Real Estate Investment Properties for Sale in Winter Garden, FL

Looking for investment property in Winter Garden, FL with high ROI ?

Explore a variety of short-term homes & houses in Winter Garden, FL. Invest wisely with VRBO & Winter Garden, FL Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Investment Property for Sale in Winter Garden, FL

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
No properties are listed in Winter Garden, Florida at the moment.
Other Investment Properties for Sale in Florida
921 Lighthouse Lagoon Court Panama City Beach , FL Deep water executive home with significant upgrades and a 10,000-pound boat lift accommoda...	4 beds \| 3 baths \| 3,241 sq.ft.	$974,000	Airbnb cash on cash: 1% Traditional cash on cash: 1.51% Airbnb Rental Income: $3630 Traditional Rental Income: $3304 Airbnb ROI: 1% Traditional ROI: 1.51%
5286 Wild Goose Road North Port , FL Welcome to one of the most affordable options in east Tallahassee's popular Pine Dove Esta...	3 beds \| 3 baths \| 1,947 sq.ft.	$449,900	Airbnb cash on cash: 1.47% Traditional cash on cash: 4.55% Airbnb Rental Income: $2111 Traditional Rental Income: $2868 Airbnb ROI: 1.47% Traditional ROI: 4.55%
2101 N Brentwood Circle Lecanto , FL IIMMACULATE "CAREFREE" HOME IN THE BEST-OF-BEST CENTRAL CITRUS COUNTY LOCATION! Here's an ...	3 beds \| 2 baths \| 1,691 sq.ft.	$259,900	Airbnb cash on cash: 5.96% Traditional cash on cash: 4.91% Airbnb Rental Income: $3240 Traditional Rental Income: $2253 Airbnb ROI: 5.96% Traditional ROI: 4.91%
19480 SW 100TH LOOP Dunnellon , FL Welcome to the Rainbow Springs Community and living the Florida lifestyle! As you enter t...	4 beds \| 2 baths \| 2,271 sq.ft.	$425,000	Airbnb cash on cash: 8.95% Traditional cash on cash: 5.42% Airbnb Rental Income: $5495 Traditional Rental Income: $2984 Airbnb ROI: 8.95% Traditional ROI: 5.42%
2915 E WATERS AVENUE Tampa , FL The property is right on the river! The house is very comfortable with open floor plan and...	3 beds \| 2 baths \| 1,502 sq.ft.	$575,000	Airbnb cash on cash: 1.57% Traditional cash on cash: 2.76% Airbnb Rental Income: $2912 Traditional Rental Income: $2874 Airbnb ROI: 1.57% Traditional ROI: 2.76%
7806 N VAN DYKE PLACE Tampa , FL MUST SEE!!! This FULLY RENOVATED home in the heart of Tampa - where no detail has been ove...	3 beds \| 3 baths \| 1,604 sq.ft.	$400,000	Airbnb cash on cash: 4.54% Traditional cash on cash: 4.78% Airbnb Rental Income: $3023 Traditional Rental Income: $2419 Airbnb ROI: 4.54% Traditional ROI: 4.78%
228 S SUMMERLIN AVENUE Orlando , FL Under contract-accepting backup offers. Welcome to The Brownstones, where timeless archite...	3 beds \| 4 baths \| 1,972 sq.ft.	$895,000	Airbnb cash on cash: -1.53% Traditional cash on cash: 0.71% Airbnb Rental Income: $1818 Traditional Rental Income: $3191 Airbnb ROI: -1.53% Traditional ROI: 0.71%
260 S OSCEOLA AVENUE #709 Orlando , FL Experience Luxury High-Rise Living in the Heart of Downtown Orlando Discover the ultima...	2 beds \| 3 baths \| 2,000 sq.ft.	$715,000	Airbnb cash on cash: -2.42% Traditional cash on cash: 0.42% Airbnb Rental Income: $1680 Traditional Rental Income: $3107 Airbnb ROI: -2.42% Traditional ROI: 0.42%
115 E HARVARD STREET Orlando , FL Please note: Tax roll states a 3rd bedroom, however, 3rd room does NOT have a closet. This...	3 beds \| 1 baths \| 1,130 sq.ft.	$425,000	Airbnb cash on cash: 1.96% Traditional cash on cash: 2.83% Airbnb Rental Income: $2077 Traditional Rental Income: $1887 Airbnb ROI: 1.96% Traditional ROI: 2.83%
1300 EDMUNDSHIRE LANE Orlando , FL Under contract-accepting backup offers. Seller may consider buyer concessions if made in a...	3 beds \| 2 baths \| 1,504 sq.ft.	$425,000	Airbnb cash on cash: 0.72% Traditional cash on cash: 4.38% Airbnb Rental Income: $1485 Traditional Rental Income: $2505 Airbnb ROI: 0.72% Traditional ROI: 4.38%
2614 E PINE STREET Orlando , FL Under contract-accepting backup offers. You must see this absolutely charming and beautifu...	2 beds \| 3 baths \| 1,300 sq.ft.	$330,000	Airbnb cash on cash: 0.5% Traditional cash on cash: 3.8% Airbnb Rental Income: $1680 Traditional Rental Income: $2236 Airbnb ROI: 0.5% Traditional ROI: 3.8%
4509 PATRICIA ANN COURT Orlando , FL One or more photo(s) has been virtually staged. Welcome to beautiful Holden Cove, a gorgeo...	5 beds \| 4 baths \| 3,815 sq.ft.	$1,449,000	Airbnb cash on cash: -1% Traditional cash on cash: 1.14% Airbnb Rental Income: $2032 Traditional Rental Income: $4383 Airbnb ROI: -1% Traditional ROI: 1.14%
10457 CROMWELL GROVE TERRACE Orlando , FL One or more photo(s) has been virtually staged. With four bedrooms and four full bathrooms...	4 beds \| 4 baths \| 2,890 sq.ft.	$1,890,000	Airbnb cash on cash: -1.56% Traditional cash on cash: 0.45% Airbnb Rental Income: $1475 Traditional Rental Income: $4579 Airbnb ROI: -1.56% Traditional ROI: 0.45%
9189 CAMDEN GARDENS STREET Orlando , FL One or more photo(s) has been virtually staged. Welcome to this beautifully updated and li...	4 beds \| 3 baths \| 1,504 sq.ft.	$410,000	Airbnb cash on cash: 3.28% Traditional cash on cash: 3.06% Airbnb Rental Income: $3070 Traditional Rental Income: $2284 Airbnb ROI: 3.28% Traditional ROI: 3.06%
8679 LAUREATE BOULEVARD Orlando , FL GORGEOUS LAKE NONA CRAFTMAN HOME NEAR MEDICAL CITY! Brick paved front porch with CONSERVAT...	3 beds \| 3 baths \| 2,261 sq.ft.	$645,000	Airbnb cash on cash: -0.38% Traditional cash on cash: 2.26% Airbnb Rental Income: $1824 Traditional Rental Income: $2916 Airbnb ROI: -0.38% Traditional ROI: 2.26%

