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.

Ruth Lake Investmata Tnvestmiaensent Pment Property for Sale in Oakland, MD

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Showing 74 Ruth Lake Investmata Tnvestmiaensent Pment Property listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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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.	$425,000	Airbnb cash on cash: 0.79% Traditional cash on cash: 6.13% Airbnb Rental Income: $1631 Traditional Rental Income: $3296 Airbnb ROI: 0.79% Traditional ROI: 6.13%
24 TRAILSIDE WAY Oakland, MD Tucked in the Silver Ridge community at Deep Creek Lake, this inviting home blends rustic ...	4 beds \| 4 baths \| N/A	$555,000	Airbnb cash on cash: 0.16% Traditional cash on cash: 5.16% Airbnb Rental Income: $1631 Traditional Rental Income: $3765 Airbnb ROI: 0.16% Traditional ROI: 5.16%
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%
1544 STOCKSLAGER Road Oakland, MD Enjoy lakefront living at its finest in this beautifully remodeled home with a private doc...	5 beds \| 4 baths \| 3,456 sq.ft.	$1,750,000	Airbnb cash on cash: -0.78% Traditional cash on cash: 1.2% Airbnb Rental Income: $1968 Traditional Rental Income: $4663 Airbnb ROI: -0.78% Traditional ROI: 1.2%
3749 MARYLAND Highway Oakland, MD Set on a beautiful lot in Deep Creek, Maryland, this stunning property offers the perfect ...	2 beds \| 2 baths \| 2,015 sq.ft.	$325,000	Airbnb cash on cash: 0.42% Traditional cash on cash: 5.59% Airbnb Rental Income: $1132 Traditional Rental Income: $2334 Airbnb ROI: 0.42% Traditional ROI: 5.59%
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: -0.53% Traditional cash on cash: 1.5% Airbnb Rental Income: $1631 Traditional Rental Income: $2874 Airbnb ROI: -0.53% Traditional ROI: 1.5%
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.	$799,900	Airbnb cash on cash: -0.68% Traditional cash on cash: 2.7% Airbnb Rental Income: $1631 Traditional Rental Income: $3685 Airbnb ROI: -0.68% Traditional ROI: 2.7%
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%
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.	$1,149,800	Airbnb cash on cash: -0.26% Traditional cash on cash: 2.94% Airbnb Rental Income: $1968 Traditional Rental Income: $4868 Airbnb ROI: -0.26% Traditional ROI: 2.94%
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: 1.76% Traditional cash on cash: 7.55% Airbnb Rental Income: $1631 Traditional Rental Income: $2676 Airbnb ROI: 1.76% Traditional ROI: 7.55%
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	$229,900	Airbnb cash on cash: 1.02% Traditional cash on cash: 6.1% Airbnb Rental Income: $1077 Traditional Rental Income: $1813 Airbnb ROI: 1.02% Traditional ROI: 6.1%
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%
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%
1001 SUTTER Lane Oakland, MD Discover the ultimate mountain-lake getaway in this stunning 5BR Southern-style home on a ...	5 beds \| 6 baths \| 6,550 sq.ft.	$799,000	Airbnb cash on cash: -0.16% Traditional cash on cash: 6.23% Airbnb Rental Income: $1968 Traditional Rental Income: $6210 Airbnb ROI: -0.16% Traditional ROI: 6.23%
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: -1.38% Traditional cash on cash: 0.76% Airbnb Rental Income: $1968 Traditional Rental Income: $6125 Airbnb ROI: -1.38% Traditional ROI: 0.76%
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	$359,700	Airbnb cash on cash: 1.42% Traditional cash on cash: 6.8% Airbnb Rental Income: $1631 Traditional Rental Income: $2986 Airbnb ROI: 1.42% Traditional ROI: 6.8%
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.	$314,000	Airbnb cash on cash: 0.65% Traditional cash on cash: 9.12% Airbnb Rental Income: $1148 Traditional Rental Income: $3270 Airbnb ROI: 0.65% Traditional ROI: 9.12%
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: 0.82% Traditional cash on cash: 8.94% Airbnb Rental Income: $1148 Traditional Rental Income: $2950 Airbnb ROI: 0.82% 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: 0.91% 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.	$749,000	Airbnb cash on cash: 0.35% Traditional cash on cash: 5.49% Airbnb Rental Income: $1968 Traditional Rental Income: $5042 Airbnb ROI: 0.35% Traditional ROI: 5.49%
20160 GARRETT Highway unit: 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: 0.16% Traditional cash on cash: 3.06% Airbnb Rental Income: $1132 Traditional Rental Income: $1811 Airbnb ROI: 0.16% Traditional ROI: 3.06%
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%
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.	$359,000	Airbnb cash on cash: 1.53% Traditional cash on cash: 6.93% Airbnb Rental Income: $1631 Traditional Rental Income: $2991 Airbnb ROI: 1.53% Traditional ROI: 6.93%
3930 MAYHEW INN Road Oakland, MD 2 for 1 on 2 .3 +/- acres! Remodeled 2BR 2BA cottage with auxiliary building that has an o...	3 beds \| 3 baths \| 2,227 sq.ft.	$399,900	Airbnb cash on cash: -0.14% Traditional cash on cash: 5.73% Airbnb Rental Income: $1148 Traditional Rental Income: $2967 Airbnb ROI: -0.14% Traditional ROI: 5.73%
52 DAM VIEW Drive Oakland, MD Panoramic Lake views in the Bray Run community, just minutes from Deep Creek Lake, state p...	4 beds \| 6 baths \| 3,032 sq.ft.	$1,087,900	Airbnb cash on cash: -0.56% Traditional cash on cash: 3.91% Airbnb Rental Income: $1631 Traditional Rental Income: $5698 Airbnb ROI: -0.56% Traditional ROI: 3.91%
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.	$399,000	Airbnb cash on cash: -0.04% Traditional cash on cash: 6.14% Airbnb Rental Income: $1148 Traditional Rental Income: $3081 Airbnb ROI: -0.04% Traditional ROI: 6.14%
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.	$174,900	Airbnb cash on cash: 2.79% Traditional cash on cash: 9.85% Airbnb Rental Income: $1148 Traditional Rental Income: $1944 Airbnb ROI: 2.79% Traditional ROI: 9.85%

