LevelSecond
3 Chesterford Terrace, Winchester MA 01890
Winchester, MA 01890
$1,300,000
Est. $8,122/month
About this home
Nestled at the end of a coveted cul-de-sac, 3 Chesterford Terrace presents a rare opportunity to own a timeless Winchester home on a picture-perfect 12,972 SQ FT flat lot. Designed by renowned Winchester architect Jerome Bailey Foster, this charming 3+ bed, 1.5-bath residence blends classic architectural character with an exceptional setting. Surrounded by mature landscaping & set on one of Winchester's most desirable streets, the home offers endless potential for today's buyer. Enjoy the convenience of being a short stroll to Lynch Elementary School & moments from Winchester's scenic Three Ponds area, where walking trails & outdoor recreation await. Whether you're looking to restore & enhance an architectural gem or create your dream home in an unbeatable location, this property offers a truly special combination of charm & opportunity. Rarely does a home with \setting & potential become available in Winchester. Estate Sale. Sold in as-is condition. Offers due @ noon on 7/14.
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Recently Sold Nearby
Property History
Market Insights
Property Timeline
Pending Sale
Jul 16, 2026
Offer accepted, sale pending
Listed for Sale
Jul 6, 2026
$1,300,000
Original listing
Agent: The Fenway Group
Office: Compass
| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 07/16/2026 | ⏳ Pending Sale | - | - | - | Offer accepted, sale pending |
| 07/06/2026 | 🏠 Listed for Sale | $1,300,000 | - | - | Original listing |
Tax History
| Year | Taxes | Assessment |
|---|---|---|
| 2026 | $16,176 | $1,469,000 |
Financial Details
Annual Property Tax
$16,176
Tax Year 2026
Assessed Value
$1,469,000
Facts & Features
1 Car Garage
Home Facts
Type
Residential
Style
Single Family Residence
Year Built
1933
Living Area
2,006 sq ft
Lot Size
0.30 acres
Bedrooms
3
Full Baths
1
Half Baths
1
Total Rooms
8
Interior
Heating
Steam, Natural Gas
Cooling
Window Unit(s)
Flooring
Wood, Tile
Appliances
Gas Water Heater, Range, Dishwasher, Disposal, Refrigerator, Washer, Dryer
Fireplace
None
Fireplaces
2
Basement
Full, Partially Finished, Bulkhead
Laundry
In Basement
Features
None
Exterior
Construction
None
Architecture
Cape
Roof
Shingle
Features
Deck - Wood
Pool
None
Spa
None
Fencing
None
Patio/Porch
Deck - Wood
Parking
Garage Spaces
1
Has Garage
Yes
Features
Paved Drive
Total Spaces
2
Utilities
Electric
None
Water
Public
Sewer
Public Sewer
Gas
None
Other
None
Financial
Annual Tax
$16,176
Assessed Value
$1,469,000
HOA & Community
Fee Includes
None
Amenities
None
Optional Fee Includes
None
MA Disclosures
Seller Disclosures
Some Asbestos Insulation In Basement. Broken Tiles In Bath. Glass In Sunroom Window To Be Replaced. Ring Door Bell Not Included. Garage Door Motor Not Working. Estate Sale- Sold In As-is Condition. Seller Will Review Offers At Noon On Tues 7/14 But Reserves Right To Accept An Offer Before Then.
Additional Details
Possession
None
Accepted Financing
None
Structure Type
[]
Sq Ft Source
Public Record
Documents
None
County
Middlesex
Total market time (incl. prior listings)
10 days
Property Overview
Property Type
Single Family Residence
Listing Type
For Sale
Year Built
1933
Bedrooms
3
Full Bathrooms
1
Half Bathrooms
1
Living Area
2,006 sq ft
Total Rooms
8
Room Details
Interactive room guide
Floor Layout
Finished Area
2,006 sq ft above grade
LevelSecond
LevelSecond
LevelSecond
LevelFirst
LevelFirst
LevelFirst
LevelFirst
Display Options
Outdoor Areas
Patio & porchDeck - Wood
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.
