Oakland Real Estate, Homes and Condos for sale

All Oakland homes currently listed for sale in Oakland as of 05/23/2019 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."
$1,375,000
144 HAWTHORNE LN, Oakland MD 21550
5
BEDS
4
BATHS
4,419
SQFT
$311
$/SQFT
1.46
ACRES
1992
BUILT
"Magnificent lakefront home! This home it situated on a picturesque 1.47 acre level lakefront lot. Offering a type A dock, 175 feet of lakefront, stunning views and a quiet location. This home boasts five bedrooms, an open floorplan, updated kitchen and master bath and views from almost every room. The outside area is just as pleasing, featuring a large lakefront deck for your enjoyment with family and friends."
$1,374,000
139 PARADISE LN, Oakland MD 21550
5
BEDS
5
BATHS
3,607
SQFT
$381
$/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 - $1,399,000 TO $1,374,000 
$1,199,000
299 RANDALL WAY, Oakland MD 21550
5
BEDS
3
BATHS
3,864
SQFT
$310
$/SQFT
2.00
ACRES
1993
BUILT
"Distinctive Lake Front home offering spacious living with amazing lake views. Open floor plan, vaulted ceilings, natural stained trim and hardwood doors, freshly painted and ready to move in! New roof on house in 2018, new roof on carriage house in 2017! High efficiency furnace installed in main house and carriage in 2017! 200' of unobstructed lake view, situated on over 2+ acres! Enjoy your mornings and watch the sunrise from the expansive deck overlooking the lake, or on those rainy mornings take shelter on the covered areas!. Full day lit walkout basement, offering the potential of more sleeping areas, game room, home offices, the list is endless! Sliders open to stone patio for entertaining! 2012 Aluminum dock, offering 30' boat slip. 20 KW Genarac Backup Generator conveys! Carriage apartment offers 1000 sq ft of living area with a covered and finished entrance, full bath and complete kitchen. 30' x 40' roof top deck with full view of lake!So much to offer here in this quiet cove with deep water!"
$999,999
2094 PARADISE POINT RD, Oakland MD 21550
4
BEDS
4
BATHS
2,812
SQFT
$356
$/SQFT
0.67
ACRES
2001
BUILT
"Simply amazing lakefront opportunity! Want a vacation home that is a constant reminder that you are at the lake? This is it. 'Clearview' lives up to its name AND its location on Paradise Point! Must see to appreciate the sprawling shoreline, boasting 387 feet of gorgeous, flat & accessible lakefront land. Open and spacious, the shoreline is still remarkably private and dotted with mature trees and just the right mix of sun and shade. Each window inside offers an amazing piece of a panoramic view of the lake, which wraps around the house. The gleaming hardwood floors and white stone fireplace give the room a clean alluring feel perfect for entertaining your guests. The large open kitchen and dining room offer even more views. The screened in porch is the ideal place for enjoying your morning coffee or for spending time conversing with loved ones on a quiet relaxing evening. Home offers 4 bedrooms (2 masters), and 3.5 baths. Throw in an attached AND detached garage and you have the recipe for the perfect lake home!"
$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 
$779,000
203 SKIPPERS POINT RD, Oakland MD 21550
6
BEDS
6
BATHS
2,736
SQFT
$285
$/SQFT
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 - $819,900 TO $779,000 
$629,900
1470 PARADISE POINT RD, Oakland MD 21550
3
BEDS
3
BATHS
2,358
SQFT
$267
$/SQFT
0.60
ACRES
2001
BUILT
"This 3BR level Lake Front property has a main floor Master and 2 car garage access. Conveniently located Mid Lake and 10 minutes to Ski Slopes. Open concept living with deck overlooking large backyard. House generator for convenience. 2 large bedrooms upstairs with lake views. 2 car garage plus 2 additional sheds for equipment and recreational toys. Full unfinished basement with plenty of indoor storage or could be converted to Recreation room, also has walk out to backyard area. Dock is ready for your boat and swimming. Come take a look at this great lake front property!"
* NEW LISTING 
$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."
