- Any
- $ 100,000
- $ 150,000
- $ 200,000
- $ 400,000
- $ 800,000
- Any
- $ 200,000
- $ 300,000
- $ 400,000
- $ 600,000
- $ 1,000,000
- Any
- 1
- 2
- 3
- 4
- 5
- Any
- 1
- 2
- 3
- 4
- 5
- Any
- 1
- 2
- 3
- 4
- 5
- Any
- 1
- 2
- 3
- 4
- 5
22 Properties Available In 21550
- Default
- Price-High To Low
- Price-Low To High
- Newest Listings
- Beds (Most)
- Baths (Most)
- Year Built (Newest)
- Square Feet (Biggest)
![145 LOWER PENN POINT DR, Oakland, MD 21550](https://img.chime.me/imageemb/mls-listing/76/803521250798/b4c3ef17/1738873535/w600_original_LMqxDoIwEIfxJ7L3P0qb4sbmYuJA4tiAYKl6seH6_jGo4-_Lt9ZajkTTltNaD7LMeQSbss3ml-Sl5vaW_0BZxrQoAQAFWEeW0VDngv9y147YoA2RnfXxeo7-oqynth-eXX8feDKPkj4BAAD__w-jpg.webp)
$ 997,900
145 LOWER PENN POINT DR, Oakland, MD 21550
Single Family Home
MLS# MDGA2008610
Listed by Emillie H. Albrecht of Real Broker, LLC
![Bright MLS (BMLS)](https://cdn.chime.me/image/fs01/sitebuild/20181002/19/h80_original_23509894589943826-png.webp)
![202 DEERFIELD DR, Oakland, MD 21550](https://img.chime.me/imageemb/mls-listing/76/803525730772/9cb5c565/1738338688/w600_original_yigpKbDS108qykzPKNHNTU3JTDQw1CsoStGDCOXmFOsl5-dCFehn5iampxbrGxgYGOhbGBib6hubmBrpW5obWoC5IB6IE29kYGIRb2hqbBYf7hvvWhRVmloVahmc72keYWAWoJdVkA4IAAD__w-jpg.webp)
$ 320,500
202 DEERFIELD DR, Oakland, MD 21550
Single Family Home
MLS# MDGA2008628
Listed by Sharon K Kay Murray of Coldwell Banker Home Town Realty
![Bright MLS (BMLS)](https://cdn.chime.me/image/fs01/sitebuild/20181002/19/h80_original_23509894589943826-png.webp)
![476 GARRETT HWY, Oakland, MD 21550](https://img.chime.me/imageemb/mls-listing/76/803526131712/f41cc22b/1737056933/w600_original_yigpKbDS108qykzPKNHNTU3JTDQw1CsoStGDCOXmFOsl5-dCFehn5iampxbrGxgYGOhbGBib6hsbWFjomxtaQrggHogTb2RgYhFvaGpsFh_uGx-QZBRY6lzo42FSauLp5B2ol1WQDggAAP__-jpg.webp)
$ 250,000
476 GARRETT HWY, Oakland, MD 21550
Single Family Home
MLS# MDGA2008630
Listed by Brent Daniel Housley of Railey Realty, Inc.
![Bright MLS (BMLS)](https://cdn.chime.me/image/fs01/sitebuild/20181002/19/h80_original_23509894589943826-png.webp)
![15 VILLAGE DR #1, Oakland, MD 21550](https://img.chime.me/imageemb/mls-listing/76/803521381846/3173ecf8/1737167776/w600_original_LMpBCsIwEEbhEzXzJ7E6egB3YsGFuArRlnSKgyHN_ZGSLr_Hm2vNF6J3kTTXTqdRIqzJZTQt6Xc1n5_uA4nGNK0EAMTwPTl_YuIzN27aEBwOHGzvj-F5C26wneq9POKwvCBXs-T0DwAA__8-jpg.webp)
$ 530,000
15 VILLAGE DR #1, Oakland, MD 21550
Condo
MLS# MDGA2008612
Listed by Dale M Carpenter of Railey Realty, Inc.
