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The Chesapeake Bay gives life to the DMV area, with its incredible resource of entertainment, food, and culture. Running alongside both Maryland and Virginia, the Chesapeake Bay and its subsequent waterways draw visitors and residents alike to its peaceful waters. The western side of the Chesapeake Bay begins north of Baltimore and rides down past Annapolis on to Newport News, VA. The Chesapeake Bay Bridge is a 4.35 mile passage from Annapolis to the Eastern Shore, which has become a popular destination for tourists and those looking for a second home getaway. The Eastern Shore boasts classic nautical towns like Kent Island, St. Michaels, Oxford and Cambridge. Many residents from the DMV area travel over the Chesapeake Bay and continue on to the Delmarva Beaches.
Min. Price
Max. Price
Beds
Baths
27 OLD SOUTH RIVER RD EDGEWATER, MD 21037
$18,000,000
4 Beds 3 Baths 2,756 SqFt Listing No. MDAA2118916 Property Type: House camera (32)
Details
6150 OXFORD RD EASTON, MD 21601
$12,500,000
2 Beds 1 | 2 Baths 2,388 SqFt Listing No. MDTA2011914 Property Type: House camera Virtual Tour camera (52)
Details
29245 HOWELL POINT RD TRAPPE, MD 21673
$11,000,000
4 Beds 3 | 2 Baths 6,000 SqFt Listing No. MDTA2012732 Property Type: House
Details
6010 SHIPYARD LN EASTON, MD 21601
$9,900,000
5 Beds 4 | 2 Baths 14,935 SqFt Listing No. MDTA2005396 Property Type: House camera Virtual Tour camera (71)
Details
27295 SOUTHSIDE ISLAND CREEK RD TRAPPE, MD 21673
$8,750,000
6 Beds 4 | 2 Baths 9,566 SqFt Listing No. MDTA2006798 Property Type: House camera Virtual Tour camera (91)
Details
125 S WINCHESTER RD ANNAPOLIS, MD 21409
$8,750,000
5 Beds 5 | 2 Baths 11,269 SqFt Listing No. MDAA2132598 Property Type: House camera Virtual Tour camera (47)
Details
8620 BOZMAN NEAVITT SAINT MICHAELS, MD 21663
$8,495,000
6 Beds 7 | 4 Baths 17,402 SqFt Listing No. MDTA2010616 Property Type: House camera Virtual Tour camera (60)
Details
3750 WINDY HILL RD TRAPPE, MD 21673
$8,400,000
3 Beds 2 Baths 1,966 SqFt Listing No. MDTA2012586 Property Type: House camera (55)
Details
7508 COOPER POINT RD BOZMAN, MD 21612
$7,500,000
6 Beds 6 | 2 Baths 8,476 SqFt Listing No. MDTA2012566 Property Type: House camera Virtual Tour camera (98)
Details
7090 COOPER POINT RD BOZMAN, MD 21612
$7,500,000
5 Beds 4 | 2 Baths 10,000 SqFt Listing No. MDTA2011288 Property Type: House camera Virtual Tour camera (86)
Details
5499 ANDERBY HALL RD ROYAL OAK, MD 21662
$6,000,000
3 Beds 4 Baths 5,921 SqFt Listing No. MDTA2011958 Property Type: House camera Virtual Tour camera (87)
Details
1 SHIPWRIGHT HARBOR ANNAPOLIS, MD 21401
$5,898,000
3 Beds 3 | 1 Baths 3,108 SqFt Listing No. MDAA2132250 Property Type: House camera Virtual Tour camera (39)
Details
 27 OLD SOUTH RIVER RD, EDGEWATER, MD 21037
camera (32)
price

$18,000,000

beds

4 4 Beds

baths

3 3 Baths

lot size

2,756 SqFt 2,756 SqFt

listing no.

MDAA2118916 Listing No. MDAA2118916

property type

House Property Type: House

gallery photos

camera (32)

 6150 OXFORD RD, EASTON, MD 21601
camera VIRTUAL TOUR camera (52)
price

$12,500,000

beds

2 2 Beds

baths

1 | 2 1 | 2 Baths

lot size

2,388 SqFt 2,388 SqFt

listing no.

