150

Newest Homes for Sale in Oakland, MD

Section Image Section Image
  • approx. 1720 Lake Shore Dr, Oakland, MD 21550
    approx. 1720 Lake Shore Dr, Oakland, MD 21550
    approx. 1720 Lake Shore Dr, Oakland, MD 21550
    /3

    $250,000

    • Land
    • 9.66 Acres
    • $25,880 per Acre

    approx. 1720 Lake Shore Dr, Oakland, MD 21550

    9.66 ACRE OF HEAVEN. MATURE TIMBER. CONVENIET TO ALL LOCAL SHOPPING AND RECREATIONAL AMENITIES.

    Robert Custer Custer Realty & Auction

    approx. 1720 Lake Shore Dr, Oakland, MD 21550
  • 254 Little Mountain Rd, Oakland, MD 21550
    254 Little Mountain Rd, Oakland, MD 21550
    254 Little Mountain Rd, Oakland, MD 21550
    /53

    $340,000

    Coming Soon
    • 4 Beds
    • 2 Baths
    • 1,792 Sq Ft

    254 Little Mountain Rd, Oakland, MD 21550

    Escape to the mountains at 254 Little Mountain Road, where privacy, comfort, and outdoor adventure come together on nearly 5 acres in the sought-after Backbone Ridge community. Surrounded by mature trees and mountain scenery. Inside, you'll find warm wood accents and a cozy wood-burning fireplace that anchors the inviting living space. Multiple gathering areas provide flexibility for

    Amy Skipper Railey Realty, Inc.

    254 Little Mountain Rd, Oakland, MD 21550
  • 12 Arrowhead Ln, Oakland, MD 21550
    12 Arrowhead Ln, Oakland, MD 21550
    12 Arrowhead Ln, Oakland, MD 21550
    /59

    $739,000

    • 3 Beds
    • 3 Baths
    • 1,650 Sq Ft

    12 Arrowhead Ln, Oakland, MD 21550

    Arrowhead 3BR, 3 full BA lakefront, end-unit condo, WITH a dedicated dock slip! Easy walk out to level lakefront just steps to your dock slip! 3 Level unit includes an updated kitchen, cozy wood burning fireplace, multiple living areas, lakefront patio & deck with great water views! Enjoy a private, level lakefront peninsula boasting a large common lakefront area! Surrounded by mature pine trees,

    Julie Mead The KW Collective

    12 Arrowhead Ln, Oakland, MD 21550
  • Lot 18 Buck Dr, Oakland, MD 21550
    Lot 18 Buck Dr, Oakland, MD 21550
    /2

    $19,900

    • Land
    • 1.35 Acres
    • $14,741 per Acre

    Lot 18 Buck Dr, Oakland, MD 21550

    This 1.352 acre lot borders Buck Drive and also Antelope Drive. Perc approved for a three bedroom home with a sand mound system. Wooded lot just waiting on your house plans. 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.

    Kevin Liller Railey Realty, Inc.

    Lot 18 Buck Dr, Oakland, MD 21550
  • 0 Maple Del Ln, Oakland, MD 21550
    0 Maple Del Ln, Oakland, MD 21550
    0 Maple Del Ln, Oakland, MD 21550
    /7

    $42,000

    • Land
    • 1.05 Acres
    • $40,000 per Acre

    0 Maple Del Ln, Oakland, MD 21550

    Lot 6 Maple Del is a mostly wooded , 1.05 acre lot near the western parts of Deep Creek Lake, Red Run cove and centrally located off Mayhew Inn Rd. There is a small stream running through the property and huge boulders strewn throughout, making it a fantastic setting for a wooded retreat. Incredible location near state parks and Deep Creek Lake area amenities. Public sewer available with sewer

    Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    0 Maple Del Ln, Oakland, MD 21550
  • 1256 Boiling Spring Rd, Oakland, MD 21550
    1256 Boiling Spring Rd, Oakland, MD 21550
    1256 Boiling Spring Rd, Oakland, MD 21550
    /43

    $220,000

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

    1256 Boiling Spring Rd, Oakland, MD 21550

    Perfect family home nestled in a beautifully wooded area in Deer Park! Spacious 3 bedroom, 2 bath home with a primary suite, main floor laundry, and tons of storage space in the basement. The backyard is fenced in perfectly for privacy, children and/or animals. Let your imagination go wild with all the unfinished space in the basement that you can transform into additional living space. Brand new

    Angie House Railey Realty, Inc.

    1256 Boiling Spring Rd, Oakland, MD 21550
  • 428 Sam Snead Cir, Oakland, MD 21550
    428 Sam Snead Cir, Oakland, MD 21550
    428 Sam Snead Cir, Oakland, MD 21550
    /86

    $599,000

    • 5 Beds
    • 3.5 Baths
    • 3,542 Sq Ft

    428 Sam Snead Cir, Oakland, MD 21550

    Welcome to this beautifully appointed 5-bedroom, 3.5-bath home located in one of Oakland’s most desirable neighborhoods—Country Club Acres, bordering The Golf Club at Oakland. Offering the perfect blend of modern style, comfort, and convenience, this spacious home is designed to accommodate both everyday living and entertaining. Step inside to discover an inviting open-concept floor plan

    Justin Liller Railey Realty, Inc.

    428 Sam Snead Cir, Oakland, MD 21550
  • 1499 Foster Rd, Oakland, MD 21550
    1499 Foster Rd, Oakland, MD 21550
    1499 Foster Rd, Oakland, MD 21550
    /64

    $415,000

    • 4 Beds
    • 2 Baths
    • 2,234 Sq Ft

    1499 Foster Rd, Oakland, MD 21550

    Welcome to Ricky's Retreat, a beautifully renovated mountain retreat nestled on 1.17 private wooded acres in the heart of Garrett County. Ideally located just minutes from Deep Creek Lake, Wisp Resort, Swallow Falls State Park, and downtown Oakland, this turnkey property offers the perfect balance of privacy, recreation, and modern comfort. Originally built as a raised ranch, the home has

    Kelsey Meyers Railey Realty, Inc.

    1499 Foster Rd, Oakland, MD 21550
  • 6 Cedar Ln, Oakland, MD 21550
    6 Cedar Ln, Oakland, MD 21550
    6 Cedar Ln, Oakland, MD 21550
    /17

    $19,000

    • Land
    • 21,344 Sq Ft
    • $38,776 per Acre

    6 Cedar Ln, Oakland, MD 21550

    Discover the perfect place to build your mountain getaway, full-time residence, or adventure basecamp. Located within the highly sought-after Yough Mountain Resort community, this property offers access to more than 2,000 acres of private wilderness to explore and enjoy year-round. This land is at the top of the mountain where it is generally quieter. It has been surveyed for a well site and has

    Danielle Luscombe Taylor-Made Deep Creek Real Estate, LLC

    6 Cedar Ln, Oakland, MD 21550
  • 20160 Garrett Hwy Unit C307, Oakland, MD 21550
    20160 Garrett Hwy Unit C307, Oakland, MD 21550
    20160 Garrett Hwy Unit C307, Oakland, MD 21550
    /49

    $379,500

    • 1 Bed
    • 1 Bath
    • 636 Sq Ft

    20160 Garrett Hwy Unit C307, Oakland, MD 21550

    Experience the best of Deep Creek Lake from this beautifully situated 2-story, 1-bedroom, 1-bath condominium at Will O' The Wisp. Offering 636 square feet of comfortable living space and spectacular lake views, this waterfront retreat is the perfect personal getaway, year-round residence, or vacation rental investment. Enjoy your morning coffee while taking in panoramic views of the water, then

    Justin Liller Railey Realty, Inc.

    20160 Garrett Hwy Unit C307, Oakland, MD 21550
  • 511 Hilltop Rd, Oakland, MD 21550
    511 Hilltop Rd, Oakland, MD 21550
    511 Hilltop Rd, Oakland, MD 21550
    /51

    $434,900

    • 4 Beds
    • 3 Baths
    • 2,406 Sq Ft

    511 Hilltop Rd, Oakland, MD 21550

    Tucked away on a quiet cul-de-sac in the desirable Royal Charlotte community, this stunning 4-bedroom, 3-bathroom home is the kind of property you'll fall in love with the moment you arrive. Surrounded by the beauty and tranquility of the mountains and accessed by county-maintained roads, this impeccably maintained home showcases pride of ownership throughout. From the expansive Trex decking that

