OUR EXCLUSIVE LISTINGS

Chesapeake Bayfront

$1,495,000

Status: Active

“Gliding Gander” is a marvelous Chesapeake Bayfront property situated on 9 acres with endless broad views of the Chesapeake. Property features include 675’ of riprapped shoreline, gentle slope to water’s edge, 3 bedroom 3 bath rambler style home with large rooms, a heated pole building, a waterfowl pond, and additional storage building. The location is excellent and private while being centrally located between Historic Chestertown and Rock Hall. Priced to sell at $1,495,000.

For Sale: Merrythought Estate Rock Hall Maryland Chesapeake Bay
For Sale: Merrythought Estate Rock Hall Maryland Chesapeake Bay
For Sale: Merrythought Estate Rock Hall Maryland Chesapeake Bay
For Sale: Merrythought Estate Rock Hall Maryland Chesapeake Bay
For Sale: Merrythought Estate Rock Hall Maryland Chesapeake Bay
For Sale: Merrythought Estate Rock Hall Maryland Chesapeake Bay
For Sale: Merrythought Estate Rock Hall Maryland Chesapeake Ba
For Sale: Merrythought Estate Rock Hall Maryland Chesapeake Ba
For Sale: Merrythought Estate Rock Hall Maryland Chesapeake Ba
For Sale: Merrythought Estate Rock Hall Maryland Chesapeake Ba
For Sale: Merrythought Estate Rock Hall Maryland Chesapeake Ba
For Sale: Merrythought Estate Rock Hall Maryland Chesapeake Ba
For Sale: Merrythought Estate Rock Hall Maryland Chesapeake Ba
For Sale: Merrythought Estate Rock Hall Maryland Chesapeake Ba
For Sale: Merrythought Estate Rock Hall Maryland Chesapeake Ba
For Sale: Merrythought Estate Rock Hall Maryland Chesapeake Ba

Merrythought

$1,499,000

Status: Active

Address: 4324 Eastern Neck Rd, Rock Hall, MD

Welcome to Merrythought - Situated on 8.50 +/- acres with approximately 320 feet of protected shoreline on the Chesapeake Bay, this property offers incredible views and remarkable craftsmanship. The custom brick home features a first floor master suite, heart pine and brick floors, radiant floor heat, 6 bedrooms, 6 full bathroom, 3 fireplaces and an in-law suite above the 3 car garage. A large covered porch is westward facing for sunsets over the bay. Just a short drive to Eastern Neck Island Wildlife Refuge and Downtown Rock Hall. With some personal touch this property offers the new owner a great opportunity to build equity and enjoy waterfront living!

Fairlee Creek Home for Sale
Fairlee Creek Home for Sale
Fairlee Creek Home for Sale
Fairlee Creek Home for Sale
Fairlee Creek Home for Sale
Fairlee Creek Home for Sale
Fairlee Creek Home for Sale

Two Homes on Fairlee Creek 

$1,075,000

Status: Active

Water, water everywhere! This incredibly unique property is situated on a sheltered deep-water creek offering a westerly, southwesterly exposure with uncompromised sunsets. Fairlee Creek offers one of the most convenient boating accesses on the upper Chesapeake Bay. This 1.9 acre property comes improved with 2 homes, a deep water dock with 5-6' depth, an outdoor barbeque patio overlooking the creek, and 575+/- feet of secure shoreline. One of the two homes on this spectacular property is conte-levered above the water offering the feeling of being on a yacht with panoramic views from every room. The second home is a three bedroom, comfortable, one floor rambler with lovely screen porch overlooking the creek. The location of this property is notable in that it is centrally located in unspoiled Kent County and convenient to both historic Chestertown and the bayfront town of Rock Hall. Great Oak Marina and Resort is a short stroll of golf cart ride away where the residents of Great Oak Estates may share in the use of the establishment's facilities including the pool, restaurant, beach, and 9-hole golf course. Great Oak Estates is a fun-filled neighborhood where the residents interact well together and the spirits are active in the summertime and peaceful in the wintertime! $1,075,000.