MDTA2011914 Listing No. MDTA2011914

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (52)

 29245 HOWELL POINT RD, TRAPPE, MD 21673
price

$11,000,000

beds

4 4 Beds

baths

3 | 2 3 | 2 Baths

lot size

6,000 SqFt 6,000 SqFt

listing no.

MDTA2012732 Listing No. MDTA2012732

property type

House Property Type: House

 6010 SHIPYARD LN, EASTON, MD 21601
camera VIRTUAL TOUR camera (71)
price

$9,900,000

beds

5 5 Beds

baths

4 | 2 4 | 2 Baths

lot size

14,935 SqFt 14,935 SqFt

listing no.

MDTA2005396 Listing No. MDTA2005396

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (71)

 27295 SOUTHSIDE ISLAND CREEK RD, TRAPPE, MD 21673
camera VIRTUAL TOUR camera (91)
price

$8,750,000

beds

6 6 Beds

baths

4 | 2 4 | 2 Baths

lot size

9,566 SqFt 9,566 SqFt

listing no.

MDTA2006798 Listing No. MDTA2006798

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (91)

 125 S WINCHESTER RD, ANNAPOLIS, MD 21409
Coming Soon
camera VIRTUAL TOUR camera (47)
price

$8,750,000

beds

5 5 Beds

baths

5 | 2 5 | 2 Baths

lot size

11,269 SqFt 11,269 SqFt

listing no.

MDAA2132598 Listing No. MDAA2132598

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (47)

 8620 BOZMAN NEAVITT, SAINT MICHAELS, MD 21663
camera VIRTUAL TOUR camera (60)
price

$8,495,000

beds

6 6 Beds

baths

7 | 4 7 | 4 Baths

lot size

17,402 SqFt 17,402 SqFt

listing no.

MDTA2010616 Listing No. MDTA2010616

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (60)

 3750 WINDY HILL RD, TRAPPE, MD 21673
camera (55)
price

$8,400,000

beds

3 3 Beds

baths

2 2 Baths

lot size

1,966 SqFt 1,966 SqFt

listing no.

MDTA2012586 Listing No. MDTA2012586

property type

House Property Type: House

gallery photos

camera (55)

 7508 COOPER POINT RD, BOZMAN, MD 21612
camera VIRTUAL TOUR camera (98)
price

$7,500,000

beds

6 6 Beds

baths

6 | 2 6 | 2 Baths

lot size

8,476 SqFt 8,476 SqFt

listing no.

MDTA2012566 Listing No. MDTA2012566

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (98)

 7090 COOPER POINT RD, BOZMAN, MD 21612
camera VIRTUAL TOUR camera (86)
price

$7,500,000

beds

5 5 Beds

baths

4 | 2 4 | 2 Baths

lot size

10,000 SqFt 10,000 SqFt

listing no.

MDTA2011288 Listing No. MDTA2011288

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (86)

 5499 ANDERBY HALL RD, ROYAL OAK, MD 21662
camera VIRTUAL TOUR camera (87)
price

$6,000,000

beds

3 3 Beds

baths

4 4 Baths

lot size

5,921 SqFt 5,921 SqFt

listing no.

MDTA2011958 Listing No. MDTA2011958

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (87)

 1 SHIPWRIGHT HARBOR, ANNAPOLIS, MD 21401
Coming Soon
camera VIRTUAL TOUR camera (39)
price

$5,898,000

beds

3 3 Beds

baths

3 | 1 3 | 1 Baths

lot size

3,108 SqFt 3,108 SqFt

listing no.

MDAA2132250 Listing No. MDAA2132250

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (39)

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The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Compass participates, and is provided by BRIGHT through a licensing agreement. Real estate listings held by brokerage firms other than Compass are marked with the IDX icon, 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 Closed or are no longer being offered for sale. Home sale information is not to be construed as an appraisal and may not be used as such for any purpose. BRIGHT MLS is a provider of this home sale information and has compiled content from various sources. Some properties represented may not have actually sold due to reporting errors. Some real estate firms do not participate in IDX and their listings do not appear on this website. Some properties listed with participating firms do not appear on this website at the request of the seller. Information Deemed Reliable But Not Guaranteed.
BRIGHT(MRIS/Trend) data last updated at February 27, 2026, 3:50 PM ET
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