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4 Oakland CirWinchester, MA 01890

For Sale

$1,599,000

Smart Buyer Rebate $7,995

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

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

Full MLS Disclaimers

Rebate estimate is indicative only and based on listing price and estimated buyer's agent commission paid by owner, if applicable. Final rebates are subject to Terms of Use and may vary due to final negotiated transaction terms.