Experience the perfect blend of timeless elegance & modern luxury in this stunning 5-6-bedroom home, set on one of the town’s most picturesque streets. The stunning state of art chef’s kitchen was just completed & seamlessly connects to a butler’s pantry w/ wet bar & wine chiller, leading to an elegant dining room w/ fireplace. The oversized family room is bathed in natural light w/walls of striking arched windows & a screen porch leading to a deck & custom stone patio overlooking a large level yard. The second floor showcases 4 spacious bedrooms, 2 baths including a generously sized primary/currently using BR 4 for walk in closet. The 3rd floor offers 2 additional bedrooms, office & full bath. The finished walk-out lower level offers great space for movie nights, a gym & storage w/direct entry 2 car+ garage & mudroom. Close to the town center, train to Boston, Mystic Lakes beach, playgrounds & scenic trails, this exceptional home offers both charm & convenience in a top neighborhood!
Sold for $3,025,000
$3,025,000
21 Sheffield W, Winchester, MA 01890
6beds
5,198sqft
Single Family Residence
Built in 1910
0.39 Acres Lot
$3,035,800 Zestimate®
$582/sqft
$7,563 Estimated rent
Home value
$3,035,800
$2.79M - $3.31M
$7,563/mo
Zestimate® history
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List your homeWhat's special
Screen porchOversized family roomCustom stone patioFinished walk-out lower levelLarge level yardWine chillerTimeless elegance
Zillow last checked:
Listing updated:
Listed by:
Kim Covino & Co. Team 781-249-3854,
Compass 781-219-0313,
Kim Covino 781-249-3854
Bought with:
Kim Covino & Co. Team
Compass
Source: MLS PIN,MLS#: 73350559
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 6
- Bathrooms: 5
- Full bathrooms: 3
- 1/2 bathrooms: 2
Primary bedroom
- Features: Bathroom - Full, Bathroom - Double Vanity/Sink, Ceiling Fan(s), Walk-In Closet(s), Closet/Cabinets - Custom Built, Flooring - Hardwood, Recessed Lighting, Closet - Double
- Level: Second
- Area: 380
- Dimensions: 20 x 19
Bedroom 2
- Features: Bathroom - Full, Ceiling Fan(s), Closet, Flooring - Hardwood
- Level: Second
- Area: 240
- Dimensions: 16 x 15
Bedroom 3
- Features: Bathroom - Full, Ceiling Fan(s), Closet, Flooring - Hardwood
- Level: Second
- Area: 209
- Dimensions: 19 x 11
Bedroom 4
- Features: Ceiling Fan(s), Closet, Flooring - Hardwood
- Level: Third
- Area: 360
- Dimensions: 20 x 18
Bedroom 5
- Features: Flooring - Hardwood, Lighting - Overhead
- Level: Third
- Area: 168
- Dimensions: 14 x 12
Primary bathroom
- Features: Yes
Bathroom 1
- Features: Bathroom - Half, Pedestal Sink
- Level: First
- Area: 25
- Dimensions: 5 x 5
Bathroom 2
- Features: Bathroom - Full, Bathroom - Double Vanity/Sink, Bathroom - Tiled With Shower Stall, Lighting - Sconce, Lighting - Overhead
- Level: Second
- Area: 90
- Dimensions: 15 x 6
Bathroom 3
- Features: Bathroom - Full, Bathroom - Tiled With Tub & Shower, Lighting - Overhead
- Level: Second
- Area: 63
- Dimensions: 9 x 7
Dining room
- Features: Lighting - Sconce, Lighting - Overhead, Crown Molding
- Level: First
- Area: 208
- Dimensions: 16 x 13
Family room
- Features: Recessed Lighting
- Level: Basement
- Area: 216
- Dimensions: 18 x 12
Kitchen
- Features: Flooring - Hardwood, Pantry, Kitchen Island, Exterior Access, Remodeled, Stainless Steel Appliances, Wine Chiller, Lighting - Pendant, Lighting - Overhead
- Level: First
- Area: 288
- Dimensions: 24 x 12
Living room
- Features: Beamed Ceilings, Closet/Cabinets - Custom Built, Flooring - Hardwood, French Doors, Lighting - Overhead
- Level: First
- Area: 462
- Dimensions: 22 x 21
Office
