Looking for something truly special? Don't miss this unique offering, located in the vibrant heart of Chestertown's Historic and Arts & Entertainment Districts! Boasting a legacy of over half a century under the stewardship of one devoted family, this multi-family property presents a rare opportunity for visionary investors and passionate renovators alike.Situated on a generous lot, steeped in the rich history of Chestertown and prominently featured on historic maps as the Laurence Lots, this property offers a canvas brimming with potential. Whether you envision revitalizing it into a majestic single-family residence or retaining its current configuration with a townhouse on one side and two apartments on the other, the possibilities are boundless.While the property stands as a testament to enduring charm and character, it's essential to note that significant settling has occurred over the years. As such, unlocking its full potential will necessitate considerable renovation efforts. This property is a bona fide fixer-upper and is exclusively offered in its current as is condition, awaiting the transformative touch of its next custodian.With its prime location , this property represents not only an investment opportunity but a chance to become part of Chestertown's storied legacy. Seize the chance to breathe new life into this home and craft a future brimming with possibility. Embrace the challenge, unleash your creativity, and make your mark on Chestertown's captivating tapestry of history and culture. Located squarely in the Arts & Entertainment District and Enterprise Zone, both residential and commercial uses are permitted.Schedule your viewing today and prepare to embark on an unforgettable journey of restoration and renewal!
Listing Courtesy of BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company / Cheryl Hurt
$395,000
Chestertown Area Townhome
Active
349 High Street Chestertown, MD 21620
7 Bed
4 Baths
3664 sqft
MLS# MDKE2004076
Looking for something truly special? Don't miss this unique offering, located in the vibrant heart of Chestertown's Historic and Arts & Entertainment Districts!Boasting a legacy of over half a century under the stewardship of one devoted family, this multi-family property presents a rare opportunity for visionary investors and passionate renovators alike. Situated on a generous lot, steeped in the rich history of Chestertown and prominently featured on historic maps as the Laurence Lots, this property offers a canvas brimming with potential.Whether you envision revitalizing it into a majestic single-family residence or retaining its current configuration with a townhouse on one side and two apartments on the other, the possibilities are boundless. While the property stands as a testament to enduring charm and character, it's essential to note that significant settling has occurred over the years. As such, unlocking its full potential will necessitate considerable renovation efforts.This property is a bona fide fixer-upper and is exclusively offered in its current as is condition, awaiting the transformative touch of its next custodian. With its prime location , this property represents not only an investment opportunity but a chance to become part of Chestertown's storied legacy. Located squarely in the Arts & Entertainment District and Enterprise Zone, both residential and commercial uses are permitted.Seize the chance to breathe new life into this home and craft a future brimming with possibility. Embrace the challenge, unleash your creativity, and make your mark on Chestertown's captivating tapestry of history and culture.Schedule your viewing today and prepare to embark on an unforgettable journey of restoration and renewal!
Listing Courtesy of BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company / Cheryl Hurt
$20,000
Chestertown Area Land
Active
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
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
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
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
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
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
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
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
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
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
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
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
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
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.
$139,000
Crumpton Area Land
Active
220 Shoals Road Crumpton, MD 21628
Bed
0 Baths
sqft
MLS# MDQA2009172
Two fantastic building parcels just off the Chester River. 1.36 acres total on a cul-de-sac at the end of a quiet road. Perc approved and ready for you to design your dream home on the Eastern Shore. Crabbing, fishing, swimming, birdwatching, you name it! Bring your house plans or just camp out and build a fire. Level building area sits on a small bluff well above the water: no flood zone! Public boat landing only a few blocks away. Easy access to Route 301. 90 minutes to Philadelphia, South Jersey, and Washington D.C. 30 minutes to Middletown, Delaware and tax-free shopping. Less than 15 minutes to historic downtown Chestertown. Founded in 1706, Chestertown sits on the banks of the Chester and is home to Washington College. Enjoy the historic homes, local shopping, restaurants, art galleries, and waterfront parks. Chestertown is home to many festivals and an award-winning weekly Farmer's Market. Property is marked by sign. Perc approval and survey on file. Parcels sold together, not separate. Drive-bys permitted. Do not enter property without an appointment.
