10,549

Oakland, MD Homes

Section Image
  • /20

    $55,000

    Sold Nov 17, 2025

    19 Pheasant Run, Oakland, MD 21550

    • Land
    • 2.84 Acres
    • $19,366 per Acre

    Last Sold Summary

    • 12 Days On Market

    Last Listing Agent Kathy Gibson Railey Realty, Inc.

    19 Pheasant Run, Oakland, MD 21550
    • /49

      Est $365,486

      Not Listed For Sale

      19398 Garrett Hwy, Oakland, MD 21550

      • 5 Beds
      • 2 Baths
      • 2,414 Sq Ft
      • Built 1940
      19398 Garrett Hwy, Oakland, MD 21550

      Last Sold Summary

      • 168 Days On Market

      Last Listing Agent Chris Nichols Taylor-Made Deep Creek Real Estate, LLC

  • /82

    $699,000

    $166K PRICE DROP
    • 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, two

    Melissa Long Railey Realty, Inc.

    1909 Pysell Crosscut Rd, Oakland, MD 21550
  • /18

    $160,000

    Sold Aug 28, 2025

    0 Betts Ln Unit MDGA2009850, Oakland, MD 21550

    • Land
    • 25 Acres
    • $6,400 per Acre

    Last Sold Summary

    • 44 Days On Market

    Last Listing Agent Ally Litten Mountainside Home Realty

    0 Betts Ln Unit MDGA2009850, Oakland, MD 21550
    • /33

      Est $258,821

      Not Listed For Sale

      1070 Sunrise Dr, Oakland, MD 21550

      • 4 Beds
      • 3 Baths
      • 2,144 Sq Ft
      • Built 1988
      1070 Sunrise Dr, Oakland, MD 21550

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Nick Fratz-Orr Railey Realty, Inc.

  • /60

    $164,000

    • 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
  • /2

    $200,000

    Sold Feb 27, 2026

    0 Laurel Run Rd, Oakland, MD 21550

    • Land
    • 70 Acres
    • $2,857 per Acre

    Last Sold Summary

    • 0 Days On Market

    Last Listing Agent Andrew Eiswert Railey Realty, Inc.

    0 Laurel Run Rd, Oakland, MD 21550
    • /48

      Est $467,777

      Not Listed For Sale

      482 Pergin Farm Rd, Oakland, MD 21550

      • 3 Beds
      • 1.5 Baths
      • 2,160 Sq Ft
      • Built 1980
      482 Pergin Farm Rd, Oakland, MD 21550

      Last Sold Summary

      • 128 Days On Market

      Last Listing Agent Nina Beitzel Railey Realty, Inc.

  • /9

    $3,500

    • Land
    • 20,908 Sq Ft
    • $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 throughout the community, as well as an abundance 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

    Elizabeth Broadwater Taylor-Made Deep Creek Real Estate, LLC

    LOT 2 Beaver Run Rd, Oakland, MD 21550
  • /73

    $1,800,000

    Sold Jun 12, 2026

    62 Duck Cove Rd, Oakland, MD 21550

    • 4 Beds
    • 4 Baths
    • 4,150 Sq Ft
    • Built 1980

    Last Sold Summary

    • 5% Below List Price
    • $434/SF
    • 13 Days On Market

    Current Estimated Value $1,795,605

    Last Listing Agent Nick Fratz-Orr Railey Realty, Inc.

    62 Duck Cove Rd, Oakland, MD 21550
    • /46

      Est $1,427,067

      Not Listed For Sale

      2127 Lake Shore Dr, Oakland, MD 21550

      • 3 Beds
      • 3 Baths
      • 2,546 Sq Ft
      • Built 1960
      2127 Lake Shore Dr, Oakland, MD 21550

      Last Sold Summary

      • 20 Days On Market

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

  • /52

    $749,900

    • 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 with an available home warranty. 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

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

    25 Silver Tree Ln, Oakland, MD 21550
  • /53

    $1,500,000

    Sold Dec 01, 2025

    1674 Paradise Point Rd, Oakland, MD 21550

    • 4 Beds
    • 2.5 Baths
    • 2,340 Sq Ft
    • Built 1955

    Last Sold Summary

    • $641/SF
    • 465 Days On Market

    Current Estimated Value $1,556,815

    Last Listing Agent Jon Bell Railey Realty, Inc.

    1674 Paradise Point Rd, Oakland, MD 21550
    • /97

      Est $2,409,035

      Not Listed For Sale

      1738 Paradise Point Rd, Oakland, MD 21550

      • 7 Beds
      • 5.5 Baths
      • 4,260 Sq Ft
      • Built 2002
      1738 Paradise Point Rd, Oakland, MD 21550

      Last Sold Summary

      • 127 Days On Market

      Last Listing Agent Jon Bell Railey Realty, Inc.

