Tildens Grove
A guard-gated Windermere custom-estate community with resort amenities.
Live the MaxLife.
$2.1M
Median Price
$1.4M – $4M
175
Homes
$104–$317
Monthly HOA
2003
Established
Windermere Elementary
School Zone
Search Homes for Sale in Tildens Grove
First access
Get notified when a Tildens Grove home hits the market.
VIP members see new Tildens Grove inventory 48 hours before Zillow.
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), 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
HOA $104–$317/month (confirmed via public listing data, Apr 2026). Includes 24/7 staffed guard gate, resort-style pool, clubhouse, fitness room, tennis courts, and playground. 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
Schools named for the area: Windermere Elementary, Bridgewater Middle (STEM magnet), and Olympia High. Assignment follows the street address, so check each home in OCPS Find My School before you write an offer. 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
- HOA $104–$317/month — confirmed via public listing data, Apr 2026
- Includes 24/7 guard gate, pool, clubhouse, fitness room, tennis courts, playground
- All exterior changes require architectural review (4–6 week review window)
- Short-term rentals prohibited; 7-month minimum lease
- Paint, roof, landscape, and fencing require pre-approval
Education
School assignments
- Windermere Elementary
- Bridgewater Middle (STEM magnet)
- Olympia High School
- Windermere Prep (private)
School zone assignments change. Verify with the Orange County school district 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.
Active MLS Inventory
Search homes in Tildens Grove
Be first to see new Tildens Grove listings.
Get notified when a home in Tildens Grove hits the market — VIP list members see new Tildens Grove inventory 48 hours before it appears on Zillow.
Get Tildens Grove AlertsActive MLS Inventory
Homes near Tildens Grove
Nothing is listed in Tildens Grove right now. Showing homes in Windermere. Many Tildens Grove homes sell off-market — get notified first when new inventory comes available.
$3,150,000
1815 Windermere Rd
Windermere, FL 34786
4 bd · 5 ba · 4,290 sqft
Not Applicable
MLS ID #O6447555, BALDWIN PARK REALTY LLC.
Listing provided by Stellar MLS
$597,000
8576 Powder Ridge Trl
Windermere, FL 34786
4 bd · 4 ba · 2,661 sqft
Windermere Trails
MLS ID #O6447414, WRA BUSINESS & REAL ESTATE.
Listing provided by Stellar MLS
$2,390,000
6544 Cartmel Ln
Windermere, FL 34786
5 bd · 5 ba · 4,185 sqft
Reserve At Lake Butler Sound Unit 2
This property is under contract. Contact us for backup offer opportunities.
MLS ID #O6447314, FLORIDA CONNEXION PROPERTIES.
Listing provided by Stellar MLS
$775,000
8291 Procida Isle Ln
Windermere, FL 34786
4 bd · 3 ba · 2,224 sqft
Windermere Isle Ph 2
MLS ID #O6436040, KELLER WILLIAMS REALTY AT THE LAKES.
Listing provided by Stellar MLS
$559,900
5231 Lemon Twist Ln
Windermere, FL 34786
4 bd · 4 ba · 2,311 sqft
Summerport Ph 03
MLS ID #S5160165, AGENT TRUST REALTY CORPORATION.
Listing provided by Stellar MLS
$485,000
13424 Hopkinton Ct
Windermere, FL 34786
4 bd · 2 ba · 2,190 sqft
Lakes/Windermere-Peachtree
MLS ID #O6438808, WEMERT GROUP REALTY LLC.
Listing provided by Stellar MLS
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 transitional architecture.
$850K – $1.8M · 320 homes
Explore Parkside →
Own a home in Tildens Grove?
Find out what it's worth today.
Get a free, agent-prepared valuation grounded in actual Windermere sales — plus a clear picture of what it costs to sell in Florida and how to keep more at closing.
Want Tildens Grove homes first?
Hand-picked Tildens Grove matches — 48 hours before MLS. Two to three per month.
Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Based on information submitted to the MLS GRID as of October 26, 2026. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
All or a portion of the multiple listing information is provided by Stellar MLS, from a copyrighted compilation of listings. The compilation of listings and each individual listing are © 2026 Stellar MLS. All rights reserved.
Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA