Henderson Real Estate

Henderson Real Estate

Welcome to Henderson, Maryland—a charming gem nestled in Caroline County that offers a delightful blend of small-town charm and natural beauty. With a population of just over 200 residents, this quaint community provides a peaceful retreat from the hustle and bustle of larger cities while still offering convenient access to urban amenities.

Henderson’s picturesque landscape is characterized by rolling fields, lush greenery, and serene waterways, making it a haven for nature lovers and outdoor enthusiasts alike. The nearby Choptank River offers ample opportunities for fishing, kayaking, and leisurely strolls along its banks, while the surrounding countryside is perfect for hiking and exploring the great outdoors.

The heart of Henderson is its strong sense of community. Residents take pride in their town, often coming together for local events and gatherings that celebrate the area’s rich history and vibrant culture. The town's close-knit atmosphere fosters lasting friendships, making it an ideal place for families and individuals seeking a supportive environment.

For those who appreciate history, Henderson boasts several historical landmarks and sites that reflect its rich heritage. The town's proximity to larger cities like Easton and Cambridge allows residents to enjoy a variety of shopping, dining, and entertainment options without sacrificing the tranquility of rural living.

Whether you’re looking to settle down in a peaceful environment, enjoy the beauty of nature, or become part of a welcoming community, Henderson, MD, is the perfect place to call home. Come explore all that this delightful town has to offer—you might just find your dream home among its charming streets!

Newest Listings in Henderson

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

Discover the possibilities on this 14.71± acre wooded parcel on Trunk Line Rd in Henderson, MD, now offered at $224,900. Perc approved for a conventional septic system serving a 4+ bedroom dwelling, this property offers the opportunity to build a custom home while enjoying the privacy and space of a rural setting. With approximately 466 feet of road frontage along Trunk Line Road and a designated sewage reserve area shown on the recorded plat, the property provides flexibility for your future plans. The mature woods make this parcel well-suited for outdoor recreation, hiking, wildlife observation, and, subject to applicable laws and regulations, hunting. Whether you’re looking to build a primary residence, weekend retreat, or private getaway, this property offers a peaceful setting with convenient access to nearby towns, shopping, dining, and major travel routes. No builder tie-in. Buyer is responsible for verifying all information and performing due diligence regarding permits, utilities, zoning, land use, and building plans.

Trunk Rd, Henderson

Listing courtesy of The Parker Group. Contact: 3022176692

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

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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Crystal Scott

Crystal Scott is a Licensed REALTOR with Keller Williams Capital Properties. After devoting 15 years of her life to serving as a Registered Nurse in the Surgical/Trauma Intensive Care Unit (ICU) at Mary Washington Hospital, Crystal seamlessly transitioned into the world of real estate. Her passion for the housing market had always burned bright alongside her nursing career, and she eventually took the bold step of obtaining her real estate license.The dynamic environment of the ICU instilled in Crystal a profound sense of compassion, unwavering dedication, and the importance of being a steadfast advocate for those entrusted to her care. She learned firsthand the value of meticulous attention to detail, the ability to thrive under pressure, and the commitment to giving her all each and every day. It also taught her that tomorrow is not promised and to live life to the fullest and follow your dreams.These invaluable lessons seamlessly transitioned into her role as a REALTOR. Crystal approaches each client interaction with the same blend of empathy, professionalism, and dedication that defined her nursing career. Whether assisting clients in finding their dream home or guiding them through the process of selling their property, she is committed to making the experience as seamless, exciting, and stress-free as possible.Crystal understands that buying or selling a home is one of life’s most significant decisions, regardless of the price point. As such, she leverages her expertise and insights to empower her clients to make informed decisions that align with their unique goals and aspirations. With Crystal by your side, you can trust that she will navigate every step of the home buying or selling journey with integrity, transparency, and unwavering commitment to your best interests.

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