2,844

Saint Michaels, MD Homes

Section Image
  • 360 Perry Cabin Dr Unit 48, Saint Michaels, MD 21663
    360 Perry Cabin Dr Unit 48, Saint Michaels, MD 21663
    360 Perry Cabin Dr Unit 48, Saint Michaels, MD 21663
    /42

    $965,000 Pending

    • 3 Beds
    • 2.5 Baths
    • 1,836 Sq Ft

    360 Perry Cabin Dr Unit 48, Saint Michaels, MD 21663

    Professional photos coming. Welcome to historic St. Michaels on the Miles River. This 3 bedroom, 2.5 bath townhouse comes with a designated deep water ( 6 Ft. MLW) boat slip ( #360). Enjoy the tranquil views from your back deck or the balcony off the primary bedroom. The ensuite primary bedroom enjoys water views and a private bath, providing a peaceful retreat. Downstairs flooring is hardwood,

    Meg Moran Long & Foster Real Estate, Inc.

    360 Perry Cabin Dr Unit 48, Saint Michaels, MD 21663
  • 24629 Beverly Rd, Saint Michaels, MD 21663
    24629 Beverly Rd, Saint Michaels, MD 21663
    24629 Beverly Rd, Saint Michaels, MD 21663
    /93

    $7,000,000 Sold Aug 28, 2025

    24629 Beverly Rd, Saint Michaels, MD 21663

    • 5 Beds
    • 7 Baths
    • 10,309 Sq Ft
    • Built 2002

    Last Sold Summary

    • $679/SF
    • 472 Days On Market

    Current Estimated Value $6,659,207

    Last Listing Agent Clifford Meredith Meredith Fine Properties

    24629 Beverly Rd, Saint Michaels, MD 21663
    • 23338 Mallard Point Ln, McDaniel, MD 21647
      23338 Mallard Point Ln, McDaniel, MD 21647
      23338 Mallard Point Ln, McDaniel, MD 21647
      /52

      Est $656,937 Not Listed For Sale

      23338 Mallard Point Ln, McDaniel, MD 21647

      • 4 Beds
      • 3 Baths
      • 2,324 Sq Ft
      • Built 1989
      23338 Mallard Point Ln, McDaniel, MD 21647

      Last Sold Summary

      • 37% Above List Price
      • $207/SF
      • 10 Days On Market
      • Last Sold Price $480,000
      • May 08, 2023

      Last Listing Agent Kathleen Coale Benson & Mangold, LLC

  • 228 Perry Cabin Dr Unit 228 / 226, Saint Michaels, MD 21663
    228 Perry Cabin Dr Unit 228 / 226, Saint Michaels, MD 21663
    228 Perry Cabin Dr Unit 228 / 226, Saint Michaels, MD 21663
    /119

    $1,995,000

    • 6 Beds
    • 6 Baths
    • 4,089 Sq Ft

    228 Perry Cabin Dr Unit 228 / 226, Saint Michaels, MD 21663

    Check out the NEW aerial photos! An exceptional opportunity in The Homes at Perry Cabin -- a rare double residence offering approximately 4,000 square feet, six bedrooms, and six full baths in a premier Saint Michaels waterfront community. adjacent to the renowned Inn at Perry Cabin and overlooking Fogg Cove just off the Miles River. This turnkey home features expansive living areas and a

    Maureen McHugh Chesapeake Bay Real Estate Plus, LLC

    228 Perry Cabin Dr Unit 228 / 226, Saint Michaels, MD 21663
  • 25500 Chance Farm Rd, Royal Oak, MD 21662
    25500 Chance Farm Rd, Royal Oak, MD 21662
    25500 Chance Farm Rd, Royal Oak, MD 21662
    /43

    $2,190,000 Sold Dec 19, 2025

    25500 Chance Farm Rd, Royal Oak, MD 21662

    • 4 Beds
    • 3.5 Baths
    • 3,248 Sq Ft
    • Built 1989

    Last Sold Summary

    • $674/SF
    • 65 Days On Market

    Current Estimated Value $2,145,565

    Last Listing Agent Laura Carney TTR Sotheby's International Realty

    25500 Chance Farm Rd, Royal Oak, MD 21662
    • 24564 New Post Rd, Saint Michaels, MD 21663
      24564 New Post Rd, Saint Michaels, MD 21663
      24564 New Post Rd, Saint Michaels, MD 21663
      /66

