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
609 Southern Pines Dr Oakland, MD Welcome to your next dream home! Nestled on a 4-acre wooded lot, this custom built residen...	4 beds \| 2 baths \| 2,030 sq.ft.	$440,000	Airbnb cash on cash: 0.73% Traditional cash on cash: 5.89% Airbnb Rental Income: $1631 Traditional Rental Income: $3296 Airbnb ROI: 0.73% Traditional ROI: 5.89%
65 VILLAGE Drive unit: 6 #6 Oakland, MD One of Deep Creek Lake's best performing vacation rental properties! Over 65 Village Drive...	3 beds \| 3 baths \| 1,740 sq.ft.	$625,000	Airbnb cash on cash: -1.3% Traditional cash on cash: 2.18% Airbnb Rental Income: $1148 Traditional Rental Income: $2798 Airbnb ROI: -1.3% Traditional ROI: 2.18%
444 WOODLANDS HILL Lane Oakland, MD Welcome to 444 Woodlands Hill Ln, in Oakland, MD. Nestled in the private community of The ...	4 beds \| 6 baths \| 4,744 sq.ft.	$1,199,990	Airbnb cash on cash: -1.03% Traditional cash on cash: 3.91% Airbnb Rental Income: $1631 Traditional Rental Income: $6676 Airbnb ROI: -1.03% Traditional ROI: 3.91%
565 GLENDALE Road unit: 116 #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.	$169,000	Airbnb cash on cash: 1.92% Traditional cash on cash: 7.08% Airbnb Rental Income: $1077 Traditional Rental Income: $1539 Airbnb ROI: 1.92% Traditional ROI: 7.08%
175 ROMAN RIDGE Road unit: 15 #15 Oakland, MD Welcome to one of the most spacious and inviting homes in Trader's Landing. This rare stan...	4 beds \| 5 baths \| 3,192 sq.ft.	$537,500	Airbnb cash on cash: 0.19% Traditional cash on cash: 8.55% Airbnb Rental Income: $1631 Traditional Rental Income: $5368 Airbnb ROI: 0.19% Traditional ROI: 8.55%
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: -0.1% Traditional cash on cash: 3.29% Airbnb Rental Income: $1148 Traditional Rental Income: $2510 Airbnb ROI: -0.1% 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: -0.2% Traditional cash on cash: 1.81% Airbnb Rental Income: $1968 Traditional Rental Income: $2858 Airbnb ROI: -0.2% Traditional ROI: 1.81%
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: 0.6% Traditional cash on cash: 4.69% Airbnb Rental Income: $1631 Traditional Rental Income: $3200 Airbnb ROI: 0.6% Traditional ROI: 4.69%
20160 GARRETT Highway unit: H708 #H708 Oakland, MD Welcome to Will O' the Wisp Condominiums, where premium upgrades meet penthouse-level lake...	1 beds \| 1 baths \| 550 sq.ft.	$289,900	Airbnb cash on cash: 0.47% Traditional cash on cash: 3.48% Airbnb Rental Income: $1077 Traditional Rental Income: $1530 Airbnb ROI: 0.47% Traditional ROI: 3.48%
285 LAKE SHORE Drive Oakland, MD Nestled on 1.52 private acres with 500 feet of frontage on Deep Creek Lake, this 5-bedroom...	5 beds \| 5 baths \| 2,593 sq.ft.	$1,199,000	Airbnb cash on cash: -0.29% Traditional cash on cash: 2.78% Airbnb Rental Income: $1968 Traditional Rental Income: $4868 Airbnb ROI: -0.29% Traditional ROI: 2.78%
565 GLENDALE Road unit: 106 B #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	$239,900	Airbnb cash on cash: 0.94% Traditional cash on cash: 5.81% Airbnb Rental Income: $1077 Traditional Rental Income: $1813 Airbnb ROI: 0.94% Traditional ROI: 5.81%
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: 0.45% Traditional cash on cash: 4.15% Airbnb Rental Income: $1631 Traditional Rental Income: $3055 Airbnb ROI: 0.45% Traditional ROI: 4.15%
163 CRESTVIEW Drive Oakland, MD Welcome to 163 Crestview Drive - a beautifully maintained 3-bedroom, 2.5-bath home nestled...	3 beds \| 3 baths \| 1,416 sq.ft.	$315,000	Airbnb cash on cash: 0.66% Traditional cash on cash: 6.09% Airbnb Rental Income: $1148 Traditional Rental Income: $2376 Airbnb ROI: 0.66% Traditional ROI: 6.09%
