Caroline County Real Estate

The only Eastern Shore County not bordered by water, Caroline County is known as the “Green Garden County” for its rich heritage of commercial agriculture. Its 120,000 acres of farmland represent more than half of the county’s total acreage. Caroline County’s forests, wetlands, rivers and streams provide critical habitats for endangered plants and animals, as well as spawning and nursery areas for Chesapeake Bay fish species. Outdoor enthusiasts will enjoy hiking, canoeing and cycling through the county’s 8,000-plus acres of wildlife sanctuaries, nature preserves and public parks. Recreational activities are plentiful; boating, camping, hang-gliding, bird watching, fishing and hunting abound. Small, historic towns dot the landscape and offer varied guest accommodations, from quaint bed-and-breakfast inns to a modern, 60-unit Best Western Hotel. Caroline County is within 50-95 miles of major metropolitan areas including Annapolis, Baltimore, Washington, DC and Philadelphia, PA. Approximately 55% of residents work outside of Caroline County or out of state. A hand-engraved crown stone in the famous Mason-Dixon Line is located in the Caroline County town of Marydel and marks the division between Maryland and Delaware at that point. Caroline County was the site of at least three “stations” associated with the Underground Railroad in helping slaves escape during the Civil War.

Caroline County Real Estate offers several charming towns to choose from, such as Denton, Federalsburg, Goldsboro, Greensboro, Henderson, Hillsboro, Marydel, Preston, Ridgely, and Templeville.

The county’s 8,000-plus acres of wildlife sanctuaries, nature preserves, parks and campgrounds and public and private campgrounds provide miles of hiking trails and plenty of places to camp, hunt and even hang-glide. Canoeing, kayaking, fishing, boating and bird-watching await the water and nature enthusiast on 100 acres of freshwater lakes, eight public boat ramps, a well-maintained county marina, and miles and miles of rivers and creeks. (link tourcaroline website)

Caroline Country Club, located in Denton is situated along the Choptank River near the village of Willison, a private 18-home golf course open to the public on Mondays.

Caroline County offers numerous Marinas, Boat Ramps & Landings such as Choptank Marina, Crouse Park, Ganey's Wharf, Hillsboro Boat Ramp, Martinak State Park, Marina Park, Christian Park, Stoney Point Landing and Gilpin Point Landing.

Looking for delicious dining – I recommend: Market Street Public House, Snappy’s Bar & Grill, Lily Pad Café, Katie Mae’s and Ridgley Diner.

Click here for upcoming Caroline County events!

Search Caroline County, Maryland Eastern Shore Homes for Sale

Looking for Caroline County homes for sale on the Maryland Eastern Shore? Search our local listings database for access to listings in the Caroline County Real Estate market and surrounding areas. Whether you want to buy or sell Caroline County real estate you can browse through properties or find a wide variety of real estate resources available on this website.

Find Caroline County Real Estate Professionals

If you are looking for a REALTOR in Caroline County, choose Barbara Watkins! As your Caroline County Real Estate Agent Barbara Watkins can assist you with all of your home buying and selling needs on the Maryland Eastern Shore, including access to the local listings database with easy to use tools to search Caroline County homes for sale, provide a Comparative Market Analysis to determine your home value in Talbot County, and offer our experience and knowledge to make the home buying or selling process easier for you and your family. Contact Barbara Watkins today to get your home search started in Caroline County on the beautiful Eastern Shore of Maryland!

Queen Anne's County was established in 1706. The County was named for Queen Anne (1665-1714), who ruled Great Britain and Ireland from 1702 to 1714. It is populated by small towns that welcome tourists and shoppers, as well as those interested in visiting lovely restored historic sites. Queen Annes County is located on the central part of the Chesapeake's eastern shore, north of Talbot County and south of Kent County. Queen Anne’s County also offers several antique shops, a collection of outlet stores, Chesapeake College, public parks, trails, landings and the famous Wye Aspen institute near Wye Island. Residents and visitors of Queen Anne’s County can enjoy museums, historic homes and churches, historic court houses, train stations and Wye Mills working grist mill. There are 10 main towns incorporated in the county: Barclay, Centreville, Church Hill, Grasonville, Queen Anne, Queenstown, Sudersville, Kent Island and Stevensville. Centreville, the County seat, is centrally located between the major job centers of Annapolis, Baltimore, Delaware and Washington, D.C.

