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 on 10/17/25
$1,651,000
4 Oakland Cir, Winchester, MA 01890
3beds
2,368sqft
Single Family Residence
Built in 1951
10,019 Square Feet Lot
$1,656,700 Zestimate®
$697/sqft
$4,794 Estimated rent
Owner options
What's special
Zillow last checked: 8 hours ago
Listing updated: October 17, 2025 at 09:26am
Listed by:
Surabhi Rathi,
Redfin Corp.
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: 2
- Parking features: Attached, Paved Drive, Off Street, Paved
- Attached garage spaces: 1
- Has uncovered spaces: Yes
Features
- Patio & porch: Deck
- Exterior features: Deck
Lot
- Size: 10,019 sqft
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 & neighborhood
Community
- Community features: Public Transportation, Shopping, Park, Medical Facility, Laundromat, House of Worship, Public School
Location
- Region: Winchester
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Estimated market value
$1,656,700