2,809

Homes in ZIP Code 21663

Section Image
  • 106 E Chestnut St, Saint Michaels, MD 21663
    106 E Chestnut St, Saint Michaels, MD 21663
    106 E Chestnut St, Saint Michaels, MD 21663
    /39

    $1,325,000 Pending

    • 2 Beds
    • 2.5 Baths
    • 2,282 Sq Ft

    106 E Chestnut St, Saint Michaels, MD 21663

    Luxury Restoration in the Heart of Historic St. Michaels Welcome to 106 E. Chestnut Street, where historic charm and modern luxury come together in one of the Eastern Shore’s most beloved waterfront towns. Completely renovated down to the studs, this exceptional home has been thoughtfully reimagined to preserve its classic character while introducing high-end systems, refined finishes, and modern

    Justin Pokrywka Taylor Properties

    106 E Chestnut St, Saint Michaels, MD 21663
  • 24318 Oakwood Park Rd, Saint Michaels, MD 21663
    24318 Oakwood Park Rd, Saint Michaels, MD 21663
    24318 Oakwood Park Rd, Saint Michaels, MD 21663
    /44

    $1,130,000 Sold Feb 06, 2026

    24318 Oakwood Park Rd, Saint Michaels, MD 21663

    • 3 Beds
    • 3 Baths
    • 2,085 Sq Ft
    • Built 1968

    Last Sold Summary

    • $542/SF
    • 73 Days On Market

    Current Estimated Value $1,137,034

    Last Listing Agent Kathleen Eder Compass

    24318 Oakwood Park Rd, Saint Michaels, MD 21663
    • 104 Mulberry St, Saint Michaels, MD 21663
      104 Mulberry St, Saint Michaels, MD 21663
      104 Mulberry St, Saint Michaels, MD 21663
      /72

      Est $1,265,485 Not Listed For Sale

      104 Mulberry St, Saint Michaels, MD 21663

      • 3 Beds
      • 2.5 Baths
      • 1,938 Sq Ft
      • Built 1786
      104 Mulberry St, Saint Michaels, MD 21663

      Last Sold Summary

      • 2% Below List Price
      • $668/SF
      • Last Sold Price $1,295,000
      • Feb 21, 2025

      Last Listing Agent Tom Crouch Benson & Mangold, LLC

  • 9180 Saint Michaels Rd, Saint Michaels, MD 21663
    9180 Saint Michaels Rd, Saint Michaels, MD 21663
    9180 Saint Michaels Rd, Saint Michaels, MD 21663
    /66

    $1,685,000

    • 5 Beds
    • 5 Baths
    • 4,728 Sq Ft

    9180 Saint Michaels Rd, Saint Michaels, MD 21663

    UNIQUE PROPERTY RIGHT OUTSIDE OF HISTORIC ST MICHAELS TOWN LIMITS ACROSS THE LINK AT PERRY CABIN. THIS FABULOUS HOME OFFERS SPACE FOR GATHERINGS WITH FAMILY OR FRIENDS BUT ALSO FEELS COZY FOR EMPTY NESTERS THAT LOVE TO ENTERTAIN. THERE ARE NO RESTRICTIONS THAT PROHIBIT VACATION RENTAL, THERE SHOULD BE SPACE FOR AN INGROUND POOL .ORIGINALLY BUILD IN 1973 THE CURRENT OWNER GUTTED THE HOME, ALL

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    9180 Saint Michaels Rd, Saint Michaels, MD 21663
  • 9217 Martingham Dr, Saint Michaels, MD 21663
    9217 Martingham Dr, Saint Michaels, MD 21663
    9217 Martingham Dr, Saint Michaels, MD 21663
    /63

    $625,000 Sold Aug 07, 2025

    9217 Martingham Dr, Saint Michaels, MD 21663

    • 3 Beds
    • 2.5 Baths
    • 1,945 Sq Ft
    • Built 1988

    Last Sold Summary

    • $321/SF
    • 3 Days On Market

    Current Estimated Value $621,268

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

    9217 Martingham Dr, Saint Michaels, MD 21663
    • 120 W Chestnut St, Saint Michaels, MD 21663
      120 W Chestnut St, Saint Michaels, MD 21663
      120 W Chestnut St, Saint Michaels, MD 21663
      /30

      Est $851,926 Not Listed For Sale

      120 W Chestnut St, Saint Michaels, MD 21663

      • 2 Beds
      • 2.5 Baths
      • 1,218 Sq Ft
      • Built 1840
      120 W Chestnut St, Saint Michaels, MD 21663

      Last Sold Summary

      • 6% Above List Price
      • $657/SF
      • 37 Days On Market
      • Last Sold Price $800,000
      • Aug 25, 2023

      Last Listing Agent Robert G. Shannahan Shoreline Realty

  • 938 Marea Terrace, Saint Michaels, MD 21663
    938 Marea Terrace, Saint Michaels, MD 21663
    938 Marea Terrace, Saint Michaels, MD 21663
    /108

    $2,249,000

    • 4 Beds
    • 5.5 Baths
    • 3,000 Sq Ft

    938 Marea Terrace, Saint Michaels, MD 21663

    Fabulous in-town St. Michaels waterfront property – This coastal style waterfront residence, built in 2020, offers approximately 3,000 square feet of thoughtfully designed, sophisticated yet relaxed waterfront living space on San Domingo Creek. Located within town limits, the property enjoys direct access to the St. Michaels Nature Trail, allowing effortless walkability to shops, dining, and

    Carolina Barksdale Benson & Mangold, LLC

    938 Marea Terrace, Saint Michaels, MD 21663
  • 9191 Deepwater Point Rd, Saint Michaels, MD 21663
    9191 Deepwater Point Rd, Saint Michaels, MD 21663
    9191 Deepwater Point Rd, Saint Michaels, MD 21663
    /103

    $2,725,000 Sold Jul 28, 2025

    9191 Deepwater Point Rd, Saint Michaels, MD 21663

    • 5 Beds
    • 4 Baths
    • 5,088 Sq Ft
    • Built 1988

    Last Sold Summary

    • $536/SF
    • 187 Days On Market

    Current Estimated Value $2,671,072

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

    9191 Deepwater Point Rd, Saint Michaels, MD 21663
    • 106 W Chestnut St, Saint Michaels, MD 21663
      106 W Chestnut St, Saint Michaels, MD 21663
      106 W Chestnut St, Saint Michaels, MD 21663
      /46

      Est $1,276,516 Not Listed For Sale

      106 W Chestnut St, Saint Michaels, MD 21663

      • 4 Beds
      • 4 Baths
      • 3,522 Sq Ft
      • Built 1871
      106 W Chestnut St, Saint Michaels, MD 21663

      Last Sold Summary

      • 16% Above List Price
      • $312/SF
      • 30 Days On Market
      • Last Sold Price $1,100,000
      • Jun 08, 2023

      Last Listing Agent Eddie Mangold Benson & Mangold, LLC

  • 1206 Washington Dr, Saint Michaels, MD 21663
    1206 Washington Dr, Saint Michaels, MD 21663
    1206 Washington Dr, Saint Michaels, MD 21663
    /18

    $499,900

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

    1206 Washington Dr, Saint Michaels, MD 21663

    This well-maintained duplex 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 currently 100%

    Chuck Mangold Benson & Mangold, LLC

    1206 Washington Dr, Saint Michaels, MD 21663
  • 7361 Solitude Rd, Saint Michaels, MD 21663
    7361 Solitude Rd, Saint Michaels, MD 21663
    7361 Solitude Rd, Saint Michaels, MD 21663
    /23

    $1,202,000 Sold Feb 19, 2026

    7361 Solitude Rd, Saint Michaels, MD 21663

    • 3 Beds
    • 2 Baths
    • 2,012 Sq Ft
    • Built 1967

    Last Sold Summary

    • 1% Above List Price
    • $597/SF
    • 4 Days On Market

    Current Estimated Value $1,176,544

    Last Listing Agent Brian Gearhart Benson & Mangold, LLC

    7361 Solitude Rd, Saint Michaels, MD 21663
    • 122 W Chestnut St, Saint Michaels, MD 21663
      122 W Chestnut St, Saint Michaels, MD 21663
      122 W Chestnut St, Saint Michaels, MD 21663
      /53

      Est $1,180,333 Not Listed For Sale

      122 W Chestnut St, Saint Michaels, MD 21663

      • 4 Beds
      • 3.5 Baths
      • 1,890 Sq Ft
      • Built 1975
      122 W Chestnut St, Saint Michaels, MD 21663

      Last Sold Summary

      • $622/SF
      • 28 Days On Market
      • Last Sold Price $1,175,000
      • Sep 11, 2024

      Last Listing Agent Wink Cowee Benson & Mangold, LLC

  • 114 E Chew Ave, Saint Michaels, MD 21663
    114 E Chew Ave, Saint Michaels, MD 21663
    114 E Chew Ave, Saint Michaels, MD 21663
    /57

    $1,250,000

    • 3 Beds
    • 2.5 Baths
    • 2,336 Sq Ft

    114 E Chew Ave, Saint Michaels, MD 21663

    The George E. Shockley House (c. 1890) is a rare historic gem in the heart of St. Michaels, just moments from the harbor, fine dining, unique shops, walking trails, and the renowned Chesapeake Bay Maritime Museum. Beautifully preserved and enhanced with significant structural improvements by Victor MacSorley, this distinguished residence blends period charm with modern comfort and is notably not

    Wink Cowee Benson & Mangold, LLC

    114 E Chew Ave, Saint Michaels, MD 21663
  • 113 Thompson St, Saint Michaels, MD 21663
    113 Thompson St, Saint Michaels, MD 21663
    113 Thompson St, Saint Michaels, MD 21663
    /61

    $580,000 Sold Oct 31, 2025

    113 Thompson St, Saint Michaels, MD 21663

    • 3 Beds
    • 2 Baths
    • 1,566 Sq Ft
    • Built 1900

    Last Sold Summary

    • $370/SF
    • 69 Days On Market

    Current Estimated Value $593,745

    Last Listing Agent Kim Lally EXP Realty, LLC

    113 Thompson St, Saint Michaels, MD 21663
    • 417 Water St, Saint Michaels, MD 21663
      417 Water St, Saint Michaels, MD 21663
      417 Water St, Saint Michaels, MD 21663
      /65

      Est $1,520,493 Not Listed For Sale

      417 Water St, Saint Michaels, MD 21663

      • 3 Beds
      • 3.5 Baths
      • 2,579 Sq Ft
      • Built 1880
      417 Water St, Saint Michaels, MD 21663

      Last Sold Summary

      • 9% Below List Price
      • $649/SF
      • 55 Days On Market
      • Last Sold Price $1,675,000
      • Apr 25, 2024

      Last Listing Agent Clifford Meredith Meredith Fine Properties

  • 504 Seymour Ave, Saint Michaels, MD 21663
    504 Seymour Ave, Saint Michaels, MD 21663
    504 Seymour Ave, Saint Michaels, MD 21663
    /85

    $1,200,000 Open Sat 12PM - 2PM

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

    504 Seymour Ave, Saint Michaels, MD 21663

    Charming yet completely reimagined, this beautifully remodeled home offers refined Eastern Shore living at its best. Set on beautifully landscaped grounds featuring lovely water views and a partially fenced rear yard with paver patio. Thoughtfully designed and updated the main level features a modern kitchen with newer appliances, cozy breakfast room, living room with fireplace, formal dining

    Barbara Watkins Benson & Mangold, LLC

    504 Seymour Ave, Saint Michaels, MD 21663
  • 109 Chesapeake Ave, Saint Michaels, MD 21663
    109 Chesapeake Ave, Saint Michaels, MD 21663
    /2

    $865,000 Sold Aug 12, 2025

    109 Chesapeake Ave, Saint Michaels, MD 21663

    • 4 Beds
    • 2.5 Baths
    • 2,168 Sq Ft
    • Built 2022

    Last Sold Summary

    • $399/SF
    • 2 Days On Market

    Current Estimated Value $832,780

    Last Listing Agent Christopher Coppola Compass

    109 Chesapeake Ave, Saint Michaels, MD 21663
    • 7709 Quaker Neck Rd, Bozman, MD 21663
      7709 Quaker Neck Rd, Bozman, MD 21663
      7709 Quaker Neck Rd, Bozman, MD 21663
      /39

      Not Listed For Sale

      7709 Quaker Neck Rd, Bozman, MD 21663

      • 4 Beds
      • 2.5 Baths
      • 3,360 Sq Ft
      • Built 1977
      7709 Quaker Neck Rd, Bozman, MD 21663

      Last Sold Summary

      • $450/SF
      • 4 Days On Market
      • Last Sold Price $1,512,500
      • Nov 15, 2024

      Last Listing Agent Robert Lacaze TTR Sotheby's International Realty

  • 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 Pending

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

    121 W Chestnut St, St. Michaels, MD 21663

    121 West Chestnut Street is a true gem among the historic houses in St. Michaels. First time offered in a decade, the 1890 colonial embodies all the desirable features of an older home on the exterior – an inviting covered front porch, wood shingle siding, a two-bay center hall two story architecture, bracing chimneys on each end and true divided double hung windows in the front. Once inside,

    Carolina Barksdale Benson & Mangold, LLC

    121 W Chestnut St, St. Michaels, MD 21663
  • 25913 Royal Oak Rd, Royal Oak, MD 21662
    25913 Royal Oak Rd, Royal Oak, MD 21662
    25913 Royal Oak Rd, Royal Oak, MD 21662
    /34

    $525,000 Sold Apr 24, 2026

    25913 Royal Oak Rd, Royal Oak, MD 21662

    • 4 Beds
    • 2 Baths
    • 2,023 Sq Ft
    • Built 1900

    Last Sold Summary

    • 5% Above List Price
    • $260/SF
    • 4 Days On Market

    Current Estimated Value $542,201

    Last Listing Agent Pamela Ackermann-Doll RE/MAX Executive

    25913 Royal Oak Rd, Royal Oak, MD 21662
    • 24700 Deepwater Point Dr Unit 8, Saint Michaels, MD 21663
      24700 Deepwater Point Dr Unit 8, Saint Michaels, MD 21663
      24700 Deepwater Point Dr Unit 8, Saint Michaels, MD 21663
      /34

      Not Listed For Sale

      24700 Deepwater Point Dr Unit 8, Saint Michaels, MD 21663

      • 2 Beds
      • 2.5 Baths
      • 1,652 Sq Ft
      • Built 1979
      24700 Deepwater Point Dr Unit 8, Saint Michaels, MD 21663

      Last Sold Summary

      • $207/SF
      • 54 Days On Market
      • Last Sold Price $342,000
      • Sep 27, 2024

      Last Listing Agent Janet Powers Berkshire Hathaway Homeservice Homesale Realty

  • 202 E Chestnut St, Saint Michaels, MD 21663
    202 E Chestnut St, Saint Michaels, MD 21663
    202 E Chestnut St, Saint Michaels, MD 21663
    /39

    $1,275,000

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

    202 E Chestnut St, Saint Michaels, MD 21663

    Known as the William J. Wrightson House, this distinguished circa 1897 residence in the heart of St. Michaels beautifully blends timeless elegance and refined architectural detail with the comforts and conveniences of modern living. Lovingly restored from top to bottom, the home has undergone extensive renovations and improvements, including all new HVAC systems, tankless hot water system,

    Laura Carney TTR Sotheby's International Realty

    202 E Chestnut St, 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

    $505,000 Sold Jul 09, 2025

    400 Railroad Ave, Saint Michaels, MD 21663

    • 3 Beds
    • 2 Baths
    • 1,674 Sq Ft
    • Built 1930

    Last Sold Summary

    • $302/SF
    • 62 Days On Market

    Current Estimated Value $531,724

    Last Listing Agent Monica Penwell TTR Sotheby's International Realty

    400 Railroad Ave, Saint Michaels, MD 21663
    • 0 Pea Neck Rd Unit MDTA2008994, Saint Michaels, MD 21663
      0 Pea Neck Rd Unit MDTA2008994, Saint Michaels, MD 21663
      0 Pea Neck Rd Unit MDTA2008994, Saint Michaels, MD 21663
      /6

      Not Listed For Sale

      0 Pea Neck Rd Unit MDTA2008994, Saint Michaels, MD 21663

      0 Pea Neck Rd Unit MDTA2008994, Saint Michaels, MD 21663

      Last Sold Summary

      • 16 Days On Market
      • Last Sold Price $685,000
      • Feb 07, 2025

      Last Listing Agent Coard Benson Benson & Mangold, LLC

  • 107 W Chestnut St, Saint Michaels, MD 21663
    107 W Chestnut St, Saint Michaels, MD 21663
    107 W Chestnut St, Saint Michaels, MD 21663
    /105

    $1,225,000

    • 3 Beds
    • 2 Baths
    • 1,914 Sq Ft

    107 W Chestnut St, Saint Michaels, MD 21663

    Your picture-perfect St. Michaels Bungalow on the coveted W. Chestnut Street. The owners completed a full renovation in 2023. Designer finishes throughout. Attention to detail, light placement and thoughtful preservation of its original style. The screened front porch welcomes you in with it's beautiful woodwork and sets the pace for this Chic, move-in ready Shore Home. Situated on a double lot

