A Rare Opportunity in the Heart of Historic ChestertownDiscover a truly special offering in the vibrant core of Chestertown’s Historic and Arts & Entertainment Districts. Owned by the same family for over 50 years, this multi-family property sits on a generous double lot known historically as the Laurence Lots—featured on original town maps and steeped in local heritage.Brimming with character and potential, the property currently features a townhouse on one side and two apartments on the other, offering a flexible layout ideal for renovation, income generation, or a creative reimagining. Whether you're envisioning a stately single-family residence, a dynamic live/work space, or a thoughtfully restored multi-unit investment, the possibilities are as expansive as the lot itself.That said, this is not a turnkey property. Significant settling has occurred over the years, and a substantial renovation will be required to bring it back to life. Offered strictly as-is, this is a true fixer-upper for the visionary buyer ready to take on a transformative project.Situated within both the Arts & Entertainment District and Enterprise Zone, this location supports both residential and business uses—making it an ideal candidate for those looking to merge lifestyle, business, and history. **See updated zoning info and description from town office in Documents.Bring your vision, creativity, and tools—and seize the chance to breathe new life into a piece of Chestertown’s storied past. Opportunities like this don’t come along often.Schedule your showing today and imagine the future you can build here.
Listing Courtesy of BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company / Cheryl Hurt
$395,000 (USD)
Chestertown Area Townhome
Pending
349 High Street Chestertown, MD 21620
7 Bed
4 Baths
3664 sqft
MLS# MDKE2004076
A Rare Opportunity in the Heart of Historic ChestertownDiscover a truly special offering in the vibrant core of Chestertown’s Historic and Arts & Entertainment Districts. Owned by the same family for over 50 years, this multi-family property sits on a generous double lot known historically as the Laurence Lots—featured on original town maps and steeped in local heritage.Brimming with character and potential, the property currently features a townhouse on one side and two apartments on the other, offering a flexible layout ideal for renovation, income generation, or a creative reimagining. Whether you're envisioning a stately single-family residence, a dynamic live/work space, or a thoughtfully restored multi-unit investment, the possibilities are as expansive as the lot itself.That said, this is not a turnkey property. Significant settling has occurred over the years, and a substantial renovation will be required to bring it back to life. Offered strictly as-is, this is a true fixer-upper for the visionary buyer ready to take on a transformative project.Situated within both the Arts & Entertainment District and Enterprise Zone, this location supports both residential and business uses—making it an ideal candidate for those looking to merge lifestyle, business, and history.Bring your vision, creativity, and tools—and seize the chance to breathe new life into a piece of Chestertown’s storied past. Opportunities like this don’t come along often.Schedule your showing today and imagine the future you can build here.**See updated zoning info from the town in documents
Listing Courtesy of BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company / Cheryl Hurt
$20,000 (USD)
Chestertown Area Land
Pending
Elm Road Chestertown, MD 21620
Bed
0 Baths
sqft
MLS# MDKE2003590
One parcel comprised of 2 cleared lots in Tolchester Estates. The community is on the Chesapeake Bay and the residents have access to the beach and there is a marina close by.County states water/sewer allocation is available. Buyer to confirm with due diligence.
Listing Courtesy of BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company / Cheryl Hurt
$863,900 (USD)
Chestertown Area Residential Home
Sold
212 N Queen Street Chestertown, MD 21620
5 Bed
6 Baths
3756 sqft
18th century historic home in downtown Chestertown with a separate carriage house! The main home features 3 bedrooms all with en-suite baths. The carriage house has an additional 2 bedrooms and 2 baths with separate laundry and a brick patio. Entrances to the property from Queen St. and Horsey Lane, 2 driveways with plenty of parking spaces. Original wood flooring throughout much of the house. The first floor features a living room, dining room, kitchen, and half bath. New owner to add vanity and toilet to one of the upstairs baths. Second-floor laundry room. Lovely landscaping and fenced-in yard between the main house and the carriage house. Just a short walk to the heart of downtown Chestertown. Definitely a rare find.
Listing Courtesy of BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company / Peter Heller
$555,000 (USD)
Chestertown Area Townhome
Sold
103 Landing Lane Chestertown, MD 21620
2 Bed
3 Baths
2100 sqft
Welcome to this charming and elegant 2 bedroom, 2.5 bathroom condo nestled in a tranquil water-oriented community near the Chester River in the historic town of Chestertown, Maryland.This gorgeous home is situated in a prime location, offering easy access to nearby shops, cafes, and restaurants. As you step inside, you'll be greeted by a warm and inviting atmosphere that seamlessly blends classic charm with modern convenience.On the main level , you'll find access from the attached garage or front porch. Off the spacious hallway you have the enclosed Washer/Dryer unit, storage closet and full bathroom. French Doors leading to the first floor study with a bedroom to the left and straight ahead to the downstairs screened in porch overlooking the serene community pond.The upper level features an open-concept living area that's perfect for entertaining. You'll love the spacious kitchen with its stainless steel appliances, sleek countertops, and ample cabinet space. The dining area is flooded with natural light, creating the perfect ambiance for family meals and gatherings with friends. Enter the upstairs porch overlooking the pond with views of the pond, this is true indoor/outdoor entertaining.The upstairs primary suite is a true retreat, complete with a luxurious en-suite bathroom featuring double sinks, shower and stunning finishes. A huge walk in closet completes this experience.This home is also ideally situated within a water-oriented community, providing easy access to boating, fishing, and other water activities. The community offers a dock, boat ramp, as well as grilling areas and a swimming pool for your enjoyment.With its stunning finishes, prime location, and luxurious amenities, this 2 bedroom, 2.5 bathroom condo is the perfect place to call home. Don't miss your chance to experience the best that Chestertown has to offer!
