10,549

Oakland, MD Homes

Section Image
  • /71

    $737,500

    • 4 Beds
    • 3.5 Baths
    • 4,377 Sq Ft

    941 Mountainview Dr, Oakland, MD 21550

    Experience the best of Deep Creek Lake living in this thoughtfully designed 4 bedroom, 3.5 bath home located in the highly desirable Mountainside community. Combining quality craftsmanship with inviting living spaces, the well planned floor plan maximizes both comfort and functionality. The finished basement provides additional living space perfect for entertaining family and friends. Situated on

    Nicole Jackson Railey Realty, Inc.

    941 Mountainview Dr, Oakland, MD 21550
  • /10

    $90,000

    Sold Jul 22, 2026

    0 Meadow Ct Unit MDGA2011316, Oakland, MD 21550

    • Land
    • 1.7 Acres
    • $52,941 per Acre

    Last Sold Summary

    • 10% Below List Price
    • 89 Days On Market

    Last Listing Agent Eric Crawford Taylor-Made Deep Creek Real Estate, LLC

    0 Meadow Ct Unit MDGA2011316, Oakland, MD 21550
    • /23

      Not Listed For Sale

      Lot 9 Birchwood Dr, Oakland, MD 21550

      Lot 9 Birchwood Dr, Oakland, MD 21550

      Last Sold Summary

      • 5 Days On Market

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

  • /62

    $765,000

    • 5 Beds
    • 3 Baths
    • 2,200 Sq Ft

    943 Paradise Heights, Oakland, MD 21550

    Welcome to this stunning 5-bedroom, 3-bath home, completed in 2023 and designed for modern mountain living. Featuring two private ensuite bedrooms, spacious living areas, and a fresh, contemporary design, this home is ready for you to enjoy from day one. This home features a stylish modern kitchen with an open layout that is perfect for entertainment. In the winter months, cozy up by the wood

    Lucas Muenchow Railey Realty, Inc.

    943 Paradise Heights, 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

    Current Estimated Value $169,776

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

    111 Knoll Crest Heights Dr, Oakland, MD 21550
    • /5

      Not Listed For Sale

      Lot #5 Swan Meadow Dr, Oakland, MD 21550

      Lot #5 Swan Meadow Dr, Oakland, MD 21550

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Rich Orr Railey Realty, Inc.

  • /45

    $1,329,000

    • 6 Beds
    • 4.5 Baths
    • 4,113 Sq Ft

    439 Paradise Heights, Oakland, MD 21550

    Stunning 6-Bedroom Kathadin Log Home with Breathtaking 180 views of Deep Creek Lake with Lake Access and a Boat Slip! This exceptional vacation home offers the perfect blend of rustic charm and modern luxury. Boasting 180-degree panoramic views of the sparkling lake, this property is a true mountain retreat. Every room is designed to capture the beauty of the surrounding landscape, with expansive

    Mike Kennedy Railey Realty, Inc.

    439 Paradise Heights, 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 $467,891

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    180 Mystic Creek Trail Unit 3A, Oakland, MD 21550
    • /4

      Not Listed For Sale

      p/o parcel 206 G Swauger Rd, Oakland, MD 21550

      p/o parcel 206 G Swauger Rd, Oakland, MD 21550

      Last Sold Summary

      Last Listing Agent Rich Orr Railey Realty, Inc.

  • /72

    $1,599,000

    $90K PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 3,714 Sq Ft

    670 Woodlands Hill Ln, Oakland, MD 21550

    Experience what may be the most spectacular view in all of Deep Creek Lake! Perched in an extraordinary setting, this exceptional Yellowstone Log Home showcases breathtaking panoramic water views that create a true “top of the world” feel. Designed to capture the scenery from every angle, the main level features an open-concept layout with soaring natural light, a stunning stone fireplace, luxury

    Nina Beitzel Railey Realty, Inc.

    670 Woodlands Hill Ln, 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 $386,073

    Last Listing Agent Justin Liller Railey Realty, Inc.

    220 N 11th St, Oakland, MD 21550
    • /103

      Est $362,758

      Not Listed For Sale

      206 N 10th St, Oakland, MD 21550

      • 4 Beds
      • 2 Baths
      • 2,772 Sq Ft
      • Built 1972
      206 N 10th St, Oakland, MD 21550

      Last Sold Summary

      • 37 Days On Market

      Last Listing Agent Kevin Liller Railey Realty, Inc.

  • /11

    $199,900

    $20K PRICE DROP
    • Land
    • 4,791 Sq Ft
    • $1,817,273 per Acre

    2 Overlook Ridge Dr S, Oakland, MD 21550

    Enjoy the best the lake has to offer from 'Overlook Ridge'! Boasting year-round lake views, yet tucked away in a peaceful and serene community setting. Short drive to the community lake access area for swimming and fishing! Dock Slips may be leased through HOA. Utilities to site and ready to build your perfect four-season Deep Creek getaway. Located just off of Rt. 219, with easy access to all

    Jon Bell Railey Realty, Inc.

    2 Overlook Ridge Dr S, Oakland, MD 21550
  • /37

    $199,000

    Sold Feb 25, 2026

    1108 Hutton Rd, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 960 Sq Ft
    • Built 1989

    Last Sold Summary

    • $207/SF
    • 3 Days On Market

    Current Estimated Value $209,163

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    1108 Hutton Rd, Oakland, MD 21550
    • /41

      Est $151,932

      Not Listed For Sale

      116 N 8th St Unit 2, Oakland, MD 21550

      • 2 Beds
      • 1 Bath
      • 1,494 Sq Ft
      • Built 1940
      116 N 8th St Unit 2, Oakland, MD 21550

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Duane Stein II Keller Williams Realty Centre

  • /71

    $824,900

    Under Contract
    • 5 Beds
    • 4 Baths
    • 3,304 Sq Ft

    113 Mountainview Ct, Oakland, MD 21550

    Experience the best of mountain living in this beautifully furnished 5-bedroom, 4-bath chalet in the desirable Mountainside community. Situated on over an acre of wooded privacy, this gorgeous home features an open floor plan with vaulted tongue-and-groove ceilings, a stunning stacked stone gas fireplace, and abundant natural light. The modern kitchen offers granite countertops, stainless steel

    Mike Fenton Railey Realty, Inc.

    113 Mountainview Ct, 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 $306,800

    Last Listing Agent Eric Crawford Taylor-Made Deep Creek Real Estate, LLC

    181 Jeffrey Ln Unit 23D, Oakland, MD 21550
    • /12

      Not Listed For Sale

      Lot 76 S Blakeslee Rd, Oakland, MD 21550

      Lot 76 S Blakeslee Rd, Oakland, MD 21550

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Betsy Spiker Holcomb Taylor-Made Deep Creek Real Estate, LLC

  • /31

    $1,650,000

    Under Contract
    • 4 Beds
    • 6 Baths
    • 5,117 Sq Ft

    3898 Underwood Rd, Oakland, MD 21550

    Unique luxury home on 23 acres with 360 degree views of Pleasant Valley. 5,100 + SQ. FT. 4 ensuite bedrooms, 2 additional powder rooms, formal living room/ballroom, informal living room, sunroom, den, pantry and large dine in kitchen. 4 fireplaces. full basement, 3 car attached garage. Whole home generator. Everything in this home is first rate. A must see for the discerning buyer

    Robert Custer Custer Realty & Auction

    3898 Underwood Rd, 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 $1,445,648

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

    1473 Pergin Farm Rd, Oakland, MD 21550
    • /38

      Not Listed For Sale

      601 Hope Ave, Oakland, MD 21550

      • 3 Beds
      • 2.5 Baths
      • 2,142 Sq Ft
      • Built 2025
      601 Hope Ave, Oakland, MD 21550

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

  • /75

    $325,000

    $25K PRICE DROP Pending
    • 4 Beds
    • 2 Baths
    • 3,352 Sq Ft

    2448 Birchwood Dr, Oakland, MD 21550

    Tucked within the sought-after Yough Mountain Resort community, this beautifully remodeled 4-bedroom, 2-bath mountain retreat blends rustic charm with thoughtful modern updates. Warm wood finishes, high ceilings, and inviting gathering spaces create a cozy lodge-style atmosphere, while upgrades throughout add comfort and convenience. The home features two full kitchens with granite countertops,

    Jon Bell Railey Realty, Inc.

    2448 Birchwood Dr, 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 $298,000

    Last Listing Agent Rich Orr Railey Realty, Inc.

    122 Earl Hauser Rd, Oakland, MD 21550
    • /10

      Est $153,000

      Not Listed For Sale

      503 Southern Pines Dr, Oakland, MD 21550

      • Built 2025
      503 Southern Pines Dr, Oakland, MD 21550

      Last Sold Summary

      • 68 Days On Market

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

  • /21

    $975,000

    $20K PRICE DROP
    • Land
    • 25,264 Sq Ft
    • $1,681,034 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
  • /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
    • /32

      Est $135,000

      Not Listed For Sale

      15 Fawn Dr, Oakland, MD 21550

      15 Fawn Dr, Oakland, MD 21550

      Last Sold Summary

      • 325 Days On Market

      Last Listing Agent Mike Fenton Railey Realty, Inc.

  • /10

    $115,000

    Pending
    • Land
    • 2.34 Acres
    • $49,145 per Acre

    926 Hutton Rd, Oakland, MD 21550

    Excellent investment opportunity available now! Flat and mostly clear 2.34 acre lot with an existing 65'x25' Steel pole building outside of zoning restrictions! With access to public utilities and existing infrastructure Possible uses could be storage or layover yard for a contractor, storage units for an investor, car lot, new home build, or any other possibility the new owner can imagine. Call

    Dan Shockey Taylor-Made Deep Creek Real Estate, LLC

    926 Hutton Rd, Oakland, MD 21550
  • /8

    $20,000

    Sold Jun 30, 2026

    460 W Liberty St, Oakland, MD 21550

    • Land
    • 13,503 Sq Ft
    • $64,516 per Acre

    Last Sold Summary

    • 20% Below List Price
    • 28 Days On Market

    Last Listing Agent Kevin Liller Railey Realty, Inc.

    460 W Liberty St, Oakland, MD 21550
    • /37

      Not Listed For Sale

      0 Hubbard Rd, Oakland, MD 21550

      0 Hubbard Rd, Oakland, MD 21550

      Last Sold Summary

      • 43 Days On Market

      Last Listing Agent Justin Liller Railey Realty, Inc.

  • /59

    $729,000

    $50K PRICE DROP Pending
    • 5 Beds
    • 1.5 Baths
    • 1,278 Sq Ft

    222 Skippers Point Rd, Oakland, MD 21550

    Lake cottage (5 Bedrooms) on large level lot with path to your own private class A dock & 25' of Lakefront, directly across the street. This comfy (one level living) cottage sits on 1.8 level acres with 2 storage garages and mature landscaping. 5BRs, open living, dinning & kitchen area, with lots of sunlight. 1 full & 1-1/2 bath, with 5 Bedrooms! Laundry room located off back of the home. Cute

    Julie Mead The KW Collective

    222 Skippers Point Rd, Oakland, MD 21550
  • /8

    $79,900

    Sold Apr 03, 2026

    Lot 2 Pergin Farm Rd, Oakland, MD 21550

    • Land
    • 3.67 Acres
    • $21,771 per Acre

    Last Sold Summary

    • 3 Days On Market

    Last Listing Agent Rich Orr Railey Realty, Inc.

    Lot 2 Pergin Farm Rd, Oakland, MD 21550
    • /22

      Not Listed For Sale

      0 Overlook Dr Unit 22 MDGA2009114, Oakland, MD 21550

      0 Overlook Dr Unit 22 MDGA2009114, Oakland, MD 21550

      Last Sold Summary

      • 84 Days On Market

      Last Listing Agent Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

  • /50

    $499,900

    $30K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,235 Sq Ft

    126 Leo Friend Rd, Oakland, MD 21550

    Perched above the treetops with panoramic lake views, this three-level retreat blends comfort with clean, considered upgrades. Vaulted ceilings and a spacious loft crown 2,235 square feet of living space, wrapped in new flooring with fresh paint inside and out. The kitchen, smartly updated with new countertops, connects to open dining and living anchored by a wood stove. A detached garage sits

    Jon Bell Railey Realty, Inc.

    126 Leo Friend Rd, Oakland, MD 21550
  • /92

    $635,000

    Sold Sep 26, 2025

    5 Arrowhead Ln, Oakland, MD 21550

    • 3 Beds
    • 3 Baths
    • 1,650 Sq Ft
    • Built 1988

    Last Sold Summary

    • $385/SF
    • 116 Days On Market

    Current Estimated Value $633,889

    Last Listing Agent Kevin Liller Railey Realty, Inc.

    5 Arrowhead Ln, Oakland, MD 21550
    • /11

      Not Listed For Sale

      Lots 14 & 17 Mallard Loop, Oakland, MD 21550

      Lots 14 & 17 Mallard Loop, Oakland, MD 21550

      Last Sold Summary

      • 4 Days On Market

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

  • /30

    $169,000

    • Land
    • 9.75 Acres
    • $17,333 per Acre

    9.75 AC. Dennett Rd, Oakland, MD 21550

    9.75 acres of prime land in a highly convenient Oakland location! This versatile property offers outstanding potential for development or the ideal setting for a private estate-sized homesite. Seller has already completed a proposed subdivision engineering plan, providing added value and future possibilities. Public water and sewer taps available per Oakland Town Administrator. Gently rolling

    Nina Beitzel Railey Realty, Inc.

    9.75 AC. Dennett Rd, Oakland, MD 21550
  • /2

    $280,000

    Sold Feb 23, 2026

    1359 Cedar Ln, Oakland, MD 21550

    • 2 Beds
    • 1.5 Baths
    • 1,440 Sq Ft
    • Built 1979

    Last Sold Summary

    • 2% Above List Price
    • $194/SF
    • 8 Days On Market

    Current Estimated Value $265,671

    Last Listing Agent Laura Newhall Taylor-Made Deep Creek Real Estate, LLC

    1359 Cedar Ln, Oakland, MD 21550
    • /68

      Est $509,672

      Not Listed For Sale

      20160 Garrett Hwy Unit F503, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,700 Sq Ft
      • Built 1972
      20160 Garrett Hwy Unit F503, Oakland, MD 21550

      Last Sold Summary

      • 0 Days On Market

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

  • /27

    $214,900

    Pending
    • 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

Showing Results 121 - 160, Page 4 of 18

How to Buy a Home How to Finance a Home How to Sell a Home