New10
$2,999,000
5 bd · 5 ba · 4,900 sqft
5 Forest Cir, Winchester, MA
Pirani & Wile Group · Gibson Sotheby's International Realty

No listing photos
4
Beds
3
Baths
6,671
Sqft
1932
Year built
Range $2,443,461 – $2,918,103 · 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 $3,873,208 in July 2025; lowest $2,322,374 in April 2020. The vertical scale starts at the series' own low, not at zero — it is drawn to show movement, not absolute size.
$536,156
Estimated monthly payment
$17,306/mo
Loan amount $2,144,626. Estimate only — your actual rate and payment depend on credit, location, and lender.
2025 roll
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
Stratton Elementary School
KG-5 · Regular · Arlington School District
448 students · 12.2:1 student–teacher
Childrens Own School
PK-PK · Montessori
15 students · 3.0:1 student–teacher
John A. Bishop Elementary School
KG-5 · Regular · Arlington School District
375 students · 12.4:1 student–teacher
McCall Middle School
6-8 · Regular · Winchester School District
1,036 students · 12.6:1 student–teacher
Van - Owen Elementary School
KG-5 · Regular · Winchester School District
441 students · 12.5:1 student–teacher
Lincoln Elementary School
KG-5 · Regular · Winchester School District
334 students · 11.1:1 student–teacher
Lynch Elementary School
KG-5 · Regular · Winchester School District
426 students · 10.8:1 student–teacher
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.
New10
$2,999,000
5 bd · 5 ba · 4,900 sqft
5 Forest Cir, Winchester, MA
Pirani & Wile Group · Gibson Sotheby's International Realty
New33$2,650,000
4 bd · 5 ba · 5,233 sqft
18 Middlesex St, Winchester, MA
Jennifer Taves · Coldwell Banker Realty - Boston
42$1,985,000
4 bd · 4 ba · 4,241 sqft
30 Surrey Rd, Winchester, MA
Anne Spry · Barrett Sotheby's International Realty
42$2,049,000
5 bd · 4 ba · 4,063 sqft
21 Amberwood Dr, Winchester, MA
Gayle Winters & Co. Team · Compass
Price Reduced41$2,195,000
5 bd · 4 ba · 5,006 sqft
276 High Street, Winchester, MA
Kim Covino & Co. Team · Compass
Price Reduced42$2,399,000
4 bd · 5 ba · 4,450 sqft
54 Squire Road, Winchester, MA
Anthony Marino · The Marino Group Collection





Within 2 miles of this home: 37+ restaurants and cafés, 3 grocery stores, 38+ parks and green spaces, and 36+ 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
Maruichi Japanese Food and Deli
Massachusetts Avenue
Upper Mystic Lake
Glen Green
Shannon Beach
Mount Pisgah
West Side Field
Ginn Field
Mystic Lakes State Park
Stone Family Playground
Opp 65 Cambridge St @ Winchester Boat Club
65 Cambridge St @ Winchester Boat Club
Cambridge Street @ Robinson Park
Cambridge St @ Myopia Rd
26 Cambridge Street
Cambridge Street @ Arlington Street
Cambridge Street @ High Street
Cambridge Street @ Church Street