24

5-Bedroom Homes for Sale in Oakland, MD

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  • 56 Bee Tree Ln, Oakland, MD 21550
    56 Bee Tree Ln, Oakland, MD 21550
    56 Bee Tree Ln, Oakland, MD 21550
    /141

    $2,845,000

    • 6 Beds
    • 7.5 Baths
    • 5,100 Sq Ft

    56 Bee Tree Ln, Oakland, MD 21550

    Unmatched EXCEPTIONAL Lakefront Living – 6 Bedrooms | 7.5 Baths | Tucked Among the PinesDiscover a rare opportunity to own a true lakefront, lakeview gem—this 5,400 sq ft, 6-bedroom, 7.5-bath home that is nestled among tall pines on an exceptional lot that sits unusually close to the water’s edge. With peaceful views across a quiet cove and expansive open-water vistas from the oversized covered

    Susan Bell Railey Realty, Inc.

    56 Bee Tree Ln, Oakland, MD 21550
  • 216 Tarn Dr, Oakland, MD 21550
    216 Tarn Dr, Oakland, MD 21550
    216 Tarn Dr, Oakland, MD 21550
    /83

    $1,250,000

    • 6 Beds
    • 4.5 Baths
    • 4,769 Sq Ft

    216 Tarn Dr, Oakland, MD 21550

    Breathtaking home located in the well-established Mountainside community. This newer home is simply stunning from the moment you enter. The cathedral ceilings, granite countertops, luxury vinyl flooring, sunroom with hot tub, and bonus room above the garage checks off all the boxes. The attention to detail is felt throughout this home, from the first level laundry room to the office/den, the

    Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    216 Tarn Dr, Oakland, MD 21550
  • 102 Mountainview Ct, Oakland, MD 21550
    102 Mountainview Ct, Oakland, MD 21550
    102 Mountainview Ct, Oakland, MD 21550
    /59

    $1,100,000

    • 7 Beds
    • 4.5 Baths
    • 5,376 Sq Ft

    102 Mountainview Ct, Oakland, MD 21550

    ***NEW PRICE*** Welcome to 'Boulder Escape'—a Luxury Log Home in a Prestigious Mountainside Community. This breathtaking 7-bedroom, 4.5-bathroom lake access lodge offers over 5,600 square feet of refined mountain living, situated on 1.6 acres of serene wooded land. Whether you're looking for the perfect vacation retreat or a forever home, this stunning property has it all.Step inside and

    Hans Perkasa Epique Realty

    102 Mountainview Ct, Oakland, MD 21550
  • 383 Penn Cove Rd, Oakland, MD 21550
    383 Penn Cove Rd, Oakland, MD 21550
    383 Penn Cove Rd, Oakland, MD 21550
    /49

    $1,599,000

    • 5 Beds
    • 3 Baths
    • 2,080 Sq Ft

    383 Penn Cove Rd, Oakland, MD 21550

    This lovely lakefront two-level ranch house is well-sited on a gently sloping 1.11 acre lot on a quiet cul-de-sac in the private Penn Cove community. The home offers beautiful views of the lake from nearly every room. With five spacious bedrooms (one of which is brand new) and a bonus room, there is ample space for accommodating family and guests. The kitchen and bathrooms have been recently

    Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    383 Penn Cove Rd, Oakland, MD 21550
  • 2463 Mayhew Inn Rd, Oakland, MD 21550
    2463 Mayhew Inn Rd, Oakland, MD 21550
    2463 Mayhew Inn Rd, Oakland, MD 21550
    /141

    $2,199,900

    • 6 Beds
    • 5.5 Baths
    • 5,389 Sq Ft

    2463 Mayhew Inn Rd, Oakland, MD 21550

    Iconic Lakeside Mountain Retreat at Deep Creek Lake! Recently Renovated, This 6 Bedroom 5.5 Bath Rental Goliath features a shiny new gourmet kitchen, updated bathrooms, several new mini split systems, a new hot tub, updated furnishings, a fresh coat of exterior stain, and new floors throughout. Complete facelift of the outdoor living space with sprawling new treks deck, fire pit, and concrete

    Jon Bell Railey Realty, Inc.

    2463 Mayhew Inn Rd, Oakland, MD 21550
  • 439 Paradise Heights, Oakland, MD 21550
    439 Paradise Heights, Oakland, MD 21550
    439 Paradise Heights, Oakland, MD 21550
    /45

    $1,379,000

    • 6 Beds
    • 4.5 Baths
    • 4,113 Sq Ft

    439 Paradise Heights, Oakland, MD 21550

    Stunning 6-Bedroom Kathadin Log Home with Breathtaking 180 views of Deep Creek Lake with Lake Access and a Boat Slip! This exceptional vacation home offers the perfect blend of rustic charm and modern luxury. Boasting 180-degree panoramic views of the sparkling lake, this property is a true mountain retreat. Every room is designed to capture the beauty of the surrounding landscape, with expansive

    Mike Kennedy Railey Realty, Inc.

    439 Paradise Heights, Oakland, MD 21550
  • 340 Grandview Dr, Oakland, MD 21550
    340 Grandview Dr, Oakland, MD 21550
    340 Grandview Dr, Oakland, MD 21550
    /28

    $1,150,000

    • 6 Beds
    • 4 Baths
    • 2,536 Sq Ft

    340 Grandview Dr, Oakland, MD 21550

    Stunning Mountaintop Retreat with stunning Lake Views in MountainsideEscape to your dream home with breathtaking views of Deep Creek Lake! This beautiful mountaintop property spans two acres and features six spacious bedrooms, perfect for family gatherings or entertaining friends. Enjoy an open floorplan complemented by two cozy propane fireplaces and elegant granite countertops

    Michael Cumerlato Jason Mitchell Group

    340 Grandview Dr, Oakland, MD 21550
  • 2725 Stockslager Rd, Oakland, MD 21550
    2725 Stockslager Rd, Oakland, MD 21550
    2725 Stockslager Rd, Oakland, MD 21550
    /108

    $2,750,000

    • 5 Beds
    • 6.5 Baths
    • 5,376 Sq Ft

    2725 Stockslager Rd, Oakland, MD 21550

    Welcome to 2725 Stockslager Road, one of Deep Creek Lake's most coveted properties. This custom-built timber frame home is set against a picturesque landscape in Western Maryland, offering breathtaking nature views and embodying mountain charm and adventure. The log home showcases impeccable craftsmanship, seamlessly blending with its natural surroundings while providing unrivaled

    Shelia McCracken Taylor Made Deep Creek Vacations & Sales

    2725 Stockslager Rd, Oakland, MD 21550
  • 339.03+/- ACRES 442 Baker Farm Rd, Oakland, MD 21550
    339.03+/- ACRES 442 Baker Farm Rd, Oakland, MD 21550
    339.03+/- ACRES 442 Baker Farm Rd, Oakland, MD 21550
    /150

    $1,899,900

    • 6 Beds
    • 3 Baths
    • 3,800 Sq Ft

    339.03+/- ACRES 442 Baker Farm Rd, Oakland, MD 21550

    OUTSTANDING 339± ACRE FARM IN OAKLAND, MD! THE FARM IS CERTIFIED ORGANIC! Just minutes from Deep Creek Lake and Mountain Lake! Easy access to the farm from 135, 219 and other local roadways. Beautiful and well-maintained property, don't miss out! 339± acre farm with incredible views and approx. 150± acres tillable! The farm features an incredible farmhouse with 5-6 bedrooms, 2.5

    Kaleb Hurley Hurley Real Estate & Auctions

    339.03+/- ACRES 442 Baker Farm Rd, Oakland, MD 21550
  • 611 E Oak St, Oakland, MD 21550
    611 E Oak St, Oakland, MD 21550
    611 E Oak St, 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
  • 433 San Francisco St, Oakland, MD 21550
    433 San Francisco St, Oakland, MD 21550
    433 San Francisco St, Oakland, MD 21550
    /66

    $599,900

    • 6 Beds
    • 2.5 Baths
    • 2,560 Sq Ft

    433 San Francisco St, Oakland, MD 21550

    Fully renovated, fully loaded, and fully ready to be your Deep Creek Lake getaway! This 6-bedroom mountain retreat is packed with upgrades—New flooring, new septic, new hot tub, and a sleek modern kitchen with concrete counters, soft-close cabinets, and stainless steel appliances. One wood-burning fireplace for the cozy nights, one propane for the lazy mornings. Two and a half bathrooms, all

    Jon Bell Railey Realty, Inc.

    433 San Francisco St, Oakland, MD 21550
  • 3472 Lake Shore Dr, Oakland, MD 21550
    3472 Lake Shore Dr, Oakland, MD 21550
    3472 Lake Shore Dr, Oakland, MD 21550
    /76

    $895,000

    • 5 Beds
    • 5.5 Baths
    • 2,904 Sq Ft

    3472 Lake Shore Dr, Oakland, MD 21550

    Situated in the sought after area of Lake Shore Drive is this expansive contemporary home with lake views! Built in 2007, this residence boasts five en suites, two stone propane fireplaces, hardwood flooring, granite countertops and a great laundry room. The heart of the home is the open concept kitchen/dining/living room area, making it ideal for everyday living and entertaining. Two levels of

    Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    3472 Lake Shore Dr, Oakland, MD 21550
  • 1001 Sutter Ln, Oakland, MD 21550
    1001 Sutter Ln, Oakland, MD 21550
    1001 Sutter Ln, Oakland, MD 21550
    /108

    $899,900

    • 5 Beds
    • 6 Baths
    • 6,588 Sq Ft

    1001 Sutter Ln, Oakland, MD 21550

    5BR, 4BA, 2HB Southern-style custom home on 2.44 private, wooded acres. Over 6500sf of IMMACULATELY finished space, this house also fronts on Broadford Lake, a 400+/- acre iconic park with a beach, swimming area, fishing, mountain bike trails, playgrounds, pavilions and community ballfields. This house is a 'must-see' to fully experience the planning and design of every feature you could

    Jay Ferguson Taylor Made Deep Creek Vacations & Sales

    1001 Sutter Ln, Oakland, MD 21550
  • 25 Silver Tree Ln, Oakland, MD 21550
    25 Silver Tree Ln, Oakland, MD 21550
    25 Silver Tree Ln, Oakland, MD 21550
    /51

    $789,999

    • 5 Beds
    • 4 Baths
    • 2,364 Sq Ft

    25 Silver Tree Ln, Oakland, MD 21550

    Beautiful lake access retreat located in the Silver Tree Landings community. This recently updated contemporary home feels warm and inviting from the moment you walk in (upgrade list available). Offering hardwood flooring, granite countertops, two stone propane fireplaces and cathedral ceilings. The abundance of windows allows the natural light to brighten any season, while offering views from

    Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    25 Silver Tree Ln, Oakland, MD 21550
  • 155 Basswood Way, Oakland, MD 21550
    155 Basswood Way, Oakland, MD 21550
    155 Basswood Way, Oakland, MD 21550
    /51

    $714,900

    • 5 Beds
    • 3 Baths
    • 2,792 Sq Ft

    155 Basswood Way, Oakland, MD 21550

    Tucked just off Lakeshore Drive, this log home nails that luxury treehouse feel. Wrapped in fresh stain (09/24) and packed with updates - "Time Is On My Side" is dialed in for comfort. Five bedrooms, three baths, including a main-level primary. Inside, modern meets rustic with a sleek kitchen, new propane fireplace, and fresh paint throughout. The lower level offers a second living area, pool

    Michael Fenton Railey Realty, Inc.

    155 Basswood Way, Oakland, MD 21550
  • 139 Overlook Ridge Dr, Oakland, MD 21550
    139 Overlook Ridge Dr, Oakland, MD 21550
    139 Overlook Ridge Dr, Oakland, MD 21550
    /73

    $949,900

    • 5 Beds
    • 4.5 Baths
    • 2,846 Sq Ft

    139 Overlook Ridge Dr, Oakland, MD 21550

    Perched atop Holiday Hill on a 1.5-acre site, you will find this contemporary home with beautiful views of Deep Creek Lake! Offering over 3,200 SF with an open floorplan and an abundance of windows, making this home feel warm and inviting while offering plenty of room to enjoy family and friends. Boasting four bedrooms, 3.5 baths, three levels of living space, hardwood flooring, two stone propane

    Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    139 Overlook Ridge Dr, Oakland, MD 21550
  • 247 Winding Trail Ln Unit 6B, Oakland, MD 21550
    247 Winding Trail Ln Unit 6B, Oakland, MD 21550
    247 Winding Trail Ln Unit 6B, Oakland, MD 21550
    /82

    $584,900

    • 5 Beds
    • 4.5 Baths
    • 3,300 Sq Ft

    247 Winding Trail Ln Unit 6B, Oakland, MD 21550

    Overlooking Deep Creek Lake, this modern townhome delivers luxury, comfort, and unbeatable convenience. Located in Timberlake Village, the 5-bedroom, 4.5-bath retreat is minutes from top restaurants, marinas, state parks, and Wisp Resort. The main level was recently reimagined with contemporary lighting and timber accents, a modern kitchen featuring granite counters, stainless appliances, and a

    Jon Bell Railey Realty, Inc.

    247 Winding Trail Ln Unit 6B, Oakland, MD 21550
  • 6652 George Washington Hwy, Oakland, MD 21550
    6652 George Washington Hwy, Oakland, MD 21550
    6652 George Washington Hwy, Oakland, MD 21550
    /33

    $760,000

    • 6 Beds
    • 2.5 Baths
    • 2,672 Sq Ft

    6652 George Washington Hwy, Oakland, MD 21550

    Beautiful home sitting on 35 acres, built by the current owners. Enter the main level into a grand foyer, with a lofty ceiling and beautiful chandelier. To the left is a separate dining room which leads to the large kitchen and living room. Off the living room is the primary bedroom with a huge walk-in closet and a full bathroom, including a newly installed walk-in shower. On the other side of

    Andrew Orr Railey Realty, Inc.

