Price Reduced21
$749,000
2 bd · 2 ba · 1,036 sqft
50 Middlesex Street #50, Winchester, MA
The North Star Group · Keller Williams Realty Evolution

No listing photos
3
Beds
1.5
Baths
1,918
Sqft
1953
Year built
Range $976,524 – $1,079,652 · as of October 21, 2026
ATTOM automated valuation model · 54 published estimates over 6.8 years · shaded band is the model's own published low-to-high range
Highest reading $1,261,000 in January 2025; lowest $742,257 in January 2020. The vertical scale starts at the series' own low, not at zero — it is drawn to show movement, not absolute size.
$205,618
Estimated monthly payment
$6,631/mo
Loan amount $822,470. Estimate only — your actual rate and payment depend on credit, location, and lender.
2026 roll
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
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
St Mary's School
PK-KG · Early Childhood Program/Child Care Center
9 students · 9.0:1 student–teacher
The Wilder School
UG-UG · Alternative/Other
2 students · 1.8:1 student–teacher
Lynch Elementary School
KG-5 · Regular · Winchester School District
426 students · 10.8:1 student–teacher
St Charles School
PK-8 · Regular
162 students · 12.1:1 student–teacher
Within 2 miles of this home: 39+ restaurants and cafés, 2 grocery stores, 35+ parks and green spaces, and 33+ transit stops.
Place data from OpenStreetMap.
Andrea's Pizza
Main Street
Gloria's Pizzeria
Main Street
Sakura Japanese
Japanese restaurant · Main Street
Mitho Restaurant
Main Street
Swanton Street Diner
Swanton Street
Arancini Italian Restaurant
Italian restaurant · Main Street
Eighty Eight Cafe
Chinese restaurant · Washington Street
Dunkin
Main Street
Stop & Shop
Main Street
Whole Foods Market
Cambridge Road
Aberjona River
McDonald Field
Leonard Field
Davidson Park
Bellino Park
Green Street Park
Horn Pond Brook
Elliot Park
Main Street opposite Hemingway Street
Main Street @ Canal Street
Main Street opposite Sheridan Circle
Main Street opposite Richardson Street
Main Street @ Hemingway Street
Main Street @ Sheridan Circle
Main St @ Cranes Ct
Main St @ Lydon Ct
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 Reduced21
$749,000
2 bd · 2 ba · 1,036 sqft
50 Middlesex Street #50, Winchester, MA
The North Star Group · Keller Williams Realty Evolution
Price Reduced42$999,000
3 bd · 3 ba · 2,235 sqft
53 Lake Street, Winchester, MA
Kim Covino & Co. Team · Compass
Price Reduced34$815,000
2 bd · 1 ba · 1,489 sqft
80 Nelson St, Winchester, MA
Kim Covino & Co. Team · Compass
Price Reduced34$919,000
4 bd · 3 ba · 1,719 sqft
258 Cross St, Winchester, MA
Justin Blankenship · Fiv Realty Co
41$1,049,900
3 bd · 2 ba · 1,783 sqft
28 Olive St, Winchester, MA
Ethan Forrest · The Aland Realty Group LLC
Price Reduced40$1,049,000
4 bd · 3 ba · 2,411 sqft
24 Richardson St, Winchester, MA
Andersen Group Realty · Keller Williams Realty Boston Northwest




