17

Oakland, MD Homes for Sale under $1,000,000

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  • 660 Glendale Rd, Oakland, MD 21550
    660 Glendale Rd, Oakland, MD 21550
    660 Glendale Rd, Oakland, MD 21550
    /62

    $999,000

    $301K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 2,592 Sq Ft

    660 Glendale Rd, Oakland, MD 21550

    Welcome to 660 Glendale Road — a luxury, mountain-chalet log home in the heart of Deep Creek Lake. This well appointed 5-bedroom, 3-bath home offers nearly 2,600 square feet of thoughtfully upgraded living space designed for lake life at its best. Enjoy lake views with western exposure on the expansive wraparound decks on main and lower levels. Many recent upgrades including roof, decks, covered

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    660 Glendale 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
  • 184 Upper Penn Point Dr, Oakland, MD 21550
    184 Upper Penn Point Dr, Oakland, MD 21550
    184 Upper Penn Point Dr, Oakland, MD 21550
    /53

    $920,000

    • 3 Beds
    • 2 Baths
    • 1,152 Sq Ft

    184 Upper Penn Point Dr, Oakland, MD 21550

    Welcome to this charming 3Br, 2BA home in the quiet and serene Penn Point area of Deep Creek Lake. A Type A dock slip is included and is just an easy walk or golf-cart ride from the property, making lake days more convenient and enjoyable.Inside you'll find an inviting open concept kitchen, dining, and living area that flows seamlessly onto a spacious outdoor deck. Enjoy morning coffee,

    Amy Mangum Railey Realty, Inc.

    184 Upper Penn Point Dr, Oakland, MD 21550
  • 0 Glendale Rd Lot 12 Alpine Village Subdivision, Oakland, MD 21550
    0 Glendale Rd Lot 12 Alpine Village Subdivision, Oakland, MD 21550
    0 Glendale Rd Lot 12 Alpine Village Subdivision, Oakland, MD 21550
    /21

    $975,000

    $20K PRICE DROP
    • Land
    • 25,264 Sq Ft
    • $1,681,034 per Acre

    0 Glendale Rd Lot 12 Alpine Village Subdivision, Oakland, MD 21550

    RARE OPPURTUNITY! Discover one of the final opportunities to own true lakefront on the iconic Glendale Road! This premier homesite offers approximately 75 feet of pristine Deep Creek Lake frontage in a serene no wake zone, perfect for swimming, kayaking, and peaceful lakeside enjoyment. Zoning in this area is Town Center. This allows for a larger building area within the lot with relaxed

    Lucas Muenchow Railey Realty, Inc.

    0 Glendale Rd Lot 12 Alpine Village Subdivision, 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
  • 164 Grandview Dr, Oakland, MD 21550
    164 Grandview Dr, Oakland, MD 21550
    164 Grandview Dr, Oakland, MD 21550
    /53

    $912,000

    $38K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,368 Sq Ft

    164 Grandview Dr, Oakland, MD 21550

    Experience mountain living at its finest in this breathtaking mountaintop home overlooking Deep Creek Lake. With sweeping views from almost every room, your hardest decision may be where to sit to enjoy them. Offering three levels of living space, hardwood floors ( which were recently refinished), and some new appliances. The multiple decks are ideal to enjoy family and friends while taking in

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

    164 Grandview Dr, 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
  • 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
  • 127 Paradise Heights, Oakland, MD 21550
    127 Paradise Heights, Oakland, MD 21550
    127 Paradise Heights, Oakland, MD 21550
    /24

    $999,999

    $75K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,240 Sq Ft

    127 Paradise Heights, Oakland, MD 21550

    Beautifully renovated lake access log cabin with a deeded dock slip in a quiet cove with private 29 acres of trails (ATVs/snowmobiles permitted). Recent renovations (approx. $200K) include new wrap around deck, new roof, re-stained siding, new kitchen with granite counters, new appliances, new bathrooms, new LVFs throughout the house, new 2 car garage doors, new mini-split heat and A/C units, and

    Norman Domingo XRealty.NET LLC

    127 Paradise Heights, 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 $1,000,000

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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