20 Four Winds Drive, Poughkeepsie, NY 12603
OFF MARKET

$525,800

Trulia Estimate
  • 4 Beds
  • 2.5 Baths
  • 1,968 sqft (on 0.67 acres)

20 Four Winds Drive, Poughkeepsie, NY 12603

Red Oaks Mill
Est. Refi. Payment $3,664/mo*
Refinance Your Home
Currently Off Market - Sold Oct 13, 2023 for $455,040

Home Value

Trulia Estimate
$526K
Since last month
Decreased$8K (-1.5%)
Since last year
Increased$12K (+2.3%)
Since last sale
Increased$72K (+15.9%)
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 +90% in the last 10 years
MonthEstimated value
2026
September 2026$527K
August 2026$526K
July 2026$535K
June 2026$538K
May 2026$529K
April 2026$521K
March 2026$514K
February 2026$512K
January 2026$513K
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
11 Caudie Drive, Poughkeepsie, NY
0.34
Single-Family Home
$365,000
08/18/26
3
2
1,736
4 North Drive, Poughkeepsie, NY
0.33
Single-Family Home
$450,000
07/31/26
3
2
1,660
96 Daley Road, Poughkeepsie, NY
0.40
Single-Family Home
$515,000
12/17/25
3
3
1,728
30 Daisy Lane, Poughkeepsie, NY
0.41
Single-Family Home
$480,000
07/13/26
2
2
1,968
13 Bray Farm Lane, Wappingers Falls, NY
0.61
Single-Family Home
$635,000
05/28/26
4
2.5
2,470
8 Walker Road, Poughkeepsie, NY
0.52
Single-Family Home
$388,000
04/22/26
3
1
1,412
86 Vassar Road, Poughkeepsie, NY
0.74
Single-Family Home
$429,000
05/06/26
3
2
1,773
24 Maloney Drive, Wappingers Falls, NY
0.64
Single-Family Home
$665,000
10/22/25
4
2.5
3,474
28 Red Oaks Mill Road, Poughkeepsie, NY
0.52
Single-Family Home
$425,000
03/30/26
3
1
1,302

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
22 Four Winds Drive, Poughkeepsie, NY 12603
0.02
$622,400
4
2.5
2,332
Off Market
11 Four Winds Drive, Poughkeepsie, NY 12603
0.08
$507,600
3
2
1,486
Off Market
16 Four Winds Drive, Poughkeepsie, NY 12603
0.04
$549,900
3
3
2,000
For Sale
46 Kevin Heights, Poughkeepsie, NY 12603
0.16
$475,000
4
3
2,250
For Sale
11 Robin Hill Road, Poughkeepsie, NY 12603
0.14
$484,000
3
2.5
2,567
Off Market
26 Kevin Heights, Poughkeepsie, NY 12603
0.20
$531,100
4
2.5
2,085
Off Market
40 Cochran Hill Road, Poughkeepsie, NY 12603
0.22
$427,200
2
1
1,176
Off Market
25 Cochran Hill Road, Poughkeepsie, NY 12603
0.23
$524,000
3
2
2,400
Off Market
6 North Drive, Poughkeepsie, NY 12603
0.31
$550,000
5
3
2,362
Recently Sold
55 Daley Road, Poughkeepsie, NY 12603
0.32
$1,500,000
4
5.5
5,475
For Sale
4 North Drive, Poughkeepsie, NY 12603
0.33
$450,000
3
2
1,660
Recently Sold

Local Information

  • Map ViewExplore the area around 20 Four Winds Drive.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1986
0.67 acre lot
1,968 sqft
$267/sqft
Garage

