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$1,499,999 Just Listed

  • For Sale
  • Active
  • Single Family
  • 6 Beds
  • 3 Full Baths
  • 2,658 Sq. Ft.
  • 0.23 Acres
  • 1 Car Garage
  • Updated 12 hours ago

Next open house:

Open House: 2:00 PM - 4:00 PM

Saturday 3/14 2:00 PM - 4:00 PM

65 High Street,Winchester, MA 01890

65 High StreetWinchesterMA01890

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Join us at 65 High Street on:

  • Open House: 11:00 AM - 1:00 PM

    Sunday 3/15 11:00 AM - 1:00 PM

    65 High Street,Winchester, MA 01890
    65 High StreetWinchesterMA01890
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Fantastic! The best value in Winchester in a desired neighborhood. The sunny first floor flows nicely from room to room, with hardwood floors in the living areas and a hallway leading to the 3 original bedrooms. Ideal for an office, guests, or visiting in-laws. A screen porch and patio off the dining room ideal for al fresco dining. The generous second-floor renovation features a full bath with double sinks, an exclusive-use laundry room, and 3 bedrooms, each with 3 windows for generous natural light. The backyard is private and level for grilling, gardening, and entertaining. The huge 1,165 sq ft basement is your creative space for a playroom, gym, and media room. Great school system (Ambros), and downtown convenience for commuter rail, shops, and restaurants. An amazingly beautiful backyard that's perfect for outdoor recreation. The seller will gift a pool and a ping-pong table to the new buyer in the playroom.

Full Property Details for 65 High St

General

  • Price: $1,499,999
  • Taxes: $13,499 (2025)
  • Status: Active
  • Type: Single Family
  • MLS ID: 73485189
  • Updated: 3/11/2026
  • Added to Site: 1 day(s) ago

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 3
  • Bathroom 1: 5.42 x 7.33, First
  • Bathroom 2: 9.25 x 11.83, Second
  • Bathroom 3: 8.75 x 5.92, Basement

Bedrooms

  • Total Bedrooms: 6
  • Primary Bedroom: 14.67 x 11.25, First
  • Bedroom 2: 10.00 x 11.00, First
  • Bedroom 3: 13.17 x 11.83, First
  • Bedroom 4: 10.75 x 15.67, Second

Other Rooms

  • Living Room: 20.92 x 12.00, First
  • Kitchen: 11.00 x 11.25, First
  • Dining Room: 13.00 x 11.25, First

Parking

  • Garage: Yes
  • Garage Spaces: 1
  • Parking Features: Attached, Paved Drive, Off Street

Location

  • County: Middlesex

Structural Information

  • Architectural Style: Colonial
  • Basement: Yes
  • Square Feet: 2,658
  • Year Built: 1949

Lot Features

  • Lot Size (Acres): 0.23

Financial Considerations

  • Tax Amount: $13,499
  • Tax Year: 2025

Disclosures and Reports

  • Disclosures/Rstr.: Buyer and buyer agent to do all due diligence. Tenants occupy the property under a lease agreement until September 30th, 2026. Rent $5, 000. Seller has never lived in the property. Seller and tenant have never used fireplace.
  • Property ID: 900217

Listed by K Stadium Realty INC, Anna Jung

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Listing agent

— 65 High St —

  • Anna Jung

    K Stadium Realty INC

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 65 High St

School District:Winchester School District, Winchester, MA
NameGradesDistance
Ambrose Elementary School
27 High Street, Winchester, MA 01890
K-50.2 mi
Mccall Middle School
458 Main Street, Winchester, MA 01890
6-81.3 mi
Winchester High School
80 Skillings Road, Winchester, MA 01890
9-121.6 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 65 High St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
3/11/2026
Listed
$1,499,999
76.47%
MLS
12/30/2016
Sold
$850,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 65 High St

Year
Property Taxes
Change
Tax Assessment
Change
2025
$13,499
1%
$1,217,200
3%
2024
$13,369
5%
$1,180,000
10%
2023
$12,702
3%
$1,076,400
9%
2022
$12,351
8%
$987,300
11%
2021
$11,397
4%
$888,300
—
2020
$11,006
8%
$888,300
5%
2019
$10,218
2%
$843,800
2%
2018
$10,053
-1%
$824,700
-1%
2017
$10,191
9%
$829,900
4%
2016
$9,312
3%
$797,300
7%
2015
$9,064
-2%
$746,600
2%
2014
$9,286
—
$733,500
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by K Stadium Realty INC, Anna Jung

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65 High Street, Winchester, MA 01890 (MLS# 73485189) is a Single Family property with 6 bedrooms and 3 full bathrooms. 65 High Street is currently listed for $1,499,999 and was received on March 11, 2026. Want to learn more about 65 High Street? Do you have questions about finding other Single Family real estate for sale in Winchester Highlands? You can browse all Winchester Highlands real estate or contact a Coldwell Banker agent to request more information.

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