Real Estate Investment Properties for Sale in Windley Key, FL

Looking for investment property in Windley Key, FL with high ROI ?

Explore a variety of short-term homes & houses in Windley Key, FL. Invest wisely with VRBO & Windley Key, 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 Windley Key, FL

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
No properties are listed in Windley Key, Florida at the moment.
Investment Properties for Sale in Other Cities of 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 \| N/A	$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%
7628 Preservation Road Tallahassee , FL All brick, golf course frontage in Summerbrooke! This home is stunning and has been update...	4 beds \| 4 baths \| 3,772 sq.ft.	$925,000	Airbnb cash on cash: 1.39% Traditional cash on cash: 2.21% Airbnb Rental Income: $4202 Traditional Rental Income: $4016 Airbnb ROI: 1.39% Traditional ROI: 2.21%
2661 HAWKS LANDING BOULEVARD Palm Harbor , FL Located within the gated community of Hawks Landing, 2661 Hawks Landing Blvd offers a comb...	5 beds \| 4 baths \| 5,114 sq.ft.	$2,600,000	Airbnb cash on cash: 0.94% Traditional cash on cash: 0.76% Airbnb Rental Income: $8179 Traditional Rental Income: $6207 Airbnb ROI: 0.94% Traditional ROI: 0.76%
8345 SW 200th Ct Dunnellon , FL Welcome to Your Half-Acre Florida Retreat! Set on a beautiful half-acre lot, this charmin...	2 beds \| 2 baths \| 1,249 sq.ft.	$325,000	Airbnb cash on cash: 0.35% Traditional cash on cash: 3.08% Airbnb Rental Income: $1257 Traditional Rental Income: $1694 Airbnb ROI: 0.35% Traditional ROI: 3.08%
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: -1.82% Traditional cash on cash: 2.76% Airbnb Rental Income: $728 Traditional Rental Income: $2874 Airbnb ROI: -1.82% Traditional ROI: 2.76%
2216 W Skagway Ave Tampa , FL Wonderful opportunity to own in Carroll City. This updated 4 bedroom, 2 bath home has a la...	4 beds \| 2 baths \| 2,294 sq.ft.	$427,500	Airbnb cash on cash: 0.51% Traditional cash on cash: 5.13% Airbnb Rental Income: $1132 Traditional Rental Income: $2606 Airbnb ROI: 0.51% Traditional ROI: 5.13%
8423 N Otis Ave Tampa , FL 8423 N Otis Ave, Tampa, FL 33604 \| Single Family Residential	4 beds \| 3 baths \| 1,884 sq.ft.	$425,000	Airbnb cash on cash: -0.22% Traditional cash on cash: 4.55% Airbnb Rental Income: $1132 Traditional Rental Income: $2655 Airbnb ROI: -0.22% Traditional ROI: 4.55%
1705 W Norfolk St Tampa , FL Welcome to this unique and versatile single-family home with NO HOA or CDD fees, located i...	3 beds \| 3 baths \| 2,044 sq.ft.	$549,900	Airbnb cash on cash: -0.78% Traditional cash on cash: 3.96% Airbnb Rental Income: $943 Traditional Rental Income: $3030 Airbnb ROI: -0.78% Traditional ROI: 3.96%
1311 E Sligh Ave Tampa , FL 1311 E Sligh Ave, Tampa, FL 33604 \| Single Family Residential	3 beds \| 2 baths \| 1,300 sq.ft.	$275,000	Airbnb cash on cash: -0.07% Traditional cash on cash: 5.99% Airbnb Rental Income: $902 Traditional Rental Income: $2134 Airbnb ROI: -0.07% Traditional ROI: 5.99%
375 Plymouth Rd West Palm Beach , FL Nestled in the heart of West Palm Beachâs sought-after SoSo neighborhood, this charming ...	3 beds \| 2 baths \| 1,967 sq.ft.	$2,295,000	Airbnb cash on cash: -0.53% Traditional cash on cash: 0.89% Airbnb Rental Income: $2028 Traditional Rental Income: $4540 Airbnb ROI: -0.53% Traditional ROI: 0.89%
7308 Hager Way Orlando , FL 7308 Hager Way, Orlando, FL 32822 \| Single Family Residential	3 beds \| 1 baths \| 1,152 sq.ft.	$385,000	Airbnb cash on cash: -0.13% Traditional cash on cash: 3.17% Airbnb Rental Income: $1099 Traditional Rental Income: $1920 Airbnb ROI: -0.13% Traditional ROI: 3.17%
4474 Twinview Ln Orlando , FL 4474 Twinview Ln, Orlando, FL 32814 \| Townhouse	4 beds \| 3 baths \| 3,197 sq.ft.	$1,049,000	Airbnb cash on cash: -0.72% Traditional cash on cash: 0.1% Airbnb Rental Income: $2509 Traditional Rental Income: $2699 Airbnb ROI: -0.72% Traditional ROI: 0.1%
155 S Court Ave #1603 Orlando , FL 155 S Court Ave #1603, Orlando, FL 32801 \| Condo/Coop	1 beds \| 1 baths \| 615 sq.ft.	$205,000	Airbnb cash on cash: -1.36% Traditional cash on cash: 0.69% Airbnb Rental Income: $1318 Traditional Rental Income: $1309 Airbnb ROI: -1.36% Traditional ROI: 0.69%
260 S Osceola Ave #709 Orlando , FL Experience Luxury High-Rise Living in the Heart of Downtown Orlando Discover the ultima...	2 beds \| 2 baths \| 2,000 sq.ft.	$699,900	Airbnb cash on cash: -3.81% Traditional cash on cash: -0.94% Airbnb Rental Income: $1680 Traditional Rental Income: $3107 Airbnb ROI: -3.81% Traditional ROI: -0.94%
100 S Eola Dr #911 Orlando , FL 100 S Eola Dr #911, Orlando, FL 32801 \| Condo/Coop	2 beds \| 2 baths \| 2,100 sq.ft.	$725,000	Airbnb cash on cash: -2.63% Traditional cash on cash: -0.95% Airbnb Rental Income: $1680 Traditional Rental Income: $2346 Airbnb ROI: -2.63% Traditional ROI: -0.95%

