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
11 Ledgebrook Drive unit: 11 Norwalk, CT Don't miss this rare opportunity to own a completely updated two-bedroom townhouse with st...	2 beds \| 2 baths \| 1,173 sq.ft.	$459,000	Airbnb cash on cash: -0.34% Traditional cash on cash: 2.4% Airbnb Rental Income: $2268 Traditional Rental Income: $2877 Airbnb ROI: -0.34% Traditional ROI: 2.4%
23 Heaton Street Waterbury, CT Beautiful 3-Bedroom Home Built in 2009 - Move-In Ready! Welcome to 23 Heaton Street, a wel...	3 beds \| 3 baths \| 1,716 sq.ft.	$374,995	Airbnb cash on cash: -0.35% Traditional cash on cash: 3.94% Airbnb Rental Income: $1673 Traditional Rental Income: $2715 Airbnb ROI: -0.35% Traditional ROI: 3.94%
2 Elmwood Drive unit: 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.	$2,399,000	Airbnb cash on cash: -1.79% Traditional cash on cash: 0.1% Airbnb Rental Income: $2373 Traditional Rental Income: $5995 Airbnb ROI: -1.79% Traditional ROI: 0.1%
89 Alma Street Naugatuck, CT *More Photos to come* 89 Alma Street is a charming Colonial in Naugatuck, CT. 3 Bedroo...	3 beds \| 3 baths \| 1,536 sq.ft.	$325,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.81% Airbnb Rental Income: $null Traditional Rental Income: $1900 Airbnb ROI: N/A Traditional ROI: 2.81%
18 Pasture Lane Darien, CT You won't want to miss this charming New England Cape Cod, sited on a level 1 acre, in one...	4 beds \| 4 baths \| 3,061 sq.ft.	$2,985,000	Airbnb cash on cash: -1.05% Traditional cash on cash: 0.39% Airbnb Rental Income: $2511 Traditional Rental Income: $5895 Airbnb ROI: -1.05% Traditional ROI: 0.39%
286 Moose Hill Road Monroe, CT Welcome to this well maintained ranch style home nestled away from nearby amenities, but c...	2 beds \| 3 baths \| 1,012 sq.ft.	$549,000	Airbnb cash on cash: 0.59% Traditional cash on cash: 2.7% Airbnb Rental Income: $2198 Traditional Rental Income: $2727 Airbnb ROI: 0.59% Traditional ROI: 2.7%
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.	$189,900	Airbnb cash on cash: N/A Traditional cash on cash: 10.16% Airbnb Rental Income: $null Traditional Rental Income: $2298 Airbnb ROI: N/A Traditional ROI: 10.16%
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%
16 Rockmeadow Rd #Q Norwalk, CT Enjoy true neighborhood living in the peaceful, park-like setting of this 1 bedroom condo....	1 beds \| 1 baths \| 818 sq.ft.	$300,000	Airbnb cash on cash: 0.94% Traditional cash on cash: 2.49% Airbnb Rental Income: $1758 Traditional Rental Income: $1714 Airbnb ROI: 0.94% Traditional ROI: 2.49%
1462 South Avenue Stratford, CT This absolutely charming, bright, and tastefully updated condo alternative checks every bo...	3 beds \| 2 baths \| 1,152 sq.ft.	$299,000	Airbnb cash on cash: 2.47% Traditional cash on cash: 7.73% Airbnb Rental Income: $2065 Traditional Rental Income: $3013 Airbnb ROI: 2.47% Traditional ROI: 7.73%
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%
198 Good Hill Road Oxford, CT Tranquility abounds on this sprawling old style cape home nestled in the hills of Oxford. ...	3 beds \| 2 baths \| 2,400 sq.ft.	$399,900	Airbnb cash on cash: -1.21% Traditional cash on cash: 5.87% Airbnb Rental Income: $1000 Traditional Rental Income: $3300 Airbnb ROI: -1.21% Traditional ROI: 5.87%
125 Murphys Dr #125 Groton, CT Beautiful, spacious condominium in Woods Walk Commons , a quiet, neighborhood setting. Mod...	3 beds \| 2 baths \| 1,786 sq.ft.	$400,000	Airbnb cash on cash: 0.22% Traditional cash on cash: 4.56% Airbnb Rental Income: $1805 Traditional Rental Income: $2945 Airbnb ROI: 0.22% Traditional ROI: 4.56%
1200 Route 171 Woodstock, CT Adorable Country home on 3.22 acres with remodeled appliance eat in kitchen with large bre...	3 beds \| 1 baths \| 1,390 sq.ft.	$249,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.6% Airbnb Rental Income: $null Traditional Rental Income: $2212 Airbnb ROI: N/A Traditional ROI: 6.6%
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: -0.05% Traditional cash on cash: 1.59% Airbnb Rental Income: $1952 Traditional Rental Income: $2800 Airbnb ROI: -0.05% Traditional ROI: 1.59%
106 Oakwood Road East Lyme, CT Welcome to year-round coastal living in the highly sought-after Giant's Neck Beach communi...	3 beds \| 2 baths \| 1,636 sq.ft.	$459,900	Airbnb cash on cash: 1.94% Traditional cash on cash: 4.26% Airbnb Rental Income: $2429 Traditional Rental Income: $2831 Airbnb ROI: 1.94% Traditional ROI: 4.26%
10 Dogwood Court unit: 10 Cromwell, CT Spacious and well-maintained 3-bedroom, 2.5-bath large Condo. Granite countertops and an o...	3 beds \| 3 baths \| 1,832 sq.ft.	$254,900	Airbnb cash on cash: -0.82% Traditional cash on cash: 7.92% Airbnb Rental Income: $1617 Traditional Rental Income: $3262 Airbnb ROI: -0.82% Traditional ROI: 7.92%
881 Lafayette Boulevard unit: 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.	$315,000	Airbnb cash on cash: -2.32% Traditional cash on cash: 5.76% Airbnb Rental Income: $1051 Traditional Rental Income: $3081 Airbnb ROI: -2.32% Traditional ROI: 5.76%
176 Apple Lane Roxbury, CT Stunning modern shingle-style Colonial on over 4 manicured acres + gunnite pool in the hea...	4 beds \| 5 baths \| 3,566 sq.ft.	$2,295,000	Airbnb cash on cash: -0.96% Traditional cash on cash: 2.28% Airbnb Rental Income: $1924 Traditional Rental Income: $8323 Airbnb ROI: -0.96% Traditional ROI: 2.28%
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: -0.28% Traditional cash on cash: 2.25% Airbnb Rental Income: $2246 Traditional Rental Income: $4006 Airbnb ROI: -0.28% Traditional ROI: 2.25%
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.	$1,650,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.5% Airbnb Rental Income: $null Traditional Rental Income: $7351 Airbnb ROI: N/A Traditional ROI: 1.5%
171 Flagler Avenue Stratford, CT Welcome to this beautifully maintained Cape offering timeless charm and modern comfort. Wi...	3 beds \| 2 baths \| 1,336 sq.ft.	$539,900	Airbnb cash on cash: 0.52% Traditional cash on cash: 4.33% Airbnb Rental Income: $2065 Traditional Rental Income: $3457 Airbnb ROI: 0.52% Traditional ROI: 4.33%
1030 Washington Woodbury Road Roxbury, CT Good Hope Estate. Transport yourself to this stunning European-style home with all the bel...	4 beds \| 5 baths \| 4,874 sq.ft.	$2,395,000	Airbnb cash on cash: -0.81% Traditional cash on cash: 2.3% Airbnb Rental Income: $1924 Traditional Rental Income: $8326 Airbnb ROI: -0.81% Traditional ROI: 2.3%
24 Colonial Ridge Drive New Milford, CT Move right in to this beautifully updated and meticulously maintained four-bedroom Colonia...	4 beds \| 3 baths \| 2,292 sq.ft.	$630,000	Airbnb cash on cash: 4.17% Traditional cash on cash: 4.47% Airbnb Rental Income: $4788 Traditional Rental Income: $3976 Airbnb ROI: 4.17% Traditional ROI: 4.47%
498 Root Road Coventry, CT 1990 built full dormered vinyl sided cape nicely placed on .98 acre lot. This attractive 1...	3 beds \| 3 baths \| 1,685 sq.ft.	$409,900	Airbnb cash on cash: 1.62% Traditional cash on cash: 5.21% Airbnb Rental Income: $2197 Traditional Rental Income: $3024 Airbnb ROI: 1.62% Traditional ROI: 5.21%
179 South Street Roxbury, CT Own a Piece of Roxbury History! One of Roxbury's three oldest homes, this site has been ch...	3 beds \| 2 baths \| 1,772 sq.ft.	$985,000	Airbnb cash on cash: -1.24% Traditional cash on cash: 1.85% Airbnb Rental Income: $593 Traditional Rental Income: $3139 Airbnb ROI: -1.24% Traditional ROI: 1.85%
207 Ridgefield Avenue Waterbury, CT Beautifully Updated 3-Bedroom Colonial with Modern Upgrades and Stunning Design Features W...	3 beds \| 3 baths \| 3,114 sq.ft.	$495,000	Airbnb cash on cash: -0.68% Traditional cash on cash: 4.07% Airbnb Rental Income: $1972 Traditional Rental Income: $3654 Airbnb ROI: -0.68% Traditional ROI: 4.07%
11 Willow Lane Ledyard, CT This beautiful home is waiting just for you! This wonderfully maintained home includes a n...	3 beds \| 2 baths \| 1,620 sq.ft.	$345,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.53% Airbnb Rental Income: $null Traditional Rental Income: $3040 Airbnb ROI: N/A Traditional ROI: 6.53%
16 Sunset Hill Avenue Norwalk, CT If you've been searching for a home that truly has it all - you're going to love this one!...	4 beds \| 3 baths \| 2,525 sq.ft.	$879,000	Airbnb cash on cash: 1.58% Traditional cash on cash: 2.31% Airbnb Rental Income: $4407 Traditional Rental Income: $4081 Airbnb ROI: 1.58% Traditional ROI: 2.31%
79 Santina Drive Manchester, CT Tucked at the end of a quiet cul-de-sac near the Glastonbury line, this classic Cape-style...	2 beds \| 2 baths \| 1,601 sq.ft.	$345,000	Airbnb cash on cash: 0.46% Traditional cash on cash: 4.59% Airbnb Rental Income: $1763 Traditional Rental Income: $2621 Airbnb ROI: 0.46% Traditional ROI: 4.59%
161 Abbotsford Avenue West Hartford, CT Lovely 3 bedroom colonial. Has Kitchen, dinning room and fireplaced living room. Three goo...	3 beds \| 1 baths \| 1,383 sq.ft.	$320,000	Airbnb cash on cash: 4.79% Traditional cash on cash: 4.45% Airbnb Rental Income: $3122 Traditional Rental Income: $2310 Airbnb ROI: 4.79% Traditional ROI: 4.45%
206 Highland Avenue West Haven, CT Enjoy serene, water-oriented living in this beautifully maintained home, thoughtfully upda...	2 beds \| 2 baths \| 1,030 sq.ft.	$410,000	Airbnb cash on cash: -1.84% Traditional cash on cash: 1.47% Airbnb Rental Income: $751 Traditional Rental Income: $1710 Airbnb ROI: -1.84% Traditional ROI: 1.47%

Real Estate investment in Connecticut

There are 2,783 properties available for sale in the state of Connecticut. Plainfield, Norwalk and West Hartford are the best rental property markets in Connecticut. The average median price of properties for sale in these cities are $532,483 and the average price per square foot is $0. Their average monthly cash on cash return is 3.67%.

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

There are 2,783 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 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

11 Ledgebrook Drive unit: 11

Norwalk, CT

2 beds | 2 baths | 1,173 sq.ft.

$459,000

Airbnb cash on cash: -0.34%

Traditional cash on cash: 2.4%

Airbnb Rental Income: $2268

Traditional Rental Income: $2877

Airbnb ROI: -0.34%

Traditional ROI: 2.4%

23 Heaton Street

Waterbury, CT

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

$374,995

Airbnb cash on cash: -0.35%

Traditional cash on cash: 3.94%

Airbnb Rental Income: $1673

Traditional Rental Income: $2715

Airbnb ROI: -0.35%

Traditional ROI: 3.94%

2 Elmwood Drive unit: 2

Fairfield, CT

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

$2,399,000

Airbnb cash on cash: -1.79%

Traditional cash on cash: 0.1%

Airbnb Rental Income: $2373

Traditional Rental Income: $5995

Airbnb ROI: -1.79%

Traditional ROI: 0.1%

89 Alma Street

Naugatuck, CT

3 beds | 3 baths | 1,536 sq.ft.

$325,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.81%

Airbnb Rental Income: $null

Traditional Rental Income: $1900

Airbnb ROI: N/A

Traditional ROI: 2.81%

18 Pasture Lane

Darien, CT

4 beds | 4 baths | 3,061 sq.ft.

$2,985,000

Airbnb cash on cash: -1.05%

Traditional cash on cash: 0.39%

Airbnb Rental Income: $2511

Traditional Rental Income: $5895

Airbnb ROI: -1.05%

Traditional ROI: 0.39%

286 Moose Hill Road

Monroe, CT

2 beds | 3 baths | 1,012 sq.ft.

$549,000

Airbnb cash on cash: 0.59%

Traditional cash on cash: 2.7%

Airbnb Rental Income: $2198

Traditional Rental Income: $2727

Airbnb ROI: 0.59%

Traditional ROI: 2.7%

16 Marlene Drive

Ledyard, CT

4 beds | 1 baths | 1,260 sq.ft.

$189,900

Airbnb cash on cash: N/A

Traditional cash on cash: 10.16%

Airbnb Rental Income: $null

Traditional Rental Income: $2298

Airbnb ROI: N/A

Traditional ROI: 10.16%

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