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 2025

In 2025, West Hartfordis the best city to buy investment properties. Find more investment properties today!

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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.	$374,995	Airbnb cash on cash: 0.17% Traditional cash on cash: 4.46% Airbnb Rental Income: $1673 Traditional Rental Income: $2715 Airbnb ROI: 0.17% Traditional ROI: 4.46%
2 Elmwood Drive #2 Fairfield, CT Rare offering in the coveted Southport Green complex, just steps from Southport Village an...	3 beds \| 4 baths \| 3,328 sq.ft.	$2,495,000	Airbnb cash on cash: -1.53% Traditional cash on cash: 0.29% Airbnb Rental Income: $2373 Traditional Rental Income: $5995 Airbnb ROI: -1.53% Traditional ROI: 0.29%
360 North Society Road Canterbury, CT INSTANT EQUITY when you finish this SPRAWLING Cape it COMPS out $525,000 to $550,000! OVER...	3 beds \| 2 baths \| 2,236 sq.ft.	$275,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.76% Airbnb Rental Income: $null Traditional Rental Income: $3171 Airbnb ROI: N/A Traditional ROI: 8.76%
147 Holly Hill Lane Greenwich, CT Prime opportunity to acquire a turn-key investment property featuring 9 duplex-style townh...	2 beds \| 2 baths \| 1,611 sq.ft.	$9,999,999	Airbnb cash on cash: -3.02% Traditional cash on cash: -2.78% Airbnb Rental Income: $1642 Traditional Rental Income: $3419 Airbnb ROI: -3.02% Traditional ROI: -2.78%
32 WILLINGTON AVENUE Stafford Springs, CT Completely renovated old-style Colonial that sits on1.72 private acres. Nestled in the woo...	3 beds \| 2 baths \| 1,047 sq.ft.	$349,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.4% Airbnb Rental Income: $null Traditional Rental Income: $2593 Airbnb ROI: N/A Traditional ROI: 5.4%
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: -0.23% Traditional cash on cash: 3.54% Airbnb Rental Income: $1388 Traditional Rental Income: $2560 Airbnb ROI: -0.23% Traditional ROI: 3.54%
38 Aspinall Drive Andover, CT Charming & Quaint New England 3 BR Cape Cod at end of Cul-de-Sac is steps away from Hop Ri...	3 beds \| 1 baths \| 1,008 sq.ft.	$285,000	Airbnb cash on cash: 2.66% Traditional cash on cash: 5.26% Airbnb Rental Income: $1880 Traditional Rental Income: $2075 Airbnb ROI: 2.66% Traditional ROI: 5.26%
114 Terrill Road Stratford, CT Welcome to this charming Paradise Green Ranch, perfectly situated within walking distance ...	3 beds \| 2 baths \| 1,922 sq.ft.	$424,900	Airbnb cash on cash: 1.24% Traditional cash on cash: 5.92% Airbnb Rental Income: $2065 Traditional Rental Income: $3394 Airbnb ROI: 1.24% Traditional ROI: 5.92%
28 Hillside Drive Easton, CT Don't miss this incredible home set on an expansive one-plus-acre property in Lower Easton...	4 beds \| 5 baths \| 4,780 sq.ft.	$1,200,000	Airbnb cash on cash: 1.39% Traditional cash on cash: 6.12% Airbnb Rental Income: $4891 Traditional Rental Income: $9165 Airbnb ROI: 1.39% Traditional ROI: 6.12%
109 Timber Trail Tolland, CT Welcome to 109 Timber Trail in Tolland! This beautiful 4-bedroom, 3-bath home combines tho...	4 beds \| 3 baths \| 2,884 sq.ft.	$419,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.89% Airbnb Rental Income: $null Traditional Rental Income: $4437 Airbnb ROI: N/A Traditional ROI: 8.89%
8 Bobcat Lane Warren, CT Perfectly positioned to capture breathtaking sunset views, this beautifully updated four-b...	4 beds \| 5 baths \| 5,537 sq.ft.	$1,985,000	Airbnb cash on cash: 0.21% Traditional cash on cash: 3.35% Airbnb Rental Income: $3651 Traditional Rental Income: $8633 Airbnb ROI: 0.21% Traditional ROI: 3.35%
75 West Glen Drive Stamford, CT HIGHEST AND BEST OFFERS DUE BY 10/27 5PM. Beautifully presented in Westover, this immacula...	4 beds \| 5 baths \| 4,884 sq.ft.	$2,099,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.76% Airbnb Rental Income: $null Traditional Rental Income: $9067 Airbnb ROI: N/A Traditional ROI: 2.76%
18 Roxbury Road Norwalk, CT Tall and stately, this beautiful home stands proudly at the end of a peaceful cul-de-sac. ...	3 beds \| 3 baths \| 1,987 sq.ft.	$829,000	Airbnb cash on cash: 2.33% Traditional cash on cash: 3.79% Airbnb Rental Income: $4173 Traditional Rental Income: $4416 Airbnb ROI: 2.33% Traditional ROI: 3.79%
2 Andrea Avenue Wolcott, CT Enjoy beautiful water views from this split level set across the street from Hitchcock Lak...	3 beds \| 2 baths \| 1,304 sq.ft.	$329,900	Airbnb cash on cash: 1.06% Traditional cash on cash: 6.49% Airbnb Rental Income: $1564 Traditional Rental Income: $2798 Airbnb ROI: 1.06% Traditional ROI: 6.49%
75 Lisbon Road Canterbury, CT If you love charm and character this antique former schoolhouse may be for you! Currently ...	1 beds \| 1 baths \| 782 sq.ft.	$225,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.95% Airbnb Rental Income: $null Traditional Rental Income: $1534 Airbnb ROI: N/A Traditional ROI: 4.95%
