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.
For sale
$825,000
45 Whitetail Run, Chester, NY 10918
4beds
2,732sqft
Single Family Residence, Residential
Built in 2017
10.9 Acres Lot
$-- Zestimate®
$302/sqft
$-- HOA
What's special
- 48 days |
- 392 |
- 17 |
Zillow last checked:
Listing updated:
Listed by:
Hudson Valley Home Connection 914-213-4259,
Melissa M Forsyth 914-213-4259,
Pete Wolven 845-913-6855,
Hudson Valley Home Connection
Source: OneKey® MLS as distributed by MLS GRID,MLS#: 999741
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Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 3
- Full bathrooms: 2
- 1/2 bathrooms: 1
Heating
- Propane
Cooling
- Central Air
Appliances
- Included: Dishwasher, Dryer, Microwave, Range, Refrigerator, Stainless Steel Appliance(s), Washer
- Laundry: Washer/Dryer Hookup
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)
- Windows: New Windows, Tinted Windows
- Basement: Full,Walk-Out Access
- Attic: Pull Stairs
- Number of fireplaces: 1
- Fireplace features: Living Room, Wood Burning
Interior area
- Total structure area: 2,732
- Total interior livable area: 2,732 sqft
Video & virtual tour
Property
Parking
- Total spaces: 2
- Parking features: Garage, Garage Door Opener
- Garage spaces: 2
Features
- Patio & porch: Covered, Deck, Patio, Porch, Terrace
- Exterior features: Balcony, Garden, Lighting, Mailbox
- Has view: Yes
- View description: Mountain(s), Trees/Woods
Lot
- Size: 10.9 Acres
Details
- Additional structures: Outbuilding, Pergola, Shed(s)
- Parcel number: 3320890520000003005.0000000
- Special conditions: None
- Other equipment: Negotiable
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subtype: Single Family Residence, Residential
Materials
- Frame
Condition
- Year built: 2017
Utilities & green energy
- Sewer: Septic Tank
- Water: Well
- Utilities for property: Cable Connected, Electricity Connected, Propane
Community & HOA
Community
- Security: Building Security, Security System, Smoke Detector(s)
HOA
- Has HOA: No
Location
- Region: Chester
Financial & listing details
- Price per square foot: $302/sqft
- Tax assessed value: $72,800
- Annual tax amount: $19,393
- Date on market: 5/22/2026
- Cumulative days on market: 41 days
- Listing agreement: Exclusive Right To Sell
- Electric utility on property: Yes
Estimated market value
Not available
Estimated sales range
Not available
Not available
Price history
| Date | Event | Price |
|---|---|---|
| 5/22/2026 | Listed for sale | $825,000$302/sqft |
Source: | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | -- | $72,800 |
| 2024 | -- | $72,800 |
| 2023 | -- | $72,800 |
| 2022 | -- | $72,800 |
| 2021 | -- | $72,800 |
| 2020 | -- | $72,800 -7.6% |
| 2019 | -- | $78,800 |
| 2018 | -- | $78,800 +104.1% |
| 2017 | $8,207 | $38,600 -3.5% |
| 2016 | -- | $40,000 -33.3% |
| 2015 | -- | $60,000 |
| 2014 | -- | $60,000 |
| 2013 | -- | $60,000 |
| 2012 | -- | $60,000 |
| 2011 | -- | $60,000 |
| 2010 | -- | $60,000 |
| 2009 | -- | $60,000 |
| 2007 | -- | $60,000 |
| 2006 | -- | $60,000 |
| 2005 | -- | $60,000 |
| 2004 | -- | $60,000 |
| 2002 | -- | $60,000 |
| 2001 | -- | $60,000 |
| 2000 | -- | $60,000 |
Find assessor info on the county website
Monthly payment
Estimated monthly payment$1,822
All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
See how much you could borrow to make a competitive offer.
Climate risks
Neighborhood: 10918
Nearby schools
GreatSchools rating
- 5/10North Main Street SchoolGrades: 2-5Distance: 3.1 mi
- 4/10Monroe Woodbury Middle SchoolGrades: 6-8Distance: 5.7 mi
- 7/10Monroe Woodbury High SchoolGrades: 9-12Distance: 5.7 mi
Schools provided by the listing agent
- Elementary: Central Valley Elementary School
- Middle: Monroe-Woodbury High School
- High: Monroe-Woodbury High School
Source: OneKey® MLS as distributed by MLS GRID. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
A local agent can set up tours, give advice and negotiate with sellers.
- New York
- Orange County
- Chester
- 10918
- 45 Whitetail Run





