Movoto Real Estate

Homes Under $300K Price For Sale in Oakland, MD

101 Homes
 
127 Jeffrey Ln #4, Oakland, MD 21550
  • $279,000
  • 2Bd
  • 1Ba
  • 700 Sq Ft
New 32 Hours
lot40 Dogwood Dr, Oakland, MD 21550
  • $4,500
  • 0.47 Acre
New 39 Hours
565 Glendale Rd #316, Oakland, MD 21550
  • $279,000
  • 2Bd
  • 1Ba
  • 772 Sq Ft
New 4 Days
809 N Mtn, Oakland, MD 21550
  • $20,000
  • 2Bd
  • 2Ba
  • 792 Sq Ft
New 4 Days
13 Laurel Court Ct, Oakland, MD 21550
  • $85,000
  • 0.76 Acre
New 4 Days
Whispering Pines Lane, Oakland, MD 21550
  • $20,000
  • 0.51 Acre
New 5 Days
1959 Birchwood Dr, Oakland, MD 21550
  • $235,000
  • 2Bd
  • 2Ba
  • 1,152 Sq Ft
New 7 Days
139 S Oakhall Dr, Oakland, MD 21550
  • $229,000
  • 3Bd
  • 2Ba
  • 1,612 Sq Ft
586 Bray School Rd, Oakland, MD 21550
  • $289,000
  • 4Bd
  • 2Ba
  • 2,240 Sq Ft
20160 Garett Hwy #105A, Oakland, MD 21550
  • $296,500
  • 1Bd
  • 1Ba
  • 600 Sq Ft
wild turkey lane LOT 28, Oakland, MD 21550
  • $37,500
  • 1 Acre
cedar lane LOT 66, Oakland, MD 21550
  • $6,500
  • 0.94 Acre
102 Roanoke Ave, Oakland, MD 21550
  • $74,990
  • 3Bd
  • 1Ba
  • 1,932 Sq Ft
808 N St, Oakland, MD 21550
  • $219,900
  • 2Bd
  • 2Ba
  • 1,008 Sq Ft
$10K
Yough View Drive, Oakland, MD 21550
  • $40,000
  • 2.43 Acre
lot4 Hunters Ridge Dr, Oakland, MD 21550
  • $65,000
  • 4.91 Acre
lot8 Stool Rock Rd, Oakland, MD 21550
  • $10,000
  • 0.46 Acre
24 Woodlands Hill Ln, Oakland, MD 21550
  • $137,500
  • 1.53 Acre
Grey Squirrel Road, Oakland, MD 21550
  • $40,000
  • 3.46 Acre
Mayhew Inn Road, Oakland, MD 21550
  • $169,900
  • 0.97 Acre
2560 Bray School Rd, Oakland, MD 21550
  • $249,900
  • 7.72 Acre
565 Glendale Rd #213, Oakland, MD 21550
  • $225,000
  • 1Bd
  • 1Ba
206 W Liberty St, Oakland, MD 21550
  • $149,000
  • 2Bd
  • 1Ba
  • 2,008 Sq Ft
$25.9K
40 Sunshine, Oakland, MD 21550
  • $159,000
  • 3Bd
  • 1Ba
  • 1,516 Sq Ft
$10K
Bear Drive E, Oakland, MD 21550
  • $19,900
  • 1.05 Acre
5 Laurel Brook Dr #5, Oakland, MD 21550
  • $269,900
  • 2Bd
  • 2Ba
  • 1,400 Sq Ft
robinwood drive, Oakland, MD 21550
  • $175,000
  • 3.46 Acre
22 Woodlands Hill Ln, Oakland, MD 21550
  • $159,000
  • 2.02 Acre
16 Woodlands Hill Ct, Oakland, MD 21550
  • $149,000
  • 3.29 Acre
robinwood drive, Oakland, MD 21550
  • $99,000
  • 1.84 Acre
102 N 3rd St, Oakland, MD 21550
  • $259,900
  • 3Bd
  • 2Ba
  • 1,998 Sq Ft
lot B Loch Deer Rd, Oakland, MD 21550
  • $259,000
  • 42 Acre
lot18 Buck Dr, Oakland, MD 21550
  • $19,900
  • 1.35 Acre
Maple Del Lane, Oakland, MD 21550
  • $39,500
  • 1.05 Acre
$2.5K
6 Cedar Ln, Oakland, MD 21550
  • $12,500
  • 0.49 Acre
$6.5K
3 15 Acres Woodlands Hill Ln, Oakland, MD 21550
  • $200,000
  • 3.15 Acre
lot9 Woodlands Hill Ln, Oakland, MD 21550
  • $95,000
  • 2.08 Acre
lot10 Woodlands Hill Ln, Oakland, MD 21550
  • $95,000
  • 2.6 Acre
5 Acres Lake Shore Dr, Oakland, MD 21550
  • $250,000
  • 5 Acre
Red Run Heights Road, Oakland, MD 21550
  • $49,900
  • 1.15 Acre
8760 Oakland Sang Run Rd, Oakland, MD 21550
  • $79,500
  • 2.53 Acre
$3K
6 89 Acres Woodlands Hill Dr, Oakland, MD 21550
  • $250,000
  • 6.89 Acre
9 75 Ac Dennett Rd, Oakland, MD 21550
  • $169,000
  • 9.75 Acre
206 Mayhew Inn Rd, Oakland, MD 21550
  • $224,900
  • 1Bd
  • 1Ba
Sanders Lane, Oakland, MD 21550
  • $150,000
  • 21.46 Acre
lot24 Eastview Pl, Oakland, MD 21550
  • $30,000
  • 1.01 Acre
$19K
lot233 Cumberland, Oakland, MD 21550
  • $33,000
  • 0.46 Acre
$2K
lot6 B Betts Ln, Oakland, MD 21550
  • $49,900
  • 1.38 Acre
565 Glendale Rd #306, Oakland, MD 21550
  • $249,900
  • 2Bd
  • 1Ba
  • 772 Sq Ft
132 132a Tarn Dr, Oakland, MD 21550
  • $160,000
  • 3.04 Acre
1 - 50 of 101 Homes for sale in Oakland, MD
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Oakland, MD real estate market trends

Statistics as of September 2026
$545K
Avg. list price
$259/Sqft
Avg. price/sqft
112
Homes for sale
2,165 Sqft
Avg. home size
107 Days
Avg. days on market
Movoto makes it easy to track market trends in Oakland, MD. Whether you’re entering the market or planning your next move, understanding these key metrics can guide smart decisions. Looking for more detailed housing market stats in Oakland, MD?
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Information Deemed Reliable But Not Guaranteed
The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Movoto participates, and is provided by BRIGHT through a licensing agreement.The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated: 9/22/2026. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closedor are no longer being offered for sale. Some real estate firms do not participate in IDX and their listings do not appear on this website. Some properties listed with participating firms do not appear on this website at the request of the seller. This home sale information is not to be construed as an appraisal and may not be used as such for any purpose. BRIGHTMLS is the (or a) provider of this home sale information and has compiled content from various sources. Some properties represented may not have actually solddue to reporting errors.
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