Chestertown MD Real Estate & Homes for Sale

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

Welcome to 104 Garland Avenue - a Traditional styled home with Cape Cod inspired design, offering easy one-level living with 3 bedrooms and 2 full baths in desirable Queen Annes County. Set on a corner lot with mature landscaping and inviting curb appeal, this home blends comfort and opportunity. Inside, youll find a functional layout designed for everyday living, highlighted by a thoughtfully appointed kitchen featuring custom pine cabinetry, butcher block and soapstone countertops that bring warmth and character to the space. The spacious rear screened porch with vaulted ceilings creates the perfect setting to relax, dine, or entertain nearly year-round. The second floor is framed and plumbed for an additional bath - ready for you to finish however your vision unfolds.

Theres no place like home! Welcome to the Flyway neighborhood in Chestertown, where this 4 bedroom, 3.5 bath home offers a flexible layout with both formal and casual living spaces. The front entry opens to a formal dining room and a separate bonus room that can serve as a living room, playroom, or home office. The family room with propane fireplace flows into the eat-in kitchen that features a breakfast bar, pantry, and space for a table. Just off the kitchen is a half bathroom and interior access to the 2 car garage. Sliding glass doors lead to a composite deck with steps down to the spacious fenced backyard, all situated on a 1 acre lot offering space to enjoy outdoor living. Upstairs is the primary suite with two walk-in closets and a private bath with dual vanity and walk-in shower. A secondary suite includes its own private bath and walk-in closet, while two additional bedrooms share a hall bath. Laundry is conveniently located on the upper level. Recent updates include a new roof on the home and shed (2025) and recently replaced water heaters (downstairs in 2025, upstairs in 2019). Conveniently located just minutes from downtown Chestertowns shops, restaurants, waterfront, and Washington College. Schedule your showing today!

Experience the best of waterfront living just steps outside of the heart of Downtown Chestertown. Only a few blocks from shops, restaurants, the bustling farmers market, art galleries, annual festivals, and the vibrant cultural life that defines this beloved Eastern Shore community, this exceptional property offers a rare opportunity to enjoy riverfront living with walkable in-town convenience. * With five (plus) bedrooms accommodating up to fourteen guests and three full baths, the home is designed for comfort, flexibility, and enjoyment. Multiple indoor and outdoor gathering spaces make it ideal for those seeking a full-time residence, a weekend retreat, a multi-generational destination, or a strong investment property with outstanding rental potential. * On the main level, a cozy den with a wood-burning fireplace captures Chester River views, creating a warm and welcoming spot to relax after a day on the water. Additional living spaces provide room for groups to spread out-whether entertaining, working remotely, or simply taking a quiet moment to unwind. The primary suite offers its own private vantage point with a picture window overlooking the pool and riverfront-perfect for greeting the sunrise or watching wildlife glide across the water. * Outdoor living is where this property truly shines. Enjoy a covered patio for shaded summer crab feasts, a large deck with a stone fireplace for crisp evenings, and an in-ground pool that looks out toward the shore. With immediate water access, youll launch kayaks, paddle boards, and jet skis right from your backyard-ideal for embracing the river lifestyle. A two-car attached garage provides convenient storage for gear, bikes, and all the water toys. It could also be the perfect space to keep your street legal golf cart which the Town Of Chestertown now allows! * Your new home is also just a short walk from the full-service Chestertown Marina with the potential for a transferable slip-already paid through the 2026 boating season-ensuring you can enjoy hassle-free access to Chester River fun. Additionally, it's a quick ride to the Chester River Yacht & Country Club, where you can indulge in 18 holes of golf, relax by the pool, enjoy happy hour or meals at the full restaurant and bar, and partake in a host of other fantastic member benefits. * Whether youre making it your full-time home, your getaway from the city, or your next strategic investment, this property delivers the best of Chestertown living-waterfront, walkable, and wonderfully welcoming. Embrace a lifestyle of leisure and convenience in this exceptional location.

