2,706

Saint Michaels, MD Homes

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  • 214 Madison Ave, Saint Michaels, MD 21663
    214 Madison Ave, Saint Michaels, MD 21663
    214 Madison Ave, Saint Michaels, MD 21663
    /23

    $375,000

    $24K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,743 Sq Ft

    214 Madison Ave, Saint Michaels, MD 21663

    Opportunity awaits! This 4-bedroom, 2-bathroom, two-level home offers a functional layout and plenty of potential for its next owner. The main level features beautiful hardwood floors, a galley kitchen, a separate dining room, and comfortable living spaces. Outside, you'll find a spacious yard with a storage shed, providing plenty of room for outdoor activities, gardening, or future

    Shelley Baden Berkshire Hathaway HomeServices PenFed Realty

    214 Madison Ave, Saint Michaels, MD 21663
  • 24700 Deepwater Unit 10, Saint Michaels, MD 21663
    24700 Deepwater Unit 10, Saint Michaels, MD 21663
    24700 Deepwater Unit 10, Saint Michaels, MD 21663
    /24

    $2,400 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,492 Sq Ft
    • Townhouse for Rent

    24700 Deepwater Unit 10, Saint Michaels, MD 21663

    Beautiful modern 2 bedroom townhouse in Martingham completely renovated with bedrooms on the first floor with incredible tile bath. Open floor plan is bathed in natural light. Pets are case by case.

    Jim Corson Benson & Mangold, LLC

    24700 Deepwater Unit 10, Saint Michaels, MD 21663
  • 938 Marea Terrace, Saint Michaels, MD 21663
    938 Marea Terrace, Saint Michaels, MD 21663
    /2

    $2,000,000

    Sold Jun 18, 2026

    938 Marea Terrace, Saint Michaels, MD 21663

    • 4 Beds
    • 5.5 Baths
    • 3,000 Sq Ft
    • Built 2020

    Last Sold Summary

    • 16% Below List Price
    • $667/SF
    • 83 Days On Market

    Current Estimated Value $2,032,285

    Last Listing Agent Carolina Barksdale Benson & Mangold, LLC

    938 Marea Terrace, 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

      Not Listed For Sale

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

      • 2 Beds
      • 2 Baths
      • 1,296 Sq Ft
      • Built 1978
      24580 Deepwater Point Dr Unit 4, Saint Michaels, MD 21663

      Last Sold Summary

      • 14 Days On Market

      Last Listing Agent Kim Crouch Ozman 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
  • 205 Railroad Ave Unit B, Saint Michaels, MD 21663
    205 Railroad Ave Unit B, Saint Michaels, MD 21663
    205 Railroad Ave Unit B, Saint Michaels, MD 21663
    /10

    $1,799 Per Month

    • 2 Beds
    • 1 Bath
    • Condo for Rent

    205 Railroad Ave Unit B, Saint Michaels, MD 21663

    First floor apartment one block from main street in St. Michaels. 2 bedrooms/1 bath with nice large living room and kitchen. Wood floors throughout living area, high ceilings, bright and airy. New HVAC system, most windows have been replaced. Tenant has the exclusive use of the back yard. Great location one block from main street, close to library and nature trail entrance. One year lease, good

    Carolina Barksdale Benson & Mangold, LLC

    205 Railroad Ave Unit B, Saint Michaels, MD 21663
  • 23266 Mallard Point Rd, McDaniel, MD 21647
    23266 Mallard Point Rd, McDaniel, MD 21647
    23266 Mallard Point Rd, McDaniel, MD 21647
    /23

    $514,000

    Sold Jun 03, 2026

    23266 Mallard Point Rd, McDaniel, MD 21647

    • 3 Beds
    • 2 Baths
    • 1,744 Sq Ft
    • Built 1976

    Last Sold Summary

    • 3% Above List Price
    • $295/SF
    • 8 Days On Market

    Current Estimated Value $511,849

    Last Listing Agent Tom Crouch Benson & Mangold, LLC

    23266 Mallard Point Rd, McDaniel, MD 21647
    • 106C Conner St, Saint Michaels, MD 21663
      106C Conner St, Saint Michaels, MD 21663
      106C Conner St, Saint Michaels, MD 21663
      /31

      Not Listed For Sale

      106C Conner St, Saint Michaels, MD 21663

      • 3 Beds
      • 1 Bath
      • 1,080 Sq Ft
      • Built 1998
      106C Conner St, Saint Michaels, MD 21663