- Features: Fireplace, Flooring - Hardwood
- Level: First
- Area: 143
- Dimensions: 13 x 11
Heating
- Baseboard, Natural Gas, Fireplace(s)
Cooling
- Central Air
Appliances
- Included: Oven, Dishwasher, Disposal, Range, Refrigerator, Freezer, Washer, Dryer, Wine Refrigerator, Wine Cooler
- Laundry: Sink, In Basement
Features
- Pantry, Countertops - Stone/Granite/Solid, Wet bar, Lighting - Sconce, Lighting - Pendant, Lighting - Overhead, Recessed Lighting, Home Office, Sun Room, Bedroom, Exercise Room, Wet Bar, Walk-up Attic
- Flooring: Tile, Hardwood, Flooring - Hardwood, Flooring - Wood
- Doors: French Doors
- Windows: Insulated Windows
- Basement: Full,Finished,Walk-Out Access,Interior Entry,Garage Access
- Number of fireplaces: 4
- Fireplace features: Dining Room, Living Room, Master Bedroom
Interior area
- Total structure area: 5,198
- Total interior livable area: 5,198 sqft
- Finished area above ground: 4,290
- Finished area below ground: 908
Property
Parking
- Total spaces: 8
- Parking features: Attached, Under, Garage Door Opener, Paved Drive, Paved
- Attached garage spaces: 2
- Uncovered spaces: 6
Features
- Patio & porch: Screened, Deck, Patio
- Exterior features: Porch - Screened, Deck, Patio, Rain Gutters, Professional Landscaping, Sprinkler System, Decorative Lighting, Stone Wall
- Waterfront features: Lake/Pond, 1/2 to 1 Mile To Beach, Beach Ownership(Public)
Lot
- Size: 0.39 Acres
Details
- Parcel number: M:017 B:0137 L:0
- Zoning: RDB
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subtype: Single Family Residence
Materials
- Frame
- Foundation: Concrete Perimeter
- Roof: Shingle
Condition
- Year built: 1910
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: for Gas Range
Community & HOA
Community
- Features: Public Transportation, Shopping, Pool, Tennis Court(s), Park, Walk/Jog Trails, Golf, Medical Facility, Bike Path, Highway Access, House of Worship, Private School, Public School, T-Station
- Security: Security System
- Subdivision: Flats/ Sheffield
HOA
- Has HOA: No
Location
- Region: Winchester
Financial & listing details
- Price per square foot: $582/sqft
- Tax assessed value: $2,878,100
- Annual tax amount: $31,918
- Date on market: 12/1/2025
Price history
| Date | Event | Price |
|---|---|---|
| 6/13/2025 | Sold | $3,025,000-5.4%$582/sqft |
Source: MLS PIN #73350559 Report a problem | ||
| 5/15/2025 | Contingent | $3,199,000$615/sqft |
Source: MLS PIN #73350559 Report a problem | ||
| 4/30/2025 | Price change | $3,199,000-4.5%$615/sqft |
Source: MLS PIN #73350559 Report a problem | ||
| 3/26/2025 | Listed for sale | $3,350,000-4.3%$644/sqft |
Source: MLS PIN #73350559 Report a problem | ||
| 3/26/2025 | Listing removed | $3,499,000$673/sqft |
Source: MLS PIN #73337785 Report a problem | ||
| 2/24/2025 | Listed for sale | $3,499,000+25%$673/sqft |
Source: MLS PIN #73337785 Report a problem | ||
| 5/4/2022 | Sold | $2,800,000+0%$539/sqft |
Source: MLS PIN #72948175 Report a problem | ||
| 3/9/2022 | Contingent | $2,799,999$539/sqft |
Source: MLS PIN #72948175 Report a problem | ||
| 3/3/2022 | Listed for sale | $2,799,999+55.6%$539/sqft |
Source: MLS PIN #72948175 Report a problem | ||
| 6/26/2012 | Sold | $1,800,000-2.7%$346/sqft |
Source: Public Record Report a problem | ||
| 3/18/2012 | Listing removed | $1,849,900$356/sqft |
Source: Coldwell Banker Residential Brokerage - #71165433 Report a problem | ||
| 1/30/2012 | Price change | $1,849,900-1.6%$356/sqft |
Source: Coldwell Banker Residential Brokerage - #71165433 Report a problem | ||
| 6/11/2011 | Price change | $1,879,900-1.1%$362/sqft |
Source: Coldwell Banker Residential Brokerage - #71165433 Report a problem | ||
