28 Olive StreetWinchester, MA 01890MLS Number 73595417

  • Price: $1,049,900
  • Est. Mortgage of $/month
  • 1 Day on Market
$
$
%
$/month over payments
Federal 30-year interest rate: 7.32% last updated on Oct 22, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.
Open House
28 Olive Street Winchester MA 0189028 Olive Street Winchester MA 0189028 Olive Street Winchester MA 0189028 Olive Street Winchester MA 0189028 Olive Street Winchester MA 0189028 Olive Street Winchester MA 0189028 Olive Street Winchester MA 0189028 Olive Street Winchester MA 01890
QR Code
  • 3Bedrooms
  • 0.15Acreage
  • 2Bathrooms
  • 1963Year Built

Driving Directions

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.

Open Houses

October 29th
Starts: 5:30pm
Ends: 6:30pm
October 31st
Starts: 11:00am
Ends: 12:30pm
November 1st
Starts: 12:00pm
Ends: 1:30pm
Listed by Ethan Forrest of The Aland Realty Group LLC

Ask A Question

Do not fill in this field:

I agree to receive marketing and customer service calls and text messages from The Surrealtors. To opt out, you can reply 'stop' at any time or click the unsubscribe link in the emails. Consent is not a condition of purchase. Msg/data rates may apply. Msg frequency varies. Privacy Policy.

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

More Info

Basic Information

  • Bedrooms3
  • Mls StatusNew
  • Bathroom2
  • Lot Features Corner Lot, Cleared, Level
  • Parcel Number M:0011 B:0021 L:0000,897496
  • Road Frontage DescriptionPaved

Basic Information

  • List Price$1,049,900
  • MLS Number73595417
  • Modification Date10/27/2026
  • Property SubTypeSingle Family Residence

Building

  • BasementFull, Partially Finished, Interior Entry, Bulkhead, Concrete
  • Building Area Units Square Feet
  • Construction Materials Frame
  • FireplaceYes
  • Fireplace Features Living Room
  • Fireplaces Total 1
  • FoundationConcrete Perimeter
  • Property StyleRanch
  • Rooms6
  • Window Features Insulated Windows, Screens
  • Year Built1963
  • Year Built Details Actual, Renovated Since
  • Year Built Source Public Records

Tax Information

  • Tax Assessed Value $824,700
  • Tax Year 2026
  • Taxes$9,138

Parking

  • Parking Spaces2
  • Open Parking YN Yes
  • Parking Features Paved Drive, Off Street, Paved

Location

  • Address28 Olive Street
  • Building Number28
  • CountyMiddlesex
  • StateMA
  • StreetOlive Street
  • TownWinchester
  • Zip01890

Property

  • Acreage0.15

Interior

  • Flooring Hardwood

Utilities

  • Cooling Central Air
  • Cooling YN Yes
  • Electric 200+ Amp Service
  • Heat SystemYes
  • Heating Forced Air, Heat Pump, Natural Gas, Electric
  • Sewer Public Sewer
  • Water Source Public

Amenities

  • Amenities
    • Highway Access
    • House of Worship
    • Laundromat
    • Medical Facility
    • Park
    • Public School
    • Public Transportation
    • Shopping
    • T-Station
  • Appliances IncludedGas Water Heater, Water Heater, Range, Dishwasher, Microwave, Refrigerator
  • Green Energy Efficient Thermostat

School Information

  • High School Winchester High School
  • Elementary SchoolMuraco
  • Junior HighMccall Middle School

Rooms

  • Bathroom 1 Main, First
  • Bathroom 2 Basement
  • Bathrooms Total Decimal 2
  • Bedroom 2 Main, First
  • Bedroom 3 Main, First
  • Family Room Basement
  • Full Bath2
  • Kitchen Main, First
  • Living Room Main, First
  • Main Level Bathrooms 1
  • Main Level Bedrooms 3
  • Master Bedroom Main, First

Exterior

  • Exterior Features Rain Gutters, Screens, Fenced Yard
  • Fencing Fenced
  • RoofShingle

Property Information

  • Square Feet1,783
  • Building Area Source Other
  • Living Area 1,783
  • Lot Size Square Feet 6,527
  • Lot Size Units Acres
  • Road Responsibility Public Maintained Road

Other

  • Date Listed10/27/2026
  • Farm Land Area Units Square Feet

Your Local Office

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. (MLSPIN) from third party sources, including sellers, lessors and public records, and were compiled by MLSPIN. 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 or leasing 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 or leasing. MLSPIN 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.

Hi there! How can we help you?

Contact us using the form below or give us a call.

Send Us A Message:

I agree to receive marketing and customer service calls and text messages from The Surrealtors. To opt out, you can reply 'stop' at any time or click the unsubscribe link in the emails. Consent is not a condition of purchase. Msg/data rates may apply. Msg frequency varies. Privacy Policy.

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Hi there! How can we help you?

Contact us using the form below or give us a call.

Send Us A Message:

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Hi there! How can we help you?

Contact us using the form below or give us a call.

Send Us A Message:

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

$

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.