Real Estate Investment Properties for Sale in South Portland, ME

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
35 Jefferson Street South Portland, ME This cozy and updated home nestled in the highly desirable Ferry Village neighborhood of S...	3 beds \| N/A baths \| 1,322 sq.ft.	$515,000	Airbnb cash on cash: 3.96% Traditional cash on cash: 1.7% Airbnb Rental Income: $3656 Traditional Rental Income: $1768 Airbnb ROI: 3.96% Traditional ROI: 1.7%
267 Pleasant Avenue South Portland, ME Discover this beautifully maintained 4-bedroom raised ranch located in South Portland. Thi...	4 beds \| N/A baths \| 1,880 sq.ft.	$623,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.58% Airbnb Rental Income: $null Traditional Rental Income: $3082 Airbnb ROI: N/A Traditional ROI: 3.58%
79 Massachusetts Avenue South Portland, ME Step inside and discover a home filled with light, character, and opportunity in one of So...	3 beds \| 1 baths \| 1,276 sq.ft.	$435,000	Airbnb cash on cash: 5.15% Traditional cash on cash: 4.32% Airbnb Rental Income: $3656 Traditional Rental Income: $2520 Airbnb ROI: 5.15% Traditional ROI: 4.32%
20 Noyes Street South Portland, ME This equisite 1925 Cape has unique features from yesteryear. Meticulously cared for both i...	3 beds \| N/A baths \| 1,460 sq.ft.	$499,900	Airbnb cash on cash: 4.24% Traditional cash on cash: 3.53% Airbnb Rental Income: $3656 Traditional Rental Income: $2526 Airbnb ROI: 4.24% Traditional ROI: 3.53%
753 Main Street South Portland, ME INVESTORS TAKE NOTICE!! Fantastic opportunity! Zoning and lot size allow for the addition...	N/A beds \| N/A baths \| 1,372 sq.ft.	$499,000	Airbnb cash on cash: 2.84% Traditional cash on cash: 2.28% Airbnb Rental Income: $3110 Traditional Rental Income: $2140 Airbnb ROI: 2.84% Traditional ROI: 2.28%
83 Broadway South Portland, ME Nestled in South Portland's vibrant heart, 83 Broadway invites you to embrace coastal Main...	3 beds \| N/A baths \| 1,162 sq.ft.	$575,000	Airbnb cash on cash: 3.61% Traditional cash on cash: 2.97% Airbnb Rental Income: $3656 Traditional Rental Income: $2510 Airbnb ROI: 3.61% Traditional ROI: 2.97%
91 Coach Road South Portland, ME Tucked onto a quiet, tree-lined street in South Portland, this freshly updated home strike...	3 beds \| 1 baths \| 1,496 sq.ft.	$479,000	Airbnb cash on cash: 4.42% Traditional cash on cash: 3.47% Airbnb Rental Income: $3656 Traditional Rental Income: $2430 Airbnb ROI: 4.42% Traditional ROI: 3.47%
23 Aspen Avenue South Portland, ME Still time to pick your finishes in this new colonial in Thornton Heights. This establish...	3 beds \| N/A baths \| 1,708 sq.ft.	$609,900	Airbnb cash on cash: 2.51% Traditional cash on cash: 3.76% Airbnb Rental Income: $3656 Traditional Rental Income: $3569 Airbnb ROI: 2.51% Traditional ROI: 3.76%
66 Evans Street South Portland, ME Thoughtfully designed single-level bungalow featuring quality finishes and attached garage...	2 beds \| 3 baths \| 1,315 sq.ft.	$475,000	Airbnb cash on cash: 2.9% Traditional cash on cash: 2.01% Airbnb Rental Income: $3466 Traditional Rental Income: $2302 Airbnb ROI: 2.9% Traditional ROI: 2.01%
23 Winding Way South Portland, ME Welcome home! This pristine property is offered ready to move in. A full renovation in 20...	3 beds \| 2 baths \| 1,770 sq.ft.	$639,000	Airbnb cash on cash: 2.89% Traditional cash on cash: 2.01% Airbnb Rental Income: $3656 Traditional Rental Income: $2333 Airbnb ROI: 2.89% Traditional ROI: 2.01%
77 O'neil Street South Portland, ME Meeting House Hill! Solar Powered New Construction just finished with all the amenities, ...	3 beds \| N/A baths \| 2,492 sq.ft.	$999,000	Airbnb cash on cash: 0.62% Traditional cash on cash: 0.03% Airbnb Rental Income: $3656 Traditional Rental Income: $2307 Airbnb ROI: 0.62% Traditional ROI: 0.03%
44 Myrtle Avenue South Portland, ME Rare Willard Beach opportunity! Just steps to the beach and a short walk to Scratch, Scoo...	N/A beds \| N/A baths \| 1,728 sq.ft.	$1,150,000	Airbnb cash on cash: 0.21% Traditional cash on cash: -0.53% Airbnb Rental Income: $3110 Traditional Rental Income: $1602 Airbnb ROI: 0.21% Traditional ROI: -0.53%