      Last Sold Summary

      • 157 Days On Market

      Last Listing Agent Carolina Barksdale Benson & Mangold, LLC

  • 111 Chesapeake Ave, Saint Michaels, MD 21663
    111 Chesapeake Ave, Saint Michaels, MD 21663
    111 Chesapeake Ave, Saint Michaels, MD 21663
    /40

    $949,000

    Open Fri 12PM - 2PM
    • 4 Beds
    • 2.5 Baths
    • 2,168 Sq Ft

    111 Chesapeake Ave, Saint Michaels, MD 21663

    Beautifully upgraded and thoughtfully designed, custom finishes, and every modern convenience. The gourmet kitchen features dual fuel gas cook top and electric oven in professional grade stove, quartz countertops, professional grade appliances, and premium appointments, flowing seamlessly into warm hardwood floors and a cozy gas fireplace beneath a striking coffered ceiling. Beautifully curated

    Jana Meredith Meredith Fine Properties

    111 Chesapeake Ave, 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 $1,159,062

    Last Listing Agent Brian Gearhart Benson & Mangold, LLC

    7361 Solitude Rd, 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

      • 54 Days On Market

      Last Listing Agent Janet Powers Berkshire Hathaway Homeservice Homesale Realty

  • 806 Calvert Ave, Saint Michaels, MD 21663
    806 Calvert Ave, Saint Michaels, MD 21663
    806 Calvert Ave, Saint Michaels, MD 21663
    /27

    $525,000

    • 2 Beds
    • 2 Baths
    • 851 Sq Ft

    806 Calvert Ave, Saint Michaels, MD 21663

    Located in Bentley Hay and within walking distance of Historic St. Michaels, this charming cottage would make an exceptional pied-à-terre. Enjoy two bedrooms and two bathrooms on separate levels, with tremendous privacy and rear alley access. Easy access to nearby parks is perfect for leisurely strolls. Convenient public services and amenities are just a stone's throw away, making daily errands a

    Schuyler Benson Benson & Mangold, LLC

    806 Calvert 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 $594,566

    Last Listing Agent Kim Lally EXP Realty, LLC

    113 Thompson St, 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 Listing Agent Coard Benson Benson & Mangold, LLC

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

    $425,000

    Sold Jun 15, 2026

    1206 Washington Dr, Saint Michaels, MD 21663

    • 4 Beds
    • 4 Baths
    • 2,420 Sq Ft
    • Built 1986

    Last Sold Summary

    • 15% Below List Price
    • $176/SF
    • 20 Days On Market

    Last Listing Agent Chuck Mangold Benson & Mangold, LLC

    1206 Washington Dr, Saint Michaels, MD 21663
    • 10536 Miracle House Cir, Claiborne, MD 21624
      10536 Miracle House Cir, Claiborne, MD 21624
      10536 Miracle House Cir, Claiborne, MD 21624
      /60

      Est $1,664,343

      Not Listed For Sale

      10536 Miracle House Cir, Claiborne, MD 21624

      • 3 Beds
      • 3.5 Baths
      • 3,644 Sq Ft
      • Built 1900
      10536 Miracle House Cir, Claiborne, MD 21624

      Last Sold Summary

      • 31 Days On Market

      Last Listing Agent Barbara Watkins Benson & Mangold, LLC

  • 210 Brooks Ln, Saint Michaels, MD 21663
    210 Brooks Ln, Saint Michaels, MD 21663
    210 Brooks Ln, Saint Michaels, MD 21663
    /7

    $279,000

    • 3 Beds
    • 2 Baths
    • 1,340 Sq Ft

    210 Brooks Ln, Saint Michaels, MD 21663

    Discover a prime investment opportunity in the desirable St. Michaels community. This 3-bedroom, 2-bathroom ranch-style home, built in 1960, boasts a spacious 1,340 sq. ft. of potential. With its classic vinyl siding, this property is ready for some TLA and future enhancements. The roof is less than 5 years old and layout offers flexibility, making it easy to adapt the space. The 0.17-acre lot

    Marla Baines Meredith Fine Properties

    210 Brooks Ln, Saint Michaels, MD 21663
  • 203 E Chew Ave, Saint Michaels, MD 21663
    203 E Chew Ave, Saint Michaels, MD 21663
    203 E Chew Ave, Saint Michaels, MD 21663
    /93

