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

OPEN SUN, 12PM TO 1PM

ABOUT THIS HOME
South Brookline, MA Homes for Sale
Welcome to a meticulously rebuilt modern gem in Brookline! Completely reimagined from the studs, this open-concept home features 4 bedrooms, 4 full baths, and a convenient first-floor powder room. The main level flows effortlessly, with a spacious family/living room, dining area, and a chef's kitchen equipped with Thermador appliances, sleek handle-less cabinetry, quartz countertops, and an entertainer’s island. Upstairs, a serene bedroom with an ensuite offers privacy and comfort. The lower level reveals a luxurious primary suite with a spa-like bath and walk-in closet, two additional bedrooms, and a family/playroom. Outside, you'll find a beautifully landscaped front yard and a pea

$2,349,000

4 beds4.5 baths2,715 sq ft

72 Wallis Rd, Chestnut Hill, MA 02467

Open-concept home • Quartz countertops • Thermador appliances

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
Built in 2022 by one of Boston’s premier luxury builders, this masterfully crafted residence redefines modern elegance and sophistication. From the moment you enter the dramatic two-story foyer, the home sets the stage for grand entertaining and refined living. The expansive first floor showcases palatial rooms, a formal sitting room, a library, and an expansive guest suite. At the heart of the home is a custom-designed kitchen paired with a fully outfitted prep kitchen, both featuring top-of-the-line appliances for effortless hosting. A spacious mudroom completes the main level with style and function. Upstairs, the primary suite offers the ultimate retreat: an oversized bedroom with

$9,495,000

5 beds5.5 baths7,096 sq ft

138 Woodland Rd, Chestnut Hill, MA 02467

Primary suite • Spacious mudroom • Two story foyer

ABOUT THIS HOME
South Brookline, MA Homes for Sale
Elegance and modernity define this sunlit Chestnut Hill residence on the Reservoir, offering spacious rooms, an open layout and luxurious finishes. Minutes from Boston and recently built by a local top builder for the current owners, every detail reflects meticulous craftsmanship, state-of-the-art systems and thoughtful design. A grand staircase separates entertaining areas from private spaces and expansive windows and French doors lead outside, ideal for indoor-outdoor entertaining. A gourmet kitchen with Cesar stone/wood island and top appliances, family room, screened in porch w/ fireplace and TV and an outdoor kitchen complete the 1st level. The primary suite features a marble spa-like

$9,995,000

7 beds9 baths7,240 sq ft

80 Dudley St, Brookline, MA 02445

Screened in porch • Marble spa-like bath • Custom dressing room

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 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 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

$3,150,000

— 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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NEW 14 HRS AGO

ABOUT THIS HOME
South Brookline, MA Homes for Sale
Turnkey 2 bedroom 2 full bath pristine unit at Chestnut Hill Towers. Towers amenities include: 24-hour security/concierge, year-round indoor heated swimming pool, outdoor tennis courts, pickleball court, 24-hour onsite gym access, resident lounge and game room, Minutes to the Chestnut Hill Mall and The "Street" shopping. Easy access to Longwood, Back Bay, Beacon Hill, South End and Financial District. 2 deeded garage parking spaces included in the sale.

$850,000

2 beds2 baths1,285 sq ft

250 Hammond Pond Pkwy Unit 603N, Chestnut Hill, MA 02467

Pickleball court • Resident lounge • Game room

OPEN TODAY, 12PM TO 1:30PM

ABOUT THIS HOME
South Brookline, MA Homes for Sale
Prime three-family opportunity with strong upside potential. Public record reflects 5 beds / 3 baths, while the current layout offers 7 beds / 3 baths (buyer to do due diligence). Ideal for investors or owner-occupants seeking flexible living and income potential. Conveniently located near MBTA Forest Hills with easy access to bus routes, the Orange Line, and downtown Boston. Situated on Main Street, the property features a large lot with ample off-street parking and a spacious backyard, a rare find for a multi-family in this location. The basement offers potential for an ADU (subject to zoning and city approval), providing additional value and future expansion possibilities. A well-located

$1,125,000

5 beds3 baths3,343 sq ft

3886-3888 Washington, Roslindale, MA 02131

Large lot • 5,906 sq ft lot • Built 1890

ABOUT THIS HOME
South Brookline, MA Homes for Sale
Wonderful opportunity for builder or end user. 3 bedrooms, 2.5 bathrooms, large livingroom with fireplace, diningroom, kitchen and large family room. Beautiful landscaped yard. C/A, Spaulding elementary school and Newton South HS.

