Oakland, MD homes for sale & real estate

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ABOUT THIS HOME
Oakland, MD Homes for Sale
Experience the best of Deep Creek Lake living at 758 South Blakeslee Road! Located in the highly desirable Blakeslee community, this beautifully appointed 6-bedroom, 4.5-bath retreat offers the perfect blend of luxury, comfort, and recreation. The spacious open-concept living area features soaring vaulted ceilings, expansive windows, and a stunning floor-to-ceiling stone fireplace. The beautifully updated kitchen showcases stunning countertops, stainless steel appliances, and a generous center island, seamlessly connecting to the main living and dining spaces. A spacious loft overlooks the main living area, while the expansive lower-level recreation area offers additional gathering space, s

$1,189,900

6 beds4.5 baths3,852 sq ft

758 South Blakeslee Rd, Oakland, MD 21550

Updated kitchen • Spacious loft • 1.12 acre lot

(301) 387-2000

3D WALKTHROUGH

ABOUT THIS HOME
Oakland, MD Homes for Sale
Enjoy the beauty of Deep Creek Lake from this luxury custom brick home in The Reserve at Holy Cross, one of the lake’s premier communities. Situated on more than an acre with over 250 feet of lake frontage, the property offers expansive water views, inviting outdoor spaces and over 8,600 square feet of finished living space. A sweeping brick paver driveway, mature landscaping and a covered front entrance set the tone for the warmth and architectural character found throughout. Soaring ceilings, rich wood finishes and a graceful curved staircase welcome you inside. Large windows draw the lake into the main living areas, while an open library loft adds dimension and character to the spa

$4,699,000

6 beds7 baths8,654 sq ft

31 Holy Cross Cir, Oakland, MD 21550

Five fireplaces • Lake frontage • Six burner gas range

(301) 334-8454

ABOUT THIS HOME
Oakland, MD Homes for Sale
Take a look at this 3BR-1BA home in Oakland with town water, sewer, natural gas. Home could use some TLC but is a wonderful starter or ender-upper home. Vinyl sided, from porch and deck. One car integral garage. Some hardwood flooring. Why rent when you can buy and have a lower monthly payment.

$139,900

3 beds1 bath988 sq ft

1003 E High St, Oakland, MD 21550

Vinyl sided • Hardwood flooring • Front porch

(301) 387-2000

ABOUT THIS HOME
Oakland, MD Homes for Sale
Welcome to Your Dream Retreat at Deep Creek Lake! Discover this stunning, recently remodeled home that perfectly blends modern luxury with the tranquility of nature. Nestled among picturesque blue spruce trees, this 4-bedroom, 4.5-bath residence offers an exceptional getaway for both relaxation and adventure. The open-concept living space is designed for comfort and style. Enjoy a cozy fireplace that sets the perfect ambiance for chilly evenings, making gatherings with family and friends even more special. Step outside to a large deck that provides ample space for outdoor dining and relaxation. Unwind in the hot tub while surrounded by the serene sounds of nature. Take advantage of your ver

$1,699,000

4 beds4.5 baths2,605 sq ft

1019 Lake Shore Dr, Oakland, MD 21550

Large deck • Recently remodeled • Hot tub

(301) 387-4700

ABOUT THIS HOME
Oakland, MD Homes for Sale
Discover your private mountain retreat at 1050 Christophers Way, situated on 13 acres spanning three separate parcels in the Backbone Ridge community. Showcasing breathtaking panoramic mountain views, this inviting home features warm wood accents, vaulted ceilings, a spacious loft, and a modern kitchen with stainless steel appliances. The walkout lower level offers additional living space, while the expansive deck provides the perfect setting to enjoy the spectacular scenery and peaceful surroundings. Additional features include an electric heat pump and water treatment system. Offering exceptional privacy, incredible views, and endless opportunities to enjoy the outdoors, this property is

