10,731

Oakland, MD Homes

Section Image
  • /67

    $760,000 Sold Nov 14, 2025

    62 Middleton Rd, Oakland, MD 21550

    • 3 Beds
    • 2.5 Baths
    • 2,397 Sq Ft
    • Built 1993

    Last Sold Summary

    • $317/SF
    • 113 Days On Market

    Last Listing Agent Jon Bell Railey Realty, Inc.

    62 Middleton Rd, Oakland, MD 21550
    • /83

      Est $1,663,064 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,403 Sq Ft

      2203 Lake Shore Dr, Oakland, MD 21550

      2203 Lake Shore Dr, Oakland, MD 21550
  • /10

    $995,000

    • Land
    • 0.58 Acre
    • $1,715,517 per Acre

    0 Glendale Rd Lot 12 Alpine Village Subdivision, Oakland, MD 21550

    RARE OPPURTUNITY! Discover one of the final opportunities to own true lakefront on the iconic Glendale Road! This premier homesite offers approximately 75 feet of pristine Deep Creek Lake frontage in a serene no wake zone, perfect for swimming, kayaking, and peaceful lakeside enjoyment. Zoning in this area is Town Center. This allows for a larger building area within the lot with relaxed

    Lucas Muenchow Railey Realty, Inc.

    0 Glendale Rd Lot 12 Alpine Village Subdivision, Oakland, MD 21550
  • /63

    $920,000 Sold Aug 22, 2025

    254 Middleton Rd, Oakland, MD 21550

    • 4 Beds
    • 4 Baths
    • 2,400 Sq Ft
    • Built 1994

    Last Sold Summary

    • $383/SF
    • 19 Days On Market

    Current Estimated Value $929,860

    Last Listing Agent Jon Bell Railey Realty, Inc.

    254 Middleton Rd, Oakland, MD 21550
    • /46

      Est $187,413 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 911 Sq Ft

      259 N Bradley Ln, Oakland, MD 21550

      259 N Bradley Ln, Oakland, MD 21550
  • /6

    $119,000

    • Land
    • 3.1 Acres
    • $38,387 per Acre

    0 Lot 29 Briarwood Ln Unit MDGA2008894, Oakland, MD 21550

    This is the building site you've been waiting for! Lot 29 is located in a subdivision called the View, and it lives up to the name! Offering a generous 3.10 Acres with possible lake views this attractive location is close to lake amenities while giving a sense of privacy. Call today for more information!

    Dan Shockey Taylor Made Deep Creek Vacations & Sales

    0 Lot 29 Briarwood Ln Unit MDGA2008894, Oakland, MD 21550
  • /33

    $150,000 Sold Dec 17, 2025

    111 Knoll Crest Heights Dr, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • 3,504 Sq Ft
    • Built 1971

    Last Sold Summary

    • $43/SF
    • 48 Days On Market

    Last Listing Agent Dan (Sussan) Duggan 1 Real Estate Source LLC

    111 Knoll Crest Heights Dr, Oakland, MD 21550
    • /58

      Est $477,084 Not Listed For Sale

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

      2734 Mayhew Inn Rd, Oakland, MD 21550

      2734 Mayhew Inn Rd, Oakland, MD 21550
  • /2

    $29,900

    • Land
    • 0.48 Acre
    • $62,292 per Acre

    0 N Hammond St, Oakland, MD 21550

    A practical, in‐town lot close to everything that quaint downtown Oakland has to offer. You are just minutes to local shops, schools, and restaurants. Public utilities are available and easy access to main roads, making the possibilities endless.

    Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    0 N Hammond St, Oakland, MD 21550
  • /43

    $460,000 Sold Oct 24, 2025

    180 Mystic Creek Trail Unit 3A, Oakland, MD 21550

    • 3 Beds
    • 3.5 Baths
    • 2,200 Sq Ft
    • Built 2009

    Last Sold Summary

    • $209/SF
    • 16 Days On Market

    Current Estimated Value $463,960

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    180 Mystic Creek Trail Unit 3A, Oakland, MD 21550
    • /32

      Est $1,520,316 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,956 Sq Ft

      1842 Stockslager Rd, Oakland, MD 21550

      1842 Stockslager Rd, Oakland, MD 21550
  • /27

    $239,900

    • 1 Bed
    • 1 Bath

    565 Glendale Rd Unit 106B, Oakland, MD 21550

    Ground-floor end unit with lake views at Silver Tree Suites. This one-bedroom layout packs in a gas fireplace, full bath with tub/shower, and a tidy kitchenette with microwave, dishwasher, and full fridge. Balcony doors open to Deep Creek air and filtered lake scenes. Community perks include sauna, gym, game room and more. Sold turn-key, fully furnished. Ductless units for heat and A/C. Monthly

    Jon Bell Railey Realty, Inc.

    565 Glendale Rd Unit 106B, Oakland, MD 21550
  • /32

    $139,000 Sold Aug 15, 2025

    4960 Hutton Rd, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 1,080 Sq Ft
    • Built 1971

    Last Sold Summary

    • $129/SF
    • 205 Days On Market

    Current Estimated Value $142,733

    Last Listing Agent Justin Liller Railey Realty, Inc.

    4960 Hutton Rd, Oakland, MD 21550
    • /38

      Est $265,587 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,858 Sq Ft

      87 Mitchell Dr, Oakland, MD 21550

      87 Mitchell Dr, Oakland, MD 21550
  • /27

    $245,000 Under Contract

    • 3 Beds
    • 1 Bath
    • 1,408 Sq Ft

    1570 Garrett Rd, Oakland, MD 21550

    Located between Oakland and Deep Creek Lake, this log ranch is situated on 14.82 acres, including a stream, pond, barn and outbuildings with many possibilities to include potential subdivision configurations. The log home needs some TLC and updates; it is being sold as part of an estate. Some items of personal property remain in the house and on grounds. Those items are being removed. More photos

    Dan (Sussan) Duggan 1 Real Estate Source LLC

    1570 Garrett Rd, Oakland, MD 21550
  • /51

    $838,000 Sold Feb 19, 2025

    297 Woodlands Hill Ln, Oakland, MD 21550

    • 5 Beds
    • 5 Baths
    • 3,088 Sq Ft
    • Built 2008

    Last Sold Summary

    • $271/SF
    • 12 Days On Market

    Current Estimated Value $880,941

    Last Listing Agent Roberta McNamara RE/MAX Results

    297 Woodlands Hill Ln, Oakland, MD 21550
    • /5

      Est $163,446 Not Listed For Sale

      133 Fox Den Rd, Oakland, MD 21550

      133 Fox Den Rd, Oakland, MD 21550
  • /20

    $125,000

    • 4 Beds
    • 1.5 Baths
    • 1,932 Sq Ft

    102 Roanoke Ave, Oakland, MD 21550

    Investor alert- price reduced. This house has great potential for a fix up or flip. 4-bedroom, 1.5-bath home located on a spacious corner lot in Loch Lynn. The home is conveniently located near the Loch Lynn soccer fields and just a few minutes from downtown Oakland. Lots of possibilities to make it your own! Sold AS IS. Ideal for cash or private financing due to the current condition of the

    Heather Homberg Taylor Made Deep Creek Vacations & Sales

    102 Roanoke Ave, Oakland, MD 21550
  • /72

    $310,000 Sold Jun 18, 2025

    202 Deerfield Dr, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 2,720 Sq Ft
    • Built 1987

    Last Sold Summary

    • $114/SF
    • 128 Days On Market

    Current Estimated Value $339,290

    Last Listing Agent Sharon Murray Coldwell Banker Home Town Realty

    202 Deerfield Dr, Oakland, MD 21550
    • /53

      Est $1,267,020 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,286 Sq Ft

      483 Skippers Point Rd, Oakland, MD 21550

      483 Skippers Point Rd, Oakland, MD 21550
  • /19

    $65,000

    • 792 Sq Ft

    809 N St, Oakland, MD 21550

    This home needs TLC with the possibility to rebuild on existing foundation if you want to rehab. Buyer to confirm with the county and the town of Mt. Lake Park for rebuilding stipulations. Being sold "As Is". Caution: Entering this property is at your own discretion and responsibility.RAILEY REALTY IS NOT THE CARETAKER OF PROPERTIES LISTED BY IT. PROSPECTIVE PURCHASERS AND THEIR

    Kathy Gibson Railey Realty, Inc.

    809 N St, Oakland, MD 21550
  • /108

    $370,000 Sold Oct 10, 2025

    220 N 11th St, Oakland, MD 21550

    • 4 Beds
    • 2.5 Baths
    • 3,159 Sq Ft
    • Built 1972

    Last Sold Summary

    • $117/SF
    • 12 Days On Market

    Current Estimated Value $397,278

    Last Listing Agent Justin Liller Railey Realty, Inc.

    220 N 11th St, Oakland, MD 21550
    • /35

      Est $138,624 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,656 Sq Ft

      830 N 4th St, Oakland, MD 21550

      830 N 4th St, Oakland, MD 21550
  • /11

    $23,000

    • Land
    • 0.12 Acre
    • $191,667 per Acre

    Lot 55 Gallatin Dr Unit 55, Oakland, MD 21550

    Gallatin Woods is a unique log home community located on Lakeshore Drive in the innermost part of Deep Creek Lake. Each owner may build within the building cylinder indicated on the plat and have exclusive use of the parking area and the additional land that immediately surrounds the home site. All other land within the community is condominiumized to keep the area wooded and carefree. Owners

    Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    Lot 55 Gallatin Dr Unit 55, Oakland, MD 21550
  • /45

    $435,000 Sold Jul 02, 2025

    256 Jeffrey Ln Unit 28, Oakland, MD 21550

    • 3 Beds
    • 3.5 Baths
    • 1,838 Sq Ft
    • Built 2004

    Last Sold Summary

    • $237/SF
    • 626 Days On Market

    Current Estimated Value $441,012

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

    256 Jeffrey Ln Unit 28, Oakland, MD 21550
    • /70

      Est $260,001 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,332 Sq Ft

      402 Leighton Dr, Oakland, MD 21550

      402 Leighton Dr, Oakland, MD 21550
  • /50

    $679,900 New Construction

    • 5 Beds
    • 4.5 Baths
    • 3,000 Sq Ft

    4A Mystic Creek Trail, Oakland, MD 21550

    Discover refined mountain-lake living in this new construction townhome at Mystic Creek on Deep Creek Lake. Designed with today’s lifestyle in mind, the home features a modern open-concept main level ideal for entertaining, with clean lines, abundant natural light, and seamless flow between living, dining, and kitchen spaces. This spacious residence offers three primary suites, each with upscale

    Justin Liller Railey Realty, Inc.

    4A Mystic Creek Trail, Oakland, MD 21550
  • /40

    $311,500 Sold Aug 22, 2025

    181 Jeffrey Ln Unit 23D, Oakland, MD 21550

    • 2 Beds
    • 1.5 Baths
    • 800 Sq Ft
    • Built 1997

    Last Sold Summary

    • $389/SF
    • 167 Days On Market

    Current Estimated Value $311,014

    Last Listing Agent Eric Crawford Taylor Made Deep Creek Vacations & Sales

    181 Jeffrey Ln Unit 23D, Oakland, MD 21550
    • /49

      Est $268,999 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,408 Sq Ft

      352 Fawn Dr, Oakland, MD 21550

      352 Fawn Dr, Oakland, MD 21550
  • /29

    $219,900

    • Land
    • 1.1 Acres
    • $199,909 per Acre

    47 Ridgewood Dr, Oakland, MD 21550

    Prime Lake Access Lot in Mountainside – Perfect for Your Dream Home! Nestled on a one-acre wooded lot in the sought-after Mountainside community, this homesite offers breathtaking views of Deep Creek Lake and the ideal slope for a walk-out basement. Enjoy the best of four-season living with easy access to community lake privileges, state parks, restaurants, and WISP Resort. Plus, take advantage

    Mike Fenton Railey Realty, Inc.

