68

Oakland, MD Homes for Sale under $400,000

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  • 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
    /5

    $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

    0 6 89 Acres -Woodlands Hill Dr Dr Unit MDGA2011974, Oakland, MD 21550
  • 565 Glendale Rd Unit 213-A, Oakland, MD 21550
    565 Glendale Rd Unit 213-A, Oakland, MD 21550
    565 Glendale Rd Unit 213-A, Oakland, MD 21550
    /24

    $225,000

    • 1 Bed
    • 1 Bath

    565 Glendale Rd Unit 213-A, Oakland, MD 21550

    Turnkey lakeview studio at The Suites at Silver Tree! This condo has an average annual gross rental of $25,342.Enjoy beautiful views of Deep Creek Lake from your private covered balcony while owning one of the area's most desirable vacation destinations. This fully furnished studio offers an open floor plan with a king bed, sleeper sofa, cozy gas fireplace, kitchenette, dining area, and

    Agent Photo

    Charlotte Savoy

    The KW Collective

    565 Glendale Rd Unit 213-A, Oakland, MD 21550
  • 408 M St, Oakland, MD 21550
    408 M St, Oakland, MD 21550
    408 M St, Oakland, MD 21550
    /48

    $199,000

    • 2 Beds
    • 1.5 Baths
    • 1,368 Sq Ft

    408 M St, Oakland, MD 21550

    Homes in this price range and in this good of condition are incredible rare to find! Charming and well-maintained, this 2-bedroom, 1.5-bath home offers an ideal combination of comfort, convenience, and easy living just minutes from downtown Oakland. Recent interior updates add a fresh, inviting feel, while the home's practical layout makes excellent use of the space. The attached one-car garage

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    408 M St, Oakland, MD 21550
  • 170 San Francisco St, Oakland, MD 21550
    170 San Francisco St, Oakland, MD 21550
    170 San Francisco St, Oakland, MD 21550
    /12

    $125,000

    • Land
    • 1.38 Acres
    • $90,580 per Acre

    170 San Francisco St, Oakland, MD 21550

    1.38 acres in Deep Creek Lake and WISP Resort area! Whether you envision a cozy cabin or a luxury lodge, this parcel offers the ideal blend of seclusion and accessibility. Property Highlights: Private well water source already in place, 200 AMP electric service connection, Approved perc test suitable for a 4-5 bedroom home, Privacy with convenience; close to main roads, yet tucked away for peace

    Agent Photo

    Hunter Shank

    Coldwell Banker Realty

    170 San Francisco St, Oakland, MD 21550
  • 565 Glendale Rd Unit 212 - A, Oakland, MD 21550
    565 Glendale Rd Unit 212 - A, Oakland, MD 21550
    565 Glendale Rd Unit 212 - A, Oakland, MD 21550
    /20

    $160,000

    • 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.

    565 Glendale Rd Unit 212 - A, Oakland, MD 21550
  • 24 Woodlands Hill Ln, Oakland, MD 21550
    24 Woodlands Hill Ln, Oakland, MD 21550
    24 Woodlands Hill Ln, Oakland, MD 21550
    /14

    $137,500

    • Land
    • 1.53 Acres
    • $89,869 per Acre

    24 Woodlands Hill Ln, Oakland, MD 21550

    Your Deep Creek dream starts here! Don't miss this beautiful 1.53-acre homesite in The View at Deep Creek Lake, where breathtaking mountain views and seasonal views of the lake create the perfect backdrop for your future home. Whether you're dreaming of a full-time residence, weekend escape, or investment property, you'll love the peaceful wooded setting and convenient location. Just minutes from

    Agent Photo

    Charlotte Savoy

    The KW Collective

    24 Woodlands Hill Ln, Oakland, MD 21550
  • 0 3 15 Acres Woodlands Hill Dr Unit MDGA2012042, Oakland, MD 21550
    0 3 15 Acres Woodlands Hill Dr Unit MDGA2012042, Oakland, MD 21550
    0 3 15 Acres Woodlands Hill Dr Unit MDGA2012042, Oakland, MD 21550
    /3

    $200,000

    • Land
    • 3.15 Acres
    • $63,492 per Acre

    0 3 15 Acres Woodlands Hill Dr Unit MDGA2012042, Oakland, MD 21550

    3.15 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 area parks and amenities. No HOA.

