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Waterfront Homes in Oakland, MD
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3 bedsNew constructionWith a pool

Waterfront Homes in Oakland, MD

Waterfront Homes in Oakland, MD

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19 Listings
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Waterfront Homes in Oakland, MD

19 Listings

Your local brokerage

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Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas
  1. 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

  2. 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.

  3. 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

  4. 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

  5. 565 Glendale Rd #213 — photo24Active

    $225,000

    1 bd · 1 ba · 0 sqft

    565 Glendale Rd #213, Oakland, MD

    Charlotte Savoy · The KW Collective

  6. 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

  7. 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

  8. 193 Red Run Rd #1-B-3 — photoPrice Reduced57Active

    $550,000

    2 bd · 2 ba · 1,340 sqft

    193 Red Run Rd #1-B-3, Oakland, MD

    John E McNamara Jr. · RE/MAX Results

  9. 187 Lower Penn Point Dr — photoPrice Reduced44Active

    $1,425,000

    3 bd · 2 ba · 1,695 sqft

    187 Lower Penn Point Dr, Oakland, MD

    Amy Webster Mangum · Railey Realty, Inc.

  10. 20160 Garrett Hwy #C307 — photo49Active

    $379,500

    1 bd · 1 ba · 636 sqft

    20160 Garrett Hwy #C307, Oakland, MD

    Justin D Liller · Railey Realty, Inc.

  11. 565 Glendale Rd #303B — photo34Active

    $399,900

    2 bd · 1 ba · 887 sqft

    565 Glendale Rd #303B, Oakland, MD

    Sean H Sober · Taylor-Made Deep Creek Sales

  12. 20160 Garrett Hwy #H706 — photo27Active

    $309,000

    1 bd · 1 ba · 550 sqft

    20160 Garrett Hwy #H706, Oakland, MD

    James Calvin Matthews · Taylor-Made Deep Creek Sales

  13. 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

  14. 827 Penn Point Rd — photo64Active

    $1,400,000

    5 bd · 4 ba · 2,832 sqft

    827 Penn Point Rd, Oakland, MD

    Elizabeth S Spiker Holcomb · Taylor-Made Deep Creek Sales

  15. 565 Glendale Rd #125 — photo55Active

    $329,900

    1 bd · 1 ba · 496 sqft

    565 Glendale Rd #125, Oakland, MD

    Jonathan D Bell · Railey Realty, Inc.

  16. 565 Glendale Rd #B206 — photoPrice Reduced32Active

    $299,900

    2 bd · 1 ba · 780 sqft

    565 Glendale Rd #B206, Oakland, MD

    Carlos A Espinoza · Jason Mitchell Group

  17. 47 Holy Cross — photo109Active

    $6,499,900

    7 bd · 9 ba · 11,417 sqft

    47 Holy Cross, Oakland, MD

    Jonathan D Bell · Railey Realty, Inc.

  18. 531 Glendale Rd #B302 — photoPrice Reduced29Active

    $339,900

    2 bd · 1 ba · 887 sqft

    531 Glendale Rd #B302, Oakland, MD

    Larry E Smith · Railey Realty, Inc.

  19. 565 Glendale Rd #212a — photoPrice Reduced20Active

    $175,000

    1 bd · 1 ba · 527 sqft

    565 Glendale Rd #212a, Oakland, MD

    Nick Fratz-Orr · Railey Realty, Inc.

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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.

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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: 2026-09-01 19:25:54 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 · 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.