$269,900

2 beds2 baths1,050 sq ft

1050 Christopher Way, Oakland, MD 21550

Walkout lower level • Spacious loft • Modern kitchen

(301) 387-2000

Property at 2296 Lake Shore Dr, Oakland, MD 21550, 4 beds, 2.5 baths

$909,000

4 beds2.5 baths2,796 sq ft

2296 Lake Shore Dr, Oakland, MD 21550

(301) 387-2000

Property at 503 E Alder St, Oakland, MD 21550, 4 beds, 2 baths

$149,000

4 beds2 baths2,512 sq ft

503 E Alder St, Oakland, MD 21550

(301) 722-9292

Property at 228 N 4th St, Oakland, MD 21550, 3 beds, 2 baths

$295,000

3 beds2 baths1,562 sq ft

228 N 4th St, Oakland, MD 21550

(301) 387-4700

Property at 74 Parks Rd, Oakland, MD 21550, 3 beds, 1 bath

$59,900

3 beds1 bath792 sq ft

74 Parks Rd, Oakland, MD 21550

(855) 450-0442

Property at 459 Santa Fe Trl, Oakland, MD 21550, 3 beds, 2 baths

$299,000

3 beds2 baths1,344 sq ft

459 Santa Fe Trl, Oakland, MD 21550

(301) 387-2000

Property at 565 Glendale Rd #208, Oakland, MD 21550, 1 bed, 1 bath

$178,000

1 bed1 bath484 sq ft

565 Glendale Rd #208, Oakland, MD 21550

(301) 689-8857

Property at 870 Hunters Ridge Dr, Oakland, MD 21550, 4 beds, 2.5 baths

$679,000

4 beds2.5 baths2,896 sq ft

870 Hunters Ridge Dr, Oakland, MD 21550

(301) 387-2000

Property at 216 N 12th St, Oakland, MD 21550, 3 beds, 1.5 baths

$265,000

3 beds1.5 baths1,984 sq ft

216 N 12th St, Oakland, MD 21550

(410) 879-8080

Property at 2092 Gorman Rd, Oakland, MD 21550, 4 beds, 2 baths

$349,000

4 beds2 baths4,004 sq ft

2092 Gorman Rd, Oakland, MD 21550

(301) 387-4700

Property at 251 Robinwood Dr, Oakland, MD 21550, 5 beds, 4.5 baths

$750,000

5 beds4.5 baths4,284 sq ft

251 Robinwood Dr, Oakland, MD 21550

(301) 387-4700

Property at 5423 Gorman Rd, Oakland, MD 21550, 0.5 baths

$225,000

— beds0.5 baths720 sq ft

5423 Gorman Rd, Oakland, MD 21550

(301) 387-4700

Property at 1959 Birchwood Dr, Oakland, MD 21550, 2 beds, 1.5 baths

$235,000

2 beds1.5 baths1,152 sq ft

1959 Birchwood Dr, Oakland, MD 21550

(301) 387-4700

Property at 607 Pin Oak Cir, Oakland, MD 21550, 5 beds, 3.5 baths

$499,000

5 beds3.5 baths3,800 sq ft

607 Pin Oak Cir, Oakland, MD 21550

(301) 387-2000

Property at 127 Jeffrey Ln #4, Oakland, MD 21550, 2 beds, 1 bath

$257,000

2 beds1 bath700 sq ft

127 Jeffrey Ln #4, Oakland, MD 21550

(301) 387-2000

Property at 425 E Alder St, Oakland, MD 21550, 6 beds, 4.5 baths

$449,000

6 beds4.5 baths2,752 sq ft

425 E Alder St, Oakland, MD 21550

(301) 387-2000

Property at 704 Old Crellin Rd, Oakland, MD 21550, 5 beds, 2.5 baths

$430,000

5 beds2.5 baths2,507 sq ft

704 Old Crellin Rd, Oakland, MD 21550

(301) 259-1119

Property at 1529 Paradise Point Rd, Oakland, MD 21550, 3 beds, 2.5 baths

$639,000

3 beds2.5 baths1,933 sq ft

1529 Paradise Point Rd, Oakland, MD 21550

(301) 387-4700

Property at 333 Sloan Tract Rd, Oakland, MD 21550, 4 beds, 3.5 baths

$444,700

4 beds3.5 baths1,585 sq ft

333 Sloan Tract Rd, Oakland, MD 21550

(301) 722-4700

Property at 1131 Lake Shore Dr, Oakland, MD 21550, 8 beds, 9 baths

$3,950,000

8 beds9 baths6,486 sq ft

1131 Lake Shore Dr, Oakland, MD 21550

(301) 387-4700

Property at 206 W Liberty St, Oakland, MD 21550, 2 beds, 1 bath

$129,000

2 beds1 bath2,008 sq ft

206 W Liberty St, Oakland, MD 21550

(301) 387-2000

Property at 193 Red Run Rd Unit 1-B-3, Oakland, MD 21550, 2 beds, 2 baths

$550,000