  • /28

    $79,500

    $3K PRICE DROP
    • Land
    • 2.53 Acres
    • $31,423 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
  • /64

    $695,000

    Sold Oct 09, 2025

    353 Basswood Way Unit 24, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 2,664 Sq Ft
    • Built 2005

    Last Sold Summary

    • $261/SF
    • 14 Days On Market

    Current Estimated Value $682,243

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    353 Basswood Way Unit 24, Oakland, MD 21550
    • /78

      Est $223,342

      Not Listed For Sale

      1400 Oakland Ave, Oakland, MD 21550

      • 4 Beds
      • 2 Baths
      • 1,920 Sq Ft
      • Built 1972
      1400 Oakland Ave, Oakland, MD 21550

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Justin Liller Railey Realty, Inc.

  • /124

    $3,950,000

    • 8 Beds
    • 10 Baths
    • 6,486 Sq Ft

    1131 Lake Shore Dr, Oakland, MD 21550

    Experience exceptional lakefront living in this spectacular eight-bedroom estate designed for unforgettable gatherings and year-round enjoyment. Perfectly positioned on an oversized lakefront lot with 116’ LF, this remarkable home offers easy access to the water via a walking path, and the abundance of windows fill the interior with natural light.At the heart of the home is a magnificent

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

    1131 Lake Shore Dr, Oakland, MD 21550
  • /28

    $335,000

    Sold Jul 07, 2026

    1740 Old Crellin Rd, Oakland, MD 21550

    • 3 Beds
    • 3 Baths
    • 2,288 Sq Ft
    • Built 1987

    Last Sold Summary

    • $146/SF
    • 28 Days On Market

    Current Estimated Value $326,949

    Last Listing Agent Andrew Orr The KW Collective

    1740 Old Crellin Rd, Oakland, MD 21550
    • /69

      Est $457,753

      Not Listed For Sale

      1014 Madison St, Oakland, MD 21550

      • 5 Beds
      • 3.5 Baths
      • 3,016 Sq Ft
      • Built 1988
      1014 Madison St, Oakland, MD 21550

      Last Sold Summary

      • 21 Days On Market

      Last Listing Agent Justin Liller Railey Realty, Inc.

  • /27

    $259,000

    • Land
    • 42 Acres
    • $6,167 per Acre

    Lot B Loch Deer Rd, Oakland, MD 21550

    42 Acres of un-zoned mostly wooded property located near Oakland and Deep Creek Lake MD. The property offers great opportunities for a variety of uses and also provides great views. Access to the property is off of Garrett Road via Loch Deer Road. The property has been surveyed.

    Bill Weissgerber Railey Realty, Inc.

    Lot B Loch Deer Rd, Oakland, MD 21550
  • /61

    $650,000

    Sold Aug 21, 2025

    1006 Lake Shore Dr, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 1,935 Sq Ft
    • Built 1993

    Last Sold Summary

    • $336/SF
    • 27 Days On Market

    Current Estimated Value $727,423

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    1006 Lake Shore Dr, Oakland, MD 21550
    • /24

      Est $712,675

      Not Listed For Sale

      8 Arrowhead Ln, Oakland, MD 21550

      • 3 Beds
      • 3 Baths
      • Built 1988
      8 Arrowhead Ln, Oakland, MD 21550

      Last Sold Summary

      • 80 Days On Market

      Last Listing Agent Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

  • /5

    $19,900

    • Land
    • 1.05 Acres
    • $18,952 per Acre

    0 Bear Dr E Unit MDGA2012426, Oakland, MD 21550

    Build your dream home, or vacation home. This development has 50 miles of private roads and trails perfect for ATV riding, UTVs, dirt bikes, hiking, hunting and outdoor recreation.

    Connie Leprevost Long & Foster Real Estate, Inc.

    0 Bear Dr E Unit MDGA2012426, Oakland, MD 21550
  • /53

    $245,000

    Sold Jul 17, 2026

    565 Glendale Rd Unit 103B, Oakland, MD 21550

    • 1 Bed
    • 1 Bath
    • Built 2006

    Last Sold Summary

    • 228 Days On Market

    Last Listing Agent Rachel Bruch Railey Realty, Inc.

    565 Glendale Rd Unit 103B, Oakland, MD 21550
    • /88

      Est $440,654

      Not Listed For Sale

      189 Whistle Pig Way, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,777 Sq Ft
      • Built 1998
      189 Whistle Pig Way, Oakland, MD 21550

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Debra Savage Railey Realty, Inc.

  • /22

    $294,999

    • 2 Beds
    • 1 Bath
    • 2,344 Sq Ft

    135 Jeffrey Ln Unit 19-A, Oakland, MD 21550

    Experience the best of lakeview living in this great condo at Deep Creek Lake. Offering two bedrooms, a fireplace and a lower-level family room for your enjoyment. Wake up to peaceful water views and enjoy ample space for everyday comfort and entertaining. The location is another plus, within walking distance to coffee shop, dining, and shopping. A perfect blend of size, scenery, and value!

