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Newest Homes for Sale in Oakland, MD

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  • 512 Roanoke Ave, Oakland, MD 21550
    512 Roanoke Ave, Oakland, MD 21550
    512 Roanoke Ave, Oakland, MD 21550
    /28

    $185,000

    • 2 Beds
    • 1.5 Baths
    • 960 Sq Ft

    512 Roanoke Ave, Oakland, MD 21550

    The first thing you will notice as you approach 512 Roanoke Ave in loch Lynn heights is the towering maple trees lining the street. (In early spring they provide syrup for a lucky few!) Framing this post-card perfect snap shot is a park on either side. The Loch Lynn Wetlands Trail is the beating heart of the neighborhood, and the Loch Lynn Community Park and Pavillion hosts the annual town

    Brady Harden Coldwell Banker Premier

    512 Roanoke Ave, Oakland, MD 21550
  • 208 Cliff Dr, Oakland, MD 21550
    208 Cliff Dr, Oakland, MD 21550
    208 Cliff Dr, Oakland, MD 21550
    /77

    $950,000

    • 4 Beds
    • 3 Baths
    • 2,219 Sq Ft

    208 Cliff Dr, Oakland, MD 21550

    Picture perfect, private and wooded mountain retreat featuring lake access in a prime location close to all area amenities! Seasonal lake views! This highly desirable property offers the opportunity to walk to your dock featuring TWO slips for your use. A two-minute walk at the end of the quiet road leads you to the property's deeded lake-front land and two dock slips. Nestled among the

    Kellyann Green Railey Realty, Inc.

    208 Cliff Dr, Oakland, MD 21550
  • 20160 Garrett Hwy Unit H706, Oakland, MD 21550
    20160 Garrett Hwy Unit H706, Oakland, MD 21550
    20160 Garrett Hwy Unit H706, Oakland, MD 21550
    /10

    $309,000

    • 1 Bed
    • 1 Bath
    • 550 Sq Ft

    20160 Garrett Hwy Unit H706, Oakland, MD 21550

    NOTE: New Interior Photos Coming Soon. Welcome to Will O' the Wisp Unit H706, a beautiful top-floor lakefront condo offering some of the most breathtaking views of Deep Creek Lake. Perched on the 7th floor and overlooking one of the lake's widest sections, this fully furnished two-level condo features 1 bedroom, 1 bath, and 550 square feet of comfortable, low-maintenance living - ideal as a

    Agent Photo

    James Matthews

    Taylor-Made Deep Creek Real Estate, LLC

    (240) 266-9392

    20160 Garrett Hwy Unit H706, Oakland, MD 21550
  • 1099 Table Rock Rd, Oakland, MD 21550
    1099 Table Rock Rd, Oakland, MD 21550
    1099 Table Rock Rd, Oakland, MD 21550
    /44

    $145,000

    Coming Soon
    • 1 Bed
    • 1 Bath
    • 1,800 Sq Ft

    1099 Table Rock Rd, Oakland, MD 21550

    Nestled in the scenic countryside of Southern Garrett County, on 5+ acre property along North Fork Sand Run, this two-level home provides a solid foundation for renovation or customization, making it ideal for a full-time residence or mountain getaway. In addition to the home, the property features a large detached garage perfect for vehicles, equipment, hobbies, or workshop space, along with a

    Rich Orr Railey Realty, Inc.

    1099 Table Rock Rd, Oakland, MD 21550
  • 670 Woodlands Hill Ln, Oakland, MD 21550
    670 Woodlands Hill Ln, Oakland, MD 21550
    670 Woodlands Hill Ln, Oakland, MD 21550
    /72

    $1,689,000

    • 5 Beds
    • 4.5 Baths
    • 3,714 Sq Ft

    670 Woodlands Hill Ln, Oakland, MD 21550

    Experience what may be the most spectacular view in all of Deep Creek Lake! Perched in an extraordinary setting, this exceptional Yellowstone Log Home showcases breathtaking panoramic water views that create a true “top of the world” feel. Designed to capture the scenery from every angle, the main level features an open-concept layout with soaring natural light, a stunning stone fireplace, luxury

    Nina Beitzel Railey Realty, Inc.

