Real Estate Investment Properties for Sale in Chokoloskee, FL

Looking for investment property in Chokoloskee, FL with high ROI ?

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1291 E Chokoloskee Dr CHOKOLOSKEE, FL WATERFRONT - On Chokoloskee Island, a boating and fishing destination in the Florida Everg...	2 beds \| 2 baths \| N/A	$585,000	Airbnb cash on cash: 3.84% Traditional cash on cash: 3.73% Airbnb Rental Income: $3801 Traditional Rental Income: $2922 Airbnb ROI: 3.84% Traditional ROI: 3.73%
1227 Mangrove Ln CHOKOLOSKEE, FL Imagine owning a prime piece of real estate just steps away from the sparkling waters of t...	6 beds \| 4 baths \| 2,880 sq.ft.	$539,900	Airbnb cash on cash: 3.58% Traditional cash on cash: 6.69% Airbnb Rental Income: $3801 Traditional Rental Income: $4544 Airbnb ROI: 3.58% Traditional ROI: 6.69%
123 Smallwood Drive #10B CHOKOLOSKEE, FL Laid-back condo living with great water views! This unique two-story 2BR/2BA condo has bee...	2 beds \| 2 baths \| 1,208 sq.ft.	$495,000	Airbnb cash on cash: 4.42% Traditional cash on cash: 4.36% Airbnb Rental Income: $3801 Traditional Rental Income: $2953 Airbnb ROI: 4.42% Traditional ROI: 4.36%
177 Lopez Ln CHOKOLOSKEE, FL Bonus: Property has an assumable VA loan at an attractive rate for qualified buyers (subje...	2 beds \| 2 baths \| 1,056 sq.ft.	$334,900	Airbnb cash on cash: 8.09% Traditional cash on cash: 7.05% Airbnb Rental Income: $3801 Traditional Rental Income: $2651 Airbnb ROI: 8.09% Traditional ROI: 7.05%
Investment Properties for Sale in Other Cities of Florida
14825 Front Beach Rd #511 Panama City Beach , FL BIGGEST AND BEST IN SUNRISE BEACH! HANDS DOWN THE NICEST UNIT IN THE DEVELOPMENT. BEST FLO...	3 beds \| 3 baths \| 1,565 sq.ft.	$777,000	Airbnb cash on cash: -1.81% Traditional cash on cash: -0.08% Airbnb Rental Income: $1279 Traditional Rental Income: $2128 Airbnb ROI: -1.81% Traditional ROI: -0.08%
9492 Buck Haven Trail Tallahassee , FL Located in the desirable Killearn Lakes subdivision, this home is within walking distance ...	3 beds \| 2 baths \| 1,562 sq.ft.	$339,500	Airbnb cash on cash: -0.2% Traditional cash on cash: 3.44% Airbnb Rental Income: $993 Traditional Rental Income: $1799 Airbnb ROI: -0.2% Traditional ROI: 3.44%
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.	$2,200,000	Airbnb cash on cash: -0.96% Traditional cash on cash: 3.51% Airbnb Rental Income: $2668 Traditional Rental Income: $11171 Airbnb ROI: -0.96% Traditional ROI: 3.51%
8345 SW 200TH COURT 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.	$315,000	Airbnb cash on cash: 4.53% Traditional cash on cash: 5.04% Airbnb Rental Income: $2729 Traditional Rental Income: $2237 Airbnb ROI: 4.53% Traditional ROI: 5.04%
7806 N VAN DYKE PLACE Tampa , FL Under contract-accepting backup offers. Qualified buyers gets 1% credit with preferred len...	3 beds \| 3 baths \| 1,604 sq.ft.	$350,000	Airbnb cash on cash: 0% Traditional cash on cash: 8.07% Airbnb Rental Income: $925 Traditional Rental Income: $3234 Airbnb ROI: 0% Traditional ROI: 8.07%
1705 W NORFOLK STREET 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: 4.48% Airbnb Rental Income: $943 Traditional Rental Income: $3298 Airbnb ROI: -0.78% Traditional ROI: 4.48%
8419 N OLA AVENUE Tampa , FL Move-in ready and fully upgraded! This stunning Tampa home boasts a new roof and stylish u...	3 beds \| 2 baths \| 1,120 sq.ft.	$379,000	Airbnb cash on cash: 0.26% Traditional cash on cash: 6.25% Airbnb Rental Income: $991 Traditional Rental Income: $2767 Airbnb ROI: 0.26% Traditional ROI: 6.25%
7211 N TALIAFERRO AVENUE Tampa , FL Welcome to a truly special Seminole Heights bungalow where timeless character meets though...	3 beds \| 2 baths \| 1,090 sq.ft.	$390,000	Airbnb cash on cash: -1.19% Traditional cash on cash: 4.76% Airbnb Rental Income: $902 Traditional Rental Income: $2740 Airbnb ROI: -1.19% Traditional ROI: 4.76%
375 Plymouth Road West Palm Beach , FL Welcome to 375 Plymouth Road, a turnkey residence in West Palm Beachâs coveted SoSo neig...	3 beds \| 3 baths \| 1,967 sq.ft.	$2,265,000	Airbnb cash on cash: -0.9% Traditional cash on cash: 1.01% Airbnb Rental Income: $1088 Traditional Rental Income: $4721 Airbnb ROI: -0.9% Traditional ROI: 1.01%
7308 Hager Way Orlando , FL 7308 Hager Way, Orlando, FL 32822 \| Single Family Residential	3 beds \| 1 baths \| 1,152 sq.ft.	$360,000	Airbnb cash on cash: -0.01% Traditional cash on cash: 3.91% Airbnb Rental Income: $1099 Traditional Rental Income: $2050 Airbnb ROI: -0.01% Traditional ROI: 3.91%
155 S Court Ave #1013 Orlando , FL 155 S Court Ave #1013, Orlando, FL 32801 \| Condo/Coop	1 beds \| 1 baths \| 772 sq.ft.	$269,000	Airbnb cash on cash: -2.31% Traditional cash on cash: 0.28% Airbnb Rental Income: $1318 Traditional Rental Income: $1565 Airbnb ROI: -2.31% Traditional ROI: 0.28%
322 E Central Blvd #1205 Orlando , FL 322 E Central Blvd #1205, Orlando, FL 32801 \| Condo/Coop	2 beds \| 2 baths \| 1,150 sq.ft.	$419,000	Airbnb cash on cash: -1.69% Traditional cash on cash: -0.22% Airbnb Rental Income: $1680 Traditional Rental Income: $1786 Airbnb ROI: -1.69% Traditional ROI: -0.22%
150 E ROBINSON STREET #1612 Orlando , FL This Distinguished Condo speaks for itself! No expense was spared on the new finishes. Uni...	2 beds \| 2 baths \| 1,285 sq.ft.	$689,000	Airbnb cash on cash: -2.48% Traditional cash on cash: -0.46% Airbnb Rental Income: $1693 Traditional Rental Income: $2523 Airbnb ROI: -2.48% Traditional ROI: -0.46%
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: 1.85% Airbnb Rental Income: $1318 Traditional Rental Income: $1535 Airbnb ROI: -1.36% Traditional ROI: 1.85%
300 E SOUTH STREET #6004 Orlando , FL Location, location, ...Charming one bedroom one bath on top 6th floor with Balcony overloo...	1 beds \| 1 baths \| 744 sq.ft.	$187,000	Airbnb cash on cash: -1.36% Traditional cash on cash: 3.62% Airbnb Rental Income: $1318 Traditional Rental Income: $1795 Airbnb ROI: -1.36% Traditional ROI: 3.62%

