21 Four Winds Dr
Poughkeepsie, NY 12603
Red Oaks Mill
4 Beds
2.5 Baths
3,236 sqft (on 1.48 acres)
4 Beds
2.5 Baths
3,236 sqft
(on 1.48 acres)
Local Information
- Map ViewExplore the area around 21 Four Winds Dr.
- Schools2 Elementary Schools1 Middle School1 High School
- Shop & Eat
-- mins to
Description
Welcome Home! In a neighborhood, at the end of a quiet cul-de-sac street, you'll find this attractive colonial where pride of ownership shows. The kitchen has been beautifully renovated and it is a chef's delight offering granite counters and plenty of entertaining space. The light and bright family room has vaulted ceilings, skylights and raised brick hearth gas fireplace. The formal living and dining rooms are spacious and complete with beautiful hardwood floors. Upstairs you'll find roomy bedrooms for all with the master bedroom offering an en-suite bath and generous walk in closet. The lowest level offers walkout access with bonus play space, office and workshop area. Enjoy peace and privacy on the over-sized deck and beautiful circular patio. The tree lined property has been thoughtfully planned with flowering shrubs and grasses creating a relaxing, natural retreat. Fantastic location just minutes to highways, shopping, and the Dutchess Rail Trail.
21 Four Winds Dr, Poughkeepsie, NY 12603 is a 4 bedroom, 3 bathroom, 3,236 sqft single-family home in Red Oaks Mill, built in 1986. It last sold for $362,000 on May 9, 2019. It is currently off market. The Trulia Estimate is $629,300, with a rent estimate of $4,108/month.
Home Highlights
Parking
Garage
Outdoor
Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago
Home Details for 21 Four Winds Dr
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Interior Details BasementNumber of Rooms: 8Types of Rooms: Walk In Closet, Dining RoomCeiling Fan |
Heating & Cooling Heating: Baseboard, GasAir ConditioningCooling System: CentralHeating Fuel: Baseboard |
Levels, Entrance, & Accessibility Stories: 2Floors: Tile, Carpet, Hardwood |
Appliances & Utilities DishwasherDryerRefrigeratorWasher |
Fireplace & Spa Fireplace |
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Exterior Home Features Roof: AsphaltDeckExterior: Vinyl, Brick |
Parking & Garage GarageParking Spaces: 2Parking: Garage Attached |
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Year Built Year Built: 1986Year Updated: 1990 |
Property Type / Style Property Type: Single Family HomeArchitecture: Colonial |
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Units in Building: 1 |
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Lot Area: 1.48 acres |
Price History for 21 Four Winds Dr
| Date | Price | Event | Source |
|---|---|---|---|
| 05/09/2019 | $362,000 | Sold | OneKey® MLS as distributed by MLS GRID #H4908986 |
| 03/17/2019 | $365,000 | Pending | Agent Provided |
| 02/19/2019 | $365,000 | Listed For Sale | Agent Provided |
| 12/19/2018 | $368,000 | ListingRemoved | Agent Provided |
| 09/14/2018 | $368,000 | PriceChange | Agent Provided |
| 08/28/2018 | $370,000 | PriceChange | Agent Provided |
| 08/11/2018 | $375,000 | PriceChange | Agent Provided |
| 06/19/2018 | $385,000 | Listed For Sale | Agent Provided |
| 11/25/1992 | $185,000 | 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
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | |
| Assessment | $482,000 |
Home facts updated by county records
Comparable Sales for 21 Four Winds Dr
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.31 | Single-Family Home | $515,000 | 12/17/25 | 3 | 3 | 1,728 | |
0.53 | Single-Family Home | $635,000 | 05/28/26 | 4 | 2.5 | 2,470 | |
0.35 | Single-Family Home | $536,000 | 08/13/25 | 3 | 2.5 | 2,192 | |
0.71 | Single-Family Home | $665,000 | 11/26/25 | 4 | 3.5 | 2,567 | |
0.54 | Single-Family Home | $665,000 | 10/22/25 | 4 | 2.5 | 3,474 | |
0.21 | Single-Family Home | $550,000 | 05/06/26 | 5 | 3 | 2,362 | |
0.85 | Single-Family Home | $485,000 | 02/18/26 | 4 | 2 | 1,800 | |
0.82 | Single-Family Home | $760,000 | 12/12/25 | 3 | 2.5 | 2,156 | |
1.05 | Single-Family Home | $674,500 | 10/21/25 | 4 | 3 | 2,124 | |
0.56 | Single-Family Home | $388,000 | 04/22/26 | 3 | 1 | 1,412 |
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Assigned Schools
These are the assigned schools for 21 Four Winds Dr.
- 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
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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 Review5mo ago 
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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.
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