Off Market Jun 2025 for $4.5M

$4,643,989

Est. refi paymentEst. refi $4,297/mo

•

5,744

sq ft

265 Dean Rd, Brookline, MA 02445

About this home

Nestled between Fisher Hill & Chestnut Hill, 265 Dean offers the perfect blend of urban convenience & suburban comfort. This 6+ bedroom Colonial Revival was fully gutted in 2021 to meet modern family needs while preserving its historic charm. Expansive chef's kitchen features Sub-Zero & Thermador appliances. It opens to a bright family room with custom built-ins. A larger formal living room spills onto an enormous covered porch. Upstairs, the primary suite delights w/ luxurious spa-like bath & large walk-through closet. 3 more bedrooms and convenient laundry complete this level. 4th floor has 2 more beds, a living room, office & full bath. Extraordinary basement includes a sports room, playroom, home gym & full bath. Modern upgrades include new windows, electrical, plumbing and a multi-zoned HVAC. The 1/4 acre lot has recently been leveled with significant drainage and retention work. 2 car garage. Superb convenience: walk to schools, parks, public transit & Cleveland Circle amenities.

Single-familyProperty Type

1914Year Built

9,987 sq ftLot Size

$808Est. Price/Sq.Ft.

2 garage spacesParking

Listed by Jeffrey Hamilton • Columbus and Over Group, LLC

Bought with Paul Whaley / Charlie Ring Team • Coldwell Banker Realty - Boston

Redfin checked: 2 minutes ago

•Source:MLS PIN #73337780

Redfin Estimate

$4,643,989

$144K since sold in June 2025$174K since July

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 34.8% higher than the average sale price ($3.44M) of 6 comparable homes.

SOLD APR 23, 2026
$3,318,000
A
6 beds4 baths4,633 sq ft
189 Clinton Rd, Brookline, MA 02445
SOLD APR 27, 2026
$4,100,000
B
6 beds4.5 baths5,058 sq ft
282 Buckminster Rd, Brookline, MA 02445
SOLD MAY 14, 2026
$3,285,000
C
5 beds4.5 baths3,658 sq ft
43 Druce St, Brookline, MA 02445
SOLD JUN 15, 2026
$3,300,000
D
4 beds4.5 baths3,628 sq ft
98 Spooner Rd, Chestnut Hill, MA 02467
SOLD MAR 4, 2026
$2,995,000
E
5 beds4.5 baths3,370 sq ft
323 Clark Rd, Brookline, MA 02445
SOLD JAN 15, 2026
$3,670,000
F
5 beds5.5 baths5,552 sq ft
85 Williston Rd, Brookline, MA 02445

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Earn from this home

Sell

$888,833

Est. take-home

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Est. cash available

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Rent

$8,304/mo

Redfin rental estimate

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Market trends in 02445, MA

Last updated July 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

100.2%

0.1% MoM

Median sale price

$1.2M

$85K MoM

Avg. days on market

30d

9 days MoM

Recently sold homes

7 MoM

New listings for sale

OPEN FRI, 12:30PM TO 2PM
$2,895,000
7 beds3.5 baths4,805 sq ft
71 Addington Rd, Brookline, MA 02445
OPEN SAT, 12PM TO 2PM
$2,200,000
9 beds3 baths4,364 sq ft
26 Parkway Rd, Brookline, MA 02445
OPEN SUN, 11AM TO 12PM
$4,800,000
5 beds5.5 baths4,324 sq ft
221 Gardner Rd, Brookline, MA 02445
EARLY ACCESS
Unknown
5 beds6 baths3,539 sq ft
291 Tappan St, Brookline, MA 02445
$1,495,000
3 beds2 baths1,759 sq ft
12 Kilsyth Rd #3, Brookline, MA 02445
$560,000
1 bed1 bath860 sq ft
77 Pond Ave #509, Brookline, MA 02445
$2,999,000
4 beds3.5 baths3,265 sq ft
52 Clinton Rd, Brookline, MA 02445
3D WALKTHROUGH
$6,495,000
9 beds7.5 baths8,619 sq ft
372 Warren St, Brookline, MA 02445
OPEN SAT, 11:30AM TO 12:30PM
$999,000
3 beds2 baths1,240 sq ft
1896 Beacon St Ph 3, Brookline, MA 02445
See all

