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$2,795,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 4 Full Baths
  • 1 Partial Bath
  • 4,319 Sq. Ft.
  • 0.25 Acres
  • Updated 4 hours ago

Next open house:

Open House: 11:30 AM - 1:00 PM

Saturday 5/16 11:30 AM - 1:00 PM

18 Middlesex St,Winchester, MA 01890

18 Middlesex StWinchesterMA01890

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This extraordinary European-inspired villa delivers the ambiance of a Tuscan retreat just 8 miles from Boston. Masterfully crafted with a blend of timeless elegance and modern design. A magnificent curved staircase welcomes you into the foyer, leading to sophisticated yet inviting spaces designed for everyday comfort and entertaining. At the heart of the home is a designer chef's kitchen featuring high-end appliances and finishes, bespoke cabinetry, a fireplace, and an adjoining mudroom. French doors open to an outdoor oasis with saltwater pool, lush landscaping and granite stone loggia. This home features a primary suite with a spa-like bath and walk-in closet and three en-suite secondary bedrooms. The finished lower level w/ au pair suite and other flex space. Additional conveniences: first floor radiant floors, heated driveway/walkway for year-round ease. With its premier location, this one of a kind home offers a lifestyle of luxury and convenience unlike anything on the market.

Full Property Details for 18 Middlesex St

General

  • Price: $2,795,000
  • Taxes: $23,792 (2025)
  • Status: Active
  • Type: Single Family
  • MLS ID: 73518621
  • Updated: 5/13/2026
  • Added to Site: 1 day(s) ago

Rooms

Bathrooms

  • Total Bathrooms: 5
  • Full Bathrooms: 4
  • Half Bathrooms: 1
  • Bathroom 1: 10.00 x 13.00, First
  • Bathroom 2: 10.00 x 13.00, Second
  • Bathroom 3: 8.00 x 6.00, Second

Bedrooms

  • Total Bedrooms: 4
  • Primary Bedroom: 19.00 x 13.00, First
  • Bedroom 2: 15.00 x 15.00, Second
  • Bedroom 3: 15.00 x 13.00, Second
  • Bedroom 4: 15.00 x 13.00, Basement

Other Rooms

  • Living Room: 26.00 x 19.00, First
  • Family Room: 18.00 x 11.00, First
  • Kitchen: 20.00 x 14.00, First
  • Dining Room: 15.00 x 15.00, First

Parking

  • Parking Features: Paved Drive, Off Street, Paved

Location

  • County: Middlesex

Structural Information

  • Architectural Style: Contemporary, Villa
  • Basement: Yes
  • Square Feet: 4,319
  • Year Built: 2004

Lot Features

  • Lot Size (Acres): 0.25

Financial Considerations

  • Tax Amount: $23,792
  • Tax Year: 2025

Disclosures and Reports

  • Disclosures/Rstr.: Room dimensions are approximate and for marketing purposes only.
  • Property ID: M:015 B:0016 L:0, 898747

Listed by Luxury Living Real Estate, Tina Natale

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Listing agent

— 18 Middlesex St —

  • Tina Natale

    Luxury Living Real Estate

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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 18 Middlesex St

School District:Winchester School District, Winchester, MA
NameGradesDistance
Lynch Elementary School
10 Brantwood Road, Winchester, MA 01890
K-50.5 mi
Mccall Middle School
458 Main Street, Winchester, MA 01890
6-80.6 mi
Winchester High School
80 Skillings Road, Winchester, MA 01890
9-120.4 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 18 Middlesex St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
5/13/2026
Listed
$2,795,000
90.78%
MLS
10/28/2016
Sold
$1,465,000
—
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 18 Middlesex St

Year
Property Taxes
Change
Tax Assessment
Change
2025
$238
-99%
$2,145,400
7%
2024
$22,783
24%
$2,010,900
29%
2023
$18,386
-1%
$1,558,100
5%
2022
$18,614
3%
$1,487,900
5%
2021
$18,121
4%
$1,412,400
—
2020
$17,500
9%
$1,412,400
6%
2019
$16,088
4%
$1,328,500
4%
2018
$15,536
13%
$1,274,500
14%
2017
$13,701
8%
$1,115,700
2%
2016
$12,744
7%
$1,091,100
12%
2015
$11,875
—
$978,200
4%
2014
$11,859
—
$936,700
—
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 Luxury Living Real Estate, Tina Natale

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18 Middlesex St, Winchester, MA 01890 (MLS# 73518621) is a Single Family property with 4 bedrooms, 4 full bathrooms and 1 partial bathroom. 18 Middlesex St is currently listed for $2,795,000 and was received on May 13, 2026. Want to learn more about 18 Middlesex St? 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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