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.

Investment Property for Sale in Oakland, ME

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
36 Main Street Oakland, ME Charming and full of potential, this cute Oakland home offers a fantastic in-town location...	2 beds \| 2 baths \| 1,664 sq.ft.	$220,000	Airbnb cash on cash: 0.09% Traditional cash on cash: 11.62% Airbnb Rental Income: $789 Traditional Rental Income: $2871 Airbnb ROI: 0.09% Traditional ROI: 11.62%
278 Middle Road Oakland, ME Beautifully renovated single story 2 bedroom 1.5 bath ranch located in the heart of Kenneb...	3 beds \| 2 baths \| 1,152 sq.ft.	$290,000	Airbnb cash on cash: 2.35% Traditional cash on cash: 5.54% Airbnb Rental Income: $1625 Traditional Rental Income: $2037 Airbnb ROI: 2.35% Traditional ROI: 5.54%
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: 0.17% Traditional cash on cash: 1.72% Airbnb Rental Income: $2368 Traditional Rental Income: $3217 Airbnb ROI: 0.17% 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: -1.99% Traditional cash on cash: 0.12% Airbnb Rental Income: $789 Traditional Rental Income: $2675 Airbnb ROI: -1.99% 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: -0.33% Traditional cash on cash: 3.64% Airbnb Rental Income: $1625 Traditional Rental Income: $3606 Airbnb ROI: -0.33% Traditional ROI: 3.64%
13 Junipers Lane Oakland, ME ucked away on a quiet, private dead-end road beside the Waterville Country Club, Juniper's...	2 beds \| 2 baths \| 1,064 sq.ft.	$209,000	Airbnb cash on cash: -2.13% Traditional cash on cash: 9.14% Airbnb Rental Income: $789 Traditional Rental Income: $2701 Airbnb ROI: -2.13% Traditional ROI: 9.14%
11 Church Street Oakland, ME Don't miss this in-town 2-unit multi-family property in Oakland offering strong income...	N/A beds \| 3 baths \| 2,600 sq.ft.	$299,900	Airbnb cash on cash: -0.11% Traditional cash on cash: 5.2% Airbnb Rental Income: $888 Traditional Rental Income: $2050 Airbnb ROI: -0.11% Traditional ROI: 5.2%
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: 0.82% Traditional cash on cash: 4.82% Airbnb Rental Income: $1467 Traditional Rental Income: $3086 Airbnb ROI: 0.82% 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: 1.68% Traditional cash on cash: 5.68% Airbnb Rental Income: $1625 Traditional Rental Income: $2757 Airbnb ROI: 1.68% 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: 1.56% Traditional cash on cash: 5.3% Airbnb Rental Income: $1625 Traditional Rental Income: $2721 Airbnb ROI: 1.56% 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: 1.56% Traditional cash on cash: 5.3% Airbnb Rental Income: $1625 Traditional Rental Income: $2721 Airbnb ROI: 1.56% Traditional ROI: 5.3%
98 Church Street Oakland, ME Strong cash flow and a great rental history make this three unit Oakland property a smart ...	N/A beds \| 3 baths \| 1,800 sq.ft.	$240,000	Airbnb cash on cash: 0.34% Traditional cash on cash: 6.91% Airbnb Rental Income: $888 Traditional Rental Income: $2041 Airbnb ROI: 0.34% Traditional ROI: 6.91%
38 S Greenridge Heights Oakland, ME Welcome to 38 South Greenridge Heights! This 2023 double wide boasts 3 beds, 2 baths, and ...	3 beds \| 2 baths \| 1,394 sq.ft.	$259,000	Airbnb cash on cash: 3.36% Traditional cash on cash: 11.2% Airbnb Rental Income: $1625 Traditional Rental Income: $3082 Airbnb ROI: 3.36% Traditional ROI: 11.2%

Real Estate investment in Oakland, ME

There are 13 properties for sale in the city of Oakland . The median list price in Oakland is $738,500 and the average price per square foot is $419. In May 2026, the average monthly cash on cash return in Oakland is 5.00%. The average monthly rental income in Oakland is $2,721.

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

There are 13 investment properties available for sale in Oakland.

In 2026, the best neighborhood to buy investment property is Oakland.

The ROI for Long-Term is higher than the Short-Term in Oakland with average rental income of $2,721.

Your search for investment property begins and ends here

Investment Property for Sale in Oakland, ME

36 Main Street

Oakland, ME

2 beds | 2 baths | 1,664 sq.ft.

$220,000

Airbnb cash on cash: 0.09%

Traditional cash on cash: 11.62%

Airbnb Rental Income: $789

Traditional Rental Income: $2871

Airbnb ROI: 0.09%

Traditional ROI: 11.62%

278 Middle Road

Oakland, ME

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

$290,000

Airbnb cash on cash: 2.35%

Traditional cash on cash: 5.54%

Airbnb Rental Income: $1625

Traditional Rental Income: $2037

Airbnb ROI: 2.35%

Traditional ROI: 5.54%

79 Rocky Shore Lane

Oakland, ME

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

$998,000

Airbnb cash on cash: 0.17%

Traditional cash on cash: 1.72%

Airbnb Rental Income: $2368

Traditional Rental Income: $3217

Airbnb ROI: 0.17%

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: -1.99%

Traditional cash on cash: 0.12%

Airbnb Rental Income: $789

Traditional Rental Income: $2675

Airbnb ROI: -1.99%

Traditional ROI: 0.12%

66 Brickett Point Estates

Oakland, ME

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

$659,000

Airbnb cash on cash: -0.33%

Traditional cash on cash: 3.64%

Airbnb Rental Income: $1625

Traditional Rental Income: $3606

Airbnb ROI: -0.33%

Traditional ROI: 3.64%

13 Junipers Lane

Oakland, ME

2 beds | 2 baths | 1,064 sq.ft.

$209,000

Airbnb cash on cash: -2.13%

Traditional cash on cash: 9.14%

Airbnb Rental Income: $789

Traditional Rental Income: $2701

Airbnb ROI: -2.13%

Traditional ROI: 9.14%

11 Church Street

Oakland, ME

N/A beds | 3 baths | 2,600 sq.ft.

$299,900

Airbnb cash on cash: -0.11%

Traditional cash on cash: 5.2%

Airbnb Rental Income: $888

Traditional Rental Income: $2050

Airbnb ROI: -0.11%

Traditional ROI: 5.2%

E Side Trail lot: 20-8A

Oakland, ME

4 beds | 3 baths | 2,320 sq.ft.

$550,000

Airbnb cash on cash: 0.82%

Traditional cash on cash: 4.82%

Airbnb Rental Income: $1467

Traditional Rental Income: $3086

Airbnb ROI: 0.82%