OPEN SAT, 11:30AM TO 1PM

For sale

$2,650,000

Est. $17,111/mo —

•

5,233

sq ft

18 Middlesex St, Winchester, MA 01890

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.

Single-familyProperty Type

2004Year Built

10,812 sq ftLot Size

$506Price/Sq.Ft.

2 spacesParking

Listed by Jennifer Taves • Coldwell Banker Realty - Boston

Listed by • Coldwell Banker Realty - Boston

Listing updated: Oct 22, 2026 at 11:13am

Redfin checked: a minute ago

•Source:MLS PIN #73593868

Payment calculator

$17,111 per month

Principal and interest$14,642

Property taxes

$2,071

HOA dues

Home insurance

$398

Utilities

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Affordability tools

See this home in person

This home is unavailable to tour on this day.

Next available date: Friday, October 23

Open houses

Saturday, Oct 24

11:30am - 1:00pm

Sunday, Oct 25

11:30am - 1:00pm

Nearby open houses (10)

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Around this home

Schools

K - 12
Preschool & daycare

Lynch Elementary School

Public PreK-5 • Assigned • 0.5mi

9/10

McCall Middle School

Public 6-8 • Assigned • 0.6mi

9/10

Winchester High School

Public 9-12 • Assigned • 0.5mi

10/10

Provided by GreatSchools

About North

Main

North Main, located between Winchester Center and the Middlesex Fells Reservation, is a residential and commuter-friendly Winchester neighborhood with a walkable main street and quick trail access. The neighborhood’s character concentrates around the North Main Street stretch near the Winchester Country Club entrance, where small storefronts, local services, and a steady rhythm of foot and car traffic set the tone. Housing reads as classic New England, with a mix of older colonials, capes, and well-kept multifamily homes along leafy side streets. The Middlesex Fells Reservation frames daily routines with wooded climbs and reservoir views. Winchester Country Club adds a long-standing social and landscape landmark. Downtown anchors nearby with indie stops like Book Ends and the Winchester Community Music School.

Provided by Walk Score and Local Logic

Market insights

18 Middlesex St · $2,650,000

DAYS ON MARKET

The average home goes pending in 23 days.

SALE-TO-LIST

Most homes are selling 1% above list price.

LIST PRICE

Median sale price in this area is $843,256. (68% lower than this home)

PRICE DROP

22% of homes in this area have had a price drop in the past month.

Property details

Interior
Exterior
Finance

Kitchen

Bathroom

Bedroom

Living

Dining

Interior features
Two fireplaces
Insulated windows

Bedrooms
Five bedrooms: two on the first floor, two on the second floor, and one in the basement

Bathrooms
Four full bathrooms and one half bathroom
Primary bathroom

Kitchen
Range, dishwasher, disposal, microwave, refrigerator, freezer, and wine refrigerator

Laundry & utility
Washer and dryer
Gas dryer hookup

Flooring
Marble
Stone and slate

Heating & cooling
Forced-air and radiant heating with natural gas
Central air conditioning
Thermostat

Sale and tax history for 18 Middlesex St

Sale History
Tax History

Date

Event

Price

MLS PIN #73593868

Oct 22, 2026

Listed

$2,650,000

$506/sq ft

MLS PIN #72044797

Oct 28, 2016

Sold

$1,465,000

$280/sq ft

Aug 17, 2016

Pending

—

Jul 28, 2016

Listed

$1,499,000

$286/sq ft

+25

The classic villa was created as a country retreat for discerning clients…18 Middlesex is an extraordinary modern example. Imagine feeling transported each day to Tuscany, living just minutes from Boston. European-inspired and masterfully crafted, this custom contemporary home showcases sophisticated design, top-of-the-line systems, quality material choices. Gorgeous reception hall and graceful arches lead to casually elegant living spaces, each offering unique elements, such as: stone fireplaces, antique beams and sconces, hand-crafted railings and fixtures, luxurious marble surfaces. Banks of French doors throughout lead to a private backyard oasis featuring a granite-columned loggia overlooking a pool and manicured landscape. Memorable gatherings outside and in the open concept, cook's kitchen w/adjacent family room await. Serene master retreat w/exquisite spa bath; en suite bedrooms; attic for potential expansion, three multi-use bsmnt rooms. So convenient to town, train, schools.

