Skip to main content

MLS ID KEY1046418Last updated Oct 26, 2026

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
Property gallery0 / 47
Loading photo…Photo unavailable

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

  1. Listing updated from MLS
  2. First seen on this site
  3. MLS status changed

Location

Chester Town · Orange County, NY 10918Show interactive map
5 Red Fox Run

Chester Town · Orange County, NY 10918

Google Maps directions

Estimate monthly payment

Loan detailsFixed-rate, fully amortizing loan. Edit the assumptions below; no market rate is supplied.
Property expenses (USD)
MLS amounts are prefilled when available and can be edited. Confirm what fees include. Unknown fee frequencies cannot be converted automatically.Property expenses: MLS values where available; missing values stay blank.

Estimated monthly principal & interest—

Monthly property taxNot provided

Monthly association / maintenance feesNot provided

Estimated monthly total of entered costs—

Excludes insurance, mortgage insurance, special assessments and lender fees. MLS taxes may reflect abatements or exemptions and can change.

Listing data is supplied by the MLS and may change without notice.