Hillside, CT homes for sale & real estate

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NEW 18 HRS AGO

ABOUT THIS HOME
Hillside, CT Homes for Sale
This expansive family home offers exceptional space where size truly is not an issue. A beautiful front porch welcomes you in, perfect for morning coffee or evening relaxation, and leads to a grand staircase that sets the tone for the home's classic character. Enjoy a generously sized dining room, a large family room anchored by a fireplace, and a bright sunroom just off the living room, ideal for relaxing or entertaining year-round. The home has been freshly painted and features updated bathrooms, blending comfort with timeless appeal. On street parking is complemented by a garage for added convenience. Make this house your home just in time for the holidays there's plenty of room to gathe

$284,000

4 beds3 baths2,436 sq ft

38 Kellogg St, Waterbury, CT 06710

Grand staircase • Front porch • Family room

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
Charming Circa 1905 Home in Waterbury's Town Plot 4/6 Beds 4 Baths. Discover the perfect blend of historic character and modern updates in this well-maintained 2,484 sq. ft. home. With room to grow, it's ideal for multi-generational living or a large family. The first floor welcomes you with an oversized living room featuring a cozy fireplace, an expansive dining room with French doors to a private study, and an updated kitchen with quartz countertops, a sunny eat-in area, and a butler's pantry. Upstairs, you'll find a spacious principal suite with a private bath, a junior suite, plus two additional bedrooms and a half bath. The walk-up attic offers even more potential with two bedrooms and

$349,900

4 beds2.5 baths2,484 sq ft

181 Buckingham St, Waterbury, CT 06710

Modern updates • French doors • Historic character

ABOUT THIS HOME
Hillside, CT Homes for Sale
Calling all investors! Don't miss this well-maintained 5-unit investment property offering a strong 9% CAP rate (at full occupancy). This turnkey, cash-flowing asset features a nicely updated exterior with vinyl siding, replacement windows, a 2-year-old roof, new front porches, and sits prominently on a corner lot. The unit mix includes (1) studio and (1) one-bedroom on the first floor, (2) one-bedroom units on the second floor, and (1) two-bedroom unit on the third floor, providing the potential for good rental income potential. Interior highlights include hardwood floors and updated kitchens and baths in select units. The utilities are separate and tenant-paid, minimizing owner expenses.

$500,000

5 beds5 baths3,067 sq ft

74 Holmes Ave, Waterbury, CT 06710

2 year old roof • New front porches • Updated exterior

ABOUT THIS HOME
Hillside, CT Homes for Sale
This stunning home has been completely remodelled from top to bottom with modern finishes and thoughtful upgrades. Enjoy peace of mind with a brand-new roof, freshly painted siding, new energy efficient windows, new electrical panel, and a new tankless water heater system. Inside, you'll find a brand-new kitchen featuring a tile floor, quartz countertops, new cabinets, and a brand new backsplash. The bathrooms have been fully remodeled with new wall and floor tile, vanities, and fixtures. Beautiful new hardwood floors, fresh interior paint, modern light fixtures, make this home feel brand new throughout. The main level offers a bonus room that can be used as an entertainment space or potent

$330,000

4 beds1.5 baths1,904 sq ft

18 Pine St, Waterbury, CT 06710

Brand new roof • Brand new kitchen • New cabinets

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
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 new smoke/carbon detectors, all new front-fire rated doors and emergency lighting. 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

$399,900

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 1685 days

Average home prices near Hillside, CT

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Hillside, CT real estate trends

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Median Sale Price
# of Homes Sold
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All Home Types

Median Sale Price (All Home Types)

$347,500

0.0% YoY | Nov 2025

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

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Data

Nov 2025

Growth

% YoY

Hillside, CT

$347,500

0.0%

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