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18 Middlesex StWinchester, MA 01890

For Sale

$2,795,000

Smart Buyer Rebate $13,975

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.

Listed by Tina Natale

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Luxury Living Real Estate

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617-794-8460

Last updated June 03, 2026

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Source: MLSPin #73518621

Listing Facts

  • TypeSingle-family
  • NeighborhoodNorth Main
  • Bedrooms4
  • Bathrooms5
  • Days on Prevu34
  • Taxes$23,792/year
  • Size5,233 sqft
  • Price per sqft$534

Amenities

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

Location

Mortgage Calculator

Listing History

05/13/2026
Listed by Luxury Living Real Estate
$2,795,000

Property Details for 18 Middlesex St

Association

Amenities

  • Community Features: Public Transportation, Shopping, Tennis Court(s), Walk/Jog Trails, Medical Facility, Bike Path, Conservation Area, Public School, T-Station

Exterior

Construction

  • Window Features: Insulated Windows
  • Year Built: 2004
  • Year Built Details: Actual
  • Architectural Style: Contemporary, Villa
  • Exterior Features: Patio, Covered Patio/Deck, Pool - Inground, Rain Gutters, Storage, Professional Landscaping, Sprinkler System, Decorative Lighting, Fenced Yard, Stone Wall

Features

  • Fencing: Fenced/Enclosed, Fenced
  • Patio And Porch Features: Patio, Covered
  • Pool Features: In Ground
  • Pool Private: Yes
  • Road Frontage Type: Public

Measurements

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

Financial

Taxes

  • Parcel Number: M:015 B:0016 L:0,898747
  • Tax Annual Amount: $23,792.00
  • Tax Assessed Value: $2,145,400.00
  • Tax Year: 2025

Interior

Features

  • Appliances: Gas Water Heater, Range, Dishwasher, Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer, Wine Refrigerator
  • Fireplace: Yes
  • Fireplaces Total: 2
  • Flooring: Wood, Marble, Stone / Slate
  • Interior Features: Bathroom, Central Vacuum

Measurements

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

Rooms

  • Basement: Full, Finished, Interior Entry, Sump Pump
  • Bathrooms Full: 4
  • Bathrooms Half: 1
  • Bathrooms Total Integer: 5
  • Bedrooms Total: 4
  • Rooms Total: 10

Parking

Parking

  • Open Parking Spaces: 2
  • Open Parking: Yes
  • Parking Features: Paved Drive, Off Street, Paved
  • Parking Total: 2

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
  • Has Cooling: Yes
  • Electric: Generator, 200+ Amp Service
  • Heating: Forced Air, Radiant, Natural Gas
  • Has Heating: Yes
  • Laundry Features: Gas Dryer Hookup, Washer Hookup
  • Sewer: Public Sewer
  • Utilities: For Gas Range, For Gas Dryer, Washer Hookup
  • 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 2 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 $23,792.

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

This single-family home is listed 32% above the average price for single-family homes in North Main and has been on the market for 33 more 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 34 days at $2,795,000. This home features 5,233 square feet of living space, located in Middlesex County. The median listing price for single-family homes in this area is $2,112,000. 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. Browse more 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.