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 33 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
520 Smithfield Rd Oakland, ME Open-concept Contemporary home in the heart of the Seven Lakes region. Currently a one-bed...	2 beds \| 1 baths \| 1,056 sq.ft.	$195,000	Airbnb cash on cash: 2.67% Traditional cash on cash: 6.17% Airbnb Rental Income: $1281 Traditional Rental Income: $1526 Airbnb ROI: 2.67% Traditional ROI: 6.17%
96 Oak Hill Dr Oakland, ME VIRTUAL ONLINE TOUR AVAILABLE. Gorgeous garrison with lots of room and in-ground pool in n...	4 beds \| 2 baths \| 2,496 sq.ft.	$469,900	Airbnb cash on cash: 3.22% Traditional cash on cash: 6.11% Airbnb Rental Income: $2869 Traditional Rental Income: $3471 Airbnb ROI: 3.22% Traditional ROI: 6.11%
203 Belgrade Rd Oakland, ME Adorable home with tons of potential. Newer furnace and monitor heater. Driveway was regr...	2 beds \| 2 baths \| 1,502 sq.ft.	$399,000	Airbnb cash on cash: 0.86% Traditional cash on cash: 6.08% Airbnb Rental Income: $1281 Traditional Rental Income: $2829 Airbnb ROI: 0.86% Traditional ROI: 6.08%
12 Gleason Farm Rd Oakland, ME Looking for low-maintenance one-floor living in Oakland, Maine? This beautifully maintaine...	3 beds \| 2 baths \| 1,636 sq.ft.	$458,000	Airbnb cash on cash: 1.39% Traditional cash on cash: 3.92% Airbnb Rental Income: $1968 Traditional Rental Income: $2534 Airbnb ROI: 1.39% Traditional ROI: 3.92%
278 Middle Rd Oakland, ME Price Improvement! If you've been searching for the ease and comfort of single-story livin...	2 beds \| 1 baths \| 1,152 sq.ft.	$276,500	Airbnb cash on cash: 1.41% Traditional cash on cash: 5.86% Airbnb Rental Income: $1281 Traditional Rental Income: $2037 Airbnb ROI: 1.41% Traditional ROI: 5.86%
132 Washington St Oakland, ME The perfect blend of convenience and tranquility in this charming 3 bed, 2 bath home nestl...	3 beds \| 2 baths \| 1,518 sq.ft.	$239,000	Airbnb cash on cash: 3.2% Traditional cash on cash: 10.72% Airbnb Rental Income: $1968 Traditional Rental Income: $3150 Airbnb ROI: 3.2% Traditional ROI: 10.72%
25 Gifford Place & Blake Is 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.	$895,000	Airbnb cash on cash: -1.41% Traditional cash on cash: 0.75% Airbnb Rental Income: $1281 Traditional Rental Income: $2675 Airbnb ROI: -1.41% Traditional ROI: 0.75%
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: 0.14% Traditional cash on cash: 3.64% Airbnb Rental Income: $1968 Traditional Rental Income: $3606 Airbnb ROI: 0.14% Traditional ROI: 3.64%
78 + 98 Hussey Hill Rd Oakland, ME This phenomenal home is sitting on over 28 acres w/ horse stalls, riding pens & a stocked ...	5 beds \| 4 baths \| 5,526 sq.ft.	$1,900,000	Airbnb cash on cash: -0.69% Traditional cash on cash: 2.7% Airbnb Rental Income: $987 Traditional Rental Income: $6620 Airbnb ROI: -0.69% Traditional ROI: 2.7%
Lot 20-8A East Side Trl Oakland, ME INCLUDES ATTACHED 2-CAR GARAGE AND BREEZEWAY Welcome to this thoughtfully designed new...	4 beds \| 2 baths \| 2,320 sq.ft.	$550,000	Airbnb cash on cash: 3.1% Traditional cash on cash: 4.82% Airbnb Rental Income: $2869 Traditional Rental Income: $3086 Airbnb ROI: 3.1% Traditional ROI: 4.82%
Lot 13 Jacques Ln 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: 2.4% Traditional cash on cash: 5.68% Airbnb Rental Income: $1968 Traditional Rental Income: $2757 Airbnb ROI: 2.4% Traditional ROI: 5.68%
11 Jacques Ln 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: 2.25% Traditional cash on cash: 5.3% Airbnb Rental Income: $1968 Traditional Rental Income: $2721 Airbnb ROI: 2.25% Traditional ROI: 5.3%
12 Jacques Ln 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: 2.25% Traditional cash on cash: 5.3% Airbnb Rental Income: $1968 Traditional Rental Income: $2721 Airbnb ROI: 2.25% Traditional ROI: 5.3%
Lot 19 Autumn Ln Oakland, ME Lot 19 Autumn Ln, Oakland, ME 04963 \| Single Family Residential	3 beds \| 2 baths \| 1,371 sq.ft.	$469,900	Airbnb cash on cash: 0.61% Traditional cash on cash: 1.72% Airbnb Rental Income: $1968 Traditional Rental Income: $1936 Airbnb ROI: 0.61% Traditional ROI: 1.72%
11 Village Green Cir Oakland, ME 11 Village Green Cir, Oakland, ME 04963 \| Single Family Residential	3 beds \| 2 baths \| 2,112 sq.ft.	$525,000	Airbnb cash on cash: 0.15% Traditional cash on cash: 3.98% Airbnb Rental Income: $1968 Traditional Rental Income: $3329 Airbnb ROI: 0.15% Traditional ROI: 3.98%
88 County Rd Oakland, ME 88 County Rd, Oakland, ME 04963 \| Single Family Residential	5 beds \| 2 baths \| 2,450 sq.ft.	$389,000	Airbnb cash on cash: -0.87% Traditional cash on cash: 6.88% Airbnb Rental Income: $987 Traditional Rental Income: $3460 Airbnb ROI: -0.87% Traditional ROI: 6.88%
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.	$325,000	Airbnb cash on cash: 3.43% Traditional cash on cash: 9.69% Airbnb Rental Income: $1968 Traditional Rental Income: $3366 Airbnb ROI: 3.43% Traditional ROI: 9.69%
