2,833

Saint Michaels, MD Homes

Section Image Section Image
  • 24822 Swan Rd, Saint Michaels, MD 21663
    24822 Swan Rd, Saint Michaels, MD 21663
    24822 Swan Rd, Saint Michaels, MD 21663
    /37

    $830,000 Under Contract

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

    24822 Swan Rd, Saint Michaels, MD 21663

    Located in the sought-after Martingham community and close proximity to downtown Saint Michaels, 24822 Swan Road offers the perfect balance of privacy, convenience, and Eastern Shore charm. Designed for comfortable single-level living, the home features 3 bedrooms and 3 full baths, including a spacious primary suite with a walk-in closet and an updated en-suite bath. The main living area is

    Agent Photo

    Brian Gearhart

    Benson & Mangold, LLC

    (833) 317-2015

    24822 Swan Rd, Saint Michaels, MD 21663
  • 111 Mitchell St, Saint Michaels, MD 21663
    111 Mitchell St, Saint Michaels, MD 21663
    111 Mitchell St, Saint Michaels, MD 21663
    /7

    Call for Price

    Riverwoods at Saint Michaels

    1 - 2 Beds

    111 Mitchell St, Saint Michaels, MD 21663

    111 Mitchell St, Saint Michaels, MD 21663
  • 24580 Deepwater Point Dr Unit 4, Saint Michaels, MD 21663
    24580 Deepwater Point Dr Unit 4, Saint Michaels, MD 21663
    24580 Deepwater Point Dr Unit 4, Saint Michaels, MD 21663
    /55

    $389,900 Sold May 28, 2025

    24580 Deepwater Point Dr Unit 4, Saint Michaels, MD 21663

    • 2 Beds
    • 2 Baths
    • 1,296 Sq Ft
    • Built 1978

    Last Sold Summary

    • $301/SF
    • 14 Days On Market

    Last Listing Agent Kim Crouch Ozman Benson & Mangold, LLC

    24580 Deepwater Point Dr Unit 4, Saint Michaels, MD 21663
    • 7930 Church Neck Rd, Saint Michaels, MD 21663
      7930 Church Neck Rd, Saint Michaels, MD 21663
      7930 Church Neck Rd, Saint Michaels, MD 21663
      /44

      Est $1,895,546 Not Listed For Sale

      7930 Church Neck Rd, Saint Michaels, MD 21663

      • 3 Beds
      • 3.5 Baths
      • 2,670 Sq Ft
      • Built 1982
      7930 Church Neck Rd, Saint Michaels, MD 21663

      Last Sold Summary

      • 3% Above List Price
      • $687/SF
      • 1 Day On Market

      Last Sold Price $1,833,000

      Last Listing Agent Monica Penwell TTR Sotheby's International Realty

  • 601 Cove Rd, Saint Michaels, MD 21663
    601 Cove Rd, Saint Michaels, MD 21663
    601 Cove Rd, Saint Michaels, MD 21663
    /39

    $3,250,000 Under Contract

    • 4 Beds
    • 4.5 Baths
    • 3,289 Sq Ft

    601 Cove Rd, Saint Michaels, MD 21663

    Experience tranquil waterfront living in this stunning 4BR/4.5 BA home sited on .68 acres overlooking the Miles River. This cottage-style home was completely renovated by Focus ConstructionFeaturing exquisite architectural and interior design details throughout and include custom built-ins, and a large dual-sided gas fireplace. The open floor plan offers breathtaking river views from nearly

    Agent Photo

    Brian Gearhart

    Benson & Mangold, LLC

    (855) 789-7380

    601 Cove Rd, Saint Michaels, MD 21663
  • 24362 Widgeon Place Unit 2, Saint Michaels, MD 21663
    24362 Widgeon Place Unit 2, Saint Michaels, MD 21663
    24362 Widgeon Place Unit 2, Saint Michaels, MD 21663
    /17

    $2,300 per month

    • 2 Beds
    • 2.5 Baths
    • 1,800 Sq Ft
    • Townhouse for Rent

    24362 Widgeon Place Unit 2, Saint Michaels, MD 21663

    Great Martingham 2 bedroom townhouse available immediately. Great outdoor spaces with generous open floor plan. Some furniture included if wanted. Two en-suite bedrooms. Pets case by case.