Listing Courtesy of BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company / Joseph Ciganek
$15,000
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
$1,485,000
Church Hill Area Residential Home
Coming Soon
720 SE Creek Road Church Hill, MD 21623
4 Bed
3 Baths
2972 sqft
Comfort. Nature. Luxury. All are expressed in this Contemporary waterfront home on Southeast Creek. Listen to Ospreys from your screened porch or private second floor balcony. Cool off in the pool or practice yoga in the poolside studio space. Friends from far away can come use your detached guest cottage as a tranquil retreat. Walk down your dock and go sailing with easy access to the Chester River and beyond. Gather with the ones you care about most on the central open floor plan on the main floor. Upstairs has everything you need to decompress and take in the fine Eastern Shore lifestyle. The home is less than 15 minutes from Historic Downtown Chestertown by boat or car and less than 2 hours from Washington D.C., Philadelphia, or Baltimore.
Listing Courtesy of BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company / Kristina Hyland
$1,395,000
Chestertown Area Residential Home
Active
105 High Street Chestertown, MD 21620
5 Bed
5 Baths
3243 sqft
MLS# MDKE2005002
This is your chance to own one of the most prominent homes in Chestertown's Historic District already completely upgraded and finished to suit. The Tilley Residence was rebuilt in 1863 and celebrates the Second Empire style reminiscent of the Champs-Élysées in Paris. The neighboring properties on this sought after corner are some of the area's most important including Widehall and the Custom House which was one of the original British Royal Ports of Entry to the Americas. The current owners include one of Kent County's renowned builders and craftsmen who decided to take on this restoration as a passion project to honor its beauty and significance in the community. The home was completely updated in 2024 with new HVAC, Electrical, Plumbing, roofing, and wood flooring. The floor plan was opened up to accommodate your lifestyle in 2025. New bathrooms and kitchen were custom designed. A grand 3 story staircase greets you at the foyer along with arched entryways to introduce you to the level of detail to be found throughout. The front porch allows you to sit back to watch everything happening in town or simply admire the water. The updated layout is designed for optimal flow and natural light. The primary suite captivates you with a fireplace, spacious walk in closet, and tiled shower room with views of the water from two sides. The Mansard roof allows for the full third floor. In the basement there is a partially finished space perfect for your wine cellar along with extra unfinished tidy space for storage. There is also a fenced in rear yard perfect for intimate gatherings, pets, and gardening. Off street parking is a huge plus as well with a detached garage connecting to the rear yard. Due to this property's grandeur and scope of work, the sellers are going to let you decide on finishes such as countertops, floor stains, wall colors, and fixtures to make you feel you spend wisely. Allowance lists to be provided to interested parties. Turn this important and updated piece of Chestertown History into your Legacy property.
Listing Courtesy of BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company / Michael "Murphy" O'Neill
$1,050,000
Worton Area Residential Home
Active
12440 Woods Road Worton, MD 21678
4 Bed
2 Baths
1955 sqft
MLS# MDKE2004962
This Waterfront Contemporary home is nestled on a bluff with sweeping views of Still Pond Creek. The property checks all of the boxes for your retreat including a well maintained deck, screened river room for crab feasts, private sandy beach and dock with several boat lifts. The living room has a cathedral ceiling, wood burning fireplace, and glass sliders leading you to the deck with incredible views of nature and wildlife. One of the 3 main floor bedrooms, the primary suite has an ensuite bathroom, walk-in closet, and full length windows to celebrate the property's connection with the water. On the lower level you will find another bedroom, den, workshop, and garage. Upgrades include New Heating and Cooling (2024&2025), New Roof (2024), Garage Door (2024), Plumbing and Electrical Updates (2022), Generator, Rinnai Tankless hot water heater, and Reverse Osmosis water treatment. Still Pond Creek provides direct access to the open waters of the Chesapeake Bay for prime boating opportunities however is a protected tributary making it great for water sports. The property is located in the rolling farmlands of Worton, only 15 minutes from the shops, restaurants, and galleries of downtown historic Chestertown. Philadelphia, Washington D.C., and Baltimore are all less than a 2 hour drive making this perfect for a weekend getaway or year round residence.
