SOLD OCT 14, 2026

Sold on oct 2026

$2,800,000

•

2,992

sq ft

44 Valley Rd, Chestnut Hill, MA 02467

Track this home’s value and nearby sales activity

About this home

Discover timeless elegance and exceptional versatility in this beautifully updated 1938 Cape, thoughtfully designed for today's discerning family. Offering 6 bedrooms and 3.5 baths, the home features two primary bedrooms with private ensuite baths, including a sought-after first-floor retreat ideal for multigenerational living, guests, or an au pair. The chef's kitchen is appointed with stainless steel appliances, a gas range, wall oven, stone countertops, and a center island with seating for three. A welcoming den, formal dining room, and sun-filled breakfast area provide inviting settings for both everyday life and elegant entertaining. The finished lower level offers a versatile recreation room with a dedicated laundry area. Completing the home are an attached two-car garage and two additional off-street parking spaces, blending classic New England charm with modern comfort and convenience. Close to Roland Hayes School & Brookline High School, Route 9, Chestnut Hill Reservoir, Golf Courses, Green Line (MBTA) and The Mall at Chestnut Hill. Quick drives to Newton Centre or Brookline hubs for everyday groceries and dining.

Single-familyProperty Type

1938Year Built

0.33 acresLot Size

$936Price/Sq.Ft.

2 garage spacesParking

Listed by The Kelleher Spalding Team • Gibson Sotheby's International Realty

Listed by Gibson Sotheby's International Realty

Bought with Joshua Stiles • Compass

Redfin checked: 2 minutes ago

•Source:MLS PIN #73558881

Redfin Estimate

$2,612,743

$187K since sold in October 2026$9,000 since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 1.2% lower than the average sale price ($2.64M) of 6 comparable homes.

SOLD JUN 15, 2026
$2,200,000
A
5 beds3.5 baths3,463 sq ft
401 Clinton Rd, Brookline, MA 02445
SOLD AUG 21, 2026
$2,394,900
B
4 beds3.5 baths2,996 sq ft
520 Clinton Rd, Chestnut Hill, MA 02467
SOLD JUN 26, 2026
$2,950,000
C
4 beds3.5 baths3,230 sq ft
59 Randolph, Chestnut Hill, MA 02467
SOLD JUL 29, 2026
$2,200,000
D
4 beds3.5 baths2,800 sq ft
25 Chestnut Hill Rd, Chestnut Hill, MA 02467
SOLD OCT 5, 2026
$2,900,000
E
5 beds3.5 baths6,196 sq ft
460 Heath St, Chestnut Hill, MA 02467
SOLD JUN 29, 2026
$3,215,000
F
4 beds3.5 baths3,002 sq ft
236 Mason Ter, Brookline, MA 02446

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Market trends in 02467, MA

Last updated September 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-list price

99.4%

0.1% MoM

Median sale price

$1.6M

$50K MoM

Avg. days on market

41d

15 days MoM

Recently sold homes

11 MoM

New listings for sale

OPEN SAT, 11AM TO 12PM
$2,799,999
4 beds3.5 baths3,225 sq ft
79 Randolph Rd, Chestnut Hill, MA 02467
$1,900,000
2 beds3 baths2,465 sq ft
99 Florence St Unit 10-5B, Chestnut Hill, MA 02467
$1,600,000
2 beds2.5 baths2,943 sq ft
210 Allandale Rd Unit 1C, Chestnut Hill, MA 02467
$529,000
1 bed1.5 baths899 sq ft
250 Hammond Pond Pkwy Unit 812 N, Chestnut Hill, MA 02467
$959,000
2 beds2 baths1,350 sq ft
321 Hammond Pond Pkwy #103, Chestnut Hill, MA 02467
$2,875,000
2 beds3.5 baths3,090 sq ft
99 Florence Unit 5A-50, Chestnut Hill, MA 02467
$34,000,000
7 beds13 baths19,138 sq ft
55 Singletree Rd, Chestnut Hill, MA 02467
OPEN SAT, 1:30PM TO 2:30PM
$1,589,000
4 beds3.5 baths4,345 sq ft
101 Hackensack Rd, Chestnut Hill, MA 02132
$7,995,000
8 beds7.5 baths10,219 sq ft
334 Hammond St, Chestnut Hill, MA 02467
OPEN SUN, 1PM TO 2PM
$750,000
2 beds2 baths1,285 sq ft
250 Hammond Pond Pkwy Unit 1611S, Chestnut Hill, MA 02467
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Rental estimate

