16

Oakland, MD Homes for Sale under $400,000

Section Image
  • 5024 Cranesville Rd, Oakland, MD 21550
    5024 Cranesville Rd, Oakland, MD 21550
    5024 Cranesville Rd, Oakland, MD 21550
    /67

    $399,000

    • 3 Beds
    • 2.5 Baths
    • 2,128 Sq Ft

    5024 Cranesville Rd, Oakland, MD 21550

    Just Reduced!! Charming 3-Bedroom Home with Scenic Mountain & Valley Views. Nestled on a 1.68-acre hillside in a beautiful conservation area, this 3-bedroom, 2.5-bath home combines natural charm with modern comfort. The native stone exterior and peaceful setting set the tone for this inviting residence.Inside, the main level features a spacious primary suite with a jetted tub, double vanity,

    Rich Orr Railey Realty, Inc.

    5024 Cranesville Rd, Oakland, MD 21550
  • 1167 Tall Oaks Dr, Oakland, MD 21550
    1167 Tall Oaks Dr, Oakland, MD 21550
    1167 Tall Oaks Dr, Oakland, MD 21550
    /61

    $379,000

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

    1167 Tall Oaks Dr, Oakland, MD 21550

    Log cabin on 11 private acres. Located in the gated Timbers on the Yough community featuring Youghiogheny River shared access. Home features include spacious covered deck, newly installed walkway, exterior fire pit, breakfast bar, and pellet stove. The primary bath offers dual sinks, dual shower heads and radiant floor heat!

    Kellyann Green Railey Realty, Inc.

    1167 Tall Oaks Dr, Oakland, MD 21550
  • 511 Main St, Oakland, MD 21550
    511 Main St, Oakland, MD 21550
    511 Main St, 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
  • 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
  • 697 Monte Vista Rd, Oakland, MD 21550
    697 Monte Vista Rd, Oakland, MD 21550
    697 Monte Vista Rd, Oakland, MD 21550
    /56

    $339,000

    • 5 Beds
    • 3.5 Baths
    • 3,682 Sq Ft

    697 Monte Vista Rd, Oakland, MD 21550

    Tucked away just minutes from downtown Oakland, MD, lies a home that truly surprises with over 3,500 sq. ft. of living space on 1.88 acres with breathtaking farm and mountain views. Step inside the main level, where the master suite awaits along with two additional large bedrooms and a full bath, plus a mudroom area with a convenient half bath—perfect for entertaining. Cozy evenings are made even

    Laura Newhall Taylor Made Deep Creek Real Estate

    697 Monte Vista Rd, Oakland, MD 21550
  • 3930 Mayhew Inn Rd, Oakland, MD 21550
    3930 Mayhew Inn Rd, Oakland, MD 21550
    3930 Mayhew Inn Rd, Oakland, MD 21550
    /81

    $399,900

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

    3930 Mayhew Inn Rd, Oakland, MD 21550

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

    Jay Ferguson Taylor Made Deep Creek Real Estate

    3930 Mayhew Inn Rd, Oakland, MD 21550
  • 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
  • 552 Black Oak Dr, Oakland, MD 21550
    552 Black Oak Dr, Oakland, MD 21550
    552 Black Oak Dr, Oakland, MD 21550
    /46

    $359,000

    • 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

    $369,000

    • 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
  • 723 Kings Ct, Oakland, MD 21550
    723 Kings Ct, Oakland, MD 21550
    723 Kings Ct, Oakland, MD 21550
    /67

    $359,700

    • 4 Beds
    • 2.5 Baths
    • 1,824 Sq Ft

    723 Kings Ct, Oakland, MD 21550

    "Charming two-story home situated on a beautiful .292-acre level lot in a prime location (Kings Hills Estates) Enjoy the perfect blend of comfort and convenience with spacious living areas, a serene yard ideal for outdoor entertaining. Ideally located near a top-rate Hospital, popular shopping destinations, and just minutes to Broadford Lake. Whether you're enjoying a day on the water or running

    Debra Beitzel Long & Foster Real Estate, Inc.

