21 Winston Dr
Rhinebeck, NY 12572
4 bd 3 ba 5,396 sqft Built 1993 Lot 133,729 sqft single_family
Most recent sale
$1,450,000
Nov 15, 2021
Location
Timeline: Sale, Listing & Tax History
Recorded events
| Date | Event | Price | Source |
|---|---|---|---|
| Nov 15, 2021 | Sold | $1,450,000 | MLS #402328 |
| Dec 4, 2014 | Sold | $988,750 | Public Record |
| Nov 26, 2014 | Listing removed | $1,150,000 | MidHudson |
| Nov 24, 2014 | Sold | $988,750 | HudsonValleyCatskill |
| Sep 12, 2014 | Relisted | $1,150,000 | MLS #320829 |
| Jul 1, 2014 | Listing removed | $1,150,000 | MidHudson |
| Jun 30, 2014 | Price changed | $1,150,000 | MLS #320829 |
| Jun 30, 2014 | Listing removed | $1,250,000 | ColumbiaDutchess |
| Oct 2, 2013 | Listed | $1,250,000 | MLS #93486 |
| Jan 25, 1995 | Sold | $407,000 | Public Record |
Tax assessment history
| Year | Building | Land | Total assessed | Tax paid |
|---|---|---|---|---|
| 2025 | $1,503,900 | $147,800 | $1,651,700 | $22,730 |
| 2024 | $1,306,600 | $298,400 | $1,605,000 | $23,038 |
| 2023 | $1,088,800 | $278,100 | $1,366,900 | $23,263 |
| 2022 | $844,500 | $166,400 | $1,010,900 | $21,494 |
| 2021 | $796,400 | $166,400 | $962,800 | $19,068 |
| 2020 | $796,400 | $166,400 | $962,800 | $18,825 |
| 2019 | $727,800 | $103,500 | $831,300 | $19,853 |
| 2018 | $727,800 | $103,500 | $831,300 | $19,352 |
| 2017 | $727,800 | $103,500 | $831,300 | $18,578 |
| 2016 | $727,800 | $103,500 | $831,300 | $18,145 |
| 2015 | $727,800 | $103,500 | $831,300 | $18,215 |
| 2014 | $727,800 | $103,500 | $831,300 | $18,051 |
| 2013 | $727,800 | $103,500 | $831,300 | $17,113 |
| 2012 | $727,800 | $103,500 | $831,300 | $16,612 |
| 2011 | $727,800 | $103,500 | $831,300 | $16,391 |
| 2010 | $727,800 | $103,500 | $831,300 | $15,884 |
| 2009 | $800,100 | $103,500 | $903,600 | $4,222 |
| 2008 | $828,000 | $103,500 | $931,500 | $3,963 |
| 2007 | $805,500 | $103,500 | $909,000 | $3,963 |
Property facts
Year built
1993
Property type
single_family
Stories
—
Beds
4
Baths
3
Living area
5,396 sqft
Lot size
133,729 sqft
ZIP code
12572
City
Rhinebeck
Street
Winston Dr
Coordinates
41.96527, -73.87697
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
$8,700
Gross rental yield
7.20%
Implied cap rate
4.68%
Trend-extrapolated value
—
Frequently asked questions
When did 21 Winston Dr last sell?
21 Winston Dr most recently sold on Nov 15, 2021 for $1,450,000.
What is the current tax assessment for 21 Winston Dr?
The most recent total assessment for 21 Winston Dr (year 2025) is $1,651,700 with $22,730 in property tax.
How does 21 Winston Dr's assessment compare to its last sale price?
The current assessment is 13.9% above the last sale price of $1,450,000.
When was 21 Winston Dr built?
21 Winston Dr was built in 1993.
How does 21 Winston Dr compare to others on Winston Dr?
We track 7 other properties on Winston Dr. Browse the list under "Other properties on Winston Dr" to compare beds, baths, and sale history.
What are the property facts for 21 Winston Dr?
21 Winston Dr is a 4 bed, 3 bath, 5,396 sqft, 133,729 sqft lot single_family.
Is 21 Winston Dr a flip candidate?
No — 21 Winston Dr does not appear in our flips dataset.
Is 21 Winston Dr a tax-appeal candidate?
No — 21 Winston 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
-2.3%
2026 Q1
$728.7K
2026 Q2
$724.5K
ZIP 12572 — Median Price History + Forecast
Explore nearby
Geography
Other properties on Winston Dr