    $2,125,000

    Sold Aug 05, 2026

    203 E Chew Ave, Saint Michaels, MD 21663

    • 5 Beds
    • 5.5 Baths
    • 4,673 Sq Ft
    • Built 2008

    Last Sold Summary

    • 16% Below List Price
    • $455/SF
    • 79 Days On Market

    Current Estimated Value $1,993,181

    Last Listing Agent Richard Minchik Benson & Mangold, LLC

    203 E Chew Ave, 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 $338,277

      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

      • 18 Days On Market

      Last Listing Agent Amy Berry Meredith Fine Properties

  • 925 Riverview Terrace, Saint Michaels, MD 21663
    925 Riverview Terrace, Saint Michaels, MD 21663
    925 Riverview Terrace, Saint Michaels, MD 21663
    /61

    $1,190,000

    Under Contract
    • 3 Beds
    • 2.5 Baths
    • 2,300 Sq Ft

    925 Riverview Terrace, Saint Michaels, MD 21663

    Presenting 925 Riverview Terrace, a move in ready, charming home ideally located in the sought after Bentley Hay neighborhood just minutes from historic downtown St. Michaels. This beautifully renovated & meticulously maintained home offers Miles River views, a saltwater pool, 1st floor primary bedroom, attached 2 car garage, screened in porch, hardwood floors, gardens, home office, fiber optic

    Kate Koeppen Chesapeake Bay Real Estate Plus, LLC

    925 Riverview Terrace, Saint Michaels, MD 21663
  • 8240 Tricefield Rd, Saint Michaels, MD 21663
    8240 Tricefield Rd, Saint Michaels, MD 21663
    /2

    $2,100,000

    Sold Jul 27, 2026

    8240 Tricefield Rd, Saint Michaels, MD 21663

    • 5 Beds
    • 6 Baths
    • 5,611 Sq Ft
    • Built 1989

    Last Sold Summary

    • 14% Below List Price
    • $374/SF

    Current Estimated Value $2,433,584

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

    8240 Tricefield Rd, 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 $822,802

      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

      • 5 Days On Market

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

  • 912 Calvert Ave, Saint Michaels, MD 21663
    912 Calvert Ave, Saint Michaels, MD 21663
    912 Calvert Ave, Saint Michaels, MD 21663
    /11

    $199,000

    $30K PRICE DROP
    • Land
    • 10,890 Sq Ft
    • $796,000 per Acre

    912 Calvert Ave, Saint Michaels, MD 21663

    One of the few remaining building lots in the St. Michaels area. This is a prime building lot, 75' x 150', ready for someone to design and construct a new home. Public water/sewer and high-speed internet available for hookup. Calvert Avenue is a convenient address, near a public waterfront park on the Miles River, St. Michaels Harbor, boat ramps, schools, banks, grocery stores and St. Michaels'

    Tom Crouch Benson & Mangold, LLC

    912 Calvert Ave, Saint Michaels, MD 21663
  • 9791 Pintail Place, Saint Michaels, MD 21663
    9791 Pintail Place, Saint Michaels, MD 21663
    9791 Pintail Place, Saint Michaels, MD 21663
    /80

    $3,200,000

    Sold Jul 15, 2026

    9791 Pintail Place, Saint Michaels, MD 21663

    • 5 Beds
    • 6 Baths
    • 7,300 Sq Ft
    • Built 1978

    Last Sold Summary

    • 8% Below List Price
    • $438/SF
    • 55 Days On Market

    Current Estimated Value $3,533,050

    Last Listing Agent Kathleen Eder Compass

    9791 Pintail Place, 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 $343,620

      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

      • 118 Days On Market

      Last Listing Agent Bill Wieland Benson & Mangold, LLC

  • 8209 Tricefield Rd, Saint Michaels, MD 21663
    8209 Tricefield Rd, Saint Michaels, MD 21663
    8209 Tricefield Rd, Saint Michaels, MD 21663
    /63

    $2,250,000

    $250K PRICE DROP Pending
    • 5 Beds
    • 2 Baths
    • 4,706 Sq Ft

    8209 Tricefield Rd, Saint Michaels, MD 21663

    Experience the best of Eastern Shore Living at this stunning waterfront retreat. Set on 8+ private acres, this solid brick Dutch Colonial offers timeless architecture, exceptional privacy and spectacular waterfrontage on San Domingo Creek. A long tree lined drive welcomes you to over 4400 square feet of thoughtfully designed living space. Additional highlights include a 2 car garage, paved

