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Modern Homes for Sale in Oakland, MD

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  • 211 High Point Ridge Rd, Oakland, MD 21550
    211 High Point Ridge Rd, Oakland, MD 21550
    211 High Point Ridge Rd, Oakland, MD 21550
    /99

    $1,495,000

    • 4 Beds
    • 3.5 Baths
    • 3,472 Sq Ft

    211 High Point Ridge Rd, Oakland, MD 21550

    One in a lifetime opportunity to own one of Maryland’s most distinctive homes. Built in 2019, this fully custom modern home is located on the highest elevation building lot in the state of Maryland, making it the highest elevation home in the state at our 3300 feet above sea level. Designed to take full advantage of the setting, the property offers incredible panoramic views stretching across the

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 443-3345

    211 High Point Ridge Rd, Oakland, MD 21550
  • 20160 Garrett Hwy Unit H706, Oakland, MD 21550
    20160 Garrett Hwy Unit H706, Oakland, MD 21550
    20160 Garrett Hwy Unit H706, Oakland, MD 21550
    /30

    $309,000

    • 1 Bed
    • 1 Bath
    • 550 Sq Ft

    20160 Garrett Hwy Unit H706, Oakland, MD 21550

    Welcome to Will O' the Wisp Unit H706, a beautiful top-floor lakefront condo offering some of the most breathtaking views of Deep Creek Lake. Perched on the 7th floor and overlooking one of the lake's widest sections, this fully furnished two-level condo features 1 bedroom, 1 bath, and 550 square feet of comfortable, low-maintenance living - ideal as a vacation retreat, year-round getaway, or

    Agent Photo

    James Matthews

    Taylor-Made Deep Creek Real Estate, LLC

    (240) 266-9392

    20160 Garrett Hwy Unit H706, Oakland, MD 21550
  • 47 Holy Cross Cir, Oakland, MD 21550
    47 Holy Cross Cir, Oakland, MD 21550
    47 Holy Cross Cir, Oakland, MD 21550
    /109

    $6,499,900

    • 8 Beds
    • 8.5 Baths
    • 11,417 Sq Ft

    47 Holy Cross Cir, Oakland, MD 21550

    Luxury lakefront living at its peak. This 11,417 sq ft masterpiece sits on 1.65 acres in The Reserve at Holy Cross with 345 feet of Deep Creek Lake frontage and an engineered DNR-approved sea wall. Crafted in 2016, the home features timber-framed vaulted ceilings, wide-plank hardwood floors, and panoramic lake views from nearly every room. The commercial-grade kitchen anchors the main level with

    Jon Bell Railey Realty, Inc.

    47 Holy Cross Cir, 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

    $899,900

    • 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
  • 130 Timberloft Cir Unit 14, Oakland, MD 21550
    130 Timberloft Cir Unit 14, Oakland, MD 21550
    130 Timberloft Cir Unit 14, Oakland, MD 21550
    /79

    $749,000

    • 3 Beds
    • 3 Baths
    • 1,900 Sq Ft

    130 Timberloft Cir Unit 14, Oakland, MD 21550

    Centrally located in the heart of Deep Creek Lake, this beautifully maintained 3 bedroom, 3 bath home offers breathtaking lake and mountain views year round. Designed with an open floor plan, this home is perfect for entertaining. Enjoy the stunning scenery from the spacious main-level deck, or relax in the screened-in lower level porch. A cozy fireplace on both levels adds warmth and charm,

    Nicole Jackson Railey Realty, Inc.