Listing Courtesy of BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company / Michael "Murphy" O'Neill
$775,000
Sykesville Area Residential Home
Pending
1600 Liberty Road Sykesville, MD 21784
5 Bed
4 Baths
2972 sqft
MLS# MDCR2025110
Welcome to 1600 Liberty Road: the perfect home for a growing family in a great location. Quality craftsmanship in this new construction truly shows while the list of features goes on and on: Brazilian Cherry hardwood floors, 9 foot tray ceilings, bay windows, ceramic tile kitchen and baths, brushed nickel fixtures, a electric fireplace, oversized back deck and so much more. This home has so much natural light and really celebrates the views of the surrounding farmland. The gourmet kitchen features quartz countertops with overhanging bar, stainless steel appliances, double sink, quiet-close drawers and more. The kitchen / breakfast area flow seamlessly into the expansive open concept living and formal dining rooms. Easily step out of the living room and onto the oversized back deck. The main floor also features a second living room / family room or an office space. Continuing upstairs, the luxurious owner's suite has great views of the surrounding farmland. The 3 additional comfortably sized bedrooms with large closets and another full bath complete the second floor. The fully finished basement has another bedroom with full bath and laundry room with separate exterior entrance. This completely separate space could easily be turned into a rental for extra income. Private backyard features a tall privacy fence: perfect for entertaining and plenty of space for the kids and pets. Plenty of parking with an oversized 2-car garage and concrete paved driveway. All systems and appliances come with a one-year manufacturer's warranty. Minutes away from shopping, dining, and entertainment: this property is ideally situated for an easy commuting lifestyle. Schedule an appointment today!
Listing Courtesy of BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company / Joseph Ciganek
$539,000
Kennedyville Area Residential Home
Active
11960 Flour Mill Street Kennedyville, MD 21645
7 Bed
5 Baths
3136 sqft
MLS# MDKE2004434
Welcome to 11960 Flour Mill Street. This is the perfect house for a growing family or a multi-generational household. Main House has 6 full bedrooms and 4 full bathrooms while the second floor above the garage is a spacious mother-in-law suite with a separate entrance, efficiency kitchen, full bath and walk-in closet. First floor has a bedroom and full bath and wide open floor plan in the kitchen and living rooms. Kitchen features stainless steel appliances, granite countertops and wood cabinets. Second floor has 5 bedrooms and 2 full baths. Partially finished full basement has another full bathroom and offers a range of possibilities for the next owner. This home has more room and storage than you could imagine. The Villages at Kennedyville is a quiet, local community. Less than 90 minutes to Philadelphia and Washington D.C. 30 minutes to Middletown, Delaware and tax-free shopping. Close to Turners Creek State Park, Betterton Beach and the restaurants/marinas in Galena on the Sassafras River. Just a few minutes to historic downtown Chestertown. Founded in 1706, Chestertown sits on the banks of the Chester and is home to Washington College. Enjoy the historic homes, local shopping, restaurants, art galleries, and waterfront parks. Chestertown is home to many festivals and an award-winning weekly Farmer's Market. Seller offering $7,000 credit at closing to repair the Air Conditioning units.
Listing Courtesy of BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company / Joseph Ciganek
$515,000
Chestertown Area Residential Home
Active
116 Pine Chip Road Chestertown, MD 21620
3 Bed
2 Baths
2767 sqft
MLS# MDQA2010882
Don’t let the outside fool you—this beautifully renovated 3-bedroom, 1.5-bathroom home offers three levels of living space, with over 2,200 sq. ft. above ground and an additional 550 sq. ft. below ground! Every inch of this home has been thoughtfully updated to blend modern comfort with timeless charm.Step inside to discover a stunning custom kitchen, a true chef’s dream featuring a gas stove, upgraded quartz countertops, solid wood cabinetry, and stylish open shelving—perfect for both cooking and entertaining. The spacious living areas boast brand-new LVP flooring, fresh finishes, and an inviting atmosphere throughout.Upstairs, the primary bedroom is a private retreat, complete with a mini-split AC/heat unit, a large dressing room, and a convenient half bath.Head downstairs to a versatile lower level, where an open-concept space offers endless possibilities—whether you need a media room, game area, crafting space, or home gym. The large laundry area and utility room provide added functionality.Step outside to your own backyard oasis, enclosed by a beautiful privacy fence. Enjoy the spacious patio, detached garage/barn, and storage shed—ideal for hobbies, storage, or workshop space.This home is completely move-in ready and packed with upgrades—all it needs is you! Don’t miss your chance to see this hidden gem—schedule your private showing today!
