Experience Eastern Shore waterfront living in this charming Chesapeake Bay home, where breathtaking sunset views and a relaxed coastal atmosphere create the perfect setting for everyday living or weekend escapes. Designed to embrace the waterfront lifestyle, the property offers exceptional indoor and outdoor spaces for entertaining family and friends. A brick walkway welcomes you to the inviting front porch and foyer, where hardwood floors flow throughout the home. Recently renovated, the kitchen features white cabinetry, quartz countertops and large windows that fill the space with natural light while overlooking the front yard. The spacious living room is highlighted by a cathedral ceiling and opening to a year-round sunroom surrounded by walls of windows showcasing panoramic views of the Chesapeake Bay. The primary suite features a newly renovated bath with a tile and glass shower. Two guest bedrooms, an office and two additional beautifully renovated full baths occupy the opposite wing of the home, while the second level offers a fourth bedroom with skylights. Outside, you'll find everything needed to enjoy life on the water. The waterside pool with swim deck is complemented by a screened porch, expansive patio, covered seating area and a pool house/bar complete with air conditioning and electric. The private pier provides the perfect spot for fishing, crabbing, or simply taking in the spectacular sunsets, while the rip-rapped shoreline offers lasting shoreline protection. Additional improvements include an attached two-car garage, a storage shed with electric, and a new roof installed in 2025. Situated on high ground outside of the flood zone, this exceptional waterfront property offers direct access to some of the Chesapeake Bay's best fishing, boating, waterfront restaurants and the unforgettable Eastern Shore lifestyle.
For sale
$1,250,000
5480 Windward Dr, Tilghman, MD 21671
4beds
1,936sqft
Single Family Residence
Built in 1973
0.71 Acres Lot
$1,164,400 Zestimate®
$646/sqft
$15/mo HOA
What's special
Brick walkwayAttached two-car garageExpansive patioCathedral ceilingStorage shed with electricQuartz countertopsScreened porch
- 9 days |
- 904 |
- 65 |
Likely to sell faster than
Zillow last checked:
Listing updated:
Listed by:
Kimberly Crouch 410-829-7062,
Benson & Mangold, LLC (410) 745-0415
Source: Bright MLS,MLS#: MDTA2014484
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 3
- Full bathrooms: 3
- Main level bathrooms: 3
- Main level bedrooms: 3
Rooms
- Room types: Living Room, Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Kitchen, Foyer, Sun/Florida Room, Office, Bathroom 2, Bathroom 3, Primary Bathroom
Primary bedroom
- Features: Flooring - HardWood, Ceiling Fan(s)
- Level: Main
- Area: 156 Square Feet
- Dimensions: 13 X 12
Bedroom 2
- Features: Flooring - HardWood
- Level: Main
- Area: 154 Square Feet
- Dimensions: 11 X 14
Bedroom 3
- Features: Flooring - HardWood
- Level: Main
- Area: 154 Square Feet
- Dimensions: 11 X 14
Bedroom 4
- Features: Flooring - Carpet
- Level: Upper
- Area: 294 Square Feet
- Dimensions: 21 X 14
Primary bathroom
- Features: Flooring - Ceramic Tile, Bathroom - Walk-In Shower, Walk-In Closet(s)
- Level: Main
Bathroom 2
- Features: Flooring - Ceramic Tile, Bathroom - Walk-In Shower
- Level: Main
- Area: 77 Square Feet
- Dimensions: 7 X 11
Bathroom 3
- Features: Flooring - Ceramic Tile, Bathroom - Walk-In Shower
- Level: Main
- Area: 45 Square Feet
- Dimensions: 5 X 9
Foyer
- Features: Flooring - HardWood
- Level: Main
- Area: 105 Square Feet
- Dimensions: 7 X 15
Kitchen
- Features: Flooring - HardWood
- Level: Main
- Area: 204 Square Feet
- Dimensions: 12 X 17
Living room
- Features: Flooring - HardWood, Cathedral/Vaulted Ceiling
- Level: Main
- Area: 324 Square Feet
- Dimensions: 18 X 18
Office
- Features: Flooring - HardWood
- Level: Main
- Area: 77 Square Feet
- Dimensions: 7 X 11
Other
- Features: Flooring - HardWood, Fireplace - Gas
- Level: Main
- Area: 297 Square Feet
- Dimensions: 11 X 27
Heating
- Heat Pump, Propane
Cooling
- Central Air, Electric
Appliances
- Included: Gas Water Heater, Water Heater
Features
- Has basement: No
- Number of fireplaces: 1
Interior area
- Total structure area: 1,936
- Total interior livable area: 1,936 sqft
- Finished area above ground: 1,936
- Finished area below ground: 0
Property
Parking
- Total spaces: 1
- Parking features: Storage, Garage Faces Front, Inside Entrance, Oversized, Driveway, Attached
- Attached garage spaces: 1
- Has uncovered spaces: Yes
Accessibility
- Accessibility features: None
Features
- Levels: Two
- Stories: 2
- Has private pool: Yes
- Pool features: Concrete, In Ground, Private
- On waterfront: Yes
- Waterfront features: Bay
- Body of water: Chesapeake Bay
- Frontage length: Water Frontage Ft: 110
Lot
- Size: 0.71 Acres
Details
- Additional structures: Above Grade, Below Grade
- Parcel number: 2105187656
- Zoning: R
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Contemporary
- Property subtype: Single Family Residence
Materials
- Vinyl Siding
- Foundation: Crawl Space
Condition
- New construction: No
- Year built: 1973
Utilities & green energy
- Sewer: Public Sewer
- Water: Well
Community & HOA
Community
- Subdivision: Tilghman Island
HOA
- Has HOA: Yes
- HOA fee: $185 annually
Location
- Region: Tilghman
Financial & listing details
- Price per square foot: $646/sqft
- Tax assessed value: $606,600
- Annual tax amount: $5,280
- Date on market: 7/13/2026
- Listing agreement: Exclusive Right To Sell
- Ownership: Fee Simple
Estimated market value
$1,164,400
$1.11M - $1.22M
$3,254/mo
Price history
| Date | Event | Price |
|---|---|---|
| 7/13/2026 | Listed for sale | $1,250,000+110.1%$646/sqft |
Source:  Bright MLS #MDTA2014484 Report a problem | ||
| 6/14/2011 | Sold | $595,000+88.9%$307/sqft |
Source: Public Record Report a problem | ||
| 4/29/2002 | Sold | $315,000+46.5%$163/sqft |
Source: Public Record Report a problem | ||
| 11/30/1998 | Sold | $215,000$111/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | -- | $576,900 +2.9% |
| 2024 | $5,063 +8.7% | $560,633 +3% |
| 2023 | $4,657 +11.1% | $544,367 +3.1% |
| 2022 | $4,193 +6.5% | $528,100 +0.5% |
| 2021 | $3,938 +0.5% | $525,600 +0.5% |
| 2020 | $3,919 +0.5% | $523,100 +0.5% |
| 2019 | $3,900 +7.5% | $520,600 +3.1% |
| 2018 | $3,628 +8.5% | $505,167 +3.2% |
| 2017 | $3,344 +12% | $489,733 +3.3% |
| 2016 | $2,986 | $474,300 +2.1% |
| 2015 | $2,986 +66.8% | $464,667 +2.1% |
| 2014 | $1,790 | $455,033 +2.2% |
| 2013 | -- | $445,400 |
| 2012 | -- | $445,400 |
| 2011 | -- | $445,400 -15.9% |
| 2010 | -- | $529,310 +15.5% |
| 2009 | -- | $458,386 +18.3% |
| 2008 | -- | $387,463 +22.4% |
| 2007 | -- | $316,540 +8.7% |
| 2006 | -- | $291,150 +9.6% |
| 2005 | -- | $265,760 +10.6% |
| 2004 | -- | $240,370 +7.4% |
| 2003 | -- | $223,802 +8% |
| 2002 | -- | $207,236 +8.7% |
| 2001 | -- | $190,670 |
Find assessor info on the county website
Monthly payment
Est. payment
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.Climate risks
Neighborhood: 21671
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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