Windermere gated communities: Gate by gate: staffed or electronic, the HOA, the water, and what's for sale
Fourteen gated communities with a Windermere address, each classed by its gate from dated MLS records checked with Andy, with home counts from Orange County parcel data and an HOA example that says how often it's billed.
Which Windermere communities are gated?
Is Windermere a gated community?
No, but many communities inside it are. Windermere is a town of about 2.2 square miles inside a much larger 34786 ZIP code. Within that area, communities such as Isleworth, Keene's Pointe, Lake Butler Sound and The Reserve at Belmere each have their own gate, HOA and private roads. Most of them are in unincorporated Orange County, not in the Town.
Gated Windermere in short
- "Guard" or "No Guard": the MLS records which kind of gate a community has; Andy checked the gates in October 2026.
- Two gated communities have a golf club: Isleworth and Keene's Pointe.
- Isleworth, Keene's Pointe, Lake Butler Sound, Chaine du Lac and Butler Bay sit on the Butler Chain of Lakes.
- HOA examples run from $140 a month to $3,672 a quarter, so compare them by the year.
- A gate controls who drives in. It doesn't change who may buy a home there.
The gate ledger.
Gate type from the MLS field on dated listings, checked with Andy; home counts from Orange County parcel data, and one HOA example per community with how often it's billed.
| Isleworth | Guard-staffed | About 331On about 600 acres · Andy Neal | Isleworth Golf & Country Club | Butler, Tibet-Butler, Louise, Chase, Isleworth, Blanche | $3,672 / quarterListings, Jul and Oct 2026 |
| Keene's Pointe | Guard-staffedTwo entrances | ~1,055 | Golden Bear Club | Tibet-Butler; Lake Isleworth (Unit 3); Lake Burden | $3,578 / yearListings, Aug–Sep 2026 |
| Lake Butler Sound | Guard-staffed | 213+ 1 vacant lot | — | Lake Butler | $637 / monthTwo listings, Oct 2026 |
| The Reserve at Belmere | Guard-staffed+ resident gate | 359 | — | Lake Whitney, Lake Rhea (not on the chain) | $2,662 / yearListing, Sep 30, 2026 |
| Casabella | Guard-staffed | 79 | — | — | $1,612 / quarterListing, Aug 7, 2026 |
| Bellaria | Guard-staffed | 64 | — | Pond | $1,450 / quarterListing, Jul 20, 2026 |
| Tildens Grove | Guard-staffed | 139 | — | Lake William DavisBroker page | $3,560 / yearSale, Sep 12, 2025 |
| Waterford Pointe | Guard-staffed | 76 | — | Lake Roberts | $325 / monthListing, Aug 31, 2026 |
| Belmere Village | ElectronicNo guard: Andy Neal and MLS, Nov 2026 | 397Incl. Whitney Isles | — | Ponds | Not found |
| Chaine du Lac | ElectronicNot staffed; visitors show ID at the gate | 33+ 3 vacant lots · in the Town | — | Lake Butler | $1,900 / quarterListing, Sep 3, 2026 |
| Butler Bay / Windermere Club | Electronic | 181Unit 1 in the Town | — | Lake Butler | $2,385 / yearListing, Oct 2026 |
| Glenmuir | ElectronicNot staffed; code entry | 229 | — | Ponds | $140 / monthListing, Apr 2026 |
| Windermere Reserve | ElectronicNo guard, broker page | ~30 | — | Lake Down (9 homes) | Not found |
| Estates at Windermere | ElectronicNot staffed; code entry | 66 | — | — | Not found |
| Windermere Downs | Not gatedBeach lot gated only | 204 | — | Lake Down (HOA beach lot) | Not published |
| Lake Burden South | Not gated | — | — | Lake Burden (not on the chain) | $278 / quarterListing, Oct 2026 |
| Windermere Sound | Not gatedAndy Neal, Oct 2026 | 295 | — | — | Not found |
| Lake Down Crest | Not gatedAndy Neal, Oct 2026 | 31 | — | Lake Down views | Not found |
Gate: Stellar MLS fields on dated listings (August to October 2026) or a broker page where marked; Glenmuir, Chaine du Lac, Estates at Windermere, Windermere Sound and Lake Down Crest: Andy Neal, October 2026. Homes: Orange County parcel data by plat (October 22, 2026); Isleworth: Andy Neal (November 2026); Windermere Reserve is a broker estimate. HOA: one listing's figure, not a budget; confirm for each home.
