189

Homes for Sale in 21550

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  • /5

    $89,900

    • Land
    • 15.75 Acres
    • $5,708 per Acre

    TBD 15 75 Acres Bethlehem Rd, Oakland, MD 21550

    Tucked away just minutes from town, this 15.75± acre wooded parcel offers a quiet country setting with the privacy many buyers are searching for. Located off Bethlehem Road near the Potomac State Forest, the property features largely level terrain, mature trees, and abundant wildlife—an ideal backdrop for a private residence, weekend retreat, or recreational use. The surrounding area provides

    Thomas Long Railey Realty, Inc.

    TBD 15 75 Acres Bethlehem Rd, 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
  • /59

    $220,000

    • 2 Beds
    • 1 Bath
    • 1,064 Sq Ft

    313 W Liberty St, Oakland, MD 21550

    Charming and meticulously maintained 1947 brick ranch located at the edge of Oakland town limits on a beautiful 1⁄4-acre lot. This 2-bedroom, 1-bath home features spacious rooms, natural gas heat, public utilities, and a full unfinished basement offering great storage or future potential. Ownership includes a 1⁄2 interest in a shared 2-car garage. Conveniently situated near schools, the hospital,

    Justin Liller Railey Realty, Inc.

    313 W Liberty St, 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
  • /73

    $1,087,900 New Construction

    • 4 Beds
    • 6 Baths
    • 3,032 Sq Ft

    52 Dam View Dr, Mount Lake Park, MD 21550

    Panoramic Lake views in the Bray Run community, just minutes from Deep Creek Lake, state parks, and more! Built in 2025, this 4-bedroom, 4 full bath, 2 half bath log style chalet sits on 0.59 acres of peaceful, quiet serenity. Cathedral and beamed ceilings rise above an open layout filled with abundant natural light. Two stacked-stone fireplaces anchor the main living area and the lower-level

    Mike Fenton Railey Realty, Inc.

    52 Dam View Dr, Mount Lake Park, MD 21550
  • /29

    $300,000

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

    8 Laurel Brook Dr, Oakland, MD 21550

    Fully renovated 2-bedroom, 2-bath condo is 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 feel.The thoughtfully redesigned interior offers an open-concept main floor with shiplap

    Karen Hart Cummings & Co. Realtors

    8 Laurel Brook Dr, Oakland, MD 21550
  • /18

    $4,000

    • Land
    • 0.47 Acre
    • $8,511 per Acre

    Lot 36 Fox Tail Rd, Oakland, MD 21550

    Discover your mountain escape in Yough Mountain Resort, a gated recreational community in the scenic mountains of Western Maryland, just a short drive to Deep Creek Lake. This amenity-rich community is designed for outdoor enthusiasts, offering ATV and snowmobile trails, Yough River access, nearby state parks, hunting opportunities, plus a playground and pavilion area for gathering.This

    Shannon McWilliams The KW Collective

    Lot 36 Fox Tail Rd, Oakland, MD 21550
  • /49

    $875,000

    • 5 Beds
    • 3 Baths
    • 3,178 Sq Ft

    448 Biltmore View, Mc Henry, MD 21541

    Welcome to this beautifully crafted 5-bedroom, 3-bath, two-story home in the desirable Biltmore community at Lodestone Golf Course. Built in 2022, this thoughtfully designed property blends modern mountain style with quality craftsmanship, offering solid finishes inside and out and a layout ideal for both everyday living and vacation enjoyment. The open-concept main level features spacious living

    Nina Beitzel Railey Realty, Inc.

    448 Biltmore View, Mc Henry, MD 21541
  • /64

    $1,275,000

    • 6 Beds
    • 6.5 Baths
    • 3,384 Sq Ft

    36 Irwin Way, McHenry, MD 21541

    Welcome to All The Time, a beautifully crafted mountain retreat in the heart of Deep Creek Lake and right along Lodestone Golf Course. Blending modern comfort with rustic charm, this inviting getaway is designed for unforgettable moments with family and friends. Inside, the bright open-concept living area features a cozy fireplace and plenty of space to gather after a day of adventure. The fully

    Nina Beitzel Railey Realty, Inc.

    36 Irwin Way, McHenry, MD 21541
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /25

    $335,000

    • Land
    • 70 Acres
    • $4,786 per Acre

    TBD Highway 50, Gormania, WV 26720

    This uniquely located 70+/- AC property is in close proximity to both Canaan Valley, Timberline Mountain Resort, and Deep Creek Lake, MD with approximately 1 mile of stocked trout water frontage on the North Branch of the Potomac River. An old homestead site along the river would make for a beautiful flat building site. Marketable timber with timber report available. Excellent Hunting. Property

    Steve Galusky Railey WV Properties

    TBD Highway 50, Gormania, WV 26720
  • /104

    $1,350,000

    • 5 Beds
    • 5.5 Baths
    • 3,696 Sq Ft

    615 Sandy Shores Rd, Mc Henry, MD 21541

    This stunning log home near Wisp Resort offers a luxurious retreat with seasonal views, an indoor pool house and plenty of space for indoor and outdoor living. Five-bedroom, five-and-a-half-bath masterpiece is designed for both relaxation and entertainment. Step inside to discover an open floor plan adorned with exposed beams and rich wood floors. The gourmet kitchen, equipped with high-end

    Kellyann Green Railey Realty, Inc.

