Chestertown Homes with Garden View

Chestertown Homes with Garden View

Welcome to Chestertown, Maryland, a charming riverside town that beautifully blends rich history with a vibrant community spirit. Nestled along the banks of the Chester River, Chestertown is renowned for its picturesque streets, historic architecture, and a lively arts scene. With its roots dating back to the 1700s, the town offers a unique glimpse into America’s past, making it a delightful place to call home.

One of the most enchanting features of Chestertown is the abundance of homes that boast stunning garden views. Imagine waking up each morning to the sight of blooming flowers and lush greenery right outside your window. These homes not only provide a serene escape but also create a picturesque backdrop for your daily life. Whether you’re sipping coffee on your porch or hosting a summer barbecue, the beauty of nature is always within reach in this delightful town.

Chestertown is also a hub for outdoor enthusiasts, with easy access to parks, walking trails, and the scenic riverfront. The community hosts various events throughout the year, from farmers' markets to art festivals, fostering a sense of belonging among residents. With a welcoming atmosphere and a strong sense of community, Chestertown is not just a place to live; it’s a place to thrive.

Explore the charm of Chestertown and discover your dream home with a garden view today. Experience the perfect blend of tranquility and vibrant community life in this hidden gem of Maryland!

Newest Chestertown Homes with Garden View

$499,999
4 Beds ⋅ 4 Baths
Welcome to 331 Devon Drive in Family friendly Coventry Farms. With 4 bedrooms and 3.5 bathrooms, this recently updated and meticulously maintained Colonial home offers enough space for the whole family and a harmonious blend of convenience and elegant living. The well-designed first floor - featuring tall ceilings, new dimmable recessed lighting and a wood burning fireplace - is anchored by the open-concept kitchen and living room spaces, which flow naturally to the exterior deck. The upgraded gourmet kitchen is a chef's dream, featuring upgraded countertops, stainless steel appliances, and a spacious island that invites culinary creativity. The kitchen flows effortlessly into the family room, where a cozy fireplace serves as the focal point, perfect for gathering with loved ones. The back of the house flows easily through sliding glass doors to the large back deck overlooking a large community open space with trees and a rolling field. A formal dining room off the kitchen and a large office space complete the first floor. Moving upstairs, there is brand new carpet throughout all four bedrooms. The master suite is a true retreat, complete with a walk-in closet and an en-suite bathroom. The attached garage accommodates two vehicles, while the paved driveway provides additional parking for guests. An electric vehicle charging station is great for those with an EV. The finished walkout basement with a full bathroom is a large open space offering possibilities for a second living room, home gym, entertainment area, etc. A Sunrun Solar system has significantly reduced the home's electric bill. Recent upgrades include: GE Profile SS kitchen appliances, deep farm-style sink, Trane heating / air air system, recessed lighting, fans, second floor carpet, interior and exterior paint throughout and more. Coventry Farms is just a couple minutes from downtown Chestertown. Founded in 1706, Chestertown sits on the banks of the Chester River and is home to Washington College. Enjoy the historic architecture, local shopping, restaurants, art galleries, and waterfront parks. Home to many festivals, an award-winning weekly Farmer's Market, Chestertown has a laid-back lifestyle with an endless number of social or volunteer activities. Less than 90 minutes to Washington D.C. or Philadelphia. Enjoy country living on the Eastern Shore. More photos and information to come!

331 Devon Dr, Chestertown

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

$1,295,000
4 Beds ⋅ 4 Baths
Step into your own private world, just 2.75 miles from Historic Downtown Chestertown. Tucked away at the rear of a mostly wooded 19+/- acre parcel, this exceptionally well-maintained property offers a rare combination of privacy, space, versatility, and convenience. At the heart of the property is a beautifully maintained brick residence overlooking a picturesque private pond, creating a peaceful setting that feels worlds away while remaining just minutes from town. The thoughtfully designed home is move-in ready and offers a comfortable, functional layout with quality finishes and inviting living spaces throughout. The first floor features a welcoming entry, upgraded gourmet kitchen with adjoining dining area, a spacious primary suite, and comfortable living areas that open to an expansive deck overlooking the pond. Whether enjoying a quiet morning or entertaining family and friends, the views and setting provide a stunning backdrop. Upstairs, you'll find three additional generously sized bedrooms and two full baths, providing plenty of room for family and guests. The finished walkout lower level adds another dimension to the home and offers tremendous flexibility as a game room, recreation space, home theater, gym, or private retreat, with direct access to the grounds and pond beyond. Adding even more value are two substantial, well-constructed outbuildings, each offering an incredible range of possibilities. Whether envisioned as a home office, woodworking or mechanical shop, hobby space, equipment storage, studio, or a combination of uses, these buildings make the property especially well-suited for someone seeking room to live, work, create, and store, all in one location. Surrounded by mature woods, expansive lawn, and the tranquil pond, the property offers a wonderful sense of seclusion without sacrificing proximity to the shops, restaurants, waterfront, and charm of Historic Chestertown. Properties offering this combination of acreage, privacy, substantial improvements, and proximity to town rarely become available. This is truly a one-of-a-kind Eastern Shore property that must be experienced in person to fully appreciate all it has to offer.

