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Chestertown MD Real Estate & Homes for Sale

66 Properties Found

The median home value in Chestertown, MD is $340,000. This is higher than the county median home value of $249,900. The national median home value is $308,980. The average price of homes sold in Chestertown, MD is $340,000. Approximately 44% of Chestertown homes are owned, compared to 42% rented, while 14% are vacant. Chestertown real estate listings include condos, townhomes, and single family homes for sale. Commercial properties are also available. If you like to see a property, contact Chestertown real estate agent to arrange a tour today!
Learn more about Chestertown Real Estate.


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Beds:
3
Baths:
2.00
Sq.Ft.:
1,248
Status:
NEW LISTING
MLS#:
MDKE2006096
Type:
Single Family
Subdivision:
CHESAPEAKE LANDING
Lot size:
0.73 Acres
Year built:
2021
Courtesy: TTR Sotheby's International Realty
View additional info

Tucked neatly on a corner in Chesapeake Landing, this three-quarter acre parcel is among one of the largest in the neighborhood. The 2020 custom built home exudes simple luxury. Offering three bedrooms and two full baths in a simple and efficient floorplan, is has flow and comfort in mind. It features a modern kitchen with tall quiet close cabinets, granite counter tops and a tile backsplash, stainless appliances, and an ample pantry for storage. Six-over-six oversized windows throughout the home, extra tall doors, a transom window over the front door, and a ten-foot door to the screen porch allows light to pour inside. A full and separate laundry room remove that chore from the living space and offer a dedicated work room with storage. The Primary Suite includes a generous walk-in closet and en suite bath. Since 2021, upgrades and improvements include: screened porch, Leafguard on all gutters, shed to coordinate with the home's aesthetics, asphalt driveway, thoughtful landscaping, water treatment system, and is wired for IQ Fiber (formerly ThinkBig) for internet. This home is absolutely, without question, turnkey and ready for its new stewards!

Beds:
2
Baths:
1.00
Sq.Ft.:
1,296
Status:
NEW LISTING
MLS#:
MDKE2006670
Type:
Single Family
Subdivision:
NONE AVAILABLE
Lot size:
0.09 Acres
Year built:
1900
Courtesy: Cummings & Co. Realtors
View additional info

Investor Special - Charming Colonial in Prime Chestertown Location! Welcome to 234 N College Ave, an adorable colonial full of character and potential, nestled in the heart of historic Chestertown. This short sale opportunity is a rare find for savvy investors or buyers ready to bring their vision to life. With classic colonial charm, this property offers the perfect canvas for renovation or restoration. Located near downtown Chestertown's shops, restaurants, and waterfront, the location can't be beat. Original architectural details, a cozy layout, and timeless curb appeal make this home a standout gem waiting to be polished. Don't miss your chance to invest in one of Maryland's most beloved small towns. Sold as-is. Cash or renovation loans preferred.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,900
Status:
NEW LISTING
MLS#:
MDKE2006668
Type:
Townhouse
Subdivision:
OAK HOLLOW
Lot size:
0.05 Acres
Year built:
2004
Courtesy: Cross Street Realtors LLC
View additional info

Welcome to this three-level, interior-unit townhome in the desirable Oak Hollow community of Chestertown. Conveniently located near shopping, schools, the YMCA, and historic downtown, this home offers comfortable living and low-maintenance convenience. The entry level features a one-car garage and a flexible bonus room ideal for a home office, gym, or recreation space with walk-out access to the rear yard. The main level includes a spacious living room, half bath, and an eat-in kitchen with pantry storage and adjoining dining area. Step outside to the rear deck overlooking a peaceful wooded backdrop. The upper level offers three bedrooms, including a primary suite with a private bath, plus a full hall bath and conveniently located laundry area. Whether you're a first-time homebuyer, looking to downsize, or seeking an investment property, this Oak Hollow townhome is ready for its next owner.

