Chestertown MD Real Estate & Homes for Sale

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Beds:
3
Baths:
2.00
Sq.Ft.:
1,900
Status:
Active
MLS#:
MDKE2005834
Type:
Single Family
Subdivision:
None Available
Lot size:
1.03 Acres
Year built:
2014
Courtesy: Chesapeake Real Estate Associates, LLC 443-215-4663
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ADDITIONAL INFORMATION

Price Improvement = Even More Value! Discover the perfect blend of space, privacy, and comfort at this well-maintained 3-bedroom, 2-bath, 1,900 square foot home, situated on a full acre with public water and sewer, no HOA, and a detached garage with electric! With the recent price change, this property now offers an exceptional opportunity—whether you’re looking for a primary residence, a weekend retreat, or a vacation home on Maryland’s Eastern Shore. The flexible layout and generous acreage make this home ideal for a relaxing getaway, with plenty of room for outdoor entertaining, hobbies, or storing boats, bikes, or recreational gear. Inside, enjoy an open-concept design with easy one-level living—perfect for hosting guests. Outside, a wide blacktop driveway provides ample parking for multiple vehicles, an RV, or a boat. The expansive yard offers space to garden, gather with family and friends, or unwind under the stars after a day on the water or exploring the area. Located just minutes from historic downtown Chestertown, nearby marinas, dining, shopping, and waterfront activities—with convenient access to major routes into Delaware and Pennsylvania—this property offers the ideal balance of peaceful rural living and easy travel. A rare combination of acreage, versatility, and affordability—now at an even better price. Schedule your tour today and see why this home works just as well for everyday living as it does for your Eastern Shore escape. FHA, VA, USDA, and conventional financing welcome.

Beds:
4
Baths:
2.00
Sq.Ft.:
1,625
Status:
Active
MLS#:
MDKE2005766
Type:
Single Family-Detached
Subdivision:
None Available
Lot size:
2.66 Acres
Year built:
1900
Courtesy: Coldwell Banker Chesapeake Real Estate Company 410-778-0330
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ADDITIONAL INFORMATION

Move-in ready and freshly updated in 2025! This 3-bedroom, 2-bath home offers approx. 1,600 sq. ft. of stylish living on an 2.66 acre corner lot with public water and sewer. Every detail has been thoughtfully upgraded—appliances and systems are brand new, complemented by luxury vinyl plank flooring throughout. The spacious layout includes a large mudroom and plenty of modern finishes. Located just minutes from Fairlee Creek’s public landing for easy water access, and a short drive to downtown Chestertown and Rock Hall, this home combines comfort, convenience, and Chesapeake charm. PROPERTY CAN BE PURCHASED FOR $314,000 with .39 acres after recordation this acreage will be subdivided MLS #MDKE2005074, 1.8 ACRES SUBDIVIDED INTO 4 LOTS

Beds:
2
Baths:
3.00
Sq.Ft.:
2,100
Status:
Active
MLS#:
MDKE2005670
Type:
Condo
Subdivision:
Chester River Landing
Lot size:
0.03 Acres
Year built:
2015
Courtesy: Coldwell Banker Chesapeake Real Estate Company 410-778-0330
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ADDITIONAL INFORMATION

Welcome to 103 Landing Lane: a meticulously maintained 2-bedroom townhome in the desirable waterfront community of Chester River Landing. Just a short walk or bike ride into downtown Chestertown, this elegant, turn-key home offers maintenance-free living, great amenities, and easy water access to the Chester River. The welcoming foyer seamlessly flows into the rear den or office which could be converted into a 3rd bedroom. Off the den is the first-floor bedroom and full bath. Enjoy the summer breeze from the private back screened-in porch; recently upgraded with high-tech flex screens and a ceiling waterproofing, keeping the porch dry. The real action is found upstairs. The living room – anchored by an electric fireplace with stone surround – is complemented by the oversized second story deck; perfect for grilling or watching picturesque Chester River sunsets. The modern kitchen features new stainless-steel appliances, abundant cabinet space, granite countertops and a large island with breakfast bar. Plenty of space for formal or casual dining. The second floor is finished by an oversized primary bedroom with ensuite bath and large walk-in closet. Should one desire an elevator; there are two locations where one could be built into the existing design. Leave your worries aside as the condo association takes care of all exterior maintenance, yardwork, and repairs. Boaters will enjoy the well-maintained community dock with slips available for purchase or lease (with board approval), or just drop in a kayak or paddle board, great on warm summer evenings. Other community amenities include the pool, walking paths, garden, picnic and grilling areas, and a fire pit. Founded in 1706, Chestertown sits on the banks of the Chester River and is home to Washington College. Enjoy the historic architecture, local shopping, restaurants, art galleries, and waterfront walkways and parks. Chestertown is home to many festivals and an award-winning Farmer's Market every Saturday. New YMCA with full gym, racquet sports, lap pool, sauna, etc. Don’t miss your opportunity to enjoy worry-free living along the Chester River.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,400
Status:
Active
MLS#:
MDQA2015520
Type:
Single Family-Detached
Subdivision:
Blakefield
Lot size:
1 Acres
Year built:
2025
Courtesy: Chesapeake Real Estate Associates, LLC 410-476-2201
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ADDITIONAL INFORMATION