    670 Woodlands Hill Ln, Oakland, MD 21550
  • 62 Middleton Rd, Oakland, MD 21550
    62 Middleton Rd, Oakland, MD 21550
    62 Middleton Rd, Oakland, MD 21550
    /38

    $799,900

    • 3 Beds
    • 2.5 Baths
    • 1,929 Sq Ft

    62 Middleton Rd, Oakland, MD 21550

    Lake Access with a Dock Slip located in the highly desirable Blakeslee community. This 3-bedroom, 2.5-bath mountain retreat offers the perfect mix of comfort, style, and Deep Creek Lake living. An open, inviting layout give the home a refreshed, updated feel, while the sun-filled four-season room quickly becomes the standout space of the home. A stunning pass-through stone fireplace anchors the

    Jon Bell Railey Realty, Inc.

    62 Middleton Rd, Oakland, MD 21550
  • 8760 Oakland Sang Run Rd, Oakland, MD 21550
    8760 Oakland Sang Run Rd, Oakland, MD 21550
    8760 Oakland Sang Run Rd, Oakland, MD 21550
    /28

    $82,500

    • Land
    • 2.53 Acres
    • $32,609 per Acre

    8760 Oakland Sang Run Rd, Oakland, MD 21550

    Attention outdoor enthusiasts! This 2.53 acre lot just across the road from state-owned land down to the world-famous Youghiogheny River is a whitewater lover or fisherman's dream. Complete with a gravel driveway up to a flat gravel pad and electric meter ready to go, perfect for a camper or a forever home. Perc-approved for 3 bedrooms and less than half a mile from easy public Yough access.

    Elizabeth Ware Railey Realty, Inc.

    8760 Oakland Sang Run Rd, Oakland, MD 21550
  • 277 Cheeks Ln, Oakland, MD 21550
    277 Cheeks Ln, Oakland, MD 21550
    277 Cheeks Ln, Oakland, MD 21550
    /37

    $279,000

    • 3 Beds
    • 1.5 Baths
    • 1,148 Sq Ft

    277 Cheeks Ln, Oakland, MD 21550

    Tucked away on a private lane and surrounded by the beauty of the woods, this charming 3-bedroom, 1 full bath and 1 half bath log home offers the perfect mountain retreat on 2 peaceful acres in Garrett County. Ideally located just minutes from Swallow Falls State Park, Muddy Creek Falls, and the Youghiogheny River, this cozy cabin is a dream destination for outdoor enthusiasts seeking hiking,

    Mike Kennedy Railey Realty, Inc.

    277 Cheeks Ln, Oakland, MD 21550
  • 312 Moss Creek Cir, Oakland, MD 21550
    312 Moss Creek Cir, Oakland, MD 21550
    312 Moss Creek Cir, 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
  • 0 6 89 Acres -Woodlands Hill Dr Dr Unit MDGA2011974, Oakland, MD 21550
    0 6 89 Acres -Woodlands Hill Dr Dr Unit MDGA2011974, Oakland, MD 21550
    0 6 89 Acres -Woodlands Hill Dr Dr Unit MDGA2011974, Oakland, MD 21550
    /4

    $250,000

    • Land
    • 6.89 Acres
    • $36,284 per Acre

    0 6 89 Acres -Woodlands Hill Dr Dr Unit MDGA2011974, Oakland, MD 21550

    6.89 unrestricted acres in the heart of Deep Creek Lake area, only 1/4 mile away from the lake. Ready to build your dream home with seclusion and privacy, close to all area parks and amenities.

    Agent Photo

    Brian Homberg

    Taylor-Made Deep Creek Real Estate, LLC

    (240) 307-5520

    0 6 89 Acres -Woodlands Hill Dr Dr Unit MDGA2011974, Oakland, MD 21550
  • 122 Woodlands Hill Ln, Oakland, MD 21550
    122 Woodlands Hill Ln, Oakland, MD 21550
    122 Woodlands Hill Ln, Oakland, MD 21550
    /38

    $1,200,000

    Coming Soon
    • 4 Beds
    • 3.5 Baths
    • 2,656 Sq Ft

    122 Woodlands Hill Ln, Oakland, MD 21550

    Welcome to mountain living at its finest. Nestled on 6.89 private acres, 122 Woodlands Hill Lane offers the perfect blend of seclusion, space, and comfort in one of Garrett County’s most desirable settings. This impressive 4-bedroom, 4.5-bath home features approximately 4,000 square feet of living space designed for gathering, relaxing, and enjoying the beauty of Western Maryland. The home sits

