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$1,679,900 Just Listed

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 2,483 Sq. Ft.
  • 0.33 Acres
  • 2 Car Garage
  • Updated 18 hours ago
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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.

Full Property Details for 5 Willowdale Rd

General

  • Price: $1,679,900
  • Taxes: $15,730 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MLSPin
  • MLS ID: 73572791
  • Updated: 9/8/2026
  • Added to Site: 1 day(s) ago

Interior

  • Number of Rooms: 8
  • 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
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Fireplace(s): Living Room
  • 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
  • Flooring: Wood, Tile, Carpet, Concrete, Flooring - Wall to Wall Carpet

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2
  • Main Floor Baths: 1
  • Main - Full Baths: 2
  • Bathroom 1: Full Bathroom, Tiled Bathroom with Tub and Shower, Linen Closet, Stone/Ceramic Tile Flooring, Stone/Gran, Main, First
  • Bathroom 2: Full Bathroom, Bathroom with Tub and Shower, Stone/C, Basement

Bedrooms

  • Total Bedrooms: 3
  • Primary Bedroom: Main, First
  • Bedroom 2: Hardwood Flooring, Lighting - Overhead, Crown Molding, Closet - Double, Main, First
  • Bedroom 3: Closet, Hardwood Flooring, Lighting - Overhead, Crown Molding, Main, First

Other Rooms

  • Living Room: Hardwood Flooring, Cable Hookup, Wainscoting, Crown Molding, Decorative Molding, Main, First
  • Family Room: Custom-Built Closet/Cabinets, Hardwood Flooring, Cable Hookup, Exterior Access, Open Floorplan, Recessed Lighting, Crown Molding, Main, First
  • Kitchen: Beamed Ceilings, Custom-Built Closet/Cabinets, Hardwood Flooring, Pantry, Stone/Granite/Solid Countertops, Upgraded Countertops, Kitchen Island, Cable Hookup, Chair Rail, Exterior Access, Recessed Lighting, Remodeled, Stainless Steel Appliances, Wine Chiller, Beadboard, Crown Molding, Pocket Door, Main, First
  • Dining Room: Custom-Built Closet/Cabinets, Hardwood Flooring, Exterior Access, Open Floorplan, Recessed Lighting, Lighting - Pendant, Crown Molding, Pocket Door, Main, First
  • Laundry: Electric Dryer Hookup, Washer Hookup, Lighting - Overhead, Sink, In Basement

Additional Information

  • Year Round: Yes
  • Security/Safety: Security System

Exterior

  • Exterior Features: Patio, Rain Gutters, Storage, Sprinkler System, Decorative Lighting, Screens, Garden, Stone Wall
  • Color: Beige

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 7
  • Parking Features: Attached, Under, Garage Door Opener, Workshop in Garage, Paved Drive, Off Street, Paved

Location

  • County: Middlesex
  • Subdivision: East Hill
  • Driving Directions: Pierrepont to Hollywood to Willowdale

School Information

  • Elementary School: Lincoln
  • Middle School: Mccall
  • High School: Whs

Heating & Cooling

  • Air Conditioning: Yes
  • Cooling Type: Central Air, Whole House Fan
  • Cooling Zones: 1
  • Heating Type: Baseboard, Radiant, Oil
  • Heating Fuel: Baseboard, Radiant, Oil
  • Heating Zones: 2

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: Connection for Electric Range, Connection for Electric Oven, Connection for Electric Dryer, Washer Hookup, Icemaker Connection

Structural Information

  • Architectural Style: Ranch
  • Exterior Const.: Frame
  • Basement: Yes
  • Basement Desc.: Full, Crawl Space, Finished, Interior Entry, Garage Access
  • Roof: Shingle
  • Drive-In Doors: Insulated Doors
  • Square Feet: 2,483
  • Sq. Ft. Source: Public Records
  • Year Built: 1953

Lot Features

  • Lot Size (Acres): 0.33
  • Lot Dimensions: .33
  • Frontage: Public

Water Features

  • Water Front Desc.: 1/2 to 1 Mile To Beach

Green Features

  • Energy Efficient: Thermostat

Financial Considerations

  • Price Per Sq. Ft.: $676.56
  • Tax Amount: $15,730
  • Tax Year: 2025

Disclosures and Reports

  • Exclusions: Please See Disclosures + Inclusion/Exclusion Attachments In Mls
  • Disclosures/Rstr.: LA is Seller. Radiant heated floors in kitchen, dining rm, family rm & 1st flr bath; foyer has ipe hdwd flrs; media rm is wired for surround sound & cable. Please see Disclosures + Inclusion/Exclusion attachments in MLS. NO OPEN HOUSES, shown By Private Appointment only.
  • Property ID: M:006 B:0213 L:0, 895969
Buyer's Brokerage Compensation: Contact Listing Agent
Not binding unless confirmed by separate agreement among applicable parties.

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— 5 Willowdale Rd —

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NMLS#: 1598647

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Schools serving 5 Willowdale Rd

School District:Winchester School District, Winchester, MA
NameGradesDistance
Lincoln Elementary School, Winchester, MA
161 Mystic Valley Parkway, Winchester, MA 01890
K-50.8 mi
Mccall Middle School
458 Main Street, Winchester, MA 01890
6-80.7 mi
Winchester High School
80 Skillings Road, Winchester, MA 01890
9-121.1 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 5 Willowdale Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
9/08/2026
Listed
$1,679,900
32.9%
MLS
4/08/2021
Sold
$1,264,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 5 Willowdale Rd

Year
Property Taxes
Change
Tax Assessment
Change
2025
$157
-99%
$1,418,400
5%
2024
$15,254
6%
$1,346,300
11%
2023
$14,351
8%
$1,216,200
15%
2022
$13,264
14%
$1,060,300
17%
2021
$11,594
8%
$903,700
4%
2020
$10,751
12%
$867,700
9%
2019
$9,635
4%
$795,600
5%
2018
$9,255
3%
$759,200
4%
2017
$8,969
8%
$730,400
3%
2016
$8,297
2%
$710,400
6%
2015
$8,111
10%
$668,100
15%
2014
$7,372
—
$582,300
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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5 Willowdale Rd, Winchester, MA 01890 (MLS# 73572791) is a Single Family property with 3 bedrooms and 2 full bathrooms. 5 Willowdale Rd is currently listed for $1,679,900 and was received on September 08, 2026. This property is listed by Erica Carson from our Lexington/Winchester Regional Office.Want to learn more about 5 Willowdale Rd? Do you have questions about finding other Single Family real estate for sale in Winchester Highlands? You can browse all Winchester Highlands real estate or contact a Coldwell Banker agent to request more information.

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