Real Estate Investment Properties for Sale in Connecticut

Looking for investment property in Connecticut with high ROI ?

Explore a variety of short-term homes & houses in Connecticut. Invest wisely with VRBO & Connecticut 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 Connecticut

Q: Which city in Connecticut to invest in for highest ROI on long term rental properties in 2026

In 2026, Plainfieldis the best city to buy investment properties. Find more investment properties today!

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
10 Ann Street #401 Norwalk, CT Welcome to Sono Lofts! This is one of Norwalk's Luxury SONO condominium communities. Locat...	1 beds \| 1 baths \| 834 sq.ft.	$425,000	Airbnb cash on cash: -1.58% Traditional cash on cash: 1.28% Airbnb Rental Income: $1250 Traditional Rental Income: $1992 Airbnb ROI: -1.58% Traditional ROI: 1.28%
151 Hynes Avenue Groton, CT Situated near Thames River Magnet School and Marine Science Magnet High School , as well a...	4 beds \| 3 baths \| 1,584 sq.ft.	$389,000	Airbnb cash on cash: 6.69% Traditional cash on cash: 7.37% Airbnb Rental Income: $4261 Traditional Rental Income: $3610 Airbnb ROI: 6.69% Traditional ROI: 7.37%
1150 Whitney Avenue #5 Hamden, CT PRICE REDUCED! Beautifully remodeled townhouse-style 1-bedroom condo offering the perfect ...	1 beds \| 1 baths \| 636 sq.ft.	$144,900	Airbnb cash on cash: -2.31% Traditional cash on cash: 5% Airbnb Rental Income: $882 Traditional Rental Income: $1561 Airbnb ROI: -2.31% Traditional ROI: 5%
52 Merrimac Street Danbury, CT Welcome home to this charming and updated 2-bedroom, 1.5-bath Cape offering a comfortable ...	2 beds \| 2 baths \| 1,075 sq.ft.	$349,999	Airbnb cash on cash: 1.02% Traditional cash on cash: 2.17% Airbnb Rental Income: $1551 Traditional Rental Income: $1479 Airbnb ROI: 1.02% Traditional ROI: 2.17%
258 South Road Marlborough, CT Beautifully maintained 2714 SF 3 BR-2 Bath contemporary style home w/updates & very specia...	3 beds \| 2 baths \| 2,714 sq.ft.	$629,900	Airbnb cash on cash: 1.68% Traditional cash on cash: 3.2% Airbnb Rental Income: $3346 Traditional Rental Income: $3490 Airbnb ROI: 1.68% Traditional ROI: 3.2%
42 Highland Road #5 Stamford, CT Rare opportunity to own one of just seven stand-alone townhomes in the sought-after Grand ...	3 beds \| 3 baths \| 1,988 sq.ft.	$849,000	Airbnb cash on cash: 0.46% Traditional cash on cash: 2.76% Airbnb Rental Income: $2805 Traditional Rental Income: $3963 Airbnb ROI: 0.46% Traditional ROI: 2.76%
11 Highland Avenue Darien, CT Ideally positioned just moments from downtown Darien and the train station, 11 Highland Av...	4 beds \| 4 baths \| 3,095 sq.ft.	$2,395,000	Airbnb cash on cash: -0.82% Traditional cash on cash: 2.76% Airbnb Rental Income: $2650 Traditional Rental Income: $9975 Airbnb ROI: -0.82% Traditional ROI: 2.76%
56 West Street Bolton, CT Set on a scenic two-acre lot in desirable Bolton, this beautifully renovated Colonial offe...	4 beds \| 2 baths \| 2,372 sq.ft.	$444,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.49% Airbnb Rental Income: $null Traditional Rental Income: $3600 Airbnb ROI: N/A Traditional ROI: 5.49%
71 Rhode Island Line Road Putnam, CT Boasting an impressive amount of thoughtfully designed living space, this exceptional resi...	3 beds \| 3 baths \| 2,728 sq.ft.	$649,900	Airbnb cash on cash: -0.01% Traditional cash on cash: 4.07% Airbnb Rental Income: $2116 Traditional Rental Income: $4051 Airbnb ROI: -0.01% Traditional ROI: 4.07%
15 Freedom Way #67 East Lyme, CT Come see this sunny, stylish move-in ready unit in the beach village of Niantic. This beau...	3 beds \| 3 baths \| 1,820 sq.ft.	$449,900	Airbnb cash on cash: 1.97% Traditional cash on cash: 5.09% Airbnb Rental Income: $2454 Traditional Rental Income: $3171 Airbnb ROI: 1.97% Traditional ROI: 5.09%
90 Gurdon Street Bridgeport , CT You will love this adorable house with a white picket fence in the well-established North ...	3 beds \| 2 baths \| 1,142 sq.ft.	$479,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.1% Airbnb Rental Income: $null Traditional Rental Income: $2921 Airbnb ROI: N/A Traditional ROI: 4.1%
25 Oakridge Road Trumbull, CT Corner House on the raised hill, 2 driveways and 2 sunrooms, and spacious rooms with raise...	3 beds \| 2 baths \| 4,111 sq.ft.	$860,000	Airbnb cash on cash: -0.56% Traditional cash on cash: 2.04% Airbnb Rental Income: $2313 Traditional Rental Income: $3818 Airbnb ROI: -0.56% Traditional ROI: 2.04%
4 Alan Road Danbury, CT Set within a desirable gated community in western Connecticut, this striking contemporary ...	4 beds \| 2 baths \| 2,504 sq.ft.	$579,900	Airbnb cash on cash: 0.79% Traditional cash on cash: 3.14% Airbnb Rental Income: $2798 Traditional Rental Income: $3420 Airbnb ROI: 0.79% Traditional ROI: 3.14%
50 Bulmer Drive Stratford, CT Tucked away on a quiet North End cul-de-sac, 50 Bulmer Drive offers four bedrooms, two ful...	4 beds \| 2 baths \| 1,650 sq.ft.	$619,900	Airbnb cash on cash: 1.49% Traditional cash on cash: 3.23% Airbnb Rental Income: $3505 Traditional Rental Income: $3736 Airbnb ROI: 1.49% Traditional ROI: 3.23%
157 Mountain Road Ridgefield, CT Magnificent opportunity to own on the lake! Wake up to stunning water views and enjoy the ...	2 beds \| 2 baths \| 972 sq.ft.	$649,000	Airbnb cash on cash: 1.17% Traditional cash on cash: 1.48% Airbnb Rental Income: $2903 Traditional Rental Income: $2416 Airbnb ROI: 1.17% Traditional ROI: 1.48%
14 Lincoln Street Farmington, CT Spanning 2,424 sq. ft. of heated living space, this exquisite 2004 Colonial offers 4 Bedro...	4 beds \| 3 baths \| 2,424 sq.ft.	$499,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.18% Airbnb Rental Income: $null Traditional Rental Income: $3684 Airbnb ROI: N/A Traditional ROI: 5.18%
1 East Street Danbury, CT Desirable lake community, a classic raised ranch with loads of improvements, freshly paint...	3 beds \| 3 baths \| 1,954 sq.ft.	$539,000	Airbnb cash on cash: 1.61% Traditional cash on cash: 2.47% Airbnb Rental Income: $2748 Traditional Rental Income: $2535 Airbnb ROI: 1.61% Traditional ROI: 2.47%
8 White Oak Lane Waterford, CT Welcome home to this extraordinary 4 bed, 3.5 bath Colonial, boasting over 4300 sq ft and ...	4 beds \| 4 baths \| 4,379 sq.ft.	$869,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.25% Airbnb Rental Income: $null Traditional Rental Income: $2992 Airbnb ROI: N/A Traditional ROI: 1.25%
49 Wolfpit Avenue Norwalk, CT This beautifully updated Colonial blends character with modern home convenience. Set on a ...	3 beds \| 3 baths \| 2,710 sq.ft.	$999,000	Airbnb cash on cash: -0.51% Traditional cash on cash: 1.23% Airbnb Rental Income: $2173 Traditional Rental Income: $3244 Airbnb ROI: -0.51% Traditional ROI: 1.23%
233 Hillspoint Road Westport, CT Experience waterfront living at 233 Hillspoint Road, a striking new construction home loca...	4 beds \| 5 baths \| 3,624 sq.ft.	$6,975,000	Airbnb cash on cash: -1.24% Traditional cash on cash: -0.3% Airbnb Rental Income: $2908 Traditional Rental Income: $8250 Airbnb ROI: -1.24% Traditional ROI: -0.3%
42 Castlerock Lane Bolton, CT Meticulously maintained Colonial located on a cul-de-sac in Bolton, built in 2007, offerin...	4 beds \| 4 baths \| 3,664 sq.ft.	$899,999	Airbnb cash on cash: N/A Traditional cash on cash: 3.83% Airbnb Rental Income: $null Traditional Rental Income: $5743 Airbnb ROI: N/A Traditional ROI: 3.83%
28 Headquarters Road Litchfield, CT Stimulating and easily managed home is perfect for weekending in an idyllic, small, histor...	3 beds \| 3 baths \| 3,225 sq.ft.	$985,000	Airbnb cash on cash: 0.45% Traditional cash on cash: 2.23% Airbnb Rental Income: $3077 Traditional Rental Income: $4006 Airbnb ROI: 0.45% Traditional ROI: 2.23%