* LISTED OVER 120 DAYS 
$575,000
132 TARN DR, Oakland MD 21550
5
BEDS
7
BATHS
1.00
ACRES
2019
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 
$569,000
658 LAKE SHORE DR, Oakland MD 21550
4
BEDS
5
BATHS
2,205
SQFT
$258
$/SQFT
0.42
ACRES
2016
BUILT
"Water access yes; will convey with 1/12 deeded ownership interest in a nearby lakefront parcel tax id 1218029049 with 100' lake frontage, perfect for canoeing, kayaking, swimming and relaxing by the lake, No dock eligibilityModern touch to a rustic design, this unique property boasts a beautiful outdoor living area with a full masonry fireplace and the popular mother-in-law suite over the garage."
* LISTED OVER 120 DAYS 
$540,000
1510 BROADFORD RD, Oakland MD 21550
5
BEDS
4
BATHS
2,495
SQFT
$216
$/SQFT
2.03
ACRES
2007
BUILT
"This home is in a great location with lake views. It includes a pool, 2 car garage, fire pit, covered back porch, and a large front deck over looking Broadford Lake. There are fun activities for the whole family with parks, boating, swimming, and even a personal zip line in the backyard. On 7/26/2017 this house appraised for $585,000. With 4,200 square feet of finished living space and a total of 4,672 square fee , there is room for family and friends to gather. If you would like additional information call (301)616-8771."
* PRICE LOWERED - $555,000 TO $540,000 
$535,000
4198 MARYLAND HWY, Oakland MD 21550
3
BEDS
2
BATHS
1,500
SQFT
$357
$/SQFT
1.73
ACRES
1962
BUILT
"BUSINESS PROPERTY & HOUSE$579,000 INVESTMENT OR INCOME POTENTIAL BEAUTIFUL 3 BEDROOM, 2 BATH RANCH-STYLE BRICK HOME WITH LARGE COMMERCIAL BUILDING. RENT COMMERCIAL BUILDING TO EXISTING TENANT, OPERATE YOUR OWN BUSINESS, WIDE RANGE OF POSSIBILITIES.HOUSE HAS ATTACHED 2 CAR GARAGE, SPACIOUS DEN WITH BAR AREA IN HALF OF BASEMENT, HALF PARTIAL UNFINISHED BASEMENT. CENTRAL AIR, OIL HOT WATER BASEBOARD HEATING, PROPANE FIREPLACE IN DEN. BACKYARD FEATURES IN-GROUND POOL SURROUNDED BY NICELY LANDSCAPED FOLIAGE, POOL HOUSE & GAZEBO, PRIVACY FENCE.COMMERCIAL BUILDING IS APPROXIMATELY 4,400 SQUARE FEET WITH OFFICE AREA, LARGE BAY GARAGE, WORKSHOP AREA. ALSO HAS 16~ X 32~ DETACHED GARAGE, PLENTY OF PAVED PARKING AREA, ALL ON 1.7 ACRES. CURRENT BUSINESS TENANT CAN BE PURCHASED AS AN OPTION AS WELL."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $549,000 TO $535,000 
$529,000
8 HIDDEN COVE CT, Oakland MD 21550
4
BEDS
3
BATHS
2,856
SQFT
$185
$/SQFT
0.98
ACRES
2002
BUILT
"This lake access home is located in the charming Heron Cove subdivision. Offering four bedrooms, an open floorplan and nice lake views. The dock slip is located within walking distance to this home, or ride the golf cart which is included. The propane stone fireplace is another eye catching feature of the home. The deck is ideal to enjoy family and friends while looking at beautiful Deep Creek Lake. Detached 1-car garage/toy shed. Community walking trails and tennis court, as well as a great beach area for the children to play by the water. Quiet cove centrally located to all DCL attractions."
* NEW LISTING 
$512,000
1294 SUNNYSIDE RD, Oakland MD 21550
4
BEDS
3
BATHS
2,268
SQFT
$226
$/SQFT
120.06
ACRES
1990
BUILT
"Experience mountain seclusion in picturesque Pleasant Valley. Enjoy views of 120+ acres from every room of this quality built home w/cozy woodburner, hardwood floors & spacious kitchen. Wander the paths among mature pines & hardwoods or enjoy fields & streams. Have extra value w/3 subdivided lots included. Continue ag use to keep taxes low. Mineral rights convey."
