23

Oakland, MD Homes under $300,000

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  • /47

    $300,000

    • 1 Bed
    • 1 Bath
    • 550 Sq Ft

    20160 Garrett Hwy Unit H708, Oakland, MD 21550

    Welcome to Will O' the Wisp Condominiums, where premium upgrades meet penthouse-level lakefront living at Deep Creek Lake! This fully furnished, beautifully updated, rarely available, top-floor two-level condo features one bedroom and one bath, offering 550 square feet of comfort, charm, and versatility — perfect as a vacation home, year-round retreat, or income-producing rental.Start

    Agent Photo

    Charlotte Savoy

    The KW Collective

    (301) 479-6357

    20160 Garrett Hwy Unit H708, Oakland, MD 21550
  • /20

    $215,000

    • 1 Bed
    • 1 Bath
    • 527 Sq Ft

    565 Glendale Rd Unit 212 - A, Oakland, MD 21550

    Silver Tree Suites offers 350' of pristine shoreline at Deep Creek Lake with western exposure centrally located to all area amenities. Unit 212A offers a one level floorpan with private bedroom on the second floor of building A which offers easy access to the lobby, elevator, gym, sauna, game room and patio area overlooking the lake. Condominium ownership at Silver Tree Suites offers ease of

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 923-7703

    565 Glendale Rd Unit 212 - A, Oakland, MD 21550
  • /39

    $259,000

    • 3 Beds
    • 2 Baths
    • 1,617 Sq Ft

    501 Christophers Way, Oakland, MD 21550

    Check out this opportunity to own your own mountain top chalet getaway complete with 3 bedrooms and 2 bathrooms and situated on 3 acres. A peaceful setting amongst mature trees and abundant wildlife with views of the surrounding mountains. Backbone Ridge community borders the highest point in Maryland and is conveniently located to several ski resorts, state parks, national forest & entertainment

    Dan Shockey Taylor Made Deep Creek Vacations & Sales

    501 Christophers Way, Oakland, MD 21550
  • /32

    $259,900

    • 4 Beds
    • 2 Baths
    • 1,760 Sq Ft

    413 D St, Oakland, MD 21550

    4BR, 2BA renovated home in Mountain Lake Park feels like NEW! Stripped down to the studs for a professional makeover. Stylish kitchen with stainless steel appliances and butcher block countertop, vinyl planking floors, efficient mini-split ceiling unit, modern fixtures and lighting, custom tile shower and reimagined bathroom space. Finished basement. Fenced backyard with deck and storage shed.

    Jay Ferguson Taylor Made Deep Creek Vacations & Sales

    413 D St, Oakland, MD 21550
  • /53

    $269,500

    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft

    315 Coolidge Ave, Oakland, MD 21550

    Well maintained brick rancher located in the heart of Oakland. This home offers a large kitchen open to the living room with a built-in fireplace, separate dining room, and new carpet through out. The basement is very clean, offering a clean slate for whatever you would like to do. The rear covered porch, deck and fenced in yard makes a great space to enjoy family and friends. The location is

    Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    315 Coolidge Ave, Oakland, MD 21550
  • /46

    $299,900

    • 3 Beds
    • 2 Baths
    • 1,736 Sq Ft

    1737 King Wildesen Rd, Oakland, MD 21550

    Nestled on 10 secluded acres of serene woodland and open fields, this traditional cedar-sided home offers the perfect blend of rustic charm and modern comfort—all just 10 minutes from downtown Oakland.This well-maintained home features 3 spacious bedrooms and 2 full bathrooms, including a main floor master suite for added convenience. Inside, you’ll find brand-new luxury vinyl plank (LVP)

    Justin Liller Railey Realty, Inc.

    1737 King Wildesen Rd, Oakland, MD 21550
  • /41

    $270,000

    • 1 Bed
    • 1 Bath
    • 400 Sq Ft

    83 Boston Post Rd, Oakland, MD 21550

    Escape to this delightful tiny home nestled in the breathtaking mountainous terrain of Deep Creek Lake, MD. This successful, turn-key vacation rental offers a unique blend of comfort and adventure, perfect for couples or solo travelers looking to unwind in nature. Airbnb describes this property as "One of the most loved homes on Airbnb, according to guests." While boasting a 4.94 star rating

    Brent Housley Railey Realty, Inc.

    83 Boston Post Rd, Oakland, MD 21550
  • /14

    $295,000

    • 5 Beds
    • 3 Baths
    • 1,800 Sq Ft

    611 E Oak St, Oakland, MD 21550

    Investors, this is an income producing, three unit building with three separate apartments, just a few minutes walk to downtown Oakland. Main level and upper level are two bedroom units and basement unit is a one bedroom. All units have current leases in place. One renter has been renting for 12 years, one for 10 years, and the third for eight years. The entire building is in excellent condition.

    Andrew Orr Railey Realty, Inc.

