9 Plymouth Rd, Winchester MA 01890
Winchester, MA 01890 • Winchester Highlands
$2,500,000
$2,250,000
Est. $13,168/month
Estimate assumptions
20% down, a 30-year loan at 6.5%, and $200/month estimated insurance.
Includes the supplied property-tax and HOA inputs; missing inputs contribute $0. HOA fees with an unspecified frequency are treated as monthly. PMI and closing costs are excluded.
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About this home
Welcome to 9 Plymouth Rd — a classic 1959 single-family home tucked at the end of a private road on a dead-end street, set on a private 0.52-acre lot abutting conservation land in one of Winchester's most sought-after neighborhoods. This well-appointed 11-room residence offers 5 bedrooms, 3 full baths, and 1 half bath, giving your family room to spread out and settle in. Thoughtfully updated for year-round comfort, the home features central AC, central humidification, and an air exchanger. Outside, enjoy beautifully landscaped gardens, a spacious deck overlooking the private yard, lush irrigated grounds with an invisible dog fence, and a hot tub for unwinding after a long day. A wood-burning fireplace adds warmth and character to the living space. Located just minutes from top-rated schools, Winchester Center, and convenient commuter access to Boston, this is a rare opportunity to enjoy privacy, nature, and timeless New England living in an exceptional location.
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Recently Sold Nearby
Property History
Market Insights
2
Price Changes
10%
Price Range
Property Timeline
Price Reduced
Sep 24, 2026
$2,250,000
$150,000
(-6.25%)
From $2,400,000 to $2,250,000 (-6.2%)
Price Reduced
Sep 8, 2026
$2,400,000
$100,000
(-4%)
From $2,500,000 to $2,400,000 (-4.0%)
Listed for Sale
Jul 6, 2026
$2,500,000
Original listing
Agent: Steph Crawford Group
Office: Real Broker MA, LLC
| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 09/24/2026 | ↓ Price Reduced | $2,250,000 | $150,000 | - | From $2,400,000 to $2,250,000 (-6.2%) |
| 09/08/2026 | ↓ Price Reduced | $2,400,000 | $100,000 | - | From $2,500,000 to $2,400,000 (-4.0%) |
| 07/06/2026 | 🏠 Listed for Sale | $2,500,000 | - | - | Original listing |
Tax History
| Year | Taxes | Assessment |
|---|---|---|
| 2025 | $19,088 | $1,721,200 |
Financial Details
Annual Property Tax
$19,088
Tax Year 2025
Assessed Value
$1,721,200
Facts & Features
2 Car Garage
Central AC
Home Facts
Type
Residential
Style
Single Family Residence
Year Built
1959
Living Area
4,071 sq ft
Lot Size
0.52 acres
Bedrooms
5
Full Baths
3
Total Rooms
11
Interior
Heating
Baseboard, Oil
Cooling
Central Air, None
Flooring
Wood
Appliances
Water Heater, Oven, Dishwasher, Disposal, Microwave, Range, Refrigerator, Freezer, Washer, Dryer
Fireplace
None
Fireplaces
1
Basement
Partial
Laundry
None
Features
None
Exterior
Construction
Frame
Architecture
Colonial
Roof
Shingle
Features
Deck - Wood, Rain Gutters, Hot Tub/spa, Storage, Professional Landscaping, Sprinkler System, Garden, Invisible Fence
Pool
None
Spa
Private
Fencing
Invisible
Patio/Porch
Deck - Wood
Parking
Garage Spaces
2
Has Garage
Yes
Features
Attached, Garage Door Opener, Storage, Paved Drive, Off Street, Paved
Total Spaces
4
Utilities
Electric
220 Volts
Water
Public
Sewer
Public Sewer
Gas
None
Other
None
Financial
Annual Tax
$19,088
Assessed Value
$1,721,200
HOA & Community
Fee Includes
None
Amenities
None
Optional Fee Includes
None
MA Disclosures
Lead Paint
Unknown
Seller Disclosures
None
Additional Details
Possession
None
Accepted Financing
None
Structure Type
[]
Sq Ft Source
Public Record
Documents
None
County
Middlesex
Total market time (incl. prior listings)
80 days
Property Overview
Property Type
Single Family Residence
Listing Type
For Sale
Year Built
1959
Bedrooms
5
Full Bathrooms
3
Living Area
4,071 sq ft
Total Rooms
11
Floor Layout
Interactive room guide
Floor Layout
Finished Area
4,071 sq ft above grade
FeaturesYes
Display Options
Outdoor Areas
SpaPrivate
Patio & porchDeck - Wood
