Fairlee Real Estate

Welcome to Fairlee, a picturesque subdivision nestled in the charming town of Chestertown, Maryland. This hidden gem in Kent County offers a serene lifestyle surrounded by the natural beauty of the Eastern Shore. Fairlee is known for its welcoming community atmosphere and is perfect for families, retirees, and anyone looking to enjoy the tranquility of suburban living while still being close to the vibrant culture and history of Chestertown.

The homes in Fairlee boast a variety of architectural styles, each contributing to the neighborhood’s unique character. Residents enjoy spacious lots, beautifully landscaped gardens, and modern amenities that make everyday living a breeze. The subdivision’s well-maintained streets and sidewalks invite leisurely strolls, and the friendly neighbors foster a sense of belonging that makes Fairlee feel like home.

Nature lovers will appreciate Fairlee's proximity to the Chester River, where opportunities for fishing, kayaking, and enjoying scenic views abound. The nearby parks provide ample space for picnics, hiking, and outdoor activities for all ages. Additionally, Fairlee is conveniently located just a short drive from Chestertown's historic downtown, where you can explore delightful shops, local restaurants, and cultural events that celebrate the area's rich heritage.

Whether you’re searching for your dream home or looking to invest in a community that feels like family, Fairlee offers a perfect blend of tranquility, community spirit, and access to the best of Maryland’s Eastern Shore. Come discover the charm of Fairlee, where your ideal lifestyle awaits!

Newest Listings in Fairlee

$344,000

3 Beds ⋅ 2 Baths

Looking for peaceful country living? The search is over! Nestled on 1.66 acres, this beautifully renovated 3-bedroom, 1.5-bath home offers the perfect blend of comfort, functionality, and privacy with NO HOA! In addition, there's a versatile bonus/flex room that is ideal for a home office, hobby area, or even a potential 4th bedroom to suit your needs - all on the convenience of one-level living. Step inside to discover a bright, inviting interior featuring brand-new luxury vinyl plank flooring and carpet, fresh paint throughout, and a thoughtfully updated kitchen complete with new butcher block countertops, brand-new stainless-steel appliances, and ample cabinet space. A new HVAC system, brand-new roof, and a ONE-YEAR HOME WARRANTY provide peace of mind, allowing you to move in and enjoy your new home from day one. Outside, the expansive 1.66-acre lot offers endless opportunities for gardening, entertaining, recreation, or simply enjoying the tranquility of nature. A storage shed provides additional space for tools, lawn equipment, or outdoor hobbies. Whether you're a first-time homebuyer, someone looking for convenient one-level living, or looking for a move-in-ready home with room to spread out, this property checks all the boxes! Conveniently located just minutes from historic downtown Chestertown, Rock Hall, nearby marinas, dining, shopping, and waterfront activities - with convenient access to major routes into Delaware and Pennsylvania - this property offers the ideal balance of peaceful rural living and easy travel. This is a rare combination of acreage, versatility, and affordability. In addition, this property has public water and sewer. Schedule your tour today and see why this home works just as well for everyday living as it does for your Eastern Shore escape!

9126 Fairlee Rd, Chestertown

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

$385,000

4 Beds ⋅ 3 Baths

Located in the small Eastern Shore town of Fairlee, this spacious Bi-level sits on 1.65 acres of cleared land, just a short 10-minute drive to both Chestertown and Rock Hall. The home offers 3 bedrooms and 2 bathrooms, with a finished lower level for additional living space. A large sunroom with cathedral ceilings and walls of windows is the heart of the home, filling the space with natural light. Enjoy cooking in the updated kitchen with stainless steel appliances and serving meals in the separate dining room. Outdoor living is a highlight with an enclosed back porch, decks on both the first and second floors, and plenty of open yard space. Additional features include two fireplaces, a dedicated laundry room, and a shed for storage. A detached 3-bay garage provides ample room for vehicles, hobbies, or workshop space. This property combines comfortable living with generous space inside and out, all in a convenient location close to towns and the water.

23043 Bay Shore Spur, Chestertown

Listing courtesy of Rock Hall Properties Real Estate. Contact:

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