1019 LAKE SHORE Drive Oakland, MD Tucked among the trees, Blue Spruce offers a perfect blend of modern comfort and serene na...	4 beds \| 5 baths \| 2,605 sq.ft.	$1,749,000	Airbnb cash on cash: -0.98% Traditional cash on cash: 0.19% Airbnb Rental Income: $1631 Traditional Rental Income: $3069 Airbnb ROI: -0.98% Traditional ROI: 0.19%
565 GLENDALE Road unit: 212A #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.	$199,000	Airbnb cash on cash: 1.52% Traditional cash on cash: 7.75% Airbnb Rental Income: $1077 Traditional Rental Income: $1886 Airbnb ROI: 1.52% Traditional ROI: 7.75%
611 E OAK Street Oakland, MD Investors, this is an income producing, three unit building with three separate apartments...	5 beds \| 3 baths \| 1,800 sq.ft.	$295,000	Airbnb cash on cash: 2.98% Traditional cash on cash: 5.04% Airbnb Rental Income: $1968 Traditional Rental Income: $2023 Airbnb ROI: 2.98% Traditional ROI: 5.04%
1021 E HIGH Street Oakland, MD Nestled in the convenient High Street neighborhood of Oakland, this delightful ranch-style...	3 beds \| 2 baths \| 1,520 sq.ft.	$234,000	Airbnb cash on cash: 1.39% Traditional cash on cash: 9.47% Airbnb Rental Income: $1148 Traditional Rental Income: $2555 Airbnb ROI: 1.39% Traditional ROI: 9.47%
1001 Sutter Ln Oakland, MD Discover the ultimate mountain-lake getaway in this stunning 5BR Southern-style home on a ...	5 beds \| 4 baths \| 6,550 sq.ft.	$829,000	Airbnb cash on cash: -0.19% Traditional cash on cash: 5.97% Airbnb Rental Income: $1968 Traditional Rental Income: $6210 Airbnb ROI: -0.19% Traditional ROI: 5.97%
329 LEMLEY Drive Oakland, MD Lake View Chalet at Deep Creek Lake - This 4 Bedroom 3.5 Bath Mountain Home is privately s...	4 beds \| 4 baths \| 2,632 sq.ft.	$750,000	Airbnb cash on cash: -0.3% Traditional cash on cash: 2.82% Airbnb Rental Income: $1631 Traditional Rental Income: $3356 Airbnb ROI: -0.3% Traditional ROI: 2.82%
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: 0.01% Traditional cash on cash: 3.53% Airbnb Rental Income: $1631 Traditional Rental Income: $3451 Airbnb ROI: 0.01% Traditional ROI: 3.53%
15 VILLAGE Drive unit: 1 #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	$425,000	Airbnb cash on cash: -0.12% Traditional cash on cash: 2.75% Airbnb Rental Income: $1132 Traditional Rental Income: $1895 Airbnb ROI: -0.12% Traditional ROI: 2.75%
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: -0.68% Traditional cash on cash: 2.6% Airbnb Rental Income: $1148 Traditional Rental Income: $2755 Airbnb ROI: -0.68% Traditional ROI: 2.6%
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: -0.1% Traditional cash on cash: 2.35% Airbnb Rental Income: $1968 Traditional Rental Income: $3448 Airbnb ROI: -0.1% Traditional ROI: 2.35%
723 Kings Oakland, MD ""Charming two-story home situated on a beautiful .292-acre level lot in a prime location ...	4 beds \| 2 baths \| 1,824 sq.ft.	$359,700	Airbnb cash on cash: 1.29% Traditional cash on cash: 6.39% Airbnb Rental Income: $1631 Traditional Rental Income: $2986 Airbnb ROI: 1.29% Traditional ROI: 6.39%
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.	$299,900	Airbnb cash on cash: 0.74% Traditional cash on cash: 8.47% Airbnb Rental Income: $1148 Traditional Rental Income: $2950 Airbnb ROI: 0.74% Traditional ROI: 8.47%
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: 0.91% Traditional cash on cash: 7.51% Airbnb Rental Income: $1148 Traditional Rental Income: $2447 Airbnb ROI: 0.91% Traditional ROI: 7.51%
531 GLENDALE Road unit: B302 #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: 0.13% Traditional cash on cash: 3.68% Airbnb Rental Income: $1132 Traditional Rental Income: $1981 Airbnb ROI: 0.13% Traditional ROI: 3.68%
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: 0.56% Traditional cash on cash: 4.08% Airbnb Rental Income: $1631 Traditional Rental Income: $2737 Airbnb ROI: 0.56% Traditional ROI: 4.08%
1875 PYSELL CROSSCUT Road Oakland, MD With a new price you don't want to miss this chance! Beautifully maintained 5 bedroom 5 ba...	5 beds \| 5 baths \| 3,664 sq.ft.	$769,000	Airbnb cash on cash: 0.31% Traditional cash on cash: 5.32% Airbnb Rental Income: $1968 Traditional Rental Income: $5042 Airbnb ROI: 0.31% Traditional ROI: 5.32%
66 PARADISE RIDGE Road Oakland, MD Welcome to 66 Paradise Ridge Rd, a charming single-family home in the picturesque town of ...	4 beds \| 4 baths \| 2,550 sq.ft.	$619,900	Airbnb cash on cash: 0.19% Traditional cash on cash: 3.32% Airbnb Rental Income: $1631 Traditional Rental Income: $2979 Airbnb ROI: 0.19% Traditional ROI: 3.32%
20160 GARRETT Highway unit: G507 #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.	$399,000	Airbnb cash on cash: 0.13% Traditional cash on cash: 2.96% Airbnb Rental Income: $1132 Traditional Rental Income: $1811 Airbnb ROI: 0.13% Traditional ROI: 2.96%
565 GLENDALE Road unit: 210A #210A Oakland, MD Studio unit at Silver Tree Suites, one of Deep Creek Lake's most premier condo/hotel commu...	1 beds \| 1 baths \| 382 sq.ft.	$160,000	Airbnb cash on cash: 2.25% Traditional cash on cash: 10.01% Airbnb Rental Income: $1077 Traditional Rental Income: $1895 Airbnb ROI: 2.25% Traditional ROI: 10.01%
336 PARADISE Heights Oakland, MD Architecturally unique, private and spacious lakefront home with a perfect central locatio...	5 beds \| 3 baths \| 2,826 sq.ft.	$1,449,000	Airbnb cash on cash: -0.8% Traditional cash on cash: 1.01% Airbnb Rental Income: $1968 Traditional Rental Income: $3891 Airbnb ROI: -0.8% Traditional ROI: 1.01%
697 MONTE VISTA Road Oakland, MD Tucked away just minutes from downtown Oakland, MD, lies a home that truly surprises with ...	5 beds \| 4 baths \| 3,682 sq.ft.	$339,000	Airbnb cash on cash: 2.44% Traditional cash on cash: 11.48% Airbnb Rental Income: $1968 Traditional Rental Income: $4331 Airbnb ROI: 2.44% Traditional ROI: 11.48%
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.	$865,000	Airbnb cash on cash: -0.16% Traditional cash on cash: 4.39% Airbnb Rental Income: $1631 Traditional Rental Income: $4836 Airbnb ROI: -0.16% Traditional ROI: 4.39%
961 CEDAR Lane Oakland, MD Tucked away in the woods on 1.72 acres, this stunning 4-bedroom, 2.5-bath mountain retreat...	4 beds \| 3 baths \| 1,920 sq.ft.	$379,000	Airbnb cash on cash: 1.39% Traditional cash on cash: 6.51% Airbnb Rental Income: $1631 Traditional Rental Income: $2991 Airbnb ROI: 1.39% Traditional ROI: 6.51%
104 PINE TOP Trail Oakland, MD Here's your chance to purchase a cute Chalet with just about 7 acres. .This home and acrea...	3 beds \| 4 baths \| 1,596 sq.ft.	$425,000	Airbnb cash on cash: -0.04% Traditional cash on cash: 6.41% Airbnb Rental Income: $1148 Traditional Rental Income: $3334 Airbnb ROI: -0.04% Traditional ROI: 6.41%
5024 CRANESVILLE Road Oakland, MD Just Reduced!! Charming 3-Bedroom Home with Scenic Mountain & Valley Views. Nestled on a 1...	3 beds \| 3 baths \| 2,128 sq.ft.	$440,000	Airbnb cash on cash: -0.13% Traditional cash on cash: 5.49% Airbnb Rental Income: $1148 Traditional Rental Income: $3081 Airbnb ROI: -0.13% Traditional ROI: 5.49%
63 WALLMAN Road Oakland, MD Remodeled Rancher Near the North Branch Potomac River This charming 3-bedroom, 1-bath ranc...	3 beds \| 1 baths \| 816 sq.ft.	$179,900	Airbnb cash on cash: 2.69% Traditional cash on cash: 9.56% Airbnb Rental Income: $1148 Traditional Rental Income: $1944 Airbnb ROI: 2.69% Traditional ROI: 9.56%
20160 GARRETT Highway unit: F501-701 #F501-701 Oakland, MD Lakefront living at it's best can be found in this completely renovated spacious condo. Th...	3 beds \| 2 baths \| 1,700 sq.ft.	$575,000	Airbnb cash on cash: -0.52% Traditional cash on cash: 3.24% Airbnb Rental Income: $1148 Traditional Rental Income: $2790 Airbnb ROI: -0.52% Traditional ROI: 3.24%

