5520 Leeward Lane, Tilghman, MD 21671 - Photo 1

1/1

$1,000,000

Sold
Closed
Single Family
5 Beds
2 Full Baths
1 Partial Bath
4,214 Sq. Ft.
3 Car Garage

1/1

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.

Full Property Details

Full Property Details for 5520 Leeward Ln

General

Sold For: $1,000,000
Taxes: $8,231 (2024)
Status: Closed
Type: Single Family
Source: BrightMLSMidAtlantic
MLS ID: MDTA2010832
Added to Site: 420 day(s) ago

Interior

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

Rooms

Bathrooms

Total Bathrooms: 3
Full Bathrooms: 2
Half Bathrooms: 1
Upper Floor Baths: 1
Upper - Full Baths: 1
Main Floor Baths: 2
Main - Full Baths: 1
Main - 1/2 Baths: 1

Bedrooms

Total Bedrooms: 5
Bedrooms Upper: 4
Bedrooms Main & Up: 1

Exterior

Porch/Patio/Deck: Balcony, Deck(s), Porch(es)

Parking

Garage: Yes
Garage Spaces: 3
Total Spaces: 3
Parking Type: Attached Garage, Driveway
Garage Description: Garage Door Opener

Location

County: TALBOT
Subdivision: PAW PAW COVE
Driving Directions: FROM EASTON RT. 33 THROUGH ST. MICHAELS TO TILGHMAN ISLAND. TAKE A RIGHT ON LEEWARD LANE THEN LFEFT INTO DRIVEWAY. SIGN POSTED.
Direction Faces: West

School Information

School District: Talbot County Public Schools

Heating & Cooling

Central air: Yes
Cooling Type: Ceiling Fan(s), Central A/C
Cooling Fuel: Electric
Heating Type: Heat Pump(s)
Heating Fuel: Electric, Natural Gas
Water Heater: Electric

Utilities

Sewer: Public Sewer
Water: Well
Dist. to Water: 0 Blocks

Structural Information

Architectural Style: Colonial
Structure Type: Detached
Construction: Vinyl Siding
Basement: Yes
Basement Desc.: Sump Pump
Foundation: Crawl Space
Roof: Shingle
Windows: Screens
Stories Description: Main, Upper 1
Square Feet: 4,214
Sq. Ft. Source: Assessor
Living Area: 4,214 Sq. Ft.
Finished Above Grnd: 4,214 Sq. Ft.
Year Built: 2005
Year Built Source: Assessor

Lot Features

Property View: Water
Lot Size (Acres): 1.19
Lot Size (Sq. Ft.): 51,836
Lot Size Source: Assessor
Zoning: RESIDENTIAL

Water Features

Water Front: Yes
Water View: Yes
Navigable Water: Yes
Water Access: Yes
Water Front Type: Bay
Water Front Name: CHESAPEAKE BAY

Financial Considerations

Price Per Sq. Ft.: $261.03
Assessment Year: 2025
County Tax: $8,231
County Tax Freq: Annually
Tax w/Assessment: $953,600
Tax Amount: $8,231
Tax Year: 2024
Terms: Short Sale

Disclosures and Reports

Ownership: Fee Simple
Lot Number: 13A

Listed by Keller Williams Realty, Samantha Kay Jackson
Sold by Chesapeake Bay Real Estate Plus, LLC, Dawn A Lednum

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Listing agent

— 5520 Leeward Ln —

Samantha Kay Jackson

Keller Williams Realty

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Schools

Schools serving 5520 Leeward Ln

School District:Talbot County Public Schools

Name	Grades	Distance
Tilghman Elementary School 21374 Foster Ave, Tilghman Island, MD 21671	K-6	0.8 mi
St. Michaels Middle/High School 200 Seymour Avenue, Saint Michaels, MD 21663	7-12	8.6 mi
Easton High School 723 Mecklenburg Avenue, Easton, MD 21601	9-12	15.4 mi

Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 5520 Leeward Ln

Date

Details

Price

Change

Source

6/18/2026

Sold

$1,000,000

-9.09%

MLS

4/08/2026

Price Reduced

$1,100,000

-8.33%

MLS

8/06/2025

Price Reduced

$1,200,000

-12.73%

MLS

7/18/2025

Price Reduced

$1,375,000

-21.43%

MLS

6/17/2025

Price Reduced

$1,750,000

-20.45%

MLS

5/27/2025

Listed

$2,200,000

—

MLS

Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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Farm Single-Family
Active
Updated 3 days ago

8
Beds
6
Total Baths
9,051
Sq. Ft.

Listed by TTR Sotheby's International Realty, Laura H Carney and TTR Sotheby's International Realty, Robert D Lacaze

Just Listed

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Farm Single-Family
Active
Updated 3 days ago

8
Beds
6
Total Baths
9,051
Sq. Ft.

Listed by TTR Sotheby's International Realty, Laura H Carney and TTR Sotheby's International Realty, Robert D Lacaze

Just Listed

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Single Family
Active
Updated 3 days ago

8
Beds
6
Total Baths
9,051
Sq. Ft.

Listed by TTR Sotheby's International Realty, Laura H Carney and TTR Sotheby's International Realty, Robert D Lacaze

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Just Listed

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$359,000

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Townhouse
Active
Updated 2 days ago

2
Beds
3
Total Baths
1,487
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Price Reduced

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Single Family
Active
Updated 3 days ago

5
Beds
2
Total Baths
4,706
Sq. Ft.

Listed by Chesapeake Bay Real Estate Plus, LLC, Dawn A Lednum

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Single Family
Active
Updated 7 hours ago

2
Beds
1
Total Bath
1,200
Sq. Ft.

Listed by Compass, Gretchen V Wichlinski and Compass, Jennifer Chino

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Price Reduced

-$50,000 (-2.51%)

$1,945,000

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Townhouse
Active
Updated 7 days ago

6
Beds
6
Total Baths
4,089
Sq. Ft.

Listed by Chesapeake Bay Real Estate Plus, LLC, Maureen M McHugh

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Sold

$1,050,000

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Single Family
Closed

3
Beds
3
Total Baths
3,232
Sq. Ft.

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Sold

$983,000

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Single Family
Closed

2
Beds
2
Total Baths
1,383
Sq. Ft.

Listed by Benson & Mangold, LLC, Winifred C Cowee
Sold by Compass, James M. Baldwin

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Sold

$1,130,000

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Single Family
Closed

3
Beds
3
Total Baths
2,085
Sq. Ft.

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Single Family
Closed

2
Beds
2
Total Baths
2,048
Sq. Ft.

Listed by RE/MAX Executive, Crystal M Smith
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5520 Leeward Lane, Tilghman, MD 21671 (MLS# MDTA2010832) is a Single Family property that was sold at $1,000,000 on June 18, 2026. Want to learn more about 5520 Leeward Lane? Do you have questions about finding other Single Family real estate for sale in Tilghman? You can browse all Tilghman real estate or contact a Coldwell Banker agent to request more information.

5520 Leeward Ln Tilghman, MD 21671