    Laura Newhall Taylor-Made Deep Creek Real Estate, LLC

    511 Hilltop Rd, Oakland, MD 21550
  • 250 Lehman Ln Unit 39, Oakland, MD 21550
    250 Lehman Ln Unit 39, Oakland, MD 21550
    250 Lehman Ln Unit 39, Oakland, MD 21550
    /113

    $715,000

    • 4 Beds
    • 5 Baths
    • 3,240 Sq Ft

    250 Lehman Ln Unit 39, Oakland, MD 21550

    Immaculate 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

    Richard Candy Synergy Realty

    250 Lehman Ln Unit 39, Oakland, MD 21550
  • 2967 Pysell Crosscut Rd, Oakland, MD 21550
    2967 Pysell Crosscut Rd, Oakland, MD 21550
    2967 Pysell Crosscut Rd, Oakland, MD 21550
    /64

    $400,000

    • 2 Beds
    • 1 Bath
    • 1,800 Sq Ft

    2967 Pysell Crosscut Rd, Oakland, MD 21550

    Discover the charm and comfort of this beautifully maintained manufactured home, nestled on a generous 2.07-acre lot. With a unique blend of rustic appeal and modern convenience, this property is perfect for those seeking a serene retreat without sacrificing accessibility. Step inside to find a warm and inviting interior with carpeting and laminate flooring that flows seamlessly throughout. The

    Larry Smith Railey Realty, Inc.

    2967 Pysell Crosscut Rd, Oakland, MD 21550
  • 2967 Pysell Crosscut Rd, Oakland, MD 21550
    2967 Pysell Crosscut Rd, Oakland, MD 21550
    2967 Pysell Crosscut Rd, Oakland, MD 21550
    /58

    $215,000

    • 2 Beds
    • 1 Bath
    • 1,440 Sq Ft

    2967 Pysell Crosscut Rd, Oakland, MD 21550

    This charming manufactured home offers a delightful blend of comfort and functionality, perfect for those seeking a cozy retreat. With 1,440 square feet of thoughtfully designed living space, this residence features two bedrooms and full bathroom. Step inside to discover a warm and welcoming interior. The combination dining and living area is perfect for entertaining or enjoying quiet evenings at

    Larry Smith Railey Realty, Inc.

    2967 Pysell Crosscut Rd, Oakland, MD 21550
  • 0 Pysell Crosscut Rd Unit MDGA2012040, Oakland, MD 21550
    0 Pysell Crosscut Rd Unit MDGA2012040, Oakland, MD 21550
    0 Pysell Crosscut Rd Unit MDGA2012040, Oakland, MD 21550
    /19

    $185,000

    • Land
    • 1.35 Acres
    • $137,037 per Acre

    0 Pysell Crosscut Rd Unit MDGA2012040, Oakland, MD 21550

    Discover the perfect canvas for your dream home on this expansive 1.35-acre parcel of land, where possibilities abound and nature's beauty surrounds you. Nestled in a serene setting, this property offers a unique opportunity to create a personalized retreat tailored to your lifestyle. Imagine waking up each morning to the gentle rustle of leaves and the soft sounds of nature, all while being just

    Larry Smith Railey Realty, Inc.

    0 Pysell Crosscut Rd Unit MDGA2012040, Oakland, MD 21550
  • 211 High Point Ridge Rd, Oakland, MD 21550
    211 High Point Ridge Rd, Oakland, MD 21550
    211 High Point Ridge Rd, Oakland, MD 21550
    /99

    $1,495,000

    • 4 Beds
    • 3.5 Baths
    • 3,472 Sq Ft

    211 High Point Ridge Rd, Oakland, MD 21550

    One in a lifetime opportunity to own one of Maryland’s most distinctive homes. Built in 2019, this fully custom modern home is located on the highest elevation building lot in the state of Maryland, making it the highest elevation home in the state at our 3300 feet above sea level. Designed to take full advantage of the setting, the property offers incredible panoramic views stretching across the

