Pending

$2,850,000

Est. $17,319/mo —

•

2,992

sq ft

44 Valley Rd, Chestnut Hill, MA 02467

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

$953Price/Sq.Ft.

2 garage spacesParking

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

Listed by Gibson Sotheby's International Realty

Listing updated: Aug 25, 2026 at 03:09am

Redfin checked: 2 minutes ago

•Source:MLS PIN #73558881

Payment calculator

$17,319 per month

Principal and interest$14,788

Property taxes

$2,104

HOA dues

Home insurance

$428

Utilities

Add

5 minutes to get started. No credit impact.

Affordability tools

Open houses

No upcoming open houses.

Nearby open houses (10)

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OPEN SAT, 11AM TO 1PM
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REDFIN OPEN SAT, 11:30AM TO 1:30PM3D WALKTHROUGH
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Around this home

Schools

K - 12
Preschool & daycare

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

About Chestnut

Hill

Chestnut Hill, located between Commonwealth Avenue and Route 9, is a residential and retail Newton neighborhood with granite outcrops and village-style shopping streets. The neighborhood’s character concentrates around the Chestnut Hill Mall–The Street corridor on Boylston Street, where cafés, boutiques, and polished storefronts line wide sidewalks. Pillars include the Metropolitan Waterworks Museum, the Boston College campus edge, and the historic Hammond Pond Reservation trails. Large, shingle-style and brick homes sit along curving, tree-lined roads shaped by the area’s glacial terrain. Pocket parks and reservoir paths set a steady outdoor rhythm. Commercial nodes feel curated rather than crowded, with a calm, commuter-friendly pace.

Provided by Walk Score and Local Logic

Market insights

44 Valley Rd · $2,850,000

DAYS ON MARKET

The average home goes pending in 19 days.

SALE-TO-LIST

Most homes are selling 3% above list price.

LIST PRICE

Median sale price in this area is $838,273. (71% lower than this home)

PRICE DROP

15% of homes in this area have had a price drop in the past month.

Property details

Interior
Exterior
Finance

Kitchen

Bathroom

Bedroom

Living

Dining

Interior features
Custom built closets and cabinetry
Recessed lighting throughout
Wainscoting, crown molding and decorative molding
Den
12 total rooms

Bedrooms
Primary bedroom on second floor with full bathroom, double closet and recessed lighting
Bedroom 2 on first floor with full bathroom, hardwood flooring and recessed lighting
Bedrooms 3, 4 and 5 on second floor with closets (mix of wall-to-wall carpet and hardwood flooring)

Bathrooms
Three full bathrooms and one half bath total
Primary bath present
Second-floor bathrooms feature tiled showers, stone/ceramic tile flooring and upgraded cabinetry (one remodeled)
First-floor bathroom with tiled shower, upgraded stone countertops and remodeled finishes

Kitchen
Kitchen on first floor with hardwood flooring
Stone/granite countertops and upgraded cabinets
Kitchen island and pendant lighting
Remodeled kitchen with stainless steel appliances and gas stove

Laundry & utility
Laundry located in finished basement
Washer and dryer included
Full finished basement with garage access

Flooring
Hardwood flooring in main living areas and several bedrooms
Wall-to-wall carpet in some bedrooms
Stone/ceramic tile flooring in bathrooms

Heating & cooling
Baseboard heating with natural gas
Central air conditioning

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

Finished Sq. Ft.

2,871

Unfinished Sq. Ft.

—

Total 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.

Dec 24, 2024 • Active

Residential building

Remove existing roofing and install a new roof. The work will use Iko Dynasty materials and comply with building codes and zoning bylaws.

Roofing

Jun 24, 2021 • Active

Residential electrical

Install roof-mounted solar panels and a photovoltaic system on a residential building.

Electrical

Solar

Permit history is from public records and may be incomplete or inaccurate. Redfin and its agents make no representations about the property condition or permit status. Buyers should independently verify all information.

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...
2 months ago • Brookline
Benjamin Ginsburg
Redfin Premier agent
151 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

There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

9.1 hrs

4.5 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 44 Valley Rd

$2,890,347

$40K over list price of $2.85M

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $2.2M to $4.1M.

SOLD JUN 26, 2026
$2,950,000 Last sold price
4 beds3.5 baths3,230 sq ft
59 Randolph, Chestnut Hill, MA 02467
$40/sq ft
18 years older
SOLD JUL 29, 2026
$2,200,000 Last sold price
4 beds3.5 baths2,800 sq ft
25 Chestnut Hill Rd, Chestnut Hill, MA 02467
$167/sq ft
smaller lot
13 years older
SOLD MAY 28, 2026
$4,125,000 Last sold price
5 beds4.5 baths4,001 sq ft
34 Hyslop Rd, Brookline, MA 02445
$78/sq ft
smaller lot
19 years newer
SOLD JUL 23, 2026
$2,805,000 Last sold price
5 beds4.5 baths4,694 sq ft
78 Waban Hill Rd N, Chestnut Hill, MA 02467
$355/sq ft
smaller lot
11 years older
SOLD JUN 15, 2026
$3,300,000 Last sold price
4 beds4.5 baths3,628 sq ft
98 Spooner Rd, Chestnut Hill, MA 02467
$43/sq ft
smaller lot
18 years older
SOLD APR 23, 2026
$3,318,000 Last sold price
6 beds4 baths4,633 sq ft
189 Clinton Rd, Brookline, MA 02445
$237/sq ft
smaller lot
30 years older

Rental earnings

Est. $6,013 per month, based on comparable rentals

This home is pending

The seller has accepted an offer, and this property is now .

Have questions?

James Gulden

Chestnut Hill Redfin Agent

James Gulden typically replies in about 5 minutes

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Details provided by MLS PIN and may not match the public record. Learn more.

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