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 2024

In 2024, East Hartfordis the best city to buy investment properties. Find more investment properties today!

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
70 Old Town Road #315 Vernon, CT Newly Completed Foundation, Deck, and Sidewalk Replacement . Funky Townhouse quad level wi...	2 beds \| 2 baths \| 1,063 sq.ft.	$169,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.1% Airbnb Rental Income: $null Traditional Rental Income: $2295 Airbnb ROI: N/A Traditional ROI: 8.1%
118 40 Acre Mountain Road Danbury, CT Stunning year-round views of Candlewood Lake set the stage for this contemporary Ranch sty...	3 beds \| 3 baths \| 2,755 sq.ft.	$685,000	Airbnb cash on cash: 6.68% Traditional cash on cash: 4.46% Airbnb Rental Income: $6933 Traditional Rental Income: $4167 Airbnb ROI: 6.68% Traditional ROI: 4.46%
1 Broad Street #9G Stamford, CT Welcome to Park Tower, Stamford's premier luxury residence. This stunning corner unit prov...	2 beds \| 3 baths \| 1,677 sq.ft.	$699,000	Airbnb cash on cash: -1.38% Traditional cash on cash: 0.39% Airbnb Rental Income: $3617 Traditional Rental Income: $3979 Airbnb ROI: -1.38% Traditional ROI: 0.39%
27 Waverly Road Darien, CT Welcome to 27 Waverly Road, a beautiful colonial-style home nestled in the Noroton Bay Ass...	5 beds \| 5 baths \| 4,257 sq.ft.	$3,495,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.53% Airbnb Rental Income: $null Traditional Rental Income: $6935 Airbnb ROI: N/A Traditional ROI: 0.53%
30 Coult Lane Old Lyme, CT Welcome to 30 Coult Lane, a spacious 4-bedroom, 2.5-bathroom split-level style home boasti...	4 beds \| 3 baths \| 3,076 sq.ft.	$599,000	Airbnb cash on cash: 2.06% Traditional cash on cash: 4.21% Airbnb Rental Income: $3814 Traditional Rental Income: $4196 Airbnb ROI: 2.06% Traditional ROI: 4.21%
111 Plumtrees Road Bethel, CT Discover your dream home at this beautifully crafted Colonial, completed in 2018 that offe...	4 beds \| 4 baths \| 3,447 sq.ft.	$850,000	Airbnb cash on cash: 2.04% Traditional cash on cash: 6.18% Airbnb Rental Income: $3635 Traditional Rental Income: $6119 Airbnb ROI: 2.04% Traditional ROI: 6.18%
613 Cherokee Lane #A Stratford, CT Introducing 613A Cherokee Lane! This completely renovated Oronoque Village condo sits righ...	2 beds \| 2 baths \| 1,804 sq.ft.	$439,000	Airbnb cash on cash: 0.65% Traditional cash on cash: 2.91% Airbnb Rental Income: $2487 Traditional Rental Income: $2814 Airbnb ROI: 0.65% Traditional ROI: 2.91%
5 Woodhaven Drive Portland, CT Take a 3D Tour 24/7 or Enjoy a Video Walkthrough 24/7! Here's your opportunity to sweat so...	4 beds \| 2 baths \| 2,349 sq.ft.	$299,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.05% Airbnb Rental Income: $null Traditional Rental Income: $3472 Airbnb ROI: N/A Traditional ROI: 9.05%
153 THOMPSON HILL RD Portland, CT Invest with success and buy through Auction.com. This bank-owned investment property is a ...	3 beds \| 2 baths \| 1,704 sq.ft.	$451,000	Airbnb cash on cash: 3.81% Traditional cash on cash: 3.54% Airbnb Rental Income: $3436 Traditional Rental Income: $2560 Airbnb ROI: 3.81% Traditional ROI: 3.54%
66 Wilson Avenue Trumbull, CT Tiny House! The new trend in homes is right here and is a great alternative to condo livin...	2 beds \| 2 baths \| 648 sq.ft.	$339,900	Airbnb cash on cash: 0.55% Traditional cash on cash: 4.15% Airbnb Rental Income: $1742 Traditional Rental Income: $2414 Airbnb ROI: 0.55% Traditional ROI: 4.15%
22 Boylston Street Milford, CT Welcome home to your quiet new home on Boylston Street! This charming three bedroom Cape p...	3 beds \| 2 baths \| 1,479 sq.ft.	$455,000	Airbnb cash on cash: 9.82% Traditional cash on cash: 5.42% Airbnb Rental Income: $6372 Traditional Rental Income: $3247 Airbnb ROI: 9.82% Traditional ROI: 5.42%
319 Thomaston Road #90 Watertown, CT Watertown Old Farms presents this meticulous 3 bedroom, 3 bath townhome that will WOW you ...	3 beds \| 3 baths \| 1,884 sq.ft.	$375,000	Airbnb cash on cash: 2.26% Traditional cash on cash: 6.19% Airbnb Rental Income: $2788 Traditional Rental Income: $3517 Airbnb ROI: 2.26% Traditional ROI: 6.19%
215 Neds Mountain Road Ridgefield, CT Create, retreat and entertain in this boho chic mountain oasis with a bird's eye view of t...	2 beds \| 2 baths \| 2,795 sq.ft.	$819,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.38% Airbnb Rental Income: $null Traditional Rental Income: $2823 Airbnb ROI: N/A Traditional ROI: 1.38%
149 Ash Street BRIDGEPORT, CT Recently renovated, Colonial with open floor plan, Great for owner occupied, make an offer...	4 beds \| 2 baths \| 1,888 sq.ft.	$374,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.8% Airbnb Rental Income: $null Traditional Rental Income: $3418 Airbnb ROI: N/A Traditional ROI: 6.8%
4 Ledgebrook Drive #4 Norwalk, CT Discover a perfect blend of style and sophistication in this chic unit, offering the essen...	2 beds \| 2 baths \| 1,173 sq.ft.	$399,000	Airbnb cash on cash: 5.35% Traditional cash on cash: 4.21% Airbnb Rental Income: $4409 Traditional Rental Income: $3059 Airbnb ROI: 5.35% Traditional ROI: 4.21%
243 Sunshine Circle Bridgeport , CT COME SEE!! This beautiful starter 4 Bedroom 1.5 bath home, located on the north end of Bri...	4 beds \| 2 baths \| 1,920 sq.ft.	$385,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.37% Airbnb Rental Income: $null Traditional Rental Income: $3339 Airbnb ROI: N/A Traditional ROI: 6.37%
121 Shagbark Drive #121 Derby, CT Welcome to this pristine 2-bedroom, 2-bath half-townhouse, formal living & dining room. An...	2 beds \| 3 baths \| 1,400 sq.ft.	$279,000	Airbnb cash on cash: N/A Traditional cash on cash: 6% Airbnb Rental Income: $null Traditional Rental Income: $2694 Airbnb ROI: N/A Traditional ROI: 6%
25 Adams Avenue #413 Stamford, CT Rare opportunity to own a penthouse unit in the amazing Mill River House. Quiet fourth flo...	2 beds \| 2 baths \| 1,477 sq.ft.	$570,000	Airbnb cash on cash: 1% Traditional cash on cash: 3.1% Airbnb Rental Income: $3012 Traditional Rental Income: $3439 Airbnb ROI: 1% Traditional ROI: 3.1%
35 Weekeepeemee Road Woodbury, CT Sweet 1836 Italianate style home, located in the historic Hotchkissville section of Woodbu...	3 beds \| 2 baths \| 1,959 sq.ft.	$450,000	Airbnb cash on cash: 3.2% Traditional cash on cash: 5.21% Airbnb Rental Income: $3121 Traditional Rental Income: $3256 Airbnb ROI: 3.2% Traditional ROI: 5.21%
16 David Street ENFIELD, CT Back on Market due to buyer financing issues. It's more than meets the eye with this adora...	3 beds \| 2 baths \| 1,008 sq.ft.	$279,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.58% Airbnb Rental Income: $null Traditional Rental Income: $2452 Airbnb ROI: N/A Traditional ROI: 6.58%
365 Allentown Road #31 Bristol, CT Come see this meticulously kept, nearly new colonial home in a perfect location. Fully ope...	3 beds \| 3 baths \| 1,729 sq.ft.	$399,990	Airbnb cash on cash: N/A Traditional cash on cash: 5.42% Airbnb Rental Income: $null Traditional Rental Income: $3651 Airbnb ROI: N/A Traditional ROI: 5.42%
163 Lake Road Warren, CT Listed on the CT Historic Register, the home was built 1851 by Milton & John Curtiss who e...	4 beds \| 3 baths \| 2,818 sq.ft.	$1,550,000	Airbnb cash on cash: 0.71% Traditional cash on cash: 1.25% Airbnb Rental Income: $4130 Traditional Rental Income: $4027 Airbnb ROI: 0.71% Traditional ROI: 1.25%
139 Town Hill Road Warren, CT Welcome to your own private country oasis. You couldn't ask for a better location, this sp...	4 beds \| 4 baths \| 2,754 sq.ft.	$665,000	Airbnb cash on cash: 3.63% Traditional cash on cash: 6.15% Airbnb Rental Income: $4130 Traditional Rental Income: $4816 Airbnb ROI: 3.63% Traditional ROI: 6.15%
15 Marilyn Drive North Canaan, CT A Charming Colonial with Scenic Views Welcome to this beautifully maintained 8-room colon...	4 beds \| 3 baths \| 2,162 sq.ft.	$499,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.58% Airbnb Rental Income: $null Traditional Rental Income: $3678 Airbnb ROI: N/A Traditional ROI: 5.58%
45 Milford Point Road Milford, CT Stunningly unique waterfront contemporary on private sandy beach, turn key. From the Banks...	4 beds \| 4 baths \| 2,264 sq.ft.	$2,290,000	Airbnb cash on cash: 2.02% Traditional cash on cash: 0.61% Airbnb Rental Income: $9687 Traditional Rental Income: $4898 Airbnb ROI: 2.02% Traditional ROI: 0.61%
33 Point Beach Drive Milford, CT Exquisite waterfront living directly on the water. You'll be astounded by the breathtaking...	3 beds \| 3 baths \| 2,308 sq.ft.	$999,900	Airbnb cash on cash: 3% Traditional cash on cash: 2.42% Airbnb Rental Income: $6372 Traditional Rental Income: $4574 Airbnb ROI: 3% Traditional ROI: 2.42%
86 Catalina Drive Coventry, CT Beautifully remodeled Cape oh so close to Coventry Lake! Welcome to Lake Life! Part of the...	3 beds \| 1 baths \| 1,373 sq.ft.	$299,900	Airbnb cash on cash: 9.57% Traditional cash on cash: 6.02% Airbnb Rental Income: $4334 Traditional Rental Income: $2420 Airbnb ROI: 9.57% Traditional ROI: 6.02%
16 Brookside Drive Easton, CT Welcome to 16 Brookside Drive situated on 3 acres located in the heart of Easton. FULLY FU...	3 beds \| 4 baths \| 2,937 sq.ft.	$749,999	Airbnb cash on cash: 3.4% Traditional cash on cash: 3.17% Airbnb Rental Income: $5517 Traditional Rental Income: $4244 Airbnb ROI: 3.4% Traditional ROI: 3.17%
18 Village Walk #18 Wilton, CT **Thank you for your interest in 18 Village Walk. We have received multiple offers and are...	1 beds \| 1 baths \| 698 sq.ft.	$344,000	Airbnb cash on cash: 1.8% Traditional cash on cash: 2.54% Airbnb Rental Income: $2372 Traditional Rental Income: $2025 Airbnb ROI: 1.8% Traditional ROI: 2.54%
69 Everett Street Stratford, CT Move in ready Colonial which features new/newer asphalt roof, maintenance free vinyl sidin...	3 beds \| 2 baths \| 1,443 sq.ft.	$399,900	Airbnb cash on cash: 7.85% Traditional cash on cash: 6.27% Airbnb Rental Income: $4868 Traditional Rental Income: $3276 Airbnb ROI: 7.85% Traditional ROI: 6.27%
881 Lafayette Boulevard #1C Bridgeport , CT This highly sought-after, rarely available condo in Park City Lofts offers an exceptional ...	2 beds \| 3 baths \| 1,440 sq.ft.	$289,900	Airbnb cash on cash: 0.52% Traditional cash on cash: 7.17% Airbnb Rental Income: $2006 Traditional Rental Income: $3299 Airbnb ROI: 0.52% Traditional ROI: 7.17%
48 Sidney Street EAST HAVEN, CT Lovely well-maintained colonial home on corner lot with detached garage located near cente...	3 beds \| 2 baths \| 1,260 sq.ft.	$319,000	Airbnb cash on cash: 0.22% Traditional cash on cash: 8.45% Airbnb Rental Income: $1192 Traditional Rental Income: $3271 Airbnb ROI: 0.22% Traditional ROI: 8.45%
67 River Road WASHINGTON, CT Unique Residential Compound on River Road: 3 Homes, Scenic Views, and Endless Potential. S...	3 beds \| 4 baths \| 1,934 sq.ft.	$859,000	Airbnb cash on cash: 2.36% Traditional cash on cash: 3.88% Airbnb Rental Income: $3936 Traditional Rental Income: $4304 Airbnb ROI: 2.36% Traditional ROI: 3.88%
2071 Middletown Avenue North Branford, CT Here's your chance to invest in a remarkable and rare opportunity: a beautifully renovated...	3 beds \| 3 baths \| 1,458 sq.ft.	$499,900	Airbnb cash on cash: 5.6% Traditional cash on cash: 4.95% Airbnb Rental Income: $4709 Traditional Rental Income: $3431 Airbnb ROI: 5.6% Traditional ROI: 4.95%
711 West Wakefield Boulevard Winchester, CT Build your DREAM home! Largest lot available on the lake with great views and parking! Wil...	3 beds \| 3 baths \| 2,664 sq.ft.	$1,500,000	Airbnb cash on cash: 1.46% Traditional cash on cash: 1.55% Airbnb Rental Income: $4795 Traditional Rental Income: $3932 Airbnb ROI: 1.46% Traditional ROI: 1.55%
8 Morningview Court Hamden, CT Gracious Colonial in turn key condition tucked away in Hamden! Located on a dead-end stree...	4 beds \| 3 baths \| 2,541 sq.ft.	$575,000	Airbnb cash on cash: 2.05% Traditional cash on cash: 4.45% Airbnb Rental Income: $3476 Traditional Rental Income: $3999 Airbnb ROI: 2.05% Traditional ROI: 4.45%
130 Tophet Road Roxbury, CT Set on 14 private and fully fenced acres, this truly spectacular property, once owned by W...	5 beds \| 6 baths \| 3,500 sq.ft.	$4,995,000	Airbnb cash on cash: -0.97% Traditional cash on cash: 0.43% Airbnb Rental Income: $1214 Traditional Rental Income: $7302 Airbnb ROI: -0.97% Traditional ROI: 0.43%
116 Wellers Bridge Road Roxbury, CT Extra special and super sleek Mid-Century modern in a convenient Roxbury location. Cool ma...	3 beds \| 4 baths \| 3,236 sq.ft.	$1,195,000	Airbnb cash on cash: 1.86% Traditional cash on cash: 2.94% Airbnb Rental Income: $4695 Traditional Rental Income: $4927 Airbnb ROI: 1.86% Traditional ROI: 2.94%
21 Holiday Point Road Sherman, CT [ONE OF A KIND] This house has it all. Located in the desired Atchison Cove private lake c...	4 beds \| 4 baths \| 4,854 sq.ft.	$1,250,000	Airbnb cash on cash: 1.34% Traditional cash on cash: 2.01% Airbnb Rental Income: $4986 Traditional Rental Income: $4747 Airbnb ROI: 1.34% Traditional ROI: 2.01%
5 Church Street Farmington, CT Rare opportunity to reside in the heart of "Farmington Village." This stunning 4 bed/6 bat...	4 beds \| 6 baths \| 4,431 sq.ft.	$1,250,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.98% Airbnb Rental Income: $null Traditional Rental Income: $7360 Airbnb ROI: N/A Traditional ROI: 4.98%

