17

Oakland, MD Homes for Sale under $400,000

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  • /47

    $300,000

    • 1 Bed
    • 1 Bath
    • 550 Sq Ft

    20160 Garrett Hwy Unit H708, Oakland, MD 21550

    Welcome to Will O' the Wisp Condominiums, where premium upgrades meet penthouse-level lakefront living at Deep Creek Lake! This fully furnished, beautifully updated, rarely available, top-floor two-level condo features one bedroom and one bath, offering 550 square feet of comfort, charm, and versatility — perfect as a vacation home, year-round retreat, or income-producing rental.Start

    Agent Photo

    Charlotte Savoy

    The KW Collective

    (301) 479-6357

    20160 Garrett Hwy Unit H708, Oakland, MD 21550
  • /50

    $335,000

    • 3 Beds
    • 2.5 Baths
    • 1,416 Sq Ft

    163 Crestview Dr, Oakland, MD 21550

    Welcome to 163 Crestview Drive — a beautifully maintained 3-bedroom, 2.5-bath home nestled in the Mitchell Manor neighborhood. This inviting Cape Cod offers timeless charm, modern updates, and a peaceful setting just minutes from downtown Oakland. Many recent improvements including HVAC, water treatment/filtration system, flooring and landscaping! Step inside to an open, light-filled floor plan

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 502-1143

    163 Crestview Dr, Oakland, MD 21550
  • /146

    $370,000

    • 3 Beds
    • 2 Baths
    • 2,516 Sq Ft

    321 Deer Park Hotel Rd, Oakland, MD 21550

    New Price – Now $360,000!Beautifully Updated Mountain Retreat Near Deep Creek LakeHere’s your chance to own a move-in-ready mountain retreat with major upgrades—now offered at just $360,000! Located only 10 miles from Deep Creek Lake and minutes to Oakland, this 3-bedroom, 2-bath home sits on nearly an acre and blends small-town convenience with peaceful mountain living.Step

    Thomas Long Railey Realty, Inc.

    321 Deer Park Hotel Rd, Oakland, MD 21550
  • /50

    $379,000

    • 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 Vacations & Sales

    961 Cedar Ln, Oakland, MD 21550
  • /56

    $359,000

    • 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 Vacations & Sales

    697 Monte Vista Rd, Oakland, MD 21550
  • /67

    $380,000

    • 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
  • /73

    $350,000

    • 6 Beds
    • 4 Baths
    • 3,662 Sq Ft

    3539 Underwood Rd, Oakland, MD 21550

    Picture perfect country setting. This spacious home sits on a level lot, in a lovely private setting. You are close enough to town and amenities, but this home offers the quiet country ambiance with a yard ready for fun and games. Multiple living areas and an eat in kitchen make this a perfect family home. This property also boasts two furnaces and two hot water heaters to make everyone

    Rachel Bruch Railey Realty, Inc.

    3539 Underwood Rd, Oakland, MD 21550
  • /2

    $369,000

    • 4 Beds
    • 2 Baths
    • 2,072 Sq Ft

    8946 Oakland Sang Run Rd, Oakland, MD 21550

    There are 3 adjacent parcels included with this sale :Tax ID - 1206034144, 1206020860, 1206007082All parcels together are 8 acres

    Joe Zorzit Eagle Commercial Realty

    8946 Oakland Sang Run Rd, Oakland, MD 21550
  • /62

    $315,000

    • 3 Beds
    • 1 Bath
    • 1,410 Sq Ft

    445 Dennett Rd, Oakland, MD 21550

    Updated, upgraded and move in ready, this 3 bedroom 1 bath home is located close to everything in town without the town taxes. This well maintained home offer many upgrades and features both inside and out. The kitchen is well equipped and offers a breakfast bar for 2. The upgraded bathroom is luxurious and inviting! Hardwood floors cover the main living, dining and bedroom areas. A full

    Bill Weissgerber Railey Realty, Inc.

