45 Rocky Road

Closed 8/30/23
Closed 8/30/23
Gallery Image 1
Last Sold Price
$940,000
3 beds3,235 sqft$291/sqft
45 Rocky Rd, Chester, NY 10918

Description

Just over an hour from NYC an idyllic estate on 13.9 breathtaking private acres awaits. This one-of-a-kind property offers views of Sugarloaf mountain, a gorgeous pond, heated in ground pool, outbuildings, rolling hills and custom stone-work. The home is perfectly sited at the end of a long winding driveway off a private road. The 3235-sf colonial home was built in the 1870's and has been thoughtfully expanded and updated over the years without losing any of its original charm and detail. Stepping...Just over an hour from NYC an idyllic estate on 13.9 breathtaking private acres awaits. This one-of-a-kind property offers views of Sugarloaf mountain, a gorgeous pond, heated in ground pool, outbuildings, rolling hills and custom stone-work. The home is perfectly sited at the end of a long winding driveway off a private road. The 3235-sf colonial home was built in the 1870's and has been thoughtfully expanded and updated over the years without losing any of its original charm and detail. Stepping out of the car you'll notice the stunning classic colonial with detached two car garage, gorgeous stonework, and thoughtful landscaping. Upon entering, the warmth and beauty of the original details like leaded glass, period moldings, gorgeous hardwood floors and elegant fireplaces make you feel welcome and cozy. The expansive house has a large primary suite on the first floor with access to the pool, vaulted ceilings, oversize windows with window seat, primary bath, walk-in closet and chestnut floors. There's a grand family room with oversized fireplace, soaring ceiling, beautiful oak woodwork and beams repurposed from a local mansion and plenty of windows and doors inviting the outdoors in. A smaller sitting room/library has a beautiful fireplace and original cabinetry featuring leaded glass doors updated to include a wine cooler. The dining room too has a fireplace which has been updated to convenient gas. The custom eat-in kitchen has granite countertops, stainless steel appliances and an eating nook overlooking the pond. Also on the first floor is a home office, large laundry room and full bath. Upstairs are two spacious bedrooms which both enjoy lovely views of the property, plenty of storage and a full bath. The house has newer Lenox forced Air Heat & Central Air, security system and a generator. With all the house has to offer, it may come as a surprise that the property is the star of the show...the in-ground heated pool has a lovely pool house and a pump that is less than 5 years old. Next to the pool...a Bocce Court! Several gorgeous patios surround the home and are perfect for formal or informal gatherings, large or small. The heated billiards house on top of the hill offers a fun spot to escape. There are plenty of places to wander in all four seasons and watch the varied wildlife that come to visit. ,InteriorFeatures:All Window Treatments,French Doors,Gas Stove Connection,Beamed Ceilings,Walk-In Closets,OTHERROOMS:Family Room,Laundry/Util. Room,Formal Dining Room,Foyer,Library/Study,Office/Computer Room,Breakfast Nook,ROOF:Asphalt Shingles,FLOORING:Wood,AboveGrade:3235,Basement:Interior Access,ExteriorFeatures:Landscaped,Outside Lighting
LISTING CLOSED: 08/30/2023 12:00 AM

  1. Listed by Patricia Dantzic • BHHS HUDSON VALLEY PROPERTIES RD
    C: (845) 901-7616 pdantzic@bhhshudsonvalley.com

Property Details for 45 Rocky Road

Status
Closed
MLS #
M414154
Days on Market
174
Taxes
$19,311 / year
HOA Fees
-
Condo/Co-op Fees
-
Property Type
Single Family
MLS Type
Single Family
Year Built
1870
Lot Size
13.90 AC / 605,484 SF
County
Orange County
City/Township
Chester Town
View
Mountain(s)
Architectural Style
Colonial
Waterfront
Yes
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Location

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Building Information for 45 Rocky Road

Stories-Year Built1870Building Size-Lot Size13.90 AC / 605,484 SF

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Principal and Interest

$4,778

Property Taxes

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Property Information for 45 Rocky Road

