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 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: 1.62% Traditional cash on cash: 5.89% Airbnb Rental Income: $2070 Traditional Rental Income: $3296 Airbnb ROI: 1.62% Traditional ROI: 5.89%
565 GLENDALE Road unit: 124 #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: 1.79% Traditional cash on cash: 5.99% Airbnb Rental Income: $1727 Traditional Rental Income: $1949 Airbnb ROI: 1.79% 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: -0.84% Traditional cash on cash: 2.35% Airbnb Rental Income: $1474 Traditional Rental Income: $3488 Airbnb ROI: -0.84% Traditional ROI: 2.35%
65 VILLAGE Drive unit: 6 #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: -0.84% Traditional cash on cash: 2.06% Airbnb Rental Income: $1474 Traditional Rental Income: $2798 Airbnb ROI: -0.84% Traditional ROI: 2.06%
1256 BOILING SPRING Road Oakland, MD Priced to sell 3BR, 2BA home on 1.72 acres with fenced in backyard and plenty of privacy. ...	3 beds \| 2 baths \| 1,456 sq.ft.	$215,000	Airbnb cash on cash: 2.78% Traditional cash on cash: 9.64% Airbnb Rental Income: $1474 Traditional Rental Income: $2438 Airbnb ROI: 2.78% Traditional ROI: 9.64%
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: 5.28% Traditional cash on cash: 7.08% Airbnb Rental Income: $1727 Traditional Rental Income: $1539 Airbnb ROI: 5.28% Traditional ROI: 7.08%
175 ROMAN RIDGE Road unit: 15 #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.	$547,500	Airbnb cash on cash: 0.89% Traditional cash on cash: 8.38% Airbnb Rental Income: $2070 Traditional Rental Income: $5368 Airbnb ROI: 0.89% Traditional ROI: 8.38%
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.	$759,900	Airbnb cash on cash: 0.32% Traditional cash on cash: 1.78% Airbnb Rental Income: $2416 Traditional Rental Income: $2858 Airbnb ROI: 0.32% Traditional ROI: 1.78%
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: 0.6% Traditional cash on cash: 3.39% Airbnb Rental Income: $1474 Traditional Rental Income: $2154 Airbnb ROI: 0.6% Traditional ROI: 3.39%
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: 1.34% Traditional cash on cash: 4.69% Airbnb Rental Income: $2070 Traditional Rental Income: $3200 Airbnb ROI: 1.34% 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: 2.45% Traditional cash on cash: 3.48% Airbnb Rental Income: $1727 Traditional Rental Income: $1530 Airbnb ROI: 2.45% Traditional ROI: 3.48%
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	$249,900	Airbnb cash on cash: 3.16% Traditional cash on cash: 5.54% Airbnb Rental Income: $1727 Traditional Rental Income: $1813 Airbnb ROI: 3.16% Traditional ROI: 5.54%
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: -0.43% Traditional cash on cash: 1.26% Airbnb Rental Income: $2070 Traditional Rental Income: $3578 Airbnb ROI: -0.43% 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: 1.09% Traditional cash on cash: 3.97% Airbnb Rental Income: $2070 Traditional Rental Income: $3055 Airbnb ROI: 1.09% 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: 1.31% Traditional cash on cash: 4.81% Airbnb Rental Income: $1242 Traditional Rental Income: $1638 Airbnb ROI: 1.31% Traditional ROI: 4.81%
4 LAUREL BROOK Drive unit: 4 #4 Oakland, MD Opportunites abound at this wonderfully maintained home in Laurel Brook! Whether you are l...	2 beds \| 2 baths \| N/A	$225,000	Airbnb cash on cash: 1.72% Traditional cash on cash: 6.16% Airbnb Rental Income: $1242 Traditional Rental Income: $1792 Airbnb ROI: 1.72% Traditional ROI: 6.16%
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.	$325,000	Airbnb cash on cash: 1.5% Traditional cash on cash: 5.87% Airbnb Rental Income: $1474 Traditional Rental Income: $2376 Airbnb ROI: 1.5% Traditional ROI: 5.87%
189 RED RUN Road unit: 1-C-2 #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: -0.34% Traditional cash on cash: 1.85% Airbnb Rental Income: $1242 Traditional Rental Income: $2053 Airbnb ROI: -0.34% Traditional ROI: 1.85%
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: -0.68% Traditional cash on cash: 0.46% Airbnb Rental Income: $1474 Traditional Rental Income: $2308 Airbnb ROI: -0.68% Traditional ROI: 0.46%
565 GLENDALE Road unit: 212 #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.	$210,000	Airbnb cash on cash: 4.11% Traditional cash on cash: 7.3% Airbnb Rental Income: $1727 Traditional Rental Income: $1886 Airbnb ROI: 4.11% Traditional ROI: 7.3%
