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.

Condos for Sale in Oakland, MD

Search for Condo for Sale in Oakland, Maryland. Browse all of Mashvisor’s Condo listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 24 Condo 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
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%
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.	$695,000	Airbnb cash on cash: 1.76% Traditional cash on cash: 1.86% Airbnb Rental Income: $3503 Traditional Rental Income: $2798 Airbnb ROI: 1.76% Traditional ROI: 1.86%
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%
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%
131 ROCK RIDGE LANE #12 Oakland, MD Craftsman-style home in the much sought after Silver Ridge community. Once you enter, you'...	4 beds \| 4 baths \| 2,422 sq.ft.	$509,900	Airbnb cash on cash: 5.02% Traditional cash on cash: 5.16% Airbnb Rental Income: $4304 Traditional Rental Income: $3466 Airbnb ROI: 5.02% Traditional ROI: 5.16%
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%
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%
135 JEFFREY LANE #19D Oakland, MD Wonderful lake view condo right in the heart of Deep Creek Lake! It is truly hard to beat ...	2 beds \| 2 baths \| 1,200 sq.ft.	$325,000	Airbnb cash on cash: 4.45% Traditional cash on cash: 5.1% Airbnb Rental Income: $2615 Traditional Rental Income: $2189 Airbnb ROI: 4.45% Traditional ROI: 5.1%
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%
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%
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	$299,900	Airbnb cash on cash: 5.49% Traditional cash on cash: 4.47% Airbnb Rental Income: $2748 Traditional Rental Income: $1813 Airbnb ROI: 5.49% Traditional ROI: 4.47%
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%
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%
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%
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%
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%
565 GLENDALE ROAD #125 Oakland, MD Wake up to the lake at your doorstep. This ground-level, end-unit condo puts you right whe...	1 beds \| 1 baths \| 496 sq.ft.	$349,900	Airbnb cash on cash: 4.69% Traditional cash on cash: 3.48% Airbnb Rental Income: $2748 Traditional Rental Income: $1705 Airbnb ROI: 4.69% Traditional ROI: 3.48%
565 GLENDALE ROAD #307 Oakland, MD Third-level unit at Silver Tree Suites with direct lake frontage and stunning water views....	1 beds \| 1 baths \| 832 sq.ft.	$299,900	Airbnb cash on cash: 5.16% Traditional cash on cash: 4.74% Airbnb Rental Income: $2748 Traditional Rental Income: $1983 Airbnb ROI: 5.16% Traditional ROI: 4.74%
12 ROMAN RIDGE ROAD #22B Oakland, MD SOLD TURN KEY - FULLY FURNISHED!!! As its vacation rental name describes, "Whispering Wate...	3 beds \| 4 baths \| 2,202 sq.ft.	$554,900	Airbnb cash on cash: 3.28% Traditional cash on cash: 4.22% Airbnb Rental Income: $3503 Traditional Rental Income: $3218 Airbnb ROI: 3.28% Traditional ROI: 4.22%
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.	$369,000	Airbnb cash on cash: 3.7% Traditional cash on cash: 3.68% Airbnb Rental Income: $2615 Traditional Rental Income: $1981 Airbnb ROI: 3.7% Traditional ROI: 3.68%
19956 GARRETT HIGHWAY #6 Oakland, MD Experience the best in maintenance free lakefront living on Deep Creek Lake! This 4 BR 4 B...	4 beds \| 4 baths \| 3,000 sq.ft.	$1,349,000	Airbnb cash on cash: 0.86% Traditional cash on cash: 1.77% Airbnb Rental Income: $4304 Traditional Rental Income: $4542 Airbnb ROI: 0.86% Traditional ROI: 1.77%
16 SILVER RIDGE COURT #41/2 Oakland, MD Welcome to this beautifully crafted 4 bedroom, 3 bath home nestled in the sought-after Sil...	4 beds \| 3 baths \| 2,700 sq.ft.	$589,000	Airbnb cash on cash: 4.14% Traditional cash on cash: 4.46% Airbnb Rental Income: $4304 Traditional Rental Income: $3570 Airbnb ROI: 4.14% Traditional ROI: 4.46%
180 MYSTIC CREEK TRAIL #3A Oakland, MD Discover the perfect blend of comfort and style in this finely appointed 3BR, 2.5BA vacati...	3 beds \| 4 baths \| 2,200 sq.ft.	$472,500	Airbnb cash on cash: 3.98% Traditional cash on cash: 5.4% Airbnb Rental Income: $3503 Traditional Rental Income: $3359 Airbnb ROI: 3.98% Traditional ROI: 5.4%
36 JEFFREY LANE #6B Oakland, MD Welcome to "Lakeview Loft" your perfect Deep Creek getaway! This 2-bedroom, 1-bathroom uni...	2 beds \| 1 baths \| 660 sq.ft.	$250,000	Airbnb cash on cash: 6.05% Traditional cash on cash: 4.73% Airbnb Rental Income: $2615 Traditional Rental Income: $1679 Airbnb ROI: 6.05% Traditional ROI: 4.73%

Your search for investment property begins and ends here

Condos for Sale in Oakland, MD

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%

65 VILLAGE DRIVE #6

Oakland, MD

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

$695,000

Airbnb cash on cash: 1.76%

Traditional cash on cash: 1.86%

Airbnb Rental Income: $3503

Traditional Rental Income: $2798

Airbnb ROI: 1.76%

Traditional ROI: 1.86%

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%

565 GLENDALE ROAD #303B

Oakland, MD

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%

131 ROCK RIDGE LANE #12

Oakland, MD

4 beds | 4 baths | 2,422 sq.ft.

$509,900

Airbnb cash on cash: 5.02%

Traditional cash on cash: 5.16%

Airbnb Rental Income: $4304

Traditional Rental Income: $3466

Airbnb ROI: 5.02%

Traditional ROI: 5.16%

175 ROMAN RIDGE ROAD #15

Oakland, MD

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%

565 GLENDALE ROAD #115A

Oakland, MD

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%

135 JEFFREY LANE #19D

Oakland, MD

2 beds | 2 baths | 1,200 sq.ft.

$325,000

Airbnb cash on cash: 4.45%

Traditional cash on cash: 5.1%

Airbnb Rental Income: $2615

Traditional Rental Income: $2189

Airbnb ROI: 4.45%