Recently Listed Open House 10/9 11am - 1pm
21 Amberwood Dr
Winchester, MA, 01890 $ 2,049,000
Bedrooms5 Baths3.1 Sq 4,063 Monthly Estimate*
$ 14,152
for $2,049,000 with 5 bedrooms and 3 full baths, 1 half bath. This 4,063 square foot home was built in 1973 on a lot size of 0.46.
Welcome to this beautifully appointed and exceptionally spacious home, ideally situated in a quiet, desirable West Side Winchester neighborhood within the sought-after Vinson-Owen School district. Offering an impressive combination of elegant living spaces, flexible accommodations, and thoughtful upgrades, this home provides room for everyone while easily adapting to a variety of lifestyles. At the heart of the home is the expansive granite kitchen, designed for both everyday living and entertaining. Custom cabinetry, Thermador double ovens, a Dacor warming drawer, Sub-Zero refrigerator, wine refrigerator, recessed lighting, and an impressive 50-square-foot center island create a wonderful gathering space with plenty of room for cooking, dining, and entertaining. The kitchen flows into a comfortable family room featuring a custom-built entertainment center and electric fireplace. A gracious formal dining room showcases handcrafted molding and classic wainscoting, while additional first-floor living spaces provide tremendous flexibility for a formal living room, playroom, home office, den, or whatever best suits your needs.One of the home's most appealing features is the first-floor bedroom suite with a full bath, offering exceptional versatility for extended family, guests, an au pair, or anyone seeking the convenience of first-floor living. A dedicated laundry room on this level adds even more functionality. With multiple living areas and flexible rooms throughout the first floor, there are countless ways to create private spaces for additional family members while still enjoying plenty of room to gather together.Upstairs, the generously sized primary suite provides a relaxing retreat with vaulted ceilings, recessed lighting, double closets, and a beautifully tiled private bath with double sinks. Three additional spacious bedrooms, another full bath, and additional office space provide abundant room for family, guests, work-from-home needs, hobbies, or study areas.With its generous proportions, flexible floor plan, multiple bedroom and living configurations, and outstanding West Side location, this is a home designed to grow and change with its owners. Enjoy the peace and privacy of a quiet neighborhood while being part of the wonderful Winchester community. This is more than simply a beautiful house—it is a home offering the space, versatility, and comfort today's buyers are looking for.
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Open House
10/9/2026 11:00 AM - 1:00 PM
10/10/2026 11:00 AM - 1:00 PM
10/11/2026 10:30 AM - 12:00 PM
21 Amberwood Dr Winchester, MA
* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm
List ByGayle Winters & Co. TeamListing Agent
Affordability Calculator
- Monthly Principal & Interest
- $14,152
- Monthly Property Taxes
- $1,654
- Monthly Home Insurance
- --
Default based on a 30-year fixed rate of 7.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save NearbySingle family listings in Winchester, MA
Average List Price $2,285,248
Percent of Sale Price 12%
About Winchester, MA 22,228 Population
7% Since 2002
$ 152,119 Median Income
45.68 Median Age
42% Households with Children
Trends Information provided by ATTOM Data Solutions.
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Pricing History| Date | Price | Price Change | Description |
|---|
| 10/7/2026 | $2,049,000 | | Listed Price |