Real Estate Investment Properties for Sale in Portland, ME

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
85 Upper A Street Portland, ME Serenity Cottage will steal a little piece of your heart just like it has for the current ...	2 beds \| 1 baths \| 1,000 sq.ft.	$599,900	Airbnb cash on cash: 2% Traditional cash on cash: 1.93% Airbnb Rental Income: $2790 Traditional Rental Income: $2094 Airbnb ROI: 2% Traditional ROI: 1.93%
11 Ocean Spray Road Portland, ME Breath taking views at this one of a kind Peaks Island home! This newly renovated home sit...	2 beds \| 2 baths \| 2,345 sq.ft.	$1,999,900	Airbnb cash on cash: -0.52% Traditional cash on cash: 0.11% Airbnb Rental Income: $2790 Traditional Rental Income: $3298 Airbnb ROI: -0.52% Traditional ROI: 0.11%
160 Craigie Street Portland, ME Welcome to 160 Craigie Streetâwhere history, style, and location converge in one unforge...	4 beds \| 4 baths \| 3,197 sq.ft.	$1,595,000	Airbnb cash on cash: 0.13% Traditional cash on cash: 1.44% Airbnb Rental Income: $3535 Traditional Rental Income: $4692 Airbnb ROI: 0.13% Traditional ROI: 1.44%
383 Commercial Street Portland, ME This stylish 1-bedroom, 1-bath condo at Hobson's Landing offers the perfect blend of moder...	1 beds \| 1 baths \| 777 sq.ft.	$625,000	Airbnb cash on cash: 0.39% Traditional cash on cash: 0.46% Airbnb Rental Income: $3130 Traditional Rental Income: $2460 Airbnb ROI: 0.39% Traditional ROI: 0.46%
44 Montrose Avenue Portland, ME OPEN HOUSE SUNDAY SEPTEMBER 21, 11:30 - 1:00, come on by! Welcome to the Rosemont neighbo...	3 beds \| 2 baths \| 1,582 sq.ft.	$649,000	Airbnb cash on cash: 4.23% Traditional cash on cash: 3.23% Airbnb Rental Income: $4672 Traditional Rental Income: $3095 Airbnb ROI: 4.23% Traditional ROI: 3.23%
25 High Street Portland, ME Experience luxury condo living in the heart of Portland's historic Old Port, where world-c...	2 beds \| 2 baths \| 1,164 sq.ft.	$750,000	Airbnb cash on cash: 2.7% Traditional cash on cash: 2.67% Airbnb Rental Income: $4479 Traditional Rental Income: $3519 Airbnb ROI: 2.7% Traditional ROI: 2.67%
25 Broadway Portland, ME Welcome to 25 Broadway - a beautifully maintained colonial nestled in a peaceful, sought-a...	3 beds \| 2 baths \| 1,934 sq.ft.	$695,000	Airbnb cash on cash: 4.43% Traditional cash on cash: 2.9% Airbnb Rental Income: $5214 Traditional Rental Income: $3166 Airbnb ROI: 4.43% Traditional ROI: 2.9%
119 Hennessy Drive Portland, ME Welcome to 119 Hennessy Drive, tucked away on a quiet tree-lined street in Portland's desi...	3 beds \| 1 baths \| 1,357 sq.ft.	$499,000	Airbnb cash on cash: 3.36% Traditional cash on cash: 3.31% Airbnb Rental Income: $3232 Traditional Rental Income: $2481 Airbnb ROI: 3.36% Traditional ROI: 3.31%
387 Commercial Street Portland, ME Stunning, sun-drenched corner unit with dramatic floor-to-ceiling glass. Pristine, two-b...	2 beds \| 2 baths \| 1,426 sq.ft.	$1,150,000	Airbnb cash on cash: 0.29% Traditional cash on cash: 0.4% Airbnb Rental Income: $4479 Traditional Rental Income: $3661 Airbnb ROI: 0.29% Traditional ROI: 0.4%
5 Eastern Promenade Portland, ME The Crown Jewel of Portland's Eastern Promenade. Built in 1898 for Henry Merrillâa pr...	3 beds \| 3 baths \| 1,923 sq.ft.	$3,495,000	Airbnb cash on cash: -1.04% Traditional cash on cash: -1.1% Airbnb Rental Income: $3862 Traditional Rental Income: $2846 Airbnb ROI: -1.04% Traditional ROI: -1.1%