Beds:
3
Baths:
2.00
Sq.Ft.:
2,210
Status:
NEW LISTING
MLS#:
MDKE2006626
Type:
Single Family
Subdivision:
NONE AVAILABLE
Lot size:
0.08 Acres
Year built:
1900
Courtesy: ANR Realty, LLC
View additional info

Investor Alert - Classic 2-Story Colonial Packed with Potential! Welcome to this Charming Colonial Offering the Space, Layout, and Bones that Savvy Buyers Dream of. The Spacious Kitchen, Living Areas and Bedrooms Provide Room to Breathe and Personalize. Head Out Back to Enjoy the Enclosed Rear Porch, Yard and a Convenient Storage Shed that offers Ample Space for Tools, Equipment, and More. This Home is Ready for Your Personal Touches. A Little Cosmetic Love will go a Long Way in Unlocking Serious Equity and Making this Property Truly Shine. Whether you're an Investor, Flipper, or Savvy First-Time Buyer Looking to Build Sweat Equity, This is the Opportunity You've Been Waiting For. Sold As-Is.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,404
Status:
NEW LISTING
MLS#:
MDKE2006644
Type:
Single Family
Subdivision:
CHESAPEAKE LANDING
Lot size:
0.35 Acres
Year built:
2007
Courtesy: Serhant
View additional info

Welcome home to 10572 Watonga Road, a charming Cape Cod nestled on a beautifully wooded corner lot in the desirable Chesapeake Landing community. Built in 2007 and meticulously maintained, this 3-bedroom, 2-bath home offers the perfect blend of comfort, privacy, and Eastern Shore charm. The spacious .35-acre property is surrounded by mature trees, creating peaceful wooded views from both the front and back of the home. Inside, you'll find luxury vinyl plank flooring throughout the main living areas in near-new condition, along with well-maintained carpeting in the bedrooms. Thoughtful updates include a water softener installed in 2024, a fenced yard added just two years ago, French drains, and two sump pumps designed to keep the property draining efficiently. An oversized shed provides excellent storage, while the deck offers the perfect place to enjoy your private outdoor setting. Life in Chesapeake Landing is all about enjoying nature and the water. Residents frequently spot deer, wild turkeys, turtles, and other local wildlife throughout this quiet, established neighborhood. There is no HOA, but the voluntary community association provides access to sought-after water amenities, including a community boat ramp, kayak launch, and fishing pier. The neighborhood also features Mill Brook Pond and the popular Turtle Walking Trail, giving residents even more opportunities to enjoy the outdoors. Located just minutes from historic Chestertown, you'll have easy access to everything that makes Kent County so special. Downtown Chestertown is only about seven minutes away and offers a vibrant year-round farmers market every Saturday from 9 a.m. to noon, locally owned shops, a beloved independent bookstore, and favorite dining destinations like Bad Alfred's Distilling. Also check out the sand bars at the marinas, perfect for waterfront happy hours. Whether you're drawn to the area's marinas, boating opportunities, charming small-town atmosphere, or the spacious homesites that provide room to breathe, this property delivers the true Eastern Shore lifestyle where water access is around every corner and community charm is abundant. If you've been searching for a home that combines modern convenience, natural beauty, and small-town waterfront living, 10572 Watonga Road is ready to welcome you home.

Beds:
4
Baths:
1.00
Sq.Ft.:
2,920
Status:
NEW LISTING
MLS#:
MDKE2006642
Type:
Single Family
Subdivision:
CHESTERTOWN
Lot size:
0.28 Acres
Year built:
1972
Courtesy: Blue Star Real Estate, LLC
View additional info

Great area and lot walking distance to the Chesapeake bay and Tolchester Marina. House is in need of rehab but offers quite a bit of upside in the lot and location. Buyer to verify all info

Beds:
4
Baths:
3.00
Sq.Ft.:
2,160
Status:
NEW LISTING
MLS#:
MDKE2006640
Type:
Single Family
Subdivision:
CHESAPEAKE LANDING
Lot size:
0.39 Acres
Year built:
2001
A broker reciprocity listing Courtesy: Real Broker, LLC
View additional info

Welcome home to relaxed Eastern Shore living in the waterfront community of Chesapeake Landing. This beautifully updated 2,140 sq ft Cape Cod offers the perfect blend of charm and modern comfort with 3 bedrooms, 2.5 baths, and a welcoming floor plan designed for everyday life. The main level features new flooring throughout, a spacious living area, formal dining room, and a renovated country kitchen with new appliances, new counters, and plenty of space for gathering. A main-level bedroom adds flexibility for guests or one-level living. Enjoy morning coffee or evening sunsets on the back deck overlooking the open, cleared 0.39-acre lot - perfect for gardening or outdoor fun. Additional highlights include a 2-car garage and access to community amenities with a beach, fishing pier, and pavilion. Just minutes from historic downtown Chestertown, you'll love being close to local shops, dining, marinas, and all the charm of Eastern Shore living.