No current listings for this category. Please check back again soon! 

Home for Sale 103 S Kent St. Chestertown MD 21620
Home for Sale 103 S Kent St. Chestertown
Home for Sale 103 S Kent St. Chestertown, MD
Home for Sale 103 S Kent St. Chestertown, MD
Home for Sale 103 S Kent St. Chestertown MD
Home for Sale 103 S Kent St. Chestertown, MD 21620
Home for Sale 103 S Kent St. Chestertown MD

103 S Kent St.

$349,000

Status: Active

Address: 103 S Kent St. Chestertown, MD 21620

This home has undergone a tasteful renovation including new plumbing, wiring, framing, mechanicals, and roof. The home offers a terrific floor plan with decorative touches which include built in book shelves and cabinetry, original and reclaimed wood floors, exposed brick and wainscoting. The first floor features a full bathroom and doorway leading to the rear brick patio. Upstairs features two bedrooms, a full renovated bathroom, ample storage and access to a large unfinished attic. The location makes for an easy walk to Downtown, waterfront, shops and restaurants.

Chester River Waterfront

$595,000

Status: Active

Chester River Waterfront totalling 18 acres with two bedroom elevated ranch home. Excellent hunting property with extensive frontage (1500+/- ft) on the river. Approximately 3-4 acres of hard ground and 12-14 acres of marshland. Excellent property to escape to! Asking $595,000.00

Deep Landing 

$299,000

Status: Active

"Deep Landing"

Ideal second home, retirement home or full time home! Located at Deep landing in Northern Queen Anne County within walking distance to the public boat ramp. 3 bedroom, 1 1/2 bath home with large family room, living room with fireplace, basement, 2 car garage, and additional storage building. This property included an additional recorded lot. Reasonably private setting. Asking $299,900.00

Galena MD Stone Farmhouse For Sale
Galena MD Stone Farmhouse For Sale
Galena MD Stone Farmhouse For Sale
Galena MD Stone Farmhouse For Sale
Galena MD Stone Farmhouse For Sale
Galena MD Stone Farmhouse For Sale
Galena MD Stone Farmhouse For Sale Yard

SOLD!

Galena Stone Farmhouse

Status: SOLD

Address: Galena, MD

Beautifully restored custom stone farmhouse situated on a double lot in the charming town of Galena Maryland in Northern Kent County. this property has all of the bells and whistles and would cost double the asking price to reproduce! The house is in "move-in" condition with many modern amenities. Notable features include: gleaming cherry floors, tile floors, spatial rooms with upgraded moldings, fireplace, walk-in closets, large kitchen with island, granite counter tops, upgraded tile baths , full dry clean basement with epoxy floor and built in storage shelves, second floor exterior roof top deck, two porches with mahogany decking, extensive hardscaping and a landscaping, and a fenced yard with room for garage, shop, or vegetable garden. Convenient to Sassafras River marinas, restaurants, cool grocery stores, route 301, and Middletown DE. ZONED COMMERCIAL for a multitude of uses including offices, retail, events, and B&B.

SOLD!

Glanville Lane

Status: SOLD

Address: Glanville Lane, Rock Hall, MD

This very well maintained home overlooking the Broad Chesapeake Bay is in a great condition with a semi-private location between Chestertown and Rock Hall, private but not Isolated! The views are "Out of this World" and the construction of the home is exceptional. The adjoining lot inclusion offers a wealth of opportunities and clean canvas to create your own private oasis with perhaps a pool with pool house and outdoor kitchen, a separate guest house, sport court or whatever you desire. The interior is clean, sharp and has had very little use since the present owner remodeled in mid 2000s. High end appliances and countertops, large oversized windows to take in the views, gleaming wood floors, tastefully tiled bathrooms, and clean dry basement are just a few of the many features. Elevated lawn with stable, substantially protected shoreline and ten mile views! This is an excellent opportunity to move right in and experience the greatest place on earth to live and enjoy, The Eastern Shore of Maryland! 

SOLD!

Visit handypointmd.com for more information!

Upper Chesapeake Bay 

Status: SOLD

This Majestic stately residence is perched at a perfect elevation with incredible views of undeveloped, preserved farmland and gently sloping lawn to the 1000' of white sandy beach on the Upper Chesapeake Bay. This awesome property offers ultimate privacy with the convenience to several urban centers within 90 minutes away. Historic Chestertown and the bayside town of Rock Hall are only moments away as well! Property features include a restored Georgian Colonial main residence in great condition with many original features and numerous recent updates, a large enclosed pool with attached recreation play house, 4 stall barn with 4 acre fenced pasture, tenant house, detached garages, extensive patios and landscape features, gorgeous private beach with bath house and much, much more! Come take a look and take advantage of all the value at a very reasonable asking price!

Listed and SOLD in 46 Days!

24000 Macs Lane

Status: SOLD

Address: 24000 Macs Lane, Worton, MD

This 49 acre waterfront property is one of a kind! The gently rolling pasture leads down to 2900+/- ft of shore line on Churn Creek. The property features an entry road, substantial dock with 4+/- MLW, private boat ramp with concrete pads, a waterfront gazebo, and the opportunity to build your perfect getaway or full time residence. The land is boarded by woodlands and water creating a private setting and is large enough for horses, hunting impoundments or hobby farmer. With an even blend of woodlands, waterfront and pasture the property is ideal for waterfowl, deer and turkey hunting. The Ag transfer tax has already been paid and the lot is ready to build.

3.82 Waterfront Lot on Grays Inn Creek
3.82 Waterfront Lot on Grays Inn Creek 2
3.82 Waterfront Lot on Grays Inn Creek 3
3.82 Waterfront Lot on Grays Inn Creek 4
3.82 Waterfront Lot on Grays Inn Creek 5
3.82 Waterfront Lot on Grays Inn Creek 6
3.82 Waterfront Lot on Grays Inn Creek 7

SOLD!

3.82 Waterfront Lot on Grays Inn Creek

$449,000

Status: SOLD

Address: 21648 Hill Lane, Rock Hall, MD 21661

One of the last undeveloped waterfront parcels on Grays Inn Creek. Just south of Rock Hall with easy water access to the Chesapeake Bay, this 3.8 +/- acre lot offers privacy but not isolation. The waterfront is a nice blend of boatable water and ideal for kayaking and paddle boarding. Surrounded by well maintained homes, this lot is the perfect opportunity to build a vacation or full time residence!

Lot 30 Hagy Rd, Rock Hall, MD 21661 - 6
Lot 30 Hagy Rd, Rock Hall, MD 21661 - 2
Lot 30 Hagy Rd, Rock Hall, MD 21661 - 3
Lot 30 Hagy Rd, Rock Hall, MD 21661 - 4
Lot 30 Hagy Rd, Rock Hall, MD 21661
Lot 30 Hagy Rd, Rock Hall, MD 21661 - 5

SOLD!

1.00 Acre Corner Lot with Boat Slip

$109,000

Status: SOLD

Address: Lot 30 Hagy Rd, Rock Hall, MD 21661

Lot 30 in Little Neck Farm is a 1.00 acre corner lot with beautiful views of the community pond and open space. This lot comes with a deeded deep water boat slip that allows easy access to the Rock Hall Marinas and Chesapeake Bay. The lot is boarded by evergreens and crepe myrtles that creates privacy within the community. The owners have detailed construction plans that go with the lot including building elevations, designs, and site plans. Only a few minutes to Rock Hall and 15 minutes to downtown Chestertown. A great opportunity to build your desired full time residence or weekend getaway in the quiet neighborhood of Little Neck Farm.

LISTED & SOLD in ONE DAY!

162+ Acre Grain Farm

$1,295,000

Status: SOLD

Address: 910 Millington Road, Sudlersville, MD

All tillable except barn and pond sites. Possibility for irrigation.

Waterfront condo

SOLD in 8 Days!

