
18 Middlesex St Winchester — Photo 1 of 32
Recent Drop: $100,000
$2,695,000
Winchester, MA 01890
Beds
4
Baths
4.5
SqFt
5,233
Style
Single Family
Built
2004
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.
* Analysis is based on 24 actively listed and recently sold comparable properties strictly within Winchester, MA.
Gas Water Heater • Range • Dishwasher • Disposal • Microwave • Refrigerator • Freezer • Washer • Dryer • Wine Refrigerator
Public Transportation • Shopping • Tennis Court(s) • Walk/Jog Trails • Medical Facility • Bike Path
26 x 19
15 x 15
20 x 14
18 x 11
19 x 13
15 x 15
15 x 13
15 x 13
10 x 13
10 x 13
8 x 6
Was $2,795,000
Aug 5, 2026
MLS® 73518621
May 13, 2026
MLS® 73518621
Nov 12, 2025
MLS® 73442182
Oct 10, 2025
MLS® 73442182
May 16, 2025
MLS® 73347754
Mar 19, 2025
MLS® 73347754
Nov 21, 2024
MLS® 73292156
Sep 18, 2024
MLS® 73292156
23,406
U.S. Census Bureau, ACS 2024 5-Year Estimates (B01003)
$230K
U.S. Census Bureau, ACS 2024 5-Year Estimates (B19013)
18.3%
U.S. Census Bureau, ACS 2024 5-Year Estimates (B25003)
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)
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
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