    Jim Corson Benson & Mangold, LLC

    24362 Widgeon Place Unit 2, Saint Michaels, MD 21663
  • 9529 Quail Hollow Dr Unit 503, Saint Michaels, MD 21663
    9529 Quail Hollow Dr Unit 503, Saint Michaels, MD 21663
    9529 Quail Hollow Dr Unit 503, Saint Michaels, MD 21663
    /60

    $480,000 Sold Jun 19, 2025

    9529 Quail Hollow Dr Unit 503, Saint Michaels, MD 21663

    • 3 Beds
    • 3 Baths
    • 1,800 Sq Ft
    • Built 1996

    Last Sold Summary

    • $267/SF
    • 9 Days On Market

    Last Listing Agent Eugene Smith TTR Sotheby's International Realty

    9529 Quail Hollow Dr Unit 503, Saint Michaels, MD 21663
    • 312 N Talbot St, Saint Michaels, MD 21663
      312 N Talbot St, Saint Michaels, MD 21663
      312 N Talbot St, Saint Michaels, MD 21663
      /42

      Not Listed For Sale

      312 N Talbot St, Saint Michaels, MD 21663

      • 4 Beds
      • 3 Baths
      • 2,080 Sq Ft
      • Built 2022
      312 N Talbot St, Saint Michaels, MD 21663

      Last Sold Summary

      • $326/SF
      • 527 Days On Market

      Last Sold Price $678,000

      Last Listing Agent Carolina Barksdale Benson & Mangold, LLC

  • 209 Webb Ln, Saint Michaels, MD 21663
    209 Webb Ln, Saint Michaels, MD 21663
    209 Webb Ln, Saint Michaels, MD 21663
    /33

    $229,000 Pending

    • 2 Beds
    • 1 Bath
    • 932 Sq Ft

    209 Webb Ln, Saint Michaels, MD 21663

    Wonderful opportunity to live in the quaint, picturesque and historic town of St Michaels at a great price. New carpeting, and new paint. Move in ready. Well kept, light filled townhouse with 2 bedrooms, one bath and fenced back yard. Must be primary residence. 2 assigned parking spaces. Walkable to all St Michaels has to offer.

    Agent Photo

    Harry Kaiser

    Coldwell Banker Realty

    (844) 491-6381

    209 Webb Ln, Saint Michaels, MD 21663
  • 108 Railroad Ave, Saint Michaels, MD 21663
    108 Railroad Ave, Saint Michaels, MD 21663
    108 Railroad Ave, Saint Michaels, MD 21663
    /23

    $2,500 per month

    • 2 Beds
    • 2.5 Baths
    • 1,344 Sq Ft
    • House for Rent

    108 Railroad Ave, Saint Michaels, MD 21663

    This home is just around the corner from all the best of St. Michaels. Situated on a corner lot offering a small fenced-in back yard, this historic home features all the amenities of modern living. With 2 bedrooms, 2 baths and a loft style space on the 2nd floor and an open living/dining room area on the first level, plus a eat-in kitchen an half bath, this home offers plenty of room for all. The

    Monica Penwell TTR Sotheby's International Realty

    108 Railroad Ave, Saint Michaels, MD 21663
  • 109 Bush Terrace, Saint Michaels, MD 21663
    109 Bush Terrace, Saint Michaels, MD 21663
    109 Bush Terrace, Saint Michaels, MD 21663
    /56

    $525,000 Sold Sep 26, 2025

    109 Bush Terrace, Saint Michaels, MD 21663

    • 3 Beds
    • 2.5 Baths
    • 1,848 Sq Ft
    • Built 1998

    Last Sold Summary

    • $284/SF
    • 4 Days On Market

    Current Estimated Value $520,786

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

    109 Bush Terrace, Saint Michaels, MD 21663
    • 8130 Bozman Neavitt Rd, Bozman, MD 21612
      8130 Bozman Neavitt Rd, Bozman, MD 21612
      8130 Bozman Neavitt Rd, Bozman, MD 21612
      /69

