14 Four Winds Dr, Poughkeepsie, NY 12603
Property image
Property image
OFF MARKET

$582,700

Trulia Estimate
  • 4 Beds
  • 4 Baths
  • 2,217 sqft (on 0.64 acres)

14 Four Winds Dr, Poughkeepsie, NY 12603

Red Oaks Mill
Est. Refi. Payment $3,963/mo*
Refinance Your Home
Currently Off Market - Sold Feb 15, 2023 for $475,000

Home Value

Trulia Estimate
$583K
Since last month
Decreased$7K (-1.3%)
Since last year
Increased$2K (+0.3%)
Since last sale
Increased$108K (+22.7%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +117% in the last 10 years
MonthEstimated value
2026
August 2026$583K
August 2026$581K
July 2026$590K
June 2026$593K
May 2026$582K
April 2026$570K
March 2026$566K
February 2026$577K
January 2026$579K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
96 Daley Road, Poughkeepsie, NY
0.45
Single-Family Home
$515,000
12/17/25
3
3
1,728
11 Caudie Drive, Poughkeepsie, NY
0.40
Single-Family Home
$365,000
08/18/26
3
2
1,736
27 King Drive, Poughkeepsie, NY
0.70
Single-Family Home
$700,000
04/24/26
4
4
2,529
4 North Drive, Poughkeepsie, NY
0.37
Single-Family Home
$450,000
07/31/26
3
2
1,660
13 Bray Farm Lane, Wappingers Falls, NY
0.62
Single-Family Home
$635,000
05/28/26
4
2.5
2,470
52 Clover Hill Drive, Poughkeepsie, NY
0.74
Single-Family Home
$530,000
05/13/26
5
3.5
3,143
24 Maloney Drive, Wappingers Falls, NY
0.67
Single-Family Home
$665,000
10/22/25
4
2.5
3,474
152 Bart Drive, Poughkeepsie, NY
0.92
Single-Family Home
$475,000
12/11/25
4
3.5
2,425
30 Daisy Lane, Poughkeepsie, NY
0.41
Single-Family Home
$480,000
07/13/26
2
2
1,968
1 Bray Farm Lane, Wappingers Falls, NY
0.80
Single-Family Home
$665,000
11/26/25
4
3.5
2,567

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
16 Four Winds Drive, Poughkeepsie, NY 12603
0.02
$549,900
3
3
2,000
For Sale
20 Four Winds Drive, Poughkeepsie, NY 12603
0.06
$525,800
4
2.5
1,968
Off Market
22 Four Winds Drive, Poughkeepsie, NY 12603
0.07
$622,400
4
2.5
2,332
Off Market
11 Four Winds Drive, Poughkeepsie, NY 12603
0.07
$507,600
3
2
1,486
Off Market
11 Robin Hill Road, Poughkeepsie, NY 12603
0.14
$484,000
3
2.5
2,567
Off Market
40 Cochran Hill Road, Poughkeepsie, NY 12603
0.20
$427,200
2
1
1,176
Off Market
46 Kevin Heights, Poughkeepsie, NY 12603
0.22
$475,000
4
3
2,250
For Sale
25 Cochran Hill Road, Poughkeepsie, NY 12603
0.25
$524,000
3
2
2,400
Off Market
26 Kevin Heights, Poughkeepsie, NY 12603
0.25
$531,100
4
2.5
2,085
Off Market
55 Daley Road, Poughkeepsie, NY 12603
0.30
$1,500,000
4
5.5
5,475
For Sale
6 North Drive, Poughkeepsie, NY 12603
0.36
$550,000
5
3
2,362
Recently Sold
3 Westview Drive, Poughkeepsie, NY 12603
0.37
$576,000
3
2.5
2,192
Off Market

Local Information

  • Map ViewExplore the area around 14 Four Winds Dr.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1987
0.64 acre lot
2,217 sqft
$263/sqft
Garage

About this House

This single-family home is located at 14 Four Winds Dr, Poughkeepsie, NY. 14 Four Winds Dr is in the Red Oaks Mill neighborhood in Poughkeepsie, NY and in ZIP code 12603. This property has 4 bedrooms, 4 bathrooms and approximately 2,217 sqft of floor space. This property has a lot size of 0.64 acres and was built in 1987.
14 Four Winds Dr, Poughkeepsie, NY 12603 is a 4 bedroom, 4 bathroom, 2,217 sqft single-family home in Red Oaks Mill, built in 1987. It last sold for $475,000 on Feb 15, 2023. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $582,700, with a rent estimate of $4,381/month.

Home Details for 14 Four Winds Dr

Interior Features

Interior Details
BasementNumber of Rooms: 9
Levels, Entrance, & Accessibility
Stories: 2
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1987Year Updated: 1990
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Exterior Features

Exterior Home Features
Exterior: Other
Pool
Pool
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Community

Units in Building: 1

Lot Information

Lot Area: 0.64 acres

Price and Tax history

DateEventPrice
Feb 15, 2023
Source: OneKey® MLS as distributed by MLS GRID #M412360
Sold
$475,000
Dec 28, 2022
Source: MHMLS #412360
Pending
$485,000
Nov 9, 2022
Source: MHMLS #412360
Listed For Sale
$485,000
Nov 13, 2008
Source: N/A
Sold
$380,000

Market trends in Poughkeepsie

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$411K
$5.83KMoM
Sale-to-List Price
101.1%
0.8%MoM
Price per sq ft
$236
$2MoM
Available listings
216
13MoM

Around this home

Neighborhood Overview

Red Oaks Mill
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Red Oaks Mill

At least 1 Trulia users voted on each feature.

  • 100 % Say neighbors are friendly

  • 100 % Say there are community events

  • 100 % Say they plan to stay for at least 5 years

  • 100 % Say yards are well-kept

  • 100 % Say it's quiet

  • 100 % Say there's wildlife

  • 100 % Say parking is easy

  • 100 % Say car is needed

  • 100 % Say people would walk alone at night

  • 100 % Say kids play outside

  • 100 % Say it's walkable to restaurants

  • 50 % Say it's dog friendly

Sourced by Trulia users. Learn more about our methodology.

LGBTQ Local Legal Protections

Frequently asked questions about 14 Four Winds Dr

  • What is 14 Four Winds Dr estimated to be worth?
    Trulia's estimated value for 14 Four Winds Dr in Poughkeepsie, NY is $582,700.
  • What is the price history for 14 Four Winds Dr?
    14 Four Winds Dr in Poughkeepsie, NY last sold for $475,000 in February 2023.
  • Is Poughkeepsie a buyer's or seller's market?
    Poughkeepsie is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Poughkeepsie?
    The median sale price in Poughkeepsie is $411K. That is up $5.83K from the prior month.
  • Does 14 Four Winds Dr have a pool?
    Yes, 14 Four Winds Dr in Poughkeepsie, NY has a pool.
  • How big is the lot at 14 Four Winds Dr?
    The lot at 14 Four Winds Dr in Poughkeepsie, NY is about 0.64 acres (27,878 sq ft).

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