Chestertown MD Real Estate & Homes for Sale

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Beds:
4
Baths:
3.00
Sq.Ft.:
1,972
Status:
NEW LISTING
MLS#:
MDKE2006498
Type:
Single Family-Detached
Subdivision:
The Village At Chestertown
Lot size:
0.1 Acres
Year built:
2022
Courtesy: Cross Street Realtors LLC 410-778-3779
View additional info

ADDITIONAL INFORMATION

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:
3.00
Sq.Ft.:
1,784
Status:
NEW LISTING
MLS#:
MDQA2017090
Type:
Single Family-Detached
Subdivision:
Chester Harbor
Lot size:
0.6 Acres
Year built:
2004
Courtesy: Long & Foster Real Estate, Inc. 410-643-2244
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ADDITIONAL INFORMATION

Beautiful, Well-Maintained 3BR/2.5BA Home with Upgrades – 215 Fairview Drive Owner pride shines inside and out in this exceptional home located in the charming town of Chestertown, nestled in Queen Anne's County. Built in 2004 and offering 1,784 sq ft of living space, this property blends comfort, functionality, and thoughtful updates—perfect for today’s lifestyle. This inviting home features 3 bedrooms and 2.5 baths, along with a 2-car garage and a newly paved blacktop driveway. Inside, enjoy a bright, functional layout with brand-new carpet throughout the entire upstairs, giving the home a fresh, move-in-ready feel. Additional updates include a new roof, offering peace of mind for years to come. The spacious living areas flow seamlessly, making it ideal for both everyday living and entertaining. Step outside to a large backyard with plenty of space to relax and enjoy. The property includes a children’s play area and a vegetable garden, perfect for outdoor fun and homegrown produce. Highlights: 3 Bedrooms 2.5 Bathrooms 1,784 Sq Ft Built in 2004 2-Car Garage New Roof New Carpet Upstairs Blacktop Driveway Large Backyard Children’s Play Area Vegetable Garden Conveniently located just minutes from downtown Chestertown, Washington College, local shops, dining, and the waterfront, this home offers the perfect balance of peaceful living and accessibility. Schedule your showing today—this move-in-ready home won’t last long! Professional pictures coming 5/7 .

Beds:
2
Baths:
2.00
Sq.Ft.:
1,082
Status:
NEW LISTING
MLS#:
MDKE2006494
Type:
Single Family-Detached
Subdivision:
None Available
Lot size:
0.08 Acres
Year built:
1900
Courtesy: Doug Ashley Realtors, LLC 410-810-0010
View additional info

ADDITIONAL INFORMATION

Great opportunity to own a small cottage in Chestertown. Right next to, and with direct access to the walking trails, this end of road 2 bedroom home comes with an extra lot, currently used for parking, but could also possibly be built on. Buyer to verify with county Expected on Market May 8th. More Photos to come!

Beds:
3
Baths:
3.00
Sq.Ft.:
1,624
Status:
NEW LISTING
MLS#:
MDKE2006488
Type:
Single Family-Detached
Subdivision:
Fairlee
Lot size:
6.29 Acres
Year built:
1970
Courtesy: Long & Foster Real Estate, Inc. 410-260-2800
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ADDITIONAL INFORMATION

Welcome to 9816 Fairlee Road. Be Sure to Click the Virtual Tour!! This property has been meticulously cared for by the current owners and it shows. The property sits on 6.29 acres! If you want plenty of land without giving up on high end fixtures, this is the home for you. Pride of ownership shines through in this gem of a home. The paved driveway leads to a parking pad and a beautiful piece of property. This rancher gives you plenty of space both inside and out. Recently, there was an addition of a mudroom and a second owners suite. Both owners suites have their own bathroom and walk-in shower and one even has a jetted Jacuzzi tub to help you unwind after a long day. There is upgraded flooring through-out, whether it be hardwood or tile, every room feels polished and upscale. The living room includes a woodstove that was installed in 2025 along with a new chimney pipe. There is a creek directly behind your property, which means, water is just a short stroll away. Enjoy tons of natural light in the spacious kitchen where quartz countertops are partnered with a Stainless Steel Refrigerator, built-in microwave and stove. Soft-close cabinets and drawers add to the upscale feel. This home has three spacious bedrooms and three full baths. The un-finished lower level provides you with even more space for storage or it can be your very own blank canvas to finish and increase your living space. The laundry area is in the basement and the washer and dryer will stay with the home. The sliding glass door in the kitchen allows access to your deck and backyard. Enjoy the peace and quiet. Don't be surprised if you see ducks, turkey or deer, they have been known to enjoy the 6+ acres too! The water treatment system has been thoroughly maintained and will convey with the home. High Speed Talkie internet is available. New windows installed throughout most of the home in 2020. This is an Amazing Home! It is turn-key and ready to Welcome its New Owners.

Beds:
3
Baths:
5.00
Sq.Ft.:
3,047
Status:
NEW LISTING
MLS#:
MDKE2006496
Type:
Single Family-Detached
Subdivision:
None Available
Lot size:
0.14 Acres
Year built:
1780
Courtesy: Coldwell Banker Chesapeake Real Estate Company 410-778-0330
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ADDITIONAL INFORMATION

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
Courtesy: Real Broker, LLC 855-450-0442
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ADDITIONAL INFORMATION

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!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,352
Status:
Active
MLS#:
MDKE2006342
Type:
Single Family
Subdivision:
None Available
Lot size:
2.41 Acres
Year built:
2007
Courtesy: Doug Ashley Realtors, LLC 410-810-0010
View additional info

ADDITIONAL INFORMATION

If you're looking for that secluded spot, with land, room to grow and stretch, and don't mind a project, look no further! Dream location on a private road, backing to farmland, and yet just a few miles outside of downtown Chestertown! The house is midway through a full renovation. Walls are in place, electric run, plumbing roughed-in, new siding and a brand New HVAC! All the hard stuff is done! The floor plan is open and airy with a large foyer that looks out through new french doors, to the expansive backyard. The master is good size with its own en suite bathroom. Two further bedrooms off the living room with a good size family bathroom. A seperate Laundry and mudroom make life easy for busy lives. All of this set in lush 2 acres of farmland, just a few minutes outside of Chestertown. What more could you ask for?

Beds:
3
Baths:
3.00
Sq.Ft.:
1,944
Status:
Active
MLS#:
MDKE2006416
Type:
Single Family-Detached
Subdivision:
Coventry Farms
Lot size:
0.23 Acres
Year built:
2007
Courtesy: Coldwell Banker Chesapeake Real Estate Company 410-778-0330
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ADDITIONAL INFORMATION

PRICE IMPROVEMENT: exceptional value? 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:
4
Baths:
3.00
Sq.Ft.:
2,877
Status:
Active
MLS#:
MDQA2016560
Type:
Single Family-Detached
Subdivision:
Sarah Skipper Lands
Lot size:
1.01 Acres
Year built:
2026
Courtesy: Clark & Co Realty, LLC 410-827-4663
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ADDITIONAL INFORMATION

