This report covers the complete Bears Club Villas transaction record from 2018 through 2026. It holds 25 closed sales across two distinct sub-products, with full HOA data for every transaction. It closes with a carrying cost model for current buyers and the two record-setting 2026 sales that rewrote the top of the Villa Drive market. The dataset is complete but small: 25 transactions across 14 unique addresses, spanning two distinct sub-products. Conclusions are directional indicators from the full available record, not statistically derived findings.
Two Products, One Address
Bears Club Villas is not a single product. The multiple listing service (MLS) umbrella covers two physically and financially distinct communities that share a gated entry and a golf course but differ in size, HOA structure, and price trajectory. Understanding which product you are evaluating is the prerequisite for any meaningful analysis.
The divergence in HOA trajectory is the central fact of this market. Via Del Orso fees have risen at a more moderate pace (+83% over eight years). Villa Drive fees have escalated from $2,691 per month in 2019 to $7,097 per month by 2025, a 164% increase in six years. That figure spans different unit addresses on Villa Drive. Individual unit escalation histories may differ, and the 164% represents the spread across the dataset's earliest and latest recorded fees. The caveat does not alter the directional conclusion. The 2026 records add a second caveat. The February 2026 close at 308 Villa Drive recorded a fee of $3,828 per month, unchanged from its 2021 sale. The June 2026 record at 304 Villa Drive shows $6,554. Villa Drive is not one fee schedule. Which schedule applies to a specific unit is a diligence question, not an assumption.
The HOA Escalation Record
The most important data series in this dataset is HOA fees over time. Monthly fees are MLS-reported at each transaction and represent the fee in effect on that date, providing a direct record of what buyers have actually paid.
HOA Fee at Time of Sale, 2018 to 2026
Monthly HOA reported in MLS at each closed transaction. Villa Drive (red) vs Via Del Orso (forest).
From the first Villa Drive transaction in June 2019 through May 2025, the recorded HOA increased by $4,406 per month, or $52,872 per year. A buyer who purchased a Villa Drive unit in 2021 at roughly $2,691 to $3,874 per month has seen their carrying costs approximately double in four years.
A direct comparison of HOA amounts between villas and estate homes requires context. Villa HOA fees typically bundle structural insurance, roof replacement reserves and exterior maintenance, plus landscaping and community amenities that estate homeowners pay out of pocket through separate line items. The estate HOA covers common-area maintenance, security, and shared infrastructure. The "4x" headline reflects gross fees, not net incremental cost. The relevant question for buyers is whether the rate of escalation is sustainable and the all-in carrying cost competitive with alternative product types in the same market. The data suggests it is not, at Villa Drive's current fee level.
306 Villa Drive: The Two-Sale Record
The unit at 306 Villa Drive has sold twice in this dataset. The two transactions, separated by three years, document what happens when a structurally escalating HOA intersects with a small-format condo in a market where larger product types are appreciating.
Between May 2022 and April 2025, the HOA rose 50%, from $56,712 to $85,164 annually. The property sold for $2,150,000, a $1.35 million nominal decline (38.6%) while Bears Club estate homes averaged $1,338 per square foot in 2023 and $1,935/SF in 2025.
We cannot isolate the HOA as the sole variable without knowing the property's condition, marketing history, and what offers were received at higher prices. But the directional logic is clear. When annual carrying costs reach $85,164 on a $2.15M asset, the HOA alone runs 3.96% of asset value a year, before property tax, insurance or maintenance. That arithmetic constrains the buyer pool, and a constrained buyer pool produces lower prices.
The question for any current Villa Drive buyer is which of three scenarios materializes. If HOA fees stabilize near current levels, Villa Drive pricing may find a floor and the carrying cost becomes modelable. If fees continue escalating at the observed rate, the 306 Villa Drive outcome is the reference case: a shrinking buyer pool and compressing resale values. If the association restructures its fee schedule or reserve funding, the trajectory could reverse, though the 2019-to-2025 record provides no basis for assuming this. Buyers should model all three scenarios before committing capital. Advisors should present the range, not a single assumption.
The contrast with 304 Villa Drive is instructive. Its larger unit has traded three times since 2022: $3.8 million, $4.65 million, and $5.5 million in June 2026, a 45 percent rise in three and a half years. But the buyers at that address face the street's highest fee track, $6,554 to $7,097 per month in the 2025 and 2026 records. That is the same exposure as the 306 Villa Drive owner who sold at a loss. The entry price differs. The carrying cost exposure does not.
