Tilghman On Chesapeake Homes under $900,000

Tilghman On Chesapeake Homes under $900,000

Welcome to Tilghman On Chesapeake, a picturesque subdivision nestled in the serene surroundings of Tilghman, Maryland. Located in the charming Talbot County, this waterfront community is a hidden gem that offers both tranquility and an idyllic lifestyle. With its stunning views of the Chesapeake Bay and lush landscapes, Tilghman On Chesapeake is perfect for those seeking a peaceful retreat, yet still within reach of modern conveniences.

The homes in this delightful subdivision are designed to cater to a variety of tastes and preferences, with many options available for under $900,000. These properties boast a unique blend of classic charm and contemporary amenities, making them ideal for families, retirees, or anyone looking to embrace a laid-back lifestyle by the water. Many homes feature spacious layouts, inviting outdoor spaces, and stunning views, allowing residents to fully enjoy the beauty of their surroundings.

Living in Tilghman On Chesapeake means embracing a community that values both nature and neighborly connections. Residents have access to a range of recreational activities, from boating and fishing to biking and hiking along the scenic trails. The local community is warm and welcoming, making it easy to forge lasting friendships and create cherished memories.

Whether you’re searching for a seasonal getaway or a permanent residence, Tilghman On Chesapeake offers an exceptional quality of life. Discover your dream home in this enchanting subdivision and experience the best of coastal living in Maryland!

Newest Tilghman On Chesapeake Homes under $900,000

21477 Island Club Rd, Tilghman
$895,000
4 Beds ⋅ 3 Baths
Price reduced SIGNIFICANTLY!! Beautiful views of Harris Creek and the Choptank River beyond provide a stunning backdrop for this beautifully maintained home in the established community of Tilghman on Chesapeake. A welcoming front porch framed by mature landscaping and colorful gardens leads into a bright, light-filled interior featuring soaring two-story ceilings, hardwood floors, crown moldings, and abundant natural light. Designed for both everyday living and entertaining, the gourmet kitchen opens to a spacious family room with a gas fireplace, breakfast area, and inviting sunroom. The adjoining rear deck, complete with a hot tub, provides a wonderful setting for outdoor entertaining while overlooking the beautifully landscaped grounds and tranquil water views. The main level also includes gracious formal living and dining rooms, as well as a private office. The upper level overlooks the family room below and features a spacious primary suite with a private balcony and luxurious ensuite bath with a jetted tub and walk-in shower. Three additional bedrooms—one currently used as a library—share a full hall bath. An attached two-car garage provides convenient parking and storage. Residents of Tilghman on Chesapeake enjoy an exceptional array of amenities, including a waterfront clubhouse, swimming pool, picnic area, community pier, and private boat slips available for lease, offering residents an ideal opportunity to enjoy the waterfront lifestyle of Maryland’s Eastern Shore.

21477 Island Club Rd, Tilghman

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

5559 Trafalgar Cir, Tilghman
$550,000
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:

5648 Trafalgar Cir, Tilghman
$514,888
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:

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