27 Hillside Drive, Sturbridge, MA 01566

$449,900 · For sale

27 Hillside Drive, Sturbridge

***OPEN HOUSE CANCELLED - ACCEPTED OFFER*** Welcome home to this inviting split-entry home, where hardwood floors, sun-filled living spaces, and a backyard oasis come together to create the perfect place to call home! Enter inside to discover a bright, open-concept living area featuring hardwood floors and a bay window that fills the space with natural light. The adjoining dining area offers sliding glass doors leading to the back deck, creating a seamless flow for indoor-outdoor entertaining. The spacious kitchen features crisp white cabinetry, ample countertop space, stainless steel appliances, and a center island perfect for everyday gatherings. Down the hall, you'll find three generously sized bedrooms, all boasting hardwood floors, and a full bath. The finished lower level offers even more room to spread out with a versatile bonus room featuring a picture window, perfect for a family room, home office, or recreation space—the choice is yours! A second full bath and direct access to the attached garage complete this level. Get ready to fall in love with the backyard! Step outside onto the spacious deck overlooking an expansive lawn framed by mature trees, complete with an inground pool that's sure to be the highlight of your summer! Whether you're hosting gatherings, soaking up the sunshine, or simply relaxing poolside, this outdoor retreat has something for everyone! A convenient storage shed adds the finishing touch. Don't miss your opportunity to make this wonderful property your own. Unpack and start making memories in your new home today!

About this address

27 Hillside Drive is a 3-bedroom, 2-bath single-family home for sale in Sturbridge, MA 01566 with 1,869 square feet, asking $449,900. It was built in 1970. It has been on our site since October 29, 2026.

The median asking price among the 11 other 3-bedroom single-family homes for sale in Sturbridge is $439,900. This one asks about 2% more. At $241 a square foot, it compares with a median of $273 among the 31 other single-family homes for sale in Sturbridge with a stated size.

At 1,869 square feet, it is smaller than 64% of the 11 other 3-bedroom single-family homes in Sturbridge with a stated size.

This home is assessed at $450,700 for fiscal year 2027. It last sold for $302,000 in November 2017. The assessor lists a lot of 0.95 acres.

It scores 0 out of 100 for walkability, from how close everyday places are.

The closest public schools by level are West Street (1.2 miles), Southbridge Middle School (3.5 miles) and Southbridge Academy (1.8 miles). The district decides which school serves an address.

Listing information from MLS Property Information Network (MLS PIN), MLS #73596518, deemed reliable but not guaranteed. Prices are compared with other homes listed on this site today. Trains and buses come from the transit agencies’ published schedules and schools from the National Center for Education Statistics. Distances are straight-line. Assessed values and past sales are public records from municipal assessors, published by MassGIS. An assessed value is set for taxation and may differ from market value.

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