    Agent Photo

    Brian Homberg

    Taylor-Made Deep Creek Real Estate, LLC

    (240) 290-8978

    122 Woodlands Hill Ln, Oakland, MD 21550
  • 588 Lake Forest Dr, Oakland, MD 21550
    588 Lake Forest Dr, Oakland, MD 21550
    588 Lake Forest Dr, Oakland, MD 21550
    /39

    $1,089,000

    • 3 Beds
    • 2 Baths
    • 1,411 Sq Ft

    588 Lake Forest Dr, Oakland, MD 21550

    Welcome to Cabin Dreams — a charming rustic lakefront retreat with 134’ of beautiful, gently sloped lake frontage on Deep Creek Lake. Facing the sunrise with an inviting sandy shoreline, stunning lake views, and private Type A dock, this 3-bedroom + loft, 2-bath getaway offers the perfect blend of relaxation and adventure. Inside, warm wood accents, hardwood floors, mini-split AC/heating units,

    Nina Beitzel Railey Realty, Inc.

    588 Lake Forest Dr, Oakland, MD 21550
  • 248 Tarn Dr, Oakland, MD 21550
    248 Tarn Dr, Oakland, MD 21550
    248 Tarn Dr, Oakland, MD 21550
    /70

    $1,189,000

    New Construction
    • 6 Beds
    • 5.5 Baths
    • 3,482 Sq Ft

    248 Tarn Dr, Oakland, MD 21550

    Brand new construction in the desirable Mountainside community! This thoughtfully designed 6-bedroom mountain retreat offers 4 spacious primary suites, blending modern mountain style with functionality and comfort throughout. The open floorplan features vaulted ceilings, luxury finishes, quartz countertops, and multiple gathering spaces designed for entertaining and relaxation alike. Enjoy cozy

    Lauren McCann Railey Realty, Inc.

    248 Tarn Dr, Oakland, MD 21550
  • 123 B St, Oakland, MD 21550
    123 B St, Oakland, MD 21550
    123 B St, Oakland, MD 21550
    /3

    $149,900

    • 2 Beds
    • 2 Baths
    • 1,386 Sq Ft

    123 B St, Oakland, MD 21550

    2Bd/2Ba rancher. Needs updating. 1 car garage, rear deck, storage shed in back yard. Asset Manager requests property be on the market for 3 days before reviewing offers.

    Joseph Driver Century 21 Downtown

    123 B St, Oakland, MD 21550
  • 2448 Birchwood Dr, Oakland, MD 21550
    2448 Birchwood Dr, Oakland, MD 21550
    2448 Birchwood Dr, Oakland, MD 21550
    /75

    $349,900

    • 4 Beds
    • 2 Baths
    • 3,352 Sq Ft

    2448 Birchwood Dr, Oakland, MD 21550

    Tucked within the sought-after Yough Mountain Resort community, this beautifully remodeled 4-bedroom, 2-bath mountain retreat blends rustic charm with thoughtful modern updates. Warm wood finishes, high ceilings, and inviting gathering spaces create a cozy lodge-style atmosphere, while upgrades throughout add comfort and convenience. The home features two full kitchens with granite countertops,

    Jon Bell Railey Realty, Inc.

    2448 Birchwood Dr, Oakland, MD 21550
  • 83 Bethlehem Rd, Oakland, MD 21550
    83 Bethlehem Rd, Oakland, MD 21550
    83 Bethlehem 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
  • 9.75 AC. Dennett Rd, Oakland, MD 21550
    9.75 AC. Dennett Rd, Oakland, MD 21550
    9.75 AC. Dennett Rd, Oakland, MD 21550
    /30

    $169,000

    • Land
    • 9.75 Acres
    • $17,333 per Acre

    9.75 AC. Dennett Rd, Oakland, MD 21550

    9.75 acres of prime land in a highly convenient Oakland location! This versatile property offers outstanding potential for development or the ideal setting for a private estate-sized homesite. Seller has already completed a proposed subdivision engineering plan, providing added value and future possibilities. Public water and sewer taps available per Oakland Town Administrator. Gently rolling

    Nina Beitzel Railey Realty, Inc.

