Hillside Homes for Sale

Welcome to Hillside, a picturesque neighborhood nestled in the heart of Waterbury, Connecticut. Known for its charming streets and friendly atmosphere, Hillside offers a unique blend of suburban tranquility and urban convenience. This vibrant community is characterized by its tree-lined avenues, well-kept homes, and a strong sense of camaraderie among residents.

Hillside is ideal for families, professionals, and retirees alike, offering a variety of amenities that cater to all lifestyles. The area boasts excellent schools, beautiful parks, and recreational facilities, making it a perfect place for outdoor enthusiasts. Enjoy leisurely strolls or invigorating jogs along the scenic trails, or spend quality time with loved ones at the local playgrounds and sports fields. For those who appreciate a vibrant community life, Hillside hosts regular events and gatherings, fostering connections among neighbors.

As for homes for sale in Hillside, you’ll find an array of charming properties that cater to diverse tastes and budgets. From cozy single-family homes with manicured lawns to modern townhouses with contemporary finishes, there’s something for everyone. Many homes in the neighborhood feature spacious layouts, inviting backyards, and stunning views of the surrounding landscape.

With its welcoming spirit and convenient location, Hillside is not just a place to live; it's a place to thrive. Explore the homes for sale today and discover the perfect residence where you can create lasting memories in this delightful community. Whether you’re a first-time homebuyer or looking to settle down, Hillside is ready to welcome you home.

Newest Hillside Homes for Sale

$390,000

4 Beds ⋅ 4 Baths ⋅ 24191952 MLS

Welcome to 26 Trowbridge Street, a beautifully remodeled Cape Cod-style gem in Waterbury's desirable Hillside neighborhood and a fully operational, income-producing Airbnb with documented earnings. This move-in ready home is perfect for a family or an investor, having generated over $45,000 in net rental income across Airbnb and Vrbo in just seven months, with 152 nights booked, making it a rare find for short-term rental investors or anyone entering Airbnb hosting in CT. This spacious 4-bed, 3.5-bath home offers 2,075 sq ft blending classic charm with modern upgrades. The main level features a sunlit living room, formal dining room, a half bath for guests, and an updated kitchen with ample cabinet and counter space. Upstairs, four bedrooms include a primary suite with private full bath plus an additional room ideal as an office, nursery, or walk-in closet, and popular with longer-staying guests. Outside, a detached two-car garage and a low-maintenance yard offer everyday convenience, while a private hot tub has been a guest favorite. Furnishings and hot tub can be discussed to convey. With proven multi-platform earnings, an established 5-star hosting record, and a sought-after location, this is a turnkey home ready for its next owner, whether you're moving in or investing. Schedule your showing today.

26 Trowbridge St, Waterbury

Start Your Search

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.