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
565 GLENDALE Road #306 Oakland, MD Experience the best of Deep Creek Lake living from this beautifully appointed studio loft ...	2 beds \| 1 baths \| 772 sq.ft.	$249,900	Airbnb cash on cash: 0.68% Traditional cash on cash: 5.25% Airbnb Rental Income: $1029 Traditional Rental Income: $1747 Airbnb ROI: 0.68% Traditional ROI: 5.25%
321 DEER PARK HOTEL Road Oakland, MD Double lots! Lot 4 & 5 of Hunting Ridge Estates will be sold together to bring up a total ...	3 beds \| 2 baths \| 2,476 sq.ft.	$399,900	Airbnb cash on cash: 0.12% Traditional cash on cash: 5.41% Airbnb Rental Income: $1078 Traditional Rental Income: $2692 Airbnb ROI: 0.12% Traditional ROI: 5.41%
638 GLENDALE Road Oakland, MD Spacious five-bedroom lakeview home offering the perfect blend of relaxation and warmth fr...	5 beds \| 3 baths \| 2,640 sq.ft.	$745,000	Airbnb cash on cash: -0.14% Traditional cash on cash: 2.49% Airbnb Rental Income: $1908 Traditional Rental Income: $3228 Airbnb ROI: -0.14% Traditional ROI: 2.49%
98 BEAR RUN Road Oakland, MD Make it your own! This 2-acre parcel comes with two additional parcels of 17.96 and 24.23 ...	3 beds \| 2 baths \| 1,080 sq.ft.	$550,000	Airbnb cash on cash: -0.21% Traditional cash on cash: 3.29% Airbnb Rental Income: $1078 Traditional Rental Income: $2510 Airbnb ROI: -0.21% Traditional ROI: 3.29%
25 SILVER TREE Lane Oakland, MD Beautiful lake access retreat located in the Silver Tree Landings community with an availa...	5 beds \| 4 baths \| 2,364 sq.ft.	$749,900	Airbnb cash on cash: -0.27% Traditional cash on cash: 1.81% Airbnb Rental Income: $1908 Traditional Rental Income: $2858 Airbnb ROI: -0.27% Traditional ROI: 1.81%
55 VILLAGE Drive #5 Oakland, MD Tucked in the Yellowstone Village community at Deep Creek Lake, "Dan's Mountain" is a char...	3 beds \| 3 baths \| 2,280 sq.ft.	$585,000	Airbnb cash on cash: -0.69% Traditional cash on cash: 3.66% Airbnb Rental Income: $1078 Traditional Rental Income: $3088 Airbnb ROI: -0.69% Traditional ROI: 3.66%
267 SAN FRANCISCO Street Oakland, MD Welcome to your secluded Deep Creek retreat! This stunning property offers expansive lake ...	4 beds \| 3 baths \| 3,278 sq.ft.	$899,900	Airbnb cash on cash: -0.67% Traditional cash on cash: 1.5% Airbnb Rental Income: $1496 Traditional Rental Income: $2874 Airbnb ROI: -0.67% Traditional ROI: 1.5%
8956 OAKLAND SANG RUN Road Oakland, MD Welcome to The Wise Quack - our cozy cabin in the center of Deep Creek Lake activities...a...	3 beds \| 2 baths \| 1,064 sq.ft.	$219,900	Airbnb cash on cash: 1.61% Traditional cash on cash: 9.26% Airbnb Rental Income: $1078 Traditional Rental Income: $2302 Airbnb ROI: 1.61% Traditional ROI: 9.26%
467 PARADISE RIDGE Road Oakland, MD Panoramic mountain and lake views set the tone at this lake access home in Paradise Ridge,...	4 beds \| 4 baths \| 3,780 sq.ft.	$769,900	Airbnb cash on cash: -0.82% Traditional cash on cash: 2.84% Airbnb Rental Income: $1496 Traditional Rental Income: $3685 Airbnb ROI: -0.82% Traditional ROI: 2.84%
113 JUBB MEADOWS Lane Oakland, MD Luxury Estate just outside the town of Oakland. This 4-bed, 3.5 bath is situated on 9.72 a...	4 beds \| 4 baths \| 3,185 sq.ft.	$899,900	Airbnb cash on cash: -0.82% Traditional cash on cash: 1.83% Airbnb Rental Income: $1496 Traditional Rental Income: $3274 Airbnb ROI: -0.82% Traditional ROI: 1.83%
