38
$449,900
3 bd · 2 ba · 1,869 sqft
27 Hillside Drive, Sturbridge, MA
AJ Bruce · Lamacchia Realty, Inc.

No listing photos
4
Beds
3
Baths
2,020
Sqft
1956
Year built
Range $331,476 – $439,766 · as of August 30, 2026
ATTOM automated valuation model · 54 published estimates over 6.7 years · shaded band is the model's own published low-to-high range
Highest reading $620,187 in July 2025; lowest $308,722 in January 2020. The vertical scale starts at the series' own low, not at zero — it is drawn to show movement, not absolute size.
$77,124
Estimated monthly payment
$2,573/mo
Loan amount $308,497. Estimate only — your actual rate and payment depend on credit, location, and lender.
2026 roll
School ratings (A+ to F) from HJN community data.
Burgess Elementary School
PK-6 · Regular · Sturbridge School District
842 students · 12.0:1 student–teacher
Old Sturbridge Academy Charter Public School
KG-8 · Regular · Old Sturbridge Academy Charter Public School
356 students · 14.5:1 student–teacher
Trinity Catholic Academy
PK-8 · Regular
109 students · 11.0:1 student–teacher
West Street School
2-5 · Regular · Southbridge School District
323 students · 11.2:1 student–teacher
Charlton Street School
2-5 · Regular · Southbridge School District
288 students · 13.7:1 student–teacher
Tantasqua Regional Junior High School
7-8 · Regular · Tantasqua School District
576 students · 11.7:1 student–teacher
Charlton Elementary School
PK-1 · Regular · Dudley-Charlton Regional School District
333 students · 13.0:1 student–teacher
Viewpoint Christian Academy
KG-12 · Alternative/Other
67 students · 9.6:1 student–teacher
MLS Property Information Network (MLS PIN)Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.
38
$449,900
3 bd · 2 ba · 1,869 sqft
27 Hillside Drive, Sturbridge, MA
AJ Bruce · Lamacchia Realty, Inc.
40$439,000
3 bd · 2 ba · 1,958 sqft
25 Wallace Rd, Sturbridge, MA
Jennifer McKinstry · Byrnes Real Estate Group LLC
Price Reduced38$499,900
4 bd · 3 ba · 2,741 sqft
90 Sturbridge Hills Rd #90, Sturbridge, MA
The Riel Estate Team · Keller Williams Pinnacle Central
32$379,900
3 bd · 3 ba · 1,560 sqft
16 Charlton St, Sturbridge, MA
Gracellen Riel · RE/MAX Prof Associates
Price Reduced42$439,900
3 bd · 2 ba · 2,050 sqft
37 Breakneck Rd, Sturbridge, MA
Kenneth Olson · eXp Realty LLC - Corporate Office
Price Reduced42$349,999
3 bd · 2 ba · 1,404 sqft
18 Fiske Hill Rd, Sturbridge, MA
Kathleen Sposato · Sposato Realty Group
Within 2 miles of this home: 13 restaurants and cafés, 1 grocery store, and 11 parks and green spaces.
Place data from OpenStreetMap.
Subway
Uno Pizzeria & Grill
Charlton Road
Applebee's
American restaurant · Charlton Road
Mini Sturbridge Coffee House
Frisbie's Dairy Barn
D'Angelo Grilled Sandwiches
Papa Gino's
Fresh City
Stop & Shop
Charlton Road
Walker Pond
Wells State Park
Walker Pond Road
Opacum Woods
Hobbs Brook
Opacum Pond
Herve and Mary Jane Gaumond Memorial Sanctuary
Opacum Conservation Area
Beaver Pond





Rings at ½ mile and 1 mile. Basemap © OpenMapTiles © OpenStreetMap contributors.
Open the Sturbridge camera map2 CCTV cameras mapped within ½ mile of this home. Nearest: 0.3 mi southeast. Operator named in the data: Massachusetts Department of Transportation.
| Device type | Within ½ mi | Within 1 mi |
|---|---|---|
| CCTV cameras | 2 | 8 |
Community-reported via OpenStreetMap; may be incomplete. Data as of . © OpenStreetMap contributors (ODbL)
CCTV cameras are fixed video cameras that record a street, building or other area.