18 Middlesex St Winchester, MA $ 2,795,000
18 Middlesex St
$ 2,795,000
Recently Listed
Open House 5/16 11:30am - 1pm
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18 Middlesex St

Winchester, MA, 01890
$ 2,795,000
Bedrooms4 Baths4.1 Sq 4,319

Monthly Estimate*

$ 17,209

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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 4,319 square foot home was built in 2004 on a lot size of 0.25.

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.

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Open House

5/16/2026 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

$ 2,795,000

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

$19,192
Per Month
90%
10%
0%
Monthly Principal & Interest
$17,209
Monthly Property Taxes
$1,983
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% 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 4,319 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