33565 Windswept Dr
Millsboro, DE 19966
3 bd 3 ba 1,842 sqft Built 2007 condo
Most recent sale
$369,000
Dec 3, 2021
Location
Timeline: Sale, Listing & Tax History
Recorded events
| Date | Event | Price | Source |
|---|---|---|---|
| Sep 16, 2025 | Sold | $415,000 | BrightMLS |
| Aug 8, 2025 | Price changed | $415,000 | BrightMLS |
| Jun 10, 2025 | Price changed | $425,000 | BrightMLS |
| May 30, 2025 | Price changed | $439,500 | BrightMLS |
| May 12, 2025 | Price changed | $449,500 | BrightMLS |
| Apr 25, 2025 | Price changed | $465,000 | BrightMLS |
| Mar 12, 2025 | Listed | $485,000 | BrightMLS |
| Oct 15, 2024 | Price changed | $440,000 | BrightMLS |
| Sep 6, 2024 | Price changed | $460,000 | BrightMLS |
| May 14, 2024 | Price changed | $475,000 | BrightMLS |
| Apr 19, 2024 | Listed | $489,000 | BrightMLS |
| Jul 8, 2022 | Listed | $469,000 | MLS #DESU2024878 |
| Dec 3, 2021 | Sold | $369,000 | MLS #DESU2005066 |
| Sep 23, 2021 | Price changed | $369,000 | MLS #DESU2005066 |
| Sep 9, 2021 | Listed | $399,000 | MLS #DESU2005066 |
| Jun 15, 2020 | Sold | $290,000 | Public Record |
| Mar 25, 2020 | Listed | $305,000 | MLS #DESU158458 |
| Aug 22, 2019 | Price changed | $315,900 | MLS #DESU124392 |
| Jun 20, 2019 | Price changed | $317,900 | MLS #DESU124392 |
| Dec 6, 2018 | Listed | $324,000 | MLS #DESU124392 |
| Feb 6, 2012 | Listing removed | $519,000 | BrightMLS |
| Mar 3, 2007 | Listed | $519,000 | MLS #4898161 |
| Feb 6, 2007 | Sold | $456,968 | Public Record |
Tax assessment history
| Year | Building | Land | Total assessed | Tax paid |
|---|---|---|---|---|
| 2025 | $166,250 | $25,600 | $191,850 | $819 |
| 2024 | $166,250 | $25,600 | $191,850 | $1,279 |
| 2023 | $30,150 | $800 | $30,950 | $1,278 |
| 2022 | $30,150 | $800 | $30,950 | $1,257 |
| 2021 | $30,150 | $800 | $30,950 | $1,220 |
| 2020 | $30,150 | $800 | $30,950 | $1,164 |
| 2019 | $30,150 | $800 | $30,950 | $1,159 |
| 2018 | $30,150 | $800 | $30,950 | $1,170 |
| 2017 | $30,150 | $800 | $30,950 | $1,180 |
| 2016 | $30,150 | $800 | $30,950 | $1,040 |
| 2015 | $30,150 | $800 | $30,950 | $1,072 |
| 2014 | $30,150 | $800 | $30,950 | $1,056 |
| 2013 | $30,150 | $800 | $30,950 | $1,067 |
| 2012 | — | — | $30,950 | $1,026 |
| 2011 | — | — | $30,950 | $1,035 |
Property facts
Year built
2007
Property type
condo
Stories
2
Beds
3
Baths
3
Living area
1,842 sqft
Lot size
—
ZIP code
19966
City
Millsboro
Street
Windswept Dr
Coordinates
38.60661, -75.16636
Comparable properties nearby
Block-level micro-comps
Same street, ±3 house numbers, sold in the last 24 monthsInvestment analysis
Estimates based on local averages — not personalized adviceEstimated monthly rent
$2,763
Gross rental yield
8.99%
Implied cap rate
5.84%
Trend-extrapolated value
—
Frequently asked questions
When did 33565 Windswept Dr last sell?
33565 Windswept Dr most recently sold on Dec 3, 2021 for $369,000.
What is the current tax assessment for 33565 Windswept Dr?
The most recent total assessment for 33565 Windswept Dr (year 2025) is $191,850 with $819 in property tax.
How does 33565 Windswept Dr's assessment compare to its last sale price?
The current assessment is 48.0% below the last sale price of $369,000.
When was 33565 Windswept Dr built?
33565 Windswept Dr was built in 2007.
How does 33565 Windswept Dr compare to others on Windswept Dr?
We track 8 other properties on Windswept Dr. Browse the list under "Other properties on Windswept Dr" to compare beds, baths, and sale history.
What are the property facts for 33565 Windswept Dr?
33565 Windswept Dr is a 3 bed, 3 bath, 1,842 sqft condo.
Is 33565 Windswept Dr a flip candidate?
Yes — 33565 Windswept Dr appears in our flips dataset, indicating it sold twice within a short window with a notable price change.
Is 33565 Windswept Dr a tax-appeal candidate?
No — 33565 Windswept Dr is not currently flagged as a tax-appeal candidate.
Forecast for this area
ZIP-area linear projection — not a per-property automated valuationQuarterly trend
+0.6%
Implied 1-yr
+2.5%
2026 Q3
$536.4K
2026 Q4
$539.7K
ZIP 19966 — Median Price History + Forecast
Explore nearby
Geography
Other properties on Windswept Dr