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Royal Barry Wills former home! – An architectural treasure nestled on over 1 acre of land in one of Winchester’s most serene and private settings. Designed by the renowned architect Royal Barry Wills, this iconic Cape Cod residence showcases timeless elegance with its signature gambrel roof, cypress shingle exterior, and classic New England design. Inside, three magnificent fireplaces, exquisite millwork, and a beautiful stained-glass door create a sense of warmth and refinement. The inviting eat-in kitchen opens to a charming screened porch, perfect for quiet mornings or evening gatherings overlooking the lush rose gardens. Three spacious bedrooms w/ a large primary suite on the first floor with 2.5 baths. Completing this exceptional property is a distinctive garden gazebo, an architectural complement to the main home. The possibilities are endless…a rare opportunity to own a piece of the towns heritage, blending historic craftsmanship in a top country club location!
Current real estate data for Single Family in Winchester as of Nov 24, 2025
62
Single Family Listed
69
Avg DOM
555
Avg $ / SqFt
$2,041,448
Avg List Price

Property Details

Price:
$1,950,000
MLS #:
73449729
Status:
Active Under Contract
Beds:
3
Baths:
2.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
Myopia Hill near Country club
Listed Date:
Oct 30, 2025
Finished Sq Ft:
2,443
Total Sq Ft:
2,443
Lot Size:
45,812 sqft / 1.05 acres (approx)
Year Built:
1954
TennisMyopia Hill Near Country ClubAmbroseMccallWinchester

Schools

Elementary School:
Ambrose
Middle School:
Mccall
High School:
Winchester

Interior

Appliances
Oven, Dishwasher, Disposal, Range, Refrigerator, Freezer
Bathrooms
2 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Fireplaces Total
3
Flooring
Wood, Hardwood
Heating
Baseboard, Natural Gas
Laundry Features
In Basement

Exterior

Architectural Style
Cape
Community Features
Public Transportation, Shopping, Tennis Court(s), Park, Walk/Jog Trails, Golf, Medical Facility, Bike Path, Conservation Area, Highway Access, House of Worship, Private School, Public School
Exterior Features
Porch – Screened, Patio, Covered Patio/Deck, Professional Landscaping, Sprinkler System, Screens, Garden, Stone Wall
Parking Features
Attached, Garage Door Opener, Paved Drive, Paved
Parking Spots
4
Roof
Wood

Financial

Tax Year
2025
Taxes
$17,819

Map

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Community

Property Summary

    Located in the Myopia Hill near Country club subdivision, 5 Wood Lane Winchester MA is a Single Family for sale in Winchester, MA, 01890. It is listed for $1,950,000 and features 3 beds, 3 baths, and has approximately 2,443 square feet of living space, and was originally constructed in 1954. The current price per square foot is $798. The average price per square foot for Single Family listings in Winchester is $555. The average listing price for Single Family in Winchester is $2,041,448. To schedule a showing of MLS#73449729 at 5 Wood Lane 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
5 Wood Lane
Winchester, MA