12,257

Homes in ZIP Code 21550

Section Image
    • /51

      Est $329,885 Not Listed For Sale

      18361 Garrett Hwy, Oakland, MD 21550

      • 4 Beds
      • 3 Baths
      • 2,112 Sq Ft
      • Built 1977
      18361 Garrett Hwy, Oakland, MD 21550

      Last Sold Summary

      • 23% Above List Price
      • $127/SF
      • 131 Days On Market

      Last Sold Price $268,000

      Last Listing Agent Jon Bell Railey Realty, Inc.

  • /24

    $619,900 Pending

    • 4 Beds
    • 4 Baths
    • 2,550 Sq Ft

    66 Paradise Ridge Rd, Oakland, MD 21550

    Welcome to 66 Paradise Ridge Rd, a charming single-familyhome in the picturesque town of Oakland, MD. LAKE ACCESS WITH DEEDED DOCK. Builtin 1984, this two-story residence offers a spacious layout with 4 bathrooms and 2,550square feet of finished living space. Situated on a generous 21,780-square-foot lot, theproperty provides plenty of room to roam and enjoy the natural

    Joseph Hawkins Hawkins Real Estate Company

    66 Paradise Ridge Rd, Oakland, MD 21550
  • /26

    $1,275,000 Sold Jun 02, 2025

    464 Lake Forest Dr, Oakland, MD 21550

    • 4 Beds
    • 3.5 Baths
    • 2,496 Sq Ft
    • Built 1997

    Last Sold Summary

    • $511/SF
    • 277 Days On Market

    Current Estimated Value $1,341,842

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

    464 Lake Forest Dr, Oakland, MD 21550
    • /58

      Est $459,688 Not Listed For Sale

      2734 Mayhew Inn Rd, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,536 Sq Ft
      • Built 1974
      2734 Mayhew Inn Rd, Oakland, MD 21550

      Last Sold Summary

      • 15% Above List Price
      • $260/SF
      • 2 Days On Market

      Last Sold Price $399,000

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

  • /11

    $199,900

    • Land
    • 0.11 Acre
    • $1,817,273 per Acre

    2 Overlook Ridge Dr S, Oakland, MD 21550

    Enjoy the best the lake has to offer from 'Overlook Ridge'! Boasting year-round lake views, yet tucked away in a peaceful and serene community setting. Short drive to the community lake access area for swimming and fishing! Dock Slips may be leased through HOA. Utilities to site and ready to build your perfect four-season Deep Creek getaway. Located just off of Rt. 219, with easy access to all

    Jon Bell Railey Realty, Inc.

    2 Overlook Ridge Dr S, Oakland, MD 21550
  • /9

    $145,000 Sold Jul 03, 2025

    30 Snowshoe Ct, McHenry, MD 21541

    • Land
    • 0.36 Acre
    • $402,778 per Acre

    Last Sold Summary

    • 53 Days On Market

    Last Listing Agent Mike Fenton Railey Realty, Inc.

    30 Snowshoe Ct, McHenry, MD 21541
    • /76

      Est $1,073,195 Not Listed For Sale

      1882 Marsh Hill Rd, Mc Henry, MD 21541

      • 4 Beds
      • 4.5 Baths
      • 3,216 Sq Ft
      • Built 2003
      1882 Marsh Hill Rd, Mc Henry, MD 21541

      Last Sold Summary

      • 5% Above List Price
      • $319/SF
      • 6 Days On Market

      Last Sold Price $1,025,000

      Last Listing Agent Kevin Liller Railey Realty, Inc.

  • /38

    $297,500

    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft

    505 Southern Pines Dr, Oakland, MD 21550

    Charming ranch-style home located in the desirable Southern Pines neighborhood. From the moment you enter, you’ll appreciate the warm and inviting feel of the open layout. The main level features three comfortable bedrooms, two full bathrooms, beautiful hardwood flooring, and a seamless kitchen, living, and dining area that creates an ideal space for everyday living and entertaining. The recently

    Betsy Spiker Holcomb Taylor Made Deep Creek Real Estate

    505 Southern Pines Dr, Oakland, MD 21550
  • /92

    $635,000 Sold Sep 26, 2025

    5 Arrowhead Ln, Oakland, MD 21550

    • 3 Beds
    • 3 Baths
    • 1,650 Sq Ft
    • Built 1988

    Last Sold Summary

    • $385/SF
    • 116 Days On Market

    Current Estimated Value $646,022

    Last Listing Agent Kevin Liller Railey Realty, Inc.