      Est $1,061,329 Not Listed For Sale

      8130 Bozman Neavitt Rd, Bozman, MD 21612

      • 2 Beds
      • 2 Baths
      • 1,772 Sq Ft
      • Built 1967
      8130 Bozman Neavitt Rd, Bozman, MD 21612

      Last Sold Summary

      • 5% Above List Price
      • $570/SF
      • 83 Days On Market

      Last Sold Price $1,010,000

      Last Listing Agent Debra Crouch Benson & Mangold, LLC

  • 9206 Martingham Dr, Saint Michaels, MD 21663
    9206 Martingham Dr, Saint Michaels, MD 21663
    9206 Martingham Dr, Saint Michaels, MD 21663
    /16

    $749,000 Coming Soon

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

    9206 Martingham Dr, Saint Michaels, MD 21663

    Beautiful four-bedroom contemporary home on a private one + acre lot overlooking the 12th fairway of the Links at Perry Cabin golf course. Light-filled interior features a vaulted living room with fireplace, spacious family room and dining room and a bright sunroom that opens to a relaxing private deck. The main-level primary suite includes two walk-in closets and a comfortable layout for

    Agent Photo

    Maureen McHugh

    Chesapeake Bay Real Estate Plus, LLC

    (855) 650-2313

    9206 Martingham Dr, Saint Michaels, MD 21663
  • 921 C S Talbot St Unit C, Saint Michaels, MD 21663
    921 C S Talbot St Unit C, Saint Michaels, MD 21663
    921 C S Talbot St Unit C, Saint Michaels, MD 21663
    /28

    $2,800 per month

    • 4 Beds
    • 2.5 Baths
    • 1,700 Sq Ft
    • House for Rent

    921 C S Talbot St Unit C, Saint Michaels, MD 21663

    Great location!! First floor primary bedroom! Plus 3 additional bedrooms and a full bath upstairs. Walk to town, trail, schools and pool! Breezy front porch and rear deck, large family room with fireplace for cozy nights. Lawn maintenance included !! pets on case by case. Credit report and references required.

    Drew Buniski Benson & Mangold, LLC

    921 C S Talbot St Unit C, Saint Michaels, MD 21663
  • 204 Mulberry St, Saint Michaels, MD 21663
    204 Mulberry St, Saint Michaels, MD 21663
    204 Mulberry St, Saint Michaels, MD 21663
    /40

    $1,350,000 Sold Oct 27, 2025

    204 Mulberry St, Saint Michaels, MD 21663

    • 3 Beds
    • 2.5 Baths
    • 2,320 Sq Ft
    • Built 1860

    Last Sold Summary

    • $582/SF
    • 2 Days On Market

    Current Estimated Value $1,320,379

    Last Listing Agent Laura Carney TTR Sotheby's International Realty

    204 Mulberry St, Saint Michaels, MD 21663
    • 202 Mulberry St, Saint Michaels, MD 21663
      202 Mulberry St, Saint Michaels, MD 21663
      202 Mulberry St, Saint Michaels, MD 21663
      /51

      Est $1,114,217 Not Listed For Sale

      202 Mulberry St, Saint Michaels, MD 21663

      • 4 Beds
      • 3 Baths
      • 2,703 Sq Ft
      • Built 1890
      202 Mulberry St, Saint Michaels, MD 21663

      Last Sold Summary

      • 7% Below List Price
      • $442/SF
      • 8 Days On Market

      Last Sold Price $1,196,000

      Last Listing Agent Monica Penwell TTR Sotheby's International Realty

  • 216 E Chew Ave, Saint Michaels, MD 21663
    216 E Chew Ave, Saint Michaels, MD 21663
    216 E Chew Ave, Saint Michaels, MD 21663
    /143