![Bright MLS (BMLS)](https://cdn.chime.me/image/fs01/sitebuild/20181002/19/h80_original_23509894589943826-png.webp)
![3941 PLEASANT VALLEY RD, Oakland, MD 21550](https://img.chime.me/imageemb/mls-listing/76/803513036188/a84fb7f8/1738777738/w600_original_LMpRDoIwDIDhE7m21OHiFXSv-tiAwJjSsED1_Abl8fvzj2blDNAuOY120L7LDZIrS-f-SafVPWbdB8japH4FREQIyB7IVwSBuf5x0wap8BiEPNdyj3J6v-Jtamf5DMPlGs09S_oGAAD__w-jpg.webp)
$ 200,000
3941 PLEASANT VALLEY RD, Oakland, MD 21550
Single Family Home
MLS# MDGA2008586
Listed by Ben W Maust of Railey Realty, Inc.
![Bright MLS (BMLS)](https://cdn.chime.me/image/fs01/sitebuild/20181002/19/h80_original_23509894589943826-png.webp)
![405 SUNNYSIDE RD, Oakland, MD 21550](https://img.chime.me/imageemb/mls-listing/76/803501771030/a80603df/1737745621/w600_original_LMpBDsIgEEbhE8n8QFHiHVyojbqboG0oxomknYXe3jS4_F7epFr3RPe55Ek3Mg4lwZk6D6YleS3m8Zb_QEVSHhcCAIrwgWBjR86GxlUr2KGLbIPf8vXAmtzNH_nbny992X1O5lnzLwAA__8-jpg.webp)
$ 195,000
405 SUNNYSIDE RD, Oakland, MD 21550
Single Family Home
MLS# MDGA2008552
Listed by Steve A DuBrueler of Coldwell Banker Premier
![Bright MLS (BMLS)](https://cdn.chime.me/image/fs01/sitebuild/20181002/19/h80_original_23509894589943826-png.webp)
![439 PARADISE HTS, Oakland, MD 21550](https://img.chime.me/imageemb/mls-listing/76/803467729930/f8853d94/1738959670/w600_original_LMpBDoIwEEbhE9n5S6lM3Lo2cWdcTVBIW-NgA2O4viG4_F5eNqsnosdcUraDjkPp0bg6D25P-l7c86P_gYr2aVwIAIgRWmLPkTrPOzdtkAYti4_hKLeLTNbF730K1zPU1ry6V02_AAAA__8-jpg.webp)
$ 1,379,000
439 PARADISE HTS, Oakland, MD 21550
Single Family Home
MLS# MDGA2008472
Listed by Michael N Kennedy of Railey Realty, Inc.
![Bright MLS (BMLS)](https://cdn.chime.me/image/fs01/sitebuild/20181002/19/h80_original_23509894589943826-png.webp)
![621 PARADISE HTS, Oakland, MD 21550](https://img.chime.me/imageemb/mls-listing/76/803412354778/784d3b21/1736357509/w600_original_LMqxDoIwEIfxJ7L3x2sR3QyDE666XaqQo8bTCo3PbwiOvy_fWEo-EN2mpGPZ2NCniMrlqXdrsufs7m_7D5Qs6jATAFAD9hQ47Inr3cpFC2QL30gVuJZLJ9c2nnD-4iV67PyndY-svwAAAP__-jpg.webp)
$ 749,000
621 PARADISE HTS, Oakland, MD 21550
Single Family Home
MLS# MDGA2008332
Listed by Nick Fratz-Orr of Railey Realty, Inc.
