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3898 Underwood Rd, Oakland
$1,200,000
4 Beds ⋅ 6 Baths
Unique luxury home on 23 acres with 360 degree views of Pleasant Valley. 5,100 + SQ. FT. 4 ensuite bedrooms, 2 additional powder rooms, formal living room/ballroom, informal living room, sunroom, den, pantry and large dine in kitchen. 4 fireplaces. full basement, 3 car attached garage. Whole home generator. Everything in this home is first rate. A must see for the discerning buyer

3898 Underwood Rd, Oakland

Listing courtesy of Custer Realty & Auction. Contact:

Selling Office: Unrepresented.

2173 King Wildesen Rd, Oakland
$375,000
3 Beds ⋅ 2 Baths
Experience the beauty of country living in this new construction log home nestled in a peaceful rural setting. Crafted with quality materials, this home offers the perfect blend of modern comfort. Enjoy open-concept living spaces, vaulted ceilings, and windows that allow you to enjoy the pastoral and mountain views. The large front covered porch offers a great space to enjoy family and friends while enjoying your scenic surroundings. Whether you're looking for a full-time residence or a private retreat, this is it.

2173 King Wildesen Rd, Oakland

Listing courtesy of Taylor Made Deep Creek Real Estate. Contact:

Selling Office: Taylor Made Deep Creek Real Estate.

2241 Seton Way, District Heights
$342,000
3 Beds ⋅ 4 Baths
The seller may consider concessions made by the buyer with an offer. **NEWLY RENOVATED** 3-bedroom, 3.5-bath townhome in the heart of District Heights! Filled with natural light, this impressive home features a modern kitchen with a stylish peninsula, quartz countertops, a designer tile backsplash, and brand-new stainless steel appliances The bathrooms have been fully updated with striking tile work and upscale finishes, creating a spa-like retreat. Throughout the home, you’ll find brand-new hard surface flooring, fresh designer paint, modern fixtures, and elegant details that elevate the space. The fully finished basement includes a full bath and a versatile bonus room—perfect for a guest suite, home office, or media room. Ideally located just minutes from shopping, dining, parks, and major commuter routes, this home offers the perfect blend of style, comfort, and convenience. Don’t miss the chance to make this move-in ready gem your own—schedule your private tour today!

2241 Seton Way, District Heights

Listing courtesy of Area Real Estate. Contact:

Selling Office: Samson Properties.

1740 Old Crellin Rd, Oakland
$335,000
3 Beds ⋅ 3 Baths
Come see this beautifully maintained 3-bedroom, 3-bath Colonial-style residence nestled on a private 1-acre lot along Old Crellin Road in Oakland. Offering 2,300 square feet of living space, this home combines classic charm with modern comfort in an ideal location just outside town limits. Step inside to find a spacious and inviting layout, perfect for both everyday living and entertaining. The home is in excellent condition and has been thoughtfully cared for throughout. Enjoy outdoor living on the large wraparound deck, perfect for relaxing, hosting gatherings, or taking in the peaceful surroundings of this private setting. Additional features include: * Attached 2-car garage plus a detached 1-car garage for extra storage or workshop space * Whole-house generator that conveys for added peace of mind * Generous 1-acre lot offering space, privacy, and flexibility This property offers the perfect balance of tranquility and convenience—close to town amenities while still enjoying a quiet, country feel.

1740 Old Crellin Rd, Oakland

Listing courtesy of The KW Collective. Contact:

Selling Office: Unrepresented.

531 S 3rd St, Oakland
$320,000
5 Beds ⋅ 3 Baths
BACK TO ACTIVE!!! Buyers were unable to fulfill their home sale contingency. Welcome to this beautifully crafted 5-bedroom, 3-bath Stucco home, perfectly situated on a one-acre lot in charming Oakland, MD. With its timeless exterior, durable metal roof, and two car detached garage, this property offers both classic style and long-lasting function. Step inside to discover a light-filled, well-designed layout that blends comfort and space. The fully finished basement expands the home's livable space with laundry, a half bath and large family room. Located just minutes from Deep Creek Lake, shops, dining and four-season recreation, this exceptional property combines privacy, convenience and high end living in one of Western Maryland's most desirable destinations. Whether you are looking for a primary residence in or a spacious second home, this Oakland gem delivers it all!! If an active duty solider or veteran is interested in the house, the loan (through Planet Home Lending) is assumable at 2.75%.