95 Herman Avenue Portland, ME This charming 3-bedroom, 2-bath home on Peaks Island is bathed in natural passive solar li...	3 beds \| 2 baths \| 2,108 sq.ft.	$849,000	Airbnb cash on cash: 1.46% Traditional cash on cash: 1.66% Airbnb Rental Income: $3320 Traditional Rental Income: $2737 Airbnb ROI: 1.46% Traditional ROI: 1.66%
10 Hammond Street Portland, ME Experience the perfect blend of vibrant city living and modern luxury in this stunning Eas...	2 beds \| 2 baths \| 1,283 sq.ft.	$774,000	Airbnb cash on cash: 2.17% Traditional cash on cash: 2.63% Airbnb Rental Income: $3883 Traditional Rental Income: $3382 Airbnb ROI: 2.17% Traditional ROI: 2.63%
10 Exchange Street Portland, ME Introducing Unit 307 at 10 Exchange Street â set on one of the Old Port's most iconic co...	1 beds \| 1 baths \| 565 sq.ft.	$444,000	Airbnb cash on cash: 2.08% Traditional cash on cash: 0.03% Airbnb Rental Income: $3130 Traditional Rental Income: $1567 Airbnb ROI: 2.08% Traditional ROI: 0.03%
75 Chestnut Street Portland, ME Daymark is a balanced approach to living that focuses on community, sustainability, and co...	2 beds \| 2 baths \| 1,019 sq.ft.	$699,000	Airbnb cash on cash: 0.58% Traditional cash on cash: 0.47% Airbnb Rental Income: $3800 Traditional Rental Income: $2909 Airbnb ROI: 0.58% Traditional ROI: 0.47%
1673 Westbrook Street Portland, ME Handsome Colonial in the Stroudwater area of Portland. Private back yard bordering the For...	4 beds \| 3 baths \| 3,756 sq.ft.	$599,000	Airbnb cash on cash: 2.5% Traditional cash on cash: 2.91% Airbnb Rental Income: $3515 Traditional Rental Income: $2969 Airbnb ROI: 2.5% Traditional ROI: 2.91%
95 Lane Avenue Portland, ME Welcome to 95 Lane Avenue in Portland, Maine. Located in a quiet neighborhood, this spaci...	3 beds \| 2 baths \| 1,912 sq.ft.	$565,000	Airbnb cash on cash: 5.95% Traditional cash on cash: 2.67% Airbnb Rental Income: $5214 Traditional Rental Income: $2427 Airbnb ROI: 5.95% Traditional ROI: 2.67%
244 Ray Street Portland, ME Don't miss beautifully renovated Garrison-style home nestled in the prime North Deering, P...	5 beds \| 2 baths \| 2,256 sq.ft.	$529,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.52% Airbnb Rental Income: $null Traditional Rental Income: $2874 Airbnb ROI: N/A Traditional ROI: 3.52%
21 Dow Street Portland, ME Newly renovated Condo in Historic brick building. Roofs rights above the double garage wit...	1 beds \| 1 baths \| 520 sq.ft.	$385,000	Airbnb cash on cash: 5.25% Traditional cash on cash: 2.32% Airbnb Rental Income: $3624 Traditional Rental Income: $1770 Airbnb ROI: 5.25% Traditional ROI: 2.32%
206 Chandlers Wharf Portland, ME Welcome to Chandler's Wharf â an opportunity to own a vibrant, design-forward townhouse ...	2 beds \| 3 baths \| 1,755 sq.ft.	$995,000	Airbnb cash on cash: 0.21% Traditional cash on cash: -0.97% Airbnb Rental Income: $4479 Traditional Rental Income: $2450 Airbnb ROI: 0.21% Traditional ROI: -0.97%
7 Gable Court Portland, ME Set in the wooded Ledgewood community, this end-unit townhouse offers a surprising amount ...	3 beds \| 3 baths \| 1,680 sq.ft.	$519,000	Airbnb cash on cash: 2.27% Traditional cash on cash: 1.4% Airbnb Rental Income: $3681 Traditional Rental Income: $2457 Airbnb ROI: 2.27% Traditional ROI: 1.4%
