1. Maryland
2. Tilghman
3. 5520 LEEWARD LN

5520 LEEWARD LN, Tilghman, MD 21671

• 5 beds |
• 3 baths |
• 4,214 sqft

Property Description

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 Status:

Active

Date Added:

May 27, 2025 at 05:00AM

Listing Office:

Keller Williams Realty : 3023600300

Listing Agent:

Samantha Kay Jackson : 4848899364

MLS ID:

MDTA2010832

Interior

• General: Family Room Off KitchenBreakfast AreaKitchen - Table SpaceDining AreaBuilt-InsWindow TreatmentsEntry Level BedroomUpgraded CountertopsPrimary Bath(s)Floor Plan - Open
• Rooms: Living RoomDining RoomPrimary BedroomSitting RoomBedroom 2Bedroom 3Bedroom 4KitchenFoyerBreakfast RoomBedroom 1LaundryBathroom 1Primary BathroomHalf Bath
• Appliances: DishwasherDryerExtra Refrigerator/FreezerIcemakerInstant Hot WaterMicrowaveOven/Range - GasRange HoodRefrigeratorSix Burner StoveWasherExhaust Fan
• Basement: Sump pump
• A/C: Ceiling Fan(s)Central A/C
• Heating: Heat Pump(s)ElectricNatural Gas
• Disability Feature: >84" Garage Door2+ Access Exits

Exterior

Construction

Location

Lot

Utilities

Financial

This listing courtesy of Samantha Kay Jackson, Keller Williams Realty