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Luxury Homes in Annapolis, MD
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80 listings
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3 bedsNew constructionWith a pool

Luxury Homes in Annapolis, MD

Luxury Homes in Annapolis, MD

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24 of 80 Listings
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Luxury Homes in Annapolis, MD

24 of 80 Listings

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TO

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas
  1. 139 Stilly Way — photoNew53Active

    $1,200,000

    5 bd · 5 ba · 5,575 sqft

    139 Stilly Way, Annapolis, MD

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

  2. 820 Bay Ridge Ave — photoNew48Active

    $1,875,000

    4 bd · 5 ba · 3,900 sqft

    820 Bay Ridge Ave, Annapolis, MD

    Wendy T Oliver · Coldwell Banker Realty

  3. 1610 Ridout Rd — photoNew50Active

    $1,285,000

    4 bd · 3 ba · 3,182 sqft

    1610 Ridout Rd, Annapolis, MD

    Alexandra Tower Sears · TTR Sotheby's International Realty

  4. 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

  5. 113 Sellew Rd — photo51Active

    $1,351,875

    3 bd · 5 ba · 3,100 sqft

    113 Sellew Rd, Annapolis, MD

    Alison Wisnom · Coldwell Banker Realty

  6. 3 Rusty Red Dr — photo25Active

    $1,350,000

    6 bd · 6 ba · 2,922 sqft

    3 Rusty Red Dr, Annapolis, MD

    Alison Wisnom · Coldwell Banker Realty

  7. 2915 South Ct — photo35Active

    $1,295,000

    2 bd · 2 ba · 1,744 sqft

    2915 South Ct, Annapolis, MD

    Bradley R Kappel · TTR Sotheby's International Realty

  8. 1711 Ritchie Hwy — photo36Active

    $1,199,500

    5 bd · 5 ba · 5,086 sqft

    1711 Ritchie Hwy, Annapolis, MD

    Karen Millett · Taylor Properties

  9. 7017 Bay Front Dr — photo36Active

    $1,775,000

    2 bd · 3 ba · 2,176 sqft

    7017 Bay Front Dr, Annapolis, MD

    Rebecca C King · Home Towne Real Estate

  10. 1227 Cross Rd — photo47Active

    $1,285,000

    4 bd · 3 ba · 3,398 sqft

    1227 Cross Rd, Annapolis, MD

    Patrick DeLeonibus · TTR Sotheby's International Realty

  11. 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

  12. 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

  13. 145 Prince George St — photo43Active

    $1,199,000

    3 bd · 4 ba · 1,476 sqft

    145 Prince George St, Annapolis, MD

    Daniel V Iampieri · RE/MAX Aspire

  14. 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

  15. 1668 a Homewood Landing Rd — photo27Active

    $3,595,000

    6 bd · 6 ba · 5,718 sqft

    1668 a Homewood Landing Rd, Annapolis, MD

    Colleen M Smith · EXP Realty, LLC

  16. 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

  17. 203 S Southwood Ave — photo59Active

    $1,350,000

    4 bd · 4 ba · 5,091 sqft

    203 S Southwood Ave, Annapolis, MD

    Tim Velasco · ERA Martin Associates

  18. 120 Island View Dr — photo135Active

    $1,999,900

    4 bd · 5 ba · 3,062 sqft

    120 Island View Dr, Annapolis, MD

    Boyd Grainger · Pearson Smith Realty, LLC

  19. 979 Bramleigh Ln — photo53Active

    $1,125,000

    4 bd · 4 ba · 4,080 sqft

    979 Bramleigh Ln, Annapolis, MD

    Robert J Breeden · Berkshire Hathaway HomeServices Homesale Realty

  20. 62 Southgate Ave — photoPrice Reduced71Active

    $2,250,000

    4 bd · 5 ba · 3,415 sqft

    62 Southgate Ave, Annapolis, MD

    Mary K Gordon · Coldwell Banker Realty

  21. 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

  22. 500 Sara Dr — photoPrice Reduced35Active

    $1,750,000

    4 bd · 3 ba · 4,771 sqft

    500 Sara Dr, Annapolis, MD

    Bradley R Kappel · TTR Sotheby's International Realty

  23. 268 King George St — photo40Active

    $1,575,000

    4 bd · 4 ba · 2,372 sqft

    268 King George St, Annapolis, MD

    Carol Snyder · Monument Sotheby's International Realty

  24. 48A E Lake Dr — photoPrice Reduced27Active

    $3,395,000

    4 bd · 4 ba · 4,029 sqft

    48A E Lake Dr, Annapolis, MD

    Colleen M Smith · EXP Realty, LLC

12…4

Explore Annapolis homes

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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.
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  • By feature

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    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #01-6355

    Call Thomas

    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.