2,828

Saint Michaels, MD Homes

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    • /46

      Est $1,335,348 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 3,522 Sq Ft

      106 W Chestnut St, Saint Michaels, MD 21663

      106 W Chestnut St, Saint Michaels, MD 21663
  • /41

    $349,000

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

    24362 Widgeon Place Unit 4, Saint Michaels, MD 21663

    Welcome to Martingham, a premier golf course and waterfront community located just a mile from historic St. Michaels. This Widgeon Place condo offers two en-suite bedrooms and a half bath, with a thoughtful two-level layout designed for comfort and convenience. The main level features a kitchen with a charming breakfast nook, hardwood floors, a gas fireplace, and an open-concept living area. A

    Amy Berry Meredith Fine Properties

    24362 Widgeon Place Unit 4, 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 $2,705,999

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

    9191 Deepwater Point Rd, Saint Michaels, MD 21663
    • /53

      Est $1,085,054 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 1,890 Sq Ft

      122 W Chestnut St, Saint Michaels, MD 21663

      122 W Chestnut St, Saint Michaels, MD 21663
  • /46

    $1,099,000

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

    100 Grace St, St. Michaels, MD 21663

    Located in the heart of St. Michaels' historic district, this adorable cottage has a rare zoning that allows for short term vacation rental, and it has been a very successful one. The current owner has great reviews and reports revenues of $65,000 in 2025. There is excellent bedroom separation, with one bedroom on the first floor in the back, the other on the second floor in the front. The

    Debra Crouch Benson & Mangold, LLC

    100 Grace St, St. Michaels, MD 21663
  • /53

    $547,000 Sold May 09, 2025

    23203 Stewart Way, McDaniel, MD 21647

    • 3 Beds
    • 2.5 Baths
    • 2,652 Sq Ft
    • Built 2005

    Last Sold Summary

    • $206/SF
    • 12 Days On Market

    Current Estimated Value $563,605

    Last Listing Agent Becky Wibberley Coldwell Banker Realty

    23203 Stewart Way, McDaniel, MD 21647
    • /65

      Est $1,446,939 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,579 Sq Ft

      417 Water St, Saint Michaels, MD 21663

      417 Water St, Saint Michaels, MD 21663
  • /3

    $295,000

    • Land
    • 0.55 Acre
    • $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
  • /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

    Last Listing Agent Kim Lally EXP Realty, LLC

    113 Thompson St, Saint Michaels, MD 21663
    • /34

      Not Listed For Sale

      • 2 Beds
      • 2.5 Baths
      • 1,652 Sq Ft

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

      24700 Deepwater Point Dr Unit 8, Saint Michaels, MD 21663
  • /89

    $2,998,000

    • 4 Beds
    • 6 Baths
    • 5,400 Sq Ft

    9262 Macks Ln, McDaniel, MD 21647

    Just 5-miles outside historic St. Michaels, MD...Classic "Eastern Shore Waterfront Retreat," featuring a substantial 5,400+ sq. ft. home, thoughtfully designed to capture cooling SW summer breezes and spectacular sunset views across the sparkling waters of Harris Creek. Sited on 8.26 private acres w/over 300' of natural "living Shoreline," features of the brick home include high ceilings

    Tom Crouch Benson & Mangold, LLC

    9262 Macks Ln, McDaniel, MD 21647
  • /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 $861,840

    Last Listing Agent Christopher Coppola Compass

    109 Chesapeake Ave, Saint Michaels, MD 21663
    • /60

      Est $1,605,499 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 3,644 Sq Ft

      10536 Miracle House Cir, Claiborne, MD 21624

      10536 Miracle House Cir, Claiborne, MD 21624
  • /9

    $1,795,000 Open Sat 1PM - 3PM

    • 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, seasonal farmer's market, museums and more. This home has received a fresh interior painting and

    Christopher Clinton Coldwell Banker Chesapeake Real Estate Company

    216 E Chew Ave, Saint Michaels, MD 21663
  • /44

    $1,833,000 Sold Mar 14, 2025

    7930 Church Neck Rd, Saint Michaels, MD 21663

    • 3 Beds
    • 3.5 Baths
    • 2,670 Sq Ft
    • Built 1982

    Last Sold Summary

    • $687/SF
    • 1 Day On Market

    Current Estimated Value $1,914,969

    Last Listing Agent Monica Penwell TTR Sotheby's International Realty

    7930 Church Neck Rd, Saint Michaels, MD 21663
    • /27

      Est $907,929 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,213 Sq Ft

      9792 Martingham Cir Unit B1, Saint Michaels, MD 21663

      9792 Martingham Cir Unit B1, Saint Michaels, MD 21663
  • /81

    $3,100,000

    • 4 Beds
    • 3.5 Baths
    • 4,035 Sq Ft

    23961 Lynnewood Dr, Saint Michaels, MD 21663

    Located within 2 miles of historic St. Michaels this exceptional waterfront estate blends timeless elegance with a resort-style setting. This 4,200± sq. ft. custom, single-level all brick residence showcases soaring ceilings, an abundance of natural light, and panoramic views of Broad Creek from almost every room. A huge great room featuring a large brick fireplace and open living / dining