![Bright MLS (BMLS)](https://cdn.chime.me/image/fs01/sitebuild/20181002/19/h80_original_23509894589943826-png.webp)
![339.03+/- ACRES-442 BAKER FARM RD, Oakland, MD 21550](https://img.chime.me/imageemb/mls-listing/76/803405161248/050bca2c/1733319983/w600_original_LMrBCoJAEIfxJ3LnP-rG1rFjIEVQHQdN2Z1ocNF9f8Lq-Pv4Uin5QDQsGlOpbBq1B7u8jO6X7L2652z_gdT6OK0EABTQtATPe2Lm8OWmDVKjDcK-2cmjEz0d7-cq-cs8XG9dqN0rx08AAAD__w-jpg.webp)
$ 1,899,900
339.03+/- ACRES-442 BAKER FARM RD, Oakland, MD 21550
Single Family Home
MLS# MDGA2008302
Listed by Kaleb M Hurley of Hurley Real Estate & Auctions
![Bright MLS (BMLS)](https://cdn.chime.me/image/fs01/sitebuild/20181002/19/h80_original_23509894589943826-png.webp)
![1489 MOUNTAINVIEW DR, Oakland, MD 21550](https://img.chime.me/imageemb/mls-listing/76/803358873250/3891ba96/1736346213/w600_original_LMqxDsIgFEbhJ5L7A61SV2cdXOp2U4VQqjdiYfHtDer4nZy51rwnuq4pznUjwacJRuXVq1-SR1G3p_wHSjLFUAgAyMFa6t2gyenOfNnUwAadY93bLY9HPo0vhLe_L4dy2Z0HqCXHTwAAAP__-jpg.webp)
$ 709,000
1489 MOUNTAINVIEW DR, Oakland, MD 21550
Single Family Home
MLS# MDGA2008140
Listed by Larry E Smith of Railey Realty, Inc.
![Bright MLS (BMLS)](https://cdn.chime.me/image/fs01/sitebuild/20181002/19/h80_original_23509894589943826-png.webp)
![5 LAUREL BROOK DR #5, Oakland, MD 21550](https://img.chime.me/imageemb/mls-listing/76/803361442416/ed137275/1734481868/w600_original_LMpBCoMwEEbhE5n5m7EauuzeXSHdDbFKTHFoMCn0-EV0-T3eUmu-EY1bikttdJ5SgDV5m8yRdC3m9dFzoKQhzoUAgByYqbO2J4f24K4dYtE6uVy5Ez_IsH6f2jfF3_nxG4M37xz_AQAA__8-jpg.webp)
$ 223,500
5 LAUREL BROOK DR #5, Oakland, MD 21550
Townhouse
MLS# MDGA2008150
Listed by Sherry L Nally of Berkshire Hathaway HomeServices Homesale Realty
![Bright MLS (BMLS)](https://cdn.chime.me/image/fs01/sitebuild/20181002/19/h80_original_23509894589943826-png.webp)
![17 LAUREL BROOK #17, Oakland, MD 21550](https://img.chime.me/imageemb/mls-listing/76/803325107726/dd8ee735/1738604929/w600_original_LMrBDsIgDIDhJxot4LbiC3jy7LFB17AuNhJGfH4z9fj9-dfe6xng3rSsfTBZNKN3tS3ul-y5u8fL_gOo5SI7ICICYRwhRUow0xS-PHSAA56I_Rgnvl1Zks7qBw2b5Ut7i9tq-QQAAP__-jpg.webp)
$ 285,000
17 LAUREL BROOK #17, Oakland, MD 21550
Condo
MLS# MDGA2008036
Listed by Michael Cumerlato of Jason Mitchell Group
![Bright MLS (BMLS)](https://cdn.chime.me/image/fs01/sitebuild/20181002/19/h80_original_23509894589943826-png.webp)
![5267 GEORGE WASHINGTON HWY, Oakland, MD 21550](https://img.chime.me/imageemb/mls-listing/76/803342227616/69582380/1738431133/w600_original_yigpKbDS108qykzPKNHNTU3JTDQw0isoStGDCOXmFOsl5-dCFehn5iampxbrGxgYGOhbGBgb65uYGBrpm5uYmIC5IB6IE29kYGIRb2hqbBYf7hufH5TvURQZkGdq6pWVHGzuqJdVkA4IAAD__w-jpg.webp)
$ 260,000
5267 GEORGE WASHINGTON HWY, Oakland, MD 21550
Single Family Home
MLS# MDGA2008086
