10,731

Oakland, MD Homes

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  • /47

    $289,900

    • 1 Bed
    • 1 Bath
    • 550 Sq Ft

    20160 Garrett Hwy Unit H708, Oakland, MD 21550

    Welcome to Will O' the Wisp Condominiums, where premium upgrades meet penthouse-level lakefront living at Deep Creek Lake! This fully furnished, beautifully updated, rarely available, top-floor two-level condo features one bedroom and one bath, offering 550 square feet of comfort, charm, and versatility — perfect as a vacation home, year-round retreat, or income-producing rental. Start your

    Agent Photo

    Charlotte Savoy

    The KW Collective

    (301) 479-6357

    20160 Garrett Hwy Unit H708, Oakland, MD 21550
  • /2

    $1,100 - $1,950 per month

    • 1 - 3 Beds
    • 2 Baths
    • 1,000 Sq Ft
    • Condo for Rent

    604 E Oak St, Oakland, MD 21550

    Charming 1, 2, and Three-Bedroom Apartment Recently Renovated, Prime Location' Welcome to this beautifully renovated three-bedroom apartment, where modern design meets comfort. Located in a quiet neighborhood, this home is just a short walk from downtown Oakland, offering the perfect blend of convenience and peaceful living. Complete Renovation: Enjoy a fresh and stylish space with all-new

    604 E Oak St, Oakland, MD 21550
  • /21

    $275,000 Sold Apr 11, 2025

    17 Laurel Brook Dr, Oakland, MD 21550

    • 3 Beds
    • 3 Baths
    • 1,840 Sq Ft
    • Built 1991

    Last Sold Summary

    • $149/SF
    • 171 Days On Market

    Current Estimated Value $285,188

    Last Listing Agent Michael Cumerlato Jason Mitchell Group

    17 Laurel Brook Dr, Oakland, MD 21550
    • /52

      Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,490 Sq Ft

      3094 Cranesville Rd, Oakland, MD 21550

      3094 Cranesville Rd, Oakland, MD 21550
  • /52

    $625,000

    • 3 Beds
    • 3 Baths
    • 1,740 Sq Ft

    65 Village Dr Unit 6, Oakland, MD 21550

    One of Deep Creek Lake's best performing vacation rental properties! Over 65 Village Drive offers cabin living at its finest with 3 full bedrooms and 3 full bathrooms minutes from all of Deep Creek Lake's most popular amenities. Two wood burning fireplaces give ultimate ambiance; one in the main level living room and one in the four seasons room where the hot tub is also located. Many recent

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 759-2822

    65 Village Dr Unit 6, Oakland, MD 21550
  • /25

    $2,400 per month

    • 2 Beds
    • 1 Bath
    • 3,350 Sq Ft
    • House for Rent

    604 #4 E Oak St, Oakland, MD 21550

    Charming Two-Bedroom Furnish Apartment Ready for short term lease: RecentlyRenovated, Prime Location'Welcome to this beautifully renovated two-bedroom apartment, where modern design meets comfort. Located in a quiet neighborhood, this home is just a short walk from downtown Oakland, offering the perfect blend of convenience and peaceful living.Complete Renovation: Enjoy a fresh and

    Sharon Mokhtari Fairfax Realty of Tysons

    604 #4 E Oak St, Oakland, MD 21550
  • /76

    $1,400,000 Sold Dec 04, 2025

    1989 Lake Shore Dr, Oakland, MD 21550

    • 4 Beds
    • 3.5 Baths
    • 3,008 Sq Ft
    • Built 1964

    Last Sold Summary

    • $465/SF
    • 18 Days On Market

    Last Listing Agent Justin Liller Railey Realty, Inc.

    1989 Lake Shore Dr, Oakland, MD 21550
    • /7

      Not Listed For Sale

      Lot 5 Bobcat Hill Ln, Oakland, MD 21550

      Lot 5 Bobcat Hill Ln, Oakland, MD 21550
  • /107

    $695,000

    • 4 Beds
    • 3 Baths
    • 3,242 Sq Ft

    621 Paradise Heights, Oakland, MD 21550

    Opportunity to own one of Deep Creek Lake's most unique homes! 621 Paradise Heights is a geodesic dome house offering 4 bedrooms, 3 full bathrooms and over 4300 square feet of interior space. Become the ultimate host of guests with the many entertainment spaces in the house including main level living room, parlor with wet bar, expansive deck, stacked stone fireplace, fit pit in back yard and

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 998-1539

    621 Paradise Heights, Oakland, MD 21550
  • /2

    $900 - $1,550 per month

    • 1 - 3 Beds
    • 1 Bath
    • 650 Sq Ft
    • Condo for Rent

    400 E Alder St, Oakland, MD 21550

    Newly renovated second floor apartment with 3 bedrooms freshly painted, with new floors and a fully renovated bathroom. The apartment boasts high ceilings and charming original fixtures. Located in the heart of downtown its within walking distance of shops and restaurants!

