Chesapeake Bay Waterfront

Waterfront and Water Access Properties on the Upper Chesapeake Bay

Chesapeake Bay Waterfront

Chestertown Waterfront and Water Access Homes for Sale as of 10-7-2015

Chestertown Waterfront and Water Access Homes for Sale as of 10-7-2015

Here are the Top Newest Listings of Chestertown MD Waterfront and Water Access Homes for Sale as of October 7, 2015. All Chestertown Waterfront properties are on the Chester River and there are many wonderful Water Access Communities with many full t… Read more

Chestertown Waterfront and Water Access Homes for Sale as of 8-10-2015

Chestertown Waterfront and Water Access Homes for Sale as of 8-10-2015

Here are the Top Chestertown MD Waterfront and Water Access Homes for Sale as of August 9, 2015. All Chestertown Waterfront properties are on the Chester River and there are many wonderful Water Access Communities with many full time homes as well as Rive… Read more

Chestertown Waterfront and Water Access Homes for Sale as of 6-9-2015

Here are the Top 2 Chestertown MD Waterfront and Water Access Homes for Sale as of June 9, 2015. All Chestertown Waterfront properties are on the Chester River and there are many wonderful Water Access Communities with many full time homes as well as River Front Homes and Vacation Homes.

Founded in 1706, Chestertown rose in stature when it was named one of the English colony of Maryland's six Royal Ports of Entry. The shipping boom that followed this designation made the town at the navigable head of the Chester River wealthy. In the mid-eighteenth century, Chestertown trailed only Annapolis and was considered Maryland's second leading port.

A burgeoning merchant class infused riches into the town, reflected in the many brick mansions and townhouses that sprung up along the waterfront. Another area in which Chestertown is second only to Annapolis is in its number of existing eighteenth century homes.

As of the 1790 census, Chestertown was the geographical center of population of the United States.

Chestertown was incorporated in 1805, and was named for the Chester River.

Inventories are very low, the lowest in over 5 Years. If you are considering Selling Your Chestertown Waterfront or Water Access Home, please call us for a property evaluation or simply sign up for out Free Market Analysis

 
View Details30 photosNEW

$3,900,0007 beds, 6 bathsmls no. KE8367394

FarmMagnificent 18th century estate w/1000' waterfront on Chesapeake Bay! This…Courtesy of Long & Foster Real Estate, Inc.

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View Details29 photosNEW

$3,450,0006 beds, 5.5 bathsmls no. KE7969481

FarmCreate a family compound & build an additional home on this quintessential Eastern…Courtesy of Brandywine Fine Properties Sothebys INTL Realty

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Steve Hubbell REALTOR® – of the The "Bay Property Team", Selling Cecil County Waterfront –  – The "Bay Property Team" was formed in 2006 by Susan and Steve Hubbell to specialize in helping Buyers and Sellers invest in Waterfront and Water Access Properties in Chesapeake City, Elkton, Earleville, and Warwick in Cecil County MD and local Rivers and Creeks including the Sassafras River and Chester River. We also serve, Georgetown, Galena, and Kennedyville in Kent County MD, including Chestertown, and surrounding areas. (800)-890-0381 (Equal Housing Opportunity (O)-1-(410)-398-9000)

Chestertown Waterfront and Water Access Homes for Sale as of 2-3-2015

Here are the Top 5 Chestertown MD Waterfront and Water Access Homes for Sale as of February 3, 2015. All Chestertown Waterfront properties are on the Chester River and there are many wonderful Water Access Communities with many full time homes as well as River Front Homes and Vacation Homes.

Founded in 1706, Chestertown rose in stature when it was named one of the English colony of Maryland's six Royal Ports of Entry. The shipping boom that followed this designation made the town at the navigable head of the Chester River wealthy. In the mid-eighteenth century, Chestertown trailed only Annapolis and was considered Maryland's second leading port.

A burgeoning merchant class infused riches into the town, reflected in the many brick mansions and townhouses that sprung up along the waterfront. Another area in which Chestertown is second only to Annapolis is in its number of existing eighteenth century homes.

As of the 1790 census, Chestertown was the geographical center of population of the United States.

Chestertown was incorporated in 1805, and was named for the Chester River.

