5 Vail Road, Poughkeepsie, NY 12603
Property image
Property image
FOR SALE
3D VIEW
2.24 ACRES

$699,900

Original price: $729,900
  • 5 Beds
  • 3.5 Baths
  • 2,628 sqft (on 2.24 acres)

5 Vail Road, Poughkeepsie, NY 12603

Est. Mortgage $4,882/mo*
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Home Highlights

Single-Family Home
Built in 1869
2.24 acre lot
$266/sqft
Garage

Local Information

  • Map ViewExplore the area around 5 Vail Road.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

What's unique:Pellet stoveGentle streamRaised garden bedsPerennial gardensGenerously sized bedroomsPeriod character
A remarkable blend of history, character and country living awaits on 2.24 park-like acres in the Town of LaGrange and within the Arlington School District. Built in 1869 by businessman and farmer James Howard, this distinctive 5-bedroom, 3.5-bath Hudson River bracketed-style home was once part of a working farm with cattle, orchards and vegetable crops. Remarkably, in almost 160 years, the property has had only four owners, adding to the sense of history and legacy found here. A stunning front porch welcomes you into a home filled with period character, beautiful white pine floors throughout and thoughtful details reflecting the current owner’s artistic talent and eye for design. The gracious parlor/living room features a pellet stove, while the spacious dining room provides an inviting setting for gatherings. The kitchen is truly one of a kind, with beamed ceilings, a double farmhouse sink, commercial-grade Garland range, kitchen island and an extraordinary collection of antique cabinetries individually selected by the current owners, creating a space with warmth, character and authenticity. A handsome library lined with bookshelves features wainscoting and a second pellet stove. The convenient first-floor powder room features hand-selected Mexican tile. The second floor offers a primary bedroom with en-suite bath, along with three additional generously sized bedrooms. The owner’s creative touch continues in the baths, where custom vanities of her own design add another layer of individuality and craftsmanship to the home. Continue to the walk-up attic, where a fifth bedroom and another full bath provide wonderful additional space and versatility. The grounds are equally impressive. Mature trees, manicured lawns, stone walls, perennial gardens and raised garden beds create a picturesque, park-like setting. A 16’ x 32’ in-ground pool with cabana is ready for summer enjoyment, while the beautiful courtyard provides an exceptional setting for outdoor entertaining and has even served as the backdrop for several weddings. Three walking trails and a gentle stream offer opportunities for recreation and exploring right at home. Another exceptional feature is the 24’ x 32’ two-story, three-bay garage, complete with three automatic garage doors and front, rear and side entrances. The generous second story offers tremendous flexibility and would make an ideal art studio, carpenter’s workshop, creative space or hobby area, with additional potential for future accessory living space, subject to municipal approvals. Improvements include – updated septic, 200 amp electrical service, furnace, hot water heater and water tank replaced, roof less than 10 years old and newly sealed driveway. All walls, cabinetry, closets and original moldings have been recently painted. This home is in move-in condition. Nearly 160 years of history, distinctive architecture, artisan details, beautiful grounds and exceptional versatility come together to create a truly special property - one rich in character and ready for its next chapter. Just 3 miles to the Taconic State Parkway, 10 minutes to Metro North (Poughkeepsie Station) and just minutes to Adams Fairacre Farm and the Dutchess Rail Trail leading to the Walkway Over the Hudson. Don’t miss this truly special property.
Last check for updates: about 1 hour ago
Listing by: Houlihan Lawrence Inc., 845-473-9770
Jennifer Stapleton, (914) 906-2423
Source: OneKey® MLS as distributed by MLS GRID, MLS#1059019

Home Details for 5 Vail Road

Interior Features

Interior Details
Basement: UnfinishedNumber of Rooms: 9Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Bedroom 5, Master Bathroom, Bathroom 1, Bathroom 3, Bathroom 4, Auxiliary Room, Dining Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 2628 Square Feet
Appliances & Utilities
Utilities: Electricity ConnectedAppliances: Gas Range, RefrigeratorRefrigerator
Heating & Cooling
Heating: Baseboard,OilNo CoolingAir Conditioning: NoneHas HeatingHeating Fuel: Baseboard
Gas & Electric
Has Electric on Property

Exterior Features

Exterior Home Features
Other Structures: Cabana, Garage(s), PergolaHas a Private Pool
Parking & Garage
Number of Garage Spaces: 3Number of Covered Spaces: 3No CarportHas a GarageHas Open ParkingParking Spaces: 3Parking: Detached,Driveway,Garage
Pool
Pool: In GroundPool
Water & Sewer
Sewer: Septic Tank

Days on Market

Cumulative Days on Market: 11Days on Market: 28

Property Information

Year Built
Year Built: 1869
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence, ResidentialArchitecture: Other
Building
Construction Materials: FrameNot Attached Property
Property Information
Parcel Number: 1334006361032381750000

Price & Status

Price
List Price: $699,900Price Per Sqft: $266

Active Status

MLS Status: Active

Media

Location

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

Agent Information

Listing Agent
Listing ID: 1059019

Building

Building Area
Building Area: 2628 Square Feet

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 2.24 Acres

Listing Info

Special Conditions: None

Offer

Listing Agreement Type: Exclusive Right To Sell

Miscellaneous

BasementMls Number: 1059019Attic: WalkupAttribution Contact: 845-473-9770Showing Requirements: Appointment Only, Showing Service

Price and Tax history

DateEventPrice
Oct 17, 2026
Source: OneKey® MLS as distributed by MLS GRID #1059019
PriceChange
$699,900
Price decreased by 4%
Oct 6, 2026
Source: OneKey® MLS as distributed by MLS GRID #1059019
Listed For Sale
$729,900

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. "
    1
    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."
    2
    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

Market trends in Poughkeepsie

Last updated September 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$423K
$6.71KMoM
Sale-to-List Price
101.2%
0.1%MoM
Price per sq ft
$247
$2MoM
Available listings
256
13MoM
Sourced by Trulia Market Trends

Home Value

Learn more about this home's value by checking out the value of nearby homes and how much similar homes have sold for.

