2 W Winding Rd, Poughkeepsie, NY 12601
OFF MARKET

2 W Winding Rd
Poughkeepsie, NY 12601

  • 5 Beds
  • 2 Baths
  • 2,592 sqft (on 0.30 acres)

$579,400

Trulia Estimate
as of Aug 1, 2026
Est. Refi. Payment $3,885/mo*
Refinance Your Home

$579,400

Trulia Estimate
as of Aug 1, 2026
Est. Refi. Payment $3,885/mo*
Refinance Your Home
5 Beds
2 Baths
2,592 sqft
(on 0.30 acres)

Local Information

  • Map ViewExplore the area around 2 W Winding Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1950
Lot Size
0.3 acres
Living Area
2,592 sqft
Price/Sqft
$224
Parking
Garage

About this House

This single-family home is located at 2 W Winding Rd, Poughkeepsie, NY. 2 W Winding Rd is in Poughkeepsie, NY and in ZIP code 12601. This property has 5 bedrooms, 2 bathrooms and approximately 2,592 sqft of floor space. This property has a lot size of 0.30 acres and was built in 1950.
2 W Winding Rd, Poughkeepsie, NY 12601 is a 5 bedroom, 2 bathroom, 2,592 sqft single-family home built in 1950. It last sold for $380,000 on Mar 31, 2020. It is currently off market. The Trulia Estimate is $579,400, with a rent estimate of $3,781/month.

Home Details for 2 W Winding Rd

Interior Features

Interior Details
BasementTypes of Rooms: Dining Room, Office
Heating & Cooling
Heating: Baseboard, Forced Air, GasAir ConditioningCooling System: Central, WallHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Hardwood, Linoleum Vinyl
Appliances & Utilities
DishwasherDryerRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Brick
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 1950
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Community

Units in Building: 1

Lot Information

Lot Area: 0.30 acres

Price History for 2 W Winding Rd

DatePriceEventSource
03/31/2020$380,000Sold
OneKey® MLS as distributed by MLS GRID #M387825
02/06/2020$380,000PendingAgent Provided
01/16/2020$380,000Listed For SaleAgent Provided
04/18/2012$335,000Sold
N/A
10/21/2011$385,000PriceChange
Agent Provided
09/24/2011$399,000Listed For SaleAgent Provided

Market trends in Poughkeepsie

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$405K
$25.67KMoM
Sale-to-List Price
100.3%
0.3%MoM
Price per sq ft
$234
$1MoM
Available listings
203
11MoM
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Property Tax and Assessment

Year2025
Tax
Assessment$501,100
Home facts updated by county records

Comparable Sales for 2 W Winding Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
26 Loockerman Avenue, Poughkeepsie, NY
0.04
Single-Family Home
$520,000
12/22/25
4
2.5
2,712
6 Rosalind Road, Poughkeepsie, NY
0.09
Single-Family Home
$529,000
04/10/26
3
1.5
2,138
9 Rosalind Road, Poughkeepsie, NY
0.11
Single-Family Home
$551,000
04/21/26
4
2.5
2,484
1 W Winding Road, Poughkeepsie, NY
0.03
Single-Family Home
$670,000
06/03/26
4
3.5
2,326
3 Saint Annes Road, Poughkeepsie, NY
0.24
Single-Family Home
$430,000
09/12/25
3
1.5
2,032
6 Yates Boulevard, Poughkeepsie, NY
0.27
Single-Family Home
$620,000
06/25/26
4
2
2,343
31 Bancroft Rd, Poughkeepsie, NY
0.32
Single-Family Home
$462,000
08/01/25
3
2
2,940
17 Seaman Road, Poughkeepsie, NY
0.24
Single-Family Home
$565,000
11/21/25
4
2
3,198
34 Adriance Avenue, Poughkeepsie, NY
0.21
Single-Family Home
$508,000
03/18/26
4
2.5
2,374
20 Kimball Road, Poughkeepsie, NY
0.29
Single-Family Home
$435,000
11/07/25
3
1.5
1,918

Nearby homes

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Assigned Schools

These are the assigned schools for 2 W Winding Rd.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Poughkeepsie

At least 909 Trulia users voted on each feature.

