Real Estate Investment Properties for Sale in Fleming Island, FL

Looking for investment property in Fleming Island, FL with high ROI ?

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1968 WESTEND Place Fleming Island, FL Welcome to this beautifully refreshed pool home in Fleming Island Plantation! Featuring 4 ...	4 beds \| 4 baths \| 2,481 sq.ft.	$515,000	Airbnb cash on cash: 0.02% Traditional cash on cash: 4.13% Airbnb Rental Income: $1850 Traditional Rental Income: $3334 Airbnb ROI: 0.02% Traditional ROI: 4.13%
1861 COPPER STONE Drive #D Fleming Island, FL MOVI IN READY ... Charming and meticulously maintained townhome with so many upgrades. Thi...	3 beds \| 3 baths \| 2,029 sq.ft.	$312,500	Airbnb cash on cash: 0.43% Traditional cash on cash: 4.27% Airbnb Rental Income: $1578 Traditional Rental Income: $2253 Airbnb ROI: 0.43% Traditional ROI: 4.27%
1515 VINELAND Circle #A Fleming Island, FL Enjoy natural light and a peaceful preserve backdrop in this one story end-unit townhome i...	3 beds \| 2 baths \| 1,075 sq.ft.	$254,000	Airbnb cash on cash: 1.71% Traditional cash on cash: 4.77% Airbnb Rental Income: $1578 Traditional Rental Income: $1860 Airbnb ROI: 1.71% Traditional ROI: 4.77%
2299 S BROOK Drive Fleming Island, FL Welcome to this beautifully updated home in the highly sought-after Eagle Harbor community...	4 beds \| 3 baths \| 2,855 sq.ft.	$480,000	Airbnb cash on cash: 0.32% Traditional cash on cash: 5.82% Airbnb Rental Income: $1850 Traditional Rental Income: $3820 Airbnb ROI: 0.32% Traditional ROI: 5.82%
2708 SHADE TREE Drive Fleming Island, FL Back on Market due to change of Buyers' Military Orders. Welcome to this custom built Poim...	4 beds \| 4 baths \| 3,145 sq.ft.	$899,000	Airbnb cash on cash: -0.5% Traditional cash on cash: 3.3% Airbnb Rental Income: $1850 Traditional Rental Income: $4536 Airbnb ROI: -0.5% Traditional ROI: 3.3%
1350 OAKLANDING Lane Fleming Island, FL Luxury living in Eagle Harbor's estate neighborhood, The Preserve. Built by respected buil...	4 beds \| 3 baths \| 3,905 sq.ft.	$1,200,000	Airbnb cash on cash: -0.68% Traditional cash on cash: 1.24% Airbnb Rental Income: $1850 Traditional Rental Income: $3500 Airbnb ROI: -0.68% Traditional ROI: 1.24%
1759 COUNTRY WALK Drive Fleming Island, FL 2.375% VA ASSUMABLE RATE! Move In Ready with newer Roof-2023, HVAC-2020, Hot water tank-20...	5 beds \| 4 baths \| 3,306 sq.ft.	$725,000	Airbnb cash on cash: -1.38% Traditional cash on cash: 5.86% Airbnb Rental Income: $756 Traditional Rental Income: $5335 Airbnb ROI: -1.38% Traditional ROI: 5.86%
1739 MOSS CREEK Drive Fleming Island, FL SELLER OFFERING $5,000 TOWARD BUYER CLOSING COSTS, PREPAIDS OR RATE BUYDOWN WITH ACCEPTABL...	4 beds \| 3 baths \| 2,081 sq.ft.	$439,000	Airbnb cash on cash: 0.5% Traditional cash on cash: 3.31% Airbnb Rental Income: $1850 Traditional Rental Income: $2510 Airbnb ROI: 0.5% Traditional ROI: 3.31%
1460 CREEKS EDGE Court Fleming Island, FL HIDDEN GEM 4 bedroom 2 bathroom home in the sought after Eagle Harbor Community! Beautiful...	4 beds \| 2 baths \| 2,275 sq.ft.	$489,000	Airbnb cash on cash: 0.81% Traditional cash on cash: 3.22% Airbnb Rental Income: $1850 Traditional Rental Income: $2457 Airbnb ROI: 0.81% Traditional ROI: 3.22%
2418 OLD PINE Trail Fleming Island, FL 3-bedroom, 2-bath townhome in Pine Lake at Eagle Harbor offering 1,340 square feet, a spli...	3 beds \| 2 baths \| 1,340 sq.ft.	$300,000	Airbnb cash on cash: 1.63% Traditional cash on cash: 4.07% Airbnb Rental Income: $1578 Traditional Rental Income: $1817 Airbnb ROI: 1.63% Traditional ROI: 4.07%