    400 E Alder St, Oakland, MD 21550
  • /42

    $270,000 Sold Nov 21, 2025

    11 Sunset Dr, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • Built 2000

    Last Sold Summary

    • $193/SF
    • 29 Days On Market

    Last Listing Agent Jay Ferguson Taylor Made Deep Creek Vacations & Sales

    11 Sunset Dr, Oakland, MD 21550
    • /37

      Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 3,084 Sq Ft

      278 Basswood Way Unit 19, Oakland, MD 21550

      278 Basswood Way Unit 19, Oakland, MD 21550
  • /37

    $425,000 Under Contract

    • 2 Beds
    • 1 Bath

    15 Village Dr Unit 1, Oakland, MD 21550

    Escape to a simpler time with all the modern conveniences you desire at this 2-bedroom log cabin in the Yellowstone Village. The main level envelops you with the uniqueness and charm from the great room with an old-fashioned stone fireplace to warm up the chilling evenings and furniture that begs you to sit a while, to the quaint, yet full-sized kitchen with the cutest dining table. Venture up

    Agent Photo

    Dale Carpenter

    Railey Realty, Inc.

    (240) 377-0960

    15 Village Dr Unit 1, Oakland, MD 21550
  • /20

    $1,990 per month

    • 3 Beds
    • 1 Bath
    • 3,350 Sq Ft
    • House for Rent

    604 E Oak St, Oakland, MD 21550

    Charming Three-Bedroom Apartment Recently Renovated, Prime Location'Welcome to this beautifully renovated three-bedroom apartment, where modern design meets comfort. Located in a quiet neighborhood, this home is just a short walk from downtown Oakland, offering the perfect blend of convenience and peaceful living.Complete Renovation: Enjoy a fresh and stylish space with all-new finishes,

    Sharon Mokhtari Fairfax Realty of Tysons

    604 E Oak St, Oakland, MD 21550
  • /55

    $503,000 Sold Mar 28, 2025

    180 Roman Ridge Rd Unit 18, Oakland, MD 21550

    • 4 Beds
    • 4.5 Baths
    • 2,608 Sq Ft
    • Built 2005

    Last Sold Summary

    • $193/SF
    • 232 Days On Market

    Current Estimated Value $513,612

    Last Listing Agent Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    180 Roman Ridge Rd Unit 18, Oakland, MD 21550
    • /17

      Est $132,786 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,536 Sq Ft

      2 E Center St, Oakland, MD 21550

      2 E Center St, Oakland, MD 21550
  • /55

    $275,000

    • 3 Beds
    • 2 Baths
    • 1,848 Sq Ft

    702 Sunshine Dr, Oakland, MD 21550

    Welcome to easy, one-level living at 702 Sunshine Dr! This well-maintained 3-bedroom, 2-bath home offers a functional layout with everything you need on one floor. Enjoy the convenience of an attached garage, a fenced backyard, and a covered back porch—perfect for morning coffee, outdoor dining, or relaxing in any weather. Located just minutes from downtown Oakland, this home puts you close to

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 905-4746

    702 Sunshine Dr, Oakland, MD 21550
  • /2

    $1,100 - $1,950 per month

    • 1 - 3 Beds
    • 2 Baths
    • 1,000 Sq Ft
    • Condo for Rent

    604 E Oak St, Oakland, MD 21550

    Charming 1, 2, and Three-Bedroom Apartment Recently Renovated, Prime Location' Welcome to this beautifully renovated three-bedroom apartment, where modern design meets comfort. Located in a quiet neighborhood, this home is just a short walk from downtown Oakland, offering the perfect blend of convenience and peaceful living. Complete Renovation: Enjoy a fresh and stylish space with all-new

    604 E Oak St, Oakland, MD 21550
  • /39

    $259,000 Sold Feb 25, 2025

    307 Sciota St, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • 2,144 Sq Ft
    • Built 1985

    Last Sold Summary

    • $121/SF
    • 3 Days On Market

    Current Estimated Value $258,625

    Last Listing Agent Ben Maust Railey Realty, Inc.