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.	$499,900	Airbnb cash on cash: 0.45% Traditional cash on cash: 5.03% Airbnb Rental Income: $1496 Traditional Rental Income: $3200 Airbnb ROI: 0.45% Traditional ROI: 5.03%
449 S 3RD Street Oakland, MD Welcome to this beautifully updated 1901 home in the heart of downtown Oakland, where hist...	4 beds \| 2 baths \| 1,928 sq.ft.	$275,900	Airbnb cash on cash: 1.33% Traditional cash on cash: 7.55% Airbnb Rental Income: $1496 Traditional Rental Income: $2676 Airbnb ROI: 1.33% Traditional ROI: 7.55%
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	$214,900	Airbnb cash on cash: -0.49% Traditional cash on cash: 6.58% Airbnb Rental Income: $673 Traditional Rental Income: $1813 Airbnb ROI: -0.49% Traditional ROI: 6.58%
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.	$545,000	Airbnb cash on cash: 0.23% Traditional cash on cash: 4.15% Airbnb Rental Income: $1496 Traditional Rental Income: $3055 Airbnb ROI: 0.23% Traditional ROI: 4.15%
13 LAUREL BROOK Drive #13 Oakland, MD Affordable well maintained 2 Bedroom 2 Bath townhouse style condominium less than 1 mile f...	2 beds \| 2 baths \| 1,320 sq.ft.	$245,000	Airbnb cash on cash: 0.62% Traditional cash on cash: 7.14% Airbnb Rental Income: $1029 Traditional Rental Income: $2179 Airbnb ROI: 0.62% Traditional ROI: 7.14%
2918 OAKLAND SANG RUN Road Oakland, MD This charming 3-bedroom, 1-bathroom ranch-style home in the desirable Oakland Sang Run Rd ...	3 beds \| 1 baths \| 1,382 sq.ft.	$195,000	Airbnb cash on cash: 1.17% Traditional cash on cash: 5.78% Airbnb Rental Income: $1078 Traditional Rental Income: $1562 Airbnb ROI: 1.17% Traditional ROI: 5.78%
157 JEFFREY Lane #21B Oakland, MD Nestled in the charming Traders Landing community, this delightful end-of-row townhouse of...	2 beds \| 1 baths \| 550 sq.ft.	$294,000	Airbnb cash on cash: 0.14% Traditional cash on cash: 2.87% Airbnb Rental Income: $1029 Traditional Rental Income: $1422 Airbnb ROI: 0.14% Traditional ROI: 2.87%
17921 GARRETT Highway Oakland, MD Charming and well-maintained, this 4-bedroom, 1.5-bath traditional home offers the perfect...	4 beds \| 2 baths \| 1,563 sq.ft.	$325,000	Airbnb cash on cash: 1.82% Traditional cash on cash: 7.12% Airbnb Rental Income: $1496 Traditional Rental Income: $2677 Airbnb ROI: 1.82% Traditional ROI: 7.12%
660 GLENDALE Road Oakland, MD Welcome to 660 Glendale Road - a luxury, mountain-chalet log home in the heart of Deep Cre...	5 beds \| 3 baths \| 2,592 sq.ft.	$1,100,000	Airbnb cash on cash: -0.33% Traditional cash on cash: 1.08% Airbnb Rental Income: $1908 Traditional Rental Income: $2839 Airbnb ROI: -0.33% Traditional ROI: 1.08%
127 PARADISE Heights Oakland, MD Beautifully renovated lake access log cabin with a deeded dock slip in a quiet cove with p...	3 beds \| 3 baths \| 2,240 sq.ft.	$1,075,000	Airbnb cash on cash: -1.03% Traditional cash on cash: 0.57% Airbnb Rental Income: $1078 Traditional Rental Income: $2308 Airbnb ROI: -1.03% Traditional ROI: 0.57%
565 GLENDALE Road #212A Oakland, MD Silver Tree Suites offers 350' of pristine shoreline at Deep Creek Lake with western expos...	1 beds \| 1 baths \| 527 sq.ft.	$175,000	Airbnb cash on cash: -0.17% Traditional cash on cash: 8.92% Airbnb Rental Income: $673 Traditional Rental Income: $1886 Airbnb ROI: -0.17% Traditional ROI: 8.92%
