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$2,499,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 4 Full Baths
  • 1 Partial Bath
  • 4,450 Sq. Ft.
  • 0.59 Acres
  • 2 Car Garage
  • Updated 3 hours ago
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Introducing 54 Squire Road,an exceptional newer Colonial privately sited within one of Winchester's most desirable enclaves.Set on a beautifully landscaped, wooded lot, this sun-filled residence blends timeless architecture with numerous substantial owner upgrades.Highlights include 9' ceilings, elegant millwork,a designer chef's kitchen with premium appliances,an impressive family room with custom built-ins and entertaining bar,formal dining with butler's pantry, private office,and luxurious primary suite with vaulted ceilings, walk-in closets,and spa bath.Expanded outdoor living features a custom outdoor kitchen,fire pit,and multiple patios designed for exceptional entertaining.The finished lower level offers a bonus room, home gym, mudroom, and oversized 2-car garage.Professionally landscaped with exceptional privacy, yet just moments to the Vinson-Owen School,steps to the Swim & Tennis Club,and major commuter routes.A rare opportunity to own one of Winchester's finest newer homes.

Full Property Details for 54 Squire Rd

General

  • Price: $2,499,000
  • Taxes: $21,963 (2025)
  • Status: Active
  • Type: Single Family
  • MLS ID: 73555666
  • Updated: Today (8/11/2026)
  • Added to Site: Today

Rooms

Bathrooms

  • Total Bathrooms: 5
  • Full Bathrooms: 4
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 4
  • Primary Bedroom: Second
  • Bedroom 2: Second
  • Bedroom 3: Second
  • Bedroom 4: Second

Other Rooms

  • Living Room: First
  • Family Room: Main, First
  • Kitchen: First
  • Dining Room: First
  • Office: First

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Parking Features: Attached, Under, Off Street, Driveway, Paved

Location

  • County: Middlesex

Structural Information

  • Architectural Style: Colonial
  • Basement: Yes
  • Square Feet: 4,450
  • Year Built: 2016

Lot Features

  • Lot Size (Acres): 0.59

Financial Considerations

  • Tax Amount: $21,963
  • Tax Year: 2025

Disclosures and Reports

  • Property ID: 901790

Listed by The Marino Group Collection, Anthony Marino

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Listing agent

— 54 Squire Rd —

  • Anthony Marino

    The Marino Group Collection

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 54 Squire Rd

School District:Winchester School District, Winchester, MA
NameGradesDistance
Vinson-Owen Elementary School
75 Johnson Road, Winchester, MA 01890
K-50.2 mi
Mccall Middle School
458 Main Street, Winchester, MA 01890
6-82.2 mi
Winchester High School
80 Skillings Road, Winchester, MA 01890
9-122.3 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 54 Squire Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
8/11/2026
Listed
$2,499,000
50.09%
MLS
6/15/2018
Sold
$1,665,000
—
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 54 Squire Rd

Year
Property Taxes
Change
Tax Assessment
Change
2025
$220
-99%
$1,980,400
6%
2024
$21,093
4%
$1,861,700
8%
2023
$20,342
-1%
$1,723,900
5%
2022
$20,474
3%
$1,636,600
5%
2021
$19,971
4%
$1,556,600
1%
2020
$19,162
1%
$1,546,600
-1%
2019
$18,919
3%
$1,562,300
3%
2018
$18,429
51%
$1,511,800
52%
2017
$12,241
54%
$996,800
47%
2016
$7,939
3%
$679,700
7%
2015
$7,686
-2%
$633,100
3%
2014
$7,810
—
$616,900
—
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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NMLS#: 1598647

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Listed by The Marino Group Collection, Anthony Marino

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54 Squire Road, Winchester, MA 01890 (MLS# 73555666) is a Single Family property with 4 bedrooms, 4 full bathrooms and 1 partial bathroom. 54 Squire Road is currently listed for $2,499,000 and was received on August 11, 2026. Want to learn more about 54 Squire Road? 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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