531 S 3rd St, Oakland

Listing courtesy of Charis Realty Group. Contact:

Selling Office: Lake Homes Realty, LLC.

29 Woodmont Ln, Oakland
$305,000
4 Beds ⋅ 3 Baths
Immaculate 4-bedroom/3-bath countryside home less than 10 minutes from Oakland. This property has been exceptionally well-maintained — truly move-in ready and prepared for you to make your own memories. A private in-ground pool awaits you out back - perfect for summer entertaining. Enjoy the western exposure and stunning sunsets from your elevated deck. A .86 acre lot provides a great yard and space to enjoy the outdoors. Recently added roof, A/C unit, furnace, hot water tank and pressure tank provide added value and efficiency to an already beautiful home. A truly quiet countryside setting with easy access to town. Don't miss this one! Call now for more details or to schedule your private showing!

29 Woodmont Ln, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

Selling Office: Taylor-Made Deep Creek Sales.

711 Heritage Dr, Oakland
$249,000
3 Beds ⋅ 2 Baths
Welcome to easy living at this beautifully maintained 3-bedroom ranch-style home w/ attached heated garage. Updated Modern, spacious Kitchen area, Master BR Suite w/ private bath & walk in closet. Efficient gas forced-air heating w/ central air conditioning, ensuring year-round comfort in every season. Backing to trees, the home provides a peaceful, private setting while still being centrally located just minutes from shopping & schools. Outdoor recreation is right around the corner at Broadford Lake only minutes away, featuring kayaking and canoeing, a beach and swim area, scenic walking trails, and a pavilion - perfect for enjoying Garrett County's natural beauty. Call today for your private showing.

711 Heritage Dr, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

Selling Office: Railey Realty, Inc..

1570 Garrett Rd, Oakland
$225,000
3 Beds ⋅ 1 Baths
Located between Oakland and Deep Creek Lake, this log ranch is situated on 14.82 acres, including a stream, pond, barn and outbuildings with many possibilities to include potential subdivision configurations. The log home needs some TLC and updates; it is being sold as part of an estate. Some items of personal property remain in the house and on grounds. Those items are being removed. More photos will follow once the interior is emptied. The property will be sold AS-IS.

1570 Garrett Rd, Oakland

Listing courtesy of 1 Real Estate Source LLC. Contact:

Selling Office: Taylor Made Deep Creek Vacations & Sales.

141 Truesdale Rd, Oakland
$185,000
3 Beds ⋅ 3 Baths
Bring your vision and put your own personal touch on this great starter home! This property has great bones and endless potential. Featuring three bedrooms, two and a half bathrooms, and a large/open family room; it’s ready for your creative touch. Offering a nice level yard on a dead-end lane, which feels very private. The attached 1-car garage and rear shed provide the perfect extra storage space. Located close to schools, shopping, and DCL, this home could be a perfect flip, rental, or forever home.

141 Truesdale Rd, Oakland

Listing courtesy of Taylor Made Deep Creek Vacations & Sales. Contact:

Selling Office: Railey Realty, Inc..

627 Hamill St, Oakland
$180,000
3 Beds ⋅ 1 Baths
Inviting Country 3-Bedroom Traditional Farmhouse. This updated farmhouse offers a perfect mix of character and modern upgrades. Featuring 3 bedrooms, a bright sun porch, and a detached 2-car garage, the home is designed for both comfort and convenience. Enjoy outdoor living with a fenced-in yard, back deck, and peaceful valley views. The location is ideal—just minutes from town and shopping. Recent improvements include: LVT flooring & carpet, updated stove/range, metal roof and gutters, replacement windows. Full of farmhouse charm and move-in ready. Call now for your private tour!

