13

Saint Michaels, MD Homes for Sale under $500,000

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  • 24700 Deepwater Unit 23, Saint Michaels, MD 21663
    24700 Deepwater Unit 23, Saint Michaels, MD 21663
    24700 Deepwater Unit 23, Saint Michaels, MD 21663
    /29

    $359,000

    $16K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,487 Sq Ft

    24700 Deepwater Unit 23, Saint Michaels, MD 21663

    Escape to the sought-after Swan Road Villa Townhomes, where low-maintenance living meets comfort, convenience, and lifestyle. This bright and inviting reverse-living townhome offers 2 bedrooms, 2.5 baths, and a thoughtfully designed floor plan that appeals to both full-time residents and weekend retreat seekers alike. The upper level serves as the heart of the home, featuring an open-concept

    Agent Photo

    Tracy Higgs-Wagner

    Meredith Fine Properties

    24700 Deepwater Unit 23, Saint Michaels, MD 21663
  • 9531 Quail Hollow Dr Unit 402, Saint Michaels, MD 21663
    9531 Quail Hollow Dr Unit 402, Saint Michaels, MD 21663
    9531 Quail Hollow Dr Unit 402, Saint Michaels, MD 21663
    /20

    $359,900

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

    9531 Quail Hollow Dr Unit 402, Saint Michaels, MD 21663

    Located in the desirable Martingham community, this two-bedroom, two-and-a-half-bath condominium offers comfortable living just minutes from historic downtown St. Michaels. The main level features a spacious living room with hardwood flooring and a wood-burning fireplace, a convenient half bath, and a full-season sunroom overlooking the backyard with direct access to the outdoor space. A detached

    Chuck Mangold Benson & Mangold, LLC

    9531 Quail Hollow Dr Unit 402, Saint Michaels, MD 21663
  • 1211 Washington Dr, Saint Michaels, MD 21663
    1211 Washington Dr, Saint Michaels, MD 21663
    1211 Washington Dr, Saint Michaels, MD 21663
    /14

    $499,000

    $26K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 2,420 Sq Ft

    1211 Washington Dr, Saint Michaels, MD 21663

    Desirable Rio Vista Duplex – Live in One Unit and Rent the Other! Rare opportunity to own a duplex in the sought-after Rio Vista community. Move into one unit and generate rental income from the other to help offset your mortgage payments. Properties like this seldom come on the market. Located in a water-access community, residents may enjoy dock access upon approval of the owner's application

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    1211 Washington Dr, Saint Michaels, MD 21663
  • 1215 Washington Dr, Saint Michaels, MD 21663
    1215 Washington Dr, Saint Michaels, MD 21663
    1215 Washington Dr, Saint Michaels, MD 21663
    /30

    $499,000

    $26K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 2,420 Sq Ft

    1215 Washington Dr, Saint Michaels, MD 21663

    RDesirable Rio Vista Duplex – Live in One Unit and Let Rental Income Help Pay Your Mortgage! Opportunities to own one of these sought-after duplexes are rare. Located in the desirable Rio Vista water-access community, this property offers potential dock access (subject to owner approval, application, and applicable fees). The building features two mirror-image units, each offering: A kitchen with

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    1215 Washington Dr, Saint Michaels, MD 21663
  • 912 Calvert Ave, Saint Michaels, MD 21663
    912 Calvert Ave, Saint Michaels, MD 21663
    912 Calvert Ave, Saint Michaels, MD 21663
    /11

    $219,000

    $10K PRICE DROP
    • Land
    • 10,890 Sq Ft
    • $876,000 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
  • 9818 Tilghman Island Rd, McDaniel, MD 21647
    9818 Tilghman Island Rd, McDaniel, MD 21647
    9818 Tilghman Island Rd, McDaniel, MD 21647
    /38

    $430,000

    $20K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 1,876 Sq Ft

    9818 Tilghman Island Rd, McDaniel, MD 21647

    Improved Price!! 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 Eastern Shore lifestyle:

    Valerie Brown Coldwell Banker Realty

    9818 Tilghman Island Rd, McDaniel, MD 21647
  • 24700 Deepwater Unit 20, Saint Michaels, MD 21663
    24700 Deepwater Unit 20, Saint Michaels, MD 21663
    24700 Deepwater Unit 20, Saint Michaels, MD 21663
    /58

    $385,000

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

    24700 Deepwater Unit 20, Saint Michaels, MD 21663

    Situated in the established community of Martingham, 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, energy efficiency, and long-term durability. The redesigned open floor plan creates a seamless flow throughout the main living areas, complemented by updated

