Investor market data · Florida

Winter Garden, FL Rental Market for Investors

An estimated 11% of Winter Garden's active listings could cash-flow as a short-term rental — here's what the numbers say for investors, as of August 2026.

See what pencils →Run a DSCR

$599,000Median list price727 active listings

$43,823Median STR revenue / yrprojected, gross

Homes in Winter Garden that pencil right now

A sample of active Winter Garden listings whose DSCR clears 1.25 using short-term rental income projections we accept as a direct lender. These are spread across the price range, not ranked, and current as of August 2026.

$199,999DSCR 1.69
2 bed · 2 bath · 918 sqft
Condo in 34787 · built 1984
STR revenue
$37,531/yr
Est. interest-only payment
$1,479/mo
On the market 23 days · Listed by REVEL REALTY LLC
Scout this home & market: 2-bed condo in Winter Garden
$214,000DSCR 1.39
2 bed · 2 bath · 918 sqft
Condo in 34787 · built 1983
STR revenue
$35,378/yr
Est. interest-only payment
$1,700/mo
On the market 311 days · Listed by KEY CLASSIC REALTY LLC
Scout this home & market: 2-bed condo in Winter Garden
$285,000DSCR 1.40
2 bed · 1 bath · 696 sqft
House in 34787 · built 1951
STR revenue
$41,330/yr
Est. interest-only payment
$1,970/mo
On the market 258 days · Listed by Flat Fee MLS Realty
Scout this home & market: 2-bed house in Winter Garden
$287,000DSCR 1.47
3 bed · 2 bath · 1,453 sqft
Condo in 34787 · built 2005
STR revenue
$43,357/yr
Est. interest-only payment
$1,969/mo
On the market 51 days · Listed by Wra Real Estate Solutions Llc
Scout this home & market: 3-bed condo in Winter Garden
$309,000DSCR 1.37
3 bed · 2.5 bath · 1,647 sqft
Townhouse in 34787 · built 2007
STR revenue
$42,647/yr
Est. interest-only payment
$2,072/mo
On the market 87 days · Listed by beycome.com
Scout this home & market: 3-bed townhouse in Winter Garden
$330,000DSCR 1.29
3 bed · 2 bath · 1,050 sqft
House in 34787 · built 1996
STR revenue
$41,393/yr
Est. interest-only payment
$2,131/mo
On the market 75 days · Listed by THE REAL ESTATE COLLECTION LLC
Scout this home & market: 3-bed house in Winter Garden
$339,000DSCR 1.33
2 bed · 2 bath · 1,008 sqft
House in 34787 · built 1988
STR revenue
$43,923/yr
Est. interest-only payment
$2,194/mo
On the market 124 days · Listed by STIRLING INTERNATIONAL REAL ES
Scout this home & market: 2-bed house in Winter Garden

Ask about Winter Garden deals →Run any address yourself

As of August 2026, we analyzed 727 active for-sale homes in Winter Garden, Florida. The typical listing is priced at $599,000 and is projected to generate about $43,823 a year as a short-term rental.

After setting aside an estimated 20% for operating costs, an estimated 10.5% of those homes could still cover an investor mortgage payment on short-term-rental income — below the 52.5% median across the 200 major metros we track, ranking Winter Garden #197 of 200 for cash-flow potential.

On market momentum: homes in Winter Garden sit a median of 73 days on the market, and 22% of active listings came on in just the last 30 days — a slower-moving market, which shapes how much room there is to negotiate.

For a DSCR loan — which qualifies on the property's rental income rather than your personal income — Winter Garden runs tighter once operating costs are accounted for: many listings need a below-median price, a stronger short-term-rental setup, or more money down before the income covers the payment. It's a market where running the numbers property-by-property matters.

What actually works in Winter Garden

Cash-flow is the exception rather than the rule in Winter Garden right now: 18 of the 634 Winter Garden homes, condos and townhomes we can price confidently clear a DSCR of 1.25. Nine in ten of them are priced under $339,000.

Share of those listings clearing an DSCR of 1.25, by price and bedroom count. The smaller figure is the median DSCR for that group.
Price	2 bed	3 bed	4 bed	5 bed
$150k–$250k	19%0.98	0%0.89	—	—
$250k–$350k	9%0.80	30%0.89	—	—
$350k–$500k	0%0.67	0%0.83	0%0.84	—
$500k+	—	0%0.66	0%0.64	0%0.64

Darker means a larger share of that group cash-flows. “—” means fewer than 8 active listings — too few to draw a conclusion from.

Winter Garden in full

Active for-sale homes analyzed	727
Median list price	$599,000
Median projected STR revenue (annual, gross)	$43,823
Median average daily rate (ADR)	$181
Median occupancy	68%
Median beds	4
Median size	2,178 sqft
Estimated cash-flow-positive share	10.5%
Median days on market	73 days
New listings (last 30 days)	22.0% of active