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
10 Page Court, Poughkeepsie, NY
0.12
Single-Family Home
$647,000
12/04/25
4
2.5
2,394
219 Ridgeline Drive, Poughkeepsie, NY
0.39
Single-Family Home
$638,175
12/08/25
4
2.5
2,388
211 Ridgeline Drive, Poughkeepsie, NY
0.39
Single-Family Home
$650,000
09/15/26
3
2.5
1,904
31 Hartstone Drive, Poughkeepsie, NY
0.66
Single-Family Home
$600,000
09/21/26
3
3.5
3,360
27 Sommerset Road, Poughkeepsie, NY
0.34
Single-Family Home
$820,000
12/30/25
4
2.5
5,654
8 Robert Road, Poughkeepsie, NY
0.43
Single-Family Home
$510,000
01/14/26
3
3.5
2,790
15 Orchard Road, Poughkeepsie, NY
0.51
Single-Family Home
$470,000
01/08/26
3
2
2,330
23 Robert Road, Poughkeepsie, NY
0.49
Single-Family Home
$500,000
05/05/26
3
2
2,228
23 Howard Road, Poughkeepsie, NY
0.16
Single-Family Home
$297,500
08/21/26
3
1
1,524
5 Chestnut Ridge Road, Poughkeepsie, NY
0.85
Single-Family Home
$570,000
04/13/26
3
2.5
2,722

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
12 Howard Rd, Poughkeepsie, NY 12603
0.02
$296,300
3
1
1,438
Off Market
8 Howard Rd, Poughkeepsie, NY 12603
0.06
$473,000
3
2.5
2,520
Off Market
9 Vail Rd, Poughkeepsie, NY 12603
0.06
$415,800
3
2
1,662
Off Market
9 Howard Rd, Poughkeepsie, NY 12603
0.07
$401,000
4
2
1,872
Off Market
561 Freedom Plains Rd, Poughkeepsie, NY 12603
0.07
$413,200
4
2
1,683
Off Market
1 Vail Rd, Poughkeepsie, NY 12603
0.07
$870,400
4
3
3,150
Off Market
8 Vail Rd, Poughkeepsie, NY 12603
0.08
$443,500
3
1
1,196
Off Market
12 Howard Rd, Poughkeepsie, NY 12603
0.08
-
3
1
1,438
Off Market
12 Howard Rd, Poughkeepsie, NY 12603
0.08
-
3
1
1,438
Off Market
6 Vail Rd, Poughkeepsie, NY 12603
0.08
$422,000
3
1
1,200
Off Market
14 Howard Rd, Poughkeepsie, NY 12603
0.09
$368,500
3
1
1,660
Off Market
565 Freedom Plains Road, Poughkeepsie, NY 12603
0.09
$350,000
3
1
1,540
Off Market
10 Howard Rd, Poughkeepsie, NY 12603
0.09
$545,500
3
3
2,687
Off Market
10 Vail Rd, Poughkeepsie, NY 12603
0.10
$393,400
3
1
1,308
Off Market
16 Howard Rd, Poughkeepsie, NY 12603
0.10
$348,500
2
1
1,332
Off Market
11 Vail Rd, Poughkeepsie, NY 12603
0.11
$384,200
2
1
2,320
Off Market
41 Villa Ln #2, Poughkeepsie, NY 12603
0.11
-
-
-
-
Off Market
Howard Rd, Poughkeepsie, NY 12603
0.12
-
-
-
-
Off Market
562 Freedom Plains Rd, Poughkeepsie, NY 12603
0.12
$408,500
4
1
2,437
Off Market
10 Page Court, Poughkeepsie, NY 12603
0.12
$637,600
4
2.5
2,394
Off Market

LGBTQ Local Legal Protections

Jennifer Stapleton, Houlihan Lawrence Inc., 845-473-9770
Agent Phone: (914) 906-2423
Based on information submitted to the MLS GRID as of 2026-11-03 11:33:20 PST 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

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Frequently asked questions about 5 Vail Road

  • What is the estimated monthly payment for 5 Vail Road?
    Based on a $699,900 list price with 20% down at today's rates, the estimated monthly payment for 5 Vail Road in Poughkeepsie, NY is approximately $4,946 (about $3,763 principal & interest, $1,108 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • How does the list price for 5 Vail Road compare to homes in Poughkeepsie?
    5 Vail Road in Poughkeepsie, NY is listed at $699,900, about 65% above the $423K median sale price in Poughkeepsie.
  • What do residents say about Poughkeepsie?
    Residents describe Poughkeepsie, NY as dog-friendly, easy to park in, and well-kept. Most residents say you need a car. See homes for sale in Poughkeepsie, NY.
  • What are the closest schools to 5 Vail Road?
    The closest schools to 5 Vail Road in Poughkeepsie, NY are Arlington High School (rated 6/10), Overlook Primary School, Titusville Intermediate School (Elementary, rated 4/10).
  • Does 5 Vail Road have a pool?
    Yes, 5 Vail Road in Poughkeepsie, NY has a pool.
  • How big is the lot at 5 Vail Road?
    The lot at 5 Vail Road in Poughkeepsie, NY is about 2.2 acres.
5 Vail Road, Poughkeepsie, NY 12603 is a 5 bedroom, 4 bathroom, 2,628 sqft single-family home built in 1869. This property is currently available for sale and was listed by OneKey® MLS as distributed by MLS GRID on Oct 6, 2026. The MLS # for this home is MLS# 1059019.