$325,900
2 Bed • 1.5 Bath • 1,072 Sq. Ft.2 bd · 1.5 ba · 1,072 sqft
4108 Whispering Hills
Chester, NY 10918
Listed with Keller Williams Realty
$419,000
Est. $2,968/moPine Bush, NY 12589 · Orange County
Know your budget before you tour. Get pre-qualified
A RARE PINE BUSH OPPORTUNITY WITH A LEGAL ACCESSORY APARTMENT! Set on 1.3 level acres in the Town of Crawford, 740 Wallkill Avenue is a spacious and versatile ranch offering approximately 2,177 square feet, 4 bedrooms, 2 full bathrooms, two kitchens, multiple living areas, a full basement and a 2-car garage. The legal accessory apartment creates flexibility that is difficult to find in a traditional single-family home. The layout may work for a buyer seeking separate living quarters, space for extended stays, a private work-from-home arrangement or the potential for supplemental rental income to help offset homeownership expenses, subject to applicable municipal requirements. With two kitchens and multiple living areas, the home can adapt as the owner’s needs change over time. Inside, the home features generous room sizes, first-floor bedrooms, a first-floor full bathroom, an eat-in kitchen and a den or library that could also provide space for an office, hobbies or additional storage. A wood-burning stove adds warmth and country character, while oil heat with multiple heating zones provides practical temperature control. The full basement offers additional utility and storage space. Outside, the peaceful 1.3-acre property provides a level backyard with room for gardening, outdoor activities, entertaining or simply enjoying the privacy of a country setting. The 2-car garage and additional driveway parking provide space for vehicles, equipment, hobbies and storage. The property has a private well and septic system. Located in Orange County within the Pine Bush School District, this home offers a rural Hudson Valley setting while remaining convenient to Pine Bush, Wallkill, Montgomery, Middletown-area shopping, restaurants, local services, parks and commuter routes. Buyers searching for a Pine Bush home with a legal accessory apartment, a ranch with two kitchens, separate living quarters, multigenerational flexibility, a house-hacking opportunity, a 4-bedroom home with acreage, or a Hudson Valley property with potential rental income should take a closer look at 740 Wallkill Avenue. This is more than a standard four-bedroom ranch—it is a property with built-in flexibility, usable acreage, garage and basement storage, and multiple possibilities under one roof. Buyers and their representatives should independently verify the accessory-apartment documentation, permitted use, rental requirements, square footage, taxes, school information and all other property details with the appropriate professionals and municipal authorities.
As reported by the listing office; verify enrollment with the district.
Listed with Real Estate Circuit Inc · Michelle P Gruberger · Source: OneKey MLS
Information provided by One Key MLS, and is deemed reliable but not guaranteed accurate. Data last updated: Nov 10, 2026, 12:08 PM ET. ©2026 One Key MLS.
Estimate your mortgage payment, including the principal and interest, taxes, insurance, HOA, and private mortgage insurance.
Estimated monthly payment
Representative rates
Representative rates only, indicative for comparison. Edit the interest rate for your own quote; your lender’s numbers vary with credit, points, and insurance.
Be the first to know when an Orange County home hits the market.
Market insights
Current listings
New in the last 30 days
9
Nov 2026
Average price
Active listings
$591,241
Nov 2026
Average days on market
Active listings
264 days
Nov 2026
Computed from 32 active OneKey MLS listings in Pine Bush, NY.
$325,900
2 Bed • 1.5 Bath • 1,072 Sq. Ft.2 bd · 1.5 ba · 1,072 sqft
4108 Whispering Hills
Chester, NY 10918
Listed with Keller Williams Realty
$325,000
3 Bed • 1.5 Bath • 996 Sq. Ft.3 bd · 1.5 ba · 996 sqft
98 Dupont Avenue
Newburgh, NY 12550
Listed with Howard Hanna Rand Realty
$339,500
2 Bed • 2.5 Bath • 1,241 Sq. Ft.2 bd · 2.5 ba · 1,241 sqft
33 Kensington Way
Middletown, NY 10940
Listed with KW Hudson Valley United