Cypress Bay Boulevard, Kissimmee, FL
Everything we know about Cypress Bay Boulevard in Kissimmee: 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.
114 homes sit on Cypress Bay Boulevard in Kissimmee, FL (ZIP 34743, 34744), built 1994–2008, a typical 1,667 sq ft with 3 bedrooms. 4 are for sale right now from $293,999 to $315,000. 3 closed in the last 12 months at a median of $250,000. Homes that sold since 2023 went for a median $284,998.
For sale on Cypress Bay Boulevard now
Recent sales on Cypress Bay Boulevard
| Address | Sold | Closed | Beds / baths | Sq ft |
|---|---|---|---|---|
| 2174 Cypress Bay Boulevard | $240,000 | 2026-05-28 | 3 / 2.0 | 1,177 |
| 2178 Cypress Bay Boulevard | $250,000 | 2026-05-22 | 2 / 2.0 | 1,000 |
| 2069 Cypress Bay Boulevard | $310,000 | 2026-01-22 | 3 / 2.5 | 1,725 |
The homes on Cypress Bay Boulevard
1 single-family, 113 condo/townhome/other. Built by decade: 1990s 35, 2000s 79.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 2026 Cypress Bay Boulevard | $280,000 | 2026-07-28 | 2005 | 1,382 |
| 2174 Cypress Bay Boulevard | $240,000 | 2026-05-28 | 1995 | 1,177 |
| 2178 Cypress Bay Boulevard | $250,000 | 2026-05-22 | 1994 | 1,000 |
| 2069 Cypress Bay Boulevard | $310,000 | 2026-01-22 | 2006 | 1,725 |
| 2051 Cypress Bay Boulevard | $265,000 | 2025-12-18 | 2006 | 1,382 |
| 2078 Cypress Bay Boulevard | $305,000 | 2025-07-16 | 2006 | 1,807 |
| 2181 Cypress Bay Boulevard | $240,000 | 2025-07-10 | 1995 | 1,000 |
| 2016 Cypress Bay Boulevard | $284,998 | 2025-07-07 | 2005 | 1,630 |
| 2190 Cypress Bay Boulevard | $250,000 | 2025-04-28 | 1995 | 1,177 |
| 2116 Cypress Bay Boulevard | $285,000 | 2025-04-25 | 1997 | 1,460 |
| 2140 Cypress Bay Boulevard | $287,000 | 2025-01-31 | 1996 | 1,460 |
| 2156 Cypress Bay Boulevard | $284,500 | 2024-11-08 | 1996 | 1,000 |
| 2019 Cypress Bay Blvd | $315,000 | 2024-10-04 | 2005 | 1,807 |
| 2028 Cypress Bay Boulevard | $300,000 | 2024-07-05 | 2005 | 1,824 |
| 2063 Cypress Bay Boulevard | $285,000 | 2024-06-28 | 2006 | 1,382 |
| 2132 Cypress Bay Boulevard | $259,900 | 2024-06-21 | 1996 | 1,000 |
| 2036 Cypress Bay Boulevard | $315,000 | 2024-06-03 | 2006 | 1,824 |
| 2184 Cypress Bay Boulevard | $230,000 | 2024-03-29 | 1995 | 1,177 |
| 2066 Cypress Bay Boulevard | $300,000 | 2024-03-27 | 2006 | 1,807 |
| 2120 Cypress Bay Boulevard | $240,000 | 2023-12-29 | 1997 | 1,177 |
Communities along Cypress Bay Boulevard
- Cypress Lakes Twnhm Pii · 21 homes on the street
- Cypress Lake Townhomes Phs · 16 homes on the street
- Cypress Lakes · 15 homes on the street
- Cypress Lake · 13 homes on the street
- Cypress Lakes Townhomes Pii U1 · 11 homes on the street
- Cypress Lake · 7 homes on the street
- Cypress Lakes Townhomes · 5 homes on the street
- Cypress Lakes Townhomes · 4 homes on the street
- Cypress Lakes Townhomes · 3 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 3,084 homes for sale in Kissimmee, homes for sale in 34743, homes for sale in 34744.