Hillside Homes under $1.25 million

Welcome to Hillside, a charming neighborhood nestled in the heart of Waterbury, Connecticut. Known for its picturesque streets and friendly community atmosphere, Hillside offers a delightful blend of suburban tranquility and urban convenience. With its lush green parks, tree-lined avenues, and a strong sense of community, Hillside is the perfect place for families, young professionals, and retirees alike.

One of the standout features of this neighborhood is its diverse range of homes, many of which are available for under $1.25 million. Whether you’re searching for a classic colonial, a cozy bungalow, or a modern townhouse, Hillside has something to suit every taste and lifestyle. Each property reflects the character of the neighborhood, with well-maintained lawns and inviting facades that create a warm and welcoming environment.

Residents of Hillside enjoy easy access to a variety of local amenities, including shopping centers, restaurants, and recreational facilities. The area is also well-connected to public transportation, making commuting to nearby cities a breeze. Families will appreciate the proximity to highly-rated schools and community programs that foster a strong sense of belonging.

Outdoor enthusiasts will love exploring the nearby parks and nature trails, perfect for a leisurely stroll, a morning jog, or a weekend picnic. With its vibrant community spirit, beautiful homes, and convenient location, Hillside is truly a hidden gem in Waterbury, offering an ideal setting for those looking to establish roots in Connecticut. Come discover the charm of Hillside—your dream home awaits!

Newest Hillside Homes under $1.25 million

$869,900

20 Beds ⋅ 6 Baths ⋅ 24210244 MLS

This fully updated 6-unit property consists of (2) 4-bed units and (4) 3-bed units with roughly 1,200-1,220 SF each, 100% occupied on M to M leases, providing immediate cash flow with rents significantly under market for future upside. Extensively upgraded in the last couple of years, the property features remodeled apartments, new gas meters + lines, high-efficiency combi boilers, a smart water meter with automatic leak detection and shutoff, backup boilers, and tankless water heaters. The roof is approx. 7 yrs old, further minimizing capital expenditures. Additional improvements include electronic access to all apartments and basements, sprinkler systems in the basements, LED motion-sensor lighting in common areas, a comprehensive security system, a fire/emergency alarm system with direct connection to the Fire Department, and a coin/card-operated laundry room for additional income. Apartment interiors feature new cabinets, laminate flooring, updated appliances and fixtures, vinyl replacement windows, fire-rated entry doors, and keyless remote-access entry. A true turnkey investment featuring extensive capital improvements, minimal deferred maintenance, and good unit mix. Ideally situated in Waterbury's Willow Plaza/North End neighborhood, just minutes from Downtown, shopping, dining, public transportation, and convenient access to Route 8 and I-84. Can be purchased with multiple other buildings. One or more of this property's owners is a Real Estate Licensee.

134 Chestnut Ave, Waterbury

$745,000

12 Beds ⋅ 6 Baths ⋅ 24210241 MLS

Not your average multifamily! This fully renovated 6-unit investment property has been extensively upgraded with quality improvements. The building is 100% occupied and consists of (6) spacious 2-bed, 1-bath apartments, each approx.. 800 SF. Current rents are below market, providing an excellent value-add opportunity through future rent adjustments. Each apartment has been nicely updated with white cabinetry, durable laminate flooring, updated appliances and fixtures, vinyl replacement windows, fire-rated entry doors, and keyless entry systems with remote owner access. Major mechanical improvements include high-efficiency combi boilers, backup boilers and tankless water heaters for added reliability, plus a smart water meter with automatic leak detection and shutoff to help minimize maintenance concerns. Additional building enhancements include roof approx. 4yrs old, basement sprinkler systems, LED motion-sensor lighting throughout the common areas, security system, and a fire/emergency alarm system with a direct connection to the Fire Department. A coin/card-operated laundry room provides an additional source of income. Conveniently located with easy access to shopping, restaurants, public transportation, Downtown Waterbury, Route 8, and I-84. An exceptional turnkey investment offering strong in-place income, minimal deferred maintenance, and long-term upside. Can be purchased with multiple other buildings. One or more of this property's owners is a Real Estate Licensee.

227 Hillside Ave, Waterbury

$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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Hillside Homes under $1.25 million

Newest Hillside Homes under $1.25 million

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