Real Estate Investment Properties for Sale in Waterbury, CT

Looking for investment property in Waterbury, CT with high ROI ?

Explore a variety of short-term homes & houses in Waterbury, CT. Invest wisely with VRBO & Waterbury, CT Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Investment Property for Sale in Waterbury, CT

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
23 Heaton Street Waterbury, CT Welcome to this inviting 3-bedroom, 3-bathroom home offering 1,716 sq ft of living space i...	3 beds \| 3 baths \| 1,716 sq.ft.	$399,995	Airbnb cash on cash: 0.1% Traditional cash on cash: 4.12% Airbnb Rental Income: $1673 Traditional Rental Income: $2715 Airbnb ROI: 0.1% Traditional ROI: 4.12%
207 Ridgefield Avenue Waterbury, CT Modern Colonial with Elegant Luxury Upgrades. Step into timeless sophistication with this ...	3 beds \| 3 baths \| 2,390 sq.ft.	$478,500	Airbnb cash on cash: -0.05% Traditional cash on cash: 4.86% Airbnb Rental Income: $1972 Traditional Rental Income: $3654 Airbnb ROI: -0.05% Traditional ROI: 4.86%
28 Gaylord Glen Waterbury, CT Welcome to this Bunker Hill Estate with all the bells and whistles. Set on over 2 acres of...	4 beds \| 3 baths \| 3,300 sq.ft.	$629,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.66% Airbnb Rental Income: $null Traditional Rental Income: $4745 Airbnb ROI: N/A Traditional ROI: 4.66%
509 Highland Avenue Waterbury, CT Discover this incredible town plot 2 unit investment! Each spacious apartment includes gen...	5 beds \| 2 baths \| 2,178 sq.ft.	$430,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.58% Airbnb Rental Income: $null Traditional Rental Income: $4270 Airbnb ROI: N/A Traditional ROI: 8.58%
54 Brentwood Avenue Waterbury, CT Welcome Home! This light-filled East End ranch features 2 bedrooms and 1 bath. Beautiful h...	2 beds \| 1 baths \| 932 sq.ft.	$239,000	Airbnb cash on cash: 1.25% Traditional cash on cash: 5.71% Airbnb Rental Income: $1304 Traditional Rental Income: $1905 Airbnb ROI: 1.25% Traditional ROI: 5.71%
859 Bunker Hill Avenue Waterbury, CT Welcome to 859 Bunker Hill Avenue, located in one of Waterbury's most desirable neighborho...	3 beds \| 1 baths \| 1,196 sq.ft.	$299,999	Airbnb cash on cash: 1.21% Traditional cash on cash: 5.11% Airbnb Rental Income: $1684 Traditional Rental Income: $2315 Airbnb ROI: 1.21% Traditional ROI: 5.11%
39 Glendale Drive Waterbury, CT Discover this inviting Cape located in the peaceful Bunker Hill neighborhood, perfectly si...	3 beds \| 2 baths \| 1,326 sq.ft.	$349,500	Airbnb cash on cash: 1.22% Traditional cash on cash: 2.74% Airbnb Rental Income: $1688 Traditional Rental Income: $1716 Airbnb ROI: 1.22% Traditional ROI: 2.74%
280 Ridgefield Avenue Waterbury, CT Back on the market through no fault of the seller Welcome to 280 Ridgefield Avenue in ...	4 beds \| 3 baths \| 2,458 sq.ft.	$495,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.06% Airbnb Rental Income: $null Traditional Rental Income: $3909 Airbnb ROI: N/A Traditional ROI: 5.06%
26 Highview Street Waterbury, CT Cape Cod house 3 BED 2 BATH and garage! Come in and make this lovely home your own! Perfec...	3 beds \| 2 baths \| 1,086 sq.ft.	$250,000	Airbnb cash on cash: 4.05% Traditional cash on cash: 7.54% Airbnb Rental Income: $2223 Traditional Rental Income: $2487 Airbnb ROI: 4.05% Traditional ROI: 7.54%
2603 North Main Street Waterbury, CT Welcome to this beautifully updated home offering 1,654 sq +/- between the main level and ...	2 beds \| 2 baths \| 1,654 sq.ft.	$334,900	Airbnb cash on cash: 0.54% Traditional cash on cash: 6.55% Airbnb Rental Income: $1369 Traditional Rental Income: $2844 Airbnb ROI: 0.54% Traditional ROI: 6.55%
343 Gaylord Drive Waterbury, CT Spacious high ranch. Wood floors. nice and inviting yard for gatherings. family room in t...	3 beds \| 3 baths \| 2,826 sq.ft.	$370,000	Airbnb cash on cash: 0.58% Traditional cash on cash: 9.25% Airbnb Rental Income: $1684 Traditional Rental Income: $4225 Airbnb ROI: 0.58% Traditional ROI: 9.25%
250 Orange Street Waterbury, CT Investors take notice! 2-family property featuring two identical units-each offering 3 spa...	6 beds \| 2 baths \| 2,248 sq.ft.	$349,999	Airbnb cash on cash: N/A Traditional cash on cash: 8.11% Airbnb Rental Income: $null Traditional Rental Income: $3289 Airbnb ROI: N/A Traditional ROI: 8.11%
34 Katie Lane Waterbury, CT Great Duplex Style Home featuring 5 room, 3 bedroom, 1.5 bath units, Eat-In Kitchen, Livin...	6 beds \| 4 baths \| 2,418 sq.ft.	$499,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.19% Airbnb Rental Income: $null Traditional Rental Income: $5121 Airbnb ROI: N/A Traditional ROI: 8.19%
41 Laval Street Waterbury, CT For your consideration! Lovely updated 2 family home located on a quiet street close to pa...	4 beds \| 2 baths \| 2,184 sq.ft.	$329,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.39% Airbnb Rental Income: $null Traditional Rental Income: $3377 Airbnb ROI: N/A Traditional ROI: 8.39%
354 Bradley Avenue Waterbury, CT Great Town Plot/Country Club location 6 room cape cod style home in remodeled condition on...	4 beds \| 1 baths \| 1,080 sq.ft.	$265,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.16% Airbnb Rental Income: $null Traditional Rental Income: $2506 Airbnb ROI: N/A Traditional ROI: 7.16%
263 Atwood Avenue Waterbury, CT Welcome to this well-maintained and spacious home located in a quiet, convenient neighborh...	2 beds \| 2 baths \| 1,366 sq.ft.	$284,900	Airbnb cash on cash: 0.68% Traditional cash on cash: 7% Airbnb Rental Income: $1294 Traditional Rental Income: $2588 Airbnb ROI: 0.68% Traditional ROI: 7%
211 Pembroke Avenue Waterbury, CT 3 Bed 1 Bath Ranch on 1/4 acre 1 Car Garage. Bring your vision to unlock the potential of...	3 beds \| 1 baths \| 1,072 sq.ft.	$255,000	Airbnb cash on cash: 1.91% Traditional cash on cash: 6.48% Airbnb Rental Income: $1676 Traditional Rental Income: $2306 Airbnb ROI: 1.91% Traditional ROI: 6.48%
38 Maynard Avenue Waterbury, CT Bunker Hill colonial with many updates, including new roof, windows, heating and central a...	3 beds \| 2 baths \| 2,064 sq.ft.	$375,000	Airbnb cash on cash: 0.5% Traditional cash on cash: 6.52% Airbnb Rental Income: $1564 Traditional Rental Income: $3233 Airbnb ROI: 0.5% Traditional ROI: 6.52%
27 Amber Place Waterbury, CT OMG! Stop the search! This is it! Like, close to everything: shopping, schools, highways.....	4 beds \| 3 baths \| 2,280 sq.ft.	$450,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.38% Airbnb Rental Income: $null Traditional Rental Income: $3754 Airbnb ROI: N/A Traditional ROI: 5.38%
222 PLATT ST Waterbury, CT Invest with success and buy through Auction.com. This bank-owned investment property is a ...	N/A beds \| N/A baths \| N/A	$223,000	Airbnb cash on cash: 5.21% Traditional cash on cash: 1.08% Airbnb Rental Income: $2445 Traditional Rental Income: $976 Airbnb ROI: 5.21% Traditional ROI: 1.08%