1 Mountaincrest Drive Cheshire, CT PREMIUM WOOD FLOORS JUST INSTALLED in this Mountaincrest custom colonial showcasing luxuri...	4 beds \| 5 baths \| 4,791 sq.ft.	$1,200,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.04% Airbnb Rental Income: $null Traditional Rental Income: $8439 Airbnb ROI: N/A Traditional ROI: 5.04%
338 Salisbury Road North Canaan, CT Welcome to this beautifully maintained three-bedroom home located on the peaceful outskirt...	3 beds \| 1 baths \| 1,080 sq.ft.	$299,900	Airbnb cash on cash: 5.57% Traditional cash on cash: 5.39% Airbnb Rental Income: $2850 Traditional Rental Income: $2136 Airbnb ROI: 5.57% Traditional ROI: 5.39%
785 Paradise Avenue Hamden, CT Bright, inviting, and ready to move right in! This charming Hamden home welcomes you with ...	3 beds \| 2 baths \| 2,408 sq.ft.	$404,900	Airbnb cash on cash: -0.44% Traditional cash on cash: 6.02% Airbnb Rental Income: $1352 Traditional Rental Income: $3391 Airbnb ROI: -0.44% Traditional ROI: 6.02%
44 Strawberry Hill Avenue #5L Stamford, CT Step into sophisticated city living with this beautifully appointed 2BR 2BA residence in t...	2 beds \| 2 baths \| 1,225 sq.ft.	$450,000	Airbnb cash on cash: -1.31% Traditional cash on cash: 4.48% Airbnb Rental Income: $1608 Traditional Rental Income: $3591 Airbnb ROI: -1.31% Traditional ROI: 4.48%
2437 Bedford Street #F20 Stamford, CT Nestled in a serene private enclave, this meticulously maintained condominium offers the p...	1 beds \| 2 baths \| 1,066 sq.ft.	$435,000	Airbnb cash on cash: -1.25% Traditional cash on cash: 3.26% Airbnb Rental Income: $1248 Traditional Rental Income: $2691 Airbnb ROI: -1.25% Traditional ROI: 3.26%
163 Lake Road Warren, CT Historic Elegance Meets Countryside Charm in Warren, Ct Nestled within the picturesque ex...	4 beds \| 3 baths \| 2,818 sq.ft.	$1,100,000	Airbnb cash on cash: 1.01% Traditional cash on cash: 2.16% Airbnb Rental Income: $3651 Traditional Rental Income: $4027 Airbnb ROI: 1.01% Traditional ROI: 2.16%
881 Lafayette Boulevard #1A Bridgeport , CT Act Fast! This beautifully updated 2-story condo is a rare find that won't last! Tucked aw...	2 beds \| 2 baths \| 1,452 sq.ft.	$325,000	Airbnb cash on cash: -2.19% Traditional cash on cash: 5.65% Airbnb Rental Income: $1051 Traditional Rental Income: $3081 Airbnb ROI: -2.19% Traditional ROI: 5.65%
8 Circle Drive EAST HAVEN, CT Welcome to 8 Circle Drive East Haven CT. The Home Consists of a Spacious Living Room, Eat ...	3 beds \| 1 baths \| 988 sq.ft.	$319,900	Airbnb cash on cash: 1.4% Traditional cash on cash: 4.48% Airbnb Rental Income: $1622 Traditional Rental Income: $2090 Airbnb ROI: 1.4% Traditional ROI: 4.48%
38 Elgin Street Hamden, CT Classic, charming Spring Glen Colonial with warm inviting formal living room with wood bur...	3 beds \| 2 baths \| 1,648 sq.ft.	$429,000	Airbnb cash on cash: -0.99% Traditional cash on cash: 4.24% Airbnb Rental Income: $1352 Traditional Rental Income: $3043 Airbnb ROI: -0.99% Traditional ROI: 4.24%
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.	$1,199,000	Airbnb cash on cash: 0.08% Traditional cash on cash: 2.14% Airbnb Rental Income: $3171 Traditional Rental Income: $4747 Airbnb ROI: 0.08% Traditional ROI: 2.14%
178 Scott Drive South Windsor, CT Attractive 4 bedroom colonial in residential setting within walking distance to the elemen...	4 beds \| 3 baths \| 1,960 sq.ft.	$499,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.7% Airbnb Rental Income: $null Traditional Rental Income: $3935 Airbnb ROI: N/A Traditional ROI: 5.7%
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: -0.19% Traditional cash on cash: 2.35% Airbnb Rental Income: $2246 Traditional Rental Income: $4006 Airbnb ROI: -0.19% Traditional ROI: 2.35%
165 Birchwood Drive Torrington, CT ROOM TO GROW, SPACE TO SHARE! Looking for a home that fits your expanding lifestyle? Wheth...	3 beds \| 2 baths \| 2,330 sq.ft.	$325,000	Airbnb cash on cash: 1.32% Traditional cash on cash: 5.56% Airbnb Rental Income: $1798 Traditional Rental Income: $2604 Airbnb ROI: 1.32% Traditional ROI: 5.56%
24 Hunting Ridge Drive Simsbury, CT This stunning brick Colonial sits atop Hunting Ridge Drive on a sprawling two-acre level l...	4 beds \| 6 baths \| 9,166 sq.ft.	$1,699,999	Airbnb cash on cash: N/A Traditional cash on cash: 1.61% Airbnb Rental Income: $null Traditional Rental Income: $7351 Airbnb ROI: N/A Traditional ROI: 1.61%
141 Dowd Avenue Canton, CT Exceptional Mixed-Use Opportunity in the Heart of Canton, CT Discover the charm and versat...	6 beds \| 3 baths \| 4,251 sq.ft.	$578,000	Airbnb cash on cash: 1.29% Traditional cash on cash: 7.9% Airbnb Rental Income: $2990 Traditional Rental Income: $5872 Airbnb ROI: 1.29% Traditional ROI: 7.9%
92 Pepperidge Road Portland, CT This charming 3-bedroom, 2.5-bath colonial nestled on a private 1.02-acre lot was built in...	3 beds \| 3 baths \| 2,272 sq.ft.	$489,000	Airbnb cash on cash: -0.67% Traditional cash on cash: 5.46% Airbnb Rental Income: $1388 Traditional Rental Income: $3771 Airbnb ROI: -0.67% Traditional ROI: 5.46%

