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8781 Tilghman Island Road presents a rare opportunity to own a custom-designed, Daffin-built Chesapeake Bay estate set on 21±acres between historic St. Michaels and Tilghman Island. Constructed with a timeless brick exterior and encompassing approximately 6,500± square feet, this five-bedroom, five-and-a-half-bath residence was thoughtfully designed to embrace its extraordinary waterfront setting, where expansive Chesapeake Bay views and unforgettable western sunsets become part of everyday life. The home's classic architecture is highlighted by stacked waterfront porches, a spacious front balcony, and walls of windows that capture panoramic views from nearly every principal room. Two gas fireplaces add warmth to the generous living spaces, while abundant storage and a thoughtful floor plan provide comfort and functionality for both everyday living and entertaining. The main level is anchored by a spacious waterfront primary suite featuring a walk-in closet, oversized water closet, an en-suite bath with a tile walk-in shower and a separate tub, and a private enclosed porch overlooking the Bay. Upstairs, three generously sized en-suite bedrooms offer exceptional accommodations. Two bedrooms open to the front balcony, while the waterfront suite enjoys direct access to the upper waterfront porch. The third floor offers an additional en-suite bedroom along with a versatile bonus room ideal as a home office, craft room, playroom, fitness space, or additional storage. Outside, approximately 662± feet of riprapped Chesapeake Bay shoreline frames the property, while mature trees create a beautiful natural setting. Approximately four acres lie outside of the agricultural assessment, with the remaining acreage benefiting from agricultural tax status. Positioned along the Eastern Bay Water Trail, the property offers experienced kayakers direct access to one of the region's premier paddling routes and the opportunity to explore the Chesapeake Bay from your own shoreline. A detached garage offers exceptional flexibility and could serve as a future pool house, workshop, studio, or, where permitted, guest accommodations. The home is equipped with five-zone heat pumps with central air conditioning, along with separate ductless HVAC systems serving both waterfront porches and the detached garage, providing year-round comfort throughout the property. Combining quality craftsmanship, a premier Chesapeake Bay location, and over 21± acres of land, this exceptional waterfront estate offers an increasingly rare opportunity to enjoy privacy, space, and some of the Eastern Shore's most spectacular sunset views.

5 Beds ⋅ 6 Baths

8781 Tilghman Island Road presents a rare opportunity to own a custom-designed, Daffin-built Chesapeake Bay estate set on 21±acres between historic St. Michaels and Tilghman Island. Constructed with a timeless brick exterior and encompassing approximately 6,500± square feet, this five-bedroom, five-and-a-half-bath residence was thoughtfully designed to embrace its extraordinary waterfront setting, where expansive Chesapeake Bay views and unforgettable western sunsets become part of everyday life. The home's classic architecture is highlighted by stacked waterfront porches, a spacious front balcony, and walls of windows that capture panoramic views from nearly every principal room. Two gas fireplaces add warmth to the generous living spaces, while abundant storage and a thoughtful floor plan provide comfort and functionality for both everyday living and entertaining. The main level is anchored by a spacious waterfront primary suite featuring a walk-in closet, oversized water closet, an en-suite bath with a tile walk-in shower and a separate tub, and a private enclosed porch overlooking the Bay. Upstairs, three generously sized en-suite bedrooms offer exceptional accommodations. Two bedrooms open to the front balcony, while the waterfront suite enjoys direct access to the upper waterfront porch. The third floor offers an additional en-suite bedroom along with a versatile bonus room ideal as a home office, craft room, playroom, fitness space, or additional storage. Outside, approximately 662± feet of riprapped Chesapeake Bay shoreline frames the property, while mature trees create a beautiful natural setting. Approximately four acres lie outside of the agricultural assessment, with the remaining acreage benefiting from agricultural tax status. Positioned along the Eastern Bay Water Trail, the property offers experienced kayakers direct access to one of the region's premier paddling routes and the opportunity to explore the Chesapeake Bay from your own shoreline. A detached garage offers exceptional flexibility and could serve as a future pool house, workshop, studio, or, where permitted, guest accommodations. The home is equipped with five-zone heat pumps with central air conditioning, along with separate ductless HVAC systems serving both waterfront porches and the detached garage, providing year-round comfort throughout the property. Combining quality craftsmanship, a premier Chesapeake Bay location, and over 21± acres of land, this exceptional waterfront estate offers an increasingly rare opportunity to enjoy privacy, space, and some of the Eastern Shore's most spectacular sunset views.