The Queen Anne’s County real estate community offers a multitude of housing choices from historic houses, luxury waterfront estates, water access community homes, horse farms, golf homes, and inland homes. Queen Anne’s County waterfront properties vary from deep water protected homes, broad water view, tranquil wildlife views to harbor view homes.

Located along the Chester River in Queenstown, Maryland is Queenstown Harbor. Queenstown Harbor offers single family homes and townhomes. The award-winning Queens Harbor River course was rated No. 2 by Golf Digest for "Best Public Golf Courses in Maryland." The community is just minutes to the large Queenstown Outlets shopping center, about 20 minutes from Annapolis, Maryland, and just 10 minutes from Centreville, Maryland.

The community known as Bennett’s Point divides between the Wye River and Eastern Bay. Bennett point consists of several different styles and ages of homes along the 8 mile strip. Bennett Point is close to the Queenstown Outlets, the new Queen Annes Emergency Room and many other attractions Queen Anne’s county has to offer. Kent Island and Historic St. Michaels, Maryland are both minutes by boat.

Just minutes from the Chesapeake Bay Bridge is Prospect Bay Country Club, located in Grasonville, Maryland. The community includes an 18-hole golf course, marina, clubhouse, outdoor tennis, swimming pool and many active social events to choose from. Many styles and sizes of homes from waterfront to inland and even golf view.

Experience Eastern Shore living at Wyoming on the Wye, this upscale waterfront area offers the convenience of living close to Annapolis and Easton and points west of the Bay Bridge. Deep water on the Wye River. Close to Queenstown, shopping, golf courses and the county sear of Centreville.

Located in Wye Mills, Maryland is Chesapeake College. Chesapeake College, founded in 1965 as Maryland’s first regional community college, was developed to serve the needs of the upper and middle Eastern Shore. More than a quarter-century after its founding, the College continues to respond to the growing needs of Caroline, Dorchester, Kent, Queen Anne’s, and Talbot counties, which compose its service area. Chesapeake College offers several Career & Professional studies. To name a few: Nursing, Physical Therapy, Enviormental Science, Education / Teaching, Criminal Justice, Engineering, and Hotel / Restaurant Management.

The Rufus M. and Loraine Hall Todd Performing Arts Center, located at Chesapeake College, is a state-of-the art regional performing arts center. Click here to view a calendar of events.

The Wye Oak State Park is located on State Route 662 in the community of Wye Mills in Talbot County. This park primarily existed to protect the Wye Oak Tree which toppled on June 6, 2002. A pavilion containing a section for the Wye Oak trunk and the original tree site can be viewed daily from sunrise to sunset. The park offers two interesting area landmarks. The Old Wye Mill which has been in operation since 1664 and continues to operate on a limited basis and The Wye Church which is said to be one of the oldest Episcopal Churches in the country. Across from the Old Wye Mill is the Stake Lake which offers a public landing, fishing and picnic areas.

Queenstown, Maryland offers Queenstown Premium Outlets which offers 65 outlets stores such as Polo Ralph Lauren, Michael Kors, Coach, Bath & Body Works, Nike, White House Black Market, Calvin Klein, Gucci, Talbots, Old Navy, Under Armour and many other eclectic store fronts.

Queen Anne’s County offers several golf courses to choose from. Such as Queenstown Harbor Golf, Chester River Yacht & Country Club, Prospect Bay Country Club, Blue Heron Golf Course, and Cove Creek Golf Club.

Looking for delicious dining – I recommend: Harris Crab House, Fishermans Inn, The Narrows Restaurant, Annie’s Steakhouse, Bridges, Adam’s Ribs, Cracker Barrel, The Jetty, Big Bats and Americantina.

Queen Anne’s County offers numerous Marinas such as Bay Bridge Marina, Haven Harbour, Mears Point, Swan Creek, Gratitude, Lankford Bay, North Point, Osprey Point Castle Harbor , Kentmorr Harbour Marina, Queen Anne’s Marina and Piney Narrows Yacht Haven.

Search Queen Anne’s County, Maryland Eastern Shore Homes for Sale

Looking for Queen Anne’s County homes for sale on the Maryland Eastern Shore? Search our local listings database for access to listings in the Queen Anne’s County Real Estate market and surrounding areas. Whether you want to buy or sell Queen Anne’s County real estate you can browse through properties or find a wide variety of real estate resources available on this website.

