Single Family Residence at 28 Olive St, Winchester
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$1,049,900

28 Olive St
Winchester, MA 01890
Listed by Ethan Forrest
Bedrooms
3
Bathrooms
2
Living area
1,783 sqft
Year built
1963

About this home

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.

Highlights

Fireplace

Property details

MLS
MLS Property Information Network
MLS #
73595417
Property type
Single Family Residence
Subdivision
N/A
Status
Active
Days on market
7
On market date
October 27, 2026
Stories
N/A
Total bathrooms
2
Garage spaces
N/A
Parking spaces
2
Lot size
0.15 acres
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Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card.

Elementary
Muraco Elementary
0.18 mi away · Grades 0-5
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
345
Student:teacher ratio
11.9:1
District
Winchester
Middle
McCall Middle
0.77 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
1,059
Student:teacher ratio
11.8:1
District
Winchester
High
Winchester High School
0.3 mi away · Grades 9-12
Nearest school -- attendance-zone data not available here
4.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
1,349
Student:teacher ratio
13.8:1
District
Winchester

Walkability

Blended score for Winchester's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

65
Walkable
out of 100
EPA National Walkability Index
9.5 / 20 -- Below average walkable
Google Places amenity density
90 / 100
Restaurants & cafes20
Grocery stores2
Parks14
Schools20
Transit stops20
Pharmacies3

Market position

How this listing compares to current activity in Winchester, from live MLS data.

On the market 7 days -- 85 fewer days than Winchester's current average of 92 days.
For reference, the median list price across 175 active listings in Winchester right now is $799,000.

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

Adjust tax / insurance estimates
Est. monthly payment
$6,473/mo
$209,980 down
$839,920 loan
Principal & interest$5,448
Property tax (est.)$875
Home insurance (est.)$150

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Data source: Listing information provided by MLS Property Information Network. Last updated 2 days ago.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.