Oakland, MD

Lakefront Homes for Sale in Oakland, MD

20Results

Waterfront and lakefront property are the most searched features on our site, and Oakland addresses cover much of the southern end of Deep Creek Lake. See all Oakland real estate, create a free account to save this search and receive alerts, or call Railey Realty at 301-387-2000 to speak with an agent.

Newest
New Listing
Lot 18 Laurel Court Oakland MD 21550

$85,000

Oakland, MD

Lot 18 Laurel Court

  • Land
  • 1.08 Acre
  • 9 Days on Market
MLS#: MDGA2012966
New Listing

$909,000

Oakland, MD

2296 Lake Shore Drive

  • 4 Beds
  • 3 Baths
  • 1.15 Acre
  • 2,796 SqFt
  • 12 Days on Market
MLS#: MDGA2012922

$279,000

Oakland, MD

565 Glendale Road, Unit 316

  • 2 Beds
  • 1 Bath
  • 772 SqFt
  • 33 Days on Market
MLS#: MDGA2012808
Pending

$1,100,000

Oakland, MD

2849 Shingle Camp Road

  • 3 Beds
  • 2 Baths
  • 0.34 Acres
  • 2,034 SqFt
  • 41 Days on Market
MLS#: MDGA2012730
Active Under Contract

$296,500

Oakland, MD

20160 Garett Highway, Unit 105A

  • 1 Bed
  • 1 Bath
  • 600 SqFt
  • 43 Days on Market
MLS#: MDGA2012720

$1,199,000

Oakland, MD

20698 Garrett Highway

  • 4 Beds
  • 3 Baths
  • 0.28 Acres
  • 1,844 SqFt
  • 65 Days on Market
MLS#: MDGA2012616

$3,950,000

Oakland, MD

1131 Lake Shore Drive

  • 8 Beds
  • 10 Baths
  • 1.53 Acre
  • 6,486 SqFt
  • 72 Days on Market
MLS#: MDGA2012514

$169,900

Oakland, MD

Mayhew Inn Road

  • Land
  • 0.97 Acres
  • 74 Days on Market
MLS#: MDGA2012550
Pending

$1,986,000

Oakland, MD

59 Boyd Paugh Lane

  • 5 Beds
  • 4 Baths
  • 0.88 Acres
  • 4,200 SqFt
  • 74 Days on Market
MLS#: MDGA2012512

$769,000

Oakland, MD

325 Markwood Drive

  • 4 Beds
  • 4 Baths
  • 4.35 Acres
  • 3,376 SqFt
  • 92 Days on Market
MLS#: MDGA2012328

$1,425,000

Oakland, MD

187 Lower Penn Point Drive

  • 3 Beds
  • 2 Baths
  • 0.45 Acres
  • 1,695 SqFt
  • 93 Days on Market
MLS#: MDGA2012396

$550,000

Oakland, MD

193 Red Run Road, Unit 1-B-3

  • 2 Beds
  • 2 Baths
  • 1,340 SqFt
  • 111 Days on Market
MLS#: MDGA2012232

Oakland, MD Properties on Deep Creek Lake

Lakefront listings with an Oakland address sit mostly along the coves and shoreline at the southern end of Deep Creek Lake, from older cottages to larger homes with docks and wide water views. Deep Creek Lake is the largest freshwater lake in Maryland, and summer brings boating, swimming and fishing, while winter brings skiing at Wisp a short drive north. Lakefront lots at Deep Creek are subject to buffer strip rules and dock permits, so those details are worth reviewing early. This search lists every lakefront property for sale in Oakland. Railey Realty can help you compare shoreline and dock options. See lake access homes in Swanton or browse homes with a dock.

Frequently Asked Questions

What is the buffer strip at Deep Creek Lake?
Much of the shoreline includes a state owned buffer strip, and owners of adjoining lots can apply for permits for docks and limited use.
What is there to do at Deep Creek Lake?
Boating, swimming and fishing in summer, and skiing and snowboarding at Wisp Resort in winter.

Copyright 2026 BRIGHT, All Rights Reserved.  Information Deemed Reliable But Not Guaranteed. The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Railey Realty, Inc participates, and is provided by BRIGHT through a licensing agreement. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.Data last updated October 20, 2026. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale.