Oakland Real Estate, Homes and Condos for sale

All Oakland homes currently listed for sale in Oakland as of 12/17/2018 are shown below.  You can change the search criteria at any time by pressing the 'Change Search' button below.

If you have any questions or you would like more information about any Oakland homes for sale or other Oakland real estate, please contact us and one of our knowledgeable Oakland REALTORS® would be pleased to assist you.


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$1,495,000
763 CHADDERTON SCHOOL RD, Oakland MD 21550
6
BEDS
6
BATHS
6,051
SQFT
$247
$/SQFT
1.76
ACRES
1970
BUILT
"PHENOMENAL 3 MILE VIEW OF DEEP CREEK LAKE ALL THE WAY TO THOUSAND ACRES!!! WITHOUT A DOUBT ONE OF THE VERY BEST LAKEFRONT LOTS ON DEEP CREEK! BOASTING 269 FEET OF LEVEL LAKEFRONT, 1.76 ACRES WITH QUONSET HUT, 6 BEDROOMS, 6 BATHS, STORAGE GALORE, PLENTY OF PARKING, 3 FIREPLACES AND LOADS OF PRIVACY - PROPERTIES LIKE THIS DON'T COME ON THE MARKET VERY OFTEN. MUST SEE TO APPRECIATE."
* LISTED OVER 120 DAYS 
$1,399,000
139 PARADISE LN, Oakland MD 21550
5
BEDS
5
BATHS
3,607
SQFT
$388
$/SQFT
0.20
ACRES
2004
BUILT
"Magnificent custom lakefront home with captivating interior views that feel like you're over the water! Elegant and tastefully decorated. Beautifully stone landscaped waterfront area to share your memories. Centrally located. Easy level access driveway off of quiet road. 70k gross annual rental projection potential. Weatherproof wrap-around decking. 100' lakefront w/Type A private dock. Must see!"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $1,429,000 TO $1,399,000 
$819,900
203 SKIPPERS POINT RD, Oakland MD 21550
6
BEDS
6
BATHS
0.34
ACRES
2001
BUILT
"Income producing lakefront rental w/Class A dock! Built in 2001, this home has lake fun in mind with SIX Bedrooms, 4 master suites, 5 full baths, refinished wood floors, freshly painted exterior, & hot tub! Two ground level master suites w/Soaking tubs and separate showers. Two more suites are located upstairs, along with two additional bedrooms. Excellent lake location near Wisp and state parks."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $849,900 TO $819,900 
$799,000
161 GLENDALE RD, Oakland MD 21550
6
BEDS
6
BATHS
3,455
SQFT
$231
$/SQFT
0.70
ACRES
2002
BUILT
"Lakefront home offering a dock slip, 6 bedrooms,, open floor plan, 2 wood burning stone fireplaces and lake views from most rooms. The level lakefront yard makes this ideal for enjoying Deep Creek Lake. Hardwood flooring, stainless steel appliances, lakefront deck are just a few more of the great features this home has to offer. The location is also key-minutes to restaurants, cinema & market."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $825,000 TO $799,000 
$679,900
599 PARADISE RIDGE RD, Oakland MD 21550
5
BEDS
3
BATHS
2,856
SQFT
$238
$/SQFT
0.99
ACRES
1979
BUILT
"Lake access w/dock slip Stunning lake and countryside views all 3 levels Gourmet kitchen w/new stainless steel appliances Custom tile work/Bamboo floors Steam shower upstairs Sunlight Signature sauna w/Blaupunkt sound VT soapstone wood burning stove Elfa closet system in 3 bedrooms New deck off main and basement-5/18 New fuel oil tank-4/18 Septic tank cleaned-5/18 New well pump-4/18"
$610,000
74 GRANDVIEW DR, Oakland MD 21550
5
BEDS
4
BATHS
4,135
SQFT
$148
$/SQFT
2.00
ACRES
1998
BUILT
"Exceptional, all expansive, lake views - Five bedroom - 3 1/2 baths - Open floor plan - Decks - Boat slip potential through HOA (see declarations (class A lot) and refer to HOA website) - wine room (temperature controlled) - zoned heating - Screen porch of kitchen convenient for grilling - Sauna - Wet bar - Steam shower - Master Bedroom suite with walk-thru closet - Exceptional opportunity; Is it perfect? - NO, Is it an exceptional, un-duplicated opportunity - YES - Sold as-is."
* NEW LISTING 
$599,999
4198 MARYLAND HWY, Oakland MD 21550
3
BEDS
2
BATHS
1,500
SQFT
$400
$/SQFT
1.73
ACRES
1962
BUILT
"Beautiful 3 bed 2 bath brick home, attached 2 car garage with spacious Den in bar area in basement. Approximately half of basement unfinished, full of possibilities. Central air, oil hot water baseboard heating with propane fireplace in den. Backyard features in-ground pool surrounded by nicely landscaped surroundings with pool house and gazebo, nice privacy fence. Property also includes approximately 4400 + square foot commercial shop with office area, Workshop, large 28 foot by 40 foot by 18 foot high garage Bay. Currently being used as a sign business but can be utilized for a wide range of business ventures. Also has detached garage 16 foot by 32 foot and small utility shed. Paved driveways and parking lot on 1.7 Acres. Sell all or property can be subdivided. Current business also can be a separate option."
$589,900
37 GILA TRL, Oakland MD 21550
5
BEDS
5
BATHS
3,688
SQFT
$160
$/SQFT
0.71
ACRES
2003
BUILT
"Beautiful lake access home! This home offers water views, spacious open floorplan with natural lighting in most every room. The windows in this home make you feel you are outside when you are in. The wraparound deck is an ideal place to enjoy family and friends, go down one level to find a stone patio with a hot tub. Also offers a dock slip, and a great location, just minutes to Wisp Resort."
$585,000
231 SANTA FE TRAIL RD, Oakland MD 21550
3
BEDS
3
BATHS
0.35
ACRES
2003
BUILT
"CUSTOM LOG HOME NESTLED IN THE DEEP CREEK LAKE COMMUNITY. 3 BEDROOMS AND 3 FULL BATHS. THIS HOME OFFERS A LOFT THAT CAN BE UTILIZED AS A BEDROOM AS WELL. BEAUTIFUL MOUNTAIN AND LAKE VIEW. ESTABLISHED RENTAL CLOSE TO THE WISP/219 AND LAKESHORE COMMUNITY. WONDERFUL VACATION COMMUNITY OR A PARADISE TO RAISE A FAMILY. SO MUCH FUN AND ADVENTURE TO EXPLORE. SELLERS WILL SELL ALL THREE HOMES AS A PACKAGE"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $649,000 TO $585,000 
$585,000
58 LEO FRIEND RD, Oakland MD 21550
4
BEDS
3
BATHS
0.49
ACRES
2003
BUILT
"MILLION DOLLAR VIEW NESTLED IN THE DEEP CREEK LAKE COMMUNITY. 4 BEDROOMS AND 3 FULL BATHS /LOFT. LAKE VIEW GREAT COMMUNITY TO LIVE OR VACATION IN. FULLY FURNISHED. NEAR THE WISP/219 LAKESHORE AREA. THIS HOME HAS BEEN ESTABLISHED AS A VACATION RENTAL. THE SELLERS WILL SELL ALL THREE HOMES AS A PACKAGE. PLEASE CALL FOR MORE INFORMATION. BRING ALL OFFERS! JUST REDUCED!"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $649,000 TO $585,000 
$585,000
245 SANTA FE TRAIL RD, Oakland MD 21550
3
BEDS
3
BATHS
0.44
ACRES
2003
BUILT
