Saint Michaels Maryland Homes for Sale

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114 W Chestnut Street Saint Michaels, MD MLS# MDTA2013116 - Image 1

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1 of 73

$1,350,000

Beds

4.1

Baths

3,528

Sq.Ft.

114 W Chestnut Street

Saint Michaels, MD

Courtesy of BENSON & MANGOLD, LLC

106 Chestnut Street E Saint Michaels, MD MLS# MDTA2013108 - Image 1

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Virtual Tour

1 of 86

$1,325,000

Beds

2.1

Baths

2,282

Sq.Ft.

106 Chestnut Street E

Saint Michaels, MD

Courtesy of TAYLOR PROPERTIES

114 E Chew Avenue Saint Michaels, MD MLS# MDTA2012948 - Image 1

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1 of 57

$1,250,000

Beds

2.1

Baths

2,336

Sq.Ft.

114 E Chew Avenue

Saint Michaels, MD

Courtesy of BENSON & MANGOLD, LLC

THE TIME TO SELL IS NOW!

107 W Chestnut Street Saint Michaels, MD MLS# MDTA2012552 - Image 1

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Virtual Tour

1 of 105

$1,225,000

Beds

2.0

Baths

1,914

Sq.Ft.

107 W Chestnut Street

Saint Michaels, MD

Courtesy of CHESAPEAKE BAY REAL ESTATE PLUS, LLC

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Recently Listed with Virtual Tour

1 of 93

$1,200,000

Beds

2.1

Baths

2,200

Sq.Ft.

504 Seymour Avenue

Saint Michaels, MD

Courtesy of BENSON & MANGOLD, LLC

101 Mulberry Street Saint Michaels, MD MLS# MDTA2013022 - Image 1

101 Mulberry Street Saint Michaels, MD MLS# MDTA2013022 - Image 2

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101 Mulberry Street Saint Michaels, MD MLS# MDTA2013022 - Image 38

1 of 38

OPEN HOUSE: Sunday 4/19 1:00 PM - 3:00 PM

$1,194,000

Beds

2.1

Baths

1,500

Sq.Ft.

101 Mulberry Street

Saint Michaels, MD

Courtesy of MEREDITH FINE PROPERTIES

1103 S Talbot Street Saint Michaels, MD MLS# MDTA2008124 - Image 1

1103 S Talbot Street Saint Michaels, MD MLS# MDTA2008124 - Image 2

1103 S Talbot Street Saint Michaels, MD MLS# MDTA2008124 - Image 3

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1103 S Talbot Street Saint Michaels, MD MLS# MDTA2008124 - Image 43

1103 S Talbot Street Saint Michaels, MD MLS# MDTA2008124 - Image 44

Virtual Tour

1 of 44

$1,100,000

6,950

Sq.Ft.

1103 S Talbot Street

Saint Michaels, MD

Courtesy of BENSON & MANGOLD, LLC

108 Miles Avenue Saint Michaels, MD MLS# MDTA2012368 - Image 1

108 Miles Avenue Saint Michaels, MD MLS# MDTA2012368 - Image 2

108 Miles Avenue Saint Michaels, MD MLS# MDTA2012368 - Image 3

108 Miles Avenue Saint Michaels, MD MLS# MDTA2012368 - Image 4

108 Miles Avenue Saint Michaels, MD MLS# MDTA2012368 - Image 5

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108 Miles Avenue Saint Michaels, MD MLS# MDTA2012368 - Image 25

New Construction

1 of 25

$999,000

Beds

2.1

Baths

108 Miles Avenue

Saint Michaels, MD

Courtesy of BENSON & MANGOLD, LLC

24822 Swan Road Saint Michaels, MD MLS# MDTA2012848 - Image 1

24822 Swan Road Saint Michaels, MD MLS# MDTA2012848 - Image 2

24822 Swan Road Saint Michaels, MD MLS# MDTA2012848 - Image 3

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24822 Swan Road Saint Michaels, MD MLS# MDTA2012848 - Image 35

24822 Swan Road Saint Michaels, MD MLS# MDTA2012848 - Image 36

24822 Swan Road Saint Michaels, MD MLS# MDTA2012848 - Image 37

Virtual Tour

1 of 37

$830,000

Beds

3.0

Baths

2,439

Sq.Ft.

24822 Swan Road

Saint Michaels, MD

Courtesy of BENSON & MANGOLD, LLC

Lot 16A Meadow Street Saint Michaels, MD MLS# MDTA2007414 - Image 1

Lot 16A Meadow Street Saint Michaels, MD MLS# MDTA2007414 - Image 2

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Lot 16A Meadow Street Saint Michaels, MD MLS# MDTA2007414 - Image 24

Lot 16A Meadow Street Saint Michaels, MD MLS# MDTA2007414 - Image 25

New Construction

1 of 25

$799,000

Beds

2.1

Baths

Lot 16A Meadow Street

Saint Michaels, MD

Courtesy of KELLER WILLIAMS FLAGSHIP

108 Miles Avenue Saint Michaels, MD MLS# MDTA2012358 - Image 1

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108 Miles Avenue Saint Michaels, MD MLS# MDTA2012358 - Image 23

108 Miles Avenue Saint Michaels, MD MLS# MDTA2012358 - Image 24

108 Miles Avenue Saint Michaels, MD MLS# MDTA2012358 - Image 25

New Construction

1 of 25

$779,000

Beds

2.0

Baths

1,710

Sq.Ft.

