The analysis covers 55 non-closed listing records at The Bears Club estate section, extracted from the multiple listing service (MLS) in August 2026. Bears Club Villas and cluster homes (400-series addresses) are excluded. For each listing attempt we track asking price, price per square foot, days on market (DOM) and outcome status. Counterfactual valuations use $1,590/SF, the post-2022 community average excluding the $48M record sale at 152 Bears Club Drive.
Too Early: The Sellers the Market Wasn't Ready For
The most misread listings in the Bears Club record asked too early rather than too much. They carried a number the market would eventually validate enthusiastically, just years later than the seller expected. These sellers were right about their properties. What they missed was when the Bears Club buyer would arrive at their price.
The pre-2022 Bears Club market was a fundamentally different instrument from the one that exists now. Estate homes traded at $725/SF on average from 2015 through 2019. Buyers existed for $7-10 million assets. The $12-20 million Bears Club estate (the product that trades routinely today) simply did not have a deep buyer pool before the post-COVID repricing of South Florida luxury real estate. Sellers who built or held exceptional homes priced at what they believed the properties were worth. They discovered that being correct about value and being correct about timing are different disciplines entirely.
The listing at 209 Bears Club Drive is the most instructive non-sale in the dataset. The property, a 10,490 SF custom estate built in 2009, was listed seven times between January 2014 and July 2019. The asks ranged from $8.345 million to $12.5 million. None produced a close. In 2014, $12.5 million for a Bears Club estate was a number the market had no framework for: the community's estate homes were trading in the $5-8 million range. By 2023, 136 Bears Club Drive (a 2009-built home) sold for $19.8 million. The 2014 seller was not irrational. The market simply had not yet repriced to the tier the property occupied.
The pattern is consistent across the pre-2022 non-sellers. Each of these owners built or held a labor-intensive custom property. The Bears Club buyer pool of the time, smaller, less capitalized and oriented toward a different price architecture, could not absorb it. The repricing that followed COVID revealed value in these homes rather than creating it. The value had been there, unrecognized.
The Cost of Capitulating Early
When a seller holds a custom-built estate through years of listing attempts and ultimately sells below the asking price into a market that had not yet repriced, the discount to the asking price is only part of the loss. The rest is the entire gain the post-2022 buyer captured in their place. The cards below model three cases using the post-2022 community average of $1,590/SF as the counterfactual reference rate.
Peak ask of $7.75M (Jan 2019). On market 587 days before sale. Closed at $807/SF. At the post-2022 community average of $1,590/SF, this property would be valued at approximately $13.5M today.
Peak ask of $12.995M (Oct 2017). On market 266 days before expiry. Closed at $706/SF. At $1,590/SF, this property would be valued at approximately $22.5M today.
Peak ask of $12.5M (Jan 2014). Last listed Jul 2019 at $8.345M. Approximately 2,000 cumulative days on market across all listing periods. At $1,590/SF, estimated current value is approximately $16.7M.
Counterfactual values use $1,590/SF, the post-2022 Bears Club estate average excluding the $48M record sale. Actual realized values for 138 and 161 Bears Club would depend on property condition, specific improvements, and market conditions at time of a hypothetical sale. These figures are illustrative of the repricing magnitude, not predictions.
A seller who listed 161 Bears Club Drive at $12.995M in 2017 was asking for a price the market now pays routinely. The estate at 136 Bears Club sold for $19.8M in 2023. The one at 103 Bears Club sold for $17M in 2024. The 2017 ask of $12.995M would be unremarkable in today's set of comparable sales. The Bears Club market of 2017 simply did not have a buyer for that number. A seller caught in that gap holds a finished property and a real value, with a buyer pool that has not materialized yet. The data cannot make the choice: wait for the market to arrive, or sell into the one that exists.
Too High: Asks the Market Has Never Validated
A different category of non-sale involves asks in excess of what the market has demonstrated any willingness to pay, even in the fully repriced post-2022 environment. The distinction matters: a seller asking $12M in 2017 on a property worth $15M today was right about value and wrong about timing. A seller asking $55M in a community whose all-time transaction record is $48M is operating from a different premise entirely. That record took a singular estate on 2.4 acres, built in 2021, with 25,518 total square feet.
The 126 Bears Club case is useful precisely because the property itself is substantial: 16,316 SF, built in 2020, on one of the larger lots in the community. The listing misread the ceiling of a market whose highest recorded sale at the time was $11 million. That market would not produce a close above $20 million until 2025. In a community where 17 of 33 sales since 2015 have closed since the start of 2023, no sale has exceeded $3,099/SF. An asking price of $3,371/SF requires a buyer who believes this single property exceeds the community's best sale. That buyer has not appeared.
The $/SF ceiling the market has demonstrated. Bears Club has produced exactly two transactions above $1,868/SF: 152 Bears Club Drive at $2,938/SF in February 2025 and 228 Bears Club Drive at $3,099/SF in July 2026. The first was a 2021-built estate with 25,518 total square feet and a resort-scale amenity package on 2.4 acres. The second was a 2024-built waterfront home. Every other post-2022 close has occurred between $1,210/SF and $1,868/SF. The one exception below the range is 148 Bears Club Drive at $726/SF in April 2024, a 2001 home that sold near lot value. No resale estate has ever closed above $1,868/SF.
Both: The Speculative Re-List Problem
A third category is more complex than either of the first two. These are properties that transacted at legitimate market prices, then re-entered the market at asks that require the buyer to underwrite a significant appreciation premium on a short hold. The logic is understandable: the Bears Club repriced substantially between 2022 and 2025, and a seller who bought in that window reasonably believes they bought into a rising market. The data suggests the market is more discriminating about this than sellers expect.
The 136 Bears Club situation illustrates what happens when a buyer correctly identifies an appreciating market and transacts at a legitimate price. The mistake was attempting to monetize that appreciation faster than the next buyer would confirm it. The $19.8M sale in March 2023 was well-executed: it was the market's first post-gap transaction, and $1,210/SF was a price that subsequent transactions validated as the new floor. The relist was a different exercise. It asked the market to confirm that this specific home, a 2009 build, was worth $2,625/SF at the opening ask, a figure no Bears Club resale has ever approached. The market returned its answer in March 2026. The closing price of $19.61 million, at $1,584/SF, sat inside the validated range and $190,000 below what the seller had paid three years earlier. Three years of ownership in a rising market returned slightly less than the purchase price, after 461 days of exposure and a $5 million reduction.
The posture at 228 Bears Club Drive was genuinely unusual: a seller who responded to market non-response by raising the price. Two withdrawn listings at $36.95M and $38.5M, each generating hundreds of days on market without a close, were followed by a third listing at $39M, above both prior asks. In July 2026 the strategy was vindicated in direction, if not in full. The home closed at $33.77 million, 13 percent below the final asking price but at $3,099/SF, the highest price per square foot in Bears Club history. The credential that carried it was one no prior above-ceiling listing could claim. The home was completed in 2024, sits on water frontage and had no resale equivalent in the comparable set.
Green band: post-2022 resale transaction range ($1,210-$1,868/SF). Gold bars: 2026 closed sales at their sold $/SF. Red bars: active asks above the resale ceiling. Gold dashed line: all-time record $/SF, set by the July 2026 sale at 228 Bears Club Drive.
What's Active Now: Reading the Current Inventory
Six active estate listing records (five properties, since 210 Bears Club carries two MLS records) are on the market in August 2026. The inventory looks different than it did in February because the first half of 2026 resolved most of what was open. Six estate sales closed between February and July, including the two largest transactions since the $48 million record. The only February listing that neither sold on the MLS nor remains on the market is 146 Bears Club Drive, whose $26.5 million listing was cancelled after 223 days. The public record fills in the rest. The home changed hands privately in November 2025 for $18.965 million, after a $24.775 million listing had expired. The $26.5 million listing entered the MLS on November 24, 2025.
The resolutions are worth reading closely. The sale at 118 Bears Club Drive closed at $41 million on February 27, seven percent below the $44 million ask, at $1,780/SF. It is the community's second-highest sale ever. For a 23,029 SF home built in 2010, the price per square foot landed inside the established resale range rather than above it. The 29-day path to contract followed four earlier listing attempts dating to 2019. The sale at 228 Bears Club Drive closed at $33.77 million on July 15, thirteen percent below the $39 million ask, at $3,099/SF. That is the highest price per square foot ever recorded at the Bears Club, above even the $48 million sale at 152 Bears Club Drive. Both homes that have broken the $1,868/SF resale ceiling are new construction. The home at 136 Bears Club Drive, which had asked $32.5 million after a $19.8 million purchase in 2023, closed at $19.61 million. Three other estates (124, 150, and 156 Bears Club Drive) closed between $1,566 and $1,821/SF, all inside the resale range.
The current inventory divides by construction vintage as much as by price. Two listings are priced inside the resale range. One is 135 Bears Club Drive at $12.9 million ($1,522/SF), a 2008 build in its fourth listing period since November 2024. The other is 131 Bears Club Drive at $15.95 million ($1,862/SF), a 2018 build reduced from $18.5 million across 855 continuous days on market. The 210 Bears Club dual listing, a 2024 build cut from $25.75 million to $21.9 million ($2,733 to $2,770/SF), is the one above-ceiling listing with a closed comparable behind it. The July sale at 228 Bears Club Drive, also a 2024 build, cleared $3,099/SF. The listing at 232 Bears Club Drive asks $2,478/SF on a 2010 home, a level no resale has reached. The public record shows the home changed hands privately in October 2024 for $17.65 million, after an $18.975 million listing expired. It has been asking $21.5 million since May 2025. At the top of the market sits 215 Bears Club Drive, listed in March 2026 at $47.9 million and since raised to $52.9 million. It asks $3,509/SF for a 15,075 SF waterfront home scheduled for 2027 completion. That is 13 percent above the record set at 228 in July. Only the $55 million sought at 126 Bears Club Drive in 2022 has asked more.
Resale ceiling: $1,868/SF (103 Bears Club Drive, March 2024). "Above ceiling" compares ask $/SF to $1,868. The two sales above that level ($2,938/SF at 152 Bears Club, $3,099/SF at 228 Bears Club) were both new construction. DOM for 131 Bears Club is continuous since April 2024. The 210 Bears Club address appears as two MLS records with identical price and list date. Treat the pair as a single listing for pricing analysis.
Bottom Line
The Bears Club's unsold listing record separates into two fundamentally different problems. The pre-2022 non-sellers were largely timing errors, custom estates listed into a market that could not yet absorb them. The loss of patience cost those sellers millions in appreciation they would have captured by waiting. The post-2022 non-sellers are pricing errors, and the first half of 2026 graded them. The overpriced resale at 136 Bears Club closed 40 percent below its original ask and just under its 2023 purchase price. The long-tenured ask at 131 has been cut into the resale range. The two sales that cleared above the old ceiling did so on credentials (2021 and 2024 construction, water frontage at 228) that no active resale listing carries.
For sellers pricing a Bears Club estate today: The resale range the comparable set supports is $1,210 to $1,868 per square foot. Five of the six estate sales in the first half of 2026 closed inside it. The exception was a 2024-built waterfront home. Unless your property carries that kind of credential, price to the range the comparable set supports, not the range you need the market to reach.
For buyers evaluating active inventory: Two active listings are priced inside the resale range: 135 Bears Club at $1,522/SF and 131 Bears Club at $1,862/SF. The 210 Bears Club listing is a 2024 build asking below the $3,099/SF that the July sale at 228 Bears Club validated for new construction. The remaining asks have no closed comparable behind them: a 2010 resale at $2,478/SF and a 2027 delivery priced 13 percent above the community's best sale.
The lesson the "too early" sellers illustrate: Being correct about a property's value and being correct about the market's timing are separate disciplines. The sellers who capitulated before the post-2022 repricing left $7-12M on the table. The cost of selling into the wrong market ran past the discount to ask, all the way to the entire gain the next buyer captured.
Scope: all non-closed listing records at The Bears Club in Jupiter, from BeachesMLS, extracted August 2026. Excludes Bears Club Villas, Bears Club Golf Villas Condominium, and all cluster-home (400-series address) listings. Status codes used: E (expired), L (cancelled), W (withdrawn), A (active). Where a property appears under multiple listing periods, each period is treated as a separate listing record. Cumulative DOM is the sum across all listing periods in the dataset.
Counterfactual rate ($1,590/SF): The post-2022 Bears Club estate average excluding the $48M record at 152 Bears Club Drive, computed from the August 2026 extraction. This figure models what a property that sold pre-2022 or never sold on the MLS would be worth in the current market. It is a community average, not a specific comparable. Actual value would depend on condition, improvements, the specific lot and buyer demand at the time of a hypothetical sale.
Resale $/SF ceiling ($1,868/SF): the highest per-square-foot price achieved in any Bears Club resale transaction. It was recorded at 103 Bears Club Drive (March 2024 / $17,000,000 / 9,100 SF / a 2017 build). The two transactions above this level were both new construction and are treated as a separate tier. They are 152 Bears Club Drive at $2,938/SF in February 2025 and 228 Bears Club Drive at $3,099/SF in July 2026. One post-2022 close sits below the range: 148 Bears Club Drive at $726/SF (April 2024), a 2001 home that sold near lot value.
The 118 Bears Club Drive close: February 27, 2026 at $41,000,000 ($1,780/SF), the community's second-highest sale. The February version of this report described the transaction as pending at its $44 million list price. The closed price is 6.8 percent below that figure.
The 228 Bears Club Drive close: July 15, 2026 at $33,770,000 ($3,099/SF), the community's highest recorded price per square foot. The living area figure changed across its listing periods (10,579 SF in Jan 2024, 10,706 SF in Apr 2025, 10,896 SF at sale), reflecting construction completion and remeasurement. All $/SF figures use the SF recorded in the respective listing period.
The 210 Bears Club Drive dual listing: two MLS records exist at this address with identical list price ($21,900,000, reduced from $25,750,000) and list date (December 2025). The SF figures differ slightly (7,907 and 8,013). This is treated as one property for analytical purposes. Buyers should confirm the legal property description and SF with the listing agent.
BeachesMLS (Beaches Multiple Listing Service), extracted August 2026. All listing status codes, days on market figures, ask prices, and square footage figures are MLS-reported. Closed sale prices are from MLS records confirmed against public records where available.
