5420 WINDWARD DR
Valuation
Tax & Assessment
Climate Risk
Scores 0–100; higher = greater projected risk.
Property Facts
Transaction History(3)
Sales and refinances filed with the county for this home. Not every transfer is a normal sale, so check the type before comparing prices.Assigned SchoolsThe public schools this address is zoned for. Boundaries change, so confirm with the district before you count on it.
District: Talbot County Public Schools
Neighborhood · ZIP 21671These are comparison scores, not percentages. 100 equals the national average, so 150 means about 50% above average.
Index scale: 100 = US average (tick). Lower is better.
Owner Tools
Data by ATTOM. Valuations are automated estimates, not appraisals. Photos from Google Street View and may not depict the current property state.
How this home compares
5420 Windward Dr measured against every home in its neighborhood, its ZIP code and its county, using county assessor records refreshed nightly. A home can stand out in one of those areas and look ordinary in another, because each one holds a different mix of homes.
- Worth more than 89% of homes in Tilghman 21671
- Costs more per square foot than 82% of homes in Tilghman 21671
- Bigger than 77% of homes in Tilghman 21671
- Newer than 91% of homes in Talbot County
What homes are worth in Tilghman 21671
Each bar is how many homes fall in that price range. The marker is this home.
This home is worth more than 89% of homes in Tilghman 21671.
How it measures up in Tilghman 21671
The dot is this home. The mark in the middle is the typical home in Tilghman 21671.
Pricier than 89% of homes nearby
Pricier than 82% of homes nearby
Bigger than 77% of homes nearby
Bigger than 50% of homes nearby
Newer than 88% of homes nearby
| Measure | This home | Tilghman 21671 | Talbot County |
|---|---|---|---|
| Estimated valuepricier than | $984,033 | 89% of homes | 79% of homes |
| Price per ft²pricier than | $418 | 82% of homes | 80% of homes |
| Living areabigger than | 2,352 ft² | 77% of homes | 66% of homes |
| Lot sizebigger than | 0.46 ac | 50% of homes | 52% of homes |
| Year builtnewer than | 2009 | 88% of homes | 91% of homes |
About 5420 Windward Dr
How much is 5420 Windward Dr, Tilghman, MD worth?
The TopHap Estimate for 5420 Windward Dr, Tilghman, MD is $984,033 as of Oct 21, 2026. The likely range is $905,223 to $1,062,843. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.
When did 5420 Windward Dr, Tilghman, MD last sell?
5420 Windward Dr, Tilghman, MD last sold on Feb 3, 2021 for $725,000, according to the county's recorded deed. TopHap holds 3 recorded sales for this parcel.
How big is 5420 Windward Dr, Tilghman, MD?
5420 Windward Dr, Tilghman, MD has 2.5 bathrooms, 2,352 square feet of living space and a 0.46-acre lot.
When was 5420 Windward Dr, Tilghman, MD built?
5420 Windward Dr, Tilghman, MD was built in 2009, making it 17 years old. The building has 1 story.
What schools serve 5420 Windward Dr, Tilghman, MD?
5420 Windward Dr, Tilghman, MD is assigned to Tilghman Elementary School (elementary), rated B-; St. Michaels Middle/High School (middle), rated B-. All sit in Talbot County Public Schools. Attendance boundaries change — confirm with the district before relying on an assignment.
How does 5420 Windward Dr, Tilghman, MD compare to other homes in Tilghman 21671?
Among the 676 homes in Tilghman 21671, it is worth more than 89% of them ($984,033 against a typical $483,029), its price per square foot is higher than 82% of them ($418 against a typical $280), it is bigger than 77% of them (2,352 ft² against a typical 1,720 ft²), its lot is bigger than 50% of them (0.46 ac against a typical 0.46 ac) and it is newer than 88% of them (2009 against a typical 1975). Measured against all of Talbot County, it is worth more than 79% of homes there. These shares are recounted nightly from the full county assessor record for each area, not from active listings.
What are the property taxes on 5420 Windward Dr, Tilghman, MD?
