Tilghman On Chesapeake Real Estate

Tilghman On Chesapeake Real Estate

Welcome to the picturesque community of Tilghman On Chesapeake, a hidden gem nestled on the serene shores of the Chesapeake Bay in Talbot County, Maryland. This charming subdivision offers a perfect blend of coastal living and tranquil countryside, making it an ideal destination for those seeking a peaceful retreat or a vibrant community to call home.

Tilghman On Chesapeake is characterized by its stunning waterfront properties, many of which boast breathtaking views of the bay and direct access to pristine beaches. The architecture here reflects a delightful mix of traditional and contemporary styles, creating an inviting atmosphere that resonates with both charm and sophistication. Whether you're looking for a cozy cottage or a spacious family home, this subdivision has something to suit every taste and lifestyle.

Nature enthusiasts will find themselves in paradise, with abundant opportunities for outdoor activities such as boating, fishing, kayaking, and birdwatching. The nearby Tilghman Island offers a rich tapestry of natural beauty, coupled with a warm and welcoming community spirit. Residents can enjoy leisurely strolls along scenic trails, or simply relax and soak in the stunning sunsets that paint the sky in vibrant hues.

In addition to its natural allure, Tilghman On Chesapeake is conveniently located near local shops, restaurants, and cultural attractions, ensuring that you’re never far from the amenities you need. With its unique blend of tranquility, community, and natural beauty, Tilghman On Chesapeake is more than just a place to live; it's a lifestyle waiting to be embraced. Discover your dream home in this enchanting subdivision today!

Newest Listings in Tilghman On Chesapeake

5 Beds ⋅ 4 Baths

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.

5559 Trafalgar Cir, Tilghman

Listing courtesy of Meredith Fine Properties. Contact: 4107149166

5 Beds ⋅ 5 Baths

Back on the market due to Buyers unable to fulfill home sale contingency- 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.

21485 Island Club Rd, Tilghman

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

3 Beds ⋅ 2 Baths

5654 Trafalgar Cir, Tilghman

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415

3 Beds ⋅ 2 Baths

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.

5648 Trafalgar Cir, Tilghman

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415

4 Beds ⋅ 3 Baths

PRICE IMPROVEMENT*** 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

21477 Island Club Rd, Tilghman

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

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