    Barbara Watkins Benson & Mangold, LLC

    23961 Lynnewood Dr, Saint Michaels, MD 21663
  • /40

    $739,000 Sold May 02, 2025

    919 Riverview Terrace, Saint Michaels, MD 21663

    • 3 Beds
    • 2.5 Baths
    • 2,948 Sq Ft
    • Built 2005

    Last Sold Summary

    • $251/SF
    • 8 Days On Market

    Current Estimated Value $763,286

    Last Listing Agent Tom Crouch Benson & Mangold, LLC

    919 Riverview Terrace, Saint Michaels, MD 21663
    • /53

      Est $370,493 Not Listed For Sale

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

      24345 Widgeon Place Unit 27, Saint Michaels, MD 21663

      24345 Widgeon Place Unit 27, Saint Michaels, MD 21663
  • /2

    $99,500 Coming Soon

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

    102 Gloria Ave, Saint Michaels, MD 21663

    Great opportunity to own an in-town lot in the historic waterfront town of St. Michaels. This lot is just minutes from the shops, restaurants, harbor and Chesapeake Bay Maritime Museum. Come design and build your home without historic restrictions. The street sign for this lot is Glory, but the tax record has Gloria Avenue.

    Monica Penwell TTR Sotheby's International Realty

    102 Gloria 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 $529,609

    Last Listing Agent Monica Penwell TTR Sotheby's International Realty

    400 Railroad Ave, Saint Michaels, MD 21663
    • /18

      Est $380,810 Not Listed For Sale

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

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

      24580 Deepwater Point Dr Unit 7, Saint Michaels, MD 21663
  • /68

    $1,900,000

    • 4 Beds
    • 3.5 Baths
    • 2,839 Sq Ft

    24390 Oakwood Park Rd, Saint Michaels, MD 21663

    Welcome to your private waterfront retreat just minutes from the charming, historic town of St. Michaels, Maryland. Tucked away on a quiet cul-de-sac in the serene Oakwood Park community along San Domingo Creek, this one-story residence offers four bedrooms, three and a half baths, and a harmonious blend of space and comfort. With approximately 2,839 finished square feet, all on the main level,

    Janet Larson Benson & Mangold, LLC

    24390 Oakwood Park Rd, 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 $2,995,731

    Last Listing Agent Kimberly Kepnes Monument Sotheby's International Realty

    23762 Mount Pleasant Landing Cir, Saint Michaels, MD 21663
    • /57

      Est $835,660 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,135 Sq Ft

      9792 Martingham Cir Unit B5, Saint Michaels, MD 21663

      9792 Martingham Cir Unit B5, Saint Michaels, MD 21663
  • /32

    $385,000

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

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

    Desirable Martingham Community is the location of this fabulous Quail Hollow unit nestled within the famous "links at Perry Cabin " , one of the few units with a screened porch . Enjoy the beautiful golf course views from the second floor, the first floor is private with its landscaping. Bathroom and kitchen countertops are granite, the kitchen has a space for a breakfast table, Living and

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    9545 Quail Hollow Dr Unit 205, Saint Michaels, MD 21663
  • /75

    $1,100,000 Sold Apr 24, 2025

    113 W Chestnut St, Saint Michaels, MD 21663

    • 3 Beds
    • 2.5 Baths
    • 2,548 Sq Ft
    • Built 1817

    Last Sold Summary

    • $432/SF
    • 4 Days On Market

    Current Estimated Value $1,077,891

    Last Listing Agent Carolina Barksdale Benson & Mangold, LLC

    113 W Chestnut St, Saint Michaels, MD 21663
    • /48

      Est $836,098 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,135 Sq Ft

      9794 Martingham Cir Unit D5, Saint Michaels, MD 21663

      9794 Martingham Cir Unit D5, Saint Michaels, MD 21663
  • /43

    $630,000

    • 3 Beds
    • 2.5 Baths
    • 2,496 Sq Ft

    24749 Swan Rd, Saint Michaels, MD 21663

    Special Year-End Incentive! Seller is offering a Buyer Credit at settlement toward closing costs or repairs with a ratified contract by 12/31/25.This is a rare chance to secure meaningful savings and a beautiful home in one of the Eastern Shore’s most desirable communities.Welcome to Martingham—home to the newly redesigned Pete Dye course, The Links at Perry Cabin, and just minutes from

    Steve Bealefeld Benson & Mangold, LLC

    24749 Swan Rd, 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 $590,455

    Last Listing Agent Barbara Watkins Benson & Mangold, LLC

    901 S Talbot St, Saint Michaels, MD 21663
    • /56

      Est $457,621 Not Listed For Sale

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

      24360 Widgeon Place Unit 7, Saint Michaels, MD 21663

      24360 Widgeon Place Unit 7, Saint Michaels, MD 21663
  • /65

    $1,195,000

    • 2 Beds
    • 2 Baths
    • 2,024 Sq Ft

    107 E Chestnut St, Saint Michaels, MD 21663

    St. Michaels charm in this Circa 1870 Certified Plaque home, although historical data reflects original construction between 1805-1820.Updates include plumbing ,wiring, New upstairs HVAC, encapsulated crawl space, kitchen ,upgraded light fixtures, motorized window shades and many architectural details, freshly painted in 2024 . Recently upgraded Primary bedroom window seats with cushions,

    Robert Fitton Meredith Fine Properties

    107 E Chestnut St, Saint Michaels, MD 21663
  • /29

    $360,000 Sold Dec 20, 2024

    9656 Macks Ln, McDaniel, MD 21647

    • 4 Beds
    • 2 Baths
    • 1,472 Sq Ft
    • Built 1980

    Last Sold Summary

    • $245/SF
    • 9 Days On Market

    Current Estimated Value $360,846

    Last Listing Agent Megan Carpenter Tesla Realty Group, LLC

    9656 Macks Ln, McDaniel, MD 21647
    • /31

      Est $905,681 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,213 Sq Ft

      9792 Martingham Cir, Saint Michaels, MD 21663

      9792 Martingham Cir, Saint Michaels, MD 21663
  • /43

    $2,295,000 Pending

    • 4 Beds
    • 3.5 Baths
    • 3,248 Sq Ft

    25500 Chance Farm Rd, Royal Oak, MD 21662

    Significant Price Reduction! Welcome to this exceptional waterfront retreat on 3.5 acres overlooking Solitude Creek in Royal Oak. From the moment you enter, expansive water views set the tone for gracious living. Renovated in 2023, this 3,248 sq. ft. residence offers 4 bedrooms and 3.5 baths, including a main-level waterside primary suite with spa-like bath. The gourmet kitchen with upgraded

    Laura Carney TTR Sotheby's International Realty

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

    Last Listing Agent Brian Petzold Benson & Mangold, LLC

    23854 Mount Misery Rd, Saint Michaels, MD 21663
    • /51

      Est $840,000 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,135 Sq Ft

      9792 Martingham Cir Unit 8, Saint Michaels, MD 21663

      9792 Martingham Cir Unit 8, Saint Michaels, MD 21663
  • /10

    $265,000 Under Contract

    • Land
    • 0.17 Acre
    • $1,558,824 per Acre

    0 Grace St Unit MDTA2012346, Saint Michaels, MD 21663

    This is one of the loveliest lots in St. Michaels on a gorgeous residential street surrounded by charming homes. It is conveniently located in the heart of town just one block from restaurants and shopping on S Talbot Street, along with a wonderful trail and waterfront park.

    Connor LeMire Benson & Mangold, LLC

    0 Grace St Unit MDTA2012346, Saint Michaels, MD 21663
  • /51

    $1,196,000 Sold Jan 21, 2025

    202 Mulberry St, Saint Michaels, MD 21663

    • 4 Beds
    • 3 Baths
    • 2,703 Sq Ft
    • Built 1890

    Last Sold Summary

    • $442/SF
    • 8 Days On Market

    Current Estimated Value $1,192,769

    Last Listing Agent Monica Penwell TTR Sotheby's International Realty

    202 Mulberry St, Saint Michaels, MD 21663
    • /35

      Est $443,419 Not Listed For Sale

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

      24362 Widgeon Place Unit 6, Saint Michaels, MD 21663

      24362 Widgeon Place Unit 6, Saint Michaels, MD 21663

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