Saint Michaels Maryland Homes for Sale

37 total properties

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100 Grace Street Saint Michaels, MD MLS# MDTA2012398 - Image 1

100 Grace Street Saint Michaels, MD MLS# MDTA2012398 - Image 2

100 Grace Street Saint Michaels, MD MLS# MDTA2012398 - Image 3

100 Grace Street Saint Michaels, MD MLS# MDTA2012398 - Image 4

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100 Grace Street Saint Michaels, MD MLS# MDTA2012398 - Image 7

100 Grace Street Saint Michaels, MD MLS# MDTA2012398 - Image 8

100 Grace Street Saint Michaels, MD MLS# MDTA2012398 - Image 9

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100 Grace Street Saint Michaels, MD MLS# MDTA2012398 - Image 11

100 Grace Street Saint Michaels, MD MLS# MDTA2012398 - Image 12

100 Grace Street Saint Michaels, MD MLS# MDTA2012398 - Image 13

100 Grace Street Saint Michaels, MD MLS# MDTA2012398 - Image 14

100 Grace Street Saint Michaels, MD MLS# MDTA2012398 - Image 15

100 Grace Street Saint Michaels, MD MLS# MDTA2012398 - Image 16

100 Grace Street Saint Michaels, MD MLS# MDTA2012398 - Image 17

100 Grace Street Saint Michaels, MD MLS# MDTA2012398 - Image 18

100 Grace Street Saint Michaels, MD MLS# MDTA2012398 - Image 19

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100 Grace Street Saint Michaels, MD MLS# MDTA2012398 - Image 44

100 Grace Street Saint Michaels, MD MLS# MDTA2012398 - Image 45

100 Grace Street Saint Michaels, MD MLS# MDTA2012398 - Image 46

100 Grace Street Saint Michaels, MD MLS# MDTA2012398 - Image 47

100 Grace Street Saint Michaels, MD MLS# MDTA2012398 - Image 48

Recently Listed

1 of 48

$1,099,000

100 Grace Street

Saint Michaels, MD

Courtesy of BENSON & MANGOLD, LLC

100 Grace Street Saint Michaels, MD MLS# MDTA2012378 - Image 1

100 Grace Street Saint Michaels, MD MLS# MDTA2012378 - Image 2

100 Grace Street Saint Michaels, MD MLS# MDTA2012378 - Image 3

100 Grace Street Saint Michaels, MD MLS# MDTA2012378 - Image 4

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100 Grace Street Saint Michaels, MD MLS# MDTA2012378 - Image 11

100 Grace Street Saint Michaels, MD MLS# MDTA2012378 - Image 12

100 Grace Street Saint Michaels, MD MLS# MDTA2012378 - Image 13

100 Grace Street Saint Michaels, MD MLS# MDTA2012378 - Image 14

100 Grace Street Saint Michaels, MD MLS# MDTA2012378 - Image 15

100 Grace Street Saint Michaels, MD MLS# MDTA2012378 - Image 16

100 Grace Street Saint Michaels, MD MLS# MDTA2012378 - Image 17

100 Grace Street Saint Michaels, MD MLS# MDTA2012378 - Image 18

100 Grace Street Saint Michaels, MD MLS# MDTA2012378 - Image 19

100 Grace Street Saint Michaels, MD MLS# MDTA2012378 - Image 20

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100 Grace Street Saint Michaels, MD MLS# MDTA2012378 - Image 29

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100 Grace Street Saint Michaels, MD MLS# MDTA2012378 - Image 31

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100 Grace Street Saint Michaels, MD MLS# MDTA2012378 - Image 35

100 Grace Street Saint Michaels, MD MLS# MDTA2012378 - Image 36

100 Grace Street Saint Michaels, MD MLS# MDTA2012378 - Image 37

100 Grace Street Saint Michaels, MD MLS# MDTA2012378 - Image 38

100 Grace Street Saint Michaels, MD MLS# MDTA2012378 - Image 39

100 Grace Street Saint Michaels, MD MLS# MDTA2012378 - Image 40

100 Grace Street Saint Michaels, MD MLS# MDTA2012378 - Image 41

100 Grace Street Saint Michaels, MD MLS# MDTA2012378 - Image 42

100 Grace Street Saint Michaels, MD MLS# MDTA2012378 - Image 43

100 Grace Street Saint Michaels, MD MLS# MDTA2012378 - Image 44

100 Grace Street Saint Michaels, MD MLS# MDTA2012378 - Image 45

100 Grace Street Saint Michaels, MD MLS# MDTA2012378 - Image 46

Recently Listed

1 of 46

$1,099,000

Beds

2.1

Baths

1,445

Sq.Ft.