Listing Courtesy of BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company / William "Billy" Sutton
$499,000
Betterton Area Townhome
Active
1 Bayview Road Betterton, MD 21610
3 Bed
2 Baths
2000 sqft
MLS# MDKE2005008
Rigbie Bluff is the perfect maintenance-free community in the quiet waterfront town of Betterton; known as the Jewel of the Chesapeake. Located at the confluence of the Sassafras River and Chesapeake Bay, Betterton got its reputation for its picturesque sunsets and wonderful public beach. Embrace the waterfront lifestyle and so much more without the waterfront taxes. This 3 bedroom, 2 bathroom unit is being sold fully furnished. As one of the larger units; it has plenty of room for the whole family. Natural light abounds with water views from both balconies or anywhere inside. Galley kitchen with granite countertops and stainless steel appliances. The main floor has an open floor plan, two bedrooms and a full bathroom. Large primary bedroom with ensuite bath and office space upstairs. Plenty of closet space throughout. Full basement has plenty of room for storing outdoor toys and equipment. Recent upgrades include: primary bathroom remodel, waterproof luxury vinyl plank flooring (original hardwoods underneath), carpets, Anderson windows, washer/dryer, water heater, interior doors, paint, and much more. Condo Association just finished renovating the decks and siding. Condo amenities include: private pier with water and electric, designated boat slip with 6,000 pound lift, community pool and kayak storage. Just a few steps from the water. This is the perfect weekend getaway or primary residence on the Eastern shore. Come see all that the Jewel of the Chesapeake has to offer.
Listing Courtesy of BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company / Joseph Ciganek
$485,000
Chestertown Area Residential Home
Coming Soon
101 S Mill Street Chestertown, MD 21620
2 Bed
3 Baths
1476 sqft
Historic charm with a modern floor plan. Live just around the corner walking to the shops, galleries, and restaurants of downtown Chestertown in this beautifully updated Victorian on quiet Mill Street. High end appliances such as Miele and Bosch adorn the kitchen and laundry. Easily converted back into a 3 bedroom. The backyard is well landscaped, has a covered outdoor living space, and a spacious detached hobby shed or office space. This low maintenance property with walkable lifestyle works perfectly for a weekend retreat or year round residence. Chestertown is located less than 1.5 hours from Washington D.C, Philadelphia, and Baltimore.
Listing Courtesy of BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company / Michael "Murphy" O'Neill
$309,000
Harrington Area Residential Home
Active
205 E Madison Avenue Harrington, DE 19952
3 Bed
2 Baths
1176 sqft
MLS# DEKT2032824
Charming Single-Level Living in a Prime Location!Welcome to this inviting single-family home, offering the ease of one-level living in a beautifully designed space. This residence features a thoughtfully laid-out floor plan with ample natural light and open, flowing spaces. The heart of the home is the spacious living area, seamlessly connected to a large kitchen with room for an island, perfect for entertaining. With 3 bedrooms and 2 full bathrooms, each room is designed for comfort and convenience, making it ideal for anyone seeking a low-maintenance lifestyle either as a first time home buyer or for aging in place. A split bedroom layout is ideal as the main bedroom suite adorns the entire one side of the home with a walk in closet and bath. New carpet has been installed in the living room as of 12/3/24, The home is located a few minutes from Killens Pond State Park, Harrington Raceway & Casino, and a short distance to Delaware Beaches. Make your appointment today to take advantage of owning single level living in a quiet neighborhood.
Listing Courtesy of BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company / Kristina Hyland
$309,000
Chestertown Area Residential Home
Active
909 Round Top Road Chestertown, MD 21620
3 Bed
1 Baths
1698 sqft
MLS# MDQA2011970
Need additional space, no problem! This home has a sunken den with a brick wood fireplace off the main living room that could be used as an office and a humongous 23’8 X 18’4 family room currently used as the Billards room hosting a 9ft pool table/gym off the kitchen/dinning room that was added in 2021! This room is great for entertaining & hosting large parties and could be a fantastic place to have a daycare! A voluntary HOA allows access to the communities private beach, dock and playground all located on Rosin Creek with access to the Chester River! Va loan has an assemble low interest rate for those who qualify for VA!
Listing Courtesy of BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company / Kristina Hyland
$295,000
Still Pond Area Residential Home
Pending
12664 Still Pond Road Still Pond, MD 21667
2 Bed
2 Baths
1352 sqft
MLS# MDKE2004866
Lovely restored country home in the quaint village of Still Pond.The house has many upgrades including a new roof in 2024, a remodeled Kitchen in 2023, a BAT septic system, wood floors, a screened-in front porch, and a rear mud room. Beautiful sunsets over the farm field, a quiet neighborhood, and much more.Also included is the guest cottage with Barnwood walls, and barn door. kitchen and bathroom remodeled in 2022. Rent it out, use it as an office, or for a guest cottage.Home Sweet Home is 15 minutes to downtown Chestertown and 30 minutes to Middletown. Move in ready!
Listing Courtesy of BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company / Mary Fielding
$275,000
Betterton Area Residential Home
Pending
12 Third Avenue Betterton, MD 21610
4 Bed
2 Baths
2500 sqft
MLS# MDKE2004842
Just 3 blocks from the beach, this 4 bed and 2 bath home is perfect as a full time residence or as a vacation home! With a first floor bedroom and bath makes this home ideal for one floor living. The second floor offers two large bedrooms and an additional/bonus room allows for an office, yoga studio space for whatever your needs/desires may be. The large kitchen is open to the dining and living room with another room for your private office/TV room/craft room or whatever you need it to be! A walkout basement like garage sits on the side of the home that enters into the kitchen. A tankless/instant water heater was recently installed. Update to your liking and make it your dream home by the beach! This home is being sold as is. Lender repairs could potentially be addressed for repairs by the Seller. Please note that this home will need interior paint and new carpets. it’s priced accordingly for those needs!
Listing Courtesy of BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company / Kristina Hyland
$269,975
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
$235,000
Chestertown Area Townhome
Active
300 Hilltop Lane Chestertown, MD 21620
3 Bed
3 Baths
1200 sqft
MLS# MDKE2005004
Welcome to this beautifully updated end-unit townhouse in the heart of Chestertown! Featuring 3 bedrooms and 2.5 bathrooms, this home is fresh, bright, and ready for you to move right in. The kitchen shines with freshly painted cabinets and brand-new appliances, while new flooring throughout adds a modern touch.Enjoy the convenience of a patio out back—perfect for relaxing or entertaining. Located just minutes from town, you’ll love the easy access to shopping, dining, and everything Chestertown has to offer. Easy to show—schedule your tour today!
Listing Courtesy of BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company / William "Billy" Sutton
$229,000
Betterton Area Residential Home
Active
14 Third Avenue Betterton, MD 21610
3 Bed
3 Baths
2050 sqft
MLS# MDKE2005010
A home finished your way with what could be over 3,078 square feet of living space! Complete your new Victorian style home with the finishes & colors you enjoy! Located within a .3 mile walk to Betterton Beach and the Town Dock! Public showers, rest rooms and transient boat slips are all at your disposal! The interior of the home is a blank slate and has been protected from the elements. The home features a full concrete basement, a large kitchen space with access to the garage and the wrap around porch, formal dining, living room with an octagon window setting allowing natural light to fill the room and full bath on the 1st floor. Moving up the stairs to the 2nd floor are 3 bedrooms 2 full baths, laundry and the possibility for a large 4th bedroom or playroom/game room! The large two car garage has ample space for your bikes, jet ski and all your water toys! A builder/contractor is awaiting your call, with enough notice I can have a Builder/contractor walk through with you as you discuss your needs, likes and wants along with your budget! This is not a rehab, the home was built and never finished.
