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Oakland, MD Homes for Sale with AC

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  • 62 Duck Cove Rd, Oakland, MD 21550
    62 Duck Cove Rd, Oakland, MD 21550
    62 Duck Cove Rd, Oakland, MD 21550
    /73

    $1,899,000

    • 4 Beds
    • 4 Baths
    • 4,150 Sq Ft

    62 Duck Cove Rd, Oakland, MD 21550

    One of Deep Creek Lake's most premium settings greets you on the point of this remarkable 4 bedroom, 4 bathroom lakefront home with 231' of level lakefront with eastern exposure, offering amazing sunrises looking down a long stretch of the lake toward Turkeyneck! 1 oversize attached garage space offers plenty of space for your vehicles on the street side and 2 attached garage spaces provide room

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 875-6601

    62 Duck Cove 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
  • 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
  • 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
  • 1167 Tall Oaks Dr, Oakland, MD 21550
    1167 Tall Oaks Dr, Oakland, MD 21550
    1167 Tall Oaks Dr, Oakland, MD 21550
    /61

    $379,000

    • 2 Beds
    • 2.5 Baths
    • 1,920 Sq Ft

    1167 Tall Oaks Dr, Oakland, MD 21550

    Picture perfect log cabin on 11 private, wooded acres in the gated Timbers on the Yough community featuring Youghiogheny River access. This inviting home features a metal roof, spacious covered deck, newly installed walkway, exterior fire pit, breakfast bar, and pellet stove. The primary bath offers dual sinks, an oversized soaking tub, dual shower heads and radiant floor heat!Recent updates

    Kellyann Green Railey Realty, Inc.

    1167 Tall Oaks Dr, Oakland, MD 21550
  • 163 Mitchell Dr, Oakland, MD 21550
    163 Mitchell Dr, Oakland, MD 21550
    163 Mitchell Dr, Oakland, MD 21550
    /62

    $299,000

    • 3 Beds
    • 2.5 Baths
    • 2,242 Sq Ft

    163 Mitchell Dr, Oakland, MD 21550

    Nestled in the charming Mitchell Manor community, this delightful split-level home offers a perfect blend of comfort and style. With 2,242 square feet of thoughtfully designed living space, this residence features three spacious bedrooms and two and a half bathrooms, ideal for both relaxation and entertaining. There is also a walk-in closet/dressing room to die for! Step inside to discover an

    Andrew Eiswert Railey Realty, Inc.

    163 Mitchell Dr, 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 1010 Holy Cross Dr, Oakland, MD 21550
    1010 Holy Cross Dr, Oakland, MD 21550
    1010 Holy Cross Dr, Oakland, MD 21550
    /147

    $5,150,000 Coming Soon

    • 8 Beds
    • 8.5 Baths
    • 10,300 Sq Ft

    1010 Holy Cross Dr, Oakland, MD 21550

    ICONIC. A design masterpiece of stone and timber — a true Rex Anderson build that reflects the seamless merging of inspiration and architecture. Warm, and undeniably welcoming, this home stands as a statement of craftsmanship and vision. Discover a breathtaking blend of contemporary luxury and timeless timber frame construction, perfectly positioned for privacy within the prestigious Reserve at

    Rachel Bruch Railey Realty, Inc.

    1010 Holy Cross Dr, Oakland, MD 21550
  • 222 Skippers Point Rd, Oakland, MD 21550
    222 Skippers Point Rd, Oakland, MD 21550
    222 Skippers Point Rd, Oakland, MD 21550
    /56

    $779,000

    • 5 Beds
    • 1.5 Baths
    • 1,278 Sq Ft

    222 Skippers Point Rd, Oakland, MD 21550

    Lake cottage 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 and cozy, well

    Julie Mead The KW Collective

    222 Skippers Point Rd, Oakland, MD 21550
  • 13 Laurel Brook Dr, Oakland, MD 21550
    13 Laurel Brook Dr, Oakland, MD 21550
    13 Laurel Brook Dr, Oakland, MD 21550
    /42

    $245,000

    • 2 Beds
    • 2 Baths
    • 1,320 Sq Ft

    13 Laurel Brook Dr, Oakland, MD 21550

    Affordable well maintained 2 Bedroom 2 Bath townhouse style condominium less than 1 mile from Deep Creek Lake. Offering low maintenance and a pleasant setting, the property works well for full and part time ownership. The unit offers recent upgrades and Includes 2 parking spaces along with public water, sewer and weekly trash pickup. Shown by appointment only.

    Bill Weissgerber Railey Realty, Inc.

    13 Laurel Brook Dr, Oakland, MD 21550
  • 137 Paradise Gardens Rd, Oakland, MD 21550
    137 Paradise Gardens Rd, Oakland, MD 21550
    137 Paradise Gardens Rd, Oakland, MD 21550
    /71

    $1,049,000

    • 4 Beds
    • 2 Baths
    • 2,730 Sq Ft

    137 Paradise Gardens Rd, Oakland, MD 21550

    Remodeled 4BR/2BA lakefront A-frame with two deep water dock slips! Impressive renovation from top to bottom, this home has everything you are seeking in a vacation home AND a huge, fenced in yard surrounded by massive trees, fire pit and storage building. Features include a massive stone fireplace (wood burning), hot tub with lake views, large kitchen with island, custom tile showers & bathrooms

    Jay Ferguson Taylor Made Deep Creek Real Estate

    137 Paradise Gardens Rd, Oakland, MD 21550
  • 18 Ollie North Rd, Oakland, MD 21550
    18 Ollie North Rd, Oakland, MD 21550
    18 Ollie North Rd, Oakland, MD 21550
    /48

    $289,000

    • 4 Beds
    • 2 Baths
    • 1,956 Sq Ft

    18 Ollie North Rd, Oakland, MD 21550

    Welcome to 18 Ollie North in Oakland, MD—an exceptionally well-maintained home offering comfort, functionality, and space both inside and out. This inviting 4-bedroom, 2-full bath residence spans two levels and showcases meticulous care throughout. Inside, you’ll find a bright and welcoming layout with a well-appointed kitchen featuring stainless steel appliances, perfect for everyday living or

    Nina Beitzel Railey Realty, Inc.

    18 Ollie North Rd, Oakland, MD 21550
  • 620 Crosby Dr, Oakland, MD 21550
    620 Crosby Dr, Oakland, MD 21550
    620 Crosby Dr, Oakland, MD 21550
    /62

    $739,000

    • 4 Beds
    • 3.5 Baths
    • 3,420 Sq Ft

    620 Crosby Dr, Oakland, MD 21550

    This stunning, recently built 4+ bedroom, 3.5 bath home in Country Club Acres offers modern design, thoughtful upgrades, and unmatched privacy on 3.43 wooded acres perched at the top of the mountain overlooking Oakland Golf Course and multiple ponds. The bright, open-concept layout is filled with natural light and features commercial-grade LVP flooring throughout, complemented by mid-range,

    Jay Ferguson Taylor Made Deep Creek Real Estate

    620 Crosby Dr, Oakland, MD 21550
  • 135 Jeffrey Ln Unit 19-A, Oakland, MD 21550
    135 Jeffrey Ln Unit 19-A, Oakland, MD 21550
    135 Jeffrey Ln Unit 19-A, Oakland, MD 21550
    /22

    $294,999

    • 2 Beds
    • 1 Bath
    • 2,344 Sq Ft

    135 Jeffrey Ln Unit 19-A, Oakland, MD 21550

    Experience the best of lakeview living in this great condo at Deep Creek Lake. Offering two bedrooms, a fireplace and a lower-level family room for your enjoyment. Wake up to peaceful water views and enjoy ample space for everyday comfort and entertaining. The location is another plus, within walking distance to coffee shop, dining, and shopping. A perfect blend of size, scenery, and value!

    Betsy Spiker Holcomb Taylor Made Deep Creek Real Estate

    135 Jeffrey Ln Unit 19-A, Oakland, MD 21550
  • 3930 Mayhew Inn Rd, Oakland, MD 21550
    3930 Mayhew Inn Rd, Oakland, MD 21550
    3930 Mayhew Inn Rd, Oakland, MD 21550
    /81

    $399,900

    • 3 Beds
    • 3 Baths
    • 2,227 Sq Ft

    3930 Mayhew Inn Rd, Oakland, MD 21550

    2 for 1 on 2 .3 +/- acres! Remodeled 2BR 2BA cottage with auxiliary building that has an oversized garage, multiple workshop areas and 1BR 1BA apartment on the second level. New Maryland legislation, Accessory Dwelling Units Act of 2025, will allow expanded access to use the apartment above the garage in a more meaningful manner. Cabin boasts high end finishes and open living space with a cozy

