Location

Nearby schools

School ratings (A+ to F) from HJN community data.

Childrens Own School
PK-PK · Montessori
15 students · 3.0:1 student–teacher
0.3 mi
McCall Middle School
6-8 · Regular · Winchester School District
1,036 students · 12.6:1 student–teacher
McCall Middle School school rating: A 0.6 mi
Lincoln Elementary School
KG-5 · Regular · Winchester School District
334 students · 11.1:1 student–teacher
Lincoln Elementary School school rating: A 0.7 mi
Medford High School
9-12 · Regular · Medford School District
1,195 students · 9.2:1 student–teacher
Medford High School school rating: C 0.9 mi
The Wilder School
UG-UG · Alternative/Other
2 students · 1.8:1 student–teacher
1.0 mi
St Mary's School
PK-KG · Early Childhood Program/Child Care Center
9 students · 9.0:1 student–teacher
1.0 mi
Winchester High School
9-12 · Regular · Winchester School District
1,404 students · 14.8:1 student–teacher
Winchester High School school rating: A+ 1.0 mi
Ambrose Elementary School
KG-5 · Regular · Winchester School District
398 students · 12.1:1 student–teacher
Ambrose Elementary School school rating: A 1.4 mi

Nearby places

Within 2 miles of this home: 39+ restaurants and cafés, 2 grocery stores, 38+ parks and green spaces, and 32+ transit stops.

Place data from OpenStreetMap.

Food & drink

Black Horse Tavern
Waterfield Road
0.8 mi
First House Pub
0.8 mi
Frozen Hoagies
Main Street
0.8 mi
Comella's
0.8 mi
China Sky
Converse Place
0.8 mi
Starbucks
Main Street
0.8 mi
Nourish Your Soul
0.8 mi
D'Agostino's Delicatessen
0.8 mi

Groceries

Stop & Shop
Main Street
1.1 mi
Whole Foods Market
Mystic Valley Parkway
1.7 mi

Parks & recreation

Dennett Park
0.3 mi
Brooks Parkhurst Town Forest
0.4 mi
Stone Family Playground
0.6 mi
Ginn Field
0.6 mi
Mystic Valley Parkway
0.7 mi
Manchester Field
0.7 mi
Mill Pond
0.8 mi
Brooks Pond
0.8 mi

Transit

Main Street @ Highland Avenue
0.2 mi
Main Street opposite Highland Avenue
0.2 mi
Main Street @ Marshall Road
0.3 mi
Main Street @ Everell Road
0.3 mi
Main Street @ Ridgefield Road
0.3 mi
Main Street @ Madison Avenue West
0.3 mi
Main Street @ Gateway South
0.3 mi
Main Street @ Town Way
0.3 mi

The 01890 market

Homes for sale: 57
Median list price: $1,549,000

Similar homes nearby

See all in 01890

Sources for the nearby listings shown on this page

MLS Property Information Network (MLS PIN): The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.
Listing information ©2026 MLS Property Information Network, Inc®. All Rights Reserved. Last Updated: 2026-10-23 13:33:00 UTC

Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.

No listing photos

20 Ledyard Rd, Winchester MA 01890

3

Beds

2

Baths

2,184

Sqft

1952

Year built

Estimated value: $1,444,580

Range $1,369,254 – $1,519,906 · as of August 30, 2026

How this estimate has moved

ATTOM automated valuation model · 54 published estimates over 6.7 years · shaded band is the model's own published low-to-high range

$866,455 January 2020$1,444,580 August 2026

Highest reading $1,449,404 in July 2026; lowest $856,941 in April 2020. The vertical scale starts at the series' own low, not at zero — it is drawn to show movement, not absolute size.

Public records

3 beds
2 baths
2,184 sqft
9,121 sqft lot
Built 1952
Stories: 1
Use: RESIDENTIAL
APN WINC M:006 B:0271 L:0

Estimate your monthly payment

Home price

Down payment (20%)

$288,916

Loan term

Interest rate (%)

Property tax (%/yr)

Home insurance ($/yr)

HOA ($/mo)

Estimated monthly payment

$9,379/mo

Principal & interest$7,939

Property tax$1,324

Home insurance$117

Loan amount $1,155,664. Estimate only — your actual rate and payment depend on credit, location, and lender.

Tax history

2025 roll

Land: $906,800
Structure: $269,900
Assessed total: $1,176,700
County market value: $1,160,805
Property tax billed: $130.50

Sale & deed history

January 15, 2013Not an arm's-length transfer—
September 16, 2010Arm's-length$637,000