Wittman MD Real Estate & Homes for Sale

Investor special in Wittman, MD, just minutes from the charming waterfront town of St. Michaels. This 2- bedroom, 1-bath home sits on approximately 0.317 acres and is in need of significant renovation. Property is being sold as-is. Situated on a spacious lot with a private, wooded setting, this property offers a great opportunity for investors and flippers. The existing footprint provides a solid starting point to renovate, reimagine, or rebuild to suit your vision. Surrounded by mature trees and natural landscape, the setting offers the potential for a peaceful retreat or income-producing property. Conveniently located near local marinas, dining, and all that the Eastern Shore has to offer. Bring your contractor and your vision this is a true opportunity to unlock value. Property being sold strictly as-is

Set on nearly an acre in the heart of Wittman, this cedar shake-sided home offers space, character, and a relaxed Eastern Shore lifestyle. Built in 1900, the 3-bedroom, 1.5-bath residence blends timeless charm with thoughtful updates for comfortable everyday living. Hardwood flooring runs throughout, complemented by a sun-filled dining room and a cozy living room with a gas fireplace and built-in shelving. The kitchen has been refreshed with new flooring, afarmhouse sink, updated butcher block countertops, and a new refrigerator - bright, functional, and well-suited for daily life while preserving the home's original character. Outdoors, the spacious 0.86-acre lot is dotted with mature trees and beautiful landscaping, offering plenty of room to add a deck or fence. A covered front porch and outdoor shower enhance the home's easygoing coastal feel. An oversized two-car garage with attic storage and a large driveway provide ample parking and storage. Located just 0.1 miles from Wittman Community Park, 0.3 miles from Wittman Wharf, and only 7 miles from historic downtown St. Michaels, this property offers peaceful small-town living with convenient access to waterfront amenities, dining, and shopping. A rare opportunity to enjoy space, charm, and location on Maryland's Eastern Shore.

Private Harris Creek waterfront with pool, pier boat lift and deep water access - ideal for boating kayaking and quiet days on the water. Five bedrooms and three-and-a-half baths designed for a relaxed yet refined Eastern Shore lifestyle. Featuring sun-filled interiors feature red oak floors custom built-ins multiple fireplaces and wide water views. The kitchen is designed for gathering with KitchenAid appliances granite counters a butler's pantry dry bar and an oversized island Main-level living includes a waterside primary suite with fireplace and a private guest suite along with a flexible office or den.Upstairs offers three bedrooms a full bath and a spacious family room. A screened porch expansive deck. saltwater pool and firepit patio create inviting outdoor spaces overlooking the water. Two-car garage with workshop whole-house generator and new septic system (2025). An exceptional waterfront offering just minutes to St. Michaels and Easton.

Located in the waterfront village of Wittman, close to the public landing and county park, this beautifully crafted two-story cottage blends charm and character with thoughtful design. The home features 2 bedrooms, 1.5 baths, multiple living areas and 2 office spaces . Open beams, wood floors, and architectural details create a warm, inviting atmosphere throughout. Meticulous renovations by a master carpenter include elevating the home, new foundation and accessible crawl space. This unique property offers a perfect blend of craftsmanship and Chesapeake lifestyle. Enjoy the nearby amenities of St. Michaels, Tilghman Island and Easton - restaurants, shops, museums, galleries and more. If you're searching for an escape - this just might be it!

Rental Opportunity in Wittman, MD Positioned in the desirable community of Wittman, this 3 bedroom, 2 bath home situated on 0.84 commercially zoned acreage and premier road frontage presents a compelling opportunity for investors seeking potential rental income in Talbot County. The property offers comfortable living space, a rural Eastern Shore setting, and proximity to key employment, recreation, and service hubs. In addition to the primary residence, the property includes two detached outbuildings. One is ideal for storage or retail use, and another is suited for workshop or auto repair. The lot provides open space with ample parking and a private setting while remaining conveniently located near St. Michaels, Easton, and Tilghman Island. Investment Highlights 3 Bedrooms 2 Bathrooms split between two units 0.84 acre parcel with generous yard space Two accessory structures (retail/storage (in need of repair) + versatile garage/ workshop) Strong long-term potential rental market supported by local workforce and regional amenities Minutes to marinas, dining, recreation, and Chesapeake Bay attractions Quiet rural location with easy access to surrounding towns and services An excellent offering for investors seeking a stable potential rental property in the Eastern Shore's highly regarded Talbot County market. Property is being sold As-Is. Showings by appointment only. BUYER RESPONSIBILITY TO PERFORM DUE DILIGENCE REGARDING PROPERTY LOCATION, USE, RESTRICTIONS, AND TAXES.

