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Start your journey with our top featured listings, showcasing properties that combine great value, desirable features, and strong potential. Ready for you to explore and make your own.
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ZIP Code: 21550
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36 Properties Available

36 Properties Available

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17921 GARRETT HWY, Oakland, MD 21550
1/56
Price Dropped by $34K

$325,000

4 Beds2 Baths1,563 SqFt

17921 GARRETT HWY, Oakland, MD 21550

MLS# MDGA2011818

Listed by Taylor-Made Deep Creek Sales

Bright MLS (BMLS)
127 PARADISE HTS, Oakland, MD 21550
1/24
Price Dropped by $50K

$1,025,000

3 Beds3 Baths2,240 SqFt

127 PARADISE HTS, Oakland, MD 21550

MLS# MDGA2011804

Listed by XRealty.NET LLC

Bright MLS (BMLS)
55 VILLAGE DR #5, Oakland, MD 21550
1/45
Price Dropped by $10K
3D

$585,000

3 Beds3 Baths2,280 SqFt

55 VILLAGE DR #5, Oakland, MD 21550

MLS# MDGA2011682

Listed by Railey Realty, Inc.

Bright MLS (BMLS)
215 H ST, Mountain Lake Park, MD 21550
1/55
Price Dropped by $10K

$369,000

3 Beds3 Baths2,388 SqFt

215 H ST, Mountain Lake Park, MD 21550

MLS# MDGA2011582

Listed by Railey Realty, Inc.

Bright MLS (BMLS)
660 GLENDALE RD, Oakland, MD 21550
1/62
Price Dropped by $100K

$1,100,000

5 Beds3 Baths2,592 SqFt

660 GLENDALE RD, Oakland, MD 21550

MLS# MDGA2011188

Listed by Railey Realty, Inc.

Bright MLS (BMLS)
8956 OAKLAND SANG RUN RD, Oakland, MD 21550
1/69
Price Dropped by $20K

$219,900

3 Beds2 Baths1,064 SqFt

8956 OAKLAND SANG RUN RD, Oakland, MD 21550

MLS# MDGA2011566

Listed by Taylor Properties

Bright MLS (BMLS)
654 N BRADLEY LN, Oakland, MD 21550
1/41
Price Dropped by $25K

$424,900

3 Beds2 Baths1,464 SqFt

654 N BRADLEY LN, Oakland, MD 21550

MLS# MDGA2011266

Listed by Taylor-Made Deep Creek Sales

Bright MLS (BMLS)
400 BEAR DR E, Oakland, MD 21550
1/42
Price Dropped by $9K

$279,900

2 Beds2 Baths560 SqFt

400 BEAR DR E, Oakland, MD 21550

MLS# MDGA2011462

Listed by Taylor-Made Deep Creek Sales

Bright MLS (BMLS)
222 SKIPPERS POINT RD, Oakland, MD 21550
1/57
Price Dropped by $29K

$749,900

5 Beds2 Baths1,278 SqFt

222 SKIPPERS POINT RD, Oakland, MD 21550

MLS# MDGA2011482

Listed by The KW Collective

Bright MLS (BMLS)
137 PARADISE GARDENS RD, Oakland, MD 21550
1/71
Price Dropped by $50K

$999,000

4 Beds2 Baths2,730 SqFt

137 PARADISE GARDENS RD, Oakland, MD 21550

MLS# MDGA2011454

Listed by Taylor-Made Deep Creek Sales

Bright MLS (BMLS)
74 PARKS RD, Oakland, MD 21550
1/2
Price Dropped by $5K

$64,900

3 Beds1 Bath792 SqFt

74 PARKS RD, Oakland, MD 21550

MLS# MDGA2011172

Listed by Real Broker, LLC

Bright MLS (BMLS)
157 JEFFREY LN #21B, Oakland, MD 21550
1/28
Price Dropped by $2K

$297,000

2 Beds1 Bath550 SqFt

157 JEFFREY LN #21B, Oakland, MD 21550

MLS# MDGA2011174

Listed by Taylor-Made Deep Creek Sales

Bright MLS (BMLS)
505 SOUTHERN PINES DR, Oakland, MD 21550
1/38
Price Dropped by $5K

