2,822

Saint Michaels, MD Homes

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  • 205 E Chew Ave, Saint Michaels, MD 21663
    205 E Chew Ave, Saint Michaels, MD 21663
    205 E Chew Ave, Saint Michaels, MD 21663
    /28

    $1,275,000 Pending

    • 2 Beds
    • 1.5 Baths
    • 1,780 Sq Ft

    205 E Chew Ave, Saint Michaels, MD 21663

    The Arthur K. Easter House, St. Michaels, MarylandFrom the moment you arrive, it is clear: this is no ordinary house. Located on one of St. Michaels’ most sought-after streets, the circa 1889 Arthur K. Easter House seems to have stepped from the pages of a storybook—one filled with golden light, quiet elegance, and a sense of belonging. This stylish historic home was relocated to its current

    Agent Photo

    Brian Gearhart

    Benson & Mangold, LLC

    (866) 771-9340

    205 E Chew Ave, Saint Michaels, MD 21663
  • 111 Mitchell St, Saint Michaels, MD 21663
    111 Mitchell St, Saint Michaels, MD 21663
    111 Mitchell 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
  • 9998 Wades Farm Ln, McDaniel, MD 21647
    9998 Wades Farm Ln, McDaniel, MD 21647
    9998 Wades Farm Ln, McDaniel, MD 21647
    /117

    $1,402,000 Sold Oct 15, 2025

    • 3,623 Sq Ft
    • $387/SF
    • 3 Days On Market
    • 6 Beds
    • 4 Baths
    • Built 1909

    9998 Wades Farm Ln, McDaniel, MD 21647

    Step Back in time and experience the charm of Eastern Shore living with this rare waterfront property overlooking the exciting waters of Eastern Bay. Set on 2.7 acres with secure and elevated shoreline, private dock, and powered boat lift, this estate offers the perfect balance of privacy, relaxation and endless potential.The property features two dwellings with a combined total of six

    Kelly Showell Benson & Mangold, LLC

    9998 Wades Farm Ln, McDaniel, MD 21647
    • 312 N Talbot St, Saint Michaels, MD 21663
      312 N Talbot St, Saint Michaels, MD 21663
      312 N Talbot St, Saint Michaels, MD 21663
      /42

      Est $779,100 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
  • 222 E Chestnut St, Saint Michaels, MD 21663
    222 E Chestnut St, Saint Michaels, MD 21663
    222 E Chestnut St, Saint Michaels, MD 21663
    /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
  • 101 Mulberry St, Saint Michaels, MD 21663
    101 Mulberry St, Saint Michaels, MD 21663
    101 Mulberry St, 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
  • 304 N Talbot St, Saint Michaels, MD 21663
    304 N Talbot St, Saint Michaels, MD 21663
    304 N Talbot St, Saint Michaels, MD 21663
    /42

    $785,000 Sold Oct 15, 2025

    • 2,028 Sq Ft
    • $387/SF
    • 3 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2021

    304 N Talbot St, Saint Michaels, MD 21663

    The best of St. Michaels living.Step into the heart of St. Michaels and experience the ease of in-town living. Across from the iconic Inn at Perry Cabin and just a short stroll to the Maritime Museum, boutique shops, and waterfront dining, this home offers a rare blend of modern comfort and small-town charm. Built in 2021, the two-story residence was thoughtfully designed for both relaxation

    Wink Cowee Benson & Mangold, LLC

    304 N Talbot St, Saint Michaels, MD 21663
    • 8130 Bozman Neavitt Rd, Bozman, MD 21612
      8130 Bozman Neavitt Rd, Bozman, MD 21612
      8130 Bozman Neavitt Rd, Bozman, MD 21612
      /69

      Est $1,088,546 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
  • 100 Mulberry St, St. Michaels, MD 21663
    100 Mulberry St, St. Michaels, MD 21663
    100 Mulberry St, St. Michaels, MD 21663
    /6

    $950,000

    • Studio
    • 4,172 Sq Ft

    100 Mulberry St, St. Michaels, MD 21663

    Exceptional location with ample off-street parking—this spacious and well-maintained triplex is an ideal investment in the highly desirable St. Michaels community. The first floor features a spacious 3-bedroom, 3.5-bath unit with a large kitchen, a formal dining room with a cozy wood-burning fireplace, a generous living room, and a private laundry room.Upstairs, the second floor features two

    Agent Photo

    Tracy Higgs-Wagner

    Meredith Fine Properties

    (877) 846-5106

    100 Mulberry St, St. Michaels, MD 21663
  • 24345 Widgeon Place Unit 29, Saint Michaels, MD 21663
    24345 Widgeon Place Unit 29, Saint Michaels, MD 21663
    24345 Widgeon Place Unit 29, Saint Michaels, MD 21663
    /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
  • 900 Riverview Terrace, Saint Michaels, MD 21663
    900 Riverview Terrace, Saint Michaels, MD 21663
    900 Riverview Terrace, Saint Michaels, MD 21663
    /38

    $2,700,000 Sold Oct 15, 2025

    • 3,393 Sq Ft
    • $796/SF
    • 70 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1987

    900 Riverview Terrace, Saint Michaels, MD 21663

    Welcome to this stunning brick one -story house on Riverview Terrace that you've always admired. From the moment that the front door opens, you will be captivated by the breathtaking views of the Miles River. This home offers an open floor-plan with a large great-room, dining room; kitchen, a primary bedroom suite , 2 guest rooms sharing a full bathroom,, an office and a powder room. Lovely

    Robert Lacaze TTR Sotheby's International Realty

    900 Riverview Terrace, Saint Michaels, MD 21663
    • 214 E Chestnut St, Saint Michaels, MD 21663
      214 E Chestnut St, Saint Michaels, MD 21663
      214 E Chestnut St, Saint Michaels, MD 21663
      /32

      Est $1,199,283 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
  • 9171 Deepwater Point Rd, Saint Michaels, MD 21663
    9171 Deepwater Point Rd, Saint Michaels, MD 21663
    9171 Deepwater Point Rd, Saint Michaels, MD 21663
    /41

    $1,695,000

    • 5 Beds
    • 3.5 Baths
    • 4,102 Sq Ft

    9171 Deepwater Point Rd, Saint Michaels, MD 21663

    Welcome to Saint Micheals Retreat, an extraordinary 6+/- acre property overlooking the Links at Perry Cabin Golf Course with direct water access to Long Haul Creek and Miles River. Just moments to downtown Saint Michaels, fine dining, shopping, and entertainment, this stunning makeover offers 4,100 +/- sq. ft. of single-story living designed for endless indoor/outdoor entertainment. This

    Craig Linthicum Benson & Mangold, LLC

    9171 Deepwater Point Rd, Saint Michaels, MD 21663
  • 10493 Miracle House Cir, Claiborne, MD 21624
    10493 Miracle House Cir, Claiborne, MD 21624
    10493 Miracle House Cir, Claiborne, MD 21624
    /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
  • 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

    • 2,350 Sq Ft
    • $268/SF
    • 61 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2000

    9560 Martingham Cir, Saint Michaels, MD 21663

    Located in the popular Martingham community just beyond historic St. Michaels, this well-built one-level home has a prime location, with The Links at Perry Cabin golf course right behind it. The open, spacious floor plan features a large primary suite at one end and two bedrooms and bath at the other for maximum privacy. The owners added a sunroom with a grilling deck off the side. The kitchen

    Debra Crouch Benson & Mangold, LLC

    9560 Martingham Cir, Saint Michaels, MD 21663
    • 24114 Mount Pleasant Rd, Saint Michaels, MD 21663
      24114 Mount Pleasant Rd, Saint Michaels, MD 21663
      24114 Mount Pleasant Rd, Saint Michaels, MD 21663
      /44

      Est $555,241 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
  • 408 Spinnaker Ln, Saint Michaels, MD 21663
    408 Spinnaker Ln, Saint Michaels, MD 21663
    408 Spinnaker Ln, Saint Michaels, MD 21663
    /82

    $775,000 Open Sat 1PM - 4PM

    • 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
  • 921 E S Talbot, Saint Michaels, MD 21663
    921 E S Talbot, Saint Michaels, MD 21663
    921 E S Talbot, Saint Michaels, MD 21663
    /18

    $2,800 per month

    • 4 Beds
    • 2.5 Baths
    • 2,100 Sq Ft
    • House for Rent

    921 E S Talbot, Saint Michaels, MD 21663

    Great location!! Walk to town, trail, schools and pool! Huge primary suite with vaulted ceilings and sitting room, breezy front porch and rear deck. 3 additional bedrooms, living room, separate dining room, family room with fireplace, 2 zone heat pumps, and one car attached garage. Lawn maintenance included !! pets on case by case. Credit report and references required.

