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5 Vail Road

Poughkeepsie, NY 12603 · Dutchess County

Beds
5
Baths
3.5
Sqft
2,628
Status
Active
On site
17 days

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About this home

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.

Listed with Houlihan Lawrence Inc. · Jennifer Stapleton · Source: OneKey MLS

One Key MLS

Information provided by One Key MLS, and is deemed reliable but not guaranteed accurate. Data last updated: Oct 23, 2026, 8:07 AM ET. ©2026 One Key MLS.

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$4,550.69Total / mo

Estimated monthly payment

Principal & interest
$3,447.52(75.8%)
Taxes
$903.17(19.8%)
Insurance
$200.00(4.4%)

Representative rates

Representative rates only, indicative for comparison. Edit the interest rate for your own quote; your lender’s numbers vary with credit, points, and insurance.

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Market insights

The market around Poughkeepsie, NY

Current listings

New in the last 30 days

84

Oct 2026

Average price

Active listings

$480,747

Oct 2026

Average days on market

Active listings

106 days

Oct 2026

Computed from 409 active OneKey MLS listings in Poughkeepsie, NY.

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