33 Winchester Drive, Monroe, NY 10950

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$660,000

bedrooms

bathrooms

square feet

2,220

Acreage

Open Houses

year built

1977

Full Baths

Half Baths

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Located in the desirable Monroe-Woodbury School District, this classic 2,220 sq ft colonial offers a rare combination of space, comfort, and future potential. Set on a gentle hill in a picturesque, sidewalk-lined neighborhood, the property features four spacious bedrooms, two bathrooms, and a well-balanced layout that includes a formal dining room, a living room, and a separate family room. The home sits on an unfinished basement, offering excellent storage or the opportunity to create additional living space. There is also room to expand out the back, making this a property with true long-term flexibility. A cozy pellet stove insert brings warmth and character to the main living space, while the kitchen opens to a bright, window-lined breakfast nook—ideal for casual dining and enjoying peaceful backyard views. A screened-in back deck provides a shaded outdoor retreat, leading to a beautifully maintained, heated inground swimming pool—perfect for summer afternoons or quiet night swims under the stars. Enjoy charming views of the town below from the front steps, a peaceful reminder of the home's elevated setting. Additional features include municipal utilities, pull-down access to attic storage, and a two-car garage. The location offers the convenience of walkable access to grocery stores and houses of worship, all within a well-established neighborhood. This is a home with character, comfort, and space to grow—an excellent opportunity in a prime location.

Location
Subdivision	-
County	Orange
Elementary School	Pine Tree
Middle School	Monroe-Woodbury
High School	Monroe-Woodbury

Driving directions

Open houses

None scheduled.

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MLS number: 847804

Listing agent: listing agent

Listing broker: Howard Hanna Monroe/Woodbury (845) 928-8161

Last update: Tuesday, December 2 2025 at 12:20 a.m. EST

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