Waterfront Townhome with Boat Slip

$399,500

Status: SOLD

Address: 1 Idlewhile Ave Unit #7, Betterton, MD

Perched on a hill over looking the Chesapeake Bay and Sassafras River, this townhome offers beautiful views and a spectacular location in the town of Betterton. Escape the hustle and bustle of the city to your quiet townhome with hardwood floors, gas fireplace, waterfront screen in porch, community dock and private beach. The second floor offers a master with rooftop deck overlooking the Bay, two more bedrooms and second bathroom. The third floor bedroom/family room would make a great bunk room and offers exceptional water views. This unit is low maintenance creating the perfect getaway or full time residence! Furnishings are also available for purchase

8469 Garfield Lane, Chestertown, MD
8469 Garfield Lane, Chestertown, MD
8469 Garfield Lane, Chestertown, MD
8469 Garfield Lane, Chestertown, MD
8469 Garfield Lane, Chestertown, MD
8469 Garfield Lane, Chestertown, MD
8469 Garfield Lane, Chestertown, MD
8469 Garfield Lane, Chestertown, MD
8469 Garfield Lane, Chestertown, MD
8469 Garfield Lane, Chestertown, MD
8469 Garfield Lane, Chestertown, MD
8469 Garfield Lane, Chestertown, MD
8469 Garfield Lane, Chestertown, MD
8469 Garfield Lane, Chestertown, MD
8469 Garfield Lane, Chestertown, MD
8469 Garfield Lane, Chestertown, MD

SOLD in 9 Days!

8469 Garfield Lane

$298,500

Status: SOLD

Address: 8469 Garfield Lane, Chestertown, MD

Marvelous location one mile outside of Chestertown on 2 acres elevated and overlooking a well maintained scenic horse farm. The residence has loads of potential with spacious rooms, wood floors, eat-in kitchen with brick floor, large sun room, huge first floor master bedroom and bath, screen porch, deck, dry basement and more. Two car detached garage. Bring your ideas and build equity into this property that has tons of potential.

SOLD in 7 Days!

1 Acre Corner Lot

$259,900

Status: SOLD

Address: Near Chestertown, MD

Location, Location, Location in Northern Queen Anne County on a corner 1 acre lot in a quiet and peaceful neighborhood just minutes to Chestertown. This 3 BD 1.5 BA home was built by Church Hill Lumber Co. when Church Hill Lumber Co. was thought to be the best builders around! This home needs a little TLC but has loads of potential with wood floors, fireplace, eat-in Kitchen, family room, finished dry basement, and dining room. 

SOLD

108 S Kent Street

$178,000

Status: SOLD

Address: 108 S Kent Street, Chestertown, MD

This charming Downtown Chestertown home offers a semi open floor plan and cozy feel with hardwood floors throughout! The first floor features a dining and living area, powder room and kitchen with side door that leads to landscaped backyard. Upstairs is a full bathroom with laundry, bedroom and sitting room (or second bedroom) with built in shelves and exposed brick chimney. The courtyard garden with brick walkway lead to Downtown, waterfront, shops and restaurants. Bike trails and parks for your enjoyment are nearby. The delightful home makes for easy living!

Kimbolton For Sale Rock Hall
Waterfront Estate for Sale Rock Hall MD

SOLD

Kimbolton in Rock Hall

Status: SOLD

Address: 22738 Colonel Leonard RD, Rock Hall, MD 21661

"Kimbolton", You will be wowed as soon as you turn through the tastefully fenced entrance onto the tree-lined drive at this magnificent waterfront oasis. The property consists of 66+/- acres with approximately 3/4 mile of waterfrontage on the West Fork of Langford Creek with sweeping, panoramic, broad-water views. The property is improved with a comfortable Tidewater style main residence, a caretaker's home, a 2 car detached garage with guest quarters, substantial multi slip dock with covered lift and 8' MLW, newly restored Creekside gunite pool, tennis court, several auxiliary buildings and two ponds. Many recent upgrades including new roofs, new paint, new pool restoration, landscape restoration, new sewage disposal and more. This is a true Eastern Shore retreat of the finest kind with excellent location by both land and sea. The waterfowl and deer hunting are phenomenal. There is adequate space for cattle, horses, or other livestock. The quality of life at this property is like no other, truly a once in a lifetime offering! Take the virtual tour here.

