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St. Michaels, MD Homes for Sale | Realty.com
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35 listings
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Homes for Sale in St. Michaels, MD

Homes for Sale in St. Michaels, MD

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24 of 35 Listings
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Homes for Sale in St. Michaels, MD

24 of 35 Listings

  1. 219 Webb Ln — photo36Active

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

$249,900

2 bd · 1 ba · 932 sqft

219 Webb Ln, Saint Michaels, MD

Sarah C Robins · Coldwell Banker Realty

  • 238 Perry Cabin Dr — photo71Active

    $1,275,000

    2 bd · 3 ba · 1,360 sqft

    238 Perry Cabin Dr, St Michaels, MD

    Maureen M McHugh · Chesapeake Bay Real Estate Plus, LLC

  • 7116 Pea Neck Rd — photo75Active

    $3,600,000

    4 bd · 4 ba · 2,863 sqft

    7116 Pea Neck Rd, St Michaels, MD

    Brian Gearhart · Benson & Mangold, LLC

  • 9450 Canvasback Way — photoOpen house Sun, Nov 15 · 12:00 PM51Active

    $1,895,000

    5 bd · 6 ba · 6,235 sqft

    9450 Canvasback Way, St Michaels, MD

    Melanie L Hopkins · Coldwell Banker Chesapeake Real Estate Company

  • 24560 Deepwater Point Dr #4 — photo19Active

    $385,000

    2 bd · 2 ba · 1,296 sqft

    24560 Deepwater Point Dr #4, St Michaels, MD

    Joan Wetmore · TTR Sotheby's International Realty

  • 8014 Gosling Pond Ct — photo81Active

    $775,000

    4 bd · 3 ba · 3,098 sqft

    8014 Gosling Pond Ct, St Michaels, MD

    Deborah Mangold Lipscomb · Benson & Mangold, LLC

  • 207 Brooks Ln — photo19Active

    $849,900

    3 bd · 3 ba · 1,920 sqft

    207 Brooks Ln, St Michaels, MD

    Nicole Marie Giordano · Coldwell Banker Waterman Realty

  • 700 S Talbot St — photoOpen house Sun, Nov 15 · 12:00 PM83Active

    $1,075,000

    3 bd · 3 ba · 2,061 sqft

    700 S Talbot St, St Michaels, MD

    Sharon L Rieck · Coldwell Banker Chesapeake Real Estate Company

  • 24580 Deepwater Point Drive #3 — photoPrice Reduced43Active

    $375,000

    2 bd · 2 ba · 1,296 sqft

    24580 Deepwater Point Drive #3, Saint Michaels, MD

    Cornelia C Heckenbach · Long & Foster Real Estate, Inc.

  • 24575 Deepwater Point Dr — photo30Active

    $660,000

    3 bd · 3 ba · 2,796 sqft

    24575 Deepwater Point Dr, St Michaels, MD

    John A Fifer · Brokers Realty Group, LLC

  • 806 Calvert Ave — photo27Active

    $525,000

    2 bd · 2 ba · 851 sqft

    806 Calvert Ave, St Michaels, MD

    Schuyler G. Benson · Benson & Mangold, LLC

  • 210 Brooks Ln — photo7Active

    $279,000

    3 bd · 2 ba · 1,340 sqft

    210 Brooks Ln, St Michaels, MD

    Marla Baines · Meredith Fine Properties

  • 409 Railroad Ave — photoPrice Reduced8Active

    $310,000

    3 bd · 2 ba · 1,312 sqft

    409 Railroad Ave, St Michaels, MD

    Dawn A Lednum · Chesapeake Bay Real Estate Plus, LLC

  • 7963 Pond Haven Court — photoPrice Reduced65Active

    $630,000

    3 bd · 3 ba · 3,010 sqft

    7963 Pond Haven Court, Saint Michaels, MD

    Cornelia C Heckenbach · Long & Foster Real Estate, Inc.

  • 202 E Chestnut St — photo50Active

    $1,250,000

    3 bd · 3 ba · 2,052 sqft

    202 E Chestnut St, Saint Michaels, MD

    Winifred C Cowee · Benson & Mangold, LLC

  • 23820 Mount Pleasant Landing — photoPrice Reduced63Active

    $2,800,000

    4 bd · 3 ba · 2,815 sqft

    23820 Mount Pleasant Landing, Saint Michaels, MD

    Carrie E Mock · Engel & Volkers Annapolis

  • 111 Chesapeake Ave — photo40Active

    $949,000

    4 bd · 3 ba · 2,168 sqft

    111 Chesapeake Ave, Saint Michaels, MD

    Jana Meredith · Meredith Fine Properties

  • 104 Mulberry St — photoPrice Reduced74Active

    $1,399,000

    3 bd · 3 ba · 1,938 sqft

    104 Mulberry St, Saint Michaels, MD

    Barbara Best · RE/MAX One

  • 214 Madison Ave — photoPrice Reduced23Active

    $339,000

    4 bd · 2 ba · 1,743 sqft

    214 Madison Ave, Saint Michaels, MD

    Shelley Baden · Berkshire Hathaway HomeServices PenFed Realty

  • 9531 Quail Hollow Dr #405 — photoPrice Reduced20Active

    $319,900

    2 bd · 3 ba · 1,800 sqft

    9531 Quail Hollow Dr #405, St Michaels, MD

    Chuck V Mangold Jr. · Benson & Mangold, LLC

  • 104 Madison Ave — photo1Active

    $459,900

    4 bd · 4 ba · 2,420 sqft

    104 Madison Ave, St Michaels, MD

    Chuck V Mangold Jr. · Benson & Mangold, LLC

  • 9020 Bozman Neavitt Rd — photo32Active

    $1,995,000

    4 bd · 3 ba · 3,028 sqft

    9020 Bozman Neavitt Rd, Saint Michaels, MD

    Thomas M Crouch · Benson & Mangold, LLC

  • 204 E Marengo St — photoPrice Reduced53Active

    $525,000

    2 bd · 1 ba · 1,200 sqft

    204 E Marengo St, Saint Michaels, MD

    Gretchen V Wichlinski · Compass

  • 109 W Marengo St — photoPrice Reduced32Active

    $995,000

    4 bd · 3 ba · 2,250 sqft

    109 W Marengo St, Saint Michaels, MD

    Chuck V Mangold Jr. · Benson & Mangold, LLC

  • 12
    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

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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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    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: 2026-11-13 19:58:00 UTC

    Nearby areas

    ZIP codes

    • 21613 (168)
    • 21401 (129)
    • 21601 (123)
    • 21403 (112)
    • 21666 (89)
    • 21619 (69)
    • 21122 (65)
    • 21037 (53)

    Cities

    • Annapolis (292)
    • Cambridge (168)
    • Easton (123)
    • Stevensville (89)
    • Chester (69)
    • Pasadena (65)
    • Edgewater (53)
    • Centreville (46)

    St. Michaels, MD community profile

    Population
    1,091
    Median income
    $69,309
    Housing units
    664
    People per sq. mi.
    839.2
    Area
    1.3 sq. mi.

    Source: HJN community data

    St. Michaels housing market

    October 2026 · This period is still settling

    Homes on the market · MLS, as of Oct 25, 2026

    Median list price
    $996,000
    Homes for sale
    12

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 30, 2026

    Median home size
    1,770 sq. ft.