    Dawn Lednum Chesapeake Bay Real Estate Plus, LLC

    8209 Tricefield Rd, Saint Michaels, MD 21663
  • 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

    $1,152,500

    Sold Jun 10, 2026

    114 E Chew Ave, Saint Michaels, MD 21663

    • 3 Beds
    • 2.5 Baths
    • 2,336 Sq Ft
    • Built 1890

    Last Sold Summary

    • 16% Below List Price
    • $493/SF
    • 76 Days On Market

    Current Estimated Value $1,155,956

    Last Listing Agent Wink Cowee Benson & Mangold, LLC

    114 E Chew Ave, Saint Michaels, MD 21663
    • 9545 Quail Hollow Dr Unit 206, Saint Michaels, MD 21663
      9545 Quail Hollow Dr Unit 206, Saint Michaels, MD 21663
      9545 Quail Hollow Dr Unit 206, Saint Michaels, MD 21663
      /41

      Est $416,413

      Not Listed For Sale

      9545 Quail Hollow Dr Unit 206, Saint Michaels, MD 21663

      • 3 Beds
      • 2 Baths
      • 1,752 Sq Ft
      • Built 1973
      9545 Quail Hollow Dr Unit 206, Saint Michaels, MD 21663

      Last Sold Summary

      • 33 Days On Market

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

  • 105 W Marengo St, Saint Michaels, MD 21663
    105 W Marengo St, Saint Michaels, MD 21663
    105 W Marengo St, Saint Michaels, MD 21663
    /4

    $299,900

    $49K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,656 Sq Ft

    105 W Marengo St, Saint Michaels, MD 21663

    INVESTOR SPECIAL – PRIME IN-TOWN ST. MICHAELS OPPORTUNITY! Bring your contractor, vision, and renovation plans to 105 W Marengo St. This circa-1890 home offers approximately 1,656 square feet and presents an excellent value-add opportunity for an investor, renovator, or buyer looking for a substantial project in highly desirable St. Michaels.The property is ready for renovation, providing

    Arlene Reading Witz Realty, LLC

    105 W Marengo St, Saint Michaels, MD 21663
  • 314 Cove View Dr, Saint Michaels, MD 21663
    314 Cove View Dr, Saint Michaels, MD 21663
    314 Cove View Dr, Saint Michaels, MD 21663
    /17

    $465,000

    Sold Jun 12, 2026

    314 Cove View Dr, Saint Michaels, MD 21663

    • 3 Beds
    • 2 Baths
    • 1,540 Sq Ft
    • Built 1985

    Last Sold Summary

    • 7% Below List Price
    • $302/SF
    • 3 Days On Market

    Current Estimated Value $478,827

    Last Listing Agent Tracy Higgs-Wagner Meredith Fine Properties

    314 Cove View Dr, Saint Michaels, MD 21663
    • 9531 Quail Hollow Dr Unit 403, Saint Michaels, MD 21663
      9531 Quail Hollow Dr Unit 403, Saint Michaels, MD 21663
      9531 Quail Hollow Dr Unit 403, Saint Michaels, MD 21663
      /65

      Est $362,436

      Not Listed For Sale

      9531 Quail Hollow Dr Unit 403, Saint Michaels, MD 21663

      • 2 Beds
      • 2.5 Baths
      • 1,800 Sq Ft
      • Built 1973
      9531 Quail Hollow Dr Unit 403, Saint Michaels, MD 21663

      Last Sold Summary

      • 221 Days On Market

      Last Listing Agent Kim Crouch Ozman Benson & Mangold, LLC

  • 9818 Tilghman Island Rd, McDaniel, MD 21647
    9818 Tilghman Island Rd, McDaniel, MD 21647
    9818 Tilghman Island Rd, McDaniel, MD 21647
    /38

    $399,900

    $50K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 1,876 Sq Ft

    9818 Tilghman Island Rd, McDaniel, MD 21647

    Wonderful price for a wonderful property! Don't miss out ! The Perfect Blend of Space & Proximity. Loved by one family, this 4 bedroom 2 1/2 bath home is ready for the next owner. Situated on a beautiful1-acre parcel, this property is framed by magnificent, beautifully spaced mature trees and a cool gazebo to enjoy the park-like setting. Located in desirable McDaniel, you enjoy the ultimate

    Valerie Brown Coldwell Banker Realty

    9818 Tilghman Island Rd, McDaniel, MD 21647
  • 107 E Chestnut St, Saint Michaels, MD 21663
    107 E Chestnut St, Saint Michaels, MD 21663
    107 E Chestnut St, Saint Michaels, MD 21663
    /77

    $1,135,000

    Sold Jul 27, 2026

    107 E Chestnut St, Saint Michaels, MD 21663

    • 2 Beds
    • 2 Baths
    • 2,024 Sq Ft
    • Built 1880

    Last Sold Summary

    • 3% Below List Price
    • $561/SF
    • 19 Days On Market

    Current Estimated Value $1,148,306

    Last Listing Agent Monica Penwell TTR Sotheby's International Realty

    107 E Chestnut St, Saint Michaels, MD 21663
    • 9794 Martingham Cir, Saint Michaels, MD 21663
      9794 Martingham Cir, Saint Michaels, MD 21663
      9794 Martingham Cir, Saint Michaels, MD 21663
      /34

      Est $904,202

      Not Listed For Sale

      9794 Martingham Cir, Saint Michaels, MD 21663

      • 3 Beds
      • 3 Baths
      • 2,135 Sq Ft
      • Built 1990
      9794 Martingham Cir, Saint Michaels, MD 21663

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Brian Gearhart Benson & Mangold, LLC

  • 24700 Deepwater Unit 20, Saint Michaels, MD 21663
    24700 Deepwater Unit 20, Saint Michaels, MD 21663
    24700 Deepwater Unit 20, Saint Michaels, MD 21663
    /55

    $385,000

    $14K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,477 Sq Ft

    24700 Deepwater Unit 20, Saint Michaels, MD 21663

    Whether you are looking for a full-time residence, weekend retreat, or investment property, this unit is truly move-in ready. Situated in Martingham community just minutes from St. Michaels, shops, restaurants and surrounded by the Links at Perry Cabin golf course, this beautifully updated 2-bedroom, 2.5 bath townhome has been thoughtfully renovated with an emphasis on quality craftsmanship,

    Monica Penwell TTR Sotheby's International Realty

    24700 Deepwater Unit 20, Saint Michaels, MD 21663
  • 222 E Chestnut St, Saint Michaels, MD 21663
    222 E Chestnut St, Saint Michaels, MD 21663
    /2

    $1,825,000

    Sold Aug 10, 2026

    222 E Chestnut St, Saint Michaels, MD 21663

    • 3 Beds
    • 2.5 Baths
    • 2,284 Sq Ft
    • Built 1996

    Last Sold Summary

    • 3% Below List Price
    • $799/SF
    • 110 Days On Market

    Current Estimated Value $1,858,095

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

    222 E Chestnut 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 $812,610

      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

      • 37 Days On Market

      Last Listing Agent John Cary Rosendale Realty

  • 1002 Wades Farm Ln, McDaniel, MD 21647
    1002 Wades Farm Ln, McDaniel, MD 21647
    1002 Wades Farm Ln, McDaniel, MD 21647
    /90

    $2,995,000

    • 6 Beds
    • 6.5 Baths
    • 4,656 Sq Ft

    1002 Wades Farm Ln, McDaniel, MD 21647

    With huge sunset views across Eastern Bay, this stylishly-updated property is the perfect retreat! The main house with three en-suite bedrooms overlooks a large waterside deck, saltwater pool and screened pool house. A wisteria-covered pergola leads the the 1920's two-bedroom guest house with wrap-around porch at the water's edge. The one-bedroom carriage house completes the compound. Great

    Debra Crouch Benson & Mangold, LLC

    1002 Wades Farm Ln, McDaniel, MD 21647
  • 344 Perry Cabin Dr, Saint Michaels, MD 21663
    344 Perry Cabin Dr, Saint Michaels, MD 21663
    344 Perry Cabin Dr, Saint Michaels, MD 21663
    /64

    $1,187,500

    Sold Aug 25, 2026

    344 Perry Cabin Dr, Saint Michaels, MD 21663

    • 3 Beds
    • 2.5 Baths
    • 1,836 Sq Ft
    • Built 1988

    Last Sold Summary

    • 9% Below List Price
    • $647/SF
    • 43 Days On Market

    Current Estimated Value $1,232,560

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

    344 Perry Cabin Dr, Saint Michaels, MD 21663

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