2,833

Saint Michaels, MD Homes

Section Image
  • 23201 Stewart Way, McDaniel, MD 21647
    23201 Stewart Way, McDaniel, MD 21647
    23201 Stewart Way, McDaniel, MD 21647
    /48

    $595,000

    • 3 Beds
    • 2.5 Baths
    • 2,080 Sq Ft

    23201 Stewart Way, McDaniel, MD 21647

    Tucked away down a private lane, this stunning and fully renovated 3-bedroom, 2.5-bath Cape Cod sits on a serene 3.43± acre parcel, offering exceptional privacy and a truly remarkable setting. A covered front porch welcomes you home and provides the perfect place to relax while overlooking the tranquil setting that the property offers. Inside, luxury vinyl plank flooring flows throughout the

    Kim Crouch Ozman Benson & Mangold, LLC

    23201 Stewart Way, McDaniel, MD 21647
  • 24312 Oakwood Park Rd, Saint Michaels, MD 21663
    24312 Oakwood Park Rd, Saint Michaels, MD 21663
    24312 Oakwood Park Rd, Saint Michaels, MD 21663
    /54

    $825,000 Sold Oct 28, 2025

    24312 Oakwood Park Rd, Saint Michaels, MD 21663

    • 2 Beds
    • 1 Bath
    • 836 Sq Ft
    • Built 1952

    Last Sold Summary

    • $987/SF
    • 25 Days On Market

    Current Estimated Value $828,297

    Last Listing Agent Cornelia Heckenbach Long & Foster Real Estate, Inc.

    24312 Oakwood Park Rd, Saint Michaels, MD 21663
    • 8288 Bozman Neavitt Rd, Saint Michaels, MD 21663
      8288 Bozman Neavitt Rd, Saint Michaels, MD 21663
      8288 Bozman Neavitt Rd, Saint Michaels, MD 21663
      /64

      Est $1,707,144 Not Listed For Sale

      8288 Bozman Neavitt Rd, Saint Michaels, MD 21663

      • 3 Beds
      • 2.5 Baths
      • 3,282 Sq Ft
      • Built 1998
      8288 Bozman Neavitt Rd, Saint Michaels, MD 21663

      Last Sold Summary

      • 10% Above List Price
      • $472/SF
      • 189 Days On Market

      Last Sold Price $1,550,000

      Last Listing Agent Debra Crouch Benson & Mangold, LLC

  • 111 Gloria Ave, Saint Michaels, MD 21663
    111 Gloria Ave, Saint Michaels, MD 21663
    111 Gloria Ave, Saint Michaels, MD 21663
    /30

    $450,000 Open Wed 10AM - 12PM

    • 2 Beds
    • 1.5 Baths
    • 1,125 Sq Ft

    111 Gloria Ave, Saint Michaels, MD 21663

    Essentially a NEW HOME! Extensively, tastefully and professionally renovated 1965 rancher located on a quiet residential street, just 2 blocks from downtown St. Michaels. Nearly everything is brand new, including roof shingles, siding, windows, HVAC system and new deck. New off-street parking area, sized for 2 vehicles. Inside, everything looks (and is) new, too, including attractive luxury vinyl

    Tom Crouch Benson & Mangold, LLC

    111 Gloria 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

    $750,000 Sold Mar 28, 2025

    24393 Widgeon Place, Saint Michaels, MD 21663

    • 3 Beds
    • 2.5 Baths
    • 2,459 Sq Ft
    • Built 1973

    Last Sold Summary

    • $305/SF
    • 11 Days On Market

    Current Estimated Value $739,465

    Last Listing Agent Cornelia Heckenbach Long & Foster Real Estate, Inc.

