Welcome to 5582 Trafalgar Cir (truh-FAL-gar), a beautifully maintained single-level, 3-bedroom, 2.5-bath home located in the desirable Tilghman on Chesapeake community. Built in 2023 and offering 2,110 square feet of thoughtfully designed living space, this home has been lived in for only about a year and truly shows better than new. The seller’s meticulous care and attention to detail have addressed the typical quirks of new construction, creating a move-in-ready home with refined comfort throughout. Designed for easy one-level living, the open floor plan centers around a spacious Great Room that flows seamlessly into the kitchen and dining area—ideal for both everyday living and entertaining. The kitchen features a large island, generous cabinetry, and ample counter space. The private owner’s suite provides a peaceful retreat with a walk-in closet and a well-appointed en-suite bath with dual vanities. Two additional bedrooms, a full hall bath, a convenient half bath, and a dedicated laundry area complete the layout. Step outside to an oversized deck, perfect for outdoor dining, relaxing, or hosting gatherings while enjoying community water access and a small water view. Whether you’re sipping your morning coffee or unwinding in the evening, the outdoor space enhances the home’s connection to the Chesapeake Bay lifestyle. Tilghman on Chesapeake is a water-oriented community offering amenities that include a clubhouse, pool, and marina access, all just minutes from local marinas, seafood restaurants, and the charm of Tilghman Island. This is a rare opportunity to own a like-new, single-story home with exceptional outdoor living in one of the Eastern Shore’s most sought-after waterfront communities.
TILGHMAN ISLAND. Welcome to this beautiful and spacious 5-bedroom, 3.5-bath single-family home located in the highly sought-after Tilghman on Chesapeake community. Designed for modern comfort and relaxed island living, this home offers an open-concept floor plan filled with abundant natural light and elegant finishes throughout. The gourmet kitchen is a true centerpiece, featuring granite countertops, stylish modern appliances, a large center island, and an oversized walk-in pantry—perfect for both everyday cooking and entertaining. The kitchen flows seamlessly into the living and dining areas, where a stunning gas fireplace creates a warm and inviting atmosphere for daily living and special gatherings. Upstairs, you will find a thoughtfully designed layout offering comfort and privacy. The expansive primary suite is a true retreat, complete with two separate walk-in closets and a luxurious en-suite bath. An additional generously sized ensuite bedroom provides excellent flexibility for family or guests, while the remaining bedrooms offer ample space and versatility for a home office, gym, or guest accommodations. Situated in the tranquil Tilghman on Chesapeake community, residents enjoy access to exceptional amenities, including a community pool, clubhouse, and deep-water boat slips available through the HOA. Ideally located near the Chesapeake Bay and surrounding tributaries, this home offers unparalleled access to boating, deep-water fishing, crabbing, and scenic coastal adventures. Miles of open bike trails and the peaceful charm of Tilghman Island complete the experience, making this property the perfect blend of luxury, comfort, and true Bay living.
Private Home with Pool, Bay Views, and No HOA Located in FEMA Flood Zone X (no flood insurance required and no history of water intrusion), this well-maintained home sits at the end of a private Crepe Myrtle–lined drive with no HOA and strong privacy from mature trees. The home offers two entry points: a formal front foyer and a secondary entrance into a mudroom/laundry with utility sink, storage, and access to a full bathroom. The main level includes a parlor with built-in shelving, a family room with wood-burning fireplace, and sliding doors leading to the backyard. The fireplace stack runs to the second floor and provides full-home heating. The open kitchen features granite countertops, light wood cabinetry, stainless steel appliances, and a breakfast bar with direct access to the deck and patio overlooking the pool. A separate dining room faces the front yard. There are three bedrooms, including a primary suite with walk-in closet, linen storage, and en-suite bath with jetted soaking tub and double vanity. An additional room functions as a bedroom or office. A long hallway provides extra storage. The backyard includes an in-ground pool, multiple seating areas, and views of Black Walnut Creek with glimpses of the Chesapeake Bay. Both an attached and detached garage provide ample parking and storage. The crawlspace is fully concreted. The home is equipped with two burglar alarms, fire and carbon monoxide detectors, and a custom exterior camera system. A private property with water views, outdoor living space, and no HOA restrictions.
Spacious 3,000 sqft two-story waterfront home on 3/4 acre parcel on Harris Creek where it joins the Choptank River for an 11-mile view to Cambridge. House is brick and block on the first level with redwood siding on the second level in board and batten style. 150ft heavily built and reinforced bulkhead waterfront with recently renovated 75ft long dock. Second floor includes four bedrooms with water views and a bunk room all with oak flooring recently refinished, built-in chest of drawers and closets, built in desks and bookcases. Second floor includes a great room with cathedral ceiling and outside deck facing Harris Creek, a full bath and powder room, all tiled. First floor has open area kitchen, dining/living room with adjacent full bath and utility room. Kitchen has been dismantled as a clean pallet for new owner, bring your vision. First and second floor have fireplaces with separate flues. Full attic. 700sqft attached garage and workshop. Property is equipped with a Generac generator for dependable backup power. There is an offshore duck blind for waterfowl & duck hunting which is shared with neighboring owners. Enjoy panoramic water views, boating, crabbing, fishing year-round. Experience the waterfront charm and relaxed pace of Tilghman Island living, close to museums, restaurants, shopping and marinas, truly a wonderful place to call home! Offers encouraged.
*A Once-in-a-Lifetime Chesapeake Bay Waterfront Offering – The Iconic Tilghman Island Inn* NOTE: Has public sewer and well. Welcome to a rare opportunity to own one of the most beautiful, fully reimagined waterfront hospitality properties on Maryland’s Eastern Shore. Set on five acres with sweeping views of the Chesapeake Bay, the Tilghman Island Inn is that extraordinary blend of romance, lifestyle, and investment that rarely becomes available. Established more than 50 years ago, the Inn has been transformed from top to bottom through a meticulous, comprehensive renovation. Today, it lives as a boutique luxury retreat with 20 uniquely designed guest rooms (five with gas fireplaces), a full-service waterfront restaurant and bar, expansive outdoor dining terraces, a sparkling 20' x 40' pool, lush gardens, and expansive private docking with the relaxed charm and quiet sophistication that define the Chesapeake Bay. Guests return year after year for the Inn’s serenity, sunset views, on-site dining, and proximity to St. Michaels, Easton, and Annapolis. For buyers, the value is just as clear: major improvements are already complete, systems are up to date, and recent guest ratings average about 95% across major travel platforms. Whether you envision this as a turnkey boutique hotel, a private family compound, a luxury event destination, or a future waterfront condominium development, the property is positioned for success. The Inn is legally configured as 20 residential condominium units offering flexibility. Property Features: 5-acre waterfront property, 15,000+ sq. ft. hotel and restaurant, 345 ft. vinyl seawall, 20 x 30 ft. T-Dock, 175 ft. floating dock with 7 additional boat slips, 20 uniquely designed guest rooms, 20 x 40 ft. in-ground pool, 30 x 12 ft. fully functional greenhouse, and Lush ornamental and raised bed vegetable gardens For investors seeking a premier turnkey hospitality venture or a high-value waterfront development opportunity, the Tilghman Island Inn presents a rare chance to own an Eastern Shore gem with limitless potential. **NOTE: FOR BROCHURE & VIDEO CONTACT AGENT**
Welcome to waterfront living at its finest on picturesque Tilghman Island! This beautifully maintained 3,040 sq ft Colonial offers stunning open water views and a lifestyle of comfort, elegance, and ease. Boasting four spacious bedrooms and two and a half baths, this home features a flowing floor plan with natural light, generous living spaces, and a perfect blend of indoor and outdoor living. Enjoy your morning coffee while watching boats drift by, or relax in the evening with views that will take your breath away. The home is located in a sought-after waterfront community offering fantastic amenities including a clubhouse, pool, and marina—perfect for boating, entertaining, and leisure. Whether you’re looking for a peaceful full-time residence or a weekend retreat, this home checks all the boxes. Just bring your boat and your dreams! NEW ROOF & FIREPLACE 2024, NEW APPLIANCES 2019
Built in 2025, this new construction home offers the best of Eastern Shore living in the water-privileged community of Tilghman on the Chesapeake. Enjoy the ease of one-level living and a thoughtfully designed split-bedroom floor plan. The welcoming covered front porch opens to a bright entry foyer leading to the spacious, open-concept living area. The kitchen boasts granite countertops, a center island with bar seating, a pantry and ample cabinet space, perfect for everyday living and entertaining. The kitchen overlooks the living room, featuring a cozy gas fireplace and an open dining area with a sliding glass door, ideal for adding a future deck or patio. The primary suite is privately situated off the main living space and features two walk-in closets and a luxurious bathroom with a granite double-sink vanity, tile and glass shower and a linen closet. Two additional bedrooms and a full guest bath are located on the opposite side of the home, offering privacy for guests or family members. A separate laundry/mudroom provides convenient access to the attached two-car garage. Built by Gemcraft Homes, a highly regarded regional builder, this home provides peace of mind with a 1-year builder warranty, 2-year HVAC/plumbing/electrical coverage and a 5-year structural warranty. For a separate fee, owners can enjoy the amenities of the Tilghman on the Chesapeake waterfront clubhouse, which features a pool and recreation room with an expansive deck and balcony, perfect for hosting events or gatherings. Boat slips are also available, offering easy access to the Bay. Located just moments from local restaurants, multiple boat landings, prime fishing spots and centrally positioned for boating to St. Michaels, Kent Island, Oxford, Cambridge and Annapolis. This isn’t just a home, it’s a lifestyle.
This historic property known as "The Elms" was built in 1900 and used as a fishing lodge for many years. The property sits on 2 acres, has public sewer and well water. The buildings hold virtually no value unless and extensive historic renovation were completed. Tilghman is an historic waterfront town that features a waterman's museum, marina, many restaurants, established neighborhoods/communities such as Tilghman on the Chesapeake, Fairbanks, and Black Walnut Point. This historic property offers many opportunities. Property being sold "As-Is."
Discover the essence of refined Eastern Shore living in this meticulously renovated contemporary waterfront retreat, gracefully set along the tranquil shores of Harris Creek and looking out to the Choptank River. Every detail of this remarkable home exemplifies elegance. Step inside to a breathtaking panorama of water views framed by expansive windows that fill the home with ethereal lighting. Designed for both the passionate cook and the gracious host, the gourmet kitchen features professional-grade Wolf appliances, a Cambria quartz oversized island, and custom cabinetry. The main level primary suite offers panoramic views of Harris Creek, custom millwork, and a spa-worthy bath showcasing a deep soaking tub and beautifully tiled shower. An additional main-level bedroom with private ensuite provides ideal accommodations for guests. On the second floor, three spacious bedrooms await. One a second private primary suite with custom closet and balcony. Two bedrooms, sharing a thoughtfully designed Jack and Jill bath, all centered around a loft-style lounge. Additional amenities include a thoughtfully designed mudroom and a garage with epoxy-coated floors and sleek Clopay glass garage doors. The covered porch creates a seamless space for indoor-outdoor entertaining. Situated on a large, private lot within an exclusive HOA waterfront community, the property offers a rare sense of seclusion while still providing access to coveted amenities such as a community dock and pool. With all new electric, plumbing, HVAC and more, this house has been taken down to the studs and rebuilt to its timeless architecture. From its elevated finishes to its extraordinary setting, 21485 Island Club Drive captures the essence of luxury coastal living on Maryland’s Eastern Shore.
Welcome to your Eastern Shore getaway, located at 6135 Summit Street, Tilghman, Maryland. This charming property is just a short walk from Tilghman Island's best waterfront attractions, including two marinas and three excellent dining options. This two-bedroom, one-bath home reflects pride of ownership and has been well maintained, making it ready for you to enjoy a slower pace of life on Maryland's Chesapeake Bay. The backyard pool is a highlight, offering a tranquil setting that is worth the price of admission. Relax poolside after a day spent fishing, crabbing, or sailing. Additionally, a large shed provides ample storage for all your needs. This property also presents a great investment opportunity for short-term rental or as a retirement home. Don’t miss out on this one! Make your appointment today.
Exquisitely designed renovation incorporating high end finishes makes this waterfront 3BR, 3B cottage the perfect retreat! Large great room w/dining area, fireplace & multiple seating areas gives you ample spaces to enjoy the broad, westerly views of the bay. The gourmet kitchen & pantry is a chef's dream. Screen room, private pier, separate garage w/ guest house.
Secure and Secluded Luxury Living with Bay Views & Resort-Style Backyard Property is located in FEMA Zone X, has never had water on the property and seller is not required to have flood insurance Tucked away at the end of a private Crepe Myrtle-lined drive, this well-maintained luxury retreat offers the perfect blend of tranquility, style, and function—without the constraints of an HOA. Thoughtfully landscaped grounds and mature privacy trees create a serene front yard oasis, complete with Crepe Myrtles and a welcoming covered porch ideal for morning coffee and peaceful nature views. Step inside from either the elegant front foyer or the convenient secondary entrance into the mudroom/laundry area, complete with utility sink, storage, and access to a full bathroom. The home's interior opens up beautifully, beginning with a light-filled parlor featuring built-in shelving, flowing seamlessly into a spacious family room with a fireplace and sliding glass doors that overlook the backyard. The wood burning fireplace has a stack - that stairs wrap around - to second floor, providing full home heating. Designed for connection and comfort, the open-concept kitchen boasts granite countertops, light wood cabinetry, stainless steel appliances, and a breakfast bar with clear sightlines to the backyard and pool. Entertain effortlessly with direct access from the kitchen to the shaded deck and expansive patio—perfect for summer pool parties or cozy evening gatherings. Formal dining space offers bright, natural light and a view of the front yard. The home’s three bedrooms, including a generously sized owner's suite, are positioned for both privacy and comfort. The owner’s retreat includes a walk in closet with shelving, a linen closet, and an en-suite bath featuring a jetted, extra deep, long tub and double vanity. The ten foot hallway from the owner's suite to additional room with plenty of storage. An additional room currently serves as both an office and bedroom, offering flexible space for remote work or guests. Outside, enjoy your own private haven: a large open backyard with multiple seating areas, a sparkling inground pool, and views of Black Walnut Creek and glimpses of the Chesapeake Bay. The attached and detached garages provide ample space for vehicles, hobbies, or storage. The home's crawlspace is completely concreted in. This sweet retreat is kept safe and secure with two burglar alarms, fire and carbon monoxide detectors, and custom exterior CCTV (camera) system. This property is more than a home—it’s a retreat. Peaceful, private, and perfect for entertaining.
Welcome to 5520 Leeward Lane, a private waterfront estate tucked away at the end of a quiet, tree-lined drive on Tilghman Island—a rare opportunity to own a stunning piece of Maryland’s Eastern Shore. This expansive home features panoramic water views from almost every room and delivers the ultimate blend of luxury, comfort, and natural beauty. The grand foyer sets a graceful tone, leading into a spacious main-level layout designed to impress. The expansive living room is flooded with natural light and flanked by a formal dining area, a warm and inviting den, and a breakfast nook with vaulted ceilings—all connected by elegant sight lines and polished hardwoods. A true chef’s kitchen anchors the heart of the home, outfitted with a commercial-grade gas stove, a commercial refrigerator, two dishwashers, granite countertops, and an oversized island perfect for entertaining or casual morning coffee. The main-level primary suite is a private retreat, offering dual walk-in closets, a spa-inspired bath with soaking tub and glass shower, and serene views of the surrounding landscape. A conveniently placed laundry room with a half bath adds thoughtful utility to the main floor, while the upstairs offers flexibility with four generous bedrooms, a shared full bath, and a secondary living space complete with its own kitchenette—ideal for extended guests or multigenerational living. From nearly every room, you're drawn to the shimmering water just beyond the windows. Whether enjoying sunsets from the deck, stargazing from the rooftop deck above the three-car garage, or savoring peaceful mornings with the birdsong of the bay, this home embraces its setting with elegance and ease. Attic storage above the garage ensures ample space for seasonal gear or future creative use. Tilghman Island itself is a captivating enclave, celebrated for its maritime heritage, vibrant wildlife, and relaxed coastal vibe. Here, you’ll enjoy unmatched privacy, historic charm, and proximity to waterfront dining, boutique shops, and world-class boating—just far enough to escape, yet close enough to stay connected. 5520 Leeward Lane isn’t just a home—it’s a lifestyle. A sanctuary where land, sea, and sky converge in perfect harmony. Schedule your private showing and experience Eastern Shore living redefined.
Tilghman is located in Maryland.
