2,706

Saint Michaels, MD Homes

Section Image
    • 9794 Martingham Cir Unit D5, Saint Michaels, MD 21663
      9794 Martingham Cir Unit D5, Saint Michaels, MD 21663
      9794 Martingham Cir Unit D5, Saint Michaels, MD 21663
      /48

      Est $806,552

      Not Listed For Sale

      9794 Martingham Cir Unit D5, Saint Michaels, MD 21663

      • 3 Beds
      • 3 Baths
      • 2,135 Sq Ft
      • Built 1990
      9794 Martingham Cir Unit D5, Saint Michaels, MD 21663

      Last Sold Summary

      • 53 Days On Market

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

  • 101 Seymour Ave, Saint Michaels, MD 21663
    101 Seymour Ave, Saint Michaels, MD 21663
    101 Seymour Ave, Saint Michaels, MD 21663
    /56

    $995,000

    Under Contract
    • 3 Beds
    • 2.5 Baths
    • 2,091 Sq Ft

    101 Seymour Ave, Saint Michaels, MD 21663

    Extremely well maintained, inside and out, 3 bedroom 2 1/2 bath house with an oversized 2 car detached garage, huge back yard and within walking distance to downtown St. Michael's! Since the owner purchased this house there has been a primary first floor master addition, all new windows throughout, updated stainless appliances, professional interior designer decorating, all new extensive

    Henry Gibbons-Neff Meredith Fine Properties

    101 Seymour Ave, Saint Michaels, MD 21663
  • 23854 Mount Misery Rd, Saint Michaels, MD 21663
    23854 Mount Misery Rd, Saint Michaels, MD 21663
    23854 Mount Misery Rd, Saint Michaels, MD 21663
    /52

    $1,800,000

    Sold Nov 14, 2025

    23854 Mount Misery Rd, Saint Michaels, MD 21663

    • 3 Beds
    • 3.5 Baths
    • 4,012 Sq Ft
    • Built 1996

    Last Sold Summary

    • $449/SF
    • 1 Day On Market

    Current Estimated Value $1,917,934

    Last Listing Agent Brian Petzold Benson & Mangold, LLC

    23854 Mount Misery Rd, Saint Michaels, MD 21663
    • 9792 Martingham Cir Unit 8, Saint Michaels, MD 21663
      9792 Martingham Cir Unit 8, Saint Michaels, MD 21663
      9792 Martingham Cir Unit 8, Saint Michaels, MD 21663
      /51

      Est $842,063

      Not Listed For Sale

      9792 Martingham Cir Unit 8, Saint Michaels, MD 21663

      • 3 Beds
      • 3 Baths
      • 2,135 Sq Ft
      • Built 1990
      9792 Martingham Cir Unit 8, Saint Michaels, MD 21663

      Last Sold Summary

      • 22 Days On Market

      Last Listing Agent Dawn Lednum Chesapeake Bay Real Estate Plus, LLC

  • 807 Radcliff Ave, Saint Michaels, MD 21663
    807 Radcliff Ave, Saint Michaels, MD 21663
    807 Radcliff Ave, Saint Michaels, MD 21663
    /41

    $775,000

    $85K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,027 Sq Ft

    807 Radcliff Ave, Saint Michaels, MD 21663

    ***BRAND NEW & MOVE-IN READY*** this Arts & Crafts home sits on a quaint corner lot in picturesque Saint Michaels, MD and is clad with high end finishes throughout. Step from the covered front porch into the luxurious kitchen which features stylish pistachio and linen cabinetry with satin bronze hardware, Z-Line appliances including a 36" dual fuel 6 burner range with champagne bronze

    Adam Ellison Long & Foster Real Estate, Inc.

