10,731

Oakland, MD Homes

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  • LOT 2 Beaver Run Rd, Oakland, MD 21550
    LOT 2 Beaver Run Rd, Oakland, MD 21550
    LOT 2 Beaver Run Rd, Oakland, MD 21550
    /9

    $3,500

    • Land
    • 0.48 Acre
    • $7,292 per Acre

    LOT 2 Beaver Run Rd, Oakland, MD 21550

    Tucked away in the stunning mountains of Western Maryland, this unbuildable lot provides a serene escape into nature, offering breathtaking views and abundant wildlife. Located in the Youghiogheny Mountain Resort, this membership-only lot grants exclusive access to over 50 miles of private roads and trails, ideal for ATV and side-by-side adventures. Resort amenities include a community clubhouse,

    Elizabeth Broadwater Taylor Made Deep Creek Vacations & Sales

    LOT 2 Beaver Run Rd, Oakland, MD 21550
  • 465 King Wildesen Rd, Oakland, MD 21550
    465 King Wildesen Rd, Oakland, MD 21550
    465 King Wildesen Rd, Oakland, MD 21550
    /40

    $335,000 Sold May 23, 2025

    465 King Wildesen Rd, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 768 Sq Ft
    • Built 1988

    Last Sold Summary

    • 22% Below List Price
    • $436/SF
    • 123 Days On Market

    Current Estimated Value $331,001

    Last Listing Agent ADAM MURRAY BERKSHIRE HATHAWAY HOMESERVICES TOUCHDOWN HOME PROS REALTY

    465 King Wildesen Rd, Oakland, MD 21550
    • 2276 Paradise Point Rd, Oakland, MD 21550
      2276 Paradise Point Rd, Oakland, MD 21550
      2276 Paradise Point Rd, Oakland, MD 21550
      /65

      Est $4,056,003 Not Listed For Sale

      • 8 Beds
      • 5.5 Baths
      • 8,453 Sq Ft

      2276 Paradise Point Rd, Oakland, MD 21550

      2276 Paradise Point Rd, Oakland, MD 21550
  • 25 Silver Tree Ln, Oakland, MD 21550
    25 Silver Tree Ln, Oakland, MD 21550
    25 Silver Tree Ln, Oakland, MD 21550
    /52

    $749,900

    • 5 Beds
    • 4 Baths
    • 2,364 Sq Ft

    25 Silver Tree Ln, Oakland, MD 21550

    Beautiful lake access retreat located in the Silver Tree Landings community with an available home warranty. This recently updated contemporary home feels warm and inviting from the moment you walk in (upgrade list available). Offering hardwood flooring, granite countertops, two stone propane fireplaces and cathedral ceilings. The abundance of windows allows the natural light to brighten any

    Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    25 Silver Tree Ln, Oakland, MD 21550
  • 9 & 10 Grouse Run Rd, Oakland, MD 21550
    9 & 10 Grouse Run Rd, Oakland, MD 21550
    9 & 10 Grouse Run Rd, Oakland, MD 21550
    /20

    $17,000 Sold Oct 29, 2025

    9 & 10 Grouse Run Rd, Oakland, MD 21550

    • Land
    • 0.96 Acre
    • $17,708 per Acre

    Last Sold Summary

    • 50 Days On Market

    Last Listing Agent Brent Housley Railey Realty, Inc.

    9 & 10 Grouse Run Rd, Oakland, MD 21550
    • 5289 Oakland Sang Run Rd, Oakland, MD 21550
      5289 Oakland Sang Run Rd, Oakland, MD 21550
      5289 Oakland Sang Run Rd, Oakland, MD 21550
      /56

      Est $407,872 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,638 Sq Ft

      5289 Oakland Sang Run Rd, Oakland, MD 21550

      5289 Oakland Sang Run Rd, Oakland, MD 21550
  • 0 Longview Ln, Oakland, MD 21550
    0 Longview Ln, Oakland, MD 21550
    0 Longview Ln, Oakland, MD 21550
    /9

    $49,900

    • Land
    • 1 Acre
    • $49,900 per Acre

    0 Longview Ln, Oakland, MD 21550

    1.00 Acre wooded lot loacted in George Brunson Subdivision. Close to Deep Creek Lake, Wisp Ski Resort and Oakland. Approved perc

    Linda Deremer Appalachian Realty

    0 Longview Ln, Oakland, MD 21550
  • 0 E Water St, Oakland, MD 21550
    0 E Water St, Oakland, MD 21550
    /2

    $8,000 Sold Aug 29, 2025

    0 E Water St, Oakland, MD 21550

    • Land
    • 0.33 Acre
    • $24,242 per Acre

    Last Sold Summary

    • 2 Days On Market

    Last Listing Agent Nick Fratz-Orr Railey Realty, Inc.

    0 E Water St, Oakland, MD 21550
    • 620 E Green St, Oakland, MD 21550
      620 E Green St, Oakland, MD 21550
      620 E Green St, Oakland, MD 21550
      /65

      Est $158,939 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 1,668 Sq Ft

      620 E Green St, Oakland, MD 21550

      620 E Green St, Oakland, MD 21550
  • 1737 King Wildesen Rd, Oakland, MD 21550
    1737 King Wildesen Rd, Oakland, MD 21550
    1737 King Wildesen Rd, Oakland, MD 21550
    /46

    $299,900

    • 3 Beds
    • 2 Baths
    • 1,736 Sq Ft

    1737 King Wildesen Rd, Oakland, MD 21550

    Nestled on 10 secluded acres of serene woodland and open fields, this traditional cedar-sided home offers the perfect blend of rustic charm and modern comfort—all just 10 minutes from downtown Oakland. This well-maintained home features 3 spacious bedrooms and 2 full bathrooms, including a main floor master suite for added convenience. Inside, you’ll find brand-new luxury vinyl plank (LVP)

    Justin Liller Railey Realty, Inc.

    1737 King Wildesen Rd, Oakland, MD 21550
  • 204 E St, Oakland, MD 21550
    204 E St, Oakland, MD 21550
    204 E St, Oakland, MD 21550
    /37

    $120,000 Sold Dec 04, 2025

    204 E St, Oakland, MD 21550

    • 5 Beds
    • 2 Baths
    • 2,084 Sq Ft
    • Built 1975

    Last Sold Summary

    • $58/SF
    • 1 Day On Market

    Last Listing Agent Sheila Howell Lake Homes Realty, LLC

    204 E St, Oakland, MD 21550
    • 501 G St, Oakland, MD 21550
      501 G St, Oakland, MD 21550
      501 G St, Oakland, MD 21550
      /76

      Est $223,249 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,520 Sq Ft

      501 G St, Oakland, MD 21550

      501 G St, Oakland, MD 21550
  • 143 Manor Dr, Oakland, MD 21550
    143 Manor Dr, Oakland, MD 21550
    143 Manor Dr, Oakland, MD 21550
    /48

    $299,900 Under Contract

    • 3 Beds
    • 1.5 Baths
    • 1,786 Sq Ft

    143 Manor Dr, Oakland, MD 21550

    Take a look at this brick home on great lot in Mitchell Manor. Enjoy the convenience of public sewer without the obligation to pay town taxes as this home is not located within the town limits of Oakland. Paved driveway leads to a one car garage. Electric baseboard heat with wood burning fireplace insert in the upstairs fireplace and the fireplace in the family room on lower level is also a wood

    Kevin Liller Railey Realty, Inc.

