$1,679,900
5 Willowdale Rd
Winchester, MA, 01890
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.
Property Details
Price:
$1,679,900
MLS #:
73572791
Status:
Active
Beds:
3
Baths:
2
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
East Hill
Listed Date:
Sep 8, 2026
Finished Sq Ft:
2,483
Total Sq Ft:
2,483
Lot Size:
14,318 sqft / 0.33 acres (approx)
Year Built:
1953
Schools
Elementary School:
Lincoln
Middle School:
Mccall
High School:
Whs
Interior
Above Grade Finished Area
1822
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
Bathrooms
2 Full Bathrooms
Below Grade Finished Area
661
Cooling
Central Air, Whole House Fan
Fireplaces Total
1
Flooring
Wood, Tile, Carpet, Concrete, Flooring – Wall to Wall Carpet
Heating
Baseboard, Radiant, Oil
Interior Features
Cable Hookup, Recessed Lighting, Beadboard, Closet/Cabinets – Custom Built, Lighting – Overhead, Closet, Media Room, Mud Room, Exercise Room, Central Vacuum, Wired for Sound, High Speed Internet
Laundry Features
Electric Dryer Hookup, Washer Hookup, Lighting – Overhead, Sink, In Basement
Main Level Bathrooms
1
Main Level Bedrooms
3
Exterior
Architectural Style
Ranch
Attached Garage YN
1
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
Construction Materials
Frame
Covered Spaces
2
Exterior Features
Patio, Rain Gutters, Storage, Sprinkler System, Decorative Lighting, Screens, Garden, Stone Wall
Garage Spaces
2
Green Energy Efficient
Thermostat
Open Parking Spaces
5
Open Parking YN
1
Parking Features
Attached, Under, Garage Door Opener, Workshop in Garage, Paved Drive, Off Street, Paved
Parking Spots
7
Parking Total
7
Patio And Porch Features
Patio
Roof
Shingle
Security Features
Security System
Waterfront Features
1/2 to 1 Mile To Beach
Window Features
Insulated Windows, Storm Window(s), Screens
Financial
Tax Year
2025
Taxes
$15,730
Marie Andrews is an award-winning, licensed real estate broker with licenses in Massachusetts and Florida. She has been selling real estate in the greater Boston area for over 20 years. Over the past two decades, Marie has worked for Century 21 Advanced Realty, building a reputation as a multi-million dollar producer. She has developed an extensive network of investors, lenders, and attorneys. Marie has a wide knowledge base on property management, Massachusetts real estate law, and building…
More About MarieMortgage Calculator
Map
Current real estate data for Single Family in Winchester as of Sep 11, 2026
59
Single Family Listed
62
Avg DOM
547
Avg $ / SqFt
$1,955,164
Avg List Price
Community
- Address5 Willowdale Rd Winchester MA
- SubdivisionEast Hill
- CityWinchester
- CountyMiddlesex
- Zip Code01890
Subdivisions in Winchester
- Brooks / Parkhurst / Town Forest
- Cox Road / High St Extension neighborhood
- Flats
- Flats neighborhood
- Lakeview/Wedgemere~ Near downtown & Wedgemere train station
- Macdonald field neighborhood
- Middlesex / downtown
- Near town/ Pine St neighborhood
- Old Village/ West Side
- Rangeley Historical Estate
- The Flats
- Vinson-Owen School District.
- West Side
- Winning Farm
Similar Listings Nearby
Property Summary
- Located in the East Hill subdivision, 5 Willowdale Rd Winchester MA is a Single Family for sale in Winchester, MA, 01890. It is listed for $1,679,900 and features 3 beds, 2 baths, and has approximately 2,483 square feet of living space, and was originally constructed in 1953. The current price per square foot is $677. The average price per square foot for Single Family listings in Winchester is $547. The average listing price for Single Family in Winchester is $1,955,164. To schedule a showing of MLS#73572791 at 5 Willowdale Rd in Winchester, MA, contact your Pegasus Realty LLC agent at 781-858-3505.
Courtesy of Compass. The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.
5 Willowdale Rd
Winchester, MA












