    5 Arrowhead Ln, Oakland, MD 21550
    • /38

      Est $251,642 Not Listed For Sale

      87 Mitchell Dr, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,858 Sq Ft
      • Built 1971
      87 Mitchell Dr, Oakland, MD 21550

      Last Sold Summary

      • 12% Above List Price
      • $121/SF
      • 28 Days On Market

      Last Sold Price $225,000

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

  • /33

    $399,999 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,536 Sq Ft

    2678 Mayhew Inn Rd, Deer Park, MD 21550

    Cozy up at this charming modernized cottage tucked along the wooded hillside. With an open layout, stone fireplace, and plush furnishings, this is the place to return to after a busy day around the area. Enjoy your morning coffee on the Juliet balcony or the front or back deck, or curl up in front of the newly updated wood fireplace in the living room. Enjoy some swimming, fishing, or kayaking at

    Tina Hyatt Hyatt & Company Real Estate, LLC

    2678 Mayhew Inn Rd, Deer Park, MD 21550
  • /2

    $280,000 Sold Feb 23, 2026

    1359 Cedar Ln, Oakland, MD 21550

    • 2 Beds
    • 1.5 Baths
    • 1,440 Sq Ft
    • Built 1979

    Last Sold Summary

    • 2% Above List Price
    • $194/SF
    • 8 Days On Market

    Current Estimated Value $275,476

    Last Listing Agent Laura Newhall Taylor Made Deep Creek Real Estate

    1359 Cedar Ln, Oakland, MD 21550
    • /46

      Est $1,923,155 Not Listed For Sale

      1425 Sandy Shores Rd, Mc Henry, MD 21541

      • 5 Beds
      • 5.5 Baths
      • 4,644 Sq Ft
      • Built 1998
      1425 Sandy Shores Rd, Mc Henry, MD 21541

      Last Sold Summary

      • 18% Below List Price
      • $506/SF
      • 33 Days On Market

      Last Sold Price $2,350,000

      Last Listing Agent Roxane Agostinelli The KW Collective

  • /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
  • /6

    $180,000 Sold Apr 11, 2025

    223 Old Crellin Rd, Oakland, MD 21550

    • 1 Bed
    • 1 Bath
    • 980 Sq Ft
    • Built 1986

    Last Sold Summary

    • $184/SF
    • 67 Days On Market

    Last Listing Agent Garrett Shingler Better Homes & Gardens Real Estate Old Line Group

    223 Old Crellin Rd, Oakland, MD 21550
    • /5

      Est $166,247 Not Listed For Sale

      133 Fox Den Rd, Oakland, MD 21550

      • Built 1945
      133 Fox Den Rd, Oakland, MD 21550

      Last Sold Summary

      • 85% Above List Price
      • $125/SF
      • 7 Days On Market

      Last Sold Price $90,000

      Last Listing Agent Michael Cumerlato Jason Mitchell Group

  • /56

    $339,000

    • 5 Beds
    • 3.5 Baths
    • 3,682 Sq Ft

    697 Monte Vista Rd, Oakland, MD 21550

    Tucked away just minutes from downtown Oakland, MD, lies a home that truly surprises with over 3,500 sq. ft. of living space on 1.88 acres with breathtaking farm and mountain views. Step inside the main level, where the master suite awaits along with two additional large bedrooms and a full bath, plus a mudroom area with a convenient half bath—perfect for entertaining. Cozy evenings are made even

    Laura Newhall Taylor Made Deep Creek Real Estate

    697 Monte Vista Rd, Oakland, MD 21550
  • /40

    $171,000 Sold May 30, 2025

    5459 Hutton Rd, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • 2,000 Sq Ft
    • Built 1940

    Last Sold Summary

    • $86/SF
    • 113 Days On Market

    Current Estimated Value $177,668

    Last Listing Agent Debra Beitzel Long & Foster Real Estate, Inc.

    5459 Hutton Rd, Oakland, MD 21550
    • /53

      Est $1,282,114 Not Listed For Sale

      483 Skippers Point Rd, Oakland, MD 21550

      • 4 Beds
      • 3 Baths
      • 2,286 Sq Ft
      • Built 1983
      483 Skippers Point Rd, Oakland, MD 21550

      Last Sold Summary

      • 9% Above List Price
      • $516/SF
      • 127 Days On Market

      Last Sold Price $1,180,500

      Last Listing Agent Eric Crawford Taylor Made Deep Creek Real Estate

  • /10

    $995,000

    • Land
    • 0.58 Acre
    • $1,715,517 per Acre

    0 Glendale Rd Lot 12 Alpine Village Subdivision, Oakland, MD 21550

    RARE OPPURTUNITY! Discover one of the final opportunities to own true lakefront on the iconic Glendale Road! This premier homesite offers approximately 75 feet of pristine Deep Creek Lake frontage in a serene no wake zone, perfect for swimming, kayaking, and peaceful lakeside enjoyment. Zoning in this area is Town Center. This allows for a larger building area within the lot with relaxed

    Lucas Muenchow Railey Realty, Inc.

