Main Content

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 (31)
Details
200 BRIDGEVIEW LN STEVENSVILLE, MD 21666
$14,950,000
8 Beds 7 | 3 Baths 20,013 SqFt Listing No. MDQA2011612 Property Type: House camera Virtual Tour camera (50)
Details
27772 SHARP RD EASTON, MD 21601
$13,750,000
5 Beds 7 | 2 Baths 13,228 SqFt Listing No. MDTA2010626 Property Type: House camera Virtual Tour camera (85)
Details
938 OLD COUNTY RD SEVERNA PARK, MD 21146
$12,975,000
6 Beds 8 | 3 Baths 15,737 SqFt Listing No. MDAA2104218 Property Type: House camera Virtual Tour camera (77)
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
3182 HARNESS CREEK RD ANNAPOLIS, MD 21403
$11,500,000
4 Beds 5 | 1 Baths 5,375 SqFt Listing No. MDAA2123314 Property Type: House camera Virtual Tour camera (99)
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
1900 CARROLLTON RD ANNAPOLIS, MD 21409
$8,995,000
7 Beds 6 | 3 Baths 12,200 SqFt Listing No. MDAA2105526 Property Type: House camera Virtual Tour camera (50)
Details
10770 RICH NECK RD CLAIBORNE, MD 21624
$8,875,000
7 Beds 7 | 1 Baths 10,240 SqFt Listing No. MDTA2010384 Property Type: House camera Virtual Tour camera (99)
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. MDAA2125880 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
 27 OLD SOUTH RIVER RD, EDGEWATER, MD 21037
camera (31)
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 (31)

 200 BRIDGEVIEW LN, STEVENSVILLE, MD 21666
camera VIRTUAL TOUR camera (50)
price

$14,950,000

beds

8 8 Beds

baths

7 | 3 7 | 3 Baths

lot size

20,013 SqFt 20,013 SqFt

listing no.

MDQA2011612 Listing No. MDQA2011612

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (50)

 27772 SHARP RD, EASTON, MD 21601
camera VIRTUAL TOUR camera (85)
price

$13,750,000

beds

5 5 Beds

baths

7 | 2 7 | 2 Baths

lot size

13,228 SqFt 13,228 SqFt

listing no.

MDTA2010626 Listing No. MDTA2010626

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (85)

 938 OLD COUNTY RD, SEVERNA PARK, MD 21146
camera VIRTUAL TOUR camera (77)
price

$12,975,000

beds

6 6 Beds

baths

8 | 3 8 | 3 Baths

lot size

15,737 SqFt 15,737 SqFt

listing no.

MDAA2104218 Listing No. MDAA2104218

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (77)

 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)

 3182 HARNESS CREEK RD, ANNAPOLIS, MD 21403
camera VIRTUAL TOUR camera (99)
price

$11,500,000

beds

4 4 Beds

baths

5 | 1 5 | 1 Baths

lot size

5,375 SqFt 5,375 SqFt

listing no.

MDAA2123314 Listing No. MDAA2123314

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (99)

 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)

 1900 CARROLLTON RD, ANNAPOLIS, MD 21409
camera VIRTUAL TOUR camera (50)
price

$8,995,000

beds

7 7 Beds

baths

6 | 3 6 | 3 Baths

lot size

12,200 SqFt 12,200 SqFt

listing no.

MDAA2105526 Listing No. MDAA2105526

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (50)

 10770 RICH NECK RD, CLAIBORNE, MD 21624
camera VIRTUAL TOUR camera (99)
price

$8,875,000

beds

7 7 Beds

baths

7 | 1 7 | 1 Baths

lot size

10,240 SqFt 10,240 SqFt

listing no.

MDTA2010384 Listing No. MDTA2010384

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (99)

 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
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.

MDAA2125880 Listing No. MDAA2125880

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)

© 2025 BRIGHT. All rights reserved.
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 October 23, 2025, 7:32 PM ET
Real Estate IDX Powered by iHomefinder

Get In Touch

With Matt Cheney
matt(dotted)cheney(at)compass(dotted)com 202.465.0707 DC BR600869
MD 582148
VA 0225101950