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20+ Houses for Sale in Chestnut Hill, MA

27 results

Property at 77 Payson Rd, Brookline, MA 02467
1 / 35
Active
New
Open

$849,900

77 Payson Rd, Brookline, MA 02467

3 bds
|
1 ba
|
1401 sqft
MLS® 73594577Single Family Residence
Vogt Realty Group, LLC - Patsy Brennan
Property at 79 Randolph Road, Brookline, MA 02467
1 / 35
Active
Open

$2,799,999

79 Randolph Road, Brookline, MA 02467

4 bds
|
3.5 ba
|
3225 sqft
MLS® 73592951Single Family Residence
Columbus and Over Group, LLC - Jeffrey Hamilton
Property at 198 Clyde Street, Brookline, MA 02467
1 / 33
Active
Price

$6,400,000

198 Clyde Street, Brookline, MA 02467

4 bds
|
4.5 ba
|
6521 sqft
MLS® 73500458Single Family Residence
Campion & Company Fine Homes Real Estate - Tracy Campion
Property at 79 Woodchester Dr, Newton, MA 02467
1 / 30
Active
Open

$2,495,000

79 Woodchester Dr, Newton, MA 02467

4 bds
|
4.5 ba
|
4340 sqft
MLS® 73578296Single Family Residence
Romo Realty Group - Jarrod L. Pescosolido
Property at 80 High Rock Ter, Newton, MA 02467
1 / 42
Active
Price
Open

$3,150,000

80 High Rock Ter, Newton, MA 02467

5 bds
|
6.5 ba
|
6535 sqft
MLS® 73581626Single Family Residence
REMAX Andrew Realty Services - Sissi Zhang

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Property at 284 Woodland Road, Brookline, MA 02467
1 / 38
Active
Price
Open

$2,595,000

284 Woodland Road, Brookline, MA 02467

5 bds
|
4.5 ba
|
3913 sqft
MLS® 73573502Single Family Residence
eXp Realty LLC - The Denman Group
Property at 133 Wolcott Road, Brookline, MA 02467
1 / 22
Active
Price
Open

$1,649,000

133 Wolcott Road, Brookline, MA 02467

4 bds
|
3 ba
|
2500 sqft
MLS® 73572511Single Family Residence
Coldwell Banker Realty - Brookline - Mary Lochner
Property at 30 Hackensack Road, Brookline, MA 02467
1 / 31
Active Under Contract

$995,000

30 Hackensack Road, Brookline, MA 02467

3 bds
|
1.5 ba
|
1350 sqft
MLS® 73590431Single Family Residence
Coldwell Banker Realty - Belmont - Delrose Mcshane Team
Property at 72 Beverly Rd, Brookline, MA 02467
1 / 42
Active Under Contract

$2,395,000

72 Beverly Rd, Brookline, MA 02467

4 bds
|
4.5 ba
|
4067 sqft
MLS® 73569446Single Family Residence
Coldwell Banker Realty - Brookline - Ovesen Group
Property at 334 Hammond St, Newton, MA 02467
1 / 37
Active

$7,995,000

334 Hammond St, Newton, MA 02467

8 bds
|
7.5 ba
|
10219 sqft
MLS® 73590108Single Family Residence
Douglas Elliman Real Estate - The Sarkis Team - The Sarkis Team
Property at 764 Hammond St, Brookline, MA 02467
1 / 31
Active
Price

$1,750,000

764 Hammond St, Brookline, MA 02467

4 bds
|
3 ba
|
3000 sqft
MLS® 73482825Single Family Residence
Conway - West Roxbury - Kevin Gingras
Property at 109 Wallis Road, Brookline, MA 02467
1 / 13
Active Under Contract
Price

$1,495,000

109 Wallis Road, Brookline, MA 02467

3 bds
|
2 ba
|
2100 sqft
MLS® 73579467Single Family Residence
Coldwell Banker Realty - Brookline - Jayne Friedberg
Property at 129 Rangeley Rd, Brookline, MA 02467
1 / 42
Active
Price

$4,650,000

129 Rangeley Rd, Brookline, MA 02467

6 bds
|
6.5 ba
|
6359 sqft
MLS® 73532609Single Family Residence
Keller Williams Realty - Ingvild Brown
Property at 90 Suffolk Rd, Newton, MA 02467
1 / 18
Active

$4,980,000

90 Suffolk Rd, Newton, MA 02467

5 bds
|
5.5 ba
|
5919 sqft
MLS® 73579970Single Family Residence
Coldwell Banker Realty - Brookline - Deborah M. Gordon
Property at 17 Glenoe Rd, Brookline, MA 02467
1 / 34
Active
Price
Open

$3,695,000

17 Glenoe Rd, Brookline, MA 02467

4 bds
|
4.5 ba
|
4884 sqft
MLS® 73573585Single Family Residence
Coldwell Banker Realty - Brookline - Jamie Genser
Property at 91 Grove, Brookline, MA 02467
1 / 18
Active
Price