New price, same stunning home!!! Stop scrolling — this beauty is ready for new owners to move in and make lasting memories! Welcome to this exceptional custom-built home offering nearly 3,000 sq. ft. of beautifully designed living space where luxury, comfort, and style come together effortlessly. Featuring 4 bedrooms and 2.5 baths, this home is perfectly situated on a level 1 acre lot directly across from the scenic Chester River. From the moment you step inside, you’ll love the expansive open-concept layout, soaring ceilings, and upscale finishes throughout. The gourmet kitchen is a true showstopper, complete with a large island, sleek quartz countertops, and a hidden pantry/workstation designed for both beauty and function. The inviting stone fireplace creates the perfect focal point for gathering and entertaining. Additional highlights include spacious walk-in closets, a convenient Jack-and-Jill bath, an oversized laundry room with abundant storage, a screened-in porch with vaulted ceilings, and an oversized 2-car garage. The luxurious primary suite offers a private retreat with a spa-inspired tiled shower, while the charming front porch invites you to relax and enjoy peaceful river breezes. Upstairs, the massive fourth bedroom provides endless flexibility, ideal for a recreation room, theatre room, or home office. Located just minutes from the historic waterfront town of Chestertown, founded in 1706, you’ll enjoy charming boutiques, local restaurants, seasonal festivals, the popular Farmers Market, and endless opportunities to experience the beauty of the Chester River. Home to Washington College, the area perfectly captures the charm and lifestyle of Maryland’s Beautiful Eastern Shore. Select photos have been virtually enhanced to showcase the home’s full potential. Don’t let it slip away. Contact us today for your private tour!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,304
Status:
Active
MLS#:
MDQA2016812
Type:
Single Family-Detached
Subdivision:
Char Nor Manor
Lot size:
0.34 Acres
Year built:
1971
Courtesy: RE/MAX Executive 443-274-1900
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ADDITIONAL INFORMATION

This charming 3 bedroom, 2 bathroom home offers the perfect blend of comfort, convenience, and functionality that has major upgrades including Fresh Paint throughout, Renovated Primary Bath and New carpet. The bonus office room is an essential for remote work! The property also features a large 2-car garage/workshop, you’ll have plenty of room for vehicles, projects, or storage. Step inside to a spacious living room that flows seamlessly into the kitchen, complete with gorgeous granite countertops and newer stainless-steel appliances. The cozy primary bedroom is complete with a wood-burning fireplace ideal for relaxing evenings. Enjoy your morning coffee on the welcoming front porch just across the street from views of the Chester River, or host gatherings in the fenced-in backyard with space for play and gardening. You also have peace of mind with a newer HVAC system (2023) and solar panels for a more energy efficient home! Located towards the end of this peaceful street, you’re close to Chestertown’s historic charm, Washington College, a nearby boat ramp, and tax-free shopping just across the Delaware line and still located in Queen Anne's County!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,432
Status:
Active
MLS#:
MDQA2016782
Type:
Single Family-Detached
Subdivision:
The Flyway
Lot size:
1.01 Acres
Year built:
1995
Courtesy: Northrop Realty 410-295-6579
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ADDITIONAL INFORMATION

Immaculate 3-bedroom, 2-bath home set on a breathtaking, oversized lot with exquisite mature landscaping and a truly picturesque setting. Surrounded by lush greenery and stunning trees, including a graceful willow, this property offers a serene, park-like atmosphere, with views from nearly every window resembling beautiful landscape artwork. Inside, the home features a bright, open floor plan designed for modern living. A spacious family room flows seamlessly into the generous kitchen, while a separate dining room remains open to the main living areas—perfect for everyday living and entertaining. The kitchen is highlighted by beautiful French doors leading to the back patio, offering easy access for cooking, grilling, and hosting—perfect for summer barbecues and outdoor entertaining. Palladium windows throughout enhance the home with natural light and showcase the spectacular views. The thoughtfully designed layout offers a private primary suite on one side of the home with its own attached bath. Just off the kitchen and near the primary bedroom is a separate laundry room for added convenience. Two additional bedrooms are situated on the opposite side and share a well-appointed full hall bath. Additional features include fresh paint throughout, a side-entry one-car garage, and an extra-large driveway providing ample off-street parking. Tucked away on a quiet cul-de-sac with no through traffic, this home offers a rare combination of privacy, beauty, and tranquility.