      Est $3,540,907 Not Listed For Sale

      24564 New Post Rd, Saint Michaels, MD 21663

      • 5 Beds
      • 3.5 Baths
      • 3,674 Sq Ft
      • Built 2002
      24564 New Post Rd, Saint Michaels, MD 21663

      Last Sold Summary

      • 13% Below List Price
      • $1,103/SF
      • 3 Days On Market
      • Last Sold Price $4,052,706
      • Jun 20, 2024

      Last Listing Agent Kara Chaffin Donofrio Long & Foster

  • 24561 Deepwater Point Dr, Saint Michaels, MD 21663
    24561 Deepwater Point Dr, Saint Michaels, MD 21663
    24561 Deepwater Point Dr, Saint Michaels, MD 21663
    /50

    $649,000

    • 3 Beds
    • 3 Baths
    • 2,144 Sq Ft

    24561 Deepwater Point Dr, Saint Michaels, MD 21663

    Effortless living in the Martingham community. This thoughtfully designed 3-bedroom, 3-bath rancher features a light-filled, easy-flow floorplan with two ensuite bedrooms for added privacy and versatility. The home offers a garage and separate laundry room and opens to a charming backyard deck - ideal for morning coffee or evening gatherings. The spacious backyard provides ample room for a pool,

    Maureen McHugh Chesapeake Bay Real Estate Plus, LLC

    24561 Deepwater Point Dr, Saint Michaels, MD 21663
  • 104 W Chew Ave, Saint Michaels, MD 21663
    104 W Chew Ave, Saint Michaels, MD 21663
    104 W Chew Ave, Saint Michaels, MD 21663
    /18

    $1,310,000 Sold May 16, 2025

    104 W Chew Ave, Saint Michaels, MD 21663

    • 2 Beds
    • 2 Baths
    • 2,654 Sq Ft
    • Built 1900

    Last Sold Summary

    • $494/SF

    Current Estimated Value $1,266,807

    Last Listing Agent datacorrect BrightMLS Non Subscribing Office

    104 W Chew Ave, Saint Michaels, MD 21663
    • 9510 Martingham Cir, Saint Michaels, MD 21663
      9510 Martingham Cir, Saint Michaels, MD 21663
      9510 Martingham Cir, Saint Michaels, MD 21663
      /61

      Est $783,347 Not Listed For Sale

      9510 Martingham Cir, Saint Michaels, MD 21663

      • 3 Beds
      • 2.5 Baths
      • 2,868 Sq Ft
      • Built 1992
      9510 Martingham Cir, Saint Michaels, MD 21663

      Last Sold Summary

      • 6% Above List Price
      • $258/SF
      • 2 Days On Market
      • Last Sold Price $739,000
      • Oct 11, 2024

      Last Listing Agent Dennis Medlock Coldwell Banker Realty

  • 8620 Bozman Neavitt Rd, Saint Michaels, MD 21663
    8620 Bozman Neavitt Rd, Saint Michaels, MD 21663
    8620 Bozman Neavitt Rd, Saint Michaels, MD 21663
    /60

    $8,495,000

    • 6 Beds
    • 11 Baths
    • 17,402 Sq Ft

    8620 Bozman Neavitt Rd, Saint Michaels, MD 21663

    NEW PRICE! Located minutes from downtown St. Michaels, “Aqua Vitae” the waters of life, sits on 8.6 private acres on Harris Creek, a Chesapeake Bay tributary. This custom-built offering w/ over 400’ of direct water frontage is comprised of 3 magnificent structures: a grand main residence, guest cottage, & “party barn” all highlighted by a waterside pool, pier w/ 4’ MLW, pine grove, putting green,

    Doc Keane Washington Fine Properties, LLC

    8620 Bozman Neavitt Rd, Saint Michaels, MD 21663
  • 25070 Hurley Ln, Saint Michaels, MD 21663
    25070 Hurley Ln, Saint Michaels, MD 21663
    25070 Hurley Ln, Saint Michaels, MD 21663
    /28

    $439,999 Sold Nov 06, 2025

    25070 Hurley Ln, Saint Michaels, MD 21663

    • 3 Beds
    • 2.5 Baths
    • 1,505 Sq Ft
    • Built 2003

    Last Sold Summary

    • $292/SF
    • 402 Days On Market

    Current Estimated Value $438,941

    Last Listing Agent Stephany Barrett Long & Foster Real Estate, Inc.