$1,395,000

91 Grove, Brookline, MA 02467

3 bds
|
2 ba
|
2370 sqft
MLS® 73575003Single Family Residence
The Statesmen Group, LLC - Eric Seitz
Property at 31 Kesseler Way, Newton, MA 02467
1 / 32
Active
Price

$3,499,999

31 Kesseler Way, Newton, MA 02467

6 bds
|
6 ba
|
8146 sqft
MLS® 73568425Single Family Residence
Serhant - Samantha Stumpo
Property at 9 Singletree Rd, Brookline, MA 02467
1 / 19
Active
Price
Open

$4,795,000

9 Singletree Rd, Brookline, MA 02467

4 bds
|
4.5 ba
|
6790 sqft
MLS® 73520842Single Family Residence
Coldwell Banker Realty - Brookline - Deborah M. Gordon
Property at 22 Scotney Road, Newton, MA 02467
1 / 42
Active
Price

$3,399,000

22 Scotney Road, Newton, MA 02467

7 bds
|
6.5 ba
|
6140 sqft
MLS® 73494324Single Family Residence
William Raveis R. E. & Home Services - Esin Susol Team
Property at 401 Heath Street, Brookline, MA 02467
1 / 30
Active
Open

$2,765,000

401 Heath Street, Brookline, MA 02467

5 bds
|
3.5 ba
|
4028 sqft
MLS® 73572599Single Family Residence
Compass - Hilary Maddox Team
Property at 188 Heath St, Brookline, MA 02467
1 / 41
Active
Price

$8,995,000

188 Heath St, Brookline, MA 02467

6 bds
|
6.5 ba
|
7232 sqft
MLS® 73479457Single Family Residence
Hammond Residential Real Estate - The Kennedy Lynch Team
Property at 1014 Boylston Street, Brookline, MA 02467
1 / 38
Active
Price

$16,980,000

1014 Boylston Street, Brookline, MA 02467

7 bds
|
9.5 ba
|
13343 sqft
MLS® 73445544Single Family Residence
Campion & Company Fine Homes Real Estate - Tracy Campion
Property at 331 Heath Street, Brookline, MA 02467
1 / 31
Active
Price

$3,750,000

331 Heath Street, Brookline, MA 02467

3 bds
|
3.5 ba
|
3790 sqft
MLS® 73481377Single Family Residence
Gibson Sotheby's International Realty - Bobby Morgenstern
Property at 365 Newton St, Brookline, MA 02467
1 / 35
Active

$2,399,000

365 Newton St, Brookline, MA 02467

4 bds
|
3 ba
|
3243 sqft
MLS® 73547641Single Family Residence
Blue Ocean Realty, LLC - Rose Hall
Property at 394 Hammond St, Newton, MA 02467
1 / 24
Active
Price

$5,627,000

394 Hammond St, Newton, MA 02467

9 bds
|
5.5 ba
|
8485 sqft
MLS® 73469901Single Family Residence
Coldwell Banker Realty - Boston - Michael Harper
Property at 40 Singletree Rd, Brookline, MA 02467
1 / 23
Active

$8,200,000

40 Singletree Rd, Brookline, MA 02467

6 bds
|
7.5 ba
|
9301 sqft
MLS® 73526856Single Family Residence
MGS Group Real Estate LTD - Maggie Gold Seelig
Property at 68 Clyde Street, Brookline, MA 02467
1 / 25
Active

$9,985,000

68 Clyde Street, Brookline, MA 02467

5 bds
|
7 ba
|
7300 sqft
MLS® 73478330Single Family Residence
MGS Group Real Estate LTD - Maggie Gold Seelig

Brokerage Information

Gundersheim Group Real Estate

10 Lincoln St, Newton, MA, 02461

(617) 997-8272

Market Area Served

Boston, Brookline, Newton, Needham, Wellesley, Somerville and many more.

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

Melanie Gundersheim

Greater Boston real estate, thoughtfully navigated. Combining local expertise, strategic negotiation and concierge-level personal service to help you buy, sell, and invest with confidence.

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  • 10 Lincoln St, Newton, MA, 02461
  • (617) 997-8272
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© 2026 Melanie Gundersheim. All rights reserved.
Equal Housing Opportunity. Information deemed reliable but not guaranteed.

Houses for sale in Chestnut Hill, MA: market at a glance

As of October 24, 2026, there are 27 single-family homes for sale in Chestnut Hill, MA, with a median list price of $3,399,000.

Houses for sale
27
Median list price
$3,399,000

Homes for sale near Chestnut Hill

  • Brighton, MA
  • Newton Highlands, MA
  • Brookline, MA
  • Newton, MA
  • Newton Center, MA
  • Allston, MA
  • Brookline Village, MA
  • Newtonville, MA

Common questions about Chestnut Hill, MA real estate

How many single-family homes are for sale in Chestnut Hill, MA?

As of October 24, 2026, there are 27 single-family homes for sale in Chestnut Hill, MA.

What is the median single-family home price in Chestnut Hill, MA?

The median list price of single-family homes for sale in Chestnut Hill, MA is $3,399,000.

How long do homes take to sell in Chestnut Hill, MA?

Single-family homes currently for sale show a median of about 37 days on market.