Mill Creek Waterfront

Status: SOLD

Address: 

Mill Creek Waterfront, situated at the end of a quiet cul-de-sac in Chesapeake Landing within a short ten minute drive to Chestertown or Rock Hall. This 1.5+ /- wooded acre point of land is bordered on two side s by the creek. One side slopes gently to the creek and the other offers elevated views of water, marsh and unspoiled woodland. An abundance of wildlife including deer, turkeys, herons, eagles and waterfowl frequent the property and surroundings. This site offers access to Mill Creek for canoe, kayak, and paddle board. The residence offers views of the creek from most rooms in the recently upgraded raised rancher. There are two bedrooms, living areas with fireplaces, and kitchens on both levels. The waterside barn is in need of repairs but serves as a perfect building for watersport equipment, woodshop, " man cave" or "she shed". This is the ideal property to get-a-way from it all and decompress from the hustle and bustle of a fast paced lifestyle. Utility easement runs with the property.

SOLD

LISTED & SOLD in 17 Days! 

Mill Street

Status: SOLD

Address: 105 S Mill Street, Chestertown, MD

Renovated by the editor of Historic Houses of Kent County, the Davis Duplex is the perfect blend of historic charm and modern amenities. The property features a first floor master, multiple fireplaces, large upgraded kitchen, and built in bookshelves. The dual front doors enter into the formal dining and living room and the rear of the home has a
spacious master with flex space above. Outside is a lovely slate patio and brick pathways that lead to the gardens and Downtown.

Visit the custom property website at www.105smillst.com

SOLD for OVER Asking Price!

Renovated Rancher Near Chestertown & Rock Hall

Status: SOLD

Address: 10610 Klamath Rd, Chestertown, MD 21620

Pride of ownership is evident in this renovated ranch home. The home features an open floor plan, mudroom and living room entrances, instant hot water, 3 Bedrooms, 1 and a half bathrooms and tons of natural light. The property is improved with many custom features and the major upgrades include a new septic system, roof, HVAC, flooring, kitchen and bathrooms. The deck extends from the dining room to offer a comfortable outdoor living area. The exterior is further improved with hardscaping and tasteful landscaping. Schedule your tour today!

Chester River Waterfront Cottage 3
Chester River Waterfront Cottage
Chester River Waterfront Cottage 2
Chester River Waterfront Cottage 4
Chester River Waterfront Cottage 5

SOLD

Waterfront Cottage

Status: SOLD

Address:  

Cozy Waterfront Cottage on Chester River with awesome broad river views and gorgeous sunsets. Features include 3 bedrooms, 1 bath, fireplace, rip-rapped shoreline and large storage shed. Located just down the street from a public boat launch and only 12 minute ride to Historic Chestertown. Perfect retreat or second home! $289,000

SOLD

Queen Anne's Co Waterfront

$329,000

Status: SOLD

Address: 319 Fairview Drive, Chestertown, MD

An affordable Queen Anne's County waterfront! This property features a newer bulkhead, new BAT septic system, and navigable water. Inside the fully updated ranch home is a new kitchen with custom cabinets, granite counters, stainless steel appliances, new wood floors, a gas fireplace, new Andersen windows, 3 bedrooms and updated bathrooms. Downstairs is a full partially finished basement with a workshop. Enjoy the convenience of being close to Chestertown while utilizing the Queen Anne's County amenities!

SOLD

Cape Cod

$535,000

Status: Sold

Address:  7955 Airy Hill Rd. Chestertown, MD 21620

Low maintenance Cape Cod on 6 open acres situated on the outskirts of Historic Chestertown. Master suite on first floor with 2 additional large bedrooms and bath on second floor. Additional features include wood floors, fireplace, eat-in kitchen, 2 car garage, screen porch, barn and expansive storage. Awesome views of 5 acre waterfowl pond!