    445 Dennett Rd, 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
  • /59

    $399,900

    • 2 Beds
    • 1 Bath
    • 887 Sq Ft

    565 Glendale Rd Unit 303B, Oakland, MD 21550

    Fully Renovated Penthouse at Silver Tree Suites – Been holding out for the nicest unit at Silver Tree Suites? The wait is over! This completely renovated and reimagined 2 Bedroom, 1 Bath penthouse is located on the top level of Building B and has a host of tasteful upgrades and stylish decor. Featuring year-round lake views and all-new flooring, stone, and rich hardwood finishes throughout.

    Jon Bell Railey Realty, Inc.

    565 Glendale Rd Unit 303B, Oakland, MD 21550
  • /38

    $314,900

    • 4 Beds
    • 2.5 Baths
    • 2,242 Sq Ft

    163 Mitchell Dr, Oakland, MD 21550

    3/4BR, 2.5BA, 2250sf+/- renovated home in Mitchell Manor! Newer roof in last 2 years, owner has added many upgrades inside & out. Features include a huge fenced-in backyard, attached garage with additional storage, multiple ensuites, walk-in closet, enlarged upper level deck, french doors, stone patio, outdoor sump pump, and more! Near end of cul-de-sac on low traffic street. Close to town

    Jay Ferguson Taylor Made Deep Creek Vacations & Sales

    163 Mitchell Dr, Oakland, MD 21550
  • /35

    $315,000

    • 3 Beds
    • 2 Baths
    • 1,389 Sq Ft

    473 Cumberland Rd, Oakland, MD 21550

    Nestled on a tranquil wooded hillside overlooking Deep Creek Lake, this charming home offers an exceptional opportunity for a private rural retreat while remaining close to the area’s best attractions. With delightful birdhouse accents, this cozy abode feels like your very own secluded nest. The recently updated kitchen is a culinary delight, making meal prep a breeze, while the newly renovated

    Jeremy McDonough Mr. Lister Realty

    473 Cumberland Rd, Oakland, MD 21550
  • /63

    $399,900

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

    3930 Mayhew Inn Rd, Oakland, MD 21550

    2 for 1 on 3.43 acres! Remodeled 2BR 2BA cottage with auxiliary building that has an oversized garage, multiple workshop areas and 1BR 1BA apartment on the second level. Cabin boasts high end finishes and open living space with a cozy wood burning stove. Recent upgrades include: heat pump + AC, appliances, modern kitchen, granite tops, bathrooms, some window & doors, as well as spacious decking.

    Jay Ferguson Taylor Made Deep Creek Vacations & Sales

    3930 Mayhew Inn Rd, Oakland, MD 21550
  • /55

    $349,900

    • 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 puts you right where you want to be—direct lakefront with unbeatable access to everything Deep Creek offers. Walk out to the water, hit the gym, unwind in the sauna, or challenge friends in the game room. Dutch’s at Silver Tree, The Harbor Bar, and Silvertree Marina are all within reach, making lakeside dining and boat days

    Jon Bell Railey Realty, Inc.

    565 Glendale Rd Unit 125, Oakland, MD 21550
  • /10

    $325,000

    • Land
    • 2.07 Acres
    • $157,005 per Acre

    Lot G Randall Way, Oakland, MD 21550

    Pergin Farm lake access lot with 2 acres and one boat slip. A private wooded setting in one of Deep Creeks most desirable, warm, and inviting locations.

    Russell Bounds Railey Realty, Inc.

    Lot G Randall Way, Oakland, MD 21550
  • /49

    $349,000

    • 3 Beds
    • 4 Baths
    • 1,503 Sq Ft

    522 E Green St, Oakland, MD 21550

    If you are looking for a low maintenance stone home sitting on a level lot in the town of Oakland, this is it. Offering three bedrooms (two of which are masters), a wood burning stone fireplace, tongue and groove wood walls throughout, and granite countertops. The partially fenced yard, nice back patio and attached two car garage are just a few more appealing aspects of this home. If you want

    Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    522 E Green St, Oakland, MD 21550

Home Trends in Oakland, MD

Housing Trends

Median Sale Price
$425,000
Median Single Family Sale Price
$440,000
Median Townhouse Sale Price
$560,000
Median 2 Bedroom Sale Price
$380,000
Median 1 Bedroom Sale Price
$269,950
Average Price Per Sq Ft
$277
Number of Homes for Sale
75
Last 12 months Home Sales
119
Months of Supply
7.60
Median List Price
$450,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
6%
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