55 Pitt Street Portland, ME Nestled in one of Portland's most desired Neighborhoods, you get walkability to all great ...	2 beds \| 1 baths \| 1,000 sq.ft.	$355,000	Airbnb cash on cash: -0.25% Traditional cash on cash: 2.47% Airbnb Rental Income: $1629 Traditional Rental Income: $2076 Airbnb ROI: -0.25% Traditional ROI: 2.47%
45 Eastern Promenade Portland, ME Experience incredible ocean views from the penthouse floor of this well-located condo at P...	2 beds \| 2 baths \| 1,054 sq.ft.	$695,000	Airbnb cash on cash: 0.81% Traditional cash on cash: -1.06% Airbnb Rental Income: $3896 Traditional Rental Income: $1847 Airbnb ROI: 0.81% Traditional ROI: -1.06%
62 India Street Portland, ME In immaculate condition, this absolutely adorable top-floor one-bedroom/one bath unit offe...	1 beds \| 1 baths \| 677 sq.ft.	$585,000	Airbnb cash on cash: 2.71% Traditional cash on cash: 3.92% Airbnb Rental Income: $3624 Traditional Rental Income: $3490 Airbnb ROI: 2.71% Traditional ROI: 3.92%
30 Pleasant Cove Lane Portland, ME This impeccably maintained Maine island property on Great Diamond Island, provides a sense...	4 beds \| 4 baths \| 2,969 sq.ft.	$1,690,000	Airbnb cash on cash: -0.59% Traditional cash on cash: -0.43% Airbnb Rental Income: $4586 Traditional Rental Income: $3889 Airbnb ROI: -0.59% Traditional ROI: -0.43%
51 Carleton Street Portland, ME OCCUPANCY OCTOBER 2025- SITE TOURS AVAILABLE! West End charm meets modern luxury. Historic...	4 beds \| 5 baths \| 3,089 sq.ft.	$2,099,000	Airbnb cash on cash: -0.77% Traditional cash on cash: 0.06% Airbnb Rental Income: $4673 Traditional Rental Income: $5318 Airbnb ROI: -0.77% Traditional ROI: 0.06%
6 Quartermaster Court Portland, ME Island living could not be easier! This year-round historic Quartermasters unit is located...	3 beds \| 3 baths \| 2,016 sq.ft.	$875,000	Airbnb cash on cash: -0.35% Traditional cash on cash: 0.49% Airbnb Rental Income: $3408 Traditional Rental Income: $3333 Airbnb ROI: -0.35% Traditional ROI: 0.49%
21 Chestnut Street Portland, ME This spacious, light-filled loft in downtown Portland offers the perfect blend of convenie...	1 beds \| 1 baths \| 1,024 sq.ft.	$459,000	Airbnb cash on cash: 0.8% Traditional cash on cash: 1.18% Airbnb Rental Income: $2703 Traditional Rental Income: $2224 Airbnb ROI: 0.8% Traditional ROI: 1.18%
26 Thomas Street Portland, ME Wooden beams and intricate stained glass windows frame open, flowing living spaces in this...	3 beds \| 3 baths \| 1,507 sq.ft.	$799,000	Airbnb cash on cash: 1.23% Traditional cash on cash: 1.5% Airbnb Rental Income: $4033 Traditional Rental Income: $3372 Airbnb ROI: 1.23% Traditional ROI: 1.5%
55 Carleton Street Portland, ME OCCUPANCY OCTOBER 2025- SITE TOURS AVAILABLE! West End charm meets modern luxury. Historic...	4 beds \| 5 baths \| 3,089 sq.ft.	$2,150,000	Airbnb cash on cash: -0.81% Traditional cash on cash: 0% Airbnb Rental Income: $4673 Traditional Rental Income: $5318 Airbnb ROI: -0.81% Traditional ROI: 0%
773 Congress Street Portland, ME A new roof! A new front porch! Sunfilled second floor condo conveniently located to restau...	2 beds \| 2 baths \| 1,180 sq.ft.	$549,000	Airbnb cash on cash: -0.51% Traditional cash on cash: 2.15% Airbnb Rental Income: $1629 Traditional Rental Income: $2534 Airbnb ROI: -0.51% Traditional ROI: 2.15%