    $1,795,000

    • 4 Beds
    • 3.5 Baths
    • 3,575 Sq Ft

    216 E Chew Ave, Saint Michaels, MD 21663

    Don't miss this rare opportunity. This special home offers spectacular and picturesque views of the Saint Michaels Harbor in addition to its prime location on one of Saint Michaels most desirable streets. Conveniently located near all of the in-town amenities and walkable to great restaurants, shops, brewery, winery, gallery, seasonal farmer's market, museums and more. This home has received a

    Agent Photo

    Christopher Clinton

    Coldwell Banker Chesapeake Real Estate Company

    (855) 940-3395

    216 E Chew Ave, Saint Michaels, MD 21663
  • 24345 Widgeon Place Unit 29, Saint Michaels, MD 21663
    24345 Widgeon Place Unit 29, Saint Michaels, MD 21663
    24345 Widgeon Place Unit 29, Saint Michaels, MD 21663
    /38

    $2,200 per month

    • 2 Beds
    • 2.5 Baths
    • 1,800 Sq Ft
    • Townhouse for Rent

    24345 Widgeon Place Unit 29, Saint Michaels, MD 21663

    Golf Course Town House in beautiful St. Michaels. Enjoy watching golfers just out your back slider. Renovated unit 2 bedroom, 2.5 bath unit, gas fireplace, balcony, and 1-car garage. Located in the beautiful Martingham Circle, with community pool, golf, tennis, restaurants, and a beautiful waterfront community.

    Jana Meredith Meredith Fine Properties

    24345 Widgeon Place Unit 29, 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

    $765,000 Sold May 19, 2025

    24981 Back Creek Dr, Saint Michaels, MD 21663

    • 5 Beds
    • 3.5 Baths
    • 3,166 Sq Ft
    • Built 2006

    Last Sold Summary

    • $242/SF
    • 4 Days On Market

    Current Estimated Value $777,939

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

    24981 Back Creek Dr, Saint Michaels, MD 21663
    • 24114 Mount Pleasant Rd, Saint Michaels, MD 21663
      24114 Mount Pleasant Rd, Saint Michaels, MD 21663
      24114 Mount Pleasant Rd, Saint Michaels, MD 21663
      /44

      Est $547,646 Not Listed For Sale

      24114 Mount Pleasant Rd, Saint Michaels, MD 21663

      • 3 Beds
      • 2 Baths
      • 2,036 Sq Ft
      • Built 2005
      24114 Mount Pleasant Rd, Saint Michaels, MD 21663

      Last Sold Summary

      • 14% Above List Price
      • $236/SF
      • 7 Days On Market

      Last Sold Price $480,000

      Last Listing Agent Cheri Bruce-Phipps TTR Sotheby's International Realty

  • 24700 Deepwater Point Dr Unit 1, Saint Michaels, MD 21663
    24700 Deepwater Point Dr Unit 1, Saint Michaels, MD 21663
    24700 Deepwater Point Dr Unit 1, Saint Michaels, MD 21663
    /47

    $369,000

    • 2 Beds
    • 2.5 Baths
    • 1,486 Sq Ft

    24700 Deepwater Point Dr Unit 1, Saint Michaels, MD 21663

    Price improvement! Inviting townhouse in the St. Michaels Martingham community with views across the Links at Perry Cabin fairway, offering easy Eastern Shore living. From the upstairs living areas, enjoy lovely, elevated views, abundant natural light, and a sense of openness that enhances the home’s warm, inviting feel. The upper-level living area features shining hardwood floors, and the home

    Agent Photo

    Maureen McHugh

    Chesapeake Bay Real Estate Plus, LLC

    (888) 352-1904

    24700 Deepwater Point Dr Unit 1, Saint Michaels, MD 21663
  • 10493 Miracle House Cir, Claiborne, MD 21624
    10493 Miracle House Cir, Claiborne, MD 21624
    10493 Miracle House Cir, Claiborne, MD 21624
    /18

    $2,200 per month

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • House for Rent

    10493 Miracle House Cir, Claiborne, MD 21624

    RARE Chesapeake Bay beach side rental with 2 BDR, 2BTH guest house on 2+ Acres. You can enjoy the salt air and fabulous sunsets in any season! Furnished and ready for occupancy.

