$599,000
- 4
- beds
- 2 full · 1 half
- baths
- 2,220
- sqft
- 1977
- year built
- 4
- beds
- 2 full · 1 half
- baths
- 2,220
- sqft
- 1977
- year built
- Status:
- Pending
- MLS #:
- 1016143
- County:
- Orange
- Listed By:
- Claudia Lepore - Keller Williams Realty
- Office Phone:
- (845) 928-8000
- Agent Email:
- casadolce@kw.com
Sponsoring Broker: Steven Domber, Berkshire Hathaway HomeServices Hudson Valley Properties
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.
-
- Bedrooms
- 4
-
- Bathrooms
- 2 full · 1 half
-
- Year Built
- 1977
-
- Architectural Style
- Colonial
-
- Construction Materials
- Frame, Vinyl Siding, Brick
-
- Garage Spaces
- 2.0
-
- Parking Features
- Driveway, Garage
-
- Living Area
- 2220.0
-
- Interior Features
- Eat-in Kitchen, Entrance Foyer
-
- Appliances
- Dishwasher, Refrigerator, Range
-
- Flooring
- Hardwood
-
- Patio And Porch
- Covered, Deck, Porch, Screened
-
- Pool Features
- In Ground, Private
-
- Cooling
- Wall/Window Unit(s)
-
- Heating
- Oil
-
- Basement
- Walk-Out Access, Unfinished
-
- Acres
- 0.4591
-
- Utilities
- Natural Gas Available, Electricity Connected, Sewer Connected, Water Connected
-
- Water
- Public
-
- County
- Orange
-
- City
- Monroe
-
- Zip Code
- 10950
-
- High School
- Monroe-Woodbury High School
-
- Middle School
- Monroe-Woodbury Middle School
-
- Elementary School
- Pine Tree Elementary School
-
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Price History
| 06/25/2026 | Listed | $599,000 |
| Source: OneKey MLS #1016143 | ||
| 04/20/2025 | Off Market | — |
| Source: OneKey MLS #847804 | ||
Source: MLS Data
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There are currently 60 properties available in Monroe, with 0 under contract to close soon. Properties in the city have an average sale price of $586,317 and typically spend 143 days on the market before being sold.
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Source: ez Home Search, MLS Data
Frequently Asked Questions
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How do I get more information about 33 Winchester Dr?
Click Ask a Question to talk with our team. You already know it is a 4 bed, 2 bath, listed for $599,000. We can talk through recent upgrades, potential seller motivation, how this single family residence compares to others in Monroe, and can even get you in to see the property quickly.
How much is the monthly mortgage payment for 33 Winchester Dr?
With a 20% down payment and a 30-year fixed loan at an illustrative 7.25% rate, the ez Mortgage Calculator estimates the monthly payment for 33 Winchester Dr at around $4,861. This includes estimated property taxes and insurance.
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Can I negotiate the asking price for 33 Winchester Dr?
In most cases, yes. Whether 33 Winchester Dr is priced competitively or not, your best offer depends on your personal situation, the seller's timeline, and recent activity in Monroe's market. Our preferred local partner will help you craft a strategy—factoring in comparable properties that have sold, timing, and deal structure—to make a smart, strong offer. Click here to ask about negotiation opportunities.
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What is the price per square foot for this home?
This home is listed at $599,000 with 2,220 sqft of space—that comes out to approximately $270 per square foot.
How long has this property been on the market?
33 Winchester Dr was listed on June 25, 2026, which means it's been on the market for 139 days.
Want to keep tabs on it? Click the ♥ to favorite this home and get notified of price drops or changes.
When was this house built?
This home was built in 1977, making it approximately 49 years old.
What is the lot size of this property?
33 Winchester Dr sits on a 0.46-acre lot, which is 20,038 square feet.
What schools are assigned to this property?
Based on MLS info, this home is zoned for:
- Elementary: Pine Tree Elementary School
- Middle: Monroe-Woodbury Middle School
- High: Monroe-Woodbury High School
Want to see how these schools compare? Check out our Orange County School Guide to see ratings, reviews, and more for the schools in the area.
What are the property taxes for 33 Winchester Dr?
The most recent public record shows annual property taxes for 33 Winchester Dr were approximately $17,424. This may change with reassessment or exemptions. Our local partner can verify current tax amounts and help you estimate future costs based on your situation.
Is 33 Winchester Dr still available for sale?
This home is pending sale, which means the seller has accepted an offer. You can favorite it to track status or ask our expert to help you find similar homes in this area. We'll also let you know if this property comes back on the market.
Source: ez Home Search, MLS Data
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Listing information 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. Information deemed reliable but not guaranteed by the MLS. The listing broker’s offer of compensation is made only to participants of the MLS where the listing is filed. Copyright 2026, OneKey MLS. All rights reserved.
Last Updated: November 11, 2026 at 05:17AM | Source: OneKey MLS | MLS#: 1016143
