$1,999,000
85 High St
Winchester, MA, 01890
Classic Colonial nestled within one of Winchester’s most desirable neighborhoods, offering timeless architecture, exceptional flexibility, and an enviable setting. The first floor features an updated kitchen with slider to the scenic rear yard and oversized brick patio, casual den, half bath, formal dining room, and gracious living room with fireplace and classic built-ins. Double doors lead to a spectacular all-season porch, perfectly positioned for effortless entertaining indoors or out. The second floor offers four corner bedrooms, including a spacious primary suite with double closets, ensuite bath, and convenient laundry. The walk-up third floor invites endless possibilities with an additional bedroom and abundant closet space. Approximately 500 square feet of finished lower-level flex space provides room for a home gym, teen retreat, playroom, or office. Outside, a private, level yard offers ample space for gardens, play, and entertaining, with a generous brick patio for relaxing and gathering. The two-car heated garage features a full walk-up second floor, ideal for storage or future finishing as a studio, office, or home-away-from-home retreat. Simply a beautiful home in an exceptional location—ready to be loved from day one.
Property Details
Price:
$1,999,000
MLS #:
73565817
Status:
Active
Beds:
4
Baths:
2.5
Type:
Single Family
Subtype:
Single Family Residence
Listed Date:
Aug 19, 2026
Finished Sq Ft:
3,757
Total Sq Ft:
3,757
Lot Size:
12,489 sqft / 0.29 acres (approx)
Year Built:
1931
Schools
Elementary School:
Ambrose
Middle School:
Mccall
High School:
Whs
Interior
Above Grade Finished Area
3264
Appliances
Water Heater, Oven, Dishwasher, Disposal, Range, Refrigerator, Washer, Dryer
Bathrooms
2 Full Bathrooms, 1 Half Bathroom
Below Grade Finished Area
493
Cooling
Central Air
Fireplaces Total
1
Flooring
Tile, Hardwood, Flooring – Hardwood, Laminate
Heating
Steam, Natural Gas
Interior Features
Dining Area, Breakfast Bar / Nook, Foyer, Bonus Room
Laundry Features
Second Floor, Electric Dryer Hookup, Washer Hookup
Exterior
Architectural Style
Colonial
Community Features
Public Transportation, Tennis Court(s), Park, Medical Facility, Bike Path, Conservation Area, Highway Access, House of Worship, Public School, T-Station
Covered Spaces
2
Exterior Features
Patio, Rain Gutters, Professional Landscaping, Sprinkler System, Screens, Fenced Yard
Fencing
Fenced/Enclosed, Fenced
Garage Spaces
2
Lot Features
Corner Lot, Level
Open Parking Spaces
4
Open Parking YN
1
Parking Features
Detached, Garage Door Opener, Heated Garage, Storage, Off Street, Paved
Parking Spots
6
Parking Total
6
Patio And Porch Features
Patio
Roof
Shingle
Window Features
Screens
Financial
Tax Year
2025
Taxes
$15,671
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…
More About MarieMortgage Calculator
Map
Current real estate data for Single Family in Winchester as of Aug 31, 2026
50
Single Family Listed
76
Avg DOM
559
Avg $ / SqFt
$2,067,636
Avg List Price
Community
- Address85 High St 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
- 85 High St Winchester MA is a Single Family for sale in Winchester, MA, 01890. It is listed for $1,999,000 and features 4 beds, 3 baths, and has approximately 3,757 square feet of living space, and was originally constructed in 1931. The current price per square foot is $532. The average price per square foot for Single Family listings in Winchester is $559. The average listing price for Single Family in Winchester is $2,067,636. To schedule a showing of MLS#73565817 at 85 High St 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.
85 High St
Winchester, MA








