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: 4.33% Traditional cash on cash: 5.04% Airbnb Rental Income: $2416 Traditional Rental Income: $2023 Airbnb ROI: 4.33% Traditional ROI: 5.04%
11 SUNSET Drive Oakland, MD Welcome to this beautiful 3-bedroom, 2-bathroom ranch home nestled in the quiet community ...	3 beds \| 2 baths \| 1,400 sq.ft.	$299,000	Airbnb cash on cash: 1.7% Traditional cash on cash: 6.4% Airbnb Rental Income: $1474 Traditional Rental Income: $2360 Airbnb ROI: 1.7% Traditional ROI: 6.4%
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: -1.21% Traditional cash on cash: 0.76% Airbnb Rental Income: $2416 Traditional Rental Income: $6125 Airbnb ROI: -1.21% Traditional ROI: 0.76%
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: 0.22% Traditional cash on cash: 2.82% Airbnb Rental Income: $2070 Traditional Rental Income: $3356 Airbnb ROI: 0.22% 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: 0.57% Traditional cash on cash: 3.53% Airbnb Rental Income: $2070 Traditional Rental Income: $3451 Airbnb ROI: 0.57% 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	$440,000	Airbnb cash on cash: 0.07% Traditional cash on cash: 2.62% Airbnb Rental Income: $1242 Traditional Rental Income: $1895 Airbnb ROI: 0.07% 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: -0.23% Traditional cash on cash: 2.6% Airbnb Rental Income: $1474 Traditional Rental Income: $2755 Airbnb ROI: -0.23% Traditional ROI: 2.6%
130 TIMBERLOFT Circle unit: 14 #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: -0.53% Traditional cash on cash: 2.32% Airbnb Rental Income: $1474 Traditional Rental Income: $3029 Airbnb ROI: -0.53% Traditional ROI: 2.32%
45 VILLAGE Drive unit: 4 #4 Oakland, MD Price Improved! Nestled in the serene Yellowstone Village community, 45 Village Drive offe...	2 beds \| 2 baths \| 1,096 sq.ft.	$415,000	Airbnb cash on cash: 0.14% Traditional cash on cash: 3.59% Airbnb Rental Income: $1242 Traditional Rental Income: $2188 Airbnb ROI: 0.14% Traditional ROI: 3.59%
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: 0.36% Traditional cash on cash: 2.35% Airbnb Rental Income: $2416 Traditional Rental Income: $3448 Airbnb ROI: 0.36% 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: 0.84% Traditional cash on cash: 2.95% Airbnb Rental Income: $2416 Traditional Rental Income: $3207 Airbnb ROI: 0.84% Traditional ROI: 2.95%
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: 2.32% Traditional cash on cash: 6.39% Airbnb Rental Income: $2070 Traditional Rental Income: $2986 Airbnb ROI: 2.32% 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.	$314,900	Airbnb cash on cash: 3.26% Traditional cash on cash: 9.11% Airbnb Rental Income: $2070 Traditional Rental Income: $3270 Airbnb ROI: 3.26% Traditional ROI: 9.11%
62 DUCK COVE Road Oakland, MD Panoramic lakefront living greets you on the point of this remarkable 4 bedroom, 4 bathroo...	4 beds \| 4 baths \| 4,150 sq.ft.	$1,985,000	Airbnb cash on cash: -0.86% Traditional cash on cash: 0.79% Airbnb Rental Income: $2070 Traditional Rental Income: $4578 Airbnb ROI: -0.86% Traditional ROI: 0.79%
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: 3.98% Traditional cash on cash: 5.67% Airbnb Rental Income: $1727 Traditional Rental Income: $1618 Airbnb ROI: 3.98% Traditional ROI: 5.67%
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: 1.7% Traditional cash on cash: 8.47% Airbnb Rental Income: $1474 Traditional Rental Income: $2950 Airbnb ROI: 1.7% Traditional ROI: 8.47%
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: 0.9% Traditional cash on cash: 3.38% Airbnb Rental Income: $2416 Traditional Rental Income: $3501 Airbnb ROI: 0.9% 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: 1.98% Traditional cash on cash: 7.51% Airbnb Rental Income: $1474 Traditional Rental Income: $2447 Airbnb ROI: 1.98% 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: 0.4% Traditional cash on cash: 3.68% Airbnb Rental Income: $1242 Traditional Rental Income: $1981 Airbnb ROI: 0.4% 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: 1.38% Traditional cash on cash: 4.08% Airbnb Rental Income: $2070 Traditional Rental Income: $2737 Airbnb ROI: 1.38% Traditional ROI: 4.08%

