20 Foxcroft Road
Winchester, MA, 01890
$4,399,000
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.
Current real estate data for Single Family in Winchester as of Oct 07, 2025
62
Single Family Listed
65
Avg DOM
551
Avg $ / SqFt
$2,270,911
Avg List Price
Property Details
Price:
$4,399,000
MLS #:
73431361
Status:
Pending
Beds:
5
Baths:
5.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
The Flats
Neighborhood:
wedgemere
Listed Date:
Sep 16, 2025
Finished Sq Ft:
7,679
Total Sq Ft:
7,679
Lot Size:
25,418 sqft / 0.58 acres (approx)
Year Built:
1937
Schools
Elementary School:
Ambrose
Middle School:
Mccall Middle School
High School:
Winchester High School
Interior
Appliances
Range, Oven, Dishwasher, Disposal, Trash Compactor, Microwave, Refrigerator, Washer, Dryer, Wine Refrigerator, Range Hood
Bathrooms
4 Full Bathrooms, 3 Half Bathrooms
Cooling
Central Air
Fireplaces Total
4
Flooring
Tile, Marble, Hardwood, Stone / Slate, Flooring – Hardwood, Flooring – Stone/Ceramic Tile, Flooring – Wall to Wall Carpet
Heating
Forced Air, Radiant, Natural Gas, Fireplace
Laundry Features
Closet/Cabinets – Custom Built, Flooring – Stone/Ceramic Tile, Electric Dryer Hookup, Lighting – Overhead, Second Floor
Exterior
Architectural Style
Colonial Revival
Community Features
Public Transportation, Shopping, Pool, Tennis Court(s), Park, Walk/Jog Trails, Golf, Medical Facility, Bike Path, House of Worship, Public School, T-Station
Construction Materials
Frame
Exterior Features
Patio, Pool – Inground Heated, Cabana, Professional Landscaping, Sprinkler System, Decorative Lighting, Fenced Yard, Garden
Other Structures
Cabana
Parking Features
Detached, Garage Door Opener, Heated Garage, Paved Drive, Off Street, Paved
Parking Spots
6
Roof
Slate
Security Features
Security System
Financial
Tax Year
2025
Taxes
$54,223
Map
Contact Us
Mortgage Calculator
Community
- Address20 Foxcroft Road Winchester MA
- SubdivisionThe Flats
- CityWinchester
- CountyMiddlesex
- Zip Code01890
Subdivisions in Winchester
- Close to Wright Locke Farm
- Cox Road / High St Extension neighborhood
- East SIde near town forest!!
- Everett/ Stratford
- Flats location
- FLATS location Across from Wedgemere/Oxford
- Lakeview/Wedgemere~ Near downtown & Wedgemere train station
- Ledgewood Estates
- Middlesex
- Myopia Hill/ Winchester Country Club Area
- Near VO school
- old village/ West side
- The Flats
- Top neighborhood near town center
- West side
Property Summary
- Located in the The Flats subdivision, 20 Foxcroft Road Winchester MA is a Single Family for sale in Winchester, MA, 01890. It is listed for $4,399,000 and features 5 beds, 6 baths, and has approximately 7,679 square feet of living space, and was originally constructed in 1937. The current price per square foot is $573. The average price per square foot for Single Family listings in Winchester is $551. The average listing price for Single Family in Winchester is $2,270,911. To schedule a showing of MLS#73431361 at 20 Foxcroft Road in Winchester, MA, contact your Boardwalk Real Estate Corp. agent at 781-944-7820.
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CRP: Certified Relocation Professional CRS: Certified Residential Specialist GRI: Graduate of Realtors Institute CBR: Certified Buyers Representative BSBA: Bachelor of Science in Business Administration. Babson College 1979 MBA: Master of Business Administration. Babson College 2002 James M. Joly is President and Principal-Owner of Boardwalk Real Estate Corp.,…
More About JamesCourtesy of Better Homes and Gardens Real Estate – The Shanahan Group. 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.
20 Foxcroft Road
Winchester, MA