  • 82 % Say car is needed

  • 82 % Say it's dog friendly

  • 75 % Say parking is easy

  • 69 % Say yards are well-kept

  • 68 % Say there's holiday spirit

  • 64 % Say there are sidewalks

  • 62 % Say kids play outside

  • 60 % Say there's wildlife

  • 58 % Say streets are well-lit

  • 56 % Say it's walkable to restaurants

  • 55 % Say people would walk alone at night

  • 54 % Say it's quiet

  • 52 % Say neighbors are friendly

  • 50 % Say they plan to stay for at least 5 years

  • 46 % Say it's walkable to grocery stores

  • 32 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Colleen marrin
    "I love it "
    0
    Flag
  • 97jrdwf5w2
    "The night walk over the Hudson is amazing and a can’t miss opportunity. College food trucks and pop up events keep the area hot. "
    1
    Flag
  • Jose Gonzalez
    "Poughkeepsie is an amazing town to live in. Moved from NYC and never regretting the decision. I welcome anyone who wishes to live in Poughkeepsie. "
    1
    Flag
  • Evooirene600
    "Public libraries with many programs and clubs ,for example gardening and board games. Local farms markets "
    1
    Flag
  • Andrina Simengwa
    "Public buses run on weekdays from early morning until late evening, providing transportation for commuters and local residents. On Saturdays, they operate with reduced hours but still maintain regular routes to serve shopping centers and community facilities."
    3
    Flag
  • Rebekah Hemingway
    "Ok, however im not used to the city. Except theres not a lot of busses. Theyre are busses, just not a lot. So you need a car to get where a short 14min car ride takes over 1 hr to bus or over 2- more hrs to walk some places. Say if this was albany we could catch a bus every 15-20mins 7days a week, pretty much every block and get anywhere you want."
    1
    Flag
  • Evooirene600
    "There is Traffic congestion during rush hours, moderate traffic otherwise, rt. 9 always busy, round abouts. Bridge traffic can be heavy."
    0
    Flag
  • Tiasteph2019
    "Although we only just moved into this section of the district—Crown Heights, or Nassau—we’ve actually been connected to this school community for a long time. My daughters have grown up visiting their friends here, and we’ve always known this area to be calm, peaceful, and family-friendly. "
    0
    Flag
  • Meeshzdunczyk
    "This neighborhood has great access to route 9 amenities and city of Poughkeepsie. Short drive to train stations for longer commutes"
    0
    Flag
  • Btissier323
    "There are many families here we have a tennis court and basketball court we can play pickle ball there is also a playground "
    0
    Flag
  • Trulia User
    "Mostly amazing with some days ruined by a few crazy drivers who need to retake drivers ed!!!!!!!!!!!!"
    0
    Flag
  • Edith Perez
    "The cultural diversity and the beautiful autumn colors. The Hudson River and the beautiful sunsets make this area unique. "
    1
    Flag
  • Sergio
    "Suburbs/Towns of Poughkeepsie are very safe. City of Poughkeepsie is a high crime area and should be visited with vigilance. "
    22
    Flag
  • Darryl Hendricks
    "It’s extremely quiet all year long. When someone has a party that is going to run late, they will let neighbors know ahead of time. "
    0
    Flag
  • Sarah Muller
    " Live near the town, Hyde Park School district. This spot is better than the city of Poughkeepsie, which is not so nice."
    15
    Flag
  • Trulia User
    "it's a nice area. most people pick up after their dogs. Dog owners and pups know each other.The barking is not bad at all. Most pups are friendly t"
    2
    Flag
  • Trulia User
    " I’ve lived here for 10 years and it has been a very safe and enjoyable neighborhood to live in. The schools are very good both public and parochial. There is great access to shopping, groceries and restaurants. There are lots of parks, museums and rail trails in the area. The city also has the walkway over the Hudson which is a great attraction. Access to NYVc is easy and 1:30 minutes on the train with a ride along the Hudson River. Overall the area is safe. The four seasons give a great opportunity to enjoy the holidays. "
    5
    Flag
  • Trulia User
    "I love this place. I feel safe living here and my children feel free to do what they want without having to worry about their safety. "
    1
    Flag
  • Eliasreyes.music