Inventories are very low, the lowest in over 5 Years. If you are considering Selling Your Chestertown Waterfront or Water Access Home, please call us for a property evaluation or simply sign up for out Free Market Analysis

 
View Details30 photos

$3,900,0007 beds, 6 bathsmls no. KE8367394

Single Family HomeMagnificent 18th century estate w/1000' waterfront on Chesapeake Bay! This…Courtesy of Long & Foster Real Estate, Inc.

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View Details30 photos

$3,495,0006 beds, 5.5 bathsmls no. KE7969481

Single Family HomeCreate a family compound & build an additional home on this quintessential Eastern…Courtesy of Brandywine Fine Properties Sothebys INTL Realty

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View Details30 photos

$2,995,0004 beds, 4.5 baths4314 sq. ft.mls no. KE7943447

Single Family HomeKentfields is located on Quaker Neck close to Chestertown on Maryland's beautiful…Courtesy of Lacaze Meredith Real Estate

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View Details30 photos

$2,250,0005 beds, 4.5 baths4968 sq. ft.mls no. KE6606019

Single Family HomeWaterfront farm on the Chester River with marvelous hunting off the marsh & on 2…Courtesy of Sassafras River Realty, Ltd.

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View Details19 photos

$1,575,0005 beds, 4.5 baths5000 sq. ft.mls no. KE7889885

Single Family HomeNew reduced Taxes! Gorgeous brick architecturally designed cape on a private 8+…Courtesy of Brandywine Fine Properties Sothebys INTL Realty

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Steve Hubbell REALTOR® – of the The "Bay Property Team", Selling Cecil County Waterfront –  – The "Bay Property Team" was formed in 2006 by Susan and Steve Hubbell to specialize in helping Buyers and Sellers invest in Waterfront and Water Access Properties in Chesapeake City, Elkton, Earleville, and Warwick in Cecil County MD and local Rivers and Creeks including the Sassafras River and Chester River. We also serve, Georgetown, Galena, and Kennedyville in Kent County MD, including Chestertown, and surrounding areas. (800)-890-0381 (Equal Housing Opportunity (O)-1-(410)-398-9000)

Chestertown Waterfront and Water Access Homes for Sale as of 11-3-2014

Here are the Top 5 Chestertown MD Waterfront and Water Access Homes for Sale as of November 3, 2014. All Chestertown Waterfront properties are on the Chester River and there are many wonderful Water Access Communities with many full time homes as well as River Front Homes and Vacation Homes.

Founded in 1706, Chestertown rose in stature when it was named one of the English colony of Maryland's six Royal Ports of Entry. The shipping boom that followed this designation made the town at the navigable head of the Chester River wealthy. In the mid-eighteenth century, Chestertown trailed only Annapolis and was considered Maryland's second leading port.

A burgeoning merchant class infused riches into the town, reflected in the many brick mansions and townhouses that sprung up along the waterfront. Another area in which Chestertown is second only to Annapolis is in its number of existing eighteenth century homes.

As of the 1790 census, Chestertown was the geographical center of population of the United States.

Chestertown was incorporated in 1805, and was named for the Chester River.

Inventories are very low, the lowest in over 5 Years. If you are considering Selling Your Chestertown Waterfront or Water Access Home, please call us for a property evaluation or simply sign up for out Free Market Analysis

 
View Details30 photosNEW

$3,900,0007 beds, 6 bathsmls no. KE8367394

Single Family HomeMagnificent 18th century estate w/1000' waterfront on Chesapeake Bay! This…Courtesy of Long & Foster Real Estate, Inc.

Locate on map

View Details30 photos

$3,495,0006 beds, 5.5 bathsmls no. KE7969481

Single Family HomeCreate a family compound & build an additional home on this quintessential Eastern…Courtesy of Brandywine Fine Properties Sothebys INTL Realty

Locate on map

View Details30 photos

$2,995,0004 beds, 4.5 baths4314 sq. ft.mls no. KE7943447

Single Family HomeKentfields is located on Quaker Neck close to Chestertown on Maryland's beautiful…Courtesy of Lacaze Meredith Real Estate

Locate on map

View Details30 photosNEW

$2,650,0007 beds, 4.5 baths4748 sq. ft.mls no. KE8456225

Single Family HomeEastern Shore Waterfront Farm – "Ruerden" is a magnificent 42-acre property with…Courtesy of Coldwell Banker Chesapeake Real Estate Co

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$2,250,0005 beds, 4.5 baths4968 sq. ft.mls no. KE6606019

Single Family HomeWaterfront farm on the Chester River with marvelous hunting off the marsh & on 2…Courtesy of Sassafras River Realty, Ltd.

