- 5 beds
- 3 baths
- 4,214 sqft
- ~1 acre lot
- $415 per sqft
- 2005 build
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.
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Last updated Jun 17, 2025
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MLS# MDTA2010832 —
The Building
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Year Built:2005
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Year Built Source:Assessor
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Roof:Shingle
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New Construction:No
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Construction Materials:Vinyl Siding
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Structure Type:Detached
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Architectural Style:Colonial
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Levels:2
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Main Entrance:West
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Window Features:Screens
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Accessibility Features:>84, 2+ Access Exits
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Foundation Details:Crawl Space
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Basement:Yes
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Basement Type:Sump Pump
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Total SqFt Source:Assessor
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Total Below Grade SqFt Source:Assessor
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Above Grade Finished Area Units:Square Feet
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Above Grade Finished SqFt:4214
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Above Grade Finished SqFt Source:Assessor
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Below Grade Finished Area Units:Square Feet
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Below Grade Unfinished Area Units:Square Feet
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Below Grade Finished SqFt Source:Assessor
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Below Grade Unfinished SqFt Source:Assessor
Interior
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Interior Features: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
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Room List:Living Room, Dining Room, Primary Bedroom, Sitting Room, Bedroom 2, Bedroom 3, Bedroom 4, Kitchen, Foyer, Breakfast Room, Bedroom 1, Laundry, Bathroom 1, Primary Bathroom, Half Bath
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Fireplace:No
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Living Area SqFt Source:Assessor
Room Dimensions
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Total SqFt:4214
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Living Area SqFt:4,214 Sqft
Financial & Terms
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Sale Type:Standard
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Acceptable Financing:Cash, Conventional
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Possession:Settlement
Location
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Directions:FROM EASTON RT. 33 THROUGH ST. MICHAELS TO TILGHMAN ISLAND. TAKE A RIGHT ON LEEWARD LANE THEN LFEFT INTO DRIVEWAY. SIGN POSTED.
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Latitude:38.70239346
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Longitude:-76.34317221
The Property
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Property Type:Residential
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Lot Size Units:Square Feet
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Lot Size Acres:1.19
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Lot Size Source:Assessor
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Lot SqFt:51,836 Sqft
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Zoning:RESIDENTIAL
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View:Water
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In City Limits:No
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Outdoor Living Structures:Balcony, Deck(s), Porch(es)
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Other Structures:Above Grade, Below Grade
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Waterview:Yes
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Waterfront:Yes
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Water Oriented:Yes
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Water Access:Yes
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Distance To Water:Blocks
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Water Body Name:CHESAPEAKE BAY
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Water Body Type:Bay
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Mean Low Water Feet:4
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Navigable Water:Yes
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Water Frontage In Feet:200
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Land Use Code:R
Listing Agent
- Contact info:
- Agent phone:
- (484) 889-9364
- Office phone:
- (302) 360-0300
Taxes
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Tax ID Number:2105189950
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Tax Year:2024
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Tax Lot:13A
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Tax Annual Amount:$8,231
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Tax Assessed Value:$953,600
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Year Assessed:2025
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County Tax:8231.00
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Total Taxes Payment Frequency:Annually
Beds
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Bedrooms:5
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Bedrooms Main Level:1
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Upper Level Bedrooms:4
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Upper Level 1 Bedrooms:4
Baths
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Total Baths:3
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Full Baths:2
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Half Baths:1
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Main Level Baths:2.00
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Main Level Full Baths:1
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Main Level Half Baths:1
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Upper Level Full Baths:1
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Upper Level Total Baths:1
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Upper Level Total Baths:1.00
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Upper Level Full Baths:1
Heating & Cooling
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Cooling Type:Ceiling Fan(s), Central A/C
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Central Air:Yes
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Cooling Fuel:Electric
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Heating:Yes
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Heating Type:Heat Pump(s)
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Heating Fuel:Electric, Natural Gas
Utilities
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Sewer/Septic:Public Sewer
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Hot Water:Electric
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Water Source:Well
Appliances
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Appliances:Dishwasher, Dryer, Extra Refrigerator/Freezer, Icemaker, Instant Hot Water, Microwave, Oven/Range - Gas, Range Hood, Refrigerator, Six Burner Stove, Washer, Exhaust Fan
Schools
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School District Name:Talbot County Public Schools
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School District Source:Listing Agent
The Community
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Subdivision Name:Paw Paw Cove
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Senior Community:No
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Pool:No Pool
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HOA:No
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Condo/Coop Association:No
Parking
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Total Garage and Parking Spaces:3
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Garage:Yes
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Garage Features:Garage Door Opener
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Garage Spaces:3.00
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Type of Parking:Attached Garage, Driveway
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# of Attached Garage Spaces:3
Extra Units
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Vacation Rental:No
Monthly cost estimate

Asking price
$1,750,000
Expense | Monthly cost |
---|---|
Mortgage
This calculator is intended for planning and education purposes only. It relies on assumptions and information provided by you regarding your goals, expectations and financial situation, and should not be used as your sole source of information. The output of the tool is not a loan offer or solicitation, nor is it financial or legal advice. |
$9,370
|
Taxes | $685 |
Insurance | $481 |
Utilities | $216 See report |
Total | $10,752/mo.* |
*This is an estimate |
Walk Score®
Provided by WalkScore® Inc.
Walk Score is the most well-known measure of walkability for any address. It is based on the distance to a variety of nearby services and pedestrian friendliness. Walk Scores range from 0 (Car-Dependent) to 100 (Walker’s Paradise).
Bike Score®
Provided by WalkScore® Inc.
Bike Score evaluates a location's bikeability. It is calculated by measuring bike infrastructure, hills, destinations and road connectivity, and the number of bike commuters. Bike Scores range from 0 (Somewhat Bikeable) to 100 (Biker’s Paradise).
Air Pollution Index
Provided by ClearlyEnergy
The air pollution index is calculated by county or urban area using the past three years data. The index ranks the county or urban area on a scale of 0 (best) - 100 (worst) across the United Sates.
Sale history
Date | Event | Source | Price | % Change |
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6/17/25
Jun 17, 2025
|
Price Changed | BRIGHT | $1,750,000 | -20.5% |
5/26/25
May 26, 2025
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Listed / Active | BRIGHT | $2,200,000 |