53 Winslow Road, Brookline MA 02446
Brookline, MA 02446 • Coolidge Corner
$4,250,000
Est. $24,745/month
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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!
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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
6
Full Bathrooms
4
Half Bathrooms
2
Living Area
4,865 sq ft
Total Rooms
12
Stories
4
Levels
4
Floor Layout
Interactive room guide
Floor Layout
Finished Area
3,775 sq ft above grade
1,090 sq ft below grade
Display Options
Outdoor Areas
Patio & porchDeck
Room Markers
BABathroom (4)
BRBedroom (5)
DDining (1)
KKitchen (1)
LLiving (2)
OOffice (1)
Conceptual diagram based on MLS room data. It is not to scale and is not a substitute for architectural plans or on-site measurements.
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 District
Brookline School District local
A+
School Safety
2024-25
0.4%
Low
0.3%
Suspensions
0.6%
In-School
0.1%
Emergency
5.1% below state avg
Elementary Schools
10 schools
A
Florida Ruffin Ridley School
0.4 mi
|
#40 of 352
|
Score: 58.5
Improved 3 spots from last year
+0.3 above state avg
857 students
Diverse
Diverse Student Body
Grades PK-08
Ivy Street School
0.5 mi
Grades 01-12
New England Hebrew Academy Elementary and Secondary School
0.6 mi
Grades PK-06
A+
Lawrence School
0.9 mi
|
#8 of 352
|
Score: 63.9
Improved 2 spots from last year
+5.7 above state avg
630 students
Diverse
Diverse Student Body
Grades K-08
A+
Michael Driscoll School
1.0 mi
|
#30 of 352
|
Score: 60.1
Improved 10 spots from last year
+1.9 above state avg
567 students
Diverse
Diverse Student Body
Grades PK-08
St. Mary of the Assumption School
1.0 mi
Grades PK-08
A+
Pierce School
1.0 mi
|
#27 of 352
|
Score: 60.5
Dropped 16 spots from last year
+2.3 above state avg
592 students
Very Diverse
Diverse Student Body
Grades K-08
Torah Academy Inc.
1.2 mi
Grades PK-08
Maimonides School
1.5 mi
Grades K-12
A
John D Runkle School
1.5 mi
|
#44 of 352
|
Score: 58.0
Dropped 36 spots from last year
-0.2 below state avg
476 students
Diverse
Diverse Student Body
Grades PK-08
High Schools
3 schools
JRI Bay Cove School
0.2 mi
Grades 07-12
Beaver Country Day School
3.1 mi
Grades 06-12
A+
Brookline High School
1.3 mi
|
#1 of 346
|
Score: 82.5
Improved 18 spots from last year
+24.3 above state avg
2,181 students
Diverse
21 sports
• 3,004 athletes
Strong AP Program
High Graduation Rate
College Ready Curriculum
Strong Athletics
Grades 09-12
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Monthly Payment Calculator
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Loan Amount
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After down payment
Total Interest
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Over life of loan
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Including down payment
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Down: $0
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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
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$0
Rate Impact
-0.5% Rate
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Current Rate
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+0.5% Rate
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Payment Over Time
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
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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.
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