    130 Timberloft Cir Unit 14, 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

    $229,900

    • 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
  • 654 N Bradley Ln, Oakland, MD 21550
    654 N Bradley Ln, Oakland, MD 21550
    654 N Bradley Ln, Oakland, MD 21550
    /41

    $424,900

    New Construction $25K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,464 Sq Ft

    654 N Bradley Ln, Oakland, MD 21550

    NEW CONSTRUCTION from Lyv Homes with anticipated mid-June completion. 3BR/2BA, 1464sf contemporary style home fronting on the 13th hole of the Oakland golf course. This property combines scenic views with modern design and outdoor living. Key features include multiple wood-burning fireplaces, Andersen windows, commercial-grade LVP flooring throughout, gourmet kitchen with soft-close cabinets and

    Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    654 N Bradley Ln, Oakland, MD 21550
  • 164 Grandview Dr, Oakland, MD 21550
    164 Grandview Dr, Oakland, MD 21550
    164 Grandview Dr, Oakland, MD 21550
    /50

    $950,000

    • 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
  • 1038 S Blakeslee Rd, Oakland, MD 21550
    1038 S Blakeslee Rd, Oakland, MD 21550
    1038 S Blakeslee Rd, Oakland, MD 21550
    /69

    $2,100,000

    • 5 Beds
    • 5 Baths
    • 4,074 Sq Ft

    1038 S Blakeslee Rd, Oakland, MD 21550

    Welcome to 1038 S Blakeslee Road! A spacious lakefront retreat on Deep Creek Lake offering effortless lakeside living. A Rare opportunity to own in one of Deep Creek’s most sought-after lakeside communities. This five-bedroom, five-bath home sits on a large 1.11-acre level lot with easy access to the water and generous outdoor space for recreation and entertaining. Inside, the home is warm and

    Eric Crawford Taylor-Made Deep Creek Real Estate, LLC

    1038 S Blakeslee Rd, Oakland, MD 21550
  • 565 Glendale Rd Unit 306, Oakland, MD 21550
    565 Glendale Rd Unit 306, Oakland, MD 21550
    565 Glendale Rd Unit 306, Oakland, MD 21550
    /32

    $249,900

    • 2 Beds
    • 1 Bath
    • 772 Sq Ft

    565 Glendale Rd Unit 306, Oakland, MD 21550

    Experience the best of Deep Creek Lake living from this beautifully appointed studio loft at Silver Tree Suites—one of the lake’s most sought-after locations! Offering two separate sleeping areas, a kitchenette, gas fireplace, and private balcony, this unit is designed for comfort and easy getaway living. Tastefully updated with new carpet and flooring, as well as kitchen and bathroom

    Jon Bell Railey Realty, Inc.

    565 Glendale Rd Unit 306, Oakland, MD 21550
  • 267 San Francisco St, Oakland, MD 21550
    267 San Francisco St, Oakland, MD 21550
    267 San Francisco St, Oakland, MD 21550
    /30

    $899,900

    • 4 Beds
    • 2.5 Baths
    • 3,278 Sq Ft

    267 San Francisco St, Oakland, MD 21550

    Welcome to your secluded Deep Creek retreat! This stunning property offers expansive lake views! So clear you’ll catch the slopes of Wisp in the distance. Includes 3 lots and the privacy is unmatched. This house was torn down to the foundation and a new house was built in 2009. Inside, you’ll find four spacious bedrooms, two and a half baths, and soaring vaulted ceilings and a grand fireplace.

    Bradley West HomeSmart

    267 San Francisco St, Oakland, MD 21550
  • 178 Winding Trail Ln Unit 5B, Oakland, MD 21550
    178 Winding Trail Ln Unit 5B, Oakland, MD 21550
    178 Winding Trail Ln Unit 5B, Oakland, MD 21550
    /47

    $569,000

    $20K PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 3,300 Sq Ft

    178 Winding Trail Ln Unit 5B, Oakland, MD 21550

    Tucked into a peaceful, wooded setting yet right in the heart of everything Deep Creek Lake has to offer, Whispering Pines is the ultimate turnkey mountain retreat. This impeccably maintained 5-bedroom townhome spans three levels of inviting living space and features an attached garage—perfect for hosting family, friends, or guests year-round. Enjoy the best of both worlds: a private, serene

    Nina Beitzel Railey Realty, Inc.

