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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
Pool

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

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Community

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.

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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 James
18 Middlesex St
Winchester, MA