2,828

Saint Michaels, MD Homes

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  • /38

    $2,250,000

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

    222 E Chestnut St, Saint Michaels, MD 21663

    A unique opportunity to own a completely renovated home in the heart of town featuring four deep-water, dedicated boat slips. Located at the end of one of the most coveted, tree-lined streets in St. Michaels, this home is surrounded by beautifully restored historic properties and offers incredible views of St. Michaels Harbor. The current owners have thoughtfully renovated this 3-bedroom,

    Agent Photo

    Brian Gearhart

    Benson & Mangold, LLC

    (844) 651-2546

    222 E Chestnut St, Saint Michaels, MD 21663
  • /7

    Call for Price

    Riverwoods at Saint Michaels

    1 - 2 Beds

    111 Mitchell St, Saint Michaels, MD 21663

    111 Mitchell St, Saint Michaels, MD 21663
  • /70

    $465,000 Sold Sep 18, 2025

    23336 Tunis Ln, Claiborne, MD 21624

    • 2 Beds
    • 1 Bath
    • 1,190 Sq Ft
    • Built 1900

    Last Sold Summary

    • $391/SF
    • 67 Days On Market

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

    23336 Tunis Ln, Claiborne, MD 21624
    • /42

      Est $681,100 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,080 Sq Ft

      312 N Talbot St, Saint Michaels, MD 21663

      312 N Talbot St, Saint Michaels, MD 21663
  • /2

    $229,000 Coming Soon

    • 2 Beds
    • 1 Bath
    • 932 Sq Ft

    209 Webb Ln, Saint Michaels, MD 21663

    Wonderful opportunity to live in St Michaels at a great price. New carpeting, and new paint. Move in ready. Well kept, light filled townhouse with 2 bedrooms, one bath and fenced back yard. Must be primary residence. 2 assigned parking spaces. Walkable to all the St Michaels amenities, restaurants and shops!

    Agent Photo

    Harry Kaiser

    Coldwell Banker Realty

    (844) 491-6381

    209 Webb Ln, Saint Michaels, MD 21663
  • /41

    $5,500 per month

    • 4 Beds
    • 4 Baths
    • 2,304 Sq Ft
    • House for Rent

    215 E Chew Ave, Saint Michaels, MD 21663

    Custom-built in 2019, this home masterfully blends the charm of a historic replica with today’s modern conveniences. Ideally located just a short walk from shops, restaurants, the historic St. Michaels Harbor, and the Chesapeake Bay Maritime Museum, it offers the perfect balance of comfort and lifestyle. Inside, the home features an inviting open-concept living, family, and dining area enhanced

    Jana Meredith Meredith Fine Properties

    215 E Chew Ave, Saint Michaels, MD 21663
  • /55

    $389,900 Sold May 28, 2025

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

    • 2 Beds
    • 2 Baths
    • 1,296 Sq Ft
    • Built 1978

    Last Sold Summary

    • $301/SF
    • 14 Days On Market

    Last Listing Agent Kim Crouch Ozman Benson & Mangold, LLC

    24580 Deepwater Point Dr Unit 4, Saint Michaels, MD 21663
    • /69

      Est $1,125,516 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,772 Sq Ft

      8130 Bozman Neavitt Rd, Bozman, MD 21612

      8130 Bozman Neavitt Rd, Bozman, MD 21612
  • /82

    $725,000

    • 4 Beds
    • 2.5 Baths
    • 1,957 Sq Ft

    408 Spinnaker Ln, Saint Michaels, MD 21663

    This immaculate 4 bedroom, 2.5 bath home was built in 2022 and has been thoughtfully enhanced with numerous upgrades. The owners added luxury vinyl plank flooring to the second level, Hunter Douglas plantation shutters with independent top and bottom operation, recessed lighting upstairs, and a high-end full-size Electrolux washer and dryer. Additional features include a smart home system with

    Christie Bishop Northrop Realty

    408 Spinnaker Ln, Saint Michaels, MD 21663
  • /3

    $2,000 per month

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft
    • House for Rent

    204 Madison Ave, Saint Michaels, MD 21663

    Welcome to this charming single-family home, located in the heart of Saint Michaels, St. Michaels, Maryland. This property exudes warmth and comfort with its three bedrooms and two bathrooms, featuring a floor area of 1,232 square feet, making it the perfect space for families or individuals who value comfort and convenience with the added bonus of being a pet-friendly abode.The key

    204 Madison Ave, Saint Michaels, MD 21663
  • /60

    $480,000 Sold Jun 19, 2025

    9529 Quail Hollow Dr Unit 503, Saint Michaels, MD 21663

    • 3 Beds
    • 3 Baths
    • 1,800 Sq Ft
    • Built 1996

    Last Sold Summary

    • $267/SF
    • 9 Days On Market

    Last Listing Agent Eugene Smith TTR Sotheby's International Realty

    9529 Quail Hollow Dr Unit 503, Saint Michaels, MD 21663
    • /32

      Est $1,185,008 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,823 Sq Ft

      214 E Chestnut St, Saint Michaels, MD 21663

      214 E Chestnut St, Saint Michaels, MD 21663
  • /109

    $7,900,000

    • 7 Beds
    • 7.5 Baths
    • 10,240 Sq Ft

    10770 Rich Neck Rd, Claiborne, MD 21624

    Incredible 300+ acre landmark estate located 5 miles beyond St. Michaels. Over FOUR MILES OF SHORELINE on Eastern Bay, the Miles River and Tilghman Creek. Deep protected anchorage. High land. Sandy beaches. Very livable 10,000+ sq ft home that underwent two-year renovation 2005/2006. 13 ft ceilings on first story and almost10 ft on second story. Formal and informal living areas. Chef's kitchen

    Robert G. Shannahan Shoreline Realty

    10770 Rich Neck Rd, Claiborne, MD 21624
  • /28

    $2,800 per month

    • 4 Beds
    • 2.5 Baths
    • 1,700 Sq Ft
    • House for Rent

    921 C S Talbot St Unit C, Saint Michaels, MD 21663

    Great location!! First floor primary bedroom! Plus 3 additional bedrooms and a full bath upstairs. Walk to town, trail, schools and pool! Breezy front porch and rear deck, large family room with fireplace for cozy nights. Lawn maintenance included !! pets on case by case. Credit report and references required.

    Drew Buniski Benson & Mangold, LLC

    921 C S Talbot St Unit C, Saint Michaels, MD 21663
  • /56

    $525,000 Sold Sep 26, 2025

    109 Bush Terrace, Saint Michaels, MD 21663

    • 3 Beds
    • 2.5 Baths
    • 1,848 Sq Ft
    • Built 1998

    Last Sold Summary

    • $284/SF
    • 4 Days On Market

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

    109 Bush Terrace, Saint Michaels, MD 21663
    • /44

      Est $543,067 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,036 Sq Ft

      24114 Mount Pleasant Rd, Saint Michaels, MD 21663

      24114 Mount Pleasant Rd, Saint Michaels, MD 21663
  • /33

    $825,000 Pending

    • 4 Beds
    • 2.5 Baths
    • 2,493 Sq Ft

    24420 Mallard Place, Saint Michaels, MD 21663

    This stately and well-constructed brick/wood cape cod majestically sits on a prime corner lot in the extremely desirable community of Martingham. The ideal floor-plan features a main floor primary bedroom and 3 second floor guest bedrooms. Beautiful hardwood flooring, custom built-ins, fireplace, 2 story foyer, screened porch , deck, covered front porch, circular driveway with extra parking pad,

    Robert Lacaze TTR Sotheby's International Realty

    24420 Mallard Place, Saint Michaels, MD 21663
  • /14

    $2,200 per month

    • 3 Beds
    • 2 Baths
    • 1,056 Sq Ft
    • House for Rent

    104 E Maple Ave, Saint Michaels, MD 21663

    In town Saint Michaels rancher for rent on large double lot! Property features 3 bedrooms, 2 bathrooms, updated kitchen, large backyard, driveway, and convenient location close to all that downtown Saint Michaels has to offer!

