20

Oakland, MD Homes for Sale under $900,000

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  • 100 San Francisco St, Oakland, MD 21550
    100 San Francisco St, Oakland, MD 21550
    100 San Francisco St, Oakland, MD 21550
    /52

    $645,000

    • 2 Beds
    • 2 Baths
    • 1,520 Sq Ft

    100 San Francisco St, Oakland, MD 21550

    Rare opportunity to own a thoughtfully designed container home in the Deep Creek Lake area! This distinctive 2BR/2BA retreat combines modern comfort with a private wooded setting. The open-concept interior features abundant natural light, a full kitchen, comfortable living space, and large sliders connecting the indoors to the outdoors. Enjoy a private backyard with hot tub, fire pit, and grill,

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    100 San Francisco St, Oakland, MD 21550
  • 180 Paradise Ridge Rd, Oakland, MD 21550
    180 Paradise Ridge Rd, Oakland, MD 21550
    180 Paradise Ridge Rd, Oakland, MD 21550
    /59

    $689,000

    • 4 Beds
    • 3 Baths
    • 2,402 Sq Ft

    180 Paradise Ridge Rd, Oakland, MD 21550

    Experience the best of Deep Creek Lake living at this beautifully renovated mountain retreat in the peaceful and desirable Paradise Ridge lake access community. Thoughtfully updated from top to bottom, this home blends modern comfort with the serenity of nature, creating the perfect full-time residence, vacation getaway, or potential vacation rental investment property.One of the

    Agent Photo

    Brian Homberg

    Taylor-Made Deep Creek Real Estate, LLC

    180 Paradise Ridge Rd, Oakland, MD 21550
  • 941 Mountainview Dr, Oakland, MD 21550
    941 Mountainview Dr, Oakland, MD 21550
    941 Mountainview Dr, Oakland, MD 21550
    /71

    $719,999

    $18K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 4,377 Sq Ft

    941 Mountainview Dr, Oakland, MD 21550

    Experience the best of Deep Creek Lake living in this thoughtfully designed 4 bedroom, 3.5 bath home located in the highly desirable Mountainside community. Combining quality craftsmanship with inviting living spaces, the well planned floor plan maximizes both comfort and functionality. The finished basement provides additional living space perfect for entertaining family and friends. Situated on

    Nicole Jackson Railey Realty, Inc.

    941 Mountainview Dr, Oakland, MD 21550
  • 943 Paradise Heights, Oakland, MD 21550
    943 Paradise Heights, Oakland, MD 21550
    943 Paradise Heights, Oakland, MD 21550
    /62

    $745,000

    $20K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 2,200 Sq Ft

    943 Paradise Heights, Oakland, MD 21550

    Welcome to this stunning 5-bedroom, 3-bath home, completed in 2023 and designed for modern mountain living. Featuring two private ensuite bedrooms, spacious living areas, and a fresh, contemporary design, this home is ready for you to enjoy from day one. This home features a stylish modern kitchen with an open layout that is perfect for entertainment. In the winter months, cozy up by the wood

    Lucas Muenchow Railey Realty, Inc.

    943 Paradise Heights, Oakland, MD 21550
  • 113 Jubb Meadows Ln, Oakland, MD 21550
    113 Jubb Meadows Ln, Oakland, MD 21550
    113 Jubb Meadows Ln, Oakland, MD 21550
    /69

    $869,900

    $30K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,185 Sq Ft

    113 Jubb Meadows Ln, Oakland, MD 21550

    Luxury Estate just outside the town of Oakland. This 4-bed, 3.5 bath is situated on 9.72 acres. Offering 4,555 sq ft with vaulted ceilings, open concept living, and a rustic stacked stone fireplace. Modern gourmet kitchen with a large island and granite tops. Hardwood floors and timber frame accents throughout. Attached three-car garage. Full unfinished basement ready to add up to an additional

    Jon Bell Railey Realty, Inc.

    113 Jubb Meadows Ln, Oakland, MD 21550
  • 4A Mystic Creek Trail, Oakland, MD 21550
    4A Mystic Creek Trail, Oakland, MD 21550
    4A Mystic Creek Trail, Oakland, MD 21550
    /50

    $679,900

    New Construction
    • 5 Beds
    • 4.5 Baths
    • 3,000 Sq Ft

    4A Mystic Creek Trail, Oakland, MD 21550

    Discover refined mountain-lake living in this new construction townhome at Mystic Creek on Deep Creek Lake. Designed with today’s lifestyle in mind, the home features a modern open-concept main level ideal for entertaining, with clean lines, abundant natural light, and seamless flow between living, dining, and kitchen spaces. This spacious residence offers three primary suites, each with upscale

    Justin Liller Railey Realty, Inc.

