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21663, MD - homes for sale
60 of 60 results displayed
- Open Sun, 12 to 2pmNew
$399,000Active4 beds 2 baths1,743 sq. ft.214 Madison Ave, SAINT MICHAELS, MD 21663
MLS# MDTA2014662Listed by: BERKSHIRE HATHAWAY HOMESERVICES PENFED REALTY - New
$375,000Active2 beds 2 baths1,800 sq. ft.24362 Widgeon Pl #5, SAINT MICHAELS, MD 21663
MLS# MDTA2014768Listed by: MEREDITH FINE PROPERTIES - New
$1,470,000Active3 beds 3 baths1,938 sq. ft.104 Mulberry St, SAINT MICHAELS, MD 21663
MLS# MDTA2014766Listed by: RE/MAX ONE - Open Sat, 1 to 3pm
$995,000Active3 beds 3 baths2,091 sq. ft.101 Seymour, SAINT MICHAELS, MD 21663
MLS# MDTA2014666Listed by: MEREDITH FINE PROPERTIES 
$3,200,000Pending4 beds 6 baths3,100 sq. ft.703 Riverview Ter, SAINT MICHAELS, MD 21663
MLS# MDTA2014664Listed by: MEREDITH FINE PROPERTIES
$650,000Pending3 beds 3 baths2,902 sq. ft.24895 Back Creek Dr, ST MICHAELS, MD 21663
MLS# MDTA2014610Listed by: BENSON & MANGOLD, LLC
$459,900Active4 beds 4 baths2,420 sq. ft.104 Madison Ave, ST MICHAELS, MD 21663
MLS# MDTA2014616Listed by: BENSON & MANGOLD, LLC
$1,595,000Pending4 beds 3 baths1,983 sq. ft.6905 Pea Neck, SAINT MICHAELS, MD 21663
MLS# MDTA2014500Listed by: BENSON & MANGOLD, LLC
$359,900Active2 beds 3 baths1,800 sq. ft.9531 Quail Hollow Dr #405, ST MICHAELS, MD 21663
MLS# MDTA2014522Listed by: BENSON & MANGOLD, LLC
$795,000Active3 beds 2 baths1,288 sq. ft.803 New Ln, ST MICHAELS, MD 21663
MLS# MDTA2014422Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY
$849,800Pending5 beds 5 baths3,452 sq. ft.24896 Back Creek, SAINT MICHAELS, MD 21663
MLS# MDTA2013974Listed by: MEREDITH FINE PROPERTIES
$600,000Pending4 beds 3 baths2,841 sq. ft.9206 Martingham Dr, SAINT MICHAELS, MD 21663
MLS# MDTA2014180Listed by: SAMSON PROPERTIES
$1,995,000Active4 beds 3 baths3,028 sq. ft.9020 Bozman Neavitt Rd, SAINT MICHAELS, MD 21663
MLS# MDTA2014168Listed by: BENSON & MANGOLD, LLC
$1,795,000Active3 beds 2 baths2,160 sq. ft.23776 Mount Pleasant Landing, SAINT MICHAELS, MD 21663
MLS# MDTA2014128Listed by: SHORE LIVING REAL ESTATE
$549,999Active2 beds 1 baths1,200 sq. ft.204 E Marengo St, SAINT MICHAELS, MD 21663
MLS# MDTA2014132Listed by: COMPASS
$1,300,000Pending3 beds 3 baths1,836 sq. ft.344 Perry Cabin Dr, SAINT MICHAELS, MD 21663
MLS# MDTA2014064Listed by: CHESAPEAKE BAY REAL ESTATE PLUS, LLC
$2,250,000Pending5 beds 2 baths4,706 sq. ft.8209 Tricefield, SAINT MICHAELS, MD 21663
MLS# MDTA2013748Listed by: CHESAPEAKE BAY REAL ESTATE PLUS, LLC
$995,000Active4 beds 3 baths2,250 sq. ft.109 W Marengo St, SAINT MICHAELS, MD 21663
MLS# MDTA2013980Listed by: BENSON & MANGOLD, LLC
$3,495,000Active4 beds 5 baths6,404 sq. ft.24678 New Post Rd, SAINT MICHAELS, MD 21663
MLS# MDTA2013978Listed by: BENSON & MANGOLD, LLC
$489,000Pending3 beds 3 baths2,100 sq. ft.24375 Widgeon #37, SAINT MICHAELS, MD 21663
MLS# MDTA2013878Listed by: MEREDITH FINE PROPERTIES
$309,000Pending3 beds 2 baths1,364 sq. ft.203 Canton St, ST MICHAELS, MD 21663
MLS# MDTA2013846Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
$679,000Active4 beds 3 baths2,072 sq. ft.24555 Deepwater Point, SAINT MICHAELS, MD 21663
