119

Oakland, MD Homes for Sale

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  • 621 Paradise Heights, Oakland, MD 21550
    621 Paradise Heights, Oakland, MD 21550
    621 Paradise Heights, 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
  • 157 Jeffrey Ln Unit 21B, Oakland, MD 21550
    157 Jeffrey Ln Unit 21B, Oakland, MD 21550
    157 Jeffrey Ln Unit 21B, Oakland, MD 21550
    /28

    $299,000

    • 2 Beds
    • 1 Bath
    • 550 Sq Ft

    157 Jeffrey Ln Unit 21B, Oakland, MD 21550

    Nestled in the charming Traders Landing community, this delightful end-of-row townhouse offers a perfect blend of comfort and convenience with one of the best unobstructed views of the lake in Traders Landing. This villa-style home features two cozy bedrooms and a full bathroom, ideal for relaxation and unwinding after a long day. The inviting living space is enhanced by a warm wood-burning

    Agent Photo

    James Matthews

    Taylor Made Deep Creek Real Estate

    (240) 883-5848

    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

    $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
  • 565 Glendale Rd Unit 210-A, Oakland, MD 21550
    565 Glendale Rd Unit 210-A, Oakland, MD 21550
    565 Glendale Rd Unit 210-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
  • Lot 17 Birchwood Dr, Oakland, MD 21550
    Lot 17 Birchwood Dr, Oakland, MD 21550
    Lot 17 Birchwood 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. While you cannot build on this lot, 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

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 512-9707

    Lot 17 Birchwood Dr, Oakland, MD 21550
  • Lot 18 Laurel Ct, Oakland, MD 21550
    Lot 18 Laurel Ct, Oakland, MD 21550
    Lot 18 Laurel Ct, 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
  • 170 San Francisco St, Oakland, MD 21550
    170 San Francisco St, Oakland, MD 21550
    170 San Francisco St, Oakland, MD 21550
    /12

    $129,900

    • Land
    • 1.38 Acres
    • $94,130 per Acre

    170 San Francisco St, Oakland, MD 21550

    NEW in the Deep Creek Lake and WISP Resort area: three lots at .46 acres each (total is 1.38 acres)! Whether you envision a cozy cabin or a luxury lodge, this parcel offers the ideal blend of seclusion and accessibility. Property Highlights: Private well water source already in place, 200 AMP electric service connection, Approved perc test suitable for a 4-5 bedroom home, Privacy with

    Agent Photo

    Hunter Shank

    Coldwell Banker Realty

    (240) 202-2754

    170 San Francisco St, 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

    $199,000

    • 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
  • 1240 Boy Scout Rd, Oakland, MD 21550
    1240 Boy Scout Rd, Oakland, MD 21550
    1240 Boy Scout Rd, Oakland, MD 21550
    /150

    $4,250,000

    • 7 Beds
    • 7 Baths
    • 5,695 Sq Ft

    1240 Boy Scout Rd, Oakland, MD 21550

    Welcome to Double Eagle Ranch — quite possibly the most beautiful property in Garrett County. This iconic 50-acre estate is set in the heart of Deep Creek Lake and includes its own deeded waterfront parcel with a brand-new dock, giving you private lake access just minutes from the property. Rarely does an offering combine such incredible privacy, natural beauty, and income-producing potential in

    Agent Photo

    Charlotte Savoy

    The KW Collective

    (240) 851-4712

    1240 Boy Scout Rd, 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

    $40,000

    • Land
    • 0.6 Acre
    • $66,667 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
  • Lot 13 Dogwood Dr, Oakland, MD 21550
    Lot 13 Dogwood Dr, Oakland, MD 21550
    Lot 13 Dogwood Dr, Oakland, MD 21550
    /21

    $22,500

    • Land
    • 0.58 Acre
    • $38,793 per Acre

    Lot 13 Dogwood Dr, Oakland, MD 21550

    Discover the perfect blend of privacy and potential with these two adjoining lots located in the Youghiogheny Mountain Resort community. Lot 13 Dogwood Drive offers 0.58 wooded acres of mountain serenity. Lot 13 is approved for a sand mound septic system, making it an ideal site for your future mountain cabin or getaway retreat. The community offers gated access, over 50 miles of community roads

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 875-5545

    Lot 13 Dogwood Dr, Oakland, MD 21550
  • Lot 20 Paradise Ridge Rd, Oakland, MD 21550
    Lot 20 Paradise Ridge Rd, Oakland, MD 21550
    Lot 20 Paradise Ridge Rd, Oakland, MD 21550
    /31

    $130,000

    • Land
    • 2.1 Acres
    • $61,905 per Acre

    Lot 20 Paradise Ridge Rd, Oakland, MD 21550

    Discover the perfect setting for your mountain retreat in the Paradise Ridge community at Deep Creek Lake. This beautiful 2.10 acre wooded lot is tucked away on a quiet cul-de-sac, offering privacy, natural surroundings, and a peaceful atmosphere. The property has already been approved for a conventional septic system, making it an ideal choice for building your dream home or vacation getaway.

