# 33 Winchester Drive, Monroe, NY 10950 > **TL;DR:** 4bd/3ba single family, $599,000 ($270/sqft), built 1977, 2,220 sqft. > Pool, Fireplace, Hardwood, A/C. Est. $3,204/mo. Listed 130 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $599,000 | | Price/sqft | $270 | | Bedrooms | 4 | | Bathrooms | 2 full, 1 half | | Square Feet | 2,220 | | Year Built | 1977 | | Lot Size | 19,998 sqft (0.46 acres) | | Garage | 2-car | | Property Type | Single Family (Single Family Residence) | | Status | Pending | | Days on Market | 130 | ## Why This Home Stands Out - **Pool** - Porch, Deck - **Hardwood Floors** - Hardwood flooring listed ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $3,029 | | Estimated Insurance | $175 | | **Total** | **$3,204** | ## Nearby Schools - **Elementary:** Pine Tree Elementary School - **Middle:** Monroe-Woodbury Middle School - **High:** Monroe-Woodbury High School ## Key Amenities - Pool - Fireplace - Hardwood - A/C - 2-car garage ## Property Highlights - Built in 1977 - 0.46 acre lot - Private pool - Fireplace ## Description ### Agent Description 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. ## Location - **Address:** 33 Winchester Drive, Monroe, NY 10950 - **County:** Orange County - **Coordinates:** 41.312726, -74.177268 - **Google Maps:** https://www.google.com/maps?q=41.312726,-74.177268 ## Listing Agent - **Name:** Claudia Lepore - **Brokerage:** Keller Williams Realty - **Broker Phone:** (845) 928-8000 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/33-Winchester-Dr_Monroe_NY_10950_M30396-35805?f=listhub&s=MLSLINY&m=1016143&c=propsimple) ## Photos ![33 Winchester Drive - Photo 1](http://lh.rdcpix.com/3e70f867e35aa6dd373df920bffe2a7dl-f3655867037r.jpg) ![33 Winchester Drive - Photo 2](http://lh.rdcpix.com/3e70f867e35aa6dd373df920bffe2a7dl-f2996595486r.jpg) ![33 Winchester Drive - Photo 3](http://lh.rdcpix.com/3e70f867e35aa6dd373df920bffe2a7dl-f731320291r.jpg) ![33 Winchester Drive - Photo 4](http://lh.rdcpix.com/3e70f867e35aa6dd373df920bffe2a7dl-f1258508146r.jpg) ![33 Winchester Drive - Photo 5](http://lh.rdcpix.com/3e70f867e35aa6dd373df920bffe2a7dl-f1977135588r.jpg) ![33 Winchester Drive - Photo 6](http://lh.rdcpix.com/3e70f867e35aa6dd373df920bffe2a7dl-f4094400587r.jpg) ![33 Winchester Drive - Photo 7](http://lh.rdcpix.com/3e70f867e35aa6dd373df920bffe2a7dl-f1417010132r.jpg) ![33 Winchester Drive - Photo 8](http://lh.rdcpix.com/3e70f867e35aa6dd373df920bffe2a7dl-f3438853141r.jpg) ![33 Winchester Drive - Photo 9](http://lh.rdcpix.com/3e70f867e35aa6dd373df920bffe2a7dl-f2709699560r.jpg) ![33 Winchester Drive - Photo 10](http://lh.rdcpix.com/3e70f867e35aa6dd373df920bffe2a7dl-f1831378433r.jpg) ![33 Winchester Drive - Photo 11](http://lh.rdcpix.com/3e70f867e35aa6dd373df920bffe2a7dl-f4215810906r.jpg) ![33 Winchester Drive - Photo 12](http://lh.rdcpix.com/3e70f867e35aa6dd373df920bffe2a7dl-f731112266r.jpg) ![33 Winchester Drive - Photo 13](http://lh.rdcpix.com/3e70f867e35aa6dd373df920bffe2a7dl-f4184456598r.jpg) ![33 Winchester Drive - Photo 14](http://lh.rdcpix.com/3e70f867e35aa6dd373df920bffe2a7dl-f369613202r.jpg) ![33 Winchester Drive - Photo 15](http://lh.rdcpix.com/3e70f867e35aa6dd373df920bffe2a7dl-f23826785r.jpg) ![33 Winchester Drive - Photo 16](http://lh.rdcpix.com/3e70f867e35aa6dd373df920bffe2a7dl-f1413103613r.jpg) ![33 Winchester Drive - Photo 17](http://lh.rdcpix.com/3e70f867e35aa6dd373df920bffe2a7dl-f88306609r.jpg) ![33 Winchester Drive - Photo 18](http://lh.rdcpix.com/3e70f867e35aa6dd373df920bffe2a7dl-f2309531574r.jpg) ![33 Winchester Drive - Photo 19](http://lh.rdcpix.com/3e70f867e35aa6dd373df920bffe2a7dl-f2955216965r.jpg) ![33 Winchester Drive - Photo 20](http://lh.rdcpix.com/3e70f867e35aa6dd373df920bffe2a7dl-f139936260r.jpg) ![33 Winchester Drive - Photo 