Maryland’s waterfront culture takes on three distinct forms across the Chesapeake region, each shaped by water access, heritage, and the land itself. In Fairhaven’s Tracys Landing, a rare merged-lot opportunity speaks to a multi-generational community where shoreline access is shared. On the Eastern Shore, Wilderness Estate in Trappe pairs deep-water Choptank frontage with ±234 acres of preserved farmland and mature woodlands, anchored by historic brick wings. Near Oxford, Anderson Farm offers roughly 2,000 feet of Goldsborough Creek shoreline and sunset-facing exposure beside a storied waterfowl landscape.
525 James Ave | Contact for pricing
Theresa Mills
Theresa Mills
Along the water’s edge in Fairhaven, MD, a rare opportunity unfolds across two lots—525 and 527 James Ave—being sold together and merged into one. Set within a charming waterfront community shaped by generations, this setting is defined as much by its traditions as by its access to the outdoors. Direct water access at two points within the neighborhood opens the door to easy days of boating and fishing, with the shoreline lifestyle woven into everyday routines. Neighbors often buy in and continue the legacy, lending the area a lived-in sense of continuity and connection. At its current status, the property would require a new well and holding tanks, offering a clear starting point for those exploring the idea of building a dream home. Life here is measured in simple, lasting moments on the water.
Price: Contact for pricing
- Size:
- 728 sq ft
- Contact:
- Theresa Mills, Samson Properties, 410.349.6123
Wilderness Estate Trappe Maryland | Contact for pricing
Coard Benson
Coard Benson
Along the Choptank River, Wilderness Estate unfolds across five parcels, combining architectural distinction, historical significance, and Eastern Shore charm. Preserved farmland and mature woodlands frame the setting, creating complete privacy and broad southern views, with deep water access for days shaped by the tide and open sky. The impeccably maintained residence is anchored by 18th- and 19th-century brick wings, a quietly confident expression of colonial heritage. Thoughtful updates introduce modern comforts while respecting the home’s historic character, letting old and new coexist with ease. Just minutes from Easton, Oxford, and St. Michaels, the estate balances seclusion with a connection to the region’s storied towns. Life here feels unhurried—defined by land, river light, and a sense of enduring place.
Size: 234 acres
Price: Contact for pricing
- Contact:
- Coard Benson, Benson & Mangold Real Estate, 410.310.4909
Anderson Oxford Maryland | Contact for pricing
Coard Benson
Coard Benson
Along the tranquil shores of Goldsborough Creek, Anderson Farm offers a rare stretch of waterfront in Oxford, Maryland. With approximately 2,000 feet of shoreline and coveted northwesterly exposure, the parcel is positioned for sweeping sunset views across protected waters. A preferred elevated homesite allows for construction with a 100-foot setback, balancing privacy with the ability to maximize a home’s footprint and nearly 180 degrees of waterfront presence. Woodland edges and neighboring farmland frame the setting, creating a sense of quiet continuity with the surrounding landscape. Located within a historic waterfowl staging area, the property’s natural character feels both preserved and deeply rooted in place, yet it remains just minutes from Oxford and Easton. Here, days can unfold to the rhythm of light, tide, and sky.
Size: 51.68 acres
Price: Contact for pricing
- Contact:
- Coard Benson, Benson & Mangold Real Estate, 410.310.4909
