Hillside, CT homes for sale & real estate

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ABOUT THIS HOME
Hillside, CT Homes for Sale
Architectural Masterpiece - 1901 Historic Mansion Step back into the elegance of the Gilded Age with this extraordinary historic mansion, nestled in the heart of Waterbury - once hailed as the Brass Center of the World. This distinguished estate stands as a rare architectural gem, echoing the opulence of Newport's famed cliffside mansions. Built at the height of Waterbury's industrial prominence, the home features period details throughout: soaring ceilings, intricate woodwork, leaded glass windows, and a grand staircase that speaks to a bygone era of craftsmanship and prestige. There is a full third floor for servant quarters with 4 bedrooms and 7 closets complete with its own staircase. I

$600,000

5 beds5 baths5,590 sq ft

70 Hillside Ave, Waterbury, CT 06710

Grand staircase • Period details • Leaded glass windows

ABOUT THIS HOME
Hillside, CT Homes for Sale
Experience timeless elegance in this expansive six bedroom, three bathroom residence showcasing a sophisticated open concept design. A breathtaking foyer with a dramatic staircase creates an unforgettable first impression, leading into spacious living and entertaining areas bathed in natural light. The stunning sunroom offers year round enjoyment and seamless indoor-outdoor living. Two luxurious en suite bedrooms provide the ultimate in comfort and privacy, ideal for multi-generational living or guest accommodations. With exceptional scale, thoughtful design, and architectural detail throughout, this home exemplifies refined living at its finest. * MOTIVATED SELLER * Owner holds a brokers

$289,000

6 beds3 baths2,436 sq ft

38 Kellogg St, Waterbury, CT 06710

Stunning sunroom • Breathtaking foyer • Open concept design

ABOUT THIS HOME
Hillside, CT Homes for Sale
* * Excellent Investment or Owner-Occupant Opportunity! * * Welcome to 205 Cooke Street in Waterbury-a well-maintained 3-family property offering great income potential. The 1st and 2nd floor units each feature 3 bedrooms and 1 full bath, while the 3rd floor offers 2 bedrooms, 1 full bath, and an additional room perfect for storage or a home office. The 1st floor includes active solar, helping lower energy costs, and both the 1st and 2nd floors have washer and dryer hookups for added convenience. All three units feature electric appliances, and a detached garage provides extra parking or storage space. Conveniently located near shopping, schools, and major highways. Schedule your showing

$399,900

6 beds3 baths3,439 sq ft

205 Cooke St, Waterbury, CT 06710

Near schools • Near shopping • Electric appliances

ABOUT THIS HOME
Hillside, CT Homes for Sale
Renovated mixed-use investment with 3 units. 1st floor 1350 sqft, handicap accessible. 2nd floor 2bd/1ba 1300 sqft. 3rd floor 2bd/1ba. Property features beautiful woodwork, hardwood floors throughout, new gas furnaces, 200 amp electrical, replacement windows, off street parking for 6 cars. Great location and close to downtown.

$329,000

7 beds3 baths4,075 sq ft

67 Holmes Ave, Waterbury, CT 06710

200 amp electrical • Handicap accessible • Beautiful woodwork

ABOUT THIS HOME
Hillside, CT Homes for Sale
Welcome to this spacious and beautifully updated Colonial offering 3,502 sq. ft. of living space. This impressive home features 6 bedrooms and 2.5 bathrooms, providing plenty of room for a large family or multi-generational living. With its generous layout and multiple bedrooms, this property is ideal for room rentals or a shared housing setup for steady rental income. Enjoy the convenience of a private driveway with ample parking and a detached garage. The property has been tastefully renovated with many upgrades, including a new roof, new electrical system, fresh interior paint, new windows, new heating system, and new water heater--making it truly move-in ready.