MLS# MDTA2013746Listed by: CHESAPEAKE BAY REAL ESTATE PLUS, LLC
$385,000Active2 beds 3 baths1,477 sq. ft.24700 Deepwater Point #20, SAINT MICHAELS, MD 21663
MLS# MDTA2013730Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY
$2,349,000Pending4 beds 5 baths3,300 sq. ft.962 San Domingo Ct, SAINT MICHAELS, MD 21663
MLS# MDTA2013656Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY
$993,000Active3 beds 2 baths1,362 sq. ft.8090 Bozman Neavitt Rd, BOZMAN, MD 21612
MLS# MDTA2013734Listed by: BENSON & MANGOLD, LLC
$1,650,000Pending3 beds 3 baths3,078 sq. ft.602 Landing Road, SAINT MICHAELS, MD 21663
MLS# MDTA2013718Listed by: BENSON & MANGOLD, LLC
$359,000Active2 beds 3 baths1,487 sq. ft.24700 Deepwater Point #23, SAINT MICHAELS, MD 21663
MLS# MDTA2013354Listed by: MEREDITH FINE PROPERTIES
$799,900Active3 beds 3 baths2,027 sq. ft.807 Radcliff Ave, SAINT MICHAELS, MD 21663
MLS# MDTA2013534Listed by: LONG & FOSTER REAL ESTATE, INC.
$598,000Active3 beds 2 baths2,348 sq. ft.204 Lincoln, SAINT MICHAELS, MD 21663
MLS# MDTA2013092Listed by: LONG & FOSTER REAL ESTATE, INC.
$795,000Active4 beds 3 baths1,988 sq. ft.9359 Martingham, SAINT MICHAELS, MD 21663
MLS# MDTA2013550Listed by: LONG & FOSTER REAL ESTATE, INC.
$1,679,000Active4 beds 4 baths2,839 sq. ft.24390 Oakwood Park Rd, SAINT MICHAELS, MD 21663
MLS# MDTA2012326Listed by: BENSON & MANGOLD, LLC
$1,049,000Pending3 beds 3 baths2,200 sq. ft.504 Seymour Ave, SAINT MICHAELS, MD 21663
MLS# MDTA2013438Listed by: BENSON & MANGOLD, LLC
$1,379,800Active4 beds 4 baths3,332 sq. ft.7865 Pea Neck, SAINT MICHAELS, MD 21663
MLS# MDTA2013310Listed by: MEREDITH FINE PROPERTIES
$739,000Pending4 beds 3 baths2,798 sq. ft.24965 Back Creek Dr, ST MICHAELS, MD 21663
MLS# MDTA2013112Listed by: BENSON & MANGOLD, LLC
$479,000Active3 beds 2 baths1,761 sq. ft.8000 Bozman Neavitt Rd, BOZMAN, MD 21612
MLS# MDTA2013128Listed by: BENSON & MANGOLD, LLC
$1,985,000Active3 beds 3 baths2,622 sq. ft.303 Manor, SAINT MICHAELS, MD 21663
MLS# MDTA2013226Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY
$249,000Active1.12 AcresDeepwater Point, SAINT MICHAELS, MD 21663
MLS# MDTA2013260Listed by: LONG & FOSTER REAL ESTATE, INC.
$2,000,000Active4 beds 3 baths4,492 sq. ft.7909 Church Neck, SAINT MICHAELS, MD 21663
MLS# MDTA2013238Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY
$2,149,000Active3 beds 3 baths3,017 sq. ft.7149 Drum Point, SAINT MICHAELS, MD 21663
MLS# MDTA2013096Listed by: LONG & FOSTER REAL ESTATE, INC.
$1,195,000Active4 beds 5 baths3,528 sq. ft.114 W Chestnut St, SAINT MICHAELS, MD 21663
MLS# MDTA2013116Listed by: BENSON & MANGOLD, LLC- Open Sat, 11am to 1pm
$1,179,000Active4 beds 3 baths1,500 sq. ft.101 Mulberry St, SAINT MICHAELS, MD 21663
MLS# MDTA2013022Listed by: MEREDITH FINE PROPERTIES 
$2,575,000Pending5 beds 9 baths4,394 sq. ft.205 Cherry St, SAINT MICHAELS, MD 21663
MLS# MDTA2012738Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY
$3,250,000Pending4 beds 5 baths3,289 sq. ft.601 Cove Rd, SAINT MICHAELS, MD 21663
MLS# MDTA2012912Listed by: BENSON & MANGOLD, LLC
$499,000Active4 beds 4 baths2,420 sq. ft.1211 Washington, SAINT MICHAELS, MD 21663
MLS# MDTA2012942Listed by: LONG & FOSTER REAL ESTATE, INC.
$499,000Active4 beds 4 baths2,420 sq. ft.1215 Washington, SAINT MICHAELS, MD 21663
MLS# MDTA2012950Listed by: LONG & FOSTER REAL ESTATE, INC.
$1,685,000Active5 beds 5 baths4,728 sq. ft.9180 Saint Michaels, SAINT MICHAELS, MD 21663
MLS# MDTA2012944Listed by: LONG & FOSTER REAL ESTATE, INC.
$2,275,000Pending4 beds 5 baths3,677 sq. ft.24645 Long Haul, SAINT MICHAELS, MD 21663
MLS# MDTA2012746Listed by: COLDWELL BANKER REALTY
$1,945,000Active6 beds 6 baths4,089 sq. ft.228 Perry Cabin Dr #228 / 226, SAINT MICHAELS, MD 21663
MLS# MDTA2012940Listed by: CHESAPEAKE BAY REAL ESTATE PLUS, LLC
$425,000Active3 beds 2 baths1,120 sq. ft.101 Brooks Ln, SAINT MICHAELS, MD 21663
MLS# MDTA2012900Listed by: BENSON & MANGOLD, LLC
$1,595,000Pending4 beds 4 baths3,575 sq. ft.216 E Chew Ave, SAINT MICHAELS, MD 21663
MLS# MDTA2012450Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
$779,000Active3 beds 2 baths1,710 sq. ft.108 Miles Ave, SAINT MICHAELS, MD 21663
MLS# MDTA2012358Listed by: BENSON & MANGOLD, LLC
$999,000Active3 beds 3 baths108 Miles Ave, SAINT MICHAELS, MD 21663
MLS# MDTA2012368Listed by: BENSON & MANGOLD, LLC
$295,000Active0.55 Acres108 Miles Ave, SAINT MICHAELS, MD 21663
MLS# MDTA2012348Listed by: BENSON & MANGOLD, LLC
$3,100,000Pending4 beds 4 baths4,035 sq. ft.23961 Lynnewood Dr, SAINT MICHAELS, MD 21663
MLS# MDTA2012318Listed by: BENSON & MANGOLD, LLC
$374,000Active2 beds 3 baths1,800 sq. ft.9545 Quail Hollow #205, SAINT MICHAELS, MD 21663
MLS# MDTA2012128Listed by: LONG & FOSTER REAL ESTATE, INC.
$219,000Active0.25 Acres912 Calvert Ave., SAINT MICHAELS, MD 21663
MLS# MDTA2011868Listed by: BENSON & MANGOLD, LLC
$8,495,000Active6 beds 11 baths17,402 sq. ft.8620 Bozman Neavitt, SAINT MICHAELS, MD 21663
MLS# MDTA2010616Listed by: WASHINGTON FINE PROPERTIES, LLC
$455,000Active3 beds 3 baths1,800 sq. ft.9518 Quail Hollow #702, SAINT MICHAELS, MD 21663
MLS# MDTA2012850Listed by: BENSON & MANGOLD, LLC
$799,000Active4 beds 3 bathsLot 16a Meadow St, SAINT MICHAELS, MD 21663
MLS# MDTA2007414Listed by: KELLER WILLIAMS FLAGSHIP
$1,995,000Pending3 beds 3 baths3,562 sq. ft.7369 Drum Point Rd, SAINT MICHAELS, MD 21663
MLS# MDTA2009428Listed by: MEREDITH FINE PROPERTIES
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© 2026 Better Homes and Gardens Real Estate LLC. An Anywhere Real Estate company. All rights reserved. Better Homes and Gardens® Real Estate is a registered trademark owned by Meredith Operations Corporation, licensed to Better Homes and Gardens Real Estate LLC and used with permission. Better Homes and Gardens Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Listing information is deemed reliable but is not guaranteed accurate.
Each office is independently owned and operated.
Any services or products provided by third parties are not provided by, affiliated with or related to Better Homes and Gardens Real Estate LLC, or its affiliated companies.
Protect your home and budget from life's surprises with an Assurant Home Warranty, backed by a partner that supports you through every step of homeownership. Explore Plans.
© 2026 Better Homes and Gardens Real Estate LLC. An Anywhere Real Estate company. All rights reserved. Better Homes and Gardens® Real Estate is a registered trademark owned by Meredith Operations Corporation, licensed to Better Homes and Gardens Real Estate LLC and used with permission. Better Homes and Gardens Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Listing information is deemed reliable but is not guaranteed accurate.
Each office is independently owned and operated.
Any services or products provided by third parties are not provided by, affiliated with or related to Better Homes and Gardens Real Estate LLC, or its affiliated companies.