53 Winslow Road, Brookline MA 02446

Brookline, MA 02446 • Coolidge Corner

$4,250,000

Est. $24,745/month

Beds

Baths

4,865

Sq Ft

$874

Price/Sq Ft

0.14

Acres

2005

Year Built

Parking

2 Family - 2 Units Up/Down

Type

102

Days on Market

Active Listed Mar 30, 2026 • MLS# 73493346 Copied! • Updated Jun 1, 2026

About this home

Welcome to this stunning Coolidge Corner two family constructed in 2005. Each unit has two levels with 3 bedrooms, 2.5 baths and boasts over 2300+ SF each of interior living space. Main level for each offers a sprawling, open floor plan with a beautiful dual sided gas fireplace as a contemporary centerpiece + main focal point. The elegant dining area flows into a spacious kitchen with custom maple cabinets, stainless steel appliances (gas stove, dishwasher, refrigerator, vent hood), center island complimented by sleek black granite countertops. Impressive primary bedroom suite with large closet + ensuite spa like bath. Two additional bedrooms with ample closet space. Upper unit has spacious outdoor deck. Additional highlights include high ceilings, central air conditioning, gas heating and 4 parking. Located near bustling Coolidge Corner shops, restaurants, cinema and Trader Joe’s. Easy access to train to universities, Longwood Medical area + downtown Boston!

View in the App

Save this property, schedule tours instantly, and get alerts when the price drops

Scan with phone

Get the full experience in the BMN Boston app

Public Records & Permits

BMN Estimate

Get the number an algorithm can't give you

A free agent CMA factors in condition, upgrades, and the street — the things comps alone can't see.

Recently Sold Nearby

Property History

Market Insights

Property Timeline

•

Back On Market

May 28, 2026

Active

📋

Status: Active under contract

May 13, 2026

Active → Active Under Contract

⏳

Pending Sale

May 12, 2026

Offer accepted, sale pending

🔧

Property Type Updated

Apr 3, 2026

4 Family → 2 Family - 2 Units Up/Down

🏠

Listed for Sale

Mar 30, 2026

$4,250,000

Original listing

Agent: Mary Lochner Office: Coldwell Banker Realty - Brookline

Date	Event	Price	Change	$/sqft	Details
05/28/2026	• Back On Market	-	-	-	Active
05/13/2026	📋 Status: Active under contract	-	-	-	Active → Active Under Contract
05/12/2026	⏳ Pending Sale	-	-	-	Offer accepted, sale pending
04/03/2026	🔧 Property Type Updated	-	-	-	4 Family → 2 Family - 2 Units Up/Down
03/30/2026	🏠 Listed for Sale	$4,250,000	-	-	Original listing

Tax History

Year	Taxes	Assessment
2025	$36,658	$3,714,100

Financial Details

Annual Property Tax

$36,658

Tax Year 2025

Assessed Value

$3,714,100

Facts & Features

Home Facts

Type Residential Income

Style 2 Family - 2 Units Up/Down

Year Built 2005

Living Area 4,865 sq ft

Lot Size 0.14 acres

Bedrooms 6

Full Baths 4

Half Baths 2

Total Rooms 12

Investment Metrics

Units 2

Unit 1 Rent $7,250/mo · Y

Unit 2 Rent — · N

Total Monthly Rent $7,250/mo

Gross Income $87,000

Net Operating Income $87,000

Cap Rate 2.05%

Interior

Heating None

Cooling None

Flooring Wood, Carpet

Appliances None

Fireplace None

Fireplaces 2

Basement Full, Finished

Laundry Electric Dryer Hookup

Features None

Exterior

Construction Frame

Architecture None

Roof Shingle

Features Balcony

Pool None

Spa None

Fencing None

Patio/Porch Deck

Parking

Features Paved Drive, Off Street

Total Spaces 4

Utilities

Electric 200+ Amp Service

Water Public

Sewer Public Sewer

Gas None

Other For Gas Range, For Electric Range, For Gas Oven, For Electric Oven, For Electric Dryer

Financial

Annual Tax $36,658

Assessed Value $3,714,100

HOA & Community

Fee Includes None

Amenities None

Optional Fee Includes None

MA Disclosures

Seller Disclosures None

Additional Details

Possession None

Accepted Financing None

Structure Type []

House Color Slate Blue

Sq Ft Source Public Record

Sq Ft Disclosures Unit #1 2335 SF, Unit #2 2530 SF

Documents None

County Norfolk

Total market time (incl. prior listings) 62 days

Property Overview

Property Type

2 Family - 2 Units Up/Down

Listing Type

For Sale

Year Built

2005

Bedrooms

Full Bathrooms

Half Bathrooms

Living Area

4,865 sq ft

Total Rooms

Stories

Levels

Room Details

Other Floor

Bathroom1

Bedroom5

Bedroom4

Bedroom3

Dining Room

Kitchen

Bathroom2

Bedroom2

Living Room

Bathroom3

Master Bedroom

Office

Family Room

Master Bathroom

Interior Features

Flooring: Wood, Carpet

Appliances:

Interior Features:

Windows: Insulated Windows

Basement: Full, Finished

Laundry: Electric Dryer Hookup

Security:

Construction & Materials

Year Built: 2005

Structure Type:

Exterior Materials: Frame

Roof: Shingle

Foundation: Concrete Perimeter

Stories: 4

Heating, Cooling & Utilities

Heating:

Heating Zones: 2

Cooling:

Cooling Zones: 2

Hot Water: Natural Gas

Water Source: Public

Sewer: Public Sewer

Energy Features:

Exterior & Lot

Exterior Features: Balcony

Patio & Porch: Deck

Fencing:

Other Structures:

Lot Features:

Road Surface: Paved

Parking & Garage

Total Parking Spaces: 4

Parking Features: Paved Drive, Off Street

Special Features

Fireplaces: 2

Fireplace Type:

Community Amenities: Public Transportation, Shopping, Park, Walk/Jog Trails, Medical Facility, Bike Path, Highway Access, Public School, T-Station, University

Nearby Schools

School information not available for this location.

Monthly Payment Calculator

Monthly Payment

Principal, interest, taxes & insurance

Loan Amount

After down payment

Total Interest

Over life of loan

Total Cost

Including down payment

Home Price

Down Payment

Down: $0

Interest Rate

Loan Term

Monthly Payment Breakdown

Principal & Interest $0

Property Tax $3,055

Homeowners Insurance $200

PMI (if <20% down) $0

Loan Summary

Total of 360 payments $0

Total principal paid $0

Total interest paid $0

Rate Impact

-0.5% Rate

$0/mo

Save $0/mo

Current Rate

$0/mo

+0.5% Rate

$0/mo

Cost $0/mo

Payment Over Time

Interest

Principal

Year 1

95% Interest

Year 15

50/50

Year 30

95% Principal

* Estimates only. Actual payments may vary. Consult with a lender for accurate figures.

Location

Loading map...

Neighborhood

Coolidge Corner

53 Winslow Road, Brookline MA 02446

Brookline, MA 02446

Listing Information

Listing Agent Mary Lochner

Listing Office Coldwell Banker Realty - Brookline

Office Phone 617-731-2447

Agent MLS ID BB804796

Office MLS ID AN6199

Listing Data Updated Jun 1, 2026 3:08 AM EDT

Listing information is deemed reliable but not guaranteed. Data provided by MLS Property Information Network, Inc. All information should be independently verified.

Contact Us

BMN Boston Real Estate

Douglas Elliman

(617) 800 - 9008 contact@bmnboston.com

Ask about this property — free, no obligation.

53 Winslow Road, Brookline MA 02446

About this home

Public Records & Permits

Recently Sold Nearby

Market Insights

Property Timeline

Back On Market

Status: Active under contract

Pending Sale

Property Type Updated

Listed for Sale

Tax History

Home Facts

Investment Metrics

Interior

Exterior

Parking

Utilities

Financial

HOA & Community

MA Disclosures

Additional Details

Property Overview

Other Floor

Monthly Payment Breakdown

Loan Summary

Rate Impact

Payment Over Time

Neighborhood

Customize Comparable Search

Distance & Location

Property Characteristics

Price & Value

Property Features

Market Filters

Display Options

📍 Comparable Properties Map

Market Analytics for Brookline, MA

53 Winslow Road, Brookline MA 02446

About this home

Public Records & Permits

BMN Estimate

Recently Sold Nearby

Property History

Market Insights

Property Timeline

Back On Market

Status: Active under contract

Pending Sale

Property Type Updated

Listed for Sale

Detailed History Table ▼

Tax History

Financial Details

Facts & Features

Home Facts

Investment Metrics

Interior

Exterior

Parking

Utilities

Financial

HOA & Community

MA Disclosures

Additional Details

Property Overview

Room Details

Other Floor

Interior Features

Construction & Materials

Heating, Cooling & Utilities

Exterior & Lot

Parking & Garage

Special Features

Nearby Schools

Monthly Payment Calculator

Monthly Payment Breakdown

Loan Summary

Rate Impact

Payment Over Time

Location

Neighborhood

Listing Information

Contact Us

Similar Homes for Sale

Comparable Properties

Customize Comparable Search

Distance & Location

Property Characteristics

Price & Value

Property Features

Market Filters

Display Options

📍 Comparable Properties Map

Adjust Property Details

Market Analytics for Brookline, MA

BMN Boston Real Estate

Schedule a Tour

Get the BMN Boston App