$399,000

6 beds2.5 baths3,502 sq ft

90 Pine St, Waterbury, CT 06710

Private driveway • Fresh interior paint • New roof

Property at 96 Hillside Ave, Waterbury, CT 06710, 6 beds, 3 baths

$795,000

6 beds3 baths2,333 sq ft

96 Hillside Ave, Waterbury, CT 06710

Property at 74 Holmes Ave, Waterbury, CT 06710, 5 beds, 5 baths

$525,000

5 beds5 baths3,067 sq ft

74 Holmes Ave, Waterbury, CT 06710

Property at 181 Buckingham St, Waterbury, CT 06710, 4 beds, 2.5 baths

$349,900

4 beds2.5 baths2,484 sq ft

181 Buckingham St, Waterbury, CT 06710

Property at 18 Pine St, Waterbury, CT 06710, 4 beds, 1.5 baths

$330,000

4 beds1.5 baths1,904 sq ft

18 Pine St, Waterbury, CT 06710

Property at 31 2nd Ave, Waterbury, CT 06710, 4 beds, 2 baths

$224,999

4 beds2 baths1,832 sq ft

31 2nd Ave, Waterbury, CT 06710

Property at 33 Mitchell Ave, Waterbury, CT 06710, 9 beds, 3 baths

$399,900

9 beds3 baths3,496 sq ft

33 Mitchell Ave, Waterbury, CT 06710

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ABOUT THIS HOME
Hillside, CT Homes for Sale
This two family home will not last in the market! Well maintained home with more space to add in the attic. Home is ideal for investors and owner occupants. Each unit offers spacious living areas, solid rental potential, and excellent long-term value. Whether you're looking to generate strong cash flow or live in one unit while offsetting your mortgage with rental income, this property provides the perfect opportunity. Conveniently located near shopping, schools, and major highways.

$279,900

6 beds2 baths3,075 sq ft

57 Ridgewood St, Waterbury, CT 06010

Attic space • Two family home • Conveniently located

ABOUT THIS HOME
Hillside, CT Homes for Sale
HUGE VALUE-ADD OPPORTUNITY! Oversized 3-family property with tremendous potential. Each spacious unit offers approximately 1,210 sq. ft. with 3 bedrooms and large, open floor plans-perfect for renters or owner-occupants. All utilities are separately metered, and tenant paid (gas and electric), keeping expenses low. An oversized garage in the rear provides additional income potential through storage or parking, plus there's ample off-street parking for tenants. Once renovated, this property will offer minimal maintenance and strong cash flow for years to come. Fantastic location-walking distance to Fulton Park, with easy access to downtown, highways, public transportation, and shopping. Grea

$439,900

9 beds3 baths3,636 sq ft

127 Pearl St, Waterbury, CT 06704

Oversized garage • 5,662 sq ft lot • 2 garage spots

ABOUT THIS HOME
Hillside, CT Homes for Sale
Investor Opportunity Turnkey 5-family property in the heart of Waterbury offering excellent cash flow and strong rental history. All five units are fully rented with reliable tenants, making this a great choice for any investor seeking immediate income. Each apartment features all-new kitchens and updated finishes throughout, adding to the property's appeal and minimizing maintenance concerns. The building has separate utilities, allowing for efficient management and reduced owner expenses. The roof is approximately eight years old and in great condition. Located on the bus line and close to shopping, schools, and major highways, the property offers easy access for tenants and consistent re

$500,000

8 beds— baths3,658 sq ft

28 Gilbert St, Waterbury, CT 06702

All new kitchens • Separate utilities • Easy access

ABOUT THIS HOME
Hillside, CT Homes for Sale
Investors take notice. Three units fully occupied. Two units are 3 bedroom apartments. There are open and enclosed porches. One car garage under. All tenants are month to month. Can be purchased as a package with MLS # 24100700 for $570,000.

$314,900

6 beds2 baths1,714 sq ft

238 Bishop St, Waterbury, CT 06704

Open porches • Enclosed porches • One car garage

ABOUT THIS HOME
Hillside, CT Homes for Sale
Welcome to this charming colonial styrl single family home, near parks, library, medical facilities, public transportation etc. Boasting 9 rooms, 6 bedrooms, 2 1/2 baths, 1 car garage, and driveway for 3 cars. The 3rd floor was finished to add 2 more bedrooms than the town card. Great kitchen with granite countertops and oversize island has been thoughtfully updated with stainless steel appliances and plenty of cabinets. Excellent opportunity for home ownership. This property has active solar and water filtration system. Camera surveillance in service

$375,000

4 beds1.5 baths2,280 sq ft

232 Hillside Ave, Waterbury, CT 06710

Colonial style home • Finished 3rd floor • Oversize island

ABOUT THIS HOME
Hillside, CT Homes for Sale
Open Lot with Great Opportunity to Build! Drive by and view today!

$100,000

— beds— baths— sq ft

0 N Main St, Waterbury, CT 06701

2.8 acre lot • Listed 1656 days

Average home prices near Hillside, CT

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Hillside, CT real estate trends

All Home Types trends in Hillside, CT

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$347,500

+26.4% YoY | Oct 2025

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

Oct 2025

Growth

% YoY

Hillside, CT

$347,500

+26.4%

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