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For sale
    • Price cut: $25K (8/12)
    $599,900

    39 Hillside Dr, Sturbridge, MA 01566

    4beds
    2,851sqft
    : 
    $4,026/mo
    Get pre-qualified
    Single Family Residence
    Built in 1987
    1.05 Acres Lot
    $596,200 Zestimate®
    $210/sqft
    $-- HOA

    What's special

    Select harvey replacement windowsFormal dining roomPicturesque cul-de-sacGenerously sized bedroomsExpansive sun-filled family roomStorm doors
    Nestled on 1.05 acres in Sturbridge's desirable Westville neighborhood, this beautifully maintained single-family home offers the perfect blend of privacy, natural beauty, and everyday convenience! Set within a picturesque cul-de-sac, enjoy peaceful surroundings ideal for daily walks and a nature-inspired lifestyle, all while remaining just minutes from local amenities. Step inside to a fireplaced living room that flows into a formal dining room and an expansive, sun-filled family room. An eat-in kitchen with granite countertops provides direct access to the deck, creating an easy indoor-outdoor connection, along with a convenient half bath on the main level. Upstairs features a spacious primary suite with an ensuite bathroom, additional generously sized bedrooms, and a tastefully remodeled full bath. A partially finished basement adds versatile living space, while the private, level backyard is ideal for relaxing or entertaining. Notable upgrades include a newer boiler, storm doors, garage doors (2026), a new septic system (2025), and select Harvey replacement windows. An ideal commuter location with easy access to I-90, I-84, and Route 20. Welcome Home!
    101 days
    |
    999
    |
    47
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Jim Black Group 314-325-6474,

    Real Broker MA, LLC 508-365-3532,

    Richard Jenkins 774-243-2110

    Source: MLS PIN,MLS#: 73520572

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 3
      • Full bathrooms: 2
      • 1/2 bathrooms: 1
      Primary bedroom
      • Features: Bathroom - Full, Ceiling Fan(s), Walk-In Closet(s), Flooring - Wall to Wall Carpet
      • Level: Second
      • Area: 225
      • Dimensions: 15 x 15
      Bedroom 2
      • Features: Closet, Flooring - Wall to Wall Carpet
      • Level: Second
      • Area: 195
      • Dimensions: 15 x 13
      Bedroom 3
      • Features: Closet, Flooring - Wall to Wall Carpet
      • Level: Second
      • Area: 180
      • Dimensions: 15 x 12
      Bedroom 4
      • Features: Closet, Flooring - Wall to Wall Carpet
      • Level: Second
      • Area: 110
      • Dimensions: 11 x 10
      Primary bathroom
      • Features: Yes
      Bathroom 1
      • Features: Bathroom - Full, Bathroom - With Shower Stall, Closet - Linen, Flooring - Stone/Ceramic Tile
      • Level: Second
      • Area: 55
      • Dimensions: 11 x 5
      Bathroom 2
      • Features: Bathroom - Full, Bathroom - Tiled With Tub & Shower, Flooring - Stone/Ceramic Tile, Remodeled
      • Level: Second
      • Area: 54
      • Dimensions: 9 x 6
      Bathroom 3
      • Features: Bathroom - Half, Closet, Flooring - Stone/Ceramic Tile
      • Level: First
      • Area: 30
      • Dimensions: 6 x 5
      Dining room
      • Features: Flooring - Hardwood
      • Level: First
      • Area: 140
      • Dimensions: 14 x 10
      Family room
      • Features: Flooring - Hardwood, Open Floorplan
      • Level: First
      • Area: 315
      • Dimensions: 21 x 15
      Kitchen
      • Features: Flooring - Stone/Ceramic Tile, Balcony / Deck, Countertops - Stone/Granite/Solid, Breakfast Bar / Nook, Exterior Access, Open Floorplan
      • Level: First
      • Area: 168
      • Dimensions: 14 x 12
      Living room
      • Features: Flooring - Hardwood, Open Floorplan
      • Level: First
      • Area: 195
      • Dimensions: 15 x 13
      Heating
      • Baseboard, Oil, Electric, Wood
      Cooling
      • None
      Appliances
      • Included: Water Heater, Range, Dishwasher, Microwave, Plumbed For Ice Maker
      • Laundry: Flooring - Stone/Ceramic Tile, First Floor, Electric Dryer Hookup
      Features
      • Closet, Game Room
      • Flooring: Tile, Carpet, Hardwood, Flooring - Wall to Wall Carpet
      • Doors: Insulated Doors, Storm Door(s)
      • Windows: Insulated Windows
      • Basement: Full,Partially Finished,Walk-Out Access,Interior Entry,Concrete
      • Number of fireplaces: 1
      • Fireplace features: Living Room
      Interior area
      • Total structure area: 2,851
      • Total interior livable area: 2,851 sqft
      • Finished area above ground: 2,272
      • Finished area below ground: 579

      Property

      Parking
      • Total spaces: 6
      • Parking features: Attached, Garage Door Opener, Storage, Garage Faces Side, Off Street, Paved
      • Attached garage spaces: 2
      • Uncovered spaces: 4
      Features
      • Patio & porch: Deck - Wood
      • Exterior features: Deck - Wood, Rain Gutters, Garden
      • Has view: Yes
      • View description: Scenic View(s)
      • Waterfront features: Lake/Pond, Unknown To Beach, Beach Ownership(Private)
      Lot
      • Size: 1.05 Acres
      • Features: Cul-De-Sac, Cleared, Level
      Details
      • Parcel number: M:340 B:000 L:3856039,1703078
      • Zoning: .

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Colonial
      • Property subtype: Single Family Residence
      Materials
      • Frame
      • Foundation: Concrete Perimeter
      • Roof: Shingle
      Condition
      • Year built: 1987

      Utilities & green energy

      • Electric: Circuit Breakers, 200+ Amp Service
      • Sewer: Private Sewer
      • Water: Private
      • Utilities for property: for Electric Range, for Electric Oven, for Electric Dryer, Icemaker Connection
      Green energy
      • Energy efficient items: Thermostat

      Community & HOA

      Community
      • Features: Shopping, Pool, Tennis Court(s), Park, Walk/Jog Trails, Stable(s), Golf, Medical Facility, Conservation Area, Highway Access, House of Worship, Public School
      • Subdivision: Westville
      HOA
      • Has HOA: No
      Location
      • Region: Sturbridge

      Financial & listing details

      • Price per square foot: $210/sqft
      • Tax assessed value: $500,800
      • Annual tax amount: $7,978
      • Date on market: 5/18/2026
      • Exclusions: Washer, Dryer And Refrigerator

        Estimated market value

        $596,200

        $566,000 - $626,000

        $3,807/mo

        Price history

        DateEventPrice
        8/12/2026Price change$599,900-4%$210/sqft
        Source: MLS PIN #73520572 Report a problem
        7/11/2026Listed for sale$624,900-3.1%$219/sqft
        Source: MLS PIN #73520572 Report a problem
        7/1/2026Contingent$644,900$226/sqft
        Source: MLS PIN #73520572 Report a problem
        6/8/2026Price change$644,900-0.8%$226/sqft
        Source: MLS PIN #73520572 Report a problem
        5/18/2026Listed for sale$649,900+238.5%$228/sqft
        Source: MLS PIN #73520572 Report a problem
        10/28/1994Sold$192,000+1.6%$67/sqft
        Source: Public Record Report a problem
        8/29/1990Sold$189,000-14.1%$66/sqft
        Source: Public Record Report a problem
        3/15/1988Sold$220,000$77/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$7,978 +2%$500,800 +5.5%
        2024$7,825 +3%$474,500 +12.9%
        2023$7,595 +14.1%$420,300 +20.1%
        2022$6,655 $349,900
        2021$6,655 $349,900
        2020$6,655 +4.7%$349,900 +5.4%
        2019$6,358 +1.5%$332,000 +3%
        2018$6,264 +4.5%$322,200 +4.2%
        2017$5,997 +4.4%$309,100 +3.4%
        2016$5,744 +0.7%$299,000 +0.9%
        2015$5,703 +4.8%$296,400 +4.6%
        2014$5,441 -0.7%$283,400 -7.1%
        2013$5,478 +0.7%$305,200 -1.1%
        2012$5,439 +5%$308,500 -3.5%
        2011$5,178 +5.6%$319,800 -5.1%
        2010$4,903 +9.9%$337,000 -4.4%
        2009$4,461 +5.9%$352,400 -5.3%
        2008$4,212 +1.4%$372,100 -2%
        2007$4,155 -0.6%$379,800 +7.2%
        2006$4,182 +1.3%$354,400 +6%
        2005$4,129 -6.1%$334,300 +42%
        2004$4,399 +6.1%$235,500
        2003$4,147 +10.5%$235,500 +17.5%
        2001$3,753 +9.3%$200,500 +0.5%
        1997$3,433 $199,600
        Find assessor info on the county website

        Monthly payment

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        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
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        Climate risks

        Neighborhood: 01566

        Getting around

        0 / 100
        Car-Dependent
        19 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating

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