MLS Listings for Sale in Oakland, MD

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ABOUT THIS HOME
MLS Listings for Sale in Oakland, MD
Nestled on 10 secluded acres of serene woodland and open fields, this traditional cedar-sided home offers the perfect blend of rustic charm and modern comfort—all just 10 minutes from downtown Oakland. This well-maintained home features 3 spacious bedrooms and 2 full bathrooms, including a main floor master suite for added convenience. Inside, you’ll find brand-new luxury vinyl plank (LVP) flooring that adds style and durability throughout the living spaces. The large, inviting kitchen provides plenty of room for cooking, entertaining, and gathering with loved ones. Recent upgrades include a brand-new metal roof, offering peace of mind and long-lasting durability. Outside, the p

$299,900

3 beds2 baths1,736 sq ft

1737 King Wildesen Rd, Oakland, MD 21550

10 acre lot • 4 parking spots • Pool

(301) 387-2000

3D WALKTHROUGH

ABOUT THIS HOME
MLS Listings for Sale in Oakland, MD
Welcome to Will O' the Wisp Condominiums, where premium upgrades meet penthouse-level lakefront living at Deep Creek Lake! This fully furnished, beautifully updated, rarely available, top-floor two-level condo features one bedroom and one bath, offering 550 square feet of comfort, charm, and versatility — perfect as a vacation home, year-round retreat, or income-producing rental. Start your mornings with exceptional sunrises from your private lakefront balcony — one of the best views in the building! Inside, you’ll find brand-new luxury vinyl plank flooring, updated lighting, and a show-stopping custom staircase, which replaced the outdated spiral design and was so substan

$289,900

1 bed1 bath550 sq ft

20160 Garrett Hwy Unit H708, Oakland, MD 21550

Custom staircase • Hot tubs • Lakefront balcony

(443) 574-1600

ABOUT THIS HOME
MLS Listings for Sale in Oakland, MD
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 Ski Resort. Hidden Treasure would be an ideal permanent residence or vacation home. Call today to preview!

$475,000

4 beds3.5 baths1,492 sq ft

333 Sloan Tract Rd, Oakland, MD 21550

Hardwood flooring • Walk-out access • Seasonal lake views

(301) 387-4700

ABOUT THIS HOME
MLS Listings for Sale in Oakland, MD
Welcome to your peaceful mountain escape in Laurel Brook, where convenience meets cozy comfort! This beautifully maintained 2 bed, 2 bath condo offers an easy, affordable way to enjoy life near Deep Creek Lake without the hassle of yard work or upkeep. Whether you’re dreaming of a low-maintenance full-time home, a weekend getaway, or an investment property, this one checks all the boxes. Step inside to find a warm, inviting layout designed for everyday comfort, with bright windows, natural finishes, and plenty of space to relax after a day exploring Garrett County’s great outdoors. Located just minutes from Deep Creek Lake and downtown Oakland, you’ll have quick access to

$225,000

2 beds2 baths— sq ft

4 Laurel Brook Dr #4, Oakland, MD 21550

$285 HOA • Built 1989 • Listed 163 days

(301) 387-4700

ABOUT THIS HOME
MLS Listings for Sale in Oakland, MD
Price Improved! Nestled in the serene Yellowstone Village community, 45 Village Drive offers a fully furnished 2-bedroom, 2-bathroom cabin that seamlessly blends rustic charm with modern amenities. This turnkey property is an exceptional investment opportunity, having generated gross year to date in 2025 over $41,000 in rental reservations, and demonstrated gross rental income in 2024 of over $48,000! The cabin's open-concept design features a spacious living area with vaulted ceilings, a cozy fireplace, and large windows that invite natural light and showcase the surrounding wooded landscape. The well-appointed kitchen is well equipped with appliances and ample cabinetry, making meal prepa

