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About the Listing KWBCH05 - 3333137
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.
Listing Highlights for 5520 Leeward Ln
Status
Active
Days on Site
109
Property Type
Residential
MLS ®
MDTA2010832
Year Built
2005
Total Square Footage
4,214
Lot/Acreage
1.19
Interior Details
- Bedrooms: 5
- Bathrooms: 2 Full / 1 Half
- Appliances: Dishwasher, Dryer, Extra Refrigerator/Freezer, Icemaker, Instant Hot Water, Microwave, Oven/Range - Gas, Range Hood, Refrigerator, Six Burner Stove, Washer, Exhaust Fan
- Air Cond: Ceiling Fan(s),Central A/C
- Heating: Heat Pump(s)
- Fireplaces:
- Floor:
- Above Ground Sq Ft: 4214
- Below Ground Sq Ft: 0
- Basement: Sump Pump
- Other: Family Room Off Kitchen,Breakfast Area,Kitchen - Table Space,Dining Area,Built-Ins,Window Treatments,Entry Level Bedroom,Upgraded Countertops,Primary Bath(s),Floor Plan - Open,Main Floor Bedrooms: 1
- Water: Well
Exterior Details
- Lot Description: Not New Construction,Horse Property: No,Waterfront
- Garage Capacity: 3 car
- Parking Spaces: 3
- Zoning: RESIDENTIAL
- Roof: Shingle
- Others:
- Sewer: Public Sewer
- Parking Features: Garage Door Opener,Attached Garage,Driveway,3+ Spaces,2+ Spaces,1+ Spaces
Financial Details
- Tax Amount: $8,231
- Taxes w/Assessments: N/A
- Tax/Property ID: N/A
- Tax Year: 2024
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Listing Location
Questions About..
5520 Leeward Ln Tilghman, MD 21671
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