautifully crafted moldings and millwork create a sense of warmth throughout. The gracious foyer welcomes you into an expansive living/dining area leading to a stunning chef’s kitchen. The kitchen opens to a spacious family room, complete with a gas fireplace, wet bar, and French doors that lead to serene, manicured grounds. Offering 6 bedrooms, each with en suite bathroom

$5,462,500 Last sold price

6 beds7 baths7,016 sq ft

9 Woodman Rd, Chestnut Hill, MA 02467

SOLD OCT 30, 2025

ABOUT THIS HOME
Recently Sold Home in Chestnut Hill, MA:
Nestled in Newton’s highly coveted Chestnut Hill Historic District, this newly renovated 3-bedroom, 2.5-bath contemporary home combines modern updates with timeless architectural character. Set on a private 15,000 sq. ft. lot, the home features a spacious open floor plan with soaring ceilings, exposed beams and walls of glass overlooking the wooded grounds. The dining and living rooms are anchored by a striking floor-to-ceiling stone fireplace and seamlessly connect to a screened porch and side patio, perfect for indoor-outdoor living. Recent updates include refinished hardwood floors along with thoughtfully renovated baths and kitchen, blending timeless architectural details with mod

$2,250,000 Last sold price

3 beds2.5 baths2,844 sq ft

47 Nancy Rd, Chestnut Hill, MA 02467

Property at 46 Malia Ter, Chestnut Hill, MA 02467, 5 beds, 4.5 baths

$3,036,350 Last sold price

5 beds4.5 baths3,909 sq ft

46 Malia Ter, Chestnut Hill, MA 02467

Property at 27 Suffolk Rd, Chestnut Hill, MA 02467, 6 beds, 4.5 baths

$4,400,000 Last sold price

6 beds4.5 baths5,520 sq ft

27 Suffolk Rd, Chestnut Hill, MA 02467

Property at 26 Holly Ln Unit 3E, Chestnut Hill, MA 02467, 1 bed, 1.5 baths

$700,000 Last sold price

1 bed1.5 baths901 sq ft

26 Holly Ln Unit 3E, Chestnut Hill, MA 02467

Property at 35 Jefferson Rd, Chestnut Hill, MA 02467, 5 beds, 3.5 baths

$2,245,000 Last sold price

5 beds3.5 baths3,634 sq ft

35 Jefferson Rd, Chestnut Hill, MA 02467

Property at 61 Heath St, Brookline, MA 02445, 5 beds, 6 baths

$8,000,000 Last sold price

5 beds6 baths7,000 sq ft

61 Heath St, Brookline, MA 02445

Redfin Corp.

Property at 167 Willard Rd, Brookline, MA 02445, 4 beds, 3.5 baths

$3,400,000 Last sold price

4 beds3.5 baths3,298 sq ft

167 Willard Rd, Brookline, MA 02445

Property at 35 Commonwealth Ave #404, Chestnut Hill, MA 02467, 1 bed, 1 bath

$620,000 Last sold price

1 bed1 bath786 sq ft

35 Commonwealth Ave #404, Chestnut Hill, MA 02467

Property at 23 Crafts Rd, Chestnut Hill, MA 02467, 7 beds, 8 baths

$5,100,000 Last sold price

7 beds8 baths7,140 sq ft

23 Crafts Rd, Chestnut Hill, MA 02467

Property at 24 Essex Rd, Chestnut Hill, MA 02467

$5,800,000 Last sold price

— beds— baths— sq ft

24 Essex Rd, Chestnut Hill, MA 02467

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BOUGHT WITH REDFIN OCT 23, 2025

ABOUT THIS HOME
Recently Sold Home in Chestnut Hill, MA:
Bright & sunny, spacious top floor unit in an established Brighton Place Condominium! It is currently rented as a 2 bedroom, but has a walled-off Living Room, which may be used as a 3rd bedroom. This unit has updated windows, hardwood floors. Large eat-in kitchen with tile floor and granite counter, refrigerator, range, dishwasher, disposal, and microwave. Bathroom has ceramic tile floor and bathtub surround. Deeded parking #21 is located right behind the building. Conveniently located near Commonwealth Ave and Washington Street, with easy access to shopping, restaurants, public transportation and much more! This unit is currently rented through August 2026. Very limited showings

$469,000 Last sold price

2 beds1 bath739 sq ft

28 Ransom Rd #11, Brighton, MA 02135

Redfin Corp.

