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Pending
    • $479,900

    27 Hillside Dr, Sturbridge, MA 01566

    3beds
    2,209sqft
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    Single Family Residence
    Built in 1970
    0.95 Acres Lot
    $520,600 Zestimate®
    $217/sqft
    $-- HOA

    What's special

    Brick walkwayFire pitLarge sunny backyardQuiet cul-de-sac streetInviting open-concept layoutDining areaAll hardwood flooring
    Pool Opening Soon! Welcome home to this spacious 3 BR 2 BA Home located in the desirable Hillside Drive Neighborhood! Situated on a quiet cul-de-sac street, this home offers a convenient location for commuters while being just minutes to shopping, dining and everyday amenities. The main living level features all hardwood flooring and an inviting open-concept layout, including the FPLD Living Rm, with cozy pellet stove insert, Dining Area and Kitchen with a center island-perfect for entertaining. The Primary BR enjoys direct access to the recently renovated full Bath, while 2 additional Bedrooms complete this floor. The finished lower level offers additional living area with a Family Rm, also with pellet stove, and the 2nd Full Bath, ideal for guests, at home office or recreation area. Double French Doors from the main living area lead to an expansive 14 x 24 Deck overlooking the large, sunny backyard and IG pool! Additional highlights include a fire pit, brick walkway & a 2 car garage.
    18 days
    |
    878
    |
    60
    |

    Likely to sell faster than

    Zillow last checked:

    Listing updated:

    Listed by:

    Lorraine Herbert 508-864-4232,

    RE/MAX Prof Associates 508-347-9595

    Source: MLS PIN,MLS#: 73536696

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 3
      • Bathrooms: 2
      • Full bathrooms: 2
      • Main level bathrooms: 1
      Primary bedroom
      • Features: Bathroom - Full, Cedar Closet(s), Closet, Flooring - Hardwood
      • Level: First
      Bedroom 2
      • Features: Closet, Flooring - Hardwood
      • Level: First
      Bedroom 3
      • Features: Closet, Flooring - Hardwood
      • Level: First
      Bathroom 1
      • Features: Bathroom - Full, Closet - Linen, Flooring - Stone/Ceramic Tile, Countertops - Stone/Granite/Solid, Remodeled
      • Level: Main,First
      Bathroom 2
      • Features: Bathroom - Full, Flooring - Stone/Ceramic Tile, Countertops - Upgraded
      • Level: Basement
      Dining room
      • Features: Flooring - Hardwood, French Doors, Deck - Exterior, Exterior Access, Open Floorplan
      • Level: Main,First
      Family room
      • Features: Bathroom - Full, Flooring - Wall to Wall Carpet
      • Level: Basement
      Kitchen
      • Features: Flooring - Hardwood, Pantry, Countertops - Stone/Granite/Solid, Kitchen Island, Open Floorplan, Recessed Lighting
      • Level: Main,First
      Living room
      • Features: Flooring - Hardwood, Window(s) - Bay/Bow/Box, Open Floorplan, Recessed Lighting
      • Level: Main,First
      Heating
      • Electric Baseboard, Electric, Pellet Stove
      Cooling
      • Window Unit(s)
      Appliances
      • Included: Electric Water Heater, Range, Dishwasher, Microwave, Refrigerator, Washer, Dryer, Vacuum System
      • Laundry: In Basement, Electric Dryer Hookup, Washer Hookup
      Features
      • Central Vacuum
      • Flooring: Wood, Tile, Carpet, Hardwood
      • Doors: French Doors
      • Windows: Insulated Windows, Screens
      • Basement: Finished,Walk-Out Access,Interior Entry,Garage Access,Concrete
      • Number of fireplaces: 2
      • Fireplace features: Family Room, Living Room
      Interior area
      • Total structure area: 2,209
      • Total interior livable area: 2,209 sqft
      • Finished area above ground: 1,397
      • Finished area below ground: 812

      Property

      Parking
      • Total spaces: 8
      • Parking features: Under, Garage Door Opener, Paved Drive, Off Street, Paved
      • Attached garage spaces: 2
      • Uncovered spaces: 6
      Accessibility
      • Accessibility features: No
      Features
      • Patio & porch: Deck
      • Exterior features: Deck, Pool - Inground, Rain Gutters, Screens, Fenced Yard
      • Has private pool: Yes
      • Pool features: In Ground
      • Fencing: Fenced
      • Frontage length: 150.00
      Lot
      • Size: 0.95 Acres
      • Features: Cul-De-Sac, Cleared
      Details
      • Foundation area: 1512
      • Parcel number: M:0340 B:3846 L:0027,1703070
      • Zoning: SR

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Split Entry
      • Property subtype: Single Family Residence
      Materials
      • Frame
      • Foundation: Concrete Perimeter
      • Roof: Shingle
      Condition
      • Year built: 1970

      Utilities & green energy

      • Electric: Circuit Breakers
      • Sewer: Private Sewer
      • Water: Private
      • Utilities for property: for Electric Range, for Electric Dryer, Washer Hookup

      Community & HOA

      Community
      • Subdivision: Shepard Hills Neighborhood
      HOA
      • Has HOA: No
      Location
      • Region: Sturbridge

      Financial & listing details

      • Price per square foot: $217/sqft
      • Tax assessed value: $435,100
      • Annual tax amount: $6,788
      • Date on market: 6/29/2026
      • Road surface type: Paved

        Estimated market value

        $520,600

        $495,000 - $547,000

        $3,793/mo

        Price history

        DateEventPrice
        7/5/2026Pending sale$479,900$217/sqft
        Source: MLS PIN #73536696 Report a problem
        6/26/2026Listed for sale$479,900+58.9%$217/sqft
        Source: MLS PIN #73536696 Report a problem
        11/14/2017Sold$302,000+2.4%$137/sqft
        Source: Public Record Report a problem
        9/20/2017Listed for sale$295,000+1.7%$134/sqft
        Source: The Greene Realty Group #72231493 Report a problem
        11/19/2004Sold$290,000$131/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$6,568 +3.7%$412,300 +7.4%
        2024$6,332 +5.7%$384,000 +15.8%
        2023$5,992 +14.1%$331,600 +20.1%
        2022$5,251 $276,100
        2021$5,251 $276,100
        2020$5,251 +3.9%$276,100 +4.6%
        2019$5,056 +14.6%$264,000 +16.4%
        2018$4,411 +4.6%$226,900 +4.4%
        2017$4,216 +1.2%$217,300 +0.2%
        2016$4,167 +6.2%$216,900 +6.4%
        2015$3,923 +0.2%$203,900
        2014$3,915 -3.9%$203,900 -10.1%
        2013$4,073 -3.1%$226,900 -4.8%
        2012$4,203 +8.9%$238,400
        2011$3,860 +7.4%$238,400 -3.5%
        2010$3,594 +6.6%$247,000 -7.2%
        2009$3,370 +7.6%$266,200 -3.8%
        2008$3,133 +5%$276,800 +1.5%
        2007$2,984 -3.3%$272,800 +4.4%
        2006$3,085 +7.6%$261,400 +12.6%
        2005$2,868 -5.2%$232,200 +43.4%
        2004$3,024 +6.1%$161,900
        2003$2,851 +12.4%$161,900 +19.5%
        2001$2,537 +10.6%$135,500 +1.7%
        1997$2,293 $133,300
        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: 01566

        Getting around

        2 / 100
        Car-Dependent
        14 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Burgess
        • Middle: Tantasqua Jr Hi
        • High: Tantasqua Sr Hi

        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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