New33
$2,650,000
4 bd · 5 ba · 5,233 sqft
18 Middlesex St, Winchester, MA
Jennifer Taves · Coldwell Banker Realty - Boston

No listing photos
5
Beds
2.5
Baths
4,162
Sqft
1911
Year built
Range $1,999,057 – $2,361,875 · 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 $2,623,530 in June 2024; lowest $1,141,406 in April 2020. The vertical scale starts at the series' own low, not at zero — it is drawn to show movement, not absolute size.
$436,093
Estimated monthly payment
$14,098/mo
Loan amount $1,744,373. Estimate only — your actual rate and payment depend on credit, location, and lender.
2025 roll
School ratings (A+ to F) from HJN community data.
Childrens Own School
PK-PK · Montessori
15 students · 3.0:1 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
Medford High School
9-12 · Regular · Medford School District
1,195 students · 9.2:1 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
Winchester High School
9-12 · Regular · Winchester School District
1,404 students · 14.8:1 student–teacher
Ambrose Elementary School
KG-5 · Regular · Winchester School District
398 students · 12.1:1 student–teacher
Within 2 miles of this home: 39+ restaurants and cafés, 2 grocery stores, 38+ parks and green spaces, and 33+ transit stops.
Place data from OpenStreetMap.
Black Horse Tavern
Waterfield Road
A Tavola
Italian restaurant · Church Street
Nouvelle Maison Fine Provisions
D'Agostino's Delicatessen
First House Pub
Frozen Hoagies
Main Street
Nourish Your Soul
Starbucks
Main Street
Stop & Shop
Main Street
Whole Foods Market
Mystic Valley Parkway
Brooks Parkhurst Town Forest
Ginn Field
Dennett Park
Stone Family Playground
Brooks Estate
Brooks Pond
Shannon Beach
Mystic Valley Parkway
Main Street @ Highland Avenue
Main Street opposite Highland Avenue
Main Street @ Ridgefield Road
Main Street @ Everell Road
Main Street @ Gateway South
Main Street @ Town Way
Main Street @ Marshall Road
Main Street @ Madison Avenue West
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.
New33
$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$1,599,000
4 bd · 2 ba · 2,421 sqft
4 Churchill Road, Winchester, MA
Kim Covino & Co. Team · Compass
42$1,985,000
4 bd · 4 ba · 4,241 sqft
30 Surrey Rd, Winchester, MA
Anne Spry · Barrett Sotheby's International Realty
Price Reduced30$2,750,000
6 bd · 7 ba · 6,968 sqft
14 Nassau Drive, Winchester, MA
Weidong Li · WINN Real Estate & Consulting
Price Reduced40$1,750,000
4 bd · 3 ba · 3,604 sqft
1 Overlook Way, Winchester, MA
Lynne Russo · Better Homes and Gardens Real Estate - The Shanahan Group




