Real Estate Investment Properties for Sale in Oakland, MD

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

Explore a variety of short-term homes & houses in Oakland, MD. Invest wisely with VRBO & Oakland, MD 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, MD

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
142 LEMLEY DRIVE #I Oakland, MD 3 Bedroom 2 Bath ranch style property with gorgeous lake, ski slope and mountain views AND...	3 beds \| 2 baths \| N/A	$419,000	Airbnb cash on cash: 3.99% Traditional cash on cash: 4.14% Airbnb Rental Income: $2974 Traditional Rental Income: $2347 Airbnb ROI: 3.99% Traditional ROI: 4.14%
483 SKIPPERS POINT ROAD Oakland, MD Experience the best in lake living with the stunning 4-bedroom, 3-bath lakefront retreat a...	4 beds \| 3 baths \| 2,286 sq.ft.	$1,150,000	Airbnb cash on cash: 0.06% Traditional cash on cash: 0.95% Airbnb Rental Income: $3002 Traditional Rental Income: $3271 Airbnb ROI: 0.06% Traditional ROI: 0.95%
783 MOUNTAINVIEW DRIVE Oakland, MD Beautiful, 3 bedroom, 3 bath home located in the sought after community of Mountainside at...	3 beds \| 3 baths \| 1,971 sq.ft.	$619,900	Airbnb cash on cash: 1.74% Traditional cash on cash: 2.82% Airbnb Rental Income: $2974 Traditional Rental Income: $2914 Airbnb ROI: 1.74% Traditional ROI: 2.82%
62 MIDDLETON ROAD Oakland, MD Charming Lake Home at The Blakeslee â This 3Bed 2.5Bath contemporary cabin is located in...	3 beds \| 3 baths \| 2,397 sq.ft.	$829,900	Airbnb cash on cash: 0.6% Traditional cash on cash: 1.51% Airbnb Rental Income: $2974 Traditional Rental Income: $2989 Airbnb ROI: 0.6% Traditional ROI: 1.51%
256 JEFFREY LANE #28 Oakland, MD Looking for an updated condo at Deep Creek Lake? Look no further! 256 Jeffrey Lane #28 is ...	3 beds \| 4 baths \| 1,838 sq.ft.	$465,000	Airbnb cash on cash: 3.19% Traditional cash on cash: 5.46% Airbnb Rental Income: $2974 Traditional Rental Income: $3281 Airbnb ROI: 3.19% Traditional ROI: 5.46%
522 E GREEN STREET Oakland, MD If you are looking for a low maintenance stone home sitting on a level lot in the town of ...	3 beds \| 4 baths \| 1,503 sq.ft.	$349,000	Airbnb cash on cash: 4.41% Traditional cash on cash: 6.21% Airbnb Rental Income: $2974 Traditional Rental Income: $2878 Airbnb ROI: 4.41% Traditional ROI: 6.21%
343 LAKE FOREST DRIVE Oakland, MD Discover lakeside living at its finest in this beautifully updated 5 bedroom 3 bathroom La...	5 beds \| 3 baths \| 3,162 sq.ft.	$1,249,000	Airbnb cash on cash: 1.13% Traditional cash on cash: 1.29% Airbnb Rental Income: $4337 Traditional Rental Income: $3604 Airbnb ROI: 1.13% Traditional ROI: 1.29%
98 BEAR RUN ROAD Oakland, MD TIRED OF CITY LIVING? ENJOY PLENTY OF ROOM TO ROAM ON THIS 44.35 ACRE TRACT WHICH INCLUDE...	3 beds \| 2 baths \| 1,192 sq.ft.	$874,750	Airbnb cash on cash: 1.44% Traditional cash on cash: 1.71% Airbnb Rental Income: $2974 Traditional Rental Income: $2510 Airbnb ROI: 1.44% Traditional ROI: 1.71%
20241 GARRETT HIGHWAY #6 Oakland, MD Lake View Townhouse at Lakeland Estates! This 3Bed 3Bath townhome is right in the heart of...	3 beds \| 3 baths \| 1,657 sq.ft.	$499,900	Airbnb cash on cash: 3.02% Traditional cash on cash: 4.15% Airbnb Rental Income: $2974 Traditional Rental Income: $2814 Airbnb ROI: 3.02% Traditional ROI: 4.15%