21](http://lh.rdcpix.com/3e70f867e35aa6dd373df920bffe2a7dl-f1717859861r.jpg) ![33 Winchester Drive - Photo 22](http://lh.rdcpix.com/3e70f867e35aa6dd373df920bffe2a7dl-f1613426476r.jpg) ![33 Winchester Drive - Photo 23](http://lh.rdcpix.com/3e70f867e35aa6dd373df920bffe2a7dl-f3344024364r.jpg) ![33 Winchester Drive - Photo 24](http://lh.rdcpix.com/3e70f867e35aa6dd373df920bffe2a7dl-f1941778611r.jpg) ![33 Winchester Drive - Photo 25](http://lh.rdcpix.com/3e70f867e35aa6dd373df920bffe2a7dl-f3776401253r.jpg) ![33 Winchester Drive - Photo 26](http://lh.rdcpix.com/3e70f867e35aa6dd373df920bffe2a7dl-f4053565114r.jpg) ![33 Winchester Drive - Photo 27](http://lh.rdcpix.com/3e70f867e35aa6dd373df920bffe2a7dl-f955832911r.jpg) ![33 Winchester Drive - Photo 28](http://lh.rdcpix.com/3e70f867e35aa6dd373df920bffe2a7dl-f4185136291r.jpg) ![33 Winchester Drive - Photo 29](http://lh.rdcpix.com/3e70f867e35aa6dd373df920bffe2a7dl-f2293806082r.jpg) ![33 Winchester Drive - Photo 30](http://lh.rdcpix.com/3e70f867e35aa6dd373df920bffe2a7dl-f1912165551r.jpg) ![33 Winchester Drive - Photo 31](http://lh.rdcpix.com/3e70f867e35aa6dd373df920bffe2a7dl-f3061754163r.jpg) ![33 Winchester Drive - Photo 32](http://lh.rdcpix.com/3e70f867e35aa6dd373df920bffe2a7dl-f876477411r.jpg) ![33 Winchester Drive - Photo 33](http://lh.rdcpix.com/3e70f867e35aa6dd373df920bffe2a7dl-f3281405456r.jpg) ![33 Winchester Drive - Photo 34](http://lh.rdcpix.com/3e70f867e35aa6dd373df920bffe2a7dl-f110365420r.jpg) ![33 Winchester Drive - Photo 35](http://lh.rdcpix.com/3e70f867e35aa6dd373df920bffe2a7dl-f1970582155r.jpg) ![33 Winchester Drive - Photo 36](http://lh.rdcpix.com/3e70f867e35aa6dd373df920bffe2a7dl-f3537439026r.jpg) ![33 Winchester Drive - Photo 37](http://lh.rdcpix.com/3e70f867e35aa6dd373df920bffe2a7dl-f246034430r.jpg) ![33 Winchester Drive - Photo 38](http://lh.rdcpix.com/3e70f867e35aa6dd373df920bffe2a7dl-f270948940r.jpg) ![33 Winchester Drive - Photo 39](http://lh.rdcpix.com/3e70f867e35aa6dd373df920bffe2a7dl-f696775290r.jpg) ![33 Winchester Drive - Photo 40](http://lh.rdcpix.com/3e70f867e35aa6dd373df920bffe2a7dl-f3463418460r.jpg) ![33 Winchester Drive - Photo 41](http://lh.rdcpix.com/3e70f867e35aa6dd373df920bffe2a7dl-f2809508017r.jpg) ![33 Winchester Drive - Photo 42](http://lh.rdcpix.com/3e70f867e35aa6dd373df920bffe2a7dl-f947022293r.jpg) ![33 Winchester Drive - Photo 43](http://lh.rdcpix.com/3e70f867e35aa6dd373df920bffe2a7dl-f3039315702r.jpg) ![33 Winchester Drive - Photo 44](http://lh.rdcpix.com/3e70f867e35aa6dd373df920bffe2a7dl-f595173025r.jpg) ![33 Winchester Drive - Photo 45](http://lh.rdcpix.com/3e70f867e35aa6dd373df920bffe2a7dl-f2745082404r.jpg) ![33 Winchester Drive - Photo 46](http://lh.rdcpix.com/3e70f867e35aa6dd373df920bffe2a7dl-f1473394203r.jpg) ![33 Winchester Drive - Photo 47](http://lh.rdcpix.com/3e70f867e35aa6dd373df920bffe2a7dl-f4020930868r.jpg) ![33 Winchester Drive - Photo 48](http://lh.rdcpix.com/3e70f867e35aa6dd373df920bffe2a7dl-f2622622448r.jpg) ![33 Winchester Drive - Photo 49](http://lh.rdcpix.com/3e70f867e35aa6dd373df920bffe2a7dl-f632775817r.jpg) --- **MLS#:** 1016143 | **Updated:** 2026-10-29 **Source:** listhub *Copyright © 2026 OneKey MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.* [View on PropertySimple](https://www.propertysimple.ai/listing/33-winchester-drive-monroe-ny-10950-189034d9ddc34c4c814c80732e728186) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://www.propertysimple.ai/listing/33-winchester-drive-monroe-ny-10950-189034d9ddc34c4c814c80732e728186#listing", "url": "https://www.propertysimple.ai/listing/33-winchester-drive-monroe-ny-10950-189034d9ddc34c4c814c80732e728186", "name": "33 Winchester Drive, Monroe, NY 10950", "description": "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. 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