Beds:
4
Baths:
2.00
Sq.Ft.:
1,277
Status:
NEW LISTING
MLS#:
MDKE2006026
Type:
Single Family
Subdivision:
BYFORD DEVELOPMENT
Lot size:
0.34 Acres
Year built:
1965
Courtesy: Doug Ashley Realtors, LLC
View additional info

Desirable in-town living in a peaceful neighborhood. This solid brick front rancher was totally renovated in 2022 and is still like New. The pictures tell the story. Easy one-level living with an open concept for the Living Room, Dining, and Kitchen. A really open feel. This home offers 4 bedrooms and 2 full bathrooms. If this many bedrooms are not needed, the fourth bedroom could have many other potential uses, with it being right off the kitchen and living room. Out front, you have a cozy front porch, and out from the sliding glass door it opens up to a deck and a good-size backyard. Just pick where you would like to sit for a few and relax. In the back of the yard, you have a new storage shed that is always a plus. Bring your bikes; you will have the perfect streets in this neighborhood to ride and use as you head to the Local Farmers Market. The pictures show this house perfectly. It is in such good condition and has been well cared for and maintained. All ready to move into. It won't disappoint.

Beds:
3
Baths:
1.00
Sq.Ft.:
1,967
Status:
NEW LISTING
MLS#:
MDQA2017480
Type:
Single Family
Subdivision:
NONE AVAILABLE
Lot size:
2.64 Acres
Year built:
1972
Courtesy: Keller Williams Flagship
View additional info

Welcome to country living at its finest! Nestled on approximately 2.64 acres, this solid brick rancher offers nearly 2,000 square feet of living space and endless possibilities. Enjoy the peace and privacy of a rural setting while still being conveniently located near Chestertown, Millington, and major commuter routes. The spacious lot provides room for gardening, recreation, hobbies, or simply enjoying the outdoors. Features include an attached garage, generous living areas, and the opportunity to customize and make this property your own. Whether you're looking for a primary residence, weekend retreat, or investment opportunity, this property offers exceptional potential in a picturesque Eastern Shore setting.

Beds:
2
Baths:
3.00
Sq.Ft.:
1,518
Status:
Active
MLS#:
MDKE2006614
Type:
Single Family
Subdivision:
CHESTERTOWN HISTORIC DISTRICT
Lot size:
0.08 Acres
Year built:
1820
Courtesy: Benson & Mangold, LLC
View additional info

Historic Charm in the Heart of Downtown Chestertown Step back in time and discover the character, craftsmanship, and endless potential of this circa-1820 historic home. Nestled in the heart of downtown Chestertown, this property is filled with the original architectural details and timeless charm that historic home lovers dream about. Featuring 2 spacious bedrooms with the potential for a 3rd, 3 full bathrooms, a welcoming kitchen with an eat-in area, and a generously sized dining room, this home offers a solid foundation for restoration and reimagining. While the property is in need of some repairs and renovation, it presents an incredible opportunity for the buyer who has always dreamed of owning a piece of history; or the savvy investor looking for their next restoration project. Outside, escape to your own private backyard sanctuary complete with a brick patio, fountain, and peaceful garden setting, an unexpected retreat right in town. Please note that the home is currently furnished and filled with d cor and personal property. All furniture, d cor, and contents currently in the home will be auctioned prior to settlement and are not included in the sale unless otherwise agreed upon. If you've been waiting for the right historic home to make your own, this is your chance to bring new life to a true Chestertown treasure. ???

Beds:
9
Baths:
7.00
Sq.Ft.:
6,000
Status:
Active
MLS#:
MDKE2006596
Type:
Single Family
Subdivision:
TOLCHESTER
Lot size:
9.2 Acres
Year built:
1743
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Circa 1743 with a stately 1825 addition, The Inn at Mitchell House is a rare pre-Revolutionary manor home on 9+ manicured acres on Maryland's Eastern Shore. Listed on the National Star-Spangled Banner Trail and just a mile from the Chesapeake Bay, this storied property offers a once-in-a-generation chance to own one of the region's most beloved historic estates. The grounds unfold past champion and organic fruit trees, a generous herb garden, an original 18th-century smoke house, two private bridges over Stoneybrook Pond which are all framed by woods and rolling farm fields. Inside, nine bedrooms and six-and-a-half bathrooms reveal nearly two and a half centuries of craftsmanship: original wood floors, brick floors in the dining room and kitchen, signature Bulls Eye moldings, exposed hand hewn beams, eight fireplaces and soaring 11-foot ceilings. For more than 40 years the property has operated as a successful Bed & Breakfast. An optional furniture package is available for a seamless turnkey transition. Its origins as a single-family residence also make it an extraordinary private estate, full-time home or weekend retreat. A coveted sewer allotment is included with the sale which opens the door for a future carriage house, barn, additional dwelling, stable, studio or expanded hospitality use. A new roof, a complete exterior paint job, new hot water heater, new well pump and updated electrical service were completed in 2025-2026. This delivers the rare combination of historic character and modern peace of mind. Tolchester Marina and the Shanty Beach Bar are a mile away. Rock Hall is six miles down the road and the charming historic district of Chestertown is just ten miles away. After nearly four decades of careful stewardship, the current owners are ready to pass on the privilege and the story of The Mitchell House.