    611 E Oak St, Oakland, MD 21550
  • /47

    $289,000

    • 4 Beds
    • 1.5 Baths
    • 2,304 Sq Ft

    1764 Underwood Rd, Oakland, MD 21550

    Experience a fresh start in this stunningly completely renovated stone-raised rancher, perfectly situated along the breathtaking Cherry Creek! Every detail of this home has been thoughtfully upgraded, blending modern convenience with the beauty of its natural surroundings. The main level features 3 spacious bedrooms, an updated full bath, and engineered hardwood flooring throughout. The brand-new

    Laura Newhall Taylor Made Deep Creek Vacations & Sales

    1764 Underwood Rd, Oakland, MD 21550
  • /72

    $289,900

    • 2 Beds
    • 1.5 Baths
    • 1,600 Sq Ft

    1359 Cedar Ln, Oakland, MD 21550

    Discover a harmonious blend of comfort and adventure at this charming cabin located at 1359 Cedar Lane, Oakland, MD. Boasting approximately 1,600 sq ft of thoughtfully remodeled living space, this residence features 2 cozy bedrooms and 1.5 baths. The open-concept design showcases elegant laminated hardwood flooring throughout, complemented by a contemporary kitchen and a spacious family room that

    Chris Murphy Home Towne Real Estate

    1359 Cedar Ln, Oakland, MD 21550
  • /27

    $299,900

    • 1 Bed
    • 1 Bath

    565 Glendale Rd Unit 106B, Oakland, MD 21550

    Ground-floor end unit with lake views at Silver Tree Suites. This one-bedroom layout packs in a gas fireplace, full bath with tub/shower, and a tidy kitchenette with microwave, dishwasher, and full fridge. Balcony doors open to Deep Creek air and filtered lake scenes. Community perks include sauna, gym, game room and more. Sold turn-key, fully furnished. Ductless units for heat and A/C. Monthly

    Jon Bell Railey Realty, Inc.

    565 Glendale Rd Unit 106B, Oakland, MD 21550
  • /47

    $234,900

    • 4 Beds
    • 2 Baths
    • 1,456 Sq Ft

    2805 Shady Dell Rd, Oakland, MD 21550

    Nestled in the heart of Pleasant Valley, an area known for its peaceful country charm, this 4-bedroom, 2-bath home offers a serene setting. Enclosed decks run the full length of both the front and back of the house, with an additional private deck just off the dining room. The master bedroom features access to a covered deck and includes a full bathroom, while a second spacious bedroom also opens

    Laura Newhall Taylor Made Deep Creek Vacations & Sales

    2805 Shady Dell Rd, Oakland, MD 21550
  • /15

    $209,000

    • 3 Beds
    • 2 Baths
    • 1,850 Sq Ft

    170 Tannery Rd, Oakland, MD 21550

    Charming Country Home with Pond, Views & Space to Grow! Welcome to your peaceful getaway just south of Oakland! This cozy and well-kept 3-bedroom, 2-bath home sits on 1.7 private acres and offers so much more than you’d expect — including your very own pond, with blooming lilies and fish you can catch right from your backyard. Built from solid concrete blocks and topped with a durable metal roof,

    Jonathan Minerick Homecoin.com

    170 Tannery Rd, Oakland, MD 21550
  • /22

    $235,000

    • 2 Beds
    • 2 Baths

    4 Laurel Brook Dr, Oakland, MD 21550

    Opportunites abound at this wonderfully maintained home in Laurel Brook! Whether you are looking for an affordable full time residence, a vacation home, or a potential short term or long term rental property, Laurel Brook checks all the boxes! With its excellent location, right in between Deep Creek Lake and Oakland, you are just minutes away from enjoying everything Garrett County has to

    Eric Crawford Taylor Made Deep Creek Vacations & Sales

    4 Laurel Brook Dr, Oakland, MD 21550
  • /18

    $248,900

    • 2 Beds
    • 2 Baths
    • 1,678 Sq Ft

    2571 Shady Dell Rd, Oakland, MD 21550

    They call it Pleasant Valley for a reason! The property features a 2+ acre wooded area, a serene stream, several berry plants, 2 sheds, chicken coop, and a rear deck. Front porch and a fenced-in front yard. Inside, there is a large, bright living room, an updated kitchen with plenty of cabinet space, appliances, and sliding glass doors leading to the deck. The bathrooms have been updated. Full

    Paul Macy Garrett Land Sales, PC

    2571 Shady Dell Rd, Oakland, MD 21550
  • /29

    $239,000

    • 1 Bed
    • 1 Bath

    206 Mayhew Inn Rd, Oakland, MD 21550

    Just 2.5 miles from the scenic Swallow Falls State Park, this charming 1-bedroom, 1-bath house blends cozy living with endless potential. The upper level offers a cozy living area, a full kitchen, laundry room, bedroom, and full bath. But the real bonus? A spacious 2-car garage with its own entrance. It is perfect for a workshop, extra storage, or even a rental opportunity. With separate

    Jay Quinn Taylor Made Deep Creek Vacations & Sales

    206 Mayhew Inn Rd, Oakland, MD 21550
  • /3

    $279,900

    • Land
    • 18 Acres
    • $15,550 per Acre

    0 Bear Run Rd, Oakland, MD 21550

    UNRESTRICTED RAW LAND, DIRECTLY BORDERS STATE LAND (OVER 2000 ACS - MD DEPT OF NATURAL RESOURCES), FULLY WOODED & MARKETABLE TIMBER (RECENT TIMBER EVALUATED BETWEEN $100K-120K IN 2024), TROPHY BUCK HUNTING (INCLUDES CUSTOM BUILT HUNTING BLIND), SHORT DRIVE TO DEEP CREEK LAKE, STONES THROW TO YOUGHIOGHENY RIVER, OVERLOOKS DEEP CREEK LAKE VALLEY.

    Mike Haywood The Mike Haywood Group

    0 Bear Run Rd, Oakland, MD 21550
  • /29

    $219,900

    • Land
    • 1.10 Acres
    • $199,909 per Acre

    47 Ridgewood Dr, Oakland, MD 21550

    Prime Lake Access Lot in Mountainside – Perfect for Your Dream Home! Nestled on a one-acre wooded lot in the sought-after Mountainside community, this homesite offers breathtaking views of Deep Creek Lake and the ideal slope for a walk-out basement. Enjoy the best of four-season living with easy access to community lake privileges, state parks, restaurants, and WISP Resort. Plus, take advantage

    Michael Fenton Railey Realty, Inc.

    47 Ridgewood Dr, Oakland, MD 21550
  • /25

    $239,000

    • 2 Beds
    • 1 Bath
    • 1,569 Sq Ft

    41 Fox Den Rd, Oakland, MD 21550

    Nestled in the heart of Deep Creek Lake, this charming and fully furnished cottage offers the perfect blend of relaxation and investment potential. Recently remodeled, it features a brand-new modern kitchen that seamlessly opens to the living area, refinished wood floors, and upgraded electric,. The light and airy upstairs space enhances the home's inviting atmosphere, complemented by large

    Laura Newhall Taylor Made Deep Creek Vacations & Sales

    41 Fox Den Rd, Oakland, MD 21550
  • /3

    $249,900

    • Land
    • 24 Acres
    • $10,412 per Acre

    0 Bear Run Rd, Oakland, MD 21550

    UNRESTRICTED RAW LAND, DIRECTLY BORDERS STATE LAND (OVER 2000 ACS - MD DEPT OF NATURAL RESOURCES), FULLY WOODED & MARKETABLE TIMBER (RECENT TIMBER EVALUATED BETWEEN $100K-120K IN 2024), TROPHY BUCK HUNTING (INCLUDES CUSTOM BUILT HUNTING BLIND), SHORT DRIVE TO DEEP CREEK LAKE, STONES THROW TO YOUGHIOGHENY RIVER, OVERLOOKS DEEP CREEK LAKE VALLEY.

    Mike Haywood The Mike Haywood Group

    0 Bear Run Rd, Oakland, MD 21550
  • /31

    $259,999

    • 1 Bed
    • 1 Bath
    • 785 Sq Ft

    565 Glendale Rd Unit 312, Oakland, MD 21550

    $7,500 closing cost incentive being offered with a full price offer!! Own your very own slice of peace and relaxation at Deep Creek Lake. The Suites at Silver Tree sits along 350 feet of private shoreline. The resort is a destination for many, and this unit (one of the top rental units in the building) produces an annual revenue of $25k+. One of only four loft units that has a private bedroom at

    Sara Wells O'Malley EXP Realty, LLC

    565 Glendale Rd Unit 312, Oakland, MD 21550
  • /33

    $200,000

    • 5 Beds
    • 1.5 Baths
    • 1,536 Sq Ft

    511 Main St, Oakland, MD 21550

    The property offered for sale is located on the southwest corner of Maryland Highway, State Route 135 and Main Street, Deer Park. It is 2.5 acres, more or less, which is part of Parcel 0069 Map 0073, containing 32.20 acres, more or less. The remaining 30.00 acres on the northwest side of Route 135 is not included. The 2.5 acres is an estimate of area and is subject to a survey for

    Dan (Sussan) Duggan 1 Real Estate Source LLC

    511 Main St, Oakland, MD 21550
  • /63

    $299,000

    • 1 Bed
    • 1 Bath
    • 484 Sq Ft

    565 Glendale Rd Unit 115-A, Oakland, MD 21550

    Silver Tree Suites unit facing the lake with 1 bedroom on the main level. This is vacation rental that did $27,175 in 2021, $22,225 in 2022, and $22,936 in 2023. Property has on-site management and reservations. Silver Tree Suites is a waterfront condo community that has access to the lake, fitness center, sauna, laundry & game room. Next door to one of Deep Creek Lake's finest restaurants.

    Kevin Liller Railey Realty, Inc.

    565 Glendale Rd Unit 115-A, Oakland, MD 21550
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