Keene's Pointe
Windermere's guard-gated Jack Nicklaus community on the Butler Chain.
Live the MaxLife.
$1.8M
Median Price
$900K – $5M
1,100
Homes
$250–$400
Monthly HOA
1996
Established
Windermere Elementary (A-rated)
School Zone
Background
A brief history
Keene's Pointe opened in 1996 on roughly 1,200 acres that had sat, for most of the century, as citrus groves and timber off Chase Road. The developer brought in Jack Nicklaus to route the Golden Bear Club around twelve interior lakes and a high ridge of old oaks — the course opened for members in 2000. Tiger Woods bought here in his early touring years, which pushed the community into the national conversation before the first thousand homes were even built. Build-out happened in waves through the 2000s and 2010s, with the last large section (around Lake Tibet and the Bay Hill side) closing out in the late 2010s. A handful of teardown-and-rebuild sites still turn over each year. The neighborhood is named for the Keene family, who held the land for most of the twentieth century and whose surname still sits on the front gate and the main spine road.
The feel
What it's like to live here
Keene's Pointe feels like a small town that happens to sit behind a guard. Kids ride bikes to the community pool. Residents drive golf carts to the Golden Bear Club and to Friday food-truck nights at the clubhouse lawn. The tree canopy is the thing most first-time visitors notice — Angel Oak Drive and the long spine of Keene's Pointe Drive are shaded almost fully by mature laurel and live oaks, which is rare for a community this new. Lot sizes run from about 0.3 acre in the interior sections up to 1.5 acres on Lake Tibet and Lake Sheen, with the oversized lakefront parcels commanding the biggest premiums. The architecture is mostly traditional Southern — brick, cedar shake, metal roofs, deep front porches — with a growing minority of transitional farmhouse and modern-Mediterranean rebuilds where original 1990s homes have come down. Security is 24/7 with a guard at the main gate off Chase Road and a second gate on the Bay Hill side; pre-approved guest lists are standard.
The details
What to expect
Architecture & Lots
Most original homes are traditional Southern or Georgian revival built 1998–2008, in the 3,500–6,500-square-foot range. Rebuilds since 2018 skew modern-Mediterranean or transitional farmhouse. Lots run 0.3 to 1.5 acres; expect a buffer of oaks and landscaping between neighbors. Driveways are almost always paver or brick. The architectural review board is active — exterior color changes, roof replacements, and new fences all need pre-approval.
Lifestyle & Amenities
The Golden Bear Club is a separate membership (golf, social, and sport tiers — you don't get access by buying a home). The community's own amenities include a resident pool, tennis and pickleball, a community boat launch onto Lake Tibet (which connects to the Butler Chain), a fitness center, and a private park on Lake Burden. Golf carts are street-legal on interior roads.
HOA Rules & Fees
Monthly dues run $250–$400 depending on section, with an additional one-time capital contribution at closing (typically 0.25% of purchase price). Boat lifts and new docks require architectural review — expect a four-to-six-week approval window before you can install or modify. Short-term rentals are prohibited; 30-day minimum lease terms are enforced.
Schools
Zoned for Windermere Elementary, Bridgewater Middle, and Olympia High — all highly rated Orange County schools. The community is also within reasonable driving distance of Windermere Prep and The First Academy for families considering private options.
Access & Commute
Main entrance is off Chase Road, roughly 8 minutes to Restaurant Row and 15 minutes to the 429/Western Beltway for trips north. Downtown Orlando is 25–35 minutes depending on I-4. Walt Disney World is 15 minutes. Orlando International is 30–35 minutes. The Chase Road gate backs up during school drop-off (7:30–8:15 a.m.) — the Bay Hill gate is faster on weekdays.
Community
Amenities
- Golden Bear Club — Jack Nicklaus 18-hole signature course (separate membership)
- Community boat launch with Butler Chain access via Lake Tibet
- Resident pool, tennis, and pickleball courts
- Community fitness center
- Lake Burden park and playground
- 24-hour manned gate at both entrances
- Golf-cart-friendly interior roads
Know Before You Buy
HOA rules worth knowing
- Boat lift and dock modifications require architectural review (4–6 week approval)
- Short-term rentals prohibited; 30-day minimum lease
- Exterior color, roof, and fence changes require pre-approval
- One-time capital contribution at closing (~0.25% of purchase price)
- Parking of commercial vehicles, RVs, and boats on driveways restricted
- Pre-approved guest lists required for extended stays
Education
School assignments
- Windermere Elementary (A-rated)
- Bridgewater Middle (A-rated, STEM magnet)
- Olympia High School (A-rated)
- Windermere Prep (private, 6 minutes)
- The First Academy (private, 15 minutes)
School zone assignments change. Verify with Orange County Public Schools before purchase.
Market Commentary
What the market is doing
Current median sale sits in the $1.6M–$1.9M band, with entry-level interior homes closing in the $900K–$1.2M range and Lake Tibet or Lake Burden waterfront trading from $3M to north of $5M. The biggest driver of spread isn't square footage — it's lot. A well-renovated 4,200-square-foot home on 0.4 acre in the interior will sell for roughly half of the same home on a Lake Tibet lakefront. Homes on the Golden Bear fairway also carry a ~10–15% premium over comparable interior lots. Days-on-market has averaged three to four weeks for homes priced to the comps; anything that hangs past 60 days typically needs a price correction or has a known issue (deferred maintenance on the roof, dated kitchens, a neighboring rebuild). The community tends to move fastest between late January and early May, before summer slowdown.
Recent Work
Recent sales in Windermere
1 home we've closed directly in Keene's Pointe.
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Information on this page is compiled from public records, MLS data, community associations, and broker observation. Price ranges, HOA fees, school assignments, and community amenities change — verify all details with MaxLife Realty and the relevant community association before making a purchase decision. Ryan Solberg, Broker, License #BK3354351. MaxLife Realty, 321.373.3536.