The median home value in Chestertown, MD is $314,990.
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 $314,990.
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.
Excellent Location! This charming 3-bedroom, 1-bathroom bungalow sits proudly along one of Chestertown's primary roads. Positioned in an Intense Village zone, it caters to a versatile range of usesâbe it residential or various commercial ventures. Inside, discover a spacious family room adjacent to the galley kitchen, a screened-in porch, and a detached 2-car garage with ample off-street parking, complemented by recent upgrades including a new heat-pump with central air installed in September 2021, a fresh new roof in December 2022, and new carpeting. Its proximity to Chestertown's offeringsâsuch as Washington College, the hospital, local stores, a new marina, restaurants and moreâensures convenience and accessibility. This property is brimming with potential! Please note, it is subject to an existing lease expiring on December 31, 2024.
Excellent Location! This charming 3-bedroom, 1-bathroom bungalow sits proudly along one of Chestertown's primary roads. Positioned in an Intense Village zone, it caters to a versatile range of usesâbe it residential or various commercial ventures. Inside, discover a spacious family room adjacent to the galley kitchen, a screened-in porch, and a detached 2-car garage with ample off-street parking, complemented by recent upgrades including a new heat-pump with central air installed in September 2021, a fresh new roof in December 2022, and new carpeting. Its proximity to Chestertown's offeringsâsuch as Washington College, the hospital, local stores, a new marina, restaurants and moreâensures convenience and accessibility. This property is brimming with potential! Please note, it is subject to an existing lease expiring on December 31, 2024.
Charming 3-Bed, 1.5 Bath Home with Screened Porch, Fireplace & 2-Car Garage! Welcome to your cozy retreat! This charming home, nestled on an end lot, boasts fresh carpet upstairs and a welcoming fireplace in the spacious living area. Enjoy the warmth of the fire, relax on the screened porch, and revel in the convenience of a 2-car garage and an unfinished basement for extra space. Don't miss out on this delightful family home!
Welcome to your dream country home! This charming property, nestled in a serene rural setting, offers the perfect blend of modern comfort and rustic allure. Boasting three bedrooms and two baths, this home is a haven of tranquility with a first-floor bedroom and a full bath for added convenience. The home features all new windows, new Luxury Vinyl Flooring throughout, updated bathrooms, and more. An additional office space adds functionality to the layout, catering to the demands of remote work or personal projects. The enclosed breezeway is a flexible space ready for your imagination..craft room, mudroom, playroom, sitting room, Need storage space...an oversized 2-car garage has built-in shelving, and a staircase to the walk-in attic as well as the second floor office. Relax and unwind on the deck overlooking the beautiful backyard, a perfect spot for entertaining guests or enjoying peaceful evenings surrounded by nature. Working from home is not a problem with WiFi access points on both floors, office wall jacks, and entertainment console wired jacks (for Gaming Consoles, networked entertainment centers, etc.), and a cell phone booster. The community has a voluntary HOA which covers the community common space, boat ramp, pier with boat slips. Conveniently located 15 minutes from Chestertown and Rock Hall, and a short 30 minutes to Middletown, DE and Rt. 301/Rt. 1. One Year Home Warranty is Included
Location, location, location! Located in College Heights and just a few short blocks from Washington College and a few more blocks from shopping and downtown Historic Chestertown! This home is move in ready with all new flooring throughout. Heat pump provides heating and cooling. There is a very small deck that overlooks the fenced in backyard. There is a full hallway bath as well a a half bath for the primary bedroom.
"Strawboard Mill" offers 2 brick, townhomes (each townhouse has 2 units), with metal roofs, 1 efficiency apartment and a 3 bedroom, 2 bath residence. The brick townhomes were built in 1902+/- and were used as housing for mill factory workers. There are two, 2 bedroom, 1 bath units in each townhome. Each townhome unit has washer and dryer. The efficiency unit also has a washer and dryer. All units are leased on a month to month basis. All townhome units have Lead Free Certificates from MDE. The main house, which houses the efficiency unit over the garage, was built in 2005. Current monthly rental income is $5,225 with the potential to increase to market level of about $6,500+/- and even more if you rent out the main house. The owners live in a well appointed Cape Cod that offers the possibility of a 1st floor bedroom, kitchen and family room as well as office space, 2 additional bedrooms on the second level with a "Jack n Jill" bathroom setup. There are laminate floors throughout most of the house as well as wood ceilings in most rooms. There are actually 2 garage spaces however one has been transformed into an exercise room. The rear deck overlooks the private backyard and offers a gazebo on the deck. Do you need a separate office? You are in luck! There is an attached office space with a mini split system for heating and cooling. The sellers live in the Cape Cod however you could easily rent the house to gain more income. There is potential to increase the current rent rolls to meet current rental market values. This is a rare opportunity to own, arguably, one of the finest rental properties in Chestertown!
"Strawboard Mill" offers 2 brick townhomes, with metal roofs, 1 efficiency apartment and a 3 bedroom, 2 bath residence. The brick townhomes were built in 1902+/- and were used as housing for mill factory workers. There are two, 2 bedroom, 1 bath units in each townhome. Each townhome unit has washer and dryer. The efficiency unit also has a washer and dryer. All units are leased on a month to month basis. All townhome units have Lead Free Certificates from MDE. The main house, which houses the efficiency unit over the garage, was built in 2005. Current monthly rental income is $5,225 with the potential to increase to market level of about $6,500+/- and even more if you rent out the main house. The owners live in a well appointed Cape Cod that offers the possibility of a 1st floor bedroom, kitchen and family room as well as office space, 2 additional bedrooms on the second level with a "Jack n Jill" bathroom setup. There are laminate floors throughout most of the house as well as wood ceilings in most rooms. There are actually 2 garage spaces however one has been transformed into an exercise room. The rear deck overlooks the private backyard and offers a gazebo on the deck. Do you need a separate office? You are in luck! There is an attached office space with a mini split system for heating and cooling. The sellers live in the Cape Cod however you could easily rent the house to gain more income. There is potential to increase the current rent rolls to meet current rental market values. This is a rare opportunity to own, arguably, one of the finest rental properties in Chestertown!
Welcome to this charming 3-bedroom, 1-bathroom Ranch-style home, designed for convenient single-level living. Situated on a corner lot with a screened back porch and fenced rear yard, this property offers both comfort and privacy. Step inside to discover the warm and inviting interior with beautiful hardwood floors that flow through the living spaces. The living room features a cozy fireplace, providing the perfect spot for relaxation. The kitchen has been thoughtfully updated with stainless steel appliances and granite countertops, creating a modern and functional space that beautifully complements the home's design. The three bedrooms are generously sized and offer hardwood floors, while the updated bathroom is conveniently located and features modern fixtures. The newer roof, windows and A/C system are valuable upgrades that contribute to the home's quality and energy efficiency. A one-car attached garage provides additional storage, as does the partial basement. Conveniently located in the Byford Heights neighborhood, this home offers easy access to nearby amenities, schools, and parks, making it an ideal place to call home for those seeking single-level living and convenience. Don't miss the opportunity to make this house your own. Schedule a showing today and experience the comfort and convenience of this delightful property.
Bask in the beauty of this incredible 1920s home in downtown Chestertown! At 2890 square feet, this freshly painted 5 bedroom, 3.5 bathroom property has tons of space and an oversized lot featuring a secluded backyard with mature trees, fire pit, and off-street parking, most of which are very rare to find downtown! The many updates include a brand new HVAC system and hot water heater; updated electric, new slider doors, cooktop, combination wall ovens, dishwasher, and 2nd floor bath fixtures along with a meticulously restored stairway in the entry hall. Other features include original hardwood floors on the first floor & stairway & newel post, some original windows, refinished floors on first floor, original hardwood floors on the second floor, freshly painted and repaired dormers, privacy fence, revitalized front door, and much more! Aside from the fantastic interior space, you'll fall in love with the charming front porch and lovely balcony off the second story primary bedroom. The exterior is further improved with new topsoil, grass seed, fertilizer, straw, and flowers. 204 N Mill is located on a quiet street close to downtown shops, Washington College, waterfront, restaurants, farmer's market and shopping.
Split-level home nestled in a serene wooded area, minutes from the Chester River. Ample garage parking, expansive deck, and untapped potential on a generous lot. This is a HUD home(case number 241-877191). Property is (IE) Insurable with Escrow for FHA financing in its "as-is" condition.
