Golf Course Homes for Sale in Winter Haven, FL
This page tracks every Winter Haven 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.
46 homes in golf communities are for sale or pending in Winter Haven, FL today across 22 communities. The median asking price is $322,500, from $119,000 to $879,000. Listings in Winter Haven without that feature have a median of $283,990. Most listings right now: Lake Ashton West Ph 01 (11), Cypresswood (5), Cypresswood Enclave Ph 01 (4). Updated September 28, 2026 from the MLS.
Live golf community homes in Winter Haven: the listings
90 active listings carry the flag today (12% of Winter Haven inventory), median asking $220,000, $161/sq ft, median 54 days on market. Photo cards link to the listing; refreshed nightly.
Newest golf community homes in Winter Haven
The most expensive golf community homes in Winter Haven
| Listing | Asking | Sq ft | Community |
|---|---|---|---|
| 9513 Waterford Oaks Boulevard | $750,000 | 3,611 | — |
| 4040 Palma Ceia Circle | $749,000 | 2,493 | Cypresswood Palma Ceia |
| 5365 Hogan Lane | $599,900 | 2,591 | — |
| 5268 Pebble Beach Boulevard | $579,900 | 2,354 | — |
| 6261 Pinehurst Loop | $565,000 | 2,512 | — |
| 6136 Pebble Beach Boulevard | $549,999 | 2,682 | — |
| 4 Casarena Court | $524,000 | 3,911 | — |
| 3158 Beauchamp Court | $484,900 | 2,552 | — |
| 315 Lanceolate Drive | $469,000 | 2,153 | — |
| 1814 Sandhill Lane | $462,000 | 2,550 | — |
Golf Community Homes by price
| Band | For sale | Share |
|---|---|---|
| Under $300K | 58 | 64% |
| $300K–$500K | 25 | 28% |
| $500K–$750K | 6 | 7% |
| $750K–$1M | 1 | 1% |
Winter Haven golf course homes by community
Click a community for its full guide: prices, HOA reality, insurance posture and the homes for sale.
| Community | Golf Course Homes | New build | Median list | From |
|---|---|---|---|---|
| Lake Ashton West Ph 01 | 11 | 0 | $335,000 | $279,900 |
| Cypresswood | 5 | 0 | $249,900 | $190,000 |
| Cypresswood Enclave Ph 01 | 4 | 0 | $219,950 | $214,900 |
| Eagle Pond Condo | 4 | 0 | $167,450 | $162,000 |
| Lake Ashton West Ph Ii North | 3 | 0 | $549,999 | $444,000 |
| Cypresswood Palma Ceia | 2 | 1 | $814,000 | $749,000 |
| Lake Ashton West Ph Ii South | 2 | 0 | $388,999 | $355,000 |
| Cypresswood Plantations | 1 | 0 | $484,900 | $484,900 |
| Lake Ashton West Ph 2 South | 1 | 0 | $449,900 | $449,900 |
| Lake Bess Country Club | 1 | 0 | $349,999 | $349,999 |
| Cypresswood Fairway Patio Homes | 1 | 0 | $337,000 | $337,000 |
| Cypresswood Mdws | 1 | 0 | $334,990 | $334,990 |
| Cypresswood Golf Villas Gc-2 | 1 | 0 | $270,000 | $270,000 |
| Cypresswood Patio Homes | 1 | 0 | $230,000 | $230,000 |
| Cypresswood Villas/Green Bldg | 1 | 0 | $229,000 | $229,000 |
| Cypresswood Golf Villas Gi-4 | 1 | 0 | $180,000 | $180,000 |
| Cypresswood Villas/Green | 1 | 0 | $172,500 | $172,500 |
| Cypresswood Villas On The Green | 1 | 0 | $169,000 | $169,000 |
| Cypresswood Tennis Villas | 1 | 0 | $165,000 | $165,000 |
| Cypresswood Tennis Vls | 1 | 0 | $165,000 | $165,000 |
| Cypresswood Golf Villas | 1 | 0 | $122,000 | $122,000 |
| Carefree Rv Country Club | 1 | 0 | $119,000 | $119,000 |
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 Winter Haven?
What do golf course homes cost in Winter Haven?
Which Winter Haven community has the most golf course homes for sale?
Do I have to join the golf club if I buy in a golf community?
Keep exploring Winter Haven
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- Golf Course Homes in every city
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 Winter Haven, 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.