Golf Course Homes for Sale in Windermere, FL

This page tracks every Windermere listing whose MLS record reports a golf course or golf-club community, by community, with live counts and asking prices, and the membership and fee questions that decide what a golf-community home really costs.

39 homes in golf communities are for sale or pending in Windermere, FL today across 10 communities. The median asking price is $3,999,000, from $940,000 to $19,500,000. Listings in Windermere without that feature have a median of $777,450. Most listings right now: Isleworth (19), Keenes Pointe (12), Isleworth Amd 03 (1). Updated September 28, 2026 from the MLS.

Live golf community homes in Windermere: the listings

43 active listings carry the flag today (19% of Windermere inventory), median asking $3,800,000, $819/sq ft, median 50 days on market. Photo cards link to the listing; refreshed nightly.

Newest golf community homes in Windermere

5192 Vardon Drive, golf community for sale in Windermere
$19,500,000 New
6 bd · 9 ba · 13,494 sq ft · built 2006
5192 Vardon Drive, 34786
Listing courtesy of IRWIN REALTY GROUP LLC
9343 Tibet Pointe Circle, golf community for sale in Windermere
$7,450,000 New
7 bd · 9 ba · 8,362 sq ft · built 2004
9343 Tibet Pointe Circle, 34786
Listing courtesy of NOVA REAL ESTATE SERVICES INC
5373 Isleworth Country Club Drive, golf community for sale in Windermere
$7,200,000 New
5 bd · 5.5 ba · 5,993 sq ft · built 1988
5373 Isleworth Country Club Drive, 34786
Isleworth
Listing courtesy of STOCKWORTH REALTY GROUP
5524 Worsham Court, golf community for sale in Windermere
$3,500,000 New
4 bd · 6 ba · 7,669 sq ft · built 1987
5524 Worsham Court, 34786
Isleworth
Listing courtesy of ATLIS REALTY GROUP LLC
5050 Isleworth Country Club Drive, golf community for sale in Windermere
$3,189,000 New
4 bd · 4.5 ba · 3,365 sq ft · built 1987
5050 Isleworth Country Club Drive, 34786
Isleworth
Listing courtesy of COMPASS FLORIDA LLC
6102 S Hampshire Ct, golf community for sale in Windermere
$2,240,000 New
4 bd · 5.5 ba · 4,812 sq ft · built 2002
6102 S Hampshire Ct, 34786
Keenes Pointe
Listing courtesy of SOUTHERN REALTY GROUP LLC
5036 Latrobe Drive, golf community for sale in Windermere
$18,750,000 New
6 bd · 8 ba · 15,337 sq ft · built 2027
5036 Latrobe Drive, 34786
Isleworth
Listing courtesy of ISLEWORTH REALTY LLC
8142 Tibet Butler Drive, golf community for sale in Windermere
$2,685,000 New
5 bd · 6.5 ba · 5,747 sq ft · built 2003
8142 Tibet Butler Drive, 34786
Keenes Pointe
Listing courtesy of STOCKWORTH REALTY GROUP
9921 Lake Louise Drive, golf community for sale in Windermere
$6,650,000 New
5 bd · 6 ba · 6,970 sq ft · built 2003
9921 Lake Louise Drive, 34786
Isleworth
Listing courtesy of ISLEWORTH REALTY LLC
101 Lee Street, golf community for sale in Windermere
$1,395,000
5 bd · 4 ba · 4,186 sq ft · built 1978
101 Lee Street, 34786
Windermere Town
Listing courtesy of STOCKWORTH REALTY GROUP
8342 Boyla Court, golf community for sale in Windermere
$6,700,000
8 bd · 8.5 ba · 8,133 sq ft · built 2026
8342 Boyla Court, 34786
Keenes Pointe
Listing courtesy of THE SIMON SIMAAN GROUP
9316 Gladys Garden Ct, golf community for sale in Windermere
$6,500,000
5 bd · 6.5 ba · 5,471 sq ft · built 2026
9316 Gladys Garden Ct, 34786
Isleworth
Listing courtesy of ISLEWORTH REALTY LLC
6119 Grosvenor Shore Drive, golf community for sale in Windermere
$15,900,000
8 bd · 9.5 ba · 14,068 sq ft · built 2014
