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.

Golden Highlands Investment Property for Sale in South Portland, ME

Search for Golden Highlands Investment Property for Sale in South Portland, Maine. Browse all of Mashvisor’s Golden Highlands Investment Property listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 24 Golden Highlands Investment Property listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
486 Highland Avenue South Portland, ME This 3 bedroom 2 1/2 bath home is the perfect sanctuary from the hustle and bustle of ever...	3 beds \| 3 baths \| 1,833 sq.ft.	$569,000	Airbnb cash on cash: 1.31% Traditional cash on cash: 4.62% Airbnb Rental Income: $2315 Traditional Rental Income: $3501 Airbnb ROI: 1.31% Traditional ROI: 4.62%
55 Hawthorne Lane South Portland, ME Set on nearly an acre in South Portland's Hawthorne Woods, this thoughtfully designed 3,20...	4 beds \| 3 baths \| 3,129 sq.ft.	$1,650,000	Airbnb cash on cash: -0.12% Traditional cash on cash: 0.51% Airbnb Rental Income: $4451 Traditional Rental Income: $4475 Airbnb ROI: -0.12% Traditional ROI: 0.51%
245 Broadway South Portland, ME Find your new home in the heart of one of South Portland's most walkable & bikeable locati...	2 beds \| 2 baths \| 1,060 sq.ft.	$380,000	Airbnb cash on cash: -1.96% Traditional cash on cash: 2.68% Airbnb Rental Income: $1317 Traditional Rental Income: $2563 Airbnb ROI: -1.96% Traditional ROI: 2.68%
757 Main Street South Portland, ME Welcome to this immaculate ground-floor 2-bedroom, 1-bathroom condo, offering the perfect ...	2 beds \| 1 baths \| 974 sq.ft.	$279,000	Airbnb cash on cash: -0.83% Traditional cash on cash: 2.55% Airbnb Rental Income: $1317 Traditional Rental Income: $1799 Airbnb ROI: -0.83% Traditional ROI: 2.55%
72 Ocean Street South Portland, ME There are few places anywhere in the region that deliver a complete, walkable and bikeable...	2 beds \| 2 baths \| 1,554 sq.ft.	$699,000	Airbnb cash on cash: -0.57% Traditional cash on cash: 3.51% Airbnb Rental Income: $1317 Traditional Rental Income: $3568 Airbnb ROI: -0.57% Traditional ROI: 3.51%
16 Plover Way South Portland, ME Essex Layout - Having 2400 +/- sf. with primary bedroom on 1st floor and sunroom. This 55 ...	2 beds \| 3 baths \| 2,414 sq.ft.	$886,400	Airbnb cash on cash: -1.98% Traditional cash on cash: 1.89% Airbnb Rental Income: $1317 Traditional Rental Income: $4101 Airbnb ROI: -1.98% Traditional ROI: 1.89%
14 Plover Way South Portland, ME Phase III Open - Only 1 single level & 4 2-storny w/primary on 1st floor available. New Co...	2 beds \| 3 baths \| 2,274 sq.ft.	$838,900	Airbnb cash on cash: -1.95% Traditional cash on cash: 2.13% Airbnb Rental Income: $1317 Traditional Rental Income: $4101 Airbnb ROI: -1.95% Traditional ROI: 2.13%
1238 Broadway South Portland, ME Charming Bungalow style home offering 3/4 bedrooms...all new flooring April 2026 throughou...	4 beds \| 2 baths \| 1,296 sq.ft.	$440,000	Airbnb cash on cash: 7.31% Traditional cash on cash: 6.05% Airbnb Rental Income: $4451 Traditional Rental Income: $3004 Airbnb ROI: 7.31% Traditional ROI: 6.05%
32 Robinson Street South Portland, ME Welcome to this well-maintained and thoughtfully laid out 3-bedroom home offering comforta...	3 beds \| 1 baths \| 1,040 sq.ft.	$490,000	Airbnb cash on cash: 2.58% Traditional cash on cash: 4.23% Airbnb Rental Income: $2315 Traditional Rental Income: $2493 Airbnb ROI: 2.58% Traditional ROI: 4.23%
2 Drew Road South Portland, ME Perched like the prow of a ship with panoramic waterfront vistas, 2 Drew Road presents inc...	3 beds \| 2 baths \| 2,148 sq.ft.	$3,495,000	Airbnb cash on cash: -0.5% Traditional cash on cash: 0.07% Airbnb Rental Income: $2315 Traditional Rental Income: $3589 Airbnb ROI: -0.5% Traditional ROI: 0.07%
134 - 136 Sawyer Street South Portland, ME Nestled in South Portland's historic Ferry Village, this mostly refreshed two-unit propert...	N/A beds \| 2 baths \| 2,323 sq.ft.	$619,000	Airbnb cash on cash: 1.33% Traditional cash on cash: 1.44% Airbnb Rental Income: $2751 Traditional Rental Income: $2168 Airbnb ROI: 1.33% Traditional ROI: 1.44%
