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5520 Leeward Lane

TILGHMAN, MD 21671

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.

Listing courtesy of BRIGHT / Keller Williams Realty

Last checked: Checking… • Last updated Jun 17, 2025 •

MLS# MDTA2010832 —

The Building

Year Built:

2005
Year Built Source:

Assessor
Roof:

Shingle
New Construction:

No
Construction Materials:

Vinyl Siding
Structure Type:

Detached
Architectural Style:

Colonial
Levels:

2
Main Entrance:

West
Window Features:

Screens
Accessibility Features:

>84, 2+ Access Exits
Foundation Details:

Crawl Space
Basement:

Yes
Basement Type:

Sump Pump
Total SqFt Source:

Assessor
Total Below Grade SqFt Source:

Assessor
Above Grade Finished Area Units:

Square Feet
Above Grade Finished SqFt:

4214
Above Grade Finished SqFt Source:

Assessor
Below Grade Finished Area Units:

Square Feet
Below Grade Unfinished Area Units:

Square Feet
Below Grade Finished SqFt Source:

Assessor
Below Grade Unfinished SqFt Source:

Assessor

Interior

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
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
Fireplace:

No
Living Area SqFt Source:

Assessor

Room Dimensions

Total SqFt:

4214
Living Area SqFt:

4,214 Sqft

Financial & Terms

Sale Type:

Standard
Acceptable Financing:

Cash, Conventional
Possession:

Settlement

Location

Directions:

FROM EASTON RT. 33 THROUGH ST. MICHAELS TO TILGHMAN ISLAND. TAKE A RIGHT ON LEEWARD LANE THEN LFEFT INTO DRIVEWAY. SIGN POSTED.
Latitude:

38.70239346
Longitude:

-76.34317221

The Property

Property Type:

Residential
Lot Size Units:

Square Feet
Lot Size Acres:

1.19
Lot Size Source:

Assessor
Lot SqFt:

51,836 Sqft
Zoning:

RESIDENTIAL
View:

Water
In City Limits:

No
Outdoor Living Structures:

Balcony, Deck(s), Porch(es)
Other Structures:

Above Grade, Below Grade
Waterview:

Yes
Waterfront:

Yes
Water Oriented:

Yes
Water Access:

Yes
Distance To Water:

Blocks
Water Body Name:

CHESAPEAKE BAY
Water Body Type:

Bay
Mean Low Water Feet:

4
Navigable Water:

Yes
Water Frontage In Feet:

200
Land Use Code:

R

Listing Agent

Contact info:

Taxes

Tax ID Number:

2105189950
Tax Year:

2024
Tax Lot:

13A
Tax Annual Amount:

$8,231
Tax Assessed Value:

$953,600
Year Assessed:

2025
County Tax:

8231.00
Total Taxes Payment Frequency:

Annually

Beds

Bedrooms:

5
Bedrooms Main Level:

1
Upper Level Bedrooms:

4
Upper Level 1 Bedrooms:

4

Baths

Total Baths:

3
Full Baths:

2
Half Baths:

1
Main Level Baths:

2.00
Main Level Full Baths:

1
Main Level Half Baths:

1
Upper Level Full Baths:

1
Upper Level Total Baths:

1
Upper Level Total Baths:

1.00
Upper Level Full Baths:

1

Heating & Cooling

Cooling Type:

Ceiling Fan(s), Central A/C
Central Air:

Yes
Cooling Fuel:

Electric
Heating:

Yes
Heating Type:

Heat Pump(s)
Heating Fuel:

Electric, Natural Gas

Utilities

Sewer/Septic:

Public Sewer
Hot Water:

Electric
Water Source:

Well

Appliances

Appliances:

Dishwasher, Dryer, Extra Refrigerator/Freezer, Icemaker, Instant Hot Water, Microwave, Oven/Range - Gas, Range Hood, Refrigerator, Six Burner Stove, Washer, Exhaust Fan

Schools

School District Name:

Talbot County Public Schools
School District Source:

Listing Agent

The Community

Subdivision Name:

Paw Paw Cove
Senior Community:

No
Pool:

No Pool
HOA:

No
Condo/Coop Association:

No

Parking

Total Garage and Parking Spaces:

3
Garage:

Yes
Garage Features:

Garage Door Opener
Garage Spaces:

3.00
Type of Parking:

Attached Garage, Driveway
# of Attached Garage Spaces:

3

Extra Units

Vacation Rental:

No

Monthly cost estimate

Asking price

$1,750,000

Expense	Monthly cost
Mortgage	$9,370
Taxes	$685
Insurance	$481
Utilities	$216 See report
Total	$10,752/mo.^*
	^*This is an estimate

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Bike Score®

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Air Pollution Index

Provided by ClearlyEnergy

Sale history

Date	Event	Source	Price	% Change
6/17/25 Jun 17, 2025	Price Changed	BRIGHT	$1,750,000	-20.5%
5/26/25 May 26, 2025	Listed / Active	BRIGHT	$2,200,000

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This house located in Tilghman Island, MD 21671 is currently for sale for $1,750,000. 5520 Leeward Lane is a 4,214 square foot house with 5 beds and 3 baths. This house is in the attendance area of Easton High School.

Listing Courtesy of: BRIGHT and Keller Williams Realty.

The information included in this listing is provided exclusively 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 on each listing is furnished by the owner and deemed reliable to the best of his/her knowledge, but should be verified by the purchaser. BRIGHT MLS and Estately assume no responsibility for typographical errors, misprints or misinformation. This property is offered without respect to any protected classes in accordance with the law. Some real estate firms do not participate in IDX and their listings do not appear on this website. Some properties listed with participating firms do not appear on this website at the request of the seller.