    0 Glendale Rd Lot 12 Alpine Village Subdivision, Oakland, MD 21550
  • /62

    $237,000 Sold Jun 13, 2025

    13903 Garrett Hwy, Oakland, MD 21550

    • 1 Bed
    • 3 Baths
    • 1,536 Sq Ft
    • Built 1977

    Last Sold Summary

    • $154/SF
    • 15 Days On Market

    Last Listing Agent Rich Orr Railey Realty, Inc.

    13903 Garrett Hwy, Oakland, MD 21550
    • /35

      Est $130,159 Not Listed For Sale

      830 N 4th St, Oakland, MD 21550

      • 3 Beds
      • 1 Bath
      • 1,656 Sq Ft
      • Built 1930
      830 N 4th St, Oakland, MD 21550

      Last Sold Summary

      • 40% Below List Price
      • $131/SF
      • 68 Days On Market

      Last Sold Price $216,154

      Last Listing Agent Andrew Orr The KW Collective

  • /8

    $69,000

    • Land
    • 0.66 Acre
    • $104,545 per Acre

    LOT 7 Grand Estates Dr, Sang Run, MD 21541

    Looking for the perfect spot to build your Deep Creek Lake getaway? This prime mountaintop lot in Lago Vista is ready for your dream home. With public utilities available, you can start planning your mountain retreat, full-time residence, or investment property with ease. Enjoy having Wisp Resort and Lodestone Golf Club practically in your backyard, plus all the fun and adventure of Deep Creek

    Eric Crawford Taylor Made Deep Creek Real Estate

    LOT 7 Grand Estates Dr, Sang Run, MD 21541
  • /12

    $154,900 Sold Aug 25, 2025

    Lots 54 & 53 Sloan Tract Rd, Oakland, MD 21550

    • Land
    • 0.6 Acre
    • $258,167 per Acre

    Last Sold Summary

    • 17 Days On Market

    Last Listing Agent Andrew Eiswert Railey Realty, Inc.

    Lots 54 & 53 Sloan Tract Rd, Oakland, MD 21550
    • /70

      Est $244,971 Not Listed For Sale

      402 Leighton Dr, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,332 Sq Ft
      • Built 1940
      402 Leighton Dr, Oakland, MD 21550

      Last Sold Summary

      • 14% Above List Price
      • $161/SF
      • 6 Days On Market

      Last Sold Price $215,000

      Last Listing Agent Kevin Liller Railey Realty, Inc.

  • /13

    $119,900

    • Land
    • 0.78 Acre
    • $153,718 per Acre

    120 Sundance Way, McHenry, MD 21541

    Level wooded building lot with scenic mountain views! This .78-acre homesite is centrally located minutes from Wisp Resort, Deep Creek Lake, Lodestone Golf Course, local restaurants, and nearby state parks, all while tucked away in a private mountaintop community. Ready to build with public water and sewer hookups to site. A straightforward opportunity to build your mountain dream home right in

    Mike Fenton Railey Realty, Inc.

    120 Sundance Way, McHenry, MD 21541
  • /71

    $899,900 Sold Jun 26, 2025

    145 Lower Penn Point Dr, Oakland, MD 21550

    • 3 Beds
    • 3.5 Baths
    • 2,106 Sq Ft
    • Built 2007

    Last Sold Summary

    • $427/SF
    • 135 Days On Market

    Current Estimated Value $935,867

    Last Listing Agent Emillie Albrecht Real Broker, LLC

    145 Lower Penn Point Dr, Oakland, MD 21550
    • /31

      Est $403,058 Not Listed For Sale

      1793 Kempton Rd, Oakland, MD 21550

      • 5 Beds
      • 1 Bath
      • 2,280 Sq Ft
      • Built 1880
      1793 Kempton Rd, Oakland, MD 21550

      Last Sold Summary

      • 15% Above List Price
      • $154/SF
      • 23 Days On Market

      Last Sold Price $350,000

      Last Listing Agent Linda Deremer Appalachian Realty

  • /27

    $229,900

    • 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
  • /58

    $1,425,000 Sold Oct 28, 2025

    20676 Garrett Hwy, Oakland, MD 21550

    • 5 Beds
    • 4.5 Baths
    • 2,280 Sq Ft
    • Built 2015

    Last Sold Summary

    • $625/SF
    • 17 Days On Market

    Current Estimated Value $1,432,702

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    20676 Garrett Hwy, Oakland, MD 21550
    • /67

      Est $255,224 Not Listed For Sale

      218 Weber Rd, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,605 Sq Ft
      • Built 1930
      218 Weber Rd, Oakland, MD 21550

      Last Sold Summary

      • 4% Below List Price
      • $165/SF
      • 56 Days On Market

      Last Sold Price $265,000

      Last Listing Agent Kelsey Meyers Railey Realty, Inc.