    Jay Ferguson Taylor Made Deep Creek Real Estate

    3930 Mayhew Inn Rd, Oakland, MD 21550
  • 1544 Stockslager Rd, Oakland, MD 21550
    1544 Stockslager Rd, Oakland, MD 21550
    1544 Stockslager Rd, Oakland, MD 21550
    /63

    $1,750,000

    • 5 Beds
    • 4 Baths
    • 3,456 Sq Ft

    1544 Stockslager Rd, Oakland, MD 21550

    Enjoy lakefront living at its finest in this beautifully remodeled home with a private dock. Thoughtfully updated with modern finishes including a kitchen remodel, new windows and doors, new upper balcony, new flooring throughout, and recently added mini splits on the lower level. This property offers stunning water views, an open-concept layout, five bedrooms (three of which are en suites), and

    Betsy Spiker Holcomb Taylor Made Deep Creek Real Estate

    1544 Stockslager Rd, Oakland, MD 21550
  • 565 Glendale Rd Unit 125, Oakland, MD 21550
    565 Glendale Rd Unit 125, Oakland, MD 21550
    565 Glendale Rd Unit 125, Oakland, MD 21550
    /55

    $329,900

    • 1 Bed
    • 1 Bath
    • 496 Sq Ft

    565 Glendale Rd Unit 125, Oakland, MD 21550

    Wake up to the lake at your doorstep. This ground-level, end-unit condo offers true lakefront living with unbeatable access to everything Deep Creek Lake has to offer. Enjoy effortless days on the water, then relax with on-site amenities including a fitness room, sauna, game room, and expansive lakeside decking. Walk to Dutch’s at Silver Tree, The Harbor Bar, and the marina for dining, drinks,

    Jon Bell Railey Realty, Inc.

    565 Glendale Rd Unit 125, Oakland, MD 21550
  • 1038 S Blakeslee Rd, Oakland, MD 21550
    1038 S Blakeslee Rd, Oakland, MD 21550
    1038 S Blakeslee Rd, Oakland, MD 21550
    /69

    $2,100,000

    • 5 Beds
    • 5 Baths
    • 4,074 Sq Ft

    1038 S Blakeslee Rd, Oakland, MD 21550

    Welcome to 1038 S Blakeslee Road! A spacious lakefront retreat on Deep Creek Lake offering effortless lakeside living. A Rare opportunity to own in one of Deep Creek’s most sought-after lakeside communities. This five-bedroom, five-bath home sits on a large 1.11-acre level lot with easy access to the water and generous outdoor space for recreation and entertaining. Inside, the home is warm and

    Eric Crawford Taylor Made Deep Creek Real Estate

    1038 S Blakeslee Rd, Oakland, MD 21550
  • 565 Glendale Rd Unit 124, Oakland, MD 21550
    565 Glendale Rd Unit 124, Oakland, MD 21550
    565 Glendale Rd Unit 124, Oakland, MD 21550
    /30

    $159,000

    • 1 Bed
    • 1 Bath
    • 382 Sq Ft

    565 Glendale Rd Unit 124, Oakland, MD 21550

    Public: If you are looking for an affordable way to own at Deep Creek Lake, this is it! This Silver Tree Suites unit is is main floor and beautiful. .Offering a king size bed, and a propane fireplace. The hotel offers a sitting area, sauna and workout area for your enjoyment. The Dutch's restaurant & Harbor Bar are just steps away, offering wonderful dining options while never having to leave the

    ANGELA BOSLEY Taylor Made Deep Creek Real Estate

    565 Glendale Rd Unit 124, 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
  • 53 Bird Ave, Oakland, MD 21550
    53 Bird Ave, Oakland, MD 21550
    53 Bird Ave, Oakland, MD 21550
    /34

    $239,700

    • 3 Beds
    • 3 Baths
    • 1,104 Sq Ft

    53 Bird Ave, Oakland, MD 21550

    Opportunity and a peaceful country setting on 1.55 acres in Deer Park. This 3BR, 2BA ranch offers 1,872 sq ft with solid bones and room to make it your own. The spacious kitchen with hickory cabinets, gas stove, and propane fireplace creates a warm gathering space at the heart of the home. Outside, several outbuildings—including a large shop and secondary wood shop with heat and electric, a

    Rachel Bruch Railey Realty, Inc.