SOLD BY REDFIN SEP 11, 20253D WALKTHROUGH

ABOUT THIS HOME
Recently Sold Home in Chestnut Hill, MA:
Despite the address, this home sits on a QUIET DEAD-END—the first right off Monastery Rd from Washington St. A hidden gem, it blends antique charm with modern design. The open-concept living/dining area is ideal for relaxing or entertaining. The kitchen features custom cabinetry, gas cooking, a pantry, and direct access to a fenced backyard oasis with mature trees and perennial gardens. Over the past 10 years, the home has been extensively updated for easy, worry-free living: young heating & hot water systems, new siding, roof, insulation, energy-efficient windows, and appliances. Includes an unfinished DRY basement with great storage and two side-by-side off-street parking spac

$810,000 Last sold price

3 beds1 bath978 sq ft

186 Washington St, Brighton, MA 02135

SOLD BY REDFIN SEP 30, 20253D WALKTHROUGH

ABOUT THIS HOME
Recently Sold Home in Chestnut Hill, MA:
Welcome to 4 Commonwealth Ct Unit 20—your front row seat to the city skyline! This bright and inviting top-floor unit offers sweeping, unobstructed views of Boston from your own private balcony, perched just above the sparkling outdoor pool. Enjoy hardwood floors throughout, an updated kitchen with a gas stove, and a layout designed for both comfort and function. Heat and hot water are included in the condo fee, adding to the ease of ownership. The professionally managed building boasts a brand new roof and boiler, along with a well-maintained pool for summer relaxation. Just 100' to the Green Line T, shops, and restaurants, this location offers unbeatable convenience and views you wo

$469,000 Last sold price

1 bed1 bath630 sq ft

4 Commonwealth Ct #20, Brighton, MA 02135

SOLD AUG 27, 20253D WALKTHROUGH

ABOUT THIS HOME
Recently Sold Home in Chestnut Hill, MA:
* * Top-Floor 2-Bedroom Condo in Prime Brighton Location * * Welcome to this bright and spacious top-floor 2-bedroom condo located in the heart of Brighton. Just a short walk to the Green Line MBTA, this home offers unbeatable access to public transportation, making your commute or city adventures a breeze. Enjoy the convenience of nearby shops and restaurants all within easy reach. Whether you're looking to invest or find your own place to call home, this well-situated unit is ideal for both owner-occupants and savvy investors. Don’t miss this opportunity to own a piece of one of Boston’s most vibrant neighborhoods! Virtual Tour is Available.

$410,000 Last sold price

2 beds1 bath750 sq ft

26 Chiswick Rd #13, Brighton, MA 02135

SOLD NOV 10, 2025

ABOUT THIS HOME
Recently Sold Home in Chestnut Hill, MA:
Fantastic opportunity to purchase a coveted brick single family home in an excellent location near Boston College and public transportation. The home is rented through August 2026 and rents easily each year. Features include hardwood floors, beamed ceilings in the living room and dinning room, classic wood work, large rooms, a kitchen with a separate eat-in dinning area and a separate pantry area, laundry in the basement, parking, and porches. Roof and windows replaced in 2019. This unbelievable location is close to the B train, the C+D trains, coffee shops/restaurants, Cleveland Circle, the Chestnut Hill Reservoir, Boston College and Rogers Park.

