2,829

Saint Michaels, MD Homes

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  • /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
  • /7

    Call for Price

    • 1 - 2 Beds

    111 Mitchell St, Saint Michaels, MD 21663

    Riverwoods at Saint Michaels

    111 Mitchell St, Saint Michaels, MD 21663
  • /36

    $418,000

    Sold Apr 07, 2026

    24345 Widgeon Place Unit 25, Saint Michaels, MD 21663

    • 3 Beds
    • 3 Baths
    • 1,752 Sq Ft
    • Built 1986

    Last Sold Summary

    • 4% Below List Price
    • $239/SF
    • 17 Days On Market

    Current Estimated Value $417,856

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

    24345 Widgeon Place Unit 25, 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

  • /39

    $849,000

    • 3 Beds
    • 2 Baths
    • 1,288 Sq Ft

    803 New Ln, Saint Michaels, MD 21663

    Thoughtfully reimagined from the studs out, this exceptional residence offers the character of an in-town cottage with the quality, comfort, and finishes of a newly constructed home. Every detail has been carefully considered, creating a seamless blend of timeless charm and modern design. A welcoming front porch with a classic porch swing sets the tone before stepping inside to a light-filled

    Agent Photo

    Larry Brennan

    TTR Sotheby's International Realty

    803 New Ln, Saint Michaels, MD 21663
  • /24

    $2,000 Per Month

    • 2 Beds
    • 2.5 Baths
    • Townhouse for Rent

    24700 Deepwater Unit 1, Saint Michaels, MD 21663

    GREAT RENTAL OPPORTUNITY !Inviting townhouse in the St. Michaels Martingham community with views across the Links at Perry Cabin fairway, offering easy Eastern Shore living. From the upstairs living areas, enjoy lovely, elevated views, abundant natural light, and a sense of openness that enhances the home’s warm, inviting feel. The upper-level living area features shining hardwood floors, and

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    24700 Deepwater Unit 1, 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

    Current Estimated Value $506,356

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

    109 Bush Terrace, Saint Michaels, MD 21663
    • /19

      Est $304,250

      Not Listed For Sale

      112 Mitchell St, Saint Michaels, MD 21663

      • 3 Beds
      • 1 Bath
      • 1,368 Sq Ft
      • Built 1984
      112 Mitchell St, Saint Michaels, MD 21663

      Last Sold Summary

      • 126 Days On Market

  • /135

    $1,595,000

    $200K PRICE DROP Under Contract
    • 4 Beds
    • 3.5 Baths
    • 3,575 Sq Ft

    216 E Chew Ave, Saint Michaels, MD 21663

    PRICE REDUCED: Don't miss this rare opportunity. This special home offers spectacular and picturesque views of the Saint Michaels Harbor in addition to its prime location on one of Saint Michaels most desirable streets. Conveniently located near all of the in-town amenities and walkable to great restaurants, shops, brewery, winery, gallery, seasonal farmer's market, museums and more. This home

    Agent Photo

    Christopher Clinton

    Coldwell Banker Chesapeake Real Estate Company

    216 E Chew Ave, Saint Michaels, MD 21663
  • /27

    $2,650 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

    Move in ready and 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. Very clean home! Credit report and references required. Shorter lease term may be available.

    Drew Buniski Benson & Mangold, LLC

    921 C S Talbot St Unit C, 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

    Current Estimated Value $1,304,843

    Last Listing Agent Laura Carney TTR Sotheby's International Realty

    204 Mulberry St, Saint Michaels, MD 21663
    • /59

      Est $805,970

      Not Listed For Sale

      9240 Martingham Dr, Saint Michaels, MD 21663

      • 4 Beds
      • 2.5 Baths
      • 2,910 Sq Ft
      • Built 1998
      9240 Martingham Dr, Saint Michaels, MD 21663

      Last Sold Summary

      • 3 Days On Market

  • /39

    $3,250,000

    Pending
    • 4 Beds
    • 4.5 Baths
    • 3,289 Sq Ft

    601 Cove Rd, Saint Michaels, MD 21663

    Experience tranquil waterfront living in this stunning 4BR/4.5 BA home sited on .68 acres overlooking the Miles River. This cottage-style home was completely renovated by Focus ConstructionFeaturing exquisite architectural and interior design details throughout and include custom built-ins, and a large dual-sided gas fireplace. The open floor plan offers breathtaking river views from nearly

    Agent Photo

    Brian Gearhart

    Benson & Mangold, LLC

    601 Cove Rd, Saint Michaels, MD 21663
  • /6

    $2,400 Per Month

    • 4 Beds
    • 2 Baths
    • 1,680 Sq Ft
    • House for Rent

    103 Douglas Ln, Saint Michaels, MD 21663

    St. Michaels Cape. First floor offers living room with fireplace, dining area/kitchen combo, 2 bedrooms and bath. 2nd floor features 2 bedrooms and bath. Rear deck overlooking private backyard. Storage shed. Walking distance to downtown amenities, shopping and restaurants. Rented unfurnished. No pets. Non-smokers. Credit check and references required. One year + lease. Immediate occupancy.

    Judy Moore Benson & Mangold, LLC

    103 Douglas Ln, Saint Michaels, MD 21663
  • /109

    $6,000,000

    Sold Apr 15, 2026

    10770 Rich Neck Rd, Claiborne, MD 21624

    • 8 Beds
    • 5 Baths
    • 10,240 Sq Ft
    • Built 1824

    Last Sold Summary

    • $586/SF
    • 291 Days On Market

    Current Estimated Value $5,685,987

    Last Listing Agent Robert G. Shannahan Shoreline Realty

    10770 Rich Neck Rd, Claiborne, MD 21624
    • /103

      Est $2,671,028

      Not Listed For Sale

      9191 Deepwater Point Rd, Saint Michaels, MD 21663

      • 5 Beds
      • 4 Baths
      • 5,088 Sq Ft
      • Built 1988
      9191 Deepwater Point Rd, Saint Michaels, MD 21663

      Last Sold Summary

      • 187 Days On Market

  • /57

    $1,650,000

    $75K PRICE DROP Under Contract
    • 3 Beds
    • 2.5 Baths
    • 3,078 Sq Ft

    602 Landing Rd, Saint Michaels, MD 21663

    Welcome to waterfront living in the heart of St. Michaels. This fully renovated 3-bedroom plus office, 2.5-bath home offers a thoughtful blend of modern updates and coastal charm, all set against expansive views of the Miles River. The first-floor primary suite is a true retreat, featuring a custom California Closet system and a beautifully updated bath with a walk-in shower, freestanding tub,

    Agent Photo

    Brian Gearhart

    Benson & Mangold, LLC

    602 Landing Rd, 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
  • /33

    $787,500

    Sold Jan 15, 2026

    24420 Mallard Place, Saint Michaels, MD 21663

    • 4 Beds
    • 2.5 Baths
    • 2,493 Sq Ft
    • Built 1988

    Last Sold Summary

    • $316/SF
    • 97 Days On Market

    Current Estimated Value $775,330

    Last Listing Agent Robert Lacaze TTR Sotheby's International Realty

    24420 Mallard Place, Saint Michaels, MD 21663
    • /52

      Est $844,580

      Not Listed For Sale

      504 S Talbot St, Saint Michaels, MD 21663

      • 3 Beds
      • 2.5 Baths
      • 2,072 Sq Ft
      • Built 1900
      504 S Talbot St, Saint Michaels, MD 21663

      Last Sold Summary

      • 76 Days On Market

  • /72

    $549,999

    $25K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,200 Sq Ft

    204 E Marengo St, Saint Michaels, MD 21663

    Priced to sell! The perfect weekend getaway does exist—and it's more attainable than you might think. Escape the city and discover the charm of St. Michaels, one of the Eastern Shore's most beloved waterfront towns. Known for its picturesque streets, waterfront dining, boutique shopping, wineries, marinas, and laid-back coastal lifestyle, St. Michaels offers the perfect place to relax, recharge,

    Agent Photo

    Gretchen Wichlinski

    Compass

    204 E Marengo St, Saint Michaels, MD 21663
  • /24

    $2,400 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,652 Sq Ft
    • Townhouse for Rent

    24700 Deepwater Point Dr 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 Point Dr Unit 10, 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

    Current Estimated Value $1,782,684

    Last Listing Agent Larry Brennan TTR Sotheby's International Realty

    7312 Solitude Rd, Saint Michaels, MD 21663
    • /40

      Est $752,385

      Not Listed For Sale

      24989 Back Creek Dr, Saint Michaels, MD 21663

      • 4 Beds
      • 2.5 Baths
      • 3,098 Sq Ft
      • Built 2006
      24989 Back Creek Dr, Saint Michaels, MD 21663

      Last Sold Summary

      • 0 Days On Market

  • /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
  • /44

    $1,130,000

    Sold Feb 06, 2026

    24318 Oakwood Park Rd, Saint Michaels, MD 21663

    • 3 Beds
    • 3 Baths
    • 2,085 Sq Ft
    • Built 1968

    Last Sold Summary

    • $542/SF
    • 73 Days On Market

    Current Estimated Value $1,101,169

    Last Listing Agent Kathleen Eder Compass

    24318 Oakwood Park Rd, Saint Michaels, MD 21663
    • /42

      Est $954,181

      Not Listed For Sale

      312 N Talbot St, Saint Michaels, MD 21663

      • 4 Beds
      • 3 Baths
      • 2,080 Sq Ft
      • Built 2022
      312 N Talbot St, Saint Michaels, MD 21663