62 Castlewood Lane Torrington, CT Don't wait to come view this Gem located in a quiet cul-de-sac of well maintained homes in...	3 beds \| 3 baths \| 2,287 sq.ft.	$399,900	Airbnb cash on cash: 1.58% Traditional cash on cash: 6.66% Airbnb Rental Income: $2433 Traditional Rental Income: $3741 Airbnb ROI: 1.58% Traditional ROI: 6.66%
155 Winchester Road Norfolk, CT Situated on 2.6 peaceful acres, this unique property offers exceptional space and flexibil...	4 beds \| 4 baths \| 3,770 sq.ft.	$599,000	Airbnb cash on cash: 1.53% Traditional cash on cash: 8.45% Airbnb Rental Income: $3046 Traditional Rental Income: $6221 Airbnb ROI: 1.53% Traditional ROI: 8.45%
24 Hunting Ridge Drive Simsbury, CT A truly exceptional brick Colonial, set on 2 private, level acres in Simsbury, offers pano...	4 beds \| 6 baths \| 9,166 sq.ft.	$1,595,000	Airbnb cash on cash: -2.54% Traditional cash on cash: 1.53% Airbnb Rental Income: $1813 Traditional Rental Income: $7351 Airbnb ROI: -2.54% Traditional ROI: 1.53%
280 East Street S Goshen, CT Galloway Farm is a one of a kind 1970's flat roof contemporary designed by Peter Dalton Mo...	4 beds \| 3 baths \| 2,901 sq.ft.	$1,095,000	Airbnb cash on cash: 0.45% Traditional cash on cash: 2.55% Airbnb Rental Income: $3078 Traditional Rental Income: $4513 Airbnb ROI: 0.45% Traditional ROI: 2.55%
318 Romford Road WASHINGTON, CT Nature Lover's Paradise in Washington close to Rumsey Hall Tucked away on one of Washingto...	3 beds \| 3 baths \| 2,281 sq.ft.	$749,000	Airbnb cash on cash: 0.01% Traditional cash on cash: 6.43% Airbnb Rental Income: $1692 Traditional Rental Income: $5700 Airbnb ROI: 0.01% Traditional ROI: 6.43%
1030 Washington Woodbury Road Roxbury, CT NEW PRICE - Privately set on 18.62 acres, this substantial Roxbury country estate offers s...	4 beds \| 5 baths \| 4,874 sq.ft.	$1,795,000	Airbnb cash on cash: -0.38% Traditional cash on cash: 3.39% Airbnb Rental Income: $2664 Traditional Rental Income: $8326 Airbnb ROI: -0.38% Traditional ROI: 3.39%
167 Fern Street Waterbury, CT Beautifully maintained 3-5 bedroom opportunity situated on a desirable corner lot offering...	3 beds \| 2 baths \| 2,214 sq.ft.	$369,000	Airbnb cash on cash: 2.44% Traditional cash on cash: 6.27% Airbnb Rental Income: $2366 Traditional Rental Income: $3109 Airbnb ROI: 2.44% Traditional ROI: 6.27%
104 Northwest Drive Watertown, CT Custom Craftsmanship, Unparalleled Curbside Appeal, and Pride of ownership to a Majestic M...	4 beds \| 3 baths \| 2,880 sq.ft.	$615,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.07% Airbnb Rental Income: $null Traditional Rental Income: $4421 Airbnb ROI: N/A Traditional ROI: 5.07%
24 Highview Avenue Milford, CT Located in a highly sought-after beach community, this three to four bedroom gem is situat...	3 beds \| 2 baths \| 1,980 sq.ft.	$624,999	Airbnb cash on cash: 2.09% Traditional cash on cash: 3.76% Airbnb Rental Income: $3375 Traditional Rental Income: $3599 Airbnb ROI: 2.09% Traditional ROI: 3.76%
88 Baker Road Thompson, CT Room to breathe, space to grow, and nothing left to do but move in! This turnkey 3-bedroom...	3 beds \| 2 baths \| 1,990 sq.ft.	$399,900	Airbnb cash on cash: 1.64% Traditional cash on cash: 6.36% Airbnb Rental Income: $2018 Traditional Rental Income: $3260 Airbnb ROI: 1.64% Traditional ROI: 6.36%
432 E Mountain Road Waterbury, CT Discover this beautifully updated single-family home nestled on an expansive 2.1-acre lot,...	3 beds \| 1 baths \| 1,724 sq.ft.	$421,000	Airbnb cash on cash: 1.89% Traditional cash on cash: 3.46% Airbnb Rental Income: $2561 Traditional Rental Income: $2565 Airbnb ROI: 1.89% Traditional ROI: 3.46%
2 Pilgrims Way New Milford, CT A RARE COMBINATION OF NEW ENGLAND CHARM AND MODERN LUXURY-MAKE AN OFFER TODAY! Welcome to ...	4 beds \| 3 baths \| 2,174 sq.ft.	$599,950	Airbnb cash on cash: -0.68% Traditional cash on cash: 4.1% Airbnb Rental Income: $1841 Traditional Rental Income: $4020 Airbnb ROI: -0.68% Traditional ROI: 4.1%