Beds:
2
Baths:
3.00
Sq.Ft.:
1,864
Status:
Active
MLS#:
MDKE2006360
Type:
Townhouse
Subdivision:
Oak Hollow
Lot size:
0.08 Acres
Year built:
2005
Courtesy: Chesapeake Real Estate Associates, LLC 443-215-4663
View additional info

ADDITIONAL INFORMATION

Welcome to 115 Acorn Drive in the desirable Oak Hollow community of Chestertown, Maryland—an end-unit townhome offering space, comfort, and convenience. This three-level home is ideally located near shopping, the YMCA, and local schools, making everyday living easy and accessible. The ground level features a front-entry one-car garage with interior access, leading to a versatile finished space that can be used as a home office, gym, recreation room, or additional living area. This level also offers walk-out access to the rear, adding even more functionality. Upstairs on the main level, you’ll find a spacious living room with beautiful wood flooring, perfect for relaxing or entertaining. A convenient half bath is located nearby for guests. The kitchen offers both functionality and style, featuring upgraded granite countertops, tile flooring, a pantry closet, and an island with an electric stove and downdraft ventilation system. The adjoining dining area provides a comfortable space for meals and gatherings. Just off the kitchen, step out onto a nice rear deck with a pergola that backs to trees—an ideal spot to unwind or enjoy outdoor dining. The third level features two generously sized bedrooms, including a primary suite with an attached bathroom complete with a walk-in shower. A full hall bath serves the additional bedroom, and a hall closet houses a front-load stackable washer and dryer for added convenience. Additional closets provide ample storage space. As an end unit, this home enjoys extra privacy and natural light. Located in an HOA community with very little maintenance required, this home offers easy living in a peaceful and convenient setting.

Beds:
3
Baths:
1.00
Sq.Ft.:
1,120
Status:
Active
MLS#:
MDQA2016836
Type:
Single Family-Detached
Subdivision:
Chester Harbor
Lot size:
0.55 Acres
Year built:
1978
Courtesy: Redfin Corp 301-658-6186
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ADDITIONAL INFORMATION

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:
1.00
Sq.Ft.:
1,296
Status:
Active
MLS#:
MDQA2016478
Type:
Single Family-Detached
Subdivision:
None Available
Lot size:
2.08 Acres
Year built:
1973
Courtesy: Doug Ashley Realtors, LLC 410-810-0010
View additional info

ADDITIONAL INFORMATION

OPPORTUNITY KNOCKS!! This home is being sold as-is and is ready for someone with vision and plenty of elbow grease. Located in Queen Anne's County on Pear Tree Point Rd, the property sits on a generous 2.08-acre lot bordered by farmland on one side of the road, offering peaceful views, and room to breathe. With wood floors, a spacious living room and a living/dining area, the bones are here -- just bring your ideas and your tools and make it shine again. Close to Chestertown while enjoying the benefits of Queen Anne's County living!

Beds:
4
Baths:
4.00
Sq.Ft.:
4,145
Status:
Active
MLS#:
MDKE2006350
Type:
Single Family-Detached
Subdivision:
Prestwick
Lot size:
2.29 Acres
Year built:
2018
Courtesy: Taylor Properties 301-970-2447
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ADDITIONAL INFORMATION

Exceptional custom-built 2018 one-level home on 2.28 private acres in the highly sought-after Prestwick community, ideally nestled just off the Chester River Yacht & Country Club. This thoughtfully designed residence offers a seamless blend of comfort, elegance, and functionality, featuring an open-concept layout with soaring ceilings and abundant natural light throughout. The gourmet kitchen showcases timeless off-white cabinetry, granite countertops in warm earthy tones, and a coordinating backsplash, all opening effortlessly to the expansive great room anchored by a striking stone fireplace—perfect for both everyday living and entertaining. Enjoy multiple outdoor living options including a screened porch, rear porch, and patio—each offering peaceful wooded views and backing to open space for a truly private, tranquil setting that invites you to unwind and explore. The home features rich hardwood flooring, tile, fresh carpet, and fresh neutral paint throughout. The spacious primary suite, privately situated, offers a tray ceiling, two walk-in closets, and a luxurious en-suite bath, while three additional bedrooms and two full baths are thoughtfully positioned on the opposite side—ideal for guests, family, or a dedicated home office. Additional highlights include a welcoming front porch, partially finished basement with half bath and exterior access, and flexible space for recreation, hobbies, or future customization. The attached 2-car garage is complemented by a stairway off the laundry room leading to unfinished space above—perfect for expansion or storage. A standout feature is the detached custom 3-car garage equipped with a car-lift, work benches, cabinets, a mini-split system and unfinished upper level—an incredible opportunity for additional living space. Surrounded by nature, this property offers a rare combination of privacy, craftsmanship, and subtle details that are best experienced in person. Don’t miss this rare opportunity! Built by Alton E. Darling Construction.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,232
Status:
Active
MLS#:
MDKE2006390
Type:
Single Family-Detached
Subdivision:
Tolchester Estates
Lot size:
0.33 Acres
Year built:
2003
Courtesy: Doug Ashley Realtors, LLC 410-810-0010
View additional info