Discover the charm of this stunning new construction home in the desirable Blakefield community, completed in 2025. This beautifully designed Colonial-style residence boasts 4 spacious bedrooms and 3 full bathrooms, offering ample space for relaxation and entertainment. The kitchen is a chef's dream, featuring an island, eat-in space, and modern appliances including a built-in microwave, dishwasher, electric oven/range, and refrigerator. Enjoy cozy breakfasts in the bright breakfast area or host formal dinners in the separate dining room. The luxurious touches continue with walk-in closets, a convenient upper-floor laundry, and a family room that flows effortlessly from the kitchen and a separate office making this a great option for those who work from home. A first floor bedroom is idea for a guest room, play room, in-law quarters and more. The home is adorned with luxury vinyl plank flooring and plush carpeting, creating a warm and welcoming atmosphere throughout. Set on a generous 1-acre lot that adjoins open space, this property offers a serene outdoor setting, perfect for enjoying nature or future landscaping projects. The side-entry attached garage provides easy access and additional storage. With its excellent condition and thoughtful design, this home is ready to embrace new memories. Experience the perfect blend of comfort and modern living in this exceptional property. Buy with ease when purchasing this new construction home. Seller can'tt settle until January 2026

Beds:
3
Baths:
2.00
Sq.Ft.:
1,136
Status:
Active
MLS#:
MDKE2005718
Type:
Townhouse
Subdivision:
Calvert Homes
Lot size:
0.05 Acres
Year built:
1992
Courtesy: Redfin Corp 301-658-6186
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ADDITIONAL INFORMATION

This property is primed and ready for your finishing touches—materials included! Enjoy the convenience of being just steps from historic downtown Chestertown. LVP Flooring installed on 10/04/2025 on the main and upper levels. Carpet installed on the staircase. Materials, fixtures, applicances cabinetry, washer/dryer ready to install. Discover the potential of 423 Calvert Street — a two-story, 1,136 sq. ft. townhouse built in 1992 and set on a 2,006 sq. ft. lot. This 3-bedroom, 1.5-bath home has already undergone major updates in 2025, including new flooring, appliances, fresh paint, and a newer roof. Renovations are well underway, with all remaining materials provided, giving the next owner an incredible opportunity to add the finishing touches. The property features a fenced front entry, a deep backyard with rear parking access, and plenty of outdoor space to enjoy. Ideally located near historic downtown Chestertown, you’ll find shopping, dining, entertainment, and events just minutes away, along with the waterfront park along the scenic Chester River and the nearby Washington College campus. Offered at just $135,000, this home presents exceptional value for use as a primary residence, a second home retreat, or an investment rental. All of this in Chestertown — a charming Eastern Shore community known for its rich history, vibrant arts scene, events, riverfront beauty, and welcoming small-town atmosphere.

Beds:
4
Baths:
2.00
Sq.Ft.:
2,220
Status:
Active
MLS#:
MDKE2005592
Type:
Single Family-Detached
Subdivision:
Byford Development
Lot size:
0.34 Acres
Year built:
1965
Courtesy: Cross Street Realtors LLC 410-778-3779
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ADDITIONAL INFORMATION

