148

Oakland, MD Homes for Sale

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  • /9

    $35,000

    • Land
    • 20,037 Sq Ft
    • $76,087 per Acre

    Lot 233 Cumberland Rd, Oakland, MD 21550

    Seize the opportunity to own a beautiful parcel of land just minutes from Deep Creek Lake—one of the region’s most sought-after destinations for recreation and relaxation. This nearly half-acre property offers the rare combination of no HOA and no restrictions, giving you the freedom to bring your vision to life without limitations. Whether you're dreaming of building a cozy getaway cabin, a

    Sheila Howell Lake Homes Realty, LLC

    Lot 233 Cumberland Rd, Oakland, MD 21550
  • /52

    $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
  • /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
  • /13

    $63,000

    • 792 Sq Ft

    809 N St, Oakland, MD 21550

    Bring your vision and TLC to explore the possibilities here for rehab. Mt. Lake Park home being sold "As Is" Buyer to confirm with the county and the town of Mt. Lake Park for permits and building stipulations. Take a look & enjoy the ambiance of this historic area. RAILEY REALTY IS NOT THE CARETAKER OF PROPERTIES LISTED BY IT. PROSPECTIVE PURCHASERS AND THEIR AGENTS ASSUME ALL LIABILITY

    Kathy Gibson Railey Realty, Inc.

    809 N St, Oakland, MD 21550
  • /11

    $19,500

    $6K PRICE DROP
    • Land
    • 5,227 Sq Ft
    • $162,500 per Acre

    Lot 55 Gallatin Dr Unit 55, Oakland, MD 21550

    Fantastic bargain for this homesite! Gallatin Woods is a unique log home community located on Lakeshore Drive in the innermost part of Deep Creek Lake. Each owner may build within the building cylinder indicated on the plat and have exclusive use of the parking area and the additional land that immediately surrounds the home site. All other land within the community is condominiumized to keep the

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

    Lot 55 Gallatin Dr Unit 55, 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
  • /61

    $969,000

    • 5 Beds
    • 4.5 Baths
    • 4,284 Sq Ft

    251 Robinwood Dr, Oakland, MD 21550

    One-of-a-kind Youghiogheny riverfront estate offering 400 feet of water frontage on 5+ acres and 2 separate lots. Soak in the sounds of the flowing waters and chirping birds, cloaked in a private canopy of mountain laurel, pine trees and mature hardwoods. 5BR 4.5 BA log masterpiece with attached 2 car garage and paved driveway. Thoughtful design and well maintained with spacious suites, floor to

    Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    251 Robinwood Dr, Oakland, MD 21550
  • /55

    $795,000

    • 5 Beds
    • 3.5 Baths
    • 4,230 Sq Ft

    312 Moss Creek Cir, Oakland, MD 21550

    Tucked away on a picturesque 1.83-acre parcel, this charming log home offers the perfect blend of rustic character and modern comfort. Amongst the 4,200+ SF, you will find five spacious bedrooms, two family rooms, a playroom, an office/den, a large loft, spacious pantry, granite counter tops, hardwood flooring and two fireplaces. The warm wood interior and classic log construction create a cozy,

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

    312 Moss Creek Cir, Oakland, MD 21550
  • /47

    $249,000

    • 4 Beds
    • 1 Bath
    • 1,432 Sq Ft

    106 G St, Oakland, MD 21550

    Step back in time with this charming 1900 home located in the heart of historic Mountain Lake Park. Offering 4 bedrooms, 1 bath, and 1,432 square feet, this property sits on two lots totaling 0.27 acres and is ready for its next chapter. Rich in character, the home features original woodwork, hardwood floors beneath the carpet, two fireplaces, spacious rooms, and a wraparound covered porch

    Kelsey Meyers Railey Realty, Inc.