8276 Broad Neck Rd, Chestertown

Listing courtesy of Select Land & Homes, LLC. Contact:

$315,000
3 Beds ⋅ 1 Baths
Here is 24775 Langford Road, a well-maintained 3-bedroom, 1-bath home situated on 1.27 acres in a peaceful country setting just minutes from downtown Chestertown. The property features a spacious two to three-car detached garage/workshop, offering plenty of room for vehicles, storage, hobbies, or projects. A large Trex deck provides additional outdoor living and entertaining space. The home underwent extensive renovations in 2018, including the roof, windows, siding, gutters, storm doors, HVAC system, the Well was done in 2021, and partial crawl space encapsulation. Interior improvements included refinishing of the original hardwood floors and a remodeled kitchen featuring all-wood cherry cabinetry and stainless-steel appliances. With numerous major improvements already completed, garage and workshop space, and over an acre of property, this home offers comfortable country living with convenient access to Chestertown, Rock Hall and surrounding areas.

24775 Langford Rd, Chestertown

Listing courtesy of RE/MAX Chesapeake. Contact:

$38,200,000
4 Beds ⋅ 2 Baths
Tulip Forest, a farm defined by scale, stewardship, and long-term value. Recognized as a premier sporting estate, this legacy holding property is the kind of asset that seldom comes to market on Maryland's Upper Eastern Shore. 1,054 +/- acres held intact under one ownership: 680 tillable acres, 272 acres of timber, 5 ponds, 3 impoundments, 26.75-acre wetlands restoration project, 45 acres CRP, a 3.75 mile interior gravel road system, 3 residences, and multiple farm outbuildings. At its center stands Caulk's Field House, circa 1743, a remarkably preserved residence on the ground recognized among Maryland's best-preserved War of 1812 sites. Nearly four miles of farm roads reach every corner of the property, and the ponds, impoundments, and mature timber hold waterfowl, whitetail and countless other game species. Also included beyond the farming operation: 7 acres zoned commercial, additional parcels zoned Village, and four sewer allocations secured along Georgetown Road. A working farm today, with room to grow, suited to farmers, sportsmen, conservation buyers, and investors.

8184 Rock Hall Rd, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

$335,000
3 Beds ⋅ 2 Baths
Lovingly restored rancher located on a a quiet street in sought after Chester Harbor. Generous sized corner lot, with beautiful landscaping and asphalt drive. Home had a complete renovation in 2020 inside and out and practically everything is new since then. Enter into an inviting and updated open floor plan that combines living and dining area, perfect for entertaining and large gatherings. Updated laminate plank floors throughout entire home with SS appliances and kitchen breakfast bar, plus separate dining area. Stackable laundry and half bath conveniently located just off dining area. The sun room, over looking the back garden makes a great sitting room, office, or flex space. Down the hall you'll find 3 good sized bedrooms, all with double closets, a good sized bathroom with modern vanity, laminate floors and tub shower. Outside is a gardener's oasis with mature specimen plantings, just waiting for you to make it your own!

217 Edmore Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$299,900
3 Beds ⋅ 1 Baths
MOVE IN READY!! Charming 3 bedroom ranch home in the desirable water oriented community of Chester Harbor. This recently updated home offers a wonderful blend of modern comfort, convenience and peaceful surroundings. The home features a carefully updated galley kitchen with beautiful custom countertops, soft close cabinets and stainless steel appliances. The home also offers a reverse-osmosis water system in the kitchen. Numerous updates have been completed recently, including new LVP flooring, carpet, light fixtures, a new roof in 2020, new windows in 2021, new exterior and entry doors in 2023. Perfect location for dog lovers with a recently added split-rail fence enclosing the backyard. Walking distance to Round Top Park and minutes from Downtown Chestertown where you can enjoy local restaurants, shops, waterfront attractions, the dog park and the popular farmers market every Saturday! Don't miss this opportunity to make this wonderful property your new home!