      Last Sold Summary

      • 527 Days On Market

  • /32

    $1,049,000

    • 4 Beds
    • 3 Baths
    • 2,250 Sq Ft

    109 W Marengo St, Saint Michaels, MD 21663

    This thoughtfully designed 4-bedroom, 3-bathroom home features an open-concept floor plan ideal for both everyday living and entertaining. The main-level primary suite provides a private retreat with a spacious walk-in closet and an en-suite bath complete with a double vanity and glass-enclosed shower. The living room is anchored by a cozy gas fireplace and flows seamlessly into the dining area

    Chuck Mangold Benson & Mangold, LLC

    109 W Marengo St, Saint Michaels, MD 21663
  • /39

    $1,225,000

    Sold Jun 05, 2026

    106 E Chestnut St, Saint Michaels, MD 21663

    • 2 Beds
    • 2.5 Baths
    • 2,282 Sq Ft
    • Built 1830

    Last Sold Summary

    • 8% Below List Price
    • $537/SF
    • 49 Days On Market

    Current Estimated Value $1,319,165

    Last Listing Agent Justin Pokrywka Taylor Properties

    106 E Chestnut St, Saint Michaels, MD 21663
    • /51

      Est $1,305,470

      Not Listed For Sale

      202 Mulberry St, Saint Michaels, MD 21663

      • 4 Beds
      • 3 Baths
      • 2,703 Sq Ft
      • Built 1890
      202 Mulberry St, Saint Michaels, MD 21663

      Last Sold Summary

      • 8 Days On Market

  • /29

    $650,000

    Pending
    • 3 Beds
    • 2.5 Baths
    • 2,902 Sq Ft

    24895 Back Creek Dr, Saint Michaels, MD 21663

    Situated in the Back Creek Landing community just minutes from historic downtown St. Michaels, this thoughtfully designed two-story home offers comfortable main-level living with spacious gathering areas and desirable community amenities. A covered front porch welcomes you inside, where hardwood flooring extends throughout the main level. The open kitchen features a gas cooktop, breakfast nook,

    Chuck Mangold Benson & Mangold, LLC

    24895 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 $597,320

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

    9217 Martingham Dr, Saint Michaels, MD 21663
    • /33

      Est $627,023

      Not Listed For Sale

      123 Grace St, St. Michaels, MD 21663

      • 3 Beds
      • 2 Baths
      • 720 Sq Ft
      • Built 1963
      123 Grace St, St. Michaels, MD 21663

      Last Sold Summary

      • 3 Days On Market

  • /41

    $3,495,000

    $300K PRICE DROP
    • 4 Beds
    • 5 Baths
    • 6,404 Sq Ft

    24678 New Post Rd, Saint Michaels, MD 21663

    Rare opportunity to acquire a well-appointed home with immense views and convenient proximity to St Michaels. Ideally located by land and sea in Chance Hope Farm on the Miles River at the confluence of Eastern Bay, this stunning, classic eastern shore brick colonial has everything the most decerning buyer needs. This Daffin custom-built home features a generous, main-level primary suite featuring

    Chuck Mangold Benson & Mangold, LLC

    24678 New Post Rd, Saint Michaels, MD 21663
  • /2

    $499,000

    Sold Jul 20, 2026

    934 Calvert Ave, Saint Michaels, MD 21663

    • 3 Beds
    • 2 Baths
    • 1,574 Sq Ft
    • Built 2001

    Last Sold Summary

    • $317/SF
    • 14 Days On Market

    Current Estimated Value $496,104

    Last Listing Agent Will Stone Benson & Mangold, LLC

    934 Calvert Ave, Saint Michaels, MD 21663
    • /24

      Est $534,459

      Not Listed For Sale

      112 Conner St, St. Michaels, MD 21663

      • 4 Beds
      • 2 Baths
      • 2,016 Sq Ft
      • Built 1997
      112 Conner St, St. Michaels, MD 21663

      Last Sold Summary

      • 9 Days On Market

  • /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
  • /2

    $2,000,000

    Sold Jun 18, 2026

    938 Marea Terrace, Saint Michaels, MD 21663

    • 4 Beds
    • 5.5 Baths
    • 3,000 Sq Ft
    • Built 2020

    Last Sold Summary

    • 16% Below List Price
    • $667/SF
    • 83 Days On Market

    Current Estimated Value $1,996,581

    Last Listing Agent Carolina Barksdale Benson & Mangold, LLC

    938 Marea Terrace, Saint Michaels, MD 21663
    • /30

      Est $852,000

      Not Listed For Sale

      107 Carpenter St, Saint Michaels, MD 21663

      • 2 Beds
      • 2 Baths
      • 1,228 Sq Ft
      • Built 1900
      107 Carpenter St, Saint Michaels, MD 21663

      Last Sold Summary

      • 2 Days On Market

  • /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

Showing Results 1 - 40, Page 1 of 18

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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