Hillside Real Estate

Excellent investment opportunity to acquire 13 units across two multifamily properties being offered as a package - 66 & 74 Holmes Avenue in Waterbury. This offering provides a strong combination of updated units, existing cash flow, ample off-street parking, and additional value-add potential. The properties are situated on a nice corner lot with good visibility and convenient access. 66 Holmes Avenue consists of 8 units with a desirable mix of four 3-bedroom units, two 2-bedroom units, one 1-bedroom unit, and one studio. The property has undergone extensive improvements, including completely remodeled units and replacement windows. The property offers a strong unit mix with excellent income potential. 74 Holmes Avenue consists of 5 units including one 2-bedroom, three 1-bedroom units, and one studio. Improvements include a roof approximately 2 years old, replacement windows, vinyl siding, and mostly updated units. Some renovation remains, providing an investor with the opportunity to complete improvements, increase rents, and further enhance overall property performance. A diversified unit mix, substantial improvements already completed, ample off-street parking, a desirable corner lot, and significant upside potential. An attractive opportunity for an investor looking to add scale and value to a Waterbury multifamily portfolio. Properties are being offered together as a package. Seller financing may be available for qualified buyers, subject to acceptable terms.

66-74 Holmes Ave, Waterbury

$1,450,000

14 Beds ⋅ 8 Baths ⋅ 24212158 MLS

Excellent investment opportunity to acquire 13 units across two multifamily properties being offered as a package - 66 & 74 Holmes Avenue in Waterbury. This offering provides a strong combination of updated units, existing cash flow, ample off-street parking, and additional value-add potential. The properties are situated on a nice corner lot with good visibility and convenient access. 66 Holmes Avenue consists of 8 units with a desirable mix of four 3-bedroom units, two 2-bedroom units, one 1-bedroom unit, and one studio. The property has undergone extensive improvements, including completely remodeled units and replacement windows. The property offers a strong unit mix with excellent income potential. 74 Holmes Avenue consists of 5 units including one 2-bedroom, three 1-bedroom units, and one studio. Improvements include a roof approximately 2 years old, replacement windows, vinyl siding, and mostly updated units. Some renovation remains, providing an investor with the opportunity to complete improvements, increase rents, and further enhance overall property performance. A diversified unit mix, substantial improvements already completed, ample off-street parking, a desirable corner lot, and significant upside potential. An attractive opportunity for an investor looking to add scale and value to a Waterbury multifamily portfolio. Properties are being offered together as a package. Seller financing may be available for qualified buyers, subject to acceptable terms.

66-74 Holmes Ave, Waterbury

$869,900

6 Baths ⋅ 24210247 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, 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. One or more of this property's owners is a Real Estate Licensee.

134 Chestnut Ave, Waterbury

$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

2 Baths ⋅ 24210243 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

$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

$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

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