Main St or Washington St to Cross St, turn onto Olive St.
Home type
Single Family Residence
Interior living area
1,783 sqft
Year built
1963
Lot size
6,527 sqft (about 0.15 acres)
Parking spaces
2
Price per sqft
$589/sqft
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.
Listed by Ethan Forrest · The Aland Realty Group LLC MLS PIN #73595417 · Updated 11/2/2026, 11:27:00 AM ET
Facts & features
Home overview
Property subtype
Single Family Residence
Property category
Residential
MLS status
Active
Bedrooms
3
Full bathrooms
2
Half bathrooms
0
Total bathrooms
2
Total rooms
6
Living area
1,783 sqft
Living area source
Other
Above grade finished area
958 sqft
Below grade finished area
825 sqft
Building area
1,783
Building area units
Square Feet
Building area source
Other
Area includes basement
Yes
Area disclosures
lower level square footage is approximate. Discrepancy will not be negotiated
Main level bedrooms
3
Main level bathrooms
1
Interior & systems
Heating
Forced Air · Heat Pump · Natural Gas · Electric
Heating available
Yes
Heating zones
2
Cooling
Central Air
Cooling available
Yes
Cooling zones
2
Appliances
Gas Water Heater · Water Heater · Range · Dishwasher · Microwave · Refrigerator
Public Transportation · Shopping · Park · Medical Facility · Laundromat · Highway Access · House of Worship · Public School · T-Station
Senior community
No
Taxes & property records
Annual property tax
$9,138
Tax year
2026
Assessed value
$824,700
Parcel number
M:0011 B:0021 L:0000,897496
Zoning
RG
Registry book
85926
Registry page
349
Location & listed schools
City
Winchester
County
Middlesex
State
MA
ZIP code
01890
Listed elementary school
Muraco
Listed middle school
Mccall Middle School
Listed high school
Winchester High School
Directions
Main St or Washington St to Cross St, turn onto Olive St.
Listing & disclosures
MLS number
73595417
Listing date
2026-10-27
Original entry date
2026-10-27
Status changed
2026-10-27
Listing modified
2026-11-02
Original list price
$1,049,900
Current list price
$1,049,900
List price per sqft
$588.84
Days on market
6
Property market time
6
Disclosures
The first-floor heating is provided by a Trane gas-powered furnace; the age is unknown. The first floor features new central AC. The basement heating & cooling system is a brand-new mini-split. New roof · siding · windows · electrical · kitchen · bathrooms · ceilings · lighting · & refinished HW floors.
Disclosure indicator
Y
Lead paint
Yes
Price & tax details
Current asking price$1,049,900
Original asking price$1,049,900
Listed on2026-10-27
Days on market6
Tax record supplied by MLS
Year
Property tax
Assessed value
2026
$9,138
$824,700
These records are supplied by the current listing. Assessed value is not market value; confirm taxes with the local assessor.
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SCHOOLS & EDUCATION
Schools & performance
2026 MA DESE
School names, grades and state-reported measures are listed below.
MLS school names do not guarantee attendance. Assignment can vary by school year, grade and admissions policy; confirm with the district before committing.What do these numbers mean?
DESE accountability percentiles (1–99) compare schools administering similar assessments, using up to two years of indicators. These are not test scores out of 100 or GreatSchools 1–10 ratings. Progress toward targets is a separate state measure. Consider programs, support services and your child’s needs as well.
School names link to available school or district websites.