Chestertown Homes with Inside Access Garage Description

Chestertown Homes with Inside Access Garage Description

Welcome to Chestertown, Maryland – a charming riverside town that beautifully blends history with modern living. Nestled along the banks of the Chester River, Chestertown is renowned for its picturesque landscapes, vibrant arts scene, and rich colonial heritage. With its quaint streets lined with historic buildings, local boutiques, and inviting cafes, this town offers a unique lifestyle that's both relaxed and engaging.

As you explore Chestertown, you’ll discover a community that values its history while embracing the future. The annual Chestertown Tea Party Festival, art galleries showcasing local talent, and a variety of outdoor activities along the water make this town a hub of culture and recreation. Whether you're strolling through the historic district or enjoying a sunset at the waterfront, Chestertown's charm is undeniable.

When it comes to finding your dream home in this idyllic setting, you’ll be delighted by the selection of properties available, particularly those featuring inside access garages. These homes not only provide convenience but also enhance your living experience. Imagine arriving home on a rainy day and seamlessly entering your home without stepping outside. Inside access garages offer the perfect blend of comfort and practicality, making daily life a little easier.

With Chestertown's welcoming community and beautiful surroundings, combined with homes that cater to modern needs, you'll find the perfect place to call home. Come experience the magic of Chestertown, where history meets contemporary living, and make it your own!

Newest Chestertown Homes with Inside Access Garage Description

$649,000
4 Beds ⋅ 3 Baths
Welcome to this beautifully crafted home in the water-oriented community of Great Oak Estates, just outside of Chestertown on Maryland’s Eastern Shore. Nestled in a peaceful setting that backs to woods alive with songbirds and butterflies, this high-quality residence offers an easy-flow floor plan designed for both lively gatherings and quiet private moments. A soaring two-story foyer greets guests and opens to the living room and family room, the latter featuring built-in cherry cabinets and a cozy propane fireplace. The formal dining room connects seamlessly to the kitchen and an additional casual dining space, making entertaining effortless. The kitchen showcases handmade cherry cabinetry and a brand-new refrigerator. Hardwood floors run throughout the main living areas, while brand-new carpeting softens every bedroom. On the main level, the primary suite includes its own bathroom, a walk-in closet, and plantation shutters. A second main-floor bedroom (ideal as a guest room or home office) shares convenient access to the hall bath. Completing the first floor are a large walk-in pantry and a laundry room outfitted with a brand-new washer and dryer. Upstairs you’ll find two additional spacious bedrooms, each with its own walk-in closet, plus a full bathroom. An oversized walk-in attic provides abundant storage or the perfect opportunity to create a bonus room or extra living space. Dual zone HVAC provides comfort from a newer lower level unit and an upper unit replaced in 2026. Complete roof replacement was completed in 2026 as well. A voluntary HOA opens the door to the amenities of Safe Harbor Great Oak Landing Marina—private beach area, pool, 9-hole golf course, and more. Simply walk or hop in a golf cart to reach the marina and enjoy all the water-oriented lifestyle this community has to offer. You’re also minutes from Rock Hall, with its additional marinas, charter boats, shopping, and restaurants. Less than 10 minutes away lies Chestertown and Washington College, along with more shopping, dining options, a hospital, and a wonderful Saturday morning Farmers Market, and much more. Whether you’re seeking a full-time residence or a relaxing Eastern Shore getaway, this home delivers quality craftsmanship, flexible living spaces, and convenient access to the best of Great Oak Estates and the surrounding area.

22400 Great Oak Landing Rd., Chestertown

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

$524,900
3 Beds ⋅ 3 Baths
Welcome home to this beautifully maintained and thoughtfully updated residence nestled at the end of a peaceful cul-de-sac! Originally built in 2002 and extensively renovated in 2020, this home offers the perfect combination of timeless design, modern updates, and comfortable living. Hickory flooring flows throughout the main living areas and bedrooms, while LVP flooring provides durability and easy maintenance in all bathrooms and the laundry room. The heart of the home is the impressive gourmet kitchen, featuring quartz countertops, a granite-topped island, 5-burner propane range, double wall ovens, built-in microwave, pot filler, farmhouse sink, beautiful backsplash, and abundant cabinetry for exceptional storage. Open to the spacious great room, the kitchen creates an inviting gathering space highlighted by a propane fireplace with a beautiful mantel. The living room features Anderson sliding glass doors that open to the deck, creating an easy connection between indoor and outdoor living. The spacious primary suite is a true retreat, featuring Anderson sliding glass doors leading directly to the deck, a walk-in closet, and an updated primary bath with double vanity and a large tiled shower enclosed by glass doors. The third bedroom offers clever versatility with a Murphy bed that maximizes the space while providing a comfortable guest room when needed. Step outside to enjoy the deck and partially fenced backyard, complete with a storage shed and peaceful views of the open common area behind the property. An attached two-car garage and paved driveway add convenience and functionality. Meticulously maintained and beautifully updated, this home offers a wonderful opportunity to enjoy turnkey living in a highly desirable Chestertown location, close to the town's shops, restaurants, waterfront, and amenities. Don't miss the opportunity to make this exceptional home your own!

