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18 Middlesex StWinchester, MA 01890

For Sale

$2,650,000

Smart Buyer Rebate $13,250

Inspired by the timeless villas of Europe, this exceptional residence blends classic elegance with modern design. A dramatic curved staircase and soaring architectural details introduce inviting living spaces featuring handcrafted finishes, antique beams, stone fireplaces, and expansive French doors that connect seamlessly to the outdoors. At the heart of the home, a chef’s kitchen showcases custom cabinetry, luxury appliances, and an adjoining mudroom. The outdoor setting offers a private retreat with a granite-columned loggia, heated saltwater pool, landscaped grounds with irrigation, and multiple areas for entertaining.The spa-inspired primary suite, ensuite guest bedrooms, and finished lower level with flexible bonus spaces provide comfort and versatility. Heated driveways and walkways add year-round convenience. Ideally located within walking distance of downtown, the new Lynch School, the new commuter rail station, and an array of shops and restaurants, this home offers a thoughtful balance of timeless style, modern amenities, and everyday comfort.

Listed by Jennifer Taves

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Coldwell Banker Realty - Boston

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6178779520

Last updated October 29, 2026

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Source: MLSPin #73593868

Listing Facts

  • TypeSingle-family
  • NeighborhoodNorth Main
  • Bedrooms4
  • Bathrooms5
  • Days on Prevu9
  • Taxes$24,849/year
  • Size5,233 sqft
  • Price per sqft$506

Amenities

  • Dishwasher
  • Private Outdoor Space
  • Washer/Dryer
  • Air Conditioning
  • Parking
  • Swimming Pool

Location

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Listing History

10/22/2026
Listed by Coldwell Banker Realty - Boston
$2,650,000
  1. 10/22/2026$2,650,000
    Listed by Coldwell Banker Realty - Boston

Property Details for 18 Middlesex St

Association

Amenities

  • Community Features: Pool, Tennis Court(s), Park, Golf

Exterior

Construction

  • Roof: Rubber
  • Window Features: Insulated Windows
  • Year Built: 2004
  • Year Built Details: Actual
  • Architectural Style: Contemporary, Villa
  • Construction Materials: Stone
  • Exterior Features: Rain Gutters, Storage, Garden, Lighting

Features

  • Fencing: Fenced, Stone
  • Other Structures: Storage
  • Patio And Porch Features: Patio, Covered, Deck
  • Pool Features: In Ground, Heated, Private
  • Pool Private: Yes

Measurements

  • Building Area Total: 5,233
  • Building Area Units: Square Feet
  • Lot Features: Landscaped
  • Lot Size Acres: 0.25
  • Lot Size Area: 0
  • Lot Size Square Feet: 10,812
  • Lot Size Units: Acres

Financial

Taxes

  • Parcel Number: M:0015 B:0016 L:0000,898747
  • Tax Annual Amount: $24,849.00
  • Tax Assessed Value: $2,242,700.00
  • Tax Year: 2026

Interior

Features

  • Appliances: Gas Water Heater, Range, Dishwasher, Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer, Wine Refrigerator
  • Fireplace: Yes
  • Fireplaces Total: 2
  • Flooring: Marble
  • Interior Features: Master Downstairs

Measurements

  • Living Area: 5,233
  • Living Area Source: Public Records

Rooms

  • Basement: Full, Finished, Interior Entry, Sump Pump
  • Has Basement: Yes
  • Bathrooms Full: 4
  • Bathrooms Half: 1
  • Bathrooms Total Integer: 5
  • Bedrooms Total: 4
  • Rooms Total: 8

Other

Environmental

  • Green Energy Efficient: Thermostat

Location

  • Subdivision Name: Winchester Town Center

Parking

Parking

  • Open Parking Spaces: 3
  • Open Parking: Yes
  • Parking Features: Paved, Off Street
  • Parking Total: 3

Schools

Elementary School

  • Elementary School: Lynch

High School

  • High School: Winchester

Middle or Junior School

  • Middle Or Junior School: Mccall

Utilities

Equipment

  • Cooling: Central Air, Zoned
  • Has Cooling: Yes
  • Heating: Natural Gas, Forced Air, Radiant, Zoned
  • Has Heating: Yes
  • Sewer: Public Sewer
  • Water Source: Public

Frequently Asked Questions

How many bedrooms and bathrooms does this single-family home have?

There are 4 bedrooms and 5 bathrooms in this single-family home at 18 Middlesex St.

What schools are nearby to 18 Middlesex St?

Nearby schools include the Lynch Elementary School, Mccall Middle School, and Winchester High School.

Does this single-family home have parking?

Yes, there are 3 parking spaces available for 18 Middlesex St.

What are the annual taxes for 18 Middlesex St?

Annual taxes for this single-family home are estimated at $24,849.

How does 18 Middlesex St compare to other single-family homes in North Main?

This single-family home is listed 106% above the average price for single-family homes in North Main and has been on the market for 77 less days than the typical home in this area.

What is the square footage on this single-family home?

According to the MLS, this listing is 5,233 sqft.

18 Middlesex St is a 4-bedroom, 5-bath single-family home for sale in Winchester MA 01890. On Prevu for 9 days at $2,650,000. This property features 5,233 square feet of living space, located in North Main. The median listing price for single-family homes in this area is $1,025,000. Nearby schools include Lynch Elementary School, Mccall Middle School, and Winchester High School. Additional amenities include private outdoor space, dishwasher, air conditioning, parking, swimming pool, and washer/dryer. View other single-family home listings in Middlesex County.

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.

Full MLS Disclaimers

Rebate estimate is indicative only and based on listing price and estimated buyer's agent commission paid by owner, if applicable. Final rebates are subject to Terms of Use and may vary due to final negotiated transaction terms.