Real Estate investment in Oakland, MD

There are 68 properties for sale in the city of Oakland . The median list price in Oakland is $440,000 and the average price per square foot is $200. In November 2025, the average monthly cash on cash return in Oakland is 4.00%. The average monthly rental income in Oakland is $2,803.

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

There are 68 investment properties available for sale in Oakland.

In 2025, 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 $2,803.

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: 1.62%

Traditional cash on cash: 5.89%

Airbnb Rental Income: $2070

Traditional Rental Income: $3296

Airbnb ROI: 1.62%

Traditional ROI: 5.89%

565 GLENDALE Road unit: 124 #124

Oakland, MD

1 beds | 1 baths | 382 sq.ft.

$175,000

Airbnb cash on cash: 1.79%

Traditional cash on cash: 5.99%

Airbnb Rental Income: $1727

Traditional Rental Income: $1949

Airbnb ROI: 1.79%

Traditional ROI: 5.99%

198 GRANDVIEW Drive

Oakland, MD

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

$825,000

Airbnb cash on cash: -0.84%

Traditional cash on cash: 2.35%

Airbnb Rental Income: $1474

Traditional Rental Income: $3488

Airbnb ROI: -0.84%

Traditional ROI: 2.35%

65 VILLAGE Drive unit: 6 #6

Oakland, MD

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

$650,000

Airbnb cash on cash: -0.84%

Traditional cash on cash: 2.06%

Airbnb Rental Income: $1474

Traditional Rental Income: $2798

Airbnb ROI: -0.84%

Traditional ROI: 2.06%

1256 BOILING SPRING Road

Oakland, MD

3 beds | 2 baths | 1,456 sq.ft.

$215,000

Airbnb cash on cash: 2.78%

Traditional cash on cash: 9.64%

Airbnb Rental Income: $1474

Traditional Rental Income: $2438

Airbnb ROI: 2.78%

Traditional ROI: 9.64%

565 GLENDALE Road unit: 116 #116

Oakland, MD

1 beds | 1 baths | 484 sq.ft.

$169,000

Airbnb cash on cash: 5.28%

Traditional cash on cash: 7.08%

Airbnb Rental Income: $1727

Traditional Rental Income: $1539

Airbnb ROI: 5.28%

Traditional ROI: 7.08%

175 ROMAN RIDGE Road unit: 15 #15

Oakland, MD

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

$547,500

Airbnb cash on cash: 0.89%

Traditional cash on cash: 8.38%

Airbnb Rental Income: $2070

Traditional Rental Income: $5368

Airbnb ROI: 0.89%

Traditional ROI: 8.38%

25 SILVER TREE Lane

Oakland, MD

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

$759,900

Airbnb cash on cash: 0.32%

Traditional cash on cash: 1.78%

Airbnb Rental Income: $2416

Traditional Rental Income: $2858

Airbnb ROI: 0.32%