16

Oakland, MD Homes for Sale under $300,000

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  • 20160 Garrett Hwy Unit H708, Oakland, MD 21550
    20160 Garrett Hwy Unit H708, Oakland, MD 21550
    20160 Garrett Hwy Unit H708, Oakland, MD 21550
    /47

    $289,900

    • 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 your

    Agent Photo

    Charlotte Savoy

    The KW Collective

    (301) 479-6357

    20160 Garrett Hwy Unit H708, Oakland, MD 21550
  • 702 Sunshine Dr, Oakland, MD 21550
    702 Sunshine Dr, Oakland, MD 21550
    702 Sunshine Dr, Oakland, MD 21550
    /55

    $275,000

    • 3 Beds
    • 2 Baths
    • 1,848 Sq Ft

    702 Sunshine Dr, Oakland, MD 21550

    Welcome to easy, one-level living at 702 Sunshine Dr! This well-maintained 3-bedroom, 2-bath home offers a functional layout with everything you need on one floor. Enjoy the convenience of an attached garage, a fenced backyard, and a covered back porch—perfect for morning coffee, outdoor dining, or relaxing in any weather. Located just minutes from downtown Oakland, this home puts you close to

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 905-4746

    702 Sunshine Dr, Oakland, MD 21550
  • 127 Jeffrey Ln Unit 18C, Oakland, MD 21550
    127 Jeffrey Ln Unit 18C, Oakland, MD 21550
    127 Jeffrey Ln Unit 18C, Oakland, MD 21550
    /9

    $275,000 Coming Soon

    • 3 Beds
    • 2 Baths
    • 875 Sq Ft

    127 Jeffrey Ln Unit 18C, Oakland, MD 21550

    Welcome to 127 Jeffrey Lane 18C! Centrally located at Deep Creek Lake, this unit offers convenience year round to restaurants, skiing, golf courses, Deep Creek Lake and even one of the areas most desired coffee shops just a few hundred feet away. Enjoy northeastern exposure for great sunrises overlooking the lake. The main level offers a kitchen, living room with wood burning fireplace, 2

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (301) 591-6157

    127 Jeffrey Ln Unit 18C, Oakland, MD 21550
  • 127 S Oakhall Dr, Oakland, MD 21550
    127 S Oakhall Dr, Oakland, MD 21550
    127 S Oakhall Dr, Oakland, MD 21550
    /60

    $299,000

    • 4 Beds
    • 2 Baths
    • 1,913 Sq Ft

    127 S Oakhall Dr, Oakland, MD 21550

    Welcome to this well maintained 4-bed, 2-bath ranch home on a generous corner lot in Oakland, MD. Inviting curb appeal with stone exterior and mature landscaping sets the tone. Step inside to a bright and spacious main level featuring gleaming hardwood floors, a large eat-in kitchen with ample cabinetry, and an open living area perfect for gatherings. Enjoy three main-level bedrooms and a full

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 792-8710

    127 S Oakhall Dr, Oakland, MD 21550
  • 565 Glendale Rd Unit 106B, Oakland, MD 21550
    565 Glendale Rd Unit 106B, Oakland, MD 21550
    565 Glendale Rd Unit 106B, Oakland, MD 21550
    /27

    $239,900

    • 1 Bed
    • 1 Bath

    565 Glendale Rd Unit 106B, Oakland, MD 21550

    Ground-floor end unit with lake views at Silver Tree Suites. This one-bedroom layout packs in a gas fireplace, full bath with tub/shower, and a tidy kitchenette with microwave, dishwasher, and full fridge. Balcony doors open to Deep Creek air and filtered lake scenes. Community perks include sauna, gym, game room and more. Sold turn-key, fully furnished. Ductless units for heat and A/C. Monthly

    Jon Bell Railey Realty, Inc.

    565 Glendale Rd Unit 106B, Oakland, MD 21550
  • 47 Ridgewood Dr, Oakland, MD 21550
    47 Ridgewood Dr, Oakland, MD 21550
    47 Ridgewood Dr, Oakland, MD 21550
    /29

    $219,900

    • Land
    • 1.1 Acres
    • $199,909 per Acre

    47 Ridgewood Dr, Oakland, MD 21550

    Prime Lake Access Lot in Mountainside – Perfect for Your Dream Home! Nestled on a one-acre wooded lot in the sought-after Mountainside community, this homesite offers breathtaking views of Deep Creek Lake and the ideal slope for a walk-out basement. Enjoy the best of four-season living with easy access to community lake privileges, state parks, restaurants, and WISP Resort. Plus, take advantage

    Mike Fenton Railey Realty, Inc.

    47 Ridgewood Dr, Oakland, MD 21550
  • Lot G Randall Way, Oakland, MD 21550
    Lot G Randall Way, Oakland, MD 21550
    Lot G Randall Way, Oakland, MD 21550
    /10

    $250,000

    • Land
    • 2.07 Acres
    • $120,773 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
  • 26 Green Brier Rd, Oakland, MD 21550
    26 Green Brier Rd, Oakland, MD 21550
    26 Green Brier Rd, 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
  • 181 Jeffrey Ln Unit 23-A, Oakland, MD 21550
    181 Jeffrey Ln Unit 23-A, Oakland, MD 21550
    181 Jeffrey Ln Unit 23-A, Oakland, MD 21550
    /25

    $269,900

    • 2 Beds
    • 1 Bath
    • 670 Sq Ft

    181 Jeffrey Ln Unit 23-A, Oakland, MD 21550

    Discover comfort and convenience in this charming 2-bedroom, 1-bath unit ideally located in the desirable Roman Ridge at Traders Landing community. Enjoy peaceful lake views from your covered front deck—the perfect spot to relax with your morning coffee or unwind in the evening. Inside, you’ll find a warm and inviting living space featuring a wood-burning fireplace to take the chill off during

    Larry Smith Railey Realty, Inc.

    181 Jeffrey Ln Unit 23-A, Oakland, MD 21550
  • 62 Wild Turkey Ct, Oakland, MD 21550
    62 Wild Turkey Ct, Oakland, MD 21550
    62 Wild Turkey Ct, Oakland, MD 21550
    /30

    $249,000 New Construction

    • 4 Beds
    • 3 Baths
    • 2,390 Sq Ft

    62 Wild Turkey Ct, Oakland, MD 21550

    Current new home construction project underway, but Builder not going to complete at this time due too busy. So, ready for who may wish to complete project themselves or have completed by others, or current Builder may consider completing for Buyer. Current structure is a custom engineered modular home. This is not a completed or intended by Builder to be completed house project at this time .

    Chip Smith 1 Real Estate Source LLC

    62 Wild Turkey Ct, Oakland, MD 21550
  • 315 Coolidge Ave, Oakland, MD 21550
    315 Coolidge Ave, Oakland, MD 21550
    315 Coolidge Ave, Oakland, MD 21550
    /53

    $269,500

    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft

    315 Coolidge Ave, Oakland, MD 21550

    Well maintained brick rancher located in the heart of Oakland. This home offers a large kitchen open to the living room with a built-in fireplace, separate dining room, and new carpet through out. The basement is very clean, offering a clean slate for whatever you would like to do. The rear covered porch, deck and fenced in yard makes a great space to enjoy family and friends. The location is

    Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    315 Coolidge Ave, Oakland, MD 21550
  • 565 Glendale Rd Unit 103B, Oakland, MD 21550
    565 Glendale Rd Unit 103B, Oakland, MD 21550
    565 Glendale Rd Unit 103B, Oakland, MD 21550
    /53

    $260,000

    • 1 Bed
    • 1 Bath

    565 Glendale Rd Unit 103B, Oakland, MD 21550

    Ground-floor end unit with lake views at Silver Tree Suites! This inviting one-bedroom layout features a gas fireplace, full bath with tub/shower, and a tidy kitchenette equipped with a microwave, dishwasher, and full-size refrigerator. Balcony doors open to fresh Deep Creek air and filtered lake views, with a private deck that is perfect for relaxing after a day on the water. Enjoy a variety of

    Rachel Bruch Railey Realty, Inc.