8781 Tilghman Island Rd, Wittman

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Benson & Mangold, LLC.

$1,700,000

Now Offered at $1,895,000 | Private Harris Creek Waterfront Private Harris Creek waterfront with pool, pier, boat lift and deep-water access—crafted for boating, kayaking and the best of Eastern Shore living. This five-bedroom, three-and-a-half-bath residence offers a rare blend of privacy, comfort and wide water views just minutes from St. Michaels and Easton. Sun-filled interiors feature red oak floors, custom built-ins, multiple fireplaces and an inviting layout designed for everyday living and entertaining. The kitchen is the heart of the home with KitchenAid appliances, granite countertops, oversized island seating, butler’s pantry and dry bar. Main-level living includes a waterside primary suite with fireplace, private guest suite, office or den, and additional gathering spaces. Upstairs offers three bedrooms, full bath and spacious family room. Outdoor living shines with a screened porch, expansive waterside deck, saltwater pool and firepit patio overlooking Harris Creek. Private pier with boat lift and deep-water access opens the door to endless days on the water. Additional features include a two-car garage with workshop, whole-house generator and new septic system (2025). An exceptional waterfront opportunity at an outstanding new price.

5 Beds ⋅ 4 Baths

Now Offered at $1,895,000 | Private Harris Creek Waterfront Private Harris Creek waterfront with pool, pier, boat lift and deep-water access—crafted for boating, kayaking and the best of Eastern Shore living. This five-bedroom, three-and-a-half-bath residence offers a rare blend of privacy, comfort and wide water views just minutes from St. Michaels and Easton. Sun-filled interiors feature red oak floors, custom built-ins, multiple fireplaces and an inviting layout designed for everyday living and entertaining. The kitchen is the heart of the home with KitchenAid appliances, granite countertops, oversized island seating, butler’s pantry and dry bar. Main-level living includes a waterside primary suite with fireplace, private guest suite, office or den, and additional gathering spaces. Upstairs offers three bedrooms, full bath and spacious family room. Outdoor living shines with a screened porch, expansive waterside deck, saltwater pool and firepit patio overlooking Harris Creek. Private pier with boat lift and deep-water access opens the door to endless days on the water. Additional features include a two-car garage with workshop, whole-house generator and new septic system (2025). An exceptional waterfront opportunity at an outstanding new price.

22707 Marshall Ln, Wittman

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: Unrepresented.

$995,000

Affordable Talbot County, MD waterfront home. Just a 12-minute drive beyond St. Michaels, this well-built 3 bedroom, 2.5 bath home faces west across the waters of Cummings Creek. Great sunset views from the waterside screened porch! The 1.92-acre lot is well-elevated (flood insurance is not required by mortgage lenders). The house features generous-sized rooms, including a spacious kitchen/dining room. Efficient hot-water baseboard heat and 2-zone AC. In addition to an attached garage, there is a detached 3-bay garage/workshop. Asphalt driveway and parking area. Substantial pier w/two boat slips. By boat, Tilghman Island and the open waters of Chesapeake are a short, scenic cruise downstream from the dock. This location is known for great fishing and crabbing!

3 Beds ⋅ 3 Baths

Affordable Talbot County, MD waterfront home. Just a 12-minute drive beyond St. Michaels, this well-built 3 bedroom, 2.5 bath home faces west across the waters of Cummings Creek. Great sunset views from the waterside screened porch! The 1.92-acre lot is well-elevated (flood insurance is not required by mortgage lenders). The house features generous-sized rooms, including a spacious kitchen/dining room. Efficient hot-water baseboard heat and 2-zone AC. In addition to an attached garage, there is a detached 3-bay garage/workshop. Asphalt driveway and parking area. Substantial pier w/two boat slips. By boat, Tilghman Island and the open waters of Chesapeake are a short, scenic cruise downstream from the dock. This location is known for great fishing and crabbing!

8684 Sewell Point Rd, Wittman

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Unrepresented.

