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
95 Audubon Street #339 New Haven, CT Rare find: a single level, 2 bedroom, 2 bathroom ~1400 sq.ft. unit located at a desirable ...	2 beds \| 2 baths \| 1,395 sq.ft.	$620,000	Airbnb cash on cash: -3.42% Traditional cash on cash: 0.13% Airbnb Rental Income: $915 Traditional Rental Income: $2627 Airbnb ROI: -3.42% Traditional ROI: 0.13%
2 Elmwood Drive #2 Fairfield, CT Rare opportunity in sought-after Southport Green-just steps to Southport Village and Metro...	3 beds \| 4 baths \| 3,328 sq.ft.	$2,200,000	Airbnb cash on cash: -1.8% Traditional cash on cash: 0.19% Airbnb Rental Income: $2545 Traditional Rental Income: $5995 Airbnb ROI: -1.8% Traditional ROI: 0.19%
347 New London Turnpike Stonington, CT Coming Soon! Rare opportunity to own a one-of-a-kind circa 1700 Antique Cape set on more t...	3 beds \| 3 baths \| 2,632 sq.ft.	$719,000	Airbnb cash on cash: 1.01% Traditional cash on cash: 3.8% Airbnb Rental Income: $2439 Traditional Rental Income: $3713 Airbnb ROI: 1.01% Traditional ROI: 3.8%
104 Parkway S New London, CT Looking for luxury, comfort, privacy, and CT's best private beaches? This striking modern ...	5 beds \| 5 baths \| 3,696 sq.ft.	$720,000	Airbnb cash on cash: 0.99% Traditional cash on cash: 9.92% Airbnb Rental Income: $3234 Traditional Rental Income: $8500 Airbnb ROI: 0.99% Traditional ROI: 9.92%
88 Churchill Road Hamden, CT Graciously set on a quiet street in the heart of Spring Glen, this home seamlessly blends ...	4 beds \| 3 baths \| 2,496 sq.ft.	$675,000	Airbnb cash on cash: -0.94% Traditional cash on cash: 3.45% Airbnb Rental Income: $2178 Traditional Rental Income: $4390 Airbnb ROI: -0.94% Traditional ROI: 3.45%
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.	$165,000	Airbnb cash on cash: -1.25% Traditional cash on cash: 4.75% Airbnb Rental Income: $967 Traditional Rental Income: $1561 Airbnb ROI: -1.25% Traditional ROI: 4.75%
58 Briar Woods Trail Stamford, CT Tucked into a serene, nature-filled setting, this beautifully updated contemporary ranch o...	3 beds \| 5 baths \| 4,388 sq.ft.	$1,099,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.99% Airbnb Rental Income: $null Traditional Rental Income: $7773 Airbnb ROI: N/A Traditional ROI: 4.99%
835 Monroe Turnpike Monroe, CT HIGHEST AND BEST OFFERS, DEADLINE MONDAY 6/8/26. 5 PM Set on 4.8 acres of level, private l...	4 beds \| 4 baths \| 3,826 sq.ft.	$725,000	Airbnb cash on cash: -0.9% Traditional cash on cash: 6.17% Airbnb Rental Income: $2318 Traditional Rental Income: $6522 Airbnb ROI: -0.9% Traditional ROI: 6.17%
16 Marlene Drive Ledyard, CT RARE FIND! A 4-bedroom mobile home on its own land. You heard me right. Vinyl sided, newer...	4 beds \| 1 baths \| 1,260 sq.ft.	$169,900	Airbnb cash on cash: 9.55% Traditional cash on cash: 11.43% Airbnb Rental Income: $2618 Traditional Rental Income: $2298 Airbnb ROI: 9.55% Traditional ROI: 11.43%
205 Flanders Rd Niantic, CT Investors/203(k) buyers take notice. Spacious home on corner lot in Niantic. Was formerly ...	5 beds \| 4 baths \| 2,086 sq.ft.	$505,000	Airbnb cash on cash: 4.55% Traditional cash on cash: 7.43% Airbnb Rental Income: $3916 Traditional Rental Income: $4434 Airbnb ROI: 4.55% Traditional ROI: 7.43%
56 West Street Bolton, CT Beautifully renovated and move-in ready, 56 West Street offers the space, setting, and upd...	4 beds \| 2 baths \| 2,372 sq.ft.	$499,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.87% Airbnb Rental Income: $null Traditional Rental Income: $3600 Airbnb ROI: N/A Traditional ROI: 4.87%
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%
38 Main Street Deep River, CT Nestled in the charming town of Deep River, between the villages of Essex and Chester, thi...	4 beds \| 4 baths \| 2,560 sq.ft.	$650,000	Airbnb cash on cash: -0.71% Traditional cash on cash: 7.68% Airbnb Rental Income: $1386 Traditional Rental Income: $6058 Airbnb ROI: -0.71% Traditional ROI: 7.68%
53 Prospect Street Woodstock, CT Highest and Best Deadline, WEDNESDAY 4/29 at NOON East Woodstock Sweet Escape - Where...	3 beds \| 3 baths \| 1,736 sq.ft.	$425,000	Airbnb cash on cash: 2.46% Traditional cash on cash: 6.23% Airbnb Rental Income: $2553 Traditional Rental Income: $3442 Airbnb ROI: 2.46% Traditional ROI: 6.23%
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: -0.08% Traditional cash on cash: 3.54% Airbnb Rental Income: $1466 Traditional Rental Income: $2560 Airbnb ROI: -0.08% Traditional ROI: 3.54%
23 Seymour Road #3B East Granby, CT Welcome to this charming and move-in-ready 2 bedroom, 1.5 bath home offering the perfect b...	2 beds \| 2 baths \| 1,440 sq.ft.	$219,000	Airbnb cash on cash: 2.24% Traditional cash on cash: 7.61% Airbnb Rental Income: $1966 Traditional Rental Income: $2564 Airbnb ROI: 2.24% Traditional ROI: 7.61%
20 Whitefield Drive Trumbull, CT Beautifully renovated 5 BR, 4 full bath home offering 3,132 sq ft on a private professiona...	5 beds \| 4 baths \| 3,132 sq.ft.	$949,000	Airbnb cash on cash: 0.38% Traditional cash on cash: 2.06% Airbnb Rental Income: $3388 Traditional Rental Income: $4121 Airbnb ROI: 0.38% Traditional ROI: 2.06%
14 Liberty Lane Thompson, CT Highest and best deadline Tuesday 5/5 @5pm A Homesteader's Dream ** Additional square foot...	3 beds \| 1 baths \| 1,660 sq.ft.	$399,900	Airbnb cash on cash: 0.14% Traditional cash on cash: 4.2% Airbnb Rental Income: $1240 Traditional Rental Income: $2368 Airbnb ROI: 0.14% Traditional ROI: 4.2%
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: -0.65% Traditional cash on cash: 3.16% Airbnb Rental Income: $1859 Traditional Rental Income: $3420 Airbnb ROI: -0.65% Traditional ROI: 3.16%
14 Lincoln Street Farmington, CT This exquisite 2004 Colonial offers 4 Bedrooms, 2.5 Baths, 2,213 sq. ft. of heated living ...	4 beds \| 3 baths \| 2,424 sq.ft.	$549,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.66% Airbnb Rental Income: $null Traditional Rental Income: $3684 Airbnb ROI: N/A Traditional ROI: 4.66%
128 Spring Road North Haven, CT Highest and Best offers by Monday, May 25th @6pm Tucked away in one of North Haven's mos...	3 beds \| 3 baths \| 2,428 sq.ft.	$575,000	Airbnb cash on cash: -0.34% Traditional cash on cash: 5.23% Airbnb Rental Income: $1798 Traditional Rental Income: $4299 Airbnb ROI: -0.34% Traditional ROI: 5.23%
58 Main Street Salisbury, CT Introducing: Charlotte. This lovely 1834 Antique Colonial is perfectly framed in the cente...	3 beds \| 3 baths \| 2,116 sq.ft.	$1,300,000	Airbnb cash on cash: -0.66% Traditional cash on cash: 1.38% Airbnb Rental Income: $1590 Traditional Rental Income: $3598 Airbnb ROI: -0.66% Traditional ROI: 1.38%
36 Attawan Rd Niantic, CT Beautifully Renovated Year Round Beach Home! Move right into this charming Four Bedroom, ...	3 beds \| 2 baths \| 1,786 sq.ft.	$895,000	Airbnb cash on cash: -0.14% Traditional cash on cash: 1.59% Airbnb Rental Income: $1861 Traditional Rental Income: $2800 Airbnb ROI: -0.14% Traditional ROI: 1.59%
6 Constance Street New Haven, CT Nestled on a quiet cul-de-sac in the highly desirable Lighthouse section of Morris Cove, t...	4 beds \| 3 baths \| 2,205 sq.ft.	$515,000	Airbnb cash on cash: -1.52% Traditional cash on cash: 5.47% Airbnb Rental Income: $1280 Traditional Rental Income: $4242 Airbnb ROI: -1.52% Traditional ROI: 5.47%
1113 Old Pond Lane #1113 Norwich, CT Completely remodeled and beautifully appointed, this exceptional Country Suite overlooks t...	1 beds \| 1 baths \| 576 sq.ft.	$229,000	Airbnb cash on cash: -1.93% Traditional cash on cash: 1.13% Airbnb Rental Income: $1025 Traditional Rental Income: $1328 Airbnb ROI: -1.93% Traditional ROI: 1.13%
106 County Street Norwalk, CT Nestled on a rare acre-plus parcel in a prime sought-after location near the Westport bord...	3 beds \| 2 baths \| 2,042 sq.ft.	$750,000	Airbnb cash on cash: 0.41% Traditional cash on cash: 2.87% Airbnb Rental Income: $2725 Traditional Rental Income: $3802 Airbnb ROI: 0.41% Traditional ROI: 2.87%
100 Wildcat Hill Road Harwinton, CT Completely renovated modified Cape/Colonial from the foundation up offers eight rooms, two...	3 beds \| 3 baths \| 2,292 sq.ft.	$599,000	Airbnb cash on cash: 0.82% Traditional cash on cash: 5.36% Airbnb Rental Income: $2119 Traditional Rental Income: $4115 Airbnb ROI: 0.82% Traditional ROI: 5.36%
289 New Haven Avenue #V Milford, CT Welcome home to this ultra-spacious and beautifully maintained 2-bedroom townhouse-style c...	2 beds \| 2 baths \| 1,514 sq.ft.	$449,900	Airbnb cash on cash: 0.53% Traditional cash on cash: 4.34% Airbnb Rental Income: $2124 Traditional Rental Income: $3185 Airbnb ROI: 0.53% Traditional ROI: 4.34%
102 Pumpkin Hill Road Ashford, CT Private 10.21-acre country property offering the perfect blend of comfortable living, priv...	3 beds \| 3 baths \| 2,754 sq.ft.	$525,000	Airbnb cash on cash: 0.71% Traditional cash on cash: 5.6% Airbnb Rental Income: $2172 Traditional Rental Income: $4022 Airbnb ROI: 0.71% Traditional ROI: 5.6%
3 Halletts Road New Milford, CT Welcome to this beautifully restored circa-1800 farmhouse, where historic New England char...	3 beds \| 2 baths \| 1,558 sq.ft.	$520,000	Airbnb cash on cash: 0.99% Traditional cash on cash: 4.13% Airbnb Rental Income: $2069 Traditional Rental Income: $3064 Airbnb ROI: 0.99% Traditional ROI: 4.13%
176 Apple Lane Roxbury, CT Your turnkey country escape is waiting in Roxbury - a modern shinglestyle home on 4+ manic...	4 beds \| 5 baths \| 3,566 sq.ft.	$1,995,000	Airbnb cash on cash: -1.06% Traditional cash on cash: 2.77% Airbnb Rental Income: $1700 Traditional Rental Income: $8323 Airbnb ROI: -1.06% Traditional ROI: 2.77%
66 Country Lane Hebron, CT Located in Chestnut Hollow subdivision. Home is 3,050 sq.ft plus addition 600 sq.ft finish...	4 beds \| 4 baths \| 3,836 sq.ft.	$927,400	Airbnb cash on cash: N/A Traditional cash on cash: 5.05% Airbnb Rental Income: $null Traditional Rental Income: $6593 Airbnb ROI: N/A Traditional ROI: 5.05%