    807 Radcliff Ave, Saint Michaels, MD 21663
  • 209 Webb Ln, Saint Michaels, MD 21663
    209 Webb Ln, Saint Michaels, MD 21663
    209 Webb Ln, Saint Michaels, MD 21663
    /33

    $236,000

    Sold Mar 31, 2026

    209 Webb Ln, Saint Michaels, MD 21663

    • 2 Beds
    • 1 Bath
    • 932 Sq Ft
    • Built 1981

    Last Sold Summary

    • 3% Above List Price
    • $253/SF
    • 44 Days On Market

    Current Estimated Value $229,749

    Last Listing Agent Harry Kaiser Coldwell Banker Realty

    209 Webb Ln, Saint Michaels, MD 21663
    • 24362 Widgeon Place Unit 6, Saint Michaels, MD 21663
      24362 Widgeon Place Unit 6, Saint Michaels, MD 21663
      24362 Widgeon Place Unit 6, Saint Michaels, MD 21663
      /35

      Est $397,139

      Not Listed For Sale

      24362 Widgeon Place Unit 6, Saint Michaels, MD 21663

      • 3 Beds
      • 3 Baths
      • 1,752 Sq Ft
      • Built 1986
      24362 Widgeon Place Unit 6, Saint Michaels, MD 21663

      Last Sold Summary

      • 178 Days On Market

      Last Listing Agent Skipper Marquess Coldwell Banker Realty

  • 9020 Bozman Neavitt Rd, Saint Michaels, MD 21663
    9020 Bozman Neavitt Rd, Saint Michaels, MD 21663
    9020 Bozman Neavitt Rd, Saint Michaels, MD 21663
    /32

    $1,995,000

    • 4 Beds
    • 2.5 Baths
    • 3,028 Sq Ft

    9020 Bozman Neavitt Rd, Saint Michaels, MD 21663

    Just 4 miles (five minutes) outside the historic town of St. Michaels, MD, this 15-acre property is located in an area of large, private waterfront estates. Over 400 ft. of protected shoreline. Westerly exposure provides Exceptional Sunset Views across the sparkling waters of Harris Creek! 120' x 6' pile-driven pier provides approximately 4' MLW. Sited near the water at the end of a long,

    Tom Crouch Benson & Mangold, LLC

    9020 Bozman Neavitt Rd, Saint Michaels, MD 21663
  • 9206 Martingham Dr, Saint Michaels, MD 21663
    9206 Martingham Dr, Saint Michaels, MD 21663
    9206 Martingham Dr, Saint Michaels, MD 21663
    /43

    $600,000

    Sold Sep 18, 2026

    9206 Martingham Dr, Saint Michaels, MD 21663

    • 4 Beds
    • 2.5 Baths
    • 2,841 Sq Ft
    • Built 1980

    Last Sold Summary

    • 5% Below List Price
    • $211/SF
    • 41 Days On Market

    Current Estimated Value $733,162

    Last Listing Agent Salar Hakimi Samson Properties

    9206 Martingham Dr, Saint Michaels, MD 21663
    • 24360 Widgeon Place Unit 11, Saint Michaels, MD 21663
      24360 Widgeon Place Unit 11, Saint Michaels, MD 21663
      24360 Widgeon Place Unit 11, Saint Michaels, MD 21663
      /75

      Est $351,635

      Not Listed For Sale

      24360 Widgeon Place Unit 11, Saint Michaels, MD 21663

      • 2 Beds
      • 2.5 Baths
      • 1,800 Sq Ft
      • Built 1986
      24360 Widgeon Place Unit 11, Saint Michaels, MD 21663

      Last Sold Summary

      • 78 Days On Market

      Last Listing Agent David Boutin RE/MAX One

  • 104 Mulberry St, Saint Michaels, MD 21663
    104 Mulberry St, Saint Michaels, MD 21663
    104 Mulberry St, Saint Michaels, MD 21663
    /74

    $1,399,000

    $71K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,938 Sq Ft

    104 Mulberry St, Saint Michaels, MD 21663

    This beautiful historic house is located in the heart of Saint Michaels Historic District, within walking distance of waterfront parks, the harbor, shops, restaurants, the Maritime Museum, public boat ramp & more. Known as the "Keithley House, " the original dwelling was built in 1786, followed by additions believed to be added in the 1860-1870 time span. This home is beautifully updated while

    Barbara Best RE/MAX One

    104 Mulberry St, Saint Michaels, MD 21663
  • 9560 Martingham Cir, Saint Michaels, MD 21663
    9560 Martingham Cir, Saint Michaels, MD 21663
    9560 Martingham Cir, Saint Michaels, MD 21663
    /39

    $630,000

    Sold Oct 10, 2025

    9560 Martingham Cir, Saint Michaels, MD 21663

    • 3 Beds
    • 2.5 Baths
    • 2,350 Sq Ft
    • Built 2000

    Last Sold Summary

    • $268/SF
    • 61 Days On Market

    Current Estimated Value $629,705

    Last Listing Agent Debra Crouch Benson & Mangold, LLC

    9560 Martingham Cir, Saint Michaels, MD 21663
    • 526 Tenant Cir, Saint Michaels, MD 21663
      526 Tenant Cir, Saint Michaels, MD 21663
      526 Tenant Cir, Saint Michaels, MD 21663
      /22

      Est $485,461

      Not Listed For Sale

      526 Tenant Cir, Saint Michaels, MD 21663

      • 3 Beds
      • 1 Bath
      • 1,216 Sq Ft
      • Built 1956
      526 Tenant Cir, Saint Michaels, MD 21663

      Last Sold Summary

      • 8 Days On Market

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

  • 108 Miles, Saint Michaels, MD 21663
    108 Miles, Saint Michaels, MD 21663
    108 Miles, Saint Michaels, MD 21663
    /27

    $295,000

    • Land
    • 23,958 Sq Ft
    • $536,364 per Acre

    108 Miles, Saint Michaels, MD 21663

    A rare opportunity in the heart of St. Michaels: this half-acre+ wooded parcel offers the privacy of a tucked-away retreat with the everyday convenience of an in-town location. Restaurants, shops, seasonal events, waterfront parks, and the character of the historic district are all close at hand, yet the setting feels quiet and natural. Approximately three times the size of a typical in-town lot,

    Chuck Mangold Benson & Mangold, LLC

    108 Miles, Saint Michaels, MD 21663
  • 24822 Swan Rd, Saint Michaels, MD 21663
    24822 Swan Rd, Saint Michaels, MD 21663
    24822 Swan Rd, Saint Michaels, MD 21663
    /37

    $785,000

    Sold Apr 30, 2026

    24822 Swan Rd, Saint Michaels, MD 21663

    • 3 Beds
    • 3 Baths
    • 2,439 Sq Ft
    • Built 1982

    Last Sold Summary

    • 5% Below List Price
    • $322/SF
    • 9 Days On Market

    Current Estimated Value $784,915

    Last Listing Agent Brian Gearhart Benson & Mangold, LLC

    24822 Swan Rd, Saint Michaels, MD 21663
    • 24981 Back Creek Dr, Saint Michaels, MD 21663
      24981 Back Creek Dr, Saint Michaels, MD 21663
      24981 Back Creek Dr, Saint Michaels, MD 21663
      /47

      Est $754,019

      Not Listed For Sale

      24981 Back Creek Dr, Saint Michaels, MD 21663

      • 5 Beds
      • 3.5 Baths
      • 3,166 Sq Ft
      • Built 2006
      24981 Back Creek Dr, Saint Michaels, MD 21663

      Last Sold Summary

      • 4 Days On Market

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

  • 9359 Martingham Cir, Saint Michaels, MD 21663
    9359 Martingham Cir, Saint Michaels, MD 21663
    9359 Martingham Cir, Saint Michaels, MD 21663
    /70

    $775,000

    $20K PRICE DROP Pending
    • 4 Beds
    • 3 Baths
    • 1,988 Sq Ft

    9359 Martingham Cir, Saint Michaels, MD 21663

    Stunning One-Level Luxury Living with Golf Course & Pond ViewsPerfectly positioned in one of St. Michaels' most desirable communities, this exceptional residence offers effortless one-level living with a private backyard overlooking a tranquil pond and the 4th green of The Links at Perry Cabin.Just minutes from the historic charm, fine dining, boutiques, and waterfront attractions

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    9359 Martingham Cir, Saint Michaels, MD 21663
  • 231 Madison Ave, Saint Michaels, MD 21663
    231 Madison Ave, Saint Michaels, MD 21663
    231 Madison Ave, Saint Michaels, MD 21663
    /47

    $619,000

    Sold Oct 20, 2025

    231 Madison Ave, Saint Michaels, MD 21663

    • 2 Beds
    • 2 Baths
    • 1,702 Sq Ft
    • Built 1972

    Last Sold Summary

    • $364/SF
    • 18 Days On Market

    Current Estimated Value $592,287

    Last Listing Agent Monica Penwell TTR Sotheby's International Realty

    231 Madison Ave, Saint Michaels, MD 21663
    • 204 W Chew Ave, Saint Michaels, MD 21663
      204 W Chew Ave, Saint Michaels, MD 21663
      204 W Chew Ave, Saint Michaels, MD 21663
      /76

      Est $639,828

      Not Listed For Sale

      204 W Chew Ave, Saint Michaels, MD 21663

      • 3 Beds
      • 2 Baths
      • 1,500 Sq Ft
      • Built 1890
      204 W Chew Ave, Saint Michaels, MD 21663

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Ani Gonzalez-Brunet Coldwell Banker Realty

  • 9545 Quail Hollow Dr Unit 205, Saint Michaels, MD 21663
    9545 Quail Hollow Dr Unit 205, Saint Michaels, MD 21663
    9545 Quail Hollow Dr Unit 205, Saint Michaels, MD 21663
    /40

    $374,000

    $11K PRICE DROP Pending
    • 2 Beds
    • 3 Baths
    • 1,800 Sq Ft

    9545 Quail Hollow Dr Unit 205, Saint Michaels, MD 21663

    REDUCED CLEAN UNIT ...CASUAL LIVING IN SOUTH AFTER "THE LINK AT PERRY CABIN " MARTINGHAM COMMUNITYNestled within the prestigious Quail Hollow community in desirable Martingham, this exceptional residence enjoys a prime setting overlooking the renowned Links at Perry Cabin golf course. One of the few units featuring a screened porch, this home offers the perfect blend of elegance,

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    9545 Quail Hollow Dr Unit 205, Saint Michaels, MD 21663
  • 24912 Back Creek Dr, Saint Michaels, MD 21663
    24912 Back Creek Dr, Saint Michaels, MD 21663
    24912 Back Creek Dr, Saint Michaels, MD 21663
    /66

    $765,000

    Sold Jun 03, 2026

    24912 Back Creek Dr, Saint Michaels, MD 21663

    • 3 Beds
    • 2.5 Baths
    • 3,166 Sq Ft
    • Built 2004

    Last Sold Summary

    • $242/SF
    • 162 Days On Market

    Current Estimated Value $773,211

    Last Listing Agent Kathleen Coale Benson & Mangold, LLC

    24912 Back Creek Dr, Saint Michaels, MD 21663
    • 10434 Claiborne Rd, Claiborne, MD 21624
      10434 Claiborne Rd, Claiborne, MD 21624
      10434 Claiborne Rd, Claiborne, MD 21624
      /50

      Est $593,855

      Not Listed For Sale

      10434 Claiborne Rd, Claiborne, MD 21624

      • 4 Beds
      • 2 Baths
      • 2,880 Sq Ft
      • Built 1900
      10434 Claiborne Rd, Claiborne, MD 21624

      Last Sold Summary

      • 99 Days On Market

      Last Listing Agent Darlene Wheatley Benson & Mangold, LLC

  • 114 W Chestnut St, St. Michaels, MD 21663
    114 W Chestnut St, St. Michaels, MD 21663
    114 W Chestnut St, St. Michaels, MD 21663
    /56

    $1,195,000

    • 4 Beds
    • 4 Baths
    • 3,528 Sq Ft

    114 W Chestnut St, St. Michaels, MD 21663

    Experience the quintessential coastal lifestyle in this historic gem, situated on one of the most sought-after streets in the St. Michaels historic district. Featuring timeless charm and character, this stately property perfectly blends classic architectural details (such as multiple built-ins and four working fireplaces) with modern convenience, all just a stone's throw from the town's vibrant

    Robert Lacaze TTR Sotheby's International Realty

    114 W Chestnut St, St. Michaels, MD 21663
  • 9235 Martingham Dr, Saint Michaels, MD 21663
    9235 Martingham Dr, Saint Michaels, MD 21663
    9235 Martingham Dr, Saint Michaels, MD 21663
    /30

    $699,000

    Sold Nov 13, 2025

    9235 Martingham Dr, Saint Michaels, MD 21663

    • 3 Beds
    • 3 Baths
    • 2,646 Sq Ft
    • Built 1995

    Last Sold Summary

    • $264/SF
    • 6 Days On Market

    Current Estimated Value $693,224

    Last Listing Agent Lish Gannon Dulin Benson & Mangold, LLC

    9235 Martingham Dr, Saint Michaels, MD 21663
    • 24640 Yacht Club Rd, Saint Michaels, MD 21663
      24640 Yacht Club Rd, Saint Michaels, MD 21663
      24640 Yacht Club Rd, Saint Michaels, MD 21663
      /94

      Est $2,379,637

      Not Listed For Sale

      24640 Yacht Club Rd, Saint Michaels, MD 21663

      • 10 Beds
      • 9.5 Baths
      • 6,433 Sq Ft
      • Built 1910
      24640 Yacht Club Rd, Saint Michaels, MD 21663

      Last Sold Summary

      • 31 Days On Market

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

  • 202 E Chestnut St, Saint Michaels, MD 21663
    202 E Chestnut St, Saint Michaels, MD 21663
    202 E Chestnut St, Saint Michaels, MD 21663
    /50

    $1,250,000

    • 3 Beds
    • 3 Baths
    • 2,052 Sq Ft

    202 E Chestnut St, Saint Michaels, MD 21663

    Welcome to the William J. Wrightson House, a beautifully restored c. 1897 residence where historic St. Michaels charm meets exceptional modern comfort. Located in the heart of town and just steps from the waterfront, marinas, shops, and restaurants, this distinctive 3-bedroom, 3-bath home offers an extraordinary opportunity to enjoy the very best of Eastern Shore living. Extensively renovated

    Wink Cowee Benson & Mangold, LLC

    202 E Chestnut St, Saint Michaels, MD 21663
  • 24362 Widgeon Place Unit 4, Saint Michaels, MD 21663
    24362 Widgeon Place Unit 4, Saint Michaels, MD 21663
    24362 Widgeon Place Unit 4, Saint Michaels, MD 21663
    /41

    $330,000

    Sold Mar 17, 2026

    24362 Widgeon Place Unit 4, Saint Michaels, MD 21663

    • 2 Beds
    • 2.5 Baths
    • 1,800 Sq Ft
    • Built 1986

    Last Sold Summary

    • $183/SF
    • 136 Days On Market

    Current Estimated Value $331,237

    Last Listing Agent Amy Berry Meredith Fine Properties

    24362 Widgeon Place Unit 4, Saint Michaels, MD 21663
    • 705 Riverview Terrace, Saint Michaels, MD 21663
      705 Riverview Terrace, Saint Michaels, MD 21663
      705 Riverview Terrace, Saint Michaels, MD 21663
      /72

      Est $2,747,566

      Not Listed For Sale

      705 Riverview Terrace, Saint Michaels, MD 21663

      • 4 Beds
      • 4 Baths
      • 4,000 Sq Ft
      • Built 1960
      705 Riverview Terrace, Saint Michaels, MD 21663

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent Barbara Watkins Benson & Mangold, LLC

  • 104 Madison Ave, Saint Michaels, MD 21663
    104 Madison Ave, Saint Michaels, MD 21663
    /2

    $459,900

    • 4 Beds
    • 4 Baths
    • 2,420 Sq Ft

    104 Madison Ave, Saint Michaels, MD 21663

    This well-maintained duplex with new roof in Rio Vista presents an exceptional investment opportunity, featuring two spacious units, each offering 2 bedrooms and 1.5 baths. Ideally situated just moments from the heart of historic downtown St. Michaels, residents enjoy easy access to charming shops, dining, and waterfront attractions—all while benefiting from no town taxes. With both units