    6652 George Washington Hwy, Oakland, MD 21550
  • 511 Main St, Oakland, MD 21550
    511 Main St, Oakland, MD 21550
    511 Main St, Oakland, MD 21550
    /33

    $235,000

    • 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
  • 1240 Boy Scout Rd, Oakland, MD 21550
    1240 Boy Scout Rd, Oakland, MD 21550
    1240 Boy Scout Rd, Oakland, MD 21550
    /119

    $4,750,000

    • 7 Beds
    • 7 Baths
    • 3,695 Sq Ft

    1240 Boy Scout Rd, Oakland, MD 21550

    An Iconic 50-acre Estate at Deep Creek Lake with a Deeded Boat Slip, Equestrian Amenities and Rental/Event Potential!Introducing "Double Eagle Ranch," a one-of-a-kind property at Deep Creek Lake, offering the perfect blend of luxury, outdoor adventure, and incredible income-producing potential. This 50-acre Aspen style ranch and estate is a true gem for horse lovers, nature enthusiasts,

    Charlotte Savoy The KW Collective

    1240 Boy Scout Rd, Oakland, MD 21550
  • 170 Winding Trail Ln Unit 4B, Oakland, MD 21550
    170 Winding Trail Ln Unit 4B, Oakland, MD 21550
    170 Winding Trail Ln Unit 4B, Oakland, MD 21550
    /45

    $589,000

    • 5 Beds
    • 4.5 Baths
    • 3,300 Sq Ft

    170 Winding Trail Ln Unit 4B, Oakland, MD 21550

    Spacious home located in the Timberlake Village community. This duplex home offers three levels of living space, granite counter tops, hardwood flooring, propane fireplace and an attached garage. The large kitchen and open floorplan make this an ideal permanent or vacation home. The exterior space is just as pleasing offering a covered front deck and a lower patio, which boasts a hot tub for your

    Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    170 Winding Trail Ln Unit 4B, Oakland, MD 21550
  • 3539 Underwood Rd, Oakland, MD 21550
    3539 Underwood Rd, Oakland, MD 21550
    3539 Underwood Rd, Oakland, MD 21550
    /73

    $350,000

    • 6 Beds
    • 4 Baths
    • 3,662 Sq Ft

    3539 Underwood Rd, Oakland, MD 21550

    Picture perfect country setting. This spacious home sits on a level lot, in a lovely private setting. You are close enough to town and amenities, but this home offers the quiet country ambiance with a yard ready for fun and games. Multiple living areas and an eat in kitchen make this a perfect family home. This property also boasts two furnaces and two hot water heaters to make everyone

    Rachel Bruch Railey Realty, Inc.

    3539 Underwood Rd, Oakland, MD 21550
  • 1931 Lake Shore Dr, Oakland, MD 21550
    1931 Lake Shore Dr, Oakland, MD 21550
    1931 Lake Shore Dr, Oakland, MD 21550
    /93

    $3,689,000

    • 5 Beds
    • 5.5 Baths
    • 5,100 Sq Ft

    1931 Lake Shore Dr, Oakland, MD 21550

    Deep Creek Lakes, Sunset Hills, luxury retreat offering majestic mountain & lake views. A unique lakefront property that plays a perfect host to relaxing vacations with family and friends is a low-key lifestyle centered around the outdoors. Vast stretches of glass ensure a sparkling water view is always on hand. Though sleek materials and high-end finishes abound, their low-profile design puts

    Russell Bounds Railey Realty, Inc.

    1931 Lake Shore Dr, Oakland, MD 21550
  • 41 Boyd Paugh Ln, Oakland, MD 21550
    41 Boyd Paugh Ln, Oakland, MD 21550
    41 Boyd Paugh Ln, Oakland, MD 21550
    /103

    $2,399,000

    • 7 Beds
    • 5 Baths
    • 4,691 Sq Ft

    41 Boyd Paugh Ln, Oakland, MD 21550

    Gorgeous 7 bedroom home with dock slip! This newer construction home sits on a quiet corner of Deep Creek Lake with 200 feet of lake frontage. Located in the beautiful and quiet Heron Cove community and comes with two community lake access points, one with a sandy beach area, tennis courts, and walking trails. The level lot is surrounded by trees and designed for privacy and outdoor enjoyment,

    Rachel Bruch Railey Realty, Inc.

    41 Boyd Paugh Ln, Oakland, MD 21550
Maryland Oakland

5-Bedroom Homes for Sale in Oakland, MD

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In Oakland, there are currently 24 5-bedroom homes for sale, offering expansive and versatile living spaces suitable for larger families or those desiring ample room for guests, home offices, or recreational areas. These properties provide flexibility and comfort, with generous bedroom counts accommodating various living arrangements and lifestyle needs. Whether you're in search of a spacious single-family home, a luxurious estate, or a custom-built residence with five or more bedrooms, there are options to cater to different lifestyles. Explore the selection of 5-bedroom homes for sale in Oakland and find the perfect place to meet your needs.

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