Golf Course Communities in Winter Garden, FL

Looking for golf course communities in Winter Garden, FL? Momentum tracks 44 Winter Garden communities with evidence of golf community living, each with MLS-derived pricing and market pace below — plus the local questions worth asking before you buy, and a direct line to an agent who works these communities.

Winter Garden golf course communities at a glance

Communities tracked

$594,000

Median sale price

66 days

Median days on market

528

Recent closings

The communities, by recent sales activity

Community	City	Median price	1-yr change	Days on mkt
Waterleigh · agent	Winter Garden	$722,000	–	33 d
Serenade at Ovation · agent	Winter Garden	$440,000	–	35 d
Stoneybrook West · agent	Winter Garden	$652,000	–	36 d
SIGNATURE LAKES · agent	Winter Garden	$520,000	–	50 d
HICKORY HAMMOCK · agent	Winter Garden	$908,000	–	26 d
Oakland Park · agent	Winter Garden	$1.01M	–	65 d
DEL WEBB OASIS · agent	Winter Garden	$419,000	–	35 d
SILVERLEAF RESERVE · agent	Winter Garden	$839,000	–	106 d
WEST LAKE HANCOCK ESTATES · agent	Winter Garden	$705,000	–	16 d
JOHNS LAKE POINTE · agent	Winter Garden	$694,000	–	20 d
LAKEVIEW POINTE/HORIZON WEST P · agent	Winter Garden	$539,000	–	43 d
STONEYBROOK WEST 44/134 · agent	Winter Garden	$640,000	–	94 d
STONEYBROOK WEST D · agent	Winter Garden	$568,000	–	–
LAKE COVE POINTE · agent	Winter Garden	$842,000	–	–
PANTHER VIEW · agent	Winter Garden	$554,000	–	1 d
HERITAGE/PLANT STREET · agent	Winter Garden	$621,000	–	–
SIGNATURE LKS-PCL 01B · agent	Winter Garden	$464,000	–	–
OAKS/BRANDY LAKE O · agent	Winter Garden	$530,000	–	–
ISLAND POINTE SUB · agent	Winter Garden	$465,000	–	86 d
SUMMERLAKE GRVS · agent	Winter Garden	$560,000	–	48 d
COVINGTON PARK A B D E F G & J · agent	Winter Garden	$540,000	–	–
LAKEVIEW RESERVE 46/149 · agent	Winter Garden	$594,000	–	137 d
WINTER OAKS · agent	Winter Garden	$678,000	–	1 d
TILDEN PLACE/WINTER GARDEN · agent	Winter Garden	$885,000	–	237 d
STONEYBROOK WEST I · agent	Winter Garden	$365,000	–	13 d

Communities are listed by recent closing volume in Momentum’s MLS data. Figures are aggregates, change over time, and are deemed reliable but not guaranteed.

Every other tracked golf course communities in Winter Garden

Membership, fees and what “golf community” actually means

Golf communities range from public-course neighborhoods with no obligations to bundled-golf communities where equity membership is mandatory and priced into every sale. Before you offer, get the fee stack in writing: HOA dues, club or membership minimums, food-and-beverage minimums, cart fees, and any CDD assessment on the tax bill. Ask whether membership is mandatory, optional, or waitlisted, and what the initiation fee runs. A bundled-golf bargain can stop being a bargain once the full stack is on paper.

Resale considerations in golf communities

Course health matters to resale: a closed or struggling course next to your lot changes the value story. Ask how the course is funded, whether the club is member-owned or developer-owned, and whether any redevelopment litigation exists. Homes on the course trade at premiums that vary hole by hole — comps from the same street matter more here than anywhere.

What it costs to own here

At Orange County’s typical combined millage of 16.67 mills, a purchase at $594,000 (the median across these Winter Garden golf course communities) generates roughly $9,904 a year in property tax before exemptions — about $825 a month. Florida resets the assessed value to roughly your purchase price, so the seller’s current bill is not a preview of yours; a homesteaded owner then gets the $25,000–$50,000 exemption and the 3% Save Our Homes cap going forward. Citizens Property Insurance policies in Orange County average about $1,409 a year ($117 a month) — private-market quotes vary with roof age and wind mitigation, so price coverage before your inspection window closes. All-in, our county model puts the typical monthly cost of ownership in Orange County near $2,402 (principal and interest on the typical home, tax, and insurance).

Run your exact numbers: the property tax after purchase calculator uses Orange County’s verified millage, and the buyer closing costs calculator builds the full cash-to-close.

Demand and supply in Orange County right now

In the most recent IRS migration data (2022-2023), Orange County lost a net 9,037 people to relocation, with the largest inbound flows from NY, CA, NJ. Households moving IN reported average incomes of $66,457 versus $61,323 for those leaving — the income mix of demand, straight from tax filings. Population is up about 9.0% over the recent multi-year window. On the supply side, builders pulled 13,140 residential permits in Orange County in 2025 (4,221 single-family), up 63.2% year over year. Permits are tomorrow’s inventory: a shrinking pipeline supports prices, a swelling one hands buyers leverage. Our valuation model reads the county as overvalued by about 6.9% versus its income-and-rent fundamentals.

Explore more of Winter Garden

Run the numbers in Orange County

Common questions

How many golf course communities does Winter Garden, FL have?

Momentum currently tracks 44 communities in Winter Garden with evidence of golf community living in MLS or verified amenity records. Others exist; these are the ones with active market data.

What do homes in Winter Garden golf course communities cost?

The median sale price across tracked golf course communities in Winter Garden is about $594,000, varying widely by community - see the table for community-level medians.

How does Momentum classify a community as one of the golf course communities?

A community appears here when we find golf amenities reported on MLS listings or verified amenity records for the community. We do not guess from names alone. Verify any specific amenity or restriction with the association before you rely on it.

How much is home insurance in Orange County?

Citizens Property Insurance policies in Orange County average about $1,409 a year, per Citizens filings. Private quotes vary widely with roof age, construction and wind mitigation - a wind-mitigation inspection often unlocks meaningful credits.

What are property taxes like in Orange County?

Typical combined millage in Orange County is about 16.67 mills - roughly 1.67% of assessed value a year before exemptions. Florida resets assessed value to about your purchase price when you buy, then homestead exemptions and the 3% Save Our Homes cap apply.

Community classifications are compiled from MLS-reported amenities, verified amenity records and MLS build-year data, as of 2026-06-16; they are informational, change over time, and are deemed reliable but not guaranteed — verify details with each association. Not an offer of housing to any protected class to the exclusion of others. Equal Housing Opportunity.