565 GLENDALE ROAD #115A Oakland, MD Silver Tree Suites unit facing the lake with 1 bedroom on the main level. This is vacation...	1 beds \| 1 baths \| 968 sq.ft.	$324,900	Airbnb cash on cash: 3.86% Traditional cash on cash: 4.43% Airbnb Rental Income: $2327 Traditional Rental Income: $1924 Airbnb ROI: 3.86% Traditional ROI: 4.43%
324 PENN COVE ROAD Oakland, MD Stunning log home situated on a large lot in the private Penn Cove community. This turn-ke...	4 beds \| 4 baths \| 3,820 sq.ft.	$1,250,000	Airbnb cash on cash: 0.31% Traditional cash on cash: 1.54% Airbnb Rental Income: $3002 Traditional Rental Income: $3744 Airbnb ROI: 0.31% Traditional ROI: 1.54%
82 MOUNTAINVIEW COURT Oakland, MD Lake Access Chalet in Picturesque Mountain Community â This 4 Bedroom 3.5 Bath Chalet is...	4 beds \| 4 baths \| 2,604 sq.ft.	$749,900	Airbnb cash on cash: 1.22% Traditional cash on cash: 2.7% Airbnb Rental Income: $3002 Traditional Rental Income: $3350 Airbnb ROI: 1.22% Traditional ROI: 2.7%
19956 GARRETT HIGHWAY #2 Oakland, MD Rare opportunity to own at one of Deep Creek Lake's most premier lakefront condo communiti...	4 beds \| 4 baths \| 3,012 sq.ft.	$1,299,000	Airbnb cash on cash: 0.03% Traditional cash on cash: 1.23% Airbnb Rental Income: $3002 Traditional Rental Income: $3767 Airbnb ROI: 0.03% Traditional ROI: 1.23%
473 CUMBERLAND ROAD Oakland, MD Nestled on a serene wooded hillside above Deep Creek Lake, this cozy home offers the perfe...	3 beds \| 2 baths \| 1,400 sq.ft.	$349,900	Airbnb cash on cash: 5.04% Traditional cash on cash: 5.52% Airbnb Rental Income: $2974 Traditional Rental Income: $2446 Airbnb ROI: 5.04% Traditional ROI: 5.52%
2816 STEYER MINE ROAD Oakland, MD 103 Acre Hunters and Fisherman's Paradise! Property is improved with a 3 bedroom/2 bathroo...	3 beds \| 2 baths \| 1,534 sq.ft.	$400,000	Airbnb cash on cash: 4.43% Traditional cash on cash: 5.72% Airbnb Rental Income: $2974 Traditional Rental Income: $2774 Airbnb ROI: 4.43% Traditional ROI: 5.72%
26 ARROWHEAD LANE #26 Oakland, MD Nestled in the heart of Deep Creek, with lake views and a designated dock this spacious 3-...	3 beds \| 3 baths \| 2,000 sq.ft.	$699,000	Airbnb cash on cash: 1.42% Traditional cash on cash: 2.78% Airbnb Rental Income: $2974 Traditional Rental Income: $3176 Airbnb ROI: 1.42% Traditional ROI: 2.78%
1674 PARADISE POINT ROAD Oakland, MD Beautifully remodeled lakefront home offering private dock and stunning views of Deep Cree...	4 beds \| 3 baths \| 2,340 sq.ft.	$1,689,900	Airbnb cash on cash: -0.16% Traditional cash on cash: 0.66% Airbnb Rental Income: $3002 Traditional Rental Income: $3589 Airbnb ROI: -0.16% Traditional ROI: 0.66%
450 FERN DRIVE Oakland, MD Absolutely stunning, this thoughtfully and meticulously remodeled picture-perfect 2-bedroo...	2 beds \| 1 baths \| 861 sq.ft.	$309,000	Airbnb cash on cash: 4.72% Traditional cash on cash: 4.87% Airbnb Rental Income: $2484 Traditional Rental Income: $1925 Airbnb ROI: 4.72% Traditional ROI: 4.87%
297 PARADISE POINT ROAD Oakland, MD PRIVATE MOUNTAINTOP RETREAT - 3BR, 4BA on 4 acres, less than a mile from Deep Creek Lake! ...	3 beds \| 4 baths \| 3,024 sq.ft.	$349,000	Airbnb cash on cash: 4.91% Traditional cash on cash: 7.38% Airbnb Rental Income: $2974 Traditional Rental Income: $3100 Airbnb ROI: 4.91% Traditional ROI: 7.38%
230 MOOSE CROSSING Oakland, MD Looking for a renovated home on a few acres with an oversize garage and a central location...	3 beds \| 2 baths \| 2,441 sq.ft.	$499,000	Airbnb cash on cash: 3.22% Traditional cash on cash: 4.39% Airbnb Rental Income: $2974 Traditional Rental Income: $2836 Airbnb ROI: 3.22% Traditional ROI: 4.39%
464 LAKE FOREST DRIVE Oakland, MD Truly wonderful lakefront property in the Lake Forest Drive area of Deep Creek Lake with a...	4 beds \| 4 baths \| 2,496 sq.ft.	$1,725,000	Airbnb cash on cash: -0.15% Traditional cash on cash: 0.78% Airbnb Rental Income: $3002 Traditional Rental Income: $3795 Airbnb ROI: -0.15% Traditional ROI: 0.78%
723 KINGS COURT Oakland, MD Price Reduction...Four bedroom/2.5 bath home in the highly desirable Kings Hill Estates. ...	4 beds \| 3 baths \| 1,824 sq.ft.	$390,000	Airbnb cash on cash: 4.36% Traditional cash on cash: 6.04% Airbnb Rental Income: $3002 Traditional Rental Income: $2926 Airbnb ROI: 4.36% Traditional ROI: 6.04%
180 WINDING TRAIL LANE #5A Oakland, MD Looking for ease of living here at the lake? Look no further! This 5BR/4BA condo offers ov...	5 beds \| 5 baths \| 3,000 sq.ft.	$595,000	Airbnb cash on cash: 4.19% Traditional cash on cash: 6.53% Airbnb Rental Income: $4337 Traditional Rental Income: $4723 Airbnb ROI: 4.19% Traditional ROI: 6.53%
637 BETTS LANE Oakland, MD Are you looking for a private setting on over 7 acres of land? Take a look at this newly ...	3 beds \| 2 baths \| 1,377 sq.ft.	$490,000	Airbnb cash on cash: 3.23% Traditional cash on cash: 3.57% Airbnb Rental Income: $2974 Traditional Rental Income: $2445 Airbnb ROI: 3.23% Traditional ROI: 3.57%
93 PENN POINT ROAD Oakland, MD Amazing Country Setting at Deep Creek Lake on 4 Acres. Property features two (2) homes and...	5 beds \| 6 baths \| 4,480 sq.ft.	$649,000	Airbnb cash on cash: 3.89% Traditional cash on cash: 9.21% Airbnb Rental Income: $4337 Traditional Rental Income: $6648 Airbnb ROI: 3.89% Traditional ROI: 9.21%
1073 GEORGE WASHINGTON HIGHWAY Oakland, MD Make your Farmette dreams come true! This 5 bedroom farmhouse sits upon 27 acres of beau...	5 beds \| 3 baths \| 2,910 sq.ft.	$399,000	Airbnb cash on cash: 7.68% Traditional cash on cash: 7.04% Airbnb Rental Income: $4337 Traditional Rental Income: $3188 Airbnb ROI: 7.68% Traditional ROI: 7.04%
178 WINDING TRAIL LANE #5B Oakland, MD Looking for a spacious retreat that's turn key and in tremendous condition? Look no furthe...	5 beds \| 5 baths \| 3,300 sq.ft.	$594,900	Airbnb cash on cash: 4.05% Traditional cash on cash: 6.57% Airbnb Rental Income: $4337 Traditional Rental Income: $4826 Airbnb ROI: 4.05% Traditional ROI: 6.57%
611 E OAK STREET Oakland, MD Investors, this is an income producing, three unit building with three separate apartments...	N/A beds \| N/A baths \| 1,800 sq.ft.	$309,000	Airbnb cash on cash: 0.27% Traditional cash on cash: 4.77% Airbnb Rental Income: $1084 Traditional Rental Income: $2023 Airbnb ROI: 0.27% Traditional ROI: 4.77%
35 TENDERFOOT ROAD Oakland, MD Charming 3-Bedroom Rancher Near Deep Creek Lake with Community Lake Access Discover the p...	3 beds \| 2 baths \| 1,296 sq.ft.	$425,000	Airbnb cash on cash: 3.77% Traditional cash on cash: 4.06% Airbnb Rental Income: $2974 Traditional Rental Income: $2404 Airbnb ROI: 3.77% Traditional ROI: 4.06%
39 LEO FRIEND ROAD Oakland, MD Stunning Split Lakefront Home with Breathtaking Views and Type A Dock. Discover unparallel...	3 beds \| 4 baths \| 3,897 sq.ft.	$1,090,000	Airbnb cash on cash: 0.58% Traditional cash on cash: 1.88% Airbnb Rental Income: $2974 Traditional Rental Income: $3611 Airbnb ROI: 0.58% Traditional ROI: 1.88%
234 MAPLE DEL LANE Oakland, MD 3/4 BR, 3BA well-built & cared for home, 2700sf+/- in Maple Del, a private community in th...	4 beds \| 3 baths \| 2,750 sq.ft.	$475,000	Airbnb cash on cash: 3.2% Traditional cash on cash: 5.18% Airbnb Rental Income: $3002 Traditional Rental Income: $3192 Airbnb ROI: 3.2% Traditional ROI: 5.18%
403 O STREET Oakland, MD NEWLY RENOVATED! So excited to be on the market with new carpet, paint , appliances, and r...	4 beds \| 4 baths \| 2,240 sq.ft.	$299,900	Airbnb cash on cash: 5.99% Traditional cash on cash: 9.97% Airbnb Rental Income: $3002 Traditional Rental Income: $3439 Airbnb ROI: 5.99% Traditional ROI: 9.97%
180 ROMAN RIDGE ROAD #18 Oakland, MD Nestled in the mountains of Deep Creek Lake, this lakeview home in Traders Landing appeals...	4 beds \| 5 baths \| 2,608 sq.ft.	$539,000	Airbnb cash on cash: 2.51% Traditional cash on cash: 6.5% Airbnb Rental Income: $3002 Traditional Rental Income: $4323 Airbnb ROI: 2.51% Traditional ROI: 6.5%
158 SILVER TREE LANE Oakland, MD Beautiful lake view and water access home located in the Silver Tree Landing community on ...	5 beds \| 5 baths \| 2,250 sq.ft.	$829,000	Airbnb cash on cash: 2.28% Traditional cash on cash: 3.27% Airbnb Rental Income: $4337 Traditional Rental Income: $4190 Airbnb ROI: 2.28% Traditional ROI: 3.27%
4400 SAND FLAT ROAD Oakland, MD endless uses .....vacation paradise, Turn key ABnB, farmette or quiet cabin in the woods...	4 beds \| 3 baths \| 1,824 sq.ft.	$475,000	Airbnb cash on cash: 3.36% Traditional cash on cash: 4.62% Airbnb Rental Income: $3002 Traditional Rental Income: $2875 Airbnb ROI: 3.36% Traditional ROI: 4.62%
48 JEFFREY LANE #7C Oakland, MD Take a good look at this 2-3BR/2BA condo unit in Traders Landing. C unit offers three leve...	3 beds \| 2 baths \| N/A	$349,900	Airbnb cash on cash: 4.98% Traditional cash on cash: 5.35% Airbnb Rental Income: $2974 Traditional Rental Income: $2414 Airbnb ROI: 4.98% Traditional ROI: 5.35%
15705 GARRETT HIGHWAY Oakland, MD Situated on 5.42 acres along Garrett Highway, just 3 miles from Oakland, this 1965 single ...	3 beds \| 2 baths \| 2,046 sq.ft.	$335,000	Airbnb cash on cash: 5.11% Traditional cash on cash: 6.73% Airbnb Rental Income: $2974 Traditional Rental Income: $2798 Airbnb ROI: 5.11% Traditional ROI: 6.73%
2719 BROADFORD ROAD Oakland, MD Magnificent One Level Brick Ranch style home located walking distance to Broadford Lake P...	3 beds \| 3 baths \| 4,253 sq.ft.	$599,000	Airbnb cash on cash: 2.34% Traditional cash on cash: 3.25% Airbnb Rental Income: $2974 Traditional Rental Income: $2803 Airbnb ROI: 2.34% Traditional ROI: 3.25%
849 GLENDALE ROAD Oakland, MD Construction to begin at settlement on this completely custom 5 bedroom, 3.5 bathroom lake...	5 beds \| 4 baths \| 4,599 sq.ft.	$2,699,000	Airbnb cash on cash: 0.19% Traditional cash on cash: 0.46% Airbnb Rental Income: $4337 Traditional Rental Income: $4112 Airbnb ROI: 0.19% Traditional ROI: 0.46%
1746 STOCKSLAGER ROAD Oakland, MD Charming Lakefront Craftsman on Stockslager Rd â This 5 Bedroom, 4.5 Bathroom lakefront ...	5 beds \| 5 baths \| 4,713 sq.ft.	$2,499,000	Airbnb cash on cash: -0.14% Traditional cash on cash: 0.6% Airbnb Rental Income: $4337 Traditional Rental Income: $5133 Airbnb ROI: -0.14% Traditional ROI: 0.6%

Real Estate investment in Oakland, MD

There are 58 properties for sale in the city of Oakland . The median list price in Oakland is $566,950 and the average price per square foot is $238. In November 2024, the average monthly cash on cash return in Oakland is 4.00%. The average monthly rental income in Oakland is $2,989.

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

There are 58 investment properties available for sale in Oakland.

In 2024, 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 $2,989.

Your search for investment property begins and ends here

Investment Property for Sale in Oakland, MD

142 LEMLEY DRIVE #I

Oakland, MD

3 beds | 2 baths | N/A

$419,000

Airbnb cash on cash: 3.99%

Traditional cash on cash: 4.14%

Airbnb Rental Income: $2974

Traditional Rental Income: $2347

Airbnb ROI: 3.99%

Traditional ROI: 4.14%

483 SKIPPERS POINT ROAD

Oakland, MD

4 beds | 3 baths | 2,286 sq.ft.

$1,150,000

Airbnb cash on cash: 0.06%

Traditional cash on cash: 0.95%

Airbnb Rental Income: $3002

Traditional Rental Income: $3271

Airbnb ROI: 0.06%

Traditional ROI: 0.95%

783 MOUNTAINVIEW DRIVE

Oakland, MD

3 beds | 3 baths | 1,971 sq.ft.

$619,900

Airbnb cash on cash: 1.74%

Traditional cash on cash: 2.82%

Airbnb Rental Income: $2974

Traditional Rental Income: $2914

Airbnb ROI: 1.74%

Traditional ROI: 2.82%

62 MIDDLETON ROAD

Oakland, MD

3 beds | 3 baths | 2,397 sq.ft.

$829,900

Airbnb cash on cash: 0.6%

Traditional cash on cash: 1.51%

Airbnb Rental Income: $2974

Traditional Rental Income: $2989

Airbnb ROI: 0.6%

Traditional ROI: 1.51%

256 JEFFREY LANE #28

Oakland, MD

3 beds | 4 baths | 1,838 sq.ft.

$465,000

Airbnb cash on cash: 3.19%

Traditional cash on cash: 5.46%

Airbnb Rental Income: $2974

Traditional Rental Income: $3281

Airbnb ROI: 3.19%

Traditional ROI: 5.46%

522 E GREEN STREET

Oakland, MD

3 beds | 4 baths | 1,503 sq.ft.

$349,000

Airbnb cash on cash: 4.41%

Traditional cash on cash: 6.21%

Airbnb Rental Income: $2974

Traditional Rental Income: $2878

Airbnb ROI: 4.41%

Traditional ROI: 6.21%

343 LAKE FOREST DRIVE

Oakland, MD

5 beds | 3 baths | 3,162 sq.ft.

$1,249,000

Airbnb cash on cash: 1.13%

Traditional cash on cash: 1.29%

Airbnb Rental Income: $4337

Traditional Rental Income: $3604

Airbnb ROI: 1.13%

Traditional ROI: 1.29%

98 BEAR RUN ROAD

Oakland, MD

3 beds | 2 baths | 1,192 sq.ft.

$874,750

Airbnb cash on cash: 1.44%

Traditional cash on cash: 1.71%

Airbnb Rental Income: $2974

Traditional Rental Income: $2510

Airbnb ROI: 1.44%