2,798

Homes in ZIP Code 21663

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  • /41

    $339,500 Pending

    • 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
  • /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 $621,400

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

    9217 Martingham Dr, Saint Michaels, MD 21663
    • /30

      Est $903,647 Not Listed For Sale

      • 2 Beds
      • 2.5 Baths
      • 1,218 Sq Ft

      120 W Chestnut St, Saint Michaels, MD 21663

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

    $1,099,000 Pending

    • 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
  • /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 $2,704,410

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

    9191 Deepwater Point Rd, Saint Michaels, MD 21663
    • /46

      Est $1,339,661 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
  • /27

    $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
    • /53

      Est $1,167,048 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
  • /81

    $3,100,000 Open House 2/07

    • 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
  • /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 $854,545

    Last Listing Agent Christopher Coppola Compass

    109 Chesapeake Ave, Saint Michaels, MD 21663
    • /65

      Est $1,559,821 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
  • /2

    $1,150,000

    • 2 Beds
    • 2.5 Baths
    • 1,557 Sq Ft

    320 Perry Cabin Dr, Saint Michaels, MD 21663

    Fabulous waterfront townhome in an exceptional St. Michaels setting, adjacent to the Inn at Perry Cabin with tranquil water views. Designed for comfort and easy living, this 2-bedroom, 2.5-bath residence offers a thoughtfully designed open layout with hardwood floors, fireplace, and sun-filled interiors throughout. Professional photos coming next week. The well-appointed kitchen features

    Kathy Christensen TTR Sotheby's International Realty

    320 Perry Cabin Dr, 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 $1,894,772

    Last Listing Agent Monica Penwell TTR Sotheby's International Realty

    7930 Church Neck Rd, Saint Michaels, MD 21663
    • /39

      Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 3,360 Sq Ft

      7709 Quaker Neck Rd, Bozman, MD 21663

      7709 Quaker Neck Rd, Bozman, MD 21663
  • /13

    $99,500 Pending

    • 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
  • /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 $768,652

    Last Listing Agent Tom Crouch Benson & Mangold, LLC

    919 Riverview Terrace, 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
  • /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
  • /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 $543,024

    Last Listing Agent Monica Penwell TTR Sotheby's International Realty

    400 Railroad Ave, Saint Michaels, MD 21663
    • /27

      Est $886,046 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
  • /43

    $630,000

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

    24749 Swan Rd, Saint Michaels, MD 21663

    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 the heart of historic St. Michaels. Enjoy world-class dining, boutique shopping, and waterfront charm, all right at your fingertips.Set on 1.13

    Steve Bealefeld Benson & Mangold, LLC

    24749 Swan 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 $2,993,749

    Last Listing Agent Kimberly Kepnes Monument Sotheby's International Realty

    23762 Mount Pleasant Landing Cir, Saint Michaels, MD 21663
    • /53

      Est $365,429 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
  • /105

    $1,350,000

    • 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
  • /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 $1,073,691

    Last Listing Agent Carolina Barksdale Benson & Mangold, LLC

    113 W Chestnut St, Saint Michaels, MD 21663
    • /18

      Est $369,945 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
  • /17

    $450,000 Coming Soon

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

    111 Gloria Ave, Saint Michaels, MD 21663

    Essentially a NEW HOME! Extensively, tastefully and professionally renovated 1965 rancher located on a quiet residential street, just 2 blocks from downtown St. Michaels. Nearly everything is brand new, including roof shingles, siding, windows, HVAC system and new deck. New off-street parking area, sized for 2 vehicles. Inside, everything looks (and is) new, too, including attractive luxury vinyl

    Tom Crouch Benson & Mangold, LLC

    111 Gloria Ave, 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 $605,113

    Last Listing Agent Barbara Watkins Benson & Mangold, LLC

    901 S Talbot St, Saint Michaels, MD 21663
    • /57

      Est $801,866 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
  • /25

    $779,000 New Construction

    • 3 Beds
    • 2 Baths
    • 1,710 Sq Ft

    108 Miles, Saint Michaels, MD 21663

    A rare opportunity to pair a half-acre+ wooded in-town parcel with a thoughtfully designed single-level home concept in the heart of St. Michaels. This Concept A plan illustrates a 3-bedroom, 2-bath residence totaling approximately 1,710 square feet, featuring one-level living and an attached one-car garage. Designed to maximize functionality and flow, the concept offers flexible living spaces

    Chuck Mangold Benson & Mangold, LLC

    108 Miles, 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

    Last Listing Agent Brian Petzold Benson & Mangold, LLC

    23854 Mount Misery Rd, Saint Michaels, MD 21663
    • /48

      Est $802,767 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
  • /16

    $889,800 New Construction

    • 4 Beds
    • 3.5 Baths
    • 3,100 Sq Ft

    704 Meadow St, Saint Michaels, MD 21663

    Fabulous St. Michaels location near Miles River, St. Michaels Marina, Inn & Spa, St, Michael’s Winery, area schools and so much more! Enjoy all the benefits of a coastal lifestyle in this charming & scenic historic town. Build your dream home on a attractive homesite minutes from everything and everywhere you want to be.The Pointe offers an impressive open kitchen with island, pantry and

    George Bailey Keller Williams Flagship

    704 Meadow St, 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 $641,182

    Last Listing Agent Debra Crouch Benson & Mangold, LLC

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

      Est $878,034 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
  • /57

    $470,000 Under Contract

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

    9529 Quail Hollow Dr Unit 504, Saint Michaels, MD 21663

    Kate Koeppen Chesapeake Bay Real Estate Plus, LLC

    9529 Quail Hollow Dr Unit 504, 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 $613,650

    Last Listing Agent Monica Penwell TTR Sotheby's International Realty

    231 Madison Ave, Saint Michaels, MD 21663
    • /51

      Est $809,430 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

    $149,999 Under Contract

    • Land
    • 0.14 Acre
    • $1,071,421 per Acre

    300 Perry St, Saint Michaels, MD 21663

    New price!...Great opportunity to own a buildable lot in one of Maryland's most charming waterfront towns. This spacious and level parcel offers the perfect canvas for your Eastern shore home. Nestled just blocks from the harbor, shops, restaurants, parks, marinas, and the Chesapeake Bay Maritime Museum. Walk to downtown restaurants and shops! The property combines small-town walkability with

    Tammy Durbin Long & Foster Real Estate, Inc.

    300 Perry St, Saint Michaels, MD 21663

Showing Results 41 - 80, Page 2 of 18

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