Welcome to 515 N Kent Street in the heart of Chestertown! This charming two story home features a half-circle driveway, 1-car attached garage, and inviting brick patio leading to the front door. Step inside and you’ll love the gorgeous hardwood floors throughout the main level (2022). The formal living room showcases a wood-burning fireplace with a brick mantel, creating a warm and welcoming space. The kitchen and dining room were completely updated in 2022 with custom Amish cabinetry, quartz countertops, a farm sink, and a large island—perfect for cooking and gathering. Just off the kitchen, the laundry room offers washer/dryer, ample storage, and eye-catching brick tile flooring. From here, step into the cozy family room with wood stove, built-ins, and access to the screened porch and brick patio overlooking the private backyard. A full bath with shower and matching brick tile floors is conveniently located off the family room and garage entry. Upstairs, you’ll find four spacious bedrooms with carpet and a full bath with tub/shower. The partial basement with French drain provides flexible space for storage or playroom use, with indoor/outdoor access. This home has been well maintained with numerous updates: sewer line replaced (2017), new heat pump with central AC (2018), 50-year architectural shingle roof (2019), breaker panel and hot water heater (2024). A truly move-in ready home with character, comfort, and thoughtful upgrades—don’t miss this one!

Beds:
4
Baths:
3.00
Sq.Ft.:
2,524
Status:
Active
MLS#:
MDKE2005850
Type:
Single Family-Detached
Subdivision:
Tolchester
Lot size:
1.37 Acres
Year built:
1979
Courtesy: Doug Ashley Realtors, LLC 410-810-0010
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ADDITIONAL INFORMATION

Two Story Colonial on 1.37+/- acre lot, rectangular 200 x 300 ft. Approximately 2,700 sq ft. of living area in house (estimate). 4 bedrooms, 2.5 Bathrooms. ½ basement with laundry room and fix-it shop/work bench with 2 crawl spaces. Attached two-car garage with abundant built-in shelving and free-standing cabinets for lots of storage space with garage door opener on each of 2 doors. Forced Hot Air, Fuel Oil Heating; Central Air Conditioning. Well water pump upgraded in 2016. New, top-of-the-line “Meyers” well pump, with increased HP. Public sewer so no septic systems to deal with. Four upstairs Bedrooms. The MBR and BR2 are huge. MBR has slider door to lovely Sunroom/Sitting room. The MBR features wainscotting on all walls; crown molding; custom wide molding around all 3 doors and the closet with remote controlled ceiling fan with dimmable light. Large living room with stunning fireplace. Wide, extra-long mantle, matching storage cabinets on both sides of fireplace, large picture window and crown molding. Two full bathrooms with showers are upstairs, each with new, in 2024, quiet, yet powerful Panasonic exhaust fan and LED light. One Powder Room is downstairs. Bright and airy, extra-long dining room. Tray ceiling. dimmable LED ceiling lights on separate, inner and outer ring circuits for versatility. Ceiling centerline is pre-wired (includes 3-way switches) for one or more chandelier lights; Pass-through window to kitchen with fancy tempered glass shelf. Family room with dropped ceiling bar area. Bar sink, granite counters, gorgeous glass door cabinets, wood-burning stove, versatile lighting, and a slider door to a the main level sunroom. Modern, ample-sized kitchen with movable island. Nearly new, upscale glass cooktop/oven, dishwasher and microwave. Build-in refrigerator surrounded by cabinets. Double sink, disposal and PC workstation with shelving matching cabinet. Extraordinary lighting includes under and over cabinet lights plus a ceiling fan with fancy light globes and attractive light globes over sink. MAJOR ADDITION & REHAB done in 2013: Extended DR by 13 feet and added 2nd story sunroom/sitting room on top of DR extension Total rehab of 1st floor sunroom. Top quality, long lasting architectural roof shingle for entire house; new flashing and roof vent seals. Both sunrooms have attractive, casement-style windows for exceptional ventilation. Seven Ceiling fans with attractive lighting: MBR, BR2, BR3, 2nd story sunroom/sitting room, kitchen and 2 on the porch. All four Slider Doors (servicing the porch and the 2 sunrooms) have built-in blinds for privacy and versatile light and view control. Spacious screened porch with porch swing. Massive stone and paver patio area includes three 10x10 ft flat, paved areas for table & chairs. Large Campfire ring within the patio. Two lovely, Amish garden sheds in excellent condition and loaded with options: 12x16 ft. shed installed in 2010, and a 10x14 ft. shed installed in 2021. Huge 16x18 ft. Raised Deck using long-life Trex engineered planks; custom Pergola over one corner. Deep Shaded, 10 x 12 ft Outer Patio Area with Pergola. Mature Trees for great privacy and shade, especially around property perimeter. Three-level, split rail fence on rear and side yard property lines. (Left-side fence only is owned and maintained by the neighbor.) Extra-Wide Driveway. Paved Parking for 10 vehicles! Also suitable for camping trailer or boat.

Beds:
2
Baths:
1.00
Sq.Ft.:
1,232
Status:
Active
MLS#:
MDKE2005624
Type:
Townhouse
Subdivision:
Tolchester
Lot size:
0.05 Acres
Year built:
1955
Courtesy: Doug Ashley Realtors, LLC 410-810-0010
View additional info

ADDITIONAL INFORMATION

Back on the market through no fault of the sellers. Home inspection went well. Two bedroom, one bath townhome with a nice view from the living room/patio area. NEW CARPET in living area/hallway on the main level and upstairs! Looks great! Located very close to a public landing and Tolchester Marina, which offers full service. This townhouse has outdoor storage both on the front patio area and the back patio area. New carpet and fresh paint will update this property nicely. Covered storage for bikes/yard toys and more. The townhouse is all electric with a washer/dryer located on the main level. Affordable, and the opportunity to express your own vibe and decorating skills. Call for more information.

Beds:
5
Baths:
4.00
Sq.Ft.:
4,067
Status:
Active
MLS#:
MDKE2005610
Type:
Single Family-Detached
Subdivision:
Coventry Farms
Lot size:
0.26 Acres
Year built:
2009
Courtesy: Samson Properties 301-850-0255
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ADDITIONAL INFORMATION

$$THE OWNER MUST RELOCATE. TAKE ADVANTAGE OF THE NEW PRICE IMPROVEMENT! $$ Welcome to Coventry Farms in Chestertown — where comfort, elegance, and space come together in this stunning colonial-style home! Built in 2009 and meticulously maintained, this spacious property offers over 4,000 square feet of finished living space across three levels — including a fully finished basement with a full bath, perfect for entertaining, a guest suite, or a home office setup Curb appeal abounds with an inviting brick front and an attached two-car garage. Step inside to find a bright and open main level featuring a cozy fireplace in the great room, a large formal dining area filled with natural light, and a chef's kitchen with abundant cabinetry and high-quality appliances including a wall oven, cooktop, refrigerator, dishwasher, and built-in microwave. Upstairs, retreat to your luxurious primary suite, complete with a tray ceiling, spacious layout, double vanities, soaking tub, and separate shower — a true personal oasis. Three additional bedrooms offer plenty of space for family, guests, or a home office. Enjoy year-round comfort with a two-zone HVAC system, and take advantage of the generous quarter-acre lot for outdoor activities, gardening, or future expansion. Located in the sought-after community of Coventry Farms, this move-in-ready home combines modern convenience with small-town charm. Don’t miss your opportunity to own this beautiful home — schedule your private tour today and start living the Coventry Farms lifestyle!Please use booties provided at the front door. PET FRIENDLY COMMUNITY

Beds:
4
Baths:
3.00
Sq.Ft.:
2,630
Status:
Active
MLS#:
MDKE2005584
Type:
Single Family-Detached
Subdivision:
Fairlee
Lot size:
1.65 Acres
Year built:
1974
Courtesy: Rock Hall Properties Real Estate 410-639-4003
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ADDITIONAL INFORMATION

Located in the small Eastern Shore town of Fairlee, this spacious Bi-level sits on 1.65 acres of cleared land, just a short 10-minute drive to both Chestertown and Rock Hall. The home offers 3 bedrooms and 2 bathrooms, with a finished lower level for additional living space. A large sunroom with cathedral ceilings and walls of windows is the heart of the home, filling the space with natural light. Enjoy cooking in the updated kitchen with stainless steel appliances and serving meals in the separate dining room. Outdoor living is a highlight with an enclosed back porch, decks on both the first and second floors, and plenty of open yard space. Additional features include two fireplaces, a dedicated laundry room, and a shed for storage. A detached 3-bay garage provides ample room for vehicles, hobbies, or workshop space. This property combines comfortable living with generous space inside and out, all in a convenient location close to towns and the water.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,096
Status:
Active
MLS#:
MDQA2014830
Type:
Single Family-Detached
Subdivision:
Chester Harbor
Lot size:
0.67 Acres
Year built:
1976
Courtesy: Gunther-McClary Real Estate 410-275-2118
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ADDITIONAL INFORMATION

Three bedroom one-floor living on a spacious lot in Chester Harbor! Over half an acre of nicely shaded yard space, and a short distance to the public beach on Mill Creek. 3 bedrooms and 1.5 bathrooms, open living and dining space, large sunroom/ porch with wood-burning stove, and an additional wood stove in the living room. Outside there's a small storage shed and a larger workshop/shed next to the asphalt driveway. The sunroom leads to a deck overlooking the large yard. Great community with water access. Quick ten minutes into Chestertown, and less than an hour to Middletown DE or Annapolis.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,664
Status:
Active
MLS#:
MDQA2014816
Type:
Single Family-Detached
Subdivision:
Chestertown
Lot size:
0.34 Acres
Year built:
2003
Courtesy: Cummings & Co. Realtors 410-823-0033
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ADDITIONAL INFORMATION

YOUR DIAMOND IN ROUGH.........Home is original and needs updating through out....Priced to sell. Good bones, will need a buyer with vision. Main level has a large eat in kitchen, living room area and laundry room. Upper level has 3 bedrooms, 2 full bath; including master on suite. Large deck and fenced in back yard. Minutes from The Chester Bridge.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,280
Status:
Active
MLS#:
MDKE2005688
Type:
Townhouse
Subdivision:
Chester Arms
Lot size:
0.13 Acres
Year built:
2025
Courtesy: Real Broker, LLC 855-450-0442
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ADDITIONAL INFORMATION

Brand new home in Historic Chestertown available for move-in this October. 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.

Beds:
6
Baths:
5.00
Sq.Ft.:
4,954
Status:
Active
MLS#:
MDKE2005852
Type:
Single Family-Detached
Subdivision:
Melitota
Lot size:
65.47 Acres
Year built:
1858
Courtesy: Coldwell Banker Chesapeake Real Estate Company 410-778-0330
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ADDITIONAL INFORMATION

Gobbler Hill, circa 1858 with an addition built in 1989, sits like a jewel atop one of the highest points in Kent County. Listed on the National Historic Registry, the transitional architecture is an excellent example of late Greek Revival to early Italianate. The property consists of four parcels totaling over 65 acres. Wildlife abounds on the fields of native prairie grasses, wild flowers, woods, approximately 20 tilled acres and a large pond. Impeccable attention was payed to maintaining the historic character of both the interior and exterior. From the Lincrusta wall covering, 19th century faux wood finishing, plaster medallions, white and sugar pine wood floors and crown molding on the 11 ft. ceilings to the monumental copper roof, the thoughtful restoration is stunning. The newer addition beautifully blends into the original section adding modern conveniences and natural light. The library boasts black walnut bookshelves constructed by a local craftsman. Well maintained grounds offer gardens, mature trees, a classic poured concrete in ground pool with inlaid tile and stunning views. This unique, lovingly restored piece of Kent County history is now looking for a new steward to guide it into its next chapter.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,280
Status:
Active
MLS#:
MDKE2005498
Type:
Single Family
Subdivision:
Chester Arms
Lot size:
0.07 Acres
Year built:
2023
Courtesy: Engel & Volkers Annapolis 443-292-6767
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ADDITIONAL INFORMATION

Come enjoy the this 2 year old home in Historic Chestertown. The home features 3 full bedrooms with 1 1/2 baths . It has an open concept on the main floor, kitchen has beautiful white shaker cabinetry, large island, granite countertops, stainless steel appliances, and luxury vinyl flooring. Large covered patio off the kitchen leading out to a spacious back yard. A new shed recently installed for extra storage. Upstairs features 3 good size bedrooms including a large primary suite. If you are looking for a turn key home with new features, then this home is for you.

Beds:
5
Baths:
4.00
Sq.Ft.:
3,504
Status:
Active
MLS#:
MDKE2005930
Type:
Single Family-Detached
Subdivision:
Coventry Farms
Lot size:
0.28 Acres
Year built:
2007
Courtesy: Doug Ashley Realtors, LLC 410-810-0010
View additional info

ADDITIONAL INFORMATION

311 Devon Drive is located in Coventry Farms; and being located within the Chestertown town limits offers town utilities. The front entrance welcomes you with an open two-story foyer to the second-floor balcony. To the left of the front foyer is a den and to the right is a formal dining room. The foyer hall leads into a large open area that includes a large eat-in kitchen, sunroom and family room with a gas fireplace. The home's design features an abundance of natural light due to its 9-foot ceilings and full-height glass walls on the first floor's rear. The sunroom and first floor primary suite access onto the rear deck with the view and privacy of mature trees. There is a primary bedroom suite on each level; and with there being three additional bedrooms, makes a total of five bedrooms or extra rooms for whatever the need may be. The home offers a garage as well as a full unfinished walk-out basement. The pictures prove the true beauty and spaciousness of this home. (room dimensions are approximate)