    Agent Photo

    Brian Homberg

    Taylor-Made Deep Creek Real Estate, LLC

    0 3 15 Acres Woodlands Hill Dr Unit MDGA2012042, 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
    /27

    $309,000

    • 1 Bed
    • 1 Bath
    • 550 Sq Ft

    20160 Garrett Hwy Unit H706, Oakland, MD 21550

    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 vacation retreat, year-round getaway, or

    Agent Photo

    James Matthews

    Taylor-Made Deep Creek Real Estate, LLC

    20160 Garrett Hwy Unit H706, Oakland, MD 21550
  • 0 5 Acres Lake Shore Dr, Oakland, MD 21550
    0 5 Acres Lake Shore Dr, Oakland, MD 21550
    0 5 Acres Lake Shore Dr, Oakland, MD 21550
    /3

    $250,000

    • Land
    • 5 Acres
    • $50,000 per Acre

    0 5 Acres Lake Shore Dr, Oakland, MD 21550

    5.0 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 area parks and amenities.

    Agent Photo

    Brian Homberg

    Taylor-Made Deep Creek Real Estate, LLC

    0 5 Acres Lake Shore Dr, Oakland, MD 21550
  • Lot 20 Paradise Ridge Rd, Oakland, MD 21550
    Lot 20 Paradise Ridge Rd, Oakland, MD 21550
    Lot 20 Paradise Ridge Rd, Oakland, MD 21550
    /25

    $124,000

    $6K PRICE DROP
    • Land
    • 2.1 Acres
    • $59,048 per Acre

    Lot 20 Paradise Ridge Rd, Oakland, MD 21550

    Lot 20 Paradise Ridge offers a mountaintop setting with exceptional lake and mountain views facing east toward Backbone Mountain. Enjoy relaxing morning sunrises, lake access at one of Deep Creek Lake's most premier water access points and a location that feels like you are truly away, yet only a few minutes to the most important amenities you come to enjoy here at the lake. Approved perc site on

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    Lot 20 Paradise Ridge Rd, Oakland, MD 21550
  • 157 Jeffrey Ln Unit 21B, Oakland, MD 21550
    157 Jeffrey Ln Unit 21B, Oakland, MD 21550
    157 Jeffrey Ln Unit 21B, Oakland, MD 21550
    /29

    $294,000

    $5K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 550 Sq Ft

    157 Jeffrey Ln Unit 21B, Oakland, MD 21550

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

    Agent Photo

    James Matthews

    Taylor-Made Deep Creek Real Estate, LLC

    157 Jeffrey Ln Unit 21B, Oakland, MD 21550
  • 14 Woodlands Hill Ln, Oakland, MD 21550
    14 Woodlands Hill Ln, Oakland, MD 21550
    14 Woodlands Hill Ln, Oakland, MD 21550
    /12

    $165,000

    • Land
    • 2.04 Acres
    • $80,882 per Acre

    14 Woodlands Hill Ln, Oakland, MD 21550

    Your Deep Creek dream starts here! Build the mountain retreat you've always imagined on this spectacular 2.04-acre homesite in The View at Deep Creek Lake. Offering breathtaking panoramic mountain views with seasonal views of Deep Creek Lake, this property is the perfect setting for a full-time residence, vacation home, or investment property. Enjoy the privacy of a wooded setting while being

    Agent Photo

    Charlotte Savoy

    The KW Collective

    14 Woodlands Hill Ln, Oakland, MD 21550
  • 1167 Tall Oaks Dr, Oakland, MD 21550
    1167 Tall Oaks Dr, Oakland, MD 21550
    1167 Tall Oaks Dr, Oakland, MD 21550
    /59

    $349,000

    $30K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,920 Sq Ft

    1167 Tall Oaks Dr, Oakland, MD 21550

    Log cabin on 11 private acres. Located in the gated Timbers on the Yough community. The community features shared access to the Youghiogheny River. Home features include spacious covered deck, newly installed walkway, exterior fire pit, breakfast bar, and pellet stove. Heart pine floors on main floor and stairs, reclaimed from RJ Reynolds tobacco factory built around 1900! The primary bath offers

    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
    /65

    $279,000

    $35K PRICE DROP
    • 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
  • 2 Overlook Ridge Dr S, Oakland, MD 21550
    2 Overlook Ridge Dr S, Oakland, MD 21550
    2 Overlook Ridge Dr S, Oakland, MD 21550
    /11

    $199,900

    $20K PRICE DROP
    • Land
    • 4,791 Sq Ft
    • $1,817,273 per Acre

    2 Overlook Ridge Dr S, Oakland, MD 21550

    Enjoy the best the lake has to offer from 'Overlook Ridge'! Boasting year-round lake views, yet tucked away in a peaceful and serene community setting. Short drive to the community lake access area for swimming and fishing! Dock Slips may be leased through HOA. Utilities to site and ready to build your perfect four-season Deep Creek getaway. Located just off of Rt. 219, with easy access to all

    Jon Bell Railey Realty, Inc.

