Wittman MD Real Estate & Homes for Sale

Secluded living on the Eastern Shore! Nestled between St. Michaels and Tilghman Island, this 3 bedroom, 1 full bath, 1 half bath home is located in the quiet "village" of Wittman. Large pole building with separate electric meter/breaker is idela for mechanics and outdoor enthusiasts alike. Schedule a showing today! Restricted to owner-occupants, non-profits and government agencies through 3/17/2026 11:59:59?PM CT. HUD Case #241-841431. Equal Housing Opportunity.

Exceptional custom waterfront home on Harris Creek offering an ideal setting for boating, kayaking, paddleboarding and relaxed days on the water. Perfectly suited for a discerning second-home buyer or full-time Eastern Shore living, this five-bedroom, three-and-a-half-bath residence blends thoughtful design with an effortless waterfront lifestyle. A dramatic two-story foyer welcomes you into light-filled living spaces designed for gathering and entertaining. Red oak hardwood floors complement custom built-ins, multiple fireplaces and expansive windows capture tranquil water views. The beautifully appointed kitchen features Kitchen- Aid appliances, granite countertops, butler's pantry, dry bar and an oversized island with seating, which flows seamlessly into a dining area with space for both formal meals and casual breakfast gatherings. Main-level living is a standout anchored by a waterside primary suite with fireplace and serene views. A second first-floor ensuite bedroom provides ideal guest accommodations, while a private office - also well-suited as a formal dining room - and a separate den with fireplace and water views offer flexible living spaces. Outdoor living truly defines the home. Enjoy a screened waterside porch, expansive deck, saltwater pool and patio with firepit - creating multiple settings for entertaining, relaxing and enjoying the natural surroundings. The private pier with boat lift and deep-water access completes this exceptional waterfront setting. Upstairs, three additional bedrooms, a full bath, and a welcoming family room provide comfortable accommodations for family and guests. An attached two-car garage with workshop, generous storage, thoughtful upgrades throughout, 5 KW whole house generator and a brand-new septic system installed in 2025 complete this rare Harris Creek waterfront offering.

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.

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.