Cypress Hill Road, Winter Garden, FL
Everything we know about Cypress Hill Road in Winter Garden: what is for sale, what has sold, what the homes are like and which communities the street runs through — from the MLS record and county parcel data, refreshed nightly.
74 homes sit on Cypress Hill Road in Winter Garden, FL (ZIP 34787), built 2015–2019, a typical 1,877 sq ft with 3 bedrooms. 2 are for sale right now from $355,000 to $692,900. Homes that sold since 2023 went for a median $545,000.
For sale on Cypress Hill Road now
The homes on Cypress Hill Road
43 single-family, 31 condo/townhome/other. Built by decade: 2010s 74.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 5755 Cypress Hill Road | $455,000 | 2026-08-31 | 2019 | 1,797 |
| 5561 Cypress Hill Road | $565,000 | 2026-05-06 | 2016 | 2,470 |
| 5954 Cypress Hill Road | $770,000 | 2025-10-30 | 2017 | 2,997 |
| 5979 Cypress Hill Road | $494,000 | 2025-08-27 | 2017 | 1,840 |
| 5838 Cypress Hill Road | $408,000 | 2025-06-04 | 2018 | 1,717 |
| 6124 Cypress Hill Road | $640,000 | 2025-03-18 | 2015 | 2,570 |
| 5530 Cypress Hill Road | $690,000 | 2025-02-27 | 2016 | 2,695 |
| 5615 Cypress Hill Road | $620,000 | 2025-02-21 | 2017 | 2,635 |
| 5827 Cypress Hill Road | $390,000 | 2025-01-27 | 2018 | 1,716 |
| 5585 Cypress Hill Road | $570,000 | 2024-12-09 | 2016 | 2,747 |
| 6179 Cypress Hill Road | $655,000 | 2024-11-28 | 2015 | 2,856 |
| 5961 Cypress Hill Rd | $685,000 | 2024-09-06 | 2017 | 3,170 |
| 5692 Cypress Hill Road | $453,000 | 2024-08-07 | 2019 | 1,800 |
| 5833 Cypress Hill Road | $410,000 | 2024-06-26 | 2018 | 1,716 |
| 5707 Cypress Hill Road | $440,000 | 2024-04-30 | 2019 | 1,712 |
| 5579 Cypress Hill Road | $545,000 | 2023-11-22 | 2016 | 1,997 |
| 5645 Cypress Hill Road | $479,990 | 2023-09-13 | 2016 | 1,650 |
| 5674 Cypress Hill Road | $455,000 | 2023-08-18 | 2019 | 1,800 |
| 5524 Cypress Hill Road | $830,000 | 2023-05-24 | 2015 | 4,051 |
| 6125 Cypress Hill Road | $875,000 | 2023-05-02 | 2015 | 3,711 |
Communities along Cypress Hill Road
- Orchard Hills · 22 homes on the street
- Orchard Hills · 11 homes on the street
- Orchard Hills · 11 homes on the street
- Independence · 3 homes on the street
- Signature Lakes · 3 homes on the street
- Signature Lakes · 3 homes on the street
- Signature Lakes · 3 homes on the street
- Signature Lakes · 2 homes on the street
- Signature Lakes · 2 homes on the street
- Orchard Hills · 2 homes on the street
How to read this
Home counts, build years, sizes and last sales come from the county parcel record joined to MLS history; listings and 12-month closings from the live MLS feeds as of October 15, 2026. Listings appear courtesy of the listing brokerage under IDX rules; information deemed reliable but not guaranteed. See also all 750 homes for sale in Winter Garden, homes for sale in 34787.