Active
121 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.

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 RoomMaster 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

Master 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

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

2,667 housing units permitted in the last 12 months (-2% vs the prior 12 months) — 1,709 in 5+ unit buildings

U.S. Census Bureau, Building Permits Survey (through Jun '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

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