$485,000

ENJOY Stunning SUNSETS and WATER VIEWS!! Tastefully Renovated, this 3 BR, 2 BA home is perfectly situated on 1.09 peaceful Acres overlooking the tranquil Waters of Cummings Creek. Offering true ONE LEVEL living, this turnkey property has been thoughtfully UPDATED from top to bottom in 2025! Step inside to find NEW flooring, fresh paint, stylish trim and all new interior doors with new hardware. The Eat-In Kitchen features NEW Quartz countertops, NEW GE Cafe Stainless Steel Appliances, New stainless sink, NEW White Cabinets and a new reverse osmosis system. Both Bathrooms are fully updated with stylish finishes and the spacious Primary Suite includes a huge walk-in closet! Cozy up by the wood-burning fireplace or enjoy outdoor living on the rear deck and the screened porch — perfect for soaking in all those VIEWS!! Additional features include a NEW Roof, new recessed lighting, new ceiling fans and fixtures, new HVAC and NEW washer and dryer! Flower beds have been freshly mulched and weeded and are just waiting for your personal landscape touches! New Stone Paver walkway and the New Gravel driveway create a warm welcome every time. The attached 1 Car Garage comes with a new opener for added convenience. Located just minutes from the Historic Town of Saint Michaels and close to Downtown Easton for all the dining and shopping your heart can handle! Being so close to the public boat landing offers easy access to the Choptank River for the boating enthusiast not to mention the best crabbing and fishing Maryland has to offer! Best of all it’s in a no flood zone, offering peace of mind in a serene Waterfront setting. Whether you're looking for a Weekend Retreat or a Forever Home this property checks every box. Don’t miss this rare opportunity to own a slice of the Eastern Shore lifestyle!

3 Beds ⋅ 2 Baths

ENJOY Stunning SUNSETS and WATER VIEWS!! Tastefully Renovated, this 3 BR, 2 BA home is perfectly situated on 1.09 peaceful Acres overlooking the tranquil Waters of Cummings Creek. Offering true ONE LEVEL living, this turnkey property has been thoughtfully UPDATED from top to bottom in 2025! Step inside to find NEW flooring, fresh paint, stylish trim and all new interior doors with new hardware. The Eat-In Kitchen features NEW Quartz countertops, NEW GE Cafe Stainless Steel Appliances, New stainless sink, NEW White Cabinets and a new reverse osmosis system. Both Bathrooms are fully updated with stylish finishes and the spacious Primary Suite includes a huge walk-in closet! Cozy up by the wood-burning fireplace or enjoy outdoor living on the rear deck and the screened porch — perfect for soaking in all those VIEWS!! Additional features include a NEW Roof, new recessed lighting, new ceiling fans and fixtures, new HVAC and NEW washer and dryer! Flower beds have been freshly mulched and weeded and are just waiting for your personal landscape touches! New Stone Paver walkway and the New Gravel driveway create a warm welcome every time. The attached 1 Car Garage comes with a new opener for added convenience. Located just minutes from the Historic Town of Saint Michaels and close to Downtown Easton for all the dining and shopping your heart can handle! Being so close to the public boat landing offers easy access to the Choptank River for the boating enthusiast not to mention the best crabbing and fishing Maryland has to offer! Best of all it’s in a no flood zone, offering peace of mind in a serene Waterfront setting. Whether you're looking for a Weekend Retreat or a Forever Home this property checks every box. Don’t miss this rare opportunity to own a slice of the Eastern Shore lifestyle!

22571 Crescendo Cir, Wittman

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: Unrepresented Buyer Office.

$435,000

Enjoy the ease of one-level living in this well-maintained rancher, built in 2002 and situated on 2+/- acres in the quaint village of Wittman. Offering 1,662+/- sqft, this 3-bedroom, 2-bath home provides comfortable living with plenty of room to enjoy both inside and out. Hardwood flooring welcomes you into the foyer, which opens to a spacious living room. The kitchen features ample cabinetry, generous table space and overlooks the backyard, creating the perfect setting for everyday meals or entertaining. The spacious primary bedroom features a large walk-in closet. A convenient side entry leads to the laundry room and a separate full bath. Outside, the open yard offers endless possibilities with plenty of space for gardening, recreation or simply enjoying the outdoors. The oversized detached garage provides abundant room for vehicles, a workshop, hobbies and additional storage, while the blacktop driveway adds convenience and curb appeal. A recently installed 3-ton HVAC system provides added comfort and peace of mind. Located less than ¾ of a mile from the Wittman boat landing, you'll have easy access to Cummings Creek, the Chesapeake Bay, and surrounding tributaries for boating, fishing, crabbing, kayaking, and waterfront dining. Conveniently situated between Tilghman Island and Historic downtown St. Michaels, this property offers the perfect opportunity to enjoy the relaxed lifestyle and natural beauty of Maryland's Eastern Shore.

