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.
Single-familyProperty Type
1953Year Built
0.33 acresLot Size
$664Price/Sq.Ft.
2 garage spacesParking
Listed by Erica Carson• Coldwell Banker Realty - Lexington
Listed by • Coldwell Banker Realty - Lexington
Bought with Donna Sides• Keller Williams Realty Boston Northwest
Est. $4,855 per month, based on comparable rentals
Sale and tax history for 5 Willowdale Rd
Sale History
Tax History
Date
Event
Price
MLS PIN #73572791
Oct 6, 2026
Sold
$1,649,900
$664/sq ft
Sep 23, 2026
Pending
—
Sep 13, 2026
Contingent
—
Sep 8, 2026
Listed
$1,679,900
$677/sq ft
MLS PIN #72782610
Apr 8, 2021
Sold
$1,264,000
$509/sq ft
Feb 10, 2021
Contingent
—
Feb 4, 2021
Listed
$1,250,000
$503/sq ft
+25
This extraordinary home, w/ enhancements by Royal Barry Wills Ass., exudes craftsmanship. The mahogany kitchen features a beautiful wooden island & handmade pocket plantation shutters which blend seamlessly with the cabinets. Pocket glass doors in the kitchen offer privacy or can open to the family & dining rm areas, which feature an extensive wall of windows. The family rm will wow you with the custom built cherry entertainment center with copper paneling & ebony inlays. No detail was spared with the addition of radiant heated floors in the kitchen, dining, family rm & bathroom. Foyer has built in seat and ipe hdwd floors. Closets abound in the private wing of the home- 3 bdrms & a full bath. The oversized 2 car garage leads to a 2nd mudroom area, newly renovated media room & an exercise room, which includes laundry & 2nd full bath. The private yard, designed by Zen Associates, will amaze you with its expansive patio & 2nd tier of grassy yard that will provide hours of entertainment.
Public Records
May 3, 1991
Sold
$182,500
$73/sq ft
Year
Property tax
Land + Additions
Assessment*
2026
$16,202 (+3.0%)
$1,008,700 + $453,600
$1,462,300
2025
$15,730 (+3.1%)
$1,008,700 + $409,700
$1,418,400
2024
$15,254 (+6.3%)
$936,600 + $409,700
$1,346,300
2023
$14,351 (+8.2%)
$936,600 + $409,700
$1,346,300
2022
$13,264 (+14.4%)
$756,500 + $303,800
$1,060,300
2021
$11,594 (+7.8%)
$630,400 + $273,300
$903,700
2020
$10,751 (+11.6%)
$594,400 + $273,300
$867,700
2019
$9,635 (+4.1%)
$522,300 + $273,300
$795,600
2018
$9,255 (+3.2%)
$492,600 + $266,600
$759,200
2017
$8,969 (+8.1%)
$463,800 + $266,600
$730,400
2016
$8,297 (+2.3%)
$463,800 + $246,600
$710,400
2015
$8,111 (+10.0%)
$421,500 + $246,600
$668,100
2014
$7,372 (+0.7%)
$351,200 + $231,100
$582,300
2013
$7,322 (+1.8%)
$351,200 + $222,200
$573,400
2012
$7,196 (+3.7%)
$351,200 + $222,200
$573,400
2011
$6,938 (−0.8%)
$351,200 + $222,200
$573,400
2010
$6,993 (+2.1%)
$376,500 + $231,100
$607,600
2009
$6,848
$376,500 + $231,100
$607,600
Public record
Beds
3
Baths
2
Stories
1
Lot width
—
Lot depth
—
Lot size
0.33 Acres
Year renovated
—
Sq. Ft.
2,483
Year built
1953
Style
Single Family Residential
County
Middlesex County
APN
3398347S
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Sep 16, 2026.
Property details
Parking
Parking Information
Has Garage
Has Open Parking
# of Garage Spaces: 2
# of Covered Spaces: 2
Open Parking Spaces: 5
Parking Spaces: 7
AttachedGarageYN: Yes
Parking Features: Attached, Under, Garage Door Opener, Workshop in Garage, Paved Drive, Off Street, Paved
Laundry Features: Electric Dryer Hookup, Washer Hookup, Lighting - Overhead, Sink, In Basement
Fireplace Information
Has Fireplace
# of Fireplaces (Total): 1
Fireplace Features: Living Room
Appliances
Appliances: Water Heater, Oven, Disposal, Microwave, Range, Refrigerator, Wine Refrigerator, ENERGY STAR Qualified Dryer, ENERGY STAR Qualified Dishwasher, ENERGY STAR Qualified Washer, Vacuum System, Range Hood, Plumbed For Ice Maker
Utilities: for Electric Range, for Electric Oven, for Electric Dryer, Washer Hookup, Icemaker Connection
Sewer: Public Sewer
Water Source: Public
Electric: Circuit Breakers, 150 Amp Service
Heating & Cooling
Has Heating
Has Cooling
Heating: Baseboard, Radiant, Oil
Cooling: Central Air, Whole House Fan
Location
School Information
Elementary School: Lincoln
Middle Or Junior School: Mccall
High School: Whs
Location Information
Directions: Pierrepont to Hollywood to Willowdale
UnparsedAddress: 5 Willowdale Rd, Winchester MA 01890
Community Information
Senior CommunityYN: No
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, Marina, Private School, Public School, T-Station
Public facts
Beds: 3
Baths: 2.0
Sq. Ft.: 2,483
Stories: 1.0
Lot Size: 0.33 acres
Style: Single Family Residential
Year Built: 1953
Year Renovated: —
County: Middlesex County
APN: 3398347S
Home facts updated by county records on Sep 16, 2026
Other
Miscellaneous Information
Heat Zones: 2
Listing Information
Exclusions: Please See Disclosures + Inclusion/Exclusion Attachments In Mls
StandardStatus: Closed
Around this home
Schools
Lincoln Elementary School
Public K-5 • Assigned • 0.8mi
9/10
McCall Middle School
Public 6-8 • Assigned • 0.7mi
9/10
Winchester High School
Public 9-12 • Assigned • 1.1mi
10/10
Provided by GreatSchools
Climate risks
1/10 Flood Factor
Minimal risk of a flood reaching the building in the next 30 years
3/10 Fire Factor
0.15% chance of being in a wildfire in next 30 years
5/10 Heat Factor
7 days above 97° expected this year, 15 days in 30 years
6/10 Wind Factor
50% chance of strong winds in next 30 years
3/10 Air Factor
3 unhealthy days expected this year, 3 days in 30 years
Provided by First Street
Historical weather
Winchester, MA • 01890
Average low and high temperatures (°F)
34
20
36
21
51
32
60
40
69
51
80
61
84
66
80
60
75
56
64
46
53
36
39
24
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
88/ 100
Very good sunlight
Sunscore
This home receives average direct sun exposure in Winchester. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.
8.9 hrs
5.5 hrs
JuneDecember
Provided by Shadowmap
Estimated sale price
$1.59M – $1.93M
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