Oakland MD Real Estate & Homes for Sale
The median home value in Oakland, MD is $352,500.
This is
higher than
the county median home value of $167,300.
The national median home value is $219,700.
The average price of homes sold in Oakland, MD is $352,500.
Approximately 38.58% of Oakland homes are owned,
compared to 42.53% rented, while
18.89% are vacant.
Oakland real estate listings include condos, townhomes, and single family homes for sale.
Commercial properties are also available.
If you see a property you’re interested in, contact a Oakland real estate agent to arrange a tour today! 
ADDITIONAL INFORMATIONAffordable country living, yet just 10 minutes into downtown Oakland. This 3-bedroom stone home sits on nearly 1.5 acres with an incredibly private feeling back yard and a very tastefully updated interior. Enjoy the covered front porch and the peacefulness of living in the country. The 2,200 sq ft detached garage can be used to store all the toys, add additional living space overhead, or potentially run a business. With no HOA, level land, and state road frontage, this home is a must-see. $2,450,000315 Glendale Road Oakland, MD 21550
ADDITIONAL INFORMATIONLooking for that elegant lake front property that makes you feel right at home? Look no further! This beautifully appointed 7 bedroom 4 1/2 bath offers just that! This open floor plan home has several distinct living areas and spots to get away from it all! The main level offers a gourmet kitchen with plenty of storage and cooking areas which flows right into the dining area with great views of the water! The main living room makes you feel right at home with its cathedral ceilings and massive windows to let an abundance of natural light into the home. Main level Master Suite offers a place to hide from everything and just relax. Downstairs offers large family room and 4 bedrooms . Just off the family room, you can relax in the sauna! Off the family room, the level back yard flows down to 100' of lake front and your own private dock! The upper level of the home has an loft area with incredible views and 2 other bedroom and bath. Don't miss out on your chance to be a part of this unique property here at Deep Creek Lake! 
ADDITIONAL INFORMATIONThree level end unit with some updates, including granite countertops. Close proximity to Deep Creek Lake State Park, shopping, dining and entertainment. Perfect for a second home or as an investment.More photos coming as soon as possible. $300,0003634 Hutton Road Oakland, MD 21550
ADDITIONAL INFORMATIONLocated just outside of Oakland, MD this home is close enough to all the amenities of town for convenience, but offers the advantage of living in a peaceful country setting. This 4.87 Acre Farmette property is partially fenced and was once used to raise horses. A Large two level barn gives ample storage for animals or otherwise. A young orchard to the side features Apple, and Pear trees, kiwi and blueberry bushes. The huge 7 bedroom home with 3 full and two half baths is the centerpiece. Two finished levels; Laundry, kitchen, living room, dining area , solid oak doors, 3 bedrooms (one of which is a master bedroom), and 2 bathrooms all on the main level. The second level has an additional 4 bedrooms and bathroom with a kids playroom/gaming room. A full sized partially finished basement has two half baths and was originally designed and used as a daycare, but now offers a blank canvas opportunity to finish into an area for entertaining or anything else you could imagine. Current owners have done a considerable amount of updating including a new shingle roof within the last two years, new wood flooring on the main level, newer light fixtures, and more. This property is just waiting for someone to come in and make it their own. Call to schedule a showing today, this one won't last long! $189,900214 I Street Oakland, MD 21550
ADDITIONAL INFORMATIONCharm & character throughout this 3BR Victorian home in Mt Lake Park. Known as the "Stain Glass house" you will find beautiful glass windows & fixtures in the house with one of a kind stained glass artwork. Main floor has kitchen, 1/2 bath, dinning, living, sunroom & a grand hall way that walks out to covered front porch. A large family room addition was added on the back of the main level, walking out to your backyard with carport & gazebo. Plenty of rooms on the main level you could possibly convert to a main level Bedroom? Upstairs, you will find 3 bedrooms & a full bath. The lower level/basement area has tons of storage, washer/dryer, workshops & possible garage. Pull down attic with extra insulation. Original stair way, hard wood floors, & many unique stain glass windows fill the home. Property sits on a double lot w/ 3 sheds (2 w/electric) and nice level side yard. Great bones for someone that loves history & needs plenty of room! Community recently added a park with water features & pavilion. Call today to see this cute home with lots of charm! House is being sold " As Is" 
ADDITIONAL INFORMATION3BR, 3.5BA front row + lake view condo at Roman Ridge! Attractive layout offering 2 master suites, open living room and mostly level entry. Spacious lakeside deck, gas fireplace, central A/C, brand new carpet on stairs/lower level, hot tub and plenty of parking. Lake View Lure is an established vacation rental generating $51k+ in income in 2021. All future rental income will be yours! The property will convey essentially turnkey. Roman Ridge monthly HOA fee offers tremendous value - cable TV, water, insurance, trash, pest & road/snow removal. Incredible location, close to all DCL activities and within walking distance of Traders Coffee, Brendas Pizzeria & High Mountain sports. $395,000157 E Omar Street Oakland, MD 21550
