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For sale
  • $2,795,000

    18 Middlesex St, Winchester, MA 01890

    4beds
    5,233sqft
    : 
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    Single Family Residence
    Built in 2004
    10,812 Square Feet Lot
    $2,671,900 Zestimate®
    $534/sqft
    $-- HOA

    What's special

    Handcrafted finishesAntique beamsPrivate resort-like retreatSoaring architectural detailsSun-filled living spacesAdjoining mudroomHeated saltwater pool
    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.
    45 days
    |
    1,568
    |
    53
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Tina Natale 617-794-8460,

    Luxury Living Real Estate 617-227-7007

    Source: MLS PIN,MLS#: 73518621

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      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 5
      • Full bathrooms: 4
      • 1/2 bathrooms: 1
      Primary bedroom
      • Level: First
      • Area: 247
      • Dimensions: 19 x 13
      Bedroom 2
      • Level: Second
      • Area: 225
      • Dimensions: 15 x 15
      Bedroom 3
      • Level: Second
      • Area: 195
      • Dimensions: 15 x 13
      Bedroom 4
      • Level: Basement
      • Area: 195
      • Dimensions: 15 x 13
      Bathroom 1
      • Level: First
      • Area: 130
      • Dimensions: 10 x 13
      Bathroom 2
      • Level: Second
      • Area: 130
      • Dimensions: 10 x 13
      Bathroom 3
      • Level: Second
      • Area: 48
      • Dimensions: 8 x 6
      Dining room
      • Level: First
      • Area: 225
      • Dimensions: 15 x 15
      Family room
      • Level: First
      • Area: 198
      • Dimensions: 18 x 11
      Kitchen
      • Level: First
      • Area: 280
      • Dimensions: 20 x 14
      Living room
      • Level: First
      • Area: 494
      • Dimensions: 26 x 19
      Heating
      • Forced Air, Radiant, Natural Gas
      Cooling
      • Central Air
      Appliances
      • Included: Gas Water Heater, Range, Dishwasher, Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer, Wine Refrigerator
      • Laundry: Gas Dryer Hookup, Washer Hookup
      Features
      • Bathroom, Central Vacuum
      • Flooring: Wood, Marble, Stone / Slate
      • Doors: French Doors
      • Windows: Insulated Windows
      • Basement: Full,Finished,Interior Entry,Sump Pump
      • Number of fireplaces: 2
      Interior area
      • Total structure area: 5,233
      • Total interior livable area: 5,233 sqft
      • Finished area above ground: 4,331
      • Finished area below ground: 902

      Property

      Parking
      • Total spaces: 2
      • Parking features: Paved Drive, Off Street, Paved
      • Uncovered spaces: 2
      Features
      • Patio & porch: Patio, Covered
      • Exterior features: Patio, Covered Patio/Deck, Pool - Inground, Rain Gutters, Storage, Professional Landscaping, Sprinkler System, Decorative Lighting, Fenced Yard, Stone Wall
      • Has private pool: Yes
      • Pool features: In Ground
      • Fencing: Fenced/Enclosed,Fenced
      Lot
      • Size: 10,812 Square Feet
      Details
      • Parcel number: M:015 B:0016 L:0,898747
      • Zoning: RG

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Contemporary,Villa
      • Property subtype: Single Family Residence
      Materials
      • Foundation: Concrete Perimeter
      Condition
      • Year built: 2004

      Utilities & green energy

      • Electric: Generator, 200+ Amp Service
      • Sewer: Public Sewer
      • Water: Public
      • Utilities for property: for Gas Range, for Gas Dryer, Washer Hookup

      Community & HOA

      Community
      • Features: Public Transportation, Shopping, Tennis Court(s), Walk/Jog Trails, Medical Facility, Bike Path, Conservation Area, Public School, T-Station
      • Security: Security System
      HOA
      • Has HOA: No
      Location
      • Region: Winchester

      Financial & listing details

      • Price per square foot: $534/sqft
      • Tax assessed value: $2,145,400
      • Annual tax amount: $23,792
      • Date on market: 5/13/2026
      • Road surface type: Paved

