2,798

Homes in ZIP Code 21663

Section Image
    • 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 $868,521 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

      • 9% Above List Price
      • $657/SF
      • 37 Days On Market

      Last Sold Price $800,000

      Last Listing Agent Robert G. Shannahan Shoreline Realty

  • 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
  • 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 $2,671,316

    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 $1,275,264 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

      Last Listing Agent Eddie Mangold Benson & Mangold, LLC

  • 938 Marea Terrace, Saint Michaels, MD 21663
    938 Marea Terrace, Saint Michaels, MD 21663
    938 Marea Terrace, Saint Michaels, MD 21663
    /60

    $2,390,000 Open House 4/04

    • 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
  • 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 $1,175,760

    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 $1,154,244 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

      • 2% Below List Price
      • $622/SF
      • 28 Days On Market

      Last Sold Price $1,175,000

      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
    /44

    $1,365,000

    • 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 $587,459

    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 $1,451,841 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

      • 13% Below List Price
      • $649/SF
      • 55 Days On Market

      Last Sold Price $1,675,000

      Last Listing Agent Clifford Meredith Meredith Fine Properties

  • 222 E Chestnut St, Saint Michaels, MD 21663
    222 E Chestnut St, Saint Michaels, MD 21663
    222 E Chestnut St, Saint Michaels, MD 21663
    /59

    $1,885,000

    • 3 Beds
    • 2.5 Baths
    • 2,284 Sq Ft

    222 E Chestnut St, Saint Michaels, MD 21663

    Where the harbor meanders to a close and drifting ducks replace the bustle of boats, this 2,284 square foot colonial captivates as serene dockside stillness gives way to elevated coastal personality. Whether welcoming guests from its end-of-lane circular drive or stepping ashore from one of your four boat slips, your restful retreat pampers with beautifully renovated interiors by local shop, Come

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    222 E Chestnut St, 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 $842,279

    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

      Last Listing Agent Robert Lacaze TTR Sotheby's International Realty

  • 7149 Drum Point Rd, Saint Michaels, MD 21663
    7149 Drum Point Rd, Saint Michaels, MD 21663
    7149 Drum Point Rd, Saint Michaels, MD 21663
    /72

    $2,249,000 Open House 4/04

    • 3 Beds
    • 3 Baths
    • 3,017 Sq Ft

    7149 Drum Point Rd, Saint Michaels, MD 21663

    ST MICHAELS TUCKED AWAY ON DESIRABLE DRUM POINT NEIGHBORHOOD, MINUTES FROM THE BUZZLING TOWN OF ST MICHAELS AND ITS MANY RESTAURANTS, SHOPS , CAFES, THE MOTOR MUSEUM AND THE CHESAPEAKE BAY MARITIME MUSEUM. WHERE EVER YOU TURN YOU SEE WATER. FEEL THE BREEZES , LOUNGE BY THE POOL OR NAP IN YOUR HAMMOCK UNDER THE SHADY TREES BY THE SHORELINE. THIS THREE BEDROOM SOLID BRICK HOME WITH OPEN FLOORPLAN ,

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    7149 Drum Point Rd, Saint Michaels, MD 21663
  • 919 Riverview Terrace, Saint Michaels, MD 21663
    919 Riverview Terrace, Saint Michaels, MD 21663
    919 Riverview Terrace, 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 $773,812

    Last Listing Agent Tom Crouch Benson & Mangold, LLC

    919 Riverview Terrace, Saint Michaels, MD 21663
    • 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

      Last Listing Agent Janet Powers Berkshire Hathaway Homeservice Homesale Realty

  • 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

    $1,295,000

    • 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
  • 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 $518,930

    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

      Last Listing Agent Coard Benson Benson & Mangold, LLC

  • 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

    • 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
  • 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 $2,938,876

    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 $364,800 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

      • 4% Below List Price
      • $211/SF
      • 18 Days On Market

      Last Sold Price $379,000

      Last Listing Agent Amy Berry Meredith Fine Properties

  • 108 Miles, Saint Michaels, MD 21663
    108 Miles, Saint Michaels, MD 21663
    108 Miles, Saint Michaels, MD 21663
    /25

    $999,000 New Construction

    • 3 Beds
    • 2.5 Baths

    108 Miles, Saint Michaels, MD 21663

    A rare opportunity to combine a half-acre+ wooded in-town setting with a classic Cape Cod–style home concept in the heart of St. Michaels. Concept B illustrates a two-story design featuring 3 bedrooms, 2 full baths, and 1 half bath, along with an attached two-car garage. The proposed layout offers a timeless architectural style with flexible living spaces that can be customized to suit individual

    Chuck Mangold Benson & Mangold, LLC

    108 Miles, Saint Michaels, MD 21663
  • 113 W Chestnut St, Saint Michaels, MD 21663
    113 W Chestnut St, Saint Michaels, MD 21663
    113 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 $1,054,611

    Last Listing Agent Carolina Barksdale Benson & Mangold, LLC

    113 W Chestnut 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 $359,060 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