    Dawn Lednum Chesapeake Bay Real Estate Plus, LLC

    107 W Chestnut St, Saint Michaels, MD 21663
  • 23762 Mount Pleasant Landing Cir, Saint Michaels, MD 21663
    23762 Mount Pleasant Landing Cir, Saint Michaels, MD 21663
    23762 Mount Pleasant Landing Cir, Saint Michaels, MD 21663
    /137

    $3,105,000 Sold Aug 28, 2025

    23762 Mount Pleasant Landing Cir, Saint Michaels, MD 21663

    • 4 Beds
    • 4.5 Baths
    • 2,649 Sq Ft
    • Built 1965

    Last Sold Summary

    • $1,172/SF
    • 5 Days On Market

    Current Estimated Value $2,921,517

    Last Listing Agent Kimberly Kepnes Monument Sotheby's International Realty

    23762 Mount Pleasant Landing Cir, Saint Michaels, MD 21663
    • 24345 Widgeon Place Unit 27, Saint Michaels, MD 21663
      24345 Widgeon Place Unit 27, Saint Michaels, MD 21663
      24345 Widgeon Place Unit 27, Saint Michaels, MD 21663
      /53

      Est $396,085 Not Listed For Sale

      24345 Widgeon Place Unit 27, Saint Michaels, MD 21663

      • 2 Beds
      • 2.5 Baths
      • 1,800 Sq Ft
      • Built 1986
      24345 Widgeon Place Unit 27, Saint Michaels, MD 21663

      Last Sold Summary

      • 5% Above List Price
      • $211/SF
      • 18 Days On Market
      • Last Sold Price $379,000
      • Jul 09, 2024

      Last Listing Agent Amy Berry Meredith Fine Properties

  • 101 Mulberry St, Saint Michaels, MD 21663
    101 Mulberry St, Saint Michaels, MD 21663
    101 Mulberry St, Saint Michaels, MD 21663
    /38

    $1,194,000 Open Sun 12:30PM - 2:30PM

    • 4 Beds
    • 2.5 Baths
    • 1,500 Sq Ft

    101 Mulberry St, Saint Michaels, MD 21663

    Beautifully restored Historic Victorian in the heart of Saint Michaels. This charming home has a strong rental history, last tenant was paying $4,500 a month. From the wide, welcoming front porch to the gated, manicured yard—complete with a hammock ideal for long afternoon naps—every space is designed for comfort and relaxation. A brick walkway leads to the custom beveled‐glass entry door and

    Jana Meredith Meredith Fine Properties

    101 Mulberry St, Saint Michaels, MD 21663
  • 901 S Talbot St, Saint Michaels, MD 21663
    901 S Talbot St, Saint Michaels, MD 21663
    /2

    $600,000 Sold Aug 08, 2025

    901 S Talbot St, Saint Michaels, MD 21663

    • 3 Beds
    • 2 Baths
    • 1,660 Sq Ft
    • Built 1930

    Last Sold Summary

    • $361/SF
    • 82 Days On Market

    Current Estimated Value $587,350

    Last Listing Agent Barbara Watkins Benson & Mangold, LLC

    901 S Talbot St, Saint Michaels, MD 21663
    • 24580 Deepwater Point Dr Unit 7, Saint Michaels, MD 21663
      24580 Deepwater Point Dr Unit 7, Saint Michaels, MD 21663
      24580 Deepwater Point Dr Unit 7, Saint Michaels, MD 21663
      /18

      Est $355,929 Not Listed For Sale

      24580 Deepwater Point Dr Unit 7, Saint Michaels, MD 21663

      • 2 Beds
      • 2 Baths
      • 1,296 Sq Ft
      • Built 1978
      24580 Deepwater Point Dr Unit 7, Saint Michaels, MD 21663

      Last Sold Summary

      • 3% Below List Price
      • $284/SF
      • 118 Days On Market
      • Last Sold Price $367,500
      • Aug 21, 2024

      Last Listing Agent Bill Wieland Benson & Mangold, LLC

  • 7865 Pea Neck Rd, Saint Michaels, MD 21663
    7865 Pea Neck Rd, Saint Michaels, MD 21663
    7865 Pea Neck Rd, Saint Michaels, MD 21663
    /60

    $1,379,800 New Construction

    • 4 Beds
    • 3.5 Baths
    • 3,332 Sq Ft

    7865 Pea Neck Rd, Saint Michaels, MD 21663

    Under construction by Laine Street Homes, this exceptional property offers over 3,300 sq ft of finished living space plus an additional 480 sq ft of covered outdoor living. Set on approximately 2 acres with mature trees and located just minutes from the heart of historic St. Michaels, the home blends privacy, luxury, and convenience. Designed with a main-level primary suite, the floor plan

    Jana Meredith Meredith Fine Properties

    7865 Pea Neck Rd, 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 $1,815,186

    Last Listing Agent Brian Petzold Benson & Mangold, LLC

    23854 Mount Misery Rd, Saint Michaels, MD 21663
    • 9792 Martingham Cir Unit B5, Saint Michaels, MD 21663
      9792 Martingham Cir Unit B5, Saint Michaels, MD 21663
      9792 Martingham Cir Unit B5, Saint Michaels, MD 21663
      /57

      Est $868,036 Not Listed For Sale

      9792 Martingham Cir Unit B5, Saint Michaels, MD 21663

      • 3 Beds
      • 3 Baths
      • 2,135 Sq Ft
      • Built 1990
      9792 Martingham Cir Unit B5, Saint Michaels, MD 21663

      Last Sold Summary

      • 14% Above List Price
      • $356/SF
      • 37 Days On Market
      • Last Sold Price $760,000
      • Apr 02, 2024

      Last Listing Agent John Cary Rosendale Realty

  • 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, 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
  • 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 $227,228

    Last Listing Agent Harry Kaiser Coldwell Banker Realty

    209 Webb Ln, Saint Michaels, MD 21663
    • 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 $882,633 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

      • 18% Above List Price
      • $351/SF
      • 53 Days On Market
      • Last Sold Price $750,000
      • Oct 18, 2023

      Last Listing Agent Cornelia Heckenbach Long & Foster

  • 204 Lincoln Ave, Saint Michaels, MD 21663
    204 Lincoln Ave, Saint Michaels, MD 21663
    204 Lincoln Ave, Saint Michaels, MD 21663
    /27

    $598,000

    • 3 Beds
    • 2 Baths
    • 2,348 Sq Ft

    204 Lincoln Ave, Saint Michaels, MD 21663

    RIO VISTA COMMUNITY - NO TOWN TAX - WATER FRONT PARK AT THE MILES RIVER FOR RESIDENTS ONLY.GREAT NEIGHBORHOOD RIGHT OUTSIDE OF THE BUZZING HISTORIC ST MICHAELS , GROCERY STORE , HARDWARE STORE, RESTAURANTS, BEAUTY SALON, PILATES ,YMCA , GARDEN CENTER - ALL IS JUST AROUND THE CORNER PRACTICALLY.THE HOME IS CURRENTLY RENTED, 24 HOURS SHOWING APPOINTMENT IS NEEDED.HARDWOOD FLOORS, WOOD

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    204 Lincoln Ave, 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 $633,951

    Last Listing Agent Debra Crouch Benson & Mangold, LLC

    9560 Martingham Cir, Saint Michaels, MD 21663
    • 9792 Martingham Cir, Saint Michaels, MD 21663
      9792 Martingham Cir, Saint Michaels, MD 21663
      9792 Martingham Cir, Saint Michaels, MD 21663
      /31

      Est $971,126 Not Listed For Sale

      9792 Martingham Cir, Saint Michaels, MD 21663

      • 3 Beds
      • 3 Baths
      • 2,213 Sq Ft
      • Built 1990
      9792 Martingham Cir, Saint Michaels, MD 21663

      Last Sold Summary

      • 4% Above List Price
      • $420/SF
      • 5 Days On Market
      • Last Sold Price $930,000
      • Apr 25, 2024

      Last Listing Agent Cornelia Heckenbach Long & Foster

  • 24965 Back Creek Dr, Saint Michaels, MD 21663
    24965 Back Creek Dr, Saint Michaels, MD 21663
    24965 Back Creek Dr, Saint Michaels, MD 21663
    /64

    $739,000 Open Sat 11AM - 1PM

    • 4 Beds
    • 2.5 Baths
    • 2,798 Sq Ft

    24965 Back Creek Dr, Saint Michaels, MD 21663

    Tucked into the heart of Back Creek Landing, this home offers the kind of layout and setting that just works—comfortable, well thought out, and connected to both nature and town. The main living space is designed around how people actually live. The kitchen is open and inviting, with a bright eat-in area and an elevated counter with seating—perfect for morning coffee, casual meals, or simply

    Kathleen Coale Benson & Mangold, LLC

    24965 Back Creek Dr, Saint Michaels, MD 21663

Showing Results 41 - 80, Page 2 of 18

Maryland Talbot County Saint Michaels 21663

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