Recently Listed Open House 10/29 5:30pm - 6:30pm
28 Olive St
Winchester, MA, 01890 $ 1,049,900
Bedrooms3 Baths2.0 Sq 1,783 Monthly Estimate*
$ 7,251
for $1,049,900 with 3 bedrooms and 2 full baths. This 1,783 square foot home was built in 1963 on a lot size of 0.15.
Welcome to 28 Olive Street, a renovated 3-bedroom, 2-bath ranch in Winchester with 1,783 square feet of finished living space and a top-to-bottom update that lets you move right in. The main level centers on an all-new, slightly expanded eat-in kitchen that opens to an adjacent living room. A wood-burning fireplace and shiplap accent wall anchor the living room. The main living level features refinished hardwood floors, all-new doors, trim, ceilings, and lighting, plus new central AC. Three bedrooms share a completely updated full bath. Downstairs, the finished lower level adds valuable flexible space. The spacious recreation room offers plenty of space for a media area, gym, or home office, plus a second full bathroom, recessed lighting, vinyl flooring, and its own mini-split for heating and cooling. A separate utility room keeps storage, laundry, and mechanicals out of sight. The big-ticket items are done: new roof, windows, siding, electrical service, and exterior doors. The 6,527-square-foot corner lot has a private driveway, new entry stairs, and a crisp new white vinyl fence surrounding the entire property. With the heavy lifting already complete, 28 Olive Street is a rare chance to own in Winchester without the projects. Staging and photos are being done Thursday. First showings are Thursday at the open house. Offers, if any, will be reviewed Monday at Noon.
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Open House
10/29/2026 5:30 PM - 6:30 PM
10/31/2026 11:00 AM - 12:30 PM
11/1/2026 12:00 PM - 1:30 PM
28 Olive St Winchester, MA
* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm
List ByEthan ForrestListing Agent
The Aland Realty Group LlcBroker
Affordability Calculator
- Monthly Principal & Interest
- $7,251
- Monthly Property Taxes
- $762
- Monthly Home Insurance
- --
Default based on a 30-year fixed rate of 7.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save NearbySingle family listings in Winchester, MA
Average List Price $2,348,145
Percent of Sale Price 124%
About Winchester, MA 22,228 Population
7% Since 2002
$ 152,119 Median Income
45.68 Median Age
42% Households with Children
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Pricing History| Date | Price | Price Change | Description |
|---|
| 10/27/2026 | $1,049,900 | | Listed Price |