"BEAUTIFUL CABIN NESTLED IN THE DEEP CREEK LAKE COMMUNITY. BEAUTIFUL MOUNTAINS ABOUND.FULLY FURNISHED HOME OR VACATION HOME. TRANQUIL LAKE VIEW. THIS HOME OFFERS 3 BEDROOMS AND 3 FULL BATHS. THIS HOME HAS A LOFT THAT CAN BE USED AS A 4TH BEDROOM. FAMILY FUN FOR EVERYONE. SELLERS WILL SELL ALL THREE HOMES AS A PACKAGE. PLEASE CALL FOR MORE INFORMATION. BRING ALL OFFERS! JUST REDUCED!"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $649,000 TO $585,000 
$575,000
132 TARN DR, Oakland MD 21550
5
BEDS
7
BATHS
1.00
ACRES
2017
BUILT
"This To Be Built house has it all! With 5 bedrooms and 5 full baths, it makes a perfect family get away or great rental investment property. All the amenities included in price - Hardwood floors & gas fireplace in great room.. Open floor plan to kitchen with island and dining area. Large deck on rear of home"
* LISTED OVER 120 DAYS 
$525,000
2230 HERRINGTON MANOR RD, Oakland MD 21550
3
BEDS
2
BATHS
1,868
SQFT
$281
$/SQFT
30.72
ACRES
2009
BUILT
"Beautiful horse farm with 15 stalls, indoor arena,wash/grooming stalls, locker room & lounge. Also 3 additional barns including bank barn. Almost new home with large bedrooms, two large baths with double vanities. Open floor plan with beautiful views of property. High rated wire Tensile cross fencing & paddocks. Three wells. Located 5 minutes from Oakland."
* LISTED OVER 120 DAYS 
$479,000
111 RIDGEWOOD DR, Oakland MD 21550
4
BEDS
4
BATHS
3,496
SQFT
$137
$/SQFT
1.04
ACRES
1991
BUILT
"Incredible winter views of lake! Situated on lovely wooded lot w/multiple decks all overlooking lake. Located in center of Deep Creek Lake in wonderful community w/docks, lakefront community center, tennis courts, playground. Minutes to ski slopes and short walk to lakefront. Stone fireplaces and double sided in LV/DR. Perfect location for relaxed lake living! Docks often avail for lease"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $499,000 TO $479,000 
$425,000
7 SILVER TREE LN, Oakland MD 21550
5
BEDS
4
BATHS
2,407
SQFT
$177
$/SQFT
0.29
ACRES
2004
BUILT
"This lovely lake access home is conveniently located minutes from all the Deep Creek activities. With easy walk to lake access, you can enjoy all the lake has to offer. Outside access to shed storage. Large paved parking area and triple decks. Cathedral ceilings and open living area withs lots of light. Two stone gas fireplaces. Great for investment or second home!"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $445,000 TO $425,000 
$399,000
93 SKIPPERS POINT RD, Oakland MD 21550
1
BEDS
1
BATHS
1.16
ACRES
1930
BUILT
"Beautiful wooded and very private 1.16 acre lakefront property with Type A (private) dock permit. 127' of lake frontage with seclusion and deep water by dam. Existing home is uninhabitable a tear down. Short wooded path to the lake from the gorgeous home site for your dream lakefront home! Very near Swallow Falls State Park and Wisp Resort for the perfect quiet location away from main roads."
