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For sale
    • $1,549,000

    50 Holland St, Winchester, MA 01890

    3beds
    2,640sqft
    : 
    $9,482/mo
    Get pre-qualified
    Single Family Residence
    Built in 1960
    6,625 Square Feet Lot
    $1,162,300 Zestimate®
    $587/sqft
    $-- HOA

    What's special

    Completely remodeled with exceptional custom finishes throughout, this stunning expanded cape with 3 levels, 3/4 bedrooms, 2.5-baths will exceed your expectations. The first floor features a spacious bedroom w/ full bath, an inviting living room w/ beautiful fireplace surrounded & custom built-ins, while the chef's kitchen is designed to impress with high end finishes, a large island and vaulted breakfast nook. The open floor plan flows into the dining room, complete with a custom built-in wine bar, ensuring easy entertaining. The second floor provides two very large bedrooms with great closet space and a tastefully remodeled hall bath. The beautifully finished lower level offers incredible flexibility with a cozy family room, kitchenette, laundry and 1/2 bath, with potential for a 4th BR, making it ideal for entertaining, guests, or extended living space. Step outside to an extraordinary backyard that feels like a resort! Enjoy the professionally landscaped grounds, lush gardens, and an expansive patio creating the ultimate outdoor oasis-featuring a built-in grill, pizza oven, bar seating, a hot tub, greenhouse, and shed. The retractable awnings make for comfortable shaded entertaining. It is truly a backyard that you will use all year round! Ideally located just outside Winchester center, enabling you to enjoy all the benefits of being close to town! This turn-key home is a must see, don't miss this one of a kind, move in ready home with so many recent upgrades!
    2 days
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    1,083
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    66
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    Zillow last checked:

    Listing updated:

    Listed by:

    Kim Covino & Co. Team 781-249-3854,

    Compass 781-219-0313,

    Kim Covino 781-249-3854

    Source: MLS PIN,MLS#: 73556633

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 3
      • Bathrooms: 3
      • Full bathrooms: 2
      • 1/2 bathrooms: 1
      Primary bedroom
      • Features: Ceiling Fan(s), Closet, Flooring - Hardwood
      • Level: Second
      • Area: 345
      • Dimensions: 23 x 15
      Bedroom 2
      • Features: Ceiling Fan(s), Closet, Flooring - Hardwood
      • Level: Second
      • Area: 299
      • Dimensions: 23 x 13
      Bedroom 3
      • Features: Ceiling Fan(s), Closet, Flooring - Hardwood, Deck - Exterior, Exterior Access, Slider
      • Level: First
      • Area: 180
      • Dimensions: 15 x 12
      Bathroom 1
      • Features: Bathroom - Full, Bathroom - Tiled With Tub & Shower, Flooring - Stone/Ceramic Tile, Recessed Lighting
      • Level: First
      • Area: 64
      • Dimensions: 8 x 8
      Bathroom 2
      • Features: Bathroom - Tiled With Tub & Shower, Lighting - Overhead
      • Level: Second
      • Area: 40
      • Dimensions: 8 x 5
      Bathroom 3
      • Features: Bathroom - Half
      • Level: Basement
      • Area: 110
      • Dimensions: 11 x 10
      Dining room
      • Features: Closet/Cabinets - Custom Built, Flooring - Hardwood, Wine Chiller, Lighting - Overhead
      • Level: First
      • Area: 168
      • Dimensions: 14 x 12
      Family room
      • Features: Ceiling Fan(s), Closet, Recessed Lighting
      • Level: Basement
      • Area: 221
      • Dimensions: 17 x 13
      Kitchen
      • Features: Flooring - Stone/Ceramic Tile, Dining Area, Pantry, Countertops - Stone/Granite/Solid, Kitchen Island, Exterior Access, Open Floorplan, Recessed Lighting, Stainless Steel Appliances, Wine Chiller, Lighting - Pendant
      • Level: Main,First
      • Area: 264
      • Dimensions: 22 x 12
      Living room
      • Features: Ceiling Fan(s), Closet/Cabinets - Custom Built, Flooring - Hardwood
      • Level: First
      • Area: 252
      • Dimensions: 18 x 14
      Office
      • Features: Closet, Lighting - Overhead
      • Level: Basement
      • Area: 154
      • Dimensions: 14 x 11
      Heating
      • Forced Air, Oil
      Cooling
      • Ductless
      Appliances
      • Included: Oven, Dishwasher, Disposal, Microwave, Range, Refrigerator, Freezer, Washer, Dryer, Wine Refrigerator
      • Laundry: In Basement
      Features
      • Closet, Lighting - Overhead, Wet bar, Recessed Lighting, Home Office, Kitchen, Wet Bar
      • Flooring: Hardwood
      • Windows: Screens
      • Has basement: No
      • Number of fireplaces: 1
      • Fireplace features: Living Room
      Interior area
      • Total structure area: 2,640
      • Total interior livable area: 2,640 sqft
      • Finished area above ground: 1,790
      • Finished area below ground: 850
      Video & virtual tour

      Property

      Parking
      • Total spaces: 4
      • Parking features: Paved Drive
      • Uncovered spaces: 4
      Features
      • Patio & porch: Deck, Patio, Covered
      • Exterior features: Deck, Patio, Covered Patio/Deck, Cabana, Rain Gutters, Hot Tub/Spa, Storage, Paddock, Professional Landscaping, Sprinkler System, Decorative Lighting, Screens, Fenced Yard, Garden, Stone Wall
      • Has spa: Yes
      • Spa features: Private
      • Fencing: Fenced
      Lot
      • Size: 6,625 Square Feet
      Details
      • Additional structures: Cabana
      • Parcel number: M:010 B:0086 L:0,897033
      • Zoning: RG
      • Horse amenities: Paddocks

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Cape
      • Property subtype: Single Family Residence
      Materials
      • Frame
      • Foundation: Concrete Perimeter
      • Roof: Shingle
      Condition
      • Year built: 1960

      Utilities & green energy

      • Sewer: Public Sewer
      • Water: Public
      • Utilities for property: for Electric Range

      Community & HOA

      Community
      • Features: Public Transportation, Shopping, Tennis Court(s), Park, Golf, Medical Facility, Bike Path, Conservation Area, Highway Access
      HOA
      • Has HOA: No
      Location
      • Region: Winchester

      Financial & listing details

      • Price per square foot: $587/sqft
      • Tax assessed value: $955,700
      • Annual tax amount: $10,599
      • Date on market: 7/30/2026

        Estimated market value

        $1,162,300

        $1.07M - $1.26M

        $4,117/mo

        Price history

        DateEventPrice
        7/29/2026Listed for sale$1,549,000+192.3%$587/sqft
        Source: MLS PIN #73556633 Report a problem
        8/27/2007Sold$530,000$201/sqft
        Source: Public Record Report a problem
        3/26/2004Sold$530,000$201/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$10,599 +1.4%$955,700 +3.6%
        2024$10,451 +3.3%$922,400 +7.6%
        2023$10,113 -0.3%$857,000 +5.7%
        2022$10,147 +6.6%$811,100 +9.3%
        2021$9,521 +3.5%$742,100
        2020$9,195 +14.1%$742,100 +11.5%
        2019$8,059 +3.3%$665,500 +4%
        2018$7,802 +5.1%$640,000 +5.9%
        2017$7,420 +6.9%$604,200 +1.7%
        2016$6,938 +3%$594,000 +7%
        2015$6,736 +3.6%$554,900 +8%
        2014$6,505 +3.9%$513,800 +4.8%
        2013$6,261 +4.9%$490,300 +3%
        2012$5,971 +3.7%$475,800
        2011$5,757 +4.1%$475,800 -1%
        2010$5,529 +2.1%$480,400
        2009$5,414 +7.4%$480,400 +0.8%
        2008$5,040 +5.6%$476,800 +3.2%
        2007$4,773 +1.5%$462,100 +1.9%
        2006$4,703 +11.5%$453,500 +12.1%
        2005$4,217 +8.4%$404,700 +18.4%
        2004$3,890 +2.7%$341,800 +2.7%
        2003$3,786 +11.7%$332,700 +8.5%
        2002$3,390 +19.7%$306,500 +40.4%
        2000$2,833 -5.6%$218,300 +6.5%
        1999$3,001 $205,000
        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
        79 / 100
        Very Bikeable

        Nearby schools

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

        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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