Beautiful Dutch Colonial on 3 Acres with 500 +/- feet of waterfront overlooking Worton Creek. Near Worton Creek Marina and only a short drive to Historic Chestertown or Rock Hall. Enjoy the wildlife, rural setting, and inground pool. Native plants create a very nicely landscaped home. All wall paneling is Western Red Cedar and the wood floors are 150+ years old heart pine. The game room could be used as bedroom #5. The family room has a brick wood burning fireplace, table space , breakfast bar, and exposed wood beams. Sign posted.
Pets are welcomed! Perfect for your furry friends this pet friendly home is equipped with a pet door that allows them to access the large fully fenced back yard as needed! Hard wood floors and a 2 story ceiling make the living room the place to be along with a fireplace, allows for a cozy atmosphere. The primary bedroom is located on the first floor along with the primary bath and a large walk in closet with more than adequate shelving and ample amount of storage. An unfinished walk out half basement can be used for storage, play room, gym or whatever you need it to be! Credit score must be above 630 and income should be almost 3 times the monthly rent. No smoking allowed! Once approved and at lease signing you will need $2,000 (first months rent), $2,000 (security deposit) and $800 per pet (pet deposit).
The quintessential Maryland Eastern Shore getaway, just 10 min from Downtown Chestertown & 15 min to Rock Hall. Whether full-time or part-time, this setting will offer you peace & quiet with the convenience of a small town lifestyle. The main level primary suite has a handicap accessible bathroom and the second floor Master Suite embodies luxury living. Low maintenance salt water pool, Fios/high speed internet, gourmet kitchen, generous & comfortable outdoor living spaces, and ultimate privacy. Within 90 min of Philly, DC, Baltimore, Wilmington... this waterfront historic home has been upgraded & improved. Fully & tastefully furnished with classic pieces, this cozy estate is move-in ready.
Priced To Sell Fast! Amazing Opportunity! Renovate & Resell, Buy & Hold, or Move-In and Build Some Sweat Equity. Charming 2 Level Farm House with Spacious Kitchen, Spacious Bedrooms, Hardwood Floors, .59 Acre Wooded Lot, Outbuildings, Much More!! Just Waiting For Your Personal Renovations to Make it Shine. Close to Schools, Shopping, and Commuter Routes. This Will Not Last! Sold As-Is.
Great home located in desired Coventry Farms community of Chestertown. This home offers plenty of space for entertaining boasting 4 bedrooms, 21/2 baths, master suite, large open kitchen with breakfast/sunroom, large family room, deck, inground pool, large two car garage, large level lot and more. This home also offers a full unfinished basement which could give you an additional 1200 Sq. Ft. of living space. Home is located within Chestertown limits offering plenty of entertainment, shopping, parks, beaches and more. Home shows well and is ready for its new owner. Don't miss out on this great find. All reasonable offers will be considered.
Come by this AWESOME, RENOVATED Rancher in the WATERFRONT Community of Chesapeake Landing is Chestertown. This beautifully renovated single level home is ready for it's new owner today! This home has been carefully renovated in the last few months, including new luxry vinyl plank flooring, new kitchen with white shaker cabinets, granite countertops, new bathrooms, new appliances and much more! Special financing is available for this home making it more afforable to own a home than rent one!
The only available under-construction interior townhome in The Village at Chestertown that backs to community open space with pond views! This two-story Jefferson is an open-concept townhome with three bedrooms and two and a half bathrooms. The first floor is spacious with a large, thoughtfully designed kitchen with beautiful white cabinets. stainless steel appliances, a storage closet, and a peninsula island with space for seating. The kitchen is open to the living and dining area providing your ideal space to entertain. The first floor also offers a powder room. The second floor has three large bedrooms, each with plenty of closet space, a hall bathroom, a linen closet, and a laundry closet with an included washer and dryer. The ownerâs suite offers privacy away from the other bedrooms and features a full bathroom and a walk-in closet. The included white blind package and the exclusive Smart Home® package will give you complete peace of mind. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built.
Welcome to 101 S. Kent St! Prepare to be charmed by this beautifully updated and lovingly maintained historic home, located on a peaceful and quaint street. Built in 1880, this 2 bedroom, 2.5 bath property combines classic charm with modern comfort situated in the heart of downtown Chestertown. You're just a leisurely walk away from the waterfront, shops, restaurants, and Washington College! The current owners have had this property as a profitable Air BnB/short term rental (profit & loss statement available). Features include a private patio ideal for outdoor entertaining, original hardwood flooring, built-in bookcases, wood-burning stove, exposed interior brickwork, traditional brick sidewalks. Don't miss this perfect home in charming Chestertown!
Endless possibilities for this centrally located property in Chestertown, across from Kent Plaza Shopping Center and close to Washington College and the newly built YMCA. In its past it has been a single family home, business offices, and most recently a 2 dwelling rental unit. Would also make a perfect home business with high visible road frontage and a quiet studio apartment in the rear, or a 2 bedroom home with an in-law/nanny suite at year. Either way it is easily turned back into a single family home. So many possibilities! Front Unit: 2 bedrooms, 1 full bath, large kitchen with attached laundry, separate dining room and large Living room. Entrance and parking in front. Back Unit: One bedroom efficiency with kitchenette and full bathroom. Entrance and parking in rear. Hardwood floors throughout both units except bathrooms and Kitchen. New bathroom and kitchenette in back unit. New gutters, paint and HVAC. Driveway has been extended to make 2 entrances and wrap around building for ease of getting in and out. Plenty of parking in front and rear. *Both units have active leases in place *Property could easily be turned back into a single family home by knocking through one wall as it was originally.
Endless opportunities for this centrally located property in Chestertown, across from Kent Plaza Shopping Center and close to Washington College, Dixon Valve, and the new YMCA. In its past it has been a single family home, business offices, and now a 2 dwelling rental unit. Would also make a perfect home business with high visible road frontage and a quiet studio apartment in the rear. Front Unit: 2 bedrooms, 1 full bath, large kitchen with attached laundry, separate dining room and large Living room. Entrance and parking in front. Back Unit: One bedroom efficiency with kitchenette and full bathroom. Entrance and parking in rear. Hardwood floors throughout both units except bathrooms and Kitchen. New bathroom and kitchenette in back unit. New gutters, paint and HVAC. Driveway has been extended to make 2 entrances and wrap around building for ease of getting in and out. Plenty of parking in front and rear. *Both units have active leases in place *Property could easily be turned back into a single family home
Come by this lovely BRAND NEW middle unit home in a Triplex in Historic Chestertown, available for move in in October. This home features Luxury Vinyl Flooring throughout, White Shaker Cabinets, Granite Counters, Spacious Living Room, Eat in Kitchen area, covered patio off the kitchen, spacious bedrooms including a large primary bedroom suite and much more! These homes are selling faster than they can be built, so come by today and take advantage of this opportunity while it lasts. There are only a few of these homes left ! Special financing programs available, including Zero Down payment loans and closing costs assistance programs so you can own this home for less than renting. Home is delivered at the asking price the way you see it in the photos with the exception of the siding color, which may be different.
Main Level Features Dining Room, Living Room, Family Room, Kitchen with Breakfast Nook Bump Out, Laundry Room, Half Bath, and Den. Upper Level Features Large Primary Bedroom with Walk In Closet and En Suite Bath with Shower and Soaking Tub. Lower Level Has Additional Living Space and Full Bath with Walkout to Back Yard.
Waterfront lot in the community of Chesapeake Landing, just outside of Chestertown. This lot has failed previous perc tests and is most likely not buildable.
Currently the only under-construction end-of-unit townhome available in The Village at Chestertown with pond views! This two-story Jefferson is an open-concept townhome with three bedrooms and two and a half bathrooms. The first floor is spacious with a large, thoughtfully designed kitchen with modern white cabinets. stainless steel appliances, a storage closet, and a peninsula island with space for seating. The kitchen is open to the living and dining area providing your ideal space to entertain. The first floor also offers a powder room. The second floor has three large bedrooms, each with plenty of closet space, a hall bathroom, a linen closet, and a laundry closet with an included washer and dryer. The ownerâs suite offers privacy away from the other bedrooms and features its own full bathroom and a walk-in closet. The included white blind package and the exclusive Smart Home® package will give you complete peace of mind. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built.