Homes for sale behind the gates.
The newest homes for sale in the gated communities above, from $350,000. They come straight from the MLS feed and update on their own.
Current homes for sale in Windermere's gated communities appear here.
See Windermere homes for saleListings courtesy of Stellar MLS as distributed by MLS GRID. Some IDX listings have been excluded from this website. IDX information is provided for consumers' personal, non-commercial use, is deemed reliable but is not guaranteed by MLS GRID, and each listing shows its listing brokerage, MLS number and status. Presented by Andy Neal, REALTOR®, The Agency FL, (407) 619-3517.
Two kinds of gate, two ways in.
The MLS records every gated community as one or the other. Here's what each means when you, a guest or a delivery driver arrives.
Guard-staffed gate
- MLS field
- "Gated Community - Guard"
- Visitors
- Checked in at a staffed gatehouse; Lake Butler Sound and The Reserve at Belmere ask visitors for photo ID
- Residents
- A resident lane or app: key-card entry at The Reserve at Belmere, a Gate Access app and guest lists at Isleworth
- Examples
- Isleworth, Keene's Pointe, Lake Butler Sound, The Reserve at Belmere, Casabella
Electronic gate
- MLS field
- "Gated Community - No Guard"
- Visitors
- A call box, video intercom or code from the resident; at Chaine du Lac, visitors show ID at the gate machine
- Residents
- Code, fob or phone: Chaine du Lac residents open the gate from a smartphone
- Examples
- Chaine du Lac, Butler Bay / Windermere Club, Glenmuir, Estates at Windermere
- Guests and showingsEvery visit needs the gate's OK: a name on the guest list or a call to the resident. Plan showings ahead.MLS directions; association gate systems
- Deliveries and contractorsEach association sets how couriers, movers and trades are cleared. None publishes it, so ask for the gate rules with the HOA documents.Checked October 2026
- Private roadsHOA dues usually pay for the roads. The county enforces traffic rules on private roads only under a written agreement with the owner.F.S. 316.006(3)(b)
Sources: Stellar MLS listing records (Lake Butler Sound O6443650, October 22, 2026; The Reserve at Belmere O6406297, October 2026); Florida Neighborhood Realty, The Reserve at Belmere (May 4, 2026); Isleworth Community Association resident site (accessed October 2026); ButterflyMX, Chaine du Lac (July 27, 2026); Andy Neal, October 2026 (Chaine du Lac visitor ID); Florida Statutes 316.006 (2026).
Each gated community, in brief.
The four with a full guide first, then the others, each linked to Andy's own write-up where there is one.
Isleworth
About 600 acres on six chain lakes, around the private Isleworth Golf & Country Club.
Isleworth guide · Homes for saleKeene's Pointe
About 1,055 homes on 11 plats, two staffed entrances, and the Nicklaus-designed Golden Bear Club.
Keene's Pointe guide · Homes for saleLake Butler Sound
213 homes on two plats off Chase Road; lots up to 4.78 acres, the largest on Lake Butler.
Lake Butler Sound guideThe Reserve at Belmere
359 homes off Maguire Road, around 40-acre Lake Whitney and 11-acre Lake Rhea.
Reserve at Belmere guideCasabella
79 homes on two plats, built by Toll Brothers; lots of about half an acre to 0.88 acre.
Andy's Casabella postChaine du Lac
33 homes and 3 lots on Lake Butler, annexed into the Town of Windermere in February 2025.
Andy's Chaine du Lac postGlenmuir
229 homes on two plats; the gate isn't staffed, and entry is by code.
Andy's Glenmuir postWaterford Pointe
76 homes, with community access to Lake Roberts.
Andy's Waterford Pointe postTildens Grove
139 homes on two plats; listings describe a 24-hour staffed gate.
Tildens Grove listingsEstates at Windermere
66 homes built by Park Square, 1997 to 2002, with a single gated entrance on McKinnon Road: not staffed, entry by code.
Andy's Estates postWindermere Downs
204 homes with two open entrances; only the HOA's Lake Down beach lot is gated.