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 443-3345

    211 High Point Ridge Rd, Oakland, MD 21550
  • 251 Robinwood Dr, Oakland, MD 21550
    251 Robinwood Dr, Oakland, MD 21550
    251 Robinwood Dr, Oakland, MD 21550
    /61

    $969,000

    • 5 Beds
    • 4.5 Baths
    • 4,284 Sq Ft

    251 Robinwood Dr, Oakland, MD 21550

    One-of-a-kind Youghiogheny riverfront estate offering 400 feet of water frontage on 5+ acres and 2 separate lots. 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

    Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    251 Robinwood Dr, Oakland, MD 21550
  • 2311 Boy Scout Rd, Oakland, MD 21550
    2311 Boy Scout Rd, Oakland, MD 21550
    2311 Boy Scout Rd, Oakland, MD 21550
    /78

    $1,579,900

    • 4 Beds
    • 3 Baths
    • 3,278 Sq Ft

    2311 Boy Scout Rd, Oakland, MD 21550

    Experience the best of Deep Creek Lake living from this private waterfront retreat tucked among mature trees on nearly an acre of land. With over 100 feet of lake frontage, a private Type-A dock, and a gentle distance to deep water, this property offers the kind of shoreline that's increasingly hard to find. Thoughtfully positioned to capture expansive lake views while preserving a sense of

    Jon Bell Railey Realty, Inc.

    2311 Boy Scout Rd, Oakland, MD 21550
  • 0 5 Acres Lake Shore Dr, Oakland, MD 21550
    0 5 Acres Lake Shore Dr, Oakland, MD 21550
    /2

    $250,000

    • Land
    • 5 Acres
    • $50,000 per Acre

    0 5 Acres Lake Shore Dr, Oakland, MD 21550

    5.0 unrestricted acres in the heart of Deep Creek Lake area, only 1/4 mile away from the lake. Ready to build your dream home with seclusion and privacy, close to area parks and amenities.

    Agent Photo

    Brian Homberg

    Taylor-Made Deep Creek Real Estate, LLC

    (240) 802-8705

    0 5 Acres Lake Shore Dr, Oakland, MD 21550
  • 122 Woodlands Hill Ln, Oakland, MD 21550
    122 Woodlands Hill Ln, Oakland, MD 21550
    122 Woodlands Hill Ln, Oakland, MD 21550
    /54

    $1,200,000

    • 4 Beds
    • 4.5 Baths
    • 2,656 Sq Ft

    122 Woodlands Hill Ln, Oakland, MD 21550

    Welcome to mountain living at its finest. Nestled on 6.89 private acres, 122 Woodlands Hill Lane offers the perfect blend of seclusion, space, and comfort in one of Garrett County’s most desirable settings. This impressive 4-bedroom, 4.5-bath home features approximately 4,000 square feet of living space designed for gathering, relaxing, and enjoying the beauty of Western Maryland. The home sits

    Agent Photo

    Brian Homberg

    Taylor-Made Deep Creek Real Estate, LLC

    (240) 290-8978

    122 Woodlands Hill Ln, Oakland, MD 21550
  • Lot 9 Woodlands Hill Ln, Oakland, MD 21550
    Lot 9 Woodlands Hill Ln, Oakland, MD 21550
    Lot 9 Woodlands Hill Ln, Oakland, MD 21550
    /13

    $95,000

    • Land
    • 2.08 Acres
    • $45,673 per Acre

    Lot 9 Woodlands Hill Ln, Oakland, MD 21550

    2.08 acre corner building lot in The View community at Deep Creek Lake! The lot is approved for up to a 6 bedroom septic system - a rare find which offers added flexibility for your future mountain or lake area home. Mostly wooded setting with convenient access off Lakeshore Drive and close proximity to Deep Creek Lake, Wisp Resort, restaurants, shopping, and local attractions. Lot 10 is also

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 262-4384

    Lot 9 Woodlands Hill Ln, Oakland, MD 21550
  • 0 3 15 Acres Woodlands Hill Dr Unit MDGA2012042, Oakland, MD 21550
    0 3 15 Acres Woodlands Hill Dr Unit MDGA2012042, Oakland, MD 21550
    /2

    $200,000

    • Land
    • 3.15 Acres
    • $63,492 per Acre

    0 3 15 Acres Woodlands Hill Dr Unit MDGA2012042, Oakland, MD 21550

    3.15 unrestricted acres in the heart of Deep Creek Lake area, only 1/4 mile away from the lake. Ready to build your dream home with seclusion and privacy, close to area parks and amenities. No HOA.