1923 HARBOR ISLAND Drive Fleming Island, FL Welcome to 1923 Harbor Island Drive, a remodeled 3-bedroom, 2-bath lakefront home offering...	3 beds \| 2 baths \| 1,931 sq.ft.	$455,000	Airbnb cash on cash: 0.63% Traditional cash on cash: 4.7% Airbnb Rental Income: $1578 Traditional Rental Income: $2861 Airbnb ROI: 0.63% Traditional ROI: 4.7%
1537 WINSTON Lane Fleming Island, FL Welcome to your ideal Fleming Island home and best of all, there's NO CDD! Check out this ...	3 beds \| 2 baths \| 1,904 sq.ft.	$425,000	Airbnb cash on cash: 0.44% Traditional cash on cash: 4.12% Airbnb Rental Income: $1578 Traditional Rental Income: $2591 Airbnb ROI: 0.44% Traditional ROI: 4.12%
2140 BLUE HERON COVE Drive Fleming Island, FL NO CDDs! Water views, single-story living, and big-ticket updates done! This 2,331 sq ft, ...	4 beds \| 2 baths \| 2,331 sq.ft.	$469,900	Airbnb cash on cash: 0.5% Traditional cash on cash: 3.24% Airbnb Rental Income: $1850 Traditional Rental Income: $2558 Airbnb ROI: 0.5% Traditional ROI: 3.24%
1776 CORD GRASS Lane Fleming Island, FL Welcome to 1776 Cordgrass Ln in Fleming Island! This maintained 3 bedroom 3 bathroom home ...	3 beds \| 3 baths \| 2,060 sq.ft.	$395,000	Airbnb cash on cash: 0.42% Traditional cash on cash: 4.42% Airbnb Rental Income: $1578 Traditional Rental Income: $2608 Airbnb ROI: 0.42% Traditional ROI: 4.42%
331 OAK Drive S Fleming Island, FL This Fleming Island waterfront home offers a rare chance to enjoy relaxed canal living wit...	3 beds \| 3 baths \| 2,224 sq.ft.	$715,000	Airbnb cash on cash: -0.33% Traditional cash on cash: 2.62% Airbnb Rental Income: $1578 Traditional Rental Income: $3095 Airbnb ROI: -0.33% Traditional ROI: 2.62%
544 MAJESTIC WOOD Drive Fleming Island, FL Welcome to this updated home on a spacious corner lot in Fleming Island! Improvements incl...	3 beds \| 2 baths \| 1,866 sq.ft.	$396,000	Airbnb cash on cash: 0.67% Traditional cash on cash: 3.64% Airbnb Rental Income: $1578 Traditional Rental Income: $2229 Airbnb ROI: 0.67% Traditional ROI: 3.64%
3194 CREIGHTON LANDING Road Fleming Island, FL RARE DEEDED BOAT SLIP + DOCTORS LAKE ACCESS! Discover the best of Fleming Island living in...	3 beds \| 2 baths \| 1,642 sq.ft.	$420,000	Airbnb cash on cash: 0.42% Traditional cash on cash: 3.03% Airbnb Rental Income: $1578 Traditional Rental Income: $2153 Airbnb ROI: 0.42% Traditional ROI: 3.03%
1575 CALMING WATER Drive Fleming Island, FL Meticulously Maintained & Beautifully Updated Home in Desirable Fleming Island! Welcome to...	3 beds \| 2 baths \| 1,714 sq.ft.	$397,500	Airbnb cash on cash: -0.5% Traditional cash on cash: 1.86% Airbnb Rental Income: $1578 Traditional Rental Income: $2006 Airbnb ROI: -0.5% Traditional ROI: 1.86%
696 FREDERIC Drive Fleming Island, FL 696 Frederic Drive makes a statement from the moment you arrive. Located in the coveted Hi...	4 beds \| 4 baths \| 3,906 sq.ft.	$975,000	Airbnb cash on cash: -0.17% Traditional cash on cash: 2.13% Airbnb Rental Income: $1850 Traditional Rental Income: $3447 Airbnb ROI: -0.17% Traditional ROI: 2.13%
1816 CREEKWOOD Lane Fleming Island, FL Breathtaking Water View & Preserve View ON PRIVATE CUL-DE-SAC NEW HVAC , NEW ROOF effo...	5 beds \| 4 baths \| 2,804 sq.ft.	$557,000	Airbnb cash on cash: -1.5% Traditional cash on cash: 5.22% Airbnb Rental Income: $756 Traditional Rental Income: $3937 Airbnb ROI: -1.5% Traditional ROI: 5.22%
1876 LAKE FOREST Lane Fleming Island, FL PRICE REDUCED - Under $400k. This beautifully updated Eagle Harbor home blends style, comf...	3 beds \| 2 baths \| 1,728 sq.ft.	$399,900	Airbnb cash on cash: 0.36% Traditional cash on cash: 3.06% Airbnb Rental Income: $1578 Traditional Rental Income: $2139 Airbnb ROI: 0.36% Traditional ROI: 3.06%
