$2,299,000
216 Highland Avenue
Winchester, MA, 01890
Welcome to this fully updated 5 BR, 3.5 BA Victorian showcasing elegant period detail throughout, including intricate woodwork, moldings, high ceilings & hardwood floors. The main level features a gourmet eat-in kitchen w/ quartz island & high-end stainless appliances, opening to a custom butler’s pantry w/ additional oven, sink & wine chiller. A sun-filled family room w/French doors leads to the patio, along w/ a fireplaced living room w/ built-ins, & formal dining room. Home includes 2 primary bedroom options, one on the 2nd floor & a private 3rd-floor primary suite w/ fireplace & full bath. The 2nd level also has 3 additional spacious bedrooms & two full baths, while the 3rd floor features a dramatic great room w/ beamed ceiling.Additional highlights include partially finished basement & newer heat & AC. Enjoy a wrap-around porch, patio & large fenced yard. Ideally located near town center, Middlesex Fells Reservation, Commuter Rail, Lincoln Elementary, Middle School, & Highschool.
Property Details
Price:
$2,299,000
MLS #:
73511014
Status:
Pending
Beds:
5
Baths:
3.5
Type:
Single Family
Subtype:
Single Family Residence
Listed Date:
May 1, 2026
Finished Sq Ft:
4,822
Total Sq Ft:
4,822
Lot Size:
11,156 sqft / 0.26 acres (approx)
Year Built:
1902
Schools
Elementary School:
Lincoln
Middle School:
Mccall
High School:
Winchester High
Interior
Above Grade Finished Area
3395
Appliances
Range, Dishwasher, Disposal, Refrigerator, Washer, Dryer, Wine Refrigerator
Bathrooms
3 Full Bathrooms, 1 Half Bathroom
Below Grade Finished Area
1427
Cooling
Central Air
Fireplaces Total
2
Flooring
Tile, Carpet, Laminate, Hardwood, Flooring – Stone/Ceramic Tile, Flooring – Wall to Wall Carpet
Heating
Forced Air, Electric Baseboard, Radiant, Natural Gas
Interior Features
Bathroom – Full, Bathroom – Double Vanity/Sink, Countertops – Stone/Granite/Solid, Soaking Tub, Closet, Closet/Cabinets – Custom Built, Countertops – Upgraded, Recessed Lighting, Peninsula, Beamed Ceilings, Lighting – Overhead, Bathroom, Play Room, Great Room, Wet Bar
Laundry Features
Sink, In Basement
Exterior
Architectural Style
Victorian
Community Features
Public Transportation, Shopping, Park, Medical Facility, Conservation Area, Highway Access, Public School, T-Station
Exterior Features
Porch, Patio, Rain Gutters, Professional Landscaping, Sprinkler System, Fenced Yard
Fencing
Fenced/Enclosed, Fenced
Open Parking Spaces
5
Parking Features
Off Street
Parking Spots
5
Parking Total
5
Patio And Porch Features
Porch, Patio
Roof
Slate
Security Features
Security System
Window Features
Window(s) – Picture
Financial
Tax Year
2026
Taxes
$22,931
Marie Andrews is an award-winning, licensed real estate broker with licenses in Massachusetts and Florida. She has been selling real estate in the greater Boston area for over 20 years. Over the past two decades, Marie has worked for Century 21 Advanced Realty, building a reputation as a multi-million dollar producer. She has developed an extensive network of investors, lenders, and attorneys. Marie has a wide knowledge base on property management, Massachusetts real estate law, and building…
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Map
Current real estate data for Single Family in Winchester as of Jun 20, 2026
77
Single Family Listed
52
Avg DOM
550
Avg $ / SqFt
$2,163,397
Avg List Price
Community
- Address216 Highland Avenue Winchester MA
- CityWinchester
- CountyMiddlesex
- Zip Code01890
Subdivisions in Winchester
- Brooks / Parkhurst / Town Forest
- Cox Road / High St Extension neighborhood
- Flats
- Flats neighborhood
- Lakeview/Wedgemere~ Near downtown & Wedgemere train station
- Macdonald field neighborhood
- Middlesex / downtown
- Near town/ Pine St neighborhood
- Old Village/ West Side
- Rangeley Historical Estate
- The Flats
- Vinson-Owen School District.
- West Side
- Winning Farm
Similar Listings Nearby
Property Summary
- 216 Highland Avenue Winchester MA is a Single Family for sale in Winchester, MA, 01890. It is listed for $2,299,000 and features 5 beds, 4 baths, and has approximately 4,822 square feet of living space, and was originally constructed in 1902. The current price per square foot is $477. The average price per square foot for Single Family listings in Winchester is $550. The average listing price for Single Family in Winchester is $2,163,397. To schedule a showing of MLS#73511014 at 216 Highland Avenue in Winchester, MA, contact your Pegasus Realty LLC agent at 781-858-3505.
Courtesy of Better Homes and Gardens Real Estate – The Shanahan Group. The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.
216 Highland Avenue
Winchester, MA