Nestled directly across from the breathtaking Middlesex Fells Reservation, this home offers the perfect blend of charm, space, and potential. This classic 3-bedroom, 2.5 bath Cape is beautifully situated on over half an acre in one of Winchester’s most desirable locations. The home features mostly hardwood floors throughout, a brand-new roof, and a newer heating and AC system. The second floor includes three bedrooms, including a primary suite with a walk-in closet. The first floor offers a spacious eat-in kitchen, a formal dining room, an office, and a front-to-back living room with fireplace with access to a sun porch. The lower level is ideal for a family room, complete with a fireplace. The generous lot provides exciting expansion potential without sacrificing yard space. Surrounded by nature and endless recreation opportunities just steps from your front door, this home is being sold as is and presents an incredible opportunity to make it your own.
Current real estate data for Single Family in Winchester as of Oct 28, 2025
62
Single Family Listed
69
Avg DOM
537
Avg $ / SqFt
$2,159,026
Avg List Price
Property Details
Price:
$1,650,000
MLS #:
73448388
Status:
Active
Beds:
3
Baths:
2.5
Type:
Single Family
Subtype:
Single Family Residence
Listed Date:
Oct 28, 2025
Finished Sq Ft:
1,882
Total Sq Ft:
1,882
Lot Size:
24,276 sqft / 0.56 acres (approx)
Year Built:
1936
Schools
Elementary School:
Muraco
Middle School:
Mccall
High School:
Winchester
Interior
Appliances
Range, Dishwasher, Disposal, Microwave, Refrigerator, Washer, Dryer
Bathrooms
2 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Fireplaces Total
2
Flooring
Tile, Carpet, Laminate, Hardwood, Flooring – Hardwood
Heating
Oil
Laundry Features
In Basement
Exterior
Architectural Style
Cape
Community Features
Public Transportation, Shopping, Walk/Jog Trails, Medical Facility, Bike Path, Conservation Area, Highway Access, House of Worship, Public School, T-Station
Parking Features
Paved Drive
Parking Spots
4
Financial
Tax Year
2025
Taxes
$18,565
Map
Contact Us
Mortgage Calculator
Community
- Address82 Hillcrest Parkway Winchester MA
- CityWinchester
- CountyMiddlesex
- Zip Code01890
Subdivisions in Winchester
- Close to Wright Locke Farm
- Cox Road / High St Extension neighborhood
- East SIde near town forest!!
- Everett/ Stratford
- Flats location
- FLATS location Across from Wedgemere/Oxford
- Lakeview/Wedgemere~ Near downtown & Wedgemere train station
- Ledgewood Estates
- Middlesex
- Myopia Hill/ Winchester Country Club Area
- Near VO school
- old village/ West side
- The Flats
- Top neighborhood near town center
- West side
Property Summary
- 82 Hillcrest Parkway Winchester MA is a Single Family for sale in Winchester, MA, 01890. It is listed for $1,650,000 and features 3 beds, 3 baths, and has approximately 1,882 square feet of living space, and was originally constructed in 1936. The current price per square foot is $877. The average price per square foot for Single Family listings in Winchester is $537. The average listing price for Single Family in Winchester is $2,159,026. To schedule a showing of MLS#73448388 at 82 Hillcrest Parkway in Winchester, MA, contact your Boardwalk Real Estate Corp. agent at 781-944-7820.
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CRP: Certified Relocation Professional CRS: Certified Residential Specialist GRI: Graduate of Realtors Institute CBR: Certified Buyers Representative BSBA: Bachelor of Science in Business Administration. Babson College 1979 MBA: Master of Business Administration. Babson College 2002 James M. Joly is President and Principal-Owner of Boardwalk Real Estate Corp.,…
More About JamesCourtesy 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.
82 Hillcrest Parkway
Winchester, MA








































