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
1565 ROYAL FERN Lane Fleming Island, FL Welcome to this beautifully maintained all brick home nestled in the highly sought-after g...	4 beds \| 2 baths \| 2,331 sq.ft.	$505,000	Airbnb cash on cash: 2.99% Traditional cash on cash: 2.91% Airbnb Rental Income: $3257 Traditional Rental Income: $2487 Airbnb ROI: 2.99% Traditional ROI: 2.91%
1685 PINECREST Drive Fleming Island, FL Roof 2019 & HVAC 2024. Note this home's CDD is partially paid off. **Beautiful 4BR/3BA Hom...	4 beds \| 3 baths \| 2,647 sq.ft.	$539,000	Airbnb cash on cash: 3.01% Traditional cash on cash: 3.86% Airbnb Rental Income: $3257 Traditional Rental Income: $2954 Airbnb ROI: 3.01% Traditional ROI: 3.86%
2299 S BROOK Drive Fleming Island, FL This 4 bedroom 2 1/2 bath 2 story home sits on a preserve lot on one of the best streets i...	4 beds \| 3 baths \| 2,855 sq.ft.	$586,000	Airbnb cash on cash: 2.27% Traditional cash on cash: 2.97% Airbnb Rental Income: $3257 Traditional Rental Income: $2908 Airbnb ROI: 2.27% Traditional ROI: 2.97%
1301 PORTSIDE Drive Fleming Island, FL *BRAND NEW ROOF WITH SOLAR PANELS* Nestled in the desirable Harbor Island neighborhood...	4 beds \| 2 baths \| 1,756 sq.ft.	$370,000	Airbnb cash on cash: 4.59% Traditional cash on cash: 4.46% Airbnb Rental Income: $3257 Traditional Rental Income: $2478 Airbnb ROI: 4.59% Traditional ROI: 4.46%
762 HIBERNIA FOREST Drive Fleming Island, FL Welcome to 762 Hibernia Forest Dr, a beautifully updated and move-in ready home located in...	3 beds \| 2 baths \| 1,586 sq.ft.	$439,000	Airbnb cash on cash: 3.34% Traditional cash on cash: 3.26% Airbnb Rental Income: $2916 Traditional Rental Income: $2209 Airbnb ROI: 3.34% Traditional ROI: 3.26%
132 MALLEY COVE Lane Fleming Island, FL Custom-built, ADA-friendly home in the heart of Fleming Island with no HOA or CDD fees. Qu...	4 beds \| 4 baths \| 4,184 sq.ft.	$1,100,000	Airbnb cash on cash: 0.6% Traditional cash on cash: 1.96% Airbnb Rental Income: $3257 Traditional Rental Income: $3922 Airbnb ROI: 0.6% Traditional ROI: 1.96%
4966 HARVEY GRANT Road Fleming Island, FL 20.000$ TOWARDS BUYER CLOSING COST! NEW FLOORS! This home sits on over an acre in a quiet,...	3 beds \| 2 baths \| 2,116 sq.ft.	$465,000	Airbnb cash on cash: 3.05% Traditional cash on cash: 2.92% Airbnb Rental Income: $2916 Traditional Rental Income: $2185 Airbnb ROI: 3.05% Traditional ROI: 2.92%
2746 Archer Street Fleming Island, FL Welcome to this well-maintained 4-bedroom, 2-bath home tucked in a quiet cul-de-sac. Updat...	4 beds \| 2 baths \| 1,799 sq.ft.	$385,000	Airbnb cash on cash: 4.99% Traditional cash on cash: 4.04% Airbnb Rental Income: $3257 Traditional Rental Income: $2180 Airbnb ROI: 4.99% Traditional ROI: 4.04%
1400 GIBRALTER Lane Fleming Island, FL Pool home in the heart of Fleming Island, without the CDD fees! Enjoy outdoor entertaining...	4 beds \| 3 baths \| 2,667 sq.ft.	$484,000	Airbnb cash on cash: 3.34% Traditional cash on cash: 5.59% Airbnb Rental Income: $3257 Traditional Rental Income: $3544 Airbnb ROI: 3.34% Traditional ROI: 5.59%
1477 GREENWAY Place Fleming Island, FL Great 3 Bedroom 2 bath home in Fleming Island Plantation! Roof replaced in 2020. Formal li...	3 beds \| 2 baths \| 1,922 sq.ft.	$365,000	Airbnb cash on cash: 3.45% Traditional cash on cash: 3.07% Airbnb Rental Income: $2916 Traditional Rental Income: $2113 Airbnb ROI: 3.45% Traditional ROI: 3.07%
