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21 Amberwood DrWinchester, MA 01890

For Sale

$1,999,000

Smart Buyer Rebate $9,995

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.

Listed by Gayle Winters & Co. Team

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Compass

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6176990310

Listed by Gayle Winters

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Compass

Last updated October 29, 2026

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Source: MLSPin #73588059

Listing Facts

  • TypeSingle-family
  • NeighborhoodWest Side
  • Bedrooms5
  • Bathrooms4
  • Days on Prevu24
  • Taxes$19,853/year
  • Size4,063 sqft
  • Price per sqft$492

Amenities

  • Dishwasher
  • Private Outdoor Space
  • Washer/Dryer
  • Air Conditioning
  • Parking

Location

Mortgage Calculator

Listing History

10/26/2026
Price Decreased
$1,999,000
10/07/2026
Listed by Compass
$2,049,000
  1. 10/26/2026$1,999,000
    Price Decreased
  2. 10/07/2026$2,049,000
    Listed by Compass

Property Details for 21 Amberwood Dr

Association

Amenities

  • Community Features: Park

Exterior

Construction

  • Roof: Shingle
  • Window Features: Skylight(s), Insulated Windows, Screens
  • Year Built: 1973
  • Year Built Details: Actual
  • Architectural Style: Colonial, Cape
  • Construction Materials: Frame
  • Exterior Features: Rain Gutters, Garden, Lighting

Features

  • Patio And Porch Features: Patio

Measurements

  • Building Area Total: 4,063
  • Building Area Units: Square Feet
  • Lot Size Acres: 0.46
  • Lot Size Area: 0
  • Lot Size Square Feet: 19,998
  • Lot Size Units: Acres

Financial

Taxes

  • Parcel Number: M:0026 B:0201 L:0000,901207
  • Tax Annual Amount: $19,853.00
  • Tax Assessed Value: $1,791,800.00
  • Tax Year: 2026

Interior

Features

  • Appliances: Electric Water Heater, Range, Oven, Dishwasher, Disposal, Microwave, Refrigerator, Washer, Dryer, Wine Refrigerator
  • Fireplace Features: Family Room
  • Fireplace: Yes
  • Fireplaces Total: 1
  • Flooring: Tile, Hardwood
  • Interior Features: Recessed Lighting, Open Floorplan

Measurements

  • Living Area: 4,063
  • Living Area Source: Public Records

Rooms

  • Basement: Partial, Finished, Interior Entry
  • Has Basement: Yes
  • Bathrooms Full: 3
  • Bathrooms Half: 1
  • Bathrooms Total Integer: 4
  • Bedrooms Total: 5
  • Main Level Bathrooms: 1
  • Main Level Bedrooms: 1
  • Rooms Total: 11

Parking

Parking

  • Attached Garage: Yes
  • Covered Spaces: 2
  • Garage Spaces: 2
  • Garage: Yes
  • Open Parking Spaces: 4
  • Open Parking: Yes
  • Parking Features: Paved, Attached, Garage Door Opener, Off Street, Garage
  • Parking Total: 6

Utilities

Equipment

  • Cooling: Central Air
  • Has Cooling: Yes
  • Electric: 200+ Amp Service
  • Heating: Baseboard, Electric
  • Has Heating: Yes
  • Laundry Features: Electric Dryer Hookup, Washer Hookup
  • Sewer: Public Sewer
  • Water Source: Public

Frequently Asked Questions

How many bedrooms and bathrooms does this single-family home have?

There are 5 bedrooms and 4 bathrooms in this single-family home at 21 Amberwood Dr.

Does this single-family home have parking?

Yes, there are 2 parking spaces available for 21 Amberwood Dr.

What are the annual taxes for 21 Amberwood Dr?

Annual taxes for this single-family home are estimated at $19,853.

How does 21 Amberwood Dr compare to other single-family homes in West Side?

This single-family home is listed 46% below the average price for single-family homes in West Side and has been on the market for 67 less days than the typical home in this area.

What is the square footage on this single-family home?

According to the MLS, this listing is 4,063 sqft.

21 Amberwood Dr is a 5-bedroom, 4-bath single-family home for sale in Winchester MA 01890. Listed on Prevu for 24 days at $1,999,000. This includes a recent price decrease of $50,000. This property features 4,063 square feet of living space, located in West Side. The median listing price for single-family homes in this area is $2,850,000. The home offers private outdoor space, dishwasher, air conditioning, parking, and washer/dryer. Explore more single-family home listings in Middlesex County.

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting 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, leasing or renting. 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, or as to the accuracy of any of the Images, set forth herein.

Full MLS Disclaimers

Rebate estimate is indicative only and based on listing price and estimated buyer's agent commission paid by owner, if applicable. Final rebates are subject to Terms of Use and may vary due to final negotiated transaction terms.