Date
Details
Price
Change
Source
5/22/2026
Listed
$825,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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$825,000 Sale Pending
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Property Description
Set on over 10 private acres in the rolling hills of Orange County, this exceptional custom colonial offers the rare combination of luxury, privacy, and convenience AND just minutes from the heart of Chester and major commuter routes. Built in 2017 and thoughtfully designed with over 2,700 square feet of living space, 45 Whitetail Run delivers the kind of lifestyle buyers dream about but rarely find. From the moment you enter, soaring ceilings, natural woodwork, and an open-concept layout create a warm yet sophisticated atmosphere. The heart of the home is the stunning chef's kitchen featuring granite countertops, a leathered granite kitchen island with storage, breakfast bar, 2 pantry's, and seamless flow into the dining and living spaces; perfect for entertaining or everyday living. A dramatic wood-burning fireplace anchors the living room, while oversized UV tinted windows frame peaceful mountain and wooded views in every direction. The flexible floor plan includes a highly sought-after first-floor bedroom with tray ceilings, spa-like finishes in the bath, whirlpool tub, double vanity, oversized walk-in closets, laundry and balcony. That kind of retreat style feel that makes home hard to leave. Outside, the property truly shines. Enjoy morning coffee on the covered porch, host summer gatherings on the expansive deck and patio, or unwind beneath the pergola surrounded by nature and professionally maintained grounds and gardens. The 10.9-acre setting provides exceptional privacy while still keeping you close to shopping, dining, schools, and commuter access. Additional highlights include central air, smart thermostat, walk-out basement with endless potential, oversized two-car garage, new windows, security system, drilled well, septic, propane heat, and multiple outdoor structures for storage or hobby use. A property like this doesn't just offer a home, it offers space, serenity, and a lifestyle upgrade. Welcome home to 45 Whitetail Run.
Full Property Details
Full Property Details for 45 Whitetail Run
General
- Price: $825,000
- Taxes: $19,393
- Status: Pending
- Type: Single Family
- Source: Long_Island
- MLS ID: 999741
- Updated: 8/14/2026
- Added to Site: 98 day(s) ago
Interior
- Number of Rooms: 11
- Interior Features: First Floor Bedroom, First Floor Full Bath, Breakfast Bar, Ceiling Fan(s), Double Vanity, Eat-in Kitchen, Entrance Foyer, Formal Dining, Granite Counters, High Ceilings, High Speed Internet, His and Hers Closets, Kitchen Island, Natural Woodwork, Open Floorplan, Open Kitchen, Pantry, Primary Bathroom, Master Downstairs, Recessed Lighting, Smart Thermostat, Storage, Tray Ceiling(s), Walk-In Closet(s), Washer/Dryer Hookup
- Fireplace: Yes
- Number of Fireplaces: 1
- Fireplace(s): Living Room, Wood Burning
- Appliances: Dishwasher, Dryer, Microwave, Range, Refrigerator, Stainless Steel Appliance(s), Washer
Rooms
Bathrooms
- Total Bathrooms: 3
- Full Bathrooms: 2
- Half Bathrooms: 1
Bedrooms
- Total Bedrooms: 4
Additional Information
- Security/Safety: Building Security, Security System, Smoke Detector(s)
Exterior
- Exterior Features: Balcony, Garden, Lighting, Mailbox
- Porch/Patio/Deck: Covered, Deck, Patio, Porch, Terrace
Parking
- Garage: Yes
- Garage Spaces: 2
- Parking Features: Garage, Garage Door Opener
Location
- County: Orange County
School Information
- High School District: Monroe-Woodbury
- Elementary School: Central Valley Elementary School
- Middle School: Monroe-Woodbury High School
- High School: Monroe-Woodbury High School
Heating & Cooling
- Central air: Yes
- Cooling Type: Central Air
- Heating Type: Propane
Utilities
- Sewer: Septic Tank
- Water: Well
- Utility Description: Cable Connected, Electricity Connected, Propane
Structural Information
- Architectural Style: Colonial
- Detached/Attached: Detached
- Construction: Frame
- Basement: Yes
- Basement Desc.: Full Basement, Walk-Out Access
- Windows: New Windows, Tinted Windows
- Building Size: 2732
- Square Feet: 2,732
- Year Built: 2017
Additional Structures
- Other Structures: Outbuilding, Pergola, Shed(s)
Lot Features
- Property View: Mountain(s), Trees/Woods
- Mountain views: Yes
- Lot Size (Acres): 10.9
- Lot Size (Sq. Ft.): 474,804
Financial Considerations
- Tax Amount: $19,393.88
Disclosures and Reports
- Special Conditions: None
- Property ID: 332089-052-000-0003-005.000-0000
Listed by Hudson Valley Home Connection
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Listing agents
— 45 Whitetail Run —
Hudson Valley Home Connection
Hudson Valley Home Connection
914-213-4259
NMLS#: 1598647Get Pre-Approved Today
Schools
Schools serving 45 Whitetail Run
School District:Monroe-Woodbury Central School District
| Name | Grades | Distance |
|---|---|---|
North Main Street School 212 North Main Street, Monroe, NY 10950 | 2-5 | 3.2 mi |
Smith Clove Elementary School 21 Smith Clove Rd, Woodbury, NY 10917 | K-1 | 6.1 mi |
Monroe Woodbury Middle School 199 Dunderberg Rd, Woodbury, NY 10917 | 6-8 | 5.7 mi |
Monroe Woodbury High School 155 Dunderberg Rd, Woodbury, NY 10917 | 9-12 | 5.8 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 45 Whitetail Run
Tax History
Tax History for 45 Whitetail Run
Year
Property Taxes
Change
Tax Assessment
Change
2024
$18,531
100%
$72,800
—
2021
-100%
$72,800
—
2021
$16,305
1%
$72,800
-8%
2020
$16,161
4%
$78,800
—
2018
$15,534
128%
$78,800
104%
2017
$6,801
—
$38,600
-4%
2016
$6,832
-38%
$40,000
-33%
2015
$10,964
-1%
$60,000
—
2015
$11,067
3%
$60,000
—
2013
$10,758
—
$60,000
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 45 Whitetail Run
45 Whitetail Run, Chester, NY 10918 (MLS# 999741) is a Single Family property with 4 bedrooms, 2 full bathrooms and 1 partial bathroom. 45 Whitetail Run is currently listed for $825,000 and was received on May 22, 2026. Want to learn more about 45 Whitetail Run? Do you have questions about finding other Single Family real estate for sale in Chester? You can browse all Chester real estate or contact a Coldwell Banker agent to request more information.