21 Amberwood Dr · Winchester

FOR SALE · MLS #73588059

$1,999,000

beds
5
baths
3.5
sqft
4,063

21 Amberwood Dr

Winchester, MA 01890

LOCATION

Property location

Directions

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21 Amberwood Dr, Winchester, MA 01890Open Street View

Johnson Road to Amberwood Drive

Home type
Single Family Residence
Interior living area
4,063 sqft
Year built
1973
Lot size
19,998 sqft (about 0.46 acres)
Parking spaces
6
Price per sqft
$492/sqft

About this home

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 · Compass
MLS PIN #73588059 · Updated 10/29/2026, 3:05:00 AM ET

Facts & features

Home overview
Property subtype
Single Family Residence
Property category
Residential
MLS status
Active
Bedrooms
5
Full bathrooms
3
Half bathrooms
1
Total bathrooms
3.5
Total rooms
11
Living area
4,063 sqft
Living area source
Public Record
Above grade finished area
3,535 sqft
Below grade finished area
528 sqft
Building area
4,063
Building area units
Square Feet
Building area source
Public Records
Area includes basement
Yes
Area disclosures
Measured for marketing purposes only - buyer and agent to do their due diligence.
Main level bedrooms
1
Main level bathrooms
1
Interior & systems
Heating
Electric Baseboard · Electric
Heating available
Yes
Cooling
Central Air
Cooling available
Yes
Appliances
Electric Water Heater · Range · Oven · Dishwasher · Disposal · Microwave · Refrigerator · Washer · Dryer · Wine Refrigerator
Flooring
Tile · Hardwood · Flooring - Stone/Ceramic Tile · Flooring - Hardwood
Interior features
Bathroom - Full · Bathroom - Tiled With Tub & Shower · Lighting - Sconce · Lighting - Overhead · Recessed Lighting · Lighting - Pendant · Bathroom · Office · Mud Room · Entry Hall
Laundry
Flooring - Stone/Ceramic Tile · Lighting - Overhead · Second Floor · Electric Dryer Hookup · Washer Hookup
Laundry dimensions
6'4X5'4
Basement
Partial · Finished · Interior Entry · Radon Remediation System · Slab
Fireplace
Yes
Fireplaces
1
Fireplace features
Family Room
Electrical service
200+ Amp Service
Windows
Skylight(s) · Insulated Windows · Screens
Primary bathroom features
Yes
Room details

Primary bedroom

Level
Second
Area
236.35 sqft
Length
12.83 ft
Width
18.42 ft
Features
Bathroom - Full · Skylight · Closet · Flooring - Hardwood · Recessed Lighting · Lighting - Sconce

Bedroom 2

Level
Second
Area
242.78 sqft
Length
19.17 ft
Width
12.67 ft
Features
Closet · Flooring - Hardwood · Recessed Lighting · Lighting - Sconce

Bedroom 3

Level
Second
Area
176.33 sqft
Length
15.33 ft
Width
11.5 ft
Features
Skylight · Walk-In Closet(s) · Flooring - Hardwood

Bedroom 4

Level
Second
Area
213.78 sqft
Length
12.33 ft
Width
17.33 ft
Features
Walk-In Closet(s) · Flooring - Hardwood · Lighting - Overhead

Bedroom 5

Level
Main,First
Area
196 sqft
Length
14 ft
Width
14 ft
Features
Bathroom - Full · Closet · Flooring - Hardwood · Recessed Lighting

Living room

Level
Main,First
Area
268.22 sqft
Length
22.67 ft
Width
11.83 ft
Features
Bathroom - Half · Flooring - Hardwood · Recessed Lighting

Dining room

Level
Main,First
Area
281.89 sqft
Length
19.67 ft
Width
14.33 ft
Features
Flooring - Hardwood · Recessed Lighting · Wainscoting · Lighting - Pendant

Family room

Level
Main,First
Area
319.31 sqft
Length
15.83 ft
Width
20.17 ft
Features
Closet/Cabinets - Custom Built · Flooring - Hardwood · Exterior Access · Open Floorplan · Recessed Lighting

Kitchen

Level
Main,First
Area
299.14 sqft
Length
14.83 ft
Width
20.17 ft
Features
Flooring - Hardwood · Kitchen Island · Exterior Access · Recessed Lighting · Stainless Steel Appliances · Pot Filler Faucet · Wine Chiller · Lighting - Pendant

Office

Level
Second
Area
101.44 sqft
Length
7.33 ft
Width
13.83 ft
Features
Flooring - Hardwood

Bathroom 1

Level
First
Area
40 sqft
Length
5 ft
Width
8 ft
Features
Bathroom - Half · Flooring - Stone/Ceramic Tile · Lighting - Sconce

Bathroom 2

Level
Main,First
Area
66.67 sqft
Length
12.5 ft
Width
5.33 ft
Features
Bathroom - 3/4 · Bathroom - Tiled With Shower Stall · Flooring - Stone/Ceramic Tile · Lighting - Sconce

Bathroom 3

Level
Second
Area
111.17 sqft
Length
9.67 ft
Width
11.5 ft
Features
Bathroom - Full · Bathroom - Double Vanity/Sink · Bathroom - Tiled With Shower Stall · Bathroom - With Tub · Flooring - Stone/Ceramic Tile · Lighting - Sconce

Price & tax details

Current asking price$1,999,000
Original asking price$2,049,000
Listed on2026-10-07
Days on market22
Tax record supplied by MLS
YearProperty taxAssessed value
2026$19,853$1,791,800

These records are supplied by the current listing. Assessed value is not market value; confirm taxes with the local assessor.

Mortgage calculator

Estimate principal and interest using the asking price and your loan assumptions.

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Results include principal and interest, plus property tax and HOA when MLS lists them; home and mortgage insurance and utilities are excluded. Tax uses the amount in this listing; a buyer’s actual tax may differ with reassessment or residential exemptions. The rate is your assumption, not a current market quote or loan offer.

SCHOOLS & EDUCATION

Schools & performance

2026 MA DESE

School names, grades and state-reported measures are listed below.

This listing does not name individual schools. Public school information below is context, not an attendance assignment for this address.

Nearby public schools

Sorted by straight-line distance within the city. These are not attendance boundaries or a guarantee of enrollment.

99DESE percentile

Nearby public school · not assigned

Vinson-Owen Elementary

Grades K · 1 · 2 · 3 · 4 · 5

Straight-line distance 0.32 km

Progress toward targets 93%

96DESE percentile

Nearby public school · not assigned

Ambrose Elementary

Grades K · 1 · 2 · 3 · 4 · 5

Straight-line distance 1.56 km

Progress toward targets 91%

93DESE percentile

Nearby public school · not assigned

Lynch Elementary

Grades PK · K · 1 · 2 · 3 · 4 · 5

Straight-line distance 2.06 km

Progress toward targets 78%

95DESE percentile

Nearby public school · not assigned

McCall Middle

Grades 6 · 7 · 8

Straight-line distance 3.12 km

Progress toward targets 86%

93DESE percentile

Nearby public school · not assigned

Lincoln Elementary

Grades K · 1 · 2 · 3 · 4 · 5

Straight-line distance 3.16 km

Progress toward targets 84%

97DESE percentile

Nearby public school · not assigned

Winchester High School

Grades 9 · 10 · 11 · 12

Straight-line distance 3.17 km

Progress toward targets 88%

MLS school names do not guarantee attendance. Assignment can vary by school year, grade and admissions policy; confirm with the district before committing.
What do these numbers mean?

DESE accountability percentiles (1–99) compare schools administering similar assessments, using up to two years of indicators. These are not test scores out of 100 or GreatSchools 1–10 ratings. Progress toward targets is a separate state measure. Consider programs, support services and your child’s needs as well.

School names link to available school or district websites.

Information is deemed reliable but is not guaranteed. © 2026 MLS Property Information Network, Inc. All rights reserved.

Listings updated