Hillside Real Estate

Welcome to Hillside, a hidden gem nestled in the heart of Waterbury, Connecticut! This charming neighborhood offers a delightful blend of suburban tranquility and urban convenience, making it an ideal place for families, young professionals, and retirees alike.

Hillside is characterized by its picturesque tree-lined streets, well-maintained homes, and a strong sense of community. Residents take pride in their neighborhood, often gathering for local events and enjoying the lush parks and recreational spaces that dot the area. The inviting atmosphere is enhanced by friendly neighbors who are always ready to lend a helping hand or share a smile.

One of the standout features of Hillside is its proximity to essential amenities. Within minutes, you can access a variety of shopping centers, grocery stores, and dining options, ensuring that you have everything you need right at your fingertips. Families will appreciate the highly-rated schools in the area, which provide quality education and a supportive environment for children to thrive.

For those who enjoy the great outdoors, Hillside is close to several parks and nature trails, perfect for weekend strolls, picnics, or simply unwinding amidst nature. The neighborhood’s central location also allows for easy access to nearby attractions in Waterbury, such as the beautiful Mattatuck Museum and the vibrant downtown area.

Whether you're looking to settle down or invest in a property, Hillside offers a welcoming community with a rich sense of belonging. Come explore this enchanting neighborhood and discover why so many are proud to call Hillside home!

Newest Listings in Hillside

$379,900

10 Beds ⋅ 3 Baths ⋅ 24194341 MLS

Owner-Occupants and Investors Take Notice! Excellent opportunity in the desirable Hillside neighborhood. This three-family property offers strong cash flow potential with two 3/4-bedroom, 1-bath units and one 2-bedroom, 1-bath unit. All utilities are separate and tenant-paid, including gas heat and hot water. Electrical has been updated to circuit breakers and is also tenant-paid. Exterior features include vinyl siding, replacement windows, and off-street parking for three vehicles. Great value-add opportunity for investors or owner-occupants looking to build equity and generate rental income. 8.5+% CAP at full occupancy.

37 Plaza 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

$399,900

10 Beds ⋅ 3 Baths ⋅ 24191529 MLS

Exceptional owner-occupant or investment opportunity! This massive 2-family property w/finished 3rd floor space, features a stable, income-producing 1st-floor apartment offering approximately 1,200 SF, while the expansive 2nd and 3rd floors have been combined into an impressive 2,100+ SF unit with roughly 7 bedrooms and 1.5 baths - an ideal setup for a large or extended family. The 2nd and 3rd floor units have been completely renovated and showcases beautifully refinished hardwood floors, a brand-new kitchen, updated full and half baths, fresh paint, modern fixtures, and tasteful finishes throughout, creating a true move-in-ready living space that's difficult to find. Both units are separately metered with tenant-paid utilities, helping keep owner operating expenses to a minimum. Predominantly on-street parking further reduces maintenance costs. Conveniently located in Waterbury's Willow Plaza neighborhood with easy access to Downtown, shopping, restaurants, schools, public transportation, Route 8, and I-84. Whether you're seeking strong rental income with an exceptional owner-occupant unit or a unique addition to your investment portfolio, this well-maintained multifamily offers outstanding value and versatility.

41 Plaza Ave, Waterbury

$750,000

2 Baths ⋅ 24191026 MLS

Not your average multifamily! This fully renovated 6-unit investment property has been extensively upgraded with quality improvements rarely found in comparable assets. The building is 100% occupied, offering immediate cash flow, 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.

227 Hillside Ave, Waterbury

$750,000

12 Beds ⋅ 6 Baths ⋅ 24191017 MLS

227 Hillside Ave, Waterbury

$875,000

6 Baths ⋅ 24190930 MLS

Multifamily investments with this level of renovation rarely come to market. 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, all 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 an exceptional unit mix. Ideally situated in Waterbury's desirable Willow Plaza/North End neighborhood, just minutes from Downtown, shopping, dining, public transportation, and convenient access to Route 8 and I-84.

134 Chestnut Ave, Waterbury

$875,000

20 Beds ⋅ 6 Baths ⋅ 24190921 MLS

Multifamily investments with this level of renovation rarely come to market. 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.

134 Chestnut Ave, Waterbury

$4,500,000

1 Baths ⋅ 24166907 MLS

The property located at Grove St & Cook St is a prime grocery-anchored investment opportunity featuring a brand-new Food Universe supermarket under a 25-year lease through July 15, 2048, providing long-term, stable cash flow. Food Universe is backed by Key Food Stores Co-operative Inc., a nationally recognized grocery operator with a strong network and established credit profile, supporting a highly reliable tenancy. The asset benefits from exceptional visibility and accessibility, positioned on a prominent corner with convenient access to I-84 and Route 8, and features strong site functionality including ample parking (51 spaces) and a loading dock. The surrounding area continues to strengthen, highlighted by a newly completed 44 unit residential development directly across the street, driving built-in customer traffic. Additionally, the property is located within both a federally designated Opportunity Zone and an Enterprise Zone, offering potential tax incentives and enhanced after-tax return potential. Overall, the asset offers a compelling combination of long-term contractual income, strong tenant credit support, prime visibility, and public incentive benefits in a growing supermarket.

96 Grove St, Waterbury

$1,125,000

13 Beds ⋅ 11 Baths ⋅ 24164287 MLS

Back on market, buyer did not qualify for loan. This is an 11 unit apartment building. 2 units have 2 bedrooms, kitchen, living room and 1 full bathroom. 5 units are large 1 bedroom with living room, kitchen and 1 full bathroom. 4 are smaller with 1 bedroom, kitchen and 1 full bathroom. All units are separately metered with electric. They all have electric baseboards for heat with sub panels in apartments and each have their own electric hot water heater. No furnaces to worry about and no gas in building. Owner only pays for common area lights, cameras and internet which is on a separate owners meter. Pressure reducer valve was added on main so you can control water pressure. Trash is done by city. Roof and siding are 4 years old, new locked mailboxes installed 1 year ago, 8 ring cameras from 2025, all meters and apartments are labeled. Most units have been updated over the past year and almost entire building has been painted on interior. 2 brand new canopies were built in 2026 for 2 back apartments. Only selling because owner is moving out of state. Please check out other listing MLS# 24163790 which is located right down the street, can be combined for major cashflow and easy to manage being so close.

133 Hillside Ave, Waterbury

$525,000

14 Beds ⋅ 4 Baths ⋅ 24163790 MLS

Back on the market, buyer did not qualify for loan. We have financing options with lenders that service rooming houses. This is a fully occupied 14 unit permitted rooming house with a 5 bay garage and 4 full bathrooms. 12 units are single room, 1 unit is a double room and 1 unit is a 1 bedroom apartment with full kitchen and bathroom. There are 3 other full bathrooms in common areas, 1 on each floor, all with tile. 8 hard wired ring cameras throughout, pin code locks on front door and common area bathrooms and hard wired fire system for safety and security. There are 3 coin washers and 3 coin dryers in common areas. Each unit has a microwave and fridge, apartment also has an electric stove. Entire building was insulated on all exterior walls and attic in 2025 with USA Premium Foam R-5.1, paperwork can be shown. Garage had all new doors installed in 2024 and 4 bays are rented, 1 bay is used for storage. New 40 gallon gas water heater in 2025. Heated by electric baseboards in each unit controlled by locked central thermostats. Owner pays gas, water/sewer, electric and internet, trash is done by city. Great property to add to any portfolio looking for huge cashflow. Only selling because owner is moving out of state. Combine with MLS# 24164287 which is right down the street for major cashflow and easy to manage being so close.

34 Mitchell Ave, Waterbury

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