327 SCENIC POINT Lane Fleming Island, FL Enjoy beautiful St. Johns River views and spacious three-story living in this 4-bedroom, 3...	4 beds \| 4 baths \| 2,314 sq.ft.	$419,000	Airbnb cash on cash: 0.77% Traditional cash on cash: 3.84% Airbnb Rental Income: $1850 Traditional Rental Income: $2556 Airbnb ROI: 0.77% Traditional ROI: 3.84%
413 RIVER BIRCH Lane Fleming Island, FL RATE BUY-DOWN OFFEREDWelcome to this custom brick home in the desirable Christopher Co...	3 beds \| 3 baths \| 3,123 sq.ft.	$749,000	Airbnb cash on cash: -0.53% Traditional cash on cash: 3.46% Airbnb Rental Income: $1578 Traditional Rental Income: $3911 Airbnb ROI: -0.53% Traditional ROI: 3.46%
1576 LINKSIDE Drive Fleming Island, FL Whole house Generator year round, newer roof, comfort,Luxurious Upgrades in Fleming Island...	4 beds \| 3 baths \| 2,373 sq.ft.	$550,000	Airbnb cash on cash: 0.12% Traditional cash on cash: 3.2% Airbnb Rental Income: $1850 Traditional Rental Income: $2937 Airbnb ROI: 0.12% Traditional ROI: 3.2%
2411 GOLDEN BELL Lane Fleming Island, FL Welcome to 2411 Golden Bell Lane, a Pool Home tucked onto a quiet cul-de-sac in the sought...	4 beds \| 3 baths \| 2,691 sq.ft.	$610,000	Airbnb cash on cash: 0.27% Traditional cash on cash: 3.27% Airbnb Rental Income: $1850 Traditional Rental Income: $3060 Airbnb ROI: 0.27% Traditional ROI: 3.27%
1688 SANCTUARY Way Fleming Island, FL Welcome to luxury, low-maintenance living in the highly sought-after Hawks Landing communi...	3 beds \| 3 baths \| 1,980 sq.ft.	$329,000	Airbnb cash on cash: 0.73% Traditional cash on cash: 5.86% Airbnb Rental Income: $1578 Traditional Rental Income: $2712 Airbnb ROI: 0.73% Traditional ROI: 5.86%
1600 SPRING WATER Court Fleming Island, FL Welcome to your dream home in the highly sought-after Eagle Harbor community! This beautif...	4 beds \| 3 baths \| 2,566 sq.ft.	$550,000	Airbnb cash on cash: -0.4% Traditional cash on cash: 2.16% Airbnb Rental Income: $1850 Traditional Rental Income: $2670 Airbnb ROI: -0.4% Traditional ROI: 2.16%
1952 ROSE MALLOW Lane Fleming Island, FL Luxury opportunity in prestigious Pace Island! This custom-built 2007 estate offers resort...	5 beds \| 5 baths \| 5,035 sq.ft.	$1,150,000	Airbnb cash on cash: -1.56% Traditional cash on cash: 4.89% Airbnb Rental Income: $756 Traditional Rental Income: $7337 Airbnb ROI: -1.56% Traditional ROI: 4.89%
1858 ADLER NEST Lane Fleming Island, FL Welcome to this custom home located at in Fleming Island, FL. This property is part of the...	4 beds \| 3 baths \| 2,470 sq.ft.	$550,000	Airbnb cash on cash: 0.85% Traditional cash on cash: 3.48% Airbnb Rental Income: $1850 Traditional Rental Income: $2705 Airbnb ROI: 0.85% Traditional ROI: 3.48%
1855 COPPER STONE Drive #A Fleming Island, FL Enjoy low-maintenance living in this one-story townhome with all the Eagle Harbor amenitie...	2 beds \| 2 baths \| 1,385 sq.ft.	$288,000	Airbnb cash on cash: -1.75% Traditional cash on cash: 3.36% Airbnb Rental Income: $698 Traditional Rental Income: $1777 Airbnb ROI: -1.75% Traditional ROI: 3.36%
2371 BRIDGETTE Way Fleming Island, FL This luxurious Riverfront Estate sits high above the St. Johns River, 4266 sq. ft., 5 bedr...	5 beds \| 5 baths \| 4,266 sq.ft.	$1,399,999	Airbnb cash on cash: -1.37% Traditional cash on cash: 4.46% Airbnb Rental Income: $756 Traditional Rental Income: $8025 Airbnb ROI: -1.37% Traditional ROI: 4.46%
1565 CHAIN FERN Way Fleming Island, FL New ROOF Prior to Closing with accepted offer. Welcome to Pace Island, Fleming Island's on...	4 beds \| 2 baths \| 2,227 sq.ft.	$460,000	Airbnb cash on cash: 1.04% Traditional cash on cash: 3.73% Airbnb Rental Income: $1850 Traditional Rental Income: $2509 Airbnb ROI: 1.04% Traditional ROI: 3.73%