Andy's Windermere Downs postHomes: Orange County parcel data (October 22, 2026). Builders and entrances: Toll Brothers (GrowthSpotter, 2019); Florida Neighborhood Realty, Estates at Windermere and Windermere Downs (May 2026). Chaine du Lac annexation: Orange Observer, February 5, 2025. Isleworth acreage: Isleworth Golf & Country Club. Gates at Glenmuir and Estates at Windermere: Andy Neal, October 2026.
What the gate costs each year.
Listings quote HOA dues by the month, the quarter or the year. Here each example is turned into a yearly figure, so they compare fairly.
HOA example per year, by community
One listing's figure each, annualized (monthly × 12, quarterly × 4). Not the association's budget.
Show the numbers
| Community | As listed | Per year | Listing date |
|---|---|---|---|
| Isleworth | $3,672 / quarter | $14,688 | Jul 30, 2026 |
| Lake Butler Sound | $637 / month | $7,644 | Oct 2026 |
| Chaine du Lac | $1,900 / quarter | $7,600 | Sep 3, 2026 |
| Casabella | $1,612 / quarter | $6,448 | Aug 7, 2026 |
| Bellaria | $1,450 / quarter | $5,800 | Jul 20, 2026 |
| Waterford Pointe | $325 / month | $3,900 | Aug 31, 2026 |
| Keene's Pointe | $3,578 / year | $3,578 | Aug–Sep 2026 |
| Tildens Grove | $3,560 / year | $3,560 | Sep 12, 2025 |
| The Reserve at Belmere | $2,662 / year | $2,662 | Sep 30, 2026 |
| Butler Bay / Windermere Club | $2,385 / year | $2,385 | Oct 2026 |
| Glenmuir | $140 / month | $1,680 | Apr 2026 |
Per-listing HOA fields, Stellar MLS records as shown on Bex Realty, Coldwell Banker, Weichert, Florida Neighborhood Realty and Real Geeks listing pages (dates above). Club dues, where there is a club, are extra.
- What listings say the dues coverGate staffing, private roads, common grounds and reserves; some add cable and internet (Isleworth, Butler Bay)
- Club membership is separateIsleworth Golf & Country Club and the Golden Bear Club set their own fees, apart from the HOA
- Several fees can stackSome homes pay a master HOA plus a sub-association; the Gardens of Isleworth lists two quarterly fees
- Taxes follow the Town line, not the gateMost gated communities are unincorporated; Chaine du Lac and Butler Bay Unit 1 are in the Town, with different millage
- The exact figure comes from the estoppel certificateThe association must issue it within 10 business days (F.S. 720.30851)
Often asked: is it gated?
The Town of Windermere
An incorporated town of about 2.2 square miles with public streets. Gated communities sit around it, mostly outside its limits.
Town of WindermereWindermere Downs
Two open entrances, off Park Ridge Gotha Road and Hempel Avenue. Only the HOA's Lake Down beach lot is gated.
Florida Neighborhood Realty, May 2026Windermere Sound and Lake Down Crest
Neither is gated, though some broker pages describe a keypad or fob gate. Windermere Sound has 295 homes; Lake Down Crest has 31.
Andy Neal, October 2026; Orange County parcel dataBay Hill
No single gate. Some enclaves, such as Emerson Pointe, Isle of Osprey and Bay Point, are gated. Orlando 32819.
Listing records, October 2026Buying in a gated community.
- Get the HOA disclosure summary
It must come before you sign. If it doesn't, you can cancel within 3 days of receiving it, or before closing.
F.S. 720.401 - Read the documents online
Associations with 100 or more parcels must post the declaration, rules, budget and insurance on an owner website or app.
F.S. 720.303(4)(b), since January 1, 2025 - Order the estoppel certificate
Issued within 10 business days; it states the dues and anything else owed to the association.
F.S. 720.30851 - Check the rental rules
A rental limit adopted after July 1, 2021 binds only later buyers, except limits on leases under 6 months or more than 3 a year.
F.S. 720.306(1)(h) - Ask about the club separately
Golf and social membership is its own application and its own fees, apart from buying the home.
