21 Overlook Road, Poughkeepsie, NY 12603
SOLD
DEC 3, 2025

$419,900

Trulia Estimate
  • 3 Beds
  • 1.5 Baths
  • 1,944 sqft (on 0.72 acres)

21 Overlook Road, Poughkeepsie, NY 12603

Est. Refi. Payment $2,861/mo*
Refinance Your Home
Currently Off Market - Sold Dec 3, 2025 for $399,000 (0% below list price)

Home Value

Trulia Estimate
$420K
Since last month
Increased$1K (+0.3%)
Since last year
Increased$21K (+5.2%)
Since last sale
Increased$20K (+5%)
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 +114% in the last 10 years
MonthEstimated value
2026
August 2026$419K
August 2026$419K
July 2026$418K
June 2026$421K
May 2026$408K
April 2026$410K
March 2026$409K
February 2026$406K
January 2026$404K
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
4 Verven Road, Poughkeepsie, NY
0.27
Single-Family Home
$400,000
01/30/26
3
2
1,736
42 Shamrock Circle, Poughkeepsie, NY
0.33
Single-Family Home
$465,000
11/04/25
3
1
1,573
175 Overocker Road, Poughkeepsie, NY
0.15
Single-Family Home
$455,000
08/11/26
3
2
1,388
15 Short Hill Drive, Poughkeepsie, NY
0.46
Single-Family Home
$400,000
07/20/26
3
2
1,536
40 Ireland Drive, Poughkeepsie, NY
0.30
Single-Family Home
$555,000
05/01/26
3
2.5
3,148
832 Dutchess Turnpike, Poughkeepsie, NY
0.26
Single-Family Home
$320,000
02/27/26
4
3
2,083
10 Edwin Road, Poughkeepsie, NY
0.47
Single-Family Home
$530,000
08/11/26
3
2
1,620
85 Overocker Road, Poughkeepsie, NY
0.57
Single-Family Home
$350,000
02/19/26
3
1
1,602
217 Overocker Road, Poughkeepsie, NY
0.08
Single-Family Home
$240,000
10/28/25
2
1
740

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
217 Overocker Road, Poughkeepsie, NY 12603
0.08
$254,400
2
1
740
Off Market
175 Overocker Road, Poughkeepsie, NY 12603
0.15
$455,000
3
2
1,388
Recently Sold
18 DEGARMO Road, Poughkeepsie, NY 12603
0.18
$414,100
3
2
1,864
Off Market
33 Ireland Drive, Poughkeepsie, NY 12603
0.19
$528,000
4
2.5
2,264
Off Market
832 Dutchess Turnpike, Poughkeepsie, NY 12603
0.26
$320,000
4
3
2,083
Recently Sold
4 Verven Road, Poughkeepsie, NY 12603
0.27
$400,000
3
2
1,736
Recently Sold
21 Ireland Drive, Poughkeepsie, NY 12603
0.21
$428,300
3
1.5
1,008
Off Market
833 Dutchess Turnpike, Poughkeepsie, NY 12603
0.27
$357,000
3
2
1,864
Off Market
8 Ridge Road, Poughkeepsie, NY 12603
0.29
$476,600
3
2
1,686
Off Market
1 Shamrock Circle, Poughkeepsie, NY 12603
0.26
$446,000
3
1.5
1,525
Off Market
29 DEGARMO Road, Poughkeepsie, NY 12603
0.32
$443,000
3
2
2,413
Off Market

Local Information

  • Map ViewExplore the area around 21 Overlook Road.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1812
0.72 acre lot
1,944 sqft
$205/sqft
Garage

About this House

Look no further, this is a truly charming home built in 1812, seamlessly blending historic character with modern conveniences. This beautifully maintained property features an expansive lawn, vibrant flower gardens, and a welcoming new covered porch perfect for relaxing afternoons. Inside, you’ll find plenty of daylight streaming through the many windows, highlighting the warmth and elegance of the original architecture. Formal living room with a fireplace, Extra large dining room for ultimate entertaining. The home offers several extra rooms ideal for a home office, library, or den. With its timeless charm and thoughtful updates, this unique property is a rare find. Some of the updates include all in 2022: new siding and roof on house and garage, new septic tank and fields, solar panels, Navien high efficiency natural gas unit for heat and hot water and 200 amp electrical service.
The charm and beauty of this home is waiting just for you. Home is in Arlington School District and across the street from Adams Fairacre Farm. 24 hours requested for showing appointments, there is a dog in residence.
21 Overlook Road, Poughkeepsie, NY 12603 is a 3 bedroom, 2 bathroom, 1,944 sqft single-family home built in 1812. It last sold for the $399,999 asking price on Dec 3, 2025. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $419,900, with a rent estimate of $3,378/month.
Last check for updates: about 15 hours ago
Listed by Robyn Tricinelli, (845) 661-9376
Century 21 Alliance Realty Grp, (845) 485-2700
Bought with: Non Member-MLS, (000) 000-0000, Buyer Representation Office, (000) 000-0000
Source: OneKey® MLS as distributed by MLS GRID, MLS#859031

