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150 Properties Available In Oakland
- Default
- Price-High To Low
- Price-Low To High
- Newest Listings
- Beds (Most)
- Baths (Most)
- Year Built (Newest)
- Square Feet (Biggest)

$899,900
Single Family Home
145 LOWER PENN POINT DR, Oakland, MD 21550
**SPLIT LAKE FRONT** WITH TYPE A DOCK**Discover this stunning chalet-style home located in the coveted Penn Point subdiv...
MLS# MDGA2008610
Listed by Real Broker, LLC


$397,500
Single Family Home
321 DEER PARK HOTEL RD, Oakland, MD 21550
Extensively Updated Mountain Retreat – Move-In Ready & Just 10 Miles from Deep Creek Lake<br><br>This beautifully renova...
MLS# MDGA2009244
Listed by Railey Realty, Inc.


$1,249,000
Condo
19956 GARRETT HWY #2, Oakland, MD 21550
Luxury waterfront townhome located in the pristine Creekside community! This home will be sure to check off all the boxe...
MLS# MDGA2009438
Listed by Taylor Made Deep Creek Vacations & Sales


$315,000
Single Family Home
290 CRELLIN UNDERWOOD RD, Oakland, MD 21550
Awesome 3BR/2BA Log home sitting on 2 acre lot. Third bedroom in on lower level and does not have an egress window. Full...
MLS# MDGA2009466
Listed by Railey Realty, Inc.


$315,000
Single Family Home
473 CUMBERLAND RD, Oakland, MD 21550
Nestled on a tranquil wooded hillside overlooking Deep Creek Lake, this charming home offers an exceptional opportunity ...
MLS# MDGA2009464
Listed by Mr. Lister Realty


$387,700
Single Family Home
723 KINGS, Oakland, MD 21550
"Charming two-story home situated on a beautiful .292-acre level lot in a prime location (Kings Hills Estates) Enjoy the...
MLS# MDGA2009442
Listed by Long & Foster Real Estate, Inc.


$570,000
Single Family Home
462 SKIPPERS POINT RD, Oakland, MD 21550
This 5-bedroom home offers filtered lake views and features a finished bonus room above the two-car garage. Located just...
MLS# MDGA2009418
Listed by Railey Realty, Inc.


$399,000
Single Family Home
1220 BROADFORD RD, Oakland, MD 21550
Spacious 4-Bedroom Home Near Broadford Lake! Welcome to your dream home in one of the area's most desirable neighborhood...
MLS# MDGA2009416
Listed by Railey Realty, Inc.


$674,900
Condo
5 ARROWHEAD LN #5, Oakland, MD 21550
Great location for this 3BR-3BA Arrowhead townhouse. This unit sits very close to the water and has fantastic water view...
MLS# MDGA2009392
Listed by Railey Realty, Inc.


$985,000
Single Family Home
39 LEO FRIEND RD, Oakland, MD 21550
Beautiful split Lakefront Home with Breathtaking Views and Type A Dock. Discover unparalleled lakefront living in this m...
MLS# MDGA2009372
Listed by Railey Realty, Inc.


$429,900
Single Family Home
503 SOUTHERN PINES DR, Oakland, MD 21550
Brand new and built to make life easy. Tucked in the quiet, sought-after Southern Pines community, this single-level hom...
MLS# MDGA2009360
Listed by Railey Realty, Inc.


$360,000
Single Family Home
254 LITTLE MOUNTAIN RD, Oakland, MD 21550
Welcome to 254 Little Mountain Road, a serene mountain escape nestled on nearly 5 acres in the Backbone Ridge community....
MLS# MDGA2009344
Listed by Railey Realty, Inc.


$1,200,000
Single Family Home
2849 SHINGLE CAMP RD, Oakland, MD 21550
Vintage 3BR Lakefront Dome Home with Private Type "A" Dock! & no HOA . Own a piece of Deep Creek charm with this unique ...
MLS# MDGA2009324
Listed by Railey Realty, Inc.


$495,000
Condo
20160 GARRETT HWY #D308/408, Oakland, MD 21550
Lakefront Luxury at Will O' The Wisp – Nicely renovated Unit 308/408 offers a 2 BR, 2 Bath 2- level floor plan perfect f...
MLS# MDGA2009336
Listed by Railey Realty, Inc.


$2,845,000
Single Family Home
56 BEE TREE LN, Oakland, MD 21550
Unmatched EXCEPTIONAL Lakefront Living – 6 Bedrooms | 7.5 Baths | Tucked Among the Pines<br><br>Discover a rare opportu...
MLS# MDGA2009212
Listed by Railey Realty, Inc.


$258,800
Single Family Home
116 S OAKHALL DR, Oakland, MD 21550
Move right in to this fresh and updated home. Enjoy upgrades with recent, and some brand new, finishes like Luxury Vinyl...
MLS# MDGA2009280
Listed by Keller Williams Premier Realty


$295,000
Single Family Home
611 E OAK ST, Oakland, MD 21550
Investors, this is an income producing, three unit building with three separate apartments, just a few minutes walk to d...
MLS# MDGA2009308
Listed by Railey Realty, Inc.


$669,000
Single Family Home
245 SANTA FE TRL, Oakland, MD 21550
3/4BR 3BA chalet with LAKE VIEWS! 2300sf vacation home fronting on a mountain stream, backing to woods & boulders and o...
MLS# MDGA2009286
Listed by Taylor Made Deep Creek Vacations & Sales


$369,900
Single Family Home, Townhouse
366 GLENDALE RD, Oakland, MD 21550
Discover the perfect blend of comfort and convenience at 366 Glendale Rd.<br><br>Situated just steps from Deep Creek Lak...
MLS# MDGA2009278
Listed by Keller Williams Capital Properties


$599,900
Single Family Home
433 SAN FRANCISCO ST, Oakland, MD 21550
Fully renovated, fully loaded, and fully ready to be your Deep Creek Lake getaway! This 6-bedroom mountain retreat is pa...
MLS# MDGA2009232
Listed by Railey Realty, Inc.


$1,250,000
Single Family Home
216 TARN DR, Oakland, MD 21550
Breathtaking home located in the well-established Mountainside community. This newer home is simply stunning from the mo...
MLS# MDGA2009200
Listed by Taylor Made Deep Creek Vacations & Sales


$585,000
Single Family Home
328 STOOL ROCK RD, Oakland, MD 21550
Designed and built for the sellers, this 4 bedroom, 2.5 bath home is a true showcase of craftsmanship featuring handmade...
MLS# MDGA2009150
Listed by Railey Realty, Inc.


$599,000
Single Family Home
2719 BROADFORD RD, Oakland, MD 21550
Stunning Brick Ranch Near Broadford Lake Park! This magnificent one-level brick ranch sits on a level 1.5-acre lot backi...
MLS# MDGA2009220
Listed by Railey Realty, Inc.


$1,135,000
Single Family Home
267 WOODLANDS HILL LN, Oakland, MD 21550
267 Woodlands Hill Lane offers mountain living at its finest! This custom, 2021 built chalet is designed for ultimate co...
MLS# MDGA2009170
Listed by Railey Realty, Inc.
