83 properties for sale in Kings Court, Kingstown District 2 Church Hill Queen Anne's County Maryland

Built in 1780/1-, 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

Charming and inviting! Welcome to 139 Prospect St. A delightful 3-bedroom, 1-bath rancher offering approximately 1,200 square feet of comfortable living space. This well-maintained home features thoughtful updates to the kitchen and bath, blending modern touches with classic appeal. Step onto the inviting front porch and into a spacious living room that flows seamlessly into the eat-in kitchenperfect for everyday living and easy entertaining. A private hallway leads to a generously sized primary bedroom and two additional spacious bedrooms. Outside, enjoy off-street parking and a large, deep backyard ideal for relaxing, gardening, or gathering. Conveniently located just moments from downtown Chestertowns shops, restaurants, and local attractions, this property is a wonderful opportunity as a full-time residence, weekend retreat, or investment property. An exceptional value just minutes from the charm and amenities of historic downtown Chestertown! Mortgage savings may be available for

Historic Charm in the Heart of Downtown Chestertown Step back in time and discover the character, craftsmanship, and endless potential of this circa-1820 historic home. Nestled in the heart of downtown Chestertown, this property is filled with the original architectural details and timeless charm that historic home lovers dream about. Featuring 2 spacious bedrooms with the potential for a 3rd, 3 full bathrooms, a welcoming kitchen with an eat-in area, and a generously sized dining room, this home offers a solid foundation for restoration and reimagining. While the property is in need of some repairs and renovation, it presents an incredible opportunity for the buyer who has always dreamed of owning a piece of history; or the savvy investor looking for their next restoration project. Outside, escape to your own private backyard sanctuary complete with a brick patio, fountain, and peaceful garden setting, an unexpected retreat right in town. Please note that the home is currently furnish

Fully renovated from top to bottom, this charming 3-bedroom, 1.5-bath townhome in the heart of downtown Chestertown offers the perfect blend of modern updates and convenience. Step inside to find new flooring, new carpet, fresh paint throughout, updated molding, and a beautifully renovated kitchen featuring white cabinetry, new countertops, and new appliances. Both bathrooms have been completely updated with all new fixtures and finishes. The main level offers ample living space, dinging room and new kitchen and laundry. Upstairs you will find three bedrooms and a full bathroom, with access from the primary bedroom as well. Outside, enjoy a newly fenced backyard, updated shed, and an extra-deep lot offering the potential for additional rear parking. A new roof installed in 2024 adds even more value and peace of mind. Boasting generous space and extensive upgrades throughout, this home presents an exceptional opportunity for a primary residence, weekend getaway, or investment property.

Gorgeous house on River Rd in the Queen Anne's County side of Chestertown. 3 total bedrooms and 2.5 baths. The main bedroom is on the first floor. Stunning sun room, patio and pool. 2 car garage. Living room and den

NEW PRICE One of Chestertown's Best Values! Over 2,500 square feet of 2023 construction priced comparably to many older Chestertown homes with just 1,2001,800 square feet. If you're looking for maximum living space, modern design, and exceptional value, this home deserves a closer look. This move-in ready, three-story home offers 5 bedrooms, 3.5 baths, and 2,535 square feet of thoughtfully designed living space. The inviting front porch welcomes you into an open-concept main level featuring a spacious family room, dining area, and a bright kitchen designed for everyday living and entertaining. Highlights include stainless steel appliances, a generous peninsula, large corner pantry, first-floor laundry, and convenient powder room. The private owner's suite features a spacious walk-in closet and en-suite bath with double vanity and walk-in shower. Three additional bedrooms share a full bath with double vanity, while the finished third level provides a fifth bedroom, full bath, and flexib

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

ONLINE AUCTION: Bidding begins 07/20/2026 @ 10:00 AM. Bidding ends 07/24/2026 @ 11:40 AM. List Price is Suggested Opening Bid. Deposit: $25,000. This auction takes place on the Ashland Auction Group Website Bidding Platform. Pre-auction offers may be accepted. Located along Marylands Eastern Shore in Kent County, this single-family home offers approximately 1,896 square feet of living area on a 0.51 acre lot. The home is situated along Worton Road, approximately five miles north of historic Chestertown. The location provides convenient access to shopping, dining, employment centers, recreational amenities, and the surrounding waterfront communities of Kent County. Maryland Route 297 provides connectivity throughout the Worton and Chestertown areas, while nearby routes offer access toward Rock Hall, Betterton, Cecil County, and Delaware. Each person entering the property is required to complete a right of entry agreement prior to touring the property

Charming Brick Rancher Near the Chester River This custom-built brick rancher sits in a nice Chestertown neighborhood with excellent curb appeal, a classic hipped roof, and a convenient circular driveway. The drive runs under a gable-roofed breezeway that connects to an oversized 26x40 two-car garage, which will soon have brand-new garage doors. Coming into the Home. Living Room: Walk along the cobblestone slate path and pass through the new, classic front door into a spacious living room featuring hardwood floors that run throughout the entire house. Dining & Kitchen: A curved archway leads from the living room directly into the dining room. The dining room has an entryway to the kitchen, which could easily be opened up for an even more open feel. Porch: The dining room leads right out to a comfortable porchthe perfect spot to relax and enjoy this nice, quiet neighborhood. Mudroom & Back Entry: An oversized back entry from the breezeway leads into a large mudroom and utility space. Fe

This cute as a button downtown stunner is recently updated and ready for the next owner to fall in love with the lifestyle that comes with living in the Historic District. Located on a quiet side street just a block from Chestertown's dining, shopping, and galleries, this is the perfect blend of social and tranquil. This means that walking down to Evergrain or Modern Stone Age Kitchen for a croissant and cappuccino before a morning stroll along the waterfront promenade could become part of your morning routine. The thoughtful updates over the years have opened the floor plan and allowed for a modern layout. Many serious upgrades have occurred in the past year including the kitchen and electrical service. The wood burning stove, basement for storage, and garden building are amazing benefits. Invest wisely in an amazing home while improving your quality of life in this incredible community on the water less than 2 hours from Washington DC, Philadelphia, and Baltimore

Prime location in Downtown Chestertowns Historic District offering approximately 1,785 square feet of practical living space on three levels with 4 off-street parking spaces. The RB zoning also provides flexibility for live/work arrangements, and the property has rare building expansion potential to accommodate family and/or business growth

Welcome to the epitome of Eastern Shore waterfront luxury, offered for the first time in almost 60 years. This stunning 11-acre estate offers an unparalleled lifestyle, featuring 560 feet of prime water frontage on the Chester River and a private 140-foot dock with 7 feet of mean low water, perfect for all your adventures. The heart of this property is the beautifully renovated 3-bedroom, 2 full bath, 2 half bath main home, meticulously remodeled in 2018 with the highest quality materials and fixtures. The residence boasts sweeping water views from nearly every room, allowing you to enjoy picturesque sunrises Chester River. As you enter, you are greeted by a grand living room featuring a striking five-foot fireplace set within a soaring vaulted ceiling, creating a warm and inviting atmosphere. Expansive windows frame the breathtaking views and fill the space with natural light, enhancing the open-concept design that is perfect for both relaxing and entertaining. The gourmet kitchen is

Searching for a home with peaceful country views and a beautifully designed interior? This meticulously maintained property offers the perfect blend of modern style, comfort and functionality. Inside, youll find cathedral ceilings with a beautiful wood accent beam, gorgeous LVP flooring throughout and a light, airy feel created by the neutral color palette and crisp white trim. The open floorplan is ideal for both everyday living and entertaining, centered around a stunning kitchen featuring custom tile backsplash, black farmhouse accents, matching stainless steel appliances, gas range, recessed lighting and a large center island with pendant lighting above. The spacious primary suite includes a walk in closet and private bath complete with dual vanity, standing shower and linen closet. Outside, the fully fenced backyard overlooks wide open farmland views and includes a charming shed with covered front porch, creating the perfect place to sit back, relax and enjoy peaceful surroundings

To be built! Welcome to this beautifully designed 1,980 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath, large walk-in closet, and access to the private balcony. Two additional bedrooms share a full bathroom. The upstairs is complemented by a convenient second-floor laundry. Catch a glimpse of the Chester River from the front porch or upper covered balcony, the perfect place to enjoy morning coffee or evening cocktails. Enjoy the waterfront lifestyle of the sought-after Chester River Landing community. Deep water boat slips are available for lease or purchase. The community amenities include docks, in-ground pool, grilling and outdoor dining area right on the water, large firepit, a beach to launch kayaks, ca

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!

To be built! Welcome to this beautifully designed 2,092 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 3.5 baths. Inside, an open-concept main level connects the great room, gourmet kitchen, and dining area—perfect for entertaining. There's also a private study, which could be used as additional space for guests. Upstairs, the primary suite features a spa-like bath, large walk-in closet, and sliding doors to the second floor balcony. There are two additional bedrooms, each with their own full bathroom. The upstairs is complemented by a convenient second-floor laundry. This home is designed with future needs in mind, offering the option of a residential elevator for effortless access to all levels. Enjoy the waterfront lifestyle of the sought-after Chester River Landing community. Deep water boat slips are available for lease or purchase. The community amenities include docks, in-ground pool, gr

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 fireplaceperfect for both everyday living and entertaining. Enjoy multiple outdoor living options including a screened porch, rear porch, and patioeach 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 sui

To be built! Welcome to this beautifully designed 1,980 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining areaperfect for entertaining. Upstairs, the primary suite features a spa-like bath, large walk-in closet, and access to the private balcony. Two additional bedrooms share a full bathroom. The upstairs is complemented by a convenient second-floor laundry. Catch a glimpse of the Chester River from the front porch or upper covered balcony, the perfect place to enjoy morning coffee or evening cocktails. Enjoy the waterfront lifestyle of the sought-after Chester River Landing community. Deep water boat slips are available for lease or purchase. The community amenities include docks, in-ground pool, grilling and outdoor dining area right on the water, large firepit, a beach to launch kayaks, can

To be built! Welcome to this beautifully designed 1,964 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the great room with gas fireplace, gourmet kitchen, and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath and large walk-in closet. There are two additional bedrooms that share a full bathroom. The upstairs is complemented by a convenient second-floor laundry. Enjoy the waterfront lifestyle of the sought-after Chester River Landing community. Deep water boat slips are available for lease or purchase. The community amenities include docks, in-ground pool, grilling and outdoor dining area right on the water, large firepit, a beach to launch kayaks, canoes and paddle boards, beautifully landscaped paths along the water's edge and much more! This home combines the charm of the Eastern Shore with the con

To be built! Welcome to this beautifully designed 2,784 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 4 bedrooms and 3.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining area—perfect for entertaining. There is a first floor primary bedroom for one-floor living options. Upstairs, the second primary suite features a spa-like bath, large walk-in closet, and access to the private balcony. Two additional bedrooms share a full bathroom. Catch a glimpse of the Chester River from the front porch or upper covered balcony, the perfect place to enjoy morning coffee or evening cocktails. Enjoy the waterfront lifestyle of the sought-after Chester River Landing community. Deep water boat slips are available for lease or purchase. The community amenities include docks, in-ground pool, grilling and outdoor dining area right on the water, large firepit, a beach to launch k

To be built! Welcome to this beautifully designed 2,231 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the great room, with gas fireplace, to the gourmet kitchen and dining areaperfect for entertaining. Upstairs, the primary suite features a spa-like bath, walk-in closets, and doors to the private waterfront deck. Two additional bedrooms share a full bath. The upstairs is complemented by a convenient second-floor laundry. Enjoy broad water views and breathtaking sunrises over the Chester River. The covered porch and expansive windows create a seamless connection to the outdoors, enhancing the waterfront lifestyle of this sought-after community. Deep water boat slips are available for lease or purchase. The community amenities include docks, in-ground pool, grilling and outdoor dining area right on the water, large firepit, a beach to launch

To be built! Welcome to this beautifully designed 1,980 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath, large walk-in closet, and access to the private balcony. Two additional bedrooms share a full bathroom. The upstairs is complemented by a convenient second-floor laundry. Catch a glimpse of the Chester River from the front porch or upper covered balcony, the perfect place to enjoy morning coffee or evening cocktails. Enjoy the waterfront lifestyle of the sought-after Chester River Landing community. Deep water boat slips are available for lease or purchase. The community amenities include docks, in-ground pool, grilling and outdoor dining area right on the water, large firepit, a beach to launch kayaks, ca

To be built! Welcome to this beautifully designed 1,964 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the great room with gas fireplace, gourmet kitchen, and dining areaperfect for entertaining. Upstairs, the primary suite features a spa-like bath and large walk-in closet. There are two additional bedrooms that share a full bathroom. The upstairs is complemented by a convenient second-floor laundry. Enjoy the waterfront lifestyle of the sought-after Chester River Landing community. Deep water boat slips are available for lease or purchase. The community amenities include docks, in-ground pool, grilling and outdoor dining area right on the water, large firepit, a beach to launch kayaks, canoes and paddle boards, beautifully landscaped paths along the water's edge and much more! This home combines the charm of the Eastern Shore with the conv

Price increase due to the home’s expanded footprint—over 1,200 additional square feet! To be built! Welcome to this beautifully designed 3,540 sq. Ft. home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The standard floor plan includes 4 bedrooms and 3.5 baths, with the option to expand to 5 bedrooms and 4.5 baths by adding a first-floor guest suite. Inside, an open-concept main level connects the great room, gourmet kitchen, and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath and walk-in closet, complemented by a convenient second-floor laundry. Designed with future needs in mind, this home also offers the option of a residential elevator for effortless access across all levels. Enjoy broad water views and breathtaking sunrises over the Chester River. The covered porches and expansive windows create a seamless connection to the outdoors, enhancing the waterfront lifestyle of this sought-after c