Provided by Redfin

Sale history for 265 Dean Rd

Date

Event

Price

MLS PIN #73337780

Jun 11, 2025

Sold

$4,500,000

$783/sq ft

May 2, 2025

Contingent

—

Apr 29, 2025

Price Changed

$4,595,000

$800/sq ft

Apr 8, 2025

Price Changed

$4,695,000

$817/sq ft

Feb 24, 2025

Listed

$4,995,000

$870/sq ft

MLS PIN #72668093

Aug 19, 2020

Sold

$2,241,665

$390/sq ft

Jun 10, 2020

Contingent

—

Jun 4, 2020

Listed

$2,190,000

$381/sq ft

Well maintained Fisher Hill colonial with classical details, three fireplaces in spacious living and dining room, third floor great room, located on beautiful Dean Road off Chestnut Hill Ave. Second floor master bedroom and three more bedrooms with two bathrooms. Third floor three bedrooms with bathroom/shower. Eat-in kitchen with pantry room. Basement in-law unit with separate entrance. OH showings: Saturday 06/06 1:30 - 3:00 PM, Sunday 06/07 1:30 - 3:00 PM, Monday 06/08 9:00 - 10:30 AM. Offers, if any, due at 5pm Tuesday 06/09 with expiration at 5pm Wed. 06/10.

MLS PIN #70050699

Aug 16, 2004

Sold

$1,560,000

$272/sq ft

Jul 6, 2004

Listing Removed

—

Jun 16, 2004

Listed

$1,595,000

$278/sq ft

Public Records

Jun 15, 1987

Sold

$640,000

$111/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$28,701 (+2.7%)

$1,001,000 + $1,877,700

$2,878,700

2022

$27,937 (+25.8%)

$953,300 + $1,788,300

$2,741,600

2021

$22,206 (+8.5%)

$916,600 + $1,349,300

$2,265,900

2020

$20,458 (+5.9%)

$833,300 + $1,331,600

$2,164,900

2019

$19,319 (−0.6%)

$793,600 + $1,268,200

$2,061,800

2018

$19,434 (+1.5%)

$800,200 + $1,254,100

$2,054,300

2017

$19,146 (+1.5%)

$754,800 + $1,183,100

$1,937,900

2016

$18,872 (+4.4%)

$705,500 + $1,105,600

$1,811,100

2015

$18,077 (−0.9%)

$659,300 + $1,033,300

$1,692,600

2014

$18,239 (+0.7%)

$599,500 + $1,001,800

$1,601,300

2013

$18,112 (+2.2%)

$582,000 + $972,700

$1,554,700

2012

$17,724 (+5.9%)

$582,000 + $972,700

$1,554,700

2011

$16,738 (+2.6%)

$561,500 + $919,700

$1,481,200

2010

$16,316 (+2.7%)

$561,500 + $925,800

$1,487,300

2009

$15,881

$559,800 + $925,800

$1,485,600

Tax history for 265 Dean Rd

Year

Property tax

Land + Additions

Assessment*

2023

$28,701 (+2.7%)

$1,001,000 + $1,877,700

$2,878,700

2022

$27,937 (+25.8%)

$953,300 + $1,788,300

$2,741,600

2021

$22,206 (+8.5%)

$916,600 + $1,349,300

$2,265,900

2020

$20,458 (+5.9%)

$833,300 + $1,331,600

$2,164,900

2019

$19,319 (−0.6%)

$793,600 + $1,268,200

$2,061,800

2018

$19,434 (+1.5%)

$800,200 + $1,254,100

$2,054,300

2017

$19,146 (+1.5%)

$754,800 + $1,183,100

$1,937,900

2016

$18,872 (+4.4%)

$705,500 + $1,105,600

$1,811,100

2015

$18,077 (−0.9%)

$659,300 + $1,033,300

$1,692,600

2014

$18,239 (+0.7%)

$599,500 + $1,001,800

$1,601,300

2013

$18,112 (+2.2%)

$582,000 + $972,700

$1,554,700

2012

$17,724 (+5.9%)

$582,000 + $972,700

$1,554,700

2011

$16,738 (+2.6%)

$561,500 + $919,700

$1,481,200

2010

$16,316 (+2.7%)

$561,500 + $925,800

$1,487,300

2009

$15,881

$559,800 + $925,800

$1,485,600

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Public record
Permits

Beds

Baths

4.5

Stories

Lot width

—

Lot depth

—

Lot size

10,019 Sq. Ft.

Year renovated

1968

Sq. Ft.

3,978

Year built

1915

Style

Single Family Residential

County

Norfolk County

APN

38951

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 21, 2023.

Sep 11, 2025 • Active

Residential building

Replace framing in an existing garage to allow for storage above. Apply a board and plaster finish. Replace window sashes to match the existing style.