    106 G St, Oakland, MD 21550
  • /59

    $739,000

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

    12 Arrowhead Ln, Oakland, MD 21550

    Arrowhead 3BR, 3 full BA lakefront, end-unit condo, WITH a dedicated dock slip! Easy walk out to level lakefront just steps to your dock slip! 3 Level unit includes an updated kitchen, cozy wood burning fireplace, multiple living areas, lakefront patio & deck with great water views! Enjoy a private, level lakefront peninsula boasting a large common lakefront area! Surrounded by mature pine trees,

    Julie Mead The KW Collective

    12 Arrowhead Ln, Oakland, MD 21550
  • /61

    $615,000

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

    308 Winding Trail Ln Unit 11B, Oakland, MD 21550

    5BR, 4.5BA duplex with LAKE VIEWS! Enjoy 3300sf of living space in the heart of Deep Creek Lake. Features include 3 spacious suites, multiple stacked stone fireplaces and two living room areas, plus an impressive outdoor fire pit. You will love the open kitchen/dining area and the covered back deck. Other features include wood floors, granite, instant hot water, pool table and hot tub. Attached

    Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    308 Winding Trail Ln Unit 11B, Oakland, MD 21550
  • /3

    $115,000

    • Land
    • 1 Acre
    • $115,000 per Acre

    0 Paradise Heights Rd Unit MDGA2007090, Oakland, MD 21550

    Centrally located 1-acre lake access homesite with a dock slip! This property has endless possibilities to build, and depending on where you decide to position your new home, there could be potential for lake views. Offering public sewer and no HOA fees. The only decision left to be made is what style home you will build. Just minutes to the DCL State Park, several restaurants, convenience store,

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

    0 Paradise Heights Rd Unit MDGA2007090, Oakland, MD 21550
  • /46

    $150,000

    • Land
    • 21.46 Acres
    • $6,990 per Acre

    0 Sanders Ln Unit MDGA2011678, Oakland, MD 21550

    Endless Possibilities on 21.46 Acres! A rare private setting featuring gently rolling, pastoral land along scenic Sanders Lane-just 4 miles from Oakland. Enjoy open fields, and woods on a private and a peaceful setting in a desirable area. Enjoy wide-open skies, room to roam, and the serenity of nature—all within minutes of town conveniences, and all the activities Garrett County has to offer!

    Susan Bell Railey Realty, Inc.

    0 Sanders Ln Unit MDGA2011678, Oakland, MD 21550
  • /41

    $424,900

    New Construction $25K PRICE DROP
    • 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 scenic views with modern design and outdoor living. Key features include multiple wood-burning fireplaces, Andersen windows, commercial-grade LVP flooring throughout, gourmet kitchen with soft-close cabinets and drawers, quartz countertops,

    Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    654 N Bradley Ln, Oakland, MD 21550
  • /57

    $219,000

    • 1 Bed
    • 1.5 Baths
    • 912 Sq Ft

    141 Montana Ln, Oakland, MD 21550

    Nestled on nearly 3 acres across two parcels, this chalet-style home offers a rare opportunity to create your retreat just minutes from the lake. Renovate the existing structure, or start fresh and build the lake-area retreat or cabin you’ve always imagined. The level, wooded setting provides privacy, peace, and plenty of room to expand, garden, or simply enjoy nature. With well and septic

    Larry Smith Railey Realty, Inc.

    141 Montana Ln, Oakland, MD 21550
  • /64

    $400,000

    • 2 Beds
    • 1 Bath
    • 1,800 Sq Ft

    2967 Pysell Crosscut Rd, Oakland, MD 21550

    Discover the charm and comfort of this beautifully maintained manufactured home, nestled on a generous 2.07-acre lot. With a unique blend of rustic appeal and modern convenience, this property is perfect for those seeking a serene retreat without sacrificing accessibility. Step inside to find a warm and inviting interior with carpeting and laminate flooring that flows seamlessly throughout. The

    Larry Smith Railey Realty, Inc.