    25070 Hurley Ln, Saint Michaels, MD 21663
    • 107 W Maple Ave, Saint Michaels, MD 21663
      107 W Maple Ave, Saint Michaels, MD 21663
      107 W Maple Ave, Saint Michaels, MD 21663
      /70

      Est $925,802 Not Listed For Sale

      107 W Maple Ave, Saint Michaels, MD 21663

      • 3 Beds
      • 3.5 Baths
      • 2,600 Sq Ft
      • Built 1965
      107 W Maple Ave, Saint Michaels, MD 21663

      Last Sold Summary

      • 5% Below List Price
      • $375/SF
      • 17 Days On Market
      • Last Sold Price $975,000
      • Jul 01, 2024

      Last Listing Agent Tom Crouch Benson & Mangold, LLC

  • 105 Seymour Ave, Saint Michaels, MD 21663
    105 Seymour Ave, Saint Michaels, MD 21663
    105 Seymour Ave, Saint Michaels, MD 21663
    /39

    $474,000

    • 2 Beds
    • 1 Bath
    • 1,080 Sq Ft

    105 Seymour Ave, Saint Michaels, MD 21663

    SAINT MICHAELS CHARMING COTTAGE! Welcome Home to this Adorable Cottage perfectly situated in the desirable and walkable Historic Waterfront Town of Saint Michaels! Full of natural light and warmth, this inviting home offers comfortable living spaces and thoughtful updates. A sizable .25 Acre lot with mature trees to include a pecan and walnut tree, mature flower gardens, zoysia grass and an

    Pamela Ackermann-Doll RE/MAX Executive

    105 Seymour Ave, Saint Michaels, MD 21663
  • 109 W Chew Ave, Saint Michaels, MD 21663
    109 W Chew Ave, Saint Michaels, MD 21663
    /2

    $662,500 Sold Jul 18, 2025

    109 W Chew Ave, Saint Michaels, MD 21663

    • 3 Beds
    • 2 Baths
    • 1,824 Sq Ft
    • Built 1920

    Last Sold Summary

    • $363/SF
    • 21 Days On Market

    Current Estimated Value $673,830

    Last Listing Agent Barbara Watkins Benson & Mangold, LLC

    109 W Chew Ave, Saint Michaels, MD 21663
    • 24393 Widgeon Place, Saint Michaels, MD 21663
      24393 Widgeon Place, Saint Michaels, MD 21663
      24393 Widgeon Place, Saint Michaels, MD 21663
      /53

      Est $733,847 Not Listed For Sale

      24393 Widgeon Place, Saint Michaels, MD 21663

      • 3 Beds
      • 2.5 Baths
      • 2,459 Sq Ft
      • Built 1973
      24393 Widgeon Place, Saint Michaels, MD 21663

      Last Sold Summary

      • 2% Below List Price
      • $305/SF
      • 11 Days On Market
      • Last Sold Price $750,000
      • Mar 28, 2025

      Last Listing Agent Cornelia Heckenbach Long & Foster

  • 962 San Domingo Ct, Saint Michaels, MD 21663
    962 San Domingo Ct, Saint Michaels, MD 21663
    962 San Domingo Ct, Saint Michaels, MD 21663
    /103

    $2,449,000

    • 4 Beds
    • 4.5 Baths
    • 3,300 Sq Ft

    962 San Domingo Ct, Saint Michaels, MD 21663

    This exquisite in-town St. Michaels coastal-style waterfront is a designer’s dream home. The 3,300 sq, ft. residence shows like a new model home with an unparalleled quality of finishes and level of design. Located in desirable San Domingo Cove, the community enjoys protected natural open space, beautiful water features and immediate access to the ever-popular St. Michaels Nature Trail offering

    Eugene Smith TTR Sotheby's International Realty

    962 San Domingo Ct, Saint Michaels, MD 21663
  • 226 North St, Saint Michaels, MD 21663
    226 North St, Saint Michaels, MD 21663
    226 North St, Saint Michaels, MD 21663
    /12