| 2/20/2011 | Price change | $1,899,900-29.6%$366/sqft |
Source: NRT NewEngland #71165433 Report a problem | ||
| 2/16/2011 | Price change | $2,699,000+42.1%$519/sqft |
Source: NRT NewEngland #71165433 Report a problem | ||
| 2/13/2011 | Price change | $1,899,900-29.6%$366/sqft |
Source: NRT NewEngland #71165433 Report a problem | ||
| 2/12/2011 | Price change | $2,699,000+42.1%$519/sqft |
Source: NRT NewEngland #71165433 Report a problem | ||
| 1/17/2011 | Price change | $1,899,900-4.8%$366/sqft |
Source: NRT NewEngland #71165433 Report a problem | ||
| 1/7/2011 | Price change | $1,995,000-28.7%$384/sqft |
Source: NRT NewEngland #71165433 Report a problem | ||
| 1/4/2011 | Price change | $2,799,000+40.3%$538/sqft |
Source: NRT NewEngland #71165433 Report a problem | ||
| 12/6/2010 | Price change | $1,995,000-28.7%$384/sqft |
Source: NRT NewEngland #71165433 Report a problem | ||
| 12/5/2010 | Price change | $2,799,000+40.3%$538/sqft |
Source: NRT NewEngland #71165433 Report a problem | ||
| 9/15/2010 | Listed for sale | $1,995,000$384/sqft |
Source: Nannette Shanahan #71136476 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $31,918 +1.4% | $2,878,100 +3.6% |
| 2024 | $31,462 +11% | $2,776,900 +15.6% |
| 2023 | $28,348 +1.6% | $2,402,400 +7.7% |
| 2022 | $27,902 +3.7% | $2,230,400 +6.3% |
| 2021 | $26,919 +3.6% | $2,098,100 |
| 2020 | $25,995 +8.2% | $2,098,100 +5.7% |
| 2019 | $24,035 +1.8% | $1,984,700 +2.5% |
| 2018 | $23,605 +5.6% | $1,936,400 +6.3% |
| 2017 | $22,359 +7.1% | $1,820,800 +1.9% |
| 2016 | $20,870 +1.4% | $1,786,800 +5.4% |
| 2015 | $20,579 +2.6% | $1,695,100 +6.9% |
| 2014 | $20,066 +14.7% | $1,585,000 +15.7% |
| 2013 | $17,487 +3.5% | $1,369,400 +1.8% |
| 2012 | $16,890 +3.7% | $1,345,800 |
| 2011 | $16,284 +4.8% | $1,345,800 -0.3% |
| 2010 | $15,543 +6.2% | $1,350,400 +4% |
| 2009 | $14,635 +4% | $1,298,600 -2.5% |
| 2008 | $14,072 +2.2% | $1,331,300 -0.1% |
| 2007 | $13,771 +2.1% | $1,333,100 +2.5% |
| 2006 | $13,486 -0.7% | $1,300,500 -0.2% |
| 2005 | $13,578 -6.3% | $1,303,100 +2.3% |
| 2004 | $14,496 +2.7% | $1,273,800 +2.7% |
| 2003 | $14,116 +20.7% | $1,240,400 +17.3% |
| 2002 | $11,696 +25.4% | $1,057,500 +44.3% |
| 2000 | $9,329 -5.6% | $732,700 +8.5% |
| 1999 | $9,882 | $675,000 |
Find assessor info on the county website
Neighborhood: 01890
Nearby homes
- $2,477,3005 bd3 ba4.7k sqft19 Sheffield W, Winchester, MA 01890Off Market
- $3,521,1006 bd8 ba7.8k sqft23 Sheffield W, Winchester, MA 01890Off Market
- $2,544,0004 bd3 ba4k sqft16 Sheffield W, Winchester, MA 01890Off Market
- $1,747,4006 bd4 ba3.7k sqft3 Gardner Pl, Winchester, MA 01890Off Market
- $2,193,4004 bd4 ba3.2k sqft7 Gardner Pl, Winchester, MA 01890Off Market
- $2,350,8004 bd4 ba3.9k sqft27 Sheffield W, Winchester, MA 01890Off Market
- $2,960,0005 bd5 ba4.8k sqft39 Everett Ave, Winchester, MA 01890Sold
- $2,307,2005 bd3 ba2.9k sqft17 Sheffield W, Winchester, MA 01890Off Market
Nearby schools
GreatSchools rating
- 10/10Ambrose Elementary SchoolGrades: K-5Distance: 0.3 mi
- 9/10McCall Middle SchoolGrades: 6-8Distance: 0.9 mi
- 10/10Winchester High SchoolGrades: 9-12Distance: 1.2 mi
Schools provided by the listing agent
- Elementary: Ambrose
- Middle: Mccall
- High: Whs
Source: MLS PIN. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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Estimated market value
$3,035,800
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Estimated market value
$3,035,800
- Massachusetts
- Middlesex County
- Winchester
- 01890
- 21 Sheffield W
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