    143 Manor Dr, Oakland, MD 21550
  • 5267 George Washington Hwy, Oakland, MD 21550
    5267 George Washington Hwy, Oakland, MD 21550
    5267 George Washington Hwy, Oakland, MD 21550
    /52

    $250,000 Sold Mar 21, 2025

    5267 George Washington Hwy, Oakland, MD 21550

    • 4 Beds
    • 1.5 Baths
    • 2,352 Sq Ft
    • Built 1974

    Last Sold Summary

    • $106/SF
    • 153 Days On Market

    Current Estimated Value $252,521

    Last Listing Agent Jennifer Jackson Charis Realty Group

    5267 George Washington Hwy, Oakland, MD 21550
    • 107 Pleasant Hill Cir, Oakland, MD 21550
      107 Pleasant Hill Cir, Oakland, MD 21550
      107 Pleasant Hill Cir, Oakland, MD 21550
      /35

      Est $386,529 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,384 Sq Ft

      107 Pleasant Hill Cir, Oakland, MD 21550

      107 Pleasant Hill Cir, Oakland, MD 21550
  • 0 Edgewater Dr Unit 4 MDGA2009106, Oakland, MD 21550
    0 Edgewater Dr Unit 4 MDGA2009106, Oakland, MD 21550
    0 Edgewater Dr Unit 4 MDGA2009106, Oakland, MD 21550
    /16

    $299,000

    • Land
    • 0 Acre

    0 Edgewater Dr Unit 4 MDGA2009106, Oakland, MD 21550

    Rare offering! LAKE VIEW building site with TWO BOAT SLIPS! Located off popular Lake Shore Drive in the Edgewater community, this lot features a building envelope surrounded by community green space. Deep water, somewhat flat area by the lake, feels like small little park area. Dock access is directly across the street and a short walk away away - 100 yards +/-. Paved parking area for easy

    Jay Ferguson Taylor Made Deep Creek Vacations & Sales

    0 Edgewater Dr Unit 4 MDGA2009106, Oakland, MD 21550
  • 403 O St, Oakland, MD 21550
    403 O St, Oakland, MD 21550
    403 O St, Oakland, MD 21550
    /47

    $270,000 Sold Jun 20, 2025

    403 O St, Oakland, MD 21550

    • 4 Beds
    • 3.5 Baths
    • 2,240 Sq Ft
    • Built 1976

    Last Sold Summary

    • $121/SF
    • 329 Days On Market

    Current Estimated Value $271,902

    Last Listing Agent ANGELA BOSLEY Taylor Made Deep Creek Vacations & Sales

    403 O St, Oakland, MD 21550
    • 125 Matthew Rd, Oakland, MD 21550
      125 Matthew Rd, Oakland, MD 21550
      125 Matthew Rd, Oakland, MD 21550
      /66

      Est $445,368 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,324 Sq Ft

      125 Matthew Rd, Oakland, MD 21550

      125 Matthew Rd, Oakland, MD 21550
  • 41 Fox Den Rd, Oakland, MD 21550
    41 Fox Den Rd, Oakland, MD 21550
    41 Fox Den Rd, Oakland, MD 21550
    /25

    $225,000 Under Contract

    • 2 Beds
    • 1 Bath
    • 1,569 Sq Ft

    41 Fox Den Rd, Oakland, MD 21550

    Nestled in the heart of Deep Creek Lake, this charming and fully furnished cottage offers the perfect blend of relaxation and investment potential. Recently remodeled, it features a brand-new modern kitchen that seamlessly opens to the living area, refinished wood floors, and upgraded electric,. The light and airy upstairs space enhances the home's inviting atmosphere, complemented by large

    Laura Newhall Taylor Made Deep Creek Vacations & Sales

    41 Fox Den Rd, Oakland, MD 21550
  • 1489 Mountainview Dr, Oakland, MD 21550
    1489 Mountainview Dr, Oakland, MD 21550
    1489 Mountainview Dr, Oakland, MD 21550
    /80

    $696,000 Sold Apr 02, 2025

    1489 Mountainview Dr, Oakland, MD 21550

    • 5 Beds
    • 3 Baths
    • 3,066 Sq Ft
    • Built 2001

    Last Sold Summary

    • $227/SF
    • 170 Days On Market

    Current Estimated Value $710,647

    Last Listing Agent Larry Smith Railey Realty, Inc.

    1489 Mountainview Dr, Oakland, MD 21550
    • 20488 Garrett Hwy, Oakland, MD 21550
      20488 Garrett Hwy, Oakland, MD 21550
      20488 Garrett Hwy, Oakland, MD 21550
      /6

      Est $677,123 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 840 Sq Ft

      20488 Garrett Hwy, Oakland, MD 21550

      20488 Garrett Hwy, Oakland, MD 21550
  • 98 Bear Run Rd, Oakland, MD 21550
    98 Bear Run Rd, Oakland, MD 21550
    98 Bear Run Rd, Oakland, MD 21550
    /30

    $550,000

    • 3 Beds
    • 2 Baths
    • 1,080 Sq Ft

    98 Bear Run Rd, Oakland, MD 21550

    Make it your own! This 2-acre parcel comes with two additional parcels of 17.96 and 24.23 acres for a total of 42.19 acres. The 2-acre parcel is improved by a fully furnished (26’X42’), 3-bedroom, 2-bathroom Ranch style dwelling and a large parking area. The interior offers a spacious living room, and an eat-in kitchen with all appliances, furniture and window AC units. The land is un-zoned

    Dan (Sussan) Duggan 1 Real Estate Source LLC

    98 Bear Run Rd, Oakland, MD 21550
  • 421 Penn Cove Rd, Oakland, MD 21550
    421 Penn Cove Rd, Oakland, MD 21550
    421 Penn Cove Rd, Oakland, MD 21550
    /107

    $1,350,000 Sold Sep 19, 2025

    421 Penn Cove Rd, Oakland, MD 21550

    • 4 Beds
    • 3.5 Baths
    • 4,284 Sq Ft
    • Built 1986

    Last Sold Summary

    • $315/SF
    • 54 Days On Market

    Current Estimated Value $1,414,329

    Last Listing Agent Steven Ritchie Railey Realty, Inc.

    421 Penn Cove Rd, Oakland, MD 21550
    • 739 Glendale Rd, Oakland, MD 21550
      739 Glendale Rd, Oakland, MD 21550
      739 Glendale Rd, Oakland, MD 21550
      /85

      Est $1,826,750 Not Listed For Sale

      • 6 Beds
      • 6.5 Baths
      • 4,160 Sq Ft

      739 Glendale Rd, Oakland, MD 21550

      739 Glendale Rd, Oakland, MD 21550
  • 3257 George Washington Hwy, Oakland, MD 21550
    3257 George Washington Hwy, Oakland, MD 21550
    3257 George Washington Hwy, Oakland, MD 21550
    /8

    $280,000

    • Land
    • 36.72 Acres
    • $7,625 per Acre

    3257 George Washington Hwy, Oakland, MD 21550

    Discover approximately 36.72 acres of beautiful wooded land offering privacy, mountain views, and exceptional convenience. This expansive property provides easy access to both George Washington Highway and Garrett Highway, making travel simple while still feeling tucked away in nature. Located within a 30-minute drive of Deep Creek Lake and Wisp Resort, as well as sought-after West Virginia

    Justin Liller Railey Realty, Inc.

    3257 George Washington Hwy, Oakland, MD 21550
  • 249 Marys Ln, Oakland, MD 21550
    249 Marys Ln, Oakland, MD 21550
    249 Marys Ln, Oakland, MD 21550
    /67

    $855,000 Sold May 12, 2025

    249 Marys Ln, Oakland, MD 21550

    • 5 Beds
    • 3.5 Baths
    • 2,874 Sq Ft
    • Built 2017

    Last Sold Summary

    • $297/SF
    • 7 Days On Market

    Current Estimated Value $890,056

    Last Listing Agent Jon Bell Railey Realty, Inc.