    Jason French Benson & Mangold, LLC

    104 E Maple Ave, Saint Michaels, MD 21663
  • /40

    $1,350,000 Sold Oct 27, 2025

    204 Mulberry St, Saint Michaels, MD 21663

    • 3 Beds
    • 2.5 Baths
    • 2,320 Sq Ft
    • Built 1860

    Last Sold Summary

    • $582/SF
    • 2 Days On Market

    Last Listing Agent Laura Carney TTR Sotheby's International Realty

    204 Mulberry St, Saint Michaels, MD 21663
    • /33

      Est $505,794 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 720 Sq Ft

      123 Grace St, St. Michaels, MD 21663

      123 Grace St, St. Michaels, MD 21663
  • /44

    $1,195,000

    • 3 Beds
    • 3 Baths
    • 2,085 Sq Ft

    24318 Oakwood Park Rd, Saint Michaels, MD 21663

    Welcome to Old House Cove Waterfront Retreat in St. Michaels, MDNestled on nearly half an acre with scenic frontage along Old House Cove, this quintessential Eastern Shore property offers a rare combination of waterfront serenity, literary history, and timeless design. The expansive parcel provides privacy in a highly desirable location, just minutes from the heart of St. Michael’s—one of

    Kathleen Eder Compass

    24318 Oakwood Park Rd, Saint Michaels, MD 21663
  • /53

    $3,950 per month

    • 4 Beds
    • 2.5 Baths
    • 1,500 Sq Ft
    • House for Rent

    101 Mulberry St, Saint Michaels, MD 21663

    Beautifully restored Historic Simple Victorian in the heart of Saint Michaels. From the large inviting front porch, to the gated manicured yard, hanging hammock for long afternoon naps, brick walkway into the custom bevel glass entry door into the family room. The home features rich pine floors through out the home, cherry kitchen with stainless steel appliances, granite countertops, and

    Jana Meredith Meredith Fine Properties

    101 Mulberry St, Saint Michaels, MD 21663
  • /47

    $765,000 Sold May 19, 2025

    24981 Back Creek Dr, Saint Michaels, MD 21663

    • 5 Beds
    • 3.5 Baths
    • 3,166 Sq Ft
    • Built 2006

    Last Sold Summary

    • $242/SF
    • 4 Days On Market

    Current Estimated Value $775,771

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

    24981 Back Creek Dr, Saint Michaels, MD 21663
    • /24

      Est $533,357 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,016 Sq Ft

      112 Conner St, St. Michaels, MD 21663

      112 Conner St, St. Michaels, MD 21663
  • /24

    $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 staement.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
  • /38

    $2,200 per month

    • 2 Beds
    • 2.5 Baths
    • 1,800 Sq Ft
    • Townhouse for Rent

    24345 Widgeon Place Unit 29, Saint Michaels, MD 21663

    Golf Course Town House in beautiful St. Michaels. Enjoy watching golfers just out your back slider. Renovated unit 2 bedroom, 2.5 bath unit, gas fireplace, balcony, and 1-car garage. Located in the beautiful Martingham Circle, with community pool, golf, tennis, restaurants, and a beautiful waterfront community.

    Jana Meredith Meredith Fine Properties

    24345 Widgeon Place Unit 29, Saint Michaels, MD 21663
  • /59

    $830,000 Sold Aug 01, 2025

    9240 Martingham Dr, Saint Michaels, MD 21663

    • 4 Beds
    • 2.5 Baths
    • 2,910 Sq Ft
    • Built 1998

    Last Sold Summary

    • $285/SF
    • 3 Days On Market

    Current Estimated Value $820,550

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

    9240 Martingham Dr, Saint Michaels, MD 21663
    • /50

      Est $705,778 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,015 Sq Ft

      111 Dodson Ave, Saint Michaels, MD 21663

      111 Dodson Ave, 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
  • /18

    $2,800 per month

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • House for Rent

    10493 Miracle House Cir, Claiborne, MD 21624

    RARE Chesapeake Bay beach side rental with 2 BDR, 2BTH guest house on 2+ Acres. You can enjoy the salt air and fabulous sunsets in any season! Furnished and ready for occupancy.

