Real Estate Investment Properties for Sale in Portland, CT

Looking for investment property in Portland, CT with high ROI ?

Explore a variety of short-term homes & houses in Portland, CT. Invest wisely with VRBO & Portland, CT 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 Portland, CT

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
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%
62 Cornwall Street Portland, CT Come custom build the Home of your dreams. With a wide selection of plans, and possible Op...	3 beds \| 3 baths \| 2,521 sq.ft.	$789,900	Airbnb cash on cash: -0.08% Traditional cash on cash: 4.11% Airbnb Rental Income: $1388 Traditional Rental Income: $4048 Airbnb ROI: -0.08% Traditional ROI: 4.11%
171 Bartlett Street Portland, CT Step into timeless charm at 171 Bartlett Street in Portland, CT. This 1897 farmhouse sits ...	4 beds \| 2 baths \| 2,126 sq.ft.	$469,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.01% Airbnb Rental Income: $null Traditional Rental Income: $3348 Airbnb ROI: N/A Traditional ROI: 5.01%
Investment Properties for Sale in Other Cities of Connecticut
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: 6.35% Airbnb Rental Income: $null Traditional Rental Income: $2984 Airbnb ROI: N/A Traditional ROI: 6.35%
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%
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%
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%

Real Estate investment in Portland, CT

There are 3 properties for sale in the city of Portland . The median list price in Portland is $599,000 and the average price per square foot is $241. In March 2026, the average monthly cash on cash return in Portland is 4.00%. The average monthly rental income in Portland is $3,348.

Portland, CT Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 3 investment properties available for sale in Portland.

In 2026, the best neighborhood to buy investment property is Portland.

The ROI for Short-Term is higher than the Long-Term in Portland with average rental income of $1,388.

Your search for investment property begins and ends here

Investment Property for Sale in Portland, CT

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%

62 Cornwall Street

Portland, CT

3 beds | 3 baths | 2,521 sq.ft.

$789,900

Airbnb cash on cash: -0.08%

Traditional cash on cash: 4.11%

Airbnb Rental Income: $1388

Traditional Rental Income: $4048

Airbnb ROI: -0.08%

Traditional ROI: 4.11%

171 Bartlett Street

Portland, CT

4 beds | 2 baths | 2,126 sq.ft.

$469,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.01%

Airbnb Rental Income: $null

Traditional Rental Income: $3348

Airbnb ROI: N/A

Traditional ROI: 5.01%

Investment Properties for Sale in Other Cities of Connecticut

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%

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%

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%

Naugatuck , CT

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

$325,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.35%

Airbnb Rental Income: $null

Traditional Rental Income: $2984

Airbnb ROI: N/A

Traditional ROI: 6.35%

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%

Monroe , CT

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

$549,000