Listing Courtesy of BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company / Cheryl Hurt
$360,000 (USD)
Chestertown Area Residential Home
Sold
7828 Country Club Lane Chestertown, MD 21620
4 Bed
3 Baths
2857 sqft
Sprawling brick rancher in a lovely, peaceful setting. Over 2800 sq ft. Large rooms with lots of natural light. Huge family room with cathedral ceilings and fireplace overlooking the ample rear yard. Formal living and dining rooms with hardwood floors and crown molding. HVAC is only one year old. New well pump and WIFI controlled garage door. Water heater new in 2017. Home has a grand, palatial feel with relaxing views from all the windows. Close to Chestertown and a golf cart ride to the Chester River Yacht and Country Club. High speed internet available on site.
Listing Courtesy of BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company / Elizabeth "Lisa" Raffetto
$320,000 (USD)
Chestertown Area Multi-Family Home
Sold
114 Riverside Terrace 6 Chestertown, MD 21620
2 Bed
1 Baths
896 sqft
A delightful 2 bedroom 1 bath Duplex Condo in the lovely Riverside Terrace community. The unit has been well-maintained and has breathtaking water views from the front yard and both upper and lower decks. Nestled in the heart of Historic Chestertown with easy access to town, the river, shops, Washington College, and hospital. Enjoy the beautiful tree-lined streets of this colonial-era town, the Saturday farmers' market, local theater and everything that Chestertown has to offer.
Listing Courtesy of BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company / Cheryl Hurt
$319,500 (USD)
Millington Area Residential Home
Sold
374 Hurtt Avenue Millington, MD 21651
3 Bed
2 Baths
1801 sqft
This sprawling brick rancher will take your breath away! Renovated top to bottom with updated systems, brand new stylish kitchen, luxury bathrooms, rich hardwood flooring, and a fabulous rear patio set on a large deep lot with mature trees. Single floor living with low maintenance ALL BRICK exterior, a 1 car attached garage and plenty of space for the entire gang! Minutes from Rt. 301 and commuting/shopping in Delaware, all set in a picturesque quiet small town with playground park just down the street. RECENTLY REDUCED! Come check it out today before someone else does!
Listing Courtesy of BRIGHT IDX / Village Real Estate Company LLC
$239,900 (USD)
Chestertown Area Townhome
Sold
106 Oak Leaf Drive Chestertown, MD 21620
3 Bed
3 Baths
1976 sqft
Beautiful, well maintained 3 bedroom end unit townhome. Just minutes from downtown Chestertown. Features freshly refinished hardwood floors, new carpet, new roof, vaulted master bedroom, soaking tub and separate shower in the master bath, 9 foot ceilings on the first floor, walk out second story deck, and an over-sized garage with a workshop. The home is very close to shopping and restaurants. A perfect place for weekends or year-round lifestyle living.
Listing Courtesy of BRIGHT IDX / Benson & Mangold, LLC
$230,000 (USD)
Chestertown Area Residential Home
Sold
209 Waldo Drive Chestertown, MD 21620
4 Bed
2 Baths
1728 sqft
Lovely cottage in Byford Heights, convenient location that's just minutes from the local hospital, shopping and schools. This mid-century home is move-in ready and you can take your time updating as you like...or keep it in it's current mid-century style. With 4 bedrooms and 2 full baths, there is plenty of room for a growing family. Hardwood floors throughout. Attached garage with a nice driveway provides ample parking. Large fenced in back yard with storage shed. Come see this lovely home today!
Listing Courtesy of BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company / Cheryl Hurt
$227,000 (USD)
Chestertown Area Residential Home
Sold
611 Cannon Street Chestertown, MD 21620
2 Bed
2 Baths
920 sqft
Just a few blocks away from the heart of downtown Chestertown, this bungalow could be your perfect home, or great investment property. With a large kitchen and dining room for entertaining and a living room with an abundance of natural light, this could be your happy place. The bedrooms are large, one with a half bath attached and the laundry/mud room has plenty of room for storage with a closet and cabinets.
Listing Courtesy of BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company / Cheryl Hurt
$213,000 (USD)
Crumpton Area Residential Home
Sold
306 Broad Street Crumpton, MD 21628
3 Bed
2 Baths
1414 sqft
Quiet Community, public water access block away, walking trail, Sunrise and sunset water views. Private fencing on one side, fencing for dogs in back yard. New Patio great for fire pit. Inside new wooden blinds, new luxury vinyl floor, new ceiling fan in living room, new gas stove. TAX free shopping in Middletown Delaware 15 minutes away. This is a very nice duplex.