Beds:
3
Baths:
4.00
Sq.Ft.:
2,310
Status:
Active
MLS#:
MDKE2005812
Type:
Townhouse
Subdivision:
Historic Chestertown
Lot size:
0.06 Acres
Year built:
2023
Courtesy: Gunther-McClary Real Estate 410-275-2118
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ADDITIONAL INFORMATION

Newly constructed three-bedroom townhome with all the desired attributes. Fantastic water views from the living level and bedrooms! Spacious open living space with warm hardwood floors and a gourmet kitchen. 5-burner induction range, ample cabinet space, and a large island for entertaining. The home is filled with natural light and boasts multiple balconies and a front porch for relaxing. On the second level you'll find two bedrooms and two bathrooms. There's extra room for an office nook. The third bedroom encompasses the entire third floor and has a great view of the Chester River. You'll enjoy the large back balcony with views of historic Chestertown. The third level could be used as the primary bedroom; there is a large full bathroom and closet. The townhomes have a private driveway, so you'll never worry about finding a parking space. Take advantage of the easy access to Wilmer Park and Chestertown Marina, located just across the street. This townhouse is located in the heart of all Chestertown has to offer! Just a short distance to shops, restaurants, renowned bakeries, and the year-round farmers market by Fountain Park. You will have a front-row seat to the Downrigging Festival! Not to mention the many festivals held in downtown Chestertown throughout the year.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,666
Status:
Active
MLS#:
MDQA2015154
Type:
Single Family
Subdivision:
None Available
Lot size:
0.53 Acres
Year built:
1976
Courtesy: RE/MAX Point Realty 302-426-2211
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ADDITIONAL INFORMATION

Beds:
3
Baths:
2.00
Sq.Ft.:
1,424
Status:
Active
MLS#:
MDQA2014828
Type:
Single Family-Detached
Subdivision:
Chester Harbor
Lot size:
0.34 Acres
Year built:
1997
Courtesy: Compass 410-220-5745
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ADDITIONAL INFORMATION

Welcome to 119 Darden Road, a lovely ranch-style home nestled in Chestertown, MD. This charming residence offers 3 cozy bedrooms and 2 bathrooms across 1,424 square feet of living space, perfect for comfortable living. The eat-in kitchen, complete with a handy stove, sets the stage for delightful meals and gatherings. Enjoy the warm ambiance of a fireplace in the spacious living room, enhanced by recessed lighting. Step outside to a large deck overlooking a 15,000 square foot lot, perfect for relaxation and entertainment. This home features a playground and tennis court access for leisurely afternoons. With an attached garage, air conditioning, and in-building laundry, convenience is at your fingertips. Water enthusiasts will appreciate the nearby water access, while pickleball fans can enjoy a game on the community court. Situated in a friendly neighborhood, this home combines comfort with a variety of amenities to suit your lifestyle. Whether you’re cozying up by the fireplace or exploring the outdoors, 119 Darden Road is ready to welcome you home!

Beds:
3
Baths:
3.00
Sq.Ft.:
2,034
Status:
Active
MLS#:
MDQA2015570
Type:
Single Family-Detached
Subdivision:
Sarah Skipper Lands
Lot size:
0.34 Acres
Year built:
1971
Courtesy: Coldwell Banker Chesapeake Real Estate Company 410-778-0330
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ADDITIONAL INFORMATION

Motivated Sellers!!! Welcome to 121 Primrose Road, a spacious two-story residence offering 2,034 square feet on a .345-acre lot. This well-built home delivers comfort, functionality, and potential in a peaceful setting just outside downtown Chestertown. Inside, you’ll find three bedrooms and two full baths upstairs plus a convenient half bath on the main level. The main floor features a bright living area, a classic dining space, and a large all-seasons room off the kitchen—perfect for gatherings or relaxing year-round. The full basement offers a blank slate, ready to finish as a recreation room, workshop, or extra storage. A brand-new septic system provides peace of mind, while the attached two-car garage and expansive back deck add everyday convenience. Situated on the Queen Anne’s County side of Chestertown, this property keeps you close to the shops, restaurants, and waterfront charm of downtown while offering the privacy of a quiet neighborhood.