    47 Ridgewood Dr, Oakland, MD 21550
  • /79

    $925,000 Sold Oct 07, 2025

    1473 Pergin Farm Rd, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • 2,230 Sq Ft
    • Built 1945

    Last Sold Summary

    • $415/SF
    • 93 Days On Market

    Current Estimated Value $1,530,853

    Last Listing Agent Tony Migliaccio Long & Foster Real Estate, Inc.

    1473 Pergin Farm Rd, Oakland, MD 21550
    • /31

      Est $338,622 Not Listed For Sale

      • 5 Beds
      • 1 Bath
      • 2,280 Sq Ft

      1793 Kempton Rd, Oakland, MD 21550

      1793 Kempton Rd, Oakland, MD 21550
  • /25

    $34,000

    • Land
    • 6.9 Acres
    • $4,928 per Acre

    9 Timber Falls Rd, Oakland, MD 21550

    Buildable wooded lot on Backbone Ridge—approved for a 4-bedroom traditional septic system. Perfectly positioned between Canaan Valley and Deep Creek Lake, this property offers prime access to four-season adventure: hunting, hiking, skiing, and ATV riding. Minutes from Blackwater Falls, Whitegrass XC Ski Center, and the vibrant mountain towns of Thomas and Davis

    Jesse Shimrock Railey Realty, Inc.

    9 Timber Falls Rd, Oakland, MD 21550
  • /73

    $285,000 Sold Oct 06, 2025

    122 Earl Hauser Rd, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,664 Sq Ft
    • Built 2012

    Last Sold Summary

    • $171/SF
    • 3 Days On Market

    Current Estimated Value $289,147

    Last Listing Agent Rich Orr Railey Realty, Inc.

    122 Earl Hauser Rd, Oakland, MD 21550
    • /67

      Est $278,943 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,605 Sq Ft

      218 Weber Rd, Oakland, MD 21550

      218 Weber Rd, Oakland, MD 21550
  • /3

    $135,000

    • Land
    • 1 Acre
    • $135,000 per Acre

    0 Paradise Heights Rd Unit MDGA2007090, Oakland, MD 21550

    Centrally located 1-acre lake access homesite with a dock slip! This property has endless possibilities to build, and depending on where you decide to position your new home, there could be potential for lake views. Offering public sewer and no HOA fees. The only decision left to be made is what style home you will build. Just minutes to the DCL State Park, several restaurants, convenience store,

    Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    0 Paradise Heights Rd Unit MDGA2007090, Oakland, MD 21550
  • /27

    $712,500 Sold Dec 30, 2025

    939 Glendale Rd Unit 19, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,432 Sq Ft
    • Built 1994

    Last Sold Summary

    • $498/SF
    • 91 Days On Market

    Last Listing Agent Rick Davis Richard A. Davis & Associates

    939 Glendale Rd Unit 19, Oakland, MD 21550
    • /71

      Est $885,312 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 2,665 Sq Ft

      589 Mountainview Dr, Oakland, MD 21550

      589 Mountainview Dr, Oakland, MD 21550
  • /37

    $199,000 Under Contract

    • 2 Beds
    • 1 Bath
    • 960 Sq Ft

    1108 Hutton Rd, Oakland, MD 21550

    Welcome to 1108 Hutton Rd—a charming and well-maintained home set on a level lot near the highly sought-after Crellin Elementary School. This 2-bedroom, 1-bath property offers easy one-level living with a bright, functional layout and plenty of room to grow. The clean, unfinished basement provides excellent storage or future expansion potential. Outside, enjoy a spacious yard ideal for gardening,

    Nina Beitzel Railey Realty, Inc.

    1108 Hutton Rd, Oakland, MD 21550
  • /26

    $1,275,000 Sold Jun 02, 2025

    464 Lake Forest Dr, Oakland, MD 21550

    • 4 Beds
    • 3.5 Baths
    • 2,496 Sq Ft
    • Built 1997

    Last Sold Summary

    • $511/SF
    • 277 Days On Market

    Current Estimated Value $1,294,193

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

    464 Lake Forest Dr, Oakland, MD 21550

Showing Results 161 - 200, Page 5 of 18

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