Isleworth; Golden Bear Club
-
Ask how the gate works for this homeStaffed, code or intercom: the ledger above, checked with Andy in October 2026
-
Ask how guests, deliveries and contractors get inRules differ by community and aren't published
-
Check whether the home is in the TownProperty Appraiser "Municipality" field; Chaine du Lac and Butler Bay Unit 1 are
-
On the water, check the lakeLake Whitney and Lake Burden aren't on the Butler Chain
-
Price the insurance earlySee the flood and insurance notes in the Windermere guide
Florida Statutes 720.303, 720.30851, 720.306 and 720.401 (2026). Estoppel fee caps in the statute are $250, plus $100 for rush and $150 if dues are late; DBPR's 2022 inflation adjustment raised them to $299, $119 and $179 (Shumaker client alert, July 25, 2022).
Notes from Andy.
I show my license at the gate, or the seller adds us to the guest list before the showing.Andy Neal · REALTOR®, The Agency FL · #1 in Windermere, RealTrends Verified 2025 · FL Lic. SL3396613
Two weeks after meeting Andy, he showed my wife and I a home that had not yet hit the market. Three days later, we were under contract.
Gated, on the lake, or both?
Windermere homes for sale
Every Windermere home for sale from $350,000, gated or not.
See homesLakefront on the Butler Chain
Lake by lake, with the docks, permits and flood checks that come with them.
Lakefront homesThe Windermere guide
The Town vs the 34786 address, the lakes, taxes and flood checks.
Read the guideWindermere gated communities, answered.
01Is Windermere, FL a gated community?
No. Windermere is an incorporated town of about 2.2 square miles, and most homes with a Windermere 34786 address are in unincorporated Orange County around it. Inside that area are separate gated communities, such as Isleworth, Keene's Pointe, Lake Butler Sound and The Reserve at Belmere, each with its own gate and HOA.
02Which Windermere gated communities have a staffed guard gate?
Listings from 2025 and 2026 record a staffed gate at Isleworth, Keene's Pointe, Lake Butler Sound, The Reserve at Belmere, Casabella, Bellaria, Tildens Grove and Waterford Pointe. Belmere Village, Chaine du Lac, Butler Bay, Glenmuir, Windermere Reserve and Estates at Windermere have electronic gates with no guard. Windermere Sound and Lake Down Crest aren't gated.
03What's the difference between guard-gated and gated?
A guard-gated community has a staffed gatehouse where visitors are checked in, often with photo ID. A gated community without a guard uses an electronic gate: a call box, video intercom, code or fob. Florida MLS listings record this as "Gated Community - Guard" or "Gated Community - No Guard." Neither changes who may buy a home there.
04What is the biggest gated community in Windermere?
By number of homes, Keene's Pointe, with about 1,055 homes on 11 plats, per Orange County parcel data from October 2026. Belmere Village (about 397, including Whitney Isles) and The Reserve at Belmere (359) come next. Isleworth has about 331 homes on about 600 acres.
05How much are HOA fees in Windermere gated communities?
In 2025 and 2026 listings, examples run from $140 a month at Glenmuir and $2,662 a year at The Reserve at Belmere to $637 a month at Lake Butler Sound and $3,672 a quarter at Isleworth. Dues are billed monthly, quarterly or yearly, so compare them by the year, and confirm the figure on the estoppel certificate.
06Which gated communities in Windermere have golf courses?
Two: Isleworth, with the private Isleworth Golf & Country Club, and Keene's Pointe, home to the Jack Nicklaus-designed Golden Bear Club. In both, club membership is separate from the HOA, with its own application and fees. Bay Hill Club & Lodge is nearby in Orlando 32819.
07Which gated communities are on the Butler Chain of Lakes?
Isleworth, Keene's Pointe (on Lake Tibet-Butler and Lake Isleworth), Lake Butler Sound, Chaine du Lac and Butler Bay sit on the Butler Chain. The Reserve at Belmere's Lake Whitney and Keene's Pointe's Lake Burden aren't part of the chain, so check each home's frontage and boat access.
08Is Windermere Downs a gated community?
No. Windermere Downs has two open entrances, off Park Ridge Gotha Road and Hempel Avenue. Its one gated feature is the HOA's beach lot on Lake Down, with a beach, dock and boat ramp for members.
09How do guests and deliveries get through the gate?
At a staffed gate, a resident adds the guest's name to a list or the guard calls the resident, and visitors may be asked for photo ID. Electronic gates use a call box, intercom or code. Each association sets its own rules for couriers, movers and contractors, so ask for them with the HOA documents.
10Can a gated community's HOA restrict renting out my home?
