Bent Tree Village vs Windward at Lakewood Ranch
Two Sarasota communities, compared on the numbers that decide it — price, pace, and supply — from live MLS data as of 2026-09-18.
| Metric | Bent Tree Village | Windward at Lakewood Ranch |
|---|---|---|
| Median sale price | $662K | $704K |
| Price per sq ft | $253 | $315 |
| Avg days on market | 136 days | 21 days |
| Months of supply | 2.7 mo | 3.1 mo |
| Market | Seller's Market | Seller's Market |
| 1-year price change | False | False |
| Recent closings | 36 | 51 |
The verdict
Windward at Lakewood Ranch carries the higher median price — about 6% above Bent Tree Village. Homes in Windward at Lakewood Ranch sell faster (21 days on market vs 136). Bent Tree Village is the tighter market on inventory (2.7 months of supply).
What is for sale today
| Bent Tree Village | Windward at Lakewood Ranch | |
|---|---|---|
| Homes for sale now | 8 | 13 |
| Under contract | 5 | 8 |
| Asking prices today | $410K to $1.5M | $447K to $1.48M |
| Listed in the last 7 days | 0 | 6 |
| Property types listed | Single Family Residence | Single Family Residence, Villa |
Live MLS counts, refreshed with every listing pull. Browse them: Bent Tree Village homes for sale · Windward at Lakewood Ranch homes for sale.
The homes themselves
| Bent Tree Village | Windward at Lakewood Ranch | |
|---|---|---|
| Homes (parcels) | 694 | 369 |
| Built | 1975–2016 (median 1980) | 2020–2024 (median 2023) |
| Typical living area | 2,630 sq ft | 2,316 sq ft |
| Homesteaded (owner-occupied) share | 83% | 44% |
| Vacant lots | 0 | 164 |
Housing-stock figures from the Florida Department of Revenue 2025 assessment roll (public records).
Price history, year by year
| Year | Bent Tree Village median | Windward at Lakewood Ranch median |
|---|---|---|
| 2022 | $525K (43 sales) | $420K (9 sales) |
| 2023 | $550K (15 sales) | $783K (16 sales) |
| 2024 | $750K (19 sales) | $1.1M (41 sales) |
| 2025 | $540K (32 sales) | $684K (26 sales) |
| 2026 | $738K (32 sales) | $616K (26 sales) |
Since 2022, Bent Tree Village's median sale price is +40% and Windward at Lakewood Ranch's is +47% — Windward at Lakewood Ranch has appreciated faster over that stretch.
How each one trades
| Bent Tree Village | Windward at Lakewood Ranch | |
|---|---|---|
| Sale-to-original-list | 93.0% | 100.0% |
| New-construction share of sales | 0% | 85% |
| Typical sold home | 2,748 sq ft | 2,088 sq ft |
Last 12 months of recorded closings; sale-to-original-list is the share of the first asking price sellers actually got.
Schools the listings are zoned for
| Bent Tree Village | Windward at Lakewood Ranch | |
|---|---|---|
| Elementary | Lakeview Elementary | Tatum Ridge Elementary |
| Middle | Sarasota Middle | Mcintosh Middle |
| High school | Sarasota High | Booker High |
The school most often recorded on each community's MLS listings. Always confirm a specific address with the district.
Which one fits
On budget alone, Bent Tree Village is the lower entry point (median $662K vs $704K). Buyers who want newer construction (fewer near-term roof, HVAC and re-plumb items, and easier insurance quotes in Florida) will find it in Windward at Lakewood Ranch; Bent Tree Village trades that for a more established street and, typically, larger lots. Sellers get a faster sale in Windward at Lakewood Ranch (21 days on market on average); buyers get more negotiating room where homes sit longer.
Neither number set decides it: drive both on a weekday evening, check the HOA documents and the flood zone for the exact street, and price the insurance before you write an offer. A Momentum agent who works both communities can pull the comparable sales for any two specific homes.
Questions people ask
Is Windward at Lakewood Ranch more expensive than Bent Tree Village?
Yes, on recent sales: the median sale price in Windward at Lakewood Ranch is $704,000 versus $662,000 in Bent Tree Village, about 6% higher.
Which has newer homes, Bent Tree Village or Windward at Lakewood Ranch?
Windward at Lakewood Ranch: its homes were built 2020–2024 with a median year of 2023, versus a median of 1980 in Bent Tree Village (Florida DOR assessment roll).
Which has bigger homes?
Bent Tree Village. The typical home there is 2,630 sq ft of living area, versus 2,316 sq ft in Windward at Lakewood Ranch.
Which has appreciated more, Bent Tree Village or Windward at Lakewood Ranch?
From 2022 to 2026 the median sale price rose 40% in Bent Tree Village and 47% in Windward at Lakewood Ranch (recorded MLS closings by calendar year).
Where do sellers get closer to asking price?
Windward at Lakewood Ranch — sellers there received 100.0% of the original list price over the last 12 months versus 93.0% in Bent Tree Village.
What high schools serve Bent Tree Village and Windward at Lakewood Ranch?
Listings in Bent Tree Village most often report Sarasota High; listings in Windward at Lakewood Ranch report Booker High. Zoning is set by the district and can change - verify by address.
Go deeper on each: Bent Tree Village homes, photos & schools · Windward at Lakewood Ranch homes, photos & schools
Figures are aggregates from realMLS / DBAAR, updated regularly. Thinking about either? Talk to Momentum Realty.