$287,500

3 Beds2 Baths1,248 SqFt

505 SOUTHERN PINES DR, Oakland, MD 21550

MLS# MDGA2011242

Listed by Taylor-Made Deep Creek Sales

Bright MLS (BMLS)
820 N 4TH ST, Oakland, MD 21550
1/19
Price Dropped by $10K

$40,000

2 Beds1 Bath782 SqFt

820 N 4TH ST, Oakland, MD 21550

MLS# MDGA2011246

Listed by The KW Collective

Bright MLS (BMLS)
52 DAM VIEW DR, Oakland, MD 21550
1/91
Price Dropped by $13K
3D

$1,074,900

4 Beds6 Baths3,032 SqFt

52 DAM VIEW DR, Oakland, MD 21550

MLS# MDGA2011104

Listed by Railey Realty, Inc.

Bright MLS (BMLS)
467 PARADISE RIDGE RD, Oakland, MD 21550
1/64
Price Dropped by $30K

$769,900

4 Beds4 Baths3,780 SqFt

467 PARADISE RIDGE RD, Oakland, MD 21550

MLS# MDGA2011164

Listed by Railey Realty, Inc.

Bright MLS (BMLS)
931 BLACK OAK DR, Oakland, MD 21550
1/53
Price Dropped by $5K

$339,999

3 Beds1 Bath990 SqFt

931 BLACK OAK DR, Oakland, MD 21550

MLS# MDGA2010958

Listed by Taylor-Made Deep Creek Sales

Bright MLS (BMLS)
178 WINDING TRAIL LN #5B, Oakland, MD 21550
1/47
Price Dropped by $20K

$569,000

5 Beds5 Baths3,300 SqFt

178 WINDING TRAIL LN #5B, Oakland, MD 21550

MLS# MDGA2010960

Listed by Railey Realty, Inc.

Bright MLS (BMLS)
181 JEFFREY LN #23A, Oakland, MD 21550
1/25
Price Dropped by $10K

$259,900

2 Beds1 Bath670 SqFt

181 JEFFREY LN #23A, Oakland, MD 21550

MLS# MDGA2010704

Listed by Railey Realty, Inc.

Bright MLS (BMLS)
961 CEDAR LN, Oakland, MD 21550
1/50
Price Dropped by $20K

$339,000

4 Beds3 Baths1,920 SqFt

961 CEDAR LN, Oakland, MD 21550

MLS# MDGA2010426

Listed by Taylor-Made Deep Creek Sales

Bright MLS (BMLS)
1909 PYSELL CROSSCUT RD, Oakland, MD 21550
1/82
Price Dropped by $40K

$825,000

4 Beds5 Baths2,970 SqFt

1909 PYSELL CROSSCUT RD, Oakland, MD 21550

MLS# MDGA2010462

Listed by Railey Realty, Inc.

Bright MLS (BMLS)
126 LEO FRIEND RD, Oakland, MD 21550
1/50
Price Dropped by $30K

$499,900

4 Beds3 Baths2,235 SqFt

126 LEO FRIEND RD, Oakland, MD 21550

MLS# MDGA2009940

Listed by Railey Realty, Inc.

Bright MLS (BMLS)
565 GLENDALE RD #212A, Oakland, MD 21550
1/20
Price Dropped by $10K

$175,000

1 Bed1 Bath527 SqFt

565 GLENDALE RD #212A, Oakland, MD 21550

MLS# MDGA2008680

Listed by Railey Realty, Inc.

Bright MLS (BMLS)
BETHLEHEM RD, Oakland, MD 21550
1/13
Price Dropped by $25K

$199,900

50 Acres

BETHLEHEM RD, Oakland, MD 21550

MLS# MDGA2011660

Listed by Hawkins Real Estate Company

Bright MLS (BMLS)
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GOOGLE REVIEWS - for website (1)
Samson Properties
Eunice Rancy | License ID: 0225260420
95 Dunn Drive Ste 200, Stafford, VA, 22556, USA

+1(703) 223-9415

eunice@amaryllishomes.com

Get My App

IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.

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Powered by Lofty Inc. Copyright 2026. All Rights Reserved.

GOOGLE REVIEWS - for website (1)
Samson Properties
Eunice Rancy | License ID: 0225260420
95 Dunn Drive Ste 200, Stafford, VA, 22556, USA

+1(703) 223-9415

eunice@amaryllishomes.com

Get My App

IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.

Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility

Powered by Lofty Inc. Copyright 2026. All Rights Reserved.