2,677

Homes in ZIP Code 21663

Section Image
  • /27

    $598,000

    • 3 Beds
    • 2 Baths
    • 2,348 Sq Ft

    204 Lincoln Ave, Saint Michaels, MD 21663

    Rio Vista Community – No Town Taxes! Enjoy life in the desirable Rio Vista community, featuring exclusive resident access to a waterfront park on the Miles River. Located just outside historic St. Michaels, this home offers exceptional convenience with a grocery store, hardware store, restaurants, beauty salon, Pilates studio, YMCA, and garden center all just minutes away. This solid ranch-style

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    204 Lincoln Ave, 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
  • /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
    • /69

      Est $763,752

      Not Listed For Sale

      103 Mulberry St, Saint Michaels, MD 21663

      • 4 Beds
      • 1.5 Baths
      • 1,596 Sq Ft
      • Built 1860
      103 Mulberry St, Saint Michaels, MD 21663

      Last Sold Summary

      • 149 Days On Market

      Last Listing Agent Tom Crouch Benson & Mangold, LLC

  • /64

    $3,000,000

    • 4 Beds
    • 3 Baths
    • 2,815 Sq Ft

    23820 Mount Pleasant Landing Cir, Saint Michaels, MD 21663

    Extraordinary waterfront living on 3+ acres with more than 500 feet of stunning water views—offering the privacy of being miles from civilization, yet just 1 mile from famed, historic downtown St. Michaels. Extensively renovated and meticulously cared for, this exceptional one-level living residence provides relaxed comfort, thoughtful design and effortless living in a a resort-like setting. Its

    Carrie Mock Engel & Völkers Annapolis

    23820 Mount Pleasant Landing Cir, 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
  • /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
    • /53

      Est $1,097,777

      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

      • 28 Days On Market

      Last Listing Agent Wink Cowee Benson & Mangold, LLC

  • /34

    $490,000

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

    9521 Quail Hollow Dr Unit 605, Saint Michaels, MD 21663

    With extensive updating done less than three years ago, this home in the popular Martingham community shows beautifully! The spacious, open living room with hardwood floors and fireplace overlooks a pavered patio and lots of greenspace beyond. The kitchen is up to date and well designed, and a pocket door separates it from the first floor bedroom suite, which could also be a den or office.

    Debra Crouch Benson & Mangold, LLC

    9521 Quail Hollow Dr Unit 605, 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
    • /65

      Est $1,552,208

      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

      • 55 Days On Market

      Last Listing Agent Clifford Meredith Meredith Fine Properties

  • /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
  • /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
    • /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

  • /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
  • /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
    • /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

  • /40

    $949,000

    Open Sun 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
  • /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 $3,735,696

    Last Listing Agent Kathleen Eder Compass

    9791 Pintail Place, Saint Michaels, 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

      • 4 Days On Market

      Last Listing Agent Robert Lacaze TTR Sotheby's International Realty

  • /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
  • /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
    • /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

  • /34

    $1,289,000

    Coming Soon Sep 20
    • 4 Beds
    • 2.5 Baths
    • 2,588 Sq Ft

    8410 Bozman Neavitt Rd, Bozman, MD 21612

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    8410 Bozman Neavitt Rd, Bozman, MD 21612
  • /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
    • /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

  • /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
  • /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
    • /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

  • /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
  • /34

    $525,000

    Sold Apr 24, 2026

    25913 Royal Oak Rd, Royal Oak, MD 21662

    • 4 Beds
    • 2 Baths
    • 2,023 Sq Ft
    • Built 1900

    Last Sold Summary

    • 5% Above List Price
    • $260/SF
    • 4 Days On Market

    Current Estimated Value $523,402

    Last Listing Agent Pamela Ackermann-Doll RE/MAX Executive

    25913 Royal Oak Rd, Royal Oak, MD 21662
    • /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.

  • /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
  • /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
    • /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

  • /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
  • /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
    • /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.

  • /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
  • /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 $1,917,934

    Last Listing Agent Brian Petzold Benson & Mangold, LLC

    23854 Mount Misery Rd, Saint Michaels, MD 21663

Showing Results 41 - 80, Page 2 of 18

How to Buy a Home How to Finance a Home How to Sell a Home