    24393 Widgeon Place, Saint Michaels, MD 21663
    • 313 Dodson Ave, Saint Michaels, MD 21663
      313 Dodson Ave, Saint Michaels, MD 21663
      313 Dodson Ave, Saint Michaels, MD 21663
      /14

      Est $280,145 Not Listed For Sale

      313 Dodson Ave, Saint Michaels, MD 21663

      • 3 Beds
      • 1 Bath
      • 1,056 Sq Ft
      • Built 1981
      313 Dodson Ave, Saint Michaels, MD 21663

      Last Sold Summary

      • 19% Below List Price
      • $327/SF
      • 84 Days On Market

      Last Sold Price $345,000

      Last Listing Agent Chuck Mangold Benson & Mangold, LLC

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

    $779,000 New Construction

    • 3 Beds
    • 2 Baths
    • 1,710 Sq Ft

    108 Miles, Saint Michaels, MD 21663

    A rare opportunity to pair a half-acre+ wooded in-town parcel with a thoughtfully designed single-level home concept in the heart of St. Michaels. This Concept A plan illustrates a 3-bedroom, 2-bath residence totaling approximately 1,710 square feet, featuring one-level living and an attached one-car garage. Designed to maximize functionality and flow, the concept offers flexible living spaces

    Chuck Mangold Benson & Mangold, LLC

    108 Miles, Saint Michaels, MD 21663
  • 9539 Quail Hollow Dr Unit 303, Saint Michaels, MD 21663
    9539 Quail Hollow Dr Unit 303, Saint Michaels, MD 21663
    9539 Quail Hollow Dr Unit 303, Saint Michaels, MD 21663
    /89

    $360,000 Sold Dec 05, 2025

    9539 Quail Hollow Dr Unit 303, Saint Michaels, MD 21663

    • 2 Beds
    • 2.5 Baths
    • 1,800 Sq Ft
    • Built 1973

    Last Sold Summary

    • $200/SF
    • 52 Days On Market

    Current Estimated Value $365,279

    Last Listing Agent Kim Crouch Ozman Benson & Mangold, LLC

    9539 Quail Hollow Dr Unit 303, Saint Michaels, MD 21663
    • 909 Riverview Terrace, Saint Michaels, MD 21663
      909 Riverview Terrace, Saint Michaels, MD 21663
      909 Riverview Terrace, Saint Michaels, MD 21663
      /57

      Est $810,587 Not Listed For Sale

      909 Riverview Terrace, Saint Michaels, MD 21663

      • 3 Beds
      • 2.5 Baths
      • 2,069 Sq Ft
      • Built 1956
      909 Riverview Terrace, Saint Michaels, MD 21663

      Last Sold Summary

      • 30% Above List Price
      • $302/SF
      • 68 Days On Market

      Last Sold Price $625,000

      Last Listing Agent Kathleen Coale Benson & Mangold, LLC

  • 228 Tyler Ave, Saint Michaels, MD 21663
    228 Tyler Ave, Saint Michaels, MD 21663
    228 Tyler Ave, Saint Michaels, MD 21663
    /44

    $549,900 Pending

    • 3 Beds
    • 2.5 Baths
    • 1,922 Sq Ft

    228 Tyler Ave, Saint Michaels, MD 21663

    This handsome home is nestled in the trees on a quiet cul de sac in Rio Vista. This popular neighborhood is five minutes from historic St. Michaels and offers public sewer and water with no town taxes. Rio Vista has a waterfront picnic area and boat slips for rent to residents for $225 per slip.This home has been very nicely maintained by the original owner. It offers one-level living, with a

    Debra Crouch Benson & Mangold, LLC

    228 Tyler Ave, Saint Michaels, MD 21663
  • 102 Gloria Ave, Saint Michaels, MD 21663
    102 Gloria Ave, Saint Michaels, MD 21663
    102 Gloria Ave, Saint Michaels, MD 21663
    /13

    $99,500 Sold Feb 20, 2026

    102 Gloria Ave, Saint Michaels, MD 21663

    • Land
    • 0.15 Acre
    • $663,333 per Acre

    Last Sold Summary

    • 19 Days On Market

    Current Estimated Value $223,328

    Last Listing Agent Monica Penwell TTR Sotheby's International Realty

    102 Gloria Ave, Saint Michaels, MD 21663
    • 8080 Bozman Neavitt Rd, Saint Michaels, MD 21663
      8080 Bozman Neavitt Rd, Saint Michaels, MD 21663
      8080 Bozman Neavitt Rd, Saint Michaels, MD 21663
      /80

