Oakland, MD homes for sale & real estate

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NEW 22 MINS AGO

ABOUT THIS HOME
Oakland, MD Homes for Sale
Contractors, flippers, or anyone ready to put in the work—this one is for you. Just minutes outside of Oakland in a small, peaceful community, this 4-bedroom home offers a rare chance to create something special. Most of the materials needed to finish the remodel are already on-site, saving you both time and money. What’s left is the TLC and finishing touches that will bring it all together. Sitting on 1.12 flat acres—something hard to come by in this area—you’ll find a full tennis court ready for new life, a covered porch perfect for relaxing, and a private balcony off the owner’s suite that offers peaceful views. Inside, the layout has one finished bath

$170,000

4 beds3 baths2,288 sq ft

306 Shady Acre Ln, Oakland, MD 21550

1.12 acre lot • Built 1972

(866) 525-3466

NEW 8 HRS AGO

ABOUT THIS HOME
Oakland, MD Homes for Sale
Check out the views from the deck and even inside!! Everything has been completely updated! It is being sold completely turnkey so just bring your toothbrushes and move right in. This is priced to sell so call today for a showing.

$260,000

2 beds1 bath520 sq ft

36 Jeffrey Ln Unit 6A, Oakland, MD 21550

$320 HOA • Built 1990

(866) 525-3466

COMING SOON

ABOUT THIS HOME
Oakland, MD Homes for Sale
A magnificent waterfront retreat in The Reserve at Holy Cross on the shores of Deep Creek Lake, representing the pinnacle of lake life living. This incomparable estate captures the essence of refined waterfront with a private dock, expansive outdoor entertaining spaces, and tranquil lakeside ambiance. Featuring 7 total bedrooms, 5 of which are en-suites, this home was thoughtfully designed with privacy, comfort, and flexibility in mind. Nature and luxury converge in perfect harmony with beautifully landscaped grounds creating an unmatched backdrop for lakefront gatherings, comfort and peace of mind.

$3,600,000

7 beds6.5 baths5,681 sq ft

870 Holy Cross Dr, Oakland, MD 21550

1.32 acre lot • $167 HOA • 3 garage spots

(301) 387-2000

3D WALKTHROUGH

ABOUT THIS HOME
Oakland, MD Homes for Sale
Wake up to a light mist rising over Deep Creek Lake and enjoy level lakefront living with your own private dock at the top of Red Run Cove. This stunning Katahdin Cedar Log Home sits on a quiet cul-de-sac, surrounded by mature trees that create a peaceful canopy. Relax on the expansive TimberTech back deck or unwind in the hot tub on the rear stone patio—all with incredible waterfront views. Inside, the warmth of pine and hickory fills the home; while soaring ceilings and walls of glass bathe the interior in natural light. Designed for entertaining, the open layout flows seamlessly to the lakefront deck. The home features 5 bedrooms, including a main-level primary suite, and 3.5 baths

$1,690,000

5 beds3.5 baths2,448 sq ft

272 Mccomas Beach Ter, Oakland, MD 21550

0.41 acre lot • 4 parking spots • Built 2005

(301) 387-2000

3D WALKTHROUGH

ABOUT THIS HOME
Oakland, MD Homes for Sale
If it's privacy and convenience you want, you will love this beautiful log home on a 1.6-acre site with seasonal lake views and a path that leads to restaurants and the lake! Enjoy an open floor plan, cathedral ceilings, two fireplaces, large family/game room, hot tub, block paver landscaping and lots of space to entertain. The home also boasts many recent upgrades which include new lower-level gas fireplace, new lower-level flooring, new carpet, new deck boards and marble countertops. The Mountainside Community amenities include a lakefront clubhouse, lake access and a pavilion. The location is also just minutes to Wisp Ski Resort, call today to preview.