    9.75 AC. Dennett Rd, Oakland, MD 21550
  • LOT 2 Oak Breeze Ln, Oakland, MD 21550
    LOT 2 Oak Breeze Ln, Oakland, MD 21550
    LOT 2 Oak Breeze Ln, Oakland, MD 21550
    /24

    $44,900

    • Land
    • 23,086 Sq Ft
    • $84,717 per Acre

    LOT 2 Oak Breeze Ln, Oakland, MD 21550

    Beautiful 0.53-acre corner lot in the desirable Oak Breeze Estates community! Located at the corner of Oak Breeze Lane and John Drive, this level homesite offers a wonderful setting for your dream home in one of Oakland’s established residential neighborhoods. Public water and sewer taps available per Oakland Town Administrator. Convenient location near schools, shopping, dining, and WVU Regional

    Nina Beitzel Railey Realty, Inc.

    LOT 2 Oak Breeze Ln, Oakland, MD 21550
  • 321 N 3rd St, Oakland, MD 21550
    321 N 3rd St, Oakland, MD 21550
    321 N 3rd St, Oakland, MD 21550
    /37

    $400,000

    • 5 Beds
    • 2 Baths
    • 3,660 Sq Ft

    321 N 3rd St, Oakland, MD 21550

    Spacious and beautifully maintained all-brick rancher offering approximately 3,660 square feet of living space with room for everyone! This impressive home features 5 bedrooms, 2 full bathrooms, and a fully finished basement with its own private entrance—perfect for in-law potential, extended family living, or flexible multi-generational use. Inside, you’ll find a welcoming living room with

    Christina Ford CENTURY 21 New Millennium

    321 N 3rd St, Oakland, MD 21550
  • 0 Hutton Road(2 Acres), Oakland, MD 21550
    0 Hutton Road(2 Acres), Oakland, MD 21550
    0 Hutton Road(2 Acres), Oakland, MD 21550
    /7

    $36,000

    $10K PRICE INCREASE
    • Land
    • 2 Acres
    • $18,000 per Acre

    0 Hutton Road(2 Acres), Oakland, MD 21550

    2 acres off Hutton Rd, raw land, endless possibilities. No restrictions, county zoning applies. Manly tree covered.

    Julie Mead The KW Collective

    0 Hutton Road(2 Acres), Oakland, MD 21550
  • 560 Glendale Rd, Oakland, MD 21550
    560 Glendale Rd, Oakland, MD 21550
    560 Glendale Rd, Oakland, MD 21550
    /24

    $419,000

    • 2 Beds
    • 1 Bath
    • 700 Sq Ft

    560 Glendale Rd, Oakland, MD 21550

    Charming vintage Deep Creek Lake log cabin ideally located in the heart of Deep Creek Lake just minutes from area amenities. Full of character and thoughtfully restored, this established rental property is being sold completely furnished and turnkey. Enjoy filtered lake views from the inviting covered front porch, then unwind in the hot tub or gather around the fire pit after a day on the lake.

    Lauren McCann Railey Realty, Inc.

    560 Glendale Rd, Oakland, MD 21550
  • 17921 Garrett Hwy, Oakland, MD 21550
    17921 Garrett Hwy, Oakland, MD 21550
    17921 Garrett Hwy, Oakland, MD 21550
    /56

    $359,000

    • 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
  • 565 Glendale Rd Unit 303B, Oakland, MD 21550
    565 Glendale Rd Unit 303B, Oakland, MD 21550
    565 Glendale Rd Unit 303B, Oakland, MD 21550
    /34

    $399,900

    • 2 Beds
    • 1 Bath
    • 887 Sq Ft

    565 Glendale Rd Unit 303B, Oakland, MD 21550

    Experience lakefront living at its finest in the premier unit at Silver Tree Suites! This beautifully updated 2-bedroom, 1-bath condo showcases rustic charm with custom woodworking throughout. Featuring two separate living areas, there's plenty of space to relax and entertain. Enjoy year-round lake views from the private balcony, unwind by either of the two fireplaces, and appreciate the added

