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
3
Baths
4,959
Sqft
1980
Year built
Range $1,885,399 – $2,253,915 · as of August 30, 2026
ATTOM automated valuation model · 55 published estimates over 6.7 years · shaded band is the model's own published low-to-high range
Highest reading $2,722,250 in August 2024; lowest $1,469,180 in April 2020. The vertical scale starts at the series' own low, not at zero — it is drawn to show movement, not absolute size.
$413,931
Estimated monthly payment
$13,388/mo
Loan amount $1,655,726. Estimate only — your actual rate and payment depend on credit, location, and lender.
2025 roll
Within 2 miles of this home: 37+ restaurants and cafés, 4 grocery stores, 38+ parks and green spaces, and 38+ transit stops.
Place data from OpenStreetMap.
Dunkin
Cambridge Road
Krave Kitchen & Bar
American restaurant · Cambridge Road
Sogno
Italian restaurant · Cambridge Road
Arlington Cafe
Summer Street
Sono Asian Cuisine
Summer Street
Lexington House of Pizza
McDonald's
Cambridge Road
Ninety Nine Restaurant & Pub
American restaurant · Cambridge Road
Whole Foods Market
Cambridge Road
Maruichi Japanese Food and Deli
Massachusetts Avenue
Trader Joe's
Massachusetts Avenue
Stop & Shop
Main Street
Smith Pond Conservation Area
Sachem Swamp Conservation Area
Mullen Field
Mount Pisgah
Locke Farm Conservation Area
Vernal Pool
Locke Pond
Sucker Brook Conservation Area
Winchester Drive @ Russell Road
Winchester Drive opposite Tyler Road
Russell Road @ Whipple Road
Clyde Terr @ Lawrence Ln
Forest St @ Thomas St
Whipple Road @ Fiske Road
Cambridge Street @ Wildwood Street
Cambridge Street @ Blossom Hill Road
School ratings (A+ to F) from HJN community data.
Van - Owen Elementary School
KG-5 · Regular · Winchester School District
441 students · 12.5:1 student–teacher
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
Peirce Elementary School
KG-5 · Regular · Arlington School District
318 students · 13.2:1 student–teacher
Lexington Christian Academy
6-12 · Regular
281 students · 8.1:1 student–teacher
Reeves Elementary School
KG-5 · Regular · Woburn School District
451 students · 13.7:1 student–teacher
Harrington Elementary School
KG-5 · Regular · Lexington School District
374 students · 10.0:1 student–teacher
New Covenant School
PK-5 · Regular
55 students · 7.3:1 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$1,495,000
4 bd · 3 ba · 2,973 sqft
7 Sherman Place #7, Winchester, MA
John Dean · Engel & Volkers Boston
32$1,529,000
4 bd · 4 ba · 2,709 sqft
25 Arlington St, Winchester, MA
Domingo Medina · Coldwell Banker Realty - Lexington
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 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