148 Breakwater Drive South Portland, ME Great waterfront living opportunity for a reasonable price. This clean 1 bdrm condo is the...	1 beds \| N/A baths \| 567 sq.ft.	$265,000	Airbnb cash on cash: 1.22% Traditional cash on cash: 2.33% Airbnb Rental Income: $2250 Traditional Rental Income: $1963 Airbnb ROI: 1.22% Traditional ROI: 2.33%
149 Fort Road South Portland, ME NEW PRICE Discover the quintessential coastal Maine lifestyle in this breathtaking 1-flo...	2 beds \| 2 baths \| 1,430 sq.ft.	$675,000	Airbnb cash on cash: 1.43% Traditional cash on cash: 0.36% Airbnb Rental Income: $3466 Traditional Rental Income: $2023 Airbnb ROI: 1.43% Traditional ROI: 0.36%
63 Cloyster Road South Portland, ME Remarkable shingle-style home rebuilt and reimagined from a former life as a well-loved 19...	3 beds \| N/A baths \| 2,134 sq.ft.	$1,775,000	Airbnb cash on cash: 0.68% Traditional cash on cash: 1.07% Airbnb Rental Income: $3656 Traditional Rental Income: $3500 Airbnb ROI: 0.68% Traditional ROI: 1.07%
16 Plover Way South Portland, ME Phase III Open - Only 4 single level & 6 2-storny w/primary on 1st floor available. New...	2 beds \| 3 baths \| 2,274 sq.ft.	$838,900	Airbnb cash on cash: 0.34% Traditional cash on cash: 2.13% Airbnb Rental Income: $3466 Traditional Rental Income: $4101 Airbnb ROI: 0.34% Traditional ROI: 2.13%
14 Plover Way South Portland, ME Phase III Open - Only 4 single level & 6 2-storny w/primary on 1st floor available. New...	2 beds \| N/A baths \| 2,274 sq.ft.	$838,900	Airbnb cash on cash: 0.34% Traditional cash on cash: 2.13% Airbnb Rental Income: $3466 Traditional Rental Income: $4101 Airbnb ROI: 0.34% Traditional ROI: 2.13%
115 Summit Terrace South Portland, ME Introducing a thoughtfully designed 20-unit luxury condominium community nestled in the so...	3 beds \| N/A baths \| 2,350 sq.ft.	$899,900	Airbnb cash on cash: 1.66% Traditional cash on cash: 4.3% Airbnb Rental Income: $3656 Traditional Rental Income: $5070 Airbnb ROI: 1.66% Traditional ROI: 4.3%
1238 Broadway South Portland, ME Conveniently located on Broadway. Close to all amenities South Portland has to offer. This...	4 beds \| 2 baths \| 1,144 sq.ft.	$445,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.97% Airbnb Rental Income: $null Traditional Rental Income: $3004 Airbnb ROI: N/A Traditional ROI: 5.97%
338 Ocean Street South Portland, ME Reintroduced and priced with its newly defined .35ÃÂ± acre lot, this South Portland home ...	5 beds \| N/A baths \| 2,092 sq.ft.	$650,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.65% Airbnb Rental Income: $null Traditional Rental Income: $3525 Airbnb ROI: N/A Traditional ROI: 4.65%
134 S Richland Street South Portland, ME Step inside this Meeting House Hill home at 134 S Richland Street, beautifully updated for...	3 beds \| N/A baths \| 1,536 sq.ft.	$514,500	Airbnb cash on cash: 4.74% Traditional cash on cash: 4.3% Airbnb Rental Income: $3656 Traditional Rental Income: $2646 Airbnb ROI: 4.74% Traditional ROI: 4.3%
124 Westbrook Street South Portland, ME Welcome to 124 Westbrook Street, a charming 1950 Cape nestled in the desirable Country Gar...	3 beds \| N/A baths \| 1,571 sq.ft.	$500,000	Airbnb cash on cash: 4.9% Traditional cash on cash: 4.34% Airbnb Rental Income: $3656 Traditional Rental Income: $2593 Airbnb ROI: 4.9% Traditional ROI: 4.34%
2 Drew Road South Portland, ME Perched like the prow of a ship with panoramic waterfront vistas, 2 Drew Road presents inc...	3 beds \| N/A baths \| 2,148 sq.ft.	$3,795,000	Airbnb cash on cash: -0.22% Traditional cash on cash: -0.01% Airbnb Rental Income: $3656 Traditional Rental Income: $3589 Airbnb ROI: -0.22% Traditional ROI: -0.01%
18 Elmwood Avenue South Portland, ME Classic New Englander at popular neighborhood. Walk to everything. Traditional features, m...	3 beds \| N/A baths \| 1,346 sq.ft.	$545,000	Airbnb cash on cash: 4.42% Traditional cash on cash: 4.54% Airbnb Rental Income: $3656 Traditional Rental Income: $2917 Airbnb ROI: 4.42% Traditional ROI: 4.54%
39 Morse Street South Portland, ME Bring your vision! This 4-bedroom, 1-bath home offers the perfect chance to build sweat eq...	4 beds \| 1 baths \| 1,128 sq.ft.	$349,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.72% Airbnb Rental Income: $null Traditional Rental Income: $2629 Airbnb ROI: N/A Traditional ROI: 6.72%
69 Stanford Street South Portland, ME 69 Stanford Street in South Portland is a smart, flexible investment in one of Southern Ma...	N/A beds \| N/A baths \| 2,650 sq.ft.	$790,000	Airbnb cash on cash: 1.18% Traditional cash on cash: 0.87% Airbnb Rental Income: $3110 Traditional Rental Income: $2173 Airbnb ROI: 1.18% Traditional ROI: 0.87%
26 Spurwink Avenue South Portland, ME Newly remolded & updated 3 bedrooms, 1 bath ranch. New roof, bathroom & flooring and updat...	3 beds \| N/A baths \| 1,824 sq.ft.	$464,500	Airbnb cash on cash: 5.35% Traditional cash on cash: 5.26% Airbnb Rental Income: $3656 Traditional Rental Income: $2820 Airbnb ROI: 5.35% Traditional ROI: 5.26%
5 Barnstable Road South Portland, ME Welcome to 5 Barnstable Rd, a versatile and beautifully updated Cape-style home nestled in...	2 beds \| N/A baths \| 1,498 sq.ft.	$500,000	Airbnb cash on cash: 4.56% Traditional cash on cash: 4.24% Airbnb Rental Income: $3466 Traditional Rental Income: $2549 Airbnb ROI: 4.56% Traditional ROI: 4.24%
81 Washington Avenue South Portland, ME Sweet 1940's Cape in classic South Portland neighborhood close to everything! Get ready to...	3 beds \| N/A baths \| 1,088 sq.ft.	$374,900	Airbnb cash on cash: 6.85% Traditional cash on cash: 5.56% Airbnb Rental Income: $3656 Traditional Rental Income: $2406 Airbnb ROI: 6.85% Traditional ROI: 5.56%
96 Crestview Drive South Portland, ME Welcome to 96 Crestview Drive in South Portland, Maine. This custom-built Colonial-style h...	4 beds \| N/A baths \| 4,911 sq.ft.	$1,150,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.9% Airbnb Rental Income: $null Traditional Rental Income: $3196 Airbnb ROI: N/A Traditional ROI: 1.9%
161 Stanford Street South Portland, ME The moment you walk through the entry gate, and step onto the patio you will be impressed ...	3 beds \| N/A baths \| 2,292 sq.ft.	$749,000	Airbnb cash on cash: 2.96% Traditional cash on cash: 2.77% Airbnb Rental Income: $3656 Traditional Rental Income: $2728 Airbnb ROI: 2.96% Traditional ROI: 2.77%
1 Channel Road South Portland, ME Unparalleled grandeur and pristine craftsmanship define this waterfront estate in South Po...	3 beds \| N/A baths \| 6,505 sq.ft.	$8,000,000	Airbnb cash on cash: -0.62% Traditional cash on cash: -0.59% Airbnb Rental Income: $3656 Traditional Rental Income: $3114 Airbnb ROI: -0.62% Traditional ROI: -0.59%
73 High Street South Portland, ME Investors, contractors take notice. 3 unit building gutted back to the studs after freeze...	N/A beds \| N/A baths \| 2,096 sq.ft.	$699,000	Airbnb cash on cash: 1.58% Traditional cash on cash: 1.25% Airbnb Rental Income: $3110 Traditional Rental Income: $2191 Airbnb ROI: 1.58% Traditional ROI: 1.25%
23 Bodge Street South Portland, ME Two-bedroom, two-bath ranch offering hardwood floors, a comfortable layout, and great pote...	2 beds \| N/A baths \| 1,200 sq.ft.	$349,900	Airbnb cash on cash: 6.92% Traditional cash on cash: 5.98% Airbnb Rental Income: $3466 Traditional Rental Income: $2391 Airbnb ROI: 6.92% Traditional ROI: 5.98%
46 Burwell Avenue South Portland, ME Essentially brand new inside and out! This stunning 4-bedroom, 2-bath home has been taken ...	4 beds \| N/A baths \| 1,650 sq.ft.	$624,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.05% Airbnb Rental Income: $null Traditional Rental Income: $3044 Airbnb ROI: N/A Traditional ROI: 4.05%
37 Second Street South Portland, ME OPEN HOUSE SATURDAY 10/18 10 AM - 11:30 AM Single-level 2 bed / 1 bath home in South ...	2 beds \| 1 baths \| 993 sq.ft.	$450,000	Airbnb cash on cash: 5.18% Traditional cash on cash: 3.92% Airbnb Rental Income: $3466 Traditional Rental Income: $2169 Airbnb ROI: 5.18% Traditional ROI: 3.92%

Real Estate investment in South-portland, ME

There are 36 properties for sale in the city of South Portland . The median list price in South Portland is $592,450 and the average price per square foot is $315. In October 2025, the average monthly cash on cash return in South Portland is 3.00%. The average monthly rental income in South Portland is $2,571.

South-portland, ME Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 36 investment properties available for sale in South-portland.

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

The ROI for Short-Term is higher than the Long-Term in South-portland with average rental income of $3,656.

Your search for investment property begins and ends here

Investment Property for Sale in South Portland, ME

35 Jefferson Street

South Portland, ME

3 beds | N/A baths | 1,322 sq.ft.

$515,000

Airbnb cash on cash: 3.96%

Traditional cash on cash: 1.7%

Airbnb Rental Income: $3656

Traditional Rental Income: $1768

Airbnb ROI: 3.96%

Traditional ROI: 1.7%

267 Pleasant Avenue

South Portland, ME

4 beds | N/A baths | 1,880 sq.ft.

$623,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.58%

Airbnb Rental Income: $null

Traditional Rental Income: $3082

Airbnb ROI: N/A

Traditional ROI: 3.58%

79 Massachusetts Avenue

South Portland, ME

3 beds | 1 baths | 1,276 sq.ft.

$435,000

Airbnb cash on cash: 5.15%

Traditional cash on cash: 4.32%

Airbnb Rental Income: $3656

Traditional Rental Income: $2520

Airbnb ROI: 5.15%

Traditional ROI: 4.32%

20 Noyes Street

South Portland, ME

3 beds | N/A baths | 1,460 sq.ft.

$499,900

Airbnb cash on cash: 4.24%

Traditional cash on cash: 3.53%

Airbnb Rental Income: $3656

Traditional Rental Income: $2526

Airbnb ROI: 4.24%

Traditional ROI: 3.53%

753 Main Street

South Portland, ME

N/A beds | N/A baths | 1,372 sq.ft.

$499,000

Airbnb cash on cash: 2.84%

Traditional cash on cash: 2.28%

Airbnb Rental Income: $3110

Traditional Rental Income: $2140

Airbnb ROI: 2.84%

Traditional ROI: 2.28%

83 Broadway

South Portland, ME

3 beds | N/A baths | 1,162 sq.ft.

$575,000

Airbnb cash on cash: 3.61%

Traditional cash on cash: 2.97%

Airbnb Rental Income: $3656

Traditional Rental Income: $2510

Airbnb ROI: 3.61%

Traditional ROI: 2.97%

91 Coach Road

South Portland, ME

3 beds | 1 baths | 1,496 sq.ft.

$479,000

Airbnb cash on cash: 4.42%

Traditional cash on cash: 3.47%

Airbnb Rental Income: $3656

Traditional Rental Income: $2430

Airbnb ROI: 4.42%

Traditional ROI: 3.47%

23 Aspen Avenue

South Portland, ME

3 beds | N/A baths | 1,708 sq.ft.

$609,900

Airbnb cash on cash: 2.51%

Traditional cash on cash: 3.76%

Airbnb Rental Income: $3656

Traditional Rental Income: $3569

Airbnb ROI: 2.51%