    4A Mystic Creek Trail, Oakland, MD 21550
  • 251 Robinwood Dr, Oakland, MD 21550
    251 Robinwood Dr, Oakland, MD 21550
    251 Robinwood Dr, Oakland, MD 21550
    /63

    $899,900

    $69K PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 4,284 Sq Ft

    251 Robinwood Dr, Oakland, MD 21550

    One-of-a-kind Youghiogheny riverfront estate offering 400 feet of water frontage on 5+ acres and 2 separate lots. Soak in the sounds of the flowing waters and chirping birds, cloaked in a private canopy of mountain laurel, pine trees and mature hardwoods. 5BR 4.5 BA log masterpiece with attached 2 car garage and paved driveway. Thoughtful design and well maintained with spacious suites, floor to

    Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    251 Robinwood Dr, 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

    $699,000

    $96K PRICE DROP
    • 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
  • 308 Winding Trail Ln Unit 11B, Oakland, MD 21550
    308 Winding Trail Ln Unit 11B, Oakland, MD 21550
    308 Winding Trail Ln Unit 11B, Oakland, MD 21550
    /61

    $615,000

    • 5 Beds
    • 4.5 Baths
    • 3,300 Sq Ft

    308 Winding Trail Ln Unit 11B, Oakland, MD 21550

    5BR, 4.5BA duplex with LAKE VIEWS! Enjoy 3300sf of living space in the heart of Deep Creek Lake. Features include 3 spacious suites, multiple stacked stone fireplaces and two living room areas, plus an impressive outdoor fire pit. You will love the open kitchen/dining area and the covered back deck. Other features include wood floors, granite, instant hot water, pool table and hot tub. Attached

    Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    308 Winding Trail Ln Unit 11B, Oakland, MD 21550
  • 0 Memorial Dr Unit MDGA2010668, Oakland, MD 21550
    0 Memorial Dr Unit MDGA2010668, Oakland, MD 21550
    0 Memorial Dr Unit MDGA2010668, Oakland, MD 21550
    /26

    $699,000

    • Land
    • 33.93 Acres
    • $20,601 per Acre

    0 Memorial Dr Unit MDGA2010668, Oakland, MD 21550

    Incredible Development Opportunity! Almost 34 acres of beautiful grounds zoned Residential/Industrial/Professional (RIP). This parcel would make a beautiful site for a single family or condo/townhome subdivision, business park, or industrial complex. Or, build your dream home with over 33 acres of privacy, yet close to schools, hospital, and downtown Oakland shopping. Public Water on site and

    Justin Liller Railey Realty, Inc.

    0 Memorial Dr Unit MDGA2010668, Oakland, MD 21550
  • 1529 Paradise Point Rd, Oakland, MD 21550
    1529 Paradise Point Rd, Oakland, MD 21550
    1529 Paradise Point Rd, Oakland, MD 21550
    /67

    $639,000

    • 3 Beds
    • 2.5 Baths
    • 1,933 Sq Ft

    1529 Paradise Point Rd, Oakland, MD 21550

    This exquisite Northern White Cedar Construction (naturally rot resistant) log home offers a harmonious blend of rustic charm and modern luxury. The spacious, open floor plan invites you to experience a warm and inviting atmosphere, accentuated by stunning wood floors and walls, cathedral beam ceiling, and a cozy stone fireplace with glass doors, perfect for intimate gatherings. The heart of the

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

    1529 Paradise Point Rd, Oakland, MD 21550
  • 17240 Garrett Hwy, Oakland, MD 21550
    17240 Garrett Hwy, Oakland, MD 21550
    17240 Garrett Hwy, Oakland, MD 21550
    /104

    $899,000

    $99K PRICE DROP
    • 6 Beds
    • 4.5 Baths
    • 5,547 Sq Ft

    17240 Garrett Hwy, Oakland, MD 21550

    Luxury Living Meets Timeless Country Charm! Perfectly positioned on 10.33 picturesque acres between Oakland and Deep Creek Lake, this exceptional 6-bedroom, 4.5-bath home offers the ideal blend of refined comfort, modern updates, and peaceful privacy.Step inside to discover an inviting open floor plan highlighted by soaring wood ceilings, a dramatic floor-to-ceiling stone fireplace, and

    Justin Liller Railey Realty, Inc.

    17240 Garrett Hwy, Oakland, MD 21550
  • 467 Paradise Ridge Rd, Oakland, MD 21550
    467 Paradise Ridge Rd, Oakland, MD 21550
    467 Paradise Ridge Rd, Oakland, MD 21550
    /64

    $769,900

    $30K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,780 Sq Ft

    467 Paradise Ridge Rd, Oakland, MD 21550

    Panoramic mountain and lake views set the tone at this lake access home in Paradise Ridge, one of Deep Creek’s most sought-after communities! Perched at the top of 1.29 private acres, this 4-bedroom, 3.5-bath retreat offers 3,780 finished square feet, sweeping Deep Creek Lake and mountain views, lake access, abundant outdoor living, and an established vacation-rental history.The seller is

    Jon Bell Railey Realty, Inc.

    467 Paradise Ridge Rd, Oakland, MD 21550
  • 231 Santa fe Trail, Oakland, MD 21550
    231 Santa fe Trail, Oakland, MD 21550
    231 Santa fe Trail, Oakland, MD 21550
    /38

    $629,000

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

    231 Santa fe Trail, Oakland, MD 21550

    Brand new roof July 2026! 3/4BR 3BA chalet with LAKE VIEWS! 2300sf vacation home fronting on a mountain stream, overlooking Deep Creek Lake! Enjoy an eat-in kitchen, exposed beams and a loft area that the current owners use as a 4th BR with bathroom. NO HOA! Conveys fully furnished. Features include central AC, exposed beams, updated flooring, gas fireplace on main level, lower level rec room

    Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    231 Santa fe Trail, Oakland, MD 21550
  • 395 Woodlands Hill Ln, Oakland, MD 21550
    395 Woodlands Hill Ln, Oakland, MD 21550
    395 Woodlands Hill Ln, Oakland, MD 21550
    /66

    $899,900

    • 5 Beds
    • 6 Baths
    • 3,160 Sq Ft

    395 Woodlands Hill Ln, Oakland, MD 21550

    Welcome to Happy Hoursss... Hideaway, a stunning Deep Creek Lake retreat where breathtaking views, upscale amenities, and spacious indoor-outdoor living create the perfect getaway. With 5 bedrooms and 6 full bathrooms, this beautifully appointed home comfortably accommodates family and friends while offering plenty of room to relax and entertain. The main level features an inviting open-concept

    Jon Bell Railey Realty, Inc.

    395 Woodlands Hill Ln, Oakland, MD 21550
  • 251 Robinwood Dr, Oakland, MD 21550
    251 Robinwood Dr, Oakland, MD 21550
    251 Robinwood Dr, Oakland, MD 21550
    /62

    $775,000

    • 5 Beds
    • 4.5 Baths
    • 4,284 Sq Ft

    251 Robinwood Dr, Oakland, MD 21550

    One-of-a-kind Youghiogheny riverfront estate offering 224 feet of water frontage . Soak in the sounds of the flowing waters and chirping birds, cloaked in a private canopy of mountain laurel, pine trees and mature hardwoods. 5BR 4.5 BA log masterpiece with attached 2 car garage and paved driveway. Thoughtful design and well maintained with spacious suites, floor to ceiling fireplace, log accent

    Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    251 Robinwood Dr, Oakland, MD 21550
  • 15 Byran Dr, Oakland, MD 21550
    15 Byran Dr, Oakland, MD 21550
    15 Byran Dr, Oakland, MD 21550
    /60

    $799,900

    New Construction
    • 4 Beds
    • 4 Baths

    15 Byran Dr, Oakland, MD 21550

    Experience modern mountain living in this brand-new 2026 construction. This beautifully designed 4-bedroom, 4-bath home offers two spacious levels, quality finishes, and plenty of room for family and guests. Open layout with modern kitchen, island bar, and stone fireplace. Stamped concrete patio with covered fireplace and outdoor kitchen. Over half an acre of private wooded mountain-top space

    Jon Bell Railey Realty, Inc.

    15 Byran Dr, Oakland, MD 21550
  • 25 Silver Tree Ln, Oakland, MD 21550
    25 Silver Tree Ln, Oakland, MD 21550
    25 Silver Tree Ln, Oakland, MD 21550
    /54

    $739,000

    • 5 Beds
    • 4 Baths
    • 2,364 Sq Ft

    25 Silver Tree Ln, Oakland, MD 21550

    Beautiful lake access retreat located in the Silver Tree Landings community with an available home warranty. This recently updated contemporary home feels warm and inviting from the moment you walk in (upgrade list available). Offering hardwood flooring, granite countertops, two stone propane fireplaces and cathedral ceilings. The abundance of windows allows the natural light to brighten any

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

    25 Silver Tree Ln, 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
  • 325 Markwood Dr, Oakland, MD 21550
    325 Markwood Dr, Oakland, MD 21550
    325 Markwood Dr, Oakland, MD 21550
    /66

    $769,000

    $30K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,376 Sq Ft

    325 Markwood Dr, Oakland, MD 21550

    LAKEFRONT 4BR, 3.5BA log home with over 3300sf and 4.35 acres of privacy! Lovingly maintained property with gorgeous views of the 10 acre lake from almost every room in the house! Peaceful surroundings with towering mature trees and just enough yard space in a very laid back, rural setting near Herrington Manor and Swallow Falls state parks. If that weren't impressive enough, Meadow Lake Estates

    Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    325 Markwood Dr, Oakland, MD 21550
Maryland Garrett County

Real Estate & Homes in Oakland, MD under $900,000

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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