35
$479,900
3 bd · 2 ba · 2,209 sqft
27 Hillside Dr, Sturbridge, MA
Lorraine Herbert · RE/MAX Prof Associates

No listing photos
2
Beds
1.5
Baths
816
Sqft
1950
Year built
Range $313,050 – $474,320 · 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 $471,657 in August 2025; lowest $200,564 in April 2020. The vertical scale starts at the series' own low, not at zero — it is drawn to show movement, not absolute size.
$78,737
Estimated monthly payment
$2,658/mo
Loan amount $314,948. Estimate only — your actual rate and payment depend on credit, location, and lender.
2025 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
Tantasqua Regional Junior High School
7-8 · Regular · Tantasqua School District
576 students · 11.7:1 student–teacher
Tantasqua Regional High School
9-12 · Regular · Tantasqua School District
632 students · 7.7:1 student–teacher
Tantasqua Regional Vocational
9-12 · Vocational Education · Tantasqua School District
542 students · 66.5:1 student–teacher
West Street School
2-5 · Regular · Southbridge School District
323 students · 11.2:1 student–teacher
Trinity Catholic Academy
PK-8 · Regular
109 students · 11.0:1 student–teacher
Southbridge Academy
9-12 · Special Education · Southbridge School District
21 students · 9.6:1 student–teacher
Rings at ½ mile and 1 mile. Basemap © OpenMapTiles © OpenStreetMap contributors.
Open the Sturbridge camera map2 CCTV cameras mapped within 1 mile of this home. None within ½ mile. Nearest: 0.8 mi southeast. Operator named in the data: Massachusetts Department of Transportation.
| Device type | Within ½ mi | Within 1 mi |
|---|---|---|
| CCTV cameras | 0 | 2 |
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.
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.
35
$479,900
3 bd · 2 ba · 2,209 sqft
27 Hillside Dr, Sturbridge, MA
Lorraine Herbert · RE/MAX Prof Associates
14$451,900
2 bd · 2 ba · 1,440 sqft
2 Rose Lane, Sturbridge, MA
Justin Stelmok · J.W. Management & Sales, Inc.
42$289,900
1 bd · 1 ba · 920 sqft
7 Crescent Way #101, Sturbridge, MA
Cynthia Sowa Forgit · Keller Williams Pinnacle Central
38$399,000
2 bd · 3 ba · 2,104 sqft
16 Bentwood Dr #16, Sturbridge, MA
Moira McGrath · Keller Williams Pinnacle Central
Price Reduced20$399,000
3 bd · 2 ba · 1,150 sqft
12 Fairground Rd, Sturbridge, MA
The Boston ONE Team · Serhant
35$384,000
2 bd · 3 ba · 1,876 sqft
66 Bentwood Dr #66, Sturbridge, MA
Tracy Brunette · Red Door Realty





Within 2 miles of this home: 29 restaurants and cafés, 3 grocery stores, and 25 parks and green spaces.
Place data from OpenStreetMap.
Panera Bread
New Boston Road
Ox Head Tavern
Main Street
McDonald's
Main Street
Burger King
Main Street
Sturbridge Seafood
Cedar Street Grille
Cedar Street
Wicked Licks
Veritas Restaurant
Main Street
Stop & Shop
Charlton Road
Sturbridge Marketplace at the Falls
Main Street
Micknuck's
Main Street
Cedar Lake
Herve and Mary Jane Gaumond Memorial Sanctuary
Cedar Pond Recreation Area
Opacum Pond
Sturbridge Town Beach
Opacum Conservation Area
Opacum Woods
Hobbs Brook