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ZIP Code: 21550
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217 Properties Available

217 Properties Available

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47 HOLY CROSS, Oakland, MD 21550
1/109
Active
3D

$6,499,900

8 Beds9 Baths11,417 SqFt

47 HOLY CROSS, Oakland, MD 21550

MLS# MDGA2010560

Listed by Railey Realty, Inc.

Bright MLS (BMLS)
4009 MAYHEW INN, Oakland, MD 21550
1/2
Active

$6,000,000

169 Acres Lot

4009 MAYHEW INN, Oakland, MD 21550

MLS# MDGA2007236

Listed by Jason Mitchell Group

Bright MLS (BMLS)
1010 HOLY CROSS DR, Oakland, MD 21550
1/147
Active
3D

$5,150,000

8 Beds9 Baths10,300 SqFt

1010 HOLY CROSS DR, Oakland, MD 21550

MLS# MDGA2011388

Listed by Railey Realty, Inc.

Bright MLS (BMLS)
65 ENTERPRISE DR, Oakland, MD 21550
1/67
Active

$2,799,900

5.3 Acres Lot

65 ENTERPRISE DR, Oakland, MD 21550

MLS# MDGA2010098

Listed by Railey Realty, Inc.

Bright MLS (BMLS)
19530 GARRETT HWY, Oakland, MD 21550
1/43
Active

$2,500,000

6.62 Acres Lot

19530 GARRETT HWY, Oakland, MD 21550

MLS# MDGA2010798

Listed by Railey Realty, Inc.

Bright MLS (BMLS)
83 BETHLEHEM RD, Oakland, MD 21550
1/43
Active

$2,499,900

4 Beds2 Baths2,190 SqFt

83 BETHLEHEM RD, Oakland, MD 21550

MLS# MDGA2011892

Listed by Railey Realty, Inc.

Bright MLS (BMLS)
2725 STOCKSLAGER RD, Oakland, MD 21550
1/115
Active

$2,350,000

5 Beds7 Baths5,376 SqFt

2725 STOCKSLAGER RD, Oakland, MD 21550

MLS# MDGA2008312

Listed by Taylor-Made Deep Creek Sales

Bright MLS (BMLS)
1038 S BLAKESLEE RD, Oakland, MD 21550
1/69
Active

$2,100,000

5 Beds5 Baths4,074 SqFt

1038 S BLAKESLEE RD, Oakland, MD 21550

MLS# MDGA2011370

Listed by Taylor-Made Deep Creek Sales

Bright MLS (BMLS)
209 GLENDALE RD, Oakland, MD 21550
1/89
Under Contract

$2,100,000

6 Beds5 Baths3,882 SqFt

209 GLENDALE RD, Oakland, MD 21550

MLS# MDGA2010922

Listed by Railey Realty, Inc.

Bright MLS (BMLS)
815 CHADDERTON SCHOOL RD, Oakland, MD 21550
1/110
Under Contract
3D

$1,900,000

5 Beds4 Baths4,619 SqFt

815 CHADDERTON SCHOOL RD, Oakland, MD 21550

MLS# MDGA2011092

Listed by Railey Realty, Inc.

Bright MLS (BMLS)
499 OAKLAND DR, Oakland, MD 21550
1/103
Active

$1,750,000

1.37 Acres Lot

499 OAKLAND DR, Oakland, MD 21550

MLS# MDGA2003394

Listed by Railey Realty, Inc.

Bright MLS (BMLS)
17848 GARRETT HWY, Oakland, MD 21550
1/121
Under Contract
3D

$1,700,000

5.77 Acres Lot

17848 GARRETT HWY, Oakland, MD 21550

MLS# MDGA2011286

Listed by Railey Realty, Inc.

Bright MLS (BMLS)
670 WOODLANDS HILL LN, Oakland, MD 21550
1/72
Active

$1,689,000

5 Beds5 Baths3,714 SqFt

670 WOODLANDS HILL LN, Oakland, MD 21550

MLS# MDGA2011904

Listed by Railey Realty, Inc.

Bright MLS (BMLS)
3898 3898 UNDERWOOD RD, Oakland, MD 21550
1/31
Price Dropped by $150K

$1,650,000

4 Beds6 Baths5,117 SqFt

3898 3898 UNDERWOOD RD, Oakland, MD 21550

MLS# MDGA2010508

Listed by Custer Realty & Auction

Bright MLS (BMLS)
2311 BOY SCOUT RD, Oakland, MD 21550
1/78
Active

$1,579,900

4 Beds3 Baths3,278 SqFt

2311 BOY SCOUT RD, Oakland, MD 21550

MLS# MDGA2012046

Listed by Railey Realty, Inc.

Bright MLS (BMLS)
211 HIGH POINT RIDGE RD, Oakland, MD 21550
1/99
Active

$1,495,000

4 Beds4 Baths3,472 SqFt

211 HIGH POINT RIDGE RD, Oakland, MD 21550

MLS# MDGA2011990

Listed by Railey Realty, Inc.

Bright MLS (BMLS)
827 PENN POINT RD, Oakland, MD 21550
1/64
Active

$1,400,000

5 Beds4 Baths2,832 SqFt

827 PENN POINT RD, Oakland, MD 21550

MLS# MDGA2011664

Listed by Taylor-Made Deep Creek Sales

Bright MLS (BMLS)
439 PARADISE HTS, Oakland, MD 21550
1/45
Active
3D

$1,329,000

6 Beds5 Baths4,113 SqFt

439 PARADISE HTS, Oakland, MD 21550

MLS# MDGA2008472

Listed by Railey Realty, Inc.

Bright MLS (BMLS)
122 WOODLANDS HILL LN, Oakland, MD 21550
1/54
Active

$1,200,000

4 Beds5 Baths2,656 SqFt

122 WOODLANDS HILL LN, Oakland, MD 21550

MLS# MDGA2011982

Listed by Taylor-Made Deep Creek Sales

Bright MLS (BMLS)
209 BLACK ANGUS DR, Oakland, MD 21550
1/50
Under Contract

$1,200,000

2 Beds2 Baths1,156 SqFt

209 BLACK ANGUS DR, Oakland, MD 21550

MLS# MDGA2012018

Listed by Railey Realty, Inc.

Bright MLS (BMLS)
248 TARN DR, Oakland, MD 21550
1/70
Active

$1,189,000

6 Beds6 Baths3,482 SqFt

248 TARN DR, Oakland, MD 21550

MLS# MDGA2011874

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)
588 LAKE FOREST DRIVE, Oakland, MD 21550
1/39
Pending

$1,089,000

3 Beds2 Baths1,411 SqFt

588 LAKE FOREST DRIVE, Oakland, MD 21550

MLS# MDGA2011898

Listed by Railey Realty, Inc.

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)
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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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eXp Realty
Skip Tolley
+1(410) 935-7500
skip@captainwaterfront.com

Get My App

    • Home
      Market Snapshot
    • Buy
      1. All Listings
      2. Featured Listings
      3. Sold Listings
      Contact
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      1. Home Valuation

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

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

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.
White Font
eXp Realty
Skip Tolley
+1(410) 935-7500
skip@captainwaterfront.com

Get My App

    • Home
      Market Snapshot
    • Buy
      1. All Listings
      2. Featured Listings
      3. Sold Listings
      Contact
    • Sell
      1. Home Valuation

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

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