    307 Sciota St, Oakland, MD 21550
    • /7

      Est $397,998 Not Listed For Sale

      • 1 Bed
      • 1 Bath
      • 530 Sq Ft

      1517 Upperman Rd, Oakland, MD 21550

      1517 Upperman Rd, Oakland, MD 21550
  • /9

    $275,000 Coming Soon

    • 3 Beds
    • 2 Baths
    • 875 Sq Ft

    127 Jeffrey Ln Unit 18C, Oakland, MD 21550

    Welcome to 127 Jeffrey Lane 18C! Centrally located at Deep Creek Lake, this unit offers convenience year round to restaurants, skiing, golf courses, Deep Creek Lake and even one of the areas most desired coffee shops just a few hundred feet away. Enjoy northeastern exposure for great sunrises overlooking the lake. The main level offers a kitchen, living room with wood burning fireplace, 2

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (301) 591-6157

    127 Jeffrey Ln Unit 18C, Oakland, MD 21550
  • /29

    $1,550 per month

    • 3 Beds
    • 1 Bath
    • 2,312 Sq Ft
    • Condo for Rent

    400 E Alder St Unit 3, Oakland, MD 21550

    Newly renovated second floor apartment with 3 bedrooms freshly painted, with new floors and a fully renovated bathroom. The apartment boasts high ceilings and charming original fixtures. Located in the heart of downtown its within walking distance of shops and restaurants!

    Sharon Mokhtari Fairfax Realty of Tysons

    400 E Alder St Unit 3, Oakland, MD 21550
  • /76

    $775,000 Sold Aug 25, 2025

    3472 Lake Shore Dr, Oakland, MD 21550

    • 5 Beds
    • 5.5 Baths
    • 2,904 Sq Ft
    • Built 2007

    Last Sold Summary

    • $267/SF
    • 112 Days On Market

    Current Estimated Value $790,570

    Last Listing Agent Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    3472 Lake Shore Dr, Oakland, MD 21550
    • /121

      Est $703,610 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 3,982 Sq Ft

      604 Harvey Winters Dr, Oakland, MD 21550

      604 Harvey Winters Dr, Oakland, MD 21550
  • /18

    $44,900

    • Land
    • 6.12 Acres
    • $7,337 per Acre

    Lot 6 Hoye Crest Rd, Oakland, MD 21550

    Opportunity to own over 6 acres on Backbone Mountain adjoining the Highest Point in Maryland! This lot will offer some of the best views from Maryland's highest point with western exposure. Approved perc and electric to site, ready for you to build your dream home! Residential community. No camping, no hunting. Call today to schedule a time too see this remarkable property!

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 652-2465

    Lot 6 Hoye Crest Rd, Oakland, MD 21550
  • /2

    $900 - $1,550 per month

    • 1 - 3 Beds
    • 1 Bath
    • 650 Sq Ft
    • Condo for Rent

    400 E Alder St, Oakland, MD 21550

    Newly renovated second floor apartment with 3 bedrooms freshly painted, with new floors and a fully renovated bathroom. The apartment boasts high ceilings and charming original fixtures. Located in the heart of downtown its within walking distance of shops and restaurants!

    400 E Alder St, Oakland, MD 21550
  • /43

    $132,000 Sold Aug 13, 2025

    723 E Oak St, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 988 Sq Ft
    • Built 1966

    Last Sold Summary

    • $134/SF
    • 2 Days On Market

    Current Estimated Value $136,364

    Last Listing Agent Kevin Liller Railey Realty, Inc.

    723 E Oak St, Oakland, MD 21550
    • /13

      Not Listed For Sale

      Lot 1 Betts Ln, Oakland, MD 21550

      Lot 1 Betts Ln, Oakland, MD 21550
  • /50

    $315,000

    • 3 Beds
    • 2.5 Baths
    • 1,416 Sq Ft

    163 Crestview Dr, Oakland, MD 21550

    Welcome to 163 Crestview Drive — a beautifully maintained 3-bedroom, 2.5-bath home nestled in the Mitchell Manor neighborhood. This inviting Cape Cod offers timeless charm, modern updates, and a peaceful setting just minutes from downtown Oakland. Many recent improvements including HVAC, water treatment/filtration system, flooring and landscaping! Step inside to an open, light-filled floor plan

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 502-1143

    163 Crestview Dr, Oakland, MD 21550
  • /2

    $900 - $1,550 per month

    • 1 - 3 Beds
    • 1 Bath
    • 650 Sq Ft
    • Condo for Rent

    400 E Alder St, Oakland, MD 21550

    Newly renovated second floor apartment with 3 bedrooms freshly painted, with new floors and a fully renovated bathroom. The apartment boasts high ceilings and charming original fixtures. Located in the heart of downtown its within walking distance of shops and restaurants!

