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 St Portland, CT Come custom build the Home of your dreams. With a wide selection of plans, and possible Op...	3 beds \| 2 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%
5 Coe Ave Portland, CT 5 Coe Ave, Portland, CT 06480 \| Single Family Residential	4 beds \| 3 baths \| 1,824 sq.ft.	$349,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.74% Airbnb Rental Income: $null Traditional Rental Income: $2347 Airbnb ROI: N/A Traditional ROI: 3.74%
220 Rose Hill Rd Portland, CT 220 Rose Hill Rd, Portland, CT 06480 \| Single Family Residential	3 beds \| 1 baths \| 1,428 sq.ft.	$399,900	Airbnb cash on cash: -0.78% Traditional cash on cash: 2.07% Airbnb Rental Income: $1388 Traditional Rental Income: $2038 Airbnb ROI: -0.78% Traditional ROI: 2.07%
76B Maple Rd Portland, CT 76B Maple Rd, Portland, CT 06480 \| Single Family Residential	3 beds \| 2 baths \| 1,897 sq.ft.	$650,000	Airbnb cash on cash: -1.68% Traditional cash on cash: 0.33% Airbnb Rental Income: $1388 Traditional Rental Income: $2185 Airbnb ROI: -1.68% Traditional ROI: 0.33%
9 Pear Orchard Rd #9 Portland, CT 9 Pear Orchard Rd #9, Portland, CT 06480 \| Single Family Residential	2 beds \| 2 baths \| 1,404 sq.ft.	$505,000	Airbnb cash on cash: -2.04% Traditional cash on cash: 0.76% Airbnb Rental Income: $1343 Traditional Rental Income: $2253 Airbnb ROI: -2.04% Traditional ROI: 0.76%
1263, 1306, 1316, 1318 Pecausett Mdws Portland, CT 1263, 1306, 1316, 1318 Pecausett Mdws, Portland, CT 06480 \| Other	N/A beds \| N/A baths \| N/A	$75,600	Airbnb cash on cash: N/A Traditional cash on cash: 11.63% Airbnb Rental Income: $null Traditional Rental Income: $1189 Airbnb ROI: N/A Traditional ROI: 11.63%
184 Cox Rd Portland, CT 184 Cox Rd, Portland, CT 06480 \| Other	N/A beds \| N/A baths \| N/A	$199,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.68% Airbnb Rental Income: $null Traditional Rental Income: $1189 Airbnb ROI: N/A Traditional ROI: 2.68%
Jobs Pond Rd Portland, CT Jobs Pond Rd, Portland, CT 06480 \| Other	N/A beds \| N/A baths \| N/A	$110,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.37% Airbnb Rental Income: $null Traditional Rental Income: $885 Airbnb ROI: N/A Traditional ROI: 4.37%
402 Cox Rd #8 Portland, CT 402 Cox Rd #8, Portland, CT 06480 \| Other	N/A beds \| N/A baths \| 1,817 sq.ft.	$99,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.86% Airbnb Rental Income: $null Traditional Rental Income: $1057 Airbnb ROI: N/A Traditional ROI: 6.86%
420 Cox Rd #5 Portland, CT 420 Cox Rd #5, Portland, CT 06480 \| Other	N/A beds \| N/A baths \| 1,817 sq.ft.	$99,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.86% Airbnb Rental Income: $null Traditional Rental Income: $1057 Airbnb ROI: N/A Traditional ROI: 6.86%
414 Cox Rd #6 Portland, CT 414 Cox Rd #6, Portland, CT 06480 \| Other	N/A beds \| N/A baths \| 1,817 sq.ft.	$99,999	Airbnb cash on cash: N/A Traditional cash on cash: 6.85% Airbnb Rental Income: $null Traditional Rental Income: $1057 Airbnb ROI: N/A Traditional ROI: 6.85%
426 Cox Rd #4 Portland, CT 426 Cox Rd #4, Portland, CT 06480 \| Other	N/A beds \| N/A baths \| 1,817 sq.ft.	$124,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.03% Airbnb Rental Income: $null Traditional Rental Income: $1189 Airbnb ROI: N/A Traditional ROI: 6.03%
408 Cox Rd #7 Portland, CT 408 Cox Rd #7, Portland, CT 06480 \| Other	N/A beds \| N/A baths \| 1,817 sq.ft.	$99,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.86% Airbnb Rental Income: $null Traditional Rental Income: $1057 Airbnb ROI: N/A Traditional ROI: 6.86%
444 Cox Rd #1 Portland, CT 444 Cox Rd #1, Portland, CT 06480 \| Other	N/A beds \| N/A baths \| 1,817 sq.ft.	$99,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.22% Airbnb Rental Income: $null Traditional Rental Income: $1189 Airbnb ROI: N/A Traditional ROI: 8.22%
432 Cox Rd #3 Portland, CT 432 Cox Rd #3, Portland, CT 06480 \| Other	N/A beds \| N/A baths \| 1,817 sq.ft.	$124,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.93% Airbnb Rental Income: $null Traditional Rental Income: $1057 Airbnb ROI: N/A Traditional ROI: 4.93%
438 Cox Rd #2 Portland, CT 438 Cox Rd #2, Portland, CT 06480 \| Other	N/A beds \| N/A baths \| 1,817 sq.ft.	$99,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.86% Airbnb Rental Income: $null Traditional Rental Income: $1057 Airbnb ROI: N/A Traditional ROI: 6.86%

Real Estate investment in Portland, CT

There are 18 properties for sale in the city of Portland . The median list price in Portland is $569,000 and the average price per square foot is $231. In February 2026, the average monthly cash on cash return in Portland is 5.00%. The average monthly rental income in Portland is $1,189.

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

There are 18 investment properties available for sale in Portland.

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

The ROI for Long-Term is higher than the Short-Term in Portland with average rental income of $1,189.

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 St

Portland, CT

3 beds | 2 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%

5 Coe Ave

Portland, CT

4 beds | 3 baths | 1,824 sq.ft.

$349,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.74%

Airbnb Rental Income: $null

Traditional Rental Income: $2347

Airbnb ROI: N/A

Traditional ROI: 3.74%

220 Rose Hill Rd

Portland, CT

3 beds | 1 baths | 1,428 sq.ft.

$399,900

Airbnb cash on cash: -0.78%

Traditional cash on cash: 2.07%

Airbnb Rental Income: $1388

Traditional Rental Income: $2038

Airbnb ROI: -0.78%

Traditional ROI: 2.07%

76B Maple Rd

Portland, CT

3 beds | 2 baths | 1,897 sq.ft.

$650,000

Airbnb cash on cash: -1.68%

Traditional cash on cash: 0.33%

Airbnb Rental Income: $1388

Traditional Rental Income: $2185

Airbnb ROI: -1.68%

Traditional ROI: 0.33%

9 Pear Orchard Rd #9

Portland, CT

2 beds | 2 baths | 1,404 sq.ft.

$505,000

Airbnb cash on cash: -2.04%

Traditional cash on cash: 0.76%

Airbnb Rental Income: $1343

Traditional Rental Income: $2253

Airbnb ROI: -2.04%

Traditional ROI: 0.76%

1263, 1306, 1316, 1318 Pecausett Mdws

Portland, CT

N/A beds | N/A baths | N/A

$75,600

Airbnb cash on cash: N/A

Traditional cash on cash: 11.63%

Airbnb Rental Income: $null

Traditional Rental Income: $1189

Airbnb ROI: N/A