      Est $1,076,936 Not Listed For Sale

      8080 Bozman Neavitt Rd, Saint Michaels, MD 21663

      • 3 Beds
      • 3 Baths
      • 5,869 Sq Ft
      • Built 1960
      8080 Bozman Neavitt Rd, Saint Michaels, MD 21663

      Last Sold Summary

      • 20% Above List Price
      • $153/SF
      • 9 Days On Market

      Last Sold Price $900,000

      Last Listing Agent Mary Lapides Cummings & Co Realtors

  • 926 Calvert Ave, Saint Michaels, MD 21663
    926 Calvert Ave, Saint Michaels, MD 21663
    926 Calvert Ave, Saint Michaels, MD 21663
    /39

    $436,950 Under Contract

    • 3 Beds
    • 1.5 Baths
    • 1,365 Sq Ft

    926 Calvert Ave, Saint Michaels, MD 21663

    Nestled in the historic, waterfront town of Saint Michaels, this charming colonial with one-car garage built in 2001, offers comfortable living on a private street! Lovely, level lot for quiet enjoyment surrounded by trees! Lots of nice features throughout! Brand-new carpet on upper level! Engineered hardwood floors! Large living room with lots of natural light! Kitchen with light oak cabinets,

    Dawn Baxter Berkshire Hathaway HomeServices PenFed Realty

    926 Calvert Ave, Saint Michaels, MD 21663
  • 504 S Talbot St, Saint Michaels, MD 21663
    504 S Talbot St, Saint Michaels, MD 21663
    504 S Talbot St, Saint Michaels, MD 21663
    /52

    $850,000 Sold Jul 31, 2025

    504 S Talbot St, Saint Michaels, MD 21663

    • 3 Beds
    • 2.5 Baths
    • 2,072 Sq Ft
    • Built 1900

    Last Sold Summary

    • $410/SF
    • 76 Days On Market

    Current Estimated Value $838,269

    Last Listing Agent Kim Crouch Ozman Benson & Mangold, LLC

    504 S Talbot St, Saint Michaels, MD 21663
    • 1110 Jefferson Ave, Saint Michaels, MD 21663
      1110 Jefferson Ave, Saint Michaels, MD 21663
      1110 Jefferson Ave, Saint Michaels, MD 21663
      /64

      Est $477,381 Not Listed For Sale

      1110 Jefferson Ave, Saint Michaels, MD 21663

      • 4 Beds
      • 3 Baths
      • 1,600 Sq Ft
      • Built 1984
      1110 Jefferson Ave, Saint Michaels, MD 21663

      Last Sold Summary

      • 19% Above List Price
      • $250/SF
      • 175 Days On Market

      Last Sold Price $400,000

      Last Listing Agent Christie Bishop Creig Northrop Team of Long & Foster

  • 117 Chesapeake Ave, Saint Michaels, MD 21663
    117 Chesapeake Ave, Saint Michaels, MD 21663
    117 Chesapeake Ave, Saint Michaels, MD 21663
    /4

    $165,000 Pending

    • Land
    • 0.17 Acre
    • $970,588 per Acre

    117 Chesapeake Ave, Saint Michaels, MD 21663

    End of non through street. 3 -4 blocks from historic district stores, restaurants, etc. Convenience and the quiet of seclusion in town.....As of yet no sign.

    Richard Covell Meredith Fine Properties

    117 Chesapeake Ave, Saint Michaels, MD 21663
  • 8095 Church Neck Rd, Saint Michaels, MD 21663
    8095 Church Neck Rd, Saint Michaels, MD 21663
    8095 Church Neck Rd, Saint Michaels, MD 21663
    /48

