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21550, MD - single-family homes for sale
73 of 73 results displayed
- New
$629,000Active4 beds 3 baths2,280 sq. ft.231 Santa Fe Trl, OAKLAND, MD 21550
MLS# MDGA2011082Listed by: TAYLOR MADE DEEP CREEK VACATIONS & SALES - Coming Soon
$375,000Coming Soon3 beds 2 baths2173 King Wildesen Rd, OAKLAND, MD 21550
MLS# MDGA2011098Listed by: TAYLOR MADE DEEP CREEK VACATIONS & SALES - New
$299,000Active4 beds 2 baths1,913 sq. ft.127 S Oakhall Dr, OAKLAND, MD 21550
MLS# MDGA2011068Listed by: RAILEY REALTY, INC. 
$179,000Pending3 beds 1 baths1,350 sq. ft.506 Roanoke Ave, OAKLAND, MD 21550
MLS# MDGA2011066Listed by: RAILEY REALTY, INC.- New
$275,000Active3 beds 2 baths1,848 sq. ft.702 Sunshine Dr, OAKLAND, MD 21550
MLS# MDGA2011074Listed by: RAILEY REALTY, INC. - New
$639,000Active5 beds 5 baths2,200 sq. ft.130 Mystic Creek Trl #1b, OAKLAND, MD 21550
MLS# MDGA2011072Listed by: RAILEY REALTY, INC. - New
$519,000Active4 beds 5 baths3,192 sq. ft.175 Roman Ridge Rd #15, OAKLAND, MD 21550
MLS# MDGA2011062Listed by: RAILEY REALTY, INC. 
$185,000Active3 beds 2 baths1,170 sq. ft.729 E Oak St, OAKLAND, MD 21550
MLS# MDGA2011048Listed by: RAILEY REALTY, INC.
$899,900Active4 beds 3 baths3,278 sq. ft.267 San Francisco St, OAKLAND, MD 21550
MLS# MDGA2011040Listed by: HOMESMART
$299,000Active4 beds 2 baths1,743 sq. ft.43 Sloan Tract Rd, OAKLAND, MD 21550
MLS# MDGA2011032Listed by: RAILEY REALTY, INC.
$85,000Pending3 beds 1 baths1,462 sq. ft.3416 Broadford Rd, OAKLAND, MD 21550
MLS# MDGA2011020Listed by: TAYLOR MADE DEEP CREEK VACATIONS & SALES
$249,000Pending3 beds 2 baths1,400 sq. ft.711 Heritage Drive, OAKLAND, MD 21550
MLS# MDGA2011022Listed by: RAILEY REALTY, INC.
$275,000Pending2 beds 2 baths1,440 sq. ft.1359 Cedar Ln, OAKLAND, MD 21550
MLS# MDGA2010974Listed by: TAYLOR MADE DEEP CREEK VACATIONS & SALES
$199,000Active4 beds 2 baths3395 Fingerboard Rd, OAKLAND, MD 21550
MLS# MDGA2010996Listed by: TAYLOR MADE DEEP CREEK VACATIONS & SALES
$199,000Pending2 beds 1 baths960 sq. ft.1108 Hutton Rd, OAKLAND, MD 21550
MLS# MDGA2010986Listed by: RAILEY REALTY, INC.
$359,000Active3 beds 1 baths990 sq. ft.931 Black Oak Dr, OAKLAND, MD 21550
MLS# MDGA2010958Listed by: TAYLOR MADE DEEP CREEK VACATIONS & SALES
$299,900Pending3 beds 2 baths1,786 sq. ft.143 Manor Dr, OAKLAND, MD 21550
MLS# MDGA2010990Listed by: RAILEY REALTY, INC.
$589,000Active5 beds 5 baths3,300 sq. ft.178 Winding Trail Ln #5b, OAKLAND, MD 21550
MLS# MDGA2010960Listed by: RAILEY REALTY, INC.
$85,000Active2 beds 1 baths864 sq. ft.1358 Crellin Underwood Rd, OAKLAND, MD 21550
MLS# MDGA2010946Listed by: RAILEY REALTY, INC.
$2,100,000Active6 beds 5 baths3,882 sq. ft.209 Glendale Rd, OAKLAND, MD 21550
MLS# MDGA2010922Listed by: RAILEY REALTY, INC.
$234,000Pending3 beds 2 baths1,520 sq. ft.1021 E High St, OAKLAND, MD 21550
MLS# MDGA2010932Listed by: RAILEY REALTY, INC.
$679,900Active5 beds 5 baths3,000 sq. ft.4a Mystic Creek Trl, OAKLAND, MD 21550
MLS# MDGA2010920Listed by: RAILEY REALTY, INC.
$1,199,990Pending4 beds 6 baths4,744 sq. ft.444 Woodlands Hill Ln, OAKLAND, MD 21550
MLS# MDGA2010802Listed by: COMPASS
$765,000Active4 beds 3 baths2,112 sq. ft.519 Paradise Hts, OAKLAND, MD 21550
MLS# MDGA2010792Listed by: APPALACHIAN REALTY
$829,000Active5 beds 6 baths6,550 sq. ft.1001 Sutter Ln, OAKLAND, MD 21550
MLS# MDGA2010778Listed by: RAILEY REALTY, INC.
$750,000Active5 beds 3 baths2,660 sq. ft.220 Woodlands Hill Ln, OAKLAND, MD 21550
MLS# MDGA2010752Listed by: RE/MAX REALTY GROUP
$1,800,000Active4 beds 6 baths5,117 sq. ft.3898 3898 Underwood Rd, OAKLAND, MD 21550
MLS# MDGA2010508Listed by: CUSTER REALTY & AUCTION
$75,000Active3 beds 1 baths1,488 sq. ft.60 Gorman St, OAKLAND, MD 21550
MLS# MDGA2010692Listed by: CHARIS REALTY GROUP
$6,499,900Active8 beds 9 baths11,417 sq. ft.47 Holy Cross, OAKLAND, MD 21550
MLS# MDGA2010560Listed by: RAILEY REALTY, INC.
$179,900Active3 beds 1 baths816 sq. ft.63 Wallman Rd, OAKLAND, MD 21550
MLS# MDGA2010592Listed by: RAILEY REALTY, INC.
$1,199,000Active5 beds 5 baths2,593 sq. ft.285 Lake Shore Dr, OAKLAND, MD 21550
MLS# MDGA2010466Listed by: KELLER WILLIAMS CAPITAL PROPERTIES
$949,900Pending6 beds 4 baths2,536 sq. ft.340 Grandview Dr, OAKLAND, MD 21550
MLS# MDGA2010536Listed by: RAILEY REALTY, INC.
$599,900Pending4 beds 3 baths2,436 sq. ft.77 Meadow Ct, OAKLAND, MD 21550
MLS# MDGA2010516Listed by: RAILEY REALTY, INC.
$3,950,000Active6 beds 6 baths4,354 sq. ft.282 Mccomas Beach Ter, OAKLAND, MD 21550
MLS# MDGA2010518Listed by: HUNT COUNTRY SOTHEBY'S INTERNATIONAL REALTY
$125,000Active4 beds 2 baths1,932 sq. ft.102 Roanoke Ave, OAKLAND, MD 21550
MLS# MDGA2010452Listed by: TAYLOR MADE DEEP CREEK VACATIONS & SALES
$399,000Active3 beds 3 baths2,128 sq. ft.5024 Cranesville Rd, OAKLAND, MD 21550
MLS# MDGA2010510Listed by: RAILEY REALTY, INC.
$750,000Pending4 beds 4 baths2,632 sq. ft.329 Lemley Dr, OAKLAND, MD 21550
MLS# MDGA2010512Listed by: RAILEY REALTY, INC.- $1,800,000Active4 beds 6 baths5,117 sq. ft.
3893 Underwood Rd, OAKLAND, MD 21550
MLS# MDGA2010508Listed by: CUSTER REALTY & AUCTION 
$865,000Active4 beds 5 baths2,970 sq. ft.1909 Pysell Crosscut Rd, OAKLAND, MD 21550
MLS# MDGA2010462Listed by: RAILEY REALTY, INC.
$919,000Active3 beds 4 baths3,897 sq. ft.39 Leo Friend Rd, OAKLAND, MD 21550
MLS# MDGA2010444Listed by: THE KW COLLECTIVE
$339,000Active5 beds 4 baths3,682 sq. ft.697 Monte Vista Rd, OAKLAND, MD 21550
MLS# MDGA2010454Listed by: TAYLOR MADE DEEP CREEK VACATIONS & SALES
$379,000Active4 beds 3 baths1,920 sq. ft.961 Cedar Ln, OAKLAND, MD 21550
MLS# MDGA2010426Listed by: TAYLOR MADE DEEP CREEK VACATIONS & SALES
$1,449,000Active5 beds 3 baths2,826 sq. ft.336 Paradise Hts, OAKLAND, MD 21550
MLS# MDGA2010378Listed by: RAILEY REALTY, INC.
$65,000Active-- beds -- baths792 sq. ft.809 N St, MOUNTAIN LAKE PARK, MD 21550
MLS# MDGA2010386Listed by: RAILEY REALTY, INC.
$619,900Active4 beds 4 baths2,550 sq. ft.66 Paradise Ridge Rd, OAKLAND, MD 21550
MLS# MDGA2010278Listed by: HAWKINS REAL ESTATE COMPANY
$425,000Active3 beds 4 baths1,596 sq. ft.104 Pine Top Trl, OAKLAND, MD 21550
MLS# MDGA2010178Listed by: 1 REAL ESTATE SOURCE LLC
$239,000Pending3 beds 1 baths1,199 sq. ft.5202 Hutton Rd, OAKLAND, MD 21550
MLS# MDGA2010148Listed by: RAILEY REALTY, INC.
$769,000Active5 beds 5 baths3,664 sq. ft.1875 Pysell Crosscut Rd, OAKLAND, MD 21550
MLS# MDGA2010078Listed by: TAYLOR MADE DEEP CREEK VACATIONS & SALES
$1,749,000Active4 beds 5 baths2,605 sq. ft.1019 Lake Shore Dr, OAKLAND, MD 21550
MLS# MDGA2010014Listed by: RAILEY REALTY, INC.
$245,000Pending3 beds 1 baths1,408 sq. ft.1570 Garrett Rd, OAKLAND, MD 21550
MLS# MDGA2010010Listed by: 1 REAL ESTATE SOURCE LLC
$529,900Active4 beds 3 baths2,235 sq. ft.126 Leo Friend Rd, OAKLAND, MD 21550
MLS# MDGA2009940Listed by: RAILEY REALTY, INC.
$315,000Active3 beds 3 baths1,416 sq. ft.163 Crestview Dr, OAKLAND, MD 21550
MLS# MDGA2009776Listed by: RAILEY REALTY, INC.
$475,000Active4 beds 4 baths1,492 sq. ft.333 Sloan Tract Rd, OAKLAND, MD 21550
MLS# MDGA2009836Listed by: TAYLOR MADE DEEP CREEK VACATIONS & SALES
$440,000Active4 beds 3 baths2,030 sq. ft.609 Southern Pines Dr, OAKLAND, MD 21550
MLS# MDGA2009816Listed by: BHHS TOUCHDOWN HOME PROS REALTY
$269,500Active3 beds 2 baths1,600 sq. ft.315 Coolidge Ave, OAKLAND, MD 21550
MLS# MDGA2009614Listed by: TAYLOR MADE DEEP CREEK VACATIONS & SALES
$299,900Active3 beds 2 baths1,736 sq. ft.1737 King Wildesen Rd, OAKLAND, MD 21550
MLS# MDGA2009574Listed by: RAILEY REALTY, INC.
$380,000Active4 beds 3 baths1,824 sq. ft.723 Kings, OAKLAND, MD 21550
MLS# MDGA2009442Listed by: LONG & FOSTER REAL ESTATE, INC.
$2,845,000Active6 beds 8 baths5,100 sq. ft.56 Bee Tree Ln, OAKLAND, MD 21550
MLS# MDGA2009212Listed by: RAILEY REALTY, INC.
$599,900Active6 beds 3 baths2,560 sq. ft.433 San Francisco St, OAKLAND, MD 21550
MLS# MDGA2009232Listed by: RAILEY REALTY, INC.
$585,000Active2 beds 2 baths1,584 sq. ft.355 Lonesome Pine Rd, OAKLAND, MD 21550
MLS# MDGA2009210Listed by: LAKE HOMES REALTY, LLC
$545,000Active4 beds 3 baths1,860 sq. ft.328 Stool Rock Rd, OAKLAND, MD 21550
MLS# MDGA2009150Listed by: RAILEY REALTY, INC.
$875,000Pending5 beds 5 baths2,846 sq. ft.139 Overlook Ridge Dr, OAKLAND, MD 21550
MLS# MDGA2009000Listed by: TAYLOR MADE DEEP CREEK VACATIONS & SALES
$425,000Pending3 beds 2 baths1,152 sq. ft.180 Paradise Ridge Rd, OAKLAND, MD 21550
MLS# MDGA2008834Listed by: RAILEY REALTY, INC.
$625,000Active3 beds 3 baths1,740 sq. ft.65 Village Dr #6, OAKLAND, MD 21550
MLS# MDGA2008728Listed by: RAILEY REALTY, INC.
$180,000Active5 beds 2 baths1,536 sq. ft.511 Main St, DEER PARK, MD 21550
MLS# MDGA2008298Listed by: 1 REAL ESTATE SOURCE LLC
$425,000Pending2 beds 1 baths15 Village Dr #1, OAKLAND, MD 21550
MLS# MDGA2008612Listed by: RAILEY REALTY, INC.
$4,250,000Active7 beds 7 baths5,695 sq. ft.1240 Boy Scout Rd, OAKLAND, MD 21550
MLS# MDGA2008536Listed by: THE KW COLLECTIVE
$1,329,000Active6 beds 5 baths4,113 sq. ft.439 Paradise Hts, OAKLAND, MD 21550
MLS# MDGA2008472Listed by: RAILEY REALTY, INC.
$695,000Active4 beds 3 baths3,242 sq. ft.621 Paradise Hts, OAKLAND, MD 21550
MLS# MDGA2008332Listed by: RAILEY REALTY, INC.
$2,350,000Pending5 beds 7 baths5,376 sq. ft.2725 Stockslager Rd, OAKLAND, MD 21550
MLS# MDGA2008312Listed by: TAYLOR MADE DEEP CREEK VACATIONS & SALES
$2,399,000Active7 beds 5 baths4,691 sq. ft.41 Boyd Paugh Ln, OAKLAND, MD 21550
MLS# MDGA2007342Listed by: RAILEY REALTY, INC.
$749,900Active5 beds 4 baths2,364 sq. ft.25 Silver Tree Ln, OAKLAND, MD 21550
MLS# MDGA2009038Listed by: TAYLOR MADE DEEP CREEK VACATIONS & SALES
$225,000Pending2 beds 1 baths1,569 sq. ft.41 Fox Den Rd, OAKLAND, MD 21550
MLS# MDGA2009016Listed by: TAYLOR MADE DEEP CREEK VACATIONS & SALES
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© 2026 Better Homes and Gardens Real Estate LLC. An Anywhere Real Estate company. All rights reserved. Better Homes and Gardens® Real Estate is a registered trademark owned by Meredith Operations Corporation, licensed to Better Homes and Gardens Real Estate LLC and used with permission. Better Homes and Gardens Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Listing information is deemed reliable but is not guaranteed accurate.
Each office is independently owned and operated.
Any services or products provided by third parties are not provided by, affiliated with or related to Better Homes and Gardens Real Estate LLC, or its affiliated companies.
Protect your home and budget from life's surprises with an Assurant Home Warranty, backed by a partner that supports you through every step of homeownership. Explore Plans.
© 2026 Better Homes and Gardens Real Estate LLC. An Anywhere Real Estate company. All rights reserved. Better Homes and Gardens® Real Estate is a registered trademark owned by Meredith Operations Corporation, licensed to Better Homes and Gardens Real Estate LLC and used with permission. Better Homes and Gardens Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Listing information is deemed reliable but is not guaranteed accurate.
Each office is independently owned and operated.
Any services or products provided by third parties are not provided by, affiliated with or related to Better Homes and Gardens Real Estate LLC, or its affiliated companies.