Beds:
3
Baths:
1.00
Sq.Ft.:
1,248
Status:
Active
MLS#:
MDKE2006394
Type:
Manufactured Home
Subdivision:
CHESTER HEIGHTS
Lot size:
0.69 Acres
Year built:
1975
Courtesy: Doug Ashley Realtors, LLC
View additional info

Nice basic rancher offering 3 bedrooms and a full bath, generous sized living room with a large window allowing plenty of light in. The kitchen has an eat-in counter space that opens into the dining area. This space is nice and open, as you can easily see into the living room. Still plenty of space for a table. The washer and dryer are located in the oversized storage closet with bi-fold doors in the kitchen. Has an additional coat closet as you come in the side door and a separate pantry. Nice open back yard. A solid house in proximity to town. Good place to make your own and call home, or an investment.

Beds:
3
Baths:
4.00
Sq.Ft.:
3,142
Status:
Active
MLS#:
MDKE2006468
Type:
Single Family
Subdivision:
QUAKER NECK
Lot size:
11 Acres
Year built:
1955
Courtesy: TTR Sotheby's International Realty
View additional info

Welcome to the epitome of Eastern Shore waterfront luxury, offered for the first time in almost 60 years. This stunning 11-acre estate offers an unparalleled lifestyle, featuring 560 feet of prime water frontage on the Chester River and a private 140-foot dock with 7 feet of mean low water, perfect for all your adventures. ** The heart of this property is the beautifully renovated 3-bedroom, 2 full bath, 2 half bath main home, meticulously remodeled in 2018 with the highest quality materials and fixtures. The residence boasts sweeping water views from nearly every room, allowing you to enjoy picturesque sunrises Chester River. ** As you enter, you are greeted by a grand living room featuring a striking five-foot fireplace set within a soaring vaulted ceiling, creating a warm and inviting atmosphere. Expansive windows frame the breathtaking views and fill the space with natural light, enhancing the open-concept design that is perfect for both relaxing and entertaining. ** The gourmet kitchen is a chef's dream, equipped with top-of-the-line stainless steel appliances, custom cabinetry, an oversized island with seating, and elegant custom stone and wood countertops. This thoughtfully designed space allows for effortless meal preparation and entertaining. ** Retreat to the luxurious primary suite, a true sanctuary featuring its own private walled garden, offering a serene escape for relaxation and outdoor enjoyment. The suite also includes a cozy fireplace, perfect for creating a romantic ambiance. The spa-like bathroom is designed for ultimate relaxation, a spacious glass-enclosed double head shower, and dual vanities with exquisite finishes. A generous walk-in closet provides ample storage, ensuring organization and convenience. ** The outdoor living features of this luxurious estate are truly exceptional, designed to create an idyllic sanctuary for relaxation and entertainment. At the heart of the outdoor space is a stunning waterfront concrete pool, refurbished in 2018, offering a refreshing retreat on warm summer days while providing breathtaking views of the Chester River. Surrounding the home, the professionally designed landscaping enhances the natural beauty of the property, featuring lush gardens, vibrant plantings, and mature ornamental trees. The side patio, complete with a charming brick fire pit, invites gatherings with friends and family, perfect for cozy evenings under the stars. The poolside patio off the main living room makes alfresco dining a breeze. Additionally, the private walled garden serves as a tranquil oasis, offering a serene space to unwind amidst nature, making this outdoor area the perfect complement to the luxurious lifestyle this estate offers. ** Accommodate guests or staff in the charming 3-bedroom, 2-bath guest/caretaker's cottage, built in 2013. A spacious 2.5-bay workshop provides ample storage for your outdoor equipment and hobbies. ** This exceptional property seamlessly blends luxury and tranquility, offering a unique opportunity to own a piece of paradise on the Eastern Shore. Don't miss your chance to experience the charm and elegance of this extraordinary waterfront estate!