100 Grace Street

Saint Michaels, MD

Courtesy of BENSON & MANGOLD, LLC

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

108 Miles Avenue Saint Michaels, MD MLS# MDTA2012358 - Image 2

108 Miles Avenue Saint Michaels, MD MLS# MDTA2012358 - Image 3

108 Miles Avenue Saint Michaels, MD MLS# MDTA2012358 - Image 4

108 Miles Avenue Saint Michaels, MD MLS# MDTA2012358 - Image 5

108 Miles Avenue Saint Michaels, MD MLS# MDTA2012358 - Image 6

Recently Listed

1 of 6

$779,000

Beds

2.0

Baths

1,710

Sq.Ft.

108 Miles Avenue

Saint Michaels, MD

Courtesy of BENSON & MANGOLD, LLC

THE TIME TO SELL IS NOW!

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

108 Miles Avenue Saint Michaels, MD MLS# MDTA2012368 - Image 6

Recently Listed

1 of 6

$999,000

Beds

2.1

Baths

108 Miles Avenue

Saint Michaels, MD

Courtesy of BENSON & MANGOLD, LLC

0 Grace Saint Michaels, MD MLS# MDTA2012346 - Image 1

0 Grace Saint Michaels, MD MLS# MDTA2012346 - Image 2

0 Grace Saint Michaels, MD MLS# MDTA2012346 - Image 3

0 Grace Saint Michaels, MD MLS# MDTA2012346 - Image 4

0 Grace Saint Michaels, MD MLS# MDTA2012346 - Image 5

0 Grace Saint Michaels, MD MLS# MDTA2012346 - Image 6

0 Grace Saint Michaels, MD MLS# MDTA2012346 - Image 7

0 Grace Saint Michaels, MD MLS# MDTA2012346 - Image 8

0 Grace Saint Michaels, MD MLS# MDTA2012346 - Image 9

0 Grace Saint Michaels, MD MLS# MDTA2012346 - Image 10

1 of 10

$265,000

Studio

Beds

0.0

Baths

0 Grace

Saint Michaels, MD

Courtesy of BENSON & MANGOLD, LLC

108 Miles Avenue Saint Michaels, MD MLS# MDTA2012348 - Image 1

108 Miles Avenue Saint Michaels, MD MLS# MDTA2012348 - Image 2

108 Miles Avenue Saint Michaels, MD MLS# MDTA2012348 - Image 3

Recently Listed

1 of 3

$295,000

Studio

Beds

0.0

Baths

108 Miles Avenue

Saint Michaels, MD

Courtesy of BENSON & MANGOLD, LLC

105 Seymour Avenue Saint Michaels, MD MLS# MDTA2012362 - Image 1

105 Seymour Avenue Saint Michaels, MD MLS# MDTA2012362 - Image 2

105 Seymour Avenue Saint Michaels, MD MLS# MDTA2012362 - Image 3

105 Seymour Avenue Saint Michaels, MD MLS# MDTA2012362 - Image 4

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105 Seymour Avenue Saint Michaels, MD MLS# MDTA2012362 - Image 6

105 Seymour Avenue Saint Michaels, MD MLS# MDTA2012362 - Image 7

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105 Seymour Avenue Saint Michaels, MD MLS# MDTA2012362 - Image 9

105 Seymour Avenue Saint Michaels, MD MLS# MDTA2012362 - Image 10

105 Seymour Avenue Saint Michaels, MD MLS# MDTA2012362 - Image 11

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105 Seymour Avenue Saint Michaels, MD MLS# MDTA2012362 - Image 14

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105 Seymour Avenue Saint Michaels, MD MLS# MDTA2012362 - Image 31

105 Seymour Avenue Saint Michaels, MD MLS# MDTA2012362 - Image 32

105 Seymour Avenue Saint Michaels, MD MLS# MDTA2012362 - Image 33

105 Seymour Avenue Saint Michaels, MD MLS# MDTA2012362 - Image 34

105 Seymour Avenue Saint Michaels, MD MLS# MDTA2012362 - Image 35

105 Seymour Avenue Saint Michaels, MD MLS# MDTA2012362 - Image 36

105 Seymour Avenue Saint Michaels, MD MLS# MDTA2012362 - Image 37

Recently Listed with Virtual Tour

1 of 37

$499,000

Beds

1.0

Baths

1,080

Sq.Ft.

105 Seymour Avenue

Saint Michaels, MD

Courtesy of RE/MAX EXECUTIVE

23961 Lynnewood Drive Saint Michaels, MD MLS# MDTA2012318 - Image 1

23961 Lynnewood Drive Saint Michaels, MD MLS# MDTA2012318 - Image 2

23961 Lynnewood Drive Saint Michaels, MD MLS# MDTA2012318 - Image 3

23961 Lynnewood Drive Saint Michaels, MD MLS# MDTA2012318 - Image 4

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23961 Lynnewood Drive Saint Michaels, MD MLS# MDTA2012318 - Image 8

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23961 Lynnewood Drive Saint Michaels, MD MLS# MDTA2012318 - Image 13

23961 Lynnewood Drive Saint Michaels, MD MLS# MDTA2012318 - Image 14

23961 Lynnewood Drive Saint Michaels, MD MLS# MDTA2012318 - Image 15

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23961 Lynnewood Drive Saint Michaels, MD MLS# MDTA2012318 - Image 78

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23961 Lynnewood Drive Saint Michaels, MD MLS# MDTA2012318 - Image 81

23961 Lynnewood Drive Saint Michaels, MD MLS# MDTA2012318 - Image 82

23961 Lynnewood Drive Saint Michaels, MD MLS# MDTA2012318 - Image 83

Recently Listed with Virtual Tour

1 of 83

OPEN HOUSE: Saturday 12/6 12:00 PM - 2:00 PM

$3,100,000

Beds

3.1

Baths

4,035

Sq.Ft.

23961 Lynnewood Drive

Saint Michaels, MD

Courtesy of BENSON & MANGOLD, LLC

24318 Oakwood Park Road Saint Michaels, MD MLS# MDTA2012154 - Image 1

24318 Oakwood Park Road Saint Michaels, MD MLS# MDTA2012154 - Image 2

24318 Oakwood Park Road Saint Michaels, MD MLS# MDTA2012154 - Image 3

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24318 Oakwood Park Road Saint Michaels, MD MLS# MDTA2012154 - Image 42

24318 Oakwood Park Road Saint Michaels, MD MLS# MDTA2012154 - Image 43

24318 Oakwood Park Road Saint Michaels, MD MLS# MDTA2012154 - Image 44

1 of 44

$1,195,000

Beds

3.0

Baths

2,085

Sq.Ft.

24318 Oakwood Park Road

Saint Michaels, MD

Courtesy of COMPASS

9545 Quail Hollow # 205 Saint Michaels, MD MLS# MDTA2012128 - Image 1

9545 Quail Hollow # 205 Saint Michaels, MD MLS# MDTA2012128 - Image 2

9545 Quail Hollow # 205 Saint Michaels, MD MLS# MDTA2012128 - Image 3

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9545 Quail Hollow # 205 Saint Michaels, MD MLS# MDTA2012128 - Image 30

9545 Quail Hollow # 205 Saint Michaels, MD MLS# MDTA2012128 - Image 31

9545 Quail Hollow # 205 Saint Michaels, MD MLS# MDTA2012128 - Image 32

1 of 32

$385,000

Beds

3.0

Baths

1,800

Sq.Ft.

9545 Quail Hollow # 205

Saint Michaels, MD

Courtesy of LONG & FOSTER REAL ESTATE, INC.

202 Talbot Saint Michaels, MD MLS# MDTA2011864 - Image 1

202 Talbot Saint Michaels, MD MLS# MDTA2011864 - Image 2

202 Talbot Saint Michaels, MD MLS# MDTA2011864 - Image 3

202 Talbot Saint Michaels, MD MLS# MDTA2011864 - Image 4

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202 Talbot Saint Michaels, MD MLS# MDTA2011864 - Image 17

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1 of 35

$1,295,000

202 Talbot

Saint Michaels, MD

Courtesy of TTR SOTHEBY'S INTERNATIONAL REALTY

9171 Deepwater Point Road Saint Michaels, MD MLS# MDTA2011890 - Image 1

9171 Deepwater Point Road Saint Michaels, MD MLS# MDTA2011890 - Image 2

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9171 Deepwater Point Road Saint Michaels, MD MLS# MDTA2011890 - Image 39

9171 Deepwater Point Road Saint Michaels, MD MLS# MDTA2011890 - Image 40

Virtual Tour

1 of 40

$1,635,000

Beds

3.1

Baths

4,102

Sq.Ft.

9171 Deepwater Point Road

Saint Michaels, MD

Courtesy of TTR SOTHEBY'S INTERNATIONAL REALTY

23869 New Land Drive Saint Michaels, MD MLS# MDTA2011962 - Image 1

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23869 New Land Drive Saint Michaels, MD MLS# MDTA2011962 - Image 69

Virtual Tour

1 of 69

$1,850,000

Beds

2.0

Baths

2,717

Sq.Ft.

