Oakland Real Estate

Homes for Sale in Oakland, MD Between $750,000 to $1,000,000

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All Oakland, MD Homes for Sale Between $750,000 to $1,000,000

1515 Upperman Rd, Oakland
$785,000
1 Beds ⋅ 1 Baths
150± acres of pure Western Maryland adventure. Mature woods, open fields, ponds, winding creeks, mountain views, and a boundary adjoining State Forest come together to create an extraordinary private retreat. Travel approximately two miles off the main road to the last property along a private road, where the landscape opens to a world all its own. Explore miles of your own terrain, hike, ride, wander the woods, or simply disappear into the quiet. Set beneath the impressive backdrop of Backbone Mountain, rising to approximately 3,360 feet, the possibilities for outdoor adventure feel endless. Wild, beautiful, and wonderfully secluded, this is a rare opportunity to own a remarkable piece of Garrett County with the space and setting to create a mountain escape to be enjoyed for generations.

1515 Upperman Rd, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

184 Upper Penn Point, Oakland
$895,000
3 Beds ⋅ 2 Baths
Welcome to this charming 3Br, 2BA home in the quiet and serene Penn Point area of Deep Creek Lake. A Type A dock slip is included and is just an easy walk or golf-cart ride from the property, making lake days more convenient and enjoyable. Inside you'll find an inviting open concept kitchen, dining, and living area that flows seamlessly onto a spacious outdoor deck. Enjoy morning coffee, outdoor dining, grilling and entertaining while taking in the peaceful surroundings. The home sits on just under 1/2 acre, offering plenty of space to enjoy and potential for future expanding. The large, detached garage provides exceptional storage for your boat, jet skis, lake toys, and all your recreational gear. Whether you're looking for a year-round home or a Deep Creek getaway, this property offers the perfect combination of comfort, outdoor enjoyment, and access to the lake. Deep Creek Lake is a four-season destination with boating, golfing, hiking, skiing, dining, and activities for all ages. Conveniently located on Upper Penn Point Road, you'll be close to everything Deep Creek has to offer while still enjoying the peaceful setting. Come see all this property has to offer!

184 Upper Penn Point, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

395 Woodlands Hill Ln, Oakland
$899,900
5 Beds ⋅ 6 Baths
Welcome to Happy Hoursss... Hideaway, a stunning Deep Creek Lake retreat where breathtaking views, upscale amenities, and spacious indoor-outdoor living create the perfect getaway. With 5 bedrooms and 6 full bathrooms, this beautifully appointed home comfortably accommodates family and friends while offering plenty of room to relax and entertain. The main level features an inviting open-concept kitchen, dining, and living area with stainless steel appliances, a large center island, fireplace, abundant natural light, and beautiful lake views. A main-level primary suite and additional full bath add convenience. Upstairs, a second luxurious primary suite offers a walk-in closet and spa-like bath with a jetted tub and separate shower. The lower level is designed for fun and relaxation, with three bedrooms and three full baths, a second living area, fireplace, wet bar, and access to the deck and hot tub. The entertainment continues with a plenty of space to gather. Outside, enjoy two decks, a hot tub, fire pit, grill, room for games and entertainment, expansive yard space, ample parking, and a storage building for your outdoor gear. Whether you’re soaking in the hot tub under the stars, gathering around the fire, or enjoying a quiet morning, Happy Hoursss...Hideaway delivers an unforgettable Deep Creek Lake experience in every season.

395 Woodlands Hill Ln, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

15 Byran Dr, Oakland
$799,900
4 Beds ⋅ 4 Baths
Experience modern mountain living in this brand-new 2026 construction. This beautifully designed 4-bedroom, 4-bath home offers two spacious levels, quality finishes, and plenty of room for family and guests. Open layout with modern kitchen, island bar, and stone fireplace. Stamped concrete patio with covered fireplace and outdoor kitchen. Over half an acre of private wooded mountain-top space complete with fire pit and level usable yard. Andersen Windows and LVP flooring throughout. Ideally situated just minutes from Wisp Resort, Deep Creek Lake, state parks, restaurants, shopping, and year-round recreational attractions, this home provides the perfect blend of comfort, convenience, and adventure. Whether you're looking for a full-time residence, vacation getaway, or investment opportunity, this new construction is ready to make lasting memories.

15 Byran Dr, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

325 Markwood Dr, Oakland
$769,000
4 Beds ⋅ 4 Baths
LAKEFRONT 4BR, 3.5BA log home with over 3300sf and 4.35 acres of privacy! Lovingly maintained property with gorgeous views of the 10 acre lake from almost every room in the house! Peaceful surroundings with towering mature trees and just enough yard space in a very laid back, rural setting near Herrington Manor and Swallow Falls state parks. If that weren't impressive enough, Meadow Lake Estates community is adjacent to 598 acres of DNR / state land fronting on the Youghiogheny River. Set up for one level living - bedroom suite and laundry room on first floor. Features include whole-house generator, wood-burning fireplace, a recently finished basement adding a game room and a fourth bedroom, front and rear decks (trex on back deck), covered porches, fire-pit, wrap-around driveway and a spacious loft that serves as a third living room. Must see to appreciate the solitude of this fantastic home! Furnishings negotiable. Short term rentals are not permitted in this community.

325 Markwood Dr, Oakland

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

251 Robinwood Dr, Oakland
$775,000
5 Beds ⋅ 5 Baths
One-of-a-kind Youghiogheny riverfront estate offering 224 feet of water frontage . Soak in the sounds of the flowing waters and chirping birds, cloaked in a private canopy of mountain laurel, pine trees and mature hardwoods. 5BR 4.5 BA log masterpiece with attached 2 car garage and paved driveway. Thoughtful design and well maintained with spacious suites, floor to ceiling fireplace, log accent walls and exposed beams. Features include multiple fireplaces (wood & gas), Andersen doors & windows, trex decking, hardwood floors, metal roof, custom cabinets in kitchen & bedroom suites, eat-in kitchen, and sold furnished! Enjoy a picturesque setting in a riverfront setting with NO HOA restraints for this home. Seller also offering an adjacent unbuilt riverfront lot (#9) for $175,000 MLS #MDGA2012380

251 Robinwood Dr, Oakland

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

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