192 Milton Street Portland, ME Nestled in a charming Portland neighborhood, this cape style home provides lots of room fo...	3 beds \| 2 baths \| 2,351 sq.ft.	$604,900	Airbnb cash on cash: 2.92% Traditional cash on cash: 2.7% Airbnb Rental Income: $3484 Traditional Rental Income: $2590 Airbnb ROI: 2.92% Traditional ROI: 2.7%
15 Middle Street Portland, ME In the heart of Portland's renowned India Street block, this sophisticated first-floor, th...	3 beds \| 3 baths \| 2,076 sq.ft.	$1,149,500	Airbnb cash on cash: 0.32% Traditional cash on cash: 0.75% Airbnb Rental Income: $3484 Traditional Rental Income: $3172 Airbnb ROI: 0.32% Traditional ROI: 0.75%
547 Congress Street Portland, ME The best private rooftop in Portland - just in time for summer. This luxurious loft-style ...	2 beds \| 3 baths \| 2,370 sq.ft.	$3,190,000	Airbnb cash on cash: -0.94% Traditional cash on cash: -0.59% Airbnb Rental Income: $1629 Traditional Rental Income: $2204 Airbnb ROI: -0.94% Traditional ROI: -0.59%
65 Munjoy Street Portland, ME MUNJOY HILL - A RARE FIND AT THIS PRICE POINT! CONTEMPORARY AND SPACIOUS 1BR/1 BATH ON THE...	1 beds \| 1 baths \| 739 sq.ft.	$445,000	Airbnb cash on cash: 3.66% Traditional cash on cash: 1.79% Airbnb Rental Income: $3624 Traditional Rental Income: $2049 Airbnb ROI: 3.66% Traditional ROI: 1.79%
15 Brown Street Portland, ME Experience elevated downtown living in this exceptional 3-bedroom, 2-bath residence at 15 ...	3 beds \| 2 baths \| 1,460 sq.ft.	$725,000	Airbnb cash on cash: 3.23% Traditional cash on cash: 0.89% Airbnb Rental Income: $5512 Traditional Rental Income: $2821 Airbnb ROI: 3.23% Traditional ROI: 0.89%
64 Pine Street Portland, ME OPEN HOUSE WEEKEND September 25th - 28th from 11:00 to 1:00 @ development showroom - 64 Pi...	3 beds \| 3 baths \| 1,523 sq.ft.	$1,795,000	Airbnb cash on cash: 0% Traditional cash on cash: 0.55% Airbnb Rental Income: $3484 Traditional Rental Income: $3625 Airbnb ROI: 0% Traditional ROI: 0.55%
246 Eastern Promenade Portland, ME LIVE ELEVATED AT 246 EASTERN PROMENADE Only 8 Residences Remain \| Completion Mid-Fall 202...	2 beds \| 3 baths \| 2,126 sq.ft.	$2,975,700	Airbnb cash on cash: -0.75% Traditional cash on cash: -0.2% Airbnb Rental Income: $1629 Traditional Rental Income: $2705 Airbnb ROI: -0.75% Traditional ROI: -0.2%
3 Walker Street Portland, ME First time on market in 20 years. Located in Portland's iconic West End, this top-floor-2-...	2 beds \| 1 baths \| 1,068 sq.ft.	$455,000	Airbnb cash on cash: 2.59% Traditional cash on cash: 2.47% Airbnb Rental Income: $2848 Traditional Rental Income: $2132 Airbnb ROI: 2.59% Traditional ROI: 2.47%
106 Cumberland Avenue Portland, ME Looking for awesome Munjoy Hill and Eastern Promenade location close to all amenities? Loo...	2 beds \| 2 baths \| 1,170 sq.ft.	$709,900	Airbnb cash on cash: 2.7% Traditional cash on cash: 1.95% Airbnb Rental Income: $3883 Traditional Rental Income: $2547 Airbnb ROI: 2.7% Traditional ROI: 1.95%
104 Grant Street Portland, ME Welcome to your dream condo nestled on the picturesque peninsula of Portland, where city l...	1 beds \| 1 baths \| 616 sq.ft.	$342,500	Airbnb cash on cash: 2.36% Traditional cash on cash: 5.25% Airbnb Rental Income: $1951 Traditional Rental Income: $2366 Airbnb ROI: 2.36% Traditional ROI: 5.25%