    $140,000 Sold May 09, 2025

    226 North St, Saint Michaels, MD 21663

    • Land
    • 9,147 Sq Ft
    • $666,667 per Acre

    Last Sold Summary

    • 247 Days On Market

    Current Estimated Value $145,406

    Last Listing Agent Jennifer Pogoda Redfin Corp

    226 North St, Saint Michaels, MD 21663
    • 502 Seymour Ave, Saint Michaels, MD 21663
      502 Seymour Ave, Saint Michaels, MD 21663
      502 Seymour Ave, Saint Michaels, MD 21663
      /66

      Est $782,909 Not Listed For Sale

      502 Seymour Ave, Saint Michaels, MD 21663

      • 3 Beds
      • 2.5 Baths
      • 1,774 Sq Ft
      • Built 2003
      502 Seymour Ave, Saint Michaels, MD 21663

      Last Sold Summary

      • 13% Below List Price
      • $507/SF
      • 54 Days On Market
      • Last Sold Price $900,000
      • Nov 27, 2023

      Last Listing Agent Jana Meredith Meredith Fine Properties

  • 24977 Back Creek Dr, Saint Michaels, MD 21663
    24977 Back Creek Dr, Saint Michaels, MD 21663
    24977 Back Creek Dr, Saint Michaels, MD 21663
    /70

    $749,999

    • 4 Beds
    • 3.5 Baths
    • 3,010 Sq Ft

    24977 Back Creek Dr, Saint Michaels, MD 21663

    Discover a beautifully crafted custom home tucked within the peaceful St. Michaels community, where refined design meets everyday comfort. This exceptional residence offers 4 generously sized bedrooms and 3.5 thoughtfully designed bathrooms, filled with premium details throughout. The versatile gas fireplace anchors the inviting main living space, complemented by custom built-ins that add both

    Eddie Mangold Benson & Mangold, LLC

    24977 Back Creek Dr, Saint Michaels, MD 21663
  • 7896 Hart Glen Ct, Saint Michaels, MD 21663
    7896 Hart Glen Ct, Saint Michaels, MD 21663
    7896 Hart Glen Ct, Saint Michaels, MD 21663
    /70

    $795,000 Sold Jun 30, 2025

    7896 Hart Glen Ct, Saint Michaels, MD 21663

    • 4 Beds
    • 2.5 Baths
    • 3,038 Sq Ft
    • Built 2005

    Last Sold Summary

    • $262/SF
    • 14 Days On Market

    Current Estimated Value $787,184

    Last Listing Agent Kathleen Coale Benson & Mangold, LLC

    7896 Hart Glen Ct, Saint Michaels, MD 21663
    • 201 E Marengo St, Saint Michaels, MD 21663
      201 E Marengo St, Saint Michaels, MD 21663
      201 E Marengo St, Saint Michaels, MD 21663
      /65

      Est $783,809 Not Listed For Sale

      201 E Marengo St, Saint Michaels, MD 21663

      • 3 Beds
      • 2.5 Baths
      • 2,294 Sq Ft
      • Built 1990
      201 E Marengo St, Saint Michaels, MD 21663

      Last Sold Summary

      • $342/SF
      • 95 Days On Market
      • Last Sold Price $785,000
      • Nov 17, 2023

      Last Listing Agent Wink Cowee Benson & Mangold, LLC

  • 0 Deepwater Point Dr, Saint Michaels, MD 21663
    0 Deepwater Point Dr, Saint Michaels, MD 21663
    0 Deepwater Point Dr, Saint Michaels, MD 21663
    /41

    $249,000

    • Land
    • 1.12 Acres
    • $222,321 per Acre

    0 Deepwater Point Dr, Saint Michaels, MD 21663

    ONE OF THE LAST LOTS IN MARTINGHAM ON DEEP WATER POINT DRIVE. LOCATED VERY CLOSE TO THE COMMUNITY WATERFRONT PARK WITH GAZEBO AND CHAIRS FOR PICKNICKS OR JUST RELAXING IN THE BREEZE WATCHING THE BOATS GO BY ; DROP YOUR KAYAK OR ENJOY THE SUNSETS, WALK OR BIKE THERE. THIS LOT IS CLEANED, HAS A BEAUTIFUL ENTRANCE , WATER METER, AND IS READY FOR YOU TO BUILT YOUR MAIN RESIDENCE OR WEEKEND GET AWAY.