Real Estate investment in Chokoloskee, FL

There are 4 properties for sale in the city of Chokoloskee . The median list price in Chokoloskee is $414,950 and the average price per square foot is $313. In April 2026, the average monthly cash on cash return in Chokoloskee is 6.00%. The average monthly rental income in Chokoloskee is $2,651.

Chokoloskee, FL Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 4 investment properties available for sale in Chokoloskee.

The ROI for Short-Term is higher than the Long-Term in Chokoloskee with average rental income of $3,801.

Your search for investment property begins and ends here

Investment Property for Sale in Chokoloskee, FL

1291 E Chokoloskee Dr

CHOKOLOSKEE, FL

2 beds | 2 baths | N/A

$585,000

Airbnb cash on cash: 3.84%

Traditional cash on cash: 3.73%

Airbnb Rental Income: $3801

Traditional Rental Income: $2922

Airbnb ROI: 3.84%

Traditional ROI: 3.73%

1227 Mangrove Ln

CHOKOLOSKEE, FL

6 beds | 4 baths | 2,880 sq.ft.

$539,900

Airbnb cash on cash: 3.58%

Traditional cash on cash: 6.69%

Airbnb Rental Income: $3801

Traditional Rental Income: $4544

Airbnb ROI: 3.58%

Traditional ROI: 6.69%

123 Smallwood Drive #10B

CHOKOLOSKEE, FL

2 beds | 2 baths | 1,208 sq.ft.

$495,000

Airbnb cash on cash: 4.42%

Traditional cash on cash: 4.36%

Airbnb Rental Income: $3801

Traditional Rental Income: $2953

Airbnb ROI: 4.42%

Traditional ROI: 4.36%

177 Lopez Ln

CHOKOLOSKEE, FL

2 beds | 2 baths | 1,056 sq.ft.

$334,900

Airbnb cash on cash: 8.09%

Traditional cash on cash: 7.05%

Airbnb Rental Income: $3801

Traditional Rental Income: $2651

Airbnb ROI: 8.09%

Traditional ROI: 7.05%

Investment Properties for Sale in Other Cities of Florida

Panama City Beach , FL

3 beds | 3 baths | 1,565 sq.ft.

$777,000

Airbnb cash on cash: -1.81%

Traditional cash on cash: -0.08%

Airbnb Rental Income: $1279

Traditional Rental Income: $2128

Airbnb ROI: -1.81%

Traditional ROI: -0.08%

Tallahassee , FL

3 beds | 2 baths | 1,562 sq.ft.

$339,500

Airbnb cash on cash: -0.2%

Traditional cash on cash: 3.44%

Airbnb Rental Income: $993

Traditional Rental Income: $1799

Airbnb ROI: -0.2%

Traditional ROI: 3.44%

Palm Harbor , FL

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

$2,200,000

Airbnb cash on cash: -0.96%

Traditional cash on cash: 3.51%

Airbnb Rental Income: $2668

Traditional Rental Income: $11171

Airbnb ROI: -0.96%

Traditional ROI: 3.51%

Dunnellon , FL

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

$315,000

Airbnb cash on cash: 4.53%

Traditional cash on cash: 5.04%

Airbnb Rental Income: $2729

Traditional Rental Income: $2237

Airbnb ROI: 4.53%

Traditional ROI: 5.04%

Tampa , FL

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