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 526-7577

    Lot 20 Paradise Ridge Rd, Oakland, MD 21550
  • 127 S Oakhall Dr, Oakland, MD 21550
    127 S Oakhall Dr, Oakland, MD 21550
    127 S Oakhall Dr, Oakland, MD 21550
    /60

    $285,000

    • 4 Beds
    • 2 Baths
    • 1,913 Sq Ft

    127 S Oakhall Dr, Oakland, MD 21550

    Welcome to this well maintained 4-bed, 2-bath ranch home on a generous corner lot in Oakland, MD. Inviting curb appeal with stone exterior and mature landscaping sets the tone. Step inside to a bright and spacious main level featuring gleaming hardwood floors, a large eat-in kitchen with ample cabinetry, and an open living area perfect for gatherings. Enjoy three main-level bedrooms and a full

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 792-8710

    127 S Oakhall Dr, Oakland, MD 21550
  • 127 Jeffrey Ln Unit 18C, Oakland, MD 21550
    127 Jeffrey Ln Unit 18C, Oakland, MD 21550
    127 Jeffrey Ln Unit 18C, Oakland, MD 21550
    /37

    $275,000

    • 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
  • Lot 6 Hoye Crest Rd, Oakland, MD 21550
    Lot 6 Hoye Crest Rd, Oakland, MD 21550
    Lot 6 Hoye Crest Rd, 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
  • 1001 Sutter Ln, Oakland, MD 21550
    1001 Sutter Ln, Oakland, MD 21550
    1001 Sutter Ln, Oakland, MD 21550
    /93

    $799,000

    • 5 Beds
    • 6 Baths
    • 6,550 Sq Ft

    1001 Sutter Ln, Oakland, MD 21550

    Discover the ultimate mountain–lake getaway in this stunning 5BR Southern-style home on a private 2.4-acre wooded lot bordering Broadford Lake recreational area! Located just minutes from Deep Creek Lake and Wisp Resort, this magnificent property offers over 6,500 sq ft. and delivers unforgettable space, luxury, and privacy. Step inside to soaring cathedral ceilings, skylights, oak floors, and a

    Nina Beitzel Railey Realty, Inc.

    1001 Sutter Ln, Oakland, MD 21550
  • 1019 Lake Shore Dr, Oakland, MD 21550
    1019 Lake Shore Dr, Oakland, MD 21550
    1019 Lake Shore Dr, Oakland, MD 21550
    /75

    $1,749,000

    • 4 Beds
    • 4.5 Baths
    • 2,605 Sq Ft

    1019 Lake Shore Dr, Oakland, MD 21550

    Tucked among the trees, Blue Spruce offers a perfect blend of modern comfort and serene natural beauty. This recently remodeled 4-bedroom, 4 and a half bathroom home invites you to relax, recharge, and reconnect with nature. With each bedroom offering an ensuite bathroom plus a half bath near the kitchen, this home was designed for comfort. Step inside to discover thoughtful updates throughout,

    Rachel Bruch Railey Realty, Inc.

    1019 Lake Shore Dr, Oakland, MD 21550
  • 439 Paradise Heights, Oakland, MD 21550
    439 Paradise Heights, Oakland, MD 21550
    439 Paradise Heights, Oakland, MD 21550
    /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
  • 130 Mystic Creek Trail Unit 1B, Oakland, MD 21550
    130 Mystic Creek Trail Unit 1B, Oakland, MD 21550
    130 Mystic Creek Trail Unit 1B, Oakland, MD 21550
    /71

    $639,000

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

    130 Mystic Creek Trail Unit 1B, Oakland, MD 21550

    Discover refined mountain and lake living in this quality built townhome at Mystic Creek on Deep Creek Lake, nestled in a quiet, serene setting with a truly custom feel. This spacious 5-bedroom, 4.5 bath residence offers an open concept main level ideal for entertaining, featuring hardwood floors throughout the main living area, abundant natural light, and seamless flow between the living,

    Melissa Long Railey Realty, Inc.

    130 Mystic Creek Trail Unit 1B, Oakland, MD 21550
  • 20160 Garrett Hwy Unit F501-701, Oakland, MD 21550
    20160 Garrett Hwy Unit F501-701, Oakland, MD 21550
    20160 Garrett Hwy Unit F501-701, Oakland, MD 21550
    /68

    $575,000

    • 3 Beds
    • 2 Baths
    • 1,700 Sq Ft

    20160 Garrett Hwy Unit F501-701, Oakland, MD 21550

    Lakefront living at it's best can be found in this completely renovated spacious condo. This three-level unit is the perfect place to get away together! With space to come together and space to escape, this unit promises both privacy and togetherness for a memorable Deep Creek Lake experience! The first level has a full kitchen with wine fridge and attached living room with an electric fireplace,

    Kevin Liller Railey Realty, Inc.

    20160 Garrett Hwy Unit F501-701, Oakland, MD 21550
  • 5024 Cranesville Rd, Oakland, MD 21550
    5024 Cranesville Rd, Oakland, MD 21550
    5024 Cranesville Rd, Oakland, MD 21550
    /67

    $399,000

    • 3 Beds
    • 2.5 Baths
    • 2,128 Sq Ft

    5024 Cranesville Rd, Oakland, MD 21550

    Just Reduced!! Charming 3-Bedroom Home with Scenic Mountain & Valley Views. Nestled on a 1.68-acre hillside in a beautiful conservation area, this 3-bedroom, 2.5-bath home combines natural charm with modern comfort. The native stone exterior and peaceful setting set the tone for this inviting residence.Inside, the main level features a spacious primary suite with a jetted tub, double vanity,

    Rich Orr Railey Realty, Inc.

    5024 Cranesville Rd, Oakland, MD 21550
  • 328 Stool Rock Rd, Oakland, MD 21550
    328 Stool Rock Rd, Oakland, MD 21550
    328 Stool Rock Rd, Oakland, MD 21550
    /123

    $545,000

    • 4 Beds
    • 2.5 Baths
    • 1,860 Sq Ft

    328 Stool Rock Rd, Oakland, MD 21550

    Designed and built for the sellers, this 4 bedroom, 2.5 bath home is a true showcase of craftsmanship featuring handmade woodwork crafted from trees sourced directly from the property. Many specialty items will remain, including bathroom vanities, multiple dressers, a primary suite custom TV console, a built-in bunk bed, and more. The spacious primary suite was added in 2016 and offers a separate

    Kathy Gibson Railey Realty, Inc.

    328 Stool Rock Rd, Oakland, MD 21550
  • 130 Timberloft Cir Unit 14, Oakland, MD 21550
    130 Timberloft Cir Unit 14, Oakland, MD 21550
    130 Timberloft Cir Unit 14, Oakland, MD 21550
    /79

    $749,000

    • 3 Beds
    • 3 Baths
    • 1,900 Sq Ft

    130 Timberloft Cir Unit 14, Oakland, MD 21550

    Centrally located in the heart of Deep Creek Lake, this beautifully maintained 3 bedroom, 3 bath home offers breathtaking lake and mountain views year round. Designed with an open floor plan, this home is perfect for entertaining. Enjoy the stunning scenery from the spacious main-level deck, or relax in the screened-in lower level porch. A cozy fireplace on both levels adds warmth and charm,

    Nicole Jackson Railey Realty, Inc.

    130 Timberloft Cir Unit 14, Oakland, MD 21550
  • 47 Holy Cross Cir, Oakland, MD 21550
    47 Holy Cross Cir, Oakland, MD 21550
    47 Holy Cross Cir, Oakland, MD 21550
    /109

    $6,499,900

    • 8 Beds
    • 8.5 Baths
    • 11,417 Sq Ft

    47 Holy Cross Cir, Oakland, MD 21550

    Luxury lakefront living at its peak. This 11,417 sq ft masterpiece sits on 1.65 acres in The Reserve at Holy Cross with 345 feet of Deep Creek Lake frontage and an engineered DNR-approved sea wall. Crafted in 2016, the home features timber-framed vaulted ceilings, wide-plank hardwood floors, and panoramic lake views from nearly every room. The commercial-grade kitchen anchors the main level with

    Jon Bell Railey Realty, Inc.

    47 Holy Cross Cir, Oakland, MD 21550
  • 433 San Francisco St, Oakland, MD 21550
    433 San Francisco St, Oakland, MD 21550
    433 San Francisco St, Oakland, MD 21550
    /66

    $599,900

    • 6 Beds
    • 2.5 Baths
    • 2,560 Sq Ft

    433 San Francisco St, Oakland, MD 21550

    Fully renovated, fully loaded, and fully ready to be your Deep Creek Lake getaway! This 6-bedroom mountain retreat is packed with upgrades—New flooring, new septic, new hot tub, and a sleek modern kitchen with concrete counters, soft-close cabinets, and stainless steel appliances. One wood-burning fireplace for the cozy nights, one propane for the lazy mornings. Two and a half bathrooms, all

    Jon Bell Railey Realty, Inc.

    433 San Francisco St, Oakland, MD 21550
  • 126 Leo Friend Rd, Oakland, MD 21550
    126 Leo Friend Rd, Oakland, MD 21550
    126 Leo Friend Rd, Oakland, MD 21550
    /50

    $529,900

    • 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
  • 654 N Bradley Ln, Oakland, MD 21550
    654 N Bradley Ln, Oakland, MD 21550
    654 N Bradley Ln, Oakland, MD 21550
    /12

    $449,900 New Construction

    • 3 Beds
    • 2 Baths
    • 1,464 Sq Ft

    654 N Bradley Ln, Oakland, MD 21550

    NEW CONSTRUCTION from Lyv Homes! 3BR/2BA, 1464sf contemporary style home fronting on the 13th hole of the Oakland golf course. This property combines MAJESTIC scenic views with modern design, elite finishes and outdoor living. Key features include multiple wood-burning fireplaces (inside + out), Andersen windows, commercial-grade LVP flooring throughout, gourmet kitchen with soft-close cabinets

    Jay Ferguson Taylor Made Deep Creek Real Estate

    654 N Bradley Ln, Oakland, MD 21550
  • 1875 Pysell Crosscut Rd, Oakland, MD 21550
    1875 Pysell Crosscut Rd, Oakland, MD 21550
    1875 Pysell Crosscut Rd, Oakland, MD 21550
    /67

    $769,000

    • 5 Beds
    • 5 Baths
    • 3,664 Sq Ft

    1875 Pysell Crosscut Rd, Oakland, MD 21550

    With a new price you don't want to miss this chance! Beautifully maintained 5 bedroom 5 bathroom lake area chalet. Beautifully landscaped and situated on 4 +/- acres with partial views of the south side of Deep Creek Lake. Recently Professionally appraised for $868,000! This home offers it's new owners a tremendous amount of room for storage and entertaining. As well as 3 levels of finished

    Dan Shockey Taylor Made Deep Creek Real Estate

    1875 Pysell Crosscut Rd, Oakland, MD 21550
  • 164 Grandview Dr, Oakland, MD 21550
    164 Grandview Dr, Oakland, MD 21550
    164 Grandview Dr, Oakland, MD 21550
    /50

    $950,000

    • 3 Beds
    • 2.5 Baths
    • 2,368 Sq Ft

    164 Grandview Dr, Oakland, MD 21550

    Experience mountain living at its finest in this breathtaking mountaintop home overlooking Deep Creek Lake. With sweeping views from almost every room, your hardest decision may be where to sit to enjoy them. Offering three levels of living space, hardwood floors ( which were recently refinished), and some new appliances. The multiple decks are ideal to enjoy family and friends while taking in

    Betsy Spiker Holcomb Taylor Made Deep Creek Real Estate

    164 Grandview Dr, Oakland, MD 21550
  • 355 Lonesome Pine Rd, Oakland, MD 21550
    355 Lonesome Pine Rd, Oakland, MD 21550
    355 Lonesome Pine Rd, Oakland, MD 21550
    /22

    $585,000

    • 2 Beds
    • 2 Baths
    • 1,584 Sq Ft

    355 Lonesome Pine Rd, Oakland, MD 21550

    Escape to your own private mountain retreat! This contemporary 2-bed, 2-bath home is perfectly situated on approximately 84 acres of pristine land, offering breathtaking views overlooking a picturesque 7-acre field. Expansive windows, high vaulted ceilings and an open layout maximize the stunning scenery, allowing natural light to flood the space. Whether you're seeking a peaceful getaway, an

    Brody Monahan Lake Homes Realty, LLC

    355 Lonesome Pine Rd, Oakland, MD 21550
  • 519 Paradise Heights, Oakland, MD 21550
    519 Paradise Heights, Oakland, MD 21550
    519 Paradise Heights, Oakland, MD 21550
    /17

    $765,000

    • 4 Beds
    • 3 Baths
    • 2,112 Sq Ft

    519 Paradise Heights, Oakland, MD 21550

    Secluded 4 bedroom 3 bath log home with lake access and single dock slip located in the heart of Deep Creek Lake Resort Area Full unfinished basement, front covered porch and rear deck. Call Office for particulares.

    Linda Deremer Appalachian Realty

    519 Paradise Heights, Oakland, MD 21550
  • 39 Leo Friend Rd, Oakland, MD 21550
    39 Leo Friend Rd, Oakland, MD 21550
    39 Leo Friend Rd, Oakland, MD 21550
    /33

    $875,000

    • 3 Beds
    • 3.5 Baths
    • 3,897 Sq Ft

    39 Leo Friend Rd, Oakland, MD 21550

    **In the process of having new pictures taken. To see the pictures on the prior listing, go to MSL listing

    Andrew Orr The KW Collective

    39 Leo Friend Rd, Oakland, MD 21550
  • 609 Southern Pines Dr, Oakland, MD 21550
    609 Southern Pines Dr, Oakland, MD 21550
    609 Southern Pines Dr, Oakland, MD 21550
    /50

    $425,000

    • 4 Beds
    • 2.5 Baths
    • 2,250 Sq Ft

    609 Southern Pines Dr, Oakland, MD 21550

    Welcome to your next dream home! Nestled on a 4-acre wooded lot, this custom built residence combines comfort, and convenience. Just minutes from Broadford Lake Park, healthcare, shopping, Deep Creek Lake, and Wisp Ski Resort, this peaceful property offers easy access to all the local amenities. Two story stone & cedar, 4BR, 2.5 Bath w/ 2 - car attached garage, & 2 - car detached garage. Property

    Brian Covell BERKSHIRE HATHAWAY HOMESERVICES TOUCHDOWN HOME PROS REALTY

    609 Southern Pines Dr, Oakland, MD 21550
  • 267 San Francisco St, Oakland, MD 21550
    267 San Francisco St, Oakland, MD 21550
    267 San Francisco St, Oakland, MD 21550
    /30

    $899,900

    • 4 Beds
    • 2.5 Baths
    • 3,278 Sq Ft

    267 San Francisco St, Oakland, MD 21550

    Welcome to your secluded Deep Creek retreat! This stunning property offers expansive lake views! So clear you’ll catch the slopes of Wisp in the distance. Includes 3 lots and the privacy is unmatched. This house was torn down to the foundation and a new house was built in 2009. Inside, you’ll find four spacious bedrooms, two and a half baths, and soaring vaulted ceilings and a grand fireplace.

    Bradley West HomeSmart

    267 San Francisco St, Oakland, MD 21550
  • 104 Pine Top Trail, Oakland, MD 21550
    104 Pine Top Trail, Oakland, MD 21550
    104 Pine Top Trail, Oakland, MD 21550
    /13

    $425,000

    • 3 Beds
    • 3.5 Baths
    • 1,596 Sq Ft

    104 Pine Top Trail, Oakland, MD 21550

    Here's your chance to purchase a cute Chalet with just about 7 acres. .This home and acreage is right next to the Common Grounds and gives you immediate river access.

    laura Flynn 1 Real Estate Source LLC

    104 Pine Top Trail, Oakland, MD 21550
  • 175 Roman Ridge Rd Unit 15, Oakland, MD 21550
    175 Roman Ridge Rd Unit 15, Oakland, MD 21550
    175 Roman Ridge Rd Unit 15, Oakland, MD 21550
    /53

    $519,000

    • 4 Beds
    • 4.5 Baths
    • 3,192 Sq Ft

    175 Roman Ridge Rd Unit 15, Oakland, MD 21550

    Welcome to this 4-bedroom, 4.5-bath stand-alone, multi-level unit in Traders Landing! Offering filtered lake views, ample square footage, oversized bedrooms, and multiple living spaces, this property is ideal for entertaining, large groups, or relaxed mountain-lake living. Enjoy a central Deep Creek location just minutes from Deep Creek Lake, local restaurants, shopping, and Wisp Resort.

    Nina Beitzel Railey Realty, Inc.

    175 Roman Ridge Rd Unit 15, Oakland, MD 21550
  • 333 Sloan Tract Rd, Oakland, MD 21550
    333 Sloan Tract Rd, Oakland, MD 21550
    333 Sloan Tract Rd, Oakland, MD 21550
    /43

    $475,000

    • 4 Beds
    • 3.5 Baths
    • 1,492 Sq Ft

    333 Sloan Tract Rd, Oakland, MD 21550

    Charming cabin off the coveted Lake Shore Drive offering seasonal lake views. This home has three levels of living space, hardwood flooring and a nice fireplace. The lower level is totally finished with walk-out access. There are multiple covered porches plus a hot tub that are great outdoor spaces to enjoy year round. This home feels very secluded but is just minutes to Deep Creek Lake and Wisp

    Betsy Spiker Holcomb Taylor Made Deep Creek Real Estate

    333 Sloan Tract Rd, Oakland, MD 21550
  • 24 Trailside Way, Oakland, MD 21550
    24 Trailside Way, Oakland, MD 21550
    24 Trailside Way, Oakland, MD 21550
    /43

    $555,000

    • 4 Beds
    • 3.5 Baths
    • 2,430 Sq Ft

    24 Trailside Way, Oakland, MD 21550

    Tucked in the Silver Ridge community at Deep Creek Lake, this inviting home blends rustic charm with comfortable modern living. Community trails and shared green space offer opportunities for outdoor recreation, while the wooded setting behind the home provides a sense of privacy and a peaceful natural backdrop. Step inside to an interior that reflects its surroundings, where warm wood accents,

    Jackie Ball Daley Northrop Realty

    24 Trailside Way, Oakland, MD 21550
  • 2 Overlook Ridge Dr S, Oakland, MD 21550
    2 Overlook Ridge Dr S, Oakland, MD 21550
    2 Overlook Ridge Dr S, Oakland, MD 21550
    /11

    $199,900

    • Land
    • 0.11 Acre
    • $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
  • 505 Southern Pines Dr, Oakland, MD 21550
    505 Southern Pines Dr, Oakland, MD 21550
    505 Southern Pines Dr, Oakland, MD 21550
    /38

    $297,500

    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft

    505 Southern Pines Dr, Oakland, MD 21550

    Charming ranch-style home located in the desirable Southern Pines neighborhood. From the moment you enter, you’ll appreciate the warm and inviting feel of the open layout. The main level features three comfortable bedrooms, two full bathrooms, beautiful hardwood flooring, and a seamless kitchen, living, and dining area that creates an ideal space for everyday living and entertaining. The recently

    Betsy Spiker Holcomb Taylor Made Deep Creek Real Estate

    505 Southern Pines Dr, Oakland, MD 21550

Showing Results 1 - 40, Page 1 of 3

Maryland Garrett County Oakland

Real Estate & Homes for Sale in Oakland, MD

Why Live in Oakland

When people think of Maryland, the bustling city of Baltimore and the coastal capital of Annapolis often come to mind. But there’s much more to discover in the western portion of this state, particularly in the mountain city of Oakland. “Deep Creek ...

Learn more about living in Oakland

Frequently Asked Questions

What is the average home price in Oakland, MD?
Homes for sale in Oakland, MD have an average home price of $537,380.
Are home prices dropping in Oakland?
Yes, home prices in Oakland are down 3% in the last 12 months.
How many homes have sold over the last 12 months in Oakland, MD?
136 homes have sold in Oakland, MD over the last 12 months.
What are the most popular zip codes in Oakland, MD?
The most popular zip codes in Oakland, MD include 21550, 26764, 21561, 21541 and 26720.
How much do you need to make to afford a house in Oakland?
The median home price in Oakland is $425,000. If you put a 20% down payment of $85,000 and had a 30-year fixed mortgage with an interest rate of 6.11%, your estimated principal and interest payment would be $2,060 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $88K a year to afford the median home price in Oakland. Learn how much home you can afford with our Home Affordability Calculator.
How are the schools in Oakland, MD?
Oakland, MD has highly rated public and private schools. Some of the best schools in Oakland based on Niche Grades are Swan Meadow School, Crellin Elementary School and Southern Middle School. Browse all the schools in Oakland, MD to learn more.

Home Trends in Oakland, MD

On average, homes in Oakland, MD sell after 89 days on the market compared to the national average of 55 days. The median sale price for homes in Oakland, MD over the last 12 months is $428,000, up 7% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$428,000
Median Single Family Sale Price
$405,000
Median Townhouse Sale Price
$510,000
Median 2 Bedroom Sale Price
$314,000
Median 1 Bedroom Sale Price
$229,900
Average Price Per Sq Ft
$257
Number of Homes for Sale
49
Last 12 months Home Sales
136
Months of Supply
4.30
Median List Price
$425,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
7%
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