23869 New Land Drive

Saint Michaels, MD

Courtesy of MEREDITH FINE PROPERTIES

23869 New Land Drive Saint Michaels, MD MLS# MDTA2011984 - Image 1

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23869 New Land Drive Saint Michaels, MD MLS# MDTA2011984 - Image 69

Virtual Tour

1 of 69

$1,850,000

Beds

2.0

Baths

2,717

Sq.Ft.

23869 New Land Drive

Saint Michaels, MD

Courtesy of MEREDITH FINE PROPERTIES

Bozman Neavitt Saint Michaels, MD MLS# MDTA2011976 - Image 1

Bozman Neavitt Saint Michaels, MD MLS# MDTA2011976 - Image 2

Bozman Neavitt Saint Michaels, MD MLS# MDTA2011976 - Image 3

Bozman Neavitt Saint Michaels, MD MLS# MDTA2011976 - Image 4

1 of 4

$895,000

Studio

Beds

0.0

Baths

Bozman Neavitt

Saint Michaels, MD

Courtesy of BENSON & MANGOLD, LLC

216 Brooks Saint Michaels, MD MLS# MDTA2011960 - Image 1

216 Brooks Saint Michaels, MD MLS# MDTA2011960 - Image 2

216 Brooks Saint Michaels, MD MLS# MDTA2011960 - Image 3

216 Brooks Saint Michaels, MD MLS# MDTA2011960 - Image 4

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216 Brooks Saint Michaels, MD MLS# MDTA2011960 - Image 14

216 Brooks Saint Michaels, MD MLS# MDTA2011960 - Image 15

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216 Brooks Saint Michaels, MD MLS# MDTA2011960 - Image 37

New Construction

1 of 37

$479,999

Beds

2.0

Baths

1,500

Sq.Ft.

216 Brooks

Saint Michaels, MD

Courtesy of LPT REALTY, LLC

207 Dodson Avenue Saint Michaels, MD MLS# MDTA2011910 - Image 1

207 Dodson Avenue Saint Michaels, MD MLS# MDTA2011910 - Image 2

207 Dodson Avenue Saint Michaels, MD MLS# MDTA2011910 - Image 3

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207 Dodson Avenue Saint Michaels, MD MLS# MDTA2011910 - Image 46

1 of 46

$499,900

Beds

2.0

Baths

960

Sq.Ft.

207 Dodson Avenue

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

228 Tyler Avenue Saint Michaels, MD MLS# MDTA2011870 - Image 4

228 Tyler Avenue Saint Michaels, MD MLS# MDTA2011870 - Image 5

228 Tyler Avenue Saint Michaels, MD MLS# MDTA2011870 - Image 6

228 Tyler Avenue Saint Michaels, MD MLS# MDTA2011870 - Image 7

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228 Tyler Avenue Saint Michaels, MD MLS# MDTA2011870 - Image 9

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228 Tyler Avenue Saint Michaels, MD MLS# MDTA2011870 - Image 11

228 Tyler Avenue Saint Michaels, MD MLS# MDTA2011870 - Image 12

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228 Tyler Avenue Saint Michaels, MD MLS# MDTA2011870 - Image 38

228 Tyler Avenue Saint Michaels, MD MLS# MDTA2011870 - Image 39

228 Tyler Avenue Saint Michaels, MD MLS# MDTA2011870 - Image 40

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228 Tyler Avenue Saint Michaels, MD MLS# MDTA2011870 - Image 43

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

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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Virtual Tour

1 of 82

OPEN HOUSE: Saturday 12/6 2:00 PM - 4:00 PM

$725,000

Beds

2.1

Baths

1,957

Sq.Ft.

408 Spinnaker Lane

Saint Michaels, MD

Courtesy of NORTHROP REALTY

912 Calvert Ave. Saint Michaels, MD MLS# MDTA2011868 - Image 1

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$229,000

Studio

Beds

0.0

Baths

912 Calvert Ave.

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: 38
Estimated median home price: $825,000

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	1
$200K - 300K	2
$300K - 400K	5
$400K - 500K	2
$500K - 600K	2
$600K - 700K	3
$700K - 800K	3
$800K - 900K	4
$900K - 1M	0
$1M - Max	16

Homes for Sale by Type in Saint Michaels, MD

Property Type	Count
Single Family	23
Townhouse	0
Condo	4
Commercial	6
Rental	8
Lots and Land	4
Condo/Town/CoOp	0
CoOp	0
Multi Family	0
Mobile Home	0
Farms	1

(Data as of 11/11/2025)

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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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