Listed by Jennifer Jackson of Charis Realty Group
![Bright MLS (BMLS)](https://cdn.chime.me/image/fs01/sitebuild/20181002/19/h80_original_23509894589943826-png.webp)
![1385 MOUNTAINVIEW DR, Oakland, MD 21550](https://img.chime.me/imageemb/mls-listing/76/802973156204/ce96461d/1738012929/w600_original_LMpBDsIgEEbhE8n8YiVTd8aVxq5ZTmpLANNJSeH-MVWX38tLrZUL0WvLMbWDhjmPsKZss_klXaqZVv0PlHWMoRIAEMP2xOCO2Dr-ctcOsehYjueTEz9IXR8h9d5P92G5utvTvEv8BAAA__8-jpg.webp)
$ 659,000
1385 MOUNTAINVIEW DR, Oakland, MD 21550
Single Family Home
MLS# MDGA2007024
Listed by Michael Cumerlato of Jason Mitchell Group
![Bright MLS (BMLS)](https://cdn.chime.me/image/fs01/sitebuild/20181002/19/h80_original_23509894589943826-png.webp)
![565 GLENDALE RD #115A, Oakland, MD 21550](https://img.chime.me/imageemb/mls-listing/76/802979898146/8be7133a/1738012924/w600_original_yigpKbDS108qykzPKNHNTU3JTDQw0isoStGDCOXmFOsl5-dCFehn5iampxbrGxgYGOhbGBhZgggTfSNDcwgXxANx4o0MTCziDU2NzeLDfeMjnS1zciozK7JcXExC08LK9bIK0gEBAAD__w-jpg.webp)
$ 299,000
565 GLENDALE RD #115A, Oakland, MD 21550
Condo
MLS# MDGA2007036
Listed by Kevin D Liller of Railey Realty, Inc.
![Bright MLS (BMLS)](https://cdn.chime.me/image/fs01/sitebuild/20181002/19/h80_original_23509894589943826-png.webp)
![LOT 1 BETTS LN, Oakland, MD 21550](https://img.chime.me/imageemb/mls-listing/76/803220305614/d5150056/1735414272/w600_original_LMoxDsIwDEbhExH_SSAEVjYEQgyI0Sq0dYOwiFov3B4VGL-nN5jVLdFtLDLYQru2NPCujq37JX1O7v7S_0BFG-kmAgDKiIECImjjkb6cNYMDlpn9Kia-Hvlw6sP6ne28u8g-9d49qnwCAAD__w-jpg.webp)
$ 59,000
LOT 1 BETTS LN, Oakland, MD 21550
Vacant Land
MLS# MDGA2007716
Listed by Amy White of Railey Realty, Inc.
![Bright MLS (BMLS)](https://cdn.chime.me/image/fs01/sitebuild/20181002/19/h80_original_23509894589943826-png.webp)
![17848 GARRETT HWY, Oakland, MD 21550](https://img.chime.me/imageemb/mls-listing/76/803052005356/1c307cd8/1738288932/w600_original_LMqxDsIgEIfxJ4L7t5RLdXR3cVEnUi0BDBcvlPePqTr-vny5dz0SPVpJuRuJa1kwWG2r_SWpm32-5T9QkSXFjQCAZjgQez4Q2I1f7toRRkxzGLzjcD2HavKptshq7tVPl5t9afoEAAD__w-jpg.webp)
$ 1,500,000
17848 GARRETT HWY, Oakland, MD 21550
Commercial
MLS# MDGA2007238
Listed by Michael Cumerlato of Jason Mitchell Group
![Bright MLS (BMLS)](https://cdn.chime.me/image/fs01/sitebuild/20181002/19/h80_original_23509894589943826-png.webp)
![1527 MARYLAND HIGHWAY, Oakland, MD 21550](https://img.chime.me/imageemb/mls-listing/76/802956860310/8e3bc0f0/1737588858/w600_original_LMq9DsIgFEfxJ4L7v9QPcHVx0LjpSKptKLZXCfD-MWjH38mZak0HokeOYapKxiH2YJ3yoP9JlqKfH1kHitKHsRAAkIVxtHfMBNfZH5savMHGet52O3-_eLWwsef5na9zuR1PSr9S-AYAAP__-jpg.webp)
$ 650,000
1527 MARYLAND HIGHWAY, Oakland, MD 21550
Commercial
MLS# MDGA2006980
Listed by Nick Fratz-Orr of Railey Realty, Inc.
