111 Highland Ave, Winchester MA 01890
Track this home for price, status, and open-house alerts.
About this home
Welcome to this spacious and charming Colonial offering beautiful architectural character, a flexible floor plan, and generous living space across multiple levels.Step into the welcoming foyer and discover a bright, inviting home featuring a fireplaced living room with beamed ceilings and oversized windows, complemented by a sun-filled adjoining sunroom.The beautiful kitchen features granite countertops, ample workspace, and a cozy breakfast nook with convenient access to the side yard. A separate home office and full bathroom on the first floor provide additional flexibility for working from home, guests, or everyday living.Upstairs, the spacious primary bedroom includes a walk-in closet and en-suite bathroom, along with an additional adjoining room that can serve as a nursery, private office, dressing room, or guest space. Two additional generously sized bedrooms, a full family bathroom, and a spacious landing with additional closet storage complete the second floor.The lower level offers an unheated bonus/family room with a decorative fireplace, laundry area, additional storage, and direct access to the two-car garage.Outside, enjoy a beautiful, spacious fenced backyard, perfect for relaxing, entertaining, and outdoor activities.Conveniently located near Middlesex Fells Reservation and all that Winchester has to offer, this home combines space, character, privacy, and convenience in a highly desirable residential setting.
View in the App
Save this property, schedule tours instantly, and get alerts when the price drops
Scan with phone
Public Records & Permits
Log in to view assessor & tax records, ownership history, and recent building permits for this property.
Property History
Market Insights
Property Timeline
Price Reduced
Aug 2, 2026Listed for Rent
Aug 1, 2026| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 08/02/2026 | ↓ Price Reduced | $5,500 | $200 | - | From $5,700 to $5,500 (-3.5%) |
| 08/01/2026 | 🏠 Listed for Rent | $5,700 | - | - | Original listing |
Tax History
| Year | Taxes | Assessment |
|---|---|---|
| Tax history not available | ||
Facts & Features
Home Facts
Rental Details
Interior
Exterior
Parking
Utilities
Building & Pet Policy
Additional Details
Property Overview
Floor Layout
Floor Layout
Finished Area
Display Options
Room Markers
Conceptual diagram based on MLS room data. It is not to scale and is not a substitute for architectural plans or on-site measurements.
Interior Features
Construction & Materials
Heating, Cooling & Utilities
Exterior & Lot
Parking & Garage
Special Features
Nearby Schools
Elementary Schools
10 schoolsMiddle Schools
1 schoolHigh Schools
1 schoolLocation
Neighborhood
111 Highland Ave, Winchester MA 01890
Winchester, MA 01890
Listing Information
