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.
For sale
$1,300,000
3 Chesterford Ter, Winchester, MA 01890
3beds
2,006sqft
Single Family Residence
Built in 1933
0.3 Acres Lot
$1,301,600 Zestimate®
$648/sqft
$-- HOA
What's special
Classic architectural characterSurrounded by mature landscapingCoveted cul-de-sac
- 2 days |
- 1,263 |
- 64 |
Zillow last checked:
Listing updated:
Listed by:
The Fenway Group 617-818-0079,
Compass 617-206-3333,
Scott McNeill 617-818-0079
Source: MLS PIN,MLS#: 73545054
Loading...
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 2
- Full bathrooms: 1
- 1/2 bathrooms: 1
Primary bedroom
- Level: Second
Bedroom 2
- Level: Second
Bedroom 3
- Level: Second
Bathroom 1
- Level: First
Bathroom 2
- Level: Second
Dining room
- Level: First
Kitchen
- Level: First
Living room
- Level: First
Heating
- Steam, Natural Gas
Cooling
- Window Unit(s)
Appliances
- Included: Gas Water Heater, Range, Dishwasher, Disposal, Refrigerator, Washer, Dryer
- Laundry: In Basement
Features
- Flooring: Wood, Tile
- Basement: Full,Partially Finished,Bulkhead
- Number of fireplaces: 2
Interior area
- Total structure area: 2,006
- Total interior livable area: 2,006 sqft
- Finished area above ground: 2,006
Video & virtual tour
Property
Parking
- Total spaces: 2
- Parking features: Paved Drive
- Garage spaces: 1
- Uncovered spaces: 1
Features
- Patio & porch: Deck - Wood
- Exterior features: Deck - Wood
Lot
- Size: 0.3 Acres
- Features: Wooded
Details
- Parcel number: M:019 B:0153 L:0,899819
- Zoning: RDB
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Cape
- Property subtype: Single Family Residence
Materials
- Foundation: Concrete Perimeter, Irregular
- Roof: Shingle
Condition
- Year built: 1933
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
Community & HOA
Community
- Features: Public Transportation, Shopping, Park, Walk/Jog Trails, Golf, Bike Path, Conservation Area, Highway Access, House of Worship, Private School, Public School
HOA
- Has HOA: No
Location
- Region: Winchester
Financial & listing details
- Price per square foot: $648/sqft
- Tax assessed value: $1,469,000
- Annual tax amount: $16,176
- Date on market: 7/6/2026
Estimated market value
$1,301,600
$1.24M - $1.37M
$4,606/mo
Price history
| Date | Event | Price |
|---|---|---|
| 7/6/2026 | Listed for sale | $1,300,000+87.7%$648/sqft |
Source: MLS PIN #73545054 Report a problem | ||
| 9/16/2003 | Sold | $692,500+71.8%$345/sqft |
Source: Public Record Report a problem | ||
| 8/2/1999 | Sold | $403,000$201/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $15,986 +3.2% | $1,441,500 +5.4% |
| 2024 | $15,495 +6.1% | $1,367,600 +10.5% |
| 2023 | $14,608 0% | $1,238,000 +6% |
| 2022 | $14,609 +9% | $1,167,800 +11.8% |
| 2021 | $13,407 +7.1% | $1,045,000 +3.5% |
| 2020 | $12,513 +9.9% | $1,009,900 +7.5% |
| 2019 | $11,381 +4% | $939,800 +4.7% |
| 2018 | $10,943 +7.4% | $897,700 +8.2% |
| 2017 | $10,192 +6.8% | $830,000 +1.6% |
| 2016 | $9,546 +3.3% | $817,300 +7.4% |
| 2015 | $9,239 +7.4% | $761,000 +12% |
| 2014 | $8,601 +0.6% | $679,400 +1.5% |
| 2013 | $8,548 +1.7% | $669,400 |
| 2012 | $8,401 +3.7% | $669,400 |
| 2011 | $8,100 +3.5% | $669,400 -1.6% |
| 2010 | $7,829 +2.1% | $680,200 |
| 2009 | $7,666 +3.7% | $680,200 -2.8% |
| 2008 | $7,394 +6% | $699,500 +3.6% |
| 2007 | $6,977 +2.4% | $675,400 +2.8% |
| 2006 | $6,812 +3.9% | $656,900 +4.4% |
| 2005 | $6,554 +14.7% | $629,000 +25.3% |
| 2004 | $5,714 +9.5% | $502,100 +9.5% |
| 2003 | $5,220 +12% | $458,700 +8.9% |
| 2002 | $4,661 +13.5% | $421,400 +33.4% |
| 2000 | $4,107 -5.6% | $315,900 +6.3% |
| 1999 | $4,351 | $297,200 |
Find assessor info on the county website
Monthly payment
Est. payment$--/mo
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
See how much you could borrow to make a competitive offer.
Climate risks
Neighborhood: 01890
Nearby schools
GreatSchools rating
- 8/10Lynch Elementary SchoolGrades: PK-5Distance: 0.2 mi
- 8/10McCall Middle SchoolGrades: 6-8Distance: 1.1 mi
- 10/10Winchester High SchoolGrades: 9-12Distance: 1 mi
Schools provided by the listing agent
- Elementary: Lynch Elementry
- Middle: Mccall Middle
- High: Winchester High School
Source: MLS PIN. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
A local agent can set up tours, give advice and negotiate with sellers.
- Massachusetts
- Middlesex County
- Winchester
- 01890
- 3 Chesterford Ter
Nearby cities
Nearby zip codes
Other Winchester Topics
