Realty.com
Buy

Start here

  • Homes for sale by state
  • Home buying tips
  • Before you start looking
  • The buying timeline

Afford it

  • Today's mortgage rates
  • Mortgage calculator
  • How much can I afford?
  • Get pre-approved

Make the deal

  • Writing a winning offer
  • Inspections & appraisals
  • Closing costs, itemized
  • Find a buyer's agent
Sell

Selling Options

  • What's my home worth?
  • Compare selling options
  • Get an instant cash offer
  • Buy before you sell

Resources

  • How selling works
  • When should I sell?
  • Home selling tips
  • Pricing your home
  • What's worth fixing first
  • Find a seller's agent
Home Loans
Find an Agent
Save searchAdvertiseSign In
Saved homesSaved searchesYour toursYour inquiriesRecently viewedAccount settings

Safety & registry resources

Review official public-safety information for any area from these government sources:

  • U.S. Dept. of Justice National Sex Offender Public Website (NSOPW)
  • FBI: state sex-offender registry directory
Save search
Oakland, MD Homes for Sale | Realty.com
Realty.com
Buy

Start here

  • Homes for sale by state
  • Home buying tips
  • Before you start looking
  • The buying timeline

Afford it

  • Today's mortgage rates
  • Mortgage calculator
  • How much can I afford?
  • Get pre-approved

Make the deal

  • Writing a winning offer
  • Inspections & appraisals
  • Closing costs, itemized
  • Find a buyer's agent
Save searchAdvertiseSign In
Saved homesSaved searchesYour toursYour inquiriesRecently viewedAccount settings
  • Rentals
  • Commercial

Safety & registry resources

Review official public-safety information for any area from these government sources:

  • U.S. Dept. of Justice National Sex Offender Public Website (NSOPW)
  • FBI: state sex-offender registry directory
Save search
3 beds
85 listings
Sell

Selling Options

  • What's my home worth?
  • Compare selling options
  • Get an instant cash offer
  • Buy before you sell

Resources

  • How selling works
  • When should I sell?
  • Home selling tips
  • Pricing your home
  • What's worth fixing first
  • Find a seller's agent
Home Loans
Find an Agent
New construction
With a pool

Homes for Sale in Oakland, MD

Homes for Sale in Oakland, MD

Hide Map
24 of 85 Listings
Map

Homes for Sale in Oakland, MD

24 of 85 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas
  1. 482 Pergin Farm Rd — photo34Active

    $449,000

    3 bd · 2 ba · 2,160 sqft

    482 Pergin Farm Rd, Oakland, MD

    Laura C Newhall · Taylor-Made Deep Creek Sales

  2. 333 Sloan Tract Rd — photo61Active

    $444,700

    4 bd · 4 ba · 1,585 sqft

    333 Sloan Tract Rd, Oakland, MD

    Debra A Beitzel · Long & Foster Real Estate, Inc.

  3. 20698 Garrett Hwy — photo53Active

    $1,199,000

    4 bd · 3 ba · 1,844 sqft

    20698 Garrett Hwy, Oakland, MD

    Elizabeth S Spiker Holcomb · Taylor-Made Deep Creek Sales

  4. 184 Upper Penn Point Dr — photo53Active

    $920,000

    3 bd · 2 ba · 1,152 sqft

    184 Upper Penn Point Dr, Oakland, MD

    Amy Webster Mangum · Railey Realty, Inc.

  5. 1407 Broadford Rd — photo52Active

    $399,900

    3 bd · 2 ba · 1,464 sqft

    1407 Broadford Rd, Oakland, MD

    Laura C Newhall · Taylor-Made Deep Creek Sales

  6. 395 Woodlands Hill Ln — photo66Active

    $899,900

    5 bd · 6 ba · 3,160 sqft

    395 Woodlands Hill Ln, Oakland, MD

    Jonathan D Bell · Railey Realty, Inc.

  7. 18948 Garrett Hwy — photo34Active

    $375,000

    2 bd · 2 ba · 1,404 sqft

    18948 Garrett Hwy, Oakland, MD

    Daniel Patrick Duggan Sr. · 1 Real Estate Source LLC

  8. 180 Paradise Ridge Rd — photo51Active

    $689,000

    4 bd · 3 ba · 2,402 sqft

    180 Paradise Ridge Rd, Oakland, MD

    Brian P Homberg · Taylor-Made Deep Creek Sales

  9. 1131 Lake Shore Dr — photo124Active

    $3,950,000

    8 bd · 10 ba · 6,486 sqft

    1131 Lake Shore Dr, Oakland, MD

    Elizabeth S Spiker Holcomb · Taylor-Made Deep Creek Sales

  10. 18 Mountainside Ct — photo99Active

    $799,000

    5 bd · 4 ba · 3,480 sqft

    18 Mountainside Ct, Oakland, MD

    Justin D Liller · Railey Realty, Inc.