2 beds2 baths1,340 sq ft

193 Red Run Rd Unit 1-B-3, Oakland, MD 21550

(301) 698-5005

Property at 325 Markwood Dr, Oakland, MD 21550, 4 beds, 3.5 baths

$769,000

4 beds3.5 baths3,376 sq ft

325 Markwood Dr, Oakland, MD 21550

(301) 387-4700

Property at 565 Glendale Rd #213, Oakland, MD 21550, 1 bed, 1 bath

$200,000

1 bed1 bath— sq ft

565 Glendale Rd #213, Oakland, MD 21550

(443) 574-1600

Property at 565 Glendale Rd #316, Oakland, MD 21550, 2 beds, 1 bath

$279,000

2 beds1 bath772 sq ft

565 Glendale Rd #316, Oakland, MD 21550

(301) 387-2000

Property at 482 Pergin Farm Rd, Oakland, MD 21550, 3 beds, 1.5 baths

$449,000

3 beds1.5 baths2,160 sq ft

482 Pergin Farm Rd, Oakland, MD 21550

(301) 387-4700

Property at 20698 Garrett Hwy, Oakland, MD 21550, 4 beds, 3 baths

$1,199,000

4 beds3 baths1,844 sq ft

20698 Garrett Hwy, Oakland, MD 21550

(301) 387-4700

Property at 308 Winding Trail Ln Unit 11B, Oakland, MD 21550, 5 beds, 4.5 baths

$599,999

5 beds4.5 baths3,300 sq ft

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

(301) 387-4700

Property at 187 Lower Penn Point Dr, Oakland, MD 21550, 3 beds, 2 baths

$1,425,000

3 beds2 baths1,695 sq ft

187 Lower Penn Point Dr, Oakland, MD 21550

(301) 387-2000

Property at 586 Bray School Rd, Oakland, MD 21550, 4 beds, 2 baths

$269,000

4 beds2 baths2,240 sq ft

586 Bray School Rd, Oakland, MD 21550

(301) 259-1119

Property at 181 Glotfelty Dr, Oakland, MD 21550, 3 beds, 2 baths

$374,900

3 beds2 baths1,456 sq ft

181 Glotfelty Dr, Oakland, MD 21550

(301) 387-2000

Property at 15 Byran Dr, Oakland, MD 21550, 4 beds, 4 baths

$799,900

4 beds4 baths— sq ft

15 Byran Dr, Oakland, MD 21550

(301) 387-2000

Property at 20160 Garrett Hwy Unit H706, Oakland, MD 21550, 1 bed, 1 bath

$299,000

1 bed1 bath550 sq ft

20160 Garrett Hwy Unit H706, Oakland, MD 21550

(301) 387-4700

Property at 100 San Francisco St, Oakland, MD 21550, 2 beds, 2 baths

$645,000

2 beds2 baths1,520 sq ft

100 San Francisco St, Oakland, MD 21550

(301) 387-2000

Property at 943 Paradise Hts, Oakland, MD 21550, 5 beds, 3 baths

$699,000

5 beds3 baths2,200 sq ft

943 Paradise Hts, Oakland, MD 21550

(301) 387-2000

Property at 62 Wild Turkey Ct, Oakland, MD 21550, 4 beds, 3 baths

$199,000

4 beds3 baths2,390 sq ft

62 Wild Turkey Ct, Oakland, MD 21550

(301) 387-8300

Property at 113 Jubb Meadows Ln, Oakland, MD 21550, 4 beds, 3.5 baths

$869,900

4 beds3.5 baths3,185 sq ft

113 Jubb Meadows Ln, Oakland, MD 21550

(301) 387-2000

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Average home prices near Oakland, MD

Cities

Friendsville homes for sale
$149,900
Jennings homes for sale
$180,000
Thomas homes for sale
$362,000
Davis homes for sale
$258,000
Accident homes for sale
$554,850
Swanton homes for sale
$2,062,400
Deer Park homes for sale
$323,750
Terra Alta homes for sale
$123,750
Elk Garden homes for sale
$58,500
Albright homes for sale
$64,900
Kingwood homes for sale
$277,450
Mountain Lake Park homes for sale
$249,000

Zip Codes

21550 homes for sale
$379,500

Oakland, MD real estate trends

All Home Types trends in Oakland, MD

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$329,843

+51.7% YoY | Sep 2026

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

Sep 2026

Growth

% YoY

Oakland, MD

$329,843

+51.7%

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