135 Elise Drive Waterbury, CT Everything you could want it to be! An expanded Classic Cape corner lot with 1.5 Beautiful...	4 beds \| 1 baths \| 1,504 sq.ft.	$319,500	Airbnb cash on cash: N/A Traditional cash on cash: 5.62% Airbnb Rental Income: $null Traditional Rental Income: $2656 Airbnb ROI: N/A Traditional ROI: 5.62%
78 TOROS AVENUE Waterbury, CT Invest with success and buy through Auction.com. This bank-owned investment property is a ...	3 beds \| 1.5 baths \| 1,020 sq.ft.	$241,000	Airbnb cash on cash: 3.44% Traditional cash on cash: 4.69% Airbnb Rental Income: $1984 Traditional Rental Income: $1750 Airbnb ROI: 3.44% Traditional ROI: 4.69%
76 Kenmore Avenue Waterbury, CT Welcome to this stunning and spacious Colonial home, ideally situated in the highly sought...	3 beds \| 3 baths \| 1,664 sq.ft.	$449,900	Airbnb cash on cash: -0.03% Traditional cash on cash: 3.64% Airbnb Rental Income: $1684 Traditional Rental Income: $2760 Airbnb ROI: -0.03% Traditional ROI: 3.64%
713 Bucks Hill Road Waterbury, CT Nestled on a serene dead-end street, this remarkable property spans 3.9 acres of picturesq...	2 beds \| 1 baths \| 1,134 sq.ft.	$750,000	Airbnb cash on cash: -0.72% Traditional cash on cash: 0.82% Airbnb Rental Income: $1369 Traditional Rental Income: $2033 Airbnb ROI: -0.72% Traditional ROI: 0.82%
96 Dracut Avenue Waterbury, CT This cozy ranch comes complete with a spacious eat-in kitchen, a sizable full bathroom, an...	3 beds \| 1 baths \| 1,272 sq.ft.	$260,000	Airbnb cash on cash: 2.48% Traditional cash on cash: 2.63% Airbnb Rental Income: $1984 Traditional Rental Income: $1501 Airbnb ROI: 2.48% Traditional ROI: 2.63%
00 Milton Avenue Waterbury, CT Seize the unique opportunity to personalize your dream home! This beautiful 1,384 square f...	3 beds \| 2 baths \| 1,384 sq.ft.	$330,000	Airbnb cash on cash: 1.31% Traditional cash on cash: 5.27% Airbnb Rental Income: $1984 Traditional Rental Income: $2695 Airbnb ROI: 1.31% Traditional ROI: 5.27%
59 Howard Street Waterbury, CT Better Than a Condo - No HOA, Total Privacy! Looking for a smart investment or your first ...	3 beds \| 2 baths \| 1,360 sq.ft.	$255,000	Airbnb cash on cash: 2.05% Traditional cash on cash: 2.97% Airbnb Rental Income: $1829 Traditional Rental Income: $1556 Airbnb ROI: 2.05% Traditional ROI: 2.97%
335 Raymond Street Waterbury, CT Discover the incredible potential of this charming 2-bedroom ranch, perfectly situated on ...	2 beds \| 1 baths \| 569 sq.ft.	$159,999	Airbnb cash on cash: 2.18% Traditional cash on cash: 6.57% Airbnb Rental Income: $1304 Traditional Rental Income: $1569 Airbnb ROI: 2.18% Traditional ROI: 6.57%
232 Hillside Avenue Waterbury, CT Welcome to this charming colonial styrl single family home, near parks, library, medical f...	4 beds \| 2 baths \| 2,280 sq.ft.	$375,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.02% Airbnb Rental Income: $null Traditional Rental Income: $3308 Airbnb ROI: N/A Traditional ROI: 6.02%
64 Deerwood Lane #2 Waterbury, CT Why rent when you can own this End unit- two bedroom townhouse Private parking at entry do...	2 beds \| 2 baths \| 880 sq.ft.	$179,900	Airbnb cash on cash: -0.26% Traditional cash on cash: 5.87% Airbnb Rental Income: $1369 Traditional Rental Income: $2002 Airbnb ROI: -0.26% Traditional ROI: 5.87%