    Agent Photo

    Brian Homberg

    Taylor-Made Deep Creek Real Estate, LLC

    (240) 226-3852

    0 3 15 Acres Woodlands Hill Dr Unit MDGA2012042, Oakland, MD 21550
  • 20160 Garrett Hwy Unit H706, Oakland, MD 21550
    20160 Garrett Hwy Unit H706, Oakland, MD 21550
    20160 Garrett Hwy Unit H706, Oakland, MD 21550
    /30

    $309,000

    • 1 Bed
    • 1 Bath
    • 550 Sq Ft

    20160 Garrett Hwy Unit H706, Oakland, MD 21550

    Welcome to Will O' the Wisp Unit H706, a beautiful top-floor lakefront condo offering some of the most breathtaking views of Deep Creek Lake. Perched on the 7th floor and overlooking one of the lake's widest sections, this fully furnished two-level condo features 1 bedroom, 1 bath, and 550 square feet of comfortable, low-maintenance living - ideal as a vacation retreat, year-round getaway, or

    Agent Photo

    James Matthews

    Taylor-Made Deep Creek Real Estate, LLC

    (240) 266-9392

    20160 Garrett Hwy Unit H706, Oakland, MD 21550
  • 670 Woodlands Hill Ln, Oakland, MD 21550
    670 Woodlands Hill Ln, Oakland, MD 21550
    670 Woodlands Hill Ln, Oakland, MD 21550
    /72

    $1,689,000

    • 5 Beds
    • 4.5 Baths
    • 3,714 Sq Ft

    670 Woodlands Hill Ln, Oakland, MD 21550

    Experience what may be the most spectacular view in all of Deep Creek Lake! Perched in an extraordinary setting, this exceptional Yellowstone Log Home showcases breathtaking panoramic water views that create a true “top of the world” feel. Designed to capture the scenery from every angle, the main level features an open-concept layout with soaring natural light, a stunning stone fireplace, luxury

    Nina Beitzel Railey Realty, Inc.

    670 Woodlands Hill Ln, Oakland, MD 21550
  • 460 W Liberty St, Oakland, MD 21550
    460 W Liberty St, Oakland, MD 21550
    460 W Liberty St, Oakland, MD 21550
    /8

    $24,900

    • Land
    • 13,503 Sq Ft
    • $80,323 per Acre

    460 W Liberty St, Oakland, MD 21550

    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. 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

    Kevin Liller Railey Realty, Inc.

    460 W Liberty St, Oakland, MD 21550
  • 8760 Oakland Sang Run Rd, Oakland, MD 21550
    8760 Oakland Sang Run Rd, Oakland, MD 21550
    8760 Oakland Sang Run Rd, Oakland, MD 21550
    /28

    $82,500

    • Land
    • 2.53 Acres
    • $32,609 per Acre

    8760 Oakland Sang Run Rd, Oakland, MD 21550

    Attention outdoor enthusiasts! This 2.53 acre lot just across the road from state-owned land down to the world-famous Youghiogheny River is a whitewater lover or fisherman's dream. Complete with a gravel driveway up to a flat gravel pad and electric meter ready to go, perfect for a camper or a forever home. Perc-approved for 3 bedrooms and less than half a mile from easy public Yough access.

    Elizabeth Ware Railey Realty, Inc.

    8760 Oakland Sang Run Rd, Oakland, MD 21550
  • 277 Cheeks Ln, Oakland, MD 21550
    277 Cheeks Ln, Oakland, MD 21550
    277 Cheeks Ln, Oakland, MD 21550
    /37

    $279,000

    • 3 Beds
    • 1.5 Baths
    • 1,148 Sq Ft

    277 Cheeks Ln, Oakland, MD 21550

    Tucked away on a private lane and surrounded by the beauty of the woods, this charming 3-bedroom, 1 full bath and 1 half bath log home offers the perfect mountain retreat on 2 peaceful acres in Garrett County. Ideally located just minutes from Swallow Falls State Park, Muddy Creek Falls, and the Youghiogheny River, this cozy cabin is a dream destination for outdoor enthusiasts seeking hiking,

    Mike Kennedy Railey Realty, Inc.

