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

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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: 0.03% Traditional cash on cash: 2.07% Airbnb Rental Income: $1138 Traditional Rental Income: $1706 Airbnb ROI: 0.03% 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: 0.05% Traditional cash on cash: 3.85% Airbnb Rental Income: $963 Traditional Rental Income: $2036 Airbnb ROI: 0.05% 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: -0.7% Traditional cash on cash: 3.08% Airbnb Rental Income: $1138 Traditional Rental Income: $2891 Airbnb ROI: -0.7% 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: -0.34% Traditional cash on cash: 4.25% Airbnb Rental Income: $963 Traditional Rental Income: $2247 Airbnb ROI: -0.34% Traditional ROI: 4.25%
12 Gleason Farm Road Oakland, ME Looking for low-maintenance one-floor living in Oakland, Maine? This beautifully maintaine...	3 beds \| 2 baths \| 1,636 sq.ft.	$489,000	Airbnb cash on cash: -0.27% Traditional cash on cash: 3.61% Airbnb Rental Income: $1138 Traditional Rental Income: $2534 Airbnb ROI: -0.27% Traditional ROI: 3.61%
278 Middle Road Oakland, ME Price Improvement! If you've been searching for the ease and comfort of single-story livin...	2 beds \| 2 baths \| 1,152 sq.ft.	$282,000	Airbnb cash on cash: 0.37% Traditional cash on cash: 5.73% Airbnb Rental Income: $963 Traditional Rental Income: $2037 Airbnb ROI: 0.37% Traditional ROI: 5.73%
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.	$995,000	Airbnb cash on cash: -1.79% Traditional cash on cash: 0.44% Airbnb Rental Income: $963 Traditional Rental Income: $2675 Airbnb ROI: -1.79% Traditional ROI: 0.44%
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: -0.99% Traditional cash on cash: 3.64% Airbnb Rental Income: $1138 Traditional Rental Income: $3606 Airbnb ROI: -0.99% 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: -0.21% Traditional cash on cash: 2.61% Airbnb Rental Income: $2055 Traditional Rental Income: $6620 Airbnb ROI: -0.21% Traditional ROI: 2.61%
11 Church Street Oakland, ME Don't miss this in-town 2-unit multi-family property in Oakland offering strong income...	N/A beds \| 2 baths \| 2,600 sq.ft.	$299,900	Airbnb cash on cash: 0.57% Traditional cash on cash: 5.2% Airbnb Rental Income: $1120 Traditional Rental Income: $2050 Airbnb ROI: 0.57% 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: 1.76% Traditional cash on cash: 4.82% Airbnb Rental Income: $2044 Traditional Rental Income: $3086 Airbnb ROI: 1.76% 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: 0.66% Traditional cash on cash: 5.68% Airbnb Rental Income: $1138 Traditional Rental Income: $2757 Airbnb ROI: 0.66% 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: 0.59% Traditional cash on cash: 5.3% Airbnb Rental Income: $1138 Traditional Rental Income: $2721 Airbnb ROI: 0.59% 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: 0.59% Traditional cash on cash: 5.3% Airbnb Rental Income: $1138 Traditional Rental Income: $2721 Airbnb ROI: 0.59% 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: 1.19% Traditional cash on cash: 6.91% Airbnb Rental Income: $1120 Traditional Rental Income: $2041 Airbnb ROI: 1.19% Traditional ROI: 6.91%
Pinewoods Trail lot: 45-2 Oakland, ME 3 bed/2 bath mobile home awaits you. This project will be completely turnkey. Please refer...	3 beds \| 2 baths \| 1,173 sq.ft.	$325,000	Airbnb cash on cash: 1.16% Traditional cash on cash: 8.41% Airbnb Rental Income: $1138 Traditional Rental Income: $2975 Airbnb ROI: 1.16% Traditional ROI: 8.41%
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: 0.93% Traditional cash on cash: 8.54% Airbnb Rental Income: $1138 Traditional Rental Income: $3366 Airbnb ROI: 0.93% Traditional ROI: 8.54%
20 & 21 Bass Cove Oakland, ME Looking for a waterfront home with a rare, grandfathered setting right at the shoreline th...	5 beds \| 2 baths \| 3,208 sq.ft.	$928,000	Airbnb cash on cash: -0.7% Traditional cash on cash: 2.11% Airbnb Rental Income: $2055 Traditional Rental Income: $3948 Airbnb ROI: -0.7% Traditional ROI: 2.11%
72 Cedar Village Place Oakland, ME Experience the best of Maine lakefront living with this charming 2-bedroom home on sought-...	2 beds \| 2 baths \| 1,247 sq.ft.	$775,000	Airbnb cash on cash: -0.28% Traditional cash on cash: 3.02% Airbnb Rental Income: $963 Traditional Rental Income: $3002 Airbnb ROI: -0.28% Traditional ROI: 3.02%
13 Selden Lane Oakland, ME If you've been searching for the ease of single-floor living without sacrificing space or ...	2 beds \| 2 baths \| 1,856 sq.ft.	$384,900	Airbnb cash on cash: 0.43% Traditional cash on cash: 7.79% Airbnb Rental Income: $963 Traditional Rental Income: $3271 Airbnb ROI: 0.43% Traditional ROI: 7.79%
28 Belgrade Road Oakland, ME Picturesque waterfront setting on one of Maine's most desirable lakes. For first time on t...	3 beds \| 2 baths \| 2,406 sq.ft.	$770,000	Airbnb cash on cash: -0.08% Traditional cash on cash: 3.93% Airbnb Rental Income: $1138 Traditional Rental Income: $3637 Airbnb ROI: -0.08% Traditional ROI: 3.93%

Real Estate investment in Oakland, ME

There are 21 properties for sale in the city of Oakland . The median list price in Oakland is $367,810 and the average price per square foot is $208. In June 2026, the average monthly cash on cash return in Oakland is 5.00%. The average monthly rental income in Oakland is $2,757.

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

There are 21 investment properties available for sale in Oakland.

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

The ROI for Short-Term is higher than the Long-Term in Oakland with average rental income of $1,138.

Your search for investment property begins and ends here

Investment Property 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: 0.03%

Traditional cash on cash: 2.07%

Airbnb Rental Income: $1138

Traditional Rental Income: $1706

Airbnb ROI: 0.03%

Traditional ROI: 2.07%

107 Pinewoods Trail

Oakland, ME

2 beds | 1 baths | 576 sq.ft.

$399,900

Airbnb cash on cash: 0.05%

Traditional cash on cash: 3.85%

Airbnb Rental Income: $963

Traditional Rental Income: $2036

Airbnb ROI: 0.05%

Traditional ROI: 3.85%

8 Wedgewood Drive

Oakland, ME

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

$604,000

Airbnb cash on cash: -0.7%

Traditional cash on cash: 3.08%

Airbnb Rental Income: $1138

Traditional Rental Income: $2891

Airbnb ROI: -0.7%

Traditional ROI: 3.08%

130 Middle Road

Oakland, ME

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

$379,500

Airbnb cash on cash: -0.34%

Traditional cash on cash: 4.25%

Airbnb Rental Income: $963

Traditional Rental Income: $2247

Airbnb ROI: -0.34%

Traditional ROI: 4.25%

12 Gleason Farm Road

Oakland, ME

3 beds | 2 baths | 1,636 sq.ft.

$489,000

Airbnb cash on cash: -0.27%

Traditional cash on cash: 3.61%

Airbnb Rental Income: $1138

Traditional Rental Income: $2534

Airbnb ROI: -0.27%

Traditional ROI: 3.61%

278 Middle Road

Oakland, ME

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

$282,000

Airbnb cash on cash: 0.37%

Traditional cash on cash: 5.73%

Airbnb Rental Income: $963

Traditional Rental Income: $2037

Airbnb ROI: 0.37%

Traditional ROI: 5.73%

25 Gifford Place & Blake Island

Oakland, ME

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

$995,000

Airbnb cash on cash: -1.79%

Traditional cash on cash: 0.44%

Airbnb Rental Income: $963

Traditional Rental Income: $2675

Airbnb ROI: -1.79%

Traditional ROI: 0.44%

66 Brickett Point Estates

Oakland, ME

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

$659,000

Airbnb cash on cash: -0.99%

Traditional cash on cash: 3.64%

Airbnb Rental Income: $1138

Traditional Rental Income: $3606

Airbnb ROI: -0.99%