Henderson Real Estate

Henderson Real Estate

Welcome to Henderson, Maryland – a hidden gem nestled in the heart of Caroline County. This quaint town is a perfect blend of rural charm and community spirit, making it an ideal place to call home. With a population that embodies warmth and friendliness, Henderson offers a welcoming atmosphere for families, retirees, and everyone in between.

Surrounded by picturesque landscapes, Henderson is characterized by its lush greenery, serene waterways, and beautiful farmland. The town’s proximity to the Choptank River provides ample opportunities for outdoor enthusiasts to indulge in fishing, kayaking, and leisurely strolls along the scenic banks. Nature lovers will appreciate the nearby parks and nature trails, perfect for hiking and enjoying the great outdoors.

Henderson boasts a rich history, and its small-town feel is complemented by a strong sense of community. Residents enjoy local events, farmers' markets, and seasonal festivals that bring everyone together. The town’s close-knit community ensures that newcomers feel right at home, fostering friendships that last a lifetime.

In terms of amenities, Henderson is conveniently located near larger towns, offering easy access to shopping, dining, and entertainment options. The local schools are known for their dedication to education, making it a fantastic place for families seeking quality schooling for their children.

Whether you’re looking to settle down in a peaceful environment or seeking a weekend retreat, Henderson, MD, is a charming destination that captures the essence of small-town living. Experience the tranquility and community spirit of Henderson—where your dream home awaits!

Newest Listings in Henderson

$620,000
4 Beds ⋅ 3 Baths
Privacy, space, and endless possibilities — this 5.06-acre retreat offers the lifestyle you've been looking for. Tucked into a partially wooded setting at the end of a quiet drive, 16881 Heritage Hills Ln provides the perfect blend of seclusion, functionality, and room to grow. Best of all, there's no HOA, giving you the freedom to truly enjoy your property. Built in 2005, the home offers 2,704 square feet of thoughtfully designed living space, plus an additional 300 square feet under heat, air, and electric that's ready to be finished or used as storage, a home gym, hobby room, or flex space—bringing the total conditioned space to approximately 3,000 square feet. Inside, you'll find four spacious bedrooms with the potential for a fifth bedroom or nursery connected to the primary suite, a dedicated office, two separate living areas, and a cozy family room just off the kitchen. The beautifully updated kitchen features granite countertops, stainless steel appliances (installed in 2024), and an ideal layout for entertaining. The primary suite is a true retreat with a renovated bathroom, walk-in closet, and adjoining flex space that can easily adapt to your needs. Nine-foot ceilings throughout the first floor create an open, airy feel. Step outside and you'll quickly see what makes this property special. Relax on the 16x13 screened porch with its brand-new roof, gather on the adjoining decks, or enjoy evenings around the fire pit on the paved patio. The property is already wired and ready for a hot tub, making it easy to create your own backyard oasis. A spacious outbuilding offers endless opportunities for storage, a workshop, or recreational equipment, while the attached two-car garage features a MyQ smart garage door opener with an integrated camera. With over five acres, the land offers incredible flexibility for those looking to embrace country living. Whether you envision horses, livestock, gardens, recreational trails, or simply enjoying the privacy, the possibilities are endless. Hunters will appreciate the secluded back field complete with an established food plot and tower stand already in place for the season. This home has also been meticulously maintained, with a new roof featuring a transferable warranty, new water heater (2026), new water softener (2026), and the septic system professionally serviced in 2026. Properties offering this much privacy, usable acreage, flexible living space, and modern updates are a rare find. Welcome home!

16881 Heritage Hills Ln, Henderson

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$249,999
14.71± acre perc-approved parcel on Trunk Line Rd in Henderson, MD! This beautiful wooded lot offers a conventional perc approved for 4+ bedrooms and provides an excellent opportunity to build your dream home, private retreat, or future homestead. Property features approximately 466 feet of road frontage along Trunk Line Road and includes a designated sewage reserve area shown on recorded plat. Enjoy the peaceful rural setting with plenty of privacy and room to spread out while still being conveniently located to nearby towns, shopping, dining, and major routes. No builder tie-in. Buyer to perform all due diligence regarding permits, utilities, land use, and building plans.

Trunk Rd, Henderson

Listing courtesy of The Parker Group. Contact: 3022176692
$575,000
The Melville Rd Farm is located on the east side of Melville Road and is bordered to the north by Trunk Line Road. The property includes approximately 51± acres of tillable ground along with 11± acres of wooded areas primarily situated around drainage ditches, providing natural transitions and wildlife cover. Two transmission lines run through the center of the farm, offering access corridors and open space. The soils are predominantly Ingleside loamy sand, Hambrook sandy loam, and Fallsington sandy loam, supporting a range of agricultural uses. The property is not encumbered by any conservation easements, allowing for flexibility in land use in the future.

17619 Melville Rd, Henderson

Listing courtesy of The Land Group. Contact: (410) 934-3478
$134,900
Secluded 5-Acre Perc-Approved Building Lot Nestled on a quiet country back road, this beautiful 5-acre parcel offers peace, privacy, and great potential. The front section—where the perc test has been approved—is lightly overgrown with small saplings, making for easy clearing and minimal cost to install a driveway and run utilities to your future home site. The rear portion of the property features a mix of mature hardwoods, offering a serene natural backdrop and added privacy. Abundant deer signs make this spot perfect for hunters or nature lovers looking to enjoy wildlife right in their own backyard. Whether you're dreaming of a rural retreat, homestead, or hunting getaway, this property is ready for your vision.

Trunk Line Rd, Henderson

Listing courtesy of Taylor Properties. Contact:

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