    2967 Pysell Crosscut Rd, Oakland, MD 21550
  • /2

    $134,000

    • Land
    • 1 Acre
    • $134,000 per Acre

    0 Paradise Point Rd Unit MDGA2003916, Oakland, MD 21550

    Wooded lot with spectacular views of Paradise Point area of lake. Great privacy. Sewer tap available

    John Zorzit Eagle Commercial Realty

    0 Paradise Point Rd Unit MDGA2003916, Oakland, MD 21550
  • /10

    $375,000

    • 5 Beds
    • 1.5 Baths
    • 1,536 Sq Ft

    511 Main St, Oakland, MD 21550

    The property offered for sale is 32.20 acres located on the southwest & northwest corners of Maryland Highway, State Route 135 at Main Street & Sand Flat Road, Deer Park. The Single Family Residence built in 1920 has 5 bedrooms, 1 full bathroom and 1 half bathroom. The residence is being sold "As Is". The residence is prime for renovation; the parcel may have commercial potential. The current

    Dan (Sussan) Duggan 1 Real Estate Source LLC

    511 Main St, Oakland, MD 21550
  • /6

    $4,000

    • Land
    • 20,037 Sq Ft
    • $8,696 per Acre

    0 Rhododendron Unit MDGA2010748, Oakland, MD 21550

    Here is an affordable chance to own a lot and have access to all of Youghiogheny Mountain Resort's beautiful and fun amenities!

    Jonathan Price Railey Realty, Inc.

    0 Rhododendron Unit MDGA2010748, Oakland, MD 21550
  • /24

    $16,000

    • Land
    • 21,344 Sq Ft
    • $32,653 per Acre

    21 Bear Dr E, Oakland, MD 21550

    Don’t miss this great opportunity in the gated community of Youghiogheny Mountain Resort! This flat 0.49-acre lot offers an easy build site. Perfect for your dream home or weekend escape. Enjoy access to ATV trails, hunting, and fishing, all while being just a short drive to Wisp Resort, Deep Creek Lake, and Swallow Falls State Park. Approved for a sand mound septic system and set within a

    Laura Newhall Taylor-Made Deep Creek Real Estate, LLC

    21 Bear Dr E, Oakland, MD 21550
  • /7

    $24,900

    $5K PRICE DROP
    • Land
    • 4 Acres
    • $6,225 per Acre

    Lot 7 Backbone Ridge Rd, Oakland, MD 21550

    This 4-acre building lot in the Backbone Ridge community offers breathtaking mountain views and a 3-bedroom perc approval — ready for your dream home. Perfectly positioned near Deep Creek Lake, WISP Ski Resort, Canaan Valley, Timberline Ski Resort, and Blackwater Falls State Park, outdoor adventure is just minutes away. Whether you're building a year-round residence or a weekend escape, enjoy the

    Brent Housley Railey Realty, Inc.

    Lot 7 Backbone Ridge Rd, Oakland, MD 21550
  • /11

    $49,900

    • Land
    • 1.38 Acres
    • $36,159 per Acre

    LOT 6B Betts Ln, Oakland, MD 21550

    This 1.38-acre property offers a private, quiet setting with level ground and easy access from a well maintained road. Located just a short drive from Deep Creek Lake and Oakland, MD, it gives you the feel of being in the country while still being close to town. The lot is surrounded by woods and is a great spot to enjoy nature, with plenty of wildlife in the area. A solid option for a future

    Thomas Long Railey Realty, Inc.

    LOT 6B Betts Ln, Oakland, MD 21550
  • /26

    $425,000

    • Land
    • 1.34 Acres
    • $317,164 per Acre

    LOT 25 Holy Cross Dr, Oakland, MD 21550

    Discover the perfect blend of privacy, prestige, and natural beauty with Lot 25 in The Reserve at Holy Cross—a premier wooded lakefront homesite tucked into a serene private cove on Deep Creek Lake. Boasting 1.34 acres and an impressive 251 feet of lake frontage, this exceptional lot offers the ideal setting to build your dream retreat. Enjoy direct access to the water with up to two boat slips

    Nina Beitzel Railey Realty, Inc.