The 2026 property tax bill for 5420 Windward Dr, Tilghman, MD was $7,020. The county assessed it at $761,500.
More homes on Windward Dr
- 5400 Windward Dr$1.2M5 ba · 4,280 ft² · Sold $250K · Jul 2024
- 5427 Windward Dr$574K3.5 ba · 2,289 ft² · Sold $439K · Aug 2023
- 5490 Windward Dr$1.3M2 ba · 2,046 ft² · Sold $1.2M · Nov 2022
- 5396 Windward Dr$1M4.5 ba · 3,494 ft² · Sold $238K · May 2022
- 5410 Windward Dr$875K3 ba · 2,686 ft² · Sold $800K · May 2021
- 5401 Windward Dr$405K2 ba · 1,248 ft² · Sold $225K · Dec 2018
- 5480 Windward Dr$1.3M2 ba · 1,936 ft² · Sold $595K · Jun 2011
- 5423 Windward Dr$381K2 ba · 1,378 ft² · Sold $218K · Dec 2005
- 5451 Windward Dr$300K1 ba · 1,031 ft² · Sold $240K · Aug 2005
- 5411 Windward Dr$459K2 ba · 1,568 ft² · Sold $148K · Jul 2000
- 5444 Windward Dr$727K2 ba · 1,456 ft² · Sold Mar 1999
- 5466 Windward Dr$797K2.5 ba · 2,310 ft² · Sold $178K · Dec 1994
Closest homes
- 5410 Windward Dr$875K102 ft · 3 ba · 2,686 ft² · Sold $800K · May 2021
- 5434 Windward Dr$721K104 ft · 1.5 ba · 1,416 ft² · Sold Jan 1900
- 5400 Windward Dr$1.2M206 ft · 5 ba · 4,280 ft² · Sold $250K · Jul 2024
- 5444 Windward Dr$727K207 ft · 2 ba · 1,456 ft² · Sold Mar 1999
- 5423 Windward Dr$381K230 ft · 2 ba · 1,378 ft² · Sold $218K · Dec 2005
- 5454 Windward Dr$942K302 ft · 3.5 ba · 3,140 ft² · Sold $75K · Aug 1983
- 5427 Windward Dr$574K248 ft · 3.5 ba · 2,289 ft² · Sold $439K · Aug 2023
- 5396 Windward Dr$1M328 ft · 4.5 ba · 3,494 ft² · Sold $238K · May 2022
More homes in Tilghman 21671
- 21408 Broad Cove Ln$1.3M2.5 ba · 3,037 ft² · Sold $1.3M · Sep 2026
- 5654 Trafalgar Cir$457K2 ba · 1,729 ft² · Sold $455K · Aug 2026
- 21530 Coopertown Rd$266K1 ba · 996 ft² · Sold $265K · Aug 2026
- 5960 Tilghman Island Rd$136K1 ba · 888 ft² · Sold $135K · Jul 2026
- 4940 Fairbank Rd$563K1 ba · 1,260 ft² · Sold $560K · Jul 2026
- 21486 Mission Rd$402K3 ba · 3,904 ft² · Sold $400K · Jul 2026
- 4869 Bar Neck Rd$210K2 ba · 1,070 ft² · Sold $162K · Jul 2026
- Black Walnut Point Rd18.31 ac · Sold $1.3M · Jun 2026
- 5520 Leeward Ln$1M2.5 ba · 5,093 ft² · Sold $1M · Jun 2026
- 21749 Camper Cir$277K1 ba · 1,224 ft² · Sold $275K · May 2026
- 6050 Sunset Ln$1.1M3 ba · 2,672 ft² · Sold $1.1M · Apr 2026
- 5582 Trafalgar Cir$528K2.5 ba · 2,110 ft² · Sold $523K · Apr 2026
Assigned schools
Explore the area
See this home in context
Open 5420 Windward Dr on TopHap’s interactive map to compare it against every sale nearby, overlay school zones and flood risk, and run a CMA.
Open in map