Beds:
3
Baths:
3.00
Sq.Ft.:
1,896
Status:
Active
MLS#:
MDKE2006586
Type:
Single Family
Subdivision:
THE VILLAGE AT CHESTERTOWN
Lot size:
0.09 Acres
Year built:
2023
Courtesy: Long & Foster Real Estate, Inc.
View additional info

Welcome to 102 Flying Cloud a new community known as The Village of Chestertown. This is a rare opportunity to own a home at this price and condition. Designed to with an open 1st floor features a bright white kitchen and dining area open to a large living room for entertaining and a 1/2 bathroom. The 2nd floor features 3 bedrooms 2 full bathrooms. The primary feature private bath and large closet. The exterior has large backyard for friends and family concrete driveway and freshly manicured yard. Call today for private showing today.

Beds:
4
Baths:
5.00
Sq.Ft.:
5,265
Status:
Active
MLS#:
MDKE2006502
Type:
Single Family
Subdivision:
FAIRGALE PROPERTIES
Lot size:
3.55 Acres
Year built:
2002
Courtesy: Gunther-McClary Real Estate
View additional info

Welcome to 22470 Fairgale Farm Ln, a spacious home and property perched over Fairlee Creek, with an assigned boat slip. 3.55 acres, partly wooded, exceptionally landscaped, and perfectly framed water views. Walk down to the water to enjoy the views or launch a kayak. The deep-water boat slip, outfitted with a boat lift, is just a short distance away. The home features 4 bedrooms and 5 full bathrooms, plus a large loft that could be used as an additional bedroom. The large eat-in kitchen has expansive windows that perfectly frame the water view. A great spot for entertaining! Doors in the kitchen lead to the waterfront deck, spanning the front of the home. In both sitting rooms, you'll find fireplaces that have been conveniently updated to propane. The first-floor primary bedroom opens up to the waterfront deck and offers a fantastic water view, as well as a large bathroom that was recently updated. Upstairs you'll find two waterfront bedrooms, one with an updated attached bath. There's a second full bathroom and ample closet space in the hallway. Downstairs, there are two additional full bathrooms and a large bedroom. Above the kitchen sits the light-filled loft, a great office, studio, or extra bedroom. The exterior has a generous front porch, outdoor shower, circular drive, 2-car garage, fenced dog run, and additional garage space connected to the basement. This light-filled waterfront property is located 15 minutes away from the waterfront community of Rock Hall and historic Chestertown.

Beds:
4
Baths:
2.00
Sq.Ft.:
1,325
Status:
Active
MLS#:
MDKE2006482
Type:
Single Family
Subdivision:
CHESTERTOWN
Lot size:
0.41 Acres
Year built:
1960
Courtesy: Redfin Corporation
View additional info

Welcome to this charming 4-bedroom rancher nestled in the heart of historic Chestertown, offering the perfect blend of peaceful rural living and convenient access to town amenities. Enjoy easy one-level living with a functional layout and gorgeous hardwood floors that add warmth and character throughout the home. The beautiful white kitchen features stainless steel appliances, including a gas range and microwave range hood, creating a bright and inviting space for everyday living and entertaining. The home offers four main-level bedrooms, including a comfortable owner's suite with a private ensuite bathroom. Surrounded by the beauty of Maryland's Eastern Shore, this property is ideal for those who appreciate outdoor living, with countless nearby opportunities for hunting, fishing, crabbing, boating, and exploring nature. Enjoy the charm, history, shops, dining, and waterfront attractions that make Chestertown such a sought-after destination while still embracing the peace and privacy of a rural setting. Mortgage savings may be available for buyers of this listing.

