Queen Street Gem! Located in the historic section of Chestertown, walk to the restaurants, shops, theater, farmer's market, and waterfront. Beautiful woodwork and pocket doors. Spacious rooms, hardwood flooring, solid wood doors, thick moldings, and ample closet space. Featuring 5 bedrooms and 2.5 baths, with 3 bedrooms on the second floor and 2 additional bedrooms on the 3rd floor. Bathrooms have been updated. Wide front porch. Adorable fenced-in rear courtyard. This property has a ton of character and charm. Just waiting for its new owners!

Welcome to your private oasis! This charming home boasts mature landscaping that provides both beauty and privacy on a large corner lot. Custom built Cape Cod offers a first floor primary suite, living room with fireplace and built ins, formal dining room and a kitchen with granite counters and updated appliances. There’s an open area on the 2nd level ideal for reading or watching TV. Plus 2 more bedrooms and an office. Updates include: new carpet primary BR, garage door 2024, roof Dec 2022. Enjoy the serene ambiance from the large deck, overlooking a picturesque pond with not one, but two enchanting waterfalls. The soothing sound of cascading water creates a tranquil atmosphere, perfect for relaxation and unwinding. This property is a true retreat, offering an idyllic escape right in your backyard. Located just minutes from the Chester River and Chestertown’s historic district.

Welcome to 11960 Flour Mill Street. This is the perfect house for a growing family or a multi-generational household. Main House has 6 full bedrooms and 4 full bathrooms while the second floor above the garage is a spacious mother-in-law suite with a separate entrance, efficiency kitchen, full bath and walk-in closet. First floor has a bedroom and full bath and wide open floor plan in the kitchen and living rooms. Kitchen features stainless steel appliances, granite countertops and wood cabinets. Second floor has 5 bedrooms and 2 full baths. Partially finished full basement has another full bathroom and offers a range of possibilities for the next owner. This home has more room and storage than you could imagine. The Villages at Kennedyville is a quiet, local community. Less than 90 minutes to Philadelphia and Washington D.C. 30 minutes to Middletown, Delaware and tax-free shopping. Close to Turners Creek State Park, Betterton Beach and the restaurants/marinas in Galena on the Sassafras River. Just a few minutes to historic downtown Chestertown. 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. Seller offering $7,000 credit at closing to repair the Air Conditioning units.

Welcome to the Johnson-Lindsey House, a rare opportunity to own a piece of Chesapeake City’s history. Located in the heart of the Historic District, this Federal-style home was built around 1850 by Joseph W. Lindsey, the town’s sawmill and lumber yard owner. Zoned Village Center (VC), the property offers incredible flexibility for residential or commercial use, making it ideal for those looking to blend history with modern living or business potential. Situated along the route of Chesapeake City’s beloved parades and festivals, it’s just a short walk to waterfront dining, boutique shopping, and local attractions.This charming home exudes character with its classic wood-sided Federal-style architecture and distinctive bump-out picture windows on the south side. The original cast and wrought iron fence still encloses the front courtyard, a space once adorned with a porch. With historic approval already granted, a new owner has the option to restore this feature. The front entrance welcomes you with intact stained glass and an old-style door ringer, setting the tone for the timeless beauty within.Inside, the home showcases original hardwood flooring, tall wood windows with storm covers, and six-inch floor moldings. The light-filled foyer leads into a spacious family room with floor-to-ceiling windows and an electric fireplace wired for propane. From there, the dining room offers built-in cabinetry and access to a covered side porch. The remodeled kitchen seamlessly blends old-world charm with modern updates, featuring Quartz Silestone countertops, Italian subway tile, luxury vinyl plank flooring, a new sink, stainless steel appliances, and professionally painted cabinets. Off the kitchen, a remodeled powder room and an enclosed laundry room with an antique sink provide added convenience.The second level offers a generously sized primary suite with a fully remodeled bath, including a tile walk-in shower and luxury vinyl plank flooring. Two additional bedrooms on this floor provide space for guests, family, or a potential additional full bath if desired. The third level features two more bedrooms, one currently used as storage, with ample space to add a third full bath.The backyard is a hidden retreat, offering a courtyard-style space with a side porch, a brick side patio, and a rear brick patio leading to the detached two-car garage. Very few homes in town offer garage parking, making this a rare and valuable feature. With electricity, a concrete floor, and a propane heating element, the garage could easily be transformed into a carriage house, Airbnb rental, or business space. A parking pad allows for two additional vehicles, making this property one of the few in the historic district with a backyard backing to woods and extra off-street parking.This home has been meticulously maintained with a series of updates, including five new mini-split heating and cooling units installed in 2024, along with a new storm door, professionally painted kitchen cabinets, and new ceiling fans. Recent improvements also include luxury vinyl plank flooring in the kitchen and primary bath, updated carpeting on the stairs and upper hallway, a new furnace, oil tank, and hot water heater, as well as professional interior painting. The main architectural shingle roof was replaced in 2019 with a 30-year warranty.The Johnson-Lindsey House has been featured on the Candlelight Tour and is prominently displayed on the cover of the Chesapeake City town map. Annual grant opportunities through the Maryland Historic Trust provide additional incentives for restoration and improvements. Whether you're looking for a distinctive home, a commercial opportunity, or a combination of both, this historic gem is truly one of a kind.

Don’t let the outside fool you—this beautifully renovated 3-bedroom, 1.5-bathroom home offers three levels of living space, with over 2,200 sq. ft. above ground and an additional 550 sq. ft. below ground! Every inch of this home has been thoughtfully updated to blend modern comfort with timeless charm.Step inside to discover a stunning custom kitchen, a true chef’s dream featuring a gas stove, upgraded quartz countertops, solid wood cabinetry, and stylish open shelving—perfect for both cooking and entertaining. The spacious living areas boast brand-new LVP flooring, fresh finishes, and an inviting atmosphere throughout.Upstairs, the primary bedroom is a private retreat, complete with a mini-split AC/heat unit, a large dressing room, and a convenient half bath.Head downstairs to a versatile lower level, where an open-concept space offers endless possibilities—whether you need a media room, game area, crafting space, or home gym. The large laundry area and utility room provide added functionality.Step outside to your own backyard oasis, enclosed by a beautiful privacy fence. Enjoy the spacious patio, detached garage/barn, and storage shed—ideal for hobbies, storage, or workshop space.This home is completely move-in ready and packed with upgrades—all it needs is you! Don’t miss your chance to see this hidden gem—schedule your private showing today!

Step into this one‑of‑a‑kind Dutch Colonial—no cookie‑cutter here! Full of charm and character, this beautifully maintained home sits on 1.40 private acres, has been professionally painted throughout, and offers a layout that’s both spacious and versatile.The main level features beautiful hardwood floors, while the expansive 21’ x 21’ family room boasts luxury vinyl plank flooring, combining comfort and style. A cozy sitting room with a wood‑burning fireplace invites you to relax, and the dining area includes a sliding glass door to the covered rear porch—perfect for easy indoor‑outdoor living.The oversized 26’ x 13’ kitchen is a chef’s dream with a brand‑new center island cooktop, pickled cabinets, granite countertops, and a wall oven. Also on the main level is a flex room with a closet—ideal as a home office, guest space, or bonus room—along with a convenient powder room.Upstairs offers 4 spacious bedrooms, hardwood floors, and 2 full baths. The upper level is full of charm with deep window wells, and the entire home is complete with vinyl tilt windows—easy to clean and energy‑efficient. The primary suite includes a walk‑in closet and a bathroom with a large shower.The partially finished, walk‑out basement offers endless potential for additional living space, a rec room, or home gym. Step outside to a covered rear porch, then head down to your private inground pool and pool storage—an entertainer’s dream! A detached 2‑car garage (24’ x 22’) and a peaceful setting with no HOA complete the package.All this just minutes from I‑95, shopping, dining, and marinas—an ideal location for commuters or weekend adventurers!A must‑see to appreciate the amazing work done on this home… pure perfection!!!

🏡 Water-Oriented Home with BOAT SLIP included with this property in Earleville, MDThis beautifully crafted home offers 3 bedrooms, along with 1 additional rooms on the upper level currently used as bedrooms. The property features 2 stunning full bathrooms, thoughtfully designed by the builder-owner with exceptional quality. The main level showcases barnwood floors and stainless steel appliances, all within an open-concept layout accentuated by cathedral ceilings.Additional highlights include Marvin windows throughout, Cedar Impressions siding, a deep one-car garage, a full basement, composite decking, an outdoor shower, newer well and a 30-year roof. The second-floor family room provides a spacious area for relaxation and entertainment.Located in a desirable water-oriented community, this home is just steps from scenic water views and offers convenient access to various water activities. The community features a beautiful beach, perfect for swimming, sunbathing, and family gatherings. Residents can also enjoy golf cart-friendly streets, a nearby restaurant/bar, a convenience store, and a public boat ramp.With a boat slip included, this property is ideal for water enthusiasts seeking a tranquil, community-focused lifestyle.

Historic charm with a modern floor plan. Live just around the corner walking to the shops, galleries, and restaurants of downtown Chestertown in this beautifully updated Victorian on quiet Mill Street. High end appliances such as Miele and Bosch adorn the kitchen and laundry. Easily converted back into a 3 bedroom. The backyard is well landscaped, has a covered outdoor living space, and a spacious detached hobby shed or office space. This low maintenance property with walkable lifestyle works perfectly for a weekend retreat or year round residence. Chestertown is located less than 1.5 hours from Washington D.C, Philadelphia, and Baltimore.

THERE ARE MORE PICTURES COMING. This charming 2-bedroom, 1-bathroom waterfront home is the perfect getaway for those who love the water. Nestled along the river, it offers a peaceful and relaxing atmosphere with stunning views right from your living room, thanks to the beautiful bay windows that frame the water. Enjoy the convenience of your own private boat ramp and dock, making it easy to set off on a day of boating, fishing, or crabbing. Whether you're watching the sunrise over the river, casting a line from the dock, or simply unwinding with the soothing sounds of the water, this home is a serene retreat for nature lovers and water enthusiasts alike.