Real Estate Investment Properties for Sale in Oakland, ME

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

Explore a variety of short-term homes & houses in Oakland, ME. Invest wisely with VRBO & Oakland, ME Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Single Family Homes for Sale in Oakland, ME

Search for Single Family Residential for Sale in Oakland, Maine. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 17 Single Family Residential 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
863 Kennedy Memorial Drive Oakland, ME Prime Spot on Kennedey Memorial drive in the heart of Oakland Retail District .Stunning ra...	3 beds \| 1 baths \| 1,054 sq.ft.	$495,000	Airbnb cash on cash: 0.61% Traditional cash on cash: 2.07% Airbnb Rental Income: $1460 Traditional Rental Income: $1706 Airbnb ROI: 0.61% Traditional ROI: 2.07%
107 Pinewoods Trail Oakland, ME McGrath Pond: Escape to the lake at this cozy and beautifully updated 2BR/1BA waterfront r...	2 beds \| 1 baths \| 576 sq.ft.	$399,900	Airbnb cash on cash: -0.07% Traditional cash on cash: 3.85% Airbnb Rental Income: $906 Traditional Rental Income: $2036 Airbnb ROI: -0.07% Traditional ROI: 3.85%
8 Wedgewood Drive Oakland, ME Welcome to 8 Wedgewood Dr -- a peaceful retreat offering privacy, comfort, and shared acce...	3 beds \| 3 baths \| 2,299 sq.ft.	$604,000	Airbnb cash on cash: -0.22% Traditional cash on cash: 3.08% Airbnb Rental Income: $1460 Traditional Rental Income: $2891 Airbnb ROI: -0.22% Traditional ROI: 3.08%
130 Middle Road Oakland, ME Tucked on 2.4 private acres, this 1,700+ sq ft home delivers the lifestyle you've been wai...	2 beds \| 2 baths \| 1,722 sq.ft.	$379,500	Airbnb cash on cash: -0.47% Traditional cash on cash: 4.25% Airbnb Rental Income: $906 Traditional Rental Income: $2247 Airbnb ROI: -0.47% Traditional ROI: 4.25%
278 Middle Road Oakland, ME Price Improvement! If you've been searching for the ease and comfort of single-story livin...	3 beds \| 2 baths \| 1,152 sq.ft.	$282,000	Airbnb cash on cash: 1.93% Traditional cash on cash: 5.73% Airbnb Rental Income: $1460 Traditional Rental Income: $2037 Airbnb ROI: 1.93% Traditional ROI: 5.73%
79 Rocky Shore Lane Oakland, ME Offered below appraised value - Beautifully updated year-round retreat with 100' of privat...	5 beds \| 3 baths \| 3,547 sq.ft.	$998,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.72% Airbnb Rental Income: $null Traditional Rental Income: $3217 Airbnb ROI: N/A Traditional ROI: 1.72%
25 Gifford Place & Blake Island Oakland, ME Experience the pinnacle of Maine living with this rare, year-round retreat on the shores o...	2 beds \| 2 baths \| 1,082 sq.ft.	$1,125,000	Airbnb cash on cash: -1.9% Traditional cash on cash: 0.12% Airbnb Rental Income: $906 Traditional Rental Income: $2675 Airbnb ROI: -1.9% Traditional ROI: 0.12%
66 Brickett Point Estates Oakland, ME Welcome to 66 Brickett Point Estates?an inviting four-season retreat where timeless crafts...	3 beds \| 2 baths \| 1,836 sq.ft.	$659,000	Airbnb cash on cash: -0.55% Traditional cash on cash: 3.64% Airbnb Rental Income: $1460 Traditional Rental Income: $3606 Airbnb ROI: -0.55% Traditional ROI: 3.64%
78 + 98 Hussey Hill Road Oakland, ME This phenomenal home is sitting on over 28 acres w/ horse stalls, riding pens & a stocked ...	5 beds \| 5 baths \| 5,526 sq.ft.	$1,950,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.61% Airbnb Rental Income: $null Traditional Rental Income: $6620 Airbnb ROI: N/A Traditional ROI: 2.61%
E Side Trail lot: 20-8A Oakland, ME INCLUDES ATTACHED 2-CAR GARAGE AND BREEZEWAY Welcome to this thoughtfully designed new...	4 beds \| 3 baths \| 2,320 sq.ft.	$550,000	Airbnb cash on cash: 1.19% Traditional cash on cash: 4.82% Airbnb Rental Income: $1695 Traditional Rental Income: $3086 Airbnb ROI: 1.19% Traditional ROI: 4.82%
Jacques Lane lot: 13 Oakland, ME To be built 3 bed/2 bath home in Oakland! Looking for a new construction? Here's your chan...	3 beds \| 2 baths \| 1,344 sq.ft.	$425,000	Airbnb cash on cash: 1.34% Traditional cash on cash: 5.68% Airbnb Rental Income: $1460 Traditional Rental Income: $2757 Airbnb ROI: 1.34% Traditional ROI: 5.68%
11 Jacques Lane Oakland, ME New construction! Build in process, get under contract in time to make some interior choic...	3 beds \| 2 baths \| 1,400 sq.ft.	$445,000	Airbnb cash on cash: 1.23% Traditional cash on cash: 5.3% Airbnb Rental Income: $1460 Traditional Rental Income: $2721 Airbnb ROI: 1.23% Traditional ROI: 5.3%
12 Jacques Lane Oakland, ME New construction! Build in process, get under contract in time to make some interior choic...	3 beds \| 2 baths \| 1,400 sq.ft.	$445,000	Airbnb cash on cash: 1.23% Traditional cash on cash: 5.3% Airbnb Rental Income: $1460 Traditional Rental Income: $2721 Airbnb ROI: 1.23% Traditional ROI: 5.3%
78 Ten Lots Road Oakland, ME Set on several private acres in Oakland, this classic 1800s farmhouse blends historic New ...	3 beds \| 2 baths \| 1,950 sq.ft.	$365,000	Airbnb cash on cash: 1.71% Traditional cash on cash: 8.54% Airbnb Rental Income: $1460 Traditional Rental Income: $3366 Airbnb ROI: 1.71% Traditional ROI: 8.54%
161 Small Shore Trail Oakland, ME SALMON LAKE Offered for the first time in more than 30 years, this meticulously maintained...	3 beds \| 2 baths \| 1,700 sq.ft.	$585,000	Airbnb cash on cash: 0.7% Traditional cash on cash: 5.27% Airbnb Rental Income: $1460 Traditional Rental Income: $3525 Airbnb ROI: 0.7% Traditional ROI: 5.27%
40 Lakeview Drive Oakland, ME Charming comfortable ranch in a desirable neighborhood close to Messalonskee park and boat...	3 beds \| 1 baths \| 1,390 sq.ft.	$305,000	Airbnb cash on cash: 2.24% Traditional cash on cash: 8.57% Airbnb Rental Income: $1460 Traditional Rental Income: $2844 Airbnb ROI: 2.24% Traditional ROI: 8.57%
202 Middle Road Oakland, ME Charming country ranch on a lovely private, corner lot with frontage on three roads! Conve...	2 beds \| 1 baths \| 1,522 sq.ft.	$329,000	Airbnb cash on cash: -0.82% Traditional cash on cash: 5.49% Airbnb Rental Income: $906 Traditional Rental Income: $2517 Airbnb ROI: -0.82% Traditional ROI: 5.49%

Your search for investment property begins and ends here

Single Family Homes for Sale in Oakland, ME

863 Kennedy Memorial Drive

Oakland, ME

3 beds | 1 baths | 1,054 sq.ft.

$495,000

Airbnb cash on cash: 0.61%

Traditional cash on cash: 2.07%

Airbnb Rental Income: $1460

Traditional Rental Income: $1706

Airbnb ROI: 0.61%

Traditional ROI: 2.07%

107 Pinewoods Trail

Oakland, ME

2 beds | 1 baths | 576 sq.ft.

$399,900

Airbnb cash on cash: -0.07%

Traditional cash on cash: 3.85%

Airbnb Rental Income: $906

Traditional Rental Income: $2036

Airbnb ROI: -0.07%

Traditional ROI: 3.85%

8 Wedgewood Drive

Oakland, ME

3 beds | 3 baths | 2,299 sq.ft.

$604,000

Airbnb cash on cash: -0.22%

Traditional cash on cash: 3.08%

Airbnb Rental Income: $1460

Traditional Rental Income: $2891

Airbnb ROI: -0.22%

Traditional ROI: 3.08%

130 Middle Road

Oakland, ME

2 beds | 2 baths | 1,722 sq.ft.

$379,500

Airbnb cash on cash: -0.47%

Traditional cash on cash: 4.25%

Airbnb Rental Income: $906

Traditional Rental Income: $2247

Airbnb ROI: -0.47%

Traditional ROI: 4.25%

278 Middle Road

Oakland, ME

3 beds | 2 baths | 1,152 sq.ft.

$282,000

Airbnb cash on cash: 1.93%

Traditional cash on cash: 5.73%

Airbnb Rental Income: $1460

Traditional Rental Income: $2037

Airbnb ROI: 1.93%

Traditional ROI: 5.73%

79 Rocky Shore Lane

Oakland, ME

5 beds | 3 baths | 3,547 sq.ft.

$998,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.72%

Airbnb Rental Income: $null

Traditional Rental Income: $3217

Airbnb ROI: N/A

Traditional ROI: 1.72%

25 Gifford Place & Blake Island

Oakland, ME

2 beds | 2 baths | 1,082 sq.ft.

$1,125,000

Airbnb cash on cash: -1.9%

Traditional cash on cash: 0.12%

Airbnb Rental Income: $906

Traditional Rental Income: $2675

Airbnb ROI: -1.9%

Traditional ROI: 0.12%

66 Brickett Point Estates

Oakland, ME

3 beds | 2 baths | 1,836 sq.ft.

$659,000

Airbnb cash on cash: -0.55%

Traditional cash on cash: 3.64%

Airbnb Rental Income: $1460

Traditional Rental Income: $3606

Airbnb ROI: -0.55%