18 Middlesex St Winchester, MA $ 2,795,000
18 Middlesex St
$ 2,795,000
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18 Middlesex St

Winchester, MA, 01890
$ 2,795,000
Bedrooms4 Baths4.1 Sq 5,233

Monthly Estimate*

$ 17,648

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Single Family Home for sale in Winchester, MA

for $2,795,000 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.

This European-inspired villa blends timeless elegance with modern design. A dramatic curved staircase and soaring architectural details introduce a home designed for both grand entertaining and everyday comfort. Sun-filled living spaces feature handcrafted finishes, antique beams, stone fireplaces, and expansive French doors that create a seamless connection to the outdoors. At the heart of the home is a designer chef’s kitchen w/ bespoke cabinetry, lux appliances, and an adjoining mudroom. Outside, the property transforms into a private resort-like retreat with granite-columned loggia, heated saltwater pool, landscaped grounds w/ irrigation, and multiple entertaining areas. The spa-like primary suite, ensuite guest bedrooms, finished lower level with flexible bonus spaces, and heated driveway/walkways complete this estate. A lifestyle of luxury/convenience steps away from town, commuter rail, school and walking trails.

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Single Family Active

Price

$ 2,795,000

Bedrooms

4

Full Bath

4

Half Bath

1

Property Type

Single Family

Taxes

$ 23,792

Style

Contemporary,Villa

Lot Size

0.25

Year Built

2004

Town/City

Winchester

County/Region

Middlesex

MLS | Web ID

73518621

List By
Tina Natale

Listing Agent

Luxury Living Real Estate

Broker

Affordability Calculator

$19,631
Per Month
90%
10%
0%
Monthly Principal & Interest
$17,648
Monthly Property Taxes
$1,983
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.49% 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
5/14/2026$2,795,000 Listed Price

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18 Middlesex St, Winchester, MA, 01890 is a Single Family Home for sale at $2,795,000 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