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Oakland Real Estate, Homes and Condos for sale

All Oakland homes currently listed for sale in Oakland as of 02/17/2020 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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30
$1,349,000
139 PARADISE LN, Oakland MD 21550
5
BEDS
5
BATHS
4,046
SQFT
$333
$/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. Well established vacation rental home with 70k avg gross annual rental history. Weatherproof wrap-around decking. 100' lakefront w/Type A private dock. Conveniently located to restaurants, state parks, and area amenities. Call today to schedule your tour!"
70
$1,250,000
45 STANTON LN #4, Oakland MD 21550
3
BEDS
4
BATHS
2,677
SQFT
$467
$/SQFT
2019
BUILT
"This is a chance to own the largest Circumference Log Home in the world! Gain entrance to the Log Gates of Big Timber. This is a 3 master bedroom log home which is undoubtedly the most unique home on the lake, finished in a modern Lake Tahoe design. This home offers a gourmet kitchen with professional stainless steel appliances, granite countertops, blown glass pendant lights, center island and a marble tile backsplash. Custom metal stairs with oak plank treads and hickory live edge handrails. Oak trim throughout the home. Hickory plank hardwood floors throughout. A real stone wood burning fireplace with custom log mantle. 12 foot log walls on the first floor with 25~ vaulted ceilings over the great room, corrugated metal ceilings, loft area, T&G ceilings, Pella Windows and doors, LED lighting with custom pendant lights, recessed lighting, large front porch with log truss, side log purlin porches, 1st floor laundry room, endless tankless hot water tank, bathrooms include marble rain showers with custom glass enclosures, walk in closets, 200 amp service, oversized barn style doors with modern hardware, Lenox HE furnace, real stone foundation, stone landscape, commercial composite decking.Buyers can ride their golf carts across the street to the lake, where there is a large picnic area, and each unit is assigned it's own dock slip."
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."
30
$569,900
37 GILA TRL, Oakland MD 21550
5
BEDS
5
BATHS
3,688
SQFT
$155
$/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."
* PRICE LOWERED - $589,900 TO $569,900 
37
$517,500
1195 MOUNTAINVIEW DR, Oakland MD 21550
4
BEDS
4
BATHS
2,611
SQFT
$198
$/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."
* PRICE LOWERED - $539,000 TO $517,500 
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 
20
$379,900
55 VILLAGE DR #5, Oakland MD 21550
3
BEDS
3
BATHS
2,280
SQFT
$167
$/SQFT
2006
BUILT
"Cozy chalet-style log cabin located in the Yellowstone Village community. This home offers a covered front porch, three levels of living space, three bedrooms, hardwood flooring, two family rooms and two wood burning fireplaces. The finished sunroom makes an ideal spot to enjoy family and friends while enjoying a fire by the hot tub. Centrally located in the heart of DCL just minutes to the State Park, restaurants, cinema, grocery store and Wisp Ski Resort. Established rental Dan's Mountain."
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."
26
$369,000
268 LEHMAN LN #41, Oakland MD 21550
4
BEDS
4
BATHS
2,784
SQFT
$133
$/SQFT
2007
BUILT
"Price reduced AND recent owner updates! The entire home plus all exterior decking has been re-stained AND the owner added a brand new hot tub. 4BR/3.5BA home in Gallatin Woods! Quiet, yet central, log home community off Lakeshore Drive. Enjoy the vibe of living in a beautiful forest laced with natural boulders, and the lake is a few hundred yards away. Large great room with a screened in porch and multiple gas fireplaces, inviting hot tub, hand-hewn log steps and a vaulted ceiling. Ample yard space and parking. Established vacation rental 'Keep Dreaming. This home is not a traditional condo, though it must be listed that way. Gallatin Woods community is a landominium where you have full ownership (and all decision making) of the structure of the home, as well as own the lot. The surrounding area is a form of common area that falls under condominium law in Maryland. Call for more details about this unique property!"
* PRICE LOWERED - $389,900 TO $369,000 
28
$364,700
95 GALLATIN DR #3, Oakland MD 21550
4
BEDS
4
BATHS
2,288
SQFT
$159
$/SQFT
2005
BUILT
"Custom Mountaineer Log Home. Designed to be a Tranquil Getaway, Relax on the Back Deck and Listen to the Babbling Stream & Release all of your Daily Stresses Away. Open Floor Plan, Wide Planked Yellow Pine Hardwood Floors, Spacious Kitchen Includes an Island & Breakfast Bar, Adjacent Dining Area for Entertaining Family and Friends for Those Special Dinners. On Those Chilly Evenings Cozy up to the Beautiful Wood Burning Fireplace that Includes River Rock from Ceiling to Floor. 4-Master En-Suites, Everyone Enjoys Their Own Full Bath. Private Wooded Setting Surrounded by Hemlocks, Beautiful Ferns and Oak Trees. Large Paved & Circular Driveway that Sets Back from Gallatin Drive. You are Only Minutes to all of Deep Creek Lake's Amenities; Wisp Ski Resort, ASCI White Water Rafting, Tube Run, Ice Skating, Zip Line, Cross Country Skiing, Boat Rentals, Restaurants and More.....Within minutes to Swallow Falls State Park, Herrington Manor State Park & Deep Creek Lake State Park. Call Today to Schedule a Showing of this Unique Property..."