    LOT 25 Holy Cross Dr, Oakland, MD 21550
  • /78

    $1,579,900

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

    2311 Boy Scout Rd, Oakland, MD 21550

    Experience the best of Deep Creek Lake living from this private waterfront retreat tucked among mature trees on nearly an acre of land. With over 100 feet of lake frontage, a private Type-A dock, and a gentle distance to deep water, this property offers the kind of shoreline that's increasingly hard to find. Thoughtfully positioned to capture expansive lake views while preserving a sense of

    Jon Bell Railey Realty, Inc.

    2311 Boy Scout Rd, Oakland, MD 21550
  • /58

    $215,000

    • 2 Beds
    • 1 Bath
    • 1,440 Sq Ft

    2967 Pysell Crosscut Rd, Oakland, MD 21550

    This charming manufactured home offers a delightful blend of comfort and functionality, perfect for those seeking a cozy retreat. With 1,440 square feet of thoughtfully designed living space, this residence features two bedrooms and full bathroom. Step inside to discover a warm and welcoming interior. The combination dining and living area is perfect for entertaining or enjoying quiet evenings at

    Larry Smith Railey Realty, Inc.

    2967 Pysell Crosscut Rd, Oakland, MD 21550
  • /31

    $224,900

    • 1 Bed
    • 1 Bath
    • 1,080 Sq Ft

    206 Mayhew Inn Rd, Oakland, MD 21550

    Just 2.5 miles from the scenic Swallow Falls State Park, this charming 1-bedroom, 1-bath house blends cozy living with endless potential. The upper level offers a cozy living area, a full kitchen, laundry room, bedroom, and full bath. But the real bonus? A spacious 2-car garage with its own entrance. It is perfect for a workshop, extra storage, or even a rental opportunity. With separate

    Jay Quinn Taylor-Made Deep Creek Real Estate, LLC

    206 Mayhew Inn Rd, 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
  • /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
  • /21

    $160,000

    • Land
    • 10.1 Acres
    • $15,842 per Acre

    0 Dennett Rd 10 Acres To Oakland Ave Unit MDGA2011252, Oakland, MD 21550

    Over 10 acres ready for developing off Dennett Rd. and Oakland Ave. Can be subdivided or could be large parcel to build your dream home, privacy off main streets with 3 separate entrances connecting to town roads. Engineered drawings for subdivision with grading permit in place at time of survey, is available and will be transferred with sale. (Potential up to 20 lots) Public sewar & water can be

    Julie Mead The KW Collective

    0 Dennett Rd 10 Acres To Oakland Ave Unit MDGA2011252, Oakland, MD 21550
  • /58

    $234,000

    $15K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,520 Sq Ft

    1021 E High St, Oakland, MD 21550

    ***BACK ON THE MARKET, don't miss this one a second time! Welcome home to this solid, ranch style home on one of Oakland's most convenient streets. Built in 1954, this 3-bedroom, 2-bath home delivers 1,520 sq ft of comfortable living, plus a partially finished full basement ready for your vision, whether that's a rec room, home office, or extra storage. The metal roof means peace of mind for

    Jeremy Cunningham Railey Realty, Inc.

    1021 E High St, 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
  • /56

    $325,000

    $34K PRICE DROP
    • 4 Beds
    • 1.5 Baths
    • 1,563 Sq Ft

    17921 Garrett Hwy, Oakland, MD 21550

    Charming and well-maintained, this 4-bedroom, 1.5-bath traditional home offers the perfect combination of comfort, character, and convenience. Built in 1952 and thoughtfully cared for, the home features beautifully refinished hardwood floors, inviting built-ins, and a cozy living room with a functional wood burner. With over 1,500 square feet of living space, the spacious layout includes an

    Michelle Clark Taylor-Made Deep Creek Real Estate, LLC

    17921 Garrett Hwy, Oakland, MD 21550
  • /17

    $19,000

    • Land
    • 21,344 Sq Ft
    • $38,776 per Acre

    6 Cedar Ln, Oakland, MD 21550

    Discover the perfect place to build your mountain getaway, full-time residence, or adventure basecamp. Located within the highly sought-after Yough Mountain Resort community, this property offers access to more than 2,000 acres of private wilderness to explore and enjoy year-round. This land is at the top of the mountain where it is generally quieter. It has been surveyed for a well site and has

    Danielle Luscombe Taylor-Made Deep Creek Real Estate, LLC

    6 Cedar Ln, 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, LLC

    164 Grandview Dr, Oakland, MD 21550
  • /2

    $64,900

    $5K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 792 Sq Ft

    74 Parks Rd, Oakland, MD 21550

    **Investor Special with Mountain & Water Views**Opportunity is knocking at 74 Parks Road in Oakland, Maryland! This 3-bedroom, 1-bath one story is perfectly positioned just steps from the West Virginia line and surrounded by some of the most sought-after recreation in the region.Enjoy peaceful views of Snowy Creek right from the front yard and take advantage of being just minutes from

    Emillie Albrecht Real Broker, LLC

    74 Parks Rd, Oakland, MD 21550
  • /110

    $975,000

    • 3 Beds
    • 2.5 Baths
    • 2,520 Sq Ft

    1250 Pergin Farm Rd, Oakland, MD 21550

    Frank Lloyd Wright-inspired architecture meets private Deep Creek Lake living. This one-of-a-kind home with various floor & ceiling elevations, showcases exposed barn beams, walls of glass, and a design that seamlessly blends indoor and outdoor spaces while capturing stunning lake views. The cathedral-ceiling living area features a picture-perfect lake view and a breathtaking floor-to-ceiling

    Susan Bell Railey Realty, Inc.

    1250 Pergin Farm Rd, Oakland, MD 21550
  • /43

    $2,499,900

    • 4 Beds
    • 1.5 Baths
    • 2,190 Sq Ft

    83 Bethlehem Rd, Oakland, MD 21550

    Rare opportunity to own 327+/- acres of scenic countryside featuring a mix of open pasture, mature woods, and flowing stream frontage along Block Run. This 4-bedroom, 1.5-bath farmhouse is privately tucked among rolling fields and mountain views, offering endless potential for farming, recreation, hunting, ATV trails, or a private estate. Multiple barns and outbuildings provide ample storage and

    Jon Bell Railey Realty, Inc.

    83 Bethlehem Rd, Oakland, MD 21550
  • /29

    $195,000

    • 3 Beds
    • 1 Bath
    • 1,382 Sq Ft

    2918 Oakland Sang Run Rd, Oakland, MD 21550

    This charming 3-bedroom, 1-bathroom ranch-style home in the desirable Oakland Sang Run Rd area near the Youghiogheny River offers a blend of modern upgrades and classic appeal. Recently renovated in 2022, the interior features an open floor plan with luxury vinyl tile flooring, built-ins, and a gourmet kitchen equipped with stainless steel appliances and upgraded countertops. Enjoy the

    Andrew Eiswert Railey Realty, Inc.

    2918 Oakland Sang Run Rd, Oakland, MD 21550
  • /69

    $219,900

    $45K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,064 Sq Ft

    8956 Oakland Sang Run Rd, Oakland, MD 21550

    Welcome to The Wise Quack - our cozy cabin in the center of Deep Creek Lake activities...all 4 seasons! If you’re looking for a weekend or holiday retreat, this is it! The Wise Quack is a successful short-term rental with rave reviews. The home has three bedrooms, two full bathrooms, a fully equipped kitchen, laundry room and lots of outdoor living space. There is parking for 6+ cars on the

    Lisa Irving Taylor Properties

    8956 Oakland Sang Run Rd, Oakland, MD 21550
  • /7

    $42,000

    • Land
    • 1.05 Acres
    • $40,000 per Acre

    0 Maple Del Ln, Oakland, MD 21550

    Lot 6 Maple Del is a mostly wooded , 1.05 acre lot near the western parts of Deep Creek Lake, Red Run cove and centrally located off Mayhew Inn Rd. There is a small stream running through the property and huge boulders strewn throughout, making it a fantastic setting for a wooded retreat. Incredible location near state parks and Deep Creek Lake area amenities. Public sewer available with sewer

    Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    0 Maple Del Ln, Oakland, MD 21550

Showing Results 41 - 80, Page 2 of 4

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