10,716

Oakland, MD Homes

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    • 157 Jeffrey Ln Unit 21B, Oakland, MD 21550
      157 Jeffrey Ln Unit 21B, Oakland, MD 21550
      157 Jeffrey Ln Unit 21B, Oakland, MD 21550
      /46

      Est $318,944 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 550 Sq Ft

      157 Jeffrey Ln Unit 21B, Oakland, MD 21550

      157 Jeffrey Ln Unit 21B, Oakland, MD 21550
  • 163 Crestview Dr, Oakland, MD 21550
    163 Crestview Dr, Oakland, MD 21550
    163 Crestview Dr, Oakland, MD 21550
    /50

    $335,000

    • 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
  • 1473 Pergin Farm Rd, Oakland, MD 21550
    1473 Pergin Farm Rd, Oakland, MD 21550
    1473 Pergin Farm Rd, Oakland, MD 21550
    /79

    $925,000 Sold Oct 07, 2025

    • 2,230 Sq Ft
    • $415/SF
    • 93 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1945

    1473 Pergin Farm Rd, Oakland, MD 21550

    TIME TO UNWIND at this absolutely stunning Deep Creek Lake retreat boasting million-dollar panoramic views and private lake access! This fully furnished, meticulously renovated 4-bedroom, 2-bath raised rancher is the ultimate escape—perfect for weekend getaways, full-time living, or a savvy investment—sited on 2 pristine acres in the highly sought-after Pergin Farm community, a peaceful peninsula

    Tony Migliaccio Long & Foster Real Estate, Inc.

    1473 Pergin Farm Rd, Oakland, MD 21550
    • 20230 Garrett Hwy, Oakland, MD 21550
      20230 Garrett Hwy, Oakland, MD 21550
      20230 Garrett Hwy, Oakland, MD 21550
      /45

      Est $1,334,834 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 2,470 Sq Ft

      20230 Garrett Hwy, Oakland, MD 21550

      20230 Garrett Hwy, Oakland, MD 21550
  • Lot 15 Little Mountain Rd, Oakland, MD 21550
    Lot 15 Little Mountain Rd, Oakland, MD 21550
    Lot 15 Little Mountain Rd, Oakland, MD 21550
    /9

    $23,000

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

    Lot 15 Little Mountain Rd, Oakland, MD 21550

    Welcome to Backbone Ridge, where privacy, natural beauty, and mountain living converge. This 2.71-acre parcel is perfectly situated near the highest point in Maryland, offering breathtaking mountain views and a tranquil, secluded setting.Located in one of the region’s most desirable areas, this property is ready for your dream home. The homesite is already cleared, a gravel driveway in place,

    Agent Photo

    ADAM MURRAY

    BHHS Touchdown Home Pros Realty

    (240) 797-1759

    Lot 15 Little Mountain Rd, Oakland, MD 21550
  • 122 Earl Hauser Rd, Oakland, MD 21550
    122 Earl Hauser Rd, Oakland, MD 21550
    122 Earl Hauser Rd, Oakland, MD 21550
    /73

    $285,000 Sold Oct 06, 2025

    • 1,664 Sq Ft
    • $171/SF
    • 3 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2012

    122 Earl Hauser Rd, Oakland, MD 21550

    Charming 3 Bedroom Ranch Home on 20 Private Acres & Stream. Experience peace and privacy with this well-maintained 3-bedroom, 2-bath ranch-style home, perfectly situated on 20 scenic acres featuring a mix of woods, open fields & stream. This one-level home offers a spacious layout with a primary suite that includes a double vanity and soaking tub for ultimate relaxation.Additional

    Rich Orr Railey Realty, Inc.

    122 Earl Hauser Rd, Oakland, MD 21550
    • 1368 Mountainview Dr, Oakland, MD 21550
      1368 Mountainview Dr, Oakland, MD 21550
      1368 Mountainview Dr, Oakland, MD 21550
      /76

      Est $843,535 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,830 Sq Ft

      1368 Mountainview Dr, Oakland, MD 21550

      1368 Mountainview Dr, Oakland, MD 21550
  • Lot 2 Cedar Ln, Oakland, MD 21550
    Lot 2 Cedar Ln, Oakland, MD 21550
    Lot 2 Cedar Ln, Oakland, MD 21550
    /16

    $50,000

    • Land
    • 0.6 Acre
    • $83,333 per Acre

    Lot 2 Cedar Ln, Oakland, MD 21550

    Cleared, perc approved and ready to build! Lot 2 Cedar Lane sits on a 0.6 acre level lot at the beginning of Cedar Lane which sits close to the community center, tennis courts, pavilion and only a short ride to Muddy Creek and the access to Youghiogheny River! Youghiogheny Mountain Resort offers over 50 miles of trails for riding ATV’s, side by sides, fishing at Muddy Creek and much more! The

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 594-8377

    Lot 2 Cedar Ln, 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

    • 3,735 Sq Ft
    • $498/SF
    • 88 Days On Market
    • 7 Beds
    • 6.5 Baths
    • Built 2002

    237 Glendale Rd, Oakland, MD 21550

    Almost Aspen on Deep Creek Lake! You'll be in the heart of everything Deep Creek and Garrett County have to offer with this 7 bedroom 6.5 bath lakefront modified chalet. Offering 8 separate gathering places both inside and outside of the home, you'll have the perfect opportunities to relax with your group and or getaway for some personal time. With 4 private suits, direct bath access

    Bill Weissgerber Railey Realty, Inc.

    237 Glendale Rd, Oakland, MD 21550
    • 265 Winding Trail Ln Unit 9A, Oakland, MD 21550
      265 Winding Trail Ln Unit 9A, Oakland, MD 21550
      265 Winding Trail Ln Unit 9A, Oakland, MD 21550
      /63

      Est $676,159 Not Listed For Sale

      • 5 Beds
      • 4.5 Baths
      • 4,200 Sq Ft

      265 Winding Trail Ln Unit 9A, Oakland, MD 21550

      265 Winding Trail Ln Unit 9A, Oakland, MD 21550
  • Lot 14 Dogwood Dr, Oakland, MD 21550
    Lot 14 Dogwood Dr, Oakland, MD 21550
    Lot 14 Dogwood Dr, Oakland, MD 21550
    /19

    $35,000

    • Land
    • 0.59 Acre
    • $59,322 per Acre

    Lot 14 Dogwood Dr, Oakland, MD 21550

    Buildable lot in Youghiogheny Mountain Resort! This .59 acre lot offers a level homesite with approval for a sand mound septic system. The YMR community is a gated community offering the ultimate recreational experience with over 50 miles of trails, access to state lands, Youghiogheny River and much more. Looking for a site to build your getaway? This property may be for you!

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 981-5866

    Lot 14 Dogwood Dr, Oakland, MD 21550
  • 1087 Pergin Farm Rd, Oakland, MD 21550
    1087 Pergin Farm Rd, Oakland, MD 21550
    1087 Pergin Farm Rd, Oakland, MD 21550
    /149

    $2,975,000 Sold Oct 03, 2025

    • 4,481 Sq Ft
    • $664/SF
    • 16 Days On Market
    • 6 Beds
    • 5.5 Baths
    • Built 1984

    1087 Pergin Farm Rd, Oakland, MD 21550

    Step into a home like no other—where architectural charm meets modern comfort, and lake views greet you from nearly every room. With six bedrooms and five-and-a-half baths, there’s space for everyone to relax in style. The open, light-filled main living area is anchored by a striking fireplace and a window-wrapped dining alcove with serene water views, while a wall of windows frames the gorgeous

    Susan Bell Railey Realty, Inc.

    1087 Pergin Farm Rd, Oakland, MD 21550
    • 300 Big Rock Cabin Rd, Oakland, MD 21550
      300 Big Rock Cabin Rd, Oakland, MD 21550
      300 Big Rock Cabin Rd, Oakland, MD 21550
      /47

      Est $423,881 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,216 Sq Ft

      300 Big Rock Cabin Rd, Oakland, MD 21550

      300 Big Rock Cabin Rd, Oakland, MD 21550
  • 565 Glendale Rd Unit 212 - A, Oakland, MD 21550
    565 Glendale Rd Unit 212 - A, Oakland, MD 21550
    565 Glendale Rd Unit 212 - A, Oakland, MD 21550
    /20

