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

separator

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%
198 GRANDVIEW DRIVE Oakland, MD Lake views for days and room to relax in every direction!Welcome to 198 Grandview Drive, a...	3 beds \| 3 baths \| 2,744 sq.ft.	$825,000	Airbnb cash on cash: 1.36% Traditional cash on cash: 2.35% Airbnb Rental Income: $3503 Traditional Rental Income: $3488 Airbnb ROI: 1.36% Traditional ROI: 2.35%
65 VILLAGE DRIVE #6 Oakland, MD Looking for that cozy cabin getaway at the lake? 65 Village Drive offers cabin living at i...	3 beds \| 3 baths \| 1,740 sq.ft.	$650,000	Airbnb cash on cash: 1.95% Traditional cash on cash: 2.06% Airbnb Rental Income: $3503 Traditional Rental Income: $2798 Airbnb ROI: 1.95% Traditional ROI: 2.06%
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.	$529,900	Airbnb cash on cash: 3.09% Traditional cash on cash: 3.46% Airbnb Rental Income: $3503 Traditional Rental Income: $2914 Airbnb ROI: 3.09% Traditional ROI: 3.46%
444 WOODLANDS HILL LANE Oakland, MD Experience the serenity of Deep Creek Lake from this updated luxury 4 bedroom home with ov...	4 beds \| 6 baths \| 4,744 sq.ft.	$1,249,000	Airbnb cash on cash: 0.89% Traditional cash on cash: 3.71% Airbnb Rental Income: $4304 Traditional Rental Income: $6676 Airbnb ROI: 0.89% Traditional ROI: 3.71%
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%
62 MIDDLETON ROAD Oakland, MD Tucked in the trees at The Blakeslee, this 3-bed, 2.5-bath home delivers space, style, and...	3 beds \| 3 baths \| 2,397 sq.ft.	$799,900	Airbnb cash on cash: 1.25% Traditional cash on cash: 1.6% Airbnb Rental Income: $3503 Traditional Rental Income: $2989 Airbnb ROI: 1.25% Traditional ROI: 1.6%
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%
175 ROMAN RIDGE ROAD #15 Oakland, MD Amazing and rare opportunity in Trader's Landing! These wonderful stand alone homes in thi...	4 beds \| 5 baths \| 3,192 sq.ft.	$555,000	Airbnb cash on cash: 4.45% Traditional cash on cash: 8.25% Airbnb Rental Income: $4304 Traditional Rental Income: $5368 Airbnb ROI: 4.45% Traditional ROI: 8.25%
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.	$329,000	Airbnb cash on cash: 6.16% Traditional cash on cash: 6.64% Airbnb Rental Income: $3503 Traditional Rental Income: $2878 Airbnb ROI: 6.16% Traditional ROI: 6.64%
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%
20160 GARRETT HIGHWAY #D308/408 Oakland, MD Lakefront Luxury at Will O The Wisp Nicely renovated Unit 308/408 offers a 2 BR, 2 Bath 2-...	2 beds \| 2 baths \| 1,325 sq.ft.	$485,000	Airbnb cash on cash: 2.42% Traditional cash on cash: 3.66% Airbnb Rental Income: $2615 Traditional Rental Income: $2552 Airbnb ROI: 2.42% Traditional ROI: 3.66%
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.	$1,599,900	Airbnb cash on cash: 0.62% Traditional cash on cash: 0.75% Airbnb Rental Income: $4304 Traditional Rental Income: $3589 Airbnb ROI: 0.62% Traditional ROI: 0.75%
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%
20698 GARRETT HIGHWAY Oakland, MD Beautiful lakefront home offering 89' of lakefront and a private dock. This home has been ...	4 beds \| 3 baths \| 1,844 sq.ft.	$1,299,000	Airbnb cash on cash: 1.11% Traditional cash on cash: 1.26% Airbnb Rental Income: $4304 Traditional Rental Income: $3578 Airbnb ROI: 1.11% Traditional ROI: 1.26%
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%
189 RED RUN ROAD #1-C-2 Oakland, MD 2+BR, 2BA waterfront condo at Red Run offering lake views and assigned deep water boat sli...	2 beds \| 2 baths \| 1,200 sq.ft.	$589,000	Airbnb cash on cash: 1.74% Traditional cash on cash: 1.85% Airbnb Rental Income: $2615 Traditional Rental Income: $2053 Airbnb ROI: 1.74% Traditional ROI: 1.85%
1720 PYSELL CROSSCUT ROAD Oakland, MD 'Four Winds' is a Frank Lloyd Wright inspired masterpiece at Deep Creek Lake. Restored & r...	5 beds \| 6 baths \| 8,000 sq.ft.	$999,999	Airbnb cash on cash: 2.89% Traditional cash on cash: 3.56% Airbnb Rental Income: $5609 Traditional Rental Income: $5107 Airbnb ROI: 2.89% Traditional ROI: 3.56%
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%
2719 BROADFORD ROAD Oakland, MD Stunning Brick Ranch Near Broadford Lake Park! This magnificent one-level brick ranch sits...	3 beds \| 3 baths \| 4,253 sq.ft.	$599,000	Airbnb cash on cash: 3.15% Traditional cash on cash: 3.28% Airbnb Rental Income: $3503 Traditional Rental Income: $2803 Airbnb ROI: 3.15% Traditional ROI: 3.28%
1001 SUTTER LN Oakland, MD Set on a serene 2.4-acre wooded lot, this thoughtfully crafted Southern-inspired property ...	5 beds \| 6 baths \| N/A	$879,900	Airbnb cash on cash: 3.5% Traditional cash on cash: 5.61% Airbnb Rental Income: $5609 Traditional Rental Income: $6210 Airbnb ROI: 3.5% Traditional ROI: 5.61%
2725 STOCKSLAGER ROAD Oakland, MD Welcome to 2725 Stockslager Road, one of Deep Creek Lake's most coveted properties. This c...	5 beds \| 7 baths \| 5,376 sq.ft.	$2,750,000	Airbnb cash on cash: 0.62% Traditional cash on cash: 1.26% Airbnb Rental Income: $5609 Traditional Rental Income: $6125 Airbnb ROI: 0.62% Traditional ROI: 1.26%
621 PARADISE HEIGHTS Oakland, MD Opportunity to own one of Deep Creek Lake's most unique homes! 621 Paradise Heights is a g...	4 beds \| 3 baths \| 3,242 sq.ft.	$695,000	Airbnb cash on cash: 3.44% Traditional cash on cash: 3.53% Airbnb Rental Income: $4304 Traditional Rental Income: $3451 Airbnb ROI: 3.44% Traditional ROI: 3.53%
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%
1118 LAKE SHORE DRIVE Oakland, MD Escape to Serenity: Your Dream Log Home Awaits! Nestled in the heart of a picturesque lake...	3 beds \| 2 baths \| 2,446 sq.ft.	$649,000	Airbnb cash on cash: 2.56% Traditional cash on cash: 2.6% Airbnb Rental Income: $3503 Traditional Rental Income: $2755 Airbnb ROI: 2.56% Traditional ROI: 2.6%
130 TIMBERLOFT CIRCLE #14 Oakland, MD Centrally located in the heart of Deep Creek Lake, this beautifully maintained 3 bedroom, ...	3 beds \| 3 baths \| 1,900 sq.ft.	$749,000	Airbnb cash on cash: 1.89% Traditional cash on cash: 2.32% Airbnb Rental Income: $3503 Traditional Rental Income: $3029 Airbnb ROI: 1.89% Traditional ROI: 2.32%
45 VILLAGE DRIVE #4 Oakland, MD Nestled in the serene Yellowstone Village community, 45 Village Drive offers a fully furni...	2 beds \| 2 baths \| 1,096 sq.ft.	$450,000	Airbnb cash on cash: 2.77% Traditional cash on cash: 3.24% Airbnb Rental Income: $2615 Traditional Rental Income: $2188 Airbnb ROI: 2.77% Traditional ROI: 3.24%

