27 S Jackson Dr, Poughkeepsie, NY 12603
OFF MARKET

27 S Jackson Dr
Poughkeepsie, NY 12603

  • 4 Beds
  • 3 Baths
  • 1,950 sqft (on 1 acre)

$506,300

Trulia Estimate
as of Jul 7, 2026
Est. Refi. Payment $3,411/mo*
Refinance Your Home

$506,300

Trulia Estimate
as of Jul 7, 2026
Est. Refi. Payment $3,411/mo*
Refinance Your Home
4 Beds
3 Baths
1,950 sqft
(on 1 acre)

Local Information

  • Map ViewExplore the area around 27 S Jackson Dr.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

This single-family home is located at 27 S Jackson Dr, Poughkeepsie, NY. 27 S Jackson Dr is in Poughkeepsie, NY and in ZIP code 12603. This property has 4 bedrooms, 3 bathrooms and approximately 1,950 sqft of floor space. This property has a lot size of 1 acre and was built in 1960.
27 S Jackson Dr, Poughkeepsie, NY 12603 is a 4 bedroom, 3 bathroom, 1,950 sqft single-family home built in 1960. It last sold for $265,000 on Apr 11, 2003. It is currently off market. The Trulia Estimate is $506,300, with a rent estimate of $3,924/month.

Home Highlights

Parking
Garage
Outdoor
No Info
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 27 S Jackson Dr

Interior Features

Interior Details
Basement
Heating & Cooling
Heating: Other, OtherHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 1
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1960Year Updated: 1987
Property Type / Style
Property Type: Single Family HomeArchitecture: split level

Exterior Features

Exterior Home Features
Exterior: Other
Parking & Garage
GarageParking: Garage Attached

Community

Units in Building: 1

Lot Information

Lot Area: 1 acre

Price History for 27 S Jackson Dr

DatePriceEventSource
04/11/2003$265,000Sold
N/A

Market trends in Poughkeepsie

Last updated May 2026
Buyer'sMarketSeller'sMarket
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

Year2025
Tax
Assessment$426,400
Home facts updated by county records

Comparable Sales for 27 S Jackson Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
513 Vassar Road, Poughkeepsie, NY
0.29
Single-Family Home
$425,000
11/21/25
4
2
1,672
7 Oak Bend Road, Poughkeepsie, NY
0.69
Single-Family Home
$469,000
10/17/25
4
2.5
2,006
18 Lorraine Boulevard, Poughkeepsie, NY
0.18
Single-Family Home
$505,000
08/14/25
3
2
1,552
24 Lorraine Boulevard, Poughkeepsie, NY
0.12
Single-Family Home
$330,000
06/10/26
3
1
1,222
3 N Jackson Road, Poughkeepsie, NY
0.42
Single-Family Home
$470,000
09/29/25
3
1.5
1,652
84 Hillis Terrace, Poughkeepsie, NY
0.80
Single-Family Home
$445,000
05/06/26
3
2.5
1,824
4 Ridgewood Terrace, Poughkeepsie, NY
0.36
Single-Family Home
$466,000
05/08/26
3
1.5
2,062
18 Alexander Boulevard, Poughkeepsie, NY
0.35
Single-Family Home
$449,000
10/31/25
3
1
1,800
7 Broadview Road, Poughkeepsie, NY
0.65
Single-Family Home
$485,000
02/04/26
3
2
2,304
43 Briarcliff Avenue, Poughkeepsie, NY
0.49
Single-Family Home
$470,000
01/28/26
3
1.5
2,529

Nearby homes

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Assigned Schools

These are the assigned schools for 27 S Jackson Dr.
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 906 Trulia users voted on each feature.

  • 82 % Say car is needed

  • 81 % Say it's dog friendly

  • 75 % Say parking is easy

  • 69 % Say yards are well-kept

  • 67 % Say there's holiday spirit

  • 64 % Say there are sidewalks

  • 62 % Say kids play outside

  • 59 % Say there's wildlife

  • 57 % 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

  • 51 % 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.
  • 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."
    2
    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
  • Evan
    "Very walkable downtown with several dog friendly restaurants available. Lots of local parks for Fido to enjoy sniffing."
    0
    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
    Flag
  • 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
    Flag

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Homes for sale near 27 S Jackson Dr

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Off Market Homes Near 27 S Jackson Dr

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