    400 E Alder St, Oakland, MD 21550
  • /9

    $23,000 Sold Nov 03, 2025

    Lot 15 Little Mountain Rd, Oakland, MD 21550

    • Land
    • 2.71 Acres
    • $8,487 per Acre

    Last Sold Summary

    • 34% Below List Price
    • 132 Days On Market

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

    Lot 15 Little Mountain Rd, Oakland, MD 21550
    • /30

      Not Listed For Sale

      • 1 Bed
      • 1 Bath
      • 382 Sq Ft

      565 Glendale Rd Unit 123-A, Oakland, MD 21550

      565 Glendale Rd Unit 123-A, Oakland, MD 21550
  • /33

    $160,000

    • 1 Bed
    • 1 Bath
    • 382 Sq Ft

    565 Glendale Rd Unit 210-A, Oakland, MD 21550

    Studio unit at Silver Tree Suites, one of Deep Creek Lake's most premier condo/hotel communities! Silver Tree Suites offers over 350' of pristine lakefront with western exposure. Located directly adjacent to Dutch's at Silver Tree, this location offers convenience to one of the areas most desirable restaurants, and is only 5-10 minutes to all of the local amenities and attractions you come to

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 623-5408

    565 Glendale Rd Unit 210-A, Oakland, MD 21550
  • /2

    $1,100 - $1,950 per month

    • 1 - 3 Beds
    • 2 Baths
    • 1,000 Sq Ft
    • Condo for Rent

    604 E Oak St, Oakland, MD 21550

    Charming 1, 2, and Three-Bedroom Apartment Recently Renovated, Prime Location' Welcome to this beautifully renovated three-bedroom apartment, where modern design meets comfort. Located in a quiet neighborhood, this home is just a short walk from downtown Oakland, offering the perfect blend of convenience and peaceful living. Complete Renovation: Enjoy a fresh and stylish space with all-new

    604 E Oak St, Oakland, MD 21550
  • /62

    $1,399,000 Sold Sep 05, 2025

    1589 Lake Shore Dr, Oakland, MD 21550

    • 3 Beds
    • 3 Baths
    • 1,872 Sq Ft
    • Built 2020

    Last Sold Summary

    • $747/SF
    • 3 Days On Market

    Current Estimated Value $1,440,137

    Last Listing Agent Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    1589 Lake Shore Dr, Oakland, MD 21550
    • /60

      Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,735 Sq Ft

      314 Morning Glory Dr, Oakland, MD 21550

      314 Morning Glory Dr, Oakland, MD 21550
  • /10

    $5,000

    • Land
    • 0.65 Acre
    • $7,692 per Acre

    Lot 17 Birchwood Dr, Oakland, MD 21550

    Lot 17 Birchwood Drive is a .65-acre wooded, NON-BUILDABLE membership lot located in the Youghiogheny Mountain Resort community in Oakland, MD. Nestled among mature trees, this lot's ownership offers full membership access to the community’s amenities, including over 50 miles of private roads and trails perfect for ATV riding, UTVs, dirt bikes, hiking, and outdoor recreation. Ideal for outdoor

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 512-9707

    Lot 17 Birchwood Dr, Oakland, MD 21550
  • /73

    $305,000 Sold Nov 06, 2025

    17 Driftwood Ln, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 2,092 Sq Ft
    • Built 1978

    Last Sold Summary

    • $146/SF
    • 113 Days On Market

    Current Estimated Value $309,648

    Last Listing Agent Larry Smith Railey Realty, Inc.

    17 Driftwood Ln, Oakland, MD 21550
    • /3

      Not Listed For Sale

      7 Cherrywood Dr, Oakland, MD 21550

      7 Cherrywood Dr, Oakland, MD 21550
  • /35

    $95,000

    • Land
    • 1.08 Acres
    • $87,963 per Acre

    Lot 18 Laurel Ct, Oakland, MD 21550

    Discover the perfect setting for your Deep Creek Lake getaway on this beautiful 1.08-acre homesite located at the end of a quiet cul-de-sac in the desirable Paradise Ridge community. Lot 18 Laurel Court offers a peaceful, private setting surrounded by mature trees and mountain views. Paradise Ridge features one of the nicest lake access areas on Deep Creek Lake—perfect for swimming, kayaking, and

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 916-1185

    Lot 18 Laurel Ct, Oakland, MD 21550

Showing Results 1 - 40, Page 1 of 18

Home Trends in Oakland, MD

Housing Trends

Median Sale Price
$442,500
Median Single Family Sale Price
$431,000
Median Townhouse Sale Price
$510,000
Median 2 Bedroom Sale Price
$319,000
Median 1 Bedroom Sale Price
$239,900
Average Price Per Sq Ft
$265
Number of Homes for Sale
43
Last 12 months Home Sales
136
Months of Supply
3.80
Median List Price
$435,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
11%
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