1798 COVINGTON Lane Fleming Island, FL Looking for space, style, and unbeatable outdoor living? This must-see home in Fleming Isl...	4 beds \| 2 baths \| 3,119 sq.ft.	$480,000	Airbnb cash on cash: 3.32% Traditional cash on cash: 3.27% Airbnb Rental Income: $3257 Traditional Rental Income: $2502 Airbnb ROI: 3.32% Traditional ROI: 3.27%
2918 GRANDE OAKS Way Fleming Island, FL Your Private Florida Resort Awaits! Dive into luxury at this 5-bedroom, 4-bath saltwater p...	5 beds \| 4 baths \| 2,922 sq.ft.	$680,000	Airbnb cash on cash: 4.46% Traditional cash on cash: 4.85% Airbnb Rental Income: $5355 Traditional Rental Income: $4525 Airbnb ROI: 4.46% Traditional ROI: 4.85%
1630 HIGHLAND VIEW Court Fleming Island, FL REDUCED PRICE! PAID OFF CDD BOND! No need to look any further! This immaculate home ha...	4 beds \| 3 baths \| 2,031 sq.ft.	$445,000	Airbnb cash on cash: 4.03% Traditional cash on cash: 4.25% Airbnb Rental Income: $3257 Traditional Rental Income: $2614 Airbnb ROI: 4.03% Traditional ROI: 4.25%
1601 MAJESTIC VIEW Lane Fleming Island, FL Dreams do come true with this corner lot home in the sought-after Fleming Island Plantatio...	4 beds \| 3 baths \| 2,532 sq.ft.	$485,000	Airbnb cash on cash: 2.99% Traditional cash on cash: 3.17% Airbnb Rental Income: $3257 Traditional Rental Income: $2605 Airbnb ROI: 2.99% Traditional ROI: 3.17%
1683 WATERS EDGE Drive Fleming Island, FL Nestled in the desirable community of Fleming Island, this beautifully maintained 4-bedroo...	4 beds \| 3 baths \| 2,566 sq.ft.	$675,000	Airbnb cash on cash: 1.43% Traditional cash on cash: 2.47% Airbnb Rental Income: $3257 Traditional Rental Income: $3175 Airbnb ROI: 1.43% Traditional ROI: 2.47%
1500 CALMING WATER Drive unit: 2406 #2406 Fleming Island, FL Beautiful End Unit in this gated community is being offered as MOVE IN READY! Just Freshly...	3 beds \| 3 baths \| 1,817 sq.ft.	$284,900	Airbnb cash on cash: 4.31% Traditional cash on cash: 3.24% Airbnb Rental Income: $2916 Traditional Rental Income: $1955 Airbnb ROI: 4.31% Traditional ROI: 3.24%
1896 CHATHAM VILLAGE Drive Fleming Island, FL Beautifully Updated Chatham Village builders model home in highly desired Fleming Island P...	3 beds \| 3 baths \| 2,686 sq.ft.	$489,000	Airbnb cash on cash: 2.44% Traditional cash on cash: 2.83% Airbnb Rental Income: $2916 Traditional Rental Income: $2418 Airbnb ROI: 2.44% Traditional ROI: 2.83%
1333 SOUTH SHORE Drive Fleming Island, FL Look at this gorgeous waterfront home! This mid-century, custom built home is nestled on a...	4 beds \| 3 baths \| 3,500 sq.ft.	$2,225,000	Airbnb cash on cash: -0.71% Traditional cash on cash: -0.65% Airbnb Rental Income: $3257 Traditional Rental Income: $2648 Airbnb ROI: -0.71% Traditional ROI: -0.65%
1722 MARGARETS WALK Road Fleming Island, FL Welcome to your pristine oasis in the gated Margarets Walk at Fleming Island Plantation. T...	4 beds \| 3 baths \| 3,035 sq.ft.	$725,000	Airbnb cash on cash: 1.78% Traditional cash on cash: 2.02% Airbnb Rental Income: $3257 Traditional Rental Income: $2685 Airbnb ROI: 1.78% Traditional ROI: 2.02%
1853 WESTON Circle Fleming Island, FL This beautifully updated 3-bedroom, 2-bathroom home in the heart of Fleming Island offers ...	3 beds \| 2 baths \| 1,746 sq.ft.	$369,900	Airbnb cash on cash: 3.68% Traditional cash on cash: 3.22% Airbnb Rental Income: $2916 Traditional Rental Income: $2080 Airbnb ROI: 3.68% Traditional ROI: 3.22%