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    0 Deepwater Point Dr, Saint Michaels, MD 21663
  • 106 Grace St, Saint Michaels, MD 21663
    106 Grace St, Saint Michaels, MD 21663
    106 Grace St, Saint Michaels, MD 21663
    /57

    $775,000 Sold Dec 02, 2025

    106 Grace St, Saint Michaels, MD 21663

    • 3 Beds
    • 1.5 Baths
    • 2,068 Sq Ft
    • Built 1890

    Last Sold Summary

    • $375/SF
    • 3 Days On Market

    Current Estimated Value $770,992

    Last Listing Agent Kate Koeppen Chesapeake Bay Real Estate Plus, LLC

    106 Grace St, Saint Michaels, MD 21663
    • 305 E Chew Ave, Saint Michaels, MD 21663
      305 E Chew Ave, Saint Michaels, MD 21663
      305 E Chew Ave, Saint Michaels, MD 21663
      /54

      Est $845,728 Not Listed For Sale

      305 E Chew Ave, Saint Michaels, MD 21663

      • 3 Beds
      • 2 Baths
      • 1,536 Sq Ft
      • Built 1950
      305 E Chew Ave, Saint Michaels, MD 21663

      Last Sold Summary

      • 23% Below List Price
      • $716/SF
      • 6 Days On Market
      • Last Sold Price $1,100,000
      • Apr 27, 2023

      Last Listing Agent Jana Meredith Meredith Fine Properties

  • 303 Manor St, Saint Michaels, MD 21663
    303 Manor St, Saint Michaels, MD 21663
    303 Manor St, Saint Michaels, MD 21663
    /100

    $1,985,000

    • 3 Beds
    • 3 Baths
    • 2,622 Sq Ft

    303 Manor St, Saint Michaels, MD 21663

    Welcome to "Mostly Porches" an exceptional coastal retreat with captivating views of the harbor, perfectly situated on a spacious .41 acre corner lot just around the corner from the shops and restaurants of St. Michaels. Built in 2018 with virtually maintenance-free construction, this beautifully designed home offers the ideal blend of comfort, style, and convenience in a rare St. Michaels

    Monica Penwell TTR Sotheby's International Realty

    303 Manor St, Saint Michaels, MD 21663
  • 106 Boundary Ln, Saint Michaels, MD 21663
    106 Boundary Ln, Saint Michaels, MD 21663
    106 Boundary Ln, Saint Michaels, MD 21663
    /58

    $575,000 Sold Jun 27, 2025

    106 Boundary Ln, Saint Michaels, MD 21663

    • 3 Beds
    • 2 Baths
    • 1,490 Sq Ft
    • Built 1997

    Last Sold Summary

    • $386/SF
    • 32 Days On Market

    Current Estimated Value $569,865

    Last Listing Agent Kim Crouch Ozman Benson & Mangold, LLC

    106 Boundary Ln, Saint Michaels, MD 21663
    • 111 W Maple Ave, Saint Michaels, MD 21663
      111 W Maple Ave, Saint Michaels, MD 21663
      111 W Maple Ave, Saint Michaels, MD 21663
      /48

      Est $610,703 Not Listed For Sale

      111 W Maple Ave, Saint Michaels, MD 21663

      • 2 Beds
      • 1 Bath
      • 912 Sq Ft
      • Built 1952
      111 W Maple Ave, Saint Michaels, MD 21663

      Last Sold Summary

      • 1% Below List Price
      • $674/SF
      • 1 Day On Market
      • Last Sold Price $615,000
      • Jun 27, 2024

      Last Listing Agent Kathleen Coale Benson & Mangold, LLC

  • 24830 Deepwater Point Dr, Saint Michaels, MD 21663
    24830 Deepwater Point Dr, Saint Michaels, MD 21663
    24830 Deepwater Point Dr, Saint Michaels, MD 21663
    /75

    $2,425,000 Under Contract

    • 3 Beds
    • 2.5 Baths
    • 2,875 Sq Ft

    24830 Deepwater Point Dr, Saint Michaels, MD 21663

    DREAMING OF A BEACH HOUSE ? STUNNING LOCATION , ENDLESS BREEZES AND SUNSETS.....A treasure of vantage points and chic contemporary beauty, this Martingham waterfront retreat offers rare front-row views of Miles River happenings - including the historic Log Canoe Races, Fourth of July fireworks, daily passages of billowing sails,and, on crisp days, sightlines stretching for miles. Set on 2.32