6119 Grosvenor Shore Drive, 34786
Keenes Point
Listing courtesy of PREMIER SOTHEBY'S INTL. REALTY
9904 Brentford Court, golf community for sale in Windermere
$2,250,000
5 bd · 4.5 ba · 4,504 sq ft · built 2000
9904 Brentford Court, 34786
Keenes Pointe
Listing courtesy of LAKESIDE REALTY WINDERMERE INC
9317 Gladys Garden Court, golf community for sale in Windermere
$7,999,000
6 bd · 7.5 ba · 8,038 sq ft · built 2027
9317 Gladys Garden Court, 34786
Gardens/Isleworth
Listing courtesy of CORCORAN PREMIER REALTY
6288 Blakeford Drive, golf community for sale in Windermere
$2,474,000
5 bd · 5.5 ba · 5,366 sq ft · built 2003
6288 Blakeford Drive, 34786
Keenes Pointe
Listing courtesy of NECTAR REAL ESTATE
6719 Valhalla Way, golf community for sale in Windermere
$4,495,000
5 bd · 6 ba · 6,159 sq ft · built 2007
6719 Valhalla Way, 34786
Keenes Pointe
Listing courtesy of CELEBRITY GLOBAL REALTY LLC
6055 Louise Cove Drive, golf community for sale in Windermere
$6,900,000
5 bd · 5.5 ba · 7,158 sq ft · built 2001
6055 Louise Cove Drive, 34786
Isleworth West
Listing courtesy of STOCKWORTH REALTY GROUP
2009 Woody Drive, golf community for sale in Windermere
$1,150,000
4 bd · 3 ba · 3,540 sq ft · built 1974
2009 Woody Drive, 34786
Windermere Downs
Listing courtesy of REVEL REALTY LLC
5199 Latrobe Dr, golf community for sale in Windermere
$5,300,000
6 bd · 6.5 ba · 4,665 sq ft · built 1993
5199 Latrobe Dr, 34786
Isleworth
Listing courtesy of ISLEWORTH REALTY LLC
8344 Bowden Way, golf community for sale in Windermere
$1,065,000
4 bd · 4 ba · 3,646 sq ft · built 2002
8344 Bowden Way, 34786
Keenes Pointe
Listing courtesy of ALIGN REAL ESTATE LLC
9349 Tibet Pointe Circle, golf community for sale in Windermere
$6,995,000
5 bd · 7 ba · 7,529 sq ft · built 2003
9349 Tibet Pointe Circle, 34786
Keenes Pointe
Listing courtesy of CORCORAN PREMIER REALTY
11027 Hawkshead Court, golf community for sale in Windermere
$1,549,000
5 bd · 3.5 ba · 3,486 sq ft · built 2003
11027 Hawkshead Court, 34786
reserve at lake butler sound
Listing courtesy of KENNEDY REALTY GROUP LLC
9832 Laurel Valley Drive, golf community for sale in Windermere
$11,750,000
6 bd · 8.5 ba · 11,100 sq ft · built 2004
9832 Laurel Valley Drive, 34786
Isleworth
Listing courtesy of REAL BROKER, LLC
5073 Latrobe Dr, golf community for sale in Windermere
$2,800,000
4 bd · 5 ba · 4,706 sq ft · built 1989
5073 Latrobe Dr, 34786
Isleworth
Listing courtesy of ISLEWORTH REALTY LLC
6462 Deacon Cir, golf community for sale in Windermere
$6,595,000
5 bd · 5 ba · 7,178 sq ft · built 1990
6462 Deacon Cir, 34786
Isleworth
Listing courtesy of ISLEWORTH REALTY LLC
6124 Foxfield Court, golf community for sale in Windermere
$1,250,000
4 bd · 3 ba · 2,887 sq ft · built 2001
6124 Foxfield Court, 34786
Keenes Pointe
Listing courtesy of JULIAN PROPERTIES, INC.
8525 Bowden Way, golf community for sale in Windermere
$940,000
4 bd · 3 ba · 2,357 sq ft · built 2000
8525 Bowden Way, 34786
Keenes Pointe
Listing courtesy of SOUTHERN REALTY GROUP LLC
5138 Fairway Oaks Dr, golf community for sale in Windermere
$4,999,500
4 bd · 5 ba · 4,330 sq ft · built 1994
5138 Fairway Oaks Dr, 34786
Isleworth
Listing courtesy of ISLEWORTH REALTY LLC
9144 Isleworth Gardens Drive, golf community for sale in Windermere
$4,100,000
3 bd · 4 ba · 5,004 sq ft · built 2019
9144 Isleworth Gardens Drive, 34786
Isleworth
Listing courtesy of MEGAN DOWDY REALTY, LLC