      • 2% Below List Price
      • $284/SF
      • 118 Days On Market

      Last Sold Price $367,500

      Last Listing Agent Bill Wieland Benson & Mangold, LLC

  • 1211 Washington Dr, Saint Michaels, MD 21663
    1211 Washington Dr, Saint Michaels, MD 21663
    1211 Washington Dr, Saint Michaels, MD 21663
    /14

    $525,000

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

    1211 Washington Dr, Saint Michaels, MD 21663

    DESIREABLE RIO VISTA LIVING -MOVE IN ONE SIDE OF THIS DUPLEX AND RENT THE OTHER ONE TO HELP PAYING FOR YOUR MORTGAGE. THESE DUPLEXES RARELY BECOME AVAILABLE.The duplex is located in a water access community with dock access through the owner's approved application and payment.The building consists of two units with mirrored floor plans. They offer a kitchen with small eating area, an open

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    1211 Washington Dr, 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 $591,784

    Last Listing Agent Barbara Watkins Benson & Mangold, LLC

    901 S Talbot St, 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 $838,100 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

      • 10% Above List Price
      • $356/SF
      • 37 Days On Market

      Last Sold Price $760,000

      Last Listing Agent John Cary Rosendale Realty

  • 1215 Washington Dr, Saint Michaels, MD 21663
    1215 Washington Dr, Saint Michaels, MD 21663
    1215 Washington Dr, Saint Michaels, MD 21663
    /30

    $525,000

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

    1215 Washington Dr, Saint Michaels, MD 21663

    DESIREABLE RIO VISTA LIVING -MOVE IN ONE SIDE OF THIS DUPLEX AND RENT THE OTHER ONE TO HELP PAYING FOR YOUR MORTGAGE. THESE DUPLEXES RARELY BECOME AVAILABLE. The duplex is located in a water access community with dock access through the owner's approved application and payment. The building consists of two units with mirrored floor plans. They offer a kitchen with small eating area, an open

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    1215 Washington Dr, 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 $1,812,361

    Last Listing Agent Brian Petzold Benson & Mangold, LLC

    23854 Mount Misery Rd, 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 $849,601 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

      • 13% Above List Price
      • $351/SF
      • 53 Days On Market

      Last Sold Price $750,000

      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

    • 3 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
  • 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 $640,737

    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 $915,513 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

      • 2% Below List Price
      • $420/SF
      • 5 Days On Market

      Last Sold Price $930,000

      Last Listing Agent Cornelia Heckenbach Long & Foster

  • Lot 16A Meadow St, Saint Michaels, MD 21163
    Lot 16A Meadow St, Saint Michaels, MD 21163
    Lot 16A Meadow St, Saint Michaels, MD 21163
    /25

    $799,000 New Construction

    • 4 Beds
    • 2.5 Baths

    Lot 16A Meadow St, Saint Michaels, MD 21163

    Welcome to the quaint town of St. Michaels. Waterfront dining, history and small town feel are combined to give you a perfect home for full time or vacation home.Lacrosse homes is proud to present The Pointe.Time to make your personal selections. Make this home your personal statement.Pick the exterior colors, interior feature such as flooring, cabinets, countertops and more.Make this

    George Bailey Keller Williams Flagship

    Lot 16A Meadow St, Saint Michaels, MD 21163
  • 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 $613,402

    Last Listing Agent Monica Penwell TTR Sotheby's International Realty

    231 Madison Ave, 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 $887,737 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

      • 8% Above List Price
      • $386/SF
      • 22 Days On Market

      Last Sold Price $825,000

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

  • 9791 Pintail Place, Saint Michaels, MD 21663
    9791 Pintail Place, Saint Michaels, MD 21663
    9791 Pintail Place, Saint Michaels, MD 21663
    /80

    $3,475,000 Under Contract

    • 5 Beds
    • 6 Baths
    • 7,300 Sq Ft

    9791 Pintail Place, Saint Michaels, MD 21663

    Welcome to Rivermark - a true waterfront retreat in St. Michaels on the Eastern Shore. This custom-built home is an artistic masterpiece with five octagonal interconnected wings, creating distinct yet flowing spaces and breathtaking panoramic views of Porters Creek, Miles River, Wye River and the Eastern Bay from every room.With architecture inspired by the French West Indies, this home

    Kathleen Eder Compass

    9791 Pintail Place, Saint Michaels, MD 21663
  • 24989 Back Creek Dr, Saint Michaels, MD 21663
    24989 Back Creek Dr, Saint Michaels, MD 21663
    24989 Back Creek Dr, Saint Michaels, MD 21663
    /40

    $795,000 Sold Jul 31, 2025

    24989 Back Creek Dr, Saint Michaels, MD 21663

    • 4 Beds
    • 2.5 Baths
    • 3,098 Sq Ft
    • Built 2006

    Last Sold Summary

    • $257/SF
    • 0 Days On Market

    Current Estimated Value $769,374

    Last Listing Agent Kathleen Coale Benson & Mangold, LLC

    24989 Back Creek Dr, 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 $432,307 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

      • 1% Below List Price
      • $248/SF
      • 178 Days On Market

      Last Sold Price $435,000

      Last Listing Agent Skipper Marquess Coldwell Banker (NRT-Southeast-MidAtlantic)

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