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Properties

  • 65 High Street, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 9 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,High Street,73498871
  • 65 High Street, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 9 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,High Street,73498871
  • 65 High Street, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 9 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,High Street,73498871
  • 65 High Street, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 9 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,High Street,73498871
  • 65 High Street, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 9 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,High Street,73498871
  • 65 High Street, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 9 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,High Street,73498871
  • 65 High Street, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 9 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,High Street,73498871
  • 65 High Street, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 9 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,High Street,73498871
  • 65 High Street, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 9 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,High Street,73498871
  • 65 High Street, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 9 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,High Street,73498871
  • 65 High Street, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 9 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,High Street,73498871
  • 65 High Street, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 9 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,High Street,73498871
  • 65 High Street, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 9 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,High Street,73498871
  • 65 High Street, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 9 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,High Street,73498871
  • 65 High Street, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 9 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,High Street,73498871
  • 65 High Street, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 9 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,High Street,73498871
  • 65 High Street, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 9 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,High Street,73498871
  • 65 High Street, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 9 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,High Street,73498871
  • 65 High Street, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 9 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,High Street,73498871
  • 65 High Street, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 9 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,High Street,73498871
  • 65 High Street, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 9 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,High Street,73498871
  • 65 High Street, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 9 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,High Street,73498871
  • 65 High Street, Winchester, Massachusetts, 6 Bedrooms Bedrooms, 9 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,High Street,73498871
Property Description

Exceptional opportunity in a highly desirable Winchester neighborhood! This spacious 6-bedroom home offers incredible flexibility for today’s lifestyle, perfect for multi-generational living, work-from-home setups, or growing households. The sun-filled main level 3-bedrooms feature hardwood floors and a seamless flow, ideal for both everyday living and entertaining. The updated second floor includes a full bath, private laundry, and generously sized 3 bedrooms with abundant natural light. A standout feature is the expansive 1,337 sq ft lower level – ideal for a playroom, gym, media room, or future customization. Enjoy a level, private backyard perfect for outdoor gatherings, gardening, and recreation. Conveniently located near top-rated schools, commuter rail, and Winchester center. Incredible value and space in one of Winchester’s most sought-after communities!! The seller will gift the new buyer a pool and a ping-pong table for the playroom.

Features
Heating System:
Oil, Baseboard
Cooling System:
Central Air
Basement:
Full, Finished, Bulkhead, Sump Pump
Fireplace:
Living Room
Parking:
Attached, Off Street, Paved Drive
Appliances:
Disposal, Range, Dishwasher, Microwave, Refrigerator, Washer, Dryer, Water Heater
Construction:
Frame
Exterior Unit Features:
Porch - Enclosed, Porch - Screened, Storage
Flooring:
Tile, Hardwood, Carpet, Flooring - Wall To Wall Carpet
Sewer:
Public Sewer
Style:
Colonial
Water:
Public
Disclosure:
pics were taken prior to last sale. Seller is the middle of packing, Property to be Sold as is condition Listing Agency / Agent doesn’t Warrant Listing
Electric Feature:
Circuit Breakers
Garage Parking:
Yes
Interior Features:
Bathroom - With Shower Stall, Sun Room, Bedroom, Bathroom - 3/4, Play Room
Lead Paint:
Unknown
Laundry Features:
Second Floor, Electric Dryer Hookup
Additional Information
Grade School:
Ambros
High School:
Winchester
Middle School:
Mccall
Parking Spaces:
5
Tax Year:
2025
Status:
Active
Price Per Sqft:
$527
Zoning:
RDB
Orig Price:
$1,399,800
Fireplaces:
1
Waterfront:
No
MlsStatus:
New
Address Map
City:
Winchester
State:
MA
County:
Middlesex
Postal Code:
01890
Longitude:
W72° 50' 24.7''
Latitude:
N42° 26' 38.5''
  • Google Map

Residential

65 High Street, Winchester, Massachusetts

6 Bedrooms
3 Total Bathrooms
2,658 Sqft
$1,399,800
Listing ID #73498871
Basic Details
Property Type :
Residential
Listing Type :
For Sale
Price :
$1,399,800
Bedrooms :
6
Rooms :
9
Total Bathrooms :
3
Full Bathrooms :
3
Square Footage :
2,658 Sqft
Year Built :
1949
Lot Area :
0.23 Acre
Listing ID :
73498871
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Agent info
Robb Enterprises
  • Stephen E. Robb
  • View website
  • 617-212-0251
  • srobb@robbenterprises.com

Contact Agent

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.

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