Active
144 Days on market
18 Middlesex St Winchester — Photo 1 of 32

18 Middlesex St Winchester — Photo 1 of 32

Recent Drop: $100,000

$2,795,000
$2,695,000

$2,695,000

18 Middlesex St, Winchester, MA 01890

Winchester, MA 01890

Beds

4

Baths

4.5

SqFt

5,233

Style

Single Family

Built

2004

Seller to offer a buyer credit paying up to 2% of loan size for buyer at closing that can go to a permanent or temporary rate buydown. 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.

Key facts

It was listed on May 13, 2026. The price has come down from an original $2,795,000 to $2,695,000, most recently on August 5, 2026. The annual property taxes are $23,792 (2025 tax year). It sits on a 0.25-acre (10,812 sq ft) lot.

Open Houses

Market Value Analysis

This Property
Size (SqFt) →Price →
This Property$515/sqft
Local Avg (Winchester)$543/sqft
5% BelowMarket Average

* Analysis is based on 24 actively listed and recently sold comparable properties strictly within Winchester, MA.

Property Details

Financials

Original Price$2,795,000
Annual Taxes$23,792

Parking

Garage0
Off-Street2

Interior Specifications

Total Rooms10
Fireplaces2
FlooringWood, Marble, Stone / Slate
BasementFull, Finished, Interior Entry, Sump Pump

Climate & Utilities

HeatingForced Air, Radiant, Natural Gas
CoolingCentral Air
WaterPublic
SewerPublic Sewer

Building & Exterior

Construction--
Roof--
FoundationConcrete Perimeter
ZoningRG

Property & Lot

Acres0.25
SqFt Lot10,812
Lot Features--

Amenities & Appliances

Gas Water Heater • Range • Dishwasher • Disposal • Microwave • Refrigerator • Freezer • Washer • Dryer • Wine Refrigerator

Neighborhood

Public Transportation • Shopping • Tennis Court(s) • Walk/Jog Trails • Medical Facility • Bike Path

Geography

Floorplan Breakdown

Structural Layout

Second
Bedroom 2Bedroom 3Bathroom 2Bathroom 3
First
Living RoomDining RoomKitchenFamily RoomPrimary BedroomBathroom 1
Basement
Bedroom 4
Living Room
Lvl First

26 x 19

Dining Room
Lvl First

15 x 15

Kitchen
Lvl First

20 x 14

Family Room
Lvl First

18 x 11

Primary Bedroom
Lvl First

19 x 13

Bedroom 2
Lvl Second

15 x 15

Bedroom 3
Lvl Second

15 x 13

Bedroom 4
Lvl Basement

15 x 13

Bathroom 1
Lvl First

10 x 13

Bathroom 2
Lvl Second

10 x 13

Bathroom 3
Lvl Second

8 x 6

Property History

Price Drop
$2,695,000

Was $2,795,000

Aug 5, 2026

MLS® 73518621

Listed
$2,795,000

May 13, 2026

MLS® 73518621

Terminated
$2,795,000

Nov 12, 2025

MLS® 73442182

Listed
$2,795,000

Oct 10, 2025

MLS® 73442182

Terminated
$2,695,000

May 16, 2025

MLS® 73347754

Listed
$2,695,000

Mar 19, 2025

MLS® 73347754

Terminated
$2,695,000

Nov 21, 2024

MLS® 73292156

Listed
$2,695,000

Sep 18, 2024

MLS® 73292156

Questions about this home

When was 18 Middlesex St, Winchester listed?

18 Middlesex St, Winchester was listed on May 13, 2026.

Has the price of 18 Middlesex St, Winchester changed?

The price has come down from an original $2,795,000 to $2,695,000, most recently on August 5, 2026.

What are the property taxes for 18 Middlesex St, Winchester?

The annual property taxes for 18 Middlesex St, Winchester are $23,792 (2025 tax year).

How big is the lot at 18 Middlesex St, Winchester?

18 Middlesex St, Winchester sits on a 0.25-acre (10,812 sq ft) lot.

What is the status of 18 Middlesex St, Winchester?

18 Middlesex St, Winchester is actively listed for sale.

Population

23,406

U.S. Census Bureau, ACS 2024 5-Year Estimates (B01003)

Median Household Income

$230K

U.S. Census Bureau, ACS 2024 5-Year Estimates (B19013)

Renter-Occupied Homes

18.3%

U.S. Census Bureau, ACS 2024 5-Year Estimates (B25003)

New Construction Permits — Middlesex County

2,698 housing units permitted in the last 12 months (+3% vs the prior 12 months) — 1,713 in 5+ unit buildings

U.S. Census Bureau, Building Permits Survey (through Jul '26)

ADU Potential

Massachusetts allows one accessory dwelling unit by right in single-family zoning districts statewide (M.G.L. c. 40A §3; 760 CMR 71.00, effective Feb 2025). Estimated maximum ADU size for this property: 900 sq ft (the lesser of 900 sq ft or half the 5,233 sq ft principal dwelling). Lot size: 10,812 sq ft.

Based on listing data, which indicates the property type — not the zoning district. Local dimensional, septic (Title 5), and historic-district requirements still apply. Not legal advice — verify with the municipality.

Listing Provided By

Listing Agent: Tina Natale

Listing Office: Luxury Living Real Estate

MLS® Number: 73518621