265 Dean Road, Brookline MA 02445

Brookline, MA 02445 • Chestnut Hill
$4,500,000
Est. $23,951/month
6
Beds
4.5
Baths
5,744
Sq Ft
$783
Price/Sq Ft
0.23
Acres
1914
Year Built
Single Family Residence
Type
76
Days on Market
Closed Listed Sep 30, 2025 • MLS# 73337780 Copied!

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.

Property Overview

Property Type
Single Family Residence
Listing Type
For Sale
Year Built
1914
Bedrooms
6
Full Bathrooms
4
Half Bathrooms
1
Living Area
5,744 sq ft
Total Rooms
15

Sale Statistics

Sale Overview
Original List Price: $4,995,000
Final Sale Price: $4,500,000
Difference: $495,000 (-9.9%)
Performance Metrics
90.1%
List to Sale Ratio
Sold below asking price
76
Days on Market
Extended listing
Price per Square Foot Analysis
Original $/sq ft: $870
Sale $/sq ft: $783
This property sold for $783 per square foot
Sale Summary

This property sold for 9.9% below the original asking price.

The property spent 76 days on market before selling.

Facts & Features

2 Car Garage
Central AC

Home Facts

Type Residential
Style Single Family Residence
Year Built 1914
Living Area 5,744 sq ft
Lot Size 0.23 acres
Bedrooms 6
Full Baths 4
Half Baths 1
Total Rooms 15

Interior

Heating Central, Forced Air, Ductless
Cooling Central Air, Heat Pump
Flooring None
Appliances None
Fireplace None
Fireplaces 2
Basement Full, Finished
Laundry None
Features None

Exterior

Construction None
Architecture Colonial Revival
Roof Slate
Features None
Pool None
Spa None
Fencing None
Patio/Porch None

Parking

Garage Spaces 2
Has Garage Yes
Features Detached, Paved Drive
Total Spaces 5

Utilities

Electric None
Water Public
Sewer Public Sewer
Gas None
Other None

Financial

Annual Tax $30,910
Assessed Value $3,478,200

Location

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Neighborhood

Chestnut Hill

265 Dean Road, Brookline MA 02445

Brookline, MA 02445

Walkability

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Schools

Elementary School
Hayes (Heath)
Rating information coming soon

Monthly Payment Calculator

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Estimated Monthly Payment $0

Payment Breakdown

Principal & Interest $0
Property Tax $2,576
Homeowners Insurance $200
PMI $0

Property History

Market Insights

2.1%
Price Range
78
Total Days on Market

Property Timeline

Sold
Jun 11, 2025
$4,500,000
Property sold
Days on Market: 78
🏠
Listed for Sale
Feb 24, 2025
$4,595,000
Original listing
Agent: Jeffrey Hamilton Office: Columbus and Over Group, LLC

Price & Status History

Date Event Price Change
Feb 24, 2025 New Listing Added $4,595,000

Market Statistics

Days on Market
76 days
Price per Sq Ft
$783

Tax History

Year Taxes Assessment
2025 $30,910 $3,478,200

Financial Details

Annual Property Tax
$30,910
Tax Year 2025
Assessed Value
$3,478,200

Listing Information

Listing Agent Jeffrey Hamilton
Listing Office Columbus and Over Group, LLC
Agent MLS ID CN209930
Office MLS ID AN1793

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