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A rare Winchester offering set on an acre in a wooded enclave of luxury homes near town center. Custom-built, this 5-bedroom, 4.5-bath residence combines timeless design with balanced proportions across four levels. The primary suite includes a private deck, spa-like bath with soaking tub, and gas fireplace. The chef’s kitchen features quarter-sawn oak cabinetry, high-end appliances, large island, pantry, and wet bar, opening to casual and formal spaces. A four-season sunroom leads to an outdoor oasis with extensive landscaping, stonework, patio, outdoor kitchen, built-in fireplace, and private tennis court. High ceilings, crown molding, custom quarter-sawn oak built-ins, and classic finishes are found throughout, thoughtful choices using healthy home materials. Additional highlights include a large mudroom, laundry room, and a finished lower level with family room, bath, exercise area, and ample storage. Truly unique close to town center, top-ranked schools, and easy access to Boston.
Current real estate data for Single Family in Winchester as of Oct 07, 2025
62
Single Family Listed
64
Avg DOM
551
Avg $ / SqFt
$2,270,911
Avg List Price

Property Details

Price:
$3,850,000
MLS #:
73439119
Status:
Active
Beds:
5
Baths:
4.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
Ledgewood Estates
Neighborhood:
winchesterhighlands
Listed Date:
Oct 2, 2025
Finished Sq Ft:
5,069
Total Sq Ft:
5,069
Lot Size:
43,560 sqft / 1.00 acres (approx)
Year Built:
2016
WoodedTennisWinchester HighlandsWinchesterhighlandsLedgewood EstatesLincoln Elementary SchoolMccall Middle SchoolWinchester High School

Schools

Elementary School:
Lincoln Elementary School
Middle School:
Mccall Middle School
High School:
Winchester High School

Interior

Appliances
Gas Water Heater, Range, Dishwasher, Disposal, Microwave, Refrigerator, ENERGY STAR Qualified Refrigerator, ENERGY STAR Qualified Dishwasher, Range Hood
Bathrooms
4 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air, Ductless
Fireplaces Total
2
Flooring
Wood, Tile, Flooring – Hardwood, Laminate
Heating
Forced Air, Natural Gas, Ductless
Laundry Features
First Floor

Exterior

Architectural Style
Colonial, Craftsman
Community Features
Public Transportation, Shopping, Tennis Court(s), Park, Walk/Jog Trails, Medical Facility, Conservation Area, Highway Access, Public School, T-Station
Construction Materials
Frame
Exterior Features
Porch, Deck, Patio, Tennis Court(s), Rain Gutters, Professional Landscaping, Sprinkler System, Decorative Lighting, Screens, Fenced Yard, Stone Wall
Parking Features
Attached, Garage Door Opener, Garage Faces Side, Paved Drive, Off Street, Paved
Parking Spots
6
Roof
Shingle
Security Features
Security System

Financial

Tax Year
2025
Taxes
$31,292

Map

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Property Summary

    Located in the Ledgewood Estates subdivision, 12 Ledgewood Road Winchester MA is a Single Family for sale in Winchester, MA, 01890. It is listed for $3,850,000 and features 5 beds, 5 baths, and has approximately 5,069 square feet of living space, and was originally constructed in 2016. The current price per square foot is $760. The average price per square foot for Single Family listings in Winchester is $551. The average listing price for Single Family in Winchester is $2,270,911. To schedule a showing of MLS#73439119 at 12 Ledgewood Road 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
12 Ledgewood Road
Winchester, MA