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    24830 Deepwater Point Dr, Saint Michaels, MD 21663
  • 0 Grace St Unit MDTA2012346, Saint Michaels, MD 21663
    0 Grace St Unit MDTA2012346, Saint Michaels, MD 21663
    0 Grace St Unit MDTA2012346, Saint Michaels, MD 21663
    /10

    $240,000 Sold Dec 15, 2025

    0 Grace St Unit MDTA2012346, Saint Michaels, MD 21663

    • Land
    • 7,405 Sq Ft
    • $1,411,765 per Acre

    Last Sold Summary

    • 3 Days On Market

    Last Listing Agent Connor LeMire Benson & Mangold, LLC

    0 Grace St Unit MDTA2012346, Saint Michaels, MD 21663
    • 9816 Martingham Cir, Saint Michaels, MD 21663
      9816 Martingham Cir, Saint Michaels, MD 21663
      9816 Martingham Cir, Saint Michaels, MD 21663
      /42

      Est $1,932,428 Not Listed For Sale

      9816 Martingham Cir, Saint Michaels, MD 21663

      • 3 Beds
      • 2.5 Baths
      • 3,489 Sq Ft
      • Built 1992
      9816 Martingham Cir, Saint Michaels, MD 21663

      Last Sold Summary

      • 1% Below List Price
      • $559/SF
      • 17 Days On Market
      • Last Sold Price $1,950,000
      • Oct 07, 2024

      Last Listing Agent Cornelia Heckenbach Long & Foster

  • 7909 Church Neck Rd, Saint Michaels, MD 21663
    7909 Church Neck Rd, Saint Michaels, MD 21663
    7909 Church Neck Rd, Saint Michaels, MD 21663
    /50

    $2,300,000

    • 4 Beds
    • 2.5 Baths
    • 4,492 Sq Ft

    7909 Church Neck Rd, Saint Michaels, MD 21663

    Pictures coming 4/11.Set on 19.5 private acres just minutes from historic waterfront Saint Michaels, this exceptional 4,492 sq ft residence offers the perfect blend of space, privacy, and convenience. The home features four bedrooms and two and a half baths, with expansive living areas ideal for both everyday living and entertaining, including a well-appointed chef's kitchen. The thoughtfully

    Cheri Bruce-Phipps TTR Sotheby's International Realty

    7909 Church Neck Rd, Saint Michaels, MD 21663
  • 408 Water St, Saint Michaels, MD 21663
    408 Water St, Saint Michaels, MD 21663
    408 Water St, Saint Michaels, MD 21663
    /34

    $995,000 Sold Oct 08, 2025

    408 Water St, Saint Michaels, MD 21663

    • 3 Beds
    • 2.5 Baths
    • 1,893 Sq Ft
    • Built 1972

    Last Sold Summary

    • $526/SF
    • 3 Days On Market

    Current Estimated Value $980,198

    Last Listing Agent Laura Carney TTR Sotheby's International Realty

    408 Water St, Saint Michaels, MD 21663
    • 230 Tyler Ave, Saint Michaels, MD 21663
      230 Tyler Ave, Saint Michaels, MD 21663
      230 Tyler Ave, Saint Michaels, MD 21663
      /20

      Est $623,078 Not Listed For Sale

      230 Tyler Ave, Saint Michaels, MD 21663

      • 4 Beds
      • 2.5 Baths
      • 2,279 Sq Ft
      • Built 2002
      230 Tyler Ave, Saint Michaels, MD 21663

      Last Sold Summary

      • 10% Above List Price
      • $248/SF
      • 4 Days On Market
      • Last Sold Price $565,000
      • Jul 28, 2023

      Last Listing Agent Elizabeth Tryon Coldwell Banker Realty

  • 205 Cherry St, St. Michaels, MD 21663
    205 Cherry St, St. Michaels, MD 21663
    205 Cherry St, St. Michaels, MD 21663
    /64

    $2,575,000 Under Contract

    • 5 Beds
    • 8.5 Baths
    • 4,394 Sq Ft

    205 Cherry St, St. Michaels, MD 21663

    205 Cherry Street is one of the most prestigious addresses in historic St. Michaels. Originally built as a single-family residence, it currently operates as an Inn. It is being marketed both as a 7 bedroom inn and also as a single family residence, offering 5 bedrooms (including the first floor primary bedroom suite). The original living room/office with fireplaces on the first floor are