![Bright MLS (BMLS)](https://cdn.chime.me/image/fs01/sitebuild/20181002/19/h80_original_23509894589943826-png.webp)
![3501 GEORGE WASHINGTON HWY, Oakland, MD 21550](https://img.chime.me/imageemb/mls-listing/76/802887464208/3dd0c8fb/1737419640/w600_original_yigpKbDS108qykzPKNHNTU3JTDQw0isoStGDCOXmFOsl5-dCFehn5iampxbrGxgYGOhbGBgb6hubmZroGxlZQrggHogTb2RgYhFvaGpsFh_uGx_gahJlmOGS6RcQ7Faa5Wqil1WQDggAAP__-jpg.webp)
$ 125,000
3501 GEORGE WASHINGTON HWY, Oakland, MD 21550
Commercial
MLS# MDGA2006694
Listed by Zachary J Wesolowski of Railey Realty, Inc.
![Bright MLS (BMLS)](https://cdn.chime.me/image/fs01/sitebuild/20181002/19/h80_original_23509894589943826-png.webp)
![LOT 15 OVERLOOK DR, Oakland, MD 21550](https://img.chime.me/imageemb/mls-listing/76/802874513746/521a04dc/1738449595/w600_original_NMq7DoJAEEbhJ2LmnwXMxlYaC0u1nHDLssSJE9j3jyFq-Z2cpRQ_Mw9bTkupbJ5yj0C-TfRN9tppfNtv4Gx9mncGAI4Iwo0gcv3noQMa0ESVtj7p86a66mW8dqLD49551dLq6RMAAP__-jpg.webp)
$ 29,900
LOT 15 OVERLOOK DR, Oakland, MD 21550
Vacant Land
MLS# MDGA2006656
Listed by Nina A Beitzel of Railey Realty, Inc.
![Bright MLS (BMLS)](https://cdn.chime.me/image/fs01/sitebuild/20181002/19/h80_original_23509894589943826-png.webp)
![LOT 5A VALLEY ROAD, Oakland, MD 21550](https://img.chime.me/imageemb/mls-listing/76/802078628670/9f1dfd11/1735934492/w600_original_yigpKbDS108qykzPKNHNTU3JTDQw1CsoStGDCOXmFOsl5-dCFehn5iampxbrGxgYGOhbGBgZ61taWhromxhCuSAeiBNvZGBiEW9oamwWH-4b75Js4JZVGWyZk1laFVFo5KmXVZAOCAAA__8-jpg.webp)
$ 30,000
LOT 5A VALLEY ROAD, Oakland, MD 21550
Vacant Land
MLS# MDGA2004308
Listed by Nick Fratz-Orr of Railey Realty, Inc.
![Bright MLS (BMLS)](https://cdn.chime.me/image/fs01/sitebuild/20181002/19/h80_original_23509894589943826-png.webp)
![PARADISE POINT RD, Oakland, MD 21550](https://static.chimeroi.com/image/house_default.png)
$ 170,000
PARADISE POINT RD, Oakland, MD 21550
Vacant Land
MLS# MDGA2003916
Listed by Anthony Zorzit of Eagle Commercial Realty
![Bright MLS (BMLS)](https://cdn.chime.me/image/fs01/sitebuild/20181002/19/h80_original_23509894589943826-png.webp)