    Chuck Mangold Benson & Mangold, LLC

    104 Madison Ave, Saint Michaels, MD 21663
  • 504 Seymour Ave, Saint Michaels, MD 21663
    504 Seymour Ave, Saint Michaels, MD 21663
    504 Seymour Ave, Saint Michaels, MD 21663
    /89

    $969,000

    Sold Sep 09, 2026

    504 Seymour Ave, Saint Michaels, MD 21663

    • 3 Beds
    • 2.5 Baths
    • 2,200 Sq Ft
    • Built 1990

    Last Sold Summary

    • 19% Below List Price
    • $440/SF
    • 101 Days On Market

    Current Estimated Value $1,032,988

    Last Listing Agent Barbara Watkins Benson & Mangold, LLC

    504 Seymour Ave, Saint Michaels, MD 21663
    • 7920 Church Neck Rd, Saint Michaels, MD 21663
      7920 Church Neck Rd, Saint Michaels, MD 21663
      7920 Church Neck Rd, Saint Michaels, MD 21663
      /49

      Est $2,274,012

      Not Listed For Sale

      7920 Church Neck Rd, Saint Michaels, MD 21663

      • 3 Beds
      • 3.5 Baths
      • 4,825 Sq Ft
      • Built 1997
      7920 Church Neck Rd, Saint Michaels, MD 21663

      Last Sold Summary

      Last Listing Agent datacorrect BrightMLS Non Subscribing Office

  • 10554 Miracle House Cir, Claiborne, MD 21624
    10554 Miracle House Cir, Claiborne, MD 21624
    10554 Miracle House Cir, Claiborne, MD 21624
    /54

    $725,000

    $100K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,170 Sq Ft

    10554 Miracle House Cir, Claiborne, MD 21624

    Quality construction throughout. This Custom Coastal Home has all the bells and whistles ..... hardwood cherry floors, masonry fireplace, 1st floor primary suite, double porches to enjoy the sunsets over Eastern Bay. Gourmet kitchen with stainless steel appliances. Two screened in porches for dining or sleeping. Very private with professional landscaping. Easy walk to Claiborne boat ramp, beach

    Dawn Lednum Chesapeake Bay Real Estate Plus, LLC

    10554 Miracle House Cir, Claiborne, MD 21624
  • 100 Grace St, St. Michaels, MD 21663
    100 Grace St, St. Michaels, MD 21663
    100 Grace St, St. Michaels, MD 21663
    /46

    $1,000,000

    Sold Feb 13, 2026

    100 Grace St, St. Michaels, MD 21663

    • 2 Beds
    • 2.5 Baths
    • 1,445 Sq Ft
    • Built 1890

    Last Sold Summary

    • $692/SF
    • 28 Days On Market

    Current Estimated Value $977,003

    Last Listing Agent Debra Crouch Benson & Mangold, LLC

    100 Grace St, St. Michaels, MD 21663
    • 24519 New Post Rd, Saint Michaels, MD 21663
      24519 New Post Rd, Saint Michaels, MD 21663
      24519 New Post Rd, Saint Michaels, MD 21663
      /3

      Est $2,116,840

      Not Listed For Sale

      24519 New Post Rd, Saint Michaels, MD 21663

      • 4 Beds
      • 3.5 Baths
      • 2,881 Sq Ft
      • Built 2001
      24519 New Post Rd, Saint Michaels, MD 21663

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Amy Berry Meredith Fine Properties

  • 24555 Deepwater Point Dr, Saint Michaels, MD 21663
    24555 Deepwater Point Dr, Saint Michaels, MD 21663
    24555 Deepwater Point Dr, Saint Michaels, MD 21663
    /24