$415,000

2 beds2 baths1,096 sq ft

45 Village Dr #4, Oakland, MD 21550

Open-concept design • Large windows • Tranquil setting

(301) 921-4500

Property at 531 Glendale Rd Unit B302, Oakland, MD 21550, 2 beds, 1 bath

$369,000

2 beds1 bath887 sq ft

531 Glendale Rd Unit B302, Oakland, MD 21550

(301) 387-2000

Property at 315 Coolidge Ave, Oakland, MD 21550, 3 beds, 2 baths

$269,500

3 beds2 baths1,600 sq ft

315 Coolidge Ave, Oakland, MD 21550

(301) 387-4700

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 206 Mayhew Inn Rd, Oakland, MD 21550, 1 bed, 1 bath

$229,000

1 bed1 bath— sq ft

206 Mayhew Inn Rd, Oakland, MD 21550

(301) 387-4700

Property at 175 Roman Ridge Rd #15, Oakland, MD 21550, 4 beds, 4.5 baths

$547,500

4 beds4.5 baths3,192 sq ft

175 Roman Ridge Rd #15, Oakland, MD 21550

(301) 387-4700

Property at 189 Red Run Rd Unit 1-C-2, Oakland, MD 21550, 2 beds, 2 baths

$589,000

2 beds2 baths1,200 sq ft

189 Red Run Rd Unit 1-C-2, Oakland, MD 21550

(301) 387-4700

Property at 163 Mitchell Dr, Oakland, MD 21550, 4 beds, 2.5 baths

$314,900

4 beds2.5 baths2,242 sq ft

163 Mitchell Dr, Oakland, MD 21550

(301) 387-4700

Property at 723 Kings, Oakland, MD 21550, 4 beds, 2.5 baths

$380,000

4 beds2.5 baths1,824 sq ft

723 Kings, Oakland, MD 21550

(301) 722-4700

Property at 611 E Oak St, Oakland, MD 21550, 5 beds, 3 baths

$295,000

5 beds3 baths1,800 sq ft

611 E Oak St, Oakland, MD 21550

(301) 387-2000

Property at 433 San Francisco St, Oakland, MD 21550, 6 beds, 2.5 baths

$599,900

6 beds2.5 baths2,560 sq ft

433 San Francisco St, Oakland, MD 21550

(301) 387-2000

Property at 328 Stool Rock Rd, Oakland, MD 21550, 4 beds, 2.5 baths

$565,000

4 beds2.5 baths1,860 sq ft

328 Stool Rock Rd, Oakland, MD 21550

(301) 387-2000

Property at 355 Lonesome Pine Rd, Oakland, MD 21550, 2 beds, 2 baths

$585,000

2 beds2 baths1,584 sq ft

355 Lonesome Pine Rd, Oakland, MD 21550

(866) 525-3466

Property at 25 Silver Tree Ln, Oakland, MD 21550, 5 beds, 4 baths

$759,900

5 beds4 baths2,364 sq ft

25 Silver Tree Ln, Oakland, MD 21550

(301) 387-4700

Property at 41 Fox Den Rd, Oakland, MD 21550, 2 beds, 1 bath

$239,000

2 beds1 bath1,569 sq ft

41 Fox Den Rd, Oakland, MD 21550

(301) 387-4700

Property at 565 Glendale Rd #124, Oakland, MD 21550, 1 bed, 1 bath

$175,000

1 bed1 bath382 sq ft

565 Glendale Rd #124, Oakland, MD 21550

(301) 387-4700

Property at 155 Basswood Way, Oakland, MD 21550, 5 beds, 3 baths

$699,900

5 beds3 baths2,792 sq ft

155 Basswood Way, Oakland, MD 21550

(301) 387-2000

Property at 139 Overlook Ridge Dr, Oakland, MD 21550, 5 beds, 4.5 baths

$875,000

5 beds4.5 baths2,846 sq ft

139 Overlook Ridge Dr, Oakland, MD 21550

(301) 387-4700

Property at 127 Paradise Hts, Oakland, MD 21550, 3 beds, 2.5 baths

$1,100,000

3 beds2.5 baths2,240 sq ft

127 Paradise Hts, Oakland, MD 21550

(301) 387-4700

Property at 41 Boyd Paugh Ln, Oakland, MD 21550, 7 beds, 5 baths

$2,399,000

7 beds5 baths4,691 sq ft

41 Boyd Paugh Ln, Oakland, MD 21550

(301) 387-2000

Property at 180 Paradise Ridge Rd, Oakland, MD 21550, 3 beds, 2 baths

$425,000

3 beds2 baths1,152 sq ft

180 Paradise Ridge Rd, Oakland, MD 21550

(301) 387-2000

Property at 565 Glendale Rd #312, Oakland, MD 21550, 1 bed, 1 bath