$950,000

5 beds3 baths3,492 sq ft

78 Mountainside Ct, Oakland, MD 21550

Open floor plan • Hot tub • Cathedral ceilings

(301) 387-4700

Property at 220 N 11th St, Oakland, MD 21550, 4 beds, 2.5 baths

$474,900

4 beds2.5 baths3,159 sq ft

220 N 11th St, Oakland, MD 21550

(301) 387-2000

Property at 72 Cliff Dr, Oakland, MD 21550, 3 beds, 2 baths

$585,000

3 beds2 baths2,176 sq ft

72 Cliff Dr, Oakland, MD 21550

(301) 387-2000

Property at 157 Jeffrey Ln Unit 21A, Oakland, MD 21550, 2 beds, 1 bath

$250,000

2 beds1 bath660 sq ft

157 Jeffrey Ln Unit 21A, Oakland, MD 21550

(301) 387-4700

Property at 118 Roman Ridge Rd, Oakland, MD 21550, 3 beds, 3.5 baths

$475,000

3 beds3.5 baths1,820 sq ft

118 Roman Ridge Rd, Oakland, MD 21550

(443) 574-1600

Property at 565 Glendale Rd Unit 210A, Oakland, MD 21550, 1 bed, 1 bath

$175,000

1 bed1 bath382 sq ft

565 Glendale Rd Unit 210A, Oakland, MD 21550

(301) 387-2000

Property at 197 Black Angus Dr, Oakland, MD 21550, 5 beds, 3.5 baths

$2,600,000

5 beds3.5 baths4,156 sq ft

197 Black Angus Dr, Oakland, MD 21550

(301) 387-2000

Property at 1010 Holy Cross Dr, Oakland, MD 21550, 8 beds, 8.5 baths

$5,150,000

8 beds8.5 baths10,300 sq ft

1010 Holy Cross Dr, Oakland, MD 21550

(301) 387-2000

Property at 1989 Lake Shore Dr, Oakland, MD 21550, 4 beds, 3.5 baths

$1,699,000

4 beds3.5 baths3,008 sq ft

1989 Lake Shore Dr, Oakland, MD 21550

(301) 387-2000

Property at 20160 Garrett Hwy Unit G507, Oakland, MD 21550, 2 beds, 1 bath

$429,000

2 beds1 bath912 sq ft

20160 Garrett Hwy Unit G507, Oakland, MD 21550

(301) 387-2000

Property at 2311 Boy Scout Rd, Oakland, MD 21550, 4 beds, 3 baths

$1,699,900

4 beds3 baths3,517 sq ft

2311 Boy Scout Rd, Oakland, MD 21550

(301) 387-2000

Property at 88 Knoll Crest Hts, Oakland, MD 21550, 3 beds, 2.5 baths

$219,000

3 beds2.5 baths1,867 sq ft

88 Knoll Crest Hts, Oakland, MD 21550

(301) 387-2000

Property at 66 Paradise Ridge Rd, Oakland, MD 21550, 4 beds, 4 baths

$650,000

4 beds4 baths2,550 sq ft

66 Paradise Ridge Rd, Oakland, MD 21550

(410) 413-3575

Property at 1720 Pysell Crosscut Rd, Oakland, MD 21550, 5 beds, 5.5 baths

$999,999

5 beds5.5 baths8,000 sq ft

1720 Pysell Crosscut Rd, Oakland, MD 21550

(301) 387-4700

Property at 425 Mountainview Dr, Oakland, MD 21550, 3 beds, 2.5 baths

$829,000

3 beds2.5 baths1,586 sq ft

425 Mountainview Dr, Oakland, MD 21550

(301) 387-4700

Property at 16 Silver Ridge Ct Unit 41/2, Oakland, MD 21550, 4 beds, 3 baths

$589,000

4 beds3 baths2,700 sq ft

16 Silver Ridge Ct Unit 41/2, Oakland, MD 21550

(301) 387-2000

Property at 5202 Hutton Rd, Oakland, MD 21550, 3 beds, 1 bath

$239,000

3 beds1 bath1,199 sq ft

5202 Hutton Rd, Oakland, MD 21550

(301) 387-2000

Property at 1260 Gnegy Church Rd, Oakland, MD 21550, 3 beds, 3 baths

$449,000

3 beds3 baths4,420 sq ft

1260 Gnegy Church Rd, Oakland, MD 21550

(301) 387-2000

Property at 939 Glendale Rd #19, Oakland, MD 21550, 3 beds, 2 baths

$785,000

3 beds2 baths1,432 sq ft

939 Glendale Rd #19, Oakland, MD 21550

(410) 241-3725

Property at 62 Duck Cove Rd, Oakland, MD 21550, 4 beds, 4 baths

$1,985,000

4 beds4 baths4,150 sq ft

62 Duck Cove Rd, Oakland, MD 21550

(301) 387-2000

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

$270,991

4 beds2 baths2,496 sq ft

503 E Alder St E, Oakland, MD 21550

(703) 763-1950

Property at 1875 Pysell Crosscut Rd, Oakland, MD 21550, 5 beds, 5 baths

$818,000

5 beds5 baths3,664 sq ft

1875 Pysell Crosscut Rd, Oakland, MD 21550

(301) 387-4700

Property at 20676 Garrett Hwy, Oakland, MD 21550, 5 beds, 4.5 baths

$1,499,000

5 beds4.5 baths2,280 sq ft

20676 Garrett Hwy, Oakland, MD 21550

(855) 885-4663

Property at 198 Grandview Dr, Oakland, MD 21550, 3 beds, 3 baths

$825,000

3 beds3 baths2,744 sq ft

198 Grandview Dr, Oakland, MD 21550

(410) 224-4400

Property at 783 Mountainview Dr, Oakland, MD 21550, 3 beds, 3 baths

$529,900

3 beds3 baths1,971 sq ft

783 Mountainview Dr, Oakland, MD 21550

(301) 387-2000

Property at 170 Tannery Rd, Oakland, MD 21550, 3 beds, 2 baths

$179,000

3 beds2 baths1,850 sq ft

170 Tannery Rd, Oakland, MD 21550

(888) 400-2513

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

$475,000

4 beds3.5 baths1,492 sq ft

333 Sloan Tract Rd, Oakland, MD 21550

(301) 387-4700

Property at 873 Paradise Hts, Oakland, MD 21550, 5 beds, 4 baths

$829,000

5 beds4 baths2,934 sq ft

873 Paradise Hts, Oakland, MD 21550

(301) 387-2000

Property at 126 Leo Friend Rd, Mchenry, MD 21550, 4 beds, 3 baths

$529,900

4 beds3 baths2,235 sq ft

126 Leo Friend Rd, Mchenry, MD 21550

(301) 387-2000

Property at 102 Mountainview Ct, Oakland, MD 21550, 7 beds, 4.5 baths

$900,000

7 beds4.5 baths5,376 sq ft

102 Mountainview Ct, Oakland, MD 21550

(301) 387-2000

Property at 52 Dam View Dr, Oakland, MD 21550, 4 beds, 5 baths

$1,129,995

4 beds5 baths3,032 sq ft

52 Dam View Dr, Oakland, MD 21550

(301) 387-4700

Property at 501 Christophers Way, Oakland, MD 21550, 3 beds, 2 baths

$249,000

3 beds2 baths1,617 sq ft

501 Christophers Way, Oakland, MD 21550

(301) 387-4700

Property at 104 Pine Top Trl, Oakland, MD 21550, 4 beds, 4.5 baths

$425,000

4 beds4.5 baths1,596 sq ft

104 Pine Top Trl, Oakland, MD 21550

(301) 387-8300

Property at 1118 Lake Shore Dr, Oakland, MD 21550, 3 beds, 2 baths

$649,000

3 beds2 baths2,446 sq ft

1118 Lake Shore Dr, Oakland, MD 21550

(301) 387-2000

Property at 45 Village Dr #4, Oakland, MD 21550, 2 beds, 2 baths

$450,000

2 beds2 baths1,096 sq ft

45 Village Dr #4, Oakland, MD 21550

(301) 921-4500

Property at 98 Bear Run Rd, Oakland, MD 21550, 3 beds, 2 baths

$268,900

3 beds2 baths1,080 sq ft

98 Bear Run Rd, Oakland, MD 21550

(304) 788-5540

Property at 1737 King Wildesen Rd, Oakland, MD 21550, 3 beds, 2 baths

$299,900

3 beds2 baths1,736 sq ft

1737 King Wildesen Rd, Oakland, MD 21550

(301) 387-2000

Viewing page 1 of 4

Average home prices near Oakland, MD

Cities

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$295,000
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$63,000
Accident homes for sale
$325,000
Swanton homes for sale
$1,199,500
Rowlesburg homes for sale
$104,700
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Albright homes for sale
$110,000
Elk Garden homes for sale
$88,500
Kingwood homes for sale
$180,000
Mountain Lake Park homes for sale
$290,000

Zip Codes

21550 homes for sale
$525,000

Oakland, MD real estate trends

$210K

Sale price

-23.6%
since last year

$155

Sale $/sq ft

+9.5%
since last year

Under list price

5.1%

Days on market

77.5

Down payment

—

Total homes sold

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