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MLS ID KEY1016143Last updated Sep 10, 2026

Single Family

33 Winchester Drive

Pending · Monroe · Orange County, NY 10950

Bedrooms
4 Beds
Bathrooms
3 Baths
Year built
1977
Est. monthly taxes
$1,452.03
Property gallery0 / 49
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About this home

Welcome to this classic 4-bedroom, 2.5-bath Colonial nestled in the heart of the Village of Monroe. Offering a fantastic layout, generous living spaces, and endless potential, this home is ready for its next owners to make it their own. A welcoming foyer greets you upon entry and leads to a spacious living room. There is also a formal dining room, perfect for holiday gatherings and entertaining guests. The bright, spacious kitchen features granite countertops, abundant cabinetry, and a separate breakfast area overlooking the beautifully landscaped backyard. There is also a cozy family room/den with a pellet stove that helps cut down heating costs in the winter. Off the family room you'll find a screened-in porch and adjoining deck—an ideal setting for grilling, outdoor dining, or simply relaxing while overlooking the backyard and heated in-ground pool. A convenient first-floor powder room and laundry room add to the home’s everyday functionality and round out the first floor. Upstairs, you’ll find three generously sized secondary bedrooms, a full hallway bath, and a spacious primary suite complete with its own private bath. Ample closet space can be found throughout the home. The walkout basement offers outstanding potential to create additional finished living space, a home office, gym, or recreation room. The pull down attic and an attached two-car garage provide added convenience and storage. Situated on a sidewalk-lined street with mature landscaping, this home is conveniently located near shops, restaurants, schools, parks, and major highways, making commuting and everyday errands a breeze. Lovingly maintained by its current owners, this home is ready for its next chapter. With a wonderful floor plan, spacious indoor and outdoor living areas, and endless potential to add your own personal touches, this is an opportunity you won’t want to miss. Schedule a showing today. Monroe Woodbury Schools. Connected perfectly for commuters with bus and train options close by.

Listing snapshot

Days on site
59 days
Listed on MLS
Jun 26, 2026
Full baths
2
Half baths
1
Annual property tax (MLS)
$17,424.4
Tax year
2025
Area source (MLS)
Public Records
Listing brokerage
Keller Williams Realty
MLS ID
KEY1016143
Last updated
Sep 10, 2026

General features

Property type
Single Family
Property subtype
Single Family Residence
Year built
1977
Garage
Yes
Garage spaces
2
Parking
Driveway, Garage
Water source
Public
Sewer
Public Sewer
Utilities
Electricity Connected, Natural Gas Available, Sewer Connected, Trash Collection Public, Water Connected

Interior features

Basement
Unfinished, Walk-Out Access
Heating
Oil
Cooling
Wall/Window Unit(s)
Interior
Eat-in Kitchen, Entrance Foyer, Formal Dining
Appliances
Dishwasher, Range, Refrigerator
Flooring
Hardwood
Fireplace
Yes
Fireplaces
1

Exterior features

Architectural style
Colonial
Construction materials
Brick, Frame, Vinyl Siding
Private pool
Yes

Schools (MLS)

Elementary school
Pine Tree Elementary School
Elementary school district
Monroe-Woodbury
Middle school
Monroe-Woodbury Middle School
Middle school district
Monroe-Woodbury
High school
Monroe-Woodbury High School
High school district
Monroe-Woodbury

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

Recent activity

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

Location

Monroe · Orange County, NY 10950Show interactive map
33 Winchester Drive

Monroe · Orange County, NY 10950

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.