    $679,000

    $90K PRICE DROP Pending
    • 4 Beds
    • 3 Baths
    • 2,072 Sq Ft

    24555 Deepwater Point Dr, Saint Michaels, MD 21663

    This sturdy brick ranch sits on a premium lot backing up to The Links at Perry Cabin Golf Course in St. Michaels, MD. A park like setting with mature specimen trees and shrubs. It's a 4 BR, 3 full bath, one level for easy living. New updated flooring. The Martingham Subdivision provides a waterfront community lot to enjoy the Miles River constant boat shows. Wednesday night sailboat races, fourth

    Dawn Lednum Chesapeake Bay Real Estate Plus, LLC

    24555 Deepwater Point Dr, Saint Michaels, MD 21663
  • 121 W Chestnut St, St. Michaels, MD 21663
    121 W Chestnut St, St. Michaels, MD 21663
    121 W Chestnut St, St. Michaels, MD 21663
    /57

    $1,395,000

    Sold Jun 22, 2026

    121 W Chestnut St, St. Michaels, MD 21663

    • 3 Beds
    • 2.5 Baths
    • 2,540 Sq Ft
    • Built 1890

    Last Sold Summary

    • $549/SF
    • 1 Day On Market

    Current Estimated Value $1,379,128

    Last Listing Agent Carolina Barksdale Benson & Mangold, LLC

    121 W Chestnut St, St. Michaels, MD 21663
    • 7171 Drum Point Rd, Saint Michaels, MD 21663
      7171 Drum Point Rd, Saint Michaels, MD 21663
      7171 Drum Point Rd, Saint Michaels, MD 21663
      /70

      Est $1,671,505

      Not Listed For Sale

      7171 Drum Point Rd, Saint Michaels, MD 21663

      • 4 Beds
      • 3 Baths
      • 3,000 Sq Ft
      • Built 1969
      7171 Drum Point Rd, Saint Michaels, MD 21663

      Last Sold Summary

      • 11 Days On Market

      Last Listing Agent Larry Brennan TTR Sotheby's International Realty

  • 101 Brooks Ln, Saint Michaels, MD 21663
    101 Brooks Ln, Saint Michaels, MD 21663
    101 Brooks Ln, Saint Michaels, MD 21663
    /28

    $425,000

    Pending
    • 3 Beds
    • 2 Baths
    • 1,120 Sq Ft

    101 Brooks Ln, Saint Michaels, MD 21663

    Seller will offer a 10K credit for a storage shed with full price offer! Welcome to this beautifully updated cottage in the heart of St. Michaels—where modern comfort meets Eastern Shore charm. Perfectly situated within walking distance to the town’s shops, restaurants, Rails to Trails, and the renowned Maritime Museum, this single‑level home offers both convenience and a peaceful, private

    Stacie Luhrman Benson & Mangold, LLC

    101 Brooks Ln, Saint Michaels, MD 21663
  • 24700 Deepwater Unit 23, Saint Michaels, MD 21663
    24700 Deepwater Unit 23, Saint Michaels, MD 21663
    24700 Deepwater Unit 23, Saint Michaels, MD 21663
    /29

    $335,000

    Sold Sep 21, 2026

    24700 Deepwater Unit 23, Saint Michaels, MD 21663

    • 2 Beds
    • 2.5 Baths
    • 1,487 Sq Ft
    • Built 1979

    Last Sold Summary

    • 11% Below List Price
    • $225/SF
    • 121 Days On Market

    Last Listing Agent Tracy Higgs-Wagner Meredith Fine Properties

    24700 Deepwater Unit 23, Saint Michaels, MD 21663
    • 400 Railroad Ave, Saint Michaels, MD 21663
      400 Railroad Ave, Saint Michaels, MD 21663
      400 Railroad Ave, Saint Michaels, MD 21663
      /35

      Est $509,267

      Not Listed For Sale

      400 Railroad Ave, Saint Michaels, MD 21663

      • 3 Beds
      • 2 Baths
      • 1,674 Sq Ft
      • Built 1930
      400 Railroad Ave, Saint Michaels, MD 21663

      Last Sold Summary

      • 62 Days On Market

      Last Listing Agent Monica Penwell TTR Sotheby's International Realty

Showing Results 81 - 120, Page 3 of 18

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