    $215,000

    • 1 Bed
    • 1 Bath
    • 527 Sq Ft

    565 Glendale Rd Unit 212 - A, Oakland, MD 21550

    Silver Tree Suites offers 350' of pristine shoreline at Deep Creek Lake with western exposure centrally located to all area amenities. Unit 212A offers a one level floorpan with private bedroom on the second floor of building A which offers easy access to the lobby, elevator, gym, sauna, game room and patio area overlooking the lake. Condominium ownership at Silver Tree Suites offers ease of

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 896-3828

    565 Glendale Rd Unit 212 - A, Oakland, MD 21550
  • 1101 Wheeling Ave, Oakland, MD 21550
    1101 Wheeling Ave, Oakland, MD 21550
    1101 Wheeling Ave, Oakland, MD 21550
    /24

    $85,000 Sold Oct 03, 2025

    • 1,718 Sq Ft
    • $49/SF
    • 25 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1950

    1101 Wheeling Ave, Oakland, MD 21550

    Investor Opportunity – 1101 Wheeling Ave, Oakland, MD 21550 – $190,000Attention Investors and Visionaries!Unlock the potential in this unique property located in the heart of Oakland, Maryland. Priced to move at $190,000, this hidden gem offers a perfect canvas for your next flip, rental, or renovated. Features 3 bedrooms 2 baths, 2 car garage, wrap around porch, jacuzzi and a pool!

    Tanavia Greer Long & Foster Real Estate, Inc.

    1101 Wheeling Ave, Oakland, MD 21550
    • 208 Upper Penn Point Dr, Oakland, MD 21550
      208 Upper Penn Point Dr, Oakland, MD 21550
      208 Upper Penn Point Dr, Oakland, MD 21550
      /50

      Est $616,196 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,086 Sq Ft

      208 Upper Penn Point Dr, Oakland, MD 21550

      208 Upper Penn Point Dr, Oakland, MD 21550
  • 170 Winding Trail Ln Unit 4B, Oakland, MD 21550
    170 Winding Trail Ln Unit 4B, Oakland, MD 21550
    170 Winding Trail Ln Unit 4B, Oakland, MD 21550
    /45

    $589,000

    • 5 Beds
    • 4.5 Baths
    • 3,300 Sq Ft

    170 Winding Trail Ln Unit 4B, Oakland, MD 21550

    Spacious home located in the Timberlake Village community. This duplex home offers three levels of living space, granite counter tops, hardwood flooring, propane fireplace and an attached garage. The large kitchen and open floorplan make this an ideal permanent or vacation home. The exterior space is just as pleasing offering a covered front deck and a lower patio, which boasts a hot tub for your

    Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    170 Winding Trail Ln Unit 4B, Oakland, MD 21550
  • 346 Skippers Point Rd, Oakland, MD 21550
    346 Skippers Point Rd, Oakland, MD 21550
    346 Skippers Point Rd, Oakland, MD 21550
    /73

    $530,000 Sold Oct 03, 2025

    • 1,800 Sq Ft
    • $294/SF
    • 50 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1976

    346 Skippers Point Rd, Oakland, MD 21550

    Escape to your ideal mountain-lake retreat at Deep Creek Lake with this charming chalet-style home, nestled in a peaceful, wooded setting. This warm and inviting 3-bedroom, 2-bath getaway blends rustic charm with modern comfort—perfect as a vacation home or full-time residence. Take in filtered lake views from your home and expansive deck or relax by the lake with exclusive access to a sandy

    Steven Ritchie Railey Realty, Inc.

    346 Skippers Point Rd, Oakland, MD 21550
    • 8081 Oakland Sang Run Rd, Oakland, MD 21550
      8081 Oakland Sang Run Rd, Oakland, MD 21550
      8081 Oakland Sang Run Rd, Oakland, MD 21550
      /30

      Est $410,141 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 1,867 Sq Ft

      8081 Oakland Sang Run Rd, Oakland, MD 21550

      8081 Oakland Sang Run Rd, Oakland, MD 21550
  • 439 Paradise Heights, Oakland, MD 21550
    439 Paradise Heights, Oakland, MD 21550
    439 Paradise Heights, Oakland, MD 21550
    /45

    $1,359,000

    • 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
  • 83 Boston Post Rd, Oakland, MD 21550
    83 Boston Post Rd, Oakland, MD 21550
    83 Boston Post Rd, Oakland, MD 21550
    /41

    $247,500 Sold Oct 03, 2025

    • 400 Sq Ft
    • $619/SF
    • 109 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 2019

    83 Boston Post Rd, Oakland, MD 21550

    Escape to this delightful tiny home nestled in the breathtaking mountainous terrain of Deep Creek Lake, MD. This successful, turn-key vacation rental offers a unique blend of comfort and adventure, perfect for couples or solo travelers looking to unwind in nature. Airbnb describes this property as "One of the most loved homes on Airbnb, according to guests." While boasting a 4.94 star rating

    Brent Housley Railey Realty, Inc.

    83 Boston Post Rd, Oakland, MD 21550
    • 175 Whitetail Ct Unit 36, Oakland, MD 21550
      175 Whitetail Ct Unit 36, Oakland, MD 21550
      175 Whitetail Ct Unit 36, Oakland, MD 21550
      /32

      Est $436,790 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,152 Sq Ft

      175 Whitetail Ct Unit 36, Oakland, MD 21550

      175 Whitetail Ct Unit 36, Oakland, MD 21550
  • 1931 Lake Shore Dr, Oakland, MD 21550
    1931 Lake Shore Dr, Oakland, MD 21550
    1931 Lake Shore Dr, Oakland, MD 21550
    /93

    $3,489,000

    • 5 Beds
    • 5.5 Baths
    • 5,100 Sq Ft

    1931 Lake Shore Dr, Oakland, MD 21550

    Deep Creek Lakes, Sunset Hills, luxury retreat offering majestic mountain & lake views. A unique lakefront property that plays a perfect host to relaxing vacations with family and friends is a low-key lifestyle centered around the outdoors. Vast stretches of glass ensure a sparkling water view is always on hand. Though sleek materials and high-end finishes abound, their low-profile design puts

    Russell Bounds Railey Realty, Inc.

    1931 Lake Shore Dr, Oakland, MD 21550
  • 110 W Pennington St, Oakland, MD 21550
    110 W Pennington St, Oakland, MD 21550
    110 W Pennington St, Oakland, MD 21550
    /24

    $110,000 Sold Sep 26, 2025

    • 768 Sq Ft
    • $143/SF
    • 12 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1946

    110 W Pennington St, Oakland, MD 21550

    Affordable starter home on an alley in the town of Oakland with many possibilities. This rancher offers hardwood floors, newer roof , newer siding, covered porch and a full basement that can provide more living space. The natural gas heat is another plus. You are also within walking distance to many things in downtown Oakland.

    Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    110 W Pennington St, Oakland, MD 21550
    • 6 Cedar Ln, Oakland, MD 21550
      6 Cedar Ln, Oakland, MD 21550
      6 Cedar Ln, Oakland, MD 21550
      /12

      Est $86,706 Not Listed For Sale

      6 Cedar Ln, Oakland, MD 21550

      6 Cedar Ln, Oakland, MD 21550
  • 1674 Paradise Point Rd, Oakland, MD 21550
    1674 Paradise Point Rd, Oakland, MD 21550
    1674 Paradise Point Rd, Oakland, MD 21550
    /53

    $1,599,900

    • 4 Beds
    • 2.5 Baths
    • 2,340 Sq Ft

    1674 Paradise Point Rd, Oakland, MD 21550

    Beautifully remodeled lakefront home offering private dock and stunning views of Deep Creek Lake! Located on Paradise Point Rd, this home faces south for abundant natural light. 4 Bedrooms, 2.5 Bathrooms and sold fully furnished providing a gorgeous contemporary aesthetic throughout. Brand-new roof caps the Bright and Open Space with lots of glass to bring in the scenic lake views! Cozy fireplace

    Jon Bell Railey Realty, Inc.

    1674 Paradise Point Rd, Oakland, MD 21550
  • 20160 Garrett Hwy Unit G509, Oakland, MD 21550
    20160 Garrett Hwy Unit G509, Oakland, MD 21550
    20160 Garrett Hwy Unit G509, Oakland, MD 21550
    /35

    $380,000 Sold Sep 26, 2025

    • 640 Sq Ft
    • $594/SF
    • 24 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1974

    20160 Garrett Hwy Unit G509, Oakland, MD 21550

    Experience lakefront living at its finest with this beautifully updated 2-level condo on the shores of Deep Creek Lake. Unit G509 features 2 bedrooms and 1 full bathroom, offering breathtaking lake views. The main level includes a well-appointed kitchen and a cozy living area complete with a wood-burning fireplace—perfect for year-round relaxation. Upstairs, you’ll find two spacious bedrooms with

    Tim Macauley Taylor Made Deep Creek Vacations & Sales

    20160 Garrett Hwy Unit G509, Oakland, MD 21550
    • 36 Stockslager Rd, Oakland, MD 21550
      36 Stockslager Rd, Oakland, MD 21550
      36 Stockslager Rd, Oakland, MD 21550
      /13

      Not Listed For Sale

      36 Stockslager Rd, Oakland, MD 21550

      36 Stockslager Rd, Oakland, MD 21550
  • 282 McComas Beach Terrace, Oakland, MD 21550
    282 McComas Beach Terrace, Oakland, MD 21550
    282 McComas Beach Terrace, Oakland, MD 21550
    /150

    $4,200,000 New Construction

    • 6 Beds
    • 5.5 Baths
    • 4,354 Sq Ft

    282 McComas Beach Terrace, Oakland, MD 21550

    Discover The Birch Bower, a rare architect-designed lakefront sanctuary offering 600 feet of private shoreline on Deep Creek Lake. Completed in 2021, this 6-bedroom, 5.5-bath residence exemplifies modern luxury, combining meticulous design, serene natural surroundings, and proven short-term rental performance. Offered turn-key and fully furnished, this extraordinary lakefront estate presents a

    Morgan Boyer Hunt Country Sotheby's International Realty

    282 McComas Beach Terrace, Oakland, MD 21550
  • 0 Paradise Heights Rd Unit MDGA2010024, Oakland, MD 21550
    0 Paradise Heights Rd Unit MDGA2010024, Oakland, MD 21550
    0 Paradise Heights Rd Unit MDGA2010024, Oakland, MD 21550
    /4

    $115,000 Sold Sep 26, 2025

    • Land
    • 0.52 Acre
    • $221,154 per Acre
    • 32 Days On Market

    0 Paradise Heights Rd Unit MDGA2010024, Oakland, MD 21550

    Prime 0.52 Acre Wooded Lot at Deep Creek Lake!Don’t miss this rare opportunity to own a beautiful 0.52-acre wooded and level lot in a prime Deep Creek Lake location! Nestled just minutes from Deep Creek Lake State Park, restaurants, boat rentals, marinas, and the Wisp Resort, this property offers the perfect blend of privacy and convenience.With county road frontage and access to public

    Mike Kennedy Railey Realty, Inc.

    0 Paradise Heights Rd Unit MDGA2010024, Oakland, MD 21550
    • 0 Overlook Dr, Oakland, MD 21550
      0 Overlook Dr, Oakland, MD 21550
      0 Overlook Dr, Oakland, MD 21550
      /13

      Not Listed For Sale

      0 Overlook Dr, Oakland, MD 21550

      0 Overlook Dr, Oakland, MD 21550
  • 415 Nazelrod Rd, Oakland, MD 21550
    415 Nazelrod Rd, Oakland, MD 21550
    415 Nazelrod Rd, Oakland, MD 21550
    /106

    $3,249,000 New Construction

    • 4 Beds
    • 5 Baths
    • 6,036 Sq Ft

    415 Nazelrod Rd, Oakland, MD 21550

    One of Garrett County's most unique and breathtaking mountain estates, this completely custom masterpiece was designed and built with exceptional craftsmanship and attention to detail. The 6000 +/- sq ft custom newly built home is located in the beautiful mountains of Garrett County, Maryland and offers the new owner one-of-a-kind unobstructed panoramic views, serenity, privacy and endless

    Larry Smith Railey Realty, Inc.

    415 Nazelrod Rd, Oakland, MD 21550
  • 2805 Shady Dell Rd, Oakland, MD 21550
    2805 Shady Dell Rd, Oakland, MD 21550
    2805 Shady Dell Rd, Oakland, MD 21550
    /47

    $234,900 Under Contract

    • 4 Beds
    • 2 Baths
    • 1,456 Sq Ft

    2805 Shady Dell Rd, Oakland, MD 21550

    Nestled in the heart of Pleasant Valley, an area known for its peaceful country charm, this 4-bedroom, 2-bath home offers a serene setting. Enclosed decks run the full length of both the front and back of the house, with an additional private deck just off the dining room. The master bedroom features access to a covered deck and includes a full bathroom, while a second spacious bedroom also opens

    Laura Newhall Taylor Made Deep Creek Vacations & Sales

    2805 Shady Dell Rd, Oakland, MD 21550
    • 1506 Broadford Rd, Oakland, MD 21550
      1506 Broadford Rd, Oakland, MD 21550
      1506 Broadford Rd, Oakland, MD 21550
      /98

      Est $500,915 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 2,048 Sq Ft

      1506 Broadford Rd, Oakland, MD 21550

      1506 Broadford Rd, Oakland, MD 21550
  • 102 Mountainview Ct, Oakland, MD 21550
    102 Mountainview Ct, Oakland, MD 21550
    102 Mountainview Ct, Oakland, MD 21550
    /113

    $900,000 Pending

    • 7 Beds
    • 4.5 Baths
    • 5,376 Sq Ft

    102 Mountainview Ct, Oakland, MD 21550

    Mountainside Luxury Log Home. "Boulder Escape" is a stunning 7-bedroom, 4.5 bath lake access home on 1.6 acres in this prestigious mountaintop community. This income-producing property, offering over 5600 square feet, has an open concept floor plan with amazing expansive space on all levels. You will find an easy flow throughout the living, dining, and kitchen areas. Comfort and ambiance are

    Kathy Gibson Railey Realty, Inc.

    102 Mountainview Ct, Oakland, MD 21550
  • 0 Coolidge Ave, Oakland, MD 21550
    0 Coolidge Ave, Oakland, MD 21550
    0 Coolidge Ave, Oakland, MD 21550
    /14

    $80,000 Sold Sep 26, 2025

    • Land
    • 0.46 Acre
    • $173,913 per Acre
    • 76 Days On Market

    0 Coolidge Ave, Oakland, MD 21550

    Offering six town lots with an existing garage near the heart of downtown Oakland. If you are looking to build a home close to schools, shopping, dining, hospital, and more, this is your spot!

    Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    0 Coolidge Ave, Oakland, MD 21550
    • 812 Winter Place, Oakland, MD 21550
      812 Winter Place, Oakland, MD 21550
      812 Winter Place, Oakland, MD 21550
      /4

      Est $37,602 Not Listed For Sale

      812 Winter Place, Oakland, MD 21550

      812 Winter Place, Oakland, MD 21550
  • 870 Holy Cross Dr, Oakland, MD 21550
    870 Holy Cross Dr, Oakland, MD 21550
    870 Holy Cross Dr, Oakland, MD 21550
    /93

    $3,600,000 Under Contract

    • 7 Beds
    • 6.5 Baths
    • 5,681 Sq Ft

    870 Holy Cross Dr, Oakland, MD 21550

    A magnificent waterfront retreat in The Reserve at Holy Cross on the shores of Deep Creek Lake, representing the pinnacle of lake life living. This incomparable estate captures the essence of refined waterfront with a private dock, expansive outdoor entertaining spaces, and tranquil lakeside ambiance. Featuring 7 total bedrooms, 5 of which are en-suites, this home was thoughtfully designed with

    Russell Bounds Railey Realty, Inc.

    870 Holy Cross Dr, Oakland, MD 21550
  • 5 Arrowhead Ln, Oakland, MD 21550
    5 Arrowhead Ln, Oakland, MD 21550
    5 Arrowhead Ln, Oakland, MD 21550
    /92

    $674,900 Under Contract

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

    5 Arrowhead Ln, Oakland, MD 21550

    Great location for this 3BR-3BA Arrowhead townhouse. This unit sits very close to the water and has fantastic water views of the lake and the dock. Very convenient located in Tharyerville with Arrowhead Deli, Uno's, and Garrett 8 Cinemas nearby. Level walk to the lake and dock from the deck. One BR and one BA on each of 3 levels. Lower level deck and main level deck for relaxing evenings

    Kevin Liller Railey Realty, Inc.

    5 Arrowhead Ln, Oakland, MD 21550
    • 2 Cedar Ln, Oakland, MD 21550
      2 Cedar Ln, Oakland, MD 21550
      2 Cedar Ln, Oakland, MD 21550
      /12

      Not Listed For Sale

      2 Cedar Ln, Oakland, MD 21550

      2 Cedar Ln, Oakland, MD 21550

Showing Results 41 - 80, Page 2 of 18

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