2,828

Saint Michaels, MD Homes

Section Image
  • /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
    • /12

      Est $193,871

      Not Listed For Sale

      226 North St, Saint Michaels, MD 21663

      • Built 1969
      226 North St, Saint Michaels, MD 21663

      Last Sold Summary

      • 247 Days On Market

  • /36

    $455,000

    $25K PRICE DROP
    • 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, backing to the top rated golf course The Links at Perry Cabin, 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

    Barbara Watkins Benson & Mangold, LLC

    9518 Quail Hollow Dr Unit 702, 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 $462,444

    Last Listing Agent Monica Penwell TTR Sotheby's International Realty

    25028 Maplewood Dr, Saint Michaels, MD 21663
    • /38

      Est $835,612

      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

      • 28 Days On Market

  • /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
  • /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 $6,729,740

    Last Listing Agent Clifford Meredith Meredith Fine Properties

    24629 Beverly Rd, Saint Michaels, MD 21663
    • /53

      Est $650,279

      Not Listed For Sale

      23203 Stewart Way, McDaniel, MD 21647

      • 3 Beds
      • 2.5 Baths
      • 2,652 Sq Ft
      • Built 2005
      23203 Stewart Way, McDaniel, MD 21647

      Last Sold Summary

      • 12 Days On Market

  • /49

    $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
  • /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 $2,157,485

    Last Listing Agent Laura Carney TTR Sotheby's International Realty

    25500 Chance Farm Rd, Royal Oak, MD 21662
    • /46

      Est $664,960

      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

      • 115 Days On Market

  • /52

    $1,295,000

    $155K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,816 Sq Ft

    9251 Mallard Point Ct, McDaniel, MD 21647

    Harris Creek Waterfront. This 3 bedroom, 2 bath well maintained brick one story house is the perfect getaway. Nestled on 1.63+/- acres it is the perfect blend of privacy and community. This home features a large kitchen with several entertaining areas including a cozy living room complete with a fireplace and a large living room that overlooks the huge screen porch and Harris Creek and a gracious

    Jim Corson Benson & Mangold, LLC

    9251 Mallard Point Ct, McDaniel, MD 21647
  • /36

    $539,500

    Sold Jun 30, 2026

    113 Gloria Ave, Saint Michaels, MD 21663

    • 3 Beds
    • 2 Baths
    • 1,456 Sq Ft
    • Built 1994

    Last Sold Summary

    • 12% Below List Price
    • $371/SF
    • 76 Days On Market

    Current Estimated Value $533,596

    Last Listing Agent Peter Stark Benson & Mangold, LLC

    113 Gloria Ave, Saint Michaels, MD 21663
    • /40

      Est $819,316

      Not Listed For Sale

      919 Riverview Terrace, Saint Michaels, MD 21663

      • 3 Beds
      • 2.5 Baths
      • 2,948 Sq Ft
      • Built 2005
      919 Riverview Terrace, Saint Michaels, MD 21663

      Last Sold Summary

      • 8 Days On Market

  • /50

    $2,000,000

    $600K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 4,492 Sq Ft

    7909 Church Neck Rd, Saint Michaels, MD 21663

    PRICE IMPROVEMENT.... PRIVATE Estate Living Minutes from Historic St. Michaels... Escape to nearly twenty acres of unspoiled countryside just moments from the charm and waterfront allure of historic St. Michaels. This 4,492-square-foot home offers refined comfort with four bedrooms, two and a half baths, and a gourmet kitchen designed for both everyday living and effortless entertaining. A

    Cheri Bruce-Phipps TTR Sotheby's International Realty

    7909 Church Neck Rd, 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 $441,539

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

    25070 Hurley Ln, Saint Michaels, MD 21663
    • /10

      Est $401,428

      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

      • 34 Days On Market

  • /101

    $849,000

    • 3 Beds
    • 3.5 Baths
    • 3,570 Sq Ft

    10494 Rich Neck Rd, Claiborne, MD 21624

    An Exceptional Opportunity! Unexpectedly available once again due solely to a change in the buyers' personal circumstances, this exceptional property is available through no fault of the home. If you missed it the first time, here's your opportunity to own one of the area's most distinctive and beautifully maintained residences. Ideally situated just four miles from the heart of charming St.

