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Ranch Style Homes for Sale in Saint Michaels, MD

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  • 24580 #2 Deepwater Point, Saint Michaels, MD 21663
    24580 #2 Deepwater Point, Saint Michaels, MD 21663
    24580 #2 Deepwater Point, Saint Michaels, MD 21663
    /37

    $409,500 Open Sat 11AM - 1PM

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

    24580 #2 Deepwater Point, Saint Michaels, MD 21663

    Transformative renovation in Martingham! This beautifully updated 2-bedroom, 2-bath single-level Gull Wing Villa overlooks the 6th fairway at Links at Perry Cabin, offering a serene golf course setting just minutes from the heart of St. Michaels. Thoughtfully redesigned, the home features new flooring throughout, a fully renovated kitchen and baths, and a reimagined layout that enhances both flow

    Agent Photo

    Larry Brennan

    TTR Sotheby's International Realty

    (877) 313-6280

    24580 #2 Deepwater Point, Saint Michaels, MD 21663
  • 9359 Martingham Cir, Saint Michaels, MD 21663
    9359 Martingham Cir, Saint Michaels, MD 21663
    9359 Martingham Cir, Saint Michaels, MD 21663
    /72

    $795,000

    • 4 Beds
    • 3 Baths
    • 1,988 Sq Ft

    9359 Martingham Cir, Saint Michaels, MD 21663

    FABULOUS ONE STORY LIVING WITH PRIVATE BACKYARD WITH VIEW OF THE POND OF THE 4TH GREEN OF THE LINK AT PERRY CABIN . JUST MINUTES FROM HISTORIC ST MICHAELS CENTER THE COMMUNITY IS A FAVORITE WITH ITS BEAUTIFUL WATERSIDE PARK FOR RESIDENTS ONLY OVERLOOKING THE MILES RIVER.THE HOME IS IN IMMACULATE RENOVATED CONDITION, BATHROOMS , KITCHEN, PAINT , THE ROOF WAS REPLACED IN SEPTEMBER 2025; 30 YEAR

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    9359 Martingham Cir, Saint Michaels, MD 21663
  • 8090 Bozman Neavitt Rd, Bozman, MD 21612
    8090 Bozman Neavitt Rd, Bozman, MD 21612
    8090 Bozman Neavitt Rd, Bozman, MD 21612
    /33

    $993,000

    • 3 Beds
    • 2 Baths
    • 1,362 Sq Ft

    8090 Bozman Neavitt Rd, Bozman, MD 21612

    Nestled behind spectacular Japanese Red Maples is a cozy 3 bedroom, 2 bath cottage overlooking Harris Creek with panoramic sunsets! Along with a large family room, dining room enjoy spectacular water views from the screened porch. Property is in excellent condition with a new roof, heat pump and well pump. Offered as a “turn key” investment with all furniture and fixtures. Located in historic St.

    Bill Wieland Benson & Mangold, LLC

    8090 Bozman Neavitt Rd, Bozman, MD 21612
  • 108 Miles, Saint Michaels, MD 21663
    108 Miles, Saint Michaels, MD 21663
    108 Miles, Saint Michaels, MD 21663
    /25

    $779,000 New Construction

    • 3 Beds
    • 2 Baths
    • 1,710 Sq Ft

    108 Miles, Saint Michaels, MD 21663

    A rare opportunity to pair a half-acre+ wooded in-town parcel with a thoughtfully designed single-level home concept in the heart of St. Michaels. This Concept A plan illustrates a 3-bedroom, 2-bath residence totaling approximately 1,710 square feet, featuring one-level living and an attached one-car garage. Designed to maximize functionality and flow, the concept offers flexible living spaces

    Chuck Mangold Benson & Mangold, LLC

    108 Miles, Saint Michaels, MD 21663
  • 24561 Deepwater Point Dr, Saint Michaels, MD 21663
    24561 Deepwater Point Dr, Saint Michaels, MD 21663
    24561 Deepwater Point Dr, Saint Michaels, MD 21663
    /50