Home Details for 21 Overlook Road

Interior Features

Interior Details
Basement: Storage SpaceNumber of Rooms: 10Types of Rooms: Basement
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 1Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 1944 Square Feet
Appliances & Utilities
Utilities: Cable Connected, Electricity Connected, Natural Gas ConnectedAppliances: Dishwasher, Dryer, Range, Refrigerator, Tankless Water Heater, WasherDishwasherDryerLaundry: In KitchenRefrigeratorWasher
Heating & Cooling
Heating: ENERGY STAR Qualified EquipmentHas CoolingAir Conditioning: Wall/Window Unit(s)Has HeatingHeating Fuel: ENERGY STAR Qualified Equipment
Fireplace & Spa
Number of Fireplaces: 1Fireplace: Living RoomHas a Fireplace
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Window: Wall of Windows
Levels, Entrance, & Accessibility
Levels: Two

Exterior Features

Exterior Home Features
Patio / Porch: Covered, PorchOther Structures: Garage(s)Exterior: Garden, MailboxGarden
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageParking Spaces: 6Parking: Detached,Garage,Off Street
Water & Sewer
Sewer: Septic Tank
Farm & Range
Not Allowed to Raise Horses

Days on Market

Cumulative Days on Market: 174

Property Information

Year Built
Year Built: 1812Year Renovated: 1990
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence, ResidentialArchitecture: Colonial
Building
Construction Materials: Clapboard, Vinyl SidingNot Attached Property
Property Information
Parcel Number: 1346896261025659490000

Price & Status

Price
List Price: $399,999Price Per Sqft: $205/sqft
Status Change & Dates
Off Market Date: Tue Oct 28 2025

Active Status

MLS Status: Sold

Location

Direction & Address
City: Poughkeepsie
School Information
Elementary School: Overlook Primary SchoolJr High / Middle School: Lagrange Middle SchoolHigh School: Arlington High SchoolHigh School District: Arlington

Building

Building Area
Building Area: 1944 Square Feet

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 0.72 acres

Listing Info

Special Conditions: None

Offer

Listing Agreement Type: Exclusive Right To Sell

Miscellaneous

BasementMls Number: 859031Attic: Full, Pull StairsShowing Requirements: 24 Hour Notice, Appointment Only, Combination Lock Box, Occupied, Pet(s) on Premises, Showing Service

Price and Tax history

DateEventPrice
Dec 3, 2025
Source: OneKey® MLS as distributed by MLS GRID #859031
Sold
$399,000
Oct 28, 2025
Source: OneKey® MLS as distributed by MLS GRID #859031
Pending
$399,999
Jul 17, 2025
Source: OneKey® MLS as distributed by MLS GRID #859031
PriceChange
$399,999
Price decreased by 4%
Jul 7, 2025
Source: OneKey® MLS as distributed by MLS GRID #859031
PriceChange
$415,000
Price decreased by 2%
Jun 17, 2025
Source: OneKey® MLS as distributed by MLS GRID #859031
PriceChange
$425,000
Price decreased by 2%

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.
  • cmportune@gmail.com
    "I see people walking their dogs all the time. It seems to be no problem. "
    0
    Flag
  • 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 "
    1
    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
  • 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

Based on information submitted to the MLS GRID as of 2026-09-07 08:33:19 PDT 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

Frequently asked questions about 21 Overlook Road

  • What is 21 Overlook Road estimated to be worth?
    Trulia's estimated value for 21 Overlook Road in Poughkeepsie, NY is $419,900.
  • What is the price history for 21 Overlook Road?
    21 Overlook Road in Poughkeepsie, NY last sold for $399,000 in December 2025.
  • 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 21 Overlook Road have air conditioning?
    Yes, 21 Overlook Road in Poughkeepsie, NY has air conditioning.
  • Does 21 Overlook Road have laundry facilities?
    Yes, 21 Overlook Road in Poughkeepsie, NY has in-unit laundry.

Explore by feature - Pet Friendly

80 pet-friendly rentals in Poughkeepsie, NY

Explore by feature - Garage

15 rentals with a garage in Poughkeepsie, NY

Explore by feature - Air Conditioning

122 rentals with air conditioning in Poughkeepsie, NY

Explore by feature - Pool

12 rentals with a pool in Poughkeepsie, NY

Explore by feature - Washer/dryer

82 rentals with a washer/dryer in Poughkeepsie, NY

Explore by feature - Outdoor Space

33 rentals with an outdoor space in Poughkeepsie, NY

Apartments for Rent

Skip to last item
Skip to first item

Off Market Homes Near 21 Overlook Road

Skip to last item
Skip to first item

Homes for sale near 21 Overlook Road

Skip to last item
Skip to first item
Skip to last item
  • Results are loading
Skip to first item