Complete Transaction Record
Flagged row (April 2025, 306 Villa Drive): the only transaction where HOA-to-price ratio exceeded 3%. The two units at 304 Villa Drive have traded six times since 2019. The larger unit's path ($3.8M in 2022 to $5.5M in 2026) and the street's fee escalation have run nearly in parallel.
Sale Price vs. Annual HOA Cost at Time of Sale
Each point plots sale price against the annual HOA paid by that buyer. Bubble size indicates $/SF.
The Carrying Cost Model
The model below places three Bears Club properties side by side. All estimates are approximate and intended for order-of-magnitude comparison. Mortgage assumptions (25% down, 7% fixed) are illustrative. Most buyers in this market purchase with cash or portfolio-rate financing at rates materially below the 7% illustrated here. Cash buyers should substitute their opportunity cost of capital. For a cash purchaser, the HOA becomes a larger share of total annual carrying cost. It runs roughly half at Villa Drive's higher fee schedule, versus the 16% shown in the leveraged scenario below.
Annual Carrying Cost Comparison
Estimated annual costs. Mortgage line shown for illustrative purposes (25% down, 7% fixed). Most Bears Club transactions close with cash or portfolio lending at lower rates. Property tax estimated at 1.2% of purchase price (homestead not applied). HOA from the most recent MLS sale record at each address. Option C (135 Bears Club Drive) uses active listing ask, not a closed sale.
$5,500,000, 3,282 SF
$4,750,000, 4,775 SF
$12,900,000 ask, 8,477 SF
Option A now carries a $750,000 higher purchase price than Option B, based on its June 2026 sale, and adds $26,100 per year in HOA. The estate home costs more than twice as much annually in total, but the HOA represents 2% of carrying costs and has escalated at a fraction of the villa pace. For cash buyers, the HOA differential between Villa Drive and Via Del Orso is even more pronounced as a share of total annual cost.
The 2026 Sales and the Pipeline
The February edition of this report analyzed the winter listing inventory. MLS history has since resolved it, and the resolution rewrote the top of the Villa Drive record. Two sales closed in 2026, both at $5.5 million, and both above every prior Villa Drive close.
The unit at 308 Villa Drive listed on December 20, 2025 at $5.5 million and went under contract in 34 days. It closed February 23, 2026 at the full asking price. The recorded fee was $3,828 per month, unchanged from the unit's 2021 sale record. At $1,691 per square foot, it is the highest price per square foot in the villa dataset. The unit last traded in March 2021 for $2.45 million, a 124 percent gain in five years.
The larger unit at 304 Villa Drive listed at $5,995,000 and closed June 16, 2026 at $5.5 million, 8 percent below ask. Its recorded fee was $6,554 per month ($78,648 per year), below the $7,097 recorded at the same unit's May 2025 sale. The unit had sold for $4.65 million thirteen months earlier, so the June buyer paid an 18 percent premium over that close, at $1,676 per square foot.
The two sales carry different messages. The 308 close says a Villa Drive unit with a mid-tier fee schedule can command estate-grade pricing per square foot. The 304 close says even the street's highest-fee units are appreciating. The buyer paid $850,000 more than the May 2025 buyer for the same unit and the same fee exposure. Neither close resolves the question that separates 306 Villa Drive's outcome from the rest of the street. Which fee schedule applies to a specific unit remains the first diligence item.
One property went under contract in August 2026: 441 Via Del Orso, asking $4,995,000 for 4,150 SF ($1,204 per square foot). It carries a recorded fee of $3,992 per month and listed in May. No Villa Drive or Via Del Orso listing is active. The pipeline is that single pending contract.
Bottom Line
Bears Club Villas offer Bears Club access at a fraction of the estate home price. Whether that value holds depends on which product, which unit, and what the HOA does next. Via Del Orso is the more straightforward purchase: larger, lower in HOA-to-price ratio, and more moderate in fee escalation. Villa Drive is a divided record. The same street produced two $5.5 million sales in 2026 at one end and a $1.35 million decline at the other, in the same market cycle. The variable that separates them is carrying cost, and the fee schedule now differs by unit.
