10,714

Oakland, MD Homes

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  • 1909 Pysell Crosscut Rd, Oakland, MD 21550
    1909 Pysell Crosscut Rd, Oakland, MD 21550
    1909 Pysell Crosscut Rd, Oakland, MD 21550
    /82

    $865,000

    • 4 Beds
    • 4.5 Baths
    • 2,970 Sq Ft

    1909 Pysell Crosscut Rd, Oakland, MD 21550

    Welcome to a private retreat on 4 acres with sweeping views and a large front yard, just minutes from Deep Creek Lake and Oakland. This 4-bedroom, 4.5-bath home has been carefully updated to balance comfort, practicality, and modern style.The main level features hardwood floors, radiant heat for added comfort, and open gathering spaces with quiet nooks for reading or hobbies. Upstairs,

    Melissa Long Railey Realty, Inc.

    1909 Pysell Crosscut Rd, Oakland, MD 21550
  • 5267 George Washington Hwy, Oakland, MD 21550
    5267 George Washington Hwy, Oakland, MD 21550
    5267 George Washington Hwy, Oakland, MD 21550
    /52

    $250,000 Sold Mar 21, 2025

    5267 George Washington Hwy, Oakland, MD 21550

    • 4 Beds
    • 1.5 Baths
    • 2,352 Sq Ft
    • Built 1974

    Last Sold Summary

    • $106/SF
    • 153 Days On Market

    Current Estimated Value $250,595

    Last Listing Agent Jennifer Jackson Charis Realty Group

    5267 George Washington Hwy, Oakland, MD 21550
    • 427 Lake Shore Dr, Oakland, MD 21550
      427 Lake Shore Dr, Oakland, MD 21550
      427 Lake Shore Dr, Oakland, MD 21550
      /125

      Est $2,369,370 Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 4,584 Sq Ft

      427 Lake Shore Dr, Oakland, MD 21550

      427 Lake Shore Dr, Oakland, MD 21550
  • 63 Wallman Rd, Oakland, MD 21550
    63 Wallman Rd, Oakland, MD 21550
    63 Wallman Rd, Oakland, MD 21550
    /60

    $179,900

    • 3 Beds
    • 1 Bath
    • 816 Sq Ft

    63 Wallman Rd, Oakland, MD 21550

    Remodeled Rancher Near the North Branch Potomac RiverThis charming 3-bedroom, 1-bath rancher has been completely remodeled, with all new appliances. Located within walking distance of the scenic North Branch of the Potomac River, the home offers both convenience and natural beauty at your doorstep.A recently enclosed front porch with a wood stove provides extra warmth and a welcoming spot

    Rich Orr Railey Realty, Inc.

    63 Wallman Rd, Oakland, MD 21550
  • 403 O St, Oakland, MD 21550
    403 O St, Oakland, MD 21550
    403 O St, Oakland, MD 21550
    /47

    $270,000 Sold Jun 20, 2025

    403 O St, Oakland, MD 21550

    • 4 Beds
    • 3.5 Baths
    • 2,240 Sq Ft
    • Built 1976

    Last Sold Summary

    • $121/SF
    • 329 Days On Market

    Current Estimated Value $269,679

    Last Listing Agent ANGELA BOSLEY Taylor Made Deep Creek Vacations & Sales

    403 O St, Oakland, MD 21550
    • 2276 Paradise Point Rd, Oakland, MD 21550
      2276 Paradise Point Rd, Oakland, MD 21550
      2276 Paradise Point Rd, Oakland, MD 21550
      /65

      Est $4,099,735 Not Listed For Sale

      • 8 Beds
      • 5.5 Baths
      • 8,453 Sq Ft

      2276 Paradise Point Rd, Oakland, MD 21550

      2276 Paradise Point Rd, Oakland, MD 21550
  • 175 Roman Ridge Rd Unit 15, Oakland, MD 21550
    175 Roman Ridge Rd Unit 15, Oakland, MD 21550
    175 Roman Ridge Rd Unit 15, Oakland, MD 21550
    /55

    $537,500

    • 4 Beds
    • 4.5 Baths
    • 3,192 Sq Ft

    175 Roman Ridge Rd Unit 15, Oakland, MD 21550

    Welcome to one of the most spacious and inviting homes in Trader’s Landing. This rare stand-alone property offers more than 3,100 square feet of living space spread across four beautifully designed levels, perfect for gathering with friends and family or finding a quiet spot to unwind. With 4 bedrooms and 4.5 baths, there’s plenty of room for everyone to relax comfortably. Step out onto the upper