Real Estate investment in Waterbury, CT

There are 156 properties for sale in the city of Waterbury . The median list price in Waterbury is $312,450 and the average price per square foot is $174. In October 2025, the average monthly cash on cash return in Waterbury is 6.00%. The average monthly rental income in Waterbury is $2,848.

Waterbury, CT Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 156 investment properties available for sale in Waterbury.

In 2025, the best neighborhood to buy investment property is Walnut-Orange-Walsh.

The ROI for Long-Term is higher than the Short-Term in Waterbury with average rental income of $2,848.

Your search for investment property begins and ends here

Investment Property for Sale in Waterbury, CT

23 Heaton Street

Waterbury, CT

3 beds | 3 baths | 1,716 sq.ft.

$399,995

Airbnb cash on cash: 0.1%

Traditional cash on cash: 4.12%

Airbnb Rental Income: $1673

Traditional Rental Income: $2715

Airbnb ROI: 0.1%

Traditional ROI: 4.12%

207 Ridgefield Avenue

Waterbury, CT

3 beds | 3 baths | 2,390 sq.ft.

$478,500

Airbnb cash on cash: -0.05%

Traditional cash on cash: 4.86%

Airbnb Rental Income: $1972

Traditional Rental Income: $3654

Airbnb ROI: -0.05%

Traditional ROI: 4.86%

28 Gaylord Glen

Waterbury, CT

4 beds | 3 baths | 3,300 sq.ft.

$629,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.66%

Airbnb Rental Income: $null

Traditional Rental Income: $4745

Airbnb ROI: N/A

Traditional ROI: 4.66%

509 Highland Avenue

Waterbury, CT

5 beds | 2 baths | 2,178 sq.ft.

$430,000

Airbnb cash on cash: N/A

Traditional cash on cash: 8.58%

Airbnb Rental Income: $null

Traditional Rental Income: $4270

Airbnb ROI: N/A

Traditional ROI: 8.58%

54 Brentwood Avenue

Waterbury, CT

2 beds | 1 baths | 932 sq.ft.

$239,000

Airbnb cash on cash: 1.25%

Traditional cash on cash: 5.71%

Airbnb Rental Income: $1304

Traditional Rental Income: $1905

Airbnb ROI: 1.25%

Traditional ROI: 5.71%

859 Bunker Hill Avenue

Waterbury, CT

3 beds | 1 baths | 1,196 sq.ft.

$299,999

Airbnb cash on cash: 1.21%

Traditional cash on cash: 5.11%

Airbnb Rental Income: $1684

Traditional Rental Income: $2315

Airbnb ROI: 1.21%

Traditional ROI: 5.11%

39 Glendale Drive

Waterbury, CT

3 beds | 2 baths | 1,326 sq.ft.

$349,500

Airbnb cash on cash: 1.22%

Traditional cash on cash: 2.74%

Airbnb Rental Income: $1688

Traditional Rental Income: $1716

Airbnb ROI: 1.22%

Traditional ROI: 2.74%

280 Ridgefield Avenue

Waterbury, CT

4 beds | 3 baths | 2,458 sq.ft.

$495,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.06%

Airbnb Rental Income: $null

Traditional Rental Income: $3909

Airbnb ROI: N/A