    "There are cultured festivals. High school games, the neighbors are so sweet and generous. They’ve become family to me. I don’t see myself living anywhere else"
    29
    Flag
  • Eliasreyes.music
    "There are friendly dogs everywhere. The dog park is beautiful here. People are very friendly. There are walking paths everywhere"
    8
    Flag
  • Danielle
    "My commute is okay - you def need a car to drive to places. I haven’t taken public transportation around here but college students might and it is friendly around there"
    9
    Flag
  • Danielle
    "Great families lovely neighborhood and just a great place to live. I think this is also a great neighborhood "
    2
    Flag
  • Freddie M. J.
    "easy commute to Westchester and the surrounding areas. Hopefully I will move closer to route 9 within a few months"
    1
    Flag
  • Danielle
    "Safe neighborhood, good schools and overall great environment for many famIlies and even for pets - love it"
    3
    Flag
  • Megw801
    "There are no sidewalks in this area of Poughkeepsie but I actually like that. The lack of sidewalks gives that suburban feel and I don’t like the idea of random people walking by my home."
    11
    Flag
  • Alberto B. Q.
    "there is a good choice of parks, but they are not always close by. Alternatively there are a lot of side walks."
    0
    Flag
  • Sherry M.
    "Several people have dogs and cats on the street that we live on. Neighbors are protective and keep an eye on speeders"
    0
    Flag
  • Syacab26
    "Too much traffic and very noisy. Not enough grass to play on. People don’t pay attention turning the corner."
    0
    Flag
  • Eliasreyes.music
    "It’s awesome, I love living here. It’s so peaceful, my dogs and my daughter are very happy here. My neighbors are like family to me."
    5
    Flag
  • Ciara N. D.
    "The walkway give good overlook site of town lots of event take place on walkway.. or a nice place to walk or ride bikes with family and friends "
    2
    Flag
  • Ed
    "Great schools in town. Quiet place to raise your kids. Close proximity to metro north train and access to the city is great."
    6
    Flag
  • Jamilgafur
    "Ok The neighborhood is very safe and is a good place to raise a family very quiet private a real sense of family"
    5
    Flag
  • Tawana L.
    "Nothing they would love bringing their pets to the the community just make sure you pick up after the pet too many kids that love to sit in the park "
    2
    Flag
  • Luisroddi
    "Several festivals. Like Italian festival, Greek festival, lost of college activities. Etc. the area is full of outdoors activities "
    2
    Flag
  • Csalvad1
    "My friends live here and everything is great besides road maintenance It is located close to Poughkeepsie wappingers fishkill and beacon so there is a lot to do. I the neighborhoods are friendly and it has easy access to most main roads and highways. "
    0
    Flag
  • Pearl R.
    "There are community events. However, ALL are not always welcome. For the community to be so diverse, there's a lot of prejudice and judgement. It is a small community with a lot of negativity, drugs and gangs. Not a lot of free inner city activities and/or activities with small fees aren't close for non drivers."
    5
    Flag
  • Gina G
    "We have a lake for the residents, an annual carnival and community day, the schools are great and the people in the town are really good families, we have great sports leagues an all around great place to raise your kids. "
    0
    Flag
  • Coachkathycitera
    "It’s lovely here. Peaceful and lots of nature. Very private, blue ribbon schools. It is an executive neighborhood."
    0
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  • Sas62
    "I have lived in the Spackenkill part of Poughkeepsis over 20 years. Raised my children here and love the schools. People are friendly and very nice. "
    0
    Flag
  • Jaheim G.
    "I was born and lived in Poughkeepsie until I was 10 years old. It was always great to me. I remember going down by the river and waiting for the ice cream to come. Smith Street hot dogs, TJ’s Pizza, and La Deliziosa Pastry Shop are some of the best places to eat from if you’re visiting. "
    0
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Homes for sale near 2 W Winding Rd

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Off Market Homes Near 2 W Winding Rd

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