265 Lincoln Street South Portland, ME Spacious South Portland home on a rare double corner lot and offering a bright, open floor...	4 beds \| 2 baths \| 1,781 sq.ft.	$525,000	Airbnb cash on cash: 5.97% Traditional cash on cash: 4.87% Airbnb Rental Income: $4451 Traditional Rental Income: $2979 Airbnb ROI: 5.97% Traditional ROI: 4.87%
148 Breakwater Drive South Portland, ME Wonderful opportunity to own a waterside property in South Portland's popular Breakwater C...	1 beds \| 1 baths \| 587 sq.ft.	$325,000	Airbnb cash on cash: -2% Traditional cash on cash: 1.77% Airbnb Rental Income: $1080 Traditional Rental Income: $1863 Airbnb ROI: -2% Traditional ROI: 1.77%
119 Summit Terrace South Portland, ME Introducing a thoughtfully designed 20-unit luxury condominium community nestled in the so...	3 beds \| 4 baths \| 2,350 sq.ft.	$899,900	Airbnb cash on cash: -1.02% Traditional cash on cash: 0.4% Airbnb Rental Income: $2315 Traditional Rental Income: $2929 Airbnb ROI: -1.02% Traditional ROI: 0.4%
13 Oakwood Drive South Portland, ME This beautifully maintained Colonial-style home is situated in a prime location. The well-...	3 beds \| 3 baths \| 2,891 sq.ft.	$709,900	Airbnb cash on cash: 0.13% Traditional cash on cash: 1.65% Airbnb Rental Income: $2315 Traditional Rental Income: $2749 Airbnb ROI: 0.13% Traditional ROI: 1.65%
542 Preble Street South Portland, ME This charming Dutch Colonial near Willard Beach captures the timeless appeal of a 1926 hom...	3 beds \| 1 baths \| 1,496 sq.ft.	$767,350	Airbnb cash on cash: -0.05% Traditional cash on cash: 1.04% Airbnb Rental Income: $2315 Traditional Rental Income: $2515 Airbnb ROI: -0.05% Traditional ROI: 1.04%
2 Plover Way South Portland, ME Coolidge-Single Level Layout - Having 2220 +/- sf. with a beautiful sunroom. This 55 plus ...	2 beds \| 3 baths \| 2,220 sq.ft.	$917,400	Airbnb cash on cash: -1.4% Traditional cash on cash: 2.15% Airbnb Rental Income: $1317 Traditional Rental Income: $3939 Airbnb ROI: -1.4% Traditional ROI: 2.15%
30 Kaler Road South Portland, ME Opportunity is knocking in South Portland! This 1960s classic is more than just a home--it...	3 beds \| 1 baths \| 1,165 sq.ft.	$500,000	Airbnb cash on cash: 2.51% Traditional cash on cash: 3.76% Airbnb Rental Income: $2315 Traditional Rental Income: $2322 Airbnb ROI: 2.51% Traditional ROI: 3.76%
136 Dawson Street South Portland, ME Whether you are just starting out or downsizing, 136 Dawson St will meet your needs. This ...	3 beds \| 1 baths \| 960 sq.ft.	$440,000	Airbnb cash on cash: 2.99% Traditional cash on cash: 4.24% Airbnb Rental Income: $2315 Traditional Rental Income: $2256 Airbnb ROI: 2.99% Traditional ROI: 4.24%
25 Bishop Avenue South Portland, ME Charming and well-located 3-bedroom, 1.5 bath home in the heart of South Portland! This pr...	3 beds \| 2 baths \| 1,789 sq.ft.	$600,000	Airbnb cash on cash: 0.59% Traditional cash on cash: 3.28% Airbnb Rental Income: $2315 Traditional Rental Income: $3245 Airbnb ROI: 0.59% Traditional ROI: 3.28%
802 Highland Avenue South Portland, ME Welcome to 802 Highland Ave where you will find this well landscaped/tastefully remodeled ...	3 beds \| 2 baths \| 1,570 sq.ft.	$595,000	Airbnb cash on cash: 0.62% Traditional cash on cash: 3.06% Airbnb Rental Income: $2315 Traditional Rental Income: $3097 Airbnb ROI: 0.62% Traditional ROI: 3.06%
71 Myrtle Avenue South Portland, ME Set along one of the Willard neighborhood's most desirable quiet streets, with beach acces...	5 beds \| 3 baths \| 3,784 sq.ft.	$1,950,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.4% Airbnb Rental Income: $null Traditional Rental Income: $4440 Airbnb ROI: N/A Traditional ROI: 1.4%
210 Barnstable Road South Portland, ME Beautifully updated and move-in ready, this 3-bedroom, 2.5-bath home offers comfort, style...	3 beds \| 3 baths \| 1,672 sq.ft.	$769,900	Airbnb cash on cash: 1.29% Traditional cash on cash: 3.47% Airbnb Rental Income: $2315 Traditional Rental Income: $3305 Airbnb ROI: 1.29% Traditional ROI: 3.47%
33 Sokokis Street South Portland, ME Beautifully landscaped 3 bedroom 2 full bath slit-level home on corner lot. Located in des...	3 beds \| 2 baths \| 1,654 sq.ft.	$485,000	Airbnb cash on cash: 1.28% Traditional cash on cash: 4.45% Airbnb Rental Income: $2315 Traditional Rental Income: $3179 Airbnb ROI: 1.28% Traditional ROI: 4.45%