    723 Kings Ct, Oakland, MD 21550
  • 961 Cedar Ln, Oakland, MD 21550
    961 Cedar Ln, Oakland, MD 21550
    961 Cedar Ln, Oakland, MD 21550
    /50

    $359,000

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

    961 Cedar Ln, Oakland, MD 21550

    Tucked away in the woods on 1.72 acres, this stunning 4-bedroom, 2.5-bath mountain retreat offers privacy, comfort, and plenty of space to unwind. Step inside to find a warm and inviting main level highlighted by a stone fireplace, cozy dining area, and galley-style kitchen. Relax on the screened-in porch complete with a hot tub under roof, perfect for year-round enjoyment. The finished basement

    Laura Newhall Taylor Made Deep Creek Real Estate

    961 Cedar Ln, Oakland, MD 21550
  • 931 Black Oak Dr, Oakland, MD 21550
    931 Black Oak Dr, Oakland, MD 21550
    931 Black Oak Dr, Oakland, MD 21550
    /53

    $349,999 Open House 5/16

    • 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
  • 1740 Old Crellin Rd, Oakland, MD 21550
    1740 Old Crellin Rd, Oakland, MD 21550
    1740 Old Crellin Rd, Oakland, MD 21550
    /28

    $335,000

    • 3 Beds
    • 3 Baths
    • 2,288 Sq Ft

    1740 Old Crellin Rd, Oakland, MD 21550

    Come see this beautifully maintained 3-bedroom, 3-bath Colonial-style residence nestled on a private 1-acre lot along Old Crellin Road in Oakland. Offering 2,300 square feet of living space, this home combines classic charm with modern comfort in an ideal location just outside town limits. Step inside to find a spacious and inviting layout, perfect for both everyday living and entertaining. The

    Andrew Orr The KW Collective

    1740 Old Crellin Rd, Oakland, MD 21550
  • 20160 Garrett Hwy Unit G507, Oakland, MD 21550
    20160 Garrett Hwy Unit G507, Oakland, MD 21550
    20160 Garrett Hwy Unit G507, Oakland, MD 21550
    /38

    $389,000

    • 2 Beds
    • 1 Bath
    • 912 Sq Ft

    20160 Garrett Hwy Unit G507, Oakland, MD 21550

    Experience lakefront living with this charming two-level condo at Will O the Wisp at Deep Creek Lake! Offering 2 bedrooms and 1 full bathroom, it captures breathtaking lake views from both levels. The main floor features a functional kitchen and a cozy living area with a wood-burning fireplace—perfect for relaxing after a day on the water. Upstairs, you’ll find two comfortable bedrooms and a full

    Nina Beitzel Railey Realty, Inc.

    20160 Garrett Hwy Unit G507, Oakland, MD 21550
  • 565 Glendale Rd Unit B206, Oakland, MD 21550
    565 Glendale Rd Unit B206, Oakland, MD 21550
    565 Glendale Rd Unit B206, 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
  • 8946 Oakland Sang Run Rd, Oakland, MD 21550
    8946 Oakland Sang Run Rd, Oakland, MD 21550
    /2

    $369,000

    • Land
    • 20,473 Sq Ft
    • $785,106 per Acre

    8946 Oakland Sang Run Rd, Oakland, MD 21550

    There are 3 adjacent parcels included with this sale :Tax ID - 1206034144, 1206020860, 1206007082 All parcels together are 8 acres WARNING: The house on this property is condemned and ready for tear down. Enter at your own risk.

    Joe Zorzit Eagle Commercial Realty

    8946 Oakland Sang Run Rd, Oakland, MD 21550
Maryland Garrett County Oakland

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

Home Trends in Oakland, MD

On average, homes in Oakland, MD sell after 98 days on the market compared to the national average of 56 days. The median sale price for homes in Oakland, MD over the last 12 months is $425,000, up 6% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$425,000
Median Single Family Sale Price
$422,500
Median Townhouse Sale Price
$472,500
Median 2 Bedroom Sale Price
$310,250
Median 1 Bedroom Sale Price
$217,450
Average Price Per Sq Ft
$268
Number of Homes for Sale
55
Last 12 months Home Sales
136
Months of Supply
4.90
Median List Price
$425,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
6%
How to Buy a Home How to Finance a Home How to Sell a Home

Explore the array of homes and houses for sale under $400,000 in Oakland, where you'll find 16 options tailored for those seeking affordable real estate opportunities. Whether you're interested in spacious family homes, modern townhouses, or cozy bungalows, Oakland offers a diverse range of choices to match your needs and financial considerations. Take advantage of these affordably-priced properties to make your move into the real estate market in Oakland, MD.

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group