Single Family Residence at 18 Middlesex St, Winchester MA 01890
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$2,650,000

18 Middlesex St, Winchester MA 01890
Winchester, MA 01890
Listed by Jennifer Taves
Bedrooms
4
Bathrooms
4.5
Living area
5,233 sqft
Year built
2004

About this home

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.

Highlights

Private poolFireplace

Property details

MLS
MLS Property Information Network
MLS #
73593868
Property type
Single Family Residence
Subdivision
Winchester town center
Status
Active
Days on market
1
On market date
October 22, 2026
Stories
N/A
Total bathrooms
4.5
Garage spaces
N/A
Parking spaces
2
Lot size
0.25 acres
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Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card.

Elementary
Lynch Elementary
0.46 mi away · Grades -1-5
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
506
Student:teacher ratio
11.8:1
District
Winchester
Middle
McCall Middle
0.65 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
1,059
Student:teacher ratio
11.8:1
District
Winchester
High
Winchester High School
0.43 mi away · Grades 9-12
Nearest school -- attendance-zone data not available here
4.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
1,349
Student:teacher ratio
13.8:1
District
Winchester

Walkability

Blended score for Winchester's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

75
Walkable
out of 100
EPA National Walkability Index
11.5 / 20 -- Above average walkable
Google Places amenity density
100 / 100
Restaurants & cafes20
Grocery stores4
Parks20
Schools20
Transit stops20
Pharmacies4

Market position

How this listing compares to current activity in Winchester, from live MLS data.

On the market 1 days -- 83 fewer days than Winchester's current average of 84 days.
For reference, the median list price across 178 active listings in Winchester right now is $799,000.

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

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Est. monthly payment
$16,109/mo
$530,000 down
$2,120,000 loan
Principal & interest$13,750
Property tax (est.)$2,208
Home insurance (est.)$150

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Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated 2 days ago.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.