The most expensive golf community homes in Windermere

ListingAskingSq ftCommunity
5192 Vardon Drive$19,500,00013,494—
5036 Latrobe Drive$18,750,00015,337Isleworth
6119 Grosvenor Shore Drive$15,900,00014,068Keenes Point
9832 Laurel Valley Drive$11,750,00011,100Isleworth
9317 Gladys Garden Court$7,999,0008,038Gardens/Isleworth
9343 Tibet Pointe Circle$7,450,0008,362—
5373 Isleworth Country Club Drive$7,200,0005,993Isleworth
9349 Tibet Pointe Circle$6,995,0007,529Keenes Pointe
6055 Louise Cove Drive$6,900,0007,158Isleworth West
8342 Boyla Court$6,700,0008,133Keenes Pointe

Golf Community Homes by price

BandFor saleShare
$750K–$1M12%
$1M+4298%

Windermere golf course homes by community

Click a community for its full guide: prices, HOA reality, insurance posture and the homes for sale.

CommunityGolf Course HomesNew buildMedian listFrom
Isleworth192$3,800,000$2,900,000
Keenes Pointe121$2,579,500$940,000
Isleworth Amd 0310$19,500,000$19,500,000
Keenes Point10$15,900,000$15,900,000
Isleworth 5Th Amd10$12,350,000$12,350,000
Gardens/Isleworth11$7,999,000$7,999,000
Keenes Pointe Unit 03 46/10410$7,450,000$7,450,000
Isleworth West10$6,900,000$6,900,000
Keenes Pointe 46/10410$4,495,000$4,495,000
Keene'S Pointe10$1,795,000$1,795,000

Golf community costs: membership is the number to get first

Three kinds of golf community exist and the price of a home tells you nothing about which one you are looking at: mandatory-membership clubs (an initiation fee, often five figures, plus monthly dues, both required at closing), optional-membership clubs (the course is private but the home does not require joining) and public or semi-private courses where the community simply borders the fairways. Ask the listing agent for the current membership schedule in writing, whether an initiation fee is refundable or equity-based, and whether a capital assessment is pending on the clubhouse. Add HOA and, in many newer Florida golf communities, a CDD bond that shows up on the tax bill. Our true cost of ownership calculator puts dues, taxes and insurance into one monthly number.

Questions to ask about any golf-community listing

Is membership mandatory, and what are the initiation fee and monthly dues today? Is the club member-owned or developer-owned, and is a turnover or assessment scheduled? Which holes border the lot, and has the seller had errant-ball damage claims? Is there a CDD, and how many years remain on the bond? What did the seller pay in total (HOA + club + CDD) last year? A local agent who works these communities will know which clubs are financially healthy.

Common questions

How many homes in golf communities are for sale in Windermere?
As of September 28, 2026, 39 Windermere, FL listings whose MLS record reports a golf course or golf-club community are active or pending, across 10 communities. The count updates with every MLS refresh.
What do golf course homes cost in Windermere?
The median asking price today is $3,999,000, with listings from $940,000 to $19,500,000. Windermere listings without that feature have a median of $777,450.
Which Windermere community has the most golf course homes for sale?
Isleworth has the most right now (19), followed by Keenes Pointe (12), Isleworth Amd 03 (1), Keenes Point (1).
Do I have to join the golf club if I buy in a golf community?
Only in mandatory-membership communities, where joining is a condition of purchase and the fees are due at closing. Many Florida and Georgia golf communities make membership optional or are built around public courses. The community's governing documents and the club's current fee schedule answer it for a specific home; get both before you offer.

Keep exploring Windermere

Live data: Stellar MLS, refreshed with every MLS pull; this page rebuilds on every ship. Community-level aggregates only: active and pending residential listings in Windermere, FL whose MLS record reports a golf course or golf-club community. Prices are asking prices, not values. Property features and prices only; nothing on this page describes residents. Equal Housing Opportunity.

Listings courtesy of Stellar MLS as distributed by MLS GRID.

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