Real Estate investment in Oakland, MD

There are 54 properties for sale in the city of Oakland . The median list price in Oakland is $374,000 and the average price per square foot is $196. In February 2026, the average monthly cash on cash return in Oakland is 1.00%. The average monthly rental income in Oakland is $2,576.

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

There are 54 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 $2,576.

Your search for investment property begins and ends here

Investment Property for Sale in Oakland, MD

609 Southern Pines Dr

Oakland, MD

4 beds | 2 baths | 2,030 sq.ft.

$440,000

Airbnb cash on cash: 0.73%

Traditional cash on cash: 5.89%

Airbnb Rental Income: $1631

Traditional Rental Income: $3296

Airbnb ROI: 0.73%

Traditional ROI: 5.89%

65 VILLAGE Drive unit: 6 #6

Oakland, MD

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

$625,000

Airbnb cash on cash: -1.3%

Traditional cash on cash: 2.18%

Airbnb Rental Income: $1148

Traditional Rental Income: $2798

Airbnb ROI: -1.3%

Traditional ROI: 2.18%

444 WOODLANDS HILL Lane

Oakland, MD

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

$1,199,990

Airbnb cash on cash: -1.03%

Traditional cash on cash: 3.91%

Airbnb Rental Income: $1631

Traditional Rental Income: $6676

Airbnb ROI: -1.03%

Traditional ROI: 3.91%

565 GLENDALE Road unit: 116 #116

Oakland, MD

1 beds | 1 baths | 484 sq.ft.

$169,000

Airbnb cash on cash: 1.92%

Traditional cash on cash: 7.08%

Airbnb Rental Income: $1077

Traditional Rental Income: $1539

Airbnb ROI: 1.92%

Traditional ROI: 7.08%

175 ROMAN RIDGE Road unit: 15 #15

Oakland, MD

4 beds | 5 baths | 3,192 sq.ft.

$537,500

Airbnb cash on cash: 0.19%

Traditional cash on cash: 8.55%

Airbnb Rental Income: $1631

Traditional Rental Income: $5368

Airbnb ROI: 0.19%

Traditional ROI: 8.55%

98 BEAR RUN Road

Oakland, MD

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

$550,000

Airbnb cash on cash: -0.1%

Traditional cash on cash: 3.29%

Airbnb Rental Income: $1148

Traditional Rental Income: $2510

Airbnb ROI: -0.1%

Traditional ROI: 3.29%

25 SILVER TREE Lane

Oakland, MD

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

$749,900

Airbnb cash on cash: -0.2%

Traditional cash on cash: 1.81%

Airbnb Rental Income: $1968

Traditional Rental Income: $2858

Airbnb ROI: -0.2%

Traditional ROI: 1.81%

126 LEO FRIEND Road

Oakland, MD

4 beds | 3 baths | 2,235 sq.ft.

$529,900

Airbnb cash on cash: 0.6%

Traditional cash on cash: 4.69%

Airbnb Rental Income: $1631

Traditional Rental Income: $3200

Airbnb ROI: 0.6%