Real Estate investment in Connecticut

There are 3,041 properties available for sale in the state of Connecticut. East Hartford, Middletown and Fairfield are the best rental property markets in Connecticut. The average median price of properties for sale in these cities are $467,950 and the average price per square foot is $0. Their average monthly cash on cash return is 5.00%.

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

There are 3,041 investment properties available for sale in Connecticut.

In 2024, East Hartford is the best city to buy investment properties. Find more investment properties today!

In 2024, East Hartford (7%) and Middletown (6%) 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

70 Old Town Road #315

Vernon, CT

2 beds | 2 baths | 1,063 sq.ft.

$169,900

Airbnb cash on cash: N/A

Traditional cash on cash: 8.1%

Airbnb Rental Income: $null

Traditional Rental Income: $2295

Airbnb ROI: N/A

Traditional ROI: 8.1%

118 40 Acre Mountain Road

Danbury, CT

3 beds | 3 baths | 2,755 sq.ft.

$685,000

Airbnb cash on cash: 6.68%

Traditional cash on cash: 4.46%

Airbnb Rental Income: $6933

Traditional Rental Income: $4167

Airbnb ROI: 6.68%

Traditional ROI: 4.46%

1 Broad Street #9G

Stamford, CT

2 beds | 3 baths | 1,677 sq.ft.

$699,000

Airbnb cash on cash: -1.38%

Traditional cash on cash: 0.39%

Airbnb Rental Income: $3617

Traditional Rental Income: $3979

Airbnb ROI: -1.38%

Traditional ROI: 0.39%

27 Waverly Road

Darien, CT

5 beds | 5 baths | 4,257 sq.ft.

$3,495,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.53%

Airbnb Rental Income: $null

Traditional Rental Income: $6935

Airbnb ROI: N/A

Traditional ROI: 0.53%

30 Coult Lane

Old Lyme, CT

4 beds | 3 baths | 3,076 sq.ft.

$599,000

Airbnb cash on cash: 2.06%

Traditional cash on cash: 4.21%

Airbnb Rental Income: $3814

Traditional Rental Income: $4196

Airbnb ROI: 2.06%

Traditional ROI: 4.21%

111 Plumtrees Road

Bethel, CT

4 beds | 4 baths | 3,447 sq.ft.

$850,000

Airbnb cash on cash: 2.04%

Traditional cash on cash: 6.18%

Airbnb Rental Income: $3635

Traditional Rental Income: $6119

Airbnb ROI: 2.04%

Traditional ROI: 6.18%

613 Cherokee Lane #A

Stratford, CT

2 beds | 2 baths | 1,804 sq.ft.

$439,000

Airbnb cash on cash: 0.65%

Traditional cash on cash: 2.91%

Airbnb Rental Income: $2487

Traditional Rental Income: $2814

Airbnb ROI: 0.65%

Traditional ROI: 2.91%

5 Woodhaven Drive

Portland, CT

4 beds | 2 baths | 2,349 sq.ft.

$299,000

Airbnb cash on cash: N/A

Traditional cash on cash: 9.05%

Airbnb Rental Income: $null

Traditional Rental Income: $3472

Airbnb ROI: N/A