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

    135 Jeffrey Ln Unit 19-A, Oakland, MD 21550
  • /48

    $279,000

    Sold Sep 25, 2025

    215 N 10th St, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 1,518 Sq Ft
    • Built 1973

    Last Sold Summary

    • 3% Below List Price
    • $184/SF
    • 6 Days On Market

    Current Estimated Value $299,155

    Last Listing Agent ADAM MURRAY BERKSHIRE HATHAWAY HOMESERVICES TOUCHDOWN HOME PROS REALTY

    215 N 10th St, Oakland, MD 21550
    • /45

      Est $203,230

      Not Listed For Sale

      422 Underwood Rd, Oakland, MD 21550

      • 3 Beds
      • 1 Bath
      • 960 Sq Ft
      • Built 1972
      422 Underwood Rd, Oakland, MD 21550

      Last Sold Summary

      • 17 Days On Market

      Last Listing Agent Larry Smith Railey Realty, Inc.

  • /45

    $549,900

    • 4 Beds
    • 2.5 Baths
    • 2,548 Sq Ft

    995 Betts Ln, Oakland, MD 21550

    4BR 2.5BA cabin in the woods! Over 12 wooded acres of privacy and seclusion, laced with trails and surrounded by low maintenance land. Centrally located - only a few miles to Deep Creek Lake, town of Oakland or Swallow Falls State Park. Open floor plan with vaulted ceilings, a wood burning stove and high end finishes throughout. Basement is partially finished. Spacious decking and a must-have

    Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    995 Betts Ln, Oakland, MD 21550
  • /2

    $205,000

    Sold May 20, 2026

    207 Shenandoah Ave, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 1,492 Sq Ft
    • Built 1900

    Last Sold Summary

    • 3% Above List Price
    • $137/SF
    • 6 Days On Market

    Current Estimated Value $195,138

    Last Listing Agent Laura Newhall Taylor-Made Deep Creek Real Estate, LLC

    207 Shenandoah Ave, Oakland, MD 21550
    • /27

      Not Listed For Sale

      128 Shaffer Ln, Oakland, MD 21550

      • 3 Beds
      • 1 Bath
      • 1,040 Sq Ft
      • Built 2001
      128 Shaffer Ln, Oakland, MD 21550

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Andrew Eiswert Railey Realty, Inc.

  • /46

    $285,500

    Under Contract
    • 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
  • /79

    $910,000

    Sold Sep 25, 2025

    2045 Swallow Falls Rd, Oakland, MD 21550

    • 5 Beds
    • 3.5 Baths
    • 5,416 Sq Ft
    • Built 2023

    Last Sold Summary

    • $168/SF
    • 82 Days On Market

    Current Estimated Value $947,374

    Last Listing Agent Nick Fratz-Orr Railey Realty, Inc.

    2045 Swallow Falls Rd, Oakland, MD 21550
    • /49

      Est $1,182,659

      Not Listed For Sale

      215 Lower Penn Point Dr, Oakland, MD 21550

      • 5 Beds
      • 4.5 Baths
      • 2,580 Sq Ft
      • Built 2001
      215 Lower Penn Point Dr, Oakland, MD 21550

      Last Sold Summary

      • 51 Days On Market

      Last Listing Agent Lauren McCann Railey Realty, Inc.

  • /15

    $149,000

    • Land
    • 3.29 Acres
    • $45,289 per Acre

    16 Woodlands Hill Ct, Oakland, MD 21550

    3.29-acre wooded building lot in The View community at Deep Creek Lake. This spacious parcel offers a private setting with plenty of room for your future mountain or lake area retreat. Conveniently located off Lakeshore Drive and just minutes from Deep Creek Lake, Wisp Resort, restaurants, shopping, and other area amenities. Enjoy the perfect combination of privacy and convenience in one of the

    Jon Bell Railey Realty, Inc.

    16 Woodlands Hill Ct, Oakland, MD 21550
  • /43

    $587,500

    Sold Aug 22, 2025

    307 Winding Trail Ln Unit 12B, Oakland, MD 21550

    • 5 Beds
    • 4.5 Baths
    • 3,300 Sq Ft
    • Built 2019

    Last Sold Summary

    • $178/SF
    • 9 Days On Market

    Current Estimated Value $574,608

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    307 Winding Trail Ln Unit 12B, Oakland, MD 21550
    • /74

      Est $197,414

      Not Listed For Sale

      400 E St, Oakland, MD 21550

      • 4 Beds
      • 2 Baths
      • 2,880 Sq Ft
      • Built 1900
      400 E St, Oakland, MD 21550

      Last Sold Summary

      • 98 Days On Market

      Last Listing Agent Nick Fratz-Orr Railey Realty, Inc.

  • /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
  • /7

    $14,000

    Sold Jul 24, 2026

    0 Maryland Hwy Unit MDGA2011452, Oakland, MD 21550

    • Land
    • 40,075 Sq Ft
    • $15,217 per Acre

    Last Sold Summary

    • 53% Below List Price
    • 73 Days On Market

    Last Listing Agent Dan (Sussan) Duggan 1 Real Estate Source LLC

    0 Maryland Hwy Unit MDGA2011452, Oakland, MD 21550

Showing Results 521 - 560, Page 14 of 18

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