3 Beds ⋅ 2 Baths

Enjoy the ease of one-level living in this well-maintained rancher, built in 2002 and situated on 2+/- acres in the quaint village of Wittman. Offering 1,662+/- sqft, this 3-bedroom, 2-bath home provides comfortable living with plenty of room to enjoy both inside and out. Hardwood flooring welcomes you into the foyer, which opens to a spacious living room. The kitchen features ample cabinetry, generous table space and overlooks the backyard, creating the perfect setting for everyday meals or entertaining. The spacious primary bedroom features a large walk-in closet. A convenient side entry leads to the laundry room and a separate full bath. Outside, the open yard offers endless possibilities with plenty of space for gardening, recreation or simply enjoying the outdoors. The oversized detached garage provides abundant room for vehicles, a workshop, hobbies and additional storage, while the blacktop driveway adds convenience and curb appeal. A recently installed 3-ton HVAC system provides added comfort and peace of mind. Located less than ¾ of a mile from the Wittman boat landing, you'll have easy access to Cummings Creek, the Chesapeake Bay, and surrounding tributaries for boating, fishing, crabbing, kayaking, and waterfront dining. Conveniently situated between Tilghman Island and Historic downtown St. Michaels, this property offers the perfect opportunity to enjoy the relaxed lifestyle and natural beauty of Maryland's Eastern Shore.

8658 Cummings Rd, Wittman

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Benson & Mangold, LLC.

$385,000

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.

3 Beds ⋅ 2 Baths

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.

22582 Pot Pie Rd, Wittman

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Tilghman Island Realty Inc.

$225,000

Charming farmhouse with approximately 1300 sq feet of living space on a large, picturesque lot. Perfect weekend retreat close to St. Michaels, investment property or full time residence. The second level has two bedrooms, walk-in closet, a cozy nook ideal for a home office and a recently fully renovated bathroom. First floor includes a front room suited for an office or additional full bathroom. Terrific rear deck for enjoying the outdoors. Priced below replacement cost. Large attic and shed. Not far from the community park and public boat ramp.

2 Beds ⋅ 1 Baths

Charming farmhouse with approximately 1300 sq feet of living space on a large, picturesque lot. Perfect weekend retreat close to St. Michaels, investment property or full time residence. The second level has two bedrooms, walk-in closet, a cozy nook ideal for a home office and a recently fully renovated bathroom. First floor includes a front room suited for an office or additional full bathroom. Terrific rear deck for enjoying the outdoors. Priced below replacement cost. Large attic and shed. Not far from the community park and public boat ramp.

22349 Cooper Ln, Wittman

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: TTR Sotheby's International Realty.

$176,000

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.

3 Beds ⋅ 2 Baths

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.

8784 Cummings Rd, Wittman

Listing courtesy of Brokers Realty Group, LLC. Contact:

Selling Office: Benson & Mangold, LLC.

$160,000

Very private setting. Just 10 minutes south of St. Michaels. Make this into a perfect weekend get away home. Conveniently sandwiched between St. Michael's and Tilgman Island and just right off of route 33, you will find this wonderful little opportunity to create your secluded seasonal hideout where you can enjoy all the Eastern Shore has to offer. Fishing, crabbing and swimming are just the start of your summer fun. The quaint town of St. Michael's will provide the entertainment and the fishing town of Tilgman Island will provide a bounty of seafood for the party. Come check out this remote and private place.

2 Beds ⋅ 1 Baths

Very private setting. Just 10 minutes south of St. Michaels. Make this into a perfect weekend get away home. Conveniently sandwiched between St. Michael's and Tilgman Island and just right off of route 33, you will find this wonderful little opportunity to create your secluded seasonal hideout where you can enjoy all the Eastern Shore has to offer. Fishing, crabbing and swimming are just the start of your summer fun. The quaint town of St. Michael's will provide the entertainment and the fishing town of Tilgman Island will provide a bounty of seafood for the party. Come check out this remote and private place.

22381 Cooper Ln, Wittman

Listing courtesy of Cummings & Co. Realtors. Contact:

Selling Office: Chesapeake Bay Real Estate Plus, LLC.

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