 
Steve Hubbell REALTOR® – of the The "Bay Property Team", Selling Cecil County Waterfront –  – The "Bay Property Team" was formed in 2006 by Susan and Steve Hubbell to specialize in helping Buyers and Sellers invest in Waterfront and Water Access Properties in Chesapeake City, Elkton, Earleville, and Warwick in Cecil County MD and local Rivers and Creeks including the Sassafras River and Chester River. We also serve, Georgetown, Galena, and Kennedyville in Kent County MD, including Chestertown, and surrounding areas. (800)-890-0381 (Equal Housing Opportunity (O)-1-(410)-398-9000)

Chestertown Waterfront and Water Access Homes for Sale as of 9-3-2014

Here are the Top 5 Chestertown MD Waterfront and Water Access Homes for Sale as of September 3, 2014. All Chestertown Waterfront properties are on the Chester River and there are many wonderful Water Access Communities with many full time homes as well as River Front Homes and Vacation Homes.

Founded in 1706, Chestertown rose in stature when it was named one of the English colony of Maryland's six Royal Ports of Entry. The shipping boom that followed this designation made the town at the navigable head of the Chester River wealthy. In the mid-eighteenth century, Chestertown trailed only Annapolis and was considered Maryland's second leading port.

A burgeoning merchant class infused riches into the town, reflected in the many brick mansions and townhouses that sprung up along the waterfront. Another area in which Chestertown is second only to Annapolis is in its number of existing eighteenth century homes.

As of the 1790 census, Chestertown was the geographical center of population of the United States.

Chestertown was incorporated in 1805, and was named for the Chester River.

Inventories are very low, the lowest in over 5 Years. If you are considering Selling Your Chestertown Waterfront or Water Access Home, please call us for a property evaluation or simply sign up for out Free Market Analysis

 
View Details30 photos

$3,900,0007 beds, 6 bathsmls no. KE8367394

Single Family HomeMagnificent 18th century estate w/1000' waterfront on Chesapeake Bay! This…Courtesy of Long & Foster Real Estate, Inc.

Locate on map

View Details30 photosNEW

$3,495,0006 beds, 5.5 bathsmls no. KE7969481

Single Family HomeCreate a family compound with an additional home that can fit on the property….Courtesy of Brandywine Fine Properties Sothebys INTL Realty

Locate on map

View Details30 photos

$2,995,0004 beds, 4.5 baths4314 sq. ft.mls no. KE7943447

Single Family HomeKentfields is located on Quaker Neck close to Chestertown on Maryland's beautiful…Courtesy of Lacaze Meredith Real Estate

Locate on map

View Details28 photos

$2,800,00012 beds, 12.5 baths13851 sq. ft.mls no. KE8223466

Single Family HomeEastern Shore waterfront manor on the Chesapeake Bay. Recently renovated, Great…Courtesy of Coldwell Banker Chesapeake Real Estate Co

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View Details30 photos

$2,250,0005 beds, 4.5 baths4968 sq. ft.mls no. KE6606019

Single Family HomeWaterfront farm on the Chester River with marvelous hunting off the marsh & on 2…Courtesy of Sassafras River Realty, Ltd.

Steve Hubbell REALTOR® – of the The "Bay Property Team", Selling Cecil County Waterfront –  – The "Bay Property Team" was formed in 2006 by Susan and Steve Hubbell to specialize in helping Buyers and Sellers invest in Waterfront and Water Access Properties in Chesapeake City, Elkton, Earleville, and Warwick in Cecil County MD and local Rivers and Creeks including the Sassafras River and Chester River. We also serve, Georgetown, Galena, and Kennedyville in Kent County MD, including Chestertown, and surrounding areas. (800)-890-0381 (Equal Housing Opportunity (O)-1-(410)-398-9000)

Chestertown Waterfront and Water Access Homes for Sale as of 6-3-2014

Here are the Top 5 Chestertown MD Waterfront and Water Access Homes for Sale as of June 3, 2014. All Chestertown Waterfront properties are on the Chester River and there are many wonderful Water Access Communities with many full time homes as well as River Front Homes and Vacation Homes.

