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$2,650,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 4 Full Baths
  • 1 Partial Bath
  • 5,233 Sq. Ft.
  • 0.25 Acres
  • Updated 1 day ago

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

Saturday 10/24 11:30 AM - 1:00 PM

18 Middlesex St,Winchester, MA 01890

18 Middlesex StWinchesterMA01890

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  • Open House: 11:30 AM - 1:00 PM

    Sunday 10/25 11:30 AM - 1:00 PM

    18 Middlesex St,Winchester, MA 01890
    18 Middlesex StWinchesterMA01890
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Inspired by the timeless villas of Europe, this exceptional residence blends classic elegance with modern design. A dramatic curved staircase and soaring architectural details introduce inviting living spaces featuring handcrafted finishes, antique beams, stone fireplaces, and expansive French doors that connect seamlessly to the outdoors. At the heart of the home, a chef's kitchen showcases custom cabinetry, luxury appliances, and an adjoining mudroom. The outdoor setting offers a private retreat with a granite-columned loggia, heated saltwater pool, landscaped grounds with irrigation, and multiple areas for entertaining.The spa-inspired primary suite, ensuite guest bedrooms, and finished lower level with flexible bonus spaces provide comfort and versatility. Heated driveways and walkways add year-round convenience. Ideally located within walking distance of downtown, the new Lynch School, the new commuter rail station, and an array of shops and restaurants, this home offers a thoughtful balance of timeless style, modern amenities, and everyday comfort.

Full Property Details for 18 Middlesex St

General

  • Price: $2,650,000
  • Taxes: $24,849 (2026)
  • Status: Active
  • Type: Single Family
  • Source: MLSPin
  • MLS ID: 73593868
  • Updated: 10/22/2026
  • Added to Site: 1 day(s) ago

Interior

  • Number of Rooms: 8
  • Fireplace: Yes
  • Number of Fireplaces: 2
  • Appliances: Gas Water Heater, Range, Dishwasher, Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer, Wine Refrigerator
  • Flooring: Marble, Stone / Slate

Rooms

Bathrooms

  • Total Bathrooms: 5
  • Full Bathrooms: 4
  • Half Bathrooms: 1
  • Main - Full Baths: 4
  • Main - 1/2 Baths: 1
  • Bathroom 1: 10.00 x 13.00, Second, 130 Sq. Ft.
  • Bathroom 2: 8.00 x 6.00, First, 48 Sq. Ft.
  • Bathroom 3: 8.00 x 6.00, Basement, 48 Sq. Ft.

Bedrooms

  • Total Bedrooms: 4
  • Primary Bedroom: Yes, 19.00 x 13.00, First, 247 Sq. Ft.
  • Bedroom 2: 15.00 x 15.00, Second, 225 Sq. Ft.
  • Bedroom 3: 15.00 x 13.00, Second, 195 Sq. Ft.
  • Bedroom 4: 15.00 x 13.00, Basement, 195 Sq. Ft.

Other Rooms

  • Living Room: 26.00 x 19.00, First, 494 Sq. Ft.
  • Family Room: 18.00 x 11.00, First, 198 Sq. Ft.
  • Kitchen: 20.00 x 14.00, First, 280 Sq. Ft.
  • Dining Room: 15.00 x 15.00, First, 225 Sq. Ft.
  • Laundry: Gas Dryer Hookup

Additional Information

  • Pool: Yes
  • Pool Description: Pool - Inground Heated
  • Year Round: Yes

Exterior

  • Exterior Features: Patio, Covered Patio/Deck, Pool - Inground Heated, Rain Gutters, Storage, Professional Landscaping, Sprinkler System, Decorative Lighting, Fenced Yard, Garden, Stone Wall
  • Color: natural

Parking

  • Total Spaces: 2
  • Parking Features: Paved Drive, Off Street, Paved

Location

  • County: Middlesex
  • Subdivision: Winchester town center
  • Driving Directions: Google maps best

School Information

  • Elementary School: Lynch
  • Middle School: Mccall
  • High School: Winchester

Heating & Cooling

  • Air Conditioning: Yes
  • Cooling Type: Central Air
  • Cooling Zones: 4
  • Heating Type: Forced Air, Radiant, Natural Gas
  • Heating Fuel: Forced Air, Radiant, Natural Gas
  • Heating Zones: 4

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: Connection for Gas Range, Connection for Gas Dryer

Structural Information

  • Architectural Style: Contemporary, Villa
  • Exterior Const.: Stone
  • Basement: Yes
  • Basement Desc.: Full, Finished, Interior Entry, Sump Pump
  • Square Feet: 5,233
  • Sq. Ft. Source: Public Records
  • Year Built: 2004

Lot Features

  • Lot Size (Acres): 0.25
  • Lot Dimensions: .25
  • Frontage: Public
  • Street/Road Desc.: Paved
  • Fence: Yes
  • Fencing (Description): Fenced/Enclosed, Fenced

Green Features

  • Energy Efficient: Thermostat

Financial Considerations

  • Price Per Sq. Ft.: $506.4
  • Tax Amount: $24,849
  • Tax Year: 2026
  • Terms: Contract

Disclosures and Reports

  • Disclosures/Rstr.: Some photos have been virtually enhanced
  • Property ID: M:0015 B:0016 L:0000, 898747
Buyer's Brokerage Compensation: Contact Listing Agent
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— 18 Middlesex St —

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NMLS#: 1598647

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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
9-120.5 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
10/22/2026
Listed
$2,650,000
80.89%
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
2026
$24,849
10341%
$2,242,700
5%
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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18 Middlesex St, Winchester, MA 01890 (MLS# 73593868) is a Single Family property with 4 bedrooms, 4 full bathrooms and 1 partial bathroom. 18 Middlesex St is currently listed for $2,650,000 and was received on October 22, 2026. This property is listed by Jennifer Taves from our Boston-Back Bay Office.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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