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Oakland Real Estate, Homes and Condos for sale

All Oakland homes currently listed for sale in Oakland as of 10/15/2019 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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52
$1,299,000
144 HAWTHORNE LN, Oakland MD 21550
5
BEDS
4
BATHS
4,419
SQFT
$294
$/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."
* PRICE LOWERED - $1,375,000 TO $1,299,000 
51
$815,000
153 MALLARD LOOP, Oakland MD 21550
4
BEDS
3
BATHS
3,506
SQFT
$232
$/SQFT
1.10
ACRES
1995
BUILT
"If you are looking for a home with stunning lakefront, this is it! This home offers lake views from almost every room. The floorplan flows very nicely and you feel invited outside from in. Offering four bedrooms, three baths, three levels of living space not to mention a great loft. Featuring hardwood floors in most rooms and a large stone fireplace. The outside area is just as pleasing, from the multiple lakefront decks,(some of which is covered), hot tub and just steps to the lakefront. The property also features a guest house, offering a living room and sleeping area and a wood burning fireplace. This home would be ideal for a full time residence or a great vacation home. It is also an established rental Schmidt's Lodge."
29
$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."
* PRICE LOWERED - $825,000 TO $799,000 
30
$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."
* PRICE LOWERED - $819,900 TO $779,000 
30
$749,000
19956 GARRETT HWY #3, Oakland MD 21550
4
BEDS
4
BATHS
3,012
SQFT
$249
$/SQFT
2007
BUILT
"Carefree, upscale lake front living at its best at this 4BBR/4BA Creekside Condominium. Unit has its own assigned boat dock, with lighted walkway to the docks, and assigned parking for 2 cars. Unit offers beautiful lakefront views from all three floors. There are decks off the upper floors and patio with firepit and hot tub on the ground floor. Upstairs features two master bedrooms with private bathrooms. Features include hardwood floors, granite countertops, custom tile bathrooms and showers, two stone fireplaces, wet bar with small refrigerator, lower level rec room and dual zone heating and cooling. Unit is within walking distance of dinning, shopping and entertainment. Complex features large grassy waterfront area for games and picnics. The HOA handles lawn care, snow removal and outside maintenance. high end furnishings are negotiable."
49
$724,900
295 PARADISE ACRES RD, Oakland MD 21550
3
BEDS
2
BATHS
1,584
SQFT
$458
$/SQFT
0.41
ACRES
1966
BUILT
"If you are looking for a lakefront log cabin that makes you feel right at home from the moment you walk in, this is it. This home offers a stone woodburning fireplace, hardwood flooring throughout, wood ceilings and walls not to mention a great loft area. The lake can be seen from almost every room of this home. The outside space is just as pleasing, take your pick of what to enjoy first: the hot tub, lakefront deck area, lakefront swing, playhouse, firepit or your Type A dock. The possibilities are endless at this great property."
36
$699,000
1003 LAKESHORE, Oakland MD 21550
5
BEDS
3
BATHS
2,536
SQFT
$276
$/SQFT
0.35
ACRES
1985
BUILT
"4/5 BR Gnegy-built lakefront chalet with garage on coveted Lake Shore Drive. Exposed beams, lots of natural light, open loft, massive stone fireplace, central AC, and a 'tree-top' exterior deck to enjoy the outdoors and watch the boats zoom by. In-law suite with 1/2 bath above garage. 100 feet of waterfront & a lakeside storage shed, offering a private Type A dock with plenty of sunshine and deep water. Views of Stump Point and located near the entrance to Red Run cove. The lower level is currently setup as a bedroom, but could easily be converted to a rec room for more entertaining space. One car garage with a workshop, electric & heat. Low maintenance yard with circular driveway. Close to state parks, Wisp & all things Deep Creek!"
* PRICE LOWERED - $749,000 TO $699,000 
30
$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."
32
$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."
59
$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 
34
$539,000
1195 MOUNTAINVIEW DR, Oakland MD 21550
4
BEDS
4
BATHS
2,611
SQFT
$206
$/SQFT
1.00
ACRES
1995
BUILT
"If you are looking for a beautiful mountain retreat home, this is it! This home is inviting from the moment you walk in the door. Featuring four bedrooms, open floorplan, gas fireplace, hardwood flooring and three levels of living space. The floorplan is set up to be an ideal full time or vacation home. The exterior space is just as pleasing, offering a large deck with a hot tub, lower patio area and a nice firepit area to enjoy with family and friends. You are also able to use the lakefront Mountainside clubhouse, lake access area for swimming, fishing and kayaking, as well as the community tennis court. This home is also just minutes to Wisp Ski Resort."
