18 Middlesex St
Winchester, MA, 01890
$2,795,000
A masterpiece of design and craftsmanship. Every detail has been meticulously curated, blending timeless elegance with state-of-the-art amenities.Step into a grand foyer, where a striking curved staircase sets the stage for the home’s sophisticated ambiance. Expansive living and entertaining spaces flow seamlessly, featuring soaring ceilings, custom millwork, and exquisite finishes. The Bespoke chef’s kitchen, outfitted with professional-grade appliances, a fireplace, and an adjoining mudroom, is both a culinary dream and a warm gathering place.The opulent primary suite is a private retreat, reminiscent of the world’s finest resorts, boasting a spa-inspired bath and serene views. Three additional en-suite bedrooms provide refined comfort for family or guests. Designed for effortless indoor-outdoor living, eight sets of French doors opening to a breathtaking loggia with marble columns and sparkling heated saltwater pool. Heated driveway and front walk. Shown by appointment.
Current real estate data for Single Family in Winchester as of Oct 14, 2025
64
Single Family Listed
60
Avg DOM
542
Avg $ / SqFt
$2,254,228
Avg List Price
Property Details
Price:
$2,795,000
MLS #:
73442182
Status:
Active
Beds:
4
Baths:
4.5
Type:
Single Family
Subtype:
Single Family Residence
Listed Date:
Oct 10, 2025
Finished Sq Ft:
5,233
Total Sq Ft:
5,233
Lot Size:
10,812 sqft / 0.25 acres (approx)
Year Built:
2004
Schools
Interior
Appliances
Range, Dishwasher, Disposal, Microwave, Washer, Dryer, Vacuum System – Rough-in, Range Hood
Bathrooms
4 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Fireplaces Total
2
Heating
Forced Air, Radiant, Natural Gas
Exterior
Architectural Style
Colonial
Community Features
Public Transportation, Shopping, Walk/Jog Trails, Medical Facility, Bike Path, Conservation Area, Public School
Exterior Features
Patio, Pool – Inground, Rain Gutters, Fenced Yard
Parking Features
Paved
Parking Spots
4
Roof
Rubber
Financial
Tax Year
2025
Taxes
$23,792
Map
Contact Us
Mortgage Calculator
Community
- Address18 Middlesex St Winchester MA
- CityWinchester
- CountyMiddlesex
- Zip Code01890
Subdivisions in Winchester
- Close to Wright Locke Farm
- Cox Road / High St Extension neighborhood
- East SIde near town forest!!
- Everett/ Stratford
- Flats location
- FLATS location Across from Wedgemere/Oxford
- Lakeview/Wedgemere~ Near downtown & Wedgemere train station
- Ledgewood Estates
- Middlesex
- Myopia Hill/ Winchester Country Club Area
- Near VO school
- old village/ West side
- The Flats
- Top neighborhood near town center
- West side
Property Summary
- 18 Middlesex St Winchester MA is a Single Family for sale in Winchester, MA, 01890. It is listed for $2,795,000 and features 4 beds, 5 baths, and has approximately 5,233 square feet of living space, and was originally constructed in 2004. The current price per square foot is $534. The average price per square foot for Single Family listings in Winchester is $542. The average listing price for Single Family in Winchester is $2,254,228. To schedule a showing of MLS#73442182 at 18 Middlesex St in Winchester, MA, contact your Boardwalk Real Estate Corp. agent at 781-944-7820.
Similar Listings Nearby
CRP: Certified Relocation Professional CRS: Certified Residential Specialist GRI: Graduate of Realtors Institute CBR: Certified Buyers Representative BSBA: Bachelor of Science in Business Administration. Babson College 1979 MBA: Master of Business Administration. Babson College 2002 James M. Joly is President and Principal-Owner of Boardwalk Real Estate Corp.,…
More About JamesCourtesy of Luxury Living Real Estate. The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.
18 Middlesex St
Winchester, MA