124 Wilton Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$480,000
3 Beds ⋅ 3 Baths
PICTURES COMING SOON Welcome home to this beautiful 3-bedroom, 2.5-bath residence in the charming town of Chestertown, MD. Designed for both comfortable living and effortless entertaining, this home offers spacious interiors filled with abundant natural light. The main level features a bright kitchen with Breakfast Bar that flows seamlessly into a sunny Florida room, creating the perfect space to enjoy your morning coffee or unwind while overlooking the backyard. You'll also find a formal dining room for hosting special occasions, a welcoming living room, and a cozy family room that provides plenty of space for everyday living. Downstairs, the finished basement offers versatile additional living space ideal for a recreation room, home theater, fitness area, playroom, or home office. There is enough space to do all of it. The unfinished area has full laundry and ample storage. Upstairs, the expansive owner's suite serves as a private retreat, complete with a generous walk-in closet and an ensuite bathroom featuring a soaking tub. Two additional bedrooms each offer large closets and ample space for family, guests, or a home office. A full bathroom conveniently located off the second-floor sitting area completes the upper level. Step outside to your own private backyard oasis. The landscaped yard features a refreshing in-ground swimming pool with a new tile finish and a new filtration system, making it ready for years of enjoyment. A new deck with a privacy wall extends from the home, providing the perfect setting for outdoor dining, entertaining, or relaxing poolside. Additional highlights include a large storage shed and a newly installed rock bed surrounding the pool deck that enhances both beauty and low-maintenance landscaping. For added peace of mind, the home also features a roof that is only two years old. Combining spacious living areas, thoughtful updates, exceptional outdoor amenities, and a desirable location in historic Chestertown, this home truly has something for everyone. Don't miss the opportunity to make this exceptional property your next home!

129 Trafford Dr, Chestertown

Listing courtesy of Elevated Real Estate Solutions. Contact:

$269,000
3 Beds ⋅ 2 Baths
Welcome to Chesapeake Landing! Come see this amazing home offering vaulted ceilings, huge master bath, open concept, plenty of closet space, laminate flooring, and a private secluded fenced lot. Located in a water oriented neighborhood with community boat ramp and pier and nearby restaurants and marina. Move here and enjoy all the Eastern Shore has to offer!

10540 Tonopah Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$825,000
5 Beds ⋅ 4 Baths
Custom-built home in Country Club Estates with beautiful architectural details. Spacious open living space with hardwood floors and wooden beams, glowing with ample natural light! Enjoy time on the large screened porch, finished with Ipe hardwood, overlooking the peaceful creek, woods and park like setting. Five bedrooms and 4 full bathrooms, nicely designed with privacy in mind. There's an entry-level bedroom and full bathroom. The partially finished basement offers a large bedroom or bonus room, a full bathroom, and an oversized workshop space. Upstairs you'll find two bedrooms that share a full bathroom, as well as the primary bedroom, which is nicely situated with a view of the creek/pond. Enjoy peaceful views of the creek from the slate patio, and launch a kayak to explore the water from your backyard. This property leaves little to be desired! Two-car garage, peaceful water view, cozy fireplace, large living space, nicely landscaped, and a hot tub! Under 2 miles from downtown Chestertown and a short stroll to the Chester River Yacht & Country Club.

7680 Country Club Ln, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

$1,375,000
4 Beds ⋅ 5 Baths
Welcome to 22470 Fairgale Farm Ln, a spacious home and property perched over Fairlee Creek, with an assigned boat slip.  3.55 acres, partly wooded, exceptionally landscaped, and perfectly framed water views. Walk down to the water to enjoy the views or launch a kayak.  The deep-water boat slip, outfitted with a boat lift, is just a short distance away. The home features 4 bedrooms and 5 full bathrooms, plus a large loft that could be used as an additional bedroom. The large eat-in kitchen has expansive windows that perfectly frame the water view. A great spot for entertaining! Doors in the kitchen lead to the waterfront deck, spanning the front of the home.  A new roof was installed in June, 2026. In both sitting rooms, you’ll find fireplaces that have been conveniently updated to propane. The first-floor primary bedroom opens up to the waterfront deck and offers a fantastic water view, as well as a large bathroom that was recently updated.  Upstairs you’ll find two waterfront bedrooms, one with an updated attached bath. There's a second full bathroom and ample closet space in the hallway.  Downstairs, there are two additional full bathrooms and a large bedroom. Above the kitchen sits the light-filled loft, a great office, studio, or extra bedroom.  The exterior has a generous front porch, outdoor shower, circular drive, 2-car garage, fenced dog run, and additional garage space connected to the basement.  This light-filled waterfront property is located 15 minutes away from the waterfront community of Rock Hall and historic Chestertown.

22470 Fairgale Farm Ln, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

$898,000
3 Beds ⋅ 4 Baths
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.

226 S Water St, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

$829,000
3 Beds ⋅ 4 Baths
Built Before America: A Pre-Revolutionary Home in the Heart of Chestertown's Historic District The Bedingfield Hands House, circa 1750, is more than a home—it's a living piece of Chestertown history. Nestled in the heart of the Historic District, this pre-Revolutionary residence has stood witness to generations of change while retaining the charm, craftsmanship, and character that make historic homes so special. History is woven into every corner of the property—from the prominence of past owners down to the foundation, which contains the mast of a ship. The only home downtown with such a generous private front courtyard framed by mature landscaping, vibrant seasonal gardens, brick herringbone paths, and mature trees that create a peaceful retreat just steps from town. Whether enjoying a quiet morning coffee, entertaining guests, or simply admiring the blooms, the outdoor spaces are truly a stand-out feature. Approaching the home, guests are welcomed by a wide red front door, a traditional symbol of hospitality in early America, inviting visitors inside just as it has for centuries. Inside, approximately 2,472 square feet of thoughtfully preserved living space blends historic character with modern comfort. Original wide-plank hardwood floors, period moldings and built-in cabinetry, reflect the home's 18th-century origins, while updated kitchens, baths, and central air/heat provide the conveniences expected today. To the right of the grand foyer, a cozy study lined with built-in bookshelves provides the perfect home office or library and could easily be converted into a first-floor bedroom for those seeking single-level living flexibility. A first floor full bathroom with walk in shower is located conveniently around the corner straight through the foyer. To the left of the foyer and at the forefront of the home, the stunningly preserved parlor, featuring 12x12 wavy glass windows, original panel walls and stunning gas fireplace with pine panel surround, offers an elegant setting for entertaining guests or enjoying quiet evenings at home. Just beyond, the large dining room serves as a memorable gathering space, complete with another fireplace, built-in cabinetry, and a charming pop-out window seat overlooking the side gardens. Just beyond that is a chef's kitchen featuring updated appliances, abundant storage cabinetry, generous island workspace, and a soaring tapered tray ceiling that creates an airy and inviting atmosphere. The kitchen breakfast nook is highlighted by panoramic bay window wall. Off the breakfast nook is a convenient half bath and steps to the side courtyard with pergola and a screened porch. The garage—another rarity in the Historic District—provides valuable storage and convenience. Upstairs, the spacious primary suite blends historic character with thoughtful updates, featuring a practical double closet and an en-suite bath highlighted by distinctive MacKenzie-Childs tile floors and decorative vanity hardware. Two additional generously sized bedrooms and a full bathroom provide comfortable accommodations for guests. Beyond its appeal as a private residence, it has proven itself as one of Chestertown's most successful Airbnb properties, generating approximately $32,000 in bookings last year. Whether you're seeking a full-time residence, weekend retreat, or income-producing investment, this property offers exceptional flexibility. Furniture is negotiable for a truly turnkey opportunity. Step outside and enjoy everything that makes Chestertown so beloved. Stroll to art galleries, locally owned shops, restaurants, the farmers market, and waterfront parks along the Chester River. Enjoy annual traditions such as the Tea Party Festival, Downrigging Weekend, and Dickens of a Christmas, all just moments from your front door. Become the steward of a treasured landmark while enjoying the comfort, beauty, and lifestyle that have made it one of Chestertown's most admired homes for generations.

106 Queen St S, Chestertown

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

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