38
$499,900
8 HIDDEN COVE CT, Oakland MD 21550
4
BEDS
3
BATHS
2,856
SQFT
$175
$/SQFT
0.98
ACRES
2002
BUILT
"This lake access chalet-style home is located in the charming Heron Cove subdivision. Offering four bedrooms, cathedral great room, an open floorplan and some lake views. The propane stone fireplace is another eye-catching feature of the home. The dock slip is located within walking distance to this home or take the golf cart, which is included. 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, all within a short walk. Quiet cove centrally located to all DCL attractions. Sold turn-key!"
* PRICE LOWERED - $529,000 TO $499,900 
45
$499,000
4198 MARYLAND HWY, Oakland MD 21550
3
BEDS
2
BATHS
1,500
SQFT
$333
$/SQFT
1.73
ACRES
1962
BUILT
"BUSINESS PROPERTY & HOUSE$520,000 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.POSSIBLE INCOME POTENTIAL,RENTAL INCOME OR BUSINESS OPPORTUNITY."
* PRICE LOWERED - $535,000 TO $499,000 
42
$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!"
* PRICE LOWERED - $445,000 TO $425,000 
61
$400,000
2862 FINGERBOARD RD, Oakland MD 21550
4
BEDS
4
BATHS
3,268
SQFT
$122
$/SQFT
25.00
ACRES
1930
BUILT
"HOLY MOLY! Words do not do this property justice! 25 acre workable farm with a totally remodeled custom four bedroom home! Multiple outbuildings including barns, stables, shops, and garages--most have electricity and water supply! Abundant fencing for all of your potential farming desires. Nestled against the Yough river, this could be your dream haven for recreation, relaxation, fishing, hunting, ATVs... anything you can imagine! Additional 80+ acres available for purchase!"
35
$399,900
995 BETTS LN, Oakland MD 21550
4
BEDS
3
BATHS
2,548
SQFT
$157
$/SQFT
12.50
ACRES
2009
BUILT
"10 years young, you won't want to leave this log home in the woods! Over 12 wooded acres of privacy and seclusion, laced with trails and surrounded by low maintenance land. Centrally located - only a few miles to Deep Creek Lake, town of Oakland or Swallow Falls State Park. Open floor plan with vaulted ceilings, a wood burning stove and high end finishes throughout. Basement is partially finished with a potential 4th bedroom and bathroom under construction. Spacious decking and a must-have covered porch to enjoy the outdoors. Perfect as a vacation retreat or a full time residence. Located at the end of a privately maintained road."
27
$389,900
268 LEHMAN LN #41, Oakland MD 21550
4
BEDS
4
BATHS
2,784
SQFT
$140
$/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 - $395,000 TO $389,900 
28
$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."
82
$375,000
715 TANGLEWOOD DR, Oakland MD 21550
3
BEDS
4
BATHS
6,122
SQFT
$61
$/SQFT
3.31
ACRES
2000
BUILT
"This home is perfect resort style living in the beautiful mountains surrounding Deep Creek Lake. Located in Tanglewood on 3 acres, this home is designed to enjoy outdoor living with huge multi level deck with stone outdoor fireplace and built in hot tub. Indoors are multiple living areas including upstairs and downstairs family rooms, main level game room with built in bar, lower level exercise room and large home office. Enjoy any of the three large master bedrooms all with private baths. The warm woods used throughout add to the beauty of this mountain log home."
30
$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!"
33
$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."
44
$350,000
134 SECOND, Oakland MD 21550
10
BEDS
6
BATHS
4,640
SQFT
$75
$/SQFT
0.98
ACRES
1895
BUILT
"Lovely well-maintained apartment building w/ 10 bedrooms and 5 1/2 baths! All have been updated! Prime location. Watch Autumn Glory Parade from this property! Within walking distance to downtown Oakland for shopping, restaurants, museums, Our Town Theater, etc. Grossing $2800/month. Fantastic investment or live there and rent out the remaining 4 apartments as the current owner does. All apartments are kept extremely well by tenants."
38
$349,498
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!"
* PRICE LOWERED - $349,499 TO $349,498 
48
$324,900
112 NED RUN RD, Oakland MD 21550
4
BEDS
2
BATHS
1,736
SQFT
$187
$/SQFT
10.01
ACRES
1986
BUILT
"10 acre 4 BR/2 BA log cabin with covered front porch for gazing at a spectacular mountain view. Previously a tree farm, this property has all privacy you need within a 9 mile drive to town. Open concept living/dinning area with fireplace and newly remolded kitchen. Stainless steel appliances including gas cooking stove and Granite counter tops. 4 bedrooms and 2 full baths. Main living area walks out to covered front porch with views for miles! Fenced yard around home for pets. Several storage and equipment sheds. Wooded area behind home and cleared open area in front. House generator and fresh water spring on grounds for use with water storage tank. 2 car detached garage with easy access to full basement with lots of storage! Beautiful natural landscaping, fire pit and sheds for storing equipment, wood, etc. 26 apple trees and blueberry bushes on grounds, also Wildlife food plot. This property has been will maintained and has much to offer!"
 
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