$1,185,000 Last sold price

4 beds1 bath1,612 sq ft

66 Kirkwood Rd, Brighton, MA 02135

SOLD AUG 22, 2025

ABOUT THIS HOME
Recently Sold Home in Chestnut Hill, MA:
Amazing Two-Family Home – Ideal for Owner Occupancy, Investment, or Condo Conversion. Don’t miss this exceptional opportunity to own a two-family residence perfectly situated near public transportation, Boston College, Boston Medical Center, and other major area amenities. This property is ideal for homeowners looking to offset their mortgage, savvy investors, or developers seeking a prime candidate for condo conversion. Set on a generously sized lot, this home features off-street parking, a two-car garage, and spacious decks overlooking a private, fenced-in backyard – perfect for entertaining, relaxing, or gardening. Both units offer flexible layouts with great natural li

$1,675,000 Last sold price

5 beds2 baths3,184 sq ft

236 Foster St, Brighton, MA 02135

Property at 68 Kenrick St, Brighton, MA 02135, 2 beds, 1.5 baths

$1,215,000 Last sold price

2 beds1.5 baths1,588 sq ft

68 Kenrick St, Brighton, MA 02135

Property at 146 Woodchester Dr, Chestnut Hill, MA 02467, 5 beds, 4.5 baths

$2,600,000 Last sold price

5 beds4.5 baths4,631 sq ft

146 Woodchester Dr, Chestnut Hill, MA 02467

Property at 250 Hammond Pond Pkwy Unit 707S, Chestnut Hill, MA 02467, 1 bed, 1.5 baths

$539,000 Last sold price

1 bed1.5 baths899 sq ft

250 Hammond Pond Pkwy Unit 707S, Chestnut Hill, MA 02467

Property at 16 Duxbury Rd, Newton Center, MA 02459, 3 beds, 2.5 baths

$1,338,000 Last sold price

3 beds2.5 baths2,550 sq ft

16 Duxbury Rd, Newton Center, MA 02459

Property at 77 Cotton St, Newton, MA 02458, 5 beds, 4.5 baths

$2,400,000 Last sold price

5 beds4.5 baths3,106 sq ft

77 Cotton St, Newton, MA 02458

Property at 45 Addington Rd #1, Brookline, MA 02445, 3 beds, 2 baths

$1,515,000 Last sold price

3 beds2 baths1,650 sq ft

45 Addington Rd #1, Brookline, MA 02445

Property at 144 Jordan Rd, Brookline, MA 02446, 3 beds, 1.5 baths

$1,820,000 Last sold price

3 beds1.5 baths1,943 sq ft

144 Jordan Rd, Brookline, MA 02446

Property at 310 Hammond Pond Pkwy #203, Chestnut Hill, MA 02467, 2 beds, 2 baths

$1,350,000 Last sold price

2 beds2 baths1,989 sq ft

310 Hammond Pond Pkwy #203, Chestnut Hill, MA 02467

Property at 3 Woodstock Ave #3, Brighton, MA 02135, 3 beds, 1 bath

$760,000 Last sold price

3 beds1 bath1,275 sq ft

3 Woodstock Ave #3, Brighton, MA 02135

Property at 249 Corey Rd #204, Boston, MA 02135, 1 bed, 1 bath

$772,500 Last sold price

1 bed1 bath760 sq ft

249 Corey Rd #204, Boston, MA 02135

Property at 12-32 Ransom Rd #23, Brighton, MA 02135

$28,000 Last sold price

0 beds— baths— sq ft

12-32 Ransom Rd #23, Brighton, MA 02135

Property at 185 Tappan St, Brookline, MA 02445, 5 beds, 5.5 baths

$4,350,000 Last sold price

5 beds5.5 baths3,593 sq ft

185 Tappan St, Brookline, MA 02445

Property at 12 Ransom Rd #44, Brighton, MA 02135

$29,950 Last sold price

0 beds— baths— sq ft

12 Ransom Rd #44, Brighton, MA 02135

Property at 20-28 Ransom Rd #29, Boston, MA 02135

$30,000 Last sold price

0 beds— baths— sq ft

20-28 Ransom Rd #29, Boston, MA 02135

Recently Sold Homes in Chestnut Hill

There are currently 14 recently sold homes 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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