Beds:
5
Baths:
4.00
Sq.Ft.:
2,534
Status:
Active
MLS#:
MDKE2006510
Type:
Single Family
Subdivision:
THE VILLAGE AT CHESTERTOWN
Lot size:
0.11 Acres
Year built:
2023
Courtesy: CENTURY 21 New Millennium
View additional info

NEW PRICE - Exceptional value for over 2,500 square feet of newer construction in the Village of Chestertown! A stunning 2023-built home with well-designed architectural elevations; two tone complimentary shades which beautifully compliment these unique features. The curb appeal captures your attention and the welcoming front porch invites you to slow down and relax.. your home! Step through the Craftsman style front door into a move-in ready, three-story residence offering 5 bedrooms and 3.5 baths across 2,535 square feet of thoughtfully designed living space. The main level features an open-concept layout with a spacious family room, dining area, and bright, well-appointed kitchen - perfect for both everyday living and entertaining. A convenient first-floor laundry room and powder room add to the home's functionality. The kitchen is designed with today's lifestyle in mind, featuring stainless steel appliances, a generous peninsula for gathering, and a large corner pantry providing abundant storage. Upstairs, the owner's suite offers a peaceful retreat with a spacious walk-in closet and private en-suite bath complete with double vanity and walk-in shower. Three additional bedrooms share a full hall bath with double vanity, providing comfort and convenience for family or guests. The third level expands the home's versatility with a fifth bedroom, full bath, and flexible bonus space ideal for a home office, playroom, media room, or fitness area! Ample closets throughout ensure exceptional storage options. Extras you'll love: a modern Smart Home Package offering convenience, efficiency, and peace of mind. Thoughtfully positioned against a backdrop of mature trees rather than neighboring homes, this property offers a more private outdoor experience. Seller is offering a buyer credit toward allowable closing costs - an excellent opportunity to conserve cash for personalized backyard improvements such as fencing, shed or patio after settlement! This beautifully landscaped community common area features a scenic pond with fountain, creating a welcoming neighborhood setting. Located just minutes from downtown Chestertown - known for its charming shops, restaurants, parks, waterfront atmosphere, and Washington College - you'll enjoy easy access to date nights, community events, and small-town charm at its best. This thoughtfully planned community is complete, offering a wonderful opportunity to become part of an established neighborhood. Don't miss your chance to make this exceptional home your own!

Beds:
4
Baths:
3.00
Sq.Ft.:
1,972
Status:
Active
MLS#:
MDKE2006498
Type:
Single Family
Subdivision:
THE VILLAGE AT CHESTERTOWN
Lot size:
0.1 Acres
Year built:
2022
Courtesy: Cross Street Realtors LLC
View additional info

Price Reduction! VERY motivated seller - open to all reasonable offers. Welcome to this beautifully maintained 4-bedroom, 2.5-bath home built in 2022, offering the perfect blend of modern comfort and peace of mind. Freshly painted with brand new carpet, this home features a bright, open floor plan ideal for both everyday living and entertaining. Enjoy the benefits of newer construction - major systems like the roof, HVAC, and water heater are all just a few years old, giving you confidence and low maintenance for years to come. Located in a desirable community with an affordable HOA that includes lawn mowing, you'll appreciate easy, low-maintenance living. Conveniently situated just minutes from shopping centers, restaurants, and everyday amenities. This move-in ready home is truly a must-see!

Beds:
3
Baths:
5.00
Sq.Ft.:
3,047
Status:
Active
MLS#:
MDKE2006496
Type:
Single Family
Subdivision:
NONE AVAILABLE
Lot size:
0.14 Acres
Year built:
1780
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Built in 1780/1840, "Highcroft" is in the heart of the Historic District near the Chester River. A rare in-town property that offers a 2-car garage with a second floor and a long driveway for tons of off-street parking. 3 bedrooms, 4 full baths and 1 half bath. Primary bedroom has his and hers private baths. 8.2 kw solar array on the garage. EV level 2 charger. Easy room flow from front to back for entertaining. Just steps to restaurants, bars, and shops. This is an ultra efficient "green" house.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,280
Status:
Active
MLS#:
MDKE2006446
Type:
Townhouse
Subdivision:
CHESTER ARMS
Lot size:
0.13 Acres
Year built:
2025
A broker reciprocity listing Courtesy: Real Broker, LLC
View additional info

Brand new home in Historic Chestertown available for move-in now. This home features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs you'll find generously sized bedrooms including a large primary suite with walk-in closet and private bath. Additional highlights include exclusive financing opportunities with zero down payment loans, paid closing cost programs, and discounted interest rates - making it possible to own this home for less than area rents. Delivered at the asking price as shown in the photos, this home combines modern style, comfort, and convenience in one of Chestertown's most historic locations. Ask about Special Financing Offers and how to get $7,500 or more in closing help from the builder's preferred lender and on select models, while they last!

