Location

Nearby schools

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

Muraco Elementary School
KG-5 · Regular · Winchester School District
352 students · 10.9:1 student–teacher
Muraco Elementary School school rating: A+ 0.3 mi
Acera School
KG-10 · Special Program Emphasis
144 students · 4.0:1 student–teacher
0.4 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+ 0.7 mi
St Mary's School
PK-KG · Early Childhood Program/Child Care Center
9 students · 9.0:1 student–teacher
0.7 mi
Lincoln Elementary School
KG-5 · Regular · Winchester School District
334 students · 11.1:1 student–teacher
Lincoln Elementary School school rating: A 1.0 mi
McCall Middle School
6-8 · Regular · Winchester School District
1,036 students · 12.6:1 student–teacher
McCall Middle School school rating: A 1.1 mi
Goodyear Elementary School
KG-5 · Regular · Woburn School District
352 students · 11.1:1 student–teacher
Goodyear Elementary School school rating: C- 1.1 mi

Nearby places

Within 2 miles of this home: 38+ restaurants and cafés, 3 grocery stores, 36+ parks and green spaces, and 32+ transit stops.

Place data from OpenStreetMap.

Food & drink

Eighty Eight Cafe
Chinese restaurant · Washington Street
0.3 mi
Swanton Street Diner
Swanton Street
0.5 mi
Domino's
Main Street
0.8 mi
Dunkin
Main Street
0.8 mi
Mitho Restaurant
Main Street
0.8 mi
Burger King
Main Street
0.8 mi
Toscano's Italian Kitchen
Main Street
0.8 mi
Bagels N Brew
Main Street
0.8 mi

Groceries

Stop & Shop
Main Street
0.8 mi
Natural Food Exchange
Pleasant Street
1.9 mi
Whole Foods Market
Cambridge Road
2.0 mi

Parks & recreation

Leonard Field
0.2 mi
Aberjona River
0.3 mi
Davidson Park
0.4 mi
Middlesex Fells Reservation
0.5 mi
Long Pond
0.6 mi
Highland Park
0.7 mi
Judkins Pond
0.8 mi
McDonald Field
0.8 mi

Transit

757 Main Street
0.8 mi
Main Street opposite Richardson Street
0.8 mi
Main Street @ Clark Street
0.8 mi
Main St @ Lake St
0.8 mi
Main St @ Vine St
0.9 mi
Main Street @ Canal Street
0.9 mi
Main Street opposite Hemingway Street
1.0 mi
Main Street @ Hemingway Street
1.0 mi

The 01890 market

Homes for sale: 57
Median list price: $1,529,000

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: 2026-10-22 12:46:00 UTC

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

No listing photos

21 Grayson Road, Winchester MA 01890

4

Beds

3

Baths

3,007

Sqft

1930

Year built

Estimated value: $1,486,027

Range $1,440,772 – $1,531,282 · 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

$936,698 January 2020$1,486,027 August 2026

Highest reading $1,776,279 in November 2025; lowest $936,698 in January 2020. The vertical scale starts at the series' own low, not at zero — it is drawn to show movement, not absolute size.

Public records

4 beds
3 baths
3,007 sqft
5,824 sqft lot
Built 1930
Stories: 2
Use: RESIDENTIAL
APN WINC M:002 B:0012 L:0

Estimate your monthly payment

Home price

Down payment (20%)

$297,205

Loan term

Interest rate (%)

Property tax (%/yr)

Home insurance ($/yr)

HOA ($/mo)

Estimated monthly payment

$9,645/mo

Principal & interest$8,166

Property tax$1,362

Home insurance$117

Loan amount $1,188,822. Estimate only — your actual rate and payment depend on credit, location, and lender.

Tax history

2025 roll

Land: $691,800
Structure: $621,600
Assessed total: $1,313,400
County market value: $1,614,335
Property tax billed: $145.66

Sale & deed history

July 14, 2023Arm's-length—
August 26, 2021Arm's-length$1,322,000
March 11, 2016$705,500
November 23, 2015Arm's-length—
September 30, 2008Not an arm's-length transfer—