Real Estate investment in Windley-key, FL

There are 2 properties for sale in the city of Windley Key . The median list price in Windley Key is $869,500 and the average price per square foot is $1,838. In February 2026, the average monthly cash on cash return in Windley Key is N/A%. The average monthly rental income in Windley Key is $N/A.

Windley-key, FL Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 2 investment properties available for sale in Windley-key.

The ROI for Short-Term is higher than the Long-Term in Windley-key with average rental income of $N/A.

Your search for investment property begins and ends here

Investment Property for Sale in Windley Key, FL

Investment Properties for Sale in Other Cities of Florida

Panama City Beach , FL

4 beds | 3 baths | N/A

$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%

Tallahassee , FL

4 beds | 4 baths | 3,772 sq.ft.

$925,000

Airbnb cash on cash: 1.39%

Traditional cash on cash: 2.21%

Airbnb Rental Income: $4202

Traditional Rental Income: $4016

Airbnb ROI: 1.39%

Traditional ROI: 2.21%

Palm Harbor , FL

5 beds | 4 baths | 5,114 sq.ft.

$2,600,000

Airbnb cash on cash: 0.94%

Traditional cash on cash: 0.76%

Airbnb Rental Income: $8179

Traditional Rental Income: $6207

Airbnb ROI: 0.94%

Traditional ROI: 0.76%

Dunnellon , FL

2 beds | 2 baths | 1,249 sq.ft.

$325,000

Airbnb cash on cash: 0.35%

Traditional cash on cash: 3.08%

Airbnb Rental Income: $1257

Traditional Rental Income: $1694

Airbnb ROI: 0.35%

Traditional ROI: 3.08%

Tampa , FL

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

$575,000

Airbnb cash on cash: -1.82%

Traditional cash on cash: 2.76%

Airbnb Rental Income: $728

Traditional Rental Income: $2874

Airbnb ROI: -1.82%

Traditional ROI: 2.76%

Tampa , FL

4 beds | 2 baths | 2,294 sq.ft.

$427,500

Airbnb cash on cash: 0.51%

Traditional cash on cash: 5.13%

Airbnb Rental Income: $1132

Traditional Rental Income: $2606

Airbnb ROI: 0.51%

Traditional ROI: 5.13%

Tampa , FL

4 beds | 3 baths | 1,884 sq.ft.

$425,000

Airbnb cash on cash: -0.22%

Traditional cash on cash: 4.55%

Airbnb Rental Income: $1132

Traditional Rental Income: $2655

Airbnb ROI: -0.22%

Traditional ROI: 4.55%

Tampa , FL

3 beds | 3 baths | 2,044 sq.ft.

$549,900

Airbnb cash on cash: -0.78%

Traditional cash on cash: 3.96%

Airbnb Rental Income: $943

Traditional Rental Income: $3030

Airbnb ROI: -0.78%

Traditional ROI: 3.96%

Tampa , FL

3 beds | 2 baths | 1,300 sq.ft.

$275,000

Airbnb cash on cash: -0.07%

Traditional cash on cash: 5.99%

Airbnb Rental Income: $902