Hillside Homes for Sale

Welcome to the enchanting neighborhood of Hillside, nestled in the heart of Waterbury, Connecticut. Known for its picturesque views and vibrant community, Hillside is a hidden gem in New Haven County that offers a perfect blend of suburban charm and urban convenience.

As you stroll through the tree-lined streets, you'll be captivated by the well-maintained homes that showcase a variety of architectural styles, from classic colonials to modern builds. The neighborhood is characterized by its friendly atmosphere, where neighbors greet one another with warm smiles and community events foster a sense of belonging. Families will appreciate the proximity to excellent schools, parks, and recreational facilities, making Hillside an ideal place to raise children.

For those who enjoy the outdoors, Hillside boasts several parks and green spaces, perfect for picnics, leisurely walks, or weekend sports. The nearby Mattatuck Trail offers hiking and biking opportunities, allowing residents to immerse themselves in nature while still being close to the amenities of city life.

Currently, there are a variety of homes for sale in Hillside, catering to diverse tastes and budgets. Whether you're a first-time homebuyer seeking a cozy starter home or a growing family in search of a spacious residence, Hillside has something for everyone. With its welcoming community, beautiful surroundings, and convenient location, Hillside is not just a place to live—it's a place to thrive. Come discover your dream home in this charming neighborhood today!

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

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