Real Estate investment in Connecticut

There are 2,937 properties available for sale in the state of Connecticut. West Hartford, Rocky Hill and Norwalk are the best rental property markets in Connecticut. The average median price of properties for sale in these cities are $521,633 and the average price per square foot is $0. Their average monthly cash on cash return is 4.00%.

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

There are 2,937 investment properties available for sale in Connecticut.

In 2025, West Hartford is the best city to buy investment properties. Find more investment properties today!

In 2025, West Hartford (5%) and Rocky Hill (4%) 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

23 Heaton Street

Waterbury, CT

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

$374,995

Airbnb cash on cash: 0.17%

Traditional cash on cash: 4.46%

Airbnb Rental Income: $1673

Traditional Rental Income: $2715

Airbnb ROI: 0.17%

Traditional ROI: 4.46%

2 Elmwood Drive #2

Fairfield, CT

3 beds | 4 baths | 3,328 sq.ft.

$2,495,000

Airbnb cash on cash: -1.53%

Traditional cash on cash: 0.29%

Airbnb Rental Income: $2373

Traditional Rental Income: $5995

Airbnb ROI: -1.53%

Traditional ROI: 0.29%

360 North Society Road

Canterbury, CT

3 beds | 2 baths | 2,236 sq.ft.

$275,000

Airbnb cash on cash: N/A

Traditional cash on cash: 8.76%

Airbnb Rental Income: $null

Traditional Rental Income: $3171

Airbnb ROI: N/A

Traditional ROI: 8.76%

147 Holly Hill Lane

Greenwich, CT

2 beds | 2 baths | 1,611 sq.ft.

$9,999,999

Airbnb cash on cash: -3.02%

Traditional cash on cash: -2.78%

Airbnb Rental Income: $1642

Traditional Rental Income: $3419

Airbnb ROI: -3.02%

Traditional ROI: -2.78%

32 WILLINGTON AVENUE

Stafford Springs, CT

3 beds | 2 baths | 1,047 sq.ft.

$349,900

Airbnb cash on cash: N/A

Traditional cash on cash: 5.4%

Airbnb Rental Income: $null

Traditional Rental Income: $2593

Airbnb ROI: N/A

Traditional ROI: 5.4%

153 THOMPSON HILL RD

Portland, CT

3 beds | 2 baths | 1,704 sq.ft.

$451,000

Airbnb cash on cash: -0.23%

Traditional cash on cash: 3.54%

Airbnb Rental Income: $1388

Traditional Rental Income: $2560

Airbnb ROI: -0.23%

Traditional ROI: 3.54%

38 Aspinall Drive

Andover, CT

3 beds | 1 baths | 1,008 sq.ft.

$285,000

Airbnb cash on cash: 2.66%

Traditional cash on cash: 5.26%

Airbnb Rental Income: $1880

Traditional Rental Income: $2075

Airbnb ROI: 2.66%

Traditional ROI: 5.26%

114 Terrill Road

Stratford, CT

3 beds | 2 baths | 1,922 sq.ft.

$424,900

Airbnb cash on cash: 1.24%

Traditional cash on cash: 5.92%

Airbnb Rental Income: $2065

Traditional Rental Income: $3394

Airbnb ROI: 1.24%