Listing Courtesy of BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company / Kristina Hyland
$225,000
Rock Hall Area Residential Home
Active
6121 Tolchester Road Rock Hall, MD 21661
3 Bed
1 Baths
1064 sqft
MLS# MDKE2004606
Charming 3-Bedroom Home in Rock Hall, MD – Recently Remodeled with new roof on a Spacious Lot!Welcome to this beautifully remodeled gem, originally built in 1920, located in the picturesque water-oriented town of Rock Hall. With 1,024 square feet of thoughtfully designed living space, this home seamlessly blends historic charm with modern comforts.This recently remodeled 3-bedroom, 1-bath residence offers a perfect blend of modern comfort and classic charm. Situated on a generous lot, this property provides ample outdoor space for gardening, entertaining, or simply enjoying the serene surroundings. An outdoor cinder block shed provides storage for all of your gardening and outdoor supplies. New roof just installed!Step inside to discover an inviting floor plan that showcases stunning new finishes throughout. The kitchen boasts updated appliances and countertops making it ideal for culinary enthusiasts. The three bedrooms offer cozy retreats at the end of the day. The tastefully renovated bathroom includes modern fixtures and a relaxing atmosphere.Outside, the expansive yard is a blank canvas, ready for your personal touch—whether it’s a garden, play area, or outdoor living space. Located just minutes from local shops, restaurants, and the scenic waterfront, this home combines convenience with the tranquility of small-town living.Located just moments from the picturesque waterfront and vibrant local shops, this property is an ideal retreat for those seeking a tranquil lifestyle. Don’t miss your chance to own a piece of Rock Hall’s history, fully modernized for today’s living. Schedule your showing today!
Listing Courtesy of BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company / Cheryl Hurt
$190,000
Betterton Area Residential Home
Active
1 Kent Drive Betterton, MD 21610
2 Bed
1 Baths
658 sqft
MLS# MDKE2004884
Charming Bungalow by the Bay!Discover the perfect coastal retreat in this delightful 2-bedroom bungalow, just one block from the beach! Nestled in a quaint town of only 283 residents, this home boasts beautiful hardwood ceilings, a screened front porch for relaxing evenings, and spacious back and side decks ideal for outdoor entertaining. The lower-level laundry and ample storage provide convenience, with plenty of space for kayaks, beach chairs, and more.Enjoy the town’s public docks, showers, and restrooms, or explore the nearby Hopkins Game Farm for outdoor adventures. Wine lovers will appreciate Crow Vineyard just a short drive away, while history enthusiasts can visit charming Chestertown. With a local park, tennis/pickleball courts, and a scenic picnic area, this bayfront community has something for everyone. Don’t miss your chance to own a slice of paradise!
Listing Courtesy of BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company / Kristina Hyland
$149,500
Church Hill Area Townhome
Active
515 Main Street Church Hill, MD 21623
3 Bed
1 Baths
1284 sqft
MLS# MDQA2010586
This 1909 townhouse at 515 Main Street in Church Hill, Maryland, is brimming with potential and waiting for your personal touch. Offering 3 bedrooms and 1 bathroom, this home provides plenty of space to create something special.Enjoy recent updates, including brand-new carpet in the primary bedroom and fresh flooring in both the kitchen and laundry room. A bonus room off the primary bedroom makes a great home office or nursery. The spacious laundry room at the back of the house adds convenience, while the partly fenced yard and original hardwood floors in select rooms enhance the home’s charm.Located in a picturesque small town, this property offers a unique blend of history and opportunity. The seller is eager to sell and open to negotiation—this is your chance to grab a great deal!Bring your vision and schedule a showing before it's too late!
Listing Courtesy of BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company / William "Billy" Sutton
$107,500
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
$64,000
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