OPEN HOUSE SATURDAY 3/7/26 FROM 11am-1pm HOPE TO SEE YOU THERE !!! Enjoy easy single-story living in this well-maintained 3-bedroom, 2-bath home situated on a ½-acre lot backing to peaceful farmland. Offering privacy and scenic views, this property blends comfort, space, and thoughtful upgrades throughout. Recent improvements include vinyl siding, a newer roof, and luxury vinyl plank flooring, with original hardwoods underneath for added value and charm. The spacious 12�27 eat-in kitchen is ideal for gatherings and features granite countertops and stainless steel appliances. Both bathrooms are generously sized, with the primary bath showcasing a classic cast iron tub with shower head. A newly added laundry/mudroom enhances everyday convenience and leads directly to a new 14�16 concrete patio and fenced rear yard, perfect for pets, play, or outdoor entertaining. Stay cozy during the colder months with a family room woodstove and warm forced-air heat. The detached two-car garage is topped with a durable 5-year-old metal roof, offering both storage and peace of mind. Town water and sewer add to the homes practicality. Ideally located between the historic charm of Chestertown and the waterfront town of Rock Hall, this home offers access to quaint shops, fine waterfront dining, boating, hiking and biking trails, the YMCA, and the arts and cultural events of Washington College. A wonderful opportunity to enjoy a simpler lifestyle with a little something for everyone. Approximately 1.5 hour drive to Washington, DC and the Delaware beaches. If this lifestyle is for you, call me to schedule your personal showing.

2 level townhome in sought after Tolchester Village! Features a terrific open kitchen with stainless steel appliances, nice living room/dining room combination with a slider to the patio. Bedrooms are good sized and have vaulted ceilings! Tolchester Village is a quaint community that underwent a complete renovation in 2021. Public water and sewer! Common areas include a playground. Affordable, beautiful, and low maintenance!!This property is being sold as-is, property is lender-owned and US Bank is making no representations or warranties. The property must be listed a minimum of 8 FULL days before offers can be reviewed. The first date offers can be reviewed is 3/14/2026

117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects of the building. The Sellers salvaged much of the original moldings, doors and trim to be reused and repurposed throughout the spaces to instill its original character wherever possible. The waterfront offers a floating dock, a BBQ patio & picnic area, kayak and paddle board storage, and the building amenities include off street parking and extra storage space. Choose a unit for yourself and rent the rest of them to cover your payments OR invest and rent them all for a profit! The possibilities with this iconic Chestertown address are endless. 2B - Listed for $350,000: a one bedroom, one bath with soaring ceilings, gleaming original hardwood floors, the largest bedroom in the building and the most square footage per unit above the main level. Water views from the living & dining room make this spot irresistible. BrightMLS: MDKE2006168 1A - Listed for $685,000: three bedrooms and three bathrooms spanning two floors. A walkout lower level to the waterfront, a sweeping covered porch overlooking the Chester River, a four-season sunroom, and a spacious Primary Suite with a walk-in closet and en suite bath with double vanity and tile and glass shower. The modern kitchen offers ample storage, granite countertops, cork tile flooring, and stainless appliances. Two more bedrooms and two additional full baths round out the expansive offerings that are an incomparable setting for Downtown Chestertown waterfront! BrightMLS: MDKE2006162 1B - Listed $200,000: the most cozy setting! One bed one bath Garden Level apartment. Exposed bricks, original fireplace structural detailing, and water views and access directly outside the door. BrightMLS: MDKE2006164 2A - Listed for $375,000: a two bedroom, one bath suite with 12+ foot ceilings, rooms flooded with light from the tall windows, and stunning Chester River views from every living space. The claw foot tub adds vintage whimsy to a space with modern updates throughout. BrightMLS: MDKE2006166 ALL - Purchase one for your weekend pied-à-terre on the Shore! Or� invest in the whole package for $1,600,000! BrightMLS: MDKE2006158 *Condo Association will not allow for vacation/short term rentals (6+ month minimum leases); however, the viability of each space for long term tenancy promises to be lucrative.

117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects of the building. The Sellers salvaged much of the original moldings, doors and trim to be reused and repurposed throughout the spaces to instill its original character wherever possible. The waterfront offers a floating dock, a BBQ patio & picnic area, kayak and paddle board storage, and the building amenities include off street parking and extra storage space. Choose a unit for yourself and rent the rest of them to cover your payments OR invest and rent them all for a profit! The possibilities with this iconic Chestertown address are endless. 2A - Listed for $375,000: a two bedroom, one bath suite with 12+ foot ceilings, rooms flooded with light from the tall windows, and stunning Chester River views from every living space. The claw foot tub adds vintage whimsy to a space with modern updates throughout. BrightMLS: MDKE 1A - Listed for $685,000: three bedrooms and three bathrooms spanning two floors. A walkout lower level to the waterfront, a sweeping covered porch overlooking the Chester River, a four-season sunroom, and a spacious Primary Suite with a walk-in closet and en suite bath with double vanity and tile and glass shower. The modern kitchen offers ample storage, granite countertops, cork tile flooring, and stainless appliances. Two more bedrooms and two additional full baths round out the expansive offerings that are an incomparable setting for Downtown Chestertown waterfront! BrightMLS: MDKE2006162 1B - Listed $200,000: the most cozy setting! One bed one bath Garden Level apartment. Exposed bricks, original fireplace structural detailing, and water views and access directly outside the door. BrightMLS: MDKE2006164 2B - Listed for $350,000: a one bedroom, one bath with soaring ceilings, gleaming original hardwood floors, the largest bedroom in the building and the most square footage per unit above the main level. Water views from the living & dining room make this spot irresistible. BrightMLS: MDKE ALL - Purchase one for your weekend pied-à-terre on the Shore! Or� invest in the whole package for $1,600,000! BrightMLS: MDKE2006158 *Condo Association will not allow for vacation/short term rentals (6+ month minimum leases); however, the viability of each space for long term tenancy promises to be lucrative.

117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects of the building. The Sellers salvaged much of the original moldings, doors and trim to be reused and repurposed throughout the spaces to instill its original character wherever possible. The waterfront offers a floating dock, a BBQ patio & picnic area, kayak and paddle board storage, and the building amenities include off street parking and extra storage space. Choose a unit for yourself and rent the rest of them to cover your payments OR invest and rent them all for a profit! The possibilities with this iconic Chestertown address are endless. 1B - Listed $200,000: the most cozy setting! One bed one bath Garden Level apartment. Exposed bricks, original fireplace structural detailing, and water views and access directly outside the door. BrightMLS: MDKE2006164 1A - Listed for $685,000: three bedrooms and three bathrooms spanning two floors. A walkout lower level to the waterfront, a sweeping covered porch overlooking the Chester River, a four-season sunroom, and a spacious Primary Suite with a walk-in closet and en suite bath with double vanity and tile and glass shower. The modern kitchen offers ample storage, granite countertops, cork tile flooring, and stainless appliances. Two more bedrooms and two additional full baths round out the expansive offerings that are an incomparable setting for Downtown Chestertown waterfront! BrightMLS: MDKE2006162 2A - Listed for $375,000: a two bedroom, one bath suite with 12+ foot ceilings, rooms flooded with light from the tall windows, and stunning Chester River views from every living space. The claw foot tub adds vintage whimsy to a space with modern updates throughout. BrightMLS: MDKE2006166 2B - Listed for $350,000: a one bedroom, one bath with soaring ceilings, gleaming original hardwood floors, the largest bedroom in the building and the most square footage per unit above the main level. Water views from the living & dining room make this spot irresistible. BrightMLS: MDKE2006164 ALL - Purchase one for your weekend pied-à-terre on the Shore! Or� invest in the whole package for $1,600,000! BrightMLS: MDKE2006158 *Condo Association will not allow for vacation/short term rentals (6+ month minimum leases); however, the viability of each space for long term tenancy promises to be lucrative.

117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects of the building. The Sellers salvaged much of the original moldings, doors and trim to be reused and repurposed throughout the spaces to instill its original character wherever possible. The waterfront offers a floating dock, a BBQ patio & picnic area, kayak and paddle board storage, and the building amenities include off street parking and extra storage space. Choose a unit for yourself and rent the rest of them to cover your payments OR invest and rent them all for a profit! The possibilities with this iconic Chestertown address are endless. 1A - Listed for $685,000: three bedrooms and three bathrooms spanning two floors. A walkout lower level to the waterfront, a sweeping covered porch overlooking the Chester River, a four-season sunroom, and a spacious Primary Suite with a walk-in closet and en suite bath with double vanity and tile and glass shower. The modern kitchen offers ample storage, granite countertops, cork tile flooring, and stainless appliances. Two more bedrooms and two additional full baths round out the expansive offerings that are an incomparable setting for Downtown Chestertown waterfront! BrightMLS: MDKE2006162 1B - Listed $200,000: the most cozy setting! One bed one bath Garden Level apartment. Exposed bricks, original fireplace structural detailing, and water views and access directly outside the door. BrightMLS: MDKE2006164 2A - Listed for $375,000: a two bedroom, one bath suite with 12+ foot ceilings, rooms flooded with light from the tall windows, and stunning Chester River views from every living space. The claw foot tub adds vintage whimsy to a space with modern updates throughout. BrightMLS: MDKE2006166 2B - Listed for $350,000: a one bedroom, one bath with soaring ceilings, gleaming original hardwood floors, the largest bedroom in the building and the most square footage per unit above the main level. Water views from the living & dining room make this spot irresistible. BrightMLS: MDKE2006168 ALL - Purchase one for your weekend pied-à-terre on the Shore! Or� invest in the whole package for $1,600,000! BrightMLS: MDKE2006158 *Condo Association will not allow for vacation/short term rentals (6+ month minimum leases); however, the viability of each space for long term tenancy promises to be lucrative.

**Listing price is for ALL FOUR available units for sale as an investment package! Pricing for each unit and their details are below. 117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects of the building. The Sellers salvaged much of the original moldings, doors and trim to be reused and repurposed throughout the spaces to instill its original character wherever possible. The waterfront offers a floating dock, a BBQ patio & picnic area, kayak and paddle board storage, and the building amenities include off street parking and extra storage space. Choose a unit for yourself and rent the rest of them to cover your payments OR invest and rent them all for a profit! The possibilities with this iconic Chestertown address are endless. ALL - Purchase one for your weekend pied-à-terre on the Shore! Or� invest in the whole package for $1,600,000! BrightMLS: MDKE2006158 1A - Listed for $685,000: three bedrooms and three bathrooms spanning two floors. A walkout lower level to the waterfront, a sweeping covered porch overlooking the Chester River, a four-season sunroom, and a spacious Primary Suite with a walk-in closet and en suite bath with double vanity and tile and glass shower. The modern kitchen offers ample storage, granite countertops, cork tile flooring, and stainless appliances. Two more bedrooms and two additional full baths round out the expansive offerings that are an incomparable setting for Downtown Chestertown waterfront! BrightMLS: MDKE2006162 1B - Listed $200,000: the most cozy setting! One bed one bath Garden Level apartment. Exposed bricks, original fireplace structural detailing, and water views and access directly outside the door. BrightMLS: MDKE2006164 2A - Listed for $375,000: a two bedroom, one bath suite with 12+ foot ceilings, rooms flooded with light from the tall windows, and stunning Chester River views from every living space. The claw foot tub adds vintage whimsy to a space with modern updates throughout. BrightMLS: MDKE2006166 2B - Listed for $350,000: a one bedroom, one bath with soaring ceilings, gleaming original hardwood floors, the largest bedroom in the building and the most square footage per unit above the main level. Water views from the living & dining room make this spot irresistible. BrightMLS: MDKE2006168 *Condo Association will not allow for vacation/short term rentals (6+ month minimum leases); however, the viability of each space for long term tenancy promises to be lucrative.

Enjoy three bedrooms on the main floor, including a spacious primary suite with its own private bath. The open-concept main living area seamlessly connects the kitchen, family room, and bright breakfast/sunroom - making everyday living and entertaining effortless. Hosting something more formal? A separate dining room is ready for the occasion. The second level features a generous living/rec room, plus an additional bedroom and full bath - ideal for guests or even a second primary suite. You choose how it works best for you! The basement offers finished office space and a full bath, along with abundant storage and endless possibilities to create even more living space. Two-car garage - Paved driveway-Brand-new back deck overlooking a fenced backyard- Located directly across from the community space

Currently used as a church and in the Downtown Residential R-5 zoning. This sale also includes 5 additional residential lots.

Price Improvement! This pristine rancher is barely three and a half years old and still looks brand new! Exceptionally well maintained and move-in ready! The home sits on nearly one-half acre (.457) and is one of the largest lots in the neighborhood. The lot is shaped in such a manner this it's like getting two for the price of one! There is plenty of space for play and entertaining immediately behind the house, while another equally large section of land branches off and runs behind the neighboring homes. The second section of the property can also be accessed from Cee-Jay Rd. The owner has spoken with the county and understands that a 30x40 detached garage can be built on the property. The widened driveway will easily accomodate your cars, boats, campers, and trailers. Moving inside, the kitchen features granite counter tops and stainless steel appliances. Gorgeous luxury vinyl plank flooring runs throughout the kitchen, laundry room, family room, hallway, and the two full bathrooms. All four bedrooms are carpeted. The home features an efficient heat pump system, a conditioned crawl space, and a tankless hot water heater for those long showers. The roof is protected with long-life Architectural Shingles. A new 12x16 storage shed (2025) with loft storage is included.

Welcome to 304 Hadaway Dr. This classic home has been completely reimagined and is ready for it's next chapter. Entering the home you will immediately notice the beautifully refinished original hardwood floors. As you make your way down the hallway past the newly renovated hall bath with custom tile and designer fixtures, you will find 3 spacious bedrooms. The large family room transitions into a perfectly sized dining room and conveniently placed laundry center. The kitchen is absolutely stunning, with stainless Steele appliances, granite countertops, 42" cabinets and new hardwood floors. Moving into the large primary en suit bedroom, you will fall in love with the spa like bath with a large granite vanity, custom tiled stand up shower and tile floors. The home has a brand new 30 year architectural shingle roof, new windows, furnace, water heater, flush mount lights and the whole house has been painted on the interior and exterior with Sherwin Williams designer color collection. Enjoy the large and lush front and back yards, and large driveway. All within walking distance to Washington College and the beautiful and historic town of Chestertown.

Beautifully Remodeled Two-Level Colonial Offering Timeless Charm and Modern Comfort. This home features a Brand New Kitchen with New Cabinets (2026), Quartz Counters, Stainless Steel Appliances (2026), and a Stylish Tile Backsplash. Enjoy Fully Updated Bathrooms, New Flooring Throughout, and Spacious Bedrooms Filled With Natural Light. New Modern Lighting (2026) and Fresh Custom Paint enhance the homes Clean, Contemporary Feel. Major Updates Include a Brand New HVAC System (2026) and New Windows (2026) for Energy Efficiency, Much More! Relax on the Inviting Covered Front Porch and Enjoy a Truly Move-In Ready Home Designed to Impress.