    $1,400,000 Sold Nov 21, 2025

    8095 Church Neck Rd, Saint Michaels, MD 21663

    • 4 Beds
    • 2.5 Baths
    • 3,340 Sq Ft
    • Built 1991

    Last Sold Summary

    • $419/SF
    • 26 Days On Market

    Current Estimated Value $1,452,509

    Last Listing Agent Laura Carney TTR Sotheby's International Realty

    8095 Church Neck Rd, Saint Michaels, MD 21663
    • 115 W Chew Ave, Saint Michaels, MD 21663
      115 W Chew Ave, Saint Michaels, MD 21663
      115 W Chew Ave, Saint Michaels, MD 21663
      /38

      Est $833,823 Not Listed For Sale

      115 W Chew Ave, Saint Michaels, MD 21663

      • 4 Beds
      • 2.5 Baths
      • 1,781 Sq Ft
      • Built 1890
      115 W Chew Ave, Saint Michaels, MD 21663

      Last Sold Summary

      • 9% Below List Price
      • $514/SF
      • 28 Days On Market

      Last Sold Price $915,000

      Last Listing Agent Tracy Higgs-Wagner Meredith Fine Properties

  • 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
  • 23014 Claiborne Landing Rd, Claiborne, MD 21624
    23014 Claiborne Landing Rd, Claiborne, MD 21624
    23014 Claiborne Landing Rd, Claiborne, MD 21624
    /59

    $855,000 Sold Apr 17, 2025

    23014 Claiborne Landing Rd, Claiborne, MD 21624

    • 3 Beds
    • 1.5 Baths
    • 1,790 Sq Ft
    • Built 1955

    Last Sold Summary

    • $478/SF
    • 36 Days On Market

    Current Estimated Value $850,757

    Last Listing Agent Ray Stevens Benson & Mangold, LLC

    23014 Claiborne Landing Rd, Claiborne, MD 21624
    • 220 Tyler Ave, Saint Michaels, MD 21663
      220 Tyler Ave, Saint Michaels, MD 21663
      220 Tyler Ave, Saint Michaels, MD 21663
      /46

      Est $666,012 Not Listed For Sale

      220 Tyler Ave, Saint Michaels, MD 21663

      • 5 Beds
      • 2.5 Baths
      • 2,496 Sq Ft
      • Built 1998
      220 Tyler Ave, Saint Michaels, MD 21663

      Last Sold Summary

      • 7% Above List Price
      • $250/SF
      • 115 Days On Market

      Last Sold Price $624,900

      Last Listing Agent Gary Marquardt Coldwell Banker (NRT-Southeast-MidAtlantic)

  • 105 Seymour Ave, Saint Michaels, MD 21663
    105 Seymour Ave, Saint Michaels, MD 21663
    105 Seymour Ave, Saint Michaels, MD 21663
    /41

    $474,000 Open Sat 2PM - 4PM

    • 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
  • 9545 Quail Hollow Dr Unit 206, Saint Michaels, MD 21663
    9545 Quail Hollow Dr Unit 206, Saint Michaels, MD 21663
    9545 Quail Hollow Dr Unit 206, Saint Michaels, MD 21663
    /41

    $435,000 Sold Jun 23, 2025

    9545 Quail Hollow Dr Unit 206, Saint Michaels, MD 21663

    • 3 Beds
    • 2 Baths
    • 1,752 Sq Ft
    • Built 1973

    Last Sold Summary

    • $248/SF
    • 33 Days On Market

    Current Estimated Value $433,352

    Last Listing Agent Cornelia Heckenbach Long & Foster Real Estate, Inc.

    9545 Quail Hollow Dr Unit 206, Saint Michaels, MD 21663
    • 209 E Maple Ave, Saint Michaels, MD 21663
      209 E Maple Ave, Saint Michaels, MD 21663
      209 E Maple Ave, Saint Michaels, MD 21663
      /10

      Est $390,621 Not Listed For Sale

      209 E Maple Ave, Saint Michaels, MD 21663

      • 2 Beds
      • 1 Bath
      • 920 Sq Ft
      • Built 1958
      209 E Maple Ave, Saint Michaels, MD 21663

      Last Sold Summary

      • 2% Below List Price
      • $435/SF
      • 34 Days On Market

      Last Sold Price $400,000

      Last Listing Agent Robert Lacaze TTR Sotheby's International Realty

  • 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
  • 203 Mulberry St, Saint Michaels, MD 21663
    203 Mulberry St, Saint Michaels, MD 21663
    203 Mulberry St, Saint Michaels, MD 21663
    /36

    $926,000 Sold Jan 15, 2026

    203 Mulberry St, Saint Michaels, MD 21663

    • 3 Beds
    • 2 Baths
    • 1,740 Sq Ft
    • Built 1970

    Last Sold Summary

    • 3% Above List Price
    • $532/SF
    • 0 Days On Market

    Current Estimated Value $929,177

    Last Listing Agent Brian Gearhart Benson & Mangold, LLC

    203 Mulberry St, Saint Michaels, MD 21663
    • 9789 Pintail Place, Saint Michaels, MD 21663
      9789 Pintail Place, Saint Michaels, MD 21663
      9789 Pintail Place, Saint Michaels, MD 21663
      /74

      Est $3,518,020 Not Listed For Sale

      9789 Pintail Place, Saint Michaels, MD 21663

      • 6 Beds
      • 4.5 Baths
      • 5,146 Sq Ft
      • Built 2001
      9789 Pintail Place, Saint Michaels, MD 21663

      Last Sold Summary

      • 7% Below List Price
      • $738/SF
      • 97 Days On Market

      Last Sold Price $3,800,000

      Last Listing Agent Cornelia Heckenbach Long & Foster

  • 9518 Quail Hollow Dr Unit 702, Saint Michaels, MD 21663
    9518 Quail Hollow Dr Unit 702, Saint Michaels, MD 21663
    9518 Quail Hollow Dr Unit 702, Saint Michaels, MD 21663
    /36

    $480,000

    • 3 Beds
    • 3 Baths
    • 1,800 Sq Ft

    9518 Quail Hollow Dr Unit 702, Saint Michaels, MD 21663

    Set within the sought-after Martingham community of Quail Hollow, this fully updated 3-bedroom, 3-bath townhome offers stylish, low-maintenance living just minutes from downtown St. Michaels. Extensive renovations completed between 2022 and 2024 make this home truly turnkey. The main level welcomes you with beautiful wood floors, a bright and open living area with gas fireplace, custom built-ins,

    Barbara Watkins Benson & Mangold, LLC

    9518 Quail Hollow Dr Unit 702, Saint Michaels, MD 21663
  • 23336 Tunis Ln, Claiborne, MD 21624
    23336 Tunis Ln, Claiborne, MD 21624
    23336 Tunis Ln, Claiborne, MD 21624
    /70

    $465,000 Sold Sep 18, 2025

    23336 Tunis Ln, Claiborne, MD 21624

    • 2 Beds
    • 1 Bath
    • 1,190 Sq Ft
    • Built 1900

    Last Sold Summary

    • $391/SF
    • 67 Days On Market

    Current Estimated Value $458,295

    Last Listing Agent Maureen McHugh Chesapeake Bay Real Estate Plus, LLC

    23336 Tunis Ln, Claiborne, MD 21624
    • 23863 Mount Misery Rd, Saint Michaels, MD 21663
      23863 Mount Misery Rd, Saint Michaels, MD 21663
      23863 Mount Misery Rd, Saint Michaels, MD 21663
      /34

      Est $982,816 Not Listed For Sale

      23863 Mount Misery Rd, Saint Michaels, MD 21663

      • 3 Beds
      • 5 Baths
      • 2,497 Sq Ft
      • Built 1987
      23863 Mount Misery Rd, Saint Michaels, MD 21663

      Last Sold Summary

      • 15% Above List Price
      • $342/SF
      • 7 Days On Market

      Last Sold Price $855,000

      Last Listing Agent Chuck Mangold 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
  • 205 E Chew Ave, Saint Michaels, MD 21663
    205 E Chew Ave, Saint Michaels, MD 21663
    205 E Chew Ave, Saint Michaels, MD 21663
    /28

