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$1,200,000

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 4,214 Sq. Ft.
  • 3 Car Garage
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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.

Full Property Details for 5520 Leeward Ln

General

  • Price: $1,200,000
  • Taxes: $8,231 (2024)
  • Status: Active
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: MDTA2010832
  • Updated: 12/17/2025
  • Added to Site: 280 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.: $284.77
  • Assessment Year: 2025
  • County Tax: $8,231
  • County Tax Freq: Annually
  • Tax w/Assessment: $953,600
  • Tax Amount: $8,231
  • Tax Year: 2024

Disclosures and Reports

  • Ownership: Fee Simple
  • Lot Number: 13A

Listed by Keller Williams Realty, Samantha Kay Jackson

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Listing agent

— 5520 Leeward Ln —

  • Samantha Kay Jackson

    Keller Williams Realty

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 5520 Leeward Ln

School District:Talbot County Public Schools
NameGradesDistance
Tilghman Elementary School
21374 Foster Ave, Tilghman Island, MD 21671
K-60.8 mi
St. Michaels Middle/High School
200 Seymour Avenue, Saint Michaels, MD 21663
7-128.6 mi
Easton High School
723 Mecklenburg Avenue, Easton, MD 21601
9-1215.4 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 5520 Leeward Ln Get Price Alerts and Save Property

Date
Details
Price
Change
Source
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
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 5520 Leeward Ln

Year
Property Taxes
Change
Tax Assessment
Change
2023
$7,437
—
$953,600
5%
2023
$7,437
—
$911,500
5%
2023
$7,437
13%
$869,400
5%
2022
$6,569
7%
$827,300
—
2020
$6,145
1%
$823,733
—
2021
$6,092
—
$820,167
—
2020
$6,066
4%
$816,600
—
2019
$5,838
6%
$812,967
—
2018
$5,526
4%
$809,333
—
2017
$5,310
3%
$805,700
1%
2016
$5,150
3%
$794,800
1%
2015
$5,009
4%
$783,900
1%
2014
$4,824
—
$773,000
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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Listed by Keller Williams Realty, Samantha Kay Jackson

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5520 Leeward Lane, Tilghman, MD 21671 (MLS# MDTA2010832) is a Single Family property with 5 bedrooms, 2 full bathrooms and 1 partial bathroom. 5520 Leeward Lane is currently listed for $1,200,000 and was received on May 27, 2025. 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.

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