178 WINDING TRAIL Lane #5B Oakland, MD Tucked into a peaceful, wooded setting yet right in the heart of everything Deep Creek Lak...	5 beds \| 5 baths \| 3,300 sq.ft.	$569,000	Airbnb cash on cash: 0.36% Traditional cash on cash: 6.8% Airbnb Rental Income: $1908 Traditional Rental Income: $4826 Airbnb ROI: 0.36% Traditional ROI: 6.8%
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.	$2,350,000	Airbnb cash on cash: -1.4% Traditional cash on cash: 0.76% Airbnb Rental Income: $1908 Traditional Rental Income: $6125 Airbnb ROI: -1.4% Traditional ROI: 0.76%
163 MITCHELL Drive Oakland, MD Nestled in the charming Mitchell Manor community, this delightful split-level home offers ...	3 beds \| 3 baths \| 2,242 sq.ft.	$289,000	Airbnb cash on cash: 0.57% Traditional cash on cash: 9.98% Airbnb Rental Income: $1078 Traditional Rental Income: $3270 Airbnb ROI: 0.57% Traditional ROI: 9.98%
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	$224,900	Airbnb cash on cash: -0.07% Traditional cash on cash: 5.78% Airbnb Rental Income: $673 Traditional Rental Income: $1618 Airbnb ROI: -0.07% Traditional ROI: 5.78%
1737 KING WILDESEN Road Oakland, MD Nestled on 10 secluded acres of serene woodland and open fields, this traditional cedar-si...	3 beds \| 2 baths \| 1,736 sq.ft.	$285,500	Airbnb cash on cash: 0.61% Traditional cash on cash: 8.94% Airbnb Rental Income: $1078 Traditional Rental Income: $2950 Airbnb ROI: 0.61% Traditional ROI: 8.94%
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: 0.68% Traditional cash on cash: 7.51% Airbnb Rental Income: $1078 Traditional Rental Income: $2447 Airbnb ROI: 0.68% 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.	$339,900	Airbnb cash on cash: -0.04% Traditional cash on cash: 4.07% Airbnb Rental Income: $1029 Traditional Rental Income: $1981 Airbnb ROI: -0.04% Traditional ROI: 4.07%
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: 0.3% Traditional cash on cash: 4.08% Airbnb Rental Income: $1496 Traditional Rental Income: $2737 Airbnb ROI: 0.3% Traditional ROI: 4.08%
415 NAZELROD Road Oakland, MD One of Garrett County's most unique and breathtaking mountain estates, this completely cus...	4 beds \| 5 baths \| 6,036 sq.ft.	$3,249,000	Airbnb cash on cash: -0.92% Traditional cash on cash: 0.43% Airbnb Rental Income: $1496 Traditional Rental Income: $5150 Airbnb ROI: -0.92% Traditional ROI: 0.43%
2311 BOY SCOUT Road Oakland, MD Experience the best of Deep Creek Lake living from this private waterfront retreat tucked ...	4 beds \| 3 baths \| 3,278 sq.ft.	$1,579,900	Airbnb cash on cash: -1.04% Traditional cash on cash: 0.8% Airbnb Rental Income: $1496 Traditional Rental Income: $3756 Airbnb ROI: -1.04% Traditional ROI: 0.8%
20160 GARRETT Highway #G507 Oakland, MD Experience lakefront living with this charming two-level condo at Will O the Wisp at Deep ...	2 beds \| 1 baths \| 912 sq.ft.	$389,000	Airbnb cash on cash: -0.07% Traditional cash on cash: 3.06% Airbnb Rental Income: $1029 Traditional Rental Income: $1811 Airbnb ROI: -0.07% Traditional ROI: 3.06%
1909 PYSELL CROSSCUT Road Oakland, MD Welcome to a private retreat on 4 acres with sweeping views and a large front yard, just m...	4 beds \| 5 baths \| 2,970 sq.ft.	$760,000	Airbnb cash on cash: -0.2% Traditional cash on cash: 5.13% Airbnb Rental Income: $1496 Traditional Rental Income: $4836 Airbnb ROI: -0.2% Traditional ROI: 5.13%

