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This extraordinary, fully renovated home blends rich architectural detail w/ modern luxury in one of Winchester’s most sought-after neighborhoods. Designed by a shipbuilder, this home offers 5,876 sq ft of elegant living space filled w/ natural light, coffered ceilings, crown moldings, restored hardwood floors & more. The breathtaking chef’s kitchen includes a quartzite island, 8-burner Wolf range, paneled appliances, & wine bar. The first floor features generously sized rooms that flow beautifully, offering grand entertaining spaces, 4 fireplaces, & a statement staircase. Upstairs offers 4 bedrooms & 3 updated baths, including a serene primary suite w/ fireplace, marble bath & double closets. The third floor includes 2 add’l. beds, full bath, & room for expansion. Enjoy a private fenced yard w/ lush gardens, patio, & a 2+ car garage. With timeless character and thoughtful updates throughout, this is a rare opportunity just moments from town, train, and top schools!
Current real estate data for Single Family in Winchester as of Oct 07, 2025
62
Single Family Listed
65
Avg DOM
551
Avg $ / SqFt
$2,270,911
Avg List Price

Property Details

Price:
$3,599,000
MLS #:
73420138
Status:
Pending
Beds:
6
Baths:
4.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
Everett/ Stratford
Listed Date:
Aug 20, 2025
Finished Sq Ft:
5,876
Total Sq Ft:
5,876
Lot Size:
15,316 sqft / 0.35 acres (approx)
Year Built:
1870
PoolTennisEverett/ StratfordAmbroseMccallWhs

Schools

Elementary School:
Ambrose
Middle School:
Mccall
High School:
Whs

Interior

Appliances
Range, Dishwasher, Disposal, Refrigerator, Freezer, Washer, Dryer, Wine Refrigerator, Range Hood
Bathrooms
4 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Fireplaces Total
6
Flooring
Marble, Hardwood, Flooring – Hardwood
Heating
Forced Air, Natural Gas, Fireplace(s)
Laundry Features
Second Floor

Exterior

Architectural Style
Colonial
Community Features
Public Transportation, Shopping, Pool, Tennis Court(s), Park, Walk/Jog Trails, Golf, Medical Facility, Laundromat, Bike Path, Conservation Area, Highway Access, House of Worship, Private School, Public School
Construction Materials
Frame
Exterior Features
Porch, Patio, Rain Gutters, Professional Landscaping, Sprinkler System, Decorative Lighting, Fenced Yard
Parking Features
Detached, Paved Drive
Parking Spots
6
Roof
Shingle

Financial

Tax Year
2025
Taxes
$30,837

Map

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Community

Property Summary

    Located in the Everett/ Stratford subdivision, 5 Stratford Road Winchester MA is a Single Family for sale in Winchester, MA, 01890. It is listed for $3,599,000 and features 6 beds, 5 baths, and has approximately 5,876 square feet of living space, and was originally constructed in 1870. The current price per square foot is $612. 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#73420138 at 5 Stratford 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
5 Stratford Road
Winchester, MA