Real Estate investment in Fleming-island, FL

There are 80 properties for sale in the city of Fleming Island . The median list price in Fleming Island is $459,781 and the average price per square foot is $200. In November 2026, the average monthly cash on cash return in Fleming Island is 4.00%. The average monthly rental income in Fleming Island is $2,556.

Fleming-island, FL Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 80 investment properties available for sale in Fleming-island.

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

The ROI for Short-Term is higher than the Long-Term in Fleming-island with average rental income of $1,578.

Your search for investment property begins and ends here

Investment Property for Sale in Fleming Island, FL

1968 WESTEND Place

Fleming Island, FL

4 beds | 4 baths | 2,481 sq.ft.

$515,000

Airbnb cash on cash: 0.02%

Traditional cash on cash: 4.13%

Airbnb Rental Income: $1850

Traditional Rental Income: $3334

Airbnb ROI: 0.02%

Traditional ROI: 4.13%

1861 COPPER STONE Drive #D

Fleming Island, FL

3 beds | 3 baths | 2,029 sq.ft.

$312,500

Airbnb cash on cash: 0.43%

Traditional cash on cash: 4.27%

Airbnb Rental Income: $1578

Traditional Rental Income: $2253

Airbnb ROI: 0.43%

Traditional ROI: 4.27%

1515 VINELAND Circle #A

Fleming Island, FL

3 beds | 2 baths | 1,075 sq.ft.

$254,000

Airbnb cash on cash: 1.71%

Traditional cash on cash: 4.77%

Airbnb Rental Income: $1578

Traditional Rental Income: $1860

Airbnb ROI: 1.71%

Traditional ROI: 4.77%

2299 S BROOK Drive

Fleming Island, FL

4 beds | 3 baths | 2,855 sq.ft.

$480,000

Airbnb cash on cash: 0.32%

Traditional cash on cash: 5.82%

Airbnb Rental Income: $1850

Traditional Rental Income: $3820

Airbnb ROI: 0.32%

Traditional ROI: 5.82%

2708 SHADE TREE Drive

Fleming Island, FL

4 beds | 4 baths | 3,145 sq.ft.

$899,000

Airbnb cash on cash: -0.5%

Traditional cash on cash: 3.3%

Airbnb Rental Income: $1850

Traditional Rental Income: $4536

Airbnb ROI: -0.5%

Traditional ROI: 3.3%

1350 OAKLANDING Lane

Fleming Island, FL

4 beds | 3 baths | 3,905 sq.ft.

$1,200,000

Airbnb cash on cash: -0.68%

Traditional cash on cash: 1.24%

Airbnb Rental Income: $1850

Traditional Rental Income: $3500

Airbnb ROI: -0.68%

Traditional ROI: 1.24%

1759 COUNTRY WALK Drive

Fleming Island, FL

5 beds | 4 baths | 3,306 sq.ft.

$725,000

Airbnb cash on cash: -1.38%

Traditional cash on cash: 5.86%

Airbnb Rental Income: $756

Traditional Rental Income: $5335

Airbnb ROI: -1.38%

Traditional ROI: 5.86%

1739 MOSS CREEK Drive

Fleming Island, FL

4 beds | 3 baths | 2,081 sq.ft.

$439,000

Airbnb cash on cash: 0.5%

Traditional cash on cash: 3.31%

Airbnb Rental Income: $1850

Traditional Rental Income: $2510

Airbnb ROI: 0.5%