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
13 Edwards Rd Portland, CT Walk in and fall in love with this beautifully modernized ranch. Gleaming hardwood floors...	3 beds \| 1 baths \| 1,600 sq.ft.	$389,000	Airbnb cash on cash: 1.17% Traditional cash on cash: 3.41% Airbnb Rental Income: $1762 Traditional Rental Income: $2095 Airbnb ROI: 1.17% Traditional ROI: 3.41%
19 Plumrose Ct #19 Portland, CT This is your chance to come live in the wonderful 55+ community of Bartlett Hill! This mov...	2 beds \| 2 baths \| 1,503 sq.ft.	$500,000	Airbnb cash on cash: -2.26% Traditional cash on cash: 2.05% Airbnb Rental Income: $1246 Traditional Rental Income: $2867 Airbnb ROI: -2.26% Traditional ROI: 2.05%
184 Cox Rd Portland, CT 184 Cox Rd, Portland, CT 06480 \| Other	N/A beds \| N/A baths \| N/A	$189,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.29% Airbnb Rental Income: $null Traditional Rental Income: $885 Airbnb ROI: N/A Traditional ROI: 1.29%
Jobs Pond Rd Portland, CT Jobs Pond Rd, Portland, CT 06480 \| Other	N/A beds \| N/A baths \| N/A	$99,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.09% Airbnb Rental Income: $null Traditional Rental Income: $885 Airbnb ROI: N/A Traditional ROI: 5.09%
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%
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: 6.86% Airbnb Rental Income: $null Traditional Rental Income: $1057 Airbnb ROI: N/A Traditional ROI: 6.86%
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%
57 Summer St Portland, CT 57 Summer St, Portland, CT 06480 \| Single Family Residential	4 beds \| 3 baths \| 4,390 sq.ft.	$499,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.57% Airbnb Rental Income: $null Traditional Rental Income: $4157 Airbnb ROI: N/A Traditional ROI: 5.57%
39 Old Carriage Rd Portland, CT 39 Old Carriage Rd, Portland, CT 06480 \| Single Family Residential	4 beds \| 2 baths \| 2,754 sq.ft.	$550,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.26% Airbnb Rental Income: $null Traditional Rental Income: $2347 Airbnb ROI: N/A Traditional ROI: 1.26%
152 Summer St #152 Portland, CT 152 Summer St #152, Portland, CT 06480 \| Condo/Coop	2 beds \| 2 baths \| 1,314 sq.ft.	$275,000	Airbnb cash on cash: -1.28% Traditional cash on cash: 2.59% Airbnb Rental Income: $1246 Traditional Rental Income: $1852 Airbnb ROI: -1.28% Traditional ROI: 2.59%
3 Burr St Portland, CT 3 Burr St, Portland, CT 06480 \| Single Family Residential	3 beds \| 2 baths \| 1,442 sq.ft.	$420,000	Airbnb cash on cash: -0.1% Traditional cash on cash: 2.2% Airbnb Rental Income: $1762 Traditional Rental Income: $2185 Airbnb ROI: -0.1% Traditional ROI: 2.2%
11 Lake Rd Portland, CT 11 Lake Rd, Portland, CT 06480 \| Single Family Residential	3 beds \| 1 baths \| 1,230 sq.ft.	$375,000	Airbnb cash on cash: 0.25% Traditional cash on cash: 2.19% Airbnb Rental Income: $1762 Traditional Rental Income: $1959 Airbnb ROI: 0.25% Traditional ROI: 2.19%
11 Jobs Gate 1 Portland, CT 11 Jobs Gate 1, Portland, CT 06480 \| Single Family Residential	2 beds \| 1 baths \| 732 sq.ft.	$299,000	Airbnb cash on cash: -0.59% Traditional cash on cash: 2.97% Airbnb Rental Income: $1246 Traditional Rental Income: $1852 Airbnb ROI: -0.59% Traditional ROI: 2.97%
52 Jobs Gate 2 Portland, CT 52 Jobs Gate 2, Portland, CT 06480 \| Single Family Residential	1 beds \| 1 baths \| 592 sq.ft.	$179,900	Airbnb cash on cash: -0.25% Traditional cash on cash: 3.57% Airbnb Rental Income: $924 Traditional Rental Income: $1235 Airbnb ROI: -0.25% Traditional ROI: 3.57%
182 Cox Rd Portland, CT 182 Cox Rd, Portland, CT 06480 \| Other	N/A beds \| N/A baths \| N/A	$119,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.47% Airbnb Rental Income: $null Traditional Rental Income: $1189 Airbnb ROI: N/A Traditional ROI: 6.47%
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%
279 Middle Haddam Road Portland, CT Set in one of Portland's most picturesque locations with sweeping Connecticut River views,...	4 beds \| 5 baths \| 5,572 sq.ft.	$1,099,999	Airbnb cash on cash: N/A Traditional cash on cash: 5.48% Airbnb Rental Income: $null Traditional Rental Income: $8432 Airbnb ROI: N/A Traditional ROI: 5.48%

Real Estate investment in Portland, CT

There are 18 properties for sale in the city of Portland . The median list price in Portland is $357,786 and the average price per square foot is $145. In August 2026, the average monthly cash on cash return in Portland is 5.00%. The average monthly rental income in Portland is $1,852.

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 Short-Term is higher than the Long-Term in Portland with average rental income of $1,504.

Your search for investment property begins and ends here

Investment Property for Sale in Portland, CT

13 Edwards Rd

Portland, CT

3 beds | 1 baths | 1,600 sq.ft.

$389,000

Airbnb cash on cash: 1.17%

Traditional cash on cash: 3.41%

Airbnb Rental Income: $1762

Traditional Rental Income: $2095

Airbnb ROI: 1.17%

Traditional ROI: 3.41%

19 Plumrose Ct #19

Portland, CT

2 beds | 2 baths | 1,503 sq.ft.

$500,000

Airbnb cash on cash: -2.26%

Traditional cash on cash: 2.05%

Airbnb Rental Income: $1246

Traditional Rental Income: $2867

Airbnb ROI: -2.26%

Traditional ROI: 2.05%

184 Cox Rd

Portland, CT

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

$189,900

Airbnb cash on cash: N/A

Traditional cash on cash: 1.29%

Airbnb Rental Income: $null

Traditional Rental Income: $885

Airbnb ROI: N/A

Traditional ROI: 1.29%

Jobs Pond Rd

Portland, CT

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

$99,900

Airbnb cash on cash: N/A

Traditional cash on cash: 5.09%

Airbnb Rental Income: $null

Traditional Rental Income: $885

Airbnb ROI: N/A

Traditional ROI: 5.09%

402 Cox Rd #8

Portland, CT

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

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%

432 Cox Rd #3

Portland, CT

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

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