About this House

In the town of Poughkeepsie there is a four bedroom three bathroom house for sale. Follow the road slightly uphill to your new home. Welcome to 20 Four Winds Drive. As you exit your vehicle, you can see views for miles just before you enter the home. Inside you’ll find a fantastic, comfortable layout with plenty of space to enjoy for years. Just shy of 2,000 square feet with plenty of exterior space and an attached two car garage, this home checks all of the boxes. nothing to do here but move in. Off the back, you’ll find a large deck serving as fantastic entertaining space overlooking the private backyard. An easy commute or location just minutes from the Taconic State Parkway and a short drive to the heart of Poughkeepsie. Don’t let this opportunity pass you by, book your tour today! Additional Information: ParkingFeatures:2 Car Attached,
20 Four Winds Drive, Poughkeepsie, NY 12603 is a 4 bedroom, 3 bathroom, 1,968 sqft single-family home in Red Oaks Mill, built in 1986. It last sold for $455,040 on Oct 13, 2023 (1% above the $450,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $525,800, with a rent estimate of $3,867/month.
Last check for updates: about 3 hours ago
Listed by Robert Page, (845) 309-4800
RE/MAX Town & Country, (845) 765-6128
Yesenia Pagan, (845) 770-4029
RE/MAX Town & Country, (845) 765-6128
Bought with: Colleen Bicknese, (845) 338-5252, Howard Hanna Rand Realty, (845) 338-5252
Source: OneKey® MLS as distributed by MLS GRID, MLS#H6253623

Home Details for 20 Four Winds Drive

Interior Features

Interior Details
Basement: See RemarksNumber of Rooms: 9
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 1968 Square Feet
Appliances & Utilities
Utilities: See RemarksAppliances: Dishwasher, Dryer, Refrigerator, Washer, Gas Water HeaterDishwasherDryerRefrigeratorWasher
Heating & Cooling
Heating: BaseboardHas CoolingAir Conditioning: DuctlessHas HeatingHeating Fuel: Baseboard

Exterior Features

Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas Open ParkingParking Spaces: 2Parking: Attached,Driveway,Garage
Water & Sewer
Sewer: Septic Tank

Property Information

Year Built
Year Built: 1986
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence, ResidentialArchitecture: Ranch
Building
Not Attached Property
Property Information
Included in Sale: Oven/RangeParcel Number: 1334006260048841990000

Price & Status

Price
List Price: $450,000
Status Change & Dates
Off Market Date: Thu Aug 03 2023

Active Status

MLS Status: Sold

Location

Direction & Address
City: Poughkeepsie
School Information
Elementary School: Overlook Primary SchoolHigh School: Arlington High SchoolHigh School District: Arlington

Building

Building Area
Building Area: 1968 Square Feet

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 0.67 acres

Offer

Listing Agreement Type: Exclusive Right To Sell

Miscellaneous

BasementMls Number: H6253623Attic: See RemarksAttribution Contact: (845) 765-6128Showing Requirements: Combination Lock Box

Price and Tax history

DateEventPrice
Oct 13, 2023
Source: OneKey® MLS as distributed by MLS GRID #H6253623
Sold
$455,040
Aug 4, 2023
Source: OneKey® MLS as distributed by MLS GRID #H6253623
Pending
$450,000
Jun 8, 2023
Source: OneKey® MLS as distributed by MLS GRID #H6253623
Listed For Sale
$450,000
Jun 2, 2015
Source: OneKey® MLS as distributed by MLS GRID #H4507881
Sold
$275,000
May 29, 2015
Source: Agent Provided
Listed For Sale
$289,000

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

Based on information submitted to the MLS GRID as of 2026-09-14 16:13:25 PDT All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Some IDX listings have been excluded from this website. Click here for more information

Frequently asked questions about 20 Four Winds Drive

  • What is 20 Four Winds Drive estimated to be worth?
    Trulia's estimated value for 20 Four Winds Drive in Poughkeepsie, NY is $525,800.
  • What is the price history for 20 Four Winds Drive?
    20 Four Winds Drive in Poughkeepsie, NY last sold for $455,040 in October 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 $431K. That is up $23.33K from the prior month.
  • Does 20 Four Winds Drive have air conditioning?
    Yes, 20 Four Winds Drive in Poughkeepsie, NY has air conditioning.
  • Does 20 Four Winds Drive have laundry facilities?
    Yes, 20 Four Winds Drive in Poughkeepsie, NY has in-unit laundry.

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