Single Family
5 Red Fox Run
Active · Chester Town · Orange County, NY 10918
- Bedrooms
- 4 Beds
- Bathrooms
- 4 Baths
- Year built
- 1986
- Est. monthly taxes
- $1,291.58
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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!
Listing snapshot
- Days on site
- 49 days
- Listed on MLS
- Sep 7, 2026
- Full baths
- 3
- Half baths
- 1
- Annual property tax (MLS)
- $15,499
- Tax year
- 2025
- Association / maintenance fees (MLS)
- $0 / Semi-Annually
- Fees include (MLS)
- Common Area Maintenance, Other, Snow Removal
- Area source (MLS)
- Public Records
- Listing brokerage
- Howard Hanna Rand Realty
- MLS ID
- KEY1046418
- Last updated
- Oct 26, 2026
General features
- Property type
- Single Family
- Property subtype
- Single Family Residence
- Year built
- 1986
- Garage
- Yes
- Garage spaces
- 2
- Total parking
- 5
- Parking
- Driveway, Garage, Garage Door Opener, Off Street, Oversized
- Water source
- Well
- Sewer
- Septic Tank
- Utilities
- Electricity Connected, Trash Collection Private
Interior features
- Basement
- Bilco Door(s), Full, See Remarks, Storage Space, Walk-Out Access
- Heating
- Oil
- Cooling
- None
- Interior
- First Floor Bedroom, Beamed Ceilings, Ceiling Fan(s), Crown Molding, Eat-in Kitchen, Entrance Foyer, Formal Dining, Granite Counters, High Ceilings, Natural Woodwork, Open Kitchen, Original Details, Primary Bathroom, Storage, Walk-In Closet(s), Washer/Dryer Hookup
- Appliances
- Dishwasher, Dryer, Oven, Refrigerator, Washer
- Flooring
- Carpet, Combination, Hardwood, Tile
- Fireplace
- Yes
- Fireplaces
- 2
Exterior features
- Architectural style
- Colonial
- Construction materials
- Advanced Framing Technique, Frame, Stone, Vinyl Siding
- Exterior
- Mailbox, Rain Gutters
- Private pool
- No
Schools (MLS)
- Elementary school
- North Main Street
- Elementary school district
- Monroe-Woodbury
- Middle school
- Monroe-Woodbury Middle School
- Middle school district
- Monroe-Woodbury
- High school
- Monroe-Woodbury High School
- High school district
- Monroe-Woodbury
School information is provided by the MLS. Confirm attendance eligibility with the school district.
Recent activity
- Listing updated from MLS
- First seen on this site
- MLS status changed
Location
Estimate monthly payment
Estimated monthly principal & interest—
Monthly property taxNot provided
Monthly association / maintenance feesNot provided
Estimated monthly total of entered costs—
Listing data is supplied by the MLS and may change without notice.
