Chestertown Homes with Built In Garage Description

Chestertown Homes with Built In Garage Description

Welcome to Chestertown, Maryland – a charming riverside town steeped in history and brimming with character. Nestled in Kent County along the beautiful Chester River, Chestertown is a delightful blend of scenic landscapes, rich heritage, and vibrant community life. Known for its picturesque streets lined with historic homes and flourishing local businesses, this quaint town offers a unique blend of small-town charm and modern conveniences.

One of the standout features of Chestertown is its commitment to preserving its historical roots while embracing contemporary living. The town is home to Washington College, which adds a youthful energy to the community and hosts various cultural events throughout the year. With a strong sense of community, residents enjoy a plethora of activities, from farmers' markets to art festivals and outdoor concerts.

For those looking to make Chestertown their home, the real estate market offers a variety of options, including beautiful homes with built-in garages. These properties not only provide convenience and ample storage but also enhance the overall appeal of the home. Imagine having a secure space for your vehicle, along with additional room for recreational gear or seasonal decorations.

Whether you're a first-time homebuyer or seeking a serene place to retire, Chestertown's homes with built-in garages provide the perfect blend of functionality and style. Embrace the charm of this historic town while enjoying the comforts of modern living. Come explore Chestertown – where history meets home!

Newest Chestertown Homes with Built In 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:

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