Listing Courtesy of BRIGHT IDX / Exit On The Bay
$200,000 (USD)
Kennedyville Area Residential Home
Sold
12061 Locust Grove Road Kennedyville, MD 21645
3 Bed
2 Baths
1469 sqft
Welcome to country living! This is a beautiful brick rancher in a beautiful country setting. Enjoy the peace and quiet of the surrounding Kent County farmland. Enjoy the beautiful Hardwood floors and natural colors as you walk through the front door. You will love the rear screened in porch, looking out over the trees and shrubs of Angelica Nurseries. Almost 1 acre of land for you to spread out on. You can stop over to Crow Vineyard and Winery and enjoy the winery and grass fed beef! You are close to Delaware and Tax Free Shopping , close to the water was well, stop down to Turner's Creek Park and Boat Ramp. Lots to do in the area for sure!
Listing Courtesy of BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company
$164,900 (USD)
Rock Hall Area Residential Home
Sold
6121 Tolchester Road Rock Hall, MD 21661
2 Bed
1 Baths
1165 sqft
Priced To Sell Fast! Charming 2 Level Colonial, Spacious Kitchen with QUARTZ Counters, Stainless Steel Appliances, Modern Tile Backsplash, Spacious Bedrooms, New Custom Paint, Updated Bathroom, Brand New HVAC, New Flooring, Updated Lighting, Driveway, Much More!! Close to Schools, Shopping and Commuter Routes. This Will Not Last!
Listing Courtesy of BRIGHT IDX / Anr Realty, LLC
$155,000 (USD)
Kennedyville Area Residential Home
Sold
11975 Augustine Herman Highway Kennedyville, MD 21645
3 Bed
2 Baths
1092 sqft
Lovely well-cared for home in the center of Kennedyville. 3br, 1.5ba 2 story home with large fenced in yard. New roof and flooring installed in 2019. Freshly painted and move-in ready! Should go for any financing type. Easy access to Delaware and points north. Minutes from Chestertown.
Listing Courtesy of BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company / Cheryl Hurt
$155,000 (USD)
Kennedyville Area Multi-Family Home
Sold
11937 Sparks Lane Kennedyville, MD 21645
3 Bed
3 Baths
1600 sqft
1600 SF 3 BR/2.5 BA home that shows like new located in the Village at Kennedyville offers a front porch that overlooks the community pond...full basement and garage...hardwood flooring on the first floor, beautiful cabinetry with a very spacious kitchen pantry
Listing Courtesy of BRIGHT IDX / Long & Foster Real Estate, Inc.
$15,000 (USD)
Chestertown Area Land
Active
Sheldrake Drive Chestertown, MD 21620
Bed
0 Baths
sqft
MLS# MDKE2001692
Great opportunity to own a lot in Chesapeake Landing! Currently does not have a valid perc. Water access to Worton Creek if you join the voluntary civic association! Close to Worton Marina and Chestertown.
Listing Courtesy of BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company / Peter Heller
$2,500,000 (USD)
Chestertown Area Residential Home
Active
7989 Quaker Neck Road Chestertown, MD 21620
5 Bed
5 Baths
4305 sqft
MLS# MDKE2005590
Price Improvement! Spectacular waterfront on the Chester River!! Words can't describe the uniqueness of this property. With the historic charm of an older home but high end modern upgrades, you will be living the life of luxury. Spacious rooms, magnificent views of the Chester River and your private dock with new boat lift, sandy beach, and stunning new saltwater pool. Exposed beams, scalamandre wallpaper, and multiple fireplaces. First floor owners suite featuring reclaimed pine flooring, private laundry area, walk-in closet, gas fireplace and remodeled bath with soaking tub. Second floor owner's suite with additional laundry area and remodeled bath. Breezeway to the garage. New irrigation system to all flower beds. New paint inside and out. House has had major remodels in 2000 and 2020. Town sewer. Not far from town, but the property has a private feel. Come and be amazed!!