Real Estate investment in Connecticut

There are 3,968 properties available for sale in the state of Connecticut. Plainfield, Preston and Middletown are the best rental property markets in Connecticut. The average median price of properties for sale in these cities are $391,133 and the average price per square foot is $0. Their average monthly cash on cash return is 4.67%.

Connecticut Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 3,968 investment properties available for sale in Connecticut.

In 2026, Plainfield is the best city to buy investment properties. Find more investment properties today!

In 2026, Plainfield (5%) and Preston (5%) has the highest cash on cash return for long term rentals in Connecticut.

Your search for investment property begins and ends here

Investment Property for Sale in Connecticut

10 Ann Street #401

Norwalk, CT

1 beds | 1 baths | 834 sq.ft.

$425,000

Airbnb cash on cash: -1.58%

Traditional cash on cash: 1.28%

Airbnb Rental Income: $1250

Traditional Rental Income: $1992

Airbnb ROI: -1.58%

Traditional ROI: 1.28%

151 Hynes Avenue

Groton, CT

4 beds | 3 baths | 1,584 sq.ft.

$389,000

Airbnb cash on cash: 6.69%

Traditional cash on cash: 7.37%

Airbnb Rental Income: $4261

Traditional Rental Income: $3610

Airbnb ROI: 6.69%

Traditional ROI: 7.37%

1150 Whitney Avenue #5

Hamden, CT

1 beds | 1 baths | 636 sq.ft.

$144,900

Airbnb cash on cash: -2.31%

Traditional cash on cash: 5%

Airbnb Rental Income: $882

Traditional Rental Income: $1561

Airbnb ROI: -2.31%

Traditional ROI: 5%

52 Merrimac Street

Danbury, CT

2 beds | 2 baths | 1,075 sq.ft.

$349,999

Airbnb cash on cash: 1.02%

Traditional cash on cash: 2.17%

Airbnb Rental Income: $1551

Traditional Rental Income: $1479

Airbnb ROI: 1.02%

Traditional ROI: 2.17%

258 South Road

Marlborough, CT

3 beds | 2 baths | 2,714 sq.ft.

$629,900

Airbnb cash on cash: 1.68%

Traditional cash on cash: 3.2%

Airbnb Rental Income: $3346

Traditional Rental Income: $3490

Airbnb ROI: 1.68%

Traditional ROI: 3.2%

42 Highland Road #5

Stamford, CT

3 beds | 3 baths | 1,988 sq.ft.

$849,000

Airbnb cash on cash: 0.46%

Traditional cash on cash: 2.76%

Airbnb Rental Income: $2805

Traditional Rental Income: $3963

Airbnb ROI: 0.46%

Traditional ROI: 2.76%

11 Highland Avenue

Darien, CT

4 beds | 4 baths | 3,095 sq.ft.

$2,395,000

Airbnb cash on cash: -0.82%

Traditional cash on cash: 2.76%

Airbnb Rental Income: $2650

Traditional Rental Income: $9975

Airbnb ROI: -0.82%

Traditional ROI: 2.76%

56 West Street

Bolton, CT

4 beds | 2 baths | 2,372 sq.ft.

$444,900

Airbnb cash on cash: N/A

Traditional cash on cash: 5.49%

Airbnb Rental Income: $null

Traditional Rental Income: $3600

Airbnb ROI: N/A