Beds:
4
Baths:
3.00
Sq.Ft.:
1,936
Status:
Active
MLS#:
MDKE2005928
Type:
Single Family-Detached
Subdivision:
The Village At Chestertown
Lot size:
0.09 Acres
Year built:
2023
Courtesy: Cross Street Realtors LLC 410-778-3779
View additional info

ADDITIONAL INFORMATION

Beautifully done! A MUST see! UPGRADED 2023-built Smart Home, tucked into a quiet and friendly Chestertown community. Thoughtfully enhanced throughout, the kitchen shines with new quartz countertops, a stylish backsplash, upgraded sink and faucet, and added cabinetry with elegant hardware. Fresh light fixtures bring a warm glow to the living spaces, while the laundry room offers added function with quartz surfaces and extra storage. The powder room has been transformed with a stunning vanity and modern fixtures. The second floor offers four spacious bedrooms and two full baths. As a bonus, this property is a smart home, offering comfort and convenience at your fingertips. Just a short drive to multiple marinas in Rock Hall and an easy drive to Philadelphia and Washington, D.C.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,140
Status:
Active
MLS#:
MDKE2005634
Type:
Townhouse
Subdivision:
Chester Arms
Lot size:
0.14 Acres
Year built:
2023
Courtesy: Bayside Realty 443-829-5828
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ADDITIONAL INFORMATION

?? ?? Like-New Chestertown Ranch: Pristine Condition, Ready Today! $250K ?? Skip the construction drama! Step into this stunning, move-in-ready 3-bedroom, 2-bath ranch at 100 Metcalf Rd, Chestertown, MD 21620 for just $250,000! ? Your Dream Home Checklist: ? * NO HOA! Freedom & Savings! ?? * One-Level Living: Easy breezy! ????? * Open Concept: Perfect for entertaining! ??? The heart of the home is the spectacular eat-in kitchen! You'll love the white shaker cabinets, dazzling granite countertops, and sleek stainless steel appliances. ?? The main areas feature gorgeous LVP flooring, while cozy carpet warms the bedrooms. Step outside to your private covered patio for morning coffee ? or evening relaxation. ?? With a generous 5,914 sq ft lot, there's plenty of room for fun! ?? Retreat to your private primary suite ?? with a spa-like en-suite and walk-in shower. ?? Embrace the Chestertown Life! ? This prime spot is minutes from historic downtown charm! Enjoy the weekly farmers market ??, shops, galleries ???, and waterfront festivals like the famous Downrigging Weekend ?. This golden opportunity won't last long! Be the first to call this exquisite property "home." ?? Your new beginning starts here! ??

Beds:
3
Baths:
3.00
Sq.Ft.:
2,160
Status:
Active
MLS#:
MDKE2005854
Type:
Single Family-Detached
Subdivision:
Chesapeake Landing
Lot size:
0.39 Acres
Year built:
2001
Courtesy: Real Broker, LLC 855-450-0442
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ADDITIONAL INFORMATION

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:
3
Baths:
3.00
Sq.Ft.:
1,216
Status:
Active
MLS#:
MDKE2005818
Type:
Single Family-Detached
Subdivision:
None Available
Lot size:
0.07 Acres
Year built:
1900
Courtesy: Cross Street Realtors LLC 410-778-3779
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ADDITIONAL INFORMATION

Charming Move-In Ready Colonial in the Heart of Town This beautifully updated Colonial blends timeless character with modern comfort. Ideally located within walking distance of local restaurants, shops, and the scenic waterfront, it offers the perfect combination of charm and convenience. The exterior showcases classic Colonial appeal with vibrant shutters, fresh paint, new roof, gutters, doors, and Andersen double-hung tilting sash windows.The welcoming front porch overlooks manicured flower beds that enhance curb appeal, while the private backyard provides the perfect setting for weekend gatherings and cookouts or just outdoor relaxation. Inside, the home has been thoughtfully renovated from top to bottom. Recent updates include a Mitsubishi Mini-Split heating and cooling system,Rinnai propane instant hot water heater, and 200-amp electrical service with all-new wiring, fixtures, and recessed lighting throughout. The kitchen is a true showstopper that is completely transformed with new cabinetry, quartz countertops, a center island, stainless steel appliances, and a vented range hood. Refinished rustic hardwood floors run throughout the main level, seamlessly blending old world craftsmanship with modern design. A separate Laundry room features a new washer and dryer with Electric Hookups. Upstairs, you’ll find comfortable bedrooms with Shaw carpeting and pet-proof padding and a beautifully updated bathrooms featuring tiled walls and floors, new vanity, and modern fixtures. The dry basement offers a wide step entrance from Laundry Room with excellent storage space, a new 200-amp electric panel, vapor barrier, and plenty of room for a workshop or home gym or Man Cave. Enjoy the best of in-town living with everything you need just a short stroll away. Schedule your tour today and fall in love with this move-in ready gem

