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Residential > House
Active
05/27/2025
List Price
$1,200,000$285/ft²

5520 Leeward Ln
Tilghman, MD 21671

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  • Malobo BannerMalobo Banner Square
    5520 Leeward Ln, Tilghman, MD 21671 is a 5 bed, 3 bath, 4,214 ft² house built in 2005 on a 1.190 acre lot. This house is currently on the market for $1,200,000, and it was last sold in 2004 for $330,000. The latest TopHap estimate of the house's value is $1,788,534.

    Property Valuations

    Latest estimates for 5520 Leeward Ln based on TopHap automated valuation model (AVM).

    MLS Description

    The listing agent's description. Original Listing

    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 Agents

    The listing agent for 5520 Leeward Ln is Samantha Kay Jackson.

    Current Ownership

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    Property History

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    Property Events

    Environment

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    School Information

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    Neighborhood

    This property is located in Tilghman Island, Tilghman, MD 21671.

    Market Trends

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    Copyright © 2025 Bright MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

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