627 Hamill St, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

Selling Office: Railey Realty, Inc..

729 E Oak St, Oakland
$165,000
3 Beds ⋅ 2 Baths
Great, affordable starter home located in Oakland with public water and sewer, one car detached garage, hot water natural gas heat. Two bedroom and full bath on second level and possible third bedroom on main level with 1/2 bath. Cellar basement with mechanicals. Washer and Dryer hookups, washer/dryer convey, are located on the back enclosed porch which has electric baseboard heat. Enclosed front porch also for relaxing on those warm summer evenings. Very convenient location, close to stores, hospital, shopping, etc. RAILEY REALTY IS NOT THE CARETAKER OF PROPERTIES LISTED BY IT. DURING INCLEMENT WEATHER CONDITIONS, PROSPECTIVE PURCHASERS AND THEIR AGENTS ASSUME ALL LIABILITY ASSOCIATED WITH OR BY WEATHER AT THE PROPERTY.

729 E Oak St, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

Selling Office: BHHS Touchdown Home Pros Realty.

8th & Dennett Road Street, Oakland
$150,000
A rare opportunity to acquire a high-potential 9.64 acre parcel located in the heart of Oakland. The location is very close to schools, grocery stores, restaurants, hospital and shopping. This site offers an ideal setting for residential, mixed-use, multifamily, or commercial development (subject to zoning approval). Easy access to infrastructure, with public utilities nearby at the street. This is an excellent opportunity for developers and investors seeking to build in a thriving town.

8th & Dennett Road Street, Oakland

Listing courtesy of Taylor-Made Deep Creek Sales. Contact:

Selling Office: Railey Realty, Inc..

460 W Liberty St, Oakland
$20,000
Lot within the town limits of Oakland with water and sewer hookups. This lot had a mobile home that was taken off. According to the owner, both Garrett County Planning and Zoning and the Town of Oakland have indicated that another mobile home can be placed on the lot but it has to be a NEW mobile home. According to P & Z, it must be a new mobile home and will have to be elevated 2' (three blocks) to be out of the 100 year floodplain. Buyer should verify with Garrett County Planning and Zoning and also the Town of Oakland. From a local surveyor: "You can see from the screenshot below that there is no building envelope outside of the floodplain. Any construction would need to be elevated above the 100’ floodplain + 2’ with special construction. For example, if you do an elevated house with a crawlspace, you can’t have mechanicals in the crawlspace and the crawlspace has to have flood vents installed to let water flow in and through the crawlspace. A floodplain elevation certificate would need to be done for any house for insurance and permitting. They would also need to do an MDE permit for impacts in the 100-yr floodplain, I believe." There is a two car detached garage on the lot. Property borders Town of Oakland Glades Park and Trail and directly across the street from the walking path at The Glades. Convenient location close to all town activities. RAILEY REALTY IS NOT THE CARETAKER OF PROPERTIES LISTED BY IT. DURING INCLEMENT WEATHER CONDITIONS, PROSPECTIVE PURCHASERS AND THEIR AGENTS ASSUME ALL LIABILITY ASSOCIATED WITH OR BY WEATHER AT THE PROPERTY.

460 W Liberty St, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

Selling Office: Unrepresented.

Hammond Street, Oakland
$20,000
A practical, in‑town lot close to everything that quaint downtown Oakland has to offer. You are just minutes to local shops, schools, and restaurants. Public utilities are available and easy access to main roads, making the possibilities endless.

Hammond Street, Oakland

Listing courtesy of Taylor Made Deep Creek Vacations & Sales. Contact:

Selling Office: Railey Realty, Inc..

Hammond Street, Oakland
$20,000
If you are looking for an affordable building lot located in the beautiful town of Oakland, this is it! This .54-acre lot is just steps to downtown Oakland, and minutes to restaurants, shopping, and grocery stores. Offering public water and sewer, the possibilities are endless.

Hammond Street, Oakland

Listing courtesy of Taylor Made Deep Creek Vacations & Sales. Contact:

Selling Office: Taylor Made Deep Creek Vacations & Sales.

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