    Eric Crawford Taylor Made Deep Creek Vacations & Sales

    175 Roman Ridge Rd Unit 15, Oakland, MD 21550
  • 1489 Mountainview Dr, Oakland, MD 21550
    1489 Mountainview Dr, Oakland, MD 21550
    1489 Mountainview Dr, Oakland, MD 21550
    /80

    $696,000 Sold Apr 02, 2025

    1489 Mountainview Dr, Oakland, MD 21550

    • 5 Beds
    • 3 Baths
    • 3,066 Sq Ft
    • Built 2001

    Last Sold Summary

    • $227/SF
    • 170 Days On Market

    Current Estimated Value $706,991

    Last Listing Agent Larry Smith Railey Realty, Inc.

    1489 Mountainview Dr, Oakland, MD 21550
    • 1113 White Pine Cir, Oakland, MD 21550
      1113 White Pine Cir, Oakland, MD 21550
      1113 White Pine Cir, Oakland, MD 21550
      /84

      Est $541,117 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,400 Sq Ft

      1113 White Pine Cir, Oakland, MD 21550

      1113 White Pine Cir, Oakland, MD 21550
  • LOT 2 Beaver Run Rd, Oakland, MD 21550
    LOT 2 Beaver Run Rd, Oakland, MD 21550
    LOT 2 Beaver Run Rd, Oakland, MD 21550
    /9

    $3,500

    • Land
    • 0.48 Acre
    • $7,292 per Acre

    LOT 2 Beaver Run Rd, Oakland, MD 21550

    Tucked away in the stunning mountains of Western Maryland, this unbuildable lot provides a serene escape into nature, offering breathtaking views and abundant wildlife. Located in the Youghiogheny Mountain Resort, this membership-only lot grants exclusive access to over 50 miles of private roads and trails, ideal for ATV and side-by-side adventures. Resort amenities include a community clubhouse,

    Elizabeth Broadwater Taylor Made Deep Creek Vacations & Sales

    LOT 2 Beaver Run Rd, Oakland, MD 21550
  • 421 Penn Cove Rd, Oakland, MD 21550
    421 Penn Cove Rd, Oakland, MD 21550
    421 Penn Cove Rd, Oakland, MD 21550
    /107

    $1,350,000 Sold Sep 19, 2025

    421 Penn Cove Rd, Oakland, MD 21550

    • 4 Beds
    • 3.5 Baths
    • 4,284 Sq Ft
    • Built 1986

    Last Sold Summary

    • $315/SF
    • 54 Days On Market

    Current Estimated Value $1,414,329

    Last Listing Agent Steven Ritchie Railey Realty, Inc.

    421 Penn Cove Rd, Oakland, MD 21550
    • 5289 Oakland Sang Run Rd, Oakland, MD 21550
      5289 Oakland Sang Run Rd, Oakland, MD 21550
      5289 Oakland Sang Run Rd, Oakland, MD 21550
      /56

      Est $410,402 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,638 Sq Ft

      5289 Oakland Sang Run Rd, Oakland, MD 21550

      5289 Oakland Sang Run 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
    /29

    $229,000

    • 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
  • 249 Marys Ln, Oakland, MD 21550
    249 Marys Ln, Oakland, MD 21550
    249 Marys Ln, Oakland, MD 21550
    /67

    $855,000 Sold May 12, 2025

    249 Marys Ln, Oakland, MD 21550

    • 5 Beds
    • 3.5 Baths
    • 2,874 Sq Ft
    • Built 2017

    Last Sold Summary

    • $297/SF
    • 7 Days On Market

    Current Estimated Value $869,383

    Last Listing Agent Jon Bell Railey Realty, Inc.

    249 Marys Ln, Oakland, MD 21550
    • 620 E Green St, Oakland, MD 21550
      620 E Green St, Oakland, MD 21550
      620 E Green St, Oakland, MD 21550
      /65

      Est $152,297 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 1,668 Sq Ft

      620 E Green St, Oakland, MD 21550

      620 E Green St, Oakland, MD 21550
  • 127 S Oakhall Dr, Oakland, MD 21550
    127 S Oakhall Dr, Oakland, MD 21550
    127 S Oakhall Dr, Oakland, MD 21550
    /29