    277 Cheeks Ln, Oakland, MD 21550
  • 312 Moss Creek Cir, Oakland, MD 21550
    312 Moss Creek Cir, Oakland, MD 21550
    312 Moss Creek Cir, Oakland, MD 21550
    /55

    $795,000

    • 5 Beds
    • 3.5 Baths
    • 4,230 Sq Ft

    312 Moss Creek Cir, Oakland, MD 21550

    Tucked away on a picturesque 1.83-acre parcel, this charming log home offers the perfect blend of rustic character and modern comfort. Amongst the 4,200+ SF, you will find five spacious bedrooms, two family rooms, a playroom, an office/den, a large loft, spacious pantry, granite counter tops, hardwood flooring and two fireplaces. The warm wood interior and classic log construction create a cozy,

    Betsy Spiker Holcomb Taylor-Made Deep Creek Real Estate, LLC

    312 Moss Creek Cir, Oakland, MD 21550
  • 0 6 89 Acres -Woodlands Hill Dr Dr Unit MDGA2011974, Oakland, MD 21550
    0 6 89 Acres -Woodlands Hill Dr Dr Unit MDGA2011974, Oakland, MD 21550
    0 6 89 Acres -Woodlands Hill Dr Dr Unit MDGA2011974, Oakland, MD 21550
    /4

    $250,000

    • Land
    • 6.89 Acres
    • $36,284 per Acre

    0 6 89 Acres -Woodlands Hill Dr Dr Unit MDGA2011974, Oakland, MD 21550

    6.89 unrestricted acres in the heart of Deep Creek Lake area, only 1/4 mile away from the lake. Ready to build your dream home with seclusion and privacy, close to all area parks and amenities.

    Agent Photo

    Brian Homberg

    Taylor-Made Deep Creek Real Estate, LLC

    (240) 307-5520

    0 6 89 Acres -Woodlands Hill Dr Dr Unit MDGA2011974, Oakland, MD 21550
  • 248 Tarn Dr, Oakland, MD 21550
    248 Tarn Dr, Oakland, MD 21550
    248 Tarn Dr, Oakland, MD 21550
    /70

    $1,189,000

    New Construction
    • 6 Beds
    • 5.5 Baths
    • 3,482 Sq Ft

    248 Tarn Dr, Oakland, MD 21550

    Brand new construction in the desirable Mountainside community! This thoughtfully designed 6-bedroom mountain retreat offers 4 spacious primary suites, blending modern mountain style with functionality and comfort throughout. The open floorplan features vaulted ceilings, luxury finishes, quartz countertops, and multiple gathering spaces designed for entertaining and relaxation alike. Enjoy cozy

    Lauren McCann Railey Realty, Inc.

    248 Tarn Dr, Oakland, MD 21550
  • 2448 Birchwood Dr, Oakland, MD 21550
    2448 Birchwood Dr, Oakland, MD 21550
    2448 Birchwood Dr, Oakland, MD 21550
    /75

    $349,900

    • 4 Beds
    • 2 Baths
    • 3,352 Sq Ft

    2448 Birchwood Dr, Oakland, MD 21550

    Tucked within the sought-after Yough Mountain Resort community, this beautifully remodeled 4-bedroom, 2-bath mountain retreat blends rustic charm with thoughtful modern updates. Warm wood finishes, high ceilings, and inviting gathering spaces create a cozy lodge-style atmosphere, while upgrades throughout add comfort and convenience. The home features two full kitchens with granite countertops,

    Jon Bell Railey Realty, Inc.

    2448 Birchwood Dr, Oakland, MD 21550
  • 83 Bethlehem Rd, Oakland, MD 21550
    83 Bethlehem Rd, Oakland, MD 21550
    83 Bethlehem Rd, Oakland, MD 21550
    /43

    $2,499,900

    • 4 Beds
    • 1.5 Baths
    • 2,190 Sq Ft

    83 Bethlehem Rd, Oakland, MD 21550

    Rare opportunity to own 327+/- acres of scenic countryside featuring a mix of open pasture, mature woods, and flowing stream frontage along Block Run. This 4-bedroom, 1.5-bath farmhouse is privately tucked among rolling fields and mountain views, offering endless potential for farming, recreation, hunting, ATV trails, or a private estate. Multiple barns and outbuildings provide ample storage and

    Jon Bell Railey Realty, Inc.