"Bolton Farm", available for the first time in over two decades, is an exceptional offering of rare privacy, including a renovated manor house, historic guest house, new four stall horse barn, pool and tennis. Originally known as Quaker Kemp Farm, dating back to 1790, this remarkable 115-acre waterfront estate with two deeded lots has breathtaking western views across the Chesapeake Bay. A gated entrance and mature tree-lined drive create a gracious approach to the main residence while highlighting the property's stunning water views, natural beauty with mature landscaping and specimen trees. The generous porch-front manor house blends classic architecture with relaxed coastal style with newly updated kitchen and baths. The expansive waterside living room features brick flooring and floor-to-ceiling windows and French doors that flood the space with natural light and showcase stunning water views. A formal living room and dining room sit adjacent, seamlessly connecting the rooms. The well-appointed kitchen and family rooms include a large center island, breakfast area, wet bar, high-end stainless appliances, built-ins and fireplace. A waterside screened porch extends the living space outdoors, perfect for dining and relaxation. The main floor also offers a guest or owners suite with an en-suite marble bath. The paneled mudroom and powder room complete this floor. Upstairs, the hall landing provides access to the generous primary suite which includes built-ins and a beautifully appointed en-suite marble bath. Two additional bedrooms are connected by a renovated bath. The oversized fourth bedroom suite includes a sitting room, en-suite bath and stunning views. This floor is completed with a laundry room. The third floor provides two additional guest bedrooms and a shared full bath. The lower-level basement offers excellent storage. The charming brick guest house, circa, 1790 has two-bedrooms featuring a new cedar shake roof, center hall, high ceilings, wood floors, moldings, full kitchen and renovated bath. The Equestrian and agricultural amenities include a new four-stall barn with loft game room, fenced pastures, a wooded forest, two equipment barns, and a greenhouse/garden shed. Meandering paths connect the main house, guest house, and barns. The property includes a parcel across from the main entrance to ensure additional privacy. The outdoor features give the farm the opportunity for large family occasions with numerous areas to gather and enjoy the stunning sunsets. Features include a waterside pool, covered pavilion, private tennis court, two ponds, a pier and hiking trails throughout the expansive grounds. An adjacent 37+-acre waterfront parcel (included in the total acreage) has a sandy beach and offers additional opportunity, with approvals in place for a seven-bedroom main residence and a three-bedroom guest house. With nearly 4,000 feet of riprapped shoreline, Bolton Farm represents a rare offering on Maryland's Eastern Shore.

A magnificent, stately, Daffin-built, Chesapeake Bay Brick Estate exudes excellent design and craftsmanship in this 5 bedroom (suites) , 5.5 bath 6,500 sq. ft brick home that majestically sits on 21.7 acres facing the Chesapeake Bay. Excellent construction quality and design are evident throughout this magnificent estate. Geothermal system on 1st and 2nd floors; Heat Pump for the 3rd floor; Ductless units for 1st floor porch and 2nd floor porch., 3 hot water heaters. Double porches allow you to embrace arguably the most spectacular sunsets on the Eastern Shore. The front of the property is abundant with trees that offer ultimate privacy and all but 4 acres are taxed under agricultural use, Conveniently located between St. Michaels and Tilghman Island, this Chesapeake Bay oasis will far surpass your expectations. No For Sale sign on property but the property's name 'Baycup' is on a small sign at the entrance.