Chestnut Hill, MA homes for sale & real estate

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ABOUT THIS HOME
Chestnut Hill, MA Homes for Sale
New to Market! Don’t miss this rare opportunity to own a beautifully maintained, sun-filled 3BR, 1.5BA condo in one of Brookline’s most sought-after locations. This inviting home features an open and airy floor plan with high ceilings, oversized windows, and abundant natural light throughout. Well-appointed kitchen boasts maple cabinetry, granite countertops, stainless steel appliances, gas cooking, and a spacious island with bar seating—perfect for both everyday living and entertaining. Additional highlights include two deeded side-by-side parking spaces (a true rarity in Brookline), low condo fees, new siding, roof, and gutters, fully deleaded. Enjoy an unbeatable locati

$799,000

3 beds1.5 baths1,087 sq ft

55 Reservoir Rd #2, Chestnut Hill, MA 02467

High ceilings • Oversized windows • Maple cabinetry

ABOUT THIS HOME
Chestnut Hill, MA Homes for Sale
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
Chestnut Hill, MA Homes for Sale
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
Chestnut Hill, MA Homes for Sale
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
Chestnut Hill, MA Homes for Sale
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

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 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 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 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 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 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 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

Property at 682 Hammond, Chestnut Hill, MA 02467, 5 beds, 5.5 baths

$6,748,000

5 beds5.5 baths6,551 sq ft

682 Hammond, Chestnut Hill, MA 02467

Property at 0 Glenoe Rd, Chestnut Hill, MA 02467

$2,295,000

— beds— baths— sq ft

0 Glenoe Rd, Chestnut Hill, MA 02467

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ABOUT THIS HOME
Chestnut Hill, MA Homes for Sale
Beautifully renovated 3rd-floor condo in prime Brookline! High ceilings, open layout, exposed brick, and gleaming oak hardwood floors. The modern kitchen shines with brand-new stainless-steel appliances, quartz countertops, and a striking quartz backsplash. Newly renovated bathroom with updated vanity and fixtures. Bright living and dining area with a spacious bedroom. Professionally managed building with heat and hot water included in low condo fee. Laundry on-site. Ideally located at Beacon & Englewood with easy access to the Green C Line, shops, restaurants, parks, playgrounds, Washington Square, Coolidge Corner, and Longwood Medical Area. Englewood T-stop right outside. First Open

$589,000

1 bed1 bath680 sq ft

3 Englewood Ave #9, Brookline, MA 02445

$283 HOA • Community pool • Very walkable

NEW 19 HRS AGO3D WALKTHROUGH

ABOUT THIS HOME
Chestnut Hill, MA Homes for Sale
BRAND NEW, FULLY GUT RENOVATED APARTMENT BUILDING FOR SALE OFF COMM AVE - Turnkey/Condo quality 7 unit apartment building located in a prime Allston location. ~$402,600 Gross income through 8/31/26. Lots of upside potential in the rents! All plumbing and electrical was newly updated, a full sprinkler system was installed, new energy efficient windows, designer Kitchens & Bathrooms, Gleaming New Hardwood flooring. Brand New Gas HVAC and separate water meters (Tenants pay all utilities). The property is located in between Boston College, Boston University, Saint Elizabeth's Medical Center, New Balance Headquarters as well as the ever-expanding Boston Landing mixed-use project. The subj

$5,800,000

25 beds8 baths6,690 sq ft

159-161 Allston, Allston, MA 02134

3,765 sq ft lot • Walker's paradise

NEW CONSTRUCTION

ABOUT THIS HOME
Chestnut Hill, MA Homes for Sale
3.5% COBROKE! for any P & S signed in November! Live the life of luxury on higher ground! Introducing 1515 Comm. Ave, the newest luxury condo community in the heart of vibrant Brighton. Designed and built to foster positive Feng Shui, our 102 meticulously crafted homes combine comfort and style with high-end fixtures, premium appliances and open layouts that enhance your everyday living experience. With residences ranging from Studios-3Beds, we have over 15 layouts for you to choose from. Amenities include- 24/7 concierge, co-working and private WFH spaces, fitness center equipped w/ on-demand fitness, expansive clubroom w/ catering kitchen, multi-sports simulator w/ wet bar, 2nd level

$899,000

1 bed1 bath909 sq ft

1515 Commonwealth Ave #615, Boston, MA 02135

$910 HOA • Garage • Very walkable

ABOUT THIS HOME
Chestnut Hill, MA Homes for Sale
Rare offering at the Historic Selkirk Estate. Recently built luxury townhome blending timeless design with modern convenience. Open floor plan features a chef’s kitchen with premium quartz, custom cabinetry, stainless steel appliances, & an oversized island open to bright dining/living areas. Glass doors lead to a private, wooded backyard with deck, a rare find in this location. Second floor offers two spacious en-suite bedrooms & laundry. The top floor is dedicated to a stunning primary retreat with treetop views, a walk-in closet, & spa-inspired bath. A beautifully finished home theater/media room provides flexible use for entertainment, office, gym, or play. Two dee

