Refine Search
Sort by
$38,200,000
4 Beds 2 Baths
Tulip Forest, a farm defined by scale, stewardship, and long-term value. Recognized as a premier sporting estate, this legacy holding property is the kind of asset that seldom comes to market on Maryland's Upper Eastern Shore. 1,054 +/- acres held intact under one ownership: 680 tillable acres, 272 acres of timber, 5 ponds, 3 impoundments, 26.75-acre wetlands restoration project, 45 acres CRP, a 3.75 mile interior gravel road system, 3 residences, and multiple farm outbuildings. At its center stands Caulk's Field House, circa 1743, a remarkably preserved residence on the ground recognized among Maryland's best-preserved War of 1812 sites. Nearly four miles of farm roads reach every corner of the property, and the ponds, impoundments, and mature timber hold waterfowl, whitetail and countless other game species. Also included beyond the farming operation: 7 acres zoned commercial, additional parcels zoned Village, and four sewer allocations secured along Georgetown Road. A working farm today, with room to grow, suited to farmers, sportsmen, conservation buyers, and investors.

8184 Rock Hall Rd, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact: 4434803453

$599,900
3 Beds 3 Baths
Welcome to 20714 Wilkins Avenue, a rare opportunity in the heart of charming Rock Hall. Perfectly positioned less than two blocks from the beach, this home is within walking distance of local favorites including Blue Heron Oyster House, Muskrat Alley Café, and the marinas at Osprey Point and Haven Harbour, making it easy to enjoy everything this beloved Chesapeake Bay town offers. Situated on an oversized double lot! This property offers exceptional flexibility and future potential. Whether you’re looking for room to expand, extra outdoor space, or as a short term rental with multiple accommodations, properties like this are rarely available this close to downtown. The 3-bedroom, 2.5-bath home has been thoughtfully updated with a stunning brand-new primary bathroom and new powder room while maintaining its coastal charm. A detached shed has been transformed into additional guest quarters, equipped with a propane stove and window air conditioner, creating the perfect space for visiting family and friends. Step outside to your private 18-foot, three-season gazebo, complete with electricity and perfectly positioned to overlook the water. Whether you're enjoying your morning coffee, watching boats glide in and out of the harbor, or taking in breathtaking sunsets, this inviting space offers the perfect setting to relax and enjoy the beautiful water views. With its prime location, generous lot size, and versatile layout, this property would make an exceptional full-time residence, vacation getaway, or income-producing short term rental. Opportunities like this in downtown Rock Hall don’t come along often.

20714 Wilkins Ave, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

$699,000
4 Beds 3 Baths
Enjoy a long, secluded driveway to a 2,185 sq ft home sitting on 7.9 acres of mature, heavily-forested woods with waterfront views of Grey’s Inn Creek. The home features vaulted ceilings and has access to a private pier and dock; it’s perfect for boating, fishing, crabbing, or just enjoying the outdoors. Located in Rock Hall, Maryland, known for hunting, fishing, and Chesapeake Bay boating, this property is being sold As-Is, offering a chance to remodel and complete your vision. Current owners originally built the house in 1986 as a cabin with a later add-on to the original structure. Rock Hall is a waterfront town located directly on the National Chesapeake Scenic Byway in Kent County. The boat pier will need extensive work and is non-operational. Property is being sold AS-IS with a Right-to-Inspect. Tremendous opportunity for a wooded, waterfront residence with some sweat equity.

21610 Hidden Creek Dr, Rock Hall

Listing courtesy of Whitetail Properties Real Estate, LLC. Contact:

$385,000
3 Beds 2 Baths
The Kent County State Health Department have approved percs for the following three properties: 26670 Maple Avenue Tax Map 13/Parcel 16/Deed Reference 77/422 with the recording of a 1920 dwelling, 26680 Maple Avenue Tax Map 13/Parcel 17/identified as Parcel #1 Deed Reference 249/96 with the recording of a 1940 dwelling and .5 acre parcel of land Tax Map 13/Parcel 9/identified as Parcel #2 Deed Reference 249/96 . Both homes are in need of major repair however the parcels are lovely. These residentially zoned properties present a great investment opportunity. The parcels are of a generous size, featuring front and side yards that offers great outdoor space. Still Pond is just minutes from Betterton Beach. Total size of three parcels is 1.66 +/- acre.

26670-26680 Maple Ave, Still Pond

Listing courtesy of Doug Ashley Realtors, LLC. Contact: