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.
Listed by Surabhi Rathi
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Redfin Corp.
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781-820-9495
Last updated September 07, 2025
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Source: MLSPin #73426639
Listing Facts
TypeSingle-family
NeighborhoodGrove Street
Bedrooms3
Bathrooms2
Days on Prevu3
Taxes$16,199/year
Size2,368 sqft
Price per sqft$675
Amenities
Private Outdoor Space
Parking
Location
Mortgage Calculator
Listing History
09/05/2025
Listed by Redfin Corp.
$1,599,000
Property Details for 4 Oakland Cir
Association
Amenities
Community Features: Public Transportation, Shopping, Park, Medical Facility, Laundromat, House Of Worship, Public School
Exterior
Construction
Roof: Shingle
Year Built: 1951
Year Built Details: Approximate
Architectural Style: Colonial
Construction Materials: Frame
Exterior Features: Deck
Features
Patio And Porch Features: Deck
Measurements
Building Area Total: 2,368
Building Area Units: Square Feet
Lot Size Acres: 0.23
Lot Size Area: 0
Lot Size Square Feet: 10,019
Lot Size Units: Acres
Financial
Taxes
Parcel Number: M:007 B:0112 L:0,896310
Tax Annual Amount: $16,199.00
Tax Assessed Value: $1,460,700.00
Tax Year: 2025
Interior
Features
Fireplace Features: Living Room
Fireplace: Yes
Fireplaces Total: 1
Flooring: Flooring - Hardwood
Interior Features: Closet, Closet/Cabinets - Custom Built, Home Office
Measurements
Living Area: 2,368
Living Area Source: Public Record
Rooms
Basement: Unfinished
Bathrooms Full: 2
Bathrooms Total Integer: 2
Bedrooms Total: 3
Rooms Total: 8
Other
General
Exclusions: Some Furniture For Sale See Attached.
Parking
Parking
Attached Garage: Yes
Covered Spaces: 1
Garage Spaces: 1
Garage: Yes
Open Parking: Yes
Parking Features: Attached, Paved Drive, Off Street, Paved
Parking Total: 2
Utilities
Equipment
Cooling: Window Unit(s)
Has Cooling: Yes
Heating: Baseboard, Oil
Has Heating: Yes
Laundry Features: Electric Dryer Hookup, Washer Hookup, In Basement
Sewer: Public Sewer
Water Source: Public
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