For buyers evaluating Via Del Orso: the closed set of comparable sales is anchored at $1,078 to $1,201/SF (2023 to 2025 sales). The pending contract at 441 Via Del Orso asks $1,204/SF. If it closes near ask, it confirms the top of that range.
For buyers evaluating Villa Drive: model three scenarios: HOA stabilization, continued escalation at the observed rate, and potential restructuring. At the street's higher fee schedule ($6,554 to $7,097 per month), annual HOA exceeds that of a Bears Club estate home at more than twice the purchase price. The 306 Villa Drive record documents the resale impact of a constrained buyer pool. Price the HOA trajectory into your exit strategy before you price the entry.
On fee schedules: the 2026 sale records show $3,828 per month at 308 Villa Drive and $6,554 at 304 Villa Drive, recorded four months apart on the same street. The difference is worth $32,712 per year. Confirm the unit's actual schedule with the association before pricing anything.
Scope: All 25 closed sales in BeachesMLS on Villa Drive and Via Del Orso (the Bears Club Villas and Bears Club Golf Villas subdivisions), January 2018 through August 2026. Bears Club estate homes (100 to 200 series addresses) and Trump National / Ritz Carlton properties are excluded. The dataset is complete for its scope but small (25 transactions, 14 unique addresses). Conclusions should be read as directional indicators, not statistically derived findings.
HOA figures: All HOA monthly amounts are MLS-reported at time of each individual transaction and represent the fee in effect on the date of sale, not a historical association record. HOA amounts are subject to change and can escalate between sale dates. Buyers must verify current HOA amount directly with the homeowners association before any purchase commitment.
HOA escalation calculation: the 164% Villa Drive figure runs from the earliest to the latest HOA amounts in the transaction dataset. That is $2,691/mo at the June 2019 sale of 304 Villa Drive to $7,097/mo in April 2025. This spans different unit addresses on Villa Drive. Individual unit HOA amounts and escalation histories may differ.
HOA coverage comparison: villa HOA fees typically bundle structural insurance, roof replacement reserves and exterior maintenance, plus landscaping and community amenities. Estate home HOA fees cover common-area maintenance, security and shared infrastructure. Estate owners pay structural insurance, roof, exterior maintenance and landscaping separately. Direct comparison of gross HOA amounts between product types overstates the effective delta. The carrying cost model in Section 5 provides a more complete comparison of total annual ownership cost.
Carrying cost model: All figures are estimates for illustrative purposes only. Mortgage calculations shown assume 25% down payment, 7% fixed interest rate, 30-year term. Most Bears Club buyers purchase with cash or portfolio-rate financing at materially lower rates. Property tax estimated at 1.2% of purchase price without Florida homestead exemption. Insurance estimated and will vary by coverage and carrier.
Active listing analysis: Correction (August 2026): the February edition analyzed five listings as active. MLS history shows several of those records reflected earlier listing periods rather than current inventory. The two genuine listings have since closed: 308 Villa Drive at $5.5M in February 2026 and 304 Villa Drive at $5.5M in June 2026. The active-listing section has been replaced with the closed outcomes. The two 304 Villa Drive units (2,882 SF and 3,282 SF) are distinct condominiums sharing a building address, and legal unit designations should be confirmed before any purchase.
On 306 Villa Drive: the $1.35 million price decline between May 2022 ($3.5M) and April 2025 ($2.15M) is a nominal change between two arm's-length closed sales at the same address. It does not account for improvements, condition differences, carrying costs paid by the 2022 buyer, or other factors that affect net return.
Fee records at the 2026 sales: the fee at the February 2026 sale of 308 Villa Drive ($3,828/month) matches its 2021 sale record. The fee at the June 2026 sale of 304 Villa Drive ($6,554/month) sits below the $7,097 recorded at the same unit's May 2025 sale. Whether these reflect updated assessments or reporting variance should be confirmed with the association.
Transaction data: BeachesMLS, extracted August 2026. All 25 closed sales on Villa Drive and Via Del Orso. MLS fields used: Close Date / Close Price / Living Area / HOA Fee / List Price / Days on Market. Pipeline data is current at the August 2026 extraction.
Bears Club estate home HOA reference: MLS-reported figures from closed sales in the Bears Club (100 to 200 series addresses) subdivision, used for comparison purposes only. Estate home HOA amounts are not from the same dataset as the Villas data and should be independently verified.
