
18 Middlesex St Winchester — Photo 1 of 32
Recent Drop: $100,000
$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
* Analysis is based on 24 actively listed and recently sold comparable properties strictly within Winchester, MA.
Property Details
Financials
Parking
Interior Specifications
Climate & Utilities
Building & Exterior
Property & Lot
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
Living Room
Lvl First26 x 19
Dining Room
Lvl First15 x 15
Kitchen
Lvl First20 x 14
Family Room
Lvl First18 x 11
Primary Bedroom
Lvl First19 x 13
Bedroom 2
Lvl Second15 x 15
Bedroom 3
Lvl Second15 x 13
Bedroom 4
Lvl Basement15 x 13
Bathroom 1
Lvl First10 x 13
Bathroom 2
Lvl Second10 x 13
Bathroom 3
Lvl Second8 x 6
Property History
$2,695,000
Was $2,795,000
Aug 5, 2026
MLS® 73518621
$2,795,000
May 13, 2026
MLS® 73518621
$2,795,000
Nov 12, 2025
MLS® 73442182
$2,795,000
Oct 10, 2025
MLS® 73442182
$2,695,000
May 16, 2025
MLS® 73347754
$2,695,000
Mar 19, 2025
MLS® 73347754
$2,695,000
Nov 21, 2024
MLS® 73292156
$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 Agent: Tina Natale
Listing Office: Luxury Living Real Estate
MLS® Number: 73518621







