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18 Middlesex StWinchester, MA 01890

For Sale

$2,795,000

Smart Buyer Rebate $13,975

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.

Listed by Candice Macoul

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Luxury Living Real Estate

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617-877-1998

Last updated October 24, 2025

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Source: MLSPin #73442182

Listing Facts

  • TypeSingle-family
  • NeighborhoodNorth Main
  • Bedrooms4
  • Bathrooms5
  • Days on Prevu14
  • 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

10/10/2025
Listed by Luxury Living Real Estate
$2,795,000

Property Details for 18 Middlesex St

Association

Amenities

  • Community Features: Public Transportation, Shopping, Walk/Jog Trails, Medical Facility, Bike Path, Conservation Area, Public School

Exterior

Construction

  • Roof: Rubber
  • Year Built: 2004
  • Year Built Details: Actual
  • Architectural Style: Colonial
  • Exterior Features: Patio, Pool - Inground, Rain Gutters, Fenced Yard

Features

  • Fencing: Fenced
  • Patio And Porch Features: Patio
  • Pool Features: In Ground
  • Pool Private: Yes

Measurements

  • Building Area Total: 5,233
  • Building Area Units: Square Feet
  • Lot Features: Corner Lot
  • 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: Range, Dishwasher, Disposal, Microwave, Washer, Dryer, Vacuum System - Rough-in, Range Hood
  • Fireplace: Yes
  • Fireplaces Total: 2

Measurements

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

Rooms

  • Basement: Finished
  • Bathrooms Full: 4
  • Bathrooms Half: 1
  • Bathrooms Total Integer: 5
  • Bedrooms Total: 4
  • Rooms Total: 10

Parking

Parking

  • Open Parking: Yes
  • Parking Features: Paved
  • Parking Total: 4

Utilities

Equipment

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

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.