1421 WOODLAND VIEW Drive Fleming Island, FL Included 100-Day Home Warranty with buyer activation.Welcome to your dream home! This prop...	4 beds \| 2 baths \| 1,927 sq.ft.	$345,000	Airbnb cash on cash: 5.2% Traditional cash on cash: 4.62% Airbnb Rental Income: $3257 Traditional Rental Income: $2337 Airbnb ROI: 5.2% Traditional ROI: 4.62%
1884 LAKE FOREST Lane Fleming Island, FL Final price reduction / Bring all cash offers - NO SUB-TO** Price reduced! Exceptional...	3 beds \| 2 baths \| 1,476 sq.ft.	$299,000	Airbnb cash on cash: 4.91% Traditional cash on cash: 3.71% Airbnb Rental Income: $2916 Traditional Rental Income: $1902 Airbnb ROI: 4.91% Traditional ROI: 3.71%
328 N RIDGE Drive Fleming Island, FL Live the Florida lifestyle in this 4-bedroom, 2.5-bath POOL home in Fleming Island with no...	4 beds \| 3 baths \| 2,276 sq.ft.	$515,000	Airbnb cash on cash: 2.67% Traditional cash on cash: 2.62% Airbnb Rental Income: $3257 Traditional Rental Income: $2500 Airbnb ROI: 2.67% Traditional ROI: 2.62%
560 MAJESTIC WOOD Drive Fleming Island, FL Offering $5k in Buyer concessions on offers accepted prior to September 7th Discover com...	4 beds \| 2 baths \| 2,049 sq.ft.	$369,000	Airbnb cash on cash: 5.31% Traditional cash on cash: 5.13% Airbnb Rental Income: $3257 Traditional Rental Income: $2464 Airbnb ROI: 5.31% Traditional ROI: 5.13%
1790 N LAKESHORE Drive Fleming Island, FL This exceptional 4-bedroom, 3-bath home showcases high-end finishes and thoughtful design ...	4 beds \| 3 baths \| 2,454 sq.ft.	$710,000	Airbnb cash on cash: 2.5% Traditional cash on cash: 2.83% Airbnb Rental Income: $3257 Traditional Rental Income: $2748 Airbnb ROI: 2.5% Traditional ROI: 2.83%
2448 COUNTRY SIDE Drive Fleming Island, FL Welcome to the immaculate Black Creek at Eagle Harbor neighborhood.. With 5 beds, 4 baths ...	5 beds \| 4 baths \| 2,902 sq.ft.	$541,500	Airbnb cash on cash: 5.69% Traditional cash on cash: 4.63% Airbnb Rental Income: $5355 Traditional Rental Income: $3736 Airbnb ROI: 5.69% Traditional ROI: 4.63%
2176 AUTUMN COVE Circle Fleming Island, FL Your dreams come true with this incredible home located in an exclusive resort style commu...	4 beds \| 4 baths \| 2,753 sq.ft.	$549,900	Airbnb cash on cash: 2.1% Traditional cash on cash: 3.61% Airbnb Rental Income: $3257 Traditional Rental Income: $3302 Airbnb ROI: 2.1% Traditional ROI: 3.61%
1875 GREEN SPRINGS Circle unit: B #B Fleming Island, FL Step into your dream lifestyle with this stunning 2-story townhome, perfectly nestled in t...	3 beds \| 3 baths \| 1,664 sq.ft.	$259,000	Airbnb cash on cash: 4.61% Traditional cash on cash: 3.22% Airbnb Rental Income: $2916 Traditional Rental Income: $1899 Airbnb ROI: 4.61% Traditional ROI: 3.22%
149 RIVERWOOD Drive Fleming Island, FL Come see this beautiful 4 bedroom 2.5 bath home on the St. Johns river. The living space i...	4 beds \| 3 baths \| 2,911 sq.ft.	$1,539,000	Airbnb cash on cash: 0.05% Traditional cash on cash: 0.75% Airbnb Rental Income: $3257 Traditional Rental Income: $3528 Airbnb ROI: 0.05% Traditional ROI: 0.75%
1506 WATERBRIDGE Court Fleming Island, FL Nestled within a tranquil cul-de-sac on prestigious Fleming Island, this meticulously reno...	5 beds \| 3 baths \| 2,852 sq.ft.	$649,000	Airbnb cash on cash: 5.08% Traditional cash on cash: 3.52% Airbnb Rental Income: $5355 Traditional Rental Income: $3329 Airbnb ROI: 5.08% Traditional ROI: 3.52%
