Jesse Highling

Advisor

Born and raised in Frederick County, Jesse’s passion for the outdoors and sustainable land practices has shaped his career from the very beginning. Starting in the agriculture industry, he gained hands-on experience in dairy and poultry farming, row crop production, nutrient management applications, and Non-GMO grain sales. This practical foundation gave Jesse a firsthand understanding of sustainable practices, which carried into his next professional chapter.

After transitioning into the construction field, Jesse excelled in site excavation and utilities, working on large-scale bioretention projects designed to address wastewater and storm water management. His contributions helped develop natural habitats, combining his interest in environmental stewardship with practical land-use solutions. These projects not only advanced Jesse’s technical skills but also reinforced his dedication to conservation efforts that balance human needs with environmental protection.

Now residing in Easton, Jesse took on a pivotal role in the launch of a startup hunting brand. His leadership in this venture included building strategic relationships with major outdoor brands and conservation organizations, positioning the brand as a respected player in the industry. Through his efforts, Jesse has become known as a connector within the outdoor and conservation communities, advocating for sustainable outdoor recreation and ethical land use.

As a lifelong outdoorsman and conservationist, Jesse’s mission is to inspire a love for nature while promoting responsible land stewardship. He is dedicated to helping his clients not only navigate the complexities of land ownership and investment but also understand the broader impact of their land-use decisions. Jesse’s deep roots in the mid-Atlantic outdoor community, coupled with his agriculture, construction and business development experience, make him a trusted guide for those seeking to align their land assets with sustainable practices and a passion for the outdoors.

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Listings

Featured Property

10380 Chapel Rd, Easton, MD 21601

Listing ID: 04151208

Price: $1450000

Status: active

Acres: 44.28

A rare chance to own 42.28± acres of productive farmland located in the soughtafter Chapel School District,  just minutes northeast of Easton, Maryland. In a county where quality agricultural ground is rarely brought to market, this property presents a valuable opportunity for farmers, investors, and ag-focused buyers. The farm offers approximately 30± acres of tillable land, well-suited for row crops or rotational planting, along with 6± acres of timber and the remaining acreage in the homesite and agricultural improvements. The operation includes substantial infrastructure designed for dairy use: 70± stall main barn with pasture access Dry cow barn 120' x 50' heifer barn 10-cow swing parlor 800-gallon milk tank 350,000-gallon slurrystone tank A 3,878± square-foot farmhouse (5 BR, 3 BA) accompanies the farm, offering ample space for family or farm staff. Both the residence and farm structures are sold As Is, giving the buyer an opportunity to repurpose or expand. Please note: Only the real property conveys. Cattle, machinery, and creamery processing equipment are available separately, outside of the property sale. With its tillable acreage, extensive dairy facilities, and prime Talbot County location, this is a rare opportunity to secure agricultural ground in one of Maryland’s most sought-after farming regions.
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Featured Property

3706 BESTPITCH FERRY RD, Cambridge, MD 21613

Listing ID: 13-000514

Price: $749000

Status: active

Acres: 4

Welcome to Transquaking Lodge, a truly one-of-a-kind property nestled on the banks of the Transquaking River in Cambridge, Maryland, right next to the iconic Blackwater National Wildlife Refuge. Situated on 4 scenic acres, this fully renovated waterfront lodge offers unobstructed views and direct access to one of the most celebrated wilderness destinations in the United States, as recognized by National Geographic. With over 30,000 acres of protected lands at your doorstep, you’ll enjoy unmatched access to Fishing Bay and Blackwater without the burden of private refuge ownership. This rare waterfront location cannot be duplicated under today’s development regulations, making it an extraordinary find for outdoor enthusiasts, hunters, and conservation-minded investors. Step inside the expansive 6-bedroom, 3-bath lodge featuring 2,900± square feet of open-concept living space, plus an additional 2,900± square feet of climate-controlled lower-level storage. The heart of the home is a grand stone fireplace anchoring the spacious family room—perfect for gathering after a day in the field or on the water. The open kitchen and dining area create a warm, inviting atmosphere ideal for entertaining. Originally built in the 1950s, the home was structurally elevated over 6 feet in 2011 to accommodate waterfront conditions and future-proof the property. A comprehensive renovation in 2021–2022 brought modern upgrades including a new kitchen, bathrooms, HVAC systems, insulation, well and purification system, lighting, and more, while carefully preserving the lodge’s rustic character. Outdoors, your private boat ramp provides quick and easy access to world-class hunting and fishing. Dorchester County is home to the elusive Sika deer, diverse waterfowl, wild turkey, striped bass, snakeheads, and blue crabs, all thriving in this unique ecosystem. The lower-level offers over 2,900± square feet of concrete-floor, heated storage, perfect for boats, ATVs, kayaks, and gear. Most furnishings convey with the sale (excluding select family heirlooms, taxidermy and boats), making this a turnkey opportunity for a family retreat, hunting club, or income-generating rental. Don’t miss your chance to own this rare waterfront sanctuary on Maryland’s Eastern Shore.
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Featured Property

2735 Lloyd Webb Rd, Crisfield, MD 21817

Listing ID: 12-009240

Price: $1499000

Status: active

Acres: 1119.42

Presenting, Lawson Marsh, Crisfield, Maryland – 1119.42+- acres. The habitat value of Lawson Marsh is significant both today as it was in the mid-1900s when the Ward Brothers were perfecting their decoy carving craft along Jenkins Creek and Lawson Marsh. This property includes a 7.43+- acre parcel on Lloyd Webb Rd featuring a 1,250 sq ft lodge. On the opposite side of the property along the shoreline, the various recreational activities are enhanced through the use of the cabin with pier to access the vast amount of acreage and to extend your stay on the marsh and water, as well as the offshore blind.     
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