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

No listing photos
3
Beds
2
Baths
1,768
Sqft
2001
Year built
Range $301,280 – $422,348 · 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 $580,412 in July 2025; lowest $309,582 in April 2020. The vertical scale starts at the series' own low, not at zero — it is drawn to show movement, not absolute size.
$72,363
Estimated monthly payment
$2,421/mo
Loan amount $289,451. Estimate only — your actual rate and payment depend on credit, location, and lender.
2026 roll
Within 2 miles of this home: 6 restaurants and cafés, 1 grocery store, and 10 parks and green spaces.
Place data from OpenStreetMap.
Auntie Anne's
McDonald's
Massachusetts Turnpike
Fresh City
D'Angelo Grilled Sandwiches
Papa Gino's
Subway
Stop & Shop
Charlton Road
Beaver Pond
Jennings Road Extension Open Space
Walker Pond
Upper Sibley Pond
Manor Ridge
Wells State Park
Walker Pond Road
Lower Sibley Pond
Willow Pool
School ratings (A+ to F) from HJN community data.
Charlton Elementary School
PK-1 · Regular · Dudley-Charlton Regional School District
333 students · 13.0:1 student–teacher
Burgess Elementary School
PK-6 · Regular · Sturbridge School District
842 students · 12.0:1 student–teacher
Bay Path Regional Vocational Technical High School
9-12 · Vocational Education · Southern Worcester County Regional Vocational School Distric
1,188 students · 9.7:1 student–teacher
Old Sturbridge Academy Charter Public School
KG-8 · Regular · Old Sturbridge Academy Charter Public School
356 students · 14.5:1 student–teacher
Tantasqua Regional Junior High School
7-8 · Regular · Tantasqua School District
576 students · 11.7:1 student–teacher
Viewpoint Christian Academy
KG-12 · Alternative/Other
67 students · 9.6:1 student–teacher
Trinity Catholic Academy
PK-8 · Regular
109 students · 11.0:1 student–teacher
Tantasqua Regional High School
9-12 · Regular · Tantasqua School District
632 students · 7.7:1 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.
42$389,900
2 bd · 1 ba · 1,196 sqft
16-18 Curboy Rd, Sturbridge, MA
Lisa Zemack · Zemack Real Estate
40$439,000
3 bd · 2 ba · 1,958 sqft
25 Wallace Rd, Sturbridge, MA
Jennifer McKinstry · Byrnes Real Estate Group LLC
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