2307 CROOKED PINE Lane Fleming Island, FL Motivated Seller - HUGE price improvement NEW roof with full price offer! Preferred lend...	5 beds \| 3 baths \| 3,037 sq.ft.	$550,000	Airbnb cash on cash: 6.09% Traditional cash on cash: 3.38% Airbnb Rental Income: $5355 Traditional Rental Income: $2884 Airbnb ROI: 6.09% Traditional ROI: 3.38%
6433 RIVER POINT Drive Fleming Island, FL Completely Remodeled 4 Bedroom / 3 Bathroom home with 100-ft of Waterfront, Lifetime Vinyl...	4 beds \| 3 baths \| 2,676 sq.ft.	$900,000	Airbnb cash on cash: 1.36% Traditional cash on cash: 2.57% Airbnb Rental Income: $3257 Traditional Rental Income: $3539 Airbnb ROI: 1.36% Traditional ROI: 2.57%
2518 WILLOW CREEK Drive Fleming Island, FL REDUCED!!!Welcome to this one of a kind, spacious home with many beautiful upgrades throug...	4 beds \| 4 baths \| 2,716 sq.ft.	$575,000	Airbnb cash on cash: 2.32% Traditional cash on cash: 4.67% Airbnb Rental Income: $3257 Traditional Rental Income: $3789 Airbnb ROI: 2.32% Traditional ROI: 4.67%
2479 PINEHURST Lane Fleming Island, FL Welcome to your exquisite haven in Fleming Island Plantation, where luxury meets comfort! ...	4 beds \| 4 baths \| 2,808 sq.ft.	$525,000	Airbnb cash on cash: 2.96% Traditional cash on cash: 5.96% Airbnb Rental Income: $3257 Traditional Rental Income: $3995 Airbnb ROI: 2.96% Traditional ROI: 5.96%
301 SCENIC POINT Lane Fleming Island, FL Very motivated sellers. Enjoy elevated riverfront living in this rare end-unit townhome wi...	4 beds \| 4 baths \| 2,260 sq.ft.	$480,000	Airbnb cash on cash: 2.94% Traditional cash on cash: 4.72% Airbnb Rental Income: $3257 Traditional Rental Income: $3323 Airbnb ROI: 2.94% Traditional ROI: 4.72%
1500 CALMING WATER Drive unit: 2203 #2203 Fleming Island, FL Dreams do come true with this stunning home in an established resort style gated community...	2 beds \| 2 baths \| 1,667 sq.ft.	$269,000	Airbnb cash on cash: 3.96% Traditional cash on cash: 5.15% Airbnb Rental Income: $2601 Traditional Rental Income: $2279 Airbnb ROI: 3.96% Traditional ROI: 5.15%
5640 STARLIGHT Lane Fleming Island, FL Stunning All-Brick Home with Rock Waterfall Pool Near St. Johns River - virtually No HOA r...	3 beds \| 3 baths \| 2,644 sq.ft.	$685,000	Airbnb cash on cash: 1.64% Traditional cash on cash: 2.89% Airbnb Rental Income: $2916 Traditional Rental Income: $3040 Airbnb ROI: 1.64% Traditional ROI: 2.89%
2264 LOOKOUT Landing Fleming Island, FL Welcome to Paradise! Enjoy the sound of birds and the beautiful water and tree view from y...	5 beds \| 4 baths \| 2,970 sq.ft.	$540,000	Airbnb cash on cash: 6.43% Traditional cash on cash: 7.36% Airbnb Rental Income: $5355 Traditional Rental Income: $4744 Airbnb ROI: 6.43% Traditional ROI: 7.36%
2012 BELLE GROVE Terrace Fleming Island, FL $10,000 TOWARD BUYERS' CLOSING COSTS! Don't miss this incredible opportunity to save on yo...	4 beds \| 4 baths \| 2,808 sq.ft.	$495,000	Airbnb cash on cash: 2.52% Traditional cash on cash: 5.48% Airbnb Rental Income: $3257 Traditional Rental Income: $3896 Airbnb ROI: 2.52% Traditional ROI: 5.48%
6376 ISLAND FOREST Drive unit: A #A Fleming Island, FL This freshly painted inviting 2-bedroom, 2-bathroom residence is designed for easy living ...	2 beds \| 2 baths \| 1,385 sq.ft.	$299,000	Airbnb cash on cash: 2.72% Traditional cash on cash: 2.27% Airbnb Rental Income: $2601 Traditional Rental Income: $1853 Airbnb ROI: 2.72% Traditional ROI: 2.27%

