Price Reduced42
$1,999,000
5 bd · 4 ba · 4,063 sqft
21 Amberwood Dr, Winchester, MA
Gayle Winters & Co. Team · Compass

No listing photos
5
Beds
4.5
Baths
4,658
Sqft
1925
Year built
Range $2,583,084 – $2,914,438 · 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 $3,989,897 in July 2025; lowest $1,743,539 in April 2020. The vertical scale starts at the series' own low, not at zero — it is drawn to show movement, not absolute size.
$549,752
Estimated monthly payment
$17,742/mo
Loan amount $2,199,009. Estimate only — your actual rate and payment depend on credit, location, and lender.
2025 roll
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.
Price Reduced42
$1,999,000
5 bd · 4 ba · 4,063 sqft
21 Amberwood Dr, Winchester, MA
Gayle Winters & Co. Team · Compass
32$2,650,000
4 bd · 5 ba · 5,233 sqft
18 Middlesex St, Winchester, MA
Jennifer Taves · Coldwell Banker Realty - Boston
Price Reduced42$2,400,000
6 bd · 4 ba · 3,534 sqft
7 Lakeview Terrace, Winchester, MA
Elizabeth Darby · Berkshire Hathaway HomeServices Commonwealth Real Estate
Price Reduced42$3,200,000
6 bd · 6 ba · 6,100 sqft
9 Albamont Road, Winchester, MA
Kim Covino & Co. Team · Compass
10$2,999,000
5 bd · 5 ba · 4,900 sqft
5 Forest Cir, Winchester, MA
Pirani & Wile Group · Gibson Sotheby's International Realty
41$2,950,000
6 bd · 4 ba · 4,752 sqft
18 Surrey Road, Winchester, MA
Mary Kelly · Century 21 Property Central Inc.





School ratings (A+ to F) from HJN community data.
Ambrose Elementary School
KG-5 · Regular · Winchester School District
398 students · 12.1:1 student–teacher
McCall Middle School
6-8 · Regular · Winchester School District
1,036 students · 12.6:1 student–teacher
Lincoln Elementary School
KG-5 · Regular · Winchester School District
334 students · 11.1:1 student–teacher
Childrens Own School
PK-PK · Montessori
15 students · 3.0:1 student–teacher
Winchester High School
9-12 · Regular · Winchester School District
1,404 students · 14.8:1 student–teacher
St Mary's School
PK-KG · Early Childhood Program/Child Care Center
9 students · 9.0:1 student–teacher
Lynch Elementary School
KG-5 · Regular · Winchester School District
426 students · 10.8:1 student–teacher
The Wilder School
UG-UG · Alternative/Other
2 students · 1.8:1 student–teacher
Within 2 miles of this home: 38+ restaurants and cafés, 2 grocery stores, 35+ parks and green spaces, and 31+ transit stops.
Place data from OpenStreetMap.
A Tavola
Italian restaurant · Church Street
Nouvelle Maison Fine Provisions
D'Agostino's Delicatessen
Black Horse Tavern
Waterfield Road
Nourish Your Soul
The Bagel Bar
Starbucks
Main Street
Frozen Hoagies
Main Street
Stop & Shop
Main Street
Whole Foods Market
Cambridge Road
Glen Green
Ginn Field
Palmer Playground
Shannon Beach
Stone Family Playground
Mystic Valley Parkway
Borggaard Beach
Manchester Field
Cambridge Street @ High Street
Cambridge Street @ Church Street
125 Cambridge Street opposite Oneida Road
Cambridge Street @ Oneida Road
Cambridge St @ Myopia Rd
65 Cambridge St @ Winchester Boat Club
Opp 65 Cambridge St @ Winchester Boat Club
Cambridge Street @ Foxcroft Road