    $1,175,000 Sold Nov 14, 2025

    205 E Chew Ave, Saint Michaels, MD 21663

    • 2 Beds
    • 1.5 Baths
    • 1,780 Sq Ft
    • Built 1889

    Last Sold Summary

    • $660/SF
    • 153 Days On Market

    Current Estimated Value $1,147,180

    Last Listing Agent Brian Gearhart Benson & Mangold, LLC

    205 E Chew Ave, Saint Michaels, MD 21663
    • 201 E Chew Ave, Saint Michaels, MD 21663
      201 E Chew Ave, Saint Michaels, MD 21663
      201 E Chew Ave, Saint Michaels, MD 21663
      /48

      Est $1,624,923 Not Listed For Sale

      201 E Chew Ave, Saint Michaels, MD 21663

      • 4 Beds
      • 2.5 Baths
      • 3,694 Sq Ft
      • Built 2017
      201 E Chew Ave, Saint Michaels, MD 21663

      Last Sold Summary

      • 8% Above List Price
      • $406/SF
      • 5 Days On Market

      Last Sold Price $1,500,000

      Last Listing Agent Chuck Mangold Benson & Mangold, LLC

  • 303 Manor St, Saint Michaels, MD 21663
    303 Manor St, Saint Michaels, MD 21663
    303 Manor St, Saint Michaels, MD 21663
    /104

    $1,985,000

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

    303 Manor St, Saint Michaels, MD 21663

    Welcome to "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
  • 110 Lee St, Saint Michaels, MD 21663
    110 Lee St, Saint Michaels, MD 21663
    110 Lee St, Saint Michaels, MD 21663
    /49

    $475,000 Sold Sep 18, 2025

    110 Lee St, Saint Michaels, MD 21663

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft
    • Built 2024

    Last Sold Summary

    • $317/SF
    • 79 Days On Market

    Last Listing Agent Chance Stem LPT Realty, LLC

    110 Lee St, Saint Michaels, MD 21663
    • 24997 Back Creek Dr, Saint Michaels, MD 21663
      24997 Back Creek Dr, Saint Michaels, MD 21663
      24997 Back Creek Dr, Saint Michaels, MD 21663
      /76

      Est $770,638 Not Listed For Sale

      24997 Back Creek Dr, Saint Michaels, MD 21663

      • 4 Beds
      • 2.5 Baths
      • 3,010 Sq Ft
      • Built 2003
      24997 Back Creek Dr, Saint Michaels, MD 21663

      Last Sold Summary

      • 18% Above List Price
      • $218/SF
      • 16 Days On Market

      Last Sold Price $655,000

      Last Listing Agent Barbara McCaffrey Redfin Corp

  • 7909 Church Neck Rd, Saint Michaels, MD 21663
    7909 Church Neck Rd, Saint Michaels, MD 21663
    7909 Church Neck Rd, Saint Michaels, MD 21663
    /22

    $2,300,000 Coming Soon

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

    7909 Church Neck Rd, Saint Michaels, MD 21663

    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 designed layout includes

    Cheri Bruce-Phipps TTR Sotheby's International Realty

    7909 Church Neck Rd, Saint Michaels, MD 21663
  • 25028 Maplewood Dr, Saint Michaels, MD 21663
    25028 Maplewood Dr, Saint Michaels, MD 21663
    25028 Maplewood Dr, Saint Michaels, MD 21663
    /41

    $475,000 Sold Nov 21, 2025

    25028 Maplewood Dr, Saint Michaels, MD 21663

    • 3 Beds
    • 2.5 Baths
    • 1,440 Sq Ft
    • Built 1999

    Last Sold Summary

    • $330/SF
    • 3 Days On Market

    Current Estimated Value $482,758

    Last Listing Agent Monica Penwell TTR Sotheby's International Realty

    25028 Maplewood Dr, 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 $608,816 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

      • 27% Above List Price
      • $207/SF
      • 10 Days On Market

      Last Sold Price $480,000

      Last Listing Agent Kathleen Coale Benson & Mangold, LLC

  • 205 Cherry St, St. Michaels, MD 21663
    205 Cherry St, St. Michaels, MD 21663
    205 Cherry St, St. Michaels, MD 21663
    /62

    $2,575,000

    • 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

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