MLS: #MDTA2010832, Listed By: Samantha Jackson, Keller Williams Realty, Source:Bright MLS
5520 Leeward Lane
TILGHMAN, MD 21671
5
Bed
3
Bath
4,214Sqft
1.19Acres(Lot)
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 d
Property Details
Map
Map
What's Nearby
Nearby Areas
Features
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Bedroom Information
Total beds: 5Bathroom Information
Total Baths: 3 Full Baths: 2 Half Baths: 1Room Information
Has Basement: Yes Basement: Crawl Space, Sump Pump -
Roofing Information
Shingle -
Interior Features
Built-in Features, Open Floorplan Roof: Shingle Appliances: Gas Range, Gas Oven, Cooktop, Electric Water Heater, Dishwasher, Dryer, Ice Maker, Instant Hot Water, Microwave, Range Hood, Refrigerator, Washer, Exhaust Fan Laundry Features: Laundry Room Window Features: Window Coverings, Screens, Window Treatments -
Heating & Cooling
Has Heating: Yes Heating: Exhaust Fan, Electric, Natural Gas, Heat Pump Has Cooling: Yes Cooling: Central Air, Ceiling Fan(s), Electric Water front: 1
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Building Information
Year Built: 2005 Building Area Total: 4214 Construction Materials: Vinyl Siding Stories: 2 Frontage Length: 100 Patio And Porch Features: Deck, Porch Pool Features: None Private Pool: No View: Water -
Exterior Features
Exterior Features: Balcony
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Lot Information
Lot Size Acres: 1.19 Lot Size Source: Assessor Lot Size Square Feet: 51836 Lot Description: WaterfrontProperty Information
Subdivision: PAW PAW COVE Source Property Type: Residential Postal Code Plus 4: 1154 Property SubType: Single Family Residence Direction Faces: West Levels: Two Property Age: 21
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Listing Price Information
Listing Price: $1100000
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Tax Information
Parcel Number: 2105189950 Tax Lot: 13A Tax Year: 2024 Annual Tax: $8231
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Parking Information
Parking Total: 3 Garage Door Opener, Garage, Driveway, AttachedGarage Information
Has Garage: Yes Has Attached Garage: Yes Garage Space: 3
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Location Information
Direction: FROM EASTON RT. 33 THROUGH ST. MICHAELS TO TILGHMAN ISLAND. TAKE A RIGHT ON LEEWARD LANE THEN LFEFT INTO DRIVEWAY. SIGN POSTED. WaterSource: Well
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Nearby Home Value
| Address | Estimate | Bed | Bath | Sq. Ft | Lot Size |
|---|---|---|---|---|---|
| 21642 Chicken Point Road, Tilghman, MD, 21671 | $2,695,000 | 7 | 6 | 4,151 | 4,151 SqFt |
| 21485 Island Club Road, Tilghman, MD, 21671 | $1,950,000 | 5 | 5 | 4,303 | 4,303 SqFt |
| 21572 Chicken Point Road, Tilghman, MD, 21671 | $925,000 | 2 | 3 | 1,729 | 1,729 SqFt |
| 21408 Broad Cove Lane, Tilghman, MD, 21671 | $1,399,000 | 4 | 3 | 3,037 | 3,037 SqFt |
| 21560 Chicken Point Road, Tilghman, MD, 21671 | $870,000 | 3 | 2 | 1,314 | 1,314 SqFt |
| 21552 Chicken Point Road, Tilghman, MD, 21671 | $970,000 | 5 | 2 | 2,655 | 2,655 SqFt |
| 21477 Island Club Road, Tilghman, MD, 21671 | $1,150,000 | 4 | 3 | 3,040 | 3,040 SqFt |
| 21530 Coopertown Road, Tilghman, MD, 21671 | $279,000 | 3 | 1 | 996 | 996 SqFt |
| 21524 Chicken Point Road, Tilghman, MD, 21671 | $349,000 | 4 | 2 | 1,761 | 1,761 SqFt |
| 4940 Fairbank Road, Tilghman, MD, 21671 | $580,000 | 2 | 2 | 1,260 | 1,260 SqFt |
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ByOwner last updated this listing 06/07/2026 @ 04:08
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