    Dawn Lednum Chesapeake Bay Real Estate Plus, LLC

    10493 Miracle House Cir, Claiborne, MD 21624
  • 9240 Martingham Dr, Saint Michaels, MD 21663
    9240 Martingham Dr, Saint Michaels, MD 21663
    9240 Martingham Dr, Saint Michaels, MD 21663
    /59

    $830,000 Sold Aug 01, 2025

    9240 Martingham Dr, Saint Michaels, MD 21663

    • 4 Beds
    • 2.5 Baths
    • 2,910 Sq Ft
    • Built 1998

    Last Sold Summary

    • $285/SF
    • 3 Days On Market

    Current Estimated Value $812,873

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

    9240 Martingham Dr, Saint Michaels, MD 21663
    • 123 Grace St, St. Michaels, MD 21663
      123 Grace St, St. Michaels, MD 21663
      123 Grace St, St. Michaels, MD 21663
      /33

      Est $522,962 Not Listed For Sale

      123 Grace St, St. Michaels, MD 21663

      • 3 Beds
      • 2 Baths
      • 720 Sq Ft
      • Built 1963
      123 Grace St, St. Michaels, MD 21663

      Last Sold Summary

      • 8% Above List Price
      • $674/SF
      • 3 Days On Market

      Last Sold Price $485,000

      Last Listing Agent Beth Wynne Remax 100

  • 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

    Agent Photo

    Maureen McHugh

    Chesapeake Bay Real Estate Plus, LLC

    (877) 709-5322

    228 Perry Cabin Dr Unit 228 / 226, Saint Michaels, MD 21663
  • 103 W Marengo St, Saint Michaels, MD 21663
    103 W Marengo St, Saint Michaels, MD 21663
    103 W Marengo St, Saint Michaels, MD 21663
    /39

    $545,000 Sold Jul 11, 2025

    103 W Marengo St, Saint Michaels, MD 21663

    • 2 Beds
    • 1.5 Baths
    • 1,209 Sq Ft
    • Built 1940

    Last Sold Summary

    • $451/SF
    • 51 Days On Market

    Current Estimated Value $524,685

    Last Listing Agent Cheri Bruce-Phipps TTR Sotheby's International Realty

    103 W Marengo St, Saint Michaels, MD 21663
    • 112 Conner St, St. Michaels, MD 21663
      112 Conner St, St. Michaels, MD 21663
      112 Conner St, St. Michaels, MD 21663
      /24

      Est $564,778 Not Listed For Sale

      112 Conner St, St. Michaels, MD 21663

      • 4 Beds
      • 2 Baths
      • 2,016 Sq Ft
      • Built 1997
      112 Conner St, St. Michaels, MD 21663

      Last Sold Summary

      • 8% Above List Price
      • $260/SF
      • 9 Days On Market

      Last Sold Price $525,000

      Last Listing Agent Kim Crouch Ozman Benson & Mangold, LLC

  • 204 E Marengo St, Saint Michaels, MD 21663
    204 E Marengo St, Saint Michaels, MD 21663
    204 E Marengo St, Saint Michaels, MD 21663
    /26

    $599,000 Coming Soon

    • 2 Beds
    • 1 Bath
    • 1,200 Sq Ft

    204 E Marengo St, Saint Michaels, MD 21663

    Coming Soon to Saint Michael's - the perfect weekend getaway does exist — and it’s affordable. Escape the city / suburbs and spend your weekends in the quintessential Eastern Shore town of St. Michaels, known for its picturesque streets, quaint shops, vibrant dining scene, wineries, and distilleries. This charming waterfront community has everything you need to relax, recharge, and truly enjoy

    Agent Photo

    Gretchen Wichlinski

    Compass

    (844) 461-3815

    204 E Marengo St, Saint Michaels, MD 21663
  • 103 N Harbor Rd, Saint Michaels, MD 21663
    103 N Harbor Rd, Saint Michaels, MD 21663
    103 N Harbor Rd, Saint Michaels, MD 21663
    /72