MLS PIN #30484412

Jun 7, 2002

Sold

$450,000

$86/sq ft

Apr 11, 2002

Listing Removed

—

Mar 9, 2001

Listed

$529,900

$101/sq ft

Year

Property tax

Land + Additions

Assessment*

2026

$24,849 (+4.4%)

$671,400 + $1,571,300

$2,242,700

2025

$23,792 (+29.4%)

$637,800 + $1,507,600

$2,145,400

2023

$18,386 (−1.2%)

$604,200 + $1,406,700

$2,010,900

2022

$18,614 (+2.7%)

$503,500 + $984,400

$1,487,900

2021

$18,121 (+3.5%)

$428,000 + $984,400

$1,412,400

2020

$17,500 (+8.8%)

$428,000 + $984,400

$1,412,400

2019

$16,088 (+3.6%)

$344,100 + $984,400

$1,328,500

2018

$15,536 (+13.4%)

$327,300 + $947,200

$1,274,500

2017

$13,701 (+7.5%)

$310,500 + $805,200

$1,115,700

2016

$12,744 (+7.3%)

$310,500 + $780,600

$1,091,100

2015

$11,875 (+0.1%)

$281,100 + $697,100

$978,200

2014

$11,859 (+1.0%)

$243,400 + $693,300

$936,700

2013

$11,747 (+3.6%)

$226,600 + $693,300

$919,900

2012

$11,344 (+3.7%)

$210,600 + $693,300

$903,900

2011

$10,937 (+3.2%)

$210,600 + $693,300

$903,900

2010

$10,594 (+2.1%)

$212,000 + $708,400

$920,400

2009

$10,373

$212,000 + $708,400

$920,400

Public record

Beds

Baths

3.5

Stories

Lot width

—

Lot depth

—

Lot size

0.25 Acres

Year renovated

—

Finished Sq. Ft.

4,319

Unfinished Sq. Ft.

—

Total Sq. Ft.

4,319

Year built

2004

Style

Single Family Residential

County

Middlesex County

APN

3175978S

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Sep 16, 2026.

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

5/10 Heat Factor

7 days above 98° expected this year, 15 days in 30 years

6/10 Wind Factor

54% chance of strong winds in next 30 years

3/10 Air Factor

2 unhealthy days expected this year, 3 days in 30 years

Provided by First Street

Historical weather

Winchester, MA • 01890

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

90/ 100

Exceptional sunlight

Sunscore

This home ranks in the top 23% for direct sun exposure in Winchester. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

9.9 hrs

5.7 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 18 Middlesex St

$2,655,132

$5,132 over list price of $2.65M

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $2.2M to $3.5M.

SOLD JUL 10, 2026
$2,409,000 Last sold price
5 beds4.5 baths5,881 sq ft
49 Sheridan Cir, Winchester, MA 01890
$96/sq ft
smaller lot
10 years newer
SOLD JUN 26, 2026
$3,500,000 Last sold price
5 beds3.5 baths5,128 sq ft
50 Oxford St, Winchester, MA 01890
$177/sq ft
larger lot
87 years older
SOLD SEP 2, 2026
$2,250,000 Last sold price
4 beds3 baths4,210 sq ft
6 Davey Ln, Winchester, MA 01890
$28/sq ft
larger lot
8 years older
SOLD JUN 30, 2026
$2,400,000 Last sold price
5 beds3.5 baths4,822 sq ft
216 Highland Ave, Winchester, MA 01890
$8/sq ft
102 years older
unfinished basement
SOLD AUG 14, 2026
$2,200,000 Last sold price
4 beds2.5 baths3,123 sq ft
15 Cabot St, Winchester, MA 01890
$198/sq ft
100 years older
unfinished basement
SOLD JUN 23, 2026
$2,830,000 Last sold price
5 beds3.5 baths4,792 sq ft
56 Yale St, Winchester, MA 01890
$85/sq ft
81 years older

Rental earnings

Est. $6,165 per month, based on comparable rentals

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Details provided by MLS PIN and may not match the public record. Learn more.

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Payment calculator

Affordability tools

See this home in person

Nearby open houses (10)

Around this home

Schools

Market insights

Property details

Sale and tax history for 18 Middlesex St

Public record

Climate risks

Historical weather

Sun exposure

Redfin Estimate for 18 Middlesex St

Early Access listings

Nearby similar homes

New listings for sale in 01890

More real estate resources