1003 Twin Ct, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact: 4434803453
$424,900
5 Beds ⋅ 3 Baths
Located in a beautiful waterfront community, this refreshed 5-bedroom, 2.5-bath home offers approximately 1,936 square feet of comfortable living space on approximately 0.38 acres. The property combines updated interiors, flexible living spaces, and the relaxed lifestyle of Maryland’s Eastern Shore. The home offers five generously sized bedrooms, providing comfortable space for family, guests, or work-from-home needs. The versatile fifth bedroom can function as a home office, guest room, flex space, or secondary suite, depending on your needs. The upgraded kitchen features bright white cabinetry, updated countertops and backsplash, stainless-steel Whirlpool appliances, and a KitchenAid dishwasher. The French-door refrigeratorincludes a front water and ice dispenser for added convenience. Attractive ceiling fans throughout the home add both comfort and style. The main living area is anchored by a stylish electric fireplace with custom floating shelving, creating a warm focal point for the home. With five bedrooms, the layout offers excellent flexibility, and the fifth bedroom can also serve as a home office, guest room, or additional flex space. The partially finished one-car garage offers added versatility beyond traditional vehicle parking and storage. It can also serve as a game room, entertainment area, recreation space, hobby room, home gym, or additional flex space, giving buyers even more options for how they use the home. Step outside to an expanded rear deck, hot tub, and fire-pit/seating area, ideal for relaxing or entertaining. Boating enthusiasts will appreciate the nearby seasonal marina with restaurants and a dive bar 3 blocks away and a public boat ramp approximately one mile away, providing convenient access to the area’s waterways. Additional updates include an approximately two-year-old water heater and a private well with an upgraded water-treatment/softening system, professionally serviced in 2025 with a new Clack neutralizer head installed. Whether used as a primary residence, vacation home, weekend retreat, or a home designed for entertaining, 8630 Elm Road offers space, versatility, thoughtful updates, and the Eastern Shore lifestyle in one inviting package.

8630 Elm Rd, Chestertown

Listing courtesy of Save 6, Incorporated. Contact:

$824,900
5 Beds ⋅ 4 Baths
Welcome to a breathtaking country estate where modern elegance, architectural grandeur, and total sanctuary converge across 2.23 serene acres. Spanning over 4,000 square feet of meticulously refined living space, this extraordinary five-bedroom residence has been thoughtfully crafted to offer both lavish entertaining possibilities and effortless multi-generational comfort. Upon arrival, the welcoming foyer makes a memorable first impression, framed by detailed custom millwork and flanked by a private executive office and a sophisticated study or formal dining space. Moving inward, the magnificent two-story great room commands attention with its soaring ceilings and a cozy gas fireplace crowned by a classic raised brick hearth. At the heart of the main level lies a gourmet kitchen designed for grand gatherings, showcasing fresh luxury vinyl flooring, select new appliances, and a stunning quartz-topped center island with a prep sink that easily reconfigures for multi-purpose hosting. Sunbeams flood the adjoining sunroom, creating a seamless transition to the outdoors while mirroring the warmth of the home’s main-floor primary suite. This private retreat features a spacious walk-in closet and a newly remodeled, spa-inspired bath complete with new quartz double vanities, sleek updated fixtures, a large walk-in shower, and an exquisite standalone soaking tub. Offering unmatched independence and comfort, a fully self-contained ground-level suite on the lowest level serves as the ultimate in-law or guest quarters. Complete with its own private ground-level entrance, open-concept kitchen and living area, dedicated laundry, and an accessible bath with a walk-in shower, this wing ensures total convenience without sacrificing style. A new addition to the lower level unlocks movie-theater magic with a fully furnished screening room ready for immediate enjoyment. Upstairs, four generously proportioned bedrooms accompany a beautifully refreshed hall bath. The exterior grounds are nothing short of a resort-style paradise. Step out onto the back porch to take in sweeping views of the lush landscape and expansive partially fenced yard. The sparkling in-ground pool serves as the crown jewel of the outdoor space, newly upgraded with all-new mechanicals including a dedicated heater. The owners have ordered a new, heavy duty liner, perfect for pets and kids, to be installed with the closing of the pool around the end of September. Surrounding the water, extensive custom hardscaping leads to a fireside gathering area, while an oversized gazebo with an outdoor fan offers a shady retreat on warm afternoons. With a brand-new roof installed in 2026, a newly resurfaced driveway, and space remaining for future additions, this estate represents a rare opportunity to experience sophisticated countryside living at its finest and, less than 5 minutes from Chestertown's restaurants, shopping, and Farmer's Market. Updates to the home are available in Documents

