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$3,250,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 5 Full Baths
  • 2 Partial Baths
  • 7,101 Sq. Ft.
  • 1.68 Acres
  • 2 Car Garage
  • Updated 2 hours ago

Next open house:

Open House: 1:00 PM - 2:30 PM

Saturday 4/11 1:00 PM - 2:30 PM

257 High Street,Winchester, MA 01890

257 High StreetWinchesterMA01890

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Join us at 257 High Street on:

  • Open House: 11:00 AM - 12:30 PM

    Monday 4/13 11:00 AM - 12:30 PM

    257 High Street,Winchester, MA 01890
    257 High StreetWinchesterMA01890
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See This Home
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Spectacular Winchester estate offering over 7000 sf of living space with exceptional privacy and exclusivity on an oversized lot. This grand home spans over three full levels with extraordinary living spaces highlighted by a soaring two-story family room, elegant mahogany library w/ fplc, custom built-ins. The large country kitchen offers commercial grade appliances, w access to glorious deck, mudroom, pantry & oversized 2 car garage. The 2nd floor offers a stunning master w sitting area, marble bath & walk in closet. 3 add'l BR's, all generously sized. The expansive lower level features an inviting screened "Florida room" family space that opens to a bluestone patio with fire pit, overlooking expansive meticulously maintained lawn & an outdoor shower! Additionally in the LL, there is a movie theatre, full kitchen, gym, bedroom, game room w fplc, perfect for ADU/ extended family or for everyday living and entertaining. Must see this fabulous home~ The ultimate home for hosting!

Full Property Details for 257 High St

General

  • Price: $3,250,000
  • Taxes: $26,758 (2025)
  • Status: Active
  • Type: Single Family
  • MLS ID: 73499287
  • Updated: Today (4/9/2026)
  • Added to Site: Today

Rooms

Bathrooms

  • Total Bathrooms: 7
  • Full Bathrooms: 5
  • Half Bathrooms: 2
  • Bathroom 1: 8.00 x 5.00, First
  • Bathroom 2: 10.00 x 7.00, First
  • Bathroom 3: 16.00 x 12.00, Second

Bedrooms

  • Total Bedrooms: 5
  • Primary Bedroom: 31.00 x 23.00, Second
  • Bedroom 2: 14.00 x 13.00, Second
  • Bedroom 3: 15.00 x 15.00, Second
  • Bedroom 4: 17.00 x 14.00, Second

Other Rooms

  • Living Room: 20.00 x 14.00, First
  • Family Room: 26.00 x 16.00, First
  • Kitchen: 20.00 x 15.00, Main, First
  • Dining Room: 14.00 x 13.00, First
  • Office: 9.00 x 9.00, Second

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Parking Features: Attached, Paved Drive, Paved

Location

  • County: Middlesex

Structural Information

  • Architectural Style: Colonial, Contemporary
  • Basement: Yes
  • Square Feet: 7,101
  • Year Built: 1994

Lot Features

  • Lot Size (Acres): 1.68

Financial Considerations

  • Tax Amount: $26,758
  • Tax Year: 2025

Disclosures and Reports

  • Disclosures/Rstr.: Rhino Shield* paint exterior, low maintenance* 2 driveways upper and lower~ Commercial grade ice maker included. Furnishing and some paint colors are photo edited.
  • Property ID: M:027 B:0342 L:0, 901606

Listed by Compass, Kim Covino & Co. Team and Kim Covino

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Listing agents

— 257 High St —

  • Kim Covino & Co. Team

    Compass

  • Kim Covino

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 257 High St

School District:Winchester School District, Winchester, MA
NameGradesDistance
Vinson-Owen Elementary School
75 Johnson Road, Winchester, MA 01890
K-50.4 mi
Mccall Middle School
458 Main Street, Winchester, MA 01890
6-82.3 mi
Winchester High School
80 Skillings Road, Winchester, MA 01890
9-122.4 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 257 High St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
4/09/2026
Listed
$3,250,000
441.4%
MLS
5/19/1995
Sold
$600,300
—
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 257 High St

Year
Property Taxes
Change
Tax Assessment
Change
2025
$26,758
4%
$2,412,800
6%
2024
$25,689
2%
$2,267,300
7%
2023
$25,097
11%
$2,126,900
17%
2022
$22,697
3%
$1,814,300
6%
2021
$21,994
4%
$1,714,300
—
2020
$21,240
2%
$1,714,300
—
2019
$20,760
2%
$1,714,300
3%
2018
$20,268
6%
$1,662,700
7%
2017
$19,118
7%
$1,556,800
2%
2016
$17,832
2%
$1,526,700
6%
2015
$17,452
—
$1,437,600
4%
2014
$17,491
—
$1,381,600
—
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 Compass, Kim Covino & Co. Team and Kim Covino

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257 High Street, Winchester, MA 01890 (MLS# 73499287) is a Single Family property with 5 bedrooms, 5 full bathrooms and 2 partial bathrooms. 257 High Street is currently listed for $3,250,000 and was received on April 09, 2026. Want to learn more about 257 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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