    2 Overlook Ridge Dr S, Oakland, MD 21550
  • 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
  • 13 Laurel Brook Dr, Oakland, MD 21550
    13 Laurel Brook Dr, Oakland, MD 21550
    13 Laurel Brook Dr, Oakland, MD 21550
    /42

    $259,500

    $15K PRICE INCREASE
    • 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
  • 615 E Oak St, Oakland, MD 21550
    615 E Oak St, Oakland, MD 21550
    615 E Oak St, Oakland, MD 21550
    /60

    $365,000

    • 5 Beds
    • 3 Baths
    • 2,652 Sq Ft

    615 E Oak St, Oakland, MD 21550

    PRIME INVESTMENT OPPURTUNITY! Recently renovated (including plumbing and electric) in 2025, this triplex is a rare opportunity in the heart of downtown Oakland, MD. With three separate units, you'll have the potential for three streams of rental income from one property. Buyer could live in one unit and rent the other units out to help offset mortgage costs! Whether you're a seasoned investor or

    Lucas Muenchow Railey Realty, Inc.

    615 E Oak St, Oakland, MD 21550
  • 106 G St, Oakland, MD 21550
    106 G St, Oakland, MD 21550
    106 G St, 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
  • 2560 Bray School Rd, Oakland, MD 21550
    2560 Bray School Rd, Oakland, MD 21550
    /2

    $249,900

    • Land
    • 7.72 Acres
    • $32,370 per Acre

    2560 Bray School Rd, Oakland, MD 21550

    Imagine waking up in your own private retreat, just a short walk from Deep Creek Lake. This 7.72-acre wooded parcel (Tax ID 1218036215) offers the rare combination of privacy, space, and lake access, all within Deep Creek Lake's most sought-after playground. Tucked into the Millhouse Manor subdivision, this property comes with access to a community lake area at the end of Red Run Cove, a peaceful

    Jeremy Cunningham Railey Realty, Inc.

    2560 Bray School 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
  • 141 Montana Ln, Oakland, MD 21550
    141 Montana Ln, Oakland, MD 21550
    141 Montana 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
  • 18948 Garrett Hwy, Oakland, MD 21550
    18948 Garrett Hwy, Oakland, MD 21550
    18948 Garrett Hwy, Oakland, MD 21550
    /41

    $375,000

    • 2 Beds
    • 2 Baths
    • 1,404 Sq Ft

    18948 Garrett Hwy, Oakland, MD 21550

    Enjoy all the seasons in this beautiful Cape Cod home nestled on a 1-acre private wooded lot close to Oakland and all the attractions Deep Creek Lake has to offer. Whether you are seeking a year-round permanent residence or a private seasonal getaway for summer and winter fun, this property delivers a wonderful setting with an ideal balance of privacy and convenience. The open floor plan allows

    Dan (Sussan) Duggan 1 Real Estate Source LLC

    18948 Garrett Hwy, Oakland, MD 21550
  • 0 Paradise Point Rd Unit MDGA2003916, Oakland, MD 21550
    0 Paradise Point Rd Unit MDGA2003916, Oakland, MD 21550
    /2

    $129,000

    • Land
    • 1 Acre
    • $129,000 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
  • 321 Deer Park Hotel Rd, Oakland, MD 21550
    321 Deer Park Hotel Rd, Oakland, MD 21550
    321 Deer Park Hotel Rd, Oakland, MD 21550
    /47

    $384,500

    $15K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,476 Sq Ft

    321 Deer Park Hotel Rd, Oakland, MD 21550

    Double lots! Lot 4 & 5 of Hunting Ridge Estates will be sold together to bring up a total of .96 acre on your 2476 sqft. of finished living space home awaits you including your finished basement. Metal Roof is only 4 years old. Windows and doors are only 6 years old. Location, location...Welcome to 321 Deer Park Hotel Rd. where your mountain retreat will be just outside the city limits with only

    Pamela Debnam Houwzer, LLC

    321 Deer Park Hotel Rd, Oakland, MD 21550
  • 511 Main St, Oakland, MD 21550
    511 Main St, Oakland, MD 21550
    511 Main St, Oakland, MD 21550
    /10