Custom builder selling his own home that has been well built, well maintained, and thoughtfully designed. This home is in great condition and offers just under 3,000 square feet of living space with 3 bedrooms and 2.5 baths. On everyone's wish list is the generous sized 2-car garage with extra side entrance. The first floor features an open and functional layout designed for everyday living. The kitchen is open to the breakfast area and living room, creating a cohesive main living area. The living room includes a built-in fireplace, while a formal dining room sits just off the kitchen. The kitchen features granite countertops and tile flooring, which continues through the pantry and mudroom. All other countertops throughout the home are upgraded. A spacious laundry room and pantry are conveniently located off the kitchen. The first floor also includes a powder room and a first-floor extra room ideal for a home office or study. A spacious entryway from the attached two-car garage or additional side entrance provides a practical everyday entry. The first-floor primary suite offers comfortable main-level living and includes cathedral ceilings, a private door leading to a roomy composite back deck, and an attached bathroom with marble heated flooring and a walk-in shower, along with a spacious walk-in closet. Upstairs, the home offers two bedrooms with a loft area in between , providing flexible additional living space. Custom inlay flooring is featured in the formal dining room, living room, foyer, primary suite and first-floor extra room, tastefully alternating wood types and adding subtle character. Overall, this home offers quality construction, thoughtful design, and a layout that works well for everyday living. Still more details and touches to be seen when you come to visit. This home truly is move in ready.

Welcome to 118 Little Harbor Way #202, a beautifully reimagined waterfront condo offering effortless living and sweeping panoramic views of the Chester River. Located in the highly desirable Chester River Landing community, this second-floor, 3-bedroom, 2-bath residence delivers the perfect blend of modern luxury, low maintenance, and classic Eastern Shore charm. Completely taken down to the studs and thoughtfully rebuilt, the condo feels brand new from top to bottom. The open floor plan is filled with soft, natural light and showcases wide-plank wood flooring, a cozy gas fireplace, and uninterrupted river views from the main living areas. The stunning kitchen features white quartz countertops and backsplash, a new stainless steel gas range and refrigerator, and an easy flow for both everyday living and entertaining. The primary suite is a true retreat, highlighted by a spa-like tiled shower with multiple shower heads, including a rainfall feature (with glass doors being installed soon). Both bathrooms are finished with timeless, high-quality materials designed to feel clean, classic, and calming. Step out onto the private balcony and take in peaceful, north-facing river views with soft, consistent light throughout the day-ideal for relaxing, reading, or simply watching boats drift by without the glare of direct sun. This is waterfront living at its most comfortable and serene. Additional features include elevator access to the second floor, a one-car garage, and a deeded boat slip (approximately 4 ft MLW). The community offers a waterfront pool, dock, and beautifully maintained grounds, allowing you to enjoy all the benefits of waterfront living without the upkeep. Ideally located within walking distance to historic downtown Chestertown, and just a short drive to golf, dining, and the yacht club at Chester River Yacht and Country Club, this condo is perfectly suited for those looking to downsize, simplify, or secure a refined second home on the water. Move-in ready, thoughtfully updated, and designed for relaxed coastal living-this is Eastern Shore living done right.

This affordable home is ready for you to call HOME! Spacious end-unit Townhome offers a 1,280-sq-ft floor plan with durable LVP flooring throughout the first floor. Enjoy a bright, open-concept living area where the living room flows into the kitchen, featuring a large island, stainless steel appliances, granite countertops, and white shaker cabinets. Step outside to a covered patio overlooking the side and backyard, complete with a new shed-perfect for relaxing or entertaining. The second floor is carpeted and includes a generously sized primary bedroom. and two additional bedrooms. A full bathroom on the second floor offers convenient access from the primary bedroom. Ideally located near Washington College, this home places you moments from Historic Chestertown and the Chester River. Indulge in exceptional dining, charming cafés, shopping, art galleries, the Memorial Weekend Tea Party and more.

Welcome to 24775 Langford Rd, a quiet countryside retreat just minutes from downtown Chestertown. This well-maintained three-bedroom, one-bath home sits on 1.27 acres and offers a peaceful setting with ample outdoor space. The property features a generously sized three-car detached garage/workshop and a large Trex deck with hot tub, ideal for relaxing or entertaining. In 2018, the home underwent a comprehensive renovation, with all major upgrades completed at that time, including the roof, windows, siding, gutters, storm doors HVAC system, well, and full crawl space encapsulation. The interior was also updated in 2018, highlighted by refinished original hardwood floors and a remodeled kitchen with all-wood cherry cabinets and stainless-steel appliances. With extensive updates already done, this property combines rural privacy with convenient access to town. Be sure to schedule your appointment today!

Heres the opportunity buyers wait for. A classic Colonial in sought-after Coventry Farms, priced where this neighborhood rarely plays, offering space, comfort, and the chance to build equity while you live well. Step inside and youre welcomed by a warm, traditional layout that just feels right. Accent walls add personality, the formal dining room sets the stage for holidays and celebrations, and the sunny breakfast room off the kitchen makes everyday meals easy and inviting. Stainless steel appliances and generous cabinetry keep the kitchen both functional and ready for your own finishing touches. Upstairs, the primary suite is a true retreat with bamboo flooring, a walk-in closet, and a private bath with double vanity. Three additional bedrooms provide flexible space for family, guests, home office, or hobbies-room to grow without compromise. The finished lower level delivers the bonus space everyone wants-perfect for movie nights, playroom, gym, or game space-whatever your lifestyle calls for. Outside, the corner lot offers extra breathing room, a fenced yard, and a spacious rear patio made for grilling, gatherings, or quiet evenings at home. A side-entry garage and off-street parking add everyday convenience. Solid bones. Generous space. A price point that opens the door to one of the areas most desirable communities. Move in comfortably now, personalize over time, and enjoy the kind of value thats getting harder to find-especially in Coventry Farms.

Picture Perfect Colonial in Coventry Farms - Chestertown, Maryland Welcome to 218 Camelot Drive, stunning colonial 3,932 total square feet of maintained living Situated on a beautifully landscaped corner lot in the established Coventry Farms community, this home features a fenced backyard with vinyl fencing-ideal for privacy, pets, and play. A brick paver patio with pergola and a creates multiple outdoor living zones perfect for entertaining, with direct access from the breakfast room. Inside, a light filled two story foyer welcomes you with elegant architectural details including crown molding, chair rail, wainscoting, turned stair railings, and hardwood floors throughout the main level. Neutral paint enhances the homes timeless appeal. The gourmet kitchen is designed for both everyday living and entertaining, featuring stainless steel appliances (including a French door refrigerator), custom cabinetry, pantry, granite countertops, tile backsplash, and a center island with breakfast bar. The adjoining breakfast room or bonus space, framed by picture windows and a cathedral ceiling, is perfect for morning coffee or hosting holiday celebrations. The main level offers formal living and dining rooms, a convenient powder room, and a spacious family room highlighted by a floor to ceiling stone, wood burning fireplace with raised hearth and custom stone mantel-an inviting gathering space for family and friends. Upstairs, the primary suite is thoughtfully positioned for privacy and boasts double door entry, a walk-in closet plus an additional closet, and a luxurious ensuite bath with dual vanity, soaking tub, and stall shower. Three additional generously sized bedrooms and a full hall bath complete the upper level. The finished walk out lower level expands your living space with a large recreation area, a possible fifth bedroom, full bath with stall shower, a finished bonus room ideal for a fitness area or media room, and an oversized laundry, utility, and storage area with abundant space for seasonal and long-term storage. Conveniently located just minutes from shopping and local dining favorites, and a short drive to Historic Chestertown along the Chester River, youll enjoy easy access to charming boutiques, restaurants, galleries, Washington College, and rich cultural and historical attractions.

Brand new home in Historic Chestertown available for move-in Right 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 $6,300 or more in closing help from the builders' preferred lender!

**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 convenience of nearby marinas, shopping, and dining. Located just outside of downtown Chestertown and very close to the Chester River Yacht & Country Club.