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.
Sold for $1,000,000
$1,000,000
5520 Leeward Ln, Tilghman, MD 21671
5beds
4,214sqft
Single Family Residence
Built in 2005
1.19 Acres Lot
$999,600 Zestimate®
$237/sqft
$3,765 Estimated rent
Home value
$999,600
$910,000 - $1.10M
$3,765/mo
Zestimate® history
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$5,873/mo
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List your homeWhat's special
Private waterfront estateOversized islandCommercial refrigeratorCommercial-grade gas stovePanoramic water viewsFormal dining areaGranite countertops
Zillow last checked:
Listing updated:
Listed by:
Samantha Jackson 484-889-9364,
Keller Williams Realty
Bought with:
Dawn Lednum, 78241
Chesapeake Bay Real Estate Plus, LLC
Source: Bright MLS,MLS#: MDTA2010832
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 3
- Full bathrooms: 2
- 1/2 bathrooms: 1
- Main level bathrooms: 2
- Main level bedrooms: 1
Rooms
- Room types: 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
Primary bedroom
- Level: Main
- Area: 361 Square Feet
- Dimensions: 19 X 19
Bedroom 1
- Features: Flooring - HardWood
- Level: Upper
- Area: 180 Square Feet
- Dimensions: 12 X 15
Bedroom 2
- Features: Flooring - Carpet
- Level: Upper
- Area: 196 Square Feet
- Dimensions: 14 X 14
Bedroom 3
- Features: Flooring - Carpet
- Level: Upper
- Area: 168 Square Feet
- Dimensions: 12 X 14
Bedroom 4
- Features: Flooring - Carpet
- Level: Upper
- Area: 168 Square Feet
- Dimensions: 12 X 14
Primary bathroom
- Features: Double Sink, Walk-In Closet(s), Soaking Tub
- Level: Main
- Area: 285 Square Feet
- Dimensions: 15 X 19
Bathroom 1
- Level: Upper
- Area: 25 Square Feet
- Dimensions: 5 X 5
Breakfast room
- Level: Main
- Area: 182 Square Feet
- Dimensions: 13 X 14
Dining room
- Features: Flooring - HardWood
- Level: Main
- Area: 224 Square Feet
- Dimensions: 16 X 14
Foyer
- Features: Flooring - HardWood
- Level: Main
- Area: 128 Square Feet
- Dimensions: 16 X 8
Half bath
- Level: Main
- Area: 18 Square Feet
- Dimensions: 3 X 6
Kitchen
- Features: Flooring - HardWood
- Level: Main
- Area: 256 Square Feet
- Dimensions: 16 X 16
Kitchen
- Level: Upper
- Area: 95 Square Feet
- Dimensions: 5 X 19
Laundry
- Level: Main
- Area: 114 Square Feet
- Dimensions: 6 X 19
Living room
- Features: Flooring - HardWood
- Level: Main
- Area: 552 Square Feet
- Dimensions: 24 X 23
Living room
- Level: Upper
- Area: 323 Square Feet
- Dimensions: 17 X 19
Sitting room
- Features: Flooring - HardWood
- Level: Main
- Area: 210 Square Feet
- Dimensions: 15 X 14
Heating
- Heat Pump, Electric, Natural Gas
Cooling
- Ceiling Fan(s), Central Air, Electric
Appliances
- Included: Dishwasher, Dryer, Extra Refrigerator/Freezer, Ice Maker, Instant Hot Water, Microwave, Oven/Range - Gas, Range Hood, Refrigerator, Six Burner Stove, Washer, Exhaust Fan, Electric Water Heater
- Laundry: Laundry Room
Features
- Family Room Off Kitchen, Breakfast Area, Kitchen - Table Space, Dining Area, Built-in Features, Entry Level Bedroom, Upgraded Countertops, Primary Bath(s), Open Floorplan
- Windows: Screens, Window Treatments
- Basement: Sump Pump
- Has fireplace: No
Interior area
- Total structure area: 4,214
- Total interior livable area: 4,214 sqft
- Finished area above ground: 4,214
- Finished area below ground: 0
Property
Parking
- Total spaces: 3
- Parking features: Garage Door Opener, Attached, Driveway
- Attached garage spaces: 3
- Has uncovered spaces: Yes
Accessibility
- Accessibility features: >84" Garage Door, 2+ Access Exits