Summary
Location and General Information
  • Senior Community YN: No
  • Directions: NYS Thruway to Rt 17 toward Harriman. 17W to Sugar Loaf and Warwick. Left on Kings Hwy., Left on Laroe, Right on Sugarloaf Mtn Rd., Right on Rock Ridge.
  • Property Attached: No
  • Structure Type: Detached
  • State Or Province: NY
School Information
  • School District: Contact Agent
  • Elementary School: Contact Agent
  • Middle Or Junior School: Contact Agent
  • High School District: Contact Agent
Rental
Rental
  • Seasonal Rental: No
  • RentSpree Y/N: false
Unit Information
Unit Information
  • Building Units Total: 1
Room Information
Room 1 Information
  • Room Level: Second
  • Room Type: Bedroom 2
Room 2 Information
  • Room Level: Second
  • Room Type: Bedroom 1
Room 3 Information
  • Room Level: First
  • Room Type: Kitchen
Room 4 Information
  • Room Level: First
  • Room Type: Family Room
Room 5 Information
  • Room Level: First
  • Room Type: Primary Bedroom
Room 6 Information
  • Room Level: First
  • Room Type: Dining Room
Room 7 Information
  • Room Level: First
  • Room Type: Living Room
Taxes and HOA Information
Taxes and HOA Information
  • Parcel Number: 999999
  • Tax Assessed Value: $342,500.00
  • Additional Fees: No
  • Tax Year: 2022
  • Association: No
Interior and Exterior Features
Interior Features
  • Amenities: Barn(s), Cathedral/Vaulted/High Ceiling, Colonial, High Ceilings, In Ground, Mountain(s), Oven/Range, Patio, Porch, Water Access, Waterfront, Well
  • Interior Features: Cathedral Ceiling(s), High Ceilings
  • Appliances: Dishwasher, Dryer, Microwave, Refrigerator, Washer
  • Basement: None
  • Fireplace: Yes
  • Fireplaces Total: 3
  • Location Amenities: Cathedral/Vaulted/High Ceiling, High Ceilings, Scenic View, Barn(s), Patio, Porch, In Ground Pool, Mountain Views, Water Access
  • Inclusions: Oven/Range
  • Living Area: 3235
  • Basement: No
Exterior Features
  • Exterior Property Features: In Ground, Patio, Porch, Detached, Garage, Level, Views, Wooded
  • Elevation Certificate: No
  • Patio And Porch Features: Patio, Porch
  • Construction Materials: Frame, HardiPlank Type
  • Other Structures: Barn(s)
  • Waterfront Features: Waterfront, Water Access
  • Pool Features: In Ground
  • Pool Details: In Ground
Lot Information
  • Lot Features: Level, Views, Wooded
  • Additional Parcel: No
  • Site Features: Level, Views, Wooded
Parking
  • Parking Features: Detached, Garage
Utilities
  • Cooling: Central Air
  • Heating: Forced Air
  • Heat Fuel Type: Forced Air
  • Water Source: Well
Green Features
  • Green Features: Dishwasher, Dryer, Microwave, Refrigerator, Washer, Forced Air, In Ground

Property History for 45 Rocky Road

DateEvent & SourcePriceAppreciation
Aug 30, 2023

Sold

ONEKEY #M414154

$940,000—
May 18, 2023

Pending

ONEKEY #M414154

—
Mar 9, 2023

Listed (Active)

ONEKEY #M414154

$985,000—
DateEvent & SourcePrice
08/30/2023

Sold

ONEKEY #M414154

$940,000
05/18/2023

Pending

ONEKEY #M414154

—
03/09/2023

Listed (Active)

ONEKEY #M414154

$985,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Schools near 45 Rocky Road

This home is within Monroe-Woodbury Central School District.
Rating
School
Type
Grades
Distance
North Main Street School
Public - 2 to 5
Monroe Woodbury Middle School
Public - 6 to 8
Monroe Woodbury High School
Public - 9 to 12
Pine Tree Elementary School
Public - 2 to 5
Rating
School
Distance
North Main Street School
Public2 to 5

Monroe Woodbury Middle School
Public6 to 8

Monroe Woodbury High School
Public9 to 12

Pine Tree Elementary School
Public2 to 5

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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Nearby home values

AddressSold priceBedsBathsSqftLot (Sqft)
This home: 45 Rocky Road, Chester, NY 10918
$940,000
3
3,235
605,484
21 Winding Trail, Chester, NY 10918
$315,000
3
1,960
100,188
1 Winding Trail, Chester, NY 10918
$540,000
3
2,040
52,272
3 Rocky Road, Chester, NY 10918
–
4
2
2,400
43,560
4 Rocky Road, Chester, NY 10918
–
3
1,280
43,560
388 Bull Mill Road, Chester, NY 10918
$329,000
4
2,888
82,764

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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of BHHS HUDSON VALLEY PROPERTIES RD

Based on information submitted to the MLS GRID as of 06/13/2025 05:47 PM. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Properties displayed may be listed or sold by various participants in the MLS. IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID. Use of the MLS GRID data may be subject to an end user license agreement prescribed by the applicable MLS of the Member Participant, if any, and as amended from time to time.