    $350,000

    • 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
  • 139 S Oakhall Dr, Oakland, MD 21550
    139 S Oakhall Dr, Oakland, MD 21550
    139 S Oakhall Dr, Oakland, MD 21550
    /52

    $229,000

    • 3 Beds
    • 1.5 Baths
    • 1,612 Sq Ft

    139 S Oakhall Dr, Oakland, MD 21550

    Location, location, location! Enjoy easy living in this one-level raised rancher featuring 3 bedrooms and 1.5 baths, with all bedrooms conveniently located on the main level. Beautiful hardwood floors add warmth, while the covered front porch and side covered deck offer inviting spaces to relax and enjoy the peaceful surroundings. The fenced-in backyard provides plenty of outdoor space for pets,

    Laura Newhall Taylor-Made Deep Creek Real Estate, LLC

    139 S Oakhall Dr, 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
  • 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
  • 0 Dennett Rd 10 Acres To Oakland Ave Unit MDGA2011252, Oakland, MD 21550
    0 Dennett Rd 10 Acres To Oakland Ave Unit MDGA2011252, Oakland, MD 21550
    0 Dennett Rd 10 Acres To Oakland Ave Unit MDGA2011252, 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
  • 112 E Pennington St, Oakland, MD 21550
    112 E Pennington St, Oakland, MD 21550
    112 E Pennington St, Oakland, MD 21550
    /63

    $325,000

    $25K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 2,165 Sq Ft

    112 E Pennington St, Oakland, MD 21550

    Completely rebuilt and beautifully renovated 5 bedroom 3 bathroom home! Welcome to this stunning 5-bedroom, 3-bathroom home that has been completely transformed from top to bottom with exceptional craftsmanship and modern finishes. Offering the charm of a classic home with the peace of mind of virtually all-new construction, this property is truly move-in ready. Major updates include a new

    Sheila Howell Lake Homes Realty, LLC

    112 E Pennington St, Oakland, MD 21550
  • 206 W Liberty St, Oakland, MD 21550
    206 W Liberty St, Oakland, MD 21550
    206 W Liberty St, Oakland, MD 21550
    /35

    $174,900

    $24K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 2,008 Sq Ft

    206 W Liberty St, Oakland, MD 21550

    Welcome to this charming 2 bedroom, 1 bath home in the heart of Oakland, offering endless potential and plenty of character. Step inside to an inviting open floor plan that creates a bright, spacious feel and allows for a comfortable flow between the living and kitchen areas. The large covered front porch provides the perfect spot to enjoy your morning coffee, relax after a long day, or take in

    Nicole Jackson Railey Realty, Inc.

    206 W Liberty St, Oakland, MD 21550
  • 552 Black Oak Dr, Oakland, MD 21550
    552 Black Oak Dr, Oakland, MD 21550
    552 Black Oak Dr, Oakland, MD 21550
    /46

    $349,000

    $10K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,152 Sq Ft

    552 Black Oak Dr, Oakland, MD 21550

    Looking for a vacation spot or main living, Check out this nicely remolded home in a gated community. 3 bedrooms, 1 1/2 bathrooms, main level laundry room. Great rustic touches . Detached Garage with pellet stove. Yough Mountain Resort is the ultimate mountain escape! Nestled in a quiet, secluded area, this beautifully updated retreat offers modern comfort in a rustic Access to over 50 miles of

    Connie Leprevost Long & Foster Real Estate, Inc.

    552 Black Oak Dr, Oakland, MD 21550
  • 531 Glendale Rd Unit B302, Oakland, MD 21550
    531 Glendale Rd Unit B302, Oakland, MD 21550
    531 Glendale Rd Unit B302, Oakland, MD 21550
    /29

    $339,900

    $29K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 887 Sq Ft

    531 Glendale Rd Unit B302, Oakland, MD 21550

    Experience effortless lakeside living at its finest in this spacious 2-bedroom, 1-bath unit in Silver Tree Suites—one of the largest units in the complex! This beautifully designed unit features an open floorplan centered around a cozy fireplace, perfect for relaxing after a day on the lake. A generous loft area creates a distinct separation between living and sleeping spaces, offering

    Larry Smith Railey Realty, Inc.

    531 Glendale Rd Unit B302, Oakland, MD 21550
  • 586 Bray School Rd, Oakland, MD 21550
    586 Bray School Rd, Oakland, MD 21550
    586 Bray School Rd, Oakland, MD 21550
    /32

    $289,000

    • 4 Beds
    • 2 Baths
    • 2,240 Sq Ft

    586 Bray School Rd, Oakland, MD 21550

    Spacious one level home, 4 BR with den, living room, extra office off Main BR, large back yard with huge deck. Very large main bedroom with bath and extra room (could be nursery, extra BR or office) . 2 Full baths, 2 fireplaces, Laundry and perfect location for privacy, yet close to all things fun in the Deep Creek Lake area. One mile from Deep Creek Lake, 2 miles from Swallow Falls State Park.

    Julie Mead The KW Collective

    586 Bray School Rd, Oakland, MD 21550
  • 5 Laurel Brook Dr, Oakland, MD 21550
    5 Laurel Brook Dr, Oakland, MD 21550
    5 Laurel Brook Dr, Oakland, MD 21550
    /29

    $269,900

    • 2 Beds
    • 2 Baths
    • 1,400 Sq Ft

    5 Laurel Brook Dr, Oakland, MD 21550

    Major renovations on this 2BR, 2BA Laurel brook two level townhome! Updates include new flooring, paint, fixtures, countertops, bathrooms and furnishings. One of the best dollar for dollar values still available at Deep Creek Lake and located within one mile of shopping, dining, entertainment, marinas and more! Enjoy a park-like setting with mature trees, common areas for relaxing or picnics and

    Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    5 Laurel Brook Dr, 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
  • 22 Woodlands Hill Ln, Oakland, MD 21550
    22 Woodlands Hill Ln, Oakland, MD 21550
    22 Woodlands Hill Ln, Oakland, MD 21550
    /22

    $159,000

    • Land
    • 2.02 Acres
    • $78,713 per Acre

    22 Woodlands Hill Ln, Oakland, MD 21550

    2.02-acre wooded building lot in The View community at Deep Creek Lake. This beautiful parcel offers a private setting with plenty of room for your future mountain or lake area retreat. Seasonal mountain and lake views. Conveniently located off Lakeshore Drive and just minutes from Deep Creek Lake, Wisp Resort, restaurants, shopping, and other area amenities. Enjoy the perfect combination of

    Jon Bell Railey Realty, Inc.

    22 Woodlands Hill Ln, Oakland, MD 21550
  • 40 Sunshine Ln, Oakland, MD 21550
    40 Sunshine Ln, Oakland, MD 21550
    40 Sunshine Ln, Oakland, MD 21550
    /43

    $169,000

    $10K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,516 Sq Ft

    40 Sunshine Ln, Oakland, MD 21550

    Enjoy the charm of country living with the convenience of being in downtown Crellin!Situated on nearly an acre, this inviting 3-bedroom, 1-bath home offers a bright, open layout filled with natural light.The main level features a spacious bedroom surrounded by windows, creating a warm and welcoming retreat. Upstairs, you'll find two additional bedrooms that can easily accommodate

    Danielle Luscombe Taylor-Made Deep Creek Real Estate, LLC

    40 Sunshine Ln, Oakland, MD 21550
  • 565 Glendale Rd Unit 306, Oakland, MD 21550
    565 Glendale Rd Unit 306, Oakland, MD 21550
    565 Glendale Rd Unit 306, Oakland, MD 21550
    /32

    $249,900

    • 2 Beds
    • 1 Bath
    • 772 Sq Ft

    565 Glendale Rd Unit 306, Oakland, MD 21550

    Experience the best of Deep Creek Lake living from this beautifully appointed studio loft at Silver Tree Suites—one of the lake’s most sought-after locations! Offering two separate sleeping areas, a kitchenette, gas fireplace, and private balcony, this unit is designed for comfort and easy getaway living. Tastefully updated with new carpet and flooring, as well as kitchen and bathroom

    Jon Bell Railey Realty, Inc.

    565 Glendale Rd Unit 306, Oakland, MD 21550

Showing Results 1 - 40, Page 1 of 2

Maryland Garrett County

Real Estate & Homes in Oakland, MD under $400,000

Home Prices in Oakland, MD

The median home sale price in Oakland, MD is $422,500, up 3% year-over-year. Homes in Oakland sell in 108 days on average, compared to the national average of 55 days.

Home Price Trends

Median Sale Price
$422,500
Median Single Family Sale Price
$425,000
Median Townhouse Sale Price
$460,000
Median 2 Bedroom Sale Price
$285,000
Median 1 Bedroom Sale Price
$221,950
Average Price Per Sq Ft
$278
Number of Homes for Sale
58
Last 12 months Home Sales
144
Months of Supply
4.80
Median List Price
$425,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
3%
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