* PRICE LOWERED - $384,700 TO $364,700 
30
$359,900
85 STOCKSLAGER RD, Oakland MD 21550
3
BEDS
2
BATHS
2,300
SQFT
$156
$/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 $479,500,000 giving it over 13 total acres at 123 Stockslager Road. FULLY FURNISHED WITH 2 KAYAKS TOO!"
* PRICE LOWERED - $364,900 TO $359,900 
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."
43
$349,900
412 TANGLEWOOD, Oakland MD 21550
3
BEDS
4
BATHS
3,520
SQFT
$99
$/SQFT
2.00
ACRES
2006
BUILT
"Beautiful log home located in the Tanglewood Subdivision. This home offers three bedrooms plus a main level sitting room, an open floorplan, hardwood flooring and granite counter tops. The floor-to-ceiling gas stone fireplace in the great room catches your eye from the moment you walk in. The lower level family room gives you additional space to enjoy with friends and family. An attached two-car garage is just another added feature. The exterior space is just as pleasing, offering a large front deck and a landscaped yard featuring large natural boulders, a fire pit and plenty of privacy. This home is an established rental, but would also be a great full time residence. The location is just minutes to Oakland, Swallow Falls State Park, Herrington Manor State Park and Deep Creek Lake."
38
$345,000
21651 GARRETT, Oakland MD 21550
3
BEDS
2
BATHS
1,053
SQFT
$328
$/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 - $349,000 TO $345,000 
22
$285,000
193 RED RUN RD #1-B-1, Oakland MD 21550
2
BEDS
2
BATHS
"Well-maintained one-level lake access condo with assigned boat slip. Enjoy the lovely lake views from this unit with walk-out level from your patio. Includes 2 bedrooms, 2 baths and an extra room that can be used as an office, etc. Red Run offers so many amenities such as a swimming pool, tennis courts and lots of common area. The lakefront area has deep water. Can be used as a full-time residence or vacation get-away. Very quiet atmosphere in this area. Priced right!"
33
$249,900
159 GLOTFELTY DR, Oakland MD 21550
4
BEDS
2
BATHS
3,000
SQFT
$83
$/SQFT
1.09
ACRES
1980
BUILT
"You won't believe the countless built-ins and unique features of this home! Lots of attention to detail in every room! Built-in desk in both kitchen and office plus a dry bar in game room. Flue in home in case you want to add a wood-stove. Also an outside heating unit that will burn either coal or wood can be used. Stacked stone and tongue' n groove panels accent the walls and add charm. Property includes a pavilion, patio, enclosed front porch and back porch, 3 car garage and 2 additional sheds. Property inspections are welcome, but property is being sold as-is. Fantastic location being only 5 minutes to Deep Creek Lake and 5 minutes to Oakland, MD. Private setting in a quiet neighborhood."
57
$248,900
393 FOX TAIL RD, Oakland MD 21550
3
BEDS
2
BATHS
2,496
SQFT
$100
$/SQFT
0.71
ACRES
2006
BUILT
"Find yourself tucked away in this 3BR, 2BA cabin situated on 0.71 corner acre lot. Featuring one level living, open floor plan, two living spaces, and wood burning fireplace. Master BR offers two walk-in closets with attached full bath. Basement has inside/outside access with over sized garage. The outside area offers a pull-through carport, large gravel driveway and deck for your enjoyment. Located in the desirable Yough Mtn Resort that offers 50+ miles ATV/snowmobile/hiking trails. Fishing/hunting areas! Many community amenities. Minutes from Swallow Falls, Herrington Manor and Deep Creek Lake. Call today!"
35
$245,000
522 E GREEN ST, Oakland MD 21550
3
BEDS
4
BATHS
1,503
SQFT
$163
$/SQFT
0.29
ACRES
1983
BUILT
"Attractive 3BR, 2FB/2HB stone & cedar home with 2 car garage on a corner lot near downtown Oakland. Property essentially offers one-level living and many installed handicap accessible features. Other features include: updated kitchen cabinets, granite counter-tops & backsplash, updated flooring throughout home, tongue and groove wooden accent walls, beamed ceilings, AC via 2 Mitsubishi wall units, gorgeous stone fireplace, and 2 master suites. Improved, full basement with outside access, 2 mudsinks (one in laundry area), Andersen windows, multiple heat sources (efficient hot water boiler system and woodstove). Newer architectural shingled roof, cedar shake shingles and a fully fenced backyard area with storage shed. Solid-built and well maintained - move in ready."