    83 Bethlehem Rd, Oakland, MD 21550
  • 9.75 AC. Dennett Rd, Oakland, MD 21550
    9.75 AC. Dennett Rd, Oakland, MD 21550
    9.75 AC. Dennett Rd, Oakland, MD 21550
    /30

    $169,000

    • Land
    • 9.75 Acres
    • $17,333 per Acre

    9.75 AC. Dennett Rd, Oakland, MD 21550

    9.75 acres of prime land in a highly convenient Oakland location! This versatile property offers outstanding potential for development or the ideal setting for a private estate-sized homesite. Seller has already completed a proposed subdivision engineering plan, providing added value and future possibilities. Public water and sewer taps available per Oakland Town Administrator. Gently rolling

    Nina Beitzel Railey Realty, Inc.

    9.75 AC. Dennett Rd, Oakland, MD 21550
  • 321 N 3rd St, Oakland, MD 21550
    321 N 3rd St, Oakland, MD 21550
    321 N 3rd St, Oakland, MD 21550
    /48

    $385,000

    $15K PRICE DROP
    • 5 Beds
    • 2 Baths
    • 3,660 Sq Ft

    321 N 3rd St, Oakland, MD 21550

    Reduced and Ready to go!! Perfect one level retirement retreat or 2nd vacation home! Spacious and beautifully maintained all-brick rancher offering approximately 3,660 square feet of living space with room for everyone! This impressive home features 5 bedrooms, 2 full bathrooms, and a fully finished basement with its own private entrance—perfect for in-law potential, extended family living, or

    Christina Ford CENTURY 21 New Millennium

    321 N 3rd St, Oakland, MD 21550
  • 560 Glendale Rd, Oakland, MD 21550
    560 Glendale Rd, Oakland, MD 21550
    560 Glendale Rd, Oakland, MD 21550
    /24

    $419,000

    • 2 Beds
    • 1 Bath
    • 700 Sq Ft

    560 Glendale Rd, Oakland, MD 21550

    Charming vintage Deep Creek Lake log cabin ideally located in the heart of Deep Creek Lake just minutes from area amenities. Full of character and thoughtfully restored, this established rental property is being sold completely furnished and turnkey. Enjoy filtered lake views from the inviting covered front porch, then unwind in the hot tub or gather around the fire pit after a day on the lake.

    Lauren McCann Railey Realty, Inc.

    560 Glendale Rd, Oakland, MD 21550
  • 17921 Garrett Hwy, Oakland, MD 21550
    17921 Garrett Hwy, Oakland, MD 21550
    17921 Garrett Hwy, Oakland, MD 21550
    /56

    $325,000

    Open Sun 10AM - 12:30PM $34K PRICE DROP
    • 4 Beds
    • 1.5 Baths
    • 1,563 Sq Ft

    17921 Garrett Hwy, Oakland, MD 21550

    Charming and well-maintained, this 4-bedroom, 1.5-bath traditional home offers the perfect combination of comfort, character, and convenience. Built in 1952 and thoughtfully cared for, the home features beautifully refinished hardwood floors, inviting built-ins, and a cozy living room with a functional wood burner. With over 1,500 square feet of living space, the spacious layout includes an

    Michelle Clark Taylor-Made Deep Creek Real Estate, LLC

    17921 Garrett Hwy, Oakland, MD 21550
  • 565 Glendale Rd Unit 303B, Oakland, MD 21550
    565 Glendale Rd Unit 303B, Oakland, MD 21550
    565 Glendale Rd Unit 303B, Oakland, MD 21550
    /34

    $399,900

    • 2 Beds
    • 1 Bath
    • 887 Sq Ft

    565 Glendale Rd Unit 303B, Oakland, MD 21550

    Experience lakefront living at its finest in the premier unit at Silver Tree Suites! This beautifully updated 2-bedroom, 1-bath condo showcases rustic charm with custom woodworking throughout. Featuring two separate living areas, there's plenty of space to relax and entertain. Enjoy year-round lake views from the private balcony, unwind by either of the two fireplaces, and appreciate the added