Remodel

Apr 7, 2022 • Final

Residential building

Remodel all floors and demolish the chimney down to the basement slab according to the provided plans.

Remodel

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.

Property details

Parking

Parking Information
Has Garage
Has Open Parking
# of Garage Spaces: 2
# of Covered Spaces: 2
Parking Spaces: 5
Parking Features: Detached, Paved Drive

Interior

Bathroom Information
# of Bathrooms (Full): 4
# of Bathrooms (Half): 1
Master Bathroom Features: Yes

Basement Information
Basement: Full, Finished

Fireplace Information
Has Fireplace
# of Fireplaces (Total): 2

Interior Features
# of Rooms (Total): 15

Exterior

Building Information
Building Area (Total): 5,744
Foundation Details: Concrete Perimeter
Year Built Source: Public Records
Year Built Details: Actual

Exterior Features
Roof: Slate

Property Information
Accessibility Features: No
PropertySubType: Single Family Residence

Lot Information
Lot Size (Acres): 0.23
Road Frontage Type: Public

Financial

Tax Information
Tax Annual Amount: $30,910
Tax Year: 2025

Utilities

Utility Information
Sewer: Public Sewer
Water Source: Public

Heating & Cooling
Has Heating
Has Cooling
Heating: Central, Forced Air, Ductless
Cooling: Central Air, Heat Pump

Location

Location Information
Directions: Off of Chestnut Hill Ave
UnparsedAddress: 265 Dean Road, Brookline MA 02445

Community Information
Senior CommunityYN: No
Community Features: Public Transportation, Shopping, Tennis Court(s), Park, Walk/Jog Trails, Golf, Public School, T-Station

Public facts

Beds: 6
Baths: 4.5
Sq. Ft.: 3,978
Stories: 3.0
Lot Size: 10,019 square feet
Style: Single Family Residential
Year Built: 1915
Year Renovated: 1968
County: Norfolk County
APN: 38951

Home facts updated by county records on Jul 20, 2023

Other

Miscellaneous Information
Heat Zones: 9

Listing Information
StandardStatus: Closed

Around this home

Schools
Places
Transit

Roland Hayes School

Public PreK-8 • Assigned • 0.2mi

9/10

Brookline High School

Public 9-12 • Assigned • 1.1mi

8/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

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, 15 days in 30 years

6/10 Wind Factor

54% chance of strong winds in next 30 years

3/10 Air Factor

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

Provided by First Street

Historical weather

Brookline, MA • 02445

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 9 hours in June and 4.4 hours in December, placing it below the U.S. average for solar exposure.

9 hrs

4.4 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$4.41M – $5.34M

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Nearby similar homes

OPEN SUN, 11AM TO 12PM

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3D WALKTHROUGH

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New listings for sale in 02445

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OPEN SAT, 12PM TO 2PM

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OPEN SUN, 11AM TO 12PM

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EARLY ACCESSCOMPASS COMING SOON

Unknown

5 beds6 baths3,539 sq ft

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3 beds2 baths1,759 sq ft

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3D WALKTHROUGH

$6,495,000

9 beds7.5 baths8,619 sq ft

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OPEN SAT, 11:30AM TO 12:30PM

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Home values near 265 Dean Rd

Data from public records.

Address	Redfin Estimate
237 Dean Rd, Brookline, MA 5 Beds \| 3.5 Baths \| 4414 Sq. Ft.	$4,007,100
271 Dean Rd, Brookline, MA 5 Beds \| 4.5 Baths \| 3904 Sq. Ft.	$3,708,953

Address	Redfin Estimate
249 Dean Rd, Brookline, MA 5 Beds \| 4 Baths \| 3474 Sq. Ft.	$3,532,967
275 Dean Rd, Brookline, MA 5 Beds \| 3.5 Baths \| 3289 Sq. Ft.	—

Address	Redfin Estimate
257 Dean Rd, Brookline, MA 5 Beds \| 3.5 Baths \| 3059 Sq. Ft.	$2,643,285
285 Dean Rd, Brookline, MA 4 Beds \| 4 Baths \| 3190 Sq. Ft.	$3,198,764

Property information provided by MLS PIN when last listed in 2025. This data may not match . Learn more.

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Redfin Estimate

Earn from this home

Market trends in 02445, MA

Sale history for 265 Dean Rd

Tax history for 265 Dean Rd

Public record

Property details

Around this home

Lifestyle

Local insights from Redfin agents

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 02445

Home values near 265 Dean Rd

More real estate resources