Beds:
5
Baths:
4.00
Sq.Ft.:
2,615
Status:
Active
MLS#:
MDKE2005880
Type:
Single Family-Detached
Subdivision:
The Village At Chestertown
Lot size:
0.09 Acres
Year built:
2023
Courtesy: EXP Realty, LLC 888-860-7369
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ADDITIONAL INFORMATION

Welcome to this stunning 2023 built home — a move-in ready, three-story residence offering 5 bedrooms and 3.5 baths across 2,615 sq ft of thoughtfully designed space. The first floor features an open layout with a spacious family room, dining area, and bright, well-appointed kitchen. This level also includes a convenient first-floor laundry and a powder room. The kitchen is equipped with stainless appliances, a large corner pantry, and a generous peninsula. Upstairs, the owner’s suite offers a walk-in closet and an en-suite bath with a double vanity and walk-in shower. Three additional bedrooms share a full hall bath, also with a double vanity for added convenience. The third floor provides the fifth bedroom, another full bath, and a flexible space ideal for an office, playroom, media room or storage. Extras you’ll love: modern smart features, a fully fenced yard, and a backyard upgraded with pavers and a concrete patio, perfect for grilling, entertaining, or relaxing outdoors. Plenty of closets and storage space. With everything already complete, this home blends comfort, convenience, and style.

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Andrea Conner, Maryland License 667140, Xome Inc., License 667140, [email protected], 844-400-XOME (9663), 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067
Andrea Conner, D.C. License BR200200783, Xome Inc., License CO98372739, [email protected], 844-400- 9663, 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067
Andrea Conner, PA License # RM425337, Xome Inc., PA License #RB067821, [email protected], 844-400-XOME (9663), 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067
Andrea Conner, NJ License # 1758875, Xome Inc. NJ License # 2326449, [email protected], 844-400-XOME (9663), 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067

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Chestertown Real Estate

Chestertown is located in Maryland. Chestertown, Maryland has a population of 5,557. Chestertown is less family-centric than the surrounding county with 10.61% of the households containing married families with children. The county average for households married with children is 15.86%.

The median household income in Chestertown, Maryland is $44,665. The median household income for the surrounding county is $64,451 compared to the national median of $69,021. The median age of people living in Chestertown is 39.1 years.

Chestertown Weather

The average high temperature in July is 87 degrees, with an average low temperature in January of 25.4 degrees. The average rainfall is approximately 45.1 inches per year, with 13.9 inches of snow per year.

Chestertown Map

Chestertown Real Estate Market Conditions

  • Median sales price

    $435,000
    14.5%
    change since last quarter
  • # Active listings

    158
    30-day change

Chestertown Schools and Demographics

Education near Chestertown, MD

City County
High School Graduates 88.37 90.6
College Degree - 2 year 5.13 5.64
College Degree - 4 year 42.33 37.48
Graduate Degree 16.24 9.64
Expenditures per Student 19,095 19,095
Students per Teacher 10.4 10.4

Elementary Schools near Chestertown, MD

Grades Students P/T Ratio ZIP
Centreville Elementary School PK - 02 550 17.4 21617
Church Hill Elementary School PK - 04 314 15.2 21623
H. H. Garnett Elementary PK - 05 233 11.5 21620
Kennard Elementary School 03 - 05 513 17.7 21617
Rock Hall Elementary School PK - 05 187 14.3 21661
Worton Elementary School PK - 05 277 12.7 21678

Middle Schools near Chestertown, MD

Grades Students P/T Ratio ZIP
Centreville Middle School 06 - 08 537 14.9 21617
Kent County Middle School 06 - 08 439 12.9 21620

High Schools near Chestertown, MD

Grades Students P/T Ratio ZIP
Kent County High School 09 - 12 594 13.8 21678
Queen Anne's County High School 09 - 12 1,102 14.3 21617

Demographics near Chestertown, MD

City County
Neighborhood Type Small Town
Population 5,557 19,335
Population Density 2,016 70
Median Age 39.1 47.1
People per Household 1.7 2.1
Median Household Income 44,665 64,451
Average Income per Capita 28,645 39,658

Real estate near Chestertown