Yes, if its documents allow it, but Florida limits new rules. A rental restriction adopted after July 1, 2021 generally binds only owners who buy after it passes, or who agree to it. Limits on leases shorter than six months, or more than three a year, can apply to everyone (F.S. 720.306).
11Where can I read a gated community's HOA documents before I buy?
Ask for them with your offer. Florida HOAs with 100 or more parcels must post the declaration, bylaws, rules, budget and insurance policies on an owner website or app, and the seller must give you the HOA disclosure summary before you sign the contract.
Which gate fits you?
Tell Andy what matters: a staffed gate, golf, the lake, or a lower HOA. He'll compare the communities with you and arrange gate access for showings.
Talk with Andy
A short note is enough. Andy replies personally.
Andy Neal, Realtor · The Agency FL · (407) 619-3517
Sources and how we compiled this page Updated October 2026 · 16 sources
How we compiled it
Gate type comes from the Stellar MLS "Gated Community" field on dated listings, or a broker page where the ledger says so. Andy Neal confirmed in October and November 2026 that Glenmuir, Chaine du Lac, Estates at Windermere and Belmere Village have unstaffed gates, and that Windermere Sound and Lake Down Crest aren't gated.
Home counts are Orange County residential parcels with a home. HOA examples are single listings, not budgets. Confirm anything you rely on with the association or with Andy.
- Orange County GIS, Subdivision and Parcels layers (queried October 22, 2026)
- Stellar MLS listing records via Bex Realty: Casabella MFRO6430081, Bellaria MFRW7887812, Tildens Grove MFRO6287129, Chaine du Lac MFRO6381869, Glenmuir MFRO6390271, Butler Bay MFRO6420023 ($2,590 a year, sold October 13, 2026), The Reserve at Belmere MFRO6445423, Lake Butler Sound MFRO6447314 (August to October 2026)
- Stellar MLS listing records via Coldwell Banker (Isleworth O6427447; Waterford Pointe), Weichert (Lake Butler Sound O6443650) and Real Geeks (Reserve at Belmere O6406297; Glenmuir O6398505; Lake Burden South O6432932; Isleworth West O6430931), 2026
- Florida Neighborhood Realty community pages: Reserve at Belmere (May 4, 2026), Belmere Village (April 30, 2026), Windermere Club (May 2026), Windermere Downs (May 2026), Windermere Reserve (May 2026), Estates at Windermere (May 2, 2026), Tildens Grove (May 2026), Glenmuir (May 2026); Butler Bay listing O6413242 ($2,385 a year, October 2026)
- Andy Neal, The Agency FL: gate status for Glenmuir, Chaine du Lac, Estates at Windermere, Windermere Sound and Lake Down Crest (October 2026)
- ButterflyMX, Chaine du Lac case study (updated July 27, 2026)
- Isleworth Community Association resident site, isleworthresidents.com (accessed October 2026)
- Isleworth Golf & Country Club (about 600 acres); The Golden Bear Club membership page (accessed October 2026)
- The Funk Collection, Keene's Pointe vs Isleworth (August 21, 2026): Keene's Pointe's two staffed entrances
- Town of Windermere, Information page (accessed October 2026)
- Orange Observer, Chaine du Lac annexation (February 5, 2025)
- GrowthSpotter, Toll Brothers' Casabella (October 28, 2019); Bex Realty Casabella community page, lot sizes (October 2026)
- Florida Statutes 316.006, 720.303, 720.30851, 720.306 and 720.401 (2026)
- Shumaker, DBPR estoppel fee adjustment (July 25, 2022)
- Bay Hill enclaves: listing record O6439456, Emerson Pointe (October 2026)
- Andy Neal's community posts on centralfloridalistings.co (linked on this page)
Andy Neal, Realtor, The Agency FL · 4757 The Grove Dr, Suite 124, Windermere, FL 34786 · (407) 619-3517 · Florida Sales Associate, Lic. SL3396613.
The Agency FL (H2 Collective LLC d/b/a The Agency FL), a Florida-licensed real estate brokerage, Lic. CQ1073923. Equal Housing Opportunity.
Information on this page is for general guidance and was checked in October 2026; it isn't legal, tax or insurance advice. A gate is an access-control feature of a community, not a promise about anything else. HOA figures are examples from single listings.