    Sean Sober Taylor-Made Deep Creek Real Estate, LLC

    565 Glendale Rd Unit 303B, Oakland, MD 21550
  • 2254 Garrett Rd, Oakland, MD 21550
    2254 Garrett Rd, Oakland, MD 21550
    2254 Garrett Rd, Oakland, MD 21550
    /52

    $399,000

    • 3 Beds
    • 2 Baths
    • 1,780 Sq Ft

    2254 Garrett Rd, Oakland, MD 21550

    Situated on an expansive and private 17 acres of property this Southern Garrett county home offers its new owners the unique opportunity of space and privacy all while being close to town and additional amenities. A private paved driveway leads you to an extensively updated and lovingly maintained home that has a spacious feeling 3 bedrooms and 2 full bathrooms on the main floor. A full basement

    Dan Shockey Taylor-Made Deep Creek Real Estate, LLC

    2254 Garrett Rd, Oakland, MD 21550
  • 127 Paradise Heights, Oakland, MD 21550
    127 Paradise Heights, Oakland, MD 21550
    127 Paradise Heights, Oakland, MD 21550
    /24

    $1,075,000

    • 3 Beds
    • 2.5 Baths
    • 2,240 Sq Ft

    127 Paradise Heights, Oakland, MD 21550

    Beautifully renovated lake access log cabin with a deeded dock slip in a quiet cove with private 29 acres of trails (ATVs/snowmobiles permitted). Recent renovations (approx. $200K) include new wrap around deck, new roof, re-stained siding, new kitchen with granite counters, new appliances, new bathrooms, new LVFs throughout the house, new 2 car garage doors, new mini-split heat and A/C units, and

    Norman Domingo XRealty.NET LLC

    127 Paradise Heights, Oakland, MD 21550
  • 105 Jasper Riley Rd, Oakland, MD 21550
    105 Jasper Riley Rd, Oakland, MD 21550
    105 Jasper Riley Rd, Oakland, MD 21550
    /61

    $335,000

    • 4 Beds
    • 2 Baths
    • 2,052 Sq Ft

    105 Jasper Riley Rd, Oakland, MD 21550

    Park like, setting on 1.7 acres in Pleasant Valley, 4 Br, 2BA ranch home with full basement. Close to town yet, peaceful and secluded. Home features 4 Bedrooms, primary has 2 walk-in closets & large primary bath with walk-in shower. Front living & dining areas, with main entrance from the covered front porch. Open Kitchen, breakfast nook and den area with wood burning fireplace. Opens to covered

    Julie Mead The KW Collective

    105 Jasper Riley Rd, Oakland, MD 21550
  • 638 Glendale Rd, Oakland, MD 21550
    638 Glendale Rd, Oakland, MD 21550
    638 Glendale Rd, Oakland, MD 21550
    /56

    $745,000

    • 5 Beds
    • 3 Baths
    • 2,640 Sq Ft

    638 Glendale Rd, Oakland, MD 21550

    Spacious five-bedroom lakeview home offering the perfect blend of relaxation and warmth from the moment you enter. This established rental property “Terp’s Hideaway” features an open and inviting floorplan, five bedrooms, two family rooms, and three levels of living space, making it an ideal layout for hosting family and friends. Step outside onto the large deck to take in beautiful views or

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

    638 Glendale Rd, Oakland, MD 21550
  • 8 Hidden Cove Ct, Oakland, MD 21550
    8 Hidden Cove Ct, Oakland, MD 21550
    8 Hidden Cove Ct, Oakland, MD 21550
    /65

    $949,000

    • 4 Beds
    • 3 Baths
    • 2,856 Sq Ft

    8 Hidden Cove Ct, Oakland, MD 21550

    Welcome to your perfect Deep Creek Lake retreat—where lake and mountain views, modern comforts, and year-round recreation come together. This beautifully maintained 4-bedroom, 3 full bath home offers nearby lake access with a full-time boat slip, making it ideal for both relaxation and adventure!The main level is filled with natural light thanks to an abundance of windows and doors,

    Mike Kennedy Railey Realty, Inc.

