252 Overlook Rd, Poughkeepsie, NY 12603
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Property image
OFF MARKET

252 Overlook Rd
Poughkeepsie, NY 12603

  • 3 Beds
  • 2.5 Baths
  • 2,315 sqft (on 1.55 acres)

$749,600

Trulia Estimate
as of Aug 24, 2026
Est. Refi. Payment $5,056/mo*
Refinance Your Home

$749,600

Trulia Estimate
as of Aug 24, 2026
Est. Refi. Payment $5,056/mo*
Refinance Your Home
3 Beds
2.5 Baths
2,315 sqft
(on 1.55 acres)

Home Value

Trulia Estimate
$750K
Since last month
Decreased$2K (-0.3%)
Since last year
Increased$27K (+3.7%)
Since last sale
Increased$127K (+20.4%)
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 +76% in the last 10 years
MonthEstimated value
2026
August 2026$749K
July 2026$751K
June 2026$752K
May 2026$743K
April 2026$730K
March 2026$725K
February 2026$720K
January 2026$723K
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
256 Overlook Road, Poughkeepsie, NY
0.02
Single-Family Home
$650,000
07/29/26
3
2
2,381
244 Overlook Road, Poughkeepsie, NY
0.14
Single-Family Home
$460,000
10/06/25
4
2
2,000
12 Birch Hill Drive, Poughkeepsie, NY
0.40
Single-Family Home
$400,000
01/29/26
3
3
2,198
18 Birch Hill Drive, Poughkeepsie, NY
0.43
Single-Family Home
$580,000
01/07/26
3
2
3,082
210 Overlook Road, Poughkeepsie, NY
0.56
Single-Family Home
$485,000
03/20/26
3
2.5
2,048
219 Ridgeline Drive, Poughkeepsie, NY
0.62
Single-Family Home
$638,175
12/08/25
4
2.5
2,388
194 Overlook Road, Poughkeepsie, NY
0.66
Single-Family Home
$565,000
11/19/25
4
2.5
3,396
211 Overlook Rd, Poughkeepsie, NY
0.56
Single-Family Home
$240,000
12/02/25
3
1.5
2,040
71 Ridgeline Drive, Poughkeepsie, NY
0.25
Single-Family Home
$825,000
12/18/25
4
4
3,200
36 Spruce Lane, Poughkeepsie, NY
0.30
Single-Family Home
$1,250,000
08/05/26
4
3.5
3,674

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
250 Overlook Road, Poughkeepsie, NY 12603
0.03
$567,600
4
2
2,280
Off Market
256 Overlook Road, Poughkeepsie, NY 12603
0.02
$650,000
3
2
2,381
Recently Sold
213-215 Overlook Road, Poughkeepsie, NY 12603
0.09
$611,700
5
3
1,984
Off Market
244 Overlook Road, Poughkeepsie, NY 12603
0.14
$489,700
4
2
2,000
Off Market
59 Ridgeline Drive, Poughkeepsie, NY 12603
0.22
$776,900
4
2.5
2,616
Off Market
67 Ridgeline Drive, Poughkeepsie, NY 12603
0.24
$225,000
-
-
-
Recently Sold
71 Ridgeline Drive, Poughkeepsie, NY 12603
0.25
$825,000
4
4
3,200
Recently Sold
39 Ridgeline Drive, Poughkeepsie, NY 12603
0.26
$746,200
4
3.5
3,436
Off Market
36 Spruce Lane, Poughkeepsie, NY 12603
0.30
$1,250,000
4
3.5
3,674
Recently Sold
103 Ridgeline Drive, Poughkeepsie, NY 12603
0.36
$964,800
4
4.5
4,355
Off Market
16 Birch Hill Drive, Poughkeepsie, NY 12603
0.37
-
3
2
2,947
Off Market
12 Birch Hill Drive, Poughkeepsie, NY 12603
0.40
$400,000
3
3
2,198
Recently Sold

Local Information

  • Map ViewExplore the area around 252 Overlook Rd.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
2001
Lot Size
1.55 acres
Living Area
2,315 sqft
Price/Sqft
$324
Parking
Garage

About this House

As you meander up the long drive through a canopy of trees, you'll be tempted to rest a spell on the southern-style covered porch stretching across the front of this 2300 SF Colonial home. Completely surrounded by beautiful pines & tall trees on 1.5 acres, you'll think you've arrived at a private estate away from civilization! And there's so much to take in and see, it's hard to know where to begin. From the wide entry you will notice how natural light streams into each room. How open site lines connect the kitchen & breakfast bar to the family room, dining area and outside back deck, playground & above ground pool. How the extra large rooms provide the perfect space for family gatherings and entertaining. Need to get away from it all? Luxuriate in the owner's ensuite with its spa bath & walk-in closet. Or escape to the huge dormered bonus room w/ a myriad of potential uses. There's a full unfinished walk-out basement & walk up attic waiting to be configured. Realize your dreams today.
252 Overlook Rd, Poughkeepsie, NY 12603 is a 3 bedroom, 3 bathroom, 2,315 sqft single-family home built in 2001. It last sold for $621,500 on Oct 27, 2022. It is currently off market. The Trulia Estimate is $749,600, with a rent estimate of $4,765/month.

Home Details for 252 Overlook Rd

Interior Features

Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 9
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 2001
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Exterior Features

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

Community

Units in Building: 1

Lot Information

Lot Area: 1.55 acres

Price and Tax history

DateEventPrice
Oct 27, 2022
Source: OneKey® MLS as distributed by MLS GRID #H6192240
Sold
$621,500
Aug 6, 2022
Source: MHMLS #409092
Pending
$575,000
Jun 23, 2022
Source: OneKey® MLS as distributed by MLS GRID #H6192240
Listed For Sale
$575,000
Sep 15, 2021
Source: N/A
ListingRemoved
Sep 11, 2021
Source: N/A
Listed For Sale
$550,000

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

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.
  • Lschuder
    "Lots of people own dogs, you would see constant neighbors walking them! Great neighborhood to walk or exercise."
    0
    Flag
  • 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
  • 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
    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

LGBTQ Local Legal Protections

Frequently asked questions about 252 Overlook Rd

  • What is 252 Overlook Rd estimated to be worth?
    Trulia's estimated value for 252 Overlook Rd in Poughkeepsie, NY is $749,600.
  • What is the price history for 252 Overlook Rd?
    252 Overlook Rd in Poughkeepsie, NY last sold for $621,500 in October 2022.
  • 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 252 Overlook Rd have air conditioning?
    Yes, 252 Overlook Rd in Poughkeepsie, NY has air conditioning.
  • Does 252 Overlook Rd have a pool?
    Yes, 252 Overlook Rd in Poughkeepsie, NY has a pool.

Explore by feature - Pet Friendly

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Explore by feature - Garage

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Explore by feature - Air Conditioning

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Explore by feature - Pool

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Explore by feature - Washer/dryer

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Explore by feature - Outdoor Space

31 rentals with an outdoor space in Poughkeepsie, NY

Apartments for Rent

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Off Market Homes Near 252 Overlook Rd

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