18 Middlesex St Winchester, MA $ 2,650,000
18 Middlesex St
$ 2,650,000
Recently Listed
Open House 10/24 11:30am - 1pm
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18 Middlesex St

Winchester, MA, 01890
$ 2,650,000
Bedrooms4 Baths4.1 Sq 5,233

Monthly Estimate*

$ 18,303

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Single Family Home for sale in Winchester, MA

for $2,650,000 with 4 bedrooms and 4 full baths, 1 half bath. This 5,233 square foot home was built in 2004 on a lot size of 0.25.

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.

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Open House

10/24/2026 11:30 AM - 1:00 PM
10/25/2026 11:30 AM - 1:00 PM
18 Middlesex St Winchester, MA
* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm

Single Family Active

Price

$ 2,650,000

Bedrooms

4

Full Bath

4

Half Bath

1

Property Type

Single Family

Taxes

$ 24,849

Style

Contemporary,Villa

Lot Size

0.25

Year Built

2004

Town/City

Winchester

County/Region

Middlesex

MLS | Web ID

73593868

List By
Jennifer Taves

Listing Agent

Coldwell Banker Realty - Boston

Broker

Affordability Calculator

$20,374
Per Month
90%
10%
0%
Monthly Principal & Interest
$18,303
Monthly Property Taxes
$2,071
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 7.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Pricing History
DatePricePrice ChangeDescription
10/22/2026$2,650,000 Listed Price

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18 Middlesex St, Winchester, MA, 01890 is a Single Family Home for sale at $2,650,000 with 5,233 sqft and a lot size of 0.25. 18 Middlesex St has 4 bedrooms, 4.1 baths, and was built in 2004. The property's zip code is 01890 which is in Winchester, MA