Single Family Residence at 39 Hillside Dr, Sturbridge MA 01566, Sturbridge
Single Family Residence at 39 Hillside Dr, Sturbridge MA 01566, Sturbridge, photo 2 of 41
Single Family Residence at 39 Hillside Dr, Sturbridge MA 01566, Sturbridge, photo 3 of 41
Single Family Residence at 39 Hillside Dr, Sturbridge MA 01566, Sturbridge, photo 4 of 41
Single Family Residence at 39 Hillside Dr, Sturbridge MA 01566, Sturbridge, photo 5 of 41
Single Family Residence at 39 Hillside Dr, Sturbridge MA 01566, Sturbridge, photo 6 of 41
Single Family Residence at 39 Hillside Dr, Sturbridge MA 01566, Sturbridge, photo 7 of 41
Single Family Residence at 39 Hillside Dr, Sturbridge MA 01566, Sturbridge, photo 8 of 41
Single Family Residence at 39 Hillside Dr, Sturbridge MA 01566, Sturbridge, photo 9 of 41
Single Family Residence at 39 Hillside Dr, Sturbridge MA 01566, Sturbridge, photo 10 of 41
Single Family Residence at 39 Hillside Dr, Sturbridge MA 01566, Sturbridge, photo 11 of 41
Single Family Residence at 39 Hillside Dr, Sturbridge MA 01566, Sturbridge, photo 12 of 41
Single Family Residence at 39 Hillside Dr, Sturbridge MA 01566, Sturbridge, photo 13 of 41
Single Family Residence at 39 Hillside Dr, Sturbridge MA 01566, Sturbridge, photo 14 of 41
Single Family Residence at 39 Hillside Dr, Sturbridge MA 01566, Sturbridge, photo 15 of 41
Single Family Residence at 39 Hillside Dr, Sturbridge MA 01566, Sturbridge, photo 16 of 41
Single Family Residence at 39 Hillside Dr, Sturbridge MA 01566, Sturbridge, photo 17 of 41
Single Family Residence at 39 Hillside Dr, Sturbridge MA 01566, Sturbridge, photo 18 of 41
Single Family Residence at 39 Hillside Dr, Sturbridge MA 01566, Sturbridge, photo 19 of 41
Single Family Residence at 39 Hillside Dr, Sturbridge MA 01566, Sturbridge, photo 20 of 41
Single Family Residence at 39 Hillside Dr, Sturbridge MA 01566, Sturbridge, photo 21 of 41
Single Family Residence at 39 Hillside Dr, Sturbridge MA 01566, Sturbridge, photo 22 of 41
Single Family Residence at 39 Hillside Dr, Sturbridge MA 01566, Sturbridge, photo 23 of 41
Single Family Residence at 39 Hillside Dr, Sturbridge MA 01566, Sturbridge, photo 24 of 41
Single Family Residence at 39 Hillside Dr, Sturbridge MA 01566, Sturbridge, photo 25 of 41
Single Family Residence at 39 Hillside Dr, Sturbridge MA 01566, Sturbridge, photo 26 of 41
Single Family Residence at 39 Hillside Dr, Sturbridge MA 01566, Sturbridge, photo 27 of 41
Single Family Residence at 39 Hillside Dr, Sturbridge MA 01566, Sturbridge, photo 28 of 41
Single Family Residence at 39 Hillside Dr, Sturbridge MA 01566, Sturbridge, photo 29 of 41
Single Family Residence at 39 Hillside Dr, Sturbridge MA 01566, Sturbridge, photo 30 of 41
Single Family Residence at 39 Hillside Dr, Sturbridge MA 01566, Sturbridge, photo 31 of 41
Single Family Residence at 39 Hillside Dr, Sturbridge MA 01566, Sturbridge, photo 32 of 41
Single Family Residence at 39 Hillside Dr, Sturbridge MA 01566, Sturbridge, photo 33 of 41
Single Family Residence at 39 Hillside Dr, Sturbridge MA 01566, Sturbridge, photo 34 of 41
Single Family Residence at 39 Hillside Dr, Sturbridge MA 01566, Sturbridge, photo 35 of 41
Single Family Residence at 39 Hillside Dr, Sturbridge MA 01566, Sturbridge, photo 36 of 41
Single Family Residence at 39 Hillside Dr, Sturbridge MA 01566, Sturbridge, photo 37 of 41
Single Family Residence at 39 Hillside Dr, Sturbridge MA 01566, Sturbridge, photo 38 of 41
Single Family Residence at 39 Hillside Dr, Sturbridge MA 01566, Sturbridge, photo 39 of 41
Single Family Residence at 39 Hillside Dr, Sturbridge MA 01566, Sturbridge, photo 40 of 41
Single Family Residence at 39 Hillside Dr, Sturbridge MA 01566, Sturbridge, photo 41 of 41
41 photos

$599,900

39 Hillside Dr, Sturbridge MA 01566
Sturbridge, MA 01566
Listed by Jim Black Group
Bedrooms
4
Bathrooms
2.1
Living area
2,851 sqft
Year built
1987

About this home

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!

Highlights

ViewFireplace

Property details

MLS #
73520572
Property type
Single Family Residence
Subdivision
Westville
Status
Active
Days on market
102
On market date
May 18, 2026
Stories
N/A
Total bathrooms
3
Garage spaces
2
Parking spaces
6
Lot size
1.05 acres
Loading map…

Nearby schools

Within 10 miles · public school directory data (NCES)

Elementary
West Street
1.22 mi away · Grades 1-5
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
312
Student:teacher ratio
10.8:1
District
Southbridge
Middle
Southbridge Middle School
3.5 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
407
Student:teacher ratio
12.0:1
District
Southbridge
High
Southbridge Academy
1.74 mi away · Grades 6-12
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
42
Student:teacher ratio
3.5:1
District
Southbridge

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

$
%
%
Adjust tax / insurance estimates
% / yr
$
/mo
Est. monthly payment
$3,763/mo
$119,980 down
$479,920 loan
Principal & interest$3,113
Property tax (est.)$500
Home insurance (est.)$150

Similar homes you might like

Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated 13 days ago.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.