Listing Courtesy of BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company / Peter Heller
$1,400,000 (USD)
Earleville Area Residential Home
Pending
164 Wickwire Drive Earleville, MD 21919
5 Bed
7 Baths
4755 sqft
MLS# MDCC2020112
A Rare Waterview Masterpiece Designed for the Ultimate Boating Lifestyle. Set on 1.376 acres with breathtaking water views and unforgettable sunsets, this one-of-a-kind contemporary residence delivers luxury, functionality, and resort-style living at every turn. Thoughtfully designed with the boater in mind, this exceptional home offers expansive entertaining spaces, refined finishes, and outstanding access to boating amenities. The main level showcases a dramatic living room with gas fireplace and sweeping water views, a dining room opening to the rear deck, and a stunning gourmet kitchen featuring quartzite countertops, a grand center island, Wolf 5-burner gas stove, steam oven, convection oven, butler’s pantry, and an additional pantry/storage area with refrigerator. A screened-in porch just off the kitchen creates the perfect space for relaxed water view living. Also on this level are a hall bath, office or sitting room, main-level laundry, and a luxurious primary ensuite with small deck with stunning views, double vanities, jetted tub, and a separate shower and toilet area. The second level is ideal for hosting, offering three bedrooms with three full baths, plus two additional sleeping areas thoughtfully designed for guests. The fully finished lower level continues the luxury with a gym, bedroom with full bath, additional laundry hookup, spa-like bathroom with double vanities and an oversized shower, and a rear entry perfectly suited for coming in off the water. Outdoor living is nothing short of spectacular, featuring a professionally landscaped rear patio with water feature, firepit, garden irrigation, and automatic timers. A rear garage and workshop provide ample space for water toys, gear, and golf carts. Additional highlights include a deeded boat slip with two boat lifts, 90-amp electric vehicle charger, whole-house humidifier, three-zoned HVAC, Pella windows, architectural roof (2024), automatic water shutoff system (Flow Logic), and all appliances included. An exclusive opportunity to acquire the adjacent 1.245-acre parcel, offered separately, featuring a deeded boat slip and lift, with right of first refusal extended to the purchaser. This extraordinary property offers a rare blend of luxury, privacy, and elevated water view living. Truly one of a kind—schedule your private showing today.
Listing Courtesy of BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company / Tinamarie Reamy
$1,395,500 (USD)
Chestertown Area Residential Home
Active
105 High Street Chestertown, MD 21620
0 Bed
0 Baths
3243 sqft
MLS# MDKE2005890
This masterpiece is finally complete. Rebuilt in 1863, the Tilley Residence showcases classic Second Empire style on one of Chestertown’s most prominent corners, neighboring Widehall and the Custom House.Expertly restored in 2024–2025 by one of Kent County’s premier builders, the home offers new HVAC, electrical, plumbing, roofing, flooring, and a refreshed open layout. Custom kitchen and baths balance modern comfort with timeless character. A grand three-story staircase and arched entryways welcome you inside. The front porch overlooks town and offers water views. The primary suite includes a fireplace, walk-in closet, and a tiled shower room with views from two sides. The Mansard roof provides a full third floor, and the basement includes a great wine cellar opportunity plus ample storage. A fenced rear yard, off-street parking, and a detached garage complete this rare offering—historic charm blended with modern amenities.
Listing Courtesy of BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company / Michael "Murphy" O'Neill
$950,000 (USD)
Grasonville Area Townhome
Active
110 Channel Marker Way 203 Grasonville, MD 21638
4 Bed
4 Baths
2653 sqft
MLS# MDQA2015244
This boater's paradise demonstrates the perfect blend of luxury and convenience. The property boasts three floors of sweeping waterfront views all easily accessed via your own private elevator. High end finishes can be found throughout and the home has been impeccably maintained. The first floor feels inviting with the fireplace, open kitchen, and guest bedroom with ensuite full bathroom currently being used as an office. The second floors wows you with 3 spacious bedrooms including the primary that has a walkout balcony for quiet evenings staring out over the water. The top floor provides yet another entertaining or living space with a wet bar, full bathroom, and a walk out balcony. Outdoor living in general is a highlight here with each floor allowing for a different perspective of the Eastern Shore landscape. Don't forget about the amenities of the community. Lounge out by the pool, walk to famous waterfront seafood establishments, or navigate the vast waters of the Chesapeake from your deeded 35 foot deep water boat slip just steps away. This luxury Eastern Shore destination is located just an hour from Washington, D.C. or Baltimore and less than two hours from Philadelphia.
Listing Courtesy of BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company / Michael "Murphy" O'Neill
$850,000 (USD)
Street Area Residential Home
Pending
3908 Street Road Street, MD 21154
5 Bed
5 Baths
4688 sqft
MLS# MDHR2048478
Welcome to Windwood: where meticulous pride of ownership truly shows on this classic Cape Cod on nearly 10 acres of serene, private land. With an expansive 4-bedroom main house and separate guest cottage; this home is perfect for a multi-generational family who are looking for separate spaces or for a family looking to generate more income by utilizing the guest house as a rental. This home really epitomizes quality 1960's construction and craftsmanship: solid brick and cedar siding, southern pine hardwood floors throughout, elegant keyhole crown moldings, a wonderful dining room fireplace, built-in shelving cabinets, timeless dormers, and so much more. Coming up the circle drive you are received by a peaceful front porch; perfect for enjoying summer breezes and sunsets. Inside you are greeted to a welcoming foyer with a formal living room to your right and massive dining room to your left complemented by a wood-burning fireplace with intricate wood mantle. Moving back you will find the private main-floor primary suite with ensuite and large walk-in closet. The first floor further features a TV room and a recently renovated sun-room bump. out. Continuing on, the spacious kitchen with breakfast area was renovated in 2021 and now features honey-oak built-ins, custom cabinets, granite countertops, stainless steel appliances, propane or electric stove, a generously sized island with overhang seating, and LVP flooring. As you take the wide staircase upstairs you will find more gleaming hardwood floors that were just refinished. The second floor has three generously sized bedrooms; each with large closets and a smaller office space. Each end of the second floor features large attic storage areas. The full basement is partially finished with a spacious rec or workout room with a wood burning stove and new LVP floors. Across the brick breezeway, the guest house has also been recently renovated including all new kitchen appliances, walnut cabinets, washer/dryer, new floors, and upgraded bath. In front of the guest house is an attached two-car garage with additional areas for storage and tools. The backyard is a gardener’s dream and is fully fenced for the dogs and/or little kids. A small garden area, pergola and small fishpond complete the peaceful surroundings. Several walking trails have been cut out throughout the woods where you will find a large woodshed with plenty of storage. This wonderful property has so much to offer, you won’t want to miss it. Much more info and professional photos coming soon. Stay tuned!
