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18 Middlesex St, Winchester MA 01890

$2,795,000

Estimated $19,205/month Calculator

Single Family

4 Bedrooms

Baths

5233

Total Parking: 2

10,812 (0.25)

Built in 2004

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.

This home has been viewed 4 times

Last Checked: June 4th, 2026 at 11:48am (Source: MLS PIN #73518621)

Air Conditioning

Waterview

Lead Paint Free

General Information for 18 Middlesex St, Winchester MA 01890

Listing ID73518621

Property TypeSingle Family / Detached

Price$2,795,000 ($534.11/SqFt)

StyleColonial

CityWinchester

CountyMiddlesex

Neighborhood(s)

Garage Parking0

ZoningRG

Year Built2004

Year Built SourcePublic Records

Year Built DetailsActual

Interior Features for 18 Middlesex St, Winchester MA 01890

Approximate Living Area Total5233

Living Area Includes BasementYes

Rooms10

Bedrooms4

Primary En Suite BathroomYes

BasementFull

Cooling1, Split

Fireplaces

AppliancesRange

FlooringTile

Electric220 Volts

Exterior Features for 18 Middlesex St, Winchester MA 01890

Approximate Lot Size (Acres)0.25

Approximate Lot Size (Square Feet)10812

Total Parking2

Garage Parking0

WaterPublic

SewerPublic Sewer

Lot Features

Parking Features1

Exterior FeaturesPorch

Foundation Materials

Construction Materials

Road Frontage Type

Patio & PorchCovered

Roof Material

Utility Connections110 Volts

Water ViewsNo

Water Views Features

Waterfront0

Waterfront Features

Pool FeaturesAssociation

Horse Permitted0

Horse Amenities

Disclosures for 18 Middlesex St, Winchester MA 01890

Lead PaintNone

UFFI

Living Area Includes BasementYes

Living Area Disclosure

Building Area SourcePublic Records

Special Listing Conditions

ExclusionsBasement Fridge

Compensation Based On

Financial Information for 18 Middlesex St, Winchester MA 01890

Association Fee

Association Fee Frequency

Association Fee Includes

Real Estate Tax23792

Tax Year2025

Assessed Value$2,145,400

Location Information for 18 Middlesex St, Winchester MA 01890

Elementary SchoolLynch

Middle SchoolMccall

High SchoolWinchester

Neighborhood(s)

Area AmenitiesWalk/jog Trails

Contact Information for 18 Middlesex St, Winchester MA 01890

Agent

Name: Tina Natale

Office

Name: Luxury Living Real Estate

Phone: 617-227-7007

Payment Calculator

, Interest

Property Taxes 1982.67

Principal & Interest 17221.9

HOA Dues

Term

Interest

Home Price

Down Payment

Exclusive Listing Agent

Luxury Living Real Estate

Tina Natale

Agent Phone

Office Phone

(617) 227-7007

Text Agent Call Agent Call Office

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EXIT

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