Great Oak Estates Homes with Traditional Style

Great Oak Estates Homes with Traditional Style

Welcome to Great Oak Estates, a picturesque subdivision nestled in the heart of Chestertown, Maryland. This charming community, located in Kent County, offers a perfect blend of serene countryside living and modern amenities, making it an ideal choice for families, retirees, and anyone seeking a peaceful retreat.

At Great Oak Estates, you’ll find a collection of beautifully designed traditional-style homes that exude timeless elegance and warmth. These residences feature classic architectural elements, such as gabled roofs, inviting front porches, and spacious layouts that cater to both comfort and functionality. With a variety of floor plans available, each home is thoughtfully crafted to meet the diverse needs of today’s homeowners.

The enchanting surroundings of Great Oak Estates further enhance its appeal. Lush green spaces, mature oak trees, and well-maintained walking paths create a tranquil environment where residents can enjoy nature’s beauty. The community is conveniently located just a short drive from Chestertown’s vibrant downtown, where you can explore local shops, dine at delightful eateries, and partake in cultural events throughout the year.

Families will appreciate the highly-rated schools in the area, ensuring that children receive a quality education. Additionally, outdoor enthusiasts will find ample opportunities for recreation, with nearby parks, hiking trails, and the scenic Chester River just waiting to be explored.

Discover the charm and community spirit of Great Oak Estates, where traditional-style homes and a welcoming neighborhood create the perfect backdrop for your next chapter. Come experience the lifestyle you’ve always dreamed of in this delightful corner of Maryland!

Newest Great Oak Estates Homes with Traditional Style

$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:

Start Your Search