  11. 59 Boyd Paugh Ln — photoPrice Reduced81Active

    $2,150,000

    5 bd · 4 ba · 4,200 sqft

    59 Boyd Paugh Ln, Oakland, MD

    James Calvin Matthews · Taylor-Made Deep Creek Sales

  12. 565 Glendale Rd #213 — photo24Active

    $225,000

    1 bd · 1 ba · 0 sqft

    565 Glendale Rd #213, Oakland, MD

    Charlotte Savoy · The KW Collective

  13. 5154 Maryland Hwy — photo68Active

    $460,000

    5 bd · 2 ba · 2,860 sqft

    5154 Maryland Hwy, Oakland, MD

    Wilda Charlene Deremer Aburn · Coldwell Banker Home Town Realty

  14. 181 Glotfelty Dr — photo51Active

    $399,000

    3 bd · 2 ba · 1,456 sqft

    181 Glotfelty Dr, Oakland, MD

    Kathy L Gibson · Railey Realty, Inc.

  15. 325 Markwood Dr — photo65Active

    $799,000

    4 bd · 4 ba · 3,376 sqft

    325 Markwood Dr, Oakland, MD

    Jay L Ferguson · Taylor-Made Deep Creek Sales

  16. 15 Byran Dr — photo60Active

    $799,900

    4 bd · 4 ba · 0 sqft

    15 Byran Dr, Oakland, MD

    Jonathan D Bell · Railey Realty, Inc.

  17. 40 Sunshine — photoPrice Reduced43Active

    $169,000

    3 bd · 1 ba · 1,516 sqft

    40 Sunshine, Oakland, MD

    Danielle Luscombe · Taylor-Made Deep Creek Sales

  18. 995 Betts Ln — photo45Active

    $549,900

    4 bd · 3 ba · 2,548 sqft

    995 Betts Ln, Oakland, MD

    Jay L Ferguson · Taylor-Made Deep Creek Sales

  19. 5 Laurel Brook Dr #5 — photo29Active

    $269,900

    2 bd · 2 ba · 1,400 sqft

    5 Laurel Brook Dr #5, Oakland, MD

    Jay L Ferguson · Taylor-Made Deep Creek Sales

  20. 251 Robinwood Dr — photo62Active

    $775,000

    5 bd · 5 ba · 4,284 sqft

    251 Robinwood Dr, Oakland, MD

    Jay L Ferguson · Taylor-Made Deep Creek Sales

  21. 206 W Liberty St — photoPrice Reduced35Active

    $174,900

    2 bd · 1 ba · 2,008 sqft

    206 W Liberty St, Oakland, MD

    Nicole Jackson · Railey Realty, Inc.

  22. 112 E Pennington St — photoPrice Reduced63Active

    $325,000

    5 bd · 3 ba · 2,165 sqft

    112 E Pennington St, Oakland, MD

    Sheila L Howell · Lake Homes Realty, LLC

  23. 615 E Oak St — photo60Active

    $365,000

    5 bd · 3 ba · 2,652 sqft

    615 E Oak St, Oakland, MD

    Lucas Alan Muenchow · Railey Realty, Inc.

  24. 102 N 3rd St — photo43Active

    $259,900

    3 bd · 2 ba · 1,998 sqft

    102 N 3rd St, Oakland, MD

    Kevin D Liller · Railey Realty, Inc.

12…4

Explore Oakland homes

By price

  • Under $300K
  • Under $500K
  • Under $700K
  • Luxury

By bedrooms

  • 2 beds
  • 3 beds
  • 4 beds
  • 5 beds

By type

  • Single family
  • Townhomes
  • Condos
  • Manufactured homes
  • Multi-family homes
  • Co-ops

By feature

Realty.com

L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

Equal Housing OpportunityEqual Housing Lender

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. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

© 2026 Realty.com. All rights reserved.·Privacy·Terms·California Privacy Rights·Accessibility·Licensing

Listing data & MLS disclosures

Bright MLS
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 Realty.com 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. 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.
Listing information ©2026 BRIGHT MLS®. All Rights Reserved, Information deemed reliable but not guaranteed. Data Last Updated: 2026-08-31 16:44:03 UTC
    • New construction
    • With a pool

    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #01-6355

    Call Thomas

    Oakland, MD community profile

    Population
    1,810
    Median income
    $67,177
    Housing units
    929
    People per sq. mi.
    8.8
    Area
    205.5 sq. mi.

    Source: HJN community data

    Nearby areas

    ZIP codes

    • 21550 (89)
    • 21541 (82)
    • 21561 (37)
    • 21539 (13)
    • 21536 (12)
    • 21562 (11)
    • 21531 (8)
    • 21520 (5)

    Cities

    • Mc Henry (82)
    • Swanton (37)
    • Lonaconing (13)
    • Grantsville (12)
    • Westernport (11)
    • Friendsville (8)
    • Accident (5)
    • Barton (4)

    Oakland housing market

    August 2026 · This period is still settling

    Oakland 12-month median sale price trend

    Selling at 95.6% of asking price

    Buyers here are paying below asking. MLS · 16 sales · as of Aug 28, 2026

    Homes that sold · County records, as of Aug 12, 2026

    Median sale price
    $295,500$210,000–$544,500 typical range
    Price per sq. ft.
    $273
    Sales
    15
    Paid in cash
    46.7%

    Homes on the market · MLS, as of Aug 28, 2026–Aug 31, 2026

    Median list price
    $464,900
    Homes for sale
    81
    Median days on market
    21 days

    Price trend · Assessor repeat sales, as of Aug 31, 2026

    Year-over-year
    44.6%

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026

    Median home size
    1,536 sq. ft.