Real Estate investment in Oakland, MD

There are 80 properties for sale in the city of Oakland . The median list price in Oakland is $474,900 and the average price per square foot is $216. In September 2025, the average monthly cash on cash return in Oakland is 4.00%. The average monthly rental income in Oakland is $2,789.

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

There are 80 investment properties available for sale in Oakland.

In 2025, 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 $3,503.

Your search for investment property begins and ends here

Investment Property 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%

198 GRANDVIEW DRIVE

Oakland, MD

3 beds | 3 baths | 2,744 sq.ft.

$825,000

Airbnb cash on cash: 1.36%

Traditional cash on cash: 2.35%

Airbnb Rental Income: $3503

Traditional Rental Income: $3488

Airbnb ROI: 1.36%

Traditional ROI: 2.35%

65 VILLAGE DRIVE #6

Oakland, MD

3 beds | 3 baths | 1,740 sq.ft.

$650,000

Airbnb cash on cash: 1.95%

Traditional cash on cash: 2.06%

Airbnb Rental Income: $3503

Traditional Rental Income: $2798

Airbnb ROI: 1.95%

Traditional ROI: 2.06%

783 MOUNTAINVIEW DRIVE

Oakland, MD

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

$529,900

Airbnb cash on cash: 3.09%

Traditional cash on cash: 3.46%

Airbnb Rental Income: $3503

Traditional Rental Income: $2914

Airbnb ROI: 3.09%

Traditional ROI: 3.46%

444 WOODLANDS HILL LANE

Oakland, MD

4 beds | 6 baths | 4,744 sq.ft.

$1,249,000

Airbnb cash on cash: 0.89%

Traditional cash on cash: 3.71%

Airbnb Rental Income: $4304

Traditional Rental Income: $6676

Airbnb ROI: 0.89%

Traditional ROI: 3.71%

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%

62 MIDDLETON ROAD

Oakland, MD

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

$799,900

Airbnb cash on cash: 1.25%

Traditional cash on cash: 1.6%

Airbnb Rental Income: $3503

Traditional Rental Income: $2989

Airbnb ROI: 1.25%