        Estimated market value

        $2,671,900

        $2.54M - $2.81M

        $7,947/mo

        Price history

        DateEventPrice
        5/14/2026Listed for sale$2,795,000$534/sqft
        Source: MLS PIN #73518621 Report a problem
        11/12/2025Listing removed$2,795,000$534/sqft
        Source: MLS PIN #73442182 Report a problem
        10/10/2025Listed for sale$2,795,000+3.7%$534/sqft
        Source: MLS PIN #73442182 Report a problem
        5/16/2025Listing removed$2,695,000$515/sqft
        Source: MLS PIN #73347754 Report a problem
        3/19/2025Listed for sale$2,695,000$515/sqft
        Source: MLS PIN #73347754 Report a problem
        11/21/2024Listing removed$2,695,000$515/sqft
        Source: MLS PIN #73292156 Report a problem
        9/19/2024Listed for sale$2,695,000+5.7%$515/sqft
        Source: MLS PIN #73292156 Report a problem
        11/1/2023Listing removed$2,550,000$487/sqft
        Source: MLS PIN #73147332 Report a problem
        10/13/2023Price change$2,550,000-1.9%$487/sqft
        Source: MLS PIN #73147332 Report a problem
        9/28/2023Price change$2,599,000-1.9%$497/sqft
        Source: MLS PIN #73147332 Report a problem
        8/11/2023Listed for sale$2,650,000-1.7%$506/sqft
        Source: MLS PIN #73147332 Report a problem
        7/1/2023Listing removed$2,695,000$515/sqft
        Source: MLS PIN #73107084 Report a problem
        5/4/2023Listed for sale$2,695,000+3.9%$515/sqft
        Source: MLS PIN #73107084 Report a problem
        12/13/2022Listing removed$2,595,000$496/sqft
        Source: MLS PIN #73047571 Report a problem
        11/3/2022Price change$2,595,000-3.7%$496/sqft
        Source: MLS PIN #73047571 Report a problem
        10/13/2022Listed for sale$2,695,000+84%$515/sqft
        Source: MLS PIN #73047571 Report a problem
        10/28/2016Sold$1,465,000-2.3%$280/sqft
        Source: Public Record Report a problem
        8/17/2016Pending sale$1,499,000$286/sqft
        Source: Waterfield Sotheby's International Realty #72044797 Report a problem
        7/28/2016Listed for sale$1,499,000+233.1%$286/sqft
        Source: Waterfield Sotheby's International Realty #72044797 Report a problem
        6/7/2002Sold$450,000+1700%$86/sqft
        Source: Public Record Report a problem
        5/1/2002Sold$25,000$5/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$23,792 +4.4%$2,145,400 +6.7%
        2024$22,783 +23.9%$2,010,900 +29.1%
        2023$18,386 -1.2%$1,558,100 +4.7%
        2022$18,614 +2.7%$1,487,900 +5.3%
        2021$18,121 +3.5%$1,412,400
        2020$17,500 +8.8%$1,412,400 +6.3%
        2019$16,088 +3.6%$1,328,500 +4.2%
        2018$15,536 +13.4%$1,274,500 +14.2%
        2017$13,701 +7.5%$1,115,700 +2.3%
        2016$12,744 +7.3%$1,091,100 +11.5%
        2015$11,875 +0.1%$978,200 +4.4%
        2014$11,859 +1%$936,700 +1.8%
        2013$11,747 +3.6%$919,900 +1.8%
        2012$11,344 +3.7%$903,900
        2011$10,937 +3.2%$903,900 -1.8%
        2010$10,594 +2.1%$920,400
        2009$10,373 +5.3%$920,400 -1.2%
        2008$9,847 +3.4%$931,600 +1.1%
        2007$9,521 +0.8%$921,700 +1.2%
        2006$9,446 +1.9%$910,900 +2.4%
        2005$9,272 +411.1%$889,800 +458.2%
        2004$1,814 -57.2%$159,400 -57.2%
        2003$4,242 +11.6%$372,800 +8.5%
        2002$3,801 +21.4%$343,700 +41.8%
        2000$3,132 -5.6%$242,300 +6.9%
        1999$3,317 $226,600

        Find assessor info on the county website

        Monthly payment

        Est. payment

          Payment breakdown

          Explore the cost of this home by adjusting the details. Changes won't be saved.
          All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
          HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
          Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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          Climate risks

          Neighborhood: 01890

          Getting around

          79 / 100
          Very Walkable
          60 / 100
          Bikeable

          Nearby schools

          GreatSchools rating
          Schools provided by the listing agent
          • Elementary: Lynch
          • Middle: Mccall
          • High: Winchester

          Source: MLS PIN. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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