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ActiveListed 160 days ago

$2,650,000

18 Middlesex St, Winchester, MA 01890

4
beds
4.5
baths
5,233
sqft
Lot sizeThe land that comes with the home, as reported to the MLS.
10,812 sqft
Year builtThe year the building was originally built, as reported by the listing agent.
2004
On the marketDays since the home was listed. New listings tend to move fastest.
160 days ago
Property type
Single Family Residence
Price per sqftList price divided by interior living area — handy for comparing homes of different sizes.
$506
ParkingSpaces that come with the home, as reported to the MLS.
2 spaces
Annual taxesLast annual property tax bill reported to the MLS. A new owner's bill can differ.
$23,792

What’s Special

  • Central Air
  • Patio
  • Pool - Inground
  • Fenced Yard

New Price! OH SAT & SUN 12:30-1:30. 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 all in walking distance to downtown, the new Lynch School, new commuter rail train station and many shops and restaurants.

Listing courtesy of Tina Natale, Luxury Living Real Estate · MLS PIN #73518621

Facts & Features

Status
Active
Active status flag
Active
Bedrooms
4
Bathrooms
4 full, 1 half
Living area
5,233 sqft

Interior

2
  • Bathroom
  • Central Vacuum

Exterior

10
  • Patio
  • Covered Patio/Deck
  • Pool - Inground
  • Rain Gutters
  • Storage
  • Professional Landscaping
  • Sprinkler System
  • Decorative Lighting
  • Fenced Yard

Parking

3
  • Paved Drive
  • Off Street
  • Paved

Laundry

2
  • Gas Dryer Hookup
  • Washer Hookup

Heating

3
  • Forced Air
  • Radiant
  • Natural Gas

Cooling

1
  • Central Air

Appliances

10
  • Gas Water Heater
  • Range
  • Dishwasher
  • Disposal
  • Microwave
  • Refrigerator
  • Freezer
  • Washer
  • Dryer

MLS PIN #73518621 · Listed May 13, 2026

Location

18 Middlesex St, Winchester · All Winchester homes

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting 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, leasing or renting. 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, or as to the accuracy of any of the Images, set forth herein.

$2,650,000

18 Middlesex St

19 Hancock Street1 / 40
Active

$2,199,000

4 bd · 3.5 ba · 3,570 sqft · Single Family

19 Hancock Street

Winchester, MA 01890

Listing courtesy of Vita Realty Group, Compass · MLS PIN #73572955

9 Plymouth Rd1 / 37
Active

$2,250,000

5 bd · 3 ba · 4,071 sqft · Single Family

9 Plymouth Rd

Winchester, MA 01890

Listing courtesy of Steph Crawford Group, Real Broker MA, LLC · MLS PIN #73544924

54 Squire Road1 / 42
Active

$2,399,000

4 bd · 4.5 ba · 4,450 sqft · Single Family

54 Squire Road

Winchester, MA 01890

Listing courtesy of Anthony Marino, The Marino Group Collection · MLS PIN #73555666

595 Winthrop St1 / 42
Active

$2,229,000

5 bd · 4.5 ba · 4,010 sqft · Single Family

595 Winthrop St

Medford, MA 02155

Listing courtesy of Brian & Diana Segool, Gibson Sotheby's International Realty · MLS PIN #73579159

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting 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, leasing or renting. 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, or as to the accuracy of any of the Images, set forth herein.