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

$605,600

Trulia Estimate
  • 4 Beds
  • 2.5 Baths
  • 2,359 sqft (on 0.50 acres)

2 Four Winds Dr, Poughkeepsie, NY 12603

Red Oaks Mill
Est. Refi. Payment $4,103/mo*
Refinance Your Home
Currently Off Market - Sold Nov 8, 2018 for $370,000

Home Value

Trulia Estimate
$606K
Since last month
Decreased$10K (-1.6%)
Since last year
Increased$17K (+2.9%)
Since last sale
Increased$233K (+62.9%)
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
August 2026$603K
July 2026$613K
June 2026$619K
May 2026$598K
April 2026$588K
March 2026$578K
February 2026$573K
January 2026$571K
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
0.51
Single-Family Home
$365,000
08/18/26
3
2
1,736
4 North Drive, Poughkeepsie, NY
0.47
Single-Family Home
$450,000
07/31/26
3
2
1,660
1 Davis Road, Poughkeepsie, NY
0.63
Single-Family Home
$405,000
09/03/25
3
1.5
1,619
137 Simone Dr, Poughkeepsie, NY
0.79
Single-Family Home
$560,000
07/21/26
4
3
2,539
24 Maloney Drive, Wappingers Falls, NY
0.74
Single-Family Home
$665,000
10/22/25
4
2.5
3,474
96 Daley Road, Poughkeepsie, NY
0.54
Single-Family Home
$515,000
12/17/25
3
3
1,728
28 Red Oaks Mill Road, Poughkeepsie, NY
0.56
Single-Family Home
$425,000
03/30/26
3
1
1,302
27 King Drive, Poughkeepsie, NY
0.65
Single-Family Home
$700,000
04/24/26
4
4
2,529
137 Simone Drive, Poughkeepsie, NY
0.79
Single-Family Home
$560,000
07/02/26
5
3
2,539
13 Bray Farm Lane, Wappingers Falls, NY
0.66
Single-Family Home
$635,000
05/28/26
4
2.5
2,470

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
0.14
$549,900
3
3
2,000
For Sale
11 Four Winds Drive, Poughkeepsie, NY 12603
0.15
$509,400
3
2
1,486
Off Market
20 Four Winds Drive, Poughkeepsie, NY 12603
0.18
$525,800
4
2.5
1,968
Off Market
22 Four Winds Drive, Poughkeepsie, NY 12603
0.19
$622,400
4
2.5
2,332
Off Market
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
0.23
$425,200
2
1
1,176
Off Market
55 Daley Road, Poughkeepsie, NY 12603
0.28
$1,500,000
4
5.5
5,475
For Sale
46 Kevin Heights, Poughkeepsie, NY 12603
0.34
$475,000
4
3
2,250
For Sale
10 Partners Trace, Poughkeepsie, NY 12603
0.31
$620,600
3
3
3,106
Off Market
25 Cochran Hill Road, Poughkeepsie, NY 12603
0.33
$524,000
3
2
2,400
Off Market
26 Kevin Heights, Poughkeepsie, NY 12603
0.37
$531,100
4
2.5
2,085
Off Market
14 Merry Hill Road, Poughkeepsie, NY 12603
0.38
$515,900
3
2.5
1,950
Off Market

Local Information

  • Map ViewExplore the area around 2 Four Winds Dr.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1987
Lot Size
0.5 acres
Living Area
2,359 sqft
Price/Sqft
$257
Parking
Garage

About this House

A wonderful house to call home. Lovingly cared for 4 Bedroom Colonial in the Arlington School District. Recent updates include Kitchen Renovation, New Windows, Central A/C, rejuvenated deck and porch, and roof that is 5 yrs. young. Enjoy afternoons on the rocking chair front porch, gatherings and BBQs on the back deck, and warm cozy nights watching TV by the fireplace in the welcoming Family room. Also very convenient to the beautiful and popular Dutchess Rail Trail. Be sure to schedule an appointment today to come and see this wonderful house for yourself.
2 Four Winds Dr, Poughkeepsie, NY 12603 is a 4 bedroom, 3 bathroom, 2,359 sqft single-family home in Red Oaks Mill, built in 1987. It last sold for $370,000 on Nov 8, 2018. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $605,600, with a rent estimate of $3,993/month.

Home Details for 2 Four Winds Dr

Interior Features

Heating & Cooling
Heating: Baseboard, GasAir ConditioningCooling System: CentralHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 2Floors: Other
Interior Details
Number of Rooms: 8
Appliances & Utilities
DishwasherDryerRefrigerator
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: Asphalt, Shake ShingleExterior: VinylPatio
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

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

Community

Units in Building: 1

Lot Information

Lot Area: 0.50 acres

Price and Tax history

DateEventPrice
Nov 8, 2018
Source: OneKey® MLS as distributed by MLS GRID #H4831838
Sold
$370,000
Sep 17, 2018
Source: Agent Provided
Pending
$379,900
Jul 11, 2018
Source: Agent Provided
PriceChange
$379,900
Price decreased by 21%
Jul 9, 2018
Source: Agent Provided
PriceChange
$479,900
Price increased by 26%
Jul 7, 2018
Source: Agent Provided
PriceChange
$379,900
Price decreased by 3%

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 2 Four Winds Dr

  • What is 2 Four Winds Dr estimated to be worth?
    Trulia's estimated value for 2 Four Winds Dr in Poughkeepsie, NY is $605,600.
  • What is the price history for 2 Four Winds Dr?
    2 Four Winds Dr in Poughkeepsie, NY last sold for $370,000 in November 2018.
  • 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 2 Four Winds Dr have air conditioning?
    Yes, 2 Four Winds Dr in Poughkeepsie, NY has air conditioning.
  • Does 2 Four Winds Dr have laundry facilities?
    Yes, 2 Four Winds Dr in Poughkeepsie, NY has laundry facilities.

Explore by feature - Pet Friendly

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Explore by feature - Outdoor Space

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Apartments for Rent

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Off Market Homes Near 2 Four Winds Dr

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