Welcome to 4 Oakland Circle, a spacious home tucked away on a desirable cul-de-sac in Winchester. Thoughtfully designed with oversized rooms and a versatile layout, this residence provides comfort and flexibility for a variety of lifestyles. The main level features expansive living and dining areas along with a 1st floor primary bedroom option that opens onto a private deck, plus a dedicated home office perfectly suited for remote work. Upstairs, the private primary bedroom offers a generous retreat, accompanied by a well-sized third bedroom. Large windows bring in abundant natural light, creating a warm and inviting atmosphere throughout. Step outside to enjoy the beautiful backyard, an ideal space for entertaining, gardening, or simply relaxing in a peaceful setting. With its generous floor plan, tranquil location, and close proximity to Winchester’s vibrant center, schools, this home presents an exceptional opportunity to enjoy both space and convenience.
Sold for $1,651,000
Street View
$1,651,000
4 Oakland Cir, Winchester, MA 01890
3beds
2,368sqft
Single Family Residence
Built in 1951
10,019 Square Feet Lot
$1,690,500 Zestimate®
$697/sqft
$4,572 Estimated rent
Home value
$1,690,500
$1.56M - $1.83M
$4,572/mo
Zestimate® history
Owner options
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$4,572/mo
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$4,572/mo
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$10,782/mo
Est. payment
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$10,782/mo
Est. payment
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Zillow last checked:
Listing updated:
Listed by:
Surabhi Rathi 781-820-9495,
Redfin Corp. 617-340-7803
Bought with:
Susan Condrick
Gibson Sotheby's International Realty
Source: MLS PIN,MLS#: 73426639
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 2
- Full bathrooms: 2
Primary bedroom
- Features: Closet, Flooring - Wood
- Level: Second
Bedroom 2
- Features: Closet, Flooring - Wood, Exterior Access
- Level: First
Bedroom 3
- Features: Closet, Flooring - Wood
- Level: Second
Primary bathroom
- Features: No
Bathroom 1
- Features: Bathroom - Full
- Level: First
Bathroom 2
- Features: Bathroom - Full
- Level: Second
Kitchen
- Features: Flooring - Wood, Dining Area, Balcony / Deck, Kitchen Island, Exterior Access, Stainless Steel Appliances
- Level: First
Living room
- Features: Flooring - Wood
- Level: First
Office
- Features: Closet, Closet/Cabinets - Custom Built, Flooring - Hardwood
- Level: First
Heating
- Baseboard, Oil
Cooling
- Window Unit(s)
Appliances
- Laundry: Electric Dryer Hookup, Washer Hookup, In Basement
Features
- Closet, Closet/Cabinets - Custom Built, Home Office
- Flooring: Flooring - Hardwood
- Basement: Unfinished
- Number of fireplaces: 1
- Fireplace features: Living Room
Interior area
- Total structure area: 2,368
- Total interior livable area: 2,368 sqft
- Finished area above ground: 2,368
Property
Parking
- Total spaces: 3
- Parking features: Attached, Paved Drive, Off Street, Paved
- Attached garage spaces: 1
- Uncovered spaces: 2
Features
- Patio & porch: Deck
- Exterior features: Deck
Lot
- Size: 10,019 Square Feet
Details
- Parcel number: M:007 B:0112 L:0,896310
- 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: 1951
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
Community & HOA
Community
- Features: Public Transportation, Shopping, Park, Medical Facility, Laundromat, House of Worship, Public School
HOA
- Has HOA: No
Location
- Region: Winchester
Financial & listing details
- Price per square foot: $697/sqft
- Tax assessed value: $1,460,700
- Annual tax amount: $16,199
- Date on market: 1/14/2026
- Exclusions: Some Furniture For Sale See Attached.
Price history
| Date | Event | Price |
|---|---|---|
| 10/17/2025 | Sold | $1,651,000+3.3%$697/sqft |
Source: MLS PIN #73426639 Report a problem | ||
| 9/12/2025 | Contingent | $1,599,000$675/sqft |
Source: MLS PIN #73426639 Report a problem | ||
| 9/5/2025 | Listed for sale | $1,599,000+661.4%$675/sqft |
Source: MLS PIN #73426639 Report a problem | ||
| 6/30/1992 | Sold | $210,000$89/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $16,199 +5.6% | $1,460,700 +7.9% |
| 2024 | $15,342 +1.5% | $1,354,100 +5.7% |
| 2023 | $15,112 +4.6% | $1,280,700 +10.9% |
| 2022 | $14,453 +2.6% | $1,155,300 +5.3% |
| 2021 | $14,081 +3.6% | $1,097,500 |
| 2020 | $13,598 +10.6% | $1,097,500 +8.1% |
| 2019 | $12,292 +3.4% | $1,015,000 +4.1% |
| 2018 | $11,890 +2% | $975,400 +2.8% |
| 2017 | $11,654 +6.6% | $949,000 +1.4% |
| 2016 | $10,929 +3.2% | $935,700 +7.3% |
| 2015 | $10,586 +7.2% | $872,000 +11.8% |
| 2014 | $9,876 +0.5% | $780,100 +1.4% |
| 2013 | $9,827 +1.8% | $769,500 |
| 2012 | $9,657 +3.7% | $769,500 |
| 2011 | $9,311 +5.1% | $769,500 -0.1% |
| 2010 | $8,862 +2.1% | $769,900 |
| 2009 | $8,677 +3.7% | $769,900 -2.7% |
| 2008 | $8,365 +5.2% | $791,400 +2.8% |
| 2007 | $7,954 +2.4% | $770,000 +2.8% |
| 2006 | $7,768 +4% | $749,100 +4.5% |
| 2005 | $7,471 -6.4% | $717,000 +2.3% |
| 2004 | $7,979 +2.4% | $701,100 +2.4% |
| 2003 | $7,794 +12.3% | $684,900 +9.1% |
| 2002 | $6,943 +78.9% | $627,800 +37.5% |
| 2000 | $3,882 -5.6% | $456,700 +62.6% |
| 1999 | $4,112 | $280,900 |
Find assessor info on the county website
Neighborhood: 01890
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Nearby schools
GreatSchools rating
- 10/10Ambrose Elementary SchoolGrades: K-5Distance: 0.8 mi
- 9/10McCall Middle SchoolGrades: 6-8Distance: 0.6 mi
- 10/10Winchester High SchoolGrades: 9-12Distance: 1.1 mi
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Estimated market value
$1,690,500
Get a cash offer in 3 minutes
Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$1,690,500
- Massachusetts
- Middlesex County
- Winchester
- 01890
- 4 Oakland Cir
