Nestled on 1.05 acres in a cul-de-sac neighborhood in Sturbridge, this beautifully maintained single-family home offers comfort, space, & thoughtful updates throughout! Step inside to a fireplaced living room that flows into a formal dining room & an expansive, sun-filled family room. An eat-in kitchen w/ granite countertops provides direct access to the deck, creating an easy indoor-outdoor connection, along w/ a convenient half bath on the main level. Upstairs features a spacious primary suite w/ ensuite bathroom, add'l great-sized bedrooms, & a tastefully-remodeled full bath. A partially finished basement adds versatile living space, while the private, flat backyard is ideal for outdoor enjoyment. Notable upgrades & features include a newer boiler, storm doors, garage doors (2026), new septic system (2025) & some windows have been updated w/ Harvey replacement windows. Ideal commuter location w/ ready access to I-90, I-84 and Rt 20 + minutes away from amenities! Home Sweet Home!
For sale
Price cut: $20K (7/11)
$624,900
39 Hillside Dr, Sturbridge, MA 01566
4beds
2,851sqft
Single Family Residence
Built in 1987
1.05 Acres Lot
$616,800 Zestimate®
$219/sqft
$-- HOA
What's special
Formal dining roomGreat-sized bedroomsExpansive sun-filled family roomStorm doors
- 54 days |
- 764 |
- 22 |
Zillow last checked:
Listing updated:
Listed by:
Jim Black Group 774-314-9448,
Real Broker MA, LLC 508-365-3532,
Richard Jenkins 774-243-2110
Source: MLS PIN,MLS#: 73520572
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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
HOA
- Has HOA: No
Location
- Region: Sturbridge
Financial & listing details
- Price per square foot: $219/sqft
- Tax assessed value: $500,800
- Annual tax amount: $7,978
- Date on market: 5/19/2026
- Exclusions: Washer, Dryer And Refrigerator
Estimated market value
$616,800
$586,000 - $648,000
$3,668/mo
Price history
| Date | Event | Price |
|---|---|---|
| 7/11/2026 | Listed for sale | $624,900-3.1%$219/sqft |
Source: MLS PIN #73520572 Report a problem | ||
| 7/1/2026 | Contingent | $644,900$226/sqft |
Source: MLS PIN #73520572 Report a problem | ||
| 6/8/2026 | Price change | $644,900-0.8%$226/sqft |
Source: MLS PIN #73520572 Report a problem | ||
| 5/18/2026 | Listed for sale | $649,900+238.5%$228/sqft |
Source: MLS PIN #73520572 Report a problem | ||
| 10/28/1994 | Sold | $192,000+1.6%$67/sqft |
Source: Public Record Report a problem | ||
| 8/29/1990 | Sold | $189,000-14.1%$66/sqft |
Source: Public Record Report a problem | ||
| 3/15/1988 | Sold | $220,000$77/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax 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 | $199,600 |
Find assessor info on the county website
Monthly payment
Est. payment$--/mo
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
Nearby schools
GreatSchools rating
- 6/10Burgess Elementary SchoolGrades: PK-6Distance: 2.7 mi
- 4/10Tantasqua Regional Jr High SchoolGrades: 7-8Distance: 6.3 mi
- 8/10Tantasqua Regional Sr High SchoolGrades: 9-12Distance: 6.4 mi
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A local agent can set up tours, give advice and negotiate with sellers.
A local lender can help you make sure your offer is ready when you are.
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- Massachusetts
- Worcester County
- Sturbridge
- 01566
- 39 Hillside Dr
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