    178 Winding Trail Ln Unit 5B, 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
  • 170 Cherrywood Dr, Oakland, MD 21550
    170 Cherrywood Dr, Oakland, MD 21550
    170 Cherrywood Dr, Oakland, MD 21550
    /67

    $699,000

    • 5 Beds
    • 3 Baths
    • 2,560 Sq Ft

    170 Cherrywood Dr, Oakland, MD 21550

    4/5BR 3BA custom home (3900+ total sf!) on 8+ acres of peaceful tranquility! Conveys with 2 lots (6 & 7) totaling 8.05 acres of wooded land in a laid back HOA that allows chickens & embraces the outdoor amenities Garrett County offers. Private and secluded rural location that is just minutes from town, schools, shopping and dining. This home was custom designed for work from home professionals -

    Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    170 Cherrywood Dr, Oakland, MD 21550
  • 333 Sloan Tract Rd, Oakland, MD 21550
    333 Sloan Tract Rd, Oakland, MD 21550
    333 Sloan Tract Rd, Oakland, MD 21550
    /43

    $475,000

    • 4 Beds
    • 3.5 Baths
    • 1,492 Sq Ft

    333 Sloan Tract Rd, Oakland, MD 21550

    Charming cabin off the coveted Lake Shore Drive offering seasonal lake views. This home has three levels of living space, hardwood flooring and a nice fireplace. The lower level is totally finished with walk-out access. There are multiple covered porches plus a hot tub that are great outdoor spaces to enjoy year round. This home feels very secluded but is just minutes to Deep Creek Lake and Wisp

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

    333 Sloan Tract Rd, Oakland, MD 21550
  • 428 Sam Snead Cir, Oakland, MD 21550
    428 Sam Snead Cir, Oakland, MD 21550
    428 Sam Snead Cir, Oakland, MD 21550
    /86

    $599,000

    • 5 Beds
    • 3.5 Baths
    • 3,542 Sq Ft

    428 Sam Snead Cir, Oakland, MD 21550

    Welcome to this beautifully appointed 5-bedroom, 3.5-bath home located in one of Oakland’s most desirable neighborhoods—Country Club Acres, bordering The Golf Club at Oakland. Offering the perfect blend of modern style, comfort, and convenience, this spacious home is designed to accommodate both everyday living and entertaining. Step inside to discover an inviting open-concept floor plan

    Justin Liller Railey Realty, Inc.

    428 Sam Snead Cir, Oakland, MD 21550
  • 25 Silver Tree Ln, Oakland, MD 21550
    25 Silver Tree Ln, Oakland, MD 21550
    25 Silver Tree Ln, Oakland, MD 21550
    /52

    $749,900

    • 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
  • 248 Tarn Dr, Oakland, MD 21550
    248 Tarn Dr, Oakland, MD 21550
    248 Tarn Dr, Oakland, MD 21550
    /70

    $1,189,000

    New Construction
    • 6 Beds
    • 5.5 Baths
    • 3,482 Sq Ft

    248 Tarn Dr, Oakland, MD 21550

    Brand new construction in the desirable Mountainside community! This thoughtfully designed 6-bedroom mountain retreat offers 4 spacious primary suites, blending modern mountain style with functionality and comfort throughout. The open floorplan features vaulted ceilings, luxury finishes, quartz countertops, and multiple gathering spaces designed for entertaining and relaxation alike. Enjoy cozy

    Lauren McCann Railey Realty, Inc.

    248 Tarn Dr, Oakland, MD 21550
Maryland Garrett County Oakland

Real Estate & Homes for Sale in Oakland, MD

Home Prices in Oakland, MD

The median home sale price in Oakland, MD is $420,000, up 4% year-over-year. Homes in Oakland sell in 95 days on average, compared to the national average of 58 days.

Home Price Trends

Median Sale Price
$420,000
Median Single Family Sale Price
$400,000
Median Townhouse Sale Price
$472,500
Median 2 Bedroom Sale Price
$275,000
Median 1 Bedroom Sale Price
$229,900
Average Price Per Sq Ft
$274
Number of Homes for Sale
59
Last 12 months Home Sales
141
Months of Supply
5.00
Median List Price
$405,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
4%
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