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"Tranquil Waters" is a rare Chesapeake Bay waterfront retreat on Tilghman Island, comprehensively renovated to the highest standard and designed to capture panoramic water views from nearly every room. This extraordinary residence blends refined coastal architecture with the relaxed elegance of Eastern Shore living. Dramatic walls of glass, soaring ceilings, and open living spaces flood the home with natural light while framing endless Bay views, spectacular sunrises, and unforgettable sunsets. The fully renovated interior includes a redesigned chef's kitchen, spa-inspired baths, new windows and sliding doors, updated trim and fireplace features, and extensive system upgrades throughout. Exceptional waterfront amenities include expansive Trex decking, deep-water dockage, a heated indoor pool and spa pavilion, and seamless indoor-outdoor living designed for entertaining and year-round enjoyment. Major capital improvements include new HVAC systems, roof replacement, hot water heater, air purification system, decking, windows, doors, and more, offering true turnkey peace of mind. Beyond its appeal as a private waterfront retreat, "Tranquil Waters" has enjoyed a Successfull Luxury Vacation Rental history, creating an appealing opportunity for buyers seeking both lifestyle and INVESTMENT POTENTIAL. Equally suited as a luxury primary residence, waterfront getaway, or private retreat, "Tranquil Waters" delivers the ultimate Eastern Shore lifestyle: water, light, privacy, and complete escape.

7 Beds ⋅ 6 Baths

"Tranquil Waters" is a rare Chesapeake Bay waterfront retreat on Tilghman Island, comprehensively renovated to the highest standard and designed to capture panoramic water views from nearly every room. This extraordinary residence blends refined coastal architecture with the relaxed elegance of Eastern Shore living. Dramatic walls of glass, soaring ceilings, and open living spaces flood the home with natural light while framing endless Bay views, spectacular sunrises, and unforgettable sunsets. The fully renovated interior includes a redesigned chef's kitchen, spa-inspired baths, new windows and sliding doors, updated trim and fireplace features, and extensive system upgrades throughout. Exceptional waterfront amenities include expansive Trex decking, deep-water dockage, a heated indoor pool and spa pavilion, and seamless indoor-outdoor living designed for entertaining and year-round enjoyment. Major capital improvements include new HVAC systems, roof replacement, hot water heater, air purification system, decking, windows, doors, and more, offering true turnkey peace of mind. Beyond its appeal as a private waterfront retreat, "Tranquil Waters" has enjoyed a Successfull Luxury Vacation Rental history, creating an appealing opportunity for buyers seeking both lifestyle and INVESTMENT POTENTIAL. Equally suited as a luxury primary residence, waterfront getaway, or private retreat, "Tranquil Waters" delivers the ultimate Eastern Shore lifestyle: water, light, privacy, and complete escape.

21642 Chicken Point Rd, Tilghman

Listing courtesy of Chesapeake Bay Real Estate Plus, LLC. Contact:

$1,750,000

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.

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:

$1,200,000

Unique Tilghman Island Property. Zoned Residential-Commercial. Situated on a 2.74 acre fenced yard. This 2450 sq ft Stone Rancher has many upgrades, new 2 car garage and 24 new commercial slips. The possibilities are endless....... Vacation Rental, 24 brand new slips, typically rent from 175.00-225.00 monthly. Develop a new fishing center, crabbing tours, sunsets cruises. Let's see what you can dream up??

3 Beds ⋅ 3 Baths

Unique Tilghman Island Property. Zoned Residential-Commercial. Situated on a 2.74 acre fenced yard. This 2450 sq ft Stone Rancher has many upgrades, new 2 car garage and 24 new commercial slips. The possibilities are endless....... Vacation Rental, 24 brand new slips, typically rent from 175.00-225.00 monthly. Develop a new fishing center, crabbing tours, sunsets cruises. Let's see what you can dream up??

21441 Dogwood Cove Rd, Tilghman

Listing courtesy of Chesapeake Bay Real Estate Plus, LLC. Contact:

$329,000

Live the Tilghman Island lifestyle just steps from the Chesapeake Bay. Perfectly positioned in the heart of historic Tilghman Island, this updated four-bedroom home offers the ability to enjoy one of Maryland's most authentic waterfront communities without the waterfront price tag. Walk to marinas, waterfront restaurants, charter fishing, Tilghman Wharf, and the iconic drawbridge, or spend your days exploring the Chesapeake by boat, kayak, or bicycle. Originally inspired by one of Tilghman's classic "W" homes, the residence blends timeless island character with modern updates. Inside, you'll find a spacious, open floor plan featuring an updated kitchen with granite countertops, stainless steel appliances, and abundant cabinetry, along with beautifully renovated bathrooms, new flooring, and a flexible layout that includes a first-floor bedroom and full bath—ideal for guests or one-level living. Three additional bedrooms and another updated full bath are located upstairs, providing plenty of space for family and friends. A new HVAC system adds year-round comfort, while the generous yard offers room for gardening, entertaining, or simply relaxing after a day on the water. Whether you're searching for a full-time residence, a weekend retreat, or an investment in one of the Eastern Shore's most charming villages, this home delivers exceptional value at an attractive price point. Experience the slower pace, rich maritime heritage, and unmatched sense of community that make Tilghman Island one of the Chesapeake Bay's hidden gems.

4 Beds ⋅ 2 Baths

Live the Tilghman Island lifestyle just steps from the Chesapeake Bay. Perfectly positioned in the heart of historic Tilghman Island, this updated four-bedroom home offers the ability to enjoy one of Maryland's most authentic waterfront communities without the waterfront price tag. Walk to marinas, waterfront restaurants, charter fishing, Tilghman Wharf, and the iconic drawbridge, or spend your days exploring the Chesapeake by boat, kayak, or bicycle. Originally inspired by one of Tilghman's classic "W" homes, the residence blends timeless island character with modern updates. Inside, you'll find a spacious, open floor plan featuring an updated kitchen with granite countertops, stainless steel appliances, and abundant cabinetry, along with beautifully renovated bathrooms, new flooring, and a flexible layout that includes a first-floor bedroom and full bath—ideal for guests or one-level living. Three additional bedrooms and another updated full bath are located upstairs, providing plenty of space for family and friends. A new HVAC system adds year-round comfort, while the generous yard offers room for gardening, entertaining, or simply relaxing after a day on the water. Whether you're searching for a full-time residence, a weekend retreat, or an investment in one of the Eastern Shore's most charming villages, this home delivers exceptional value at an attractive price point. Experience the slower pace, rich maritime heritage, and unmatched sense of community that make Tilghman Island one of the Chesapeake Bay's hidden gems.

21524 Chicken Point Rd, Tilghman

Listing courtesy of Benson & Mangold, LLC. Contact:

$300,000

REAL ESTATE AUCTION featuring ON SITE and SIMULCAST BIDDING!! Online Bidding Opens - Thursday, October 29, 2026. Live On Site Auction - Friday, October 30, 2026 at 12:00 noon. List price is opening bid only. Live Auction Bidders – A $40,000 deposit, payable by cashier’s check, will be required of the purchaser at time and place of sale. Online Auction Bidders – A $40,000 deposit, payable by cashier’s check or wire transfer, is due from all online bidders prior to bidding platform approval. That deposit to be applied to the purchase price for the purchaser, and all other deposits returned within 1 business day. A once in a lifetime opportunity to purchase a waterfront restaurant building with tiki bar in one of the most sought after locations on Maryland’s Eastern Shore. Located at the gateway to Tilghman Island and facing the Tilghman Island Drawbridge, considered to be the busiest on the East Coast, the property features ample exposure to both boat and vehicle traffic. The auction provides an opportunity for both users and investors to purchase a trophy waterfront property in a truly unique, desirable location with extensive long-term potential.

6136 Tilghman Island Rd, Tilghman

Listing courtesy of A.J. Billig & Company. Contact:

$269,000

This well-maintained home offers a peaceful Eastern Shore lifestyle with easy access to boating, fishing, crabbing, local marinas, and waterfront dining. Enjoy the relaxed island atmosphere while still being just a short drive from historic St. Michaels and other nearby amenities. The property features comfortable living spaces, a spacious yard, and the opportunity to enjoy all that Tilghman Island has to offer. Whether you're looking for a primary residence, vacation retreat, or investment opportunity, this home provides the perfect setting to experience Maryland's Chesapeake Bay lifestyle. Currently priced significantly under current appraised value!!!

3 Beds ⋅ 1 Baths

This well-maintained home offers a peaceful Eastern Shore lifestyle with easy access to boating, fishing, crabbing, local marinas, and waterfront dining. Enjoy the relaxed island atmosphere while still being just a short drive from historic St. Michaels and other nearby amenities. The property features comfortable living spaces, a spacious yard, and the opportunity to enjoy all that Tilghman Island has to offer. Whether you're looking for a primary residence, vacation retreat, or investment opportunity, this home provides the perfect setting to experience Maryland's Chesapeake Bay lifestyle. Currently priced significantly under current appraised value!!!

21647 Camper Cir, Tilghman

Listing courtesy of Keller Williams Realty. Contact:

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