ADDITIONAL INFORMATIONCustom 3BR, 2.5BA home on historic Second Street near downtown Oakland. Every exterior angle of this home offers a distinct design feature and boasts quality construction. Built in 1991, this home is one of the most modern homes available in the historic district and is conveniently located along the world famous Autumn Glory parade route, In fact, this private corner lot is the very first to see the start of the annual parade, marching up Omar St. and making the turn onto 2nd St. Entertain your guests in the open, grassy lawn or on your exterior deck, soaking in the sunshine. Enjoy the convenience of an over-sized garage, an attached carport and a paved driveway for overflow parking. Mostly level entry into the home, loaded with handicap accessible features and design. Interior features include a functional kitchen with hand crafted cabinetry, open living room area with abundant natural light and attractive window placement, 3 spacious bedrooms to choose from with a main level master suite. You will be comfortable in any climate with the efficient hot water baseboard heating system and 4 mini split A/C units. Add in a tankless hot water, a huge basement area for additional living space or storage and built-ins cabinets for maximum storage capabilities. This home has been immaculately maintained and well cared for - no expense has been spared. If you have errands or business in town, you are only a few blocks away from the hospital, library & post office, as well as every shop, restaurant, entertainment option or event that downtown Oakland has to offer! $104,900716 E Reese Street Oakland, MD 21550
ADDITIONAL INFORMATIONGreat opportunity to own a 3 bedroom 2 bath home in Oakland in this price range. Ready to move in and sits on a double lot with detached garage! New roof as well!!! Public water and sewer. $139,90011 Obrien Street Oakland, MD 21550
ADDITIONAL INFORMATIONAn excellent home waiting for its new owner! This 3 bedroom, 1 bedroom split level home offers many recent upgrades including metal roof, electric furnace and remodeled bathroom on the main level, all at an affordable price! Call today to schedule a private showing! 
ADDITIONAL INFORMATION5BR 4BA with lake access & filtered lake views! Enjoy 2 levels of lake living, complete with 2 gas fireplaces, open kitchen & living areas, spacious bedrooms and an inviting covered porch area on the deck. $56k in vacation rental income, 'Crosswinds' is the home you have been searching for. Convenience is the key - enjoy walking distance to your community lake access area, just a few hundred feet away. Rent a boat or jet ski at Silver Tree marina and visit Dutches at Silver Tree restaurant and bar - right next door! You are a short drive to DCL state park, Honi-Honi & other area shopping/entertainment. Pride of ownership is evident throughout - owners have continually re-invested in the property; most recently a brand new hot tub (April 22). The hot tub is perfectly placed in a vibrant outdoor oasis, nestled by a small stream that feeds into the lake. Silver Tree Landing is an attractive, well designed community off of coveted Glendale Rd. $600,00060 Gallatin Drive Oakland, MD 21550
ADDITIONAL INFORMATIONBeautiful log style home in the Gallatin Woods community. Prime location off Lake Shore Drive, you will be in the heart of everything Deep Creek Lake and the surrounding area has to offer. 5 minutes to Wisp Ski Resort or Deep Creek Lake State Park, dining, shopping, etc. The native stone fireplace, hardwood floors, and log beam vaulted ceiling give this home the true feeling of a mountain retreat. Outside, enjoy relaxing around the firepit or soaking in the hot tub while being surrounded by a private wooded landscape. This is a must see! Call me today for more information or to schedule your private tour! $169,000609 I Street Oakland, MD 21550
ADDITIONAL INFORMATIONThree bedrooms, one bath, a nice size kitchen with dining area, and a large living room with a gas fireplace. There is also a mini-split installed in the living room which cools the entire house. Outside, the back yard is fenced in, there is a deck, and there is a four car parking area. The house and property are very well taken care of, and are in very good condition. $2,895,000289 Glendale Road Oakland, MD 21550
ADDITIONAL INFORMATIONExperience 'Enchanted Lakefront' with this stunning 8 bedroom home! Enjoy all four seasons with room for everyone! Established, income producing vacation rental in the heart of Deep Creek Lake. Centrally located on Glendale Road, this sprawling home features three levels of living space, private dock, beautiful hardscaping patio area, lakeside deck, and so much more. Sit around the outdoor firepit on a warm summer evening or inside in front of the fireplace in the winter months. This one won't last! $2,200,0002411 Lake Shore Drive Oakland, MD 21550
ADDITIONAL INFORMATIONElegant 4/5BR lakefront home with a whopping 382+ ft of waterfront - nearly 1.5 acres in total! Fully renovated in 2008, this home offers a contemporary lodge vibe - 3 stacked stone + wood burning fireplaces, beamed ceilings wood floors and accents. Peaceful, quiet setting and just enough trees for privacy while maintaining views of the water. Features include multiple master suites, custom tile bathrooms, eat-in kitchen, multiple living areas, attractive fixtures, instant hot water and unique design throughout. Magnificently maintained property boasts a wraparound lakefront deck, a screened porch with fireplace and elaborate hardscaping designs while offering an otherwise low maintenance yard. 2 paved parking areas. Conveys mostly furnished with high end, quality furniture & decor package. Includes an separate .10+ acre parcel with 30 ft waterfront and a Type A dock (non-buildable). Deep water access and wide views of the lake with western exposure from the house and dock. Must see! 