Room Markers
OOffice (1)
KKitchen (1)
BRBedroom (5)
BABathroom (4)
DDining (1)
LLiving (2)
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
Appliances:
Water Heater, Oven, Dishwasher, Disposal, Microwave, Range, Refrigerator, Freezer, Washer, Dryer
Interior Features:
Windows:
Insulated Windows
Basement:
Partial
Laundry:
Security:
Construction & Materials
Style:
Colonial
Year Built:
1959
Structure Type:
Exterior Materials:
Frame
Roof:
Shingle
Foundation:
Concrete Perimeter
Heating, Cooling & Utilities
Heating:
Baseboard, Oil
Heating Zones:
5
Cooling:
Central Air, None
Cooling Zones:
5
Hot Water:
Water Source:
Public
Sewer:
Public Sewer
Energy Features:
Exterior & Lot
Exterior Features:
Deck - Wood, Rain Gutters, Hot Tub/Spa, Storage, Professional Landscaping, Sprinkler System, Garden, Invisible Fence
Patio & Porch:
Deck - Wood
Fencing:
Invisible
Other Structures:
Lot Features:
Road Surface:
Paved
Parking & Garage
Garage Spaces:
2
Garage Type:
Attached
Total Parking Spaces:
4
Parking Features:
Attached, Garage Door Opener, Storage, Paved Drive, Off Street, Paved
Special Features
Fireplaces:
1
Fireplace Type:
Spa/Hot Tub:
Yes
Spa Features:
Private
Community Amenities:
Park, Walk/Jog Trails, Golf, Bike Path, Conservation Area, Highway Access, Public School
Nearby Schools
School District
Winchester School District local
A+
School Safety
2024-25
0.1%
Very Low (Safest)
0.1%
Suspensions
0.1%
In-School
5.4% below state avg
Elementary Schools
3 schools
A+
Vinson-Owen Elementary School
0.6 mi
|
#46 of 825
|
Score: 62.7
Improved 106 spots from last year
+4.5 above state avg
387 students
Diverse
Rising School
Strong Attendance
Grades PK-05
A+
Ambrose Elementary School
0.8 mi
|
#13 of 825
|
Score: 65.8
Improved 34 spots from last year
+7.6 above state avg
377 students
Moderate
Rising School
Strong Attendance
Grades K-05
A-
M. Norcross Stratton Elementary School
0.9 mi
|
#186 of 825
|
Score: 55.7
Dropped 44 spots from last year
-2.5 below state avg
423 students
Diverse
Diverse Student Body
Strong Attendance
Grades K-05
Middle Schools
3 schools
A+
Ottoson Middle School
1.4 mi
|
#4 of 352
|
Score: 65.7
Improved 13 spots from last year
+7.5 above state avg
977 students
Diverse
Strong Attendance
Grades 07-08
A+
McCall Middle School
1.9 mi
|
#15 of 352
|
Score: 62.8
Dropped 2 spots from last year
+4.6 above state avg
1,053 students
Diverse
Strong Attendance
Grades 06-08
A+
Gibbs School
2.5 mi
|
#32 of 352
|
Score: 59.9
Improved 7 spots from last year
+1.7 above state avg
480 students
Diverse
Strong Attendance
Grades 06
High Schools
3 schools
Lexington Christian Academy
1.2 mi
Grades 06-12
Arlington Catholic High School
2.0 mi
17 sports
• 1,412 athletes
Strong Athletics
Grades 09-12
A+
Winchester High School
2.1 mi
|
#16 of 346
|
Score: 74.0
Improved 19 spots from last year
+15.8 above state avg
1,418 students
Diverse
20 sports
• 2,818 athletes
Strong AP Program
High Graduation Rate
College Ready Curriculum
Strong Athletics
Grades 09-12
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Loan Amount
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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
$1,591
Homeowners Insurance
$200
PMI (if <20% down)
$0
Loan Summary
Total of 360 payments
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$0
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$0
Rate Impact
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Payment Over Time
Year 1
95% Interest
Year 15
50/50
Year 30
95% Principal
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Location
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Neighborhood
Winchester Highlands
9 Plymouth Rd, Winchester MA 01890
Winchester, MA 01890
Listing Information
Listing Agent
Steph Crawford Group
Listing Office
Real Broker MA, LLC
Office Phone
855-450-0442
Agent MLS ID
TM355651
Office MLS ID
AN4866
Listing Data Updated
Sep 24, 2026 3:30 PM 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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