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
4
Beds
4.5
Baths
4,857
Sqft
2010
Year built
Range $2,374,548 – $2,787,513 · as of April 23, 2026
ATTOM automated valuation model · 52 published estimates over 6.3 years · shaded band is the model's own published low-to-high range
Highest reading $2,640,305 in June 2023; lowest $691,980 in August 2025. The vertical scale starts at the series' own low, not at zero — it is drawn to show movement, not absolute size.
$516,206
Estimated monthly payment
$16,667/mo
Loan amount $2,064,825. 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
Van - Owen Elementary School
KG-5 · Regular · Winchester School District
441 students · 12.5:1 student–teacher
Stratton Elementary School
KG-5 · Regular · Arlington School District
448 students · 12.2:1 student–teacher
Lynch Elementary School
KG-5 · Regular · Winchester School District
426 students · 10.8:1 student–teacher
McCall Middle School
6-8 · Regular · Winchester School District
1,036 students · 12.6:1 student–teacher
Peirce Elementary School
KG-5 · Regular · Arlington School District
318 students · 13.2:1 student–teacher
Lincoln Elementary School
KG-5 · Regular · Winchester School District
334 students · 11.1:1 student–teacher
John A. Bishop Elementary School
KG-5 · Regular · Arlington School District
375 students · 12.4:1 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.
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
Price Reduced38$1,899,000
4 bd · 3 ba · 3,757 sqft
85 High St, Winchester, MA
Catherine Albiani · Better Homes and Gardens Real Estate - The Shanahan Group





Within 2 miles of this home: 37+ restaurants and cafés, 4 grocery stores, 36+ parks and green spaces, and 35+ transit stops.
Place data from OpenStreetMap.
Dunkin
Cambridge Road
Krave Kitchen & Bar
American restaurant · Cambridge Road
Sogno
Italian restaurant · Cambridge Road
A Tavola
Italian restaurant · Church Street
Nouvelle Maison Fine Provisions
D'Agostino's Delicatessen
Black Horse Tavern
Waterfield Road
Playa Bowls
Whole Foods Market
Cambridge Road
Stop & Shop
Main Street
Maruichi Japanese Food and Deli
Massachusetts Avenue
Trader Joe's
Massachusetts Avenue
Mount Pisgah
West Side Field
Glen Green
Sachem Swamp Conservation Area
Mullen Field
Smith Pond Conservation Area
Upper Mystic Lake
Rindge St Conservation
Cambridge Street @ Oneida Road
Cambridge Street @ Blossom Hill Road
125 Cambridge Street opposite Oneida Road
Cambridge Street @ Foxcroft Road
Cambridge Street @ High Street
Cambridge Street @ Church Street
Cambridge St @ Myopia Rd
Cambridge Street @ Wildwood Street