Real Estate investment in Winter-garden, FL

There are 0 properties for sale in the city of Winter Garden . The median list price in Winter Garden is $598,400 and the average price per square foot is $250. In October 2025, the average monthly cash on cash return in Winter Garden is 3.00%. The average monthly rental income in Winter Garden is $2,702.

Winter-garden, FL Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 0 investment properties available for sale in Winter-garden.

In 2025, the best neighborhood to buy investment property is Winter Garden.

The ROI for Long-Term is higher than the Short-Term in Winter-garden with average rental income of $2,702.

Your search for investment property begins and ends here

Investment Property for Sale in Winter Garden, FL

Other Investment Properties for Sale in Florida

Panama City Beach , FL

4 beds | 3 baths | 3,241 sq.ft.

$974,000

Airbnb cash on cash: 1%

Traditional cash on cash: 1.51%

Airbnb Rental Income: $3630

Traditional Rental Income: $3304

Airbnb ROI: 1%

Traditional ROI: 1.51%

North Port , FL

3 beds | 3 baths | 1,947 sq.ft.

$449,900

Airbnb cash on cash: 1.47%

Traditional cash on cash: 4.55%

Airbnb Rental Income: $2111

Traditional Rental Income: $2868

Airbnb ROI: 1.47%

Traditional ROI: 4.55%

Lecanto , FL

3 beds | 2 baths | 1,691 sq.ft.

$259,900

Airbnb cash on cash: 5.96%

Traditional cash on cash: 4.91%

Airbnb Rental Income: $3240

Traditional Rental Income: $2253

Airbnb ROI: 5.96%

Traditional ROI: 4.91%

Dunnellon , FL

4 beds | 2 baths | 2,271 sq.ft.

$425,000

Airbnb cash on cash: 8.95%

Traditional cash on cash: 5.42%

Airbnb Rental Income: $5495

Traditional Rental Income: $2984

Airbnb ROI: 8.95%

Traditional ROI: 5.42%

Tampa , FL

3 beds | 2 baths | 1,502 sq.ft.

$575,000

Airbnb cash on cash: 1.57%

Traditional cash on cash: 2.76%

Airbnb Rental Income: $2912

Traditional Rental Income: $2874

Airbnb ROI: 1.57%

Traditional ROI: 2.76%

Tampa , FL

3 beds | 3 baths | 1,604 sq.ft.

$400,000

Airbnb cash on cash: 4.54%

Traditional cash on cash: 4.78%

Airbnb Rental Income: $3023

Traditional Rental Income: $2419

Airbnb ROI: 4.54%

Traditional ROI: 4.78%

Orlando , FL

3 beds | 4 baths | 1,972 sq.ft.

$895,000

Airbnb cash on cash: -1.53%

Traditional cash on cash: 0.71%

Airbnb Rental Income: $1818

Traditional Rental Income: $3191

Airbnb ROI: -1.53%

Traditional ROI: 0.71%

Orlando , FL

2 beds | 3 baths | 2,000 sq.ft.

$715,000

Airbnb cash on cash: -2.42%

Traditional cash on cash: 0.42%

Airbnb Rental Income: $1680

Traditional Rental Income: $3107

Airbnb ROI: -2.42%

Traditional ROI: 0.42%

Orlando , FL

3 beds | 1 baths | 1,130 sq.ft.

$425,000

Airbnb cash on cash: 1.96%

Traditional cash on cash: 2.83%

Airbnb Rental Income: $2077