Listing Courtesy of BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company / Joseph Ciganek
$624,900 (USD)
Stevensville Area Townhome
Coming Soon
222 Moorings Circle 126 Stevensville, MD 21666
3 Bed
3 Baths
2074 sqft
Welcome home to refined coastal living on Maryland’s Eastern Shore in this beautifully designed 3-bedroom, 3-bath home located in the premier 55+ community of Bay Bridge Cove in Stevensville, Maryland.This lovely and well-maintained home was built in 2022 and offers 2,074 square feet over two levels. The home blends light-filled spaces with effortless, low-maintenance living just minutes from the Chesapeake Bay.Soaring cathedral ceilings elevate the main living area, where a propane fireplace creates a warm focal point for entertaining or just relaxing. The kitchen is designed for gathering, featuring granite countertops, a custom backsplash, stainless steel appliances, and an expansive center island with cabinetry on both sides — ideal for casual breakfasts or evenings entertaining friends and neighbors. A dining area is located between the kitchen and living area, completing the truly open concept. Enjoy your morning coffee or curl up and read a good book in the sunroom located just off the living room, featuring lovely views of the tree lined open space at the rear of the home — no neighbors behind you! The main-level primary suite offers tray ceilings, dual closets, double vanities, and a beautifully tiled walk-in shower — a peaceful retreat at day’s end. A second bedroom and full bath on the main level provide convenience for guests, while the upper level offers a private third bedroom with full bath and a spacious family room with custom railing overlook, perfect for extended stays or additional living space.Other features of the home include a welcoming gated courtyard with charming bistro lighting, perfect for a little gardening, or unwinding at the end of the day. Beautiful custom blinds are tailored to each room, ceiling fans are located throughout, and the front and rear storm doors provide even more light into this light and airy home. The two-car garage has ample space for your vehicles, water toys, or just some extra storage. The lawn irrigation system helps to maintain a plush lawn, and lawn maintenance is included in the HOA, allowing you to enjoy the community lifestyle Bay Bridge Cove residents embrace.Bay Bridge Cove residents settle into a vibrant, resort-style setting with an oversized clubhouse with fitness center, meeting and gathering spaces, full kitchen, community pool, pickleball, and bocce. Activities abound at this gathering spot all year round! The walking/biking trails are throughout the community, as well as a dog park for your furry family members, and even a community garden for those fresh summer vegetables.Ideally located just minutes from the Chesapeake Bay, area golf courses, waterfront dining, shopping, and multiple marinas. Annapolis is a short 15 minutes away, Washington DC is about an hour, and Atlantic Coast beaches are approximately a 2-hour drive. This home offers the perfect balance of coastal charm, convenience, and active adult living, and is just waiting for you to call this HOME! Schedule your private tour today!
Listing Courtesy of BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company / Terri Kulp
$575,000 (USD)
Elkton Area Residential Home
Pending
55 River Road Elkton, MD 21921
3 Bed
0 Baths
2168 sqft
MLS# MDCC2020238
Stunning Waterfront Home on the Elk River in Locust Point! Welcome to 55 River Road, Elkton, MD 21921, offering beautiful Elk River views and approximately 2,200± sq. ft. of total living space. This 3-bedroom, 3 full bathroom home features an open floor plan with immediate water views upon entry. Interior highlights include crown molding, plantation shutters, luxury LVP flooring, and fresh paint throughout (currently in progress).The eat-in kitchen is complete with granite countertops, dining area, and all appliances included. Enjoy water views from the spacious living room with a sliding door leading to a newer composite deck and paver patio, ideal for outdoor entertaining.The primary bedroom offers an en-suite bath with tiled walk-in shower and custom shelving. The finished lower level includes a side entrance and provides flexible space for a home office, family room, or additional living area.Recent updates include a new Architectural Lifetime roof (2024), Gutters/Downspouts (2024) new propane HVAC system (2024), and new bulkhead (2021). Conveniently located near multiple marinas and a community boat ramp.
Listing Courtesy of BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company / Tinamarie Reamy
$385,000 (USD)
Elkton Area Residential Home
Pending
37 Jesse Boyd Circle Elkton, MD 21921
4 Bed
3 Baths
1856 sqft
MLS# MDCC2019508
Welcome home to this move-in ready home featuring 4 bedrooms and 3 full baths. The upper level features a large light-filled living room with windows on the front and side of the home. The living room opens into the combined kitchen and dining area. The kitchen features a new backsplash, stainless steel appliances, new faucet, and a kitchen island perfect for food prep, serving area, and plenty of additional cabinet storage underneath. The adjoining dining area provides ample space for your dining needs and offers convenient access to the nice-sized deck, perfect for outdoor dining and barbecuing. The deck has steps down to the rear yard for all of your outdoor activities. The partially fenced rear yard could easily be enclosed to provide safety and privacy. The remaining upper level features the upper level primary suite with full bathroom, and the other 2 bedrooms share a full hall bathroom. The lower level features the 4th bedroom with walk-in closet and adjoining full spa bathroom. This room can also function as a family room with full wet bar if you just need a little more relaxing space. This level is finished off with a laundry/utility room and garage entry. The location of the home is perfect for commuters and is less than 10 minutes to I-95 and a short trip to Delaware for work and tax free shopping, as well as all points south along the I-95 corridor to Washington, DC. Recreation abounds with a short trip to Elk Neck State Park, approximately 30 minutes away. The park features the Turkey Point Lighthouse which sits on a high bluff overlooking the Chesapeake Bay, Elk, and Northeast Rivers. The park offers campgrounds, rustic cabins, swimming, fishing, crabbing, miles of trails for hikers and bikers, as well as boat and canoe/kayak launches. This home is ready and waiting for you to come home! Schedule your tour today, don't wait! SHOWINGS BEGIN 11/2/25
Listing Courtesy of BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company / Terri Kulp
$350,000 (USD)
Chestertown Area Residential Home
Pending
121 Primrose Road Chestertown, MD 21620
3 Bed
3 Baths
2034 sqft
MLS# MDQA2015570
Motivated Seller. Welcome to 121 Primrose Road, a well-built two-story home offering 2,034 square feet of living space on a .345-acre lot, located just outside downtown Chestertown in a quiet setting.The upper level includes three bedrooms and two full bathrooms, while the main level offers a convenient half bath. The first floor features a bright living area, a traditional dining space, and a spacious all-seasons room off the kitchen—ideal for everyday living or entertaining. The full basement provides excellent potential for future finishing, storage, or workspace.Recent improvements include newly installed LVP flooring in the downstairs bathroom and sunroom, completed this month. A brand-new septic system adds peace of mind, while the attached two-car garage and large rear deck enhance functionality and outdoor enjoyment.Situated on the Queen Anne’s County side of Chestertown, the property offers easy access to downtown shops, dining, and waterfront amenities, while still enjoying the feel of a peaceful neighborhood.
Listing Courtesy of BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company / William "Billy" Sutton
$349,000 (USD)
Earleville Area Residential Home
Active
16 Florida Avenue Earleville, MD 21919
3 Bed
0 Baths
1431 sqft
MLS# MDCC2020236
Welcome to 16 Florida Avenue, Earleville, MD, a beautifully renovated ranch-style home offering over 1,431 sq. ft. of living space, ideally located on a quiet back street in a desirable water-oriented community with beach access.This 3-bedroom, 1 full bath home was completely renovated down to the studs in 2021, allowing the next owner to enjoy the benefits of extensive upgrades throughout. The open floor plan seamlessly connects the living room, dining area, and kitchen, creating a functional and inviting living space.The kitchen features white cabinetry, black granite countertops, and GE stainless steel appliances, while the home is enhanced by ¾-inch thick, 3-inch wide sanded and stained hardwood floors. A spacious family room offers a wood stove and slate flooring, providing additional living and entertaining space.Major improvements include all new plumbing and electrical systems (2021), Andersen Low-E windows, and a Pella sliding door with built-in blinds in the primary bedroom. The updated full bath features a tile surround, and the home is equipped with a high-efficiency Amana heat pump, 50-year architectural shingles, and updated siding.Additional highlights include a stackable washer and dryer, a large front deck, storage shed, and seasonal water views. Residents enjoy access to community amenities including boating, watersports, and beach access.A thoughtfully renovated, move-in-ready home offering comfort, quality, and lifestyle in a waterfront community.
Listing Courtesy of BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company / Tinamarie Reamy
$345,000 (USD)
Chestertown Area Residential Home
Pending
204 Rolling Road Chestertown, MD 21620
3 Bed
2 Baths
2296 sqft
MLS# MDKE2005896
Live with ease in this beautifully updated and maintained one floor home in downtown Chestertown. The current owners put a large addition on the house that includes a family room with wood burning stove, sunroom, and primary suite with en suite bathroom and walk in closet. A large laundry room on the main floor and updated kitchen with tons of counter space were other valuable design updates. The basement provides ample partially finished storage space in a completely dry environment due to serious structural improvements, sump pump and french drain system. Bring your hobby down there or your trusty work bench. The roof, HVAC, and hot water heater are all less than 10 years old. The front yard provides a polished experience with tasteful landscaping. The rear yard is quite large for a house in town and includes a raised bed garden and tidy shed. Experience the relaxed lifestyle of Chestertown with the Historic District's shops, Washington College, and the Margo Bailey park just a short walk away.
Listing Courtesy of BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company / Michael "Murphy" O'Neill
$320,000 (USD)
Sudlersville Area Residential Home
Sold
204 Church Street S Sudlersville, MD 21668
3 Bed
3 Baths
1616 sqft
Welcome to 204 S Church Street — a charming 3BR/3BA home in the heart of Sudlersville!This beautifully maintained and thoughtfully updated home offers comfort, style, and modern conveniences. One of its standout features is the spacious first-floor primary bedroom complete with a private en-suite bathroom, offering ease and accessibility rarely found in homes of this style. This home boasts 3-bedrooms and 3 full bathrooms and features a wrap-around porch perfect for morning coffee or evening relaxation.Inside, you'll find an inviting layout with granite countertops in the kitchen, a cozy fireplace in the living area, and dual-zone HVAC to keep you comfortable year-round. The home is equipped with a tankless water heater, ensuring endless hot water and energy efficiency.Enjoy privacy and room to play in the fully fenced-in yard, ideal for pets, gardening, or entertaining. O head over to nearby Sudlersville Park!This move-in-ready gem offers the perfect combination of small-town living and modern amenities.Don’t miss your chance to make it yours!
Listing Courtesy of BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company / Cheryl Hurt
$314,900 (USD)
Chestertown Area Residential Home
Pending
213 Central Drive Chestertown, MD 21620
3 Bed
2 Baths
1232 sqft
MLS# MDQA2015648
Great rancher in Chester Harbor on the Queen Anne's County side of Chestertown. Fresh paint and carpet throughout. Both bathrooms are completely remodeled. The kitchen could use updating, but the space is great and the appliances are in excellent condition. Plenty of room to add a kitchen island and still have space for a table. Nice 2 car detached pole barn style garage. Fenced back yard. This property has a lot to offer!
Listing Courtesy of BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company / Peter Heller
$295,000 (USD)
Chestertown Area Townhome
Active
107 Oak Leaf Drive Chestertown, MD 21620
3 Bed
3 Baths
1947 sqft
MLS# MDKE2006114
Desirable end-unit, 3-story townhome located in the heart of Chestertown, just moments from downtown and adjacent to the new YMCA. This well-maintained home features newer carpet and paint, a one-year-old stove (purchased new for $4,000), and a hot water heater just two years old. A newer full-size stackable washer and dryer adds convenience.Enjoy both sunrise and sunset views with an east-facing front that fills the home with beautiful morning light and a west-facing rear offering stunning evening sunsets. The balcony has been recently stained, and the first-floor patio has been thoughtfully converted into a deck with built-in wood flower boxes—perfect for outdoor enjoyment.The versatile first level offers flexible space ideal for a bedroom, office, or exercise room, complete with a gas fireplace and sliding door access to the deck. The garage includes a built-in loft, workbench, and shelving for added storage and functionality.Upstairs, the primary suite features a vaulted ceiling and a spacious en-suite bath with soaking tub and walk-in shower. A mature maple tree enhances the backyard setting, providing charm and seasonal beauty.Move-in ready and ideally located—this home offers comfort, updates, and convenience all in one.
Listing Courtesy of BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company / Kristina Hyland
$270,000 (USD)
Millington Area Residential Home
Active
356 Cypress Street Millington, MD 21651
3 Bed
2 Baths
1508 sqft
MLS# MDKE2005972
Looking for a 3 bed farmhouse in Millington with classic charm and modern updates? This warm and friendly 1920 single family home offers 1508 square feet on a 0.17 acre lot with a 2021 roof, vinyl siding, three second floor bedrooms, one full bath, and a half bath off the kitchen. A wrapped front and side porch sets the tone, while a rear wooden deck opens to the yard for easy outdoor living. The heated rear garage includes driveway parking and a setup that allows welder hookup, ideal for hobby work or small trades. Inside, the layout provides a cozy front living space, practical kitchen flow, and natural light throughout. Located in Millington with quick access to Route 301.
Listing Courtesy of BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company / William "Billy" Sutton
$269,975 (USD)
Chestertown Area Residential Home
Sold
106 Pine Street Chestertown, MD 21620
3 Bed
1 Baths
1376 sqft
Clean, classic mid-century style ranch with REAL wood floors. archways, knotty pine kitchen, a big front porch, large yard, off-street parking and bonus alley access in rear with possible room for a detached garage (buyer to verify) New upgraded electrical service and GFCI outlets, fresh paint, floors refinished and more. Walk to conveniences from this move-in ready charmer in upper Chestertown.
Listing Courtesy of BRIGHT IDX / Doug Ashley Realtors, LLC
$250,000 (USD)
Worton Area Residential Home
Active
25044 Travis Trail Worton, MD 21678
3 Bed
2 Baths
1278 sqft
MLS# MDKE2006000
Welcome to this sweet ranch-style home in Worton, Maryland, tucked into a quiet little neighborhood of Knight’s Landing surrounded by beautiful farmland. It’s the perfect spot if you’re looking for peaceful living without feeling far from everything—just under five minutes to the local high school, community center, and park. Cozy, convenient, and easy on the budget, this home offers small-town vibes with everyday essentials close by.