    $2,325,000 Sold May 09, 2025

    103 N Harbor Rd, Saint Michaels, MD 21663

    • 4 Beds
    • 4.5 Baths
    • 3,732 Sq Ft
    • Built 1954

    Last Sold Summary

    • $623/SF
    • 6 Days On Market

    Current Estimated Value $2,289,119

    Last Listing Agent Barbara Watkins Benson & Mangold, LLC

    103 N Harbor Rd, Saint Michaels, MD 21663
    • 107 Carpenter St, Saint Michaels, MD 21663
      107 Carpenter St, Saint Michaels, MD 21663
      107 Carpenter St, Saint Michaels, MD 21663
      /30

      Est $774,864 Not Listed For Sale

      107 Carpenter St, Saint Michaels, MD 21663

      • 2 Beds
      • 2 Baths
      • 1,228 Sq Ft
      • Built 1900
      107 Carpenter St, Saint Michaels, MD 21663

      Last Sold Summary

      • 6% Below List Price
      • $668/SF
      • 2 Days On Market

      Last Sold Price $820,000

      Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

  • 24345 Widgeon Place Unit 25, Saint Michaels, MD 21663
    24345 Widgeon Place Unit 25, Saint Michaels, MD 21663
    24345 Widgeon Place Unit 25, Saint Michaels, MD 21663
    /36

    $435,000 Under Contract

    • 3 Beds
    • 3 Baths
    • 1,752 Sq Ft

    24345 Widgeon Place Unit 25, Saint Michaels, MD 21663

    Welcome to 24345 Widgeon Place #25, a premier end-unit townhome in the waterfront community of Martingham, located just a mile from historic St. Michaels and adjacent to the Inn at Perry Cabin Links golf course. This light-filled home features three bedrooms and three full baths, including a rare first-floor bedroom with an ensuite. The open-concept main level offers hardwood floors, a

    Agent Photo

    Maureen McHugh

    Chesapeake Bay Real Estate Plus, LLC

    (888) 787-3513

    24345 Widgeon Place Unit 25, Saint Michaels, MD 21663
  • 24420 Mallard Place, Saint Michaels, MD 21663
    24420 Mallard Place, Saint Michaels, MD 21663
    24420 Mallard Place, Saint Michaels, MD 21663
    /33

    $787,500 Sold Jan 15, 2026

    24420 Mallard Place, Saint Michaels, MD 21663

    • 4 Beds
    • 2.5 Baths
    • 2,493 Sq Ft
    • Built 1988

    Last Sold Summary

    • $316/SF
    • 97 Days On Market

    Current Estimated Value $796,688

    Last Listing Agent Robert Lacaze TTR Sotheby's International Realty

    24420 Mallard Place, Saint Michaels, MD 21663
    • 111 Dodson Ave, Saint Michaels, MD 21663
      111 Dodson Ave, Saint Michaels, MD 21663
      111 Dodson Ave, Saint Michaels, MD 21663
      /50

      Est $711,656 Not Listed For Sale

      111 Dodson Ave, Saint Michaels, MD 21663

      • 4 Beds
      • 2.5 Baths
      • 2,015 Sq Ft
      • Built 2021
      111 Dodson Ave, Saint Michaels, MD 21663

      Last Sold Summary

      • 14% Above List Price
      • $310/SF
      • 106 Days On Market

      Last Sold Price $625,000

      Last Listing Agent Cheri Bruce-Phipps TTR Sotheby's International Realty

  • 408 Spinnaker Ln, Saint Michaels, MD 21663
    408 Spinnaker Ln, Saint Michaels, MD 21663
    408 Spinnaker Ln, Saint Michaels, MD 21663
    /82

    $699,000 Open Sat 1PM - 3PM

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

    408 Spinnaker Ln, Saint Michaels, MD 21663

    OPEN HOUSE Sat 3/21 2 - 4pm and Sun 3/22 10-12pm. This immaculate 4 bedroom, 2.5 bath home was built in 2022 and has been thoughtfully enhanced with numerous upgrades. The owners added luxury vinyl plank flooring to the second level, Hunter Douglas plantation shutters with independent top and bottom operation, recessed lighting upstairs, and a high-end full-size Electrolux washer and dryer.