    Maureen McHugh Chesapeake Bay Real Estate Plus, LLC

    10494 Rich Neck Rd, Claiborne, MD 21624
  • /2

    $600,000

    Sold May 15, 2026

    23201 Stewart Way, McDaniel, MD 21647

    • 3 Beds
    • 2.5 Baths
    • 2,080 Sq Ft
    • Built 2004

    Last Sold Summary

    • 1% Above List Price
    • $288/SF
    • 9 Days On Market

    Current Estimated Value $603,673

    Last Listing Agent Kim Crouch Ozman Benson & Mangold, LLC

    23201 Stewart Way, McDaniel, MD 21647
    • /74

      Est $3,405,648

      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

      • 97 Days On Market

  • /64

    $2,575,000

    Pending
    • 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
  • /82

    $675,000

    Sold May 21, 2026

    408 Spinnaker Ln, Saint Michaels, MD 21663

    • 4 Beds
    • 2.5 Baths
    • 1,957 Sq Ft
    • Built 2022

    Last Sold Summary

    • $345/SF
    • 204 Days On Market

    Current Estimated Value $684,580

    Last Listing Agent Christie Bishop Northrop Realty

    408 Spinnaker Ln, Saint Michaels, MD 21663
    • /34

      Est $961,381

      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

      • 7 Days On Market

  • /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
  • /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 $761,640

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

    106 Grace St, Saint Michaels, MD 21663
    • /48

      Est $1,582,175

      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

      • 5 Days On Market

  • /30

    $425,000

    Sold May 18, 2026

    111 Gloria Ave, Saint Michaels, MD 21663

    • 2 Beds
    • 1.5 Baths
    • 1,125 Sq Ft
    • Built 1965

    Last Sold Summary

    • 6% Below List Price
    • $378/SF
    • 83 Days On Market

    Current Estimated Value $404,468

    Last Listing Agent Tom Crouch Benson & Mangold, LLC

    111 Gloria Ave, Saint Michaels, MD 21663
    • /76

      Est $763,051

      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

      • 16 Days On Market

  • /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
    • /66

      Est $3,408,874

      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

      • 3 Days On Market

  • /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 $957,450

    Last Listing Agent Laura Carney TTR Sotheby's International Realty

    408 Water St, Saint Michaels, MD 21663
    • /61

      Est $776,065

      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

      • 2 Days On Market

  • /42

    $947,000

    Sold May 13, 2026

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

    • 3 Beds
    • 2.5 Baths
    • 1,836 Sq Ft
    • Built 1988

    Last Sold Summary

    • 2% Below List Price
    • $516/SF
    • 3 Days On Market

    Current Estimated Value $954,220

    Last Listing Agent Meg Moran Long & Foster Real Estate, Inc.

    360 Perry Cabin Dr Unit 48, Saint Michaels, MD 21663
    • /70

      Est $960,784

      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

      • 17 Days On Market

  • /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 $746,233

    Last Listing Agent Wink Cowee Benson & Mangold, LLC

    304 N Talbot St, Saint Michaels, MD 21663
    • /53

      Est $715,317

      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

      • 11 Days On Market

  • /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 $2,595,363

    Last Listing Agent Robert Lacaze TTR Sotheby's International Realty

    900 Riverview Terrace, Saint Michaels, MD 21663
    • /66

      Est $794,545

      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

      • 54 Days On Market

  • /41

    $925,000

    Sold Aug 11, 2025

    7841 Pea Neck Rd, Saint Michaels, MD 21663

    • 3 Beds
    • 3.5 Baths
    • 3,069 Sq Ft
    • Built 2008

    Last Sold Summary

    • $301/SF
    • 1 Day On Market

    Current Estimated Value $913,464

    Last Listing Agent Dennis Covey Meredith Fine Properties

    7841 Pea Neck Rd, Saint Michaels, MD 21663
    • /65

      Est $786,153

      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

      • 95 Days On Market

Showing Results 161 - 200, Page 5 of 18

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