Find Queen Anne’s County Real Estate Professionals

If you are looking for a REALTOR in Queen Anne’s County, choose Barbara Watkins! As your Queen Anne’s County Real Estate Agent Barbara Watkins can assist you with all of your home buying and selling needs on the Maryland Eastern Shore, including access to the local listings database with easy to use tools to search Queen Anne’s County homes for sale, provide a Comparative Market Analysis to determine your home value in Queen Anne’s County, and offer our experience and knowledge to make the home buying or selling process easier for you and your family. Contact Barbara Watkins today to get your home search started in Queen Anne’s County on the beautiful Eastern Shore of Maryland!

Dorchester County

Dorchester County is often called “The Heart of Chesapeake Country,” because of its shape and its mid-shore location. An area of 600 square miles of land and 100 square miles of water makes it the largest county on Maryland’s Eastern Shore. Its shoreline along the Chesapeake Bay and the Choptank River totals 1700 miles, including islands and streams. Boaters and other sportsmen share the waterways with commercial watermen, who continue to harvest oysters and Maryland blue crabs. The 25,000-acre Blackwater National Wildlife Refuge provides safe habitat for a diverse population of birds, mammals and waterfowl. Because of its location along the Atlantic Flyway, Blackwater NWR serves as a wintering area for migrating ducks and Canada geese. The colorful history of Dorchester County includes such notables as slave trader Patty Cannon, sharpshooter Annie Oakley and Underground Railroad “conductor” Harriet Tubman, who helped more than 300 slaves escape to freedom during the Civil War. Two modern industrial parks are located in Dorchester County and accommodate both large and small businesses. Manufacturing accounts for nearly one-fourth of total employment, with the balance represented in the service and trade industries.

The Dorchester County real estate community offers a multitude of housing choices from historic “in town” houses, waterfront cottages, luxury waterfront estates, water access community homes, to condominiums, townhouses, and interior home sites.

Dorchester County, Maryland Waterfront properties vary from deep water protected homes, broad water view, tranquil wildlife views to harbor front and marina view homes. In town you will find colonial period homes, new homes, craftsman, Victorian and contemporary style homes. The historic homes along the beautiful brick- and tree-lined High Street were once owned by governors, statesmen, lawyers and other notable figures.

Some popular destinations are the fishing bridge, Sailwinds Park, the Cambridge Yacht Club, and the Cambridge Municipal Yacht Basin. Try to time your visit to see the Power Boat Regatta, usually at the end of July.

Quaint towns are scattered throughout Dorchester County, from the northern agricultural areas to the waterfront villages on three islands encompassed by the Chesapeake Bay and its tributaries. These towns include: Cambridge, Church Creek, East New Market, Elliots Island, Hoopers Island, Hurlock, Secretary, Taylors Island and Vienna.

Dorchester County is known for its delectable seafood—jumbo lump crab, rockfish, oysters, and more—fresh from local waters. Many of the restaurants are waterside—and some are accessible by boat. I recommend: The High Spot, Bistro Poplar, Bluepoint, Jimmy & Sooks, Leaky Petes, Portside and The Sucide Bridge.

You can reach Dorchester County, Maryland by boat, a short drive from Annapolis, Baltimore, Washington DC or Philadelphia. This small well- preserved County is a great place to visit and an even better place to call home. The Cambridge Dorchester Regional Airport is just minutes from downtown Cambridge.

Search Dorchester County, Maryland Eastern Shore Homes for Sale

Looking for Dorchester County homes for sale on the Maryland Eastern Shore? Search our local listings database for access to listings in the Dorchester County Real Estate market and surrounding areas. Whether you want to buy or sell Dorchester County real estate you can browse through properties or find a wide variety of real estate resources available on this website.

Find Dorchester County Real Estate Professionals

If you are looking for a REALTOR in Dorchester County, choose Barbara Watkins! As your Dorchester County Real Estate Agent Barbara Watkins can assist you with all of your home buying and selling needs on the Maryland Eastern Shore, including access to the local listings database with easy to use tools to search Dorchester County homes for sale, provide a Comparative Market Analysis to determine your home value in Dorchester County, and offer our experience and knowledge to make the home buying or selling process easier for you and your family. Contact Barbara Watkins today to get your home search started in Dorchester County on the beautiful Eastern Shore of Maryland!