    $315,000

    • 4 Beds
    • 2 Baths
    • 2,183 Sq Ft

    127 S Oakhall Dr, Oakland, MD 21550

    Cozy, well maintained 4 bedroom, 2 bathroom ranch style home with full finished basement on a corner lot in Mountain Lake Park. Beautifully finished Hardwood flooring on main level, with a large kitchen/dining area, living room, three bedrooms, and a full bathroom. In the lower level, there is a large family room, full bathroom, a bedroom, and bonus room, that has been used for storage, an

    Andrew Orr The KW Collective

    127 S Oakhall Dr, Oakland, MD 21550
  • 939 Glendale Rd, Oakland, MD 21550
    939 Glendale Rd, Oakland, MD 21550
    939 Glendale Rd, Oakland, MD 21550
    /61

    $820,000 Sold Sep 02, 2025

    939 Glendale Rd, Oakland, MD 21550

    • 3 Beds
    • 3 Baths
    • Built 1990

    Last Sold Summary

    • 18 Days On Market

    Current Estimated Value $825,699

    Last Listing Agent Sean Sober Taylor Made Deep Creek Vacations & Sales

    939 Glendale Rd, Oakland, MD 21550
    • 501 G St, Oakland, MD 21550
      501 G St, Oakland, MD 21550
      501 G St, Oakland, MD 21550
      /76

      Est $226,582 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,520 Sq Ft

      501 G St, Oakland, MD 21550

      501 G St, Oakland, MD 21550
  • 0 Longview Ln, Oakland, MD 21550
    0 Longview Ln, Oakland, MD 21550
    0 Longview Ln, Oakland, MD 21550
    /9

    $49,900

    • Land
    • 1 Acre
    • $49,900 per Acre

    0 Longview Ln, Oakland, MD 21550

    1.00 Acre wooded lot loacted in George Brunson Subdivision. Close to Deep Creek Lake, Wisp Ski Resort and Oakland. Approved perc

    Linda Deremer Appalachian Realty

    0 Longview Ln, Oakland, MD 21550
  • 237 Glendale Rd, Oakland, MD 21550
    237 Glendale Rd, Oakland, MD 21550
    237 Glendale Rd, Oakland, MD 21550
    /100

    $1,860,000 Sold Oct 06, 2025

    237 Glendale Rd, Oakland, MD 21550

    • 7 Beds
    • 6.5 Baths
    • 3,735 Sq Ft
    • Built 2002

    Last Sold Summary

    • $498/SF
    • 88 Days On Market

    Last Listing Agent Bill Weissgerber Railey Realty, Inc.

    237 Glendale Rd, Oakland, MD 21550
    • 107 Pleasant Hill Cir, Oakland, MD 21550
      107 Pleasant Hill Cir, Oakland, MD 21550
      107 Pleasant Hill Cir, Oakland, MD 21550
      /35

      Est $384,646 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,384 Sq Ft

      107 Pleasant Hill Cir, Oakland, MD 21550

      107 Pleasant Hill Cir, Oakland, MD 21550
  • 1737 King Wildesen Rd, Oakland, MD 21550
    1737 King Wildesen Rd, Oakland, MD 21550
    1737 King Wildesen Rd, 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
  • 416 Shenandoah Ave, Oakland, MD 21550
    416 Shenandoah Ave, Oakland, MD 21550
    416 Shenandoah Ave, Oakland, MD 21550
    /56

    $157,000 Sold Aug 29, 2025

    416 Shenandoah Ave, Oakland, MD 21550

    • 3 Beds
    • 1.5 Baths
    • 975 Sq Ft
    • Built 1940

    Last Sold Summary

    • $161/SF
    • 4 Days On Market

    Current Estimated Value $152,978

    Last Listing Agent Rich Orr Railey Realty, Inc.

    416 Shenandoah Ave, Oakland, MD 21550
    • 125 Matthew Rd, Oakland, MD 21550
      125 Matthew Rd, Oakland, MD 21550
      125 Matthew Rd, Oakland, MD 21550
      /66

      Est $442,783 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,324 Sq Ft

      125 Matthew Rd, Oakland, MD 21550

      125 Matthew Rd, Oakland, MD 21550
  • 0 Edgewater Dr Unit 4 MDGA2009106, Oakland, MD 21550
    0 Edgewater Dr Unit 4 MDGA2009106, Oakland, MD 21550
    0 Edgewater Dr Unit 4 MDGA2009106, Oakland, MD 21550
    /16

    $299,000

    • Land
    • 0 Acre

    0 Edgewater Dr Unit 4 MDGA2009106, Oakland, MD 21550

    Rare offering! LAKE VIEW building site with TWO BOAT SLIPS! Located off popular Lake Shore Drive in the Edgewater community, this lot features a building envelope surrounded by community green space. Deep water, somewhat flat area by the lake, feels like small little park area. Dock access is directly across the street and a short walk away away - 100 yards +/-. Paved parking area for easy

    Jay Ferguson Taylor Made Deep Creek Vacations & Sales

    0 Edgewater Dr Unit 4 MDGA2009106, Oakland, MD 21550
  • 12 Roman Ridge Rd Unit 22B, Oakland, MD 21550
    12 Roman Ridge Rd Unit 22B, Oakland, MD 21550
    12 Roman Ridge Rd Unit 22B, Oakland, MD 21550
    /51

    $425,000 Sold Oct 22, 2025

    12 Roman Ridge Rd Unit 22B, Oakland, MD 21550

    • 3 Beds
    • 3.5 Baths
    • 2,202 Sq Ft
    • Built 2012

    Last Sold Summary

    • $193/SF
    • 130 Days On Market

    Last Listing Agent Andrew Eiswert Railey Realty, Inc.

    12 Roman Ridge Rd Unit 22B, Oakland, MD 21550
    • 20488 Garrett Hwy, Oakland, MD 21550
      20488 Garrett Hwy, Oakland, MD 21550
      20488 Garrett Hwy, Oakland, MD 21550
      /6

      Est $684,831 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 840 Sq Ft

      20488 Garrett Hwy, Oakland, MD 21550

      20488 Garrett Hwy, Oakland, MD 21550
  • 41 Fox Den Rd, Oakland, MD 21550
    41 Fox Den Rd, Oakland, MD 21550
    41 Fox Den Rd, 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
  • 0 Hutton Rd Unit MDGA2008936, Oakland, MD 21550
    0 Hutton Rd Unit MDGA2008936, Oakland, MD 21550
    0 Hutton Rd Unit MDGA2008936, Oakland, MD 21550
    /3

    $13,000 Sold Apr 14, 2025

    0 Hutton Rd Unit MDGA2008936, Oakland, MD 21550

    • Land
    • 2 Acres
    • $6,500 per Acre

    Last Sold Summary

    • 35 Days On Market

    Last Listing Agent Julie Mead The KW Collective

    0 Hutton Rd Unit MDGA2008936, Oakland, MD 21550
    • 739 Glendale Rd, Oakland, MD 21550
      739 Glendale Rd, Oakland, MD 21550
      739 Glendale Rd, Oakland, MD 21550
      /85

      Est $1,822,610 Not Listed For Sale

      • 6 Beds
      • 6.5 Baths
      • 4,160 Sq Ft

      739 Glendale Rd, Oakland, MD 21550

      739 Glendale Rd, Oakland, MD 21550
  • 98 Bear Run Rd, Oakland, MD 21550
    98 Bear Run Rd, Oakland, MD 21550
    98 Bear Run Rd, Oakland, MD 21550
    /30

    $550,000

    • 3 Beds
    • 2 Baths
    • 1,080 Sq Ft

    98 Bear Run Rd, Oakland, MD 21550

    Make it your own! This 2-acre parcel comes with two additional parcels of 17.96 and 24.23 acres for a total of 42.19 acres. The 2-acre parcel is improved by a fully furnished (26’X42’), 3-bedroom, 2-bathroom Ranch style dwelling and a large parking area. The interior offers a spacious living room, and an eat-in kitchen with all appliances, furniture and window AC units. The land is un-zoned

    Dan (Sussan) Duggan 1 Real Estate Source LLC

    98 Bear Run Rd, Oakland, MD 21550
  • 216 Tarn Dr, Oakland, MD 21550
    216 Tarn Dr, Oakland, MD 21550
    216 Tarn Dr, Oakland, MD 21550
    /86

    $1,100,000 Sold Aug 27, 2025

    216 Tarn Dr, Oakland, MD 21550

    • 6 Beds
    • 4.5 Baths
    • 4,769 Sq Ft
    • Built 2020

    Last Sold Summary

    • $231/SF
    • 122 Days On Market

    Current Estimated Value $1,119,839

    Last Listing Agent Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    216 Tarn Dr, Oakland, MD 21550
    • 723 E Alder St, Oakland, MD 21550
      723 E Alder St, Oakland, MD 21550
      723 E Alder St, Oakland, MD 21550
      /73

      Est $242,111 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,764 Sq Ft

      723 E Alder St, Oakland, MD 21550

      723 E Alder St, Oakland, MD 21550
  • 3257 George Washington Hwy, Oakland, MD 21550
    3257 George Washington Hwy, Oakland, MD 21550
    3257 George Washington Hwy, Oakland, MD 21550
    /8

    $280,000

    • Land
    • 36.72 Acres
    • $7,625 per Acre

    3257 George Washington Hwy, Oakland, MD 21550

    Discover approximately 36.72 acres of beautiful wooded land offering privacy, mountain views, and exceptional convenience. This expansive property provides easy access to both George Washington Highway and Garrett Highway, making travel simple while still feeling tucked away in nature. Located within a 30-minute drive of Deep Creek Lake and Wisp Resort, as well as sought-after West Virginia

    Justin Liller Railey Realty, Inc.

    3257 George Washington Hwy, Oakland, MD 21550
  • 157 Jeffrey Ln Unit 21C, Oakland, MD 21550
    157 Jeffrey Ln Unit 21C, Oakland, MD 21550
    157 Jeffrey Ln Unit 21C, Oakland, MD 21550
    /21

    $295,000 Sold Dec 23, 2025

    157 Jeffrey Ln Unit 21C, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 752 Sq Ft
    • Built 1997

    Last Sold Summary

    • $392/SF
    • 21 Days On Market

    Last Listing Agent James Matthews Taylor Made Deep Creek Vacations & Sales

    157 Jeffrey Ln Unit 21C, Oakland, MD 21550
    • 943 S Blakeslee Rd, Oakland, MD 21550
      943 S Blakeslee Rd, Oakland, MD 21550
      943 S Blakeslee Rd, Oakland, MD 21550
      /130

      Est $1,178,083 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 3,426 Sq Ft

      943 S Blakeslee Rd, Oakland, MD 21550

      943 S Blakeslee Rd, Oakland, MD 21550
  • 132 &132A Tarn Dr, Oakland, MD 21550
    132 &132A Tarn Dr, Oakland, MD 21550
    132 &132A Tarn Dr, Oakland, MD 21550
    /29

    $175,000

    • Land
    • 3.04 Acres
    • $57,566 per Acre

    132 &132A Tarn Dr, Oakland, MD 21550

    3+ Acre Lake Access Homesite in Mountainside CommunityLots 132 & 132A offer a rare opportunity to own 3.04 acres of lake access property in the highly desirable Mountainside Community. Located at the end of a quiet cul-de-sac on Tarn Drive, these combined lots are officially recorded as one building site—providing ultimate privacy and a perfect setting to build your dream home. Public water &

    Rich Orr Railey Realty, Inc.

    132 &132A Tarn Dr, Oakland, MD 21550
  • 946 Glendale Rd, Oakland, MD 21550
    946 Glendale Rd, Oakland, MD 21550
    946 Glendale Rd, Oakland, MD 21550
    /100

    $1,765,000 Sold Mar 14, 2025

    946 Glendale Rd, Oakland, MD 21550

    • 7 Beds
    • 6.5 Baths
    • 3,546 Sq Ft
    • Built 2001

    Last Sold Summary

    • $498/SF
    • 16 Days On Market

    Current Estimated Value $1,784,264

    Last Listing Agent Jon Bell Railey Realty, Inc.

    946 Glendale Rd, Oakland, MD 21550
    • 223 N 2nd St, Oakland, MD 21550
      223 N 2nd St, Oakland, MD 21550
      223 N 2nd St, Oakland, MD 21550
      /88

      Est $407,559 Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 3,120 Sq Ft

      223 N 2nd St, Oakland, MD 21550

      223 N 2nd St, Oakland, MD 21550
  • Lot 53 Mountainview Dr, Oakland, MD 21550
    Lot 53 Mountainview Dr, Oakland, MD 21550
    Lot 53 Mountainview Dr, Oakland, MD 21550
    /5

    $124,900

    • Land
    • 1.02 Acres
    • $122,451 per Acre

    Lot 53 Mountainview Dr, Oakland, MD 21550

    Ready to build lot in Deep Creek Lake's Mountainside Subdivision. This wooded lot is relatively level can be connected to public water and has an approved percolation test for an onsite septic system. Build you dream home in this mountaintop community with homes values ranging up to $2,000,000.

    Richard Saunders Samson Properties

    Lot 53 Mountainview Dr, Oakland, MD 21550

Showing Results 361 - 400, Page 10 of 18

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