20 & 21 Bass Cv 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.	$878,000	Airbnb cash on cash: -1.69% Traditional cash on cash: 2.36% Airbnb Rental Income: $987 Traditional Rental Income: $3948 Airbnb ROI: -1.69% Traditional ROI: 2.36%
72 Cedar Village Pl Oakland, ME Experience the best of Maine lakefront living with this charming 2-bedroom home on sought-...	2 beds \| 1 baths \| 1,247 sq.ft.	$775,000	Airbnb cash on cash: 0.03% Traditional cash on cash: 2.97% Airbnb Rental Income: $1281 Traditional Rental Income: $3002 Airbnb ROI: 0.03% Traditional ROI: 2.97%
13 Selden Ln 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.	$349,900	Airbnb cash on cash: 1.37% Traditional cash on cash: 8.66% Airbnb Rental Income: $1281 Traditional Rental Income: $3271 Airbnb ROI: 1.37% Traditional ROI: 8.66%
28 Belgrade Rd Oakland, ME Picturesque waterfront setting on one of Maine's most desirable lakes. On the market for t...	3 beds \| 2 baths \| 2,406 sq.ft.	$759,000	Airbnb cash on cash: 0.92% Traditional cash on cash: 4.01% Airbnb Rental Income: $1968 Traditional Rental Income: $3637 Airbnb ROI: 0.92% Traditional ROI: 4.01%
28 Jacques Ln #9 & 10 Oakland, ME New Construction!! Duplex to be built! Public water & sewer will be connected. Call us tod...	4 beds \| 2 baths \| 2,718 sq.ft.	$569,000	Airbnb cash on cash: 1.62% Traditional cash on cash: 6.66% Airbnb Rental Income: $2869 Traditional Rental Income: $4881 Airbnb ROI: 1.62% Traditional ROI: 6.66%
7 Hemlock Ests Oakland, ME Welcome to Wildewood Estates, a vibrant lakeside community in the Belgrade Lakes region wi...	4 beds \| 2 baths \| 1,973 sq.ft.	$619,000	Airbnb cash on cash: 2.55% Traditional cash on cash: 6.22% Airbnb Rental Income: $2869 Traditional Rental Income: $4326 Airbnb ROI: 2.55% Traditional ROI: 6.22%
62 Axtell Dr Oakland, ME 62 Axtell Dr, Oakland, ME 04963 \| Single Family Residential	3 beds \| 2 baths \| 2,100 sq.ft.	$485,900	Airbnb cash on cash: 0.64% Traditional cash on cash: 4.53% Airbnb Rental Income: $1968 Traditional Rental Income: $3219 Airbnb ROI: 0.64% Traditional ROI: 4.53%
28 Jacques Ln #7 & 8 Oakland, ME 28 Jacques Ln #7 & 8, Oakland, ME 04963 \| Single Family Residential	4 beds \| 2 baths \| 2,718 sq.ft.	$569,000	Airbnb cash on cash: 1.62% Traditional cash on cash: 1.8% Airbnb Rental Income: $2869 Traditional Rental Income: $2298 Airbnb ROI: 1.62% Traditional ROI: 1.8%
28 Jacques Ln #1 & 2 Oakland, ME 28 Jacques Ln #1 & 2, Oakland, ME 04963 \| Single Family Residential	4 beds \| 2 baths \| 2,718 sq.ft.	$569,000	Airbnb cash on cash: 1.62% Traditional cash on cash: 1.8% Airbnb Rental Income: $2869 Traditional Rental Income: $2298 Airbnb ROI: 1.62% Traditional ROI: 1.8%
28 Jacques Ln #3 & 4 Oakland, ME 28 Jacques Ln #3 & 4, Oakland, ME 04963 \| Single Family Residential	4 beds \| 2 baths \| 2,718 sq.ft.	$569,000	Airbnb cash on cash: 1.62% Traditional cash on cash: 1.8% Airbnb Rental Income: $2869 Traditional Rental Income: $2298 Airbnb ROI: 1.62% Traditional ROI: 1.8%
28 Jacques Ln #5 & 6 Oakland, ME 28 Jacques Ln #5 & 6, Oakland, ME 04963 \| Single Family Residential	4 beds \| 2 baths \| 2,718 sq.ft.	$569,000	Airbnb cash on cash: 1.62% Traditional cash on cash: 4.67% Airbnb Rental Income: $2869 Traditional Rental Income: $3822 Airbnb ROI: 1.62% Traditional ROI: 4.67%
Lot 8 Autumn Ln Oakland, ME Lot 8 Autumn Ln, Oakland, ME 04963 \| Single Family Residential	3 beds \| 2 baths \| 1,535 sq.ft.	$489,900	Airbnb cash on cash: 0.49% Traditional cash on cash: 4.42% Airbnb Rental Income: $1968 Traditional Rental Income: $3251 Airbnb ROI: 0.49% Traditional ROI: 4.42%
113 & 121 High St Oakland, ME 113 & 121 High St, Oakland, ME 04963 \| Single Family Residential	2 beds \| 2 baths \| 2,920 sq.ft.	$1,299,000	Airbnb cash on cash: -1.7% Traditional cash on cash: -1.18% Airbnb Rental Income: $1281 Traditional Rental Income: $1511 Airbnb ROI: -1.7% Traditional ROI: -1.18%
Lot 10 Autumn Ln Oakland, ME Lot 10 Autumn Ln, Oakland, ME 04963 \| Single Family Residential	2 beds \| 2 baths \| 1,085 sq.ft.	$429,900	Airbnb cash on cash: -0.53% Traditional cash on cash: 4.21% Airbnb Rental Income: $1281 Traditional Rental Income: $2790 Airbnb ROI: -0.53% Traditional ROI: 4.21%
Lot 15 Autumn Ln Oakland, ME Lot 15 Autumn Ln, Oakland, ME 04963 \| Single Family Residential	4 beds \| 2 baths \| 1,870 sq.ft.	$594,900	Airbnb cash on cash: 1.35% Traditional cash on cash: 1.52% Airbnb Rental Income: $2869 Traditional Rental Income: $2298 Airbnb ROI: 1.35% Traditional ROI: 1.52%
Lot 14 Autumn Ln Oakland, ME Lot 14 Autumn Ln, Oakland, ME 04963 \| Single Family Residential	2 beds \| 2 baths \| 1,205 sq.ft.	$439,900	Airbnb cash on cash: -0.58% Traditional cash on cash: 0.96% Airbnb Rental Income: $1281 Traditional Rental Income: $1511 Airbnb ROI: -0.58% Traditional ROI: 0.96%

