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5 Red Fox Run

Chester, NY 10918 · Orange County

Beds
4
Baths
3.5
Sqft
2,960
Status
Active
On site
11 days

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About this home

Custom-built by renowned builder Lou Tedaldi, this one-owner Center Hall Colonial offers nearly 3,000 sq. ft. of exceptionally crafted living space nestled on 6.2 pristine, park-like acres. Set on an exclusive private road shared by only 9 homes, this sanctuary delivers total privacy and tranquility while remaining in the highly sought after Monroe-Woodbury School District and close to all local amenities, major routes, and shopping. Inside, beautiful hardwood floors, custom crown and chair rail moldings, and oversized windows with screens bring continuous natural light throughout. The main level features a welcoming foyer with two coat closets, a formal living room with a cozy brick fireplace, and a family room also featuring its own brick fireplace. The gourmet eat-in kitchen boasts granite countertops, a double electric oven, abundant cabinet space, surplus counters, and Tiffany-style lighting, opening via sliders directly onto the back deck. Enjoy formal meals in the dining room, which features sliders out to a spacious, light-filled screened back porch with ceiling fan, perfect for effortless outdoor entertaining. A major highlight of the main level is a versatile 16x24 bonus addition featuring custom woodworking, a beamed ceiling, a bay window, and an ADA-accessible level including a full bathroom, ideal for a luxurious main floor primary suite, guest wing, or private office. Main floor laundry and a half bath add extra convenience. Upstairs, discover four generously sized bedrooms, including an expansive primary suite with hardwood flooring, a spacious walk-in closet, and an en-suite full bath with double vanity. The second bedroom is exceptionally large, easily serving as an alternate primary, while the remaining bedrooms offer ample closet space and bright, oversized windows.The property continues to impress with incredible functional spaces: Two Basements: Main walk-out basement with shelving, a dedicated workshop area, and a sound-proof room (perfect for a media room or studio). Plus a second insulated basement under the addition with separate exterior access. Property Grounds: Stone-faced concrete foundation, iconic Hudson Valley stone walls, manicured lawn, mature landscaping, storage shed, and surrounding private woods. Modern Comforts & Accessibility: ADA-accessible 2-car garage with ramp entry, full-house propane automatic generator, whole-house alarm system, 4-zone oil heating, attic fan, and 30-year shingle roof. An extraordinary property combining top-tier craftsmanship, flexible living spaces, and unmatched outdoor beauty!

Listed with Howard Hanna Rand Realty · Gina Dudgeon · Source: OneKey MLS

One Key MLS

Information provided by One Key MLS, and is deemed reliable but not guaranteed accurate. Data last updated: Sep 17, 2026, 9:07 PM ET. ©2026 One Key MLS.

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Estimate your mortgage payment, including the principal and interest, taxes, insurance, HOA, and Private Mortgage Insurance.

$4,959.66Total / mo

Estimated Monthly Payment

Principal & interest
$3,344.58 (67.4%)
Taxes
$1,415.08 (28.5%)
Insurance
$200.00 (4.0%)

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 Chester, NY

Current Listings

New in the last 30 days

26

Sep 2026

Average Price

Active listings

$911,991

Sep 2026

Average Days on Market

Active listings

136 days

Sep 2026

Computed from 108 active OneKey MLS listings in Chester, NY.

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