    615 Sandy Shores Rd, Mc Henry, MD 21541
  • /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
  • /19

    $295,000

    • Land
    • 8.48 Acres
    • $34,788 per Acre

    26 Green Brier Rd, Oakland, MD 21550

    8.48± acres offering excellent commercial or residential potential. Property features an existing well and septic system, with easy access and outstanding visibility. Conveniently located just minutes from the Oakland city limits outside of Zoning Districts. Ideal opportunity for development or investment.

    Rich Orr Railey Realty, Inc.

    26 Green Brier Rd, Oakland, MD 21550
  • /19

    $74,900

    • Land
    • 0.44 Acre
    • $170,227 per Acre

    39 Greenstone Way, Mc Henry, MD 21541

    Level building site in the gated Lodestone community atop the mountain at Wisp Resort! This .44-acre lot offers golf course views, paved road access, and an easy build setup with public water and public sewer available. Located minutes from Wisp ski slopes, the ASCI Whitewater Course, Lodestone Golf Course, and the restaurants, shops, and marinas at Deep Creek Lake. The HOA provides road

    Mike Fenton Railey Realty, Inc.

    39 Greenstone Way, Mc Henry, MD 21541
  • /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
  • /61

    $185,000

    • 3 Beds
    • 1.5 Baths
    • 1,170 Sq Ft

    729 E Oak St, Oakland, MD 21550

    Great, affordable starter home located in Oakland with public water and sewer, one car detached garage, hot water natural gas heat. Two bedroom and full bath on second level and possible third bedroom on main level with 1/2 bath. Cellar basement with mechanicals. Washer and Dryer hookups, washer/dryer convey, are located on the back enclosed porch which has electric baseboard heat. Enclosed front

    Kevin Liller Railey Realty, Inc.

    729 E Oak St, Oakland, MD 21550
  • /10

    $995,000

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

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

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

    Lucas Muenchow Railey Realty, Inc.

    0 Glendale Rd Lot 12 Alpine Village Subdivision, Oakland, MD 21550
  • /15

    $64,900

    • Land
    • 0.71 Acre
    • $91,408 per Acre

    2 Fern Loop, Sang Run, MD 21541

    A clean .71-acre building lot in Sandy Shores Heights—level, partially wooded, with utilities to site. Minutes from Lodestone, Wisp, and Deep Creek Lake... this property sits in a quiet golf side loop with mountain views and paved access. Water and sewer taps included. Road maintenance and snow removal covered by HOA fees. Call today for details!

    Mike Fenton Railey Realty, Inc.

    2 Fern Loop, Sang Run, MD 21541
  • /11

    $125,000

    • Land
    • 0.7 Acre
    • $178,571 per Acre

    Lot 115 Biltmore View, McHenry, MD 21541

    Premium golf-front building lot located in a private, gated community and ideally situated near all Deep Creek Lake amenities, including Wisp Ski Resort, the ASCI Whitewater Course, and Fork Run Trails. This .7-acre level, wooded parcel offers potential views of the golf course and surrounding mountain landscape—an exceptional setting to build your dream home in the heart of Deep Creek Lake.

    Kellyann Green Railey Realty, Inc.

    Lot 115 Biltmore View, McHenry, MD 21541
  • /18

    $104,000

    • Land
    • 0.89 Acre
    • $116,854 per Acre

    72 Sundance Way, McHenry, MD 21541

    Beautiful Wooded Building Lot adjoining Lodestone Golf Course - The private wooded parcel offers nearly a full acre of level building space and backs directly up to Hole #6's green at Lodestone Golf Course! Located in McHenry MD, you're minutes from local establishments, state parks, and Deep Creek Lake. Less than a mile from the slopes at WISP Resort, your future dream home is perched perfectly

    Mike Fenton Railey Realty, Inc.

    72 Sundance Way, McHenry, MD 21541
  • /20

    $189,000 New Construction

    • 4 Beds
    • 2 Baths

    3395 Fingerboard Rd, Oakland, MD 21550

    6+ acre homestead with a 4BR, 2BA home currently under construction. Sellers plans have changed and they will not be finishing the house. The structure is under roof, mostly framed-in with building materials on site that will convey with the sale. A new well has been drilled and septic permit is approved for 4BRs. Located just outside of town limits, this parcel has impressive mountain views and

    Jay Ferguson Taylor Made Deep Creek Real Estate

    3395 Fingerboard Rd, 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
  • /13

    $119,900

    • Land
    • 0.78 Acre
    • $153,718 per Acre

    120 Sundance Way, McHenry, MD 21541

    Level wooded building lot with scenic mountain views! This .78-acre homesite is centrally located minutes from Wisp Resort, Deep Creek Lake, Lodestone Golf Course, local restaurants, and nearby state parks, all while tucked away in a private mountaintop community. Ready to build with public water and sewer hookups to site. A straightforward opportunity to build your mountain dream home right in

    Mike Fenton Railey Realty, Inc.

    120 Sundance Way, McHenry, MD 21541
  • /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
  • /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
  • /37

    $85,000

    • 2 Beds
    • 1 Bath
    • 864 Sq Ft

    1358 Crellin Underwood Rd, Oakland, MD 21550

    Charming 2-bedroom, 1-bath home offering a fantastic opportunity for buyers looking to add their own personal touch. Recent updates include a metal roof, 2 propane wall unit heaters, and a hot water heater. Enjoy the back covered deck overlooking the woods and the youghiogheny river below. This property needs a bit of TLC but is full of potential and character. Located in a highly desirable

    Lucas Muenchow Railey Realty, Inc.

    1358 Crellin Underwood 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
  • /24

    $225,000

    • Land
    • 1.33 Acres
    • $169,173 per Acre

    Lot 94 Wisp Adventure Rd, McHenry, MD 21541

    Oversized mountain-view lot in North Camp Ridge, ideally located just minutes from Wisp Resort amenities. This centrally located parcel offers the perfect setting to build your custom vacation home or mountain retreat. Enjoy expansive, unobstructed mountain views and the privacy that comes with a generously sized lot, while still being close to skiing, golf, hiking, lake activities, dining, and

    Larry Smith Railey Realty, Inc.

    Lot 94 Wisp Adventure Rd, McHenry, MD 21541
  • /13

    $115,000

    • Land
    • 0.5 Acre
    • $230,000 per Acre

    6 Irwin Way, Sang Run, MD 21541

    Wooded, level half-acre homesite tucked inside the Lodestone Golf Course! Located on a private cul-de-sac, Lot 6 sits off the beaten path while keeping you close to Deep Creek Lake, Wisp Resort, state parks, and all the local spots. Public water and sewer hookups available. Quick and easy access to Fork Run Recreation Area with over 8 miles of hiking and biking trails, rock climbing and more! A

    Jon Bell Railey Realty, Inc.

    6 Irwin Way, Sang Run, MD 21541
  • /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
  • /50

    $679,900 New Construction

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

    4A Mystic Creek Trail, Oakland, MD 21550

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

    Justin Liller Railey Realty, Inc.

    4A Mystic Creek Trail, Oakland, MD 21550
  • /110

    $759,000

    • 3 Beds
    • 3.5 Baths
    • 2,570 Sq Ft

    105 Mountain Overlook Ct, McHenry, MD 21550

    Luxury Mountaintop Ski Chalet with scenic Deep Creek Lake Access for year-round enjoyment. Just minutes from Wisp's ski slopes and ASCI Whitewater, this fantastic location is ideal for exciting summer adventures and winter skiing with effortless connections to the Ski Lodge, easy-access mountaintop ski parking, lift tickets, on-site community amenities, and everything you need. Exceptional

    Nina Beitzel Railey Realty, Inc.

    105 Mountain Overlook Ct, McHenry, MD 21550
  • /30

    $249,000 New Construction

    • 4 Beds
    • 3 Baths
    • 2,390 Sq Ft

    62 Wild Turkey Ct, Oakland, MD 21550

    Current new home construction project underway, but Builder not going to complete at this time due too busy. So, ready for who may wish to complete project themselves or have completed by others, or current Builder may consider completing for Buyer. Current structure is a custom engineered modular home. This is not a completed or intended by Builder to be completed house project at this time .

    Chip Smith 1 Real Estate Source LLC

    62 Wild Turkey Ct, Oakland, MD 21550
  • /32

    $309,000

    • 2 Beds
    • 1 Bath
    • 780 Sq Ft

    565 Glendale Rd Unit B206, Oakland, MD 21550

    Charming true 1-bedroom + loft (can be used as 2nd bedroom) condo at Silver Tree Suites, LAKEFRONT living at its finest! This spacious second-floor unit features a private balcony, fully equipped kitchenette, cozy gas fireplace and abundant natural light. Enjoy resort-style amenities including a fitness center, sauna, on-site laundry and game room, plus steps-away fine dining at Dutch’s at Silver

    Carlos Espinoza Jason Mitchell Group

    565 Glendale Rd Unit B206, Oakland, MD 21550

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