    8 Hidden Cove Ct, Oakland, MD 21550
  • 39 Leo Friend Rd, Oakland, MD 21550
    39 Leo Friend Rd, Oakland, MD 21550
    39 Leo Friend Rd, Oakland, MD 21550
    /59

    $875,000

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

    39 Leo Friend Rd, Oakland, MD 21550

    Stunning split lakefront retreat with sweeping views and Type-A dock. Experience exceptional lake life in this beautifully maintained one owner home offering breathtaking lake views and timeless craftsmanship in a serene landscaped setting. This impressive 3 bedroom 3.5 bathroom residence welcomes you through an elegant foyer with soaring cathedral ceilings and a striking oak staircase that sets

    Laura Newhall Taylor-Made Deep Creek Real Estate, LLC

    39 Leo Friend Rd, Oakland, MD 21550
  • 206 Mayhew Inn Rd, Oakland, MD 21550
    206 Mayhew Inn Rd, Oakland, MD 21550
    206 Mayhew Inn 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
  • 55 Village Dr Unit 5, Oakland, MD 21550
    55 Village Dr Unit 5, Oakland, MD 21550
    55 Village Dr Unit 5, Oakland, MD 21550
    /45

    $595,000

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

    55 Village Dr Unit 5, Oakland, MD 21550

    Tucked in the Yellowstone Village community at Deep Creek Lake, “Dan’s Mountain” is a charming log cabin retreat offering the perfect blend of mountain serenity and convenient access to the area’s top attractions. This 3-bedroom, 3-bathroom home comfortably accommodates guests spanning over 3 levels with a bonus enlcosed porch area. Warm wood interiors and a classic cabin feel welcome you inside,

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 358-4206

    55 Village Dr Unit 5, Oakland, MD 21550
  • 1875 Pysell Crosscut Rd, Oakland, MD 21550
    1875 Pysell Crosscut Rd, Oakland, MD 21550
    1875 Pysell Crosscut Rd, Oakland, MD 21550
    /62

    $735,000

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

    1875 Pysell Crosscut Rd, Oakland, MD 21550

    Check out this beautifully built and maintained 5 bedroom 5 bathroom lake area chalet style home. Located on the Southern side of the lake, near the headwaters of Deep Creek. The namesake stream that feeds into the nearby lake. This property offers it's new owners a tremendous amount of room for storage and entertaining and three levels of finished living space. The top floor is designed as an

    Dan Shockey Taylor-Made Deep Creek Real Estate, LLC

    1875 Pysell Crosscut Rd, Oakland, MD 21550
  • 0 Sanders Ln Unit MDGA2011678, Oakland, MD 21550
    0 Sanders Ln Unit MDGA2011678, Oakland, MD 21550
    0 Sanders Ln Unit MDGA2011678, 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
  • 827 Penn Point Rd, Oakland, MD 21550
    827 Penn Point Rd, Oakland, MD 21550
    827 Penn Point Rd, Oakland, MD 21550
    /64

    $1,400,000

    • 5 Beds
    • 3.5 Baths
    • 2,832 Sq Ft

    827 Penn Point Rd, Oakland, MD 21550

    Custom built by the original owners and thoughtfully expanded with a recent addition, this exceptional five-bedroom, 3.5-bath home is set on 100 feet of split lakefront in desirable Penn Cove. Featuring a coveted Type A dock permit, lakeside fire pit and pavilion, and easy shoreline access, the property is designed to embrace lake living in every season. Set on a generously sized lot with

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

    827 Penn Point Rd, Oakland, MD 21550
  • 0 Bethlehem Rd, Oakland, MD 21550
    0 Bethlehem Rd, Oakland, MD 21550
    0 Bethlehem Rd, Oakland, MD 21550
    /13

    $229,500

    $20K PRICE DROP
    • Land
    • 50 Acres
    • $4,590 per Acre

    0 Bethlehem Rd, Oakland, MD 21550

    50 Acres. Two Parcels. Zero Restrictions. Located along Bethlehem Road in Oakland, Garrett County, Maryland, this extraordinary 50-acre opportunity — comprised of two adjacent 25-acre parcels — is one of the rarest and most breathtaking pieces of unrestricted land available anywhere in western Maryland today. No zoning, no HOA, no flood zone, and no wetlands — every acre entirely and permanently

    Joseph Hawkins Hawkins Real Estate Company

    0 Bethlehem Rd, Oakland, MD 21550
  • 215 H St, Oakland, MD 21550
    215 H St, Oakland, MD 21550
    215 H St, Oakland, MD 21550
    /55

    $379,000

    • 3 Beds
    • 3 Baths
    • 2,388 Sq Ft

    215 H St, Oakland, MD 21550

    Welcome to the Maggie Watson Cottage, where historic charm meets modern convenience in the heart of Mountain Lake Park. This beautifully renovated home offers 3 bedrooms and 3 full bathrooms, thoughtfully updated to provide today’s comforts while preserving its timeless character. The interior features updated paint, both refinished and brand new hardwood flooring, and a modern gourmet kitchen

    Rachel Bruch Railey Realty, Inc.