Real Estate investment in Portland, ME

There are 91 properties for sale in the city of Portland . The median list price in Portland is $695,000 and the average price per square foot is $401. In October 2025, the average monthly cash on cash return in Portland is 2.00%. The average monthly rental income in Portland is $3,097.

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

There are 91 investment properties available for sale in Portland.

In 2025, the best neighborhood to buy investment property is Libbytown.

The ROI for Short-Term is higher than the Long-Term in Portland with average rental income of $3,862.

Your search for investment property begins and ends here

Investment Property for Sale in Portland, ME

85 Upper A Street

Portland, ME

2 beds | 1 baths | 1,000 sq.ft.

$599,900

Airbnb cash on cash: 2%

Traditional cash on cash: 1.93%

Airbnb Rental Income: $2790

Traditional Rental Income: $2094

Airbnb ROI: 2%

Traditional ROI: 1.93%

11 Ocean Spray Road

Portland, ME

2 beds | 2 baths | 2,345 sq.ft.

$1,999,900

Airbnb cash on cash: -0.52%

Traditional cash on cash: 0.11%

Airbnb Rental Income: $2790

Traditional Rental Income: $3298

Airbnb ROI: -0.52%

Traditional ROI: 0.11%

160 Craigie Street

Portland, ME

4 beds | 4 baths | 3,197 sq.ft.

$1,595,000

Airbnb cash on cash: 0.13%

Traditional cash on cash: 1.44%

Airbnb Rental Income: $3535

Traditional Rental Income: $4692

Airbnb ROI: 0.13%

Traditional ROI: 1.44%

383 Commercial Street

Portland, ME

1 beds | 1 baths | 777 sq.ft.

$625,000

Airbnb cash on cash: 0.39%

Traditional cash on cash: 0.46%

Airbnb Rental Income: $3130

Traditional Rental Income: $2460

Airbnb ROI: 0.39%

Traditional ROI: 0.46%

44 Montrose Avenue

Portland, ME

3 beds | 2 baths | 1,582 sq.ft.

$649,000

Airbnb cash on cash: 4.23%

Traditional cash on cash: 3.23%

Airbnb Rental Income: $4672

Traditional Rental Income: $3095

Airbnb ROI: 4.23%

Traditional ROI: 3.23%

25 High Street

Portland, ME

2 beds | 2 baths | 1,164 sq.ft.

$750,000

Airbnb cash on cash: 2.7%

Traditional cash on cash: 2.67%

Airbnb Rental Income: $4479

Traditional Rental Income: $3519

Airbnb ROI: 2.7%

Traditional ROI: 2.67%

25 Broadway

Portland, ME

3 beds | 2 baths | 1,934 sq.ft.

$695,000

Airbnb cash on cash: 4.43%

Traditional cash on cash: 2.9%

Airbnb Rental Income: $5214

Traditional Rental Income: $3166

Airbnb ROI: 4.43%

Traditional ROI: 2.9%

119 Hennessy Drive

Portland, ME

3 beds | 1 baths | 1,357 sq.ft.

$499,000

Airbnb cash on cash: 3.36%

Traditional cash on cash: 3.31%

Airbnb Rental Income: $3232

Traditional Rental Income: $2481

Airbnb ROI: 3.36%