Your search for investment property begins and ends here

Single Family Homes for Sale in Oakland, ME

520 Smithfield Rd

Oakland, ME

2 beds | 1 baths | 1,056 sq.ft.

$195,000

Airbnb cash on cash: 2.67%

Traditional cash on cash: 6.17%

Airbnb Rental Income: $1281

Traditional Rental Income: $1526

Airbnb ROI: 2.67%

Traditional ROI: 6.17%

96 Oak Hill Dr

Oakland, ME

4 beds | 2 baths | 2,496 sq.ft.

$469,900

Airbnb cash on cash: 3.22%

Traditional cash on cash: 6.11%

Airbnb Rental Income: $2869

Traditional Rental Income: $3471

Airbnb ROI: 3.22%

Traditional ROI: 6.11%

203 Belgrade Rd

Oakland, ME

2 beds | 2 baths | 1,502 sq.ft.

$399,000

Airbnb cash on cash: 0.86%

Traditional cash on cash: 6.08%

Airbnb Rental Income: $1281

Traditional Rental Income: $2829

Airbnb ROI: 0.86%

Traditional ROI: 6.08%

12 Gleason Farm Rd

Oakland, ME

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

$458,000

Airbnb cash on cash: 1.39%

Traditional cash on cash: 3.92%

Airbnb Rental Income: $1968

Traditional Rental Income: $2534

Airbnb ROI: 1.39%

Traditional ROI: 3.92%

278 Middle Rd

Oakland, ME

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

$276,500

Airbnb cash on cash: 1.41%

Traditional cash on cash: 5.86%

Airbnb Rental Income: $1281

Traditional Rental Income: $2037

Airbnb ROI: 1.41%

Traditional ROI: 5.86%

132 Washington St

Oakland, ME

3 beds | 2 baths | 1,518 sq.ft.

$239,000

Airbnb cash on cash: 3.2%

Traditional cash on cash: 10.72%

Airbnb Rental Income: $1968

Traditional Rental Income: $3150

Airbnb ROI: 3.2%

Traditional ROI: 10.72%

25 Gifford Place & Blake Is

Oakland, ME

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

$895,000

Airbnb cash on cash: -1.41%

Traditional cash on cash: 0.75%

Airbnb Rental Income: $1281

Traditional Rental Income: $2675

Airbnb ROI: -1.41%

Traditional ROI: 0.75%

66 Brickett Point Estates

Oakland, ME

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

$659,000

Airbnb cash on cash: 0.14%

Traditional cash on cash: 3.64%

Airbnb Rental Income: $1968

Traditional Rental Income: $3606

Airbnb ROI: 0.14%