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

Registered offenders on the map

Save search

Registered offenders on the map

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
Single-Family Homes in Oakland, MD
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

Registered offenders on the map

Save search
3 beds
35 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

Single-Family Homes in Oakland, MD

Single-Family Homes in Oakland, MD

Hide Map
24 of 35 Listings
Map

Single-Family Homes in Oakland, MD

24 of 35 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas
  1. 1959 Birchwood Dr — photo36Active

    $235,000

    2 bd · 2 ba · 1,152 sqft

    1959 Birchwood Dr, Oakland, MD

    Laura C Newhall · Taylor-Made Deep Creek Sales

  2. 1529 Paradise Point Rd — photo67Active

    $639,000

    3 bd · 3 ba · 1,933 sqft

    1529 Paradise Point Rd, Oakland, MD

    Elizabeth S Spiker Holcomb · Taylor-Made Deep Creek Sales

  3. 607 Pin Oak Cir — photo77Active

    $499,000

    5 bd · 4 ba · 3,800 sqft

    607 Pin Oak Cir, Oakland, MD

    Rachel Bruch · Railey Realty, Inc.

  4. 139 S Oakhall Dr — photo52Active

    $229,000

    3 bd · 2 ba · 1,612 sqft

    139 S Oakhall Dr, Oakland, MD

    Laura C Newhall · Taylor-Made Deep Creek Sales

  5. 102 Roanoke Ave — photo38Active

    $74,990

    3 bd · 1 ba · 1,932 sqft

    102 Roanoke Ave, Oakland, MD

    Heidi J Heiderman · Samson Properties

  6. 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

  7. 100 San Francisco St — photo52Active

    $645,000

    2 bd · 2 ba · 1,520 sqft

    100 San Francisco St, Oakland, MD

    Nick Fratz-Orr · Railey Realty, Inc.

  8. 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

  9. 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.

  10. 18948 Garrett Hwy — photo41Active

    $375,000

    2 bd · 2 ba · 1,404 sqft

    18948 Garrett Hwy, Oakland, MD

    Daniel Patrick Duggan Sr. · 1 Real Estate Source LLC

  11. 180 Paradise Ridge Rd — photo59Active

    $689,000

    4 bd · 3 ba · 2,402 sqft

    180 Paradise Ridge Rd, Oakland, MD

    Brian P Homberg · Taylor-Made Deep Creek Sales

  12. 15 Byran Dr — photo60Active

    $799,900

    4 bd · 4 ba · 0 sqft

    15 Byran Dr, Oakland, MD

    Jonathan D Bell · Railey Realty, Inc.

  13. 325 Markwood Dr — photoPrice Reduced66Active

    $769,000

    4 bd · 4 ba · 3,376 sqft

    325 Markwood Dr, Oakland, MD

    Jay L Ferguson · Taylor-Made Deep Creek Sales

  14. 40 Sunshine — photoPrice Reduced43Active

    $159,000

    3 bd · 1 ba · 1,516 sqft

    40 Sunshine, Oakland, MD

    Danielle Luscombe · Taylor-Made Deep Creek Sales

  15. 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

  16. 206 W Liberty St — photoPrice Reduced35Active

    $149,000

    2 bd · 1 ba · 2,008 sqft

    206 W Liberty St, Oakland, MD

    Nicole Jackson · Railey Realty, Inc.

  17. 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

  18. 941 Mountainview Dr — photoPrice Reduced60Active

    $719,999

    4 bd · 4 ba · 4,377 sqft

    941 Mountainview Dr, Oakland, MD

    Nicole Jackson · Railey Realty, Inc.

  19. 122 Woodlands Hill Ln — photoPrice Reduced59Active

    $1,089,000

    4 bd · 5 ba · 2,656 sqft

    122 Woodlands Hill Ln, Oakland, MD

    Brian P Homberg · Taylor-Made Deep Creek Sales

  20. 560 Glendale Rd — photoPrice Reduced24Active

    $374,900

    2 bd · 1 ba · 700 sqft

    560 Glendale Rd, Oakland, MD

    Lauren McCann · Railey Realty, Inc.

  21. 127 Paradise Hts — photoPrice Reduced24Active

    $999,999

    3 bd · 3 ba · 2,240 sqft

    127 Paradise Hts, Oakland, MD

    Norman S Domingo · XRealty.NET LLC

  22. 251 Robinwood Dr — photoPrice Reduced63Active

    $899,900

    5 bd · 5 ba · 4,284 sqft

    251 Robinwood Dr, Oakland, MD

    Jay L Ferguson · Taylor-Made Deep Creek Sales

  23. 83 Bethlehem Rd — photo43Active

    $2,499,900

    4 bd · 2 ba · 2,190 sqft

    83 Bethlehem Rd, Oakland, MD

    Jonathan D Bell · Railey Realty, Inc.

  24. 400 Bear Dr E — photoPrice Reduced42Active

    $235,000

    2 bd · 2 ba · 560 sqft

    400 Bear Dr E, Oakland, MD

    Danielle Luscombe · Taylor-Made Deep Creek Sales

12

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: 2026-09-19 12:00:59 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

    Oakland housing market

    August 2026

    Oakland 12-month median sale price trend

    Selling at 95.5% of asking price

    Buyers here are paying below asking. MLS · 21 sales · as of Aug 31, 2026

    Homes that sold · County records, as of Aug 27, 2026

    Median sale price
    $289,250$116,000–$684,250 typical range
    Price per sq. ft.
    $281
    Sales
    26
    Paid in cash
    46.2%

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

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

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

    Year-over-year
    41.5%

    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.