    Christie Bishop Northrop Realty

    408 Spinnaker Ln, Saint Michaels, MD 21663
  • 7312 Solitude Rd, Saint Michaels, MD 21663
    7312 Solitude Rd, Saint Michaels, MD 21663
    7312 Solitude Rd, Saint Michaels, MD 21663
    /43

    $1,800,000 Sold Oct 09, 2025

    7312 Solitude Rd, Saint Michaels, MD 21663

    • 4 Beds
    • 3 Baths
    • 3,308 Sq Ft
    • Built 1920

    Last Sold Summary

    • $544/SF
    • 1 Day On Market

    Current Estimated Value $1,808,751

    Last Listing Agent Larry Brennan TTR Sotheby's International Realty

    7312 Solitude Rd, Saint Michaels, MD 21663
    • 107 Chesapeake Ave, Saint Michaels, MD 21663
      107 Chesapeake Ave, Saint Michaels, MD 21663
      107 Chesapeake Ave, Saint Michaels, MD 21663
      /56

      Est $729,483 Not Listed For Sale

      107 Chesapeake Ave, Saint Michaels, MD 21663

      • 3 Beds
      • 2.5 Baths
      • 2,026 Sq Ft
      • Built 2022
      107 Chesapeake Ave, Saint Michaels, MD 21663

      Last Sold Summary

      • 15% Above List Price
      • $313/SF
      • 103 Days On Market

      Last Sold Price $635,000

      Last Listing Agent Jennifer Pogoda Redfin Corp

  • 114 W Chestnut St, St. Michaels, MD 21663
    114 W Chestnut St, St. Michaels, MD 21663
    114 W Chestnut St, St. Michaels, MD 21663
    /52

    $1,350,000

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

    114 W Chestnut St, St. Michaels, MD 21663

    Ideally located in the heart of the St. Michaels Historic District, this beautifully maintained three-story home offers exceptional walkability just a half block from the waterfront, scenic walking trail, public park and kayak launch, as well as the shops, restaurants, and other amenities that make St. Michaels such a sought-after place to live. A welcoming front porch introduces an inviting

    Wink Cowee Benson & Mangold, LLC

    114 W Chestnut St, St. 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 $1,156,299

    Last Listing Agent Kathleen Eder Compass

    24318 Oakwood Park Rd, Saint Michaels, MD 21663
    • 8941 Bozman Neavitt Rd, Saint Michaels, MD 21663
      8941 Bozman Neavitt Rd, Saint Michaels, MD 21663
      8941 Bozman Neavitt Rd, Saint Michaels, MD 21663
      /71

      Est $3,877,899 Not Listed For Sale

      8941 Bozman Neavitt Rd, Saint Michaels, MD 21663

      • 4 Beds
      • 4.5 Baths
      • 4,459 Sq Ft
      • Built 2001
      8941 Bozman Neavitt Rd, Saint Michaels, MD 21663

      Last Sold Summary

      • 22% Below List Price
      • $1,121/SF
      • 0 Days On Market

      Last Sold Price $5,000,000

      Last Listing Agent Chuck Mangold Benson & Mangold, LLC

  • 106 E Chestnut St, Saint Michaels, MD 21663
    106 E Chestnut St, Saint Michaels, MD 21663
    106 E Chestnut St, Saint Michaels, MD 21663
    /86

    $1,325,000

    • 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

Showing Results 1 - 40, Page 1 of 18

Maryland Talbot County Saint Michaels

Real Estate & Homes

Home Trends in Saint Michaels, MD

On average, homes in Saint Michaels, MD sell after 72 days on the market compared to the national average of 55 days. The median sale price for homes in Saint Michaels, MD over the last 12 months is $795,000, up 11% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$795,000
Median Single Family Sale Price
$800,000
Median Townhouse Sale Price
$470,000
Median 2 Bedroom Sale Price
$339,000
Average Price Per Sq Ft
$422
Number of Homes for Sale
36
Last 12 months Home Sales
71
Months of Supply
6.10
Median List Price
$799,999
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
11%
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