    565 Glendale Rd Unit 103B, Oakland, MD 21550
  • 0 Lake Shore Dr Unit MDGA2010464, Oakland, MD 21550
    0 Lake Shore Dr Unit MDGA2010464, Oakland, MD 21550
    0 Lake Shore Dr Unit MDGA2010464, Oakland, MD 21550
    /24

    $248,500

    • Land
    • 3.32 Acres
    • $74,849 per Acre

    0 Lake Shore Dr Unit MDGA2010464, Oakland, MD 21550

    OAKLAND, MD – 3.318 UNRESTRICTED ACRES “READY TO BUILD” THAT VACATION HOME OR FULL TIME RESIDENCE. THE SUBJECT PROPERTY IS IN THE DEEP CREEK LAKE RESORT AREA. ALL AMENITIES ASSOCIATED WITH A MAJOR RESORT AREA ARE WITHIN A SHORT DRIVE OF THE SUBJECT PROPERTY. FULLY WOODED. MATURE HARDWOOD THRU-OUT. LEVEL TOPOGRAPHY. CLOSE PROXIMITY TO BOAT LAUNCH.

    Mike Haywood The Mike Haywood Group

    0 Lake Shore Dr Unit MDGA2010464, Oakland, MD 21550
  • 1737 King Wildesen Rd, Oakland, MD 21550
    1737 King Wildesen Rd, Oakland, MD 21550
    1737 King Wildesen Rd, Oakland, MD 21550
    /46

    $299,900

    • 3 Beds
    • 2 Baths
    • 1,736 Sq Ft

    1737 King Wildesen Rd, Oakland, MD 21550

    Nestled on 10 secluded acres of serene woodland and open fields, this traditional cedar-sided home offers the perfect blend of rustic charm and modern comfort—all just 10 minutes from downtown Oakland. This well-maintained home features 3 spacious bedrooms and 2 full bathrooms, including a main floor master suite for added convenience. Inside, you’ll find brand-new luxury vinyl plank (LVP)

    Justin Liller Railey Realty, Inc.

    1737 King Wildesen Rd, Oakland, MD 21550
  • 0 Edgewater Dr Unit 4 MDGA2009106, Oakland, MD 21550
    0 Edgewater Dr Unit 4 MDGA2009106, Oakland, MD 21550
    0 Edgewater Dr Unit 4 MDGA2009106, Oakland, MD 21550
    /16

    $299,000

    • Land
    • 0 Acre

    0 Edgewater Dr Unit 4 MDGA2009106, Oakland, MD 21550

    Rare offering! LAKE VIEW building site with TWO BOAT SLIPS! Located off popular Lake Shore Drive in the Edgewater community, this lot features a building envelope surrounded by community green space. Deep water, somewhat flat area by the lake, feels like small little park area. Dock access is directly across the street and a short walk away away - 100 yards +/-. Paved parking area for easy

    Jay Ferguson Taylor Made Deep Creek Vacations & Sales

    0 Edgewater Dr Unit 4 MDGA2009106, Oakland, MD 21550
  • 3257 George Washington Hwy, Oakland, MD 21550
    3257 George Washington Hwy, Oakland, MD 21550
    3257 George Washington Hwy, Oakland, MD 21550
    /8

    $280,000

    • Land
    • 36.72 Acres
    • $7,625 per Acre

    3257 George Washington Hwy, Oakland, MD 21550

    Discover approximately 36.72 acres of beautiful wooded land offering privacy, mountain views, and exceptional convenience. This expansive property provides easy access to both George Washington Highway and Garrett Highway, making travel simple while still feeling tucked away in nature. Located within a 30-minute drive of Deep Creek Lake and Wisp Resort, as well as sought-after West Virginia

    Justin Liller Railey Realty, Inc.

    3257 George Washington Hwy, Oakland, MD 21550
Maryland Garrett County Oakland

Real Estate & Homes in Oakland, MD under $300,000

Home Trends in Oakland, MD

On average, homes in Oakland, MD sell after 88 days on the market compared to the national average of 53 days. The median sale price for homes in Oakland, MD over the last 12 months is $442,500, up 11% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$442,500
Median Single Family Sale Price
$431,000
Median Townhouse Sale Price
$510,000
Median 2 Bedroom Sale Price
$319,000
Median 1 Bedroom Sale Price
$239,900
Average Price Per Sq Ft
$265
Number of Homes for Sale
43
Last 12 months Home Sales
136
Months of Supply
3.80
Median List Price
$435,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
11%
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Browse a range of homes for sale under $300,000 in Oakland, offering accessible options for prospective buyers. With 16 listings available, there's a variety of affordable properties to explore, from charming starter homes to spacious family residences. These homes present an excellent opportunity to enter the housing market and secure a property that fits both your preferences and your budget in Oakland, MD.

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