# 420 E CYPRESS Street, Winter Garden, FL 34787 > **TL;DR:** 3bd/2ba single family, $400,000 ($248/sqft), built 1950, 1,616 sqft. > A/C. Est. $2,140/mo. Listed 151 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $400,000 | | Price/sqft | $248 | | Bedrooms | 3 | | Bathrooms | 2 full | | Square Feet | 1,616 | | Year Built | 1950 | | Lot Size | 8,276 sqft (0.19 acres) | | Stories | 1 | | Property Type | Single Family (Single Family Residence) | | Status | Active | | Days on Market | 151 | ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $2,023 | | Estimated Insurance | $117 | | **Total** | **$2,140** | ## Nearby Schools - **Elementary:** Maxey Elem - **Middle:** Lakeview Middle - **High:** West Orange High ## Key Amenities - A/C ## Property Highlights - Built in 1950 - 0.19 acre lot ## Description ### Agent Description Welcome to this stunning, fully renovated and fully furnished home, perfectly situated on an oversized lot in one of Winter Garden's most exciting and rapidly growing areas. Whether you're looking for a primary residence, a turnkey investment, or a second home, this move-in-ready property offers the perfect blend of comfort, style, and convenience. Inside, you'll find an open-concept floor plan filled with natural light, featuring all-new flooring, recessed lighting throughout, energy-efficient double-pane windows, and a beautifully updated kitchen complete with stainless steel appliances. Major improvements include a new roof and a 3.5-ton AC system, providing peace of mind for years to come. Step outside and enjoy the spacious, fully fenced backyard, offering plenty of room for entertaining, pets, play, or simply relaxing outdoors. Located just one mile from Historic Downtown Winter Garden, you'll enjoy easy access to award-winning dining, shopping, farmers markets, and community events, all while living in a welcoming, family-friendly neighborhood. Fully furnished, beautifully updated, and truly move-in ready, this home offers a rare opportunity to enjoy all that Winter Garden has to offer from day one. ## Location - **Address:** 420 E CYPRESS Street, Winter Garden, FL 34787 - **County:** Orange - **Neighborhood:** OVERSTREET CRATE - **Coordinates:** 28.555835, -81.578749 - **Google Maps:** https://www.google.com/maps?q=28.555835,-81.578749 ## Virtual Tour & Media - **Video Tour:** https://www.propertypanorama.com/instaview/stellar/O6412414 ## Listing Agent - **Name:** Trevor Zwick - **Brokerage:** Keller Williams Elite Partners III Realty - **Broker Phone:** (321) 527-5111 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/420-E-Cypress-St_Winter-Garden_FL_34787_M68049-76787?f=listhub&s=MFRMLSFL&m=O6412414&c=propsimple) ## Photos ![420 E CYPRESS Street - Photo 1](http://lh.rdcpix.com/7aa6d729f2dbb758f2258ce3803daa91l-f4193920275r.jpg) ![420 E CYPRESS Street - Photo 2](http://lh.rdcpix.com/7aa6d729f2dbb758f2258ce3803daa91l-f2470651985r.jpg) ![420 E CYPRESS Street - Photo 3](http://lh.rdcpix.com/7aa6d729f2dbb758f2258ce3803daa91l-f17633468r.jpg) ![420 E CYPRESS Street - Photo 4](http://lh.rdcpix.com/7aa6d729f2dbb758f2258ce3803daa91l-f297235702r.jpg) ![420 E CYPRESS Street - Photo 5](http://lh.rdcpix.com/7aa6d729f2dbb758f2258ce3803daa91l-f1751719414r.jpg) ![420 E CYPRESS Street - Photo 6](http://lh.rdcpix.com/7aa6d729f2dbb758f2258ce3803daa91l-f4231330493r.jpg) ![420 E CYPRESS Street - Photo 7](http://lh.rdcpix.com/7aa6d729f2dbb758f2258ce3803daa91l-f3233173146r.jpg) ![420 E CYPRESS Street - Photo 8](http://lh.rdcpix.com/7aa6d729f2dbb758f2258ce3803daa91l-f4179712353r.jpg) ![420 E CYPRESS Street - Photo 9](http://lh.rdcpix.com/7aa6d729f2dbb758f2258ce3803daa91l-f3843274585r.jpg) ![420 E CYPRESS Street - Photo 10](http://lh.rdcpix.com/7aa6d729f2dbb758f2258ce3803daa91l-f145382913r.jpg) ![420 E CYPRESS Street - Photo 11](http://lh.rdcpix.com/7aa6d729f2dbb758f2258ce3803daa91l-f955005114r.jpg) ![420 E CYPRESS Street - Photo 12](http://lh.rdcpix.com/7aa6d729f2dbb758f2258ce3803daa91l-f257954182r.jpg) ![420 E CYPRESS Street - Photo 13](http://lh.rdcpix.com/7aa6d729f2dbb758f2258ce3803daa91l-f3487663053r.jpg) ![420 E CYPRESS Street - Photo 14](http://lh.rdcpix.com/7aa6d729f2dbb758f2258ce3803daa91l-f4514930r.jpg) ![420 E CYPRESS Street - Photo 15](http://lh.rdcpix.com/7aa6d729f2dbb758f2258ce3803daa91l-f3670685816r.jpg) ![420 E CYPRESS Street - Photo 16](http://lh.rdcpix.com/7aa6d729f2dbb758f2258ce3803daa91l-f1311970958r.jpg) ![420 E CYPRESS Street - Photo 17](http://lh.rdcpix.com/7aa6d729f2dbb758f2258ce3803daa91l-f2743512818r.jpg) ![420 E CYPRESS Street - Photo 18](http://lh.rdcpix.com/7aa6d729f2dbb758f2258ce3803daa91l-f3501490655r.jpg) ![420 E CYPRESS Street - Photo 19](http://lh.rdcpix.com/7aa6d729f2dbb758f2258ce3803daa91l-f2901549814r.jpg) ![420 E CYPRESS Street - Photo 20](http://lh.rdcpix.com/7aa6d729f2dbb758f2258ce3803daa91l-f3920199432r.jpg) ![420 E CYPRESS Street - Photo 21](http://lh.rdcpix.com/7aa6d729f2dbb758f2258ce3803daa91l-f212127840r.jpg) ![420 E CYPRESS Street - Photo 22](http://lh.rdcpix.com/7aa6d729f2dbb758f2258ce3803daa91l-f3857008164r.jpg) ![420 E CYPRESS Street - Photo 23](http://lh.rdcpix.com/7aa6d729f2dbb758f2258ce3803daa91l-f2005518523r.jpg) ![420 E CYPRESS Street - Photo 24](http://lh.rdcpix.com/7aa6d729f2dbb758f2258ce3803daa91l-f3887496577r.jpg) ![420 E CYPRESS Street - Photo 25](http://lh.rdcpix.com/7aa6d729f2dbb758f2258ce3803daa91l-f1538695553r.jpg) ![420 E CYPRESS Street - Photo 26](http://lh.rdcpix.com/7aa6d729f2dbb758f2258ce3803daa91l-f2035685239r.jpg) ![420 E CYPRESS Street - Photo 27](http://lh.rdcpix.com/7aa6d729f2dbb758f2258ce3803daa91l-f228430267r.jpg) ![420 E CYPRESS Street - Photo 28](http://lh.rdcpix.com/7aa6d729f2dbb758f2258ce3803daa91l-f233245246r.jpg) ![420 E CYPRESS Street - Photo 29](http://lh.rdcpix.com/7aa6d729f2dbb758f2258ce3803daa91l-f3204956849r.jpg) --- **MLS#:** O6412414 | **Updated:** 2026-10-27 **Source:** listhub *Copyright © 2026 Stellar 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/420-e-cypress-street-winter-garden-fl-34787-5ef4eee152c449d8b80642d30bc842b9) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://www.propertysimple.ai/listing/420-e-cypress-street-winter-garden-fl-34787-5ef4eee152c449d8b80642d30bc842b9#listing", "url": "https://www.propertysimple.ai/listing/420-e-cypress-street-winter-garden-fl-34787-5ef4eee152c449d8b80642d30bc842b9", "name": "420 E CYPRESS Street, Winter Garden, FL 34787", "description": "Welcome to this stunning, fully renovated and fully furnished home, perfectly situated on an oversized lot in one of Winter Garden's most exciting and rapidly growing areas. 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