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Dana Ubele

dana@thepropertyalliance.com +1(856) 888-1133

Listed by Samantha Kay Jackson • Keller Williams Realty

$ 1,200,000

Est. payment -/mo

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Active

5520 LEEWARD LN Tilghman, MD 21671

5 Beds

3 Baths

4,214 SqFt

UPDATED:

Key Details

Property Type Single Family Home

Sub Type Detached

Listing Status Active

Purchase Type For Sale

Square Footage 4,214 sqft

Price per Sqft $284

Subdivision Paw Paw Cove

MLS Listing ID MDTA2010832

Style Colonial

Bedrooms 5

Full Baths 2

Half Baths 1

HOA Y/N N

Abv Grd Liv Area 4,214

Year Built 2005

Available Date 2025-05-27

Annual Tax Amount $8,231

Tax Year 2024

Lot Size 1.190 Acres

Acres 1.19

Property Sub-Type Detached

Source BRIGHT

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.

Location

State MD

County Talbot

Zoning RESIDENTIAL

Direction West

Rooms

Other Rooms 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

Basement Sump Pump

Main Level Bedrooms 1

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

Hot Water Electric

Heating Heat Pump(s)

Cooling Ceiling Fan(s), Central A/C

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

Fireplace N

Window Features Screens

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

Heat Source Electric, Natural Gas

Exterior

Exterior Feature Balcony, Deck(s), Porch(es)

Parking Features Garage Door Opener

Garage Spaces 3.0

Water Access Y

View Water

Roof Type Shingle

Accessibility >84\" Garage Door, 2+ Access Exits

Porch Balcony, Deck(s), Porch(es)

Attached Garage 3

Total Parking Spaces 3

Garage Y

Building

Story 2

Foundation Crawl Space

Above Ground Finished SqFt 4214

Sewer Public Sewer

Water Well

Architectural Style Colonial

Level or Stories 2

Additional Building Above Grade, Below Grade

New Construction N

Schools

School District Talbot County Public Schools

Others

Senior Community No

Tax ID 2105189950

Ownership Fee Simple

SqFt Source 4214

Acceptable Financing Cash, Conventional

Listing Terms Cash, Conventional

Financing Cash,Conventional

Special Listing Condition Short Sale

Dana Ubele

Broker | License ID: 0448855

+1(856) 888-1133

Dana Ubele

5520 LEEWARD LN Tilghman, MD 21671

Key Details

Location

Rooms

Interior

Exterior

Building

Schools

Others

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5520 LEEWARD LN