Real Estate investment in Oakland, MD

There are 91 properties for sale in the city of Oakland . The median list price in Oakland is $242,855 and the average price per square foot is $119. In July 2026, the average monthly cash on cash return in Oakland is 2.00%. The average monthly rental income in Oakland is $2,582.

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

There are 91 investment properties available for sale in Oakland.

In 2026, 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 $2,582.

Your search for investment property begins and ends here

Investment Property for Sale in Oakland, MD

565 GLENDALE Road #306

Oakland, MD

2 beds | 1 baths | 772 sq.ft.

$249,900

Airbnb cash on cash: 0.68%

Traditional cash on cash: 5.25%

Airbnb Rental Income: $1029

Traditional Rental Income: $1747

Airbnb ROI: 0.68%

Traditional ROI: 5.25%

321 DEER PARK HOTEL Road

Oakland, MD

3 beds | 2 baths | 2,476 sq.ft.

$399,900

Airbnb cash on cash: 0.12%

Traditional cash on cash: 5.41%

Airbnb Rental Income: $1078

Traditional Rental Income: $2692

Airbnb ROI: 0.12%

Traditional ROI: 5.41%

638 GLENDALE Road

Oakland, MD

5 beds | 3 baths | 2,640 sq.ft.

$745,000

Airbnb cash on cash: -0.14%

Traditional cash on cash: 2.49%

Airbnb Rental Income: $1908

Traditional Rental Income: $3228

Airbnb ROI: -0.14%

Traditional ROI: 2.49%

98 BEAR RUN Road

Oakland, MD

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

$550,000

Airbnb cash on cash: -0.21%

Traditional cash on cash: 3.29%

Airbnb Rental Income: $1078

Traditional Rental Income: $2510

Airbnb ROI: -0.21%

Traditional ROI: 3.29%

25 SILVER TREE Lane

Oakland, MD

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

$749,900

Airbnb cash on cash: -0.27%

Traditional cash on cash: 1.81%

Airbnb Rental Income: $1908

Traditional Rental Income: $2858

Airbnb ROI: -0.27%

Traditional ROI: 1.81%

55 VILLAGE Drive #5

Oakland, MD

3 beds | 3 baths | 2,280 sq.ft.

$585,000

Airbnb cash on cash: -0.69%

Traditional cash on cash: 3.66%

Airbnb Rental Income: $1078

Traditional Rental Income: $3088

Airbnb ROI: -0.69%

Traditional ROI: 3.66%

267 SAN FRANCISCO Street

Oakland, MD

4 beds | 3 baths | 3,278 sq.ft.

$899,900

Airbnb cash on cash: -0.67%

Traditional cash on cash: 1.5%

Airbnb Rental Income: $1496

Traditional Rental Income: $2874

Airbnb ROI: -0.67%

Traditional ROI: 1.5%

8956 OAKLAND SANG RUN Road

Oakland, MD

3 beds | 2 baths | 1,064 sq.ft.

$219,900

Airbnb cash on cash: 1.61%

Traditional cash on cash: 9.26%

Airbnb Rental Income: $1078

Traditional Rental Income: $2302

Airbnb ROI: 1.61%