Founded in 1706, Chestertown rose in stature when it was named one of the English colony of Maryland's six Royal Ports of Entry. The shipping boom that followed this designation made the town at the navigable head of the Chester River wealthy. In the mid-eighteenth century, Chestertown trailed only Annapolis and was considered Maryland's second leading port.

A burgeoning merchant class infused riches into the town, reflected in the many brick mansions and townhouses that sprung up along the waterfront. Another area in which Chestertown is second only to Annapolis is in its number of existing eighteenth century homes.

As of the 1790 census, Chestertown was the geographical center of population of the United States.

Chestertown was incorporated in 1805, and was named for the Chester River.

Inventories are very low, the lowest in over 5 Years. If you are considering Selling Your Chestertown Waterfront or Water Access Home, please call us for a property evaluation or simply sign up for out Free Market Analysis

 
View Details30 photos

$3,695,000.006 beds, 5.5 bathsmls no. KE7969481

Single Family HomeCreate a family compound with an additional home that can fit on the property….Courtesy of Brandywine Fine Properties Sothebys INTL Realty

Locate on map

View Details30 photos

$3,495,000.004 beds, 4.5 baths4314 sq. ft.mls no. KE7943447

Single Family HomeKentfields is located on Quaker Neck close to Chestertown on Maryland's beautiful…Courtesy of Lacaze Meredith Real Estate

Locate on map

View Details28 photos

$3,050,000.0012 beds, 12.5 baths13851 sq. ft.mls no. KE8223466

Single Family HomeEastern Shore waterfront manor on the Chesapeake Bay. Recently renovated, Great…Courtesy of Coldwell Banker Chesapeake Real Estate Co

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View Details30 photos

$2,250,000.005 beds, 4.5 baths4968 sq. ft.mls no. KE6606019

Single Family HomeWaterfront farm on the Chester River with marvelous hunting off the marsh & on 2…Courtesy of Sassafras River Realty, Ltd.

Locate on map

View Details23 photosNEW

$1,575,000.005 beds, 4.5 baths5000 sq. ft.mls no. KE7889885

Single Family HomeTimeless cape sited on a private 8+ acre waterfront lot complete with dock, boat…Courtesy of Brandywine Fine Properties Sothebys INTL Realty

Locate on map

Steve Hubbell REALTOR® – of the The "Bay Property Team", Selling Cecil County Waterfront –  – The "Bay Property Team" was formed in 2006 by Susan and Steve Hubbell to specialize in helping Buyers and Sellers invest in Waterfront and Water Access Properties in Chesapeake City, Elkton, Earleville, and Warwick in Cecil County MD and local Rivers and Creeks including the Sassafras River and Chester River. We also serve, Georgetown, Galena, and Kennedyville in Kent County MD, including Chestertown, and surrounding areas. (800)-890-0381 (Equal Housing Opportunity (O)-1-(410)-398-9000)

Chestertown Waterfront and Water Access Homes for Sale as of 4-2-2014

Here are the Top 5 Chestertown MD Waterfront and Water Access Homes for Sale as of April 2, 2014. All Chestertown Waterfront properties are on the Chester River and there are many wonderful Water Access Communities with many full time homes as well as River Front Homes and Vacation Homes.

Founded in 1706, Chestertown rose in stature when it was named one of the English colony of Maryland's six Royal Ports of Entry. The shipping boom that followed this designation made the town at the navigable head of the Chester River wealthy. In the mid-eighteenth century, Chestertown trailed only Annapolis and was considered Maryland's second leading port.

A burgeoning merchant class infused riches into the town, reflected in the many brick mansions and townhouses that sprung up along the waterfront. Another area in which Chestertown is second only to Annapolis is in its number of existing eighteenth century homes.

As of the 1790 census, Chestertown was the geographical center of population of the United States.

Chestertown was incorporated in 1805, and was named for the Chester River.

Inventories are very low, the lowest in over 5 Years. If you are considering Selling Your Chestertown Waterfront or Water Access Home, please call us for a property evaluation or simply sign up for out Free Market Analysis

 
View Details30 photos

$3,695,000.006 beds, 5.5 bathsmls no. KE7969481

Single Family HomeCreate a family compound with an additional home that can fit on the property….Courtesy of Brandywine Fine Properties Sothebys INTL Realty

Locate on map

View Details30 photos

$3,495,000.004 beds, 4.5 baths4314 sq. ft.mls no. KE7943447

Single Family HomeKentfields is located on Quaker Neck close to Chestertown on Maryland's beautiful…Courtesy of Lacaze Meredith Real Estate

Locate on map

View Details28 photos

$3,050,000.0012 beds, 12.5 baths13851 sq. ft.mls no. KE8223466

Single Family HomeEastern Shore waterfront manor on the Chesapeake Bay. Recently renovated, Great…Courtesy of Coldwell Banker Chesapeake Real Estate Co

Locate on map

View Details30 photos

$2,250,000.005 beds, 4.5 baths4968 sq. ft.mls no. KE6606019

Single Family HomeWaterfront farm on the Chester River with marvelous hunting off the marsh & on 2…Courtesy of Sassafras River Realty, Ltd.

Locate on map

View Details23 photos

$1,675,000.005 beds, 4.5 baths5000 sq. ft.mls no. KE7889885

Single Family HomeTimeless cape sited on a private 8+ acre waterfront lot complete with dock, boat…Courtesy of Brandywine Fine Properties Sothebys INTL Realty

Locate on map​

Steve Hubbell REALTOR® – of the The "Bay Property Team", Selling Cecil County Waterfront –  – The "Bay Property Team" was formed in 2006 by Susan and Steve Hubbell to specialize in helping Buyers and Sellers invest in Waterfront and Water Access Properties in Chesapeake City, Elkton, Earleville, and Warwick in Cecil County MD and local Rivers and Creeks including the Sassafras River and Chester River. We also serve, Georgetown, Galena, and Kennedyville in Kent County MD, including Chestertown, and surrounding areas. (800)-890-0381 (Equal Housing Opportunity (O)-1-(410)-398-9000)

Chestertown Waterfront and Water Access Homes for Sale as of 2-12-2014

Here are the Top 5 Chestertown MD Waterfront and Water Access Homes for Sale as of February 12, 2014. All Chestertown Waterfront properties are on the Chester River and there are many wonderful Water Access Communities with many full time homes as well as River Front Homes and Vacation Homes.

Founded in 1706, Chestertown rose in stature when it was named one of the English colony of Maryland's six Royal Ports of Entry. The shipping boom that followed this designation made the town at the navigable head of the Chester River wealthy. In the mid-eighteenth century, Chestertown trailed only Annapolis and was considered Maryland's second leading port.

A burgeoning merchant class infused riches into the town, reflected in the many brick mansions and townhouses that sprung up along the waterfront. Another area in which Chestertown is second only to Annapolis is in its number of existing eighteenth century homes.

As of the 1790 census, Chestertown was the geographical center of population of the United States.

Chestertown was incorporated in 1805, and was named for the Chester River.

Inventories are very low, the lowest in over 5 Years. If you are considering Selling Your Chestertown Waterfront or Water Access Home, please call us for a property evaluation or simply sign up for out Free Market Analysis

 
View Details30 photos

$3,695,000.006 beds, 5.5 bathsmls no. KE7969481

Single Family HomeCreate a family compound with an additional home that can fit on the property….Courtesy of Brandywine Fine Properties Sothebys INTL Realty

Locate on map

View Details30 photos

$3,495,000.004 beds, 4.5 baths4314 sq. ft.mls no. KE7943447

Single Family HomeKentfields is located on Quaker Neck close to Chestertown on Maryland's beautiful…Courtesy of Lacaze Meredith Real Estate

Locate on map

View Details28 photosNEW

$3,050,000.0012 beds, 12.5 baths13851 sq. ft.mls no. KE8223466

Single Family HomeEastern Shore waterfront manor on the Chesapeake Bay. Recently renovated, Great…Courtesy of Coldwell Banker Chesapeake Real Estate Co

Locate on map

View Details30 photos

$2,250,000.005 beds, 4.5 baths4968 sq. ft.mls no. KE6606019

Single Family HomeWaterfront farm on the Chester River with marvelous hunting off the marsh & on 2…Courtesy of Sassafras River Realty, Ltd.

Locate on map

View Details23 photos

$1,675,000.005 beds, 4.5 baths5000 sq. ft.mls no. KE7889885

Single Family HomeTimeless cape sited on a private 8+ acre waterfront lot complete with dock, boat…Courtesy of Brandywine Fine Properties Sothebys INTL Realty

Locate on map​

Steve Hubbell REALTOR® – of the The "Bay Property Team", Selling Cecil County Waterfront –  – The "Bay Property Team" was formed in 2006 by Susan and Steve Hubbell to specialize in helping Buyers and Sellers invest in Waterfront and Water Access Properties in Chesapeake City, Elkton, Earleville, and Warwick in Cecil County MD and local Rivers and Creeks including the Sassafras River and Chester River. We also serve, Georgetown, Galena, and Kennedyville in Kent County MD, including Chestertown, and surrounding areas. (800)-890-0381 (Equal Housing Opportunity (O)-1-(410)-398-9000)

Chestertown MD Waterfront and Water Access Homes for Sale as of 1-11-2014

Here are the Top 5 Chestertown MD Waterfront and Water Access Homes for Sale as of Janyary 11, 2014. All Chestertown Waterfront properties are on the Chester River and there are many wonderful Water Access Communities with many full time homes as well as River Front Homes and Vacation Homes.

Founded in 1706, Chestertown rose in stature when it was named one of the English colony of Maryland's six Royal Ports of Entry. The shipping boom that followed this designation made the town at the navigable head of the Chester River wealthy. In the mid-eighteenth century, Chestertown trailed only Annapolis and was considered Maryland's second leading port.

A burgeoning merchant class infused riches into the town, reflected in the many brick mansions and townhouses that sprung up along the waterfront. Another area in which Chestertown is second only to Annapolis is in its number of existing eighteenth century homes.

As of the 1790 census, Chestertown was the geographical center of population of the United States.

Chestertown was incorporated in 1805, and was named for the Chester River.

Inventories are very low, the lowest in over 5 Years. If you are considering Selling Your Chestertown Waterfront or Water Access Home, please call us for a property evaluation or simply sign up for out Free Market Analysis

View Details30 photosNEW

$4,900,000.007 beds, 6 bathsmls no. KE7315421

FarmHistorically significant home on 21 acres, 1000' on the Chesapeake Bay. Modern 4…Courtesy of Chesapeake Real Estate Associates, LLC

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View Details30 photos

$3,695,000.006 beds, 5.5 bathsmls no. KE7969481

FarmCreate a family compound with an additional home that can fit on the property….Courtesy of Brandywine Fine Properties Sothebys INTL Realty

Locate on map

View Details30 photos

$3,495,000.004 beds, 4.5 baths4314 sq. ft.mls no. KE7943447

FarmKentfields is located on Quaker Neck close to Chestertown on Maryland's beautiful…Courtesy of Lacaze Meredith Real Estate

Locate on map

View Details28 photos

$3,050,000.0012 beds, 12.5 baths13851 sq. ft.mls no. KE8223466

Single Family HomeEastern Shore waterfront manor on the Chesapeake Bay. Recently renovated, Great…Courtesy of Coldwell Banker Chesapeake Real Estate Co

Locate on map

View Details30 photos

$2,250,000.005 beds, 4.5 baths4968 sq. ft.mls no. KE6606019

FarmWaterfront farm on the Chester River with marvelous hunting off the marsh & on 2…Courtesy of Sassafras River Realty, Ltd.

Locate on map

Steve Hubbell REALTOR® – of the The "Bay Property Team", Selling Cecil County Waterfront –  – The "Bay Property Team" was formed in 2006 by Susan and Steve Hubbell to specialize in helping Buyers and Sellers invest in Waterfront and Water Access Properties in Chesapeake City, Elkton, Earleville, and Warwick in Cecil County MD and local Rivers and Creeks including the Sassafras River and Chester River. We also serve, Georgetown, Galena, and Kennedyville in Kent County MD, including Chestertown, and surrounding areas. (800)-890-0381 (Equal Housing Opportunity (O)-1-(410)-398-9000)