Oakland Real Estate, Homes and Condos for sale

All Oakland homes currently listed for sale in Oakland as of 03/18/2019 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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$1,399,000
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 
$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."
* NEW LISTING 
$819,900
203 SKIPPERS POINT RD, Oakland MD 21550
6
BEDS
6
BATHS
2,736
SQFT
$300
$/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 - $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 
$659,000
501 WOODLANDS HILL, Oakland MD 21550
5
BEDS
5
BATHS
3,750
SQFT
$176
$/SQFT
1.49
ACRES
2008
BUILT
"Must see this Amazing view! Beautiful Lindal home with a 180 degree views of the mountain and lake, but totally private. 5 bedrooms, 5 baths. Parking for 5 cars. Comes completely turn-key. All furniture, hot tub,pool table, dishes, linens. ....Come start your vacation right now!"
* NEW LISTING 
$659,000
599 PARADISE RIDGE RD, Oakland MD 21550
5
BEDS
3
BATHS
2,652
SQFT
$248
$/SQFT
0.99
ACRES
1979
BUILT
"LOCATION - LOCATION - LOCATION. This 5 bedroom, 1A property has it all! Incredible, unobstructed, 180 degree view from all 3 levels of Deep Creek Lake and the surrounding mountains; nestled in a quiet neighborhood; assigned dock slip; lake recreation area (with pavilions, tables, swimming docks and canoe/kayak rack); proximity to theaters, state parks (hiking and cross-country), WISP slopes and the best restaurants (1-2 miles).This home has been updated with granite counters in the kitchen and all bathrooms, slate entryway and basement, hardwood floors throughout, luxury steam shower and lots of storage. This house is ready to move in and enjoy Deep Creek Lake life!"
$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."
* 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."
$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."
$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!"
* NEW LISTING 
$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
231 SANTA FE TRAIL RD, Oakland MD 21550
3
BEDS
3
BATHS
15,246
SQFT
$28
$/SQFT
0.35
ACRES
2003
BUILT
"JUST REDUCED! DON'T MISS THIS ONE!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 - $585,000 TO $420,000 
$420,000
58 LEO FRIEND RD, Oakland MD 21550
4
BEDS
3
BATHS
21,344
SQFT
$20
$/SQFT
0.49
ACRES
2003
BUILT
"JUST REDUCED! DON'T MISS THIS ONE!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 - $585,000 TO $420,000 
$420,000
245 SANTA FE TRAIL RD, Oakland MD 21550
3
BEDS
3
BATHS
191,666
SQFT
$2
$/SQFT
0.44
ACRES
2003
BUILT
"JUST REDUCED! DON'T MISS THIS ONE!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 - $585,000 TO $420,000 
$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."
$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."
$397,500
268 LEHMAN LN #41, Oakland MD 21550
4
BEDS
4
BATHS
2,784
SQFT
$143
$/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!"
* PRICE LOWERED - $399,000 TO $397,500 
$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
113 HUMMINGBIRD CT, Oakland MD 21550
4
BEDS
2
BATHS
2,632
SQFT
$142
$/SQFT
5.30
ACRES
2002
BUILT
"Prime location at Deep Creek Lake, located just off Lake Shore Drive. Nestled among 5 acres of privacy this lake access home boasts finished rec room on lower level, stone fireplace in living room, and large deck to enjoy nature."
$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."
$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 
$330,000
16 WANDERER LN #C-3, Oakland MD 21550
3
BEDS
2
BATHS
1975
BUILT
"Totally furnished 3/bed/2bath lakefront townhouse w/ assigned boat slip is MOVE-IN READY! This model features the LARGE master w/ renovated master bath! The great room with fireplace offers huge space for family fun! Covered deck is perfect for sunsets & stairs connect to the ground floor! Patio perfect for grilling! Enjoy the swim dock & large sandy beach. ! Rustic community use cabin, volleyball & tennis/basketball court."
 
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