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$1,750,000
28 Days On Site

5520 LEEWARD LANE
TILGHMAN, MD 21671

For Sale|Single Family Residence|Active
5
Beds
3
Total Baths
2
Full Baths
1
Partial Bath
4,214
SqFt
$415
/SqFt
2005
Built
Subdivision:
PAW PAW COVE
County:
TALBOT
Listing courtesy of Keller Williams Realty

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5520 LEEWARD LANE5520 LEEWARD LANE5520 LEEWARD LANE5520 LEEWARD LANE
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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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Listing Snapshot
Price 
$1,750,000
Days On Site 
28 Days
Bedrooms 
5
Inside Area (SqFt) 
4,214 sqft
Total Baths 
3
Full Baths 
2
Partial Baths 
1
Lot Size 
1.19 Acres
Year Built 
2005
MLS® Number 
MDTA2010832
Status 
Active
Property Tax 
$8,231
HOA/Condo/Coop Fees 
N/A
Sq Ft Source 
Assessor
Friends & Family
Recent Activity
4 days agoPrice changed to $1,750,000
4 days agoListing updated with changes from the MLS®
4 weeks agoStatus changed to Active
4 weeks agoListing first seen on site
General Features
Acres 
1.19
Attached Garage 
Yes
Direction Faces 
West
Garage 
Yes
Garage Spaces 
3
Parking 
Garage Door OpenerGarageDrivewayAttached
Parking Spaces 
3
Property Sub Type 
Single Family Residence
Sewer 
Public Sewer
Special Circumstances 
Standard
SqFt Above 
4214
Stories 
Two
Style 
Colonial
Water Source 
Well
Zoning 
RESIDENTIAL
Interior Features
Appliances 
Gas RangeGas OvenCooktopElectric Water HeaterDishwasherDryerIce MakerInstant Hot WaterMicrowaveRange HoodRefrigeratorWasherExhaust Fan
Basement 
Crawl SpaceSump Pump
Cooling 
Central AirCeiling Fan(s)Electric
Heating 
Exhaust FanElectricNatural GasHeat Pump
Interior 
Built-in FeaturesOpen Floorplan
Laundry Features 
Laundry Room
Main Level Bedrooms 
1
Window Features 
Window CoveringsScreensWindow Treatments
Dining Room 
Level - Main
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Exterior Features
Construction Details 
Vinyl Siding
Exterior 
Balcony
Frontage 
Bay/HarborWaterfront
Lot Features 
Waterfront
Patio And Porch 
DeckPorch
Pool Features 
None
Roof 
Shingle
View 
Water
Waterfront 
Yes
Waterfront Features 
CHESAPEAKE BAY
Waterview 
Water
Windows/Doors 
Window CoveringsScreensWindow Treatments
Community Features
School District 
TALBOT COUNTY PUBLIC SCHOOLS
Schools
School District
TALBOT COUNTY PUBLIC SCHOOLS
Elementary School
Unknown
Middle School
Unknown
High School
Unknown
Listing courtesy of Keller Williams Realty



The real estate listing information is provided by Bright MLS is for the consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumer may be interested in purchasing. Any information relating to real estate for sale or lease referenced on this web site comes from the Internet Data Exchange (IDX) program of the Bright MLS. This web site references real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. The accuracy of all information is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. Properties in listings may have been sold or may no longer be available. The data contained herein is copyrighted by Bright MLS and is protected by all applicable copyright laws. Any unauthorized collection or dissemination of this information is in violation of copyright laws and is strictly prohibited. Copyright © 2020 Bright MLS. All rights reserved.

Neighborhood & Commute
Source: Walkscore
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