    Drew Buniski Benson & Mangold, LLC

    921 E S Talbot, Saint Michaels, MD 21663
  • 7312 Solitude Rd, Saint Michaels, MD 21663
    7312 Solitude Rd, Saint Michaels, MD 21663
    7312 Solitude Rd, Saint Michaels, MD 21663
    /51

    $1,800,000 Sold Oct 09, 2025

    • 3,308 Sq Ft
    • $544/SF
    • 1 Day On Market
    • 4 Beds
    • 3 Baths
    • Built 1920

    7312 Solitude Rd, Saint Michaels, MD 21663

    Find your bliss on Solitude Creek! This exceptional four-bedroom, three-bath residence boasts 3,300 square feet of meticulously crafted interiors, featuring a gourmet kitchen appointed with a Wolf six-burner range and Sub-Zero refrigeration—perfect for culinary enthusiasts and entertaining on a grand scale.Enjoy a newly constructed dock with water, electric, and a floating kayak launch. With

    Larry Brennan TTR Sotheby's International Realty

    7312 Solitude Rd, Saint Michaels, MD 21663
    • 123 Grace St, St. Michaels, MD 21663
      123 Grace St, St. Michaels, MD 21663
      123 Grace St, St. Michaels, MD 21663
      /33

      Est $559,763 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
  • 9171 Deepwater Point Rd, Saint Michaels, MD 21663
    9171 Deepwater Point Rd, Saint Michaels, MD 21663
    9171 Deepwater Point Rd, Saint Michaels, MD 21663
    /40

    $1,635,000 Open Sun 10AM - 12PM

    • 4 Beds
    • 3.5 Baths
    • 4,102 Sq Ft

    9171 Deepwater Point Rd, Saint Michaels, MD 21663

    Welcome to Saint Michaels Retreat—an extraordinary 6-acre property overlooking the Links at Perry Cabin Golf Course with direct water access to Long Haul Creek and the Miles River. Just minutes from downtown Saint Michaels, this stunningly renovated residence offers over 4,100 sq. ft. of one-level living, thoughtfully designed for effortless indoor and outdoor entertaining. Inside, expansive

    Laura Carney TTR Sotheby's International Realty

    9171 Deepwater Point Rd, Saint Michaels, MD 21663
  • 320 Perry Cabin Dr, Saint Michaels, MD 21663
    320 Perry Cabin Dr, Saint Michaels, MD 21663
    320 Perry Cabin Dr, Saint Michaels, MD 21663
    /16

    $1,000,000 Sold Oct 08, 2025

    • 1,557 Sq Ft
    • $642/SF
    • 1 Day On Market
    • 2 Beds
    • 2.5 Baths
    • Built 1988

    320 Perry Cabin Dr, Saint Michaels, MD 21663

    Enjoy coastal living while still being walking distance to the historic town of St. Michaels. This beautiful 2 BR, 2.5 BA townhome located adjacent to the Inn at Perry Cabin is move in ready. Amazing Views of the Miles River with an open floor plan, and an enclosed bonus sunroom with wet-bar and dual beverage/wine fridge. Gourmet kitchen with beautiful cabinetry, SS appliances & Silestone

    Maureen McHugh Chesapeake Bay Real Estate Plus, LLC

    320 Perry Cabin Dr, Saint Michaels, MD 21663
    • 112 Conner St, St. Michaels, MD 21663
      112 Conner St, St. Michaels, MD 21663
      112 Conner St, St. Michaels, MD 21663
      /24

      Est $536,513 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
  • 23869 New Land Dr, St. Michaels, MD 21663
    23869 New Land Dr, St. Michaels, MD 21663
    23869 New Land Dr, St. Michaels, MD 21663
    /69

    $1,850,000

    • 3 Beds
    • 2 Baths
    • 2,717 Sq Ft

    23869 New Land Dr, St. Michaels, MD 21663

    Welcome to Heron Cove Farm, a beautiful waterfront paradise situated on the banks of Broad Creek, just outside of Historic Saint Michaels, MD. This masterfully renovated home offers the convenience of one level living in a private setting of over 15 acres creating the feel of a peaceful escape, yet only two miles from the restaurants, shops and social network of town. Whether you enjoy relaxing

    Keith Hensley Meredith Fine Properties

    23869 New Land Dr, St. Michaels, MD 21663
  • 408 Water St, Saint Michaels, MD 21663
    408 Water St, Saint Michaels, MD 21663
    408 Water St, Saint Michaels, MD 21663
    /34

    $995,000 Sold Oct 08, 2025

    • 1,893 Sq Ft
    • $526/SF
    • 3 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1972

    408 Water St, Saint Michaels, MD 21663

    Ideally located in the heart of historic St. Michaels with views of the harbor, this beautifully renovated 3BR/2.5BA coastal-style home offers one-level living, and is the perfect blend of timeless charm and modern comfort. The open floor plan seamlessly connects the living room—anchored by a wood-burning fireplace—to the dining area and gourmet kitchen, creating an inviting space for both

    Laura Carney TTR Sotheby's International Realty

    408 Water St, Saint Michaels, MD 21663
    • 111 Dodson Ave, Saint Michaels, MD 21663
      111 Dodson Ave, Saint Michaels, MD 21663
      111 Dodson Ave, Saint Michaels, MD 21663
      /50

      Est $687,999 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
  • 107 E Chestnut St, Saint Michaels, MD 21663
    107 E Chestnut St, Saint Michaels, MD 21663
    107 E Chestnut St, Saint Michaels, MD 21663
    /65

    $1,295,000

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

    107 E Chestnut St, Saint Michaels, MD 21663

    St. Michaels charm in this Circa 1870 Certified Plaque home, although historical data reflects original construction between 1805-1820.Updates include plumbing ,wiring, New upstairs HVAC, encapsulated crawl space, kitchen ,upgraded light fixtures, motorized window shades and many architectural details, freshly painted in 2024 . Recently upgraded Primary bedroom window seats with cushions,

    Robert Fitton Meredith Fine Properties

    107 E Chestnut St, Saint Michaels, MD 21663
  • 602 S Talbot St, Saint Michaels, MD 21663
    602 S Talbot St, Saint Michaels, MD 21663
    602 S Talbot St, Saint Michaels, MD 21663
    /46

    $740,000 Sold Oct 02, 2025

    • 2,433 Sq Ft
    • $304/SF
    • 844 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1890

    602 S Talbot St, Saint Michaels, MD 21663

    ***NEW PRICE IMPROVEMENT..... MUST SEE THIS Charming 4-Bedroom Home with Guest Cottage in Saint Michaels, MDHome was under contract with a lovely couple trying to move their family to St. Michaels. WE GET IT- It's a Great place to live. Unfortunately, after waiting, and waiting and giving multiple extensions because the seller understood they really loved this home-- They just could not

    Cheri Bruce-Phipps TTR Sotheby's International Realty

    602 S Talbot St, Saint Michaels, MD 21663
    • 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 $902,776 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
  • 24318 Oakwood Park Rd, Saint Michaels, MD 21663
    24318 Oakwood Park Rd, Saint Michaels, MD 21663
    24318 Oakwood Park Rd, Saint Michaels, MD 21663
    /99

    $1,249,000

    • 3 Beds
    • 3 Baths
    • 1,612 Sq Ft

    24318 Oakwood Park Rd, Saint Michaels, MD 21663

    St Michaels is just 2 miles away... Oakwood park known to be a slice of Eastern Shore heaven. This one story cottage with a dreamy porch and carriage house serves as the owners get away and vacation rental. Features are riprap shoreline and a boat ramp, the Carriage house with second floor guest and a balcony overlooking San Domingo Creek, a 2 car garage with workshop, laundry space and

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    24318 Oakwood Park Rd, Saint Michaels, MD 21663
  • 109 Bush Terrace, Saint Michaels, MD 21663
    109 Bush Terrace, Saint Michaels, MD 21663
    109 Bush Terrace, Saint Michaels, MD 21663
    /56

    $519,000 Under Contract

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

    109 Bush Terrace, Saint Michaels, MD 21663

    St Michaels immaculate three bedroom home. The Builder owner just recently renovated this great home. All new floors, bathrooms, new kitchen, redesigned first floor plan. Fabulous primary suite on first floor with gorgeous bathroom and large walk in closet . Welcoming laundry room and half a bath with accent wall. The large shady screened porch will be your second living and dining room in

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    109 Bush Terrace, 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 $1,334,029 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
  • 216 E Chew Ave, Saint Michaels, MD 21663
    216 E Chew Ave, Saint Michaels, MD 21663
    216 E Chew Ave, Saint Michaels, MD 21663
    /56

    $1,899,000

    • 4 Beds
    • 3.5 Baths
    • 3,575 Sq Ft

    216 E Chew Ave, Saint Michaels, MD 21663

    Experience and enjoy captivating views of the St Michaels Harbor from every room in the house. Conveniently situated in the heart of downtown St Michaels within walking distance to casual and fine dining. The floorplan includes 4 bedrooms, 3 full baths and 1 half bath. Total bedroom and bath count includes a separate guest suite with full kitchen. The newer addition is an octagon great room with

    Daphne Cawley TTR Sotheby's International Realty

    216 E Chew Ave, Saint Michaels, MD 21663
  • 110 Lee St, Saint Michaels, MD 21663
    110 Lee St, Saint Michaels, MD 21663
    110 Lee St, Saint Michaels, MD 21663
    /49

    $479,999 Pending

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft

    110 Lee St, Saint Michaels, MD 21663

    Welcome to 110 Lee Street, a brand-new single-level home tucked away in the heart of charming St. Michaels, Maryland. Thoughtfully designed and just completed in 2024, this home captures the perfect balance of modern elegance and small-town warmth, offering a lifestyle that’s as relaxed as it is refined.Step inside and experience an open-concept floor plan that effortlessly connects the

    Chance Stem LPT Realty, LLC

    110 Lee St, 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 $1,144,858 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
  • 24318 Oakwood Park Rd, Saint Michaels, MD 21663
    24318 Oakwood Park Rd, Saint Michaels, MD 21663
    24318 Oakwood Park Rd, Saint Michaels, MD 21663
    /6

    $1,238,000 Coming Soon

    • 3 Beds
    • 3 Baths
    • 1,612 Sq Ft

    24318 Oakwood Park Rd, Saint Michaels, MD 21663

    Welcome to Old House Cove Waterfront Retreat in St. Michael’s, 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
  • 23336 Tunis Ln, Claiborne, MD 21624
    23336 Tunis Ln, Claiborne, MD 21624
    23336 Tunis Ln, Claiborne, MD 21624
    /70

    $465,000 Sold Sep 18, 2025

    • 1,190 Sq Ft
    • $391/SF
    • 67 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1900

    23336 Tunis Ln, Claiborne, MD 21624

    *NEW AERIAL PHOTOS OF BOAT RAMP/LANDING/BEACH* The charming Eastern Shore Waterman’s Cottage, located at 23336 Tunis Lane in Claiborne, MD, was originally built in 1900 and fully renovated in 2017. Additional features include a modern kitchen with stainless steel appliances and a propane stove, as well as a bathroom with Carrera marble, heated floors, and a towel warmer. The home has been

    Maureen McHugh Chesapeake Bay Real Estate Plus, LLC

    23336 Tunis Ln, Claiborne, MD 21624
    • 417 Water St, Saint Michaels, MD 21663
      417 Water St, Saint Michaels, MD 21663
      417 Water St, Saint Michaels, MD 21663
      /65

      Est $1,541,526 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
  • 9545 Quail Hollow Dr Unit 205, Saint Michaels, MD 21663
    9545 Quail Hollow Dr Unit 205, Saint Michaels, MD 21663
    9545 Quail Hollow Dr Unit 205, Saint Michaels, MD 21663
    /32

    $385,000 Open Sat 11AM - 1PM

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

    9545 Quail Hollow Dr Unit 205, Saint Michaels, MD 21663

    Desirable Martingham Community is the location of this fabulous Quail Hollow unit nestled within the famous "links at Perry Cabin " , one of the few units with a screened porch . Enjoy the beautiful golf course views from the second floor, the first floor is private with its landscaping. Bathroom and kitchen countertops are granite, the kitchen has a space for a breakfast table, Living and

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    9545 Quail Hollow Dr Unit 205, Saint Michaels, MD 21663
  • 204 W Chew Ave, Saint Michaels, MD 21663
    204 W Chew Ave, Saint Michaels, MD 21663
    204 W Chew Ave, Saint Michaels, MD 21663
    /76

    $660,000 Sold Sep 16, 2025

    • 1,500 Sq Ft
    • $440/SF
    • 4 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1890

    204 W Chew Ave, Saint Michaels, MD 21663

    St. Michaels Renovated Historic Gem: Step into a turnkey, fully renovated 1890 historic home that blends timeless charm with modern luxury. Completely transformed in 2023—inside and out—this move-in-ready residence is the perfect pied-a-terre, vacation retreat, or low-maintenance full-time home.Just one block from the heart of historic St. Michaels, a vibrant waterfront town on Maryland’s

    Ani Gonzalez-Brunet Coldwell Banker Realty

    204 W Chew Ave, Saint Michaels, MD 21663

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Maryland Talbot County Saint Michaels

Real Estate & Homes

Home Trends in Saint Michaels, MD

On average, homes in Saint Michaels, MD sell after 66 days on the market compared to the national average of 52 days. The median sale price for homes in Saint Michaels, MD over the last 12 months is $795,000, up 18% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$795,000
Median Single Family Sale Price
$830,000
Median Townhouse Sale Price
$392,450
Median 2 Bedroom Sale Price
$368,500
Average Price Per Sq Ft
$414
Number of Homes for Sale
22
Last 12 months Home Sales
67
Months of Supply
3.90
Median List Price
$799,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
18%
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