    249 Marys Ln, Oakland, MD 21550
    • 723 E Alder St, Oakland, MD 21550
      723 E Alder St, Oakland, MD 21550
      723 E Alder St, Oakland, MD 21550
      /73

      Est $246,939 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,764 Sq Ft

      723 E Alder St, Oakland, MD 21550

      723 E Alder St, Oakland, MD 21550
  • 285 Lake Shore Dr, Oakland, MD 21550
    285 Lake Shore Dr, Oakland, MD 21550
    285 Lake Shore Dr, Oakland, MD 21550
    /47

    $1,199,000

    • 5 Beds
    • 4.5 Baths
    • 2,593 Sq Ft

    285 Lake Shore Dr, Oakland, MD 21550

    Nestled on 1.52 private acres with 500 feet of frontage on Deep Creek Lake, this 5-bedroom, 4.5-bath home combines comfort with exceptional waterfront living. The open floor plan features soaring two-story ceilings with exposed beams, wood flooring, upgraded countertops, and a striking brick fireplace. Outdoor spaces include multiple decks, balconies, porches, and a hot tub—perfect for

    Terring Wang Keller Williams Capital Properties

    285 Lake Shore Dr, Oakland, MD 21550
  • 939 Glendale Rd, Oakland, MD 21550
    939 Glendale Rd, Oakland, MD 21550
    939 Glendale Rd, Oakland, MD 21550
    /61

    $820,000 Sold Sep 02, 2025

    939 Glendale Rd, Oakland, MD 21550

    • 3 Beds
    • 3 Baths
    • Built 1990

    Last Sold Summary

    • 18 Days On Market

    Current Estimated Value $836,535

    Last Listing Agent Sean Sober Taylor Made Deep Creek Vacations & Sales

    939 Glendale Rd, Oakland, MD 21550
    • 943 S Blakeslee Rd, Oakland, MD 21550
      943 S Blakeslee Rd, Oakland, MD 21550
      943 S Blakeslee Rd, Oakland, MD 21550
      /130

      Est $1,170,887 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 3,426 Sq Ft

      943 S Blakeslee Rd, Oakland, MD 21550

      943 S Blakeslee Rd, Oakland, MD 21550
  • Lot 53 Mountainview Dr, Oakland, MD 21550
    Lot 53 Mountainview Dr, Oakland, MD 21550
    Lot 53 Mountainview Dr, Oakland, MD 21550
    /5

    $124,900

    • Land
    • 1.02 Acres
    • $122,451 per Acre

    Lot 53 Mountainview Dr, Oakland, MD 21550

    Ready to build lot in Deep Creek Lake's Mountainside Subdivision. This wooded lot is relatively level can be connected to public water and has an approved percolation test for an onsite septic system. Build you dream home in this mountaintop community with homes values ranging up to $2,000,000.

    Richard Saunders Samson Properties

    Lot 53 Mountainview Dr, Oakland, MD 21550
  • 237 Glendale Rd, Oakland, MD 21550
    237 Glendale Rd, Oakland, MD 21550
    237 Glendale Rd, Oakland, MD 21550
    /100

    $1,860,000 Sold Oct 06, 2025

    237 Glendale Rd, Oakland, MD 21550

    • 7 Beds
    • 6.5 Baths
    • 3,735 Sq Ft
    • Built 2002

    Last Sold Summary

    • $498/SF
    • 88 Days On Market

    Current Estimated Value $1,883,037

    Last Listing Agent Bill Weissgerber Railey Realty, Inc.

    237 Glendale Rd, Oakland, MD 21550
    • 223 N 2nd St, Oakland, MD 21550
      223 N 2nd St, Oakland, MD 21550
      223 N 2nd St, Oakland, MD 21550
      /88

      Est $406,120 Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 3,120 Sq Ft

      223 N 2nd St, Oakland, MD 21550

      223 N 2nd St, Oakland, MD 21550
  • 1358 Crellin Underwood Rd, Oakland, MD 21550
    1358 Crellin Underwood Rd, Oakland, MD 21550
    1358 Crellin Underwood Rd, Oakland, MD 21550
    /37

    $85,000

    • 2 Beds
    • 1 Bath
    • 864 Sq Ft

    1358 Crellin Underwood Rd, Oakland, MD 21550

    Charming 2-bedroom, 1-bath home offering a fantastic opportunity for buyers looking to add their own personal touch. Recent updates include a metal roof, 2 propane wall unit heaters, and a hot water heater. Enjoy the back covered deck overlooking the woods and the youghiogheny river below. This property needs a bit of TLC but is full of potential and character. Located in a highly desirable

    Lucas Muenchow Railey Realty, Inc.