Real Estate investment in Fleming-island, FL

There are 75 properties for sale in the city of Fleming Island . The median list price in Fleming Island is $489,000 and the average price per square foot is $203. In September 2025, the average monthly cash on cash return in Fleming Island is 4.00%. The average monthly rental income in Fleming Island is $2,564.

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

There are 75 investment properties available for sale in Fleming-island.

In 2025, the best neighborhood to buy investment property is Fleming Island.

The ROI for Long-Term is higher than the Short-Term in Fleming-island with average rental income of $2,564.

Your search for investment property begins and ends here

Investment Property for Sale in Fleming Island, FL

1565 ROYAL FERN Lane

Fleming Island, FL

4 beds | 2 baths | 2,331 sq.ft.

$505,000

Airbnb cash on cash: 2.99%

Traditional cash on cash: 2.91%

Airbnb Rental Income: $3257

Traditional Rental Income: $2487

Airbnb ROI: 2.99%

Traditional ROI: 2.91%

1685 PINECREST Drive

Fleming Island, FL

4 beds | 3 baths | 2,647 sq.ft.

$539,000

Airbnb cash on cash: 3.01%

Traditional cash on cash: 3.86%

Airbnb Rental Income: $3257

Traditional Rental Income: $2954

Airbnb ROI: 3.01%

Traditional ROI: 3.86%

2299 S BROOK Drive

Fleming Island, FL

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

$586,000

Airbnb cash on cash: 2.27%

Traditional cash on cash: 2.97%

Airbnb Rental Income: $3257

Traditional Rental Income: $2908

Airbnb ROI: 2.27%

Traditional ROI: 2.97%

1301 PORTSIDE Drive

Fleming Island, FL

4 beds | 2 baths | 1,756 sq.ft.

$370,000

Airbnb cash on cash: 4.59%

Traditional cash on cash: 4.46%

Airbnb Rental Income: $3257

Traditional Rental Income: $2478

Airbnb ROI: 4.59%

Traