Airbnb Properties for Sale in Oakland, MD

Looking for a vacation rental investment in Oakland, MD with high ROI ?

Explore a range of newly added short-term rental homes in Oakland, MD. Make a smart investment with newly available Airbnb properties and find the ideal high-ROI property for sale.

Airbnb For Sale in Oakland, MD

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
609 Southern Pines Drive Oakland, MD Welcome to your next dream home! Nestled on a 4-acre wooded lot, this custom built residen...	4 beds \| 3 baths \| 2,250 sq.ft.	$440,000	Airbnb cash on cash: 6.14% Traditional cash on cash: 5.89% Airbnb Rental Income: $4304 Traditional Rental Income: $3296 Airbnb ROI: 6.14% Traditional ROI: 5.89%
565 GLENDALE ROAD #124 Oakland, MD Public: If you are looking for an affordable way to own at Deep Creek Lake, this is it! Th...	1 beds \| 1 baths \| 382 sq.ft.	$175,000	Airbnb cash on cash: 6.9% Traditional cash on cash: 5.99% Airbnb Rental Income: $2748 Traditional Rental Income: $1949 Airbnb ROI: 6.9% Traditional ROI: 5.99%
565 GLENDALE ROAD #116 Oakland, MD Don't miss this rare opportunity to own a beautifully updated 1-bedroom unit at Silver Tre...	1 beds \| 1 baths \| 484 sq.ft.	$179,000	Airbnb cash on cash: 9.94% Traditional cash on cash: 6.64% Airbnb Rental Income: $2748 Traditional Rental Income: $1539 Airbnb ROI: 9.94% Traditional ROI: 6.64%
565 GLENDALE ROAD #303B Oakland, MD Fully Renovated Penthouse at Silver Tree Suites Been holding out for the nicest unit at Si...	2 beds \| 1 baths \| 887 sq.ft.	$399,900	Airbnb cash on cash: 3.35% Traditional cash on cash: 3.32% Airbnb Rental Income: $2615 Traditional Rental Income: $1981 Airbnb ROI: 3.35% Traditional ROI: 3.32%
321 DEER PARK HOTEL ROAD Oakland, MD New Price Now $360,000! Beautifully Updated Mountain Retreat Near Deep Creek Lake Heres yo...	3 beds \| 2 baths \| 2,516 sq.ft.	$360,000	Airbnb cash on cash: 6.3% Traditional cash on cash: 6.18% Airbnb Rental Income: $3503 Traditional Rental Income: $2692 Airbnb ROI: 6.3% Traditional ROI: 6.18%
98 BEAR RUN ROAD Oakland, MD TIRED OF CITY LIVING? ENJOY PLENTY OF ROOM TO ROAM ON THIS 2 ACRE TRACT WHICH INCLUDES A F...	3 beds \| 2 baths \| 1,080 sq.ft.	$268,900	Airbnb cash on cash: 9.01% Traditional cash on cash: 8.14% Airbnb Rental Income: $3503 Traditional Rental Income: $2510 Airbnb ROI: 9.01% Traditional ROI: 8.14%
25 SILVER TREE LANE Oakland, MD Beautiful lake access retreat located in the Silver Tree Landings community. This recently...	5 beds \| 4 baths \| 2,364 sq.ft.	$767,500	Airbnb cash on cash: 4.02% Traditional cash on cash: 1.75% Airbnb Rental Income: $5609 Traditional Rental Income: $2858 Airbnb ROI: 4.02% Traditional ROI: 1.75%
180 PARADISE RIDGE ROAD Oakland, MD Discover your perfect Deep Creek Lake getaway in the desirable Ridge at Paradise Point com...	3 beds \| 2 baths \| 1,152 sq.ft.	$425,000	Airbnb cash on cash: 4.84% Traditional cash on cash: 3.39% Airbnb Rental Income: $3503 Traditional Rental Income: $2154 Airbnb ROI: 4.84% Traditional ROI: 3.39%
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 \| 484 sq.ft.	$299,000	Airbnb cash on cash: 5.52% Traditional cash on cash: 4.89% Airbnb Rental Income: $2748 Traditional Rental Income: $1924 Airbnb ROI: 5.52% Traditional ROI: 4.89%
126 LEO FRIEND ROAD Oakland, MD Perched above the treetops with panoramic lake views, this three-level retreat blends comf...	4 beds \| 3 baths \| 2,235 sq.ft.	$529,900	Airbnb cash on cash: 5.09% Traditional cash on cash: 4.69% Airbnb Rental Income: $4304 Traditional Rental Income: $3200 Airbnb ROI: 5.09% Traditional ROI: 4.69%
20160 GARRETT HIGHWAY #H708 Oakland, MD Welcome to Will O' the Wisp Condominiums, where premium upgrades meet penthouse-level lake...	1 beds \| 1 baths \| 550 sq.ft.	$300,000	Airbnb cash on cash: 5.35% Traditional cash on cash: 3.33% Airbnb Rental Income: $2748 Traditional Rental Income: $1530 Airbnb ROI: 5.35% Traditional ROI: 3.33%
1473 PERGIN FARM RD Oakland, MD TIME TO UNWIND at this absolutely stunning Deep Creek Lake retreat boasting million-dollar...	4 beds \| 2 baths \| N/A	$999,500	Airbnb cash on cash: 2.17% Traditional cash on cash: 1.48% Airbnb Rental Income: $4304 Traditional Rental Income: $2753 Airbnb ROI: 2.17% Traditional ROI: 1.48%
473 CUMBERLAND ROAD Oakland, MD Nestled on a tranquil wooded hillside overlooking Deep Creek Lake, this charming home offe...	3 beds \| 2 baths \| 1,389 sq.ft.	$315,000	Airbnb cash on cash: 7.19% Traditional cash on cash: 6.23% Airbnb Rental Income: $3503 Traditional Rental Income: $2446 Airbnb ROI: 7.19% Traditional ROI: 6.23%
565 GLENDALE ROAD #106 B Oakland, MD Ground-floor end unit with lake views at Silver Tree Suites. This one-bedroom layout packs...	1 beds \| 1 baths \| N/A	$269,900	Airbnb cash on cash: 6.2% Traditional cash on cash: 5.07% Airbnb Rental Income: $2748 Traditional Rental Income: $1813 Airbnb ROI: 6.2% Traditional ROI: 5.07%
328 STOOL ROCK ROAD Oakland, MD Designed and built for the sellers, this 4 bedroom, 2.5 bath home is a true showcase of cr...	4 beds \| 3 baths \| 1,860 sq.ft.	$565,000	Airbnb cash on cash: 4.62% Traditional cash on cash: 3.97% Airbnb Rental Income: $4304 Traditional Rental Income: $3055 Airbnb ROI: 4.62% Traditional ROI: 3.97%
41 FOX DEN ROAD Oakland, MD Nestled in the heart of Deep Creek Lake, this charming and fully furnished cottage offers ...	2 beds \| 1 baths \| 1,569 sq.ft.	$239,000	Airbnb cash on cash: 6.37% Traditional cash on cash: 4.81% Airbnb Rental Income: $2615 Traditional Rental Income: $1638 Airbnb ROI: 6.37% Traditional ROI: 4.81%
4 LAUREL BROOK DRIVE #4 Oakland, MD Opportunites abound at this wonderfully maintained home in Laurel Brook! Whether you are l...	2 beds \| 2 baths \| N/A	$230,000	Airbnb cash on cash: 6.92% Traditional cash on cash: 6.01% Airbnb Rental Income: $2615 Traditional Rental Income: $1792 Airbnb ROI: 6.92% Traditional ROI: 6.01%
163 CRESTVIEW DRIVE Oakland, MD Welcome to 163 Crestview Drive a beautifully maintained 3-bedroom, 2.5-bath home nestled i...	3 beds \| 3 baths \| 1,416 sq.ft.	$335,000	Airbnb cash on cash: 6.8% Traditional cash on cash: 5.67% Airbnb Rental Income: $3503 Traditional Rental Income: $2376 Airbnb ROI: 6.8% Traditional ROI: 5.67%
127 PARADISE HEIGHTS Oakland, MD Beautifully renovated lake access log home located in the centrally located Paradise Cove ...	3 beds \| 3 baths \| 2,240 sq.ft.	$1,199,000	Airbnb cash on cash: 0.84% Traditional cash on cash: 0.46% Airbnb Rental Income: $3503 Traditional Rental Income: $2308 Airbnb ROI: 0.84% Traditional ROI: 0.46%
565 GLENDALE ROAD #212 Oakland, MD Silver Tree Suites offers 350' of pristine shoreline at Deep Creek Lake with western expos...	1 beds \| 1 baths \| 527 sq.ft.	$215,000	Airbnb cash on cash: 8.17% Traditional cash on cash: 7.11% Airbnb Rental Income: $2748 Traditional Rental Income: $1886 Airbnb ROI: 8.17% Traditional ROI: 7.11%
15 VILLAGE DRIVE #1 Oakland, MD Escape to a simpler time with all the modern conveniences you desire at this 2-bedroom log...	2 beds \| 1 baths \| N/A	$440,000	Airbnb cash on cash: 2.85% Traditional cash on cash: 2.62% Airbnb Rental Income: $2615 Traditional Rental Income: $1895 Airbnb ROI: 2.85% Traditional ROI: 2.62%
139 OVERLOOK RIDGE DRIVE Oakland, MD Perched atop Holiday Hill on a 1.5-acre site, you will find this contemporary home with be...	5 beds \| 5 baths \| 2,846 sq.ft.	$875,000	Airbnb cash on cash: 3.62% Traditional cash on cash: 2.35% Airbnb Rental Income: $5609 Traditional Rental Income: $3448 Airbnb ROI: 3.62% Traditional ROI: 2.35%
155 BASSWOOD WAY Oakland, MD Tucked just off Lakeshore Drive, this log home nails that luxury treehouse feel. Wrapped i...	5 beds \| 3 baths \| 2,792 sq.ft.	$699,900	Airbnb cash on cash: 4.91% Traditional cash on cash: 2.95% Airbnb Rental Income: $5609 Traditional Rental Income: $3207 Airbnb ROI: 4.91% Traditional ROI: 2.95%
565 GLENDALE ROAD #125 Oakland, MD Wake up to the lake at your doorstep. This ground-level, end-unit condo puts you right whe...	1 beds \| 1 baths \| 496 sq.ft.	$349,900	Airbnb cash on cash: 4.69% Traditional cash on cash: 3.48% Airbnb Rental Income: $2748 Traditional Rental Income: $1705 Airbnb ROI: 4.69% Traditional ROI: 3.48%
565 GLENDALE ROAD #307 Oakland, MD Third-level unit at Silver Tree Suites with direct lake frontage and stunning water views....	1 beds \| 1 baths \| 832 sq.ft.	$299,900	Airbnb cash on cash: 5.16% Traditional cash on cash: 4.74% Airbnb Rental Income: $2748 Traditional Rental Income: $1983 Airbnb ROI: 5.16% Traditional ROI: 4.74%
723 KINGS Oakland, MD ""Charming two-story home situated on a beautiful .292-acre level lot in a prime location ...	4 beds \| 3 baths \| N/A	$380,000	Airbnb cash on cash: 7.54% Traditional cash on cash: 6.39% Airbnb Rental Income: $4304 Traditional Rental Income: $2986 Airbnb ROI: 7.54% Traditional ROI: 6.39%
163 MITCHELL DRIVE Oakland, MD 3/4BR, 2.5BA, 2250sf+/- renovated home in Mitchell Manor! Newer roof in last 2 years, owne...	4 beds \| 3 baths \| 2,242 sq.ft.	$324,900	Airbnb cash on cash: 9.22% Traditional cash on cash: 8.8% Airbnb Rental Income: $4304 Traditional Rental Income: $3270 Airbnb ROI: 9.22% Traditional ROI: 8.8%
206 MAYHEW INN ROAD Oakland, MD Just 2.5 miles from the scenic Swallow Falls State Park, this charming 1-bedroom, 1-bath h...	1 beds \| 1 baths \| N/A	$229,000	Airbnb cash on cash: 7.9% Traditional cash on cash: 5.67% Airbnb Rental Income: $2748 Traditional Rental Income: $1618 Airbnb ROI: 7.9% Traditional ROI: 5.67%
969 HOYES RUN ROAD Oakland, MD Tucked among towering pines and hardwoods, this fully TURN KEY 5-bedroom log chalet blends...	5 beds \| 3 baths \| 3,614 sq.ft.	$725,000	Airbnb cash on cash: 4.83% Traditional cash on cash: 3.38% Airbnb Rental Income: $5609 Traditional Rental Income: $3501 Airbnb ROI: 4.83% Traditional ROI: 3.38%
315 COOLIDGE AVENUE Oakland, MD Well maintained brick rancher located in the heart of Oakland. This home offers a large ki...	3 beds \| 2 baths \| 1,600 sq.ft.	$269,500	Airbnb cash on cash: 8.63% Traditional cash on cash: 7.51% Airbnb Rental Income: $3503 Traditional Rental Income: $2447 Airbnb ROI: 8.63% Traditional ROI: 7.51%
531 GLENDALE ROAD #B302 Oakland, MD Experience effortless lakeside living at its finest in this spacious 2-bedroom, 1-bath uni...	2 beds \| 1 baths \| 887 sq.ft.	$369,000	Airbnb cash on cash: 3.7% Traditional cash on cash: 3.68% Airbnb Rental Income: $2615 Traditional Rental Income: $1981 Airbnb ROI: 3.7% Traditional ROI: 3.68%
501 CHRISTOPHERS WAY Oakland, MD Check out this opportunity to own your own mountain top chalet getaway complete with 3 bed...	3 beds \| 2 baths \| 1,617 sq.ft.	$249,000	Airbnb cash on cash: 9.39% Traditional cash on cash: 8.12% Airbnb Rental Income: $3503 Traditional Rental Income: $2433 Airbnb ROI: 9.39% Traditional ROI: 8.12%
333 SLOAN TRACT ROAD Oakland, MD Charming cabin off the coveted Lake Shore Drive offering seasonal lake views. This home ha...	4 beds \| 4 baths \| 1,492 sq.ft.	$475,000	Airbnb cash on cash: 5.57% Traditional cash on cash: 4.08% Airbnb Rental Income: $4304 Traditional Rental Income: $2737 Airbnb ROI: 5.57% Traditional ROI: 4.08%
511 E GREEN STREET Oakland, MD A must see complete renovation in Oakland! Taken down to the studs and updated with new wi...	4 beds \| 2 baths \| 1,880 sq.ft.	$309,000	Airbnb cash on cash: 9.81% Traditional cash on cash: 7.78% Airbnb Rental Income: $4304 Traditional Rental Income: $2808 Airbnb ROI: 9.81% Traditional ROI: 7.78%
20676 GARRETT HIGHWAY Oakland, MD CENTRAL DEEP CREEK LAKEFRONT LOG HOME ***Fully Furnished 5BR w/ Dock, Hot Tub & Fireplaces...	5 beds \| 5 baths \| 2,280 sq.ft.	$1,499,000	Airbnb cash on cash: 1.44% Traditional cash on cash: 0.97% Airbnb Rental Income: $5609 Traditional Rental Income: $3831 Airbnb ROI: 1.44% Traditional ROI: 0.97%
873 PARADISE HEIGHTS Oakland, MD Escape to Sage Mountain Retreat, a beautifully crafted 5-bedroom, 4-bath custom home nestl...	5 beds \| 4 baths \| 2,934 sq.ft.	$829,000	Airbnb cash on cash: 3.84% Traditional cash on cash: 2.55% Airbnb Rental Income: $5609 Traditional Rental Income: $3492 Airbnb ROI: 3.84% Traditional ROI: 2.55%
1570 GARRETT ROAD Oakland, MD Located between Oakland and Deep Creek Lake, this log ranch is situated on 14.82 acres, in...	3 beds \| 1 baths \| 1,408 sq.ft.	$300,000	Airbnb cash on cash: 7.78% Traditional cash on cash: 5.96% Airbnb Rental Income: $3503 Traditional Rental Income: $2214 Airbnb ROI: 7.78% Traditional ROI: 5.96%
1260 GNEGY CHURCH ROAD Oakland, MD Discover space, privacy, and mountain charm on this stunning property nestled on over 76.0...	3 beds \| 3 baths \| 4,420 sq.ft.	$449,000	Airbnb cash on cash: 4.51% Traditional cash on cash: 3.94% Airbnb Rental Income: $3503 Traditional Rental Income: $2493 Airbnb ROI: 4.51% Traditional ROI: 3.94%
5202 HUTTON ROAD Oakland, MD Charming ranch-style home offering 3 bedrooms, 1 full bath, and loads of potential! This o...	3 beds \| 1 baths \| 1,199 sq.ft.	$239,000	Airbnb cash on cash: 9.95% Traditional cash on cash: 7.15% Airbnb Rental Income: $3503 Traditional Rental Income: $2097 Airbnb ROI: 9.95% Traditional ROI: 7.15%
215 N 10th Street Oakland, MD Welcome home to this recently renovated ranch featuring 3 bedrooms, 1 bathroom, and approx...	3 beds \| 1 baths \| 1,518 sq.ft.	$289,000	Airbnb cash on cash: 7.93% Traditional cash on cash: 5.89% Airbnb Rental Income: $3503 Traditional Rental Income: $2174 Airbnb ROI: 7.93% Traditional ROI: 5.89%

Vacation Rentals in Oakland

There are 45 vacation rental properties available for sale in the city of Oakland . The median list price of Airbnb properties available for sale in Oakland is $475,000 and the average price per square foot is $214. The cash on cash return on vacation rentals in Oakland is 4.00%. The average monthly short term rental income in Oakland is $3,503.

Oakland, MD Short Term Rentals FAQs for Buyers, Sellers and Investors

There are 45 Airbnb properties available for sale in Oakland.

In 2025, the best neighborhood to buy short term rental property is Oakland.

In September 2025, the average Airbnb occupancy rate in Oakland is 33%.

Airbnb data on vacation rentals in Oakland, MD is available at Mashvisor. You can access data such as listings, real-time pricing trends, Oakland, MD market insights, guest information and booking details, seasonality trends and historical Oakland, MD Airbnb performance data.

Your search for investment property begins and ends here

Airbnb For Sale in Oakland, MD

609 Southern Pines Drive

Oakland, MD

4 beds | 3 baths | 2,250 sq.ft.

$440,000

Airbnb cash on cash: 6.14%

Traditional cash on cash: 5.89%

Airbnb Rental Income: $4304

Traditional Rental Income: $3296

Airbnb ROI: 6.14%

Traditional ROI: 5.89%

565 GLENDALE ROAD #124

Oakland, MD

1 beds | 1 baths | 382 sq.ft.

$175,000

Airbnb cash on cash: 6.9%

Traditional cash on cash: 5.99%

Airbnb Rental Income: $2748

Traditional Rental Income: $1949

Airbnb ROI: 6.9%

Traditional ROI: 5.99%

565 GLENDALE ROAD #116

Oakland, MD

1 beds | 1 baths | 484 sq.ft.

$179,000

Airbnb cash on cash: 9.94%

Traditional cash on cash: 6.64%

Airbnb Rental Income: $2748

Traditional Rental Income: $1539

Airbnb ROI: 9.94%

Traditional ROI: 6.64%

565 GLENDALE ROAD #303B

Oakland, MD

2 beds | 1 baths | 887 sq.ft.

$399,900

Airbnb cash on cash: 3.35%

Traditional cash on cash: 3.32%

Airbnb Rental Income: $2615

Traditional Rental Income: $1981

Airbnb ROI: 3.35%

Traditional ROI: 3.32%

321 DEER PARK HOTEL ROAD

Oakland, MD

3 beds | 2 baths | 2,516 sq.ft.

$360,000

Airbnb cash on cash: 6.3%

Traditional cash on cash: 6.18%

Airbnb Rental Income: $3503

Traditional Rental Income: $2692

Airbnb ROI: 6.3%

Traditional ROI: 6.18%

98 BEAR RUN ROAD

Oakland, MD

3 beds | 2 baths | 1,080 sq.ft.

$268,900

Airbnb cash on cash: 9.01%

Traditional cash on cash: 8.14%

Airbnb Rental Income: $3503

Traditional Rental Income: $2510

Airbnb ROI: 9.01%

Traditional ROI: 8.14%

25 SILVER TREE LANE

Oakland, MD

5 beds | 4 baths | 2,364 sq.ft.

$767,500

Airbnb cash on cash: 4.02%

Traditional cash on cash: 1.75%

Airbnb Rental Income: $5609

Traditional Rental Income: $2858

Airbnb ROI: 4.02%

Traditional ROI: 1.75%

180 PARADISE RIDGE ROAD

Oakland, MD

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

$425,000

Airbnb cash on cash: 4.84%

Traditional cash on cash: 3.39%

Airbnb Rental Income: $3503

Traditional Rental Income: $2154

Airbnb ROI: 4.84%