









































20 Foxcroft Road, Winchester MA 01890
About this home
A rare opportunity to own one of The Flats’ most celebrated homes! This 1930s Colonial Revival w/ classic curb appeal & elegant proportions sits on over ½ acre of estate-like grounds featuring heated pool, patios, pergola & multiple areas for effortless entertaining. Inside, a grand foyer & sweeping staircase introduce gracious rooms w/ exquisite millwork & superb flow, equally suited for relaxed family living or refined gatherings. Highlights include eat-in chef’s kitchen w/ island & timeless finishes, butler’s pantry, stately dining rm, large living & family rms & private study. Upstairs offers a luxurious primary suite w/ marble bath & dressing rm, plus 4 add’l BRs, 3 en suite. Lower level features versatile family/game rms & wine cellar. Carriage house (2007) w/ 4 garage bays, cabana bath & studio/gym offers endless possibilities & ADU potential. Moments to town center, top rated schools & train, this iconic home is where elegance & livability come together in perfect balance.
Facts & Features
Property Overview
Interior Features
Exterior & Structure
Lot & Land
Parking & Garage
Utilities & Systems
Community & HOA
Financial & Tax Information
Additional Details
Location
Neighborhood
Wedgemere - The Flats
20 Foxcroft Road, Winchester MA 01890
Winchester, MA 01890
Walkability
Schools
Monthly Payment Calculator
Payment Breakdown
Property History
Market Insights
Property Timeline
Pending Sale
Sep 17, 2025Listed for Sale
Sep 16, 2025Date | Event | Price | Change | $/sqft | Details |
---|---|---|---|---|---|
09/17/2025 | ⏳ Pending Sale | - | - | - | Offer accepted, sale pending |
09/16/2025 | 🏠 Listed for Sale | $4,399,000 | - | - | Original listing |