42
$2,049,000
5 bd · 4 ba · 4,063 sqft
21 Amberwood Dr, Winchester, MA
Gayle Winters & Co. Team · Compass

No listing photos
5
Beds
3.5
Baths
3,780
Sqft
1951
Year built
Range $1,893,502 – $2,048,740 · as of August 30, 2026
ATTOM automated valuation model · 54 published estimates over 6.7 years · shaded band is the model's own published low-to-high range
Highest reading $2,614,382 in August 2024; lowest $1,447,792 in January 2020. The vertical scale starts at the series' own low, not at zero — it is drawn to show movement, not absolute size.
$394,224
Estimated monthly payment
$12,842/mo
Loan amount $1,576,897. Estimate only — your actual rate and payment depend on credit, location, and lender.
2025 roll
Rings at ½ mile and 1 mile. Basemap © OpenMapTiles © OpenStreetMap contributors.
Open the Winchester camera map3 license-plate readers mapped within 1 mile of this home, all identified as Flock Safety devices. None within ½ mile. Nearest: 0.7 mi north. Operator named in the data: Woburn Police.
| Device type | Within ½ mi | Within 1 mi |
|---|---|---|
| License-plate readers | 0 | 3 |
| of which Flock Safety | 0 | 3 |
Community-reported via OpenStreetMap; may be incomplete. Data as of . © OpenStreetMap contributors (ODbL)
License-plate readers (ALPR) are fixed cameras that photograph passing vehicles and read their plates. Records are typically shared with the agency or association that operates the camera.
Flock Safety is a company whose plate-reader cameras are used by police departments, cities, HOAs and businesses. Its devices are usually solar-powered and pole-mounted.
Within 2 miles of this home: 36+ restaurants and cafés, 3 grocery stores, 36+ parks and green spaces, and 33+ transit stops.
Place data from OpenStreetMap.
Wendy's
Montvale Avenue
Polcari's Restaurant
Italian restaurant · Montvale Avenue
Bickford's Grille
Montvale Avenue
Eighty Eight Cafe
Chinese restaurant · Washington Street
McDonald's
Montvale Avenue
Dunkin
Montvale Avenue
Sam Walker’s American Tavern
Rainin Road
Swanton Street Diner
Swanton Street
Stop & Shop
Main Street
Natural Food Exchange
Pleasant Street
Apna Bazar
Davidson Park
Leonard Field
Leland Park
Aberjona River
Burbank Pond
Dikes Pond
Unicorn Park
Middlesex Fells Reservation
Montvale Ave @ Washington St
42 Central St
Central St @ Montvale Ave
Montvale Ave @ I93 ramp
Montvale Ave @ I93
Central St @ Washington Circle
Central St @ Pine Street
Pine St @ Floyd St
MLS Property Information Network (MLS PIN)Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.
42
$2,049,000
5 bd · 4 ba · 4,063 sqft
21 Amberwood Dr, Winchester, MA
Gayle Winters & Co. Team · Compass
32$1,529,000
4 bd · 4 ba · 2,709 sqft
25 Arlington St, Winchester, MA
Domingo Medina · Coldwell Banker Realty - Lexington
39$2,399,000
4 bd · 4 ba · 3,550 sqft
63 Wedgemere Avenue, Winchester, MA
Paula R. Sughrue · Better Homes and Gardens Real Estate - The Shanahan Group
New41$1,399,000
5 bd · 2 ba · 2,071 sqft
15 Lloyd Street, Winchester, MA
Kim Covino & Co. Team · Compass
41$1,850,000
4 bd · 3 ba · 3,604 sqft
1 Overlook Way, Winchester, MA
Lynne Russo · Better Homes and Gardens Real Estate - The Shanahan Group
Price Reduced41$2,195,000
5 bd · 4 ba · 5,006 sqft
276 High Street, Winchester, MA
Kim Covino & Co. Team · Compass





School ratings (A+ to F) from HJN community data.
Acera School
KG-10 · Special Program Emphasis
144 students · 4.0:1 student–teacher
Muraco Elementary School
KG-5 · Regular · Winchester School District
352 students · 10.9:1 student–teacher
Goodyear Elementary School
KG-5 · Regular · Woburn School District
352 students · 11.1:1 student–teacher
Shamrock Elementary School
KG-5 · Regular · Woburn School District
284 students · 10.4:1 student–teacher
Winchester High School
9-12 · Regular · Winchester School District
1,404 students · 14.8:1 student–teacher
The Wilder School
UG-UG · Alternative/Other
2 students · 1.8:1 student–teacher
St Mary's School
PK-KG · Early Childhood Program/Child Care Center
9 students · 9.0:1 student–teacher
South Elementary School
PK-4 · Regular · Stoneham School District
347 students · 12.3:1 student–teacher