    Monica Penwell TTR Sotheby's International Realty

    24700 Deepwater Unit 20, Saint Michaels, MD 21663
  • 108 Miles, Saint Michaels, MD 21663
    108 Miles, Saint Michaels, MD 21663
    108 Miles, Saint Michaels, MD 21663
    /27

    $295,000

    • Land
    • 23,958 Sq Ft
    • $536,364 per Acre

    108 Miles, Saint Michaels, MD 21663

    A rare opportunity in the heart of St. Michaels: this half-acre+ wooded parcel offers the privacy of a tucked-away retreat with the everyday convenience of an in-town location. Restaurants, shops, seasonal events, waterfront parks, and the character of the historic district are all close at hand, yet the setting feels quiet and natural. Approximately three times the size of a typical in-town lot,

    Chuck Mangold Benson & Mangold, LLC

    108 Miles, 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
    /40

    $374,000

    $11K PRICE DROP
    • 2 Beds
    • 3 Baths
    • 1,800 Sq Ft

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

    REDUCED CLEAN UNIT ...CASUAL LIVING IN SOUTH AFTER "THE LINK AT PERRY CABIN " MARTINGHAM COMMUNITY Nestled within the prestigious Quail Hollow community in desirable Martingham, this exceptional residence enjoys a prime setting overlooking the renowned Links at Perry Cabin golf course. One of the few units featuring a screened porch, this home offers the perfect blend of elegance, comfort,

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    9545 Quail Hollow Dr Unit 205, Saint Michaels, MD 21663
  • 104 Madison Ave, Saint Michaels, MD 21663
    104 Madison Ave, Saint Michaels, MD 21663
    /2

    $459,900

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

    104 Madison Ave, 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

    104 Madison 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
  • 9518 Quail Hollow Dr Unit 702, Saint Michaels, MD 21663
    9518 Quail Hollow Dr Unit 702, Saint Michaels, MD 21663
    9518 Quail Hollow Dr Unit 702, Saint Michaels, MD 21663
    /36

    $455,000

    $25K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,800 Sq Ft

    9518 Quail Hollow Dr Unit 702, Saint Michaels, MD 21663

    Set within the sought-after Martingham community of Quail Hollow, backing to the top rated golf course The Links at Perry Cabin, this fully updated 3-bedroom, 3-bath townhome offers stylish, low-maintenance living just minutes from downtown St. Michaels. Extensive renovations completed between 2022 and 2024 make this home truly turnkey. The main level welcomes you with beautiful wood floors, a

    Barbara Watkins Benson & Mangold, LLC

    9518 Quail Hollow Dr Unit 702, Saint Michaels, MD 21663
  • 0 Deepwater Point Dr, Saint Michaels, MD 21663
    0 Deepwater Point Dr, Saint Michaels, MD 21663
    0 Deepwater Point Dr, Saint Michaels, MD 21663
    /41

    $249,000

    • Land
    • 1.12 Acres
    • $222,321 per Acre

    0 Deepwater Point Dr, Saint Michaels, MD 21663

    ONE OF THE LAST LOTS IN MARTINGHAM ON DEEP WATER POINT DRIVE. LOCATED VERY CLOSE TO THE COMMUNITY WATERFRONT PARK WITH GAZEBO AND CHAIRS FOR PICKNICKS OR JUST RELAXING IN THE BREEZE WATCHING THE BOATS GO BY ; DROP YOUR KAYAK OR ENJOY THE SUNSETS, WALK OR BIKE THERE. THIS LOT IS CLEANED, HAS A BEAUTIFUL ENTRANCE , WATER METER, AND IS READY FOR YOU TO BUILT YOUR MAIN RESIDENCE OR WEEKEND GET AWAY.

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    0 Deepwater Point Dr, Saint Michaels, MD 21663
Maryland Talbot County

Real Estate & Homes in Saint Michaels, MD under $500,000

Home Prices in Saint Michaels, MD

The median home sale price in Saint Michaels, MD is $780,000, up 6% year-over-year. Homes in Saint Michaels sell in 75 days on average, compared to the national average of 56 days.

Home Price Trends

Median Sale Price
$780,000
Median Single Family Sale Price
$830,000
Median Townhouse Sale Price
$440,000
Median 2 Bedroom Sale Price
$404,500
Average Price Per Sq Ft
$416
Number of Homes for Sale
34
Last 12 months Home Sales
76
Months of Supply
5.40
Median List Price
$800,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
6%
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