    $649,000

    • 3 Beds
    • 3 Baths
    • 2,144 Sq Ft

    24561 Deepwater Point Dr, Saint Michaels, MD 21663

    Effortless living in the Martingham community. This thoughtfully designed 3-bedroom, 3-bath rancher features a light-filled, easy-flow floorplan with two ensuite bedrooms for added privacy and versatility. The home offers a garage and separate laundry room and opens to a charming backyard deck - ideal for morning coffee or evening gatherings. The spacious backyard provides ample room for a pool,

    Maureen McHugh Chesapeake Bay Real Estate Plus, LLC

    24561 Deepwater Point Dr, 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

    $499,000

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

    23266 Mallard Point Rd, McDaniel, MD 21647

    Just a 10-minute drive from Historic St. Michaels, MD (approximately 6 miles), this attractive 1-level, 3-bedroom, two bath home is in "turn-key/move-in condition." Extensively updated 2025-26, the house shows like brand new! Inside: New luxury vinyl floors throughout; All-new kitchen cabinets, quartzite countertops, Frigidaire stainless appliances, New bathrooms. Great floor plan includes a

    Tom Crouch Benson & Mangold, LLC

    23266 Mallard Point Rd, McDaniel, MD 21647
  • 1206 Washington Dr, Saint Michaels, MD 21663
    1206 Washington Dr, Saint Michaels, MD 21663
    1206 Washington Dr, Saint Michaels, MD 21663
    /18

    $499,900

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

    1206 Washington Dr, Saint Michaels, MD 21663

    This well-maintained duplex in Rio Vista presents an exceptional investment opportunity, featuring two spacious units, each offering 2 bedrooms and 1.5 baths. Ideally situated just moments from the heart of historic downtown St. Michaels, residents enjoy easy access to charming shops, dining, and waterfront attractions—all while benefiting from no town taxes. With both units currently 100%

    Chuck Mangold Benson & Mangold, LLC

    1206 Washington Dr, Saint Michaels, MD 21663
  • 23961 Lynnewood Dr, Saint Michaels, MD 21663
    23961 Lynnewood Dr, Saint Michaels, MD 21663
    23961 Lynnewood Dr, Saint Michaels, MD 21663
    /68

    $3,100,000

    • 4 Beds
    • 3.5 Baths
    • 4,035 Sq Ft

    23961 Lynnewood Dr, Saint Michaels, MD 21663

    Located within 2 miles of historic St. Michaels this exceptional waterfront estate blends timeless elegance with a resort-style setting. This 4,200± sq. ft. custom, single-level all brick residence showcases soaring ceilings, an abundance of natural light, and panoramic views of Broad Creek from almost every room. A huge great room featuring a large brick fireplace and open living / dining

    Barbara Watkins Benson & Mangold, LLC

    23961 Lynnewood Dr, Saint Michaels, MD 21663
  • 24390 Oakwood Park Rd, Saint Michaels, MD 21663
    24390 Oakwood Park Rd, Saint Michaels, MD 21663
    24390 Oakwood Park Rd, Saint Michaels, MD 21663
    /68

    $1,679,000

    • 4 Beds
    • 3.5 Baths
    • 2,839 Sq Ft

    24390 Oakwood Park Rd, Saint Michaels, MD 21663

    Significant price improvement! Welcome to your private waterfront retreat just minutes from the charming, historic town of St. Michaels, Maryland. Tucked away on a quiet cul-de-sac in the serene Oakwood Park community along San Domingo Creek, this one-story residence offers four bedrooms, three and a half baths, and a harmonious blend of space and comfort. With approximately 2,839 finished square

    Janet Larson Benson & Mangold, LLC

    24390 Oakwood Park Rd, Saint Michaels, MD 21663
  • 100 Bush Terrace, Saint Michaels, MD 21663
    100 Bush Terrace, Saint Michaels, MD 21663
    100 Bush Terrace, Saint Michaels, MD 21663
    /40

