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MLS ID KEY1002140Last updated Sep 2, 2026

Single Family

41 Philip Drive

Pending · Montgomery · Orange County, NY 12549

Bedrooms
4 Beds
Bathrooms
4 Baths
Year built
2004
Est. monthly taxes
$1,164.88
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About this home

Welcome to 41 Philip Drive, a beautifully maintained Colonial built by Hillside Homes and set within Montgomery’s desirable Winding Oaks subdivision. Located on a quiet cul-de-sac and positioned on a private, landscaped lot backing to woods, this home offers exceptional curb appeal with a long paved driveway, mature trees, and a peaceful residential setting. Inside, the home features a bright, comfortable layout with hardwood floors, abundant natural light, and inviting spaces designed for everyday living and entertaining. The open kitchen and breakfast area include warm wood cabinetry, generous counter space, recessed lighting, a center island with seating, and sliding glass doors that extend the living space outdoors. The kitchen flows naturally into the surrounding living and dining areas, creating an ideal environment for gathering. The spacious family room enhances the home’s appeal with hardwood floors, a vaulted ceiling, ceiling fan, large windows, and a welcoming fireplace that anchors the room. A formal dining area provides an elegant setting for meals and celebrations, while the overall floor plan offers flexibility for work, relaxation, and hosting. The primary suite includes a private bath with double sinks for added comfort and convenience. The finished lower level adds approximately 1,200 square feet of versatile bonus space, offering multiple rooms ideal for a media room, playroom, fitness area, office, hobby space, or guest accommodations, complete with an additional full bathroom. Outdoors, the property features a fully usable backyard bordered by mature woods, creating a private and picturesque setting. Expansive lawn areas and established landscaping offer ample room for recreation, gardening, outdoor dining, or simply enjoying the tranquility of the surroundings. A whole-house generator adds valuable peace of mind year-round. Located in the scenic Hudson Valley, this home provides convenient access to Montgomery’s shopping, dining, parks, schools, commuter routes, and regional attractions. With its timeless design, generous living spaces, wooded privacy, and inviting indoor-outdoor flow, 41 Philip Drive presents an exceptional opportunity in one of Montgomery’s most sought-after neighborhoods.

Listing snapshot

Days on site
59 days
Listed on MLS
May 29, 2026
Full baths
3
Half baths
1
Annual property tax (MLS)
$13,978.51
Tax year
2025
Area source (MLS)
Plans
Listing brokerage
Stonewall Realty Group LLC
MLS ID
KEY1002140
Last updated
Sep 2, 2026

General features

Property type
Single Family
Property subtype
Single Family Residence
Year built
2004
Garage
Yes
Garage spaces
2
Parking
Driveway, Garage, Off Street
Water source
Well
Sewer
Septic Tank
Utilities
See Remarks

Interior features

Basement
Finished, Full, Walk-Out Access
Heating
Oil
Cooling
Central Air
Interior
Built-in Features, Cathedral Ceiling(s), Ceiling Fan(s), Chandelier, Chefs Kitchen, Double Vanity, Eat-in Kitchen, Entrance Foyer, Formal Dining, Granite Counters, High Ceilings, Kitchen Island, Open Floorplan, Open Kitchen, Primary Bathroom, Storage, Walk Through Kitchen, Walk-In Closet(s), Washer/Dryer Hookup
Appliances
Dishwasher, Dryer, Microwave, Oven, Range, Refrigerator, Stainless Steel Appliance(s), Washer
Fireplaces
1

Exterior features

Architectural style
Colonial
Construction materials
Vinyl Siding
Private pool
No

Schools (MLS)

Elementary school
Montgomery Elementary School
Elementary school district
Valley Central (Montgomery)
Middle school
Valley Central Middle School
Middle school district
Valley Central (Montgomery)
High school
Valley Central High School
High school district
Valley Central (Montgomery)

School information is provided by the MLS. Confirm attendance eligibility with the school district.

Recent activity

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

Location

Montgomery · Orange County, NY 12549Show interactive map
41 Philip Drive

Montgomery · Orange County, NY 12549

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.