$229,000

1 bed1 bath785 sq ft

565 Glendale Rd #312, Oakland, MD 21550

(888) 860-7369

Property at 3084 Lake Shore Dr, Oakland, MD 21550, 4 beds, 3 baths

$625,000

4 beds3 baths2,464 sq ft

3084 Lake Shore Dr, Oakland, MD 21550

(301) 387-2000

Property at 65 Village Dr #6, Oakland, MD 21550, 3 beds, 3 baths

$650,000

3 beds3 baths1,740 sq ft

65 Village Dr #6, Oakland, MD 21550

(301) 387-2000

Property at 565 Glendale Rd #212, Oakland, MD 21550, 1 bed, 1 bath

$210,000

1 bed1 bath527 sq ft

565 Glendale Rd #212, Oakland, MD 21550

(301) 387-2000

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

$1,299,000

4 beds3 baths1,844 sq ft

20698 Garrett Hwy, Oakland, MD 21550

(301) 387-4700

Property at 15 Village Dr #1, Oakland, MD 21550, 2 beds, 1 bath

$440,000

2 beds1 bath— sq ft

15 Village Dr #1, Oakland, MD 21550

(301) 387-2000

Property at 1240 Boy Scout Rd, Oakland, MD 21550, 7 beds, 6 baths

$4,390,000

7 beds6 baths5,695 sq ft

1240 Boy Scout Rd, Oakland, MD 21550

(443) 574-1600

Property at 439 Paradise Hts, Oakland, MD 21550, 6 beds, 4.5 baths

$1,329,000

6 beds4.5 baths4,113 sq ft

439 Paradise Hts, Oakland, MD 21550

(301) 387-2000

Property at 621 Paradise Hts, Oakland, MD 21550, 4 beds, 3 baths

$695,000

4 beds3 baths3,242 sq ft

621 Paradise Hts, Oakland, MD 21550

(301) 387-2000

$369,000

4 beds2 baths2,072 sq ft

8946 Oakland Sang Run Rd, Oakland, MD 21550

(410) 426-2700

Property at 170 San Francisco St, Oakland, MD 21550

$129,900

— beds— baths— sq ft

170 San Francisco St, Oakland, MD 21550

(717) 757-2717

Property at Fox Tail Rd, Oakland, MD 21550

$39,500

— beds— baths— sq ft

Fox Tail Rd, Oakland, MD 21550

(301) 387-2000

Property at Lot 40 Big Piney Dr, Oakland, MD 21550

$17,000

— beds— baths— sq ft

Lot 40 Big Piney Dr, Oakland, MD 21550

(301) 387-4700

Property at 123 Mountainview Ct, Oakland, MD 21550

$221,000

— beds— baths— sq ft

123 Mountainview Ct, Oakland, MD 21550

(301) 387-2000

Property at Lots 13/17 Dogwood Dr, Oakland, MD 21550

$32,000

— beds— baths— sq ft

Lots 13/17 Dogwood Dr, Oakland, MD 21550

(301) 387-2000

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MLS Listings for Sale in Oakland

There are currently 130 mls listings for sale in Oakland at a median listing price of $440K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Oakland stay on the market for 149 days. This map is refreshed with the newest listings in Oakland every 15 minutes.

In the past month, 5 homes have been sold in Oakland. In addition to houses in Oakland, there was also 1 condo, 3 townhouses, and 1 multi-family unit for sale in Oakland last month. Find your dream home in Oakland using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Oakland are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Oakland. Our Oakland real estate stats and trends will give you more information about home buying and selling trends in Oakland. If you're looking to sell your home in the Oakland area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Oakland with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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MLS Listings for Sale in Oakland, MD

MLS Listings for Sale in Oakland

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