  • /42

    $245,000 Coming Soon

    • 2 Beds
    • 2 Baths
    • 1,320 Sq Ft

    13 Laurel Brook Dr, Oakland, MD 21550

    Affordable well maintained 2 Bedroom 2 Bath townhouse style condominium less than 1 mile from Deep Creek Lake. Offering low maintenance and a pleasant setting, the property works well for full and part time ownership. The unit offers recent upgrades and Includes 2 parking spaces along with public water, sewer and weekly trash pickup. Shown by appointment only.

    Bill Weissgerber Railey Realty, Inc.

    13 Laurel Brook Dr, Oakland, MD 21550
  • /35

    $285,000 Sold Jul 03, 2025

    506 Cedar Ln, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • Built 1979

    Last Sold Summary

    • $212/SF
    • 16 Days On Market

    Current Estimated Value $290,311

    Last Listing Agent Laura Newhall Taylor Made Deep Creek Real Estate

    506 Cedar Ln, Oakland, MD 21550
    • /71

      Est $840,251 Not Listed For Sale

      589 Mountainview Dr, Oakland, MD 21550

      • 4 Beds
      • 4 Baths
      • 2,665 Sq Ft
      • Built 1993
      589 Mountainview Dr, Oakland, MD 21550

      Last Sold Summary

      • 23% Above List Price
      • $257/SF
      • 247 Days On Market

      Last Sold Price $685,000

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

  • /19

    $65,000

    • 792 Sq Ft

    809 N St, Oakland, MD 21550

    This home needs TLC with the possibility to rebuild on existing foundation if you want to rehab. Buyer to confirm with the county and the town of Mt. Lake Park for rebuilding stipulations. Being sold "As Is". Caution: Entering this property is at your own discretion and responsibility.RAILEY REALTY IS NOT THE CARETAKER OF PROPERTIES LISTED BY IT. PROSPECTIVE PURCHASERS AND THEIR

    Kathy Gibson Railey Realty, Inc.

    809 N St, Oakland, MD 21550
  • /28

    $339,000 Sold Aug 01, 2025

    20160 Garrett Hwy Unit H712, Oakland, MD 21550

    • 1 Bed
    • 1 Bath
    • 450 Sq Ft
    • Built 1972

    Last Sold Summary

    • $753/SF
    • 124 Days On Market

    Last Listing Agent Larry Smith Railey Realty, Inc.

    20160 Garrett Hwy Unit H712, Oakland, MD 21550
    • /90

      Est $1,487,893 Not Listed For Sale

      3037 Shingle Camp Rd, Mc Henry, MD 21541

      • 4 Beds
      • 6 Baths
      • 3,008 Sq Ft
      • Built 2002
      3037 Shingle Camp Rd, Mc Henry, MD 21541

      Last Sold Summary

      • 18% Below List Price
      • $600/SF
      • 3 Days On Market

      Last Sold Price $1,805,000

      Last Listing Agent Jon Bell Railey Realty, Inc.

  • /29

    $75,000

    • Land
    • 0.6 Acre
    • $125,000 per Acre

    40 Fern Loop, Sang Run, MD 21541

    Escape to the mountains and relax on your own piece of paradise on "Fern Loop". Build your dream home on this beautiful wooded homesite-"Lot 40" in the peaceful community of Sandy Shores Heights. On the mountaintop with easy access to the Lodestone Golf Course and a convenient hop to Deep Creek Lake, Fork Run, Yough River & Wisp Ski Resort. Utilities to site with public water & sewer hookups

    Kathy Gibson Railey Realty, Inc.

    40 Fern Loop, Sang Run, MD 21541
  • /4

    $3,000 Sold Oct 24, 2025

    Lot 27 Stool Rock Rd, Oakland, MD 21550

    • Land
    • 0.51 Acre
    • $5,882 per Acre

    Last Sold Summary

    • 67 Days On Market

    Last Listing Agent Elizabeth Broadwater Taylor Made Deep Creek Real Estate

    Lot 27 Stool Rock Rd, Oakland, MD 21550
    • /38

      Est $532,000 Not Listed For Sale

      193 Red Run Rd Unit 1A2, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,300 Sq Ft
      • Built 1978
      193 Red Run Rd Unit 1A2, Oakland, MD 21550

      Last Sold Summary

      • 3% Below List Price
      • $423/SF
      • 6 Days On Market

      Last Sold Price $550,000

      Last Listing Agent Jay Ferguson Taylor Made Deep Creek Real Estate

Showing Results 201 - 240, Page 6 of 18

How to Buy a Home How to Finance a Home How to Sell a Home