    53 Bird Ave, 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

    $292,500

    • 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
  • 62 Whispering Pines Ln, Oakland, MD 21550
    62 Whispering Pines Ln, Oakland, MD 21550
    62 Whispering Pines Ln, Oakland, MD 21550
    /77

    $930,000

    • 4 Beds
    • 3.5 Baths
    • 2,464 Sq Ft

    62 Whispering Pines Ln, Oakland, MD 21550

    Tucked away on just over 7 acres of serene, wooded privacy, this stunning custom Yellowstone log home offers the perfect blend of rustic charm and modern comfort—just minutes from Swallow Falls State Park and only 10 minutes to Deep Creek Lake and Wisp Resort. The inviting open main level is designed for effortless entertaining, highlighted by a warm gas fireplace in the family room, a spacious

    Justin Liller Railey Realty, Inc.

    62 Whispering Pines Ln, Oakland, MD 21550
  • 467 Paradise Ridge Rd, Oakland, MD 21550
    467 Paradise Ridge Rd, Oakland, MD 21550
    467 Paradise Ridge Rd, Oakland, MD 21550
    /60

    $799,900

    • 4 Beds
    • 3.5 Baths
    • 3,780 Sq Ft

    467 Paradise Ridge Rd, Oakland, MD 21550

    Panoramic mountain and lake views set the tone at this lake access home in Paradise Ridge, one of Deep Creek’s most sought-after communities! Perched at the top of the hill on 1.29 acres, this 4-bedroom, 3 full and 1 half bath retreat offers 3,780 finished square feet across three levels. Abundant glass frames the surrounding ridgelines with views of Deep Creek Lake from every room in the house!

    Jon Bell Railey Realty, Inc.

    467 Paradise Ridge Rd, Oakland, MD 21550
  • 8 Laurel Brook Dr, Oakland, MD 21550
    8 Laurel Brook Dr, Oakland, MD 21550
    8 Laurel Brook Dr, Oakland, MD 21550
    /30

    $284,900

    • 2 Beds
    • 2 Baths
    • 1,340 Sq Ft

    8 Laurel Brook Dr, Oakland, MD 21550

    Re-positioned price to sell. Beautiful Renovated 2-bedroom, 2-bath condo is Turnkey Ready Now for Part-time, Full-time Living or Rental, located in this quiet desirable Laurel Brook community, close to the lake, local activities, and everyday amenities. Warm, welcoming, and filled with natural light, the home features mountain views and a skylight in the living room that enhances the open airy

    Karen Hart Cummings & Co. Realtors

    8 Laurel Brook Dr, Oakland, MD 21550
  • 815 Chadderton School Rd, Oakland, MD 21550
    815 Chadderton School Rd, Oakland, MD 21550
    815 Chadderton School Rd, Oakland, MD 21550
    /110

    $1,900,000

    • 5 Beds
    • 3.5 Baths
    • 4,619 Sq Ft

    815 Chadderton School Rd, Oakland, MD 21550

    Experience lakefront living at its finest in this exceptional 5-bedroom, 3.5-bath home offering over 4,600 square feet of living space on a private lot of more than one acre. Featuring an incredibly spacious primary suite on the main level, as well as an additional master suite on the second level, this home is ideal for both full-time living and hosting guests. Enjoy breathtaking lake views from

    Kevin Liller Railey Realty, Inc.

    815 Chadderton School Rd, Oakland, MD 21550
  • 231 Santa fe Trail, Oakland, MD 21550
    231 Santa fe Trail, Oakland, MD 21550
    231 Santa fe Trail, Oakland, MD 21550
    /37

    $629,000

    • 4 Beds
    • 3 Baths
    • 2,280 Sq Ft

    231 Santa fe Trail, Oakland, MD 21550

    3/4BR 3BA chalet with LAKE VIEWS! 2300sf vacation home fronting on a mountain stream, overlooking Deep Creek Lake! Enjoy an eat-in kitchen, exposed beams and a loft area that the current owners use as a 4th BR with bathroom. NO HOA! Conveys fully furnished. Features include central AC, exposed beams, updated flooring, gas fireplace on main level, lower level rec room with pool table and

    Jay Ferguson Taylor Made Deep Creek Real Estate

    231 Santa fe Trail, Oakland, MD 21550
  • 232 Jeffrey Ln Unit 33, Oakland, MD 21550
    232 Jeffrey Ln Unit 33, Oakland, MD 21550
    232 Jeffrey Ln Unit 33, Oakland, MD 21550
    /39

    $425,000

    • 2 Beds
    • 2.5 Baths
    • 2,960 Sq Ft

    232 Jeffrey Ln Unit 33, Oakland, MD 21550

    Turn-key and fully furnished, this beautifully maintained duplex offers the perfect blend of comfort, views, and location in the heart of Deep Creek Lake. Featuring an open, inviting floor plan, the home is designed for both everyday enjoyment and effortless entertaining. The main level features a spacious living area with a stone-surround fireplace, abundant natural light, and a seamless flow to

    Sean Brink Samson Properties

    232 Jeffrey Ln Unit 33, 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

    $509,000

    • 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
  • 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
  • 931 Black Oak Dr, Oakland, MD 21550
    931 Black Oak Dr, Oakland, MD 21550
    931 Black Oak Dr, Oakland, MD 21550
    /53

    $349,999

    • 3 Beds
    • 1 Bath
    • 990 Sq Ft

    931 Black Oak Dr, Oakland, MD 21550

    Very motivated sellers!!!Escape to Your Profitable Mountain Sanctuary: The Yough Mountain CabinUnveiling the Ultimate Turnkey Retreat & High-Performing InvestmentNestled in the breathtaking heart of the exclusive Yough Mountain Resort, this stunning 3-bedroom cabin offers the perfect harmony of rustic soul and modern investment savvy. Whether you are looking for a private family getaway

    ANGELA BOSLEY Taylor Made Deep Creek Real Estate

    931 Black Oak Dr, Oakland, MD 21550
  • 178 Winding Trail Ln Unit 5B, Oakland, MD 21550
    178 Winding Trail Ln Unit 5B, Oakland, MD 21550
    178 Winding Trail Ln Unit 5B, Oakland, MD 21550
    /47

    $589,000

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

    178 Winding Trail Ln Unit 5B, Oakland, MD 21550

    Tucked into a peaceful, wooded setting yet right in the heart of everything Deep Creek Lake has to offer, Whispering Pines is the ultimate turnkey mountain retreat. This impeccably maintained 5-bedroom townhome spans three levels of inviting living space and features an attached garage—perfect for hosting family, friends, or guests year-round. Enjoy the best of both worlds: a private, serene

    Nina Beitzel Railey Realty, Inc.

    178 Winding Trail Ln Unit 5B, Oakland, MD 21550
  • 209 Glendale Rd, Oakland, MD 21550
    209 Glendale Rd, Oakland, MD 21550
    209 Glendale Rd, Oakland, MD 21550
    /89

    $2,100,000

    • 6 Beds
    • 4.5 Baths
    • 3,882 Sq Ft

    209 Glendale Rd, Oakland, MD 21550

    If you're in the market for location, convenience, and rental income, this inviting 6 Bedroom 4.5 bath Lakefront home is calling for you! Located in the heart of the action on Deep Creek Lake, the 3 level chateau has been updated and upgraded both inside and out. Restaurants, the movie theatre, shopping and Deep Creek Lake State Park are all within walking distance. Offering an open layout with

    Bill Weissgerber Railey Realty, Inc.

    209 Glendale Rd, Oakland, MD 21550

Showing Results 1 - 40, Page 1 of 2

Maryland Garrett County Oakland

Homes for Sale with AC in Oakland, MD

Home Trends in Oakland, MD

On average, homes in Oakland, MD sell after 96 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 $407,000, down 1% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$407,000
Median Single Family Sale Price
$402,500
Median Townhouse Sale Price
$460,000
Median 2 Bedroom Sale Price
$310,250
Median 1 Bedroom Sale Price
$217,450
Average Price Per Sq Ft
$263
Number of Homes for Sale
54
Last 12 months Home Sales
139
Months of Supply
4.70
Median List Price
$405,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-1%
How to Buy a Home How to Finance a Home How to Sell a Home

In Oakland, there are currently 68 homes for sale with air conditioning, providing cool relief during warm summer months. These properties are equipped with modern amenities like central air conditioning systems or individual units, ensuring residents stay comfortable even in hot weather. Whether it's a single-family home or a townhouse, homes for sale with air conditioning offer a pleasant atmosphere year-round. Explore the selection of homes for sale with AC in Oakland, MD and enjoy the comfort they provide.

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