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Photo 1 of 32 — 18 Middlesex St, Winchester, MA 01890
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18 Middlesex St, Winchester, MA 01890

Middlesex County

Key Facts

4Beds
5Baths
5,233Sq Ft
2004Year Built
0.25Lot (acres)

Description

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.

Property Information

Property Type

Residential

Sub-Type

Single Family Residence

Year Built

2004

Living Area

5,233 sq ft

Lot Size

0.25 acres

Parking Spaces

2

Zoning

RG

Days on Market

21

MLS® Listing#

73518621

Property Features

Interior

Central VacuumMaster Downstairs

Exterior

Rain GuttersStorageLighting

Appliances

Gas Water HeaterRangeDishwasherDisposalMicrowaveRefrigeratorFreezerWasherDryerWine Refrigerator

Cooling

Central AirZoned

Heating

Natural GasForced AirRadiantZoned

Flooring

WoodMarble

Basement

FullFinishedInterior EntrySump Pump

Pool

In GroundPrivate

Parking

PavedOff Street

Laundry

Gas Dryer HookupWasher Hookup

Patio

PatioCoveredDeck

Fencing

Fenced

Lot Features

Landscaped

Foundation

Concrete Perimeter

Windows

Insulated Windows

Security

Security System

Other Structures

Storage

Community

Tennis Court(s)

Sewer

Public Sewer

Water Source

Public

Rooms

  • Bathroom 110x13First
  • Bathroom 210x13Second
  • Bathroom 38x6Second
  • Bedroom 215x15Second
  • Bedroom 315x13Second
  • Bedroom 415x13Basement
  • Dining Room15x15First
  • Family Room18x11First
  • Kitchen20x14First
  • Living Room26x19First
  • Master Bedroom19x13First

Schools

Elementary:
Lynch
Middle:
Mccall
High:
Winchester

Financial Details

HOA

None

Annual Taxes

$23,792

Tax year 2025

Assessed Value

$2,145,400

Parcel Number

M:015 B:0016 L:0,898747

Directions

Google Maps

Affordability Calculator

$559,000

Estimated monthly payment

$14,876/mo

Principal $2,236,000 · Est. interest $3,119,419 over 30 yrs

Neighborhood Market Statistics

How this home compares to active listings in Winchester, MA

$1,000,000
Median Listing Price
39
Median Days on Market
2,497
Median Sq Ft
$530
Median Price / Sq Ft
46
Active Listings
  • This home’s price is 180% above the area median.
  • Its price per sq ft is 1% above the area median.

Market statistics compiled from active EXIT Realty® and MLS listings in Winchester, MA.

Location

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Points of Interest in Winchester, MA

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Nearby Homes

Similar Homes Nearby

Similar Home Values

Comparable nearby listings and their asking prices.

AddressPriceBedsBathsSq Ft
26 N Gateway, Winchester, MA$2,099,000443,210
276 High Street, Winchester, MA$2,195,000545,006
14 Hillside Ave, Winchester, MA$2,300,000453,881
53 Winford Way, Winchester, MA$2,399,000545,083
78 Bacon Street, Winchester, MA$2,499,000545,230
9 Plymouth Rd, Winchester, MA$2,500,000534,071

Moving Cost Estimate

EXIT Agents in Winchester

Listing Courtesy: Luxury Living Real Estate - 6172277007

Presented by: Tina Natale

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein. Copyright ©2026 MLS Property Information Network, Inc. All Rights Reserved.

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Data provided by MLS Property Information Network. MLS® Listing#73518621. © 2026EXIT Realty®. All rights reserved.