Much of Talbot County’s history and character is defined by its 600-plus miles of tidal shoreline. In colonial times, the shipbuilding industry flourished in Talbot County. Some early settlers made their living trading tobacco for manufactured goods with English vessels that anchored off the plantation wharves. Today, the tobacco industry has been replaced by vegetable and poultry farming but the water still fosters the harvesting and processing of seafood, as well as tourism and associated water sports. Nature enthusiasts will delight in bird watching and other activities throughout the 950 acres of forests, meadows and wetlands. The charming, small towns of Talbot County are rich in culture and history, with a remarkable collection of museums, art galleries, theatres, inns, restaurants and boutiques.

The uniqueness of Talbot County belongs to its small towns and their treasury of history, heritage, culture and architecture. Charming historic downtown areas are filled with a phenomenal assortment of art galleries, antiques, museums, theatres, and boutiques - all within an easy stroll. Romantic restaurants and small inns complement the serenity and natural beauty of these very special places and endless experiences. Isn't it time to escape to Talbot County and explore these extraordinary small towns of St. Michaels, Easton, Oxford, Wye Mills and Tilghman Island.

The town of Easton, MD is the arts and cultural center of Talbot County, MD. It is also the most populated, with over 15,000 residents. The town attracts many visitors, who come to the area to enjoy outdoor activities like boating, sailing, fishing and crabbing. Residents and visitors to the area can also have access to an array of local shops, relaxing spas, live music venues, casual and fine dining and live theater. The town of Easton has a small-town ambiance while at the same time offering as much or more to do than communities many times its size.

The town of Oxford, MD is a charming, water bound village with a population of less than 1,000. It is also one of the oldest towns in America, founded in 1694, which means it holds a ton of history. Located near the mouth of the Tred Avon River, the town is centered around maritime activities, such as crabbing, fishing, sailing, etc. It has retained its historic charm through the years.

If you are looking for a fun, exhilarating, all embracing town that offers an array of unusual boutique shops, exceptional eateries, an old fashion soda fountain, wineries, a brewery, scenic river cruises, and educational museums St. Michaels, Maryland is the perfect place to live. The town is a collage of handsome churches, colonial, federal and Victorian homes, historic heritage, diverse artistic talents and pleasant southern culture.

Tilghman Island is best described as an “old fashioned waterman’s community.” It is located on the southernmost tip of the county, and it is a popular place to live for those involved in the seafood business. It’s also a popular destination for those interested in fishing trips and other water adventures.

The Talbot County Real Estate community offers a multitude of housing choices from historic “in town” houses, waterfront cottages, luxury waterfront estates, golf community homes, water access community homes, to condominiums, townhouses, and interior home sites. Talbot County Waterfront properties vary from deep water protected homes, broad water view, to wildlife and tranquil view homes. In the towns of Easton, Oxford, and St. Michaels you will find colonial period homes, new homes, craftsman, Victorian and contemporary style homes.

Talbot County, Maryland is just a short drive from Annapolis, Baltimore, Washington DC or Philadelphia, and you can fly into Easton’s municipal Airport.

Looking for delicious dining – I recommend: Bannings Tavern, Bartlett Pear Inn, Martinis, Mason’s, Out of the Fire, Ava’s, Theos, Harbour Lights, Latitude 38, Pope’s Taven, The Robert Morris Inn, Mitchum’s Steak House, Hidden Gem, Harrison House and Tilghman Island Inn.

Talbot County offers many marinas such as St. Michaels Harbour Inn, St Michaels Marina, Oxford Boat Yard, Mears Yacht Haven, Easton Point Marina, Tilghman Island Marina, Tilghman on Chesapeake and Knapps Narrows Marina.

Search Talbot County, Maryland Eastern Shore Homes for Sale

Looking for Talbot County homes for sale on the Maryland Eastern Shore? Search our local listings database for access to listings in the Talbot County Real Estate market and surrounding areas. Whether you want to buy or sell Talbot County real estate you can browse through properties or find a wide variety of real estate resources available on this website.

Find Talbot County Real Estate Professionals

If you are looking for a REALTOR in Talbot County, choose Barbara Watkins. As your Talbot County Real Estate Agent Barbara Watkins can assist you with all of your home buying and selling needs on the Maryland Eastern Shore, including access to the local listings database with easy to use tools to search Talbot County homes for sale, provide a Comparative Market Analysis to determine your home value in Talbot County, and offer our experience and knowledge to make the home buying or selling process easier for you and your family. Contact Barbara Watkins today to get your home search started in Talbot County on the beautiful Eastern Shore of Maryland!