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Attention renovators and investors! This Cape-style home in need of significant renovation offers 7 rooms, 4 bedrooms, and 2 full baths. Features include a fireplace living room, dining room, and hardwood flooring throughout. Enjoy a private yard for outdoor enjoyment. Prime location directly across from the Middlesex Fells Reservation and minutes to Winchester Center, schools, shops, and restaurants. Great potential to restore or redevelop in one of Winchester’s most desirable areas. All offers due Tuesday the 28th at 12 PM.
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:
$1,199,900
MLS #:
73447622
Status:
Pending
Beds:
4
Baths:
2
Type:
Single Family
Subtype:
Single Family Residence
Neighborhood:
winchesterhighlands
Listed Date:
Oct 24, 2025
Finished Sq Ft:
1,755
Total Sq Ft:
1,755
Lot Size:
12,458 sqft / 0.29 acres (approx)
Year Built:
1939
TennisWinchester HighlandsWinchesterhighlandsMuracoMccallWinchester High

Schools

Elementary School:
Muraco
Middle School:
Mccall
High School:
Winchester High

Interior

Appliances
Water Heater, Range, Refrigerator, Range Hood
Bathrooms
2 Full Bathrooms
Cooling
None
Fireplaces Total
1
Flooring
Vinyl, Hardwood
Heating
Hot Water, Oil
Laundry Features
Electric Dryer Hookup, Washer Hookup, In Basement

Exterior

Architectural Style
Cape
Community Features
Public Transportation, Shopping, Tennis Court(s), Park, Walk/Jog Trails, Medical Facility, Conservation Area, Highway Access, House of Worship, Public School, T-Station
Construction Materials
Frame
Exterior Features
Patio, Rain Gutters, Storage, Screens, Fenced Yard
Parking Features
Attached, Paved Drive, Off Street
Parking Spots
2
Roof
Shingle

Financial

Tax Year
2025
Taxes
$16,431

Map

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Community

Property Summary

    102 Hillcrest Pkwy Winchester MA is a Single Family for sale in Winchester, MA, 01890. It is listed for $1,199,900 and features 4 beds, 2 baths, and has approximately 1,755 square feet of living space, and was originally constructed in 1939. The current price per square foot is $684. 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#73447622 at 102 Hillcrest Pkwy 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
102 Hillcrest Pkwy
Winchester, MA