Your search for investment property begins and ends here

Ruth Lake Investmata Tnvestmiaensent Pment Property for Sale in Oakland, MD

609 Southern Pines Drive

Oakland, MD

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

$425,000

Airbnb cash on cash: 0.79%

Traditional cash on cash: 6.13%

Airbnb Rental Income: $1631

Traditional Rental Income: $3296

Airbnb ROI: 0.79%

Traditional ROI: 6.13%

24 TRAILSIDE WAY

Oakland, MD

4 beds | 4 baths | N/A

$555,000

Airbnb cash on cash: 0.16%

Traditional cash on cash: 5.16%

Airbnb Rental Income: $1631

Traditional Rental Income: $3765

Airbnb ROI: 0.16%

Traditional ROI: 5.16%

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%

1544 STOCKSLAGER Road

Oakland, MD

5 beds | 4 baths | 3,456 sq.ft.

$1,750,000

Airbnb cash on cash: -0.78%

Traditional cash on cash: 1.2%

Airbnb Rental Income: $1968

Traditional Rental Income: $4663

Airbnb ROI: -0.78%

Traditional ROI: 1.2%

3749 MARYLAND Highway

Oakland, MD

2 beds | 2 baths | 2,015 sq.ft.

$325,000

Airbnb cash on cash: 0.42%

Traditional cash on cash: 5.59%

Airbnb Rental Income: $1132

Traditional Rental Income: $2334

Airbnb ROI: 0.42%

Traditional ROI: 5.59%

267 SAN FRANCISCO Street

Oakland, MD

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

$899,900

Airbnb cash on cash: -0.53%

Traditional cash on cash: 1.5%

Airbnb Rental Income: $1631

Traditional Rental Income: $2874

Airbnb ROI: -0.53%

Traditional ROI: 1.5%

467 PARADISE RIDGE Road

Oakland, MD

4 beds | 4 baths | 3,780 sq.ft.

$799,900

Airbnb cash on cash: -0.68%

Traditional cash on cash: 2.7%

Airbnb Rental Income: $1631

Traditional Rental Income: $3685

Airbnb ROI: -0.68%