ADDITIONAL INFORMATION

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:
2
Baths:
3.00
Sq.Ft.:
1,867
Status:
Active
MLS#:
MDKE2006224
Type:
Townhouse
Subdivision:
Oak Hollow
Lot size:
0.08 Acres
Year built:
2004
Courtesy: Doug Ashley Realtors, LLC 410-810-0010
View additional info

ADDITIONAL INFORMATION

This beautifully maintained end-unit townhome, owned by its original owner, has been meticulously cared for and is now ready for its next chapter. The end-unit location provides additional natural light, creating a bright and inviting atmosphere throughout. The home has been freshly painted and features brand-new carpeting, while the ceramic tile and hardwood flooring in other areas are in excellent condition. The kitchen is equipped with a full set of newer appliances, offering both style and reliability, and the home also includes a newer washer and dryer—giving you the convenience of updated, move-in ready essentials from day one. Major systems have already been taken care of, including a new heating and cooling system (inside and out), a new hot water heater, and a newer roof and shutters. A flexible bonus room on the ground level currently houses the washer and dryer and can easily serve as a home office, TV room, or additional living space—whatever suits your needs. There is also an additional washer and dryer hookup on the upper level if preferred. Step out from the kitchen onto a private balcony, perfect for relaxing or entertaining. Truly move-in ready, this home offers a clean slate to make your own, along with the peace of mind that comes from years of thoughtful maintenance—making it feel like the perfect townhome.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,499
Status:
Active
MLS#:
MDKE2006378
Type:
Single Family-Detached
Subdivision:
Chesapeake Landing
Lot size:
0.35 Acres
Year built:
2020
Courtesy: Chesapeake Real Estate Associates, LLC 443-215-4663
View additional info

ADDITIONAL INFORMATION

Offers due Wednesday 4/22 by 6PM! Welcome to this beautifully upgraded 3-bedroom, 2-bath Cape Cod, just six years young and perfectly situated in the sought-after Chesapeake Landing community! Ideally located directly across from the Turtle Trail and Millbrook Pond, you’ll love the peaceful, water-oriented setting with nearby access to a community boat ramp, fishing pier, Worton Creek marina, and new restaurant opening soon. This is far from your typical builder-grade home—the current owners have thoughtfully enhanced every inch. The kitchen truly shines with custom upgrades including a built-in pantry, stunning butcher block countertops, island addition, and bar-top seating—plus a full suite of high-end appliances (yes, even a refrigerator with a large touchscreen!). The flexible floor plan offers the best of both worlds with a dedicated dining room and a first-floor bedroom, ideal for guests or one-level living. Outside, enjoy an extended patio, freshly graded yard, and a new storage shed, creating the perfect outdoor space for relaxing or entertaining. With motivated sellers who have already found their next home, this is an incredible opportunity to move right in and start enjoying all that Chesapeake Landing has to offer. Don’t miss your chance to make it yours!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,120
Status:
Active
MLS#:
MDQA2016688
Type:
Single Family-Detached
Subdivision:
Chestertown
Lot size:
1.1 Acres
Year built:
2007
Courtesy: Northrop Realty 410-295-6579
View additional info

ADDITIONAL INFORMATION

Meticulously maintained and full of charm, this delightful three-bedroom, two-bath rambler is perfectly situated on an oversized double lot, offering both comfort and exceptional outdoor space. From the moment you arrive, you’ll appreciate the care and attention this home has received, making it truly move-in ready. Step inside to a bright and inviting open floor plan designed for easy living and entertaining. The spacious living room features a soaring cathedral ceiling and a ceiling fan, creating an airy and welcoming atmosphere. This space flows seamlessly into the kitchen and dining area, allowing for effortless gatherings with family and friends. The dining area is enhanced by a beautiful custom chair rail molding detail that adds character and elegance, while sliding glass doors provide abundant natural light and direct access to the backyard, perfect for indoor-outdoor living. The kitchen is both functional and stylish, offering warm wood cabinetry, recessed lighting, and a vaulted ceiling that adds to the home’s open and spacious feel. The bedroom area includes a comfortable primary suite complete with a private ensuite bath, along with two additional bedrooms, each featuring ceiling fans for year-round comfort. A well-appointed hall bath conveniently serves the two additional bedrooms, providing both functionality and privacy for family members or guests. Step outside and discover an incredible backyard retreat that truly sets this property apart. Fully enclosed with a privacy fence, the expansive yard offers plenty of room to relax, play, or entertain. Enjoy evenings on the patio, stroll along the walking paths, or unwind under the beautiful gazebo. A cozy fire pit creates the perfect gathering spot for cooler nights. One of the standout features of this property is the impressive three-bay workshop with electric, ideal for hobbyists, craftsmen, or anyone in need of substantial workspace and storage. With its thoughtful updates, inviting layout, and exceptional outdoor amenities, this home offers a rare opportunity to enjoy both comfort and versatility in a peaceful setting.

Beds:
3
Baths:
1.00
Sq.Ft.:
1,408
Status:
Active
MLS#:
MDQA2016250
Type:
Single Family-Detached
Subdivision:
Chester Harbor
Lot size:
0.34 Acres
Year built:
1975
Courtesy: Cross Street Realtors LLC 410-778-3779
View additional info

ADDITIONAL INFORMATION

Located in the water-oriented community of Chester Harbor just outside of historic Chestertown, 154 Longfellow Drive offers the ideal blend of convenience and Eastern Shore living. This single-level home is situated on a cleared and fenced 0.34 acre-parcel and a voluntary HOA fee provides access to the community boat ramp and waterfront park. Less than a mile and a half from Route 213, enjoy efficient commuting and quick access to Chestertown, Church Hill, Centreville, Easton, and Kent Island. Inside the home, enjoy an updated full bath, a new HVAC system and well pump, a six year old septic system (flushed in 2025), as well as a large, partially finished basement - perfect for storage.

Beds:
2
Baths:
1.00
Sq.Ft.:
912
Status:
Active
MLS#:
MDKE2006364
Type:
Single Family-Detached
Subdivision:
Tolchester Estates
Lot size:
0.37 Acres
Year built:
1952
Courtesy: RE/MAX Leading Edge 410-224-3200
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ADDITIONAL INFORMATION

MOVE IN READY!! Adorable, Affordable, move in ready & two blocks from the Chesapeake Bay! Appliances, roof, waterproof vinyl plank flooring, stove, dishwasher recently upgraded, beautifully tiled bathroom flooring. Freshly painted, Bright and inviting updated kitchen, Spacious Dining/family rm with vaulted ceilings, ceiling fan. Enjoy fishing or relaxing at the private community beach or head over to Tolchester Marina & The Shanty Beach Bar, dining & shopping. just a very quick trip to entertainment, or boating. Great location, private lot just 10 minutes from downtown Chestertown or Rock Hall where you can enjoy shops, marinas, dining and regular events. Level lot with plenty of potential.

Beds:
3
Baths:
4.00
Sq.Ft.:
2,172
Status:
Active
MLS#:
MDKE2006354
Type:
Townhouse
Subdivision:
Chestertown Historic District
Lot size:
0.09 Acres
Year built:
2025
Courtesy: Gunther-McClary Real Estate 410-275-2118
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ADDITIONAL INFORMATION

Newly constructed three-bedroom townhome with fantastic water views from the living level and bedrooms! Spacious open living space featuring 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. You'll love the warm hardwood floors throughout the home. On the second level you'll find two bedrooms and two bathrooms. 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.:
1,588
Status:
Active
MLS#:
MDKE2006316
Type:
Single Family-Detached
Subdivision:
Mile Tree Village
Lot size:
0.41 Acres
Year built:
1980
Courtesy: Coldwell Banker Chesapeake Real Estate Company 410-778-0330
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ADDITIONAL INFORMATION

*****PRICED $30,000 UNDER THE RECENT APPRAISED VALUE***** One floor living, a wood burning fireplace, and hardwood floors help this represent the cozy but elevated Eastern Shore lifestyle. The Mile Tree Village community is tucked on a quiet cul-de-sac with views of the Chester River. The home has been thoughtfully improved with major 2021 updates including joist replacement, flooring, crawl space encapsulation, and rear fencing all performed by the greatest hits list of Kent County craftsmen, along with freshly stained rough-cut cedar siding in 2025. An oversized two-car garage, serene courtyard with water feature, and a spacious, partially shaded backyard with deck seating create a setting that feels both private and inviting—all just a short walk to downtown shops, restaurants, Washington College, and the town’s parks.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,271
Status:
Active
MLS#:
MDQA2016758
Type:
Single Family-Detached
Subdivision:
Pine Cove
Lot size:
0.5 Acres
Year built:
2017
Courtesy: Coldwell Banker Waterman Realty 410-643-5005
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ADDITIONAL INFORMATION

Welcome to Pine Cove. A small peaceful enclave of homes that sits oh so close to the Chester River and the Deep Landing Boat Launch. Surrounded by working farms and pastoral views this beautifully maintained home is just 9 years young. Boasting an open concept layout with soaring cathedral ceilings in the main living areas, a gourmet kitchen with granite counters, stainless-steel appliances, and hardwood floors throughout, you will fall in love with this idyllic rural retreat. One level living is the key to comfort and ease. Two bedrooms and a full bath on one side of the house and a gorgeous Owners suite on the other side with a generous walk-in closet and Spa like bath with stand-up shower and a soaking tub. A double vanity ensures room for all your needs. Laundry and mechanicals are just off the hallway by the owner's suite and garage access is just off the main foyer. Storage shelving in the double size garage will stay with the home and there is an additional storage shed in the back yard. The back yard is fully fenced with a pretty vinyl fence just the right size for small pets. You will also find garden beds and bird feeder poles. The rear of the house boasts a custom deck for your entertaining pleasure. Many perennials and lovely landscaping bring the front and back yards to life and attracts birds and pollinators alike. It's a short walk down to the local Boat ramp and the river for your summer activities. Come and see how this beautiful turnkey home can be yours!

Beds:
3
Baths:
1.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDQA2016720
Type:
Single Family-Detached
Subdivision:
Chester Harbor
Lot size:
0.34 Acres
Year built:
1974
Courtesy: Doug Ashley Realtors, LLC 410-810-0010
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ADDITIONAL INFORMATION

There is so much potential for this 3 bedroom, 1 bath ranch, in need of a little updating, with attached carport located in Chester Harbor. There is a full unfinished basement and a 3 car detached garage all situated on 2 parcels that include 5 lots. Chester harbor offers water access to Rosin Creek.

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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

    $457,500
    14.5%
    change since last quarter
  • # Active listings

    113
    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