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3 bedsNew constructionWith a pool
5 Bedroom Homes in Annapolis, MD
31 listings

5 Bedroom Homes in Annapolis, MD

5 Bedroom Homes in Annapolis, MD

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24 of 31 Listings
Map

5 Bedroom Homes in Annapolis, MD

24 of 31 Listings

  1. 139 Stilly Way — photoNew53

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas
Active

$1,200,000

5 bd · 5 ba · 5,575 sqft

139 Stilly Way, Annapolis, MD

Cheryl Jersey-Lecourt · Long & Foster Real Estate, Inc.

  • 1603 Waters Ridge Ct — photo95Active

    $1,495,000

    5 bd · 5 ba · 3,752 sqft

    1603 Waters Ridge Ct, Annapolis, MD

    Christina J Palmer · Keller Williams Flagship

  • 101 Carraway Ln — photo44Active

    $695,000

    5 bd · 5 ba · 3,432 sqft

    101 Carraway Ln, Annapolis, MD

    Bradley R Kappel · TTR Sotheby's International Realty

  • 8 Revell St — photo59Active

    $1,349,000

    5 bd · 2 ba · 2,600 sqft

    8 Revell St, Annapolis, MD

    Rachel Holmes · Coldwell Banker Realty

  • 1711 Ritchie Hwy — photo36Active

    $1,199,500

    5 bd · 5 ba · 5,086 sqft

    1711 Ritchie Hwy, Annapolis, MD

    Karen Millett · Taylor Properties

  • 206 Bowen Ct — photoPrice Reduced46Active

    $950,000

    5 bd · 4 ba · 4,564 sqft

    206 Bowen Ct, Annapolis, MD

    Arianit Musliu · Redfin Corp

  • 111 Ellershaw Ct — photo67Active

    $1,349,000

    5 bd · 5 ba · 3,600 sqft

    111 Ellershaw Ct, Annapolis, MD

    Ryan C Turner · Coldwell Banker Realty

  • 1825 Johnson Rd — photo41Active

    $1,050,000

    5 bd · 4 ba · 3,028 sqft

    1825 Johnson Rd, Annapolis, MD

    Pier H Butler · Curtis Real Estate Company

  • 14 E Lake Dr — photo49Active

    $3,997,000

    5 bd · 7 ba · 6,234 sqft

    14 E Lake Dr, Annapolis, MD

    Bradley R Kappel · TTR Sotheby's International Realty

  • 3280 Arundel On The Bay Rd — photoPrice Reduced31Active

    $750,000

    5 bd · 5 ba · 3,144 sqft

    3280 Arundel On The Bay Rd, Annapolis, MD

    Deanna L Marshall · The KW Collective

  • 1979 Baltimore Annapolis Blvd — photo83Active

    $3,000,000

    5 bd · 2 ba · 5,522 sqft

    1979 Baltimore Annapolis Blvd, Annapolis, MD

    Alison Wisnom · Coldwell Banker Realty

  • 1309 Hawkins Ln — photoPrice Reduced48Active

    $645,000

    5 bd · 3 ba · 1,830 sqft

    1309 Hawkins Ln, Annapolis, MD

    sandra K. Libby · Long & Foster Real Estate, Inc.

  • 1486 Downham Market — photo87Active

    $2,999,900

    5 bd · 5 ba · 5,260 sqft

    1486 Downham Market, Annapolis, MD

    Wendy T Oliver · Coldwell Banker Realty

  • 112 Speicher Dr — photoPrice Reduced38Active

    $949,000

    5 bd · 4 ba · 2,912 sqft

    112 Speicher Dr, Annapolis, MD

    Christine M Leonard · Redfin Corp

  • 1614 Annesley Ct — photo46Active

    $2,250,000

    5 bd · 7 ba · 8,278 sqft

    1614 Annesley Ct, Annapolis, MD

    Bradley R Kappel · TTR Sotheby's International Realty

  • 140 Spa Dr — photo89Active

    $4,600,000

    5 bd · 4 ba · 5,095 sqft

    140 Spa Dr, Annapolis, MD

    Biana Arentz · Coldwell Banker Realty

  • 3733 Thomas Point Rd — photoPrice Reduced46Active

    $2,685,000

    5 bd · 5 ba · 5,082 sqft

    3733 Thomas Point Rd, Annapolis, MD

    Bradley R Kappel · TTR Sotheby's International Realty

  • 1322 Windsor Ridge Ln — photoPrice Reduced98Active

    $1,699,000

    5 bd · 6 ba · 4,648 sqft

    1322 Windsor Ridge Ln, Annapolis, MD

    Elizabeth Jean DuLaney · EXP Realty, LLC

  • 217 Lockwood Ct — photoPrice Reduced66Active

    $4,500,000

    5 bd · 4 ba · 4,107 sqft

    217 Lockwood Ct, Annapolis, MD

    sandra K. Libby · Long & Foster Real Estate, Inc.

  • 202 Wardour Dr — photoPrice Reduced59Active

    $1,599,000

    5 bd · 2 ba · 2,100 sqft

    202 Wardour Dr, Annapolis, MD

    David Orso · Berkshire Hathaway HomeServices PenFed Realty

  • 5 Franklin St — photo47Active

    $12,500,000

    5 bd · 7 ba · 5,993 sqft

    5 Franklin St, Annapolis, MD

    Bradley R Kappel · TTR Sotheby's International Realty

  • 83 Market St — photoPrice Reduced51Active

    $2,295,000

    5 bd · 4 ba · 3,178 sqft

    83 Market St, Annapolis, MD

    Elizabeth C Dooner · Coldwell Banker Realty

  • 8 Spa View Cir — photoPrice Reduced56Active

    $11,500,000

    5 bd · 6 ba · 6,061 sqft

    8 Spa View Cir, Annapolis, MD

    Georgeann A Berkinshaw · Coldwell Banker Realty

  • 2035 Maidstone Farm Rd — photo58Active

    $8,750,000

    5 bd · 7 ba · 7,105 sqft

    2035 Maidstone Farm Rd, Annapolis, MD

    Georgeann A Berkinshaw · Coldwell Banker Realty

  • 12

    Explore Annapolis homes

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    By type

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    • With a pool
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    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #01-6355

    Call Thomas

    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: 2026-09-03 04:06:07 UTC

    Annapolis, MD community profile

    Population
    42,070
    Median income
    $97,319
    Housing units
    18,886
    People per sq. mi.
    704.7
    Area
    59.7 sq. mi.

    Source: HJN community data

    Annapolis housing market

    August 2026 · This period is still settling

    Annapolis 12-month median sale price trend

    Selling at 100.0% of asking price

    Sales here are closing essentially at asking. MLS · 101 sales · as of Aug 31, 2026

    Homes that sold · County records, as of Aug 17, 2026

    Median sale price
    $720,000$480,000–$1,180,000 typical range
    Price per sq. ft.
    $329
    Sales
    57
    Paid in cash
    35.1%

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

    Median list price
    $697,000
    Homes for sale
    258
    Median days on market
    10 days

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

    Year-over-year
    22.8%

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

    Median home size
    1,920 sq. ft.