Listing Courtesy of BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company / Jyaire "Jay" McCall
$249,000 (USD)
Ocean City Area Condominium
Active
203 33rd Street 10202 Ocean City, MD 21842
1 Bed
1 Baths
548 sqft
MLS# MDWO2031416
Enjoy coastal living this fall and beyond with this meticulously maintained, fully furnished, turn-key 1-bedroom, 1-bath condo in Ocean City, MD. Perfectly situated on the first floor, you’ll appreciate the ease of access—no stairs to climb when bringing in luggage or supplies. Inside, the open-concept kitchen and living area provide a bright, welcoming space to relax or entertain. Step outside to your spacious balcony, complete with comfortable furniture, hurricane shutters, and a convenient storage shed for beach gear and toys. Recent upgrades include a new washer/dryer (2023), refrigerator (2019), and a Google Nest thermostat that allows you to control the climate remotely. After a day at the beach, rinse off in the community’s outdoor shower before heading inside. Parking is included for added convenience.Just two short blocks from the ocean and within walking distance to the historic Ocean City Boardwalk, Jolly Roger Amusement & Splash Mountain Water Park, plus countless restaurants and shops—this location offers the best of everything. The Jamaica Daybreak Condo Association recently completed extensive exterior renovations (May 2025), with all assessment fees already paid in full by the seller—giving buyers peace of mind. With some of the lowest condo fees in the area at just $325/month, you’ll also enjoy discounted cable TV and internet. Lovingly owned for 20 years and never rented, this condo is move-in ready and waiting for its next chapter.
Listing Courtesy of BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company / Joseph Ciganek
$225,000 (USD)
Earleville Area Land
Pending
Wickwire Drive Earleville, MD 21919
Bed
0 Baths
sqft
MLS# MDCC2020118
LOT for sale!!! An exceptional opportunity to enhance a premier waterfront lifestyle. This 1.245-acre water-view homesite in Sunset Pointe includes a deeded boat slip and lift
Listing Courtesy of BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company / Tinamarie Reamy
$107,500 (USD)
Chestertown Area Residential Home
Sold
7121 Quaker Neck Road Chestertown, MD 21620
3 Bed
1 Baths
930 sqft
Great Investment Opportunity – Fixer-Upper on 1 Acre LotAttention DIYers, investors, and renovators! This small home, located on a beautiful 1-acre lot, is a diamond in the rough, offering endless potential for the right buyer. Nestled in the quiet, rural setting of Quaker Neck just 1.5 miles from downtown Chestertown, this property is the perfect canvas for a major rehab project.The home, which is in need of significant repairs and updates, is being sold as-is, providing a great opportunity to bring your vision to life. Whether you're looking to restore it to its original charm or transform it into something entirely new, this property offers a solid foundation for your renovation ideas.Property Highlights:* 1-acre lot with plenty of space for expansion, gardening, or outdoor activities* Small house with potential to become a cozy retreat or a profitable rental* Quiet, rural location for privacy and peace of mind* Easy access to Chestertown for shopping and Quaker Neck Landing for water fun!Please note: This home needs extensive repairs and will not qualify for traditional financing, so it's ideal for cash buyers or those with renovation experience. Buyer to perform due diligence. Sellers are willing to provide architectural drawings & site plans for their planned renovation.Don’t miss this opportunity to turn a fixer-upper into your dream home or next big project. Schedule a showing today and imagine the possibilities!
Listing Courtesy of BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company / Cheryl Hurt
$80,000 (USD)
Betterton Area Land
Active
First Avenue Betterton, MD 21610
Bed
0 Baths
sqft
MLS# MDKE2005654
PRICE REDUCTION!!Wonderful lot in Betterton, only 2 blocks from the beach, and your chance to make wonderful memories in this community known as the Jewel of the Chesapeake. Betterton sits right on the upper Chesapeake Bay at the mouth of the Sassafras River, an extremely popular boating area. The beach is beautiful with calm waters and amenities for a perfect day at the beach. This community is certainly a treasure and one of the areas best kept secrets! Don't miss out on your chance to build your dream home in one of the best little spots in Maryland! Water/Sewer Allocation is available through the town.
Listing Courtesy of BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company / Terri Kulp
$59,000 (USD)
Chestertown Area Land
Active
Old Morgnec Road Chestertown, MD 21620
Bed
0 Baths
sqft
MLS# MDKE2004974
(Lot 2 - .685 acres & Lot 3 - .689 acres) Conveniently located slightly off 291, in a private area on a dead-end road, this property is close to Chestertown and minutes away from route 301. Lots sit high off the road level and adorned with young saplings. Soil evaluation from 2011 approved for 3 beds and a 2,000 sq ft home, located just outside the critical area. Lots being sold together!
Listing Courtesy of BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company / Kristina Hyland
$58,000 (USD)
Rock Hall Area Land
Active
Sharp Street Rock Hall, MD 21661
Bed
0 Baths
sqft
MLS# MDKE2005760
Come build your dream home. Located right off E Sharp Street on Chesapeake Villa is your .46 acre lot. Location is perfect to everything Rock Hall has to offer, from shops to restaurants to the water. Come check it out today.Lot has water/sewer hookup available, contact town of rock hall to confirm fees.
Listing Courtesy of BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company / William "Billy" Sutton