Open House:

Saturday, 6/20 11:00-1:00PM

Beds:
3
Baths:
3.00
Sq.Ft.:
2,880
Status:
Active
MLS#:
MDKE2006416
Type:
Single Family
Subdivision:
COVENTRY FARMS
Lot size:
0.23 Acres
Year built:
2007
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

PRICE IMPROVEMENT: Priced below 2025 Appraisal!! Instant equity! NOTE: Zillow's property taxes are incorrect: correct annual property taxes are $4,338. Welcome to 103 Trafford Drive; an exceptionally maintained 3 bedroom home just minutes from downtown Chestertown. Nestled in family-friendly Coventry Farms Community, this Colonial-style residence has been recently updated in all the right places for modern convenience and classic charm. Brand new kitchen cabinets, countertops, and appliances, 5-inch oak hardwood floors, back patio, washer/dryer are just a few up the recent updates. Some of the timeless interior features include a wood burning fireplace, tray ceilings, baseboard and crown moldings, chair railings, . Inside you are greeted by a traditional layout with a formal dining room and formal living room or office space. The front of the home flows seamlessly to the back where the heart of the home is: the newly renovated kitchen and living room space punctuated with a wood-burning fireplace. Recent kitchen improvements include: custom maple wood cabinets, quartz countertops, Frigidaire and LG stainless steel appliances, and a reverse osmosis water treatment system. The spacious and private back yard has a thick tree line to the back and has been elevated by a new concrete patio and wood steps and newly planted pine trees for additional privacy. Going upstairs one will find brand new 5-inch red oak hardwood floor throughout: and no thresholds! The spacious primary bedroom features an ensuite bath with jetted soaking tub and an oversized walk-in closet. The full basement could easily be turned into a fourth bedroom with electric, lighting, ductwork, and roughed-in plumbing all ready to go. Oversized two-car garage offers additional storage or parking. Don't miss this opportunity. This stunning home has been meticulously maintained and upgraded in all the right spots; offering exceptional elegance and modern comfort. 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. Less than 90 minutes to Philadelphia and Washington D.C. Come see what Chestertown life is all about. Some furnishings may convey.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,232
Status:
Active
MLS#:
MDKE2006390
Type:
Single Family
Subdivision:
TOLCHESTER ESTATES
Lot size:
0.33 Acres
Year built:
2003
Courtesy: Doug Ashley Realtors, LLC
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Welcome to Tolchester Estates, a charming community near the Chesapeake Bay. This 3-bedroom, 2-bath rancher features updated HVAC, gas cooking, an upgraded propane hot water heater, and a recently replaced roof system in March 2026. The property is served by public sewer for added ease and reliability. Step outside to a large rear deck, perfect for entertaining or relaxing while enjoying the peaceful surroundings. The home also offers plenty of storage space in the attic, providing added convenience and functionality. Residents enjoy access to a private community beach and boat ramp. Also conveniently located within walking distance to Tolchester Marina and Shanty Beach Bar, offering outdoor entertainment throughout the summer months. Approximately 10 minutes to Rock Hall and 20 minutes to Chestertown, this home offers the perfect blend of comfort and rural living. Enjoy all that Tolchester has to offer at 8706 Elm.