    215 H St, Oakland, MD 21550
  • Lot 24 Eastview Ct, Oakland, MD 21550
    Lot 24 Eastview Ct, Oakland, MD 21550
    Lot 24 Eastview Ct, Oakland, MD 21550
    /21

    $49,000

    • Land
    • 1.01 Acres
    • $48,515 per Acre

    Lot 24 Eastview Ct, Oakland, MD 21550

    The perfect setting for your Deep Creek Lake getaway! Lot 24 Eastview Place is a 1.01-acre homesite in the Overlook community, offering water access to Deep Creek Lake. Situated on a quiet cul-de-sac, this cleared lot is ready for your dream home with approval already in place for a 3-bedroom septic system. Enjoy the ideal blend of privacy and convenience, just minutes from local dining,

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 730-4641

    Lot 24 Eastview Ct, Oakland, MD 21550
  • 815 L St, Oakland, MD 21550
    815 L St, Oakland, MD 21550
    815 L St, Oakland, MD 21550
    /17

    $39,000

    • Land
    • 12,196 Sq Ft
    • $139,286 per Acre

    815 L St, Oakland, MD 21550

    815 L Street offers a corner lot setting in Mountain Lake Park. This gently sloped homesite has a survey plat completed with setbacks shown for your future homesite plans. Public water/sewer, natural gas and electric are available. Less than one mile from Broadford Lake and only minutes to schools, groceries and everything you need in Oakland and Southern Garrett County!

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 696-4098

    815 L St, Oakland, MD 21550
  • 170 Cherrywood Dr, Oakland, MD 21550
    170 Cherrywood Dr, Oakland, MD 21550
    170 Cherrywood Dr, Oakland, MD 21550
    /67

    $699,000

    • 5 Beds
    • 3 Baths
    • 2,560 Sq Ft

    170 Cherrywood Dr, Oakland, MD 21550

    4/5BR 3BA custom home (3900+ total sf!) on 8+ acres of peaceful tranquility! Conveys with 2 lots (6 & 7) totaling 8.05 acres of wooded land in a laid back HOA that allows chickens & embraces the outdoor amenities Garrett County offers. Private and secluded rural location that is just minutes from town, schools, shopping and dining. This home was custom designed for work from home professionals -

    Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    170 Cherrywood Dr, Oakland, MD 21550
  • Lot 233 Cumberland Rd, Oakland, MD 21550
    Lot 233 Cumberland Rd, Oakland, MD 21550
    Lot 233 Cumberland Rd, Oakland, MD 21550
    /8

    $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

Showing Results 1 - 40, Page 1 of 4

Maryland Garrett County Oakland

Newest Listings for Sale in Oakland, MD

Frequently Asked Questions

What is the average home price in Oakland, MD?
Homes for sale in Oakland, MD have an average home price of $569,331.
How many homes have sold over the last 12 months in Oakland, MD?
140 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 21520.
How much do you need to make to afford a house in Oakland?
The median home price in Oakland is $419,000. If you put a 20% down payment of $83,800 and had a 30-year fixed mortgage with an interest rate of 6.51%, your estimated principal and interest payment would be $2,120 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $91K 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 96 days on the market compared to the national average of 58 days. The median sale price for homes in Oakland, MD over the last 12 months is $422,500, up 6% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$422,500
Median Single Family Sale Price
$405,000
Median Townhouse Sale Price
$460,000
Median 2 Bedroom Sale Price
$311,500
Median 1 Bedroom Sale Price
$217,450
Average Price Per Sq Ft
$274
Number of Homes for Sale
61
Last 12 months Home Sales
140
Months of Supply
5.20
Median List Price
$419,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
6%
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