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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 Nov 17, 2025
63
Single Family Listed
67
Avg DOM
554
Avg $ / SqFt
$2,056,473
Avg List Price

Property Details

Price:
$1,650,000
MLS #:
73448388
Status:
Pending
Beds:
3
Baths:
2.5
Type:
Single Family
Subtype:
Single Family Residence
Listed Date:
Oct 27, 2025
Finished Sq Ft:
1,882
Total Sq Ft:
1,882
Lot Size:
24,276 sqft / 0.56 acres (approx)
Year Built:
1936
MuracoMccallWinchester

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

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Community

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 $554. The average listing price for Single Family in Winchester is $2,056,473. 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 James
82 Hillcrest Parkway
Winchester, MA