$2,795,000
18 Middlesex St
Winchester, MA, 01890
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.
Property Details
Price:
$2,795,000
MLS #:
73518621
Status:
Active
Beds:
4
Baths:
4.5
Type:
Single Family
Subtype:
Single Family Residence
Listed Date:
May 13, 2026
Finished Sq Ft:
5,233
Total Sq Ft:
5,233
Lot Size:
10,812 sqft / 0.25 acres (approx)
Year Built:
2004
Schools
Elementary School:
Lynch
Middle School:
Mccall
High School:
Winchester
Interior
Above Grade Finished Area
4331
Appliances
Gas Water Heater, Range, Dishwasher, Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer, Wine Refrigerator
Bathrooms
4 Full Bathrooms, 1 Half Bathroom
Below Grade Finished Area
902
Cooling
Central Air
Fireplaces Total
2
Flooring
Wood, Marble, Stone / Slate
Heating
Forced Air, Radiant, Natural Gas
Interior Features
Bathroom, Central Vacuum
Laundry Features
Gas Dryer Hookup, Washer Hookup
Exterior
Architectural Style
Contemporary, Villa
Community Features
Public Transportation, Shopping, Tennis Court(s), Walk/Jog Trails, Medical Facility, Bike Path, Conservation Area, Public School, T-Station
Exterior Features
Patio, Covered Patio/Deck, Pool – Inground, Rain Gutters, Storage, Professional Landscaping, Sprinkler System, Decorative Lighting, Fenced Yard, Stone Wall
Fencing
Fenced/Enclosed, Fenced
Open Parking Spaces
2
Open Parking YN
1
Parking Features
Paved Drive, Off Street, Paved
Parking Spots
2
Parking Total
2
Patio And Porch Features
Patio, Covered
Security Features
Security System
Window Features
Insulated Windows
Financial
Tax Year
2025
Taxes
$23,792
Marie Andrews is an award-winning, licensed real estate broker with licenses in Massachusetts and Florida. She has been selling real estate in the greater Boston area for over 20 years. Over the past two decades, Marie has worked for Century 21 Advanced Realty, building a reputation as a multi-million dollar producer. She has developed an extensive network of investors, lenders, and attorneys. Marie has a wide knowledge base on property management, Massachusetts real estate law, and building…
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Map
Current real estate data for Single Family in Winchester as of Jul 12, 2026
70
Single Family Listed
67
Avg DOM
542
Avg $ / SqFt
$2,029,207
Avg List Price
Community
- Address18 Middlesex St Winchester MA
- CityWinchester
- CountyMiddlesex
- Zip Code01890
Subdivisions in Winchester
- Brooks / Parkhurst / Town Forest
- Cox Road / High St Extension neighborhood
- Flats
- Flats neighborhood
- Lakeview/Wedgemere~ Near downtown & Wedgemere train station
- Macdonald field neighborhood
- Middlesex / downtown
- Near town/ Pine St neighborhood
- Old Village/ West Side
- Rangeley Historical Estate
- The Flats
- Vinson-Owen School District.
- West Side
- Winning Farm
Similar Listings Nearby
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 $2,029,207. To schedule a showing of MLS#73518621 at 18 Middlesex St in Winchester, MA, contact your Pegasus Realty LLC agent at 781-858-3505.
Courtesy 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