Real Estate investment in Connecticut

There are 4,017 properties available for sale in the state of Connecticut. Plainfield, Norwalk and New Fairfield are the best rental property markets in Connecticut. The average median price of properties for sale in these cities are $633,000 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 4,017 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 (6%) and Norwalk (3%) 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

95 Audubon Street #339

New Haven, CT

2 beds | 2 baths | 1,395 sq.ft.

$620,000

Airbnb cash on cash: -3.42%

Traditional cash on cash: 0.13%

Airbnb Rental Income: $915

Traditional Rental Income: $2627

Airbnb ROI: -3.42%

Traditional ROI: 0.13%

2 Elmwood Drive #2

Fairfield, CT

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

$2,200,000

Airbnb cash on cash: -1.8%

Traditional cash on cash: 0.19%

Airbnb Rental Income: $2545

Traditional Rental Income: $5995

Airbnb ROI: -1.8%

Traditional ROI: 0.19%

347 New London Turnpike

Stonington, CT

3 beds | 3 baths | 2,632 sq.ft.

$719,000

Airbnb cash on cash: 1.01%

Traditional cash on cash: 3.8%

Airbnb Rental Income: $2439

Traditional Rental Income: $3713

Airbnb ROI: 1.01%

Traditional ROI: 3.8%

104 Parkway S

New London, CT

5 beds | 5 baths | 3,696 sq.ft.

$720,000

Airbnb cash on cash: 0.99%

Traditional cash on cash: 9.92%

Airbnb Rental Income: $3234

Traditional Rental Income: $8500

Airbnb ROI: 0.99%

Traditional ROI: 9.92%

88 Churchill Road

Hamden, CT

4 beds | 3 baths | 2,496 sq.ft.

$675,000

Airbnb cash on cash: -0.94%

Traditional cash on cash: 3.45%

Airbnb Rental Income: $2178

Traditional Rental Income: $4390

Airbnb ROI: -0.94%

Traditional ROI: 3.45%

1150 Whitney Avenue #5

Hamden, CT

1 beds | 1 baths | 636 sq.ft.

$165,000

Airbnb cash on cash: -1.25%

Traditional cash on cash: 4.75%

Airbnb Rental Income: $967

Traditional Rental Income: $1561

Airbnb ROI: -1.25%

Traditional ROI: 4.75%

58 Briar Woods Trail

Stamford, CT

3 beds | 5 baths | 4,388 sq.ft.

$1,099,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.99%

Airbnb Rental Income: $null

Traditional Rental Income: $7773

Airbnb ROI: N/A

Traditional ROI: 4.99%

835 Monroe Turnpike

Monroe, CT

4 beds | 4 baths | 3,826 sq.ft.

$725,000

Airbnb cash on cash: -0.9%

Traditional cash on cash: 6.17%

Airbnb Rental Income: $2318

Traditional Rental Income: $6522

Airbnb ROI: -0.9%