Location

Nearby schools

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

McCall Middle School
6-8 · Regular · Winchester School District
1,036 students · 12.6:1 student–teacher
McCall Middle School school rating: A 0.4 mi
Lincoln Elementary School
KG-5 · Regular · Winchester School District
334 students · 11.1:1 student–teacher
Lincoln Elementary School school rating: A 0.4 mi
Childrens Own School
PK-PK · Montessori
15 students · 3.0:1 student–teacher
0.5 mi
St Mary's School
PK-KG · Early Childhood Program/Child Care Center
9 students · 9.0:1 student–teacher
0.7 mi
The Wilder School
UG-UG · Alternative/Other
2 students · 1.8:1 student–teacher
0.7 mi
Winchester High School
9-12 · Regular · Winchester School District
1,404 students · 14.8:1 student–teacher
Winchester High School school rating: A+ 0.8 mi
Ambrose Elementary School
KG-5 · Regular · Winchester School District
398 students · 12.1:1 student–teacher
Ambrose Elementary School school rating: A 1.0 mi
Medford High School
9-12 · Regular · Medford School District
1,195 students · 9.2:1 student–teacher
Medford High School school rating: C 1.2 mi

Nearby places

Within 2 miles of this home: 39+ restaurants and cafés, 2 grocery stores, 36+ parks and green spaces, and 32+ transit stops.

Place data from OpenStreetMap.

Food & drink

Black Horse Tavern
Waterfield Road
0.5 mi
A Tavola
Italian restaurant · Church Street
0.5 mi
Nouvelle Maison Fine Provisions
0.5 mi
D'Agostino's Delicatessen
0.5 mi
First House Pub
0.5 mi
Frozen Hoagies
Main Street
0.5 mi
Nourish Your Soul
0.5 mi
Starbucks
Main Street
0.5 mi

Groceries

Stop & Shop
Main Street
0.8 mi
Whole Foods Market
Cambridge Road
1.8 mi

Parks & recreation

Stone Family Playground
0.1 mi
Ginn Field
0.2 mi
Mystic Valley Parkway
0.3 mi
Manchester Field
0.3 mi
Brooks Parkhurst Town Forest
0.4 mi
Mill Pond
0.5 mi
Town Common
0.5 mi
Chefalo Park
0.6 mi

Transit

Main Street @ Lincolnshire Way
0.1 mi
Main Street @ Chestnut Street
0.1 mi
Main Street @ Madison Avenue West
0.1 mi
Main Street @ Marshall Road
0.1 mi
Wedgemere
0.2 mi
Main Street @ Mystic Avenue
0.2 mi
Main Street @ Prospect Street
0.2 mi
Main Street @ Everell Road
0.2 mi

The 01890 market

Homes for sale: 53
Median list price: $1,650,000

Similar homes nearby

See all in 01890

36Active
$1,899,000
4 bd · 3 ba · 3,757 sqft
85 High Street, Winchester, MA
Catherine Albiani · Better Homes and Gardens Real Estate - The Shanahan Group

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

No listing photos

20 Winslow Rd, Winchester MA 01890

3

Beds

4

Baths

3,005

Sqft

1926

Year built

Estimated value: $1,932,961

Range $1,840,340 – $2,025,582 · 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

$1,302,682 January 2020$1,932,961 August 2026

Highest reading $2,125,782 in November 2025; lowest $1,269,174 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
4 baths
3,005 sqft
6,695 sqft lot
Built 1926
Stories: 2
Use: RESIDENTIAL
APN WINC M:008 B:0058 L:0

Estimate your monthly payment

Home price

Down payment (20%)

$386,592

Loan term

Interest rate (%)

Property tax (%/yr)

Home insurance ($/yr)

HOA ($/mo)

Estimated monthly payment

$12,427/mo

Principal & interest$10,538

Property tax$1,772

Home insurance$117

Loan amount $1,546,369. Estimate only — your actual rate and payment depend on credit, location, and lender.

Tax history

2026 roll

Land: $859,200
Structure: $768,200
Assessed total: $1,627,400
County market value: $1,903,019
Property tax billed: $18,032

Sale & deed history

September 27, 2023Arm's-length$1,725,000
December 15, 2017Arm's-length—
January 29, 2013Not an arm's-length transfer—
December 29, 2010Arm's-length$597,500

The 01890 market

Homes for sale: 53
Median list price: $1,650,000

Nearby schools

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

Similar homes nearby

See all in 01890

36Active
$1,899,000
4 bd · 3 ba · 3,757 sqft
85 High Street, Winchester, MA
Catherine Albiani · Better Homes and Gardens Real Estate - The Shanahan Group

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

42Active

$1,699,000

4 bd · 3 ba · 2,736 sqft

3 Sunset Road, Winchester, MA

Kim Covino & Co. Team · Compass

Price Reduced42Active

$1,499,000

4 bd · 2 ba · 2,421 sqft

4 Churchill Road, Winchester, MA

Kim Covino & Co. Team · Compass

Price Reduced40Active

$2,149,000

4 bd · 4 ba · 3,570 sqft

19 Hancock Street, Winchester, MA

Vita Realty Group · Compass

Price Reduced41Active

$1,744,000

3 bd · 4 ba · 3,010 sqft

1 Town Way, Winchester, MA

Vita Realty Group · Compass

Price Reduced42Active

$2,299,000

4 bd · 5 ba · 4,450 sqft

54 Squire Road, Winchester, MA

Anthony Marino · The Marino Group Collection

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: 2026-11-03 08:05:00 UTC