Real Estate Investment Properties for Sale in Enterprise, FL

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1336 Kettledrum Trail ENTERPRISE, FL Discover this one-of-a-kind 4BR/3.5BA estate in the sought-after Stone Island community. S...	4 beds \| 4 baths \| 3,712 sq.ft.	$599,900	Airbnb cash on cash: -0.23% Traditional cash on cash: 3.89% Airbnb Rental Income: $1574 Traditional Rental Income: $3431 Airbnb ROI: -0.23% Traditional ROI: 3.89%
1498 STONE TRAIL ENTERPRISE, FL Investorâs Dream in Stone Island, Florida! This fixer-upper is a blank canvas, ready for...	3 beds \| 2 baths \| 1,916 sq.ft.	$299,000	Airbnb cash on cash: 0.31% Traditional cash on cash: 6.14% Airbnb Rental Income: $1394 Traditional Rental Income: $2612 Airbnb ROI: 0.31% Traditional ROI: 6.14%
1475 WARRIOR TRAIL ENTERPRISE, FL Experience the best of Florida living at 1475 Warrior Trail! Springs! ** BUYER PERK: LENDE...	4 beds \| 3 baths \| 3,021 sq.ft.	$1,149,000	Airbnb cash on cash: -0.32% Traditional cash on cash: 1.66% Airbnb Rental Income: $1574 Traditional Rental Income: $3244 Airbnb ROI: -0.32% Traditional ROI: 1.66%
1385 ENTERPRISE OSTEEN ROAD ENTERPRISE, FL NO HOA. BEAUTIFULLY TREED 4.3 ACRES WITH MATURE PLANTS AND CANOPY OF OAKS EVERYWHERE. LARG...	4 beds \| 2 baths \| 1,811 sq.ft.	$500,000	Airbnb cash on cash: -0.11% Traditional cash on cash: 2.54% Airbnb Rental Income: $1574 Traditional Rental Income: $2360 Airbnb ROI: -0.11% Traditional ROI: 2.54%
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 Enterprise, FL

There are 4 properties for sale in the city of Enterprise . The median list price in Enterprise is $299,999 and the average price per square foot is $145. In February 2026, the average monthly cash on cash return in Enterprise is 3.00%. The average monthly rental income in Enterprise is $2,928.

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

There are 4 investment properties available for sale in Enterprise.

In 2026, the best neighborhood to buy investment property is ENTERPRISE.

The ROI for Short-Term is higher than the Long-Term in Enterprise with average rental income of $1,574.

Your search for investment property begins and ends here

Investment Property for Sale in Enterprise, FL

1336 Kettledrum Trail

ENTERPRISE, FL

4 beds | 4 baths | 3,712 sq.ft.

$599,900

Airbnb cash on cash: -0.23%

Traditional cash on cash: 3.89%

Airbnb Rental Income: $1574

Traditional Rental Income: $3431

Airbnb ROI: -0.23%

Traditional ROI: 3.89%

1498 STONE TRAIL

ENTERPRISE, FL

3 beds | 2 baths | 1,916 sq.ft.

$299,000

Airbnb cash on cash: 0.31%

Traditional cash on cash: 6.14%

Airbnb Rental Income: $1394

Traditional Rental Income: $2612

Airbnb ROI: 0.31%

Traditional ROI: 6.14%

1475 WARRIOR TRAIL

ENTERPRISE, FL

4 beds | 3 baths | 3,021 sq.ft.

$1,149,000

Airbnb cash on cash: -0.32%

Traditional cash on cash: 1.66%

Airbnb Rental Income: $1574

Traditional Rental Income: $3244

Airbnb ROI: -0.32%

Traditional ROI: 1.66%

1385 ENTERPRISE OSTEEN ROAD

ENTERPRISE, FL

4 beds | 2 baths | 1,811 sq.ft.

$500,000

Airbnb cash on cash: -0.11%

Traditional cash on cash: 2.54%

Airbnb Rental Income: $1574

Traditional Rental Income: $2360

Airbnb ROI: -0.11%

Traditional ROI: 2.54%

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.