$1,799,000

3 beds3.5 baths2,760 sq ft

24 Selkirk Unit 24-4, Boston, MA 02135

$400 HOA • Community pool • Very walkable

ABOUT THIS HOME
Chestnut Hill, MA Homes for Sale
R4 zoning. Currently a legal 4 family. Changed from a 3 family to 4 family in 2000. Development opportunity. Attention investors, developers, owner occupants. Rehab project located in lovely Brighton neighborhood area bordering Brookline. Short distance to MBTA green C, D, B lines. Value add opportunity. 17 room, 8 bedrooms, 5 full baths and 2 half baths. 11 parking spaces including large garage. No leases in place. Motivated seller. Offered in “AS IS” condition. 12,949 sqft lot. Total area of home 8032 sqft. Do not miss this opportunity. Buyer to perform due diligence prior to submitting offer. Nearby Chestnut Hill Reservoir, Boston College, and vibrant Beacon Street neighborh

$2,500,000

8 beds6 baths5,093 sq ft

155 Kilsyth Rd, Brighton, MA 02135

0.3 acre lot • 3 garage spots • Community pool

ABOUT THIS HOME
Chestnut Hill, MA Homes for Sale
Experience effortless Newton living in this move-in ready and updated home at 266 Langley Road unit 1— a beautifully appointed 3 bedroom townhouse in the heart of Newton Centre that truly lives like a single family. This residence offers bright, open living spaces, high ceilings, and effortless day-to-day functionality. The kitchen opens to a dining area and living room with direct access to a private deck — perfect for relaxing, entertaining, or everyday living. Three generously sized bedrooms on the upper level include a serene primary suite with ample closet space and a well-appointed bath in addition to a private second family room as well. Exceptional location near Newton C

$1,550,000

3 beds2.5 baths2,035 sq ft

266 Langley Rd #1, Newton, MA 02459

$350 HOA • Somewhat walkable

Property at 250 Hammond Pond Pkwy Unit 614S, Chestnut Hill, MA 02467, 2 beds, 2 baths

$789,000

2 beds2 baths1,240 sq ft

250 Hammond Pond Pkwy Unit 614S, Chestnut Hill, MA 02467

Property at 97 Strathmore Rd #4, Brighton, MA 02135, 1 bed, 1 bath

$499,000

1 bed1 bath719 sq ft

97 Strathmore Rd #4, Brighton, MA 02135

Property at 44 Irving St, Newton Center, MA 02459, 4 beds, 2 baths

$1,375,000

4 beds2 baths2,408 sq ft

44 Irving St, Newton Center, MA 02459

Property at 16 Eastburn Unit A, Brighton, MA 02135, 2 beds, 2.5 baths

$800,000

2 beds2.5 baths1,420 sq ft

16 Eastburn Unit A, Brighton, MA 02135

Property at 230 Washington St #11, Brighton, MA 02135, 1 bed, 1 bath

$699,000

1 bed1 bath712 sq ft

230 Washington St #11, Brighton, MA 02135

Property at 1515 Commonwealth Ave #303, Boston, MA 02135, 1 bed, 1 bath

$769,000

1 bed1 bath717 sq ft

1515 Commonwealth Ave #303, Boston, MA 02135

Property at 39 Union St, Brighton, MA 02135, 9 beds, 3 baths

$2,099,000

9 beds3 baths3,615 sq ft

39 Union St, Brighton, MA 02135

Property at 250 Hammond Pond Pkwy Unit 1604N, Chestnut Hill, MA 02467, 1 bed, 1.5 baths

$599,000

1 bed1.5 baths899 sq ft

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

Property at 799 Heath St #2, Chestnut Hill, MA 02467, 4 beds, 2.5 baths

$1,749,000

4 beds2.5 baths2,366 sq ft

799 Heath St #2, Chestnut Hill, MA 02467

Property at 173-175 Warren St, Newton Center, MA 02459, 7 beds, 2 baths

$1,800,000

7 beds2 baths2,476 sq ft

173-175 Warren St, Newton Center, MA 02459

Property at 90 Addington #2, Brookline, MA 02445, 5 beds, 3.5 baths

$3,195,000

5 beds3.5 baths3,250 sq ft

90 Addington #2, Brookline, MA 02445

Property at 1304 Commonwealth Ave #5, Boston, MA 02134, 3 beds, 2.5 baths

$1,190,000

3 beds2.5 baths1,985 sq ft

1304 Commonwealth Ave #5, Boston, MA 02134

Property at 36 Colborne Rd, Brighton, MA 02135, 27 beds, 19 baths

$8,500,000

27 beds19 baths10,455 sq ft

36 Colborne Rd, 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

Average home prices near Chestnut Hill, MA

Cities

Neighborhoods

Jamaica Plain homes for sale
$794,000
Roslindale homes for sale
$710,000
Fenway-Kenmore homes for sale
$1,737,500
Cambridgeport homes for sale
$970,000
Brighton homes for sale
$748,000
Mission Hill homes for sale
$504,950
Fenway / Kenmore Square homes for sale
$1,229,000
Allston homes for sale
$598,000
West Roxbury homes for sale
$806,950
Coolidge Corner homes for sale
$1,710,000

Chestnut Hill, MA real estate trends

All Home Types trends in Chestnut Hill, MA

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$1,814,000

-10.4% YoY | Sep 2025

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

Sep 2025

Growth

% YoY

Chestnut Hill, MA

$1,814,000

-10.4%

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