This report covers the complete Bears Club Villas transaction record from 2018 through 2025: 20 closed sales across two distinct sub-products, with full HOA data for every transaction, a carrying cost model for current buyers, and a property-by-property analysis of the five active listings. The dataset is complete but small: 20 transactions across 12 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 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 moderate pace (+47% over seven 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 HOA Escalation Record
The most important data series in this dataset is not price per square foot. It 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 2025
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, exterior maintenance, 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 not whether the villa HOA is higher in absolute terms, but whether the rate of escalation is sustainable and whether the all-in carrying cost is 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
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 $1,303/SF 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 effective cost of ownership is 3.96% annually from HOA alone, 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. That address has appreciated 195% since 2019, from $1,575,000 to $4,650,000. But the 2025 buyer at $4,650,000 now faces the same $7,097/month HOA as the 306 Villa Drive buyer 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%. 304 Villa Drive has traded five times since 2019; its price appreciation (+195%) and HOA escalation (+164%) 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: approximately 35 to 40% at Villa Drive's current fee level, versus the 20% 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 most recent MLS sale record. Option C (135 Bears Club Drive) uses active listing ask, not a closed sale.
$4,650,000, 3,282 SF
$4,750,000, 4,775 SF
$12,900,000 ask, 8,477 SF
Options A and B are priced within $100,000 of each other, but Option A's HOA adds $32,616 per year in incremental carrying cost. 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.
Active Listings, Analyzed
Five Bears Club Villas properties are currently listed, ranging from $1.895 million to $5.995 million. The analysis below reflects market context based on closed comparable sales and is not a valuation opinion or pricing recommendation for any specific property. All HOA figures are MLS-reported at time of listing; buyers should verify current rates directly with the homeowners association before any purchase commitment, as rates may have changed since the listing was entered.
This unit at 304 Villa Drive sold in May 2025 for $4,650,000, the highest price in the dataset for this address. The current ask represents a $1,345,000 premium over a closing eight months prior at the same unit. The $2,080/SF ask would represent a 47% premium over the $1,417/SF recorded at this address in May 2025—the highest $/SF in the dataset. The listed HOA of $6,554/month is below the $7,097/month recorded at the May 2025 sale; confirm whether this reflects an updated assessment or a data entry variance before proceeding.
The closest comparable is 437 Via Del Orso (May 2025, $5,075,000, $1,078/SF, identical HOA). This ask at $1,212/SF is $575,000 above that comp. The +12% premium may be defensible depending on condition, but 307 days without a sale indicates the market has not accepted the current price. A reduction toward the $5,075,000 to $5,200,000 range would align with the most recent comparable.
Sold March 2023 for $3,640,000 at $1,150/SF with the same $3,874/month HOA recorded on the current listing. The $450,000 premium (12.4%) is modest, and the HOA has not escalated on this unit, notably below the $7,097/month appearing on other Villa Drive addresses. At 161 DOM, the market has not confirmed the ask, but the HOA structure here is the most favorable among current Villa Drive listings.
Sold March 2021 for $2,450,000 at $753/SF with a $3,828/month HOA. The current ask at $830/SF with a listed HOA of $1,800/month represents a significant departure from the prior recorded fee. If the $1,800 figure is accurate and stable, this is the most HOA-favorable active listing in the dataset. A $2,028/month difference from the prior transaction is material and warrants direct confirmation with the association before any offer.
Two active listings exist simultaneously at 304 Villa Drive: this one at $1,895,000 and the $5,995,000 listing above. The different square footages (2,882 SF vs. 3,282 SF) indicate distinct condominium units sharing a building address. The $658/SF ask is below the $685/SF recorded at the August 2021 sale on what appears to be the same floor plan. The $2,692/month HOA matches 2019–2020 records—dramatically below the $7,097/month on the larger 304 Villa Drive listing. If accurate and structurally stable, this is the only Villa Drive listing where the carrying cost arithmetic differs materially from the rest of the street.
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 195% appreciation at one address and a $1.35 million decline at another, in the same market cycle. The variable was carrying cost trajectory, and that trajectory has not stabilized.
For buyers evaluating Via Del Orso: the 2025 comp set is anchored at $1,078 to $1,148/SF. 426 Via Del Orso has sat 307 days at $575,000 above the closest comparable. The market has indicated where the ceiling sits. Engage at or near the comp level.
For buyers evaluating Villa Drive: model three scenarios—HOA stabilization, continued escalation at the observed rate, and potential restructuring. At current levels, annual HOA exceeds that of a Bears Club estate home at four times 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.
At 308 Villa Drive ($1,800/month listed HOA): if the MLS figure is accurate and reflects a structurally different fee schedule, this is the only Villa Drive listing where the carrying cost arithmetic changes materially. This is the first number to verify.
Scope: All 20 closed sales in BeachesMLS with subdivision names containing "BEARS CLUB VILLAS," "BEARS CLUB GOLF VILLAS," or equivalent designations, January 2018 through May 2025. 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 (20 transactions, 12 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 escalation figure is calculated from the earliest to latest HOA amounts in the transaction dataset ($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, exterior maintenance, 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: The commentary on active listings reflects market context based on closed comparable sales as of February 2026. It is not a valuation opinion, appraisal, or pricing recommendation for any specific property. Listing prices, HOA figures, and days on market are as reported in MLS at the time of data extraction and may have changed. Two listings exist at 304 Villa Drive with different square footages (2,882 SF and 3,282 SF); these appear to represent distinct condominium units sharing a building address. Legal unit designations should be confirmed before any purchase.
306 Villa Drive: The $1.35 million price decline between May 2022 ($3.5M) and April 2025 ($2.15M) is a nominal price 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.
Active listing DOM and date discrepancies: Two listings show potential inconsistencies between listed date and days on market as of the February 17, 2026 data extraction. 304 Villa Drive ($5,995,000) shows 28 DOM, consistent with a January 2026 listing date rather than December 2025 as originally recorded; this may reflect a re-listing after an initial December entry. 304 Villa Drive ($1,895,000) shows 52 DOM, consistent with a late December 2025 entry rather than January 2026. Both should be verified against MLS history before publication.
Transaction data: BeachesMLS, extracted February 2026. All 20 closed sales in Bears Club Villas / Bears Club Golf Villas Condominium subdivisions. MLS fields used: Close Date, Close Price, Living Area, Property Condition, HOA Fee. Active listing data current as of February 17, 2026.
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.
