20 Four Winds Drive
Poughkeepsie, NY 12603
Red Oaks Mill
4 Beds
2.5 Baths
1,968 sqft (on 0.67 acres)
4 Beds
2.5 Baths
1,968 sqft
(on 0.67 acres)
Local Information
- Map ViewExplore the area around 20 Four Winds Drive.
- Schools2 Elementary Schools1 Middle School1 High School
- Shop & Eat
-- mins to
Description
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). It is currently off market. The Trulia Estimate is $536,600, with a rent estimate of $3,924/month.
Home Highlights
Parking
Garage
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
180+ days ago
Home Details for 20 Four Winds Drive
|
|---|
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 |
|
|---|
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 |
|
|---|
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 List Price: $450,000 |
Status Change & Dates Off Market Date: Thu Aug 03 2023 |
|
|---|
MLS Status: Sold |
|
|---|
Direction & Address City: Poughkeepsie |
School Information Elementary School: Overlook Primary SchoolHigh School: Arlington High SchoolHigh School District: Arlington |
|
|---|
Building Area Building Area: 1968 Square Feet |
|
|---|
Not Senior Community |
|
|---|
No HOA |
|
|---|
Lot Area: 0.67 acres |
|
|---|
Listing Agreement Type: Exclusive Right To Sell |
|
|---|
BasementMls Number: H6253623Attic: See RemarksAttribution Contact: (845) 765-6128Showing Requirements: Combination Lock Box |
Last check for updates: about 12 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
Price History for 20 Four Winds Drive
| Date | Price | Event | Source |
|---|---|---|---|
| 10/13/2023 | $455,040 | Sold | OneKey® MLS as distributed by MLS GRID #H6253623 |
| 08/04/2023 | $450,000 | Pending | OneKey® MLS as distributed by MLS GRID #H6253623 |
| 06/08/2023 | $450,000 | Listed For Sale | OneKey® MLS as distributed by MLS GRID #H6253623 |
| 06/02/2015 | $275,000 | Sold | OneKey® MLS as distributed by MLS GRID #H4507881 |
| 05/29/2015 | $289,000 | Listed For Sale | Agent Provided |
| 04/20/2015 | $289,000 | ListingRemoved | Agent Provided |
| 03/02/2015 | $289,000 | Listed For Sale | Agent Provided |
| 11/09/2012 | $254,800 | Sold | OneKey® MLS as distributed by MLS GRID #M307801 |
| 08/03/2012 | $249,900 | PriceChange | Agent Provided |
| 07/04/2012 | $254,900 | PriceChange | Agent Provided |
| 06/02/2012 | $269,000 | Listed For Sale | Agent Provided |
| 01/24/1995 | $166,500 | Sold | N/A |
Market trends in Poughkeepsie
Last updated May 2026
Avg. sale price
$380K
$4KMoM
Sale-to-List Price
100.0%
0.1%MoM
Price per sq ft
$236
$2MoM
Available listings
192
28MoM
- Results are loading
Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | |
| Assessment | $457,500 |
Home facts updated by county records
Comparable Sales for 20 Four Winds Drive
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.33 | Single-Family Home | $536,000 | 08/13/25 | 3 | 2.5 | 2,192 | |
0.40 | Single-Family Home | $515,000 | 12/17/25 | 3 | 3 | 1,728 | |
0.61 | Single-Family Home | $635,000 | 05/28/26 | 4 | 2.5 | 2,470 | |
0.52 | Single-Family Home | $388,000 | 04/22/26 | 3 | 1 | 1,412 | |
0.74 | Single-Family Home | $429,000 | 05/06/26 | 3 | 2 | 1,773 | |
0.64 | Single-Family Home | $665,000 | 10/22/25 | 4 | 2.5 | 3,474 | |
0.52 | Single-Family Home | $425,000 | 03/30/26 | 3 | 1 | 1,302 | |
0.81 | Single-Family Home | $405,000 | 09/03/25 | 3 | 1.5 | 1,619 | |
0.74 | Single-Family Home | $700,000 | 04/24/26 | 4 | 4 | 2,529 | |
0.31 | Single-Family Home | $550,000 | 05/06/26 | 5 | 3 | 2,362 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.
OFF MARKETBHHS Hudson Valley Properties
OFF MARKETBHHS Hudson Valley Properties
OFF MARKETBHHS Hudson Valley Properties
OFF MARKETBHHS Hudson Valley Properties
OFF MARKETNeil Charles Real Estate, LLC
SOLDMAY 6, 2026Keller Williams Realty HV Nort, Closed
FOR SALENEW CONSTRUCTION
3D VIEW71.67 ACRESListing by: Giner Real Estate Inc.
OFF MARKETColdwell Banker Realty
SOLDDEC 17, 2025Houlihan Lawrence Inc.
OFF MARKETCentury 21 Alliance Rlty Group
Assigned Schools
These are the assigned schools for 20 Four Winds Drive.
- Arlington High School
- 9-12
- Public
- 2472 Students
6/10GreatSchools RatingParent Rating AverageArlington High School is a fabulous school with tremendous opportunities for both academic and athletic success. They have copious amounts of student engagement and clubs to join, and everyone fits in somewhere. You have to be proactive in finding these opportunities, though, in order to cultivate personal success. The school's large population doesn't really encourage hand holding, so it's important that your child is speaking up and being their own advocate when it comes to their academics and extracurriculars. They have so many AP courses that really helped me jumpstart my college career and graduate in 3.5 years instead of 4. As a proud alumni, my experiences at Arlington were a major factor in my successful post-college career.Other Review6mo ago - Overlook Primary School
- K-2
- Public
- 394 Students
NAGreatSchools RatingParent Rating AverageOverlook School continue to impress me. My son had Mrs.Pakrad for Kindergarten and she was an absolute gem! Such a thoughtful and caring teacher who truly took time to understand each child and taught them in a way that helped them be successful. The school also has wonderful support services and activities outside of school hours - we live the monthly Friday morning family walks. The playground is excellent and they continue to make improvements to the school. We have really enjoyed being a park of the community.Note in my review I have special education a neutral rating because we do not use these services.Parent Review10mo ago - Titusville Intermediate School
- 3-5
- Public
- 425 Students
4/10GreatSchools RatingParent Rating AverageGreat teachers...great curriculum...great kids!!Parent Review15y ago - Union Vale Middle School
- 6-8
- Public
- 990 Students
3/10GreatSchools RatingParent Rating AverageMy little girl attended this school only for a few months , she is autistic and needs alot of support, which this horrible school did not give her, the principal has no clue how to run a school and treats parents as if they were villains, they have no idea how to deal with special needs children and my little girl is safe now in a different school! They lied too, they said the teacher that was awful with my daughter retired and they kept her there working with innocent children!!! This principal needs to take a lesson from other principals on how to treat parents with respect!!!!! Beware parents this school does meet the requirements to take care of special needs children!!!!Parent Review4mo ago 
Check out schools near 20 Four Winds Drive.
Neighborhood Overview
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
LGBTQ Local Legal Protections
Apartments for Rent
PET FRIENDLYHoulihan-Parnes Realtors
PET FRIENDLYBaxter Property Management
PET FRIENDLYFidelity Real Estate Management LLC
See more homes for rent inPoughkeepsie
Explore by feature - Pet Friendly
- SPECIAL OFFERPET FRIENDLYHoulihan-Parnes Realtors
SPECIAL OFFERPET FRIENDLYRose Associates
PET FRIENDLYHub Realty Associates
PET FRIENDLYHub Realty Associates
NEW - 1 DAY AGOPET FRIENDLY
PET FRIENDLYVentus Capital
SPECIAL OFFERPET FRIENDLYLease UP! LLC
NEW - 1 DAY AGOPET FRIENDLYBaxter Property Management
PET FRIENDLYBaxter Property Management
PET FRIENDLY
Explore by feature - Garage
- PET FRIENDLYBaxter Property Management
APPLY INSTANTLYPET FRIENDLYFaze One Funding
NEW - 1 DAY AGOFURNISHEDeXp Realty
Berkshire Hathaway HomeServices Hudson Valley Properties
Explore by feature - Air Conditioning
- SPECIAL OFFERPET FRIENDLYHoulihan-Parnes Realtors
- PET FRIENDLYHub Realty Associates
- PET FRIENDLYHub Realty Associates
- NEW - 1 DAY AGOPET FRIENDLY
- PET FRIENDLYVentus Capital
PET FRIENDLY- NEW - 1 DAY AGOPET FRIENDLYBaxter Property Management
- PET FRIENDLYBaxter Property Management
- PET FRIENDLY
- PET FRIENDLYBaxter Property Management
Explore by feature - Pool
- PET FRIENDLYHub Realty Associates
- PET FRIENDLYHub Realty Associates
- NEW - 1 DAY AGOPET FRIENDLY
- PET FRIENDLYVentus Capital
- APPLY INSTANTLYPET FRIENDLYFaze One Funding
- APPLY INSTANTLYPET FRIENDLYFURNISHED
Explore by feature - Washer/dryer
- SPECIAL OFFERPET FRIENDLYHoulihan-Parnes Realtors
- PET FRIENDLYHub Realty Associates
- PET FRIENDLYHub Realty Associates
- NEW - 1 DAY AGOPET FRIENDLY
- PET FRIENDLYVentus Capital
- SPECIAL OFFERPET FRIENDLYLease UP! LLC
- NEW - 1 DAY AGOPET FRIENDLYBaxter Property Management
- PET FRIENDLYBaxter Property Management
- PET FRIENDLY
Explore by feature - Outdoor Space
APPLY INSTANTLY- PET FRIENDLYFidelity Real Estate Management LLC
NEW - 2 DAYS AGOAPPLY INSTANTLYPET FRIENDLY
APPLY INSTANTLYPET FRIENDLY
APPLY INSTANTLY
APPLY INSTANTLYPET FRIENDLY
APPLY INSTANTLYPET FRIENDLY
Homes for sale near 20 Four Winds Drive
OPEN SUN, 2-4PM1 ACREListing by: BHHS Hudson Valley Properties
0.59 ACRESListing by: BHHS Hudson Valley Properties
0.39 ACRESListing by: BHHS Hudson Valley Properties
0.5 ACRESListing by: KW MidHudson
1.55 ACRESListing by: BHHS Hudson Valley Properties
See more homes for sale inPoughkeepsie
Off Market Homes Near 20 Four Winds Drive
SOLDJUL 7, 2026Weichert Realtors
SOLDJUL 6, 2026Compass Greater NY, LLC
SOLDJUL 2, 2026BHHS Hudson Valley Properties
SOLDJUL 2, 2026Houlihan Lawrence Inc.
SOLDJUL 1, 2026Keller Williams Realty Partner
SOLDJUL 1, 2026Westchester Dream Home Realty
SOLDJUN 30, 2026Houlihan Lawrence Inc.
SOLDJUN 29, 2026Amodio Real Estate & Prop, Closed- See more homes for sale inPoughkeepsie
Based on information submitted to the MLS GRID as of 2026-02-06 15:18:24 PST. 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