* LISTED OVER 120 DAYS 
$479,500
201 SANDY BEACH LN, Oakland MD 21550
3
BEDS
2
BATHS
1,893
SQFT
$253
$/SQFT
1.11
ACRES
2010
BUILT
"10 years young, this modern 3BR 2BA chalet offers privacy, luxury and room to expand. Cathedral ceilings, hardwood floors and a wall of windows create a welcoming ambiance in the great room. Othe features include eat-in kitchen, granite tops, custom tile baths, expansive deck, hot tub and a full basement with rough-in for additional bath and room for more bedrooms or a rec room. Its a short walk to the community tennis courts and your deep water, dedicated boat slip. Sandy Beach is a highly sought after community. You will love being off-the-beaten-path yet still within a short drive from Wisp Resort, the Adventure Sports Center International, restaurants, shops and much more!"
$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 
$420,000
297 PARADISE POINT RD, Oakland MD 21550
3
BEDS
4
BATHS
1,512
SQFT
$278
$/SQFT
4.00
ACRES
2005
BUILT
"Welcome to this cozy fully renovated home.With astonishing views from the top of the hill to take in the wonderful scenery, this home has so much to offer.Upper level features 3 bedrooms and 2 full baths all completely redone with beautiful hardwood flooring throughout, new windows for natural light.Basement has a huge recreational area w/ 2 full baths. Sitting on 4 acres of land and new driveway and more!"
$399,900
175 ROMAN RIDGE RD #15, Oakland MD 21550
4
BEDS
5
BATHS
3,192
SQFT
$125
$/SQFT
2006
BUILT
"Lovely lake view detached condo with loads of room. Tastefully furnished with 3 living areas and space for another bedroom & bath! Enjoy family and friends on the spacious deck. Hot tub location offers privacy. All bedrooms are master suites. So many extras! Never rented and well-maintained."
* LISTED OVER 120 DAYS 
$395,000
268 LEHMAN LN #41, Oakland MD 21550
4
BEDS
4
BATHS
2,784
SQFT
$142
$/SQFT
2007
BUILT
"Cabin in Gallatin Woods! Quiet, yet central, log home community off Lakeshore Drive; absorb the vibe of the forest and the large natural boulders surrounding the community. Upon arrival, enjoy the ambiance that only a custom log home provides, along with multiple gas fireplaces, a screened porch, inviting hot tub, hand-hewn log steps and a vaulted ceiling. Extensive decking and ample yard space!"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $397,500 TO $395,000 
$369,900
85 STOCKSLAGER RD, Oakland MD 21550
3
BEDS
2
BATHS
2,300
SQFT
$161
$/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
412 TANGLEWOOD DRIVE, Oakland MD 21550
3
BEDS
4
BATHS
2,112
SQFT
$170
$/SQFT
2.00
ACRES
2006
BUILT
"Highest quality cabin perched in a forested setting. Quality at every turn offers; Granite Counter tops, custom cabinetry, Hardwood Floors throughout, 22' Native Stone Fireplace, Vaulted ceilings lovingly finished in Tongue & Groove by a true wood craftsman. Main level Bedroom provides a private bath with Jacuzzi tub and 2 upstairs bedrooms with 2 full bathrooms. Full, partially finished walkout basement waiting for your finishing touches. Attached 500 s.f. garage & paved driveway completes the home. Well established Vacation Rental income to help with costs if desired. To a buyer, please review a note from the homeowner to a buyer prospect (We only share this client info, we do not offer tax advice)....As an owner and client of your rental services over the last 13 years, I am glad to comment on the tax shelter potential of owning a property that is not rented full time during the year. This includes looking at the impact of the Trump tax cuts. First of all if you rent a unit full time for the whole year, you do NOT have significant tax shelter potential. If you rent your property in part time segments and use the property for personal purposes 8 to 11 times a year, you have a great tax shelter potential write off. This allows the owner to declare all property expenses including real estate taxes, management fees, utilities and maintenance costs plus every time you breathe on the property and there are costs. In addition, you can claim depreciation. You fill in the Schedule E at tax time. The resulting loss is recorded on your federal return and reduces your adjusted gross income. Over the years I have averaged write offs of $16,000 to $20,000 per year. The Trump tax cuts do NOT affect this process.SincerelyTerry M."
$350,000
10 WINDING TRAIL LN #1A, Oakland MD 21550
5
BEDS
5
BATHS
3,300
SQFT
$106
$/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 - $360,000 TO $350,000 
$349,900
21651 GARRETT, Oakland MD 21550
3
BEDS
2
BATHS
1,053
SQFT
$332
$/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!"
 
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