South Brookline, MA homes for sale & real estate

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ABOUT THIS HOME
South Brookline, MA Homes for Sale
A once-in-a-lifetime opportunity to own a revived Tudor masterpiece, where historic grandeur meets modern sanctuary. Nestled gracefully on a hill amongst trees & over looking the Robert T. Lynch Golf Course, this residence exudes light, warmth, and timeless sophistication. The heart of the home is a sun-filled kitchen with dual marble islands, Sub-Zero and Thermador appliances, and a dining area that opens seamlessly to the two-story deck, backyard, and heated pool—perfect for both comfortable living and extraordinary entertaining. The grand living room showcases a hand-carved and restored fireplace, oversized windows, and French doors, blending classic craftsmanship with refine

$2,799,000

4 beds3 baths3,859 sq ft

1125 W Roxbury Pkwy, Chestnut Hill, MA 02467

Dual marble islands • Serene primary suite • Two-story deck

ABOUT THIS HOME
South Brookline, MA Homes for Sale
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

Gourmet kitchen • Versatile bonus room • 2 garage spots

FOR SALE BY OWNER

ABOUT THIS HOME
South Brookline, MA Homes for Sale
Spanish Tudor residence built in 1940 and completely renovated down to the studs in 2020, featuring two newly added bedrooms, a custom Waterworks kitchen with marble countertops and cabinetry, and a home theater.

$3,800,000

6 beds5 baths5,667 sq ft

16 South St, Chestnut Hill, MA 02467

Home theater • Marble countertops • 9,200 sq ft lot

ABOUT THIS HOME
South Brookline, MA Homes for Sale
Welcome to this exceptional 3-bedroom, 3.5-bathroom townhome in the heart of Brookline’s coveted Chestnut Hill neighborhood. Spanning three floors of thoughtfully designed living space, this home features a private elevator, central air, and in-unit laundry for ultimate comfort and convenience. Enjoy seamless entry with direct access from the garage for 2 parkings spaces, and relax outdoors on multiple balconies offering natural light and a connection to the serene surroundings. Each bedroom is generously sized, including a spacious primary suite with a spa-like bath. Located moments from scenic nature trails and just steps to the upscale shops, dining, and amenities at The Street, Th

$1,750,000

3 beds3.5 baths3,070 sq ft

771 Heath St #771, Chestnut Hill, MA 02467

Multiple balconies • Scenic nature trails • Private elevator

ABOUT THIS HOME
South Brookline, MA Homes for Sale
Turn Key residence blending classic charm and modern upgrades. Added square footage from a 2021 renovation. Major upgrades include new roof and rebuilt garage (2021) with Tesla charging station, furnace and A/C (2023), and on-demand water heater (2024). Features include a renovated kitchen (2018–2020) with dual-fuel stove, open floor plan, and oak hardwoods throughout. The living room boasts a stone accent wall, gas fireplace, and pre-wired Yamaha home theatre. Upstairs includes an expanded second bedroom and a third bedroom/optional suite (2021) with spa-like en suite. Primary bath (2025) offers heated floors and built-in storage. Finished basement (2024) with new tile, heating, and

$1,700,000

3 beds3.5 baths2,426 sq ft

83 Payson Rd, Chestnut Hill, MA 02467

Spa-like en suite • Stone accent wall • Gas fireplace

Property at 171 Shaw Rd, Chestnut Hill, MA 02467, 4 beds, 5.5 baths

$2,750,000

4 beds5.5 baths4,585 sq ft

171 Shaw Rd, Chestnut Hill, MA 02467

Property at 40 Heath Hill St, Brookline, MA 02445, 7 beds, 6.5 baths

$5,195,000

7 beds6.5 baths6,560 sq ft

40 Heath Hill St, Brookline, MA 02445

Property at 71 Sears Rd, Brookline, MA 02445, 6 beds, 5 baths

$12,500,000

6 beds5 baths7,502 sq ft

71 Sears Rd, Brookline, MA 02445

Property at 382 Lee St, Brookline, MA 02445, 5 beds, 5.5 baths

$5,995,000

5 beds5.5 baths6,841 sq ft

382 Lee St, Brookline, MA 02445

Property at 173 South St, Chestnut Hill, MA 02467, 4 beds, 2.5 baths

$2,495,000

4 beds2.5 baths2,841 sq ft

173 South St, Chestnut Hill, MA 02467

Property at 72 Wallis Rd, Chestnut Hill, MA 02467, 4 beds, 4.5 baths

$2,349,000

4 beds4.5 baths2,715 sq ft

72 Wallis Rd, Chestnut Hill, MA 02467

Property at 138 Woodland Rd, Chestnut Hill, MA 02467, 5 beds, 5.5 baths

$9,495,000

5 beds5.5 baths7,096 sq ft

138 Woodland Rd, Chestnut Hill, MA 02467

Property at 140 Dudley St, Brookline, MA 02445, 5 beds, 3.5 baths

$3,198,000

5 beds3.5 baths3,648 sq ft

140 Dudley St, Brookline, MA 02445

Property at 646 Newton St #2, Chestnut Hill, MA 02467, 4 beds, 3.5 baths

$1,475,000

4 beds3.5 baths2,660 sq ft

646 Newton St #2, Chestnut Hill, MA 02467

Property at 34 Lagrange St, Chestnut Hill, MA 02467, 5 beds, 3.5 baths

$2,895,000

5 beds3.5 baths5,076 sq ft

34 Lagrange St, Chestnut Hill, MA 02467

Property at 80 Dudley St, Brookline, MA 02445, 7 beds, 9 baths

$9,995,000

7 beds9 baths7,240 sq ft

80 Dudley St, Brookline, MA 02445

Property at 21 Sargent Crossway, Brookline, MA 02445, 5 beds, 6.5 baths

$8,000,000

5 beds6.5 baths5,772 sq ft

21 Sargent Crossway, Brookline, MA 02445

Property at 100 Cottage St, Brookline, MA 02445, 6 beds, 7.5 baths

$6,995,000

6 beds7.5 baths9,380 sq ft

100 Cottage St, Brookline, MA 02445

Property at 811 Heath St, Chestnut Hill, MA 02467, 4 beds, 4.5 baths

$2,299,000

4 beds4.5 baths3,193 sq ft

811 Heath St, Chestnut Hill, MA 02467

Property at 75 Goddard Ave, Brookline, MA 02445, 7 beds, 8 baths

$6,499,000

7 beds8 baths6,000 sq ft

75 Goddard Ave, Brookline, MA 02445

Property at 809-811 Heath St #811, Chestnut Hill, MA 02467, 4 beds, 4.5 baths

$2,299,000

4 beds4.5 baths3,193 sq ft

809-811 Heath St #811, Chestnut Hill, MA 02467

Property at 79 Goddard Ave, Brookline, MA 02445

$3,500,000

— beds— baths— sq ft

79 Goddard Ave, Brookline, MA 02445

Property at 39 Clyde St, Chestnut Hill, MA 02467

$8,000,000

— beds— baths— sq ft

39 Clyde St, Chestnut Hill, MA 02467

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Average home prices near South Brookline, MA

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South Brookline, MA real estate trends

All Home Types trends in South Brookline, MA

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$1,650,000

-13.4% YoY | Oct 2025

1 year
3 year
5 year

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

Location

Data

Oct 2025

Growth

% YoY

South Brookline, MA

$1,650,000

-13.4%

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