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

$604,100

Trulia Estimate
  • 4 Beds
  • 2.5 Baths
  • 2,236 sqft (on 1 acre)

5 Four Winds Dr, Poughkeepsie, NY 12603

Red Oaks Mill
Est. Refi. Payment $4,211/mo*
Refinance Your Home
Currently Off Market - Sold Aug 24, 2021 for $470,000

Home Value

Trulia Estimate
$604K
Since last month
Decreased$7K (-1.1%)
Since last year
Increased$17K (+3%)
Since last sale
Increased$134K (+28.5%)
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 +113% in the last 10 years
MonthEstimated value
2026
September 2026$604K
August 2026$602K
July 2026$611K
June 2026$614K
May 2026$598K
April 2026$591K
March 2026$583K
February 2026$580K
January 2026$578K
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
0.46
Single-Family Home
$515,000
12/17/25
3
3
1,728
13 Bray Farm Lane, Wappingers Falls, NY
0.59
Single-Family Home
$635,000
05/28/26
4
2.5
2,470
4 North Drive, Poughkeepsie, NY
0.39
Single-Family Home
$450,000
07/31/26
3
2
1,660
30 Daisy Lane, Poughkeepsie, NY
0.48
Single-Family Home
$480,000
07/13/26
2
2
1,968
11 Caudie Drive, Poughkeepsie, NY
0.43
Single-Family Home
$365,000
08/18/26
3
2
1,736
229 Maloney Road, Wappingers Falls, NY
0.82
Single-Family Home
$485,000
02/18/26
4
2
1,800
27 King Drive, Poughkeepsie, NY
0.72
Single-Family Home
$700,000
04/24/26
4
4
2,529
38 S View Ct, Poughkeepsie, NY
0.89
Single-Family Home
$674,500
10/21/25
4
3
2,124
1 Bray Farm Lane, Wappingers Falls, NY
0.76
Single-Family Home
$665,000
11/26/25
4
3.5
2,567
137 Simone Dr, Poughkeepsie, NY
0.79
Single-Family Home
$560,000
07/21/26
4
3
2,539

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
11 Four Winds Drive, Poughkeepsie, NY 12603
0.07
$505,100
3
2
1,486
Off Market
16 Four Winds Drive, Poughkeepsie, NY 12603
0.10
$549,900
3
3
2,000
For Sale
20 Four Winds Drive, Poughkeepsie, NY 12603
0.13
$527,400
4
2.5
1,968
Off Market
22 Four Winds Drive, Poughkeepsie, NY 12603
0.14
$622,400
4
2.5
2,332
Off Market
55 Daley Road, Poughkeepsie, NY 12603
0.23
$1,500,000
4
5.5
5,475
For Sale
11 Robin Hill Road, Poughkeepsie, NY 12603
0.22
$484,000
3
2.5
2,567
Off Market
40 Cochran Hill Road, Poughkeepsie, NY 12603
0.26
$427,200
2
1
1,176
Off Market
46 Kevin Heights, Poughkeepsie, NY 12603
0.29
$475,000
4
3
2,250
For Sale
26 Kevin Heights, Poughkeepsie, NY 12603
0.30
$531,100
4
2.5
2,085
Off Market
25 Cochran Hill Road, Poughkeepsie, NY 12603
0.33
$528,100
3
2
2,400
Off Market
6 North Drive, Poughkeepsie, NY 12603
0.37
$550,000
5
3
2,362
Recently Sold
4 North Drive, Poughkeepsie, NY 12603
0.39
$450,000
3
2
1,660
Recently Sold

Local Information

  • Map ViewExplore the area around 5 Four Winds Dr.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1986
1 acre lot
2,236 sqft
$270/sqft
Garage

About this House

This 4 bedroom, 2.5 bathroom, center hall colonial sits on a beautifully manicured 1 acre lot. Enter through the front door, to the left you will find a large formal living room w/fireplace and to the right the family room. The main level of the house continues with a spacious eat in kitchen with tile flooring, granite counters, and stainless steel appliances. Enjoy meals in the formal dining room. Updated powder room. The upstairs includes 4 great size bedrooms and the master bedroom w/ ensuite master bath and walk-in Closet. The lower level is finished w/ tile flooring, laundry room and access to the 2 car garage. Great space for home office space/remote learning or gaming area. Screened in porch off the kitchen that provides a great space to enjoy some fresh air...this leads to an uncovered deck area that overlooks the great back yard. Plenty of room to put up an above ground pool where previous one used to be. Centrally located to commuter routes, schools, shopping and the rail trail.
5 Four Winds Dr, Poughkeepsie, NY 12603 is a 4 bedroom, 3 bathroom, 2,236 sqft single-family home in Red Oaks Mill, built in 1986. It last sold for $470,000 on Aug 24, 2021. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $604,100, with a rent estimate of $3,911/month.

Home Details for 5 Four Winds Dr

Interior Features

Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 9Types of Rooms: Recreation Room
Heating & Cooling
Air ConditioningCooling System: Central
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1986Year 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: 1 acre

Price and Tax history

DateEventPrice
Aug 24, 2021
Source: OneKey® MLS as distributed by MLS GRID #H6122064
Sold
$470,000
Jun 11, 2021
Source: MHMLS #400067
Pending
$450,000
Jun 8, 2021
Source: OneKey® MLS as distributed by MLS GRID #H6122064
Listed For Sale
$450,000
Dec 16, 1998
Source: N/A
Sold
$216,000

Market trends in Poughkeepsie

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$431K
$23.33KMoM
Sale-to-List Price
101.0%
0.1%MoM
Price per sq ft
$244
$7MoM
Available listings
243
26MoM

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 5 Four Winds Dr

  • What is 5 Four Winds Dr estimated to be worth?
    Trulia's estimated value for 5 Four Winds Dr in Poughkeepsie, NY is $604,100.
  • What is the price history for 5 Four Winds Dr?
    5 Four Winds Dr in Poughkeepsie, NY last sold for $470,000 in August 2021.
  • 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 $431K. That is up $23.33K from the prior month.
  • Does 5 Four Winds Dr have air conditioning?
    Yes, 5 Four Winds Dr in Poughkeepsie, NY has air conditioning.
  • Does 5 Four Winds Dr have a pool?
    Yes, 5 Four Winds Dr in Poughkeepsie, NY has a pool.

Explore by feature - Pet Friendly

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Explore by feature - Pool

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Explore by feature - Outdoor Space

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