
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.
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
Master 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
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 Agent: Tina Natale
Listing Office: Luxury Living Real Estate
MLS® Number: 73518621
Open Houses
Browse More Homes in Winchester
Explore other active listings in the area.
$1,299,000253 Pond StWinchester, MA4 bd2 ba3,307 sqft
$2,995,0008 Priscilla LaneWinchester, MA5 bd6 ba6,500 sqft
$2,249,00011 Locke StWinchester, MA5 bd4 ba4,368 sqft
$1,650,000117 HighlandWinchester, MA5 bd4 ba3,722 sqft
$3,149,00037 Mayflower RoadWinchester, MA7 bd8 ba8,540 sqft
$2,849,0007 Viking RdWinchester, MA5 bd5 ba5,058 sqft