Your search for investment property begins and ends here

Golden Highlands Investment Property for Sale in South Portland, ME

486 Highland Avenue

South Portland, ME

3 beds | 3 baths | 1,833 sq.ft.

$569,000

Airbnb cash on cash: 1.31%

Traditional cash on cash: 4.62%

Airbnb Rental Income: $2315

Traditional Rental Income: $3501

Airbnb ROI: 1.31%

Traditional ROI: 4.62%

55 Hawthorne Lane

South Portland, ME

4 beds | 3 baths | 3,129 sq.ft.

$1,650,000

Airbnb cash on cash: -0.12%

Traditional cash on cash: 0.51%

Airbnb Rental Income: $4451

Traditional Rental Income: $4475

Airbnb ROI: -0.12%

Traditional ROI: 0.51%

245 Broadway

South Portland, ME

2 beds | 2 baths | 1,060 sq.ft.

$380,000

Airbnb cash on cash: -1.96%

Traditional cash on cash: 2.68%

Airbnb Rental Income: $1317

Traditional Rental Income: $2563

Airbnb ROI: -1.96%

Traditional ROI: 2.68%

757 Main Street

South Portland, ME

2 beds | 1 baths | 974 sq.ft.

$279,000

Airbnb cash on cash: -0.83%

Traditional cash on cash: 2.55%

Airbnb Rental Income: $1317

Traditional Rental Income: $1799

Airbnb ROI: -0.83%

Traditional ROI: 2.55%

72 Ocean Street

South Portland, ME

2 beds | 2 baths | 1,554 sq.ft.

$699,000

Airbnb cash on cash: -0.57%

Traditional cash on cash: 3.51%

Airbnb Rental Income: $1317

Traditional Rental Income: $3568

Airbnb ROI: -0.57%

Traditional ROI: 3.51%

16 Plover Way

South Portland, ME

2 beds | 3 baths | 2,414 sq.ft.

$886,400

Airbnb cash on cash: -1.98%

Traditional cash on cash: 1.89%

Airbnb Rental Income: $1317

Traditional Rental Income: $4101

Airbnb ROI: -1.98%

Traditional ROI: 1.89%

14 Plover Way

South Portland, ME

2 beds | 3 baths | 2,274 sq.ft.

$838,900

Airbnb cash on cash: -1.95%

Traditional cash on cash: 2.13%

Airbnb Rental Income: $1317

Traditional Rental Income: $4101

Airbnb ROI: -1.95%

Traditional ROI: 2.13%

1238 Broadway

South Portland, ME

4 beds | 2 baths | 1,296 sq.ft.

$440,000

Airbnb cash on cash: 7.31%

Traditional cash on cash: 6.05%

Airbnb Rental Income: $4451

Traditional Rental Income: $3004

Airbnb ROI: 7.31%