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39 Hillside DrSturbridge, MA 01566

For Sale

$599,900

Smart Buyer Rebate - Ask

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!

Listed by Jim Black Group

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Real Broker MA, LLC

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3143256474

Listed by Richard Jenkins

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Real Broker MA, LLC

Last updated September 09, 2026

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Source: MLSPin #73520572

Listing Facts

  • TypeSingle-family
  • NeighborhoodSturbridge
  • Bedrooms4
  • Bathrooms3
  • Days on Prevu166
  • Taxes$7,978/year
  • Size2,851 sqft
  • Price per sqft$210

Amenities

  • Dishwasher
  • Private Outdoor Space
  • Parking
  • Swimming Pool

Location

Mortgage Calculator

Listing History

08/12/2026
Price Decreased
$599,900
07/11/2026
Status changed to Active
$624,900
07/11/2026
Price Decreased
$624,900
07/01/2026
Status changed to In Contract
$644,900
06/08/2026
Price Decreased
$644,900
05/18/2026
Listed by Real Broker MA, LLC
$649,900
  1. 08/12/2026$599,900
    Price Decreased
  2. 07/11/2026$624,900
    Status changed to Active
  3. 07/11/2026$624,900
    Price Decreased
  4. 07/01/2026$644,900
    Status changed to In Contract
  5. 06/08/2026$644,900
    Price Decreased
  6. 05/18/2026$649,900
    Listed by Real Broker MA, LLC

Property Details for 39 Hillside Dr

Association

Amenities

  • Community Features: Pool, Tennis Court(s), Park, Stable(s), Golf

Exterior

Construction

  • Roof: Shingle
  • Window Features: Insulated Windows
  • Year Built: 1987
  • Year Built Details: Actual
  • Architectural Style: Colonial
  • Construction Materials: Frame
  • Exterior Features: Rain Gutters, Garden

Features

  • Patio And Porch Features: Deck
  • View: Scenic

Measurements

  • Building Area Total: 2,851
  • Building Area Units: Square Feet
  • Lot Features: Cul-De-Sac, Cleared, Level
  • Lot Size Acres: 1.05
  • Lot Size Area: 1
  • Lot Size Square Feet: 45,738
  • Lot Size Units: Acres

Financial

Taxes

  • Parcel Number: M:340 B:000 L:3856039,1703078
  • Tax Annual Amount: $7,978.00
  • Tax Assessed Value: $500,800.00
  • Tax Year: 2025

Interior

Features

  • Appliances: Water Heater, Range, Dishwasher, Microwave, Plumbed For Ice Maker
  • Fireplace Features: Living Room
  • Fireplace: Yes
  • Fireplaces Total: 1
  • Flooring: Tile, Carpet, Hardwood
  • Interior Features: Walk-In Closet(s), Open Floorplan

Measurements

  • Living Area: 2,851

Rooms

  • Basement: Full, Partially Finished, Walk-Out Access, Interior Entry, Concrete
  • Has Basement: Yes
  • Bathrooms Full: 2
  • Bathrooms Half: 1
  • Bathrooms Total Integer: 3
  • Bedrooms Total: 4
  • Rooms Total: 9

Other

Environmental

  • Green Energy Efficient: Thermostat

General

  • Exclusions: Washer, Dryer And Refrigerator

Location

  • Subdivision Name: Westville

Parking

Parking

  • Attached Garage: Yes
  • Covered Spaces: 2
  • Garage Spaces: 2
  • Garage: Yes
  • Open Parking Spaces: 4
  • Open Parking: Yes
  • Parking Features: Attached, Garage Door Opener, Storage, Garage Faces Side, Off Street, Paved, Garage
  • Parking Total: 6

Utilities

Equipment

  • Electric: Circuit Breakers, 200+ Amp Service
  • Heating: Baseboard, Oil, Electric, Wood, Zoned
  • Has Heating: Yes
  • Laundry Features: Electric Dryer Hookup
  • Sewer: Private Sewer
  • Water Source: Private

Frequently Asked Questions

How many bedrooms and bathrooms does this single-family home have?

There are 4 bedrooms and 3 bathrooms in this single-family home at 39 Hillside Dr.

Does this single-family home have parking?

Yes, there are 2 parking spaces available for 39 Hillside Dr.

What are the annual taxes for 39 Hillside Dr?

Annual taxes for this single-family home are estimated at $7,978.

How does 39 Hillside Dr compare to other single-family homes in Sturbridge?

This single-family home is listed 6% above the average price for single-family homes in Sturbridge and has been on the market for 70 more days than the typical home in this area.

What is the square footage on this single-family home?

According to the MLS, this listing is 2,851 sqft.

39 Hillside Dr is a 4-bedroom, 3-bath single-family home for sale in Sturbridge MA 01566. Available on Prevu for 166 days at $599,900. This includes a recent price decrease of $25,000. This home features 2,851 square feet of living space, located in Sturbridge. The median listing price for single-family homes in this area is $465,000. Additional amenities include private outdoor space, dishwasher, parking, and swimming pool. Browse more single-family home listings in Worcester County.

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

Full MLS Disclaimers

Rebate estimate is indicative only and based on listing price and estimated buyer's agent commission paid by owner, if applicable. Final rebates are subject to Terms of Use and may vary due to final negotiated transaction terms.