    Robert Lacaze TTR Sotheby's International Realty

    205 Cherry St, St. Michaels, MD 21663
  • 9998 Wades Farm Ln, McDaniel, MD 21647
    9998 Wades Farm Ln, McDaniel, MD 21647
    9998 Wades Farm Ln, McDaniel, MD 21647
    /117

    $1,402,000 Sold Oct 15, 2025

    9998 Wades Farm Ln, McDaniel, MD 21647

    • 6 Beds
    • 4 Baths
    • 3,623 Sq Ft
    • Built 1909

    Last Sold Summary

    • $387/SF
    • 3 Days On Market

    Current Estimated Value $1,360,473

    Last Listing Agent Kelly Showell Benson & Mangold, LLC

    9998 Wades Farm Ln, McDaniel, MD 21647
    • 515 Tenant Cir, Saint Michaels, MD 21663
      515 Tenant Cir, Saint Michaels, MD 21663
      515 Tenant Cir, Saint Michaels, MD 21663
      /92

      Est $1,471,364 Not Listed For Sale

      515 Tenant Cir, Saint Michaels, MD 21663

      • 4 Beds
      • 3 Baths
      • 2,485 Sq Ft
      • Built 1972
      515 Tenant Cir, Saint Michaels, MD 21663

      Last Sold Summary

      • 5% Above List Price
      • $563/SF
      • 35 Days On Market
      • Last Sold Price $1,400,000
      • Mar 15, 2024

      Last Listing Agent Connie Loveland Benson & Mangold, LLC

  • 108 Miles, Saint Michaels, MD 21663
    108 Miles, Saint Michaels, MD 21663
    108 Miles, Saint Michaels, MD 21663
    /25

    $999,000 New Construction

    • 3 Beds
    • 2.5 Baths

    108 Miles, Saint Michaels, MD 21663

    A rare opportunity to combine a half-acre+ wooded in-town setting with a classic Cape Cod–style home concept in the heart of St. Michaels. Concept B illustrates a two-story design featuring 3 bedrooms, 2 full baths, and 1 half bath, along with an attached two-car garage. The proposed layout offers a timeless architectural style with flexible living spaces that can be customized to suit individual

    Chuck Mangold Benson & Mangold, LLC

    108 Miles, Saint Michaels, MD 21663
  • 304 N Talbot St, Saint Michaels, MD 21663
    304 N Talbot St, Saint Michaels, MD 21663
    304 N Talbot St, Saint Michaels, MD 21663
    /42

    $785,000 Sold Oct 15, 2025

    304 N Talbot St, Saint Michaels, MD 21663

    • 3 Beds
    • 2.5 Baths
    • 2,028 Sq Ft
    • Built 2021

    Last Sold Summary

    • $387/SF
    • 3 Days On Market

    Current Estimated Value $771,347

    Last Listing Agent Wink Cowee Benson & Mangold, LLC

    304 N Talbot St, Saint Michaels, MD 21663
    • 407 Seymour Ave, Saint Michaels, MD 21663
      407 Seymour Ave, Saint Michaels, MD 21663
      407 Seymour Ave, Saint Michaels, MD 21663
      /37

      Est $480,310 Not Listed For Sale

      407 Seymour Ave, Saint Michaels, MD 21663

      • 3 Beds
      • 1.5 Baths
      • 1,918 Sq Ft
      • Built 1980
      407 Seymour Ave, Saint Michaels, MD 21663

      Last Sold Summary

      • 2% Above List Price
      • $245/SF
      • 1 Day On Market
      • Last Sold Price $469,999
      • Apr 09, 2024

      Last Listing Agent Jamie Taraila Keller Williams Realty Central-Delaware

  • 900 Riverview Terrace, Saint Michaels, MD 21663
    900 Riverview Terrace, Saint Michaels, MD 21663
    900 Riverview Terrace, Saint Michaels, MD 21663
    /38

    $2,700,000 Sold Oct 15, 2025

    900 Riverview Terrace, Saint Michaels, MD 21663

    • 3 Beds
    • 2.5 Baths
    • 3,393 Sq Ft
    • Built 1987

    Last Sold Summary

    • $796/SF
    • 70 Days On Market

    Current Estimated Value $2,655,394

    Last Listing Agent Robert Lacaze TTR Sotheby's International Realty

    900 Riverview Terrace, Saint Michaels, MD 21663

Showing Results 161 - 200, Page 5 of 18

Maryland Talbot County Saint Michaels

Real Estate & Homes

How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group