Features
- Levels: Two
- Stories: 2
- Patio & porch: Deck, Porch
- Exterior features: Balcony
- Pool features: None
- Has view: Yes
- View description: Water
- Has water view: Yes
- Water view: Water
- Waterfront features: Bay
- Body of water: Chesapeake Bay
- Frontage length: Water Frontage Ft: 100
Lot
- Size: 1.19 Acres
Details
- Additional structures: Above Grade, Below Grade
- Parcel number: 2105189950
- Zoning: RESIDENTIAL
- Special conditions: Short Sale
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subtype: Single Family Residence
Materials
- Vinyl Siding
- Foundation: Crawl Space
- Roof: Shingle
Condition
- New construction: No
- Year built: 2005
Utilities & green energy
- Sewer: Public Sewer
- Water: Well
Community & HOA
Community
- Subdivision: Paw Paw Cove
HOA
- Has HOA: No
Location
- Region: Tilghman
Financial & listing details
- Price per square foot: $237/sqft
- Tax assessed value: $953,600
- Annual tax amount: $8,231
- Date on market: 5/27/2025
- Listing agreement: Exclusive Right To Sell
- Listing terms: Cash,Conventional
- Ownership: Fee Simple
Price history
| Date | Event | Price |
|---|---|---|
| 6/18/2026 | Sold | $1,000,000-9.1%$237/sqft |
Source:  Bright MLS #MDTA2010832 Report a problem | ||
| 5/6/2026 | Contingent | $1,100,000$261/sqft |
Source: Bright MLS #MDTA2010832 Report a problem | ||
| 4/8/2026 | Price change | $1,100,000-8.3%$261/sqft |
Source: Bright MLS #MDTA2010832 Report a problem | ||
| 8/6/2025 | Price change | $1,200,000-12.7%$285/sqft |
Source: Bright MLS #MDTA2010832 Report a problem | ||
| 7/18/2025 | Price change | $1,375,000-21.4%$326/sqft |
Source: Bright MLS #MDTA2010832 Report a problem | ||
| 6/17/2025 | Price change | $1,750,000-20.5%$415/sqft |
Source: Bright MLS #MDTA2010832 Report a problem | ||
| 5/27/2025 | Listed for sale | $2,200,000+2488.2%$522/sqft |
Source: Bright MLS #MDTA2010832 Report a problem | ||
| 2/5/1996 | Sold | $85,000$20/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | -- | $953,600 +4.6% |
| 2024 | $8,231 +10.7% | $911,500 +4.8% |
| 2023 | $7,437 +13.2% | $869,400 +5.1% |
| 2022 | $6,569 +6.4% | $827,300 +0.4% |
| 2021 | $6,171 +0.4% | $823,733 +0.4% |
| 2020 | $6,145 +0.4% | $820,167 +0.4% |
| 2019 | $6,118 +4.8% | $816,600 +0.4% |
| 2018 | $5,838 +5.6% | $812,967 +0.4% |
| 2017 | $5,526 +8.2% | $809,333 +0.5% |
| 2016 | $5,108 | $805,700 +1.4% |
| 2015 | $5,108 +18.9% | $794,800 +1.4% |
| 2014 | $4,294 | $783,900 +1.4% |
| 2013 | -- | $773,000 |
| 2012 | -- | $773,000 |
| 2011 | -- | $773,000 -24.4% |
| 2010 | -- | $1,022,930 +14% |
| 2009 | -- | $897,456 +16.3% |
| 2008 | -- | $771,983 +19.4% |
| 2007 | -- | $646,510 +8.2% |
| 2006 | -- | $597,512 +8.9% |
| 2005 | -- | $548,516 +258.5% |
| 2004 | -- | $153,000 +9.3% |
| 2003 | -- | $139,932 +10.3% |
| 2002 | -- | $126,866 +11.5% |
| 2001 | -- | $113,800 |
Find assessor info on the county website
Neighborhood: 21671
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Nearby schools
GreatSchools rating
- 4/10Tilghman Elementary SchoolGrades: PK-5Distance: 0.8 mi
- 5/10St. Michaels Middle/High SchoolGrades: 6-12Distance: 8.6 mi
Schools provided by the listing agent
- District: Talbot County Public Schools
Source: Bright MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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Estimated market value
$999,600
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Estimated market value
$999,600
- Maryland
- Talbot County
- Tilghman
- 21671
- 5520 Leeward Ln
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