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Open House Oct 19, 2025
12:00 – 01:30
Open House Oct 18, 2025
12:00 – 01:30
NEW PRICE & UPDATES BEAUTIFULLY REIMAGINED!Welcome home to this stunning brick ranch tucked on a quiet cul-de-sac in Winchester’s coveted West Side. Every space has been thoughtfully designed, blending classic craftsmanship with distinct elegance. The bright open layout invites you in with a chef’s granite and stainless kitchen, sun-filled family room framed by floor-to-ceiling windows, and French doors opening to a new composite deck and tranquil backyard. Gather in the elegant dining room and sunken living room with fireplace, or retreat to the serene primary suite with sitting area and spa-inspired bath. A flexible fifth bedroom or office with private entrance is perfect for guests or in-laws. The finished lower level offers a game room, gym, wine storage, cedar closet, and more. Spectacular & unbeatable location and neighborhood awaits you! Move-in ready, moments to Winchester Center, top schools, and commuter access—where timeless style meets effortless living.
Current real estate data for Single Family in Winchester as of Oct 14, 2025
64
Single Family Listed
60
Avg DOM
542
Avg $ / SqFt
$2,254,228
Avg List Price

Property Details

Price:
$2,125,000
MLS #:
73442291
Status:
Active
Beds:
5
Baths:
3.5
Type:
Single Family
Subtype:
Single Family Residence
Listed Date:
Oct 10, 2025
Finished Sq Ft:
6,232
Total Sq Ft:
6,232
Lot Size:
25,535 sqft / 0.59 acres (approx)
Year Built:
1980
PoolTennisVinson OwenMccallWinchester High School

Schools

Elementary School:
Vinson Owen
Middle School:
Mccall
High School:
Winchester High School

Interior

Appliances
Water Heater
Bathrooms
3 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Fireplaces Total
2
Flooring
Tile, Laminate, Hardwood
Heating
Baseboard, Oil, Propane
Laundry Features
In Basement

Exterior

Architectural Style
Contemporary, Ranch
Community Features
Pool, Tennis Court(s), Golf, Medical Facility, Bike Path, Conservation Area, House of Worship, Public School, T-Station
Construction Materials
Frame
Exterior Features
Deck – Composite, Patio, Rain Gutters, Professional Landscaping
Parking Features
Attached, Garage Door Opener, Heated Garage, Paved Drive, Off Street, Driveway, Stone/Gravel
Parking Spots
4
Roof
Shingle
Security Features
Security System

Financial

Tax Year
2025
Taxes
$19,385

Map

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Community

Property Summary

    5 Azalea Road Winchester MA is a Single Family for sale in Winchester, MA, 01890. It is listed for $2,125,000 and features 5 beds, 4 baths, and has approximately 6,232 square feet of living space, and was originally constructed in 1980. The current price per square foot is $341. The average price per square foot for Single Family listings in Winchester is $542. The average listing price for Single Family in Winchester is $2,254,228. To schedule a showing of MLS#73442291 at 5 Azalea 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 Azalea Road
Winchester, MA