Property Description

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 tap to expand

Amenities

  • Bike Path
  • Conservation Area
  • Golf Course
  • Highway Access
  • House of Worship
  • Laundromat
  • Marina
  • Medical Facility
  • Park
  • Private School
  • Public School
  • Public Transportation
  • Shopping
  • Swimming Pool
  • T-Station
  • Tennis Court
  • Walk/Jog Trails

Kitchen, Dining, and Appliances

  • Beadboard, Cable Hookup, Ceiling - Beamed, Chair Rail, Closet/Cabinets - Custom Built, Countertops - Stone/Granite/Solid, Countertops - Upgraded, Crown Molding, Exterior Access, Flooring - Hardwood, Kitchen Island, Pantry, Pocket Door, Recessed Lighting, Remodeled, Stainless Steel Appliances, Wine Chiller
  • Dishwasher - ENERGY STAR, Disposal, Dryer - ENERGY STAR, Microwave, Range, Refrigerator, Refrigerator - Wine Storage, Vacuum System, Vent Hood, Wall Oven, Washer - ENERGY STAR
  • Dining Room Features: Closet/Cabinets - Custom Built, Crown Molding, Exterior Access, Flooring - Hardwood, Lighting - Pendant, Open Floor Plan, Pocket Door, Recessed Lighting

Bathrooms

  • Full Baths: 2
  • Bathroom 1 Features: Bathroom - Full, Bathroom - Tiled With Tub & Shower, Closet - Linen, Countertops - Stone/Granite/Solid, Double Vanity, Flooring - Stone/Ceramic Tile, Lighting - Overhead, Lighting - Sconce, Recessed Lighting, Remodeled
  • Bathroom 2 Level: Basement
  • Bathroom 2 Features: Bathroom - Full, Bathroom - With Tub & Shower, Flooring - Stone/Ceramic Tile, Lighting - Overhead, Pocket Door

Bedrooms

  • Bedrooms: 3
  • Master Bedroom Features: Closet - Double, Crown Molding, Flooring - Hardwood, Lighting - Overhead
  • Master Bedroom Features: Closet - Double, Crown Molding, Flooring - Hardwood, Lighting - Overhead
  • Master Bedroom Features: Closet, Crown Molding, Flooring - Hardwood, Lighting - Overhead

Other Rooms

  • Total Rooms: 8
  • Living Room Features: Cable Hookup, Crown Molding, Decorative Molding, Fireplace, Flooring - Hardwood, Wainscoting
  • Family Room Features: Cable Hookup, Closet/Cabinets - Custom Built, Crown Molding, Exterior Access, Flooring - Hardwood, Open Floor Plan, Recessed Lighting
  • Laundry Room Features: Crawl, Finished, Full, Garage Access, Interior Access

Utilities

  • Heating: Hot Water Baseboard, Oil, Radiant
  • Heat Zones: 2
  • Hot Water: Other (See Remarks)
  • Cooling: Central Air
  • Cooling Zones: 1
  • Electric Info: 150 Amps, Circuit Breakers
  • Energy Features: Insulated Doors, Insulated Windows, Prog. Thermostat, Storm Windows
  • Utility Connections: Icemaker Connection, Washer Hookup, for Electric Dryer, for Electric Oven, for Electric Range
  • Water: City/Town Water
  • Sewer: City/Town Sewer

Garage & Parking

  • Garage Parking: Attached, Garage Door Opener, Under, Work Area
  • Garage Spaces: 2
  • Parking Features: Off-Street, Paved Driveway
  • Parking Spaces: 7

Interior Features

  • Square Feet: 2483
  • Fireplaces: 1
  • Interior Features: Cable Available, Central Vacuum, Internet Available - Fiber-Optic, Security System, Whole House Fan
  • Accessability Features: Unknown

Construction

  • Year Built: 1953
  • Type: Detached
  • Style: Ranch
  • Construction Type: Frame
  • Foundation Info: Poured Concrete
  • Roof Material: Asphalt/Fiberglass Shingles
  • Flooring Type: Concrete, Tile, Wall to Wall Carpet, Wood
  • Lead Paint: Certified Treated
  • Warranty: No

Exterior & Lot

  • Exterior Features: Decorative Lighting, Garden Area, Gutters, Patio, Screens, Sprinkler System, Stone Wall, Storage Shed
  • Road Type: Public
  • Distance to Beach: 1/2 to 1 Mile

Other Information

  • MLS ID# 73572791
  • Last Updated: 09/08/26
  • HOA: No
  • Reqd Own Association: Unknown

Property History tap to expand

Date Event Price Price/Sq Ft Source
09/08/2026New$1,679,900$677MLSPIN

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Map

Seller's Representative: Erica Carson, Coldwell Banker Realty - Lexington
Sub Agent Compensation: n/a
Buyer Agent Compensation: n/a
Facilitator Compensation: n/a
Compensation Based On: n/a
Sub-Agency Relationship Offered: No

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MLS PIN data last updated at 2026-09-08 08:16:00