    Sean Sober Taylor-Made Deep Creek Real Estate, LLC

    565 Glendale Rd Unit 303B, Oakland, MD 21550
  • 127 Paradise Heights, Oakland, MD 21550
    127 Paradise Heights, Oakland, MD 21550
    127 Paradise Heights, Oakland, MD 21550
    /24

    $1,025,000

    $50K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,240 Sq Ft

    127 Paradise Heights, Oakland, MD 21550

    Beautifully renovated lake access log cabin with a deeded dock slip in a quiet cove with private 29 acres of trails (ATVs/snowmobiles permitted). Recent renovations (approx. $200K) include new wrap around deck, new roof, re-stained siding, new kitchen with granite counters, new appliances, new bathrooms, new LVFs throughout the house, new 2 car garage doors, new mini-split heat and A/C units, and

    Norman Domingo XRealty.NET LLC

    127 Paradise Heights, Oakland, MD 21550
  • 638 Glendale Rd, Oakland, MD 21550
    638 Glendale Rd, Oakland, MD 21550
    638 Glendale Rd, Oakland, MD 21550
    /56

    $745,000

    • 5 Beds
    • 3 Baths
    • 2,640 Sq Ft

    638 Glendale Rd, Oakland, MD 21550

    Spacious five-bedroom lakeview home offering the perfect blend of relaxation and warmth from the moment you enter. This established rental property “Terp’s Hideaway” features an open and inviting floorplan, five bedrooms, two family rooms, and three levels of living space, making it an ideal layout for hosting family and friends. Step outside onto the large deck to take in beautiful views or

    Betsy Spiker Holcomb Taylor-Made Deep Creek Real Estate, LLC

    638 Glendale Rd, Oakland, MD 21550
  • 206 Mayhew Inn Rd, Oakland, MD 21550
    206 Mayhew Inn Rd, Oakland, MD 21550
    206 Mayhew Inn Rd, Oakland, MD 21550
    /31

    $224,900

    • 1 Bed
    • 1 Bath
    • 1,080 Sq Ft

    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 Real Estate, LLC

    206 Mayhew Inn Rd, Oakland, MD 21550

Showing Results 1 - 40, Page 1 of 4

Maryland Garrett County Oakland

Newest Listings for Sale in Oakland, MD

Frequently Asked Questions

What is the average home price in Oakland, MD?
Homes for sale in Oakland, MD have an average home price of $571,527.
How many homes have sold over the last 12 months in Oakland, MD?
141 homes have sold in Oakland, MD over the last 12 months.
What is the average household income in Oakland, MD?
The average household income in Oakland, MD is $73K.
What are the most popular zip codes in Oakland, MD?
The most popular zip codes in Oakland, MD include 21550, 26764, 21561, 21541 and 21520.
How much do you need to make to afford a house in Oakland?
The median home price in Oakland is $415,000. If you put a 20% down payment of $83,000 and had a 30-year fixed mortgage with an interest rate of 6.52%, your estimated principal and interest payment would be $2,100 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $90K a year to afford the median home price in Oakland. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Oakland is $73K.
How are the schools in Oakland, MD?
Oakland, MD has highly rated public and private schools. Some of the best schools in Oakland based on Niche Grades are Swan Meadow School, Crellin Elementary School and Southern Middle School. Browse all the schools in Oakland, MD to learn more.

Home Prices in Oakland, MD

The median home sale price in Oakland, MD is $420,000, up 4% year-over-year. Homes in Oakland sell in 96 days on average, compared to the national average of 58 days.

Home Price Trends

Median Sale Price
$420,000
Median Single Family Sale Price
$405,000
Median Townhouse Sale Price
$472,500
Median 2 Bedroom Sale Price
$275,000
Median 1 Bedroom Sale Price
$229,900
Average Price Per Sq Ft
$278
Number of Homes for Sale
58
Last 12 months Home Sales
141
Months of Supply
4.90
Median List Price
$415,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
4%
How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group