View 107 W Chestnut Street Saint Michaels, MD MLS# MDTA2012552
$1,295,000
3

Beds

2.0

Baths

1,914

Sq.Ft.

107 W Chestnut Street

Saint Michaels, MD

Bright
Courtesy of CHESAPEAKE BAY REAL ESTATE PLUS, LLC
View 209 Webb Lane Saint Michaels, MD MLS# MDTA2012448
$229,000
2

Beds

1.0

Baths

932

Sq.Ft.

209 Webb Lane

Saint Michaels, MD

Bright
Courtesy of COLDWELL BANKER REALTY
View 216 E Chew Ave Saint Michaels, MD MLS# MDTA2012450
    1 of 143
    OPEN HOUSE: Saturday 3/21 12:00 PM - 2:00 PM
    $1,795,000
    4

    Beds

    3.1

    Baths

    3,575

    Sq.Ft.

    216 E Chew Ave

    Saint Michaels, MD

    Bright
    Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
    The time to sell is now! THE TIME TO SELL IS NOW!
    View 105 Seymour Avenue Saint Michaels, MD MLS# MDTA2012362
    $474,000
    2

    Beds

    1.0

    Baths

    1,080

    Sq.Ft.

    105 Seymour Avenue

    Saint Michaels, MD

    Bright
    Courtesy of RE/MAX EXECUTIVE
    View 108 Miles Avenue Saint Michaels, MD MLS# MDTA2012358
    • New Construction
    1 of 25
    $779,000
    3

    Beds

    2.0

    Baths

    1,710

    Sq.Ft.

    108 Miles Avenue

    Saint Michaels, MD

    Bright
    Courtesy of BENSON & MANGOLD, LLC
    View 108 Miles Avenue Saint Michaels, MD MLS# MDTA2012368
    • New Construction
    1 of 25
    $999,000
    3

    Beds

    2.1

    Baths

    108 Miles Avenue

    Saint Michaels, MD

    Bright
    Courtesy of BENSON & MANGOLD, LLC
    View 108 Miles Avenue Saint Michaels, MD MLS# MDTA2012348
    $295,000
    Studio

    Beds

    0.0

    Baths

    108 Miles Avenue

    Saint Michaels, MD

    Bright
    Courtesy of BENSON & MANGOLD, LLC
    View 9545 Quail Hollow # 205 Saint Michaels, MD MLS# MDTA2012128
    $385,000
    2

    Beds

    3.0

    Baths

    1,800

    Sq.Ft.

    9545 Quail Hollow # 205

    Saint Michaels, MD

    Bright
    Courtesy of LONG & FOSTER REAL ESTATE, INC.
    View 216 Brooks Saint Michaels, MD MLS# MDTA2011960
    • New Construction
    1 of 37
    $479,999
    3

    Beds

    2.0

    Baths

    1,500

    Sq.Ft.

    216 Brooks

    Saint Michaels, MD

    Bright
    Courtesy of LPT REALTY, LLC
    View 228 Tyler Avenue Saint Michaels, MD MLS# MDTA2011870
    $549,900
    3

    Beds

    2.1

    Baths

    1,922

    Sq.Ft.

    228 Tyler Avenue

    Saint Michaels, MD

    Bright
    Courtesy of BENSON & MANGOLD, LLC
    View 408 Spinnaker Lane Saint Michaels, MD MLS# MDTA2011880
    • Virtual Tour
    1 of 82
    OPEN HOUSE: Saturday 3/21 2:00 PM - 4:00 PM
    $699,000
    4

    Beds

    2.1

    Baths

    1,957

    Sq.Ft.

    408 Spinnaker Lane

    Saint Michaels, MD

    Bright
    Courtesy of NORTHROP REALTY
    View 912 Calvert Ave. Saint Michaels, MD MLS# MDTA2011868
    $219,000
    Studio

    Beds

    0.0

    Baths

    912 Calvert Ave.

    Saint Michaels, MD

    Bright
    Courtesy of BENSON & MANGOLD, LLC
    View 24977 Back Creek Drive Saint Michaels, MD MLS# MDTA2010224
    $749,999
    4

    Beds

    3.1

    Baths

    3,010

    Sq.Ft.

    24977 Back Creek Drive

    Saint Michaels, MD

    Bright
    Courtesy of BENSON & MANGOLD, LLC
    View 24749 Swan Road Saint Michaels, MD MLS# MDTA2010756
    $630,000
    3

    Beds

    2.1

    Baths

    2,496

    Sq.Ft.

    24749 Swan Road

    Saint Michaels, MD

    Bright
    Courtesy of BENSON & MANGOLD, LLC
    View 312 S Talbot Saint Michaels, MD MLS# MDTA2010570
    $595,000
    2,100

    Sq.Ft.

    312 S Talbot

    Saint Michaels, MD

    Bright
    Courtesy of BENSON & MANGOLD, LLC
    View Lot 16A Meadow Street Saint Michaels, MD MLS# MDTA2007414
    $799,000
    4

    Beds

    2.1

    Baths

    Lot 16A Meadow Street

    Saint Michaels, MD

    Bright
    Courtesy of KELLER WILLIAMS FLAGSHIP
    View 1103 S Talbot Street Saint Michaels, MD MLS# MDTA2008124
    $1,100,000
    6,950

    Sq.Ft.

    1103 S Talbot Street

    Saint Michaels, MD

    Bright
    Courtesy of BENSON & MANGOLD, LLC

    About Saint Michaels

    Located on the picturesque banks of the Miles River, the storybook setting of this pleasant harbor village attracts visitors by land and sea.  St. Michaels offers a pleasing mix of unique shops, fascinating museums and fine dining establishments, with all the charm of a colonial village.  However, you don’t have to stroll through a museum exhibit to see remnants of the harbor’s illustrious past.  Ancient clippers, schooners, skipjacks, log canoes, and bugeyes are all part of the dock atmosphere, along with hard-working watermen and pleasure boaters.  The quiet charm of this peaceful haven is most evident along historic streets lined with meticulously restored homes.  Today, St. Michaels attracts those who desire to escape the rush of city life or boating and sailing enthusiasts who want to live in close proximity to the waterfront.

    Listings in Saint Michaels, MD

    46

    Estimated median home price

    $749,500
    Saint Michaels MD Homes for Sale & Properties

    Weichert Realtors is one of the nation's leading providers of Saint Michaels, Maryland real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Saint Michaels, MD.

    Homes for Sale by Price in Saint Michaels, MD

    PriceCount
    $0 - 100K0
    $100K - 200K1
    $200K - 300K3
    $300K - 400K4
    $400K - 500K8
    $500K - 600K4
    $600K - 700K2
    $700K - 800K4
    $800K - 900K1
    $900K - 1M1
    $1M - Max18

    Homes for Sale by Type in Saint Michaels, MD

    Property TypeCount
    Single Family30
    Townhouse4
    Condo6
    Commercial3
    Rental8
    Lots and Land3
    Condo/Town/CoOp0
    CoOp0
    Multi Family0
    Mobile Home0
    Farms0

    (Data as of 3/18/2026)

    Information deemed reliable but not guaranteed.

    Information Deemed Reliable But Not Guaranteed. The data relating to real estate for sale on this website appears in part through the BrightMLS Broker ReciprocitySM program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Weichert, Realtors® participates, and is provided by BrightMLS through a licensing agreement.

    Real estate listings held by brokerage firms other than Weichert, Realtors® are marked with the Broker Reciprocity icon (a little black house) and detailed information about each listing includes the name of the listing broker.

    The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

    Some properties which appear for sale on this website may no longer be available because they are under contract, have sold or are no longer being offered for sale.

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