    $480,000

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft

    100 Bush Terrace, Saint Michaels, MD 21663

    This home allows for a 3.12% FHA Assumable Loan! Welcome to easy Eastern Shore living in the charming waterfront town of St. Michaels! This 3-bedroom, 2 bath, 1,232 sq. ft. home is located in the desirable community of Rio Vista offering direct access to the Miles River, complete with a community dock, boat slips, and boat ramp — perfect for boating, crabbing, paddleboarding, or sunset cruises.

    Cheri Bruce-Phipps TTR Sotheby's International Realty

    100 Bush Terrace, Saint Michaels, MD 21663
  • 113 Gloria Ave, Saint Michaels, MD 21663
    113 Gloria Ave, Saint Michaels, MD 21663
    113 Gloria Ave, Saint Michaels, MD 21663
    /36

    $539,500

    • 3 Beds
    • 2 Baths
    • 1,456 Sq Ft

    113 Gloria Ave, Saint Michaels, MD 21663

    Situated on a corner lot just minutes from downtown St. Michaels, this 3-bedroom, 2-bath home offers easy access to local shops, restaurants, and the Maritime Museum. Inside, the living room is filled with natural light from a large bay window and features LVP flooring, recessed lighting, and updated fixtures throughout. The kitchen and dining area provide an open, functional layout with direct

    Peter Stark Benson & Mangold, LLC

    113 Gloria Ave, Saint Michaels, MD 21663
  • 101 Brooks Ln, Saint Michaels, MD 21663
    101 Brooks Ln, Saint Michaels, MD 21663
    101 Brooks Ln, Saint Michaels, MD 21663
    /28

    $425,000

    • 3 Beds
    • 2 Baths
    • 1,120 Sq Ft

    101 Brooks Ln, Saint Michaels, MD 21663

    Welcome to this beautifully updated cottage in the heart of St. Michaels—where modern comfort meets Eastern Shore charm. Perfectly situated within walking distance to the town’s shops, restaurants, Rails to Trails, and the renowned Maritime Museum, this single‐level home offers both convenience and a peaceful, private setting. Sitting on nearly a quarter acre, the property features a fully fenced

    Stacie Luhrman Benson & Mangold, LLC

    101 Brooks Ln, Saint Michaels, MD 21663
  • 111 Gloria Ave, Saint Michaels, MD 21663
    111 Gloria Ave, Saint Michaels, MD 21663
    111 Gloria Ave, Saint Michaels, MD 21663
    /30

    $435,000

    • 2 Beds
    • 1.5 Baths
    • 1,125 Sq Ft

    111 Gloria Ave, Saint Michaels, MD 21663

    Essentially a NEW HOME! Extensively, tastefully and professionally renovated 1965 rancher located on a quiet residential street, just 2 blocks from downtown St. Michaels. Nearly everything is brand new, including roof shingles, siding, windows, HVAC system and new deck. New off-street parking area, sized for 2 vehicles. Inside, everything looks (and is) new, including attractive luxury vinyl

    Tom Crouch Benson & Mangold, LLC

    111 Gloria Ave, Saint Michaels, MD 21663
Maryland Talbot County Saint Michaels

Real Estate & Homes for Sale in Saint Michaels, MD

Home Trends in Saint Michaels, MD

On average, homes in Saint Michaels, MD sell after 79 days on the market compared to the national average of 57 days. The median sale price for homes in Saint Michaels, MD over the last 12 months is $775,000, up 9% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$775,000
Median Single Family Sale Price
$799,000
Median Townhouse Sale Price
$470,000
Median 2 Bedroom Sale Price
$349,500
Average Price Per Sq Ft
$412
Number of Homes for Sale
44
Last 12 months Home Sales
73
Months of Supply
7.20
Median List Price
$795,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
9%
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