Keene’s Pointe Homes in Windermere
Fourteen villages, a Jack Nicklaus course at the center, and the Butler Chain at the edges. Keene’s Pointe is Windermere’s gated golf community built to be used, from the club to the trails to the water.
Updated October 2026
$1.65M
Median closed sale, 12 months to October 2026
1,000
About how many custom homes sit behind one staffed gate
14
Villages, each with its own price band
61
Closed sales, 12 months to October 2026
Living in Keene’s Pointe
Keene’s Pointe is a staffed, gated community of roughly a thousand custom homes arranged into fourteen villages around The Golden Bear Club and its Jack Nicklaus Signature golf course, with frontage and resident access on the Butler Chain of Lakes.
If Isleworth is Windermere’s old guard, Keene’s Pointe is its everyday address. The lots are generous, the architecture is custom without being theatrical, and the community actually gets used: golf carts to the club, kayaks on the interior lakes, and the A-rated school zone that anchors this side of town.
The club is the social center for members, but the parks, trails and playgrounds serve every resident. The wider context, the Butler Chain, the schools and how Keene’s Pointe compares with the town’s other gates, is in our Windermere guide.
Keene’s Pointe home prices
The housing stock is custom, built out mostly through the 2000s and 2010s with newer builds still appearing on remaining lots. What you pay is driven less by square footage than by position: interior street, golf frontage, interior lake, or the Butler Chain itself.
Over the twelve months to October 2026, Stellar MLS shows 61 closed sales at a median of $1,650,000. The middle half sold between about $1.27 million and $2.95 million, from a low of $945,000 to a top sale of $13.2 million, with a median of 45 days on market. The position ranges in the table are our guide; the week to week picture is a phone call to (813) 992-3073.
| Position | Typical range | What you’re paying for |
|---|---|---|
| Interior streets | From about $950K to $3.5M | The gate, the schools, the address |
| Golf & interior lakes | About $2.5M to $6.5M | Nicklaus fairways or private water views |
| Butler Chain lakefront | About $3.5M to $7.5M+ | Skiable water, docks, the top of the market |
| Community median | $1.65M | 61 sales, twelve months to October 2026; moves with the sales mix |
What Keene’s Pointe offers
The gate, the golf and the lakes, without stepping all the way up to Isleworth pricing.
One staffed gate around fourteen villages. The Golden Bear Club and its Jack Nicklaus Signature course for those who join, and the water and the trails for every resident. Resale depth, too: a thousand homes behind one respected gate produce steady, readable comps. This side of town sits in an A-rated school zone; confirm any specific address with the Orange County Public Schools locator before you write an offer.
What it does not offer: life without HOA structure, or a walk to dinner. For town center energy and new construction, Hamlin is fifteen minutes away and a different world. We show both without a preferred outcome. The commission is the same, and the point is that you end up in the right one.
What our clients say
“Within about 48 hours of listing the property, we had around five offers! … He’s knowledgeable, responsive, honest, and genuinely cares about helping his clients.”
Buying in Keene’s Pointe: our advice
What we tell every buyer before they tour a single home here.
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Pick the village before the house
The fourteen villages differ in lot size, age, architecture and price band, and two similar houses in different villages can behave very differently at resale. We rank villages against your budget and habits before we tour a single home.
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Decide the club question early
Membership at The Golden Bear Club is a separate decision from the purchase, and social life here does divide between club members and everyone else. Structures and fees change, so we confirm the current picture with the club before you write an offer, not after.
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Read the water carefully
Butler Chain frontage, interior lake frontage and lake access are three different assets at three different prices. Skiable water with a dock is the blue chip; a view across a pond is pleasant but should not be priced like the Chain.
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Budget the whole carry
HOA dues, possible club costs, insurance on larger homes and the upkeep a community like this expects all belong in the math before you fall in love. We put the full monthly picture on one page early, because that is what we would want shown to us.
Keene’s Pointe homes for sale
See every Keene’s Pointe home on the market today, then call us and we will tell you which village each one sits in and how it compares.
Keene’s Pointe questions
What buyers ask us most. Something else? Call (813) 992-3073.
How much do Keene’s Pointe homes cost in 2026?
Over the twelve months to October 2026, Keene’s Pointe had 61 closed sales on Stellar MLS at a median of $1,650,000, from a low of $945,000 to a top sale of $13.2 million. As a guide, interior streets run from about $950,000 to $3.5 million, golf and interior lake positions roughly $2.5 million to $6.5 million, and Butler Chain lakefront from about $3.5 million up. The median moves with the mix of what happens to sell.
Do you have to join the Golden Bear Club?
No. Membership is a separate decision, and plenty of residents live happily without it. Social life does tend to divide between club members and everyone else, and membership structures and fees change, so we confirm the current picture with the club before our clients write an offer.
Is there Butler Chain access?
Yes, beyond the lakefront estates themselves the community includes lake access for residents, which is a meaningful part of the value here. The difference between direct frontage, deeded access and a view is large, and it shows up in resale.
What are the fourteen villages?
Each village has its own character, lot sizes and price band, from established custom streets to golf frontage and lakefront. Which one fits you depends on budget, whether golf or water matters more, and how close to the club you want to be. That is a conversation, not a chart, and we are glad to have it.
Keene’s Pointe or Isleworth?
Keene’s Pointe is larger, spread across fourteen villages, and starts lower. Isleworth is smaller, more private and more expensive. We live in Windermere and are glad to walk both with you.
Which Keene’s Pointe village is yours?
One call and we will rank the fourteen against your budget, your golf habits and the water you want. We live ten minutes from the gate.