Change Real Estate Presents:

5520 Leeward Lane
Tilghman MD 21671

For Sale: $1,100,000.00 Active

List Date: 2025-05-27

Tilghman
5 bedrooms
3 bathrooms
4,214 build ft2
51,836 land ft2

About This Property

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 Agent: Samantha Kay Jackson. Keller Williams Realty 484-889-9364 samantha@griffinhigginsteam.com

Property Features

Location Information
County:
Subdivision: PAW PAW COVE
click to open map in a new window
Interior Features
Appliances: Dishwasher, Dryer, Extra Refrigerator/Freezer, Icemaker, Instant Hot Water, Microwave, Oven/Range - Gas, Range Hood, Refrigerator, Six Burner Stove, Washer, Exhaust Fan
Interior: 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
Laundry:
Furnished: None
Flooring:
Water: Well
Cooling: Ceiling Fan(s), Central A/C
Heating: Heat Pump(s)
Fireplaces: None
Windows: Screens
Utilities:
Sewer: Public Sewer
Rooms
Room Type: Bedroom 4
Dimensions: 14 X 13
Features: Flooring - Carpet
Level: Upper 1
Room Type: Bedroom 2
Dimensions: 14 X 14
Features: Flooring - Carpet
Level: Upper 1
Room Type: Bedroom 3
Dimensions: 12 X 15
Features: Flooring - Carpet
Level: Upper 1
Room Type: Bedroom 1
Dimensions: 15 X 12
Features: Flooring - HardWood
Level: Upper 1
Room Type: Bathroom 1
Level: Upper 1
Room Type: Living Room
Level: Upper 1
Room Type: Kitchen
Level: Upper 1
Room Type: Dining Room
Features: Flooring - HardWood
Level: Main
Room Type: Foyer
Dimensions: 13 X 9
Features: Flooring - HardWood
Level: Main
Room Type: Sitting Room
Dimensions: 14 X 14
Features: Flooring - HardWood
Level: Main
Room Type: Kitchen
Dimensions: 15 X 9
Features: Flooring - HardWood
Level: Main
Room Type: Living Room
Dimensions: 16 X 14
Features: Flooring - HardWood
Level: Main
Room Type: Breakfast Room
Level: Main
Room Type: Primary Bedroom
Level: Main
Room Type: Primary Bathroom
Features: Double Sink, Walk-In Closet(s), Bathroom - Soaking Tub
Level: Main
Room Type: Laundry
Level: Main
Room Type: Half Bath
Level: Main
Exterior Features
Year Built: 2005
Legal Subdivision: *
Subdivision Name: Paw Paw Cove
Garage Spaces: 3.0
Schools
Elementary School: None
Junior High School: None
High School: None

IDXListing Courtesy of Samantha Kay Jackson. Keller Williams Realty 484-889-9364 samantha@griffinhigginsteam.com

Property Photos [Click to enlarge]

Bright © 2026 Bright, All Rights Reserved.

The data related to real estate for sale on this website comes in part from the INTERNET DATA EXCHANGE (IDX) program of the Bright MLS. Real estate listings held by brokerage firms other than this site owner are marked with the IDX logo.

IDX information is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

The information is not guaranteed. Measurements are solely for the purpose of marketing, may not be exact, and should not be relied upon for loan, valuation or other purposes. All listing information is deemed reliable but not guaranteed.

This content was last refreshed on 2026-04-16 10:59 AM. Some properties which appear for sale on this website may subsequently have sold or may no longer be available.

DMCA Notice