39 Hillside Dr Sturbridge, MA ^$ 599,900

39 Hillside Dr

^$ 599,900

Back to search

39 Hillside Dr

Sturbridge, MA, 01566

^$ 599,900

Bedrooms4 Baths2.1 Sq 2,851

Monthly Estimate*

^$ 3,788

39 Hillside Dr, Sturbridge, MA 01566 - Image 1

39 Hillside Dr, Sturbridge, MA 01566 - Image 2

39 Hillside Dr, Sturbridge, MA 01566 - Image 3

39 Hillside Dr, Sturbridge, MA 01566 - Image 4

39 Hillside Dr, Sturbridge, MA 01566 - Image 5

39 Hillside Dr, Sturbridge, MA 01566 - Image 6

39 Hillside Dr, Sturbridge, MA 01566 - Image 7

39 Hillside Dr, Sturbridge, MA 01566 - Image 8

39 Hillside Dr, Sturbridge, MA 01566 - Image 9

39 Hillside Dr, Sturbridge, MA 01566 - Image 10

39 Hillside Dr, Sturbridge, MA 01566 - Image 11

39 Hillside Dr, Sturbridge, MA 01566 - Image 12

39 Hillside Dr, Sturbridge, MA 01566 - Image 13

39 Hillside Dr, Sturbridge, MA 01566 - Image 14

39 Hillside Dr, Sturbridge, MA 01566 - Image 15

39 Hillside Dr, Sturbridge, MA 01566 - Image 16

39 Hillside Dr, Sturbridge, MA 01566 - Image 17

39 Hillside Dr, Sturbridge, MA 01566 - Image 18

39 Hillside Dr, Sturbridge, MA 01566 - Image 19

39 Hillside Dr, Sturbridge, MA 01566 - Image 20

39 Hillside Dr, Sturbridge, MA 01566 - Image 21

39 Hillside Dr, Sturbridge, MA 01566 - Image 22

39 Hillside Dr, Sturbridge, MA 01566 - Image 23

39 Hillside Dr, Sturbridge, MA 01566 - Image 24

39 Hillside Dr, Sturbridge, MA 01566 - Image 25

39 Hillside Dr, Sturbridge, MA 01566 - Image 26

39 Hillside Dr, Sturbridge, MA 01566 - Image 27

39 Hillside Dr, Sturbridge, MA 01566 - Image 28

39 Hillside Dr, Sturbridge, MA 01566 - Image 29

39 Hillside Dr, Sturbridge, MA 01566 - Image 30

39 Hillside Dr, Sturbridge, MA 01566 - Image 31

39 Hillside Dr, Sturbridge, MA 01566 - Image 32

39 Hillside Dr, Sturbridge, MA 01566 - Image 33

39 Hillside Dr, Sturbridge, MA 01566 - Image 34

39 Hillside Dr, Sturbridge, MA 01566 - Image 35

39 Hillside Dr, Sturbridge, MA 01566 - Image 36

39 Hillside Dr, Sturbridge, MA 01566 - Image 37

39 Hillside Dr, Sturbridge, MA 01566 - Image 38

39 Hillside Dr, Sturbridge, MA 01566 - Image 39

39 Hillside Dr, Sturbridge, MA 01566 - Image 40

39 Hillside Dr, Sturbridge, MA 01566 - Image 41

Single Family Home for sale in Sturbridge, MA

for $599,900 with 4 bedrooms and 2 full baths, 1 half bath. This 2,851 square foot home was built in 1987 on a lot size of 1.05.

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!

Single Family Active

Price

^$ 599,900

Bedrooms

Full Bath

Half Bath

Property Type

Single Family

Taxes

^$ 7,978

Style

Colonial

Lot Size

1.05

Year Built

1987

Town/City

Sturbridge

County/Region

Worcester

MLS | Web ID

73520572

List By

Jim Black Group

Listing Agent

Real Broker Ma, Llc

Broker

Affordability Calculator

$4,453

Per Month

Monthly Principal & Interest: $3,788
Monthly Property Taxes: $665
Monthly Home Insurance: --

Set your offer price

Down Payment

Loan Term

Interest Rate

Yearly Property Taxes

Yearly Home Insurance

Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

Learn more about how to save

Discover how much house you can afford

Your dream home may be within reach.

Learn More about how to save

THE TIME TO SELL IS NOW! What's my home worth?

Nearby

Trends

Single family listings in Sturbridge, MA

Average List Price ^$587,018

Percent of Sale Price 2%

About Sturbridge, MA

9,470 Population

21% Since 2002

^$88,155 Median Income

44.38 Median Age

33% Households with Children

View more area information

Trends Information provided by ATTOM Data Solutions.

Neighborhood & Schools

MLS Property Information Network, Inc rules require that you sign in here to see more detail on this property.

Pricing History

Date	Price	Price Change	Description
8/12/2026	$599,900	-4.00%	Price Down
7/11/2026	$624,900	-3.10%	Price Down
6/8/2026	$644,900	-0.77%	Price Down
5/18/2026	$649,900		Listed Price

Map

More homes like this one

homes for you

See all

39 Hillside Dr, Sturbridge, MA, 01566 is a Single Family Home for sale at $599,900 with 2,851 sqft and a lot size of 1.05. 39 Hillside Dr has 4 bedrooms, 2.1 baths, and was built in 1987. The property's zip code is 01566 which is in Sturbridge, MA

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

Data is updated as of 8/19/2026.

The real estate information and related content displayed on this site is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

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 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 or leasing 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 or leasing. 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 Name

*Email

*Phone

I am interested in financing options

Get more info

By submitting the form, you agree that Weichert^® may contact you via phone or text about your inquiry, which may involve the use of automated means. You are not required to consent as a condition of purchasing any property, goods or services. For any other information please read our privacy policy.

Get more info

Looking for an Associate?

Already Working with an Associate?

39 Hillside Dr

Single Family Home for sale in Sturbridge, MA

Affordability Calculator

Neighborhood & Schools

Map

More homes like this one

Get more info about this home