Single Family Residence at 5 Willowdale Rd, Winchester MA 01890, Winchester
Single Family Residence at 5 Willowdale Rd, Winchester MA 01890, Winchester, photo 2 of 42
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Single Family Residence at 5 Willowdale Rd, Winchester MA 01890, Winchester, photo 4 of 42
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Single Family Residence at 5 Willowdale Rd, Winchester MA 01890, Winchester, photo 12 of 42
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Single Family Residence at 5 Willowdale Rd, Winchester MA 01890, Winchester, photo 24 of 42
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42 photos

$1,679,900

5 Willowdale Rd, Winchester MA 01890
Winchester, MA 01890
Listed by Erica Carson
Bedrooms
3
Bathrooms
2
Living area
2,483 sqft
Year built
1953

About this home

Distinctive in both design and craftsmanship, this custom expanded Ranch combines balanced architectural proportions, generous living space, and everyday comfort in Winchester’s highly sought-after East Hill neighborhood. A welcoming foyer with built-in bench opens to warm, light-filled interiors curated to feel both connected and intimate. At the heart of the home, the expansive mahogany kitchen features a substantial wood center island, handmade pocket plantation shutters that disappear seamlessly behind custom cabinetry, updated countertops and backsplash, a concealed illuminated bar cabinet, beverage fridge, and dual-zone wine fridge. Paned-glass pocket doors can separate the kitchen or open it to the adjoining dining and family rooms, where radiant-heated floors create a warm, inviting setting and a wall of windows connects the interior space beautifully to the surrounding landscape. The family room’s custom cherry entertainment center, finished with copper paneling and ebony inlays, reflects the extraordinary attention to detail found throughout. A formal living room with fireplace and custom millwork provides a separate space to gather or unwind. Tucked into a private wing are three well-proportioned bedrooms with hardwood floors and generous closets, along with a renovated full bath featuring a double vanity, deep soaking tub, and radiant-heated floor. The finished lower level offers remarkable flexibility with a media room wired for surround sound, exercise room, second full bath, laundry, mudroom area, abundant temperature-controlled storage, and direct access to an oversized two-car garage with workspace. Outside, the backyard and stone patio provide an equally peaceful and private extension of the interior living space. Mature plantings, stone walls, a potting shed, and an irrigation system complete this wide, one-third-acre lot. Central air, central vacuum, extensive built-ins and storage, plus new interior doors and crown molding throughout the bedroom wing add comfort and convenience. Polished, distinctive, and genuinely inviting, 5 Willowdale Road is a home of enduring quality that feels every bit as special as it looks. NO OPEN HOUSES, shown By Private Appointment only.

Highlights

Fireplace

Property details

MLS #
73572791
Property type
Single Family Residence
Subdivision
East Hill
Status
Active
Days on market
17
On market date
September 8, 2026
Stories
N/A
Total bathrooms
2
Garage spaces
2
Parking spaces
7
Lot size
0.33 acres
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Nearby schools

Within 10 miles · public school directory data (NCES)

Elementary
Lincoln Elementary
0.78 mi away · Grades 0-5
Nearest school -- attendance-zone data not available here
4.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
347
Student:teacher ratio
12.4:1
District
Winchester
Middle
McCall Middle
0.72 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
1,059
Student:teacher ratio
11.8:1
District
Winchester
High
Medford High
0.8 mi away · Grades 9-12
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
1,207
Student:teacher ratio
9.7:1
District
Medford

Walkability

Blended score for Winchester's center: EPA's National Walkability Index (street network, transit, land-use mix) combined with nearby-amenity density. 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

74
Walkable
out of 100
EPA National Walkability Index
12.7 / 20 -- Above average walkable
Nearby-amenity density
90 / 100
Restaurants & cafes20
Grocery stores2
Parks16
Schools20
Transit stops20
Pharmacies3

Mortgage calculator

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Est. monthly payment
$10,267/mo
$335,980 down
$1,343,920 loan
Principal & interest$8,717
Property tax (est.)$1,400
Home insurance (est.)$150

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Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated 13 days ago.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.