108 Miles Avenue

Saint Michaels, MD

Courtesy of BENSON & MANGOLD, LLC

24977 Back Creek Drive Saint Michaels, MD MLS# MDTA2010224 - Image 1

24977 Back Creek Drive Saint Michaels, MD MLS# MDTA2010224 - Image 2

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24977 Back Creek Drive Saint Michaels, MD MLS# MDTA2010224 - Image 70

1 of 70

$749,999

Beds

3.1

Baths

3,010

Sq.Ft.

24977 Back Creek Drive

Saint Michaels, MD

Courtesy of BENSON & MANGOLD, LLC

9206 Martingham Drive Saint Michaels, MD MLS# MDTA2013200 - Image 1

9206 Martingham Drive Saint Michaels, MD MLS# MDTA2013200 - Image 2

9206 Martingham Drive Saint Michaels, MD MLS# MDTA2013200 - Image 3

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9206 Martingham Drive Saint Michaels, MD MLS# MDTA2013200 - Image 69

Virtual Tour

1 of 69

$749,000

Beds

2.1

Baths

2,841

Sq.Ft.

9206 Martingham Drive

Saint Michaels, MD

Courtesy of CHESAPEAKE BAY REAL ESTATE PLUS, LLC

408 Spinnaker Lane Saint Michaels, MD MLS# MDTA2011880 - Image 1

408 Spinnaker Lane Saint Michaels, MD MLS# MDTA2011880 - Image 2

408 Spinnaker Lane Saint Michaels, MD MLS# MDTA2011880 - Image 3

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408 Spinnaker Lane Saint Michaels, MD MLS# MDTA2011880 - Image 82

Virtual Tour

1 of 82

$699,000

Beds

2.1

Baths

1,957

Sq.Ft.

408 Spinnaker Lane

Saint Michaels, MD

Courtesy of NORTHROP REALTY

204 E Marengo Street Saint Michaels, MD MLS# MDTA2013184 - Image 1

204 E Marengo Street Saint Michaels, MD MLS# MDTA2013184 - Image 2

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204 E Marengo Street Saint Michaels, MD MLS# MDTA2013184 - Image 72

Virtual Tour

1 of 72

$599,000

Beds

1.0

Baths

1,200

Sq.Ft.

204 E Marengo Street

Saint Michaels, MD

Courtesy of COMPASS

113 Gloria Saint Michaels, MD MLS# MDTA2013264 - Image 1

113 Gloria Saint Michaels, MD MLS# MDTA2013264 - Image 2

113 Gloria Saint Michaels, MD MLS# MDTA2013264 - Image 3

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113 Gloria Saint Michaels, MD MLS# MDTA2013264 - Image 36

1 of 36

$595,000

Beds

2.0

Baths

1,456

Sq.Ft.

113 Gloria

Saint Michaels, MD

Courtesy of BENSON & MANGOLD, LLC

228 Tyler Avenue Saint Michaels, MD MLS# MDTA2011870 - Image 1

228 Tyler Avenue Saint Michaels, MD MLS# MDTA2011870 - Image 2

228 Tyler Avenue Saint Michaels, MD MLS# MDTA2011870 - Image 3

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228 Tyler Avenue Saint Michaels, MD MLS# MDTA2011870 - Image 44

1 of 44

$549,900

Beds

2.1

Baths

1,922

Sq.Ft.

228 Tyler Avenue

Saint Michaels, MD

Courtesy of BENSON & MANGOLD, LLC

1211 Washington Saint Michaels, MD MLS# MDTA2012942 - Image 1

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1211 Washington Saint Michaels, MD MLS# MDTA2012942 - Image 14

1 of 14

$525,000

Beds

2.2

Baths

2,420

Sq.Ft.

1211 Washington

Saint Michaels, MD

Courtesy of LONG & FOSTER REAL ESTATE, INC.

1215 Washington Saint Michaels, MD MLS# MDTA2012950 - Image 1

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1 of 30

$525,000

Beds

2.2

Baths

2,420

Sq.Ft.

1215 Washington

Saint Michaels, MD

Courtesy of LONG & FOSTER REAL ESTATE, INC.

9518 Quail Hollow # 702 Saint Michaels, MD MLS# MDTA2012850 - Image 1

9518 Quail Hollow # 702 Saint Michaels, MD MLS# MDTA2012850 - Image 2

9518 Quail Hollow # 702 Saint Michaels, MD MLS# MDTA2012850 - Image 3

9518 Quail Hollow # 702 Saint Michaels, MD MLS# MDTA2012850 - Image 4

9518 Quail Hollow # 702 Saint Michaels, MD MLS# MDTA2012850 - Image 5

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Virtual Tour

1 of 36

$480,000

Beds

3.0

Baths

1,800

Sq.Ft.

9518 Quail Hollow # 702

Saint Michaels, MD

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: 50
Estimated median home price: $1,197,000

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

Price	Count
$0 - 100K	0
$100K - 200K	0
$200K - 300K	3
$300K - 400K	3
$400K - 500K	5
$500K - 600K	5
$600K - 700K	1
$700K - 800K	4
$800K - 900K	1
$900K - 1M	1
$1M - Max	27

Homes for Sale by Type in Saint Michaels, MD

Property Type	Count
Single Family	38
Townhouse	3
Condo	4
Commercial	2
Rental	7
Lots and Land	3
Condo/Town/CoOp	0
CoOp	0
Multi Family	0
Mobile Home	0
Farms	0

(Data as of 4/19/2026)

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Information Deemed Reliable But Not Guaranteed. The data relating to real estate for sale on this website appears in part through the BrightMLS Broker Reciprocity^SM 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.

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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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