$1,775,000

3 beds2.5 baths1,500 sq ft

17 Tirrell Cres, Chestnut Hill, MA 02467

Landscaped yard • Fireplace • 0.33 acre lot

ABOUT THIS HOME
South Brookline, MA Homes for Sale
Discover the potential of 104 Greaton Road, a versatile two-unit multifamily home in a prime West Roxbury location, ideally situated near Centre Street shops, Hynes Playground park, and Independence Village in Chestnut Hill. The living and dining rooms feature large windows and effortless flow, perfect for relaxation and entertaining. The semi-finished attic invites creativity, offering potential for two additional bedrooms or a luxurious primary suite. Original woodwork, hardwood floors, and built-ins grace the home, adding warmth and character throughout. Multiple 3-season enclosed porches are perfect for enjoying the changing seasons and a detached garage provides ample storage space. Th

$1,100,000

4 beds2 baths2,640 sq ft

104 Greaton Rd, West Roxbury, MA 02132

Semi finished attic • Original woodwork • 5,000 sq ft lot

3D WALKTHROUGH

ABOUT THIS HOME
South Brookline, MA Homes for Sale
Open House Sat 12-1:30 PM. Beautiful brick Brookline single-family was fully-renovated by well-known local builder. Timeless curb appeal w/ all-new systems & high-end designer-selected finishes throughout. The interior features a thoughtful modern layout w/ 4 bedrooms, 3.5 bathrooms, a large bonus space & full walkout lower level, providing exceptional flexibility for living, entertaining & working from home. Set on a corner, fenced-in lot w/ plenty of parking, the property enjoys unmatched access to outdoor amenities. Directly beside the newly renovated Margaret E. Robinson Playground, w/ plenty of green space, dog-friendly Green Dog Program & multi-use courts. You&

$2,250,000

4 beds3.5 baths2,332 sq ft

209 High St, Brookline, MA 02445

Green space • Fully renovated • Multi use courts

ABOUT THIS HOME
South Brookline, MA Homes for Sale
Approved plans re-imagine this property as a sophisticated three-level single-family home that seamlessly blends historic character with modern livability. The 3,080-square-foot design transforms the existing carriage house into an open, light-filled residence featuring connected living and dining spaces, a modern kitchen with direct access to a private garden and bluestone terrace, and a functional mudroom entry. Upstairs, four well-proportioned bedrooms and 2.5 baths offer flexibility and comfort, while the finished lower level provides valuable space for a fifth bedroom, office, or gym and bathroom. The approved site plan includes two off-street parking spaces, privacy fencing, and profe

$995,000

0 beds— baths— sq ft

12 Thayer St, Brookline, MA 02445

Private garden • Bluestone terrace • Modern kitchen

Property at 44 Broadlawn Park Unit 22A, Chestnut Hill, MA 02467, 2 beds, 1 bath

$489,900

2 beds1 bath888 sq ft

44 Broadlawn Park Unit 22A, Chestnut Hill, MA 02467

Property at 675 Chestnut Hill Ave, Brookline, MA 02445, 4 beds, 2 baths

$1,999,999

4 beds2 baths1,920 sq ft

675 Chestnut Hill Ave, Brookline, MA 02445

Property at 20 Hamlet St #1, Newton, MA 02459, 3 beds, 4 baths

$1,899,000

3 beds4 baths3,669 sq ft

20 Hamlet St #1, Newton, MA 02459

Property at 19 Delford St #1, Roslindale, MA 02131, 3 beds, 1.5 baths

$599,900

3 beds1.5 baths1,580 sq ft

19 Delford St #1, Roslindale, MA 02131

Property at 142 Crafts Rd, Chestnut Hill, MA 02467, 8 beds, 6.5 baths

$8,750,000

8 beds6.5 baths9,400 sq ft

142 Crafts Rd, Chestnut Hill, MA 02467

Property at 19 Delford St, Roslindale, MA 02131, 3 beds, 1.5 baths

$599,900

3 beds1.5 baths1,580 sq ft

19 Delford St, Roslindale, MA 02131

Property at 42 Bryon Rd #6, Chestnut Hill, MA 02132, 2 beds, 1 bath

$449,900

2 beds1 bath780 sq ft

42 Bryon Rd #6, Chestnut Hill, MA 02132

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 18-20 Northbourne Rd #18, Boston, MA 02130, 2 beds, 1.5 baths

$789,000

2 beds1.5 baths1,302 sq ft

18-20 Northbourne Rd #18, Boston, MA 02130

Property at 36 Ober Rd #36, Newton, MA 02459, 2 beds, 1 bath

$795,000

2 beds1 bath881 sq ft

36 Ober Rd #36, Newton, MA 02459

Property at 63 Drumlin Rd, Newton Center, MA 02459, 6 beds, 6.5 baths

$4,580,000

6 beds6.5 baths6,653 sq ft

63 Drumlin Rd, Newton Center, MA 02459

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

$1,595,000

3 beds3 baths3,096 sq ft

38 Tanglewood Rd #38, Newton Center, MA 02459

Property at 70 Pond Brk, Chestnut Hill, MA 02467, 6 beds, 6 baths

$3,700,000

6 beds6 baths6,300 sq ft

70 Pond Brk, Chestnut Hill, MA 02467

Property at 487 Boylston St #3, Brookline, MA 02445, 4 beds, 2 baths

$1,440,000

4 beds2 baths2,276 sq ft

487 Boylston St #3, Brookline, MA 02445

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)

$1,499,000

-7.8% YoY | Nov 2025

1 year
3 year
5 year

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

Location

Data

Nov 2025

Growth

% YoY

South Brookline, MA

$1,499,000

-7.8%

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