ADDITIONAL INFORMATIONStunning lakefront property located in the sought after, no wake Red Run Cove. The property has 2 streams that you can actually catch trout in! This absolutely charming chalet is waiting for your family and friends to kick back and relax. Vaulted ceiling with a wall of glass overlooking Deep Creek Lake and the stream! This has an open kitchen/living/dining area with wood floors and a beautiful gas stone fireplace completes the picture. A private primary bedroom and bath is located on the upper level with 2 Bedrooms and a bath on the main floor. This picturesque, park like, lakefront lot is like no other. Pines trees throughout make it as beautiful in the winter as it is in the summer! Sit by the firepit next to the babbling stream or cross the second stream on a bridge that takes you to the water's edge. Launch your canoes and kayaks and explore Deep Creek Lake. The dock for your boat is just a few feet away in the Millhouse Manor docks. This property is a must see! 
ADDITIONAL INFORMATIONOne level living! 3BR 2BA home had been renovated top to bottom (2008) - stacked stone fireplace (gas), hardwood floors, attractive cabinets & countertops. Recently upgraded to a metal roof. 2 car attached garage and a large, unfinished basement for storage. Enjoy ample sunshine in the level yard or relax on the rear decking. Outbuilding negotiable. Tenant in place through mid August - $1600/mth. $129,000591 Kings Run Road Oakland, MD 21550
ADDITIONAL INFORMATIONUnique opportunity!! Enjoy a spectacular 12+ acre piece of ground with a completely renovated trailer. Rent out the trailer and use as an investment property, OR live there while you pursue building elsewhere on the property. Very central location near all Oakland & Deep Creek Lake amenities! Neighboring home is also for sale for $189k. Sellers would potentially be open to a package deal. Schedule your showing today! $189,000567 Kings Run Road Oakland, MD 21550
ADDITIONAL INFORMATIONAffordable home in a great location! This property has endless opportunities. Fix up the lower level and enjoy a very spacious home OR rent it out separately and help pay your mortgage! The main level of the home has been renovated. Perfect for first time homebuyers or anyone looking for simple living. The next door property (trailer and 12+ acres) is also for sale for $129k. Seller would consider a package deal for both. Come take a look for yourself! Beautiful setting and close to all Oakland & Deep Creek Lake area amenities. 