8999 Orchard Dr, Chestertown

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

$885,000
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:

$550,000
5 Beds ⋅ 4 Baths
103 Sutton is perfectly situated just a stone’s throw from the vibrant heart of Downtown Chestertown. This exquisite 4+ bedroom residence is designed to cater to the diverse needs of today’s Buyers, offering a harmonious blend of comfort, style, and functionality. This home is ideal for those upsizing or seeking multi-generational living. * Originally built as the community model home – and meticulously maintained since – it has ALL the extras: generous breakfast nook bump out, gas fireplace, gleaming hardwood floors, upgraded carpet, oversized windows, granite countertops, stainless appliances, dedicated home office, and a finished basement with a full bath and expansive wet bar. * As you step inside, you’ll be greeted by a two-story foyer flooded with light, dining room and den or family room. The gourmet kitchen that is a chef’s paradise, featuring high-end appliances, custom hardwood cabinetry, and a small island for an ideal triangle of space for meal prep. The open concept layout flows effortlessly into the breakfast nook and living room, providing the perfect setting for family gatherings and celebrations with friends. Click on the propane fireplace for a cozy night watching the sunset or snow flurries outside the tall windows. * The spacious primary suite is an escape through a double door entry – featuring a lighted tray ceiling, a large walk-in closet, en suite bath with soaking tub, glass shower, and a separate water closet. Three additional bedrooms all have custom trim work, generous closets, and large windows. * The finished basement is a standout feature, complete with a stylish wet bar with stone walls that transforms it into the ultimate entertainment zone, perfect for hosting game nights or movie marathons. The backyard feels private with mature trees and a gentle slope, ideal for play space. * The proximity to local parks, playgrounds, restaurants, and shopping ensures that all your family’s needs are met within minutes. Additionally, the Coventry Farms neighborhood fosters a sense of community all while being a convenient distance from Middletown, DE, Philadelphia, PA, Washington DC, Baltimore, MD, and points beyond. * This home is not just a place to live; it’s a lifestyle waiting to be embraced. Don’t miss the opportunity to make this stunning property your own. Schedule your private tour today and experience firsthand what this exceptional home has to offer.

103 Sutton Way, Chestertown

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344
$545,000
3 Beds ⋅ 3 Baths
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.

204 Double Creek Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$1,459,000
3 Beds ⋅ 3 Baths
**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 area—perfect 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 kayaks, canoes and paddle boards, beautifully landscaped paths along the water's edge and much more! Nestled in the sought-after Chester River Landing community, 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.

Little Harbor Way Unit #1, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

$499,999
2 Beds ⋅ 3 Baths
MOTIVATED SELLER - BRING OFFERS. Welcome to 103 Landing Lane: a meticulously maintained 2-bedroom townhome in the desirable waterfront community of Chester River Landing. Just a short walk or bike ride into downtown Chestertown, this elegant, turn-key home offers maintenance-free living, great amenities, and easy water access to the Chester River. The welcoming foyer seamlessly flows into the rear den or office which could be converted into a 3rd bedroom. Off the den is the first-floor bedroom and full bath. Enjoy the summer breeze from the private back screened-in porch; recently upgraded with high-tech flex screens and a ceiling waterproofing; keeping the porch dry. The real action is found upstairs. The living room – anchored by an electric fireplace with stone surround – is complemented by the oversized second story deck; perfect for grilling or watching picturesque Chester River sunsets. The modern kitchen features new stainless-steel appliances, abundant cabinet space, granite countertops and a large island with breakfast bar. Plenty of space for formal or casual dining. The second floor is finished by an oversized primary bedroom with ensuite bath and large walk-in closet. Should one desire an elevator; there are two locations where one could be built into the existing design. Leave your worries aside as the condo association takes care of all exterior maintenance, yardwork, and repairs. Boaters will enjoy the well-maintained community dock with slips available for purchase or lease (with board approval), or just drop in a kayak or paddle board; great on warm summer evenings. Other community amenities include the pool, walking paths, garden, picnic and grilling areas, and a fire pit. 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 walkways and parks. Chestertown is home to many festivals and an award-winning Farmer's Market every Saturday. New YMCA with full gym, racquet sports, lap pool, sauna, etc. Don’t miss your opportunity to enjoy worry-free living along the Chester River.

103 Landing Ln, Chestertown

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

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