Beds:
3
Baths:
1.00
Sq.Ft.:
1,120
Status:
Active
MLS#:
MDQA2016836
Type:
Single Family
Subdivision:
CHESTER HARBOR
Lot size:
0.55 Acres
Year built:
1978
Courtesy: Redfin Corp
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Welcome to 208 Central Drive, located in the desirable Chester Harbor community just minutes from historic Chestertown. This charming 3-bedroom, 1-bath home offers a wonderful blend of comfort, convenience, and value. It sits on 3 lots totaling approximately 0.55 acres, surrounded by mature trees and landscaping. Step inside to a bright, move-in-ready interior featuring brand-new wood flooring (2025) in the living room, hallway, and first bedroom. The home was thoughtfully updated with new lighting and ceiling fans throughout (2024-2025). The bathroom has been fully updated with a new tub/shower combination (2024), a stylish vanity, updated lighting and mirror (2024), a newer toilet (2023), and new flooring (2024). The kitchen includes a reverse osmosis water filtration system (2023), a new water filter (February 2026), and a stove/oven that is approximately five years old. Major systems have also been addressed, including a new water heater (2025), septic system inspection and pumping (2025), and three new electric heating units (2023). Outside, the expansive yard is a standout feature. Recently landscaped in 2024 and enhanced with fresh grass seed and treatment in 2025, the property offers plenty of space to enjoy. Outside includes a crab apple tree, a fig tree, a white pear tree, 2 white dogwood trees, and forsythia. Brand new rear screen door (2026) and a newly installed rear fence (2025) enhance both privacy and functionality, creating an ideal setting for relaxing or entertaining. Set on a generous lot with thoughtful updates throughout, this property offers exceptional value in a prime location just minutes from historic Chestertown, shops, dining, and waterfront. Enjoy water access to Rosin Creek in the community, which adds to the home's appeal for outdoor enthusiasts.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,664
Status:
Active
MLS#:
MDQA2016900
Type:
Single Family
Subdivision:
DUCKS NECK
Lot size:
0.51 Acres
Year built:
2024
Courtesy: Chesapeake Real Estate Associates, LLC
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Practically brand new and just 2 years young, this beautifully maintained home is perfectly situated in a desirable water-oriented community - offering the best of Eastern Shore living! Located in the Queen Anne's County school district and just minutes from downtown Chestertown, you'll love the convenience paired with the peaceful setting. Enjoy easy access to the Chester River - you can drive your boat to the community ramp at the end of the street, or even take a nice short walk down to the water, to spend your days crabbing, fishing, kayaking, or simply soaking in the waterfront lifestyle. Inside, this 3-bedroom, 2 full bath home features durable and stylish LVP flooring throughout and a thoughtfully designed split floor plan. The spacious primary suite is privately situated on one side of the home and offers a walk-in shower, dual vanity, and a beautifully appointed bath. On the opposite side, you'll find two additional bedrooms and a full bath with a tub/shower combo - ideal for guests or flexible living. The kitchen and living room are centrally located, creating an inviting and functional space for everyday living and entertaining. A standout bonus - an unfinished upstairs area of 544 additional SF, already in place and ready for your vision! Use it for storage now or finish it off for additional bedrooms, a home office, or recreation space. Step outside and enjoy both a charming front porch - perfect for morning coffee - and a massive back deck ideal for entertaining, grilling, or simply relaxing while taking in the peaceful surroundings. The generously sized yard with mature trees offers both privacy and room to enjoy the outdoors. Even more exciting - the county has indicated plans to pave the road in the near future. Added perk: fiber optic Talkie Internet is already available at the property, making working from home or streaming a breeze. Move-in ready, full of potential, and located in a charming waterfront community - this one checks all the boxes!

Beds:
2
Baths:
3.00
Sq.Ft.:
3,510
Status:
Active
MLS#:
MDKE2006320
Type:
Single Family
Subdivision:
CHESTERTOWN
Lot size:
2 Acres
Year built:
1977
Courtesy: Chesapeake Real Estate Associates, LLC
View additional info

Welcome to 24295 Langford Road in Chestertown, Maryland - a rare opportunity to own a peaceful slice of the countryside on 2 beautiful acres surrounded by farmland. Just minutes from downtown Chestertown, this property offers the perfect balance of privacy and convenience. If you've been searching for a home away from the hustle and bustle, this is the one. The classic brick rancher features over 1,800 square feet of living space with a full, unfinished basement offering endless potential for storage, a workshop, or future expansion. Inside, you'll find 2 comfortable bedrooms, a small room that could serve as dressing room, den or office, 2.5 baths, along with thoughtful details such as elegant pocket doors that enhance both function and flow. A cedar closet adds a touch of luxury while providing ideal storage for clothing and linens. A standout feature of the home is the inviting three-season room addition, where you can relax and take in serene views of the backyard and the surrounding natural beauty. Wildlife is abundant - enjoy frequent sightings of deer, eagles, and more right from your own home. The property also includes a very large outbuilding, ideal for a variety of uses. Whether you're looking to run a home-based business, pursue hobbies, or simply need space to store vehicles, boats, or equipment, this versatile structure offers incredible flexibility. It could even be finished into the ultimate workspace or creative studio. With its peaceful setting, generous acreage, and functional features, this property is a unique find in today's market.

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BRIGHT MLS - All information, regardless of source, should be verified by personal inspection by and/or with the appropriate professional(s). The information is not guaranteed. Measurements are solely for the purpose of marketing, may not be exact, and should not be relied upon for loan, valuation, or other purposes.

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