First Floor
Bathroom1
Dining Room
Kitchen
Living Room
Second Floor
Bedroom3
Bathroom2
Bedroom2
Master Bedroom
Other Floor
Bedroom5
Bedroom4
Bathroom3
Office
Family Room
Master Bathroom
Interior Features
Flooring:
Wood, Tile
Appliances:
Gas Water Heater, Range, Dishwasher, Disposal, Refrigerator, Washer, Dryer
Interior Features:
Windows:
Basement:
Full, Partially Finished, Bulkhead
Laundry:
In Basement
Security:
Construction & Materials
Style:
Cape
Year Built:
1933
Structure Type:
Exterior Materials:
Roof:
Shingle
Foundation:
Concrete Perimeter, Irregular
Heating, Cooling & Utilities
Heating:
Steam, Natural Gas
Heating Zones:
1
Cooling:
Window Unit(s)
Hot Water:
Water Source:
Public
Sewer:
Public Sewer
Energy Features:
Exterior & Lot
Exterior Features:
Deck - Wood
Patio & Porch:
Deck - Wood
Fencing:
Other Structures:
Lot Features:
Wooded
Road Surface:
Parking & Garage
Garage Spaces:
1
Total Parking Spaces:
2
Parking Features:
Paved Drive
Special Features
Fireplaces:
2
Fireplace Type:
Community Amenities:
Public Transportation, Shopping, Park, Walk/Jog Trails, Golf, Bike Path, Conservation Area, Highway Access, House of Worship, Private School, 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
Lynch Elementary School
0.2 mi
|
#113 of 824
|
Score: 58.6
Dropped 31 spots from last year
+0.4 above state avg
426 students
Diverse
Grades PK-05
Creative Corner School Inc
0.5 mi
Grades PK-K
A+
Ambrose Elementary School
1.0 mi
|
#11 of 824
|
Score: 66.1
Improved 36 spots from last year
+7.9 above state avg
398 students
Moderate
Rising School
Strong Attendance
Grades K-05
Middle Schools
3 schools
A+
McCall Middle School
1.1 mi
|
#16 of 352
|
Score: 62.4
Dropped 3 spots from last year
+4.2 above state avg
1,036 students
Diverse
Strong Attendance
Grades 06-08
C+
Daniel L Joyce Middle School
1.7 mi
|
#217 of 352
|
Score: 39.5
Dropped 14 spots from last year
-18.7 below state avg
455 students
Moderate
Grades 06-08
B
John F Kennedy Middle School
2.3 mi
|
#176 of 352
|
Score: 42.4
Improved 42 spots from last year
-15.8 below state avg
521 students
Diverse
Rising School
Grades 06-08
High Schools
3 schools
A+
Winchester High School
1.0 mi
|
#17 of 346
|
Score: 73.6
Improved 18 spots from last year
+15.4 above state avg
1,404 students
Diverse
20 sports
• 2,818 athletes
Strong AP Program
High Graduation Rate
College Ready Curriculum
Strong Athletics
Grades 09-12
B
Woburn High School
1.7 mi
|
#143 of 346
|
Score: 56.1
Dropped 21 spots from last year
-2.1 below state avg
1,259 students
Diverse
18 sports
• 2,056 athletes
High Graduation Rate
College Ready Curriculum
Strong Athletics
Grades 09-12
A-
Medford High School
2.4 mi
|
#94 of 346
|
Score: 60.6
Improved 24 spots from last year
+2.3 above state avg
1,195 students
Diverse
19 sports
• 1,212 athletes
Strong AP Program
Rising School
Career Tech Programs
College Ready Curriculum
Grades PK-12
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Year 1
95% Interest
Year 15
50/50
Year 30
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Location
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Neighborhood
3 Chesterford Terrace, Winchester MA 01890
Winchester, MA 01890
Listing Information
Listing Agent
The Fenway Group
Listing Office
Compass
Office Phone
617-206-3333
Agent MLS ID
TM337387
Office MLS ID
AN2383
Listing Data Updated
Jul 16, 2026 9:29 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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