28 Olive St Winchester, MA $ 1,049,900
28 Olive St
$ 1,049,900
Recently Listed
Open House 10/29 5:30pm - 6:30pm
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28 Olive St

Winchester, MA, 01890
$ 1,049,900
Bedrooms3 Baths2.0 Sq 1,783

Monthly Estimate*

$ 7,251

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Single Family Home for sale in Winchester, MA

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

Single Family Active

Price

$ 1,049,900

Bedrooms

3

Full Bath

2

Property Type

Single Family

Taxes

$ 9,138

Style

Ranch

Lot Size

0.15

Year Built

1963

Town/City

Winchester

County/Region

Middlesex

MLS | Web ID

73595417

List By
Ethan Forrest

Listing Agent

The Aland Realty Group Llc

Broker

Affordability Calculator

$8,013
Per Month
90%
10%
0%
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.
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Pricing History
DatePricePrice ChangeDescription
10/27/2026$1,049,900 Listed Price

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28 Olive St, Winchester, MA, 01890 is a Single Family Home for sale at $1,049,900 with 1,783 sqft and a lot size of 0.15. 28 Olive St has 3 bedrooms, 2.0 baths, and was built in 1963. The property's zip code is 01890 which is in Winchester, MA