* PRICE LOWERED - $259,000 TO $245,000 
36
$244,000
366 GLENDALE RD, Oakland MD 21550
3
BEDS
2
BATHS
1,392
SQFT
$175
$/SQFT
0.11
ACRES
1997
BUILT
"PRIME CENTRAL LOCATION! SHORT WALK TO DEEP CREEK LAKE, SEVERAL RESTAURANTS, LIVE MUSIC AND MOVIE THEATER. DCL STATE PARK WITHIN A COUPLE MILES. SHORT DRIVE TO SKI SLOPES . SOLD FURNISHED-TURNKEY FOR IMMEDIATE ENJOYMENT OF DEEP CREEK LAKE AND ALL LOCAL ATTRACTIONS! Twin/semi-detached completely remodeled 3 BDRM 2 BATH home meticulously maintained with filtered lake view. Public water and sewer service. HVAC heat pump and humidifier added 2018. HardiPlank low maintenance exterior siding. No HOA/ dues. ZONED TOWN RESIDENTIAL - which provides for a few selected types of small commercial uses. Honeywell home control monitoring system with remote programmable thermostat. Granite counter tops in kitchen and all baths. Tasteful decor and furnishings included so you can start enjoying a simple, quality lifestyle in DCL as a primary residence, second home or possible rental property. Easy access level driveway. Call today to schedule your showing appointment!"
* PRICE LOWERED - $259,000 TO $244,000 
50
$234,900
320 N BRADLEY LN, Oakland MD 21550
4
BEDS
2
BATHS
1,936
SQFT
$121
$/SQFT
0.90
ACRES
2004
BUILT
"Conveniently Located to Oakland's Amenities is this 4 Bedroom Ranch Home with .90 Acres! Enjoy the Gorgeous Sunsets from the Back Deck & Patio. Walking Distance to WildWood Athletic Club and the Oakland Golf Club. Open Floor Concept, Lower Level offers a Wealth of Possibilities for Additional Rooms; Plumbed for a Third Full Bath. Attached 2 Car Garage, Level Walk-Out to the Large Back-Yard Area. Fenced-In Chicken Coop, Huge Garden Area. Concrete Patio & Main Level Deck for Entertaining Family & Friends. Open Plan Dining Room that is Conveniently Located Next to the Spacious Kitchen with a Center Island, Breakfast Counter, Kitchen Window Over the Sink Views the Beautiful Back-Yard. Adjoining Bright Breakfast Room with French Doors Leading you to the Large Back Deck; Kitchen Pantry off of the Breakfast Room. Main Level Includes 4 Bedrooms Including the Master Suite-Attached Master Bath with Double Vanities, Garden Tub & Walk-In 2 Seated Shower, also a Walk-In Closet. Separate Laundry Room on the Main Level. The Lower Level offers an Office Space for Someone who Works from Home. Further Parking is Provided by the Wide Paved Driveway Which Can Accommodate up to 6 Cars. This is a Great Property in a Special Location. Call Today to Make an Appointment to View This Property..."
* PRICE LOWERED - $241,900 TO $234,900 
11
$230,000
225 CLIFFSIDE CT, Oakland MD 21550
2
BEDS
2
BATHS
1,157
SQFT
$199
$/SQFT
20.75
ACRES
2000
BUILT
"LITERALLY - up where the eagles soar! Hard to find a location isolated but accessible - but this is it! VIEWS- VIEWS - VIEWS. Multiple heat sources. Back up generator (with switch over). Over 20 acres - 20.75 acres (Lots 5 & 6). Access to Potomac State Forest. Open design with two bedrooms. Garages(detached and attached). Deck. Porch. Attached storage areas. Sold as-is."
16
$220,000
189 PLEASANT HILL CIR, Oakland MD 21550
3
BEDS
3
BATHS
1,320
SQFT
$167
$/SQFT
2.14
ACRES
1987
BUILT
"Unique Opportunity! 3BR/2.5BA Cabin on over 2 acres with a private pond. Private, yet close to town. Sit on your back deck overlooking your pond. This type of property only come around once very so often."
46
$219,900
1875 FINGERBOARD RD, Oakland MD 21550
4
BEDS
2
BATHS
1,896
SQFT
$116
$/SQFT
3.00
ACRES
1955
BUILT
"Beautiful 4 Bedroom, 1 1/2 Bath home situated on 3 acres. This home features three levels of living space including a true master suite with office connected on main level. Three bedrooms with 1/2 BA on upper level and full unfinished basement Great room offers wood burning fireplace. Separate living space with hardwood floors. Enjoy one of 3 porches, fire pit in the backyard and large fenced in garden. A gravel driveway wraps around the 2 car detached garage. This home is less than 5 minutes to WV and the town of Oakland. Call today for your private showing!"
* PRICE LOWERED - $225,900 TO $219,900 
11
$199,900
179 MITCHELL DR, Oakland MD 21550
4
BEDS
4
BATHS
3,214
SQFT
$62
$/SQFT
0.58
ACRES
1975
BUILT
"Opportunity to own a spectacular 3200sf +, 4 bedroom, 3.5 bath home with a heated in-ground pool + pool house - for under $200k! Many improvements, including an $80k+/- kitchen upgrade with solid surface counters, cabinets + high-end stainless appliances, newer pool liner, bathroom renovations, more. 2 car attached garage, potential in-law suite or 2nd master. End of cul-de-sac lot with fenced backyard and backing to private forest. All this in Mitchell Manor - no town taxes + central location + county maintained roads. Sold AS-IS."
* NEW LISTING 
 
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