ADDITIONAL INFORMATIONUnobstructed LAKE VIEWS from this awesome Four Hooppole unit. These earlier Deep Creek communities enjoyed the luxury of LOCATION and gorgeous Lakefront. A total of 48 townhomes on 10 Acres of some of the most beautiful grounds cannot be recreated. (Most condominiums are 9-10 units per acre in TC Zoning). Let's talk about the bones.......... the most important aspects of remodeling have been addressed. Before their ownership, the original Windows and Sliders were replaced with Pella. Brand New in 2022 - Carrier ductless Mini-Split HVAC unit added. Original electric baseboard still in place available for back-up heat. Individual Units per room can be independently controlled (+ Remotes) for your comfort. Download an App and warm or cool your unit before your arrival; monitor your vacation home when you are not here. Floors - goodbye to all the carpet and now we have resilient Laminate Plank Wood flooring that withstands vacation home pet and people foot traffic. Carpet only in 2 lower bedrooms. Upper Level Bedroom is its own au-suite with an adjacent open loft that can be used as a TV room, reading area or an additional non-private bedroom. Bathrooms remodeled with Ceramic Tile and Granite Countertops. Kitchen updated with Black Stainless Appliances (see photos) and quartz countertops. DECKS - upper deck has composite deck boards. Lower Deck - Building F has the unique feature of an expanded lower deck that almost doubles / triples your deck area with no common walkway fronting it. Walk on directly to the grassy lakefront and head for your boat and the lake. A private sandy beach area is another great community amenity. Tennis Courts, extra parking for boat trailers, and a rustic log cottage meeting room. SOUTHERN LAKE Beauty but only 10.6 miles to Wisp Ski Resort, Lodestone Golf; 5 miles to Arrowhead Market - Uno's - Movies and 7.6 miles to Walmart . Parking Lot was just done by association in 2021 . EXCLUSIONS: Painting with stork, painting with landscape, round gold mirror, placque: "Welcome to Lake House", LR coffee table, LR TV, and extra bed in Upper level. Any items that are not furniture including but not limited to beddings, kitchen contents, knick - knacks, personal effects do not convey and may remain wholly at sellers discretion. 
ADDITIONAL INFORMATIONViews throughout!! If you are looking for a home with a dock slip and amazing views, this is the one for you!! It is at the heart of Deep Creek Lake and walking distance to the Honi Honi Bar and many restaurants. All four bedrooms are master suites and with three levels there is plenty of room for the entire family. All you have to do is pack your clothes and move in because it is coming completely furnished and turnkey. Call today for a showing!! $120,0006471 Gorman Road Oakland, MD 21550
ADDITIONAL INFORMATIONSerious rental/development investment opportunity! 6471 Gorman Rd is an 8.7 Acre parcel located just outside of Oakland. This property offers the opportunity to have FOUR income producing rentals in one location. Currently there are three mobile homes set up, two have lease agreements in place with tenants paying utilities (54 and 77 Apache Trail), and one additional site is sitting empty with Septic and electric just waiting for a fourth unit. Don't miss this opportunity, Call today for a showing! 
ADDITIONAL INFORMATIONBeautiful 5 bedroom 3 1/2 bathroom home on 4.63 acres in the very popular Valley View Estates subdivision. This home features 3 levels of finished living space with bedrooms on every floor. With an open floor plan and a very large living room with multiple sliding doors to the large, but private deck to enjoy warm summer nights. This home features a main level master bedroom, and 2 bedrooms on the upper level as well as 2 over sized bedrooms on the lower level. There is a detached 2 car garage with stairs off the back leading to the very spacious loft storage or man cave/she shed. This home is equipped with a whole home sprinkler system with holding tank as well. Within minutes to all lake activities, restaurants, and ski area. $250,000405 Sunnyside Road Oakland, MD 21550
ADDITIONAL INFORMATIONIf you are looking for one level living in a spacious 3 bedroom home with plenty of storage and privacy then this is the home for you. This home is on a large 1.57 acre of ground just south of Oakland (County seat) where you are just a few minutes from Shopping, Schools, Churches, Restaurants and entertainment. Plenty of space in the home and an oversized 2 car attached garage. Enjoy the hot water baseboard heating system or the gas Fireplace in the Livingroom. $669,000250 Lehman Oakland, MD 21550
ADDITIONAL INFORMATIONImmaculate 4 bedroom log home in the highly sought after Gallatin Woods community. Custom built with custom finishes throughout. Granite counters, hardwood floors, 2 fireplaces, extensive hardscaped patio and outdoor fireplace, and the list of upgrades literally goes on and is available on request for the discerning buyer. Minutes from Deep Creek Lake and all of the area amenities yet tucked away in a log home community. 
ADDITIONAL INFORMATIONVery impressive 5 Bedroom home on 3+ acres offers a spacious 3,700 sq. ft. open floor plan located 15 minutes to Oakland and Deep Creek Lake. Enter through the Bright Sun Room into the Great Room & enjoy the Wood Cathedral Ceilings , Gas Fireplace on the main level. His and Her private offices make it easy for multiple work spaces to work from home. The Master Bedroom suite is 30' x 20' and offers a custom tile shower your sure to remember. Your Pets will love their private indoor suite with heated floors and outdoor access. High Efficiency Heating and Cooling systems provide very nice conditioned space throughout the home. High Speed Broadband Internet provides the Home Office and TV Steamer a variety of options for work and leisure. Lots of indoor conditioned storage and a detached 24' x 40' garage finish off this property perfect for a growing family. Call today for your Private Tour.
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