Tildens Grove
A guard-gated Windermere custom-estate community with resort amenities.
Live the MaxLife.
$2.1M
Median Price
$1.4M – $4M
175
Homes
$325–$475
Monthly HOA
2003
Established
Windermere Elementary (A-rated)
School Zone
Background
A brief history
Tildens Grove was developed starting in 2003 on a large parcel off Conroy-Windermere Road, one of the wave of guard-gated Windermere luxury communities delivered after Keene's Pointe's success. About 175 lots were released over a multi-year build-out that ran through 2012, with the majority of homes delivered as custom builds rather than production. The community was designed with a staffed 24/7 guard gate, a shared amenity center (pool, fitness, tennis), and an active architectural review that enforced tile roofs, stucco, and traditional Mediterranean vocabulary throughout. A wave of high-end renovations and a handful of teardown rebuilds have moved through the community since 2018.
The feel
What it's like to live here
Tildens Grove occupies a specific niche — it's guard-gated with 24/7 staffing (not keypad), it's Windermere-address (32836 ZIP with Windermere school zoning), and it delivers a real resort amenity footprint (pool, tennis, fitness, clubhouse). The interior is laid out as loops around a central amenity core, with streets generally no wider than two lanes and a heavy live-oak canopy on the interior roads. Lots run 0.3 to 0.8 acre, generous for this price band. Architecture is predominantly Mediterranean revival with tile roofs, circular drives, and summer kitchens, with a growing minority of transitional and modern-farmhouse rebuilds in the last five years.
The details
What to expect
Architecture & Lots
Predominantly Mediterranean revival custom homes built 2003–2012. Tile roofs, stucco, circular drives, summer kitchens, pool cages. A growing share of 2018+ transitional and modern-farmhouse rebuilds. Main homes 4,000–7,500 square feet. Lots 0.3 to 0.8 acre.
Lifestyle & Amenities
24/7 staffed guard gate, resort-style community pool, clubhouse, fitness room, tennis courts, playground. Active community event calendar (holiday gatherings, food truck nights). The amenity footprint is larger than most Windermere gated communities at this price band.
HOA Rules & Fees
Monthly dues $325–$475 including amenity center and 24/7 guard. Active architectural review — exterior changes (paint, roof, landscape, fencing) require pre-approval with typical 4-to-6-week review window. Short-term rentals prohibited; 7-month minimum lease.
Schools
Zoned for Windermere Elementary (A-rated), Bridgewater Middle (A-rated, STEM magnet), and Olympia High (A-rated). Windermere Prep (private) is 8 minutes.
Access & Commute
Seven minutes to Windermere downtown, 10 minutes to the 429/Western Beltway, 15 minutes to Disney, 15 minutes to Restaurant Row, 30 minutes to MCO and downtown Orlando.
Community
Amenities
- 24/7 staffed guard gate
- Resort-style community pool and clubhouse
- Tennis courts, fitness room, playground
- Heavy live-oak canopy on interior streets
- Active community event calendar
Know Before You Buy
HOA rules worth knowing
- Monthly HOA $325–$475 (includes 24/7 guard and amenity center)
- All exterior changes require architectural review
- Short-term rentals prohibited; 7-month minimum lease
- Paint, roof, landscape, and fencing require pre-approval
Education
School assignments
- Windermere Elementary (A-rated)
- Bridgewater Middle (A-rated, STEM magnet)
- Olympia High School (A-rated)
- Windermere Prep (private)
School zone assignments change. Verify with Orange County Public Schools before purchase.
Market Commentary
What the market is doing
Current median sits in the $1.9M–$2.3M band. Smaller interior homes trade $1.4M–$1.9M. Larger custom estates on premium lots run $2.5M–$3.5M. A handful of recent rebuilds on best-in-community lots have closed $3.7M–$4M. Price-per-square-foot runs $360 for dated originals to $475 for fully renovated or new-build. The primary value drivers are lot size, renovation status, and proximity to the community amenity core. Days-on-market has averaged 30–60 days.
Recent Work
Recent sales in Windermere
Representative closings across Windermere. Our Tildens Grove off-market pipeline is larger than what's shown here.
No recent listings shown yet for Tildens Grove. Join the VIP list to see upcoming inventory first.
Also Worth Seeing
Related communities
Windermere
Keene's Pointe
Windermere's guard-gated Jack Nicklaus community on the Butler Chain.
$900K – $5M · 1,100 homes
Explore Keene's Pointe →
Windermere
Casabella
A small Tuscan-inspired enclave behind Windermere's quieter gate.
$2M – $4.5M · 50 homes
Explore Casabella →
Windermere
Chaine du Lac
Windermere's quietest gate on the Butler Chain.
$4.5M – $15.5M · 40 homes
Explore Chaine du Lac →
Windermere
Parkside
A newer Windermere gated community with resort amenities and A-rated schools.
$850K – $1.8M · 320 homes
Explore Parkside →
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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.