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, Prestonis the best city to buy investment properties. Find more investment properties today!

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
78 Hartford Avenue Old Saybrook, CT Beach living, redefined. Welcome to 78 Hartford Avenue, a rare coastal gem perched right o...	3 beds \| 1 baths \| 890 sq.ft.	$795,000	Airbnb cash on cash: 1.25% Traditional cash on cash: 1.53% Airbnb Rental Income: $3088 Traditional Rental Income: $2586 Airbnb ROI: 1.25% Traditional ROI: 1.53%
951 Old Clinton Road #17 Westbrook, CT Redwood Commons-a boutique community of only 20 units, thoughtfully distributed among 10 a...	2 beds \| 3 baths \| 1,704 sq.ft.	$569,900	Airbnb cash on cash: -0.45% Traditional cash on cash: 4.24% Airbnb Rental Income: $1983 Traditional Rental Income: $3962 Airbnb ROI: -0.45% Traditional ROI: 4.24%
739 Rock Rimmon Road Stamford, CT Discover your dream home in this privately situated custom contemporary residence, boastin...	3 beds \| 3 baths \| 3,562 sq.ft.	$925,000	Airbnb cash on cash: 0.03% Traditional cash on cash: 3.02% Airbnb Rental Income: $2741 Traditional Rental Income: $4663 Airbnb ROI: 0.03% Traditional ROI: 3.02%
1 Broad Street #11D Stamford, CT Experience luxury living in this sun-drenched corner unit at Park Tower, a pet-friendly hi...	2 beds \| 3 baths \| 1,436 sq.ft.	$675,000	Airbnb cash on cash: -0.29% Traditional cash on cash: 3.94% Airbnb Rental Income: $2164 Traditional Rental Income: $4282 Airbnb ROI: -0.29% Traditional ROI: 3.94%
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: -2.97% Traditional cash on cash: -2.78% Airbnb Rental Income: $2158 Traditional Rental Income: $3419 Airbnb ROI: -2.97% 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%
2 Currier Court #2 Cheshire, CT Currier Woods is located in a 160-unit community known for its mature trees, private windi...	2 beds \| 2 baths \| 1,362 sq.ft.	$319,900	Airbnb cash on cash: 1.65% Traditional cash on cash: 5.6% Airbnb Rental Income: $1889 Traditional Rental Income: $2572 Airbnb ROI: 1.65% Traditional ROI: 5.6%
36 State Street Guilford, CT Don't miss this extraordinary opportunity to own a picture-perfect retreat just steps from...	1 beds \| 1 baths \| 720 sq.ft.	$450,000	Airbnb cash on cash: 0.96% Traditional cash on cash: 2.34% Airbnb Rental Income: $1902 Traditional Rental Income: $1979 Airbnb ROI: 0.96% Traditional ROI: 2.34%
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: 0.79% Traditional cash on cash: 3.54% Airbnb Rental Income: $1906 Traditional Rental Income: $2560 Airbnb ROI: 0.79% Traditional ROI: 3.54%
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: 2.2% Traditional cash on cash: 5.92% Airbnb Rental Income: $2524 Traditional Rental Income: $3394 Airbnb ROI: 2.2% Traditional ROI: 5.92%
44 Ridge Lane SHELTON, CT Meticulously Maintained and move in ready Raised Ranch. Recent upgrades include: New roof,...	3 beds \| 3 baths \| 2,242 sq.ft.	$640,000	Airbnb cash on cash: 0.68% Traditional cash on cash: 4.2% Airbnb Rental Income: $2088 Traditional Rental Income: $3652 Airbnb ROI: 0.68% Traditional ROI: 4.2%
433 Thoreau Street #433 Branford, CT Desirable Greens townhouse with 3 bedrooms, 2.5 bathrooms with two balconies and patio off...	3 beds \| 3 baths \| 1,464 sq.ft.	$270,000	Airbnb cash on cash: 1.22% Traditional cash on cash: 9.1% Airbnb Rental Income: $1880 Traditional Rental Income: $3383 Airbnb ROI: 1.22% Traditional ROI: 9.1%
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.	$369,900	Airbnb cash on cash: 0.84% Traditional cash on cash: 5.69% Airbnb Rental Income: $1564 Traditional Rental Income: $2798 Airbnb ROI: 0.84% Traditional ROI: 5.69%
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%
489 Hoyt Street Darien, CT Watch video link below! Charming New England Farmhouse with golf course views. Perfect...	4 beds \| 3 baths \| 3,630 sq.ft.	$1,649,000	Airbnb cash on cash: -0.9% Traditional cash on cash: 1.92% Airbnb Rental Income: $1633 Traditional Rental Income: $5503 Airbnb ROI: -0.9% Traditional ROI: 1.92%
1100 Guernseytown Road Watertown, CT Experience the charm of a beautifully updated Cape Cod-style home where every detail has b...	3 beds \| 1 baths \| 2,014 sq.ft.	$395,000	Airbnb cash on cash: 0.18% Traditional cash on cash: 4.53% Airbnb Rental Income: $1445 Traditional Rental Income: $2625 Airbnb ROI: 0.18% Traditional ROI: 4.53%
187 Black Hill Road Plainfield, CT Welcome home to this lovely colonial home built in 2001! This spacious home has 3 generous...	3 beds \| 3 baths \| 2,240 sq.ft.	$415,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.15% Airbnb Rental Income: $null Traditional Rental Income: $3598 Airbnb ROI: N/A Traditional ROI: 7.15%
88 Boardwalk Groton, CT Prestigious beachfront property in desirable Groton Long Point on the most desirable part ...	3 beds \| 5 baths \| 5,289 sq.ft.	$2,995,000	Airbnb cash on cash: -1.93% Traditional cash on cash: 0.33% Airbnb Rental Income: $2619 Traditional Rental Income: $8273 Airbnb ROI: -1.93% Traditional ROI: 0.33%
38 Saddle Road Norwalk, CT Welcome to Wolfpit!!! This 3/4BD thoughtfully designed ranch style home located in one of ...	4 beds \| 2 baths \| 2,135 sq.ft.	$749,000	Airbnb cash on cash: 2.99% Traditional cash on cash: 3.94% Airbnb Rental Income: $4407 Traditional Rental Income: $4147 Airbnb ROI: 2.99% Traditional ROI: 3.94%
144 Hawks Hill Road New Canaan, CT Fully Upgraded & Move-In Ready Newly renovated legal 4-bedroom, 2.5-bath Cape Cod on a cov...	4 beds \| 3 baths \| 2,306 sq.ft.	$1,415,000	Airbnb cash on cash: 0.26% Traditional cash on cash: 1.28% Airbnb Rental Income: $3354 Traditional Rental Income: $3959 Airbnb ROI: 0.26% Traditional ROI: 1.28%
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.	$1,299,000	Airbnb cash on cash: 1.35% Traditional cash on cash: 1.68% Airbnb Rental Income: $4585 Traditional Rental Income: $4027 Airbnb ROI: 1.35% Traditional ROI: 1.68%
125 Brewster Street Coventry, CT HIGHEST & BEST OFFERS DUE BY 8PM ON SATURDAY AUGUST 16. Totally remodeled home with 2 bedr...	2 beds \| 2 baths \| 1,342 sq.ft.	$370,000	Airbnb cash on cash: 1.14% Traditional cash on cash: 6.04% Airbnb Rental Income: $1696 Traditional Rental Income: $2927 Airbnb ROI: 1.14% Traditional ROI: 6.04%
8 Strawberry Ridge Road Ridgefield, CT Picture perfect New England colonial set back privately on 2.18 acres in the sought after ...	4 beds \| 3 baths \| 4,354 sq.ft.	$1,399,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.77% Airbnb Rental Income: $null Traditional Rental Income: $5515 Airbnb ROI: N/A Traditional ROI: 1.77%
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%
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: 0.69% Traditional cash on cash: 2.35% Airbnb Rental Income: $3214 Traditional Rental Income: $4006 Airbnb ROI: 0.69% Traditional ROI: 2.35%
559 Allen Road Torrington, CT Welcome to 559 Allen Road! This charming and well-built Colonial offers the perfect blend ...	4 beds \| 3 baths \| 2,205 sq.ft.	$499,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.91% Airbnb Rental Income: $null Traditional Rental Income: $4357 Airbnb ROI: N/A Traditional ROI: 6.91%
141 Dowd Avenue Canton, CT Charming and versatile property in the heart of Canton, CT, offering exceptional versatili...	4 beds \| 4 baths \| 4,251 sq.ft.	$698,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.38% Airbnb Rental Income: $null Traditional Rental Income: $5872 Airbnb ROI: N/A Traditional ROI: 6.38%
176 Laurel Hill Avenue Norwich, CT Step into this beautifully maintained Colonial featuring gleaming Oak floors throughout bo...	3 beds \| 2 baths \| 1,592 sq.ft.	$269,900	Airbnb cash on cash: -0.23% Traditional cash on cash: 8.97% Airbnb Rental Income: $986 Traditional Rental Income: $2974 Airbnb ROI: -0.23% Traditional ROI: 8.97%
4 Corcoran Avenue Stafford, CT Great news! This sought-after property is back on the market and now presents an even stro...	3 beds \| 2 baths \| 1,364 sq.ft.	$265,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.4% Airbnb Rental Income: $null Traditional Rental Income: $2716 Airbnb ROI: N/A Traditional ROI: 8.4%
253 Tophet Road Roxbury, CT Quintessential CT Mini- Estate of 2 Homes! Top restoration of 3-Bedroom/2.5 bath Victorian...	4 beds \| 4 baths \| 2,437 sq.ft.	$1,575,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.32% Airbnb Rental Income: $null Traditional Rental Income: $4372 Airbnb ROI: N/A Traditional ROI: 1.32%
78 Garnet Road Roxbury, CT Looking for a calming and peaceful property? You'll find total peace and quiet on this 15....	3 beds \| 4 baths \| 3,302 sq.ft.	$1,675,000	Airbnb cash on cash: -0.46% Traditional cash on cash: 2.25% Airbnb Rental Income: $2390 Traditional Rental Income: $6020 Airbnb ROI: -0.46% Traditional ROI: 2.25%
73 Grove Avenue Bristol, CT Welcome to 73 Grove Avenue, where space, privacy, and potential come together in one remar...	4 beds \| 3 baths \| 3,549 sq.ft.	$575,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.31% Airbnb Rental Income: $null Traditional Rental Income: $4320 Airbnb ROI: N/A Traditional ROI: 5.31%

Real Estate investment in Connecticut

There are 3,495 properties available for sale in the state of Connecticut. Preston, Hartford and Norwalk are the best rental property markets in Connecticut. The average median price of properties for sale in these cities are $474,000 and the average price per square foot is $0. Their average monthly cash on cash return is 6.00%.

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

There are 3,495 investment properties available for sale in Connecticut.

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

In 2025, Preston (8%) and Hartford (7%) 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

78 Hartford Avenue

Old Saybrook, CT

3 beds | 1 baths | 890 sq.ft.

$795,000

Airbnb cash on cash: 1.25%

Traditional cash on cash: 1.53%

Airbnb Rental Income: $3088

Traditional Rental Income: $2586

Airbnb ROI: 1.25%

Traditional ROI: 1.53%

951 Old Clinton Road #17

Westbrook, CT

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

$569,900

Airbnb cash on cash: -0.45%

Traditional cash on cash: 4.24%

Airbnb Rental Income: $1983

Traditional Rental Income: $3962

Airbnb ROI: -0.45%

Traditional ROI: 4.24%

739 Rock Rimmon Road

Stamford, CT

3 beds | 3 baths | 3,562 sq.ft.

$925,000

Airbnb cash on cash: 0.03%

Traditional cash on cash: 3.02%

Airbnb Rental Income: $2741

Traditional Rental Income: $4663

Airbnb ROI: 0.03%

Traditional ROI: 3.02%

1 Broad Street #11D

Stamford, CT

2 beds | 3 baths | 1,436 sq.ft.

$675,000

Airbnb cash on cash: -0.29%

Traditional cash on cash: 3.94%

Airbnb Rental Income: $2164

Traditional Rental Income: $4282

Airbnb ROI: -0.29%

Traditional ROI: 3.94%

147 Holly Hill Lane

Greenwich, CT

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

$9,999,999

Airbnb cash on cash: -2.97%

Traditional cash on cash: -2.78%

Airbnb Rental Income: $2158

Traditional Rental Income: $3419

Airbnb ROI: -2.97%

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%

2 Currier Court #2

Cheshire, CT

2 beds | 2 baths | 1,362 sq.ft.

$319,900

Airbnb cash on cash: 1.65%

Traditional cash on cash: 5.6%

Airbnb Rental Income: $1889

Traditional Rental Income: $2572

Airbnb ROI: 1.65%

Traditional ROI: 5.6%

36 State Street

Guilford, CT

1 beds | 1 baths | 720 sq.ft.

$450,000

Airbnb cash on cash: 0.96%

Traditional cash on cash: 2.34%

Airbnb Rental Income: $1902

Traditional Rental Income: $1979

Airbnb ROI: 0.96%