Est. $7,023 per month, based on comparable rentals

Sale and tax history for 44 Valley Rd

Sale History
Tax History

Year

Property tax

Land + Additions

Assessment*

2023

$20,309 (+2.7%)

$1,065,800 + $971,200

$2,037,000

2022

$19,768 (+8.1%)

$1,015,000 + $924,900

$1,939,900

2021

$18,281 (+9.7%)

$976,000 + $889,400

$1,865,400

2020

$16,669 (+5.9%)

$887,300 + $876,600

$1,763,900

2019

$15,741 (+0.3%)

$845,000 + $834,900

$1,679,900

2018

$15,691 (+1.5%)

$847,200 + $811,500

$1,658,700

2017

$15,460 (+1.5%)

$799,300 + $765,500

$1,564,800

2016

$15,239 (+5.0%)

$747,000 + $715,500

$1,462,500

2015

$14,518 (+0.3%)

$698,100 + $661,300

$1,359,400

2014

$14,477 (+0.7%)

$634,600 + $636,400

$1,271,000

2013

$14,376 (+2.2%)

$616,100 + $617,900

$1,234,000

2012

$14,068 (+0.8%)

$616,100 + $617,900

$1,234,000

2011

$13,952 (+3.0%)

$627,300 + $607,400

$1,234,700

2010

$13,545 (+2.8%)

$627,300 + $607,400

$1,234,700

2009

$13,178

$625,400 + $607,300

$1,232,700

Public record

Public record
Permits

Beds

Baths

3.5

Stories

Lot width

—

Lot depth

—

Lot size

0.33 Acres

Year renovated

1974

Sq. Ft.

2,871

Year built

1938

Style

Single Family Residential

County

Norfolk County

APN

39337

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 21, 2023.

Property details

Parking

Parking Information
Has Garage
Has Open Parking
# of Garage Spaces: 2
# of Covered Spaces: 2
Open Parking Spaces: 2
Parking Spaces: 4
AttachedGarageYN: Yes
Parking Features: Attached, Garage Door Opener, Off Street, Paved

Interior

Virtural Tour Information
Virtual Tour 1 (External Link)

Master Bedroom Information
Level: Second
Features: Bathroom - Full,Closet,Flooring - Wall to Wall Carpet,Recessed Lighting,Lighting - Overhead,Closet - Double

Bedroom #2 Information
Level: First
Features: Bathroom - Full,Flooring - Hardwood,Recessed Lighting,Lighting - Overhead

Bedroom #3 Information
Level: Second
Features: Closet,Flooring - Wall to Wall Carpet

Bedroom #4 Information
Level: Second
Features: Closet,Flooring - Hardwood

Bedroom #5 Information
Level: Second
Features: Closet,Flooring - Hardwood

Bathroom Information
# of Bathrooms (Full): 3
# of Bathrooms (Half): 1
Master Bathroom Features: Yes

Bathroom #1 Information
Level: Second
Features: Bathroom - Full,Bathroom - Tiled With Shower Stall,Bathroom - Tiled With Tub,Flooring - Stone/Ceramic Tile,Window(s) - Bay/Bow/Box,Countertops - Stone/Granite/Solid,Recessed Lighting

Bathroom #2 Information
Level: Second
Features: Bathroom - Full,Bathroom - Double Vanity/Sink,Bathroom - Tiled With Shower Stall,Skylight,Flooring - Stone/Ceramic Tile,Cabinets - Upgraded,Remodeled,Beadboard

Bathroom #3 Information
Level: First
Features: Bathroom - Full,Bathroom - Tiled With Shower Stall,Flooring - Stone/Ceramic Tile,Countertops - Stone/Granite/Solid,Countertops - Upgraded,Remodeled,Lighting - Sconce

Living Room Information
Level: First
Features: Flooring - Hardwood,Recessed Lighting,Wainscoting,Crown Molding,Decorative Molding

Dining Room Information
Level: Main,First
Features: Flooring - Hardwood,French Doors,Exterior Access,Recessed Lighting,Remodeled,Lighting - Sconce,Crown Molding

Kitchen Information
Level: First
Features: Flooring - Hardwood,Countertops - Stone/Granite/Solid,Kitchen Island,Cabinets - Upgraded,Recessed Lighting,Remodeled,Stainless Steel Appliances,Gas Stove,Lighting - Pendant

Basement Information
Basement: Full, Finished, Garage Access

Laundry Information
Laundry Features: In Basement

Fireplace Information
Has Fireplace
# of Fireplaces (Total): 2
Fireplace Features: Dining Room, Living Room

Appliances
Appliances: Gas Water Heater, Oven, Dishwasher, Disposal, Microwave, Range, Refrigerator, Washer, Dryer, Range Hood

Interior Features
# of Rooms (Total): 12
Flooring: Hardwood, Flooring - Hardwood
Interior Features: Closet, Closet/Cabinets - Custom Built, Recessed Lighting, Wainscoting, Crown Molding, Decorative Molding, Den

Exterior

Building Information
Building Area (Total): 2,992
Foundation Details: Concrete Perimeter
Year Built Source: Public Records
Year Built Details: Approximate

Exterior Features
Exterior Features: Professional Landscaping

Property Information
PropertySubType: Single Family Residence
Above Grade Finished Area: 2992
ADU: N

Lot Information
Lot Size (Acres): 0.33
Lot Features: Gentle Sloping
Road Frontage Type: Public

Financial

Tax Information
Tax Annual Amount: $25,245
Tax Year: 2026

Utilities

Utility Information
Utilities: for Gas Range
Sewer: Public Sewer
Water Source: Public

Heating & Cooling
Has Heating
Has Cooling
Heating: Baseboard, Natural Gas
Cooling: Central Air

Location

Location Information
Directions: From Rt 9 West turn right onto Reservoir Rd, left onto Fairway Rd and right onto Valley Rd
UnparsedAddress: 44 Valley Rd, Brookline MA 02467

Community Information
Senior CommunityYN: No
Community Features: Public Transportation, Shopping, Park, Walk/Jog Trails, Golf, Bike Path, Conservation Area, Highway Access, House of Worship, Private School, Public School

Public facts

Beds: 5
Baths: 3.5
Sq. Ft.: 2,871
Stories: 2.0
Lot Size: 0.33 acres
Style: Single Family Residential
Year Built: 1938
Year Renovated: 1974
County: Norfolk County
APN: 39337

Home facts updated by county records on Jul 20, 2023

Other

Listing Information
StandardStatus: Closed

Around this home

Schools

Roland Hayes School

Public PreK-8 • Assigned • 0.3mi

9/10

Brookline High School

Public 9-12 • Assigned • 1.4mi

8/10

Provided by GreatSchools

Local insights from Redfin agents

Brookline will continue to be a Seller's market for the foreseeable future, driven by restrictive zoning laws that have limited increases in housing production and a stable population with relatively low turnover. This has resulted in a massive...
4 weeks ago • Brookline
Benjamin Ginsburg
Redfin Premier agent
155 deals
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Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

3/10 Fire Factor

0.15% chance of being in a wildfire in next 30 years

5/10 Heat Factor

7 days above 96° expected this year, 14 days in 30 years

6/10 Wind Factor

59% chance of strong winds in next 30 years

2/10 Air Factor

1 unhealthy days expected this year, 3 days in 30 years

Provided by First Street

Historical weather

Chestnut Hill, MA • 02467

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

84/ 100

Very good sunlight

Sunscore

This home receives average direct sun exposure in Chestnut Hill. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

9.1 hrs

4.5 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$2.48M – $3.01M

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Home values near 44 Valley Rd

Data from public records.

Address	Redfin Estimate
60 Valley Rd, Chestnut Hill, MA 5 Beds \| 4.5 Baths \| 3737 Sq. Ft.	$3,631,529
14 Valley Rd, Chestnut Hill, MA 5 Beds \| 3.5 Baths \| 3000 Sq. Ft.	$2,851,629

Address	Redfin Estimate
34 Valley Rd, Chestnut Hill, MA 3 Beds \| 2.5 Baths \| 2300 Sq. Ft.	$2,405,097
43 Valley Rd, Chestnut Hill, MA 4 Beds \| 5 Baths \| 3789 Sq. Ft.	$3,713,984

Address	Redfin Estimate
22 Valley Rd, Chestnut Hill, MA 4 Beds \| 3.5 Baths \| 2836 Sq. Ft.	$2,645,944
53 Valley Rd, Chestnut Hill, MA 5 Beds \| 5.5 Baths \| 4145 Sq. Ft.	$4,691,977

Property information provided by MLS PIN when last listed in 2026. This data may not match . Learn more.

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GreatSchools Ratings provided by GreatSchools.org.

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