    1358 Crellin Underwood Rd, Oakland, MD 21550
  • 416 Shenandoah Ave, Oakland, MD 21550
    416 Shenandoah Ave, Oakland, MD 21550
    416 Shenandoah Ave, Oakland, MD 21550
    /56

    $157,000 Sold Aug 29, 2025

    416 Shenandoah Ave, Oakland, MD 21550

    • 3 Beds
    • 1.5 Baths
    • 975 Sq Ft
    • Built 1940

    Last Sold Summary

    • $161/SF
    • 4 Days On Market

    Current Estimated Value $155,200

    Last Listing Agent Rich Orr Railey Realty, Inc.

    416 Shenandoah Ave, Oakland, MD 21550
    • 375 Glendale Rd, Oakland, MD 21550
      375 Glendale Rd, Oakland, MD 21550
      375 Glendale Rd, Oakland, MD 21550
      /54

      Est $2,485,483 Not Listed For Sale

      • 8 Beds
      • 6.5 Baths
      • 5,638 Sq Ft

      375 Glendale Rd, Oakland, MD 21550

      375 Glendale Rd, Oakland, MD 21550
  • 565 Glendale Rd Unit 116, Oakland, MD 21550
    565 Glendale Rd Unit 116, Oakland, MD 21550
    565 Glendale Rd Unit 116, Oakland, MD 21550
    /29

    $169,000

    • 1 Bed
    • 1 Bath
    • 484 Sq Ft

    565 Glendale Rd Unit 116, Oakland, MD 21550

    Don't miss this rare opportunity to own a beautifully updated 1-bedroom unit at Silver Tree Suites on Deep Creek Lake! This turn-key condo features recent upgrades and is being sold fully furnished, making it perfect as a vacation getaway or income-generating rental. The unit boasts a solid rental history, offering immediate investment potential. Enjoy access to a wide range of on-site amenities,

    Nina Beitzel Railey Realty, Inc.

    565 Glendale Rd Unit 116, Oakland, MD 21550
  • 12 Roman Ridge Rd Unit 22B, Oakland, MD 21550
    12 Roman Ridge Rd Unit 22B, Oakland, MD 21550
    12 Roman Ridge Rd Unit 22B, Oakland, MD 21550
    /51

    $425,000 Sold Oct 22, 2025

    12 Roman Ridge Rd Unit 22B, Oakland, MD 21550

    • 3 Beds
    • 3.5 Baths
    • 2,202 Sq Ft
    • Built 2012

    Last Sold Summary

    • $193/SF
    • 130 Days On Market

    Current Estimated Value $439,053

    Last Listing Agent Andrew Eiswert Railey Realty, Inc.

    12 Roman Ridge Rd Unit 22B, Oakland, MD 21550
    • 9 Laurel Brook Dr, Oakland, MD 21550
      9 Laurel Brook Dr, Oakland, MD 21550
      9 Laurel Brook Dr, Oakland, MD 21550
      /18

      Est $246,411 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,200 Sq Ft

      9 Laurel Brook Dr, Oakland, MD 21550

      9 Laurel Brook Dr, Oakland, MD 21550
  • 66 Paradise Ridge Rd, Oakland, MD 21550
    66 Paradise Ridge Rd, Oakland, MD 21550
    66 Paradise Ridge Rd, Oakland, MD 21550
    /24

    $619,900

    • 4 Beds
    • 4 Baths
    • 2,550 Sq Ft

    66 Paradise Ridge Rd, Oakland, MD 21550

    Welcome to 66 Paradise Ridge Rd, a charming single-familyhome in the picturesque town of Oakland, MD. LAKE ACCESS WITH DEEDED DOCK. Builtin 1984, this two-story residence offers a spacious layout with 4 bathrooms and 2,550square feet of finished living space. Situated on a generous 21,780-square-foot lot, theproperty provides plenty of room to roam and enjoy the natural

    Joseph Hawkins Hawkins Real Estate Company

    66 Paradise Ridge Rd, Oakland, MD 21550

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