1416 Windward Rd
Milford, CT 06461
2 bd 2 ba 1,645 sqft Built 1995 condos
Most recent sale
$360,000
Jan 30, 2023
Location
Timeline: Sale, Listing & Tax History
Recorded events
| Date | Event | Price | Source |
|---|---|---|---|
| Feb 25, 2026 | Sold | $435,000 | SMARTMLS |
| Dec 29, 2025 | Listed | $435,000 | SMARTMLS |
| Jan 30, 2023 | Sold | $360,000 | SMARTMLS |
| Jan 26, 2022 | Listing removed | — | SMARTMLS |
| Jan 17, 2022 | Listed | $359,900 | SMARTMLS |
| Oct 3, 2017 | Sold | $274,000 | Public Record |
| Sep 29, 2017 | Listing removed | $279,900 | SMARTMLS |
| Aug 2, 2017 | Listing removed | $279,900 | CTMLS |
| May 8, 2017 | Listed | $279,900 | CTMLS |
| Apr 1, 2017 | Listed | $279,900 | SMARTMLS |
| Mar 17, 2017 | Listing removed | $2,200 | CTMLS |
| Feb 19, 2017 | Listed for rent | $2,200 | SMARTMLS |
| Feb 18, 2017 | Listing removed | $2,200 | SMARTMLS |
| Oct 27, 2016 | Listed for rent | $2,200 | CTMLS |
| Oct 25, 2016 | Listed for rent | $2,200 | SMARTMLS |
| Mar 31, 2006 | Sold | $336,000 | Public Record |
| Oct 28, 1996 | Sold | $134,900 | Public Record |
Tax assessment history
| Year | Building | Land | Total assessed | Tax paid |
|---|---|---|---|---|
| 2025 | $207,630 | — | $207,630 | $6,135 |
| 2023 | $207,630 | — | $207,630 | $5,641 |
| 2022 | $207,630 | — | $207,630 | $5,533 |
| 2021 | $184,920 | — | $184,920 | $5,113 |
| 2020 | $184,920 | — | $184,920 | $5,119 |
| 2019 | $184,920 | — | $184,920 | $5,124 |
| 2018 | $184,920 | — | $184,920 | $5,130 |
| 2017 | $184,920 | — | $184,920 | $5,139 |
| 2016 | $188,470 | — | $188,470 | $5,247 |
| 2015 | $188,470 | — | $188,470 | $5,255 |
| 2013 | $188,470 | — | $188,470 | $4,953 |
| 2005 | $106,050 | — | $106,050 | $3,413 |
| 2004 | $106,050 | — | $106,050 | $3,075 |
| 2003 | $106,050 | — | $106,050 | $3,097 |
Property facts
Year built
1995
Property type
condos
Stories
4
Beds
2
Baths
2
Living area
1,645 sqft
Lot size
—
ZIP code
06461
City
Milford
Street
Windward Rd
Coordinates
41.21658, -73.10563
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
$2,468
Gross rental yield
8.23%
Implied cap rate
5.35%
Trend-extrapolated value
—
Frequently asked questions
When did 1416 Windward Rd last sell?
1416 Windward Rd most recently sold on Jan 30, 2023 for $360,000.
What is the current tax assessment for 1416 Windward Rd?
The most recent total assessment for 1416 Windward Rd (year 2025) is $207,630 with $6,135 in property tax.
How does 1416 Windward Rd's assessment compare to its last sale price?
The current assessment is 42.3% below the last sale price of $360,000.
When was 1416 Windward Rd built?
1416 Windward Rd was built in 1995.
How does 1416 Windward Rd compare to others on Windward Rd?
We track 8 other properties on Windward Rd. Browse the list under "Other properties on Windward Rd" to compare beds, baths, and sale history.
What are the property facts for 1416 Windward Rd?
1416 Windward Rd is a 2 bed, 2 bath, 1,645 sqft condos.
Is 1416 Windward Rd a flip candidate?
No — 1416 Windward Rd does not appear in our flips dataset.
Is 1416 Windward Rd a tax-appeal candidate?
No — 1416 Windward Rd is not currently flagged as a tax-appeal candidate.
Forecast for this area
ZIP-area linear projection — not a per-property automated valuationQuarterly trend
-0.1%
Implied 1-yr
-0.2%
2026 Q3
$534.1K
2026 Q4
$533.8K
ZIP 06461 — Median Price History + Forecast
Explore nearby
Geography
Other properties on Windward Rd