* LISTED OVER 120 DAYS 
$389,900
15 BEAR RUN RD, Oakland MD 21550
3
BEDS
2
BATHS
1,080
SQFT
$361
$/SQFT
44.19
ACRES
1995
BUILT
"NEW PRICE! 44 magnificent wooded acres with a 3 Bedroom, 2 Bath home ~ Sits on the side of a mountain above the Yough River, some of the best Trout fishing in Maryland! No HOA or restrictions! Located in the Timber Trails neighborhood off of Oakland Sang Run Rd, - only minutes to The Wisp & Deep Creek Lake! Upper 2 lots are also accessible by a power line access road - Endless possibilities here!"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $425,000 TO $389,900 
$384,700
95 GALLATIN DR #3, Oakland MD 21550
4
BEDS
4
BATHS
2,288
SQFT
$168
$/SQFT
2005
BUILT
"Custom Mountaineer Log Home. Designed to be a Tranquil getaway, relax on the back deck and listen to the babbling stream. Open floor plan, wide planked hardwood floors, kitchen island and breakfast bar. Wood burning fireplace with river rock from ceiling to floor. 2-Master Suites, Private setting surrounded by hemlocks, beautiful ferns and oak trees. Paved driveway sets back from Gallatin Drive."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $408,700 TO $384,700 
$375,000
85 STOCKSLAGER RD, Oakland MD 21550
3
BEDS
2
BATHS
2,300
SQFT
$163
$/SQFT
1.71
ACRES
2003
BUILT
"Custom log cabin w/front porch on 1.71 acres close to Swallow Falls & Deep Creek Lake! Nestled in the woods, this home is private & offers quality construction & upgrades galore incl. a beautiful kitchen w/maple cabinets, hardwood & flagstone floors, exposed beams, custom gas FP & tons of room to spread out! Radiant heated floors, oversized log sided carport, whole house water filter & satellites! There is also an additional lot for sale that could be purchased for a combined price of $520,000 giving it over 13 total acres at 123 Stockslager Road. FULLY FURNISHED WITH 2 KAYAKS TOO!"
$360,000
10 WINDING TRAIL LN #1A, Oakland MD 21550
5
BEDS
5
BATHS
3,300
SQFT
$109
$/SQFT
2006
BUILT
"NEW PRICE! Stunning condo at Deep Creek Lake close to shopping, movie theater, restaurants, etc. Originally the model unit for Timberlake Village this has both a covered balcony & patio complete with hot tub & fire pit! Enjoy drinking coffee in the morning while listening to the stream running behind you! This turn-key town home is tastefully decorated & meticulously maintained. 3 master suites!"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $370,000 TO $360,000 
$348,900
21651 GARRETT HWY, Oakland MD 21550
3
BEDS
2
BATHS
1,200
SQFT
$291
$/SQFT
0.46
ACRES
1960
BUILT
"What a deal! Split Lakefront with Type A dock just a few minutes from WISP. Imagine sitting on your covered porch watching the boats go by or fishing from your own dock. Finish the day curled up in your living room by the native stone fireplace. This home is completely turn-key - fully furnished with a great rental history. Newer carpet, paint, driveway - well maintained. A MUST SEE!"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $349,000 TO $348,900 
$325,000
121 CRESTVIEW DR, Oakland MD 21550
3
BEDS
3
BATHS
2,288
SQFT
$142
$/SQFT
0.58
ACRES
1980
BUILT
"This beautiful home has been remodeled with gourmet kitchen and top of line appliances. Luxury bathrooms and huge walk in closet with upstairs laundry. Beautiful landscaped private yard. Large deck to enjoy outdoor living. Convenient location in Oakland with no town taxes."
$315,000
135 ROCK RIDGE LN #13, Oakland MD 21550
4
BEDS
3
BATHS
2,632
SQFT
$120
$/SQFT
2004
BUILT
"Great four bedroom home in the beautiful Silver Ridge community. This home offers an open floorplan with cathedral ceilings, two fireplaces, two family rooms and hardwood flooring. The large outdoor deck and hot tub are a great space to entertain family and friends. The location of this home is ideal, just minutes to Wisp Ski Resort, Deep Creek State Park, restaurants and the cinema."
$299,900
15822 GARRETT HWY, Oakland MD 21550
4
BEDS
4
BATHS
3,944
SQFT
$76
$/SQFT
4.06
ACRES
1986
BUILT
"This 4 bedroom home offering 4 ac private setting & amazing mtn views is located halfway between Oakland & Deep Creek. Large kitchen offers stainless steel appliances & island workspace. Lower level offers huge family room, workshop, 2nd kitchen & TONS of storage. Paved drive, 3 garage spaces & above ground pool add to the appeal. Additional 2+ acres with frontage on Route 219 also available."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $319,900 TO $299,900 
 
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