    Dawn Lednum Chesapeake Bay Real Estate Plus, LLC

    10493 Miracle House Cir, Claiborne, MD 21624
  • /39

    $545,000 Sold Jul 11, 2025

    103 W Marengo St, Saint Michaels, MD 21663

    • 2 Beds
    • 1.5 Baths
    • 1,209 Sq Ft
    • Built 1940

    Last Sold Summary

    • $451/SF
    • 51 Days On Market

    Current Estimated Value $534,421

    Last Listing Agent Cheri Bruce-Phipps TTR Sotheby's International Realty

    103 W Marengo St, Saint Michaels, MD 21663
    • /56

      Est $747,748 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,026 Sq Ft

      107 Chesapeake Ave, Saint Michaels, MD 21663

      107 Chesapeake Ave, Saint Michaels, MD 21663
  • /11

    $229,000

    • Land
    • 0.25 Acre
    • $916,000 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 schools, banks, grocery stores, boat ramps and St. Michaels' many fine shops, museums and restaurants. A public waterfront park

    Tom Crouch Benson & Mangold, LLC

    912 Calvert Ave, Saint Michaels, MD 21663
  • /72

    $2,325,000 Sold May 09, 2025

    103 N Harbor Rd, Saint Michaels, MD 21663

    • 4 Beds
    • 4.5 Baths
    • 3,732 Sq Ft
    • Built 1954

    Last Sold Summary

    • $623/SF
    • 6 Days On Market

    Current Estimated Value $2,289,533

    Last Listing Agent Barbara Watkins Benson & Mangold, LLC

    103 N Harbor Rd, Saint Michaels, MD 21663
    • /71

      Est $4,251,314 Not Listed For Sale

      • 4 Beds
      • 4.5 Baths
      • 4,459 Sq Ft

      8941 Bozman Neavitt Rd, Saint Michaels, MD 21663

      8941 Bozman Neavitt Rd, Saint Michaels, MD 21663
  • /41

    $1,995,000 Under Contract

    • 3 Beds
    • 2.5 Baths
    • 3,562 Sq Ft

    7369 Drum Point Rd, Saint Michaels, MD 21663

    This brick, French Provincial home is ideally situated minutes from downtown St. Michaels and rests on 4.8 acres along Barrett Cove off Edge Creek and the scenic Choptank River. This serene retreat boasts over 500 feet of riprapped shoreline, a kayak launch, and dock with 2.5'+ MLW and an electric boat lift.The bright and airy main house offers the ease of one-level living. The primary

    Clifford Meredith Meredith Fine Properties

    7369 Drum Point Rd, Saint Michaels, MD 21663
  • /43

    $1,800,000 Sold Oct 09, 2025

    7312 Solitude Rd, Saint Michaels, MD 21663

    • 4 Beds
    • 3 Baths
    • 3,308 Sq Ft
    • Built 1920

    Last Sold Summary

    • $544/SF
    • 1 Day On Market

    Last Listing Agent Larry Brennan TTR Sotheby's International Realty

    7312 Solitude Rd, Saint Michaels, MD 21663
    • /30

      Est $882,977 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
  • /63

    $795,000

    • 3 Beds
    • 2.5 Baths
    • 3,166 Sq Ft

    24912 Back Creek Dr, Saint Michaels, MD 21663

    Welcome to **Back Creek Landing** — one of Saint Michaels’ most desirable neighborhoods, known for its peaceful setting, friendly community, and easy access to town. Just a few minutes by bike or golf cart from downtown, this neighborhood offers the best of both worlds: close to everything, yet surrounded by nature. This beautifully maintained home invites you in with a wide front porch — perfect

    Kathleen Coale Benson & Mangold, LLC

    24912 Back Creek Dr, 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 $624,056

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

    9217 Martingham Dr, Saint Michaels, MD 21663

Showing Results 1 - 40, Page 1 of 18

Home Trends in Saint Michaels, MD

Housing Trends

Median Sale Price
$785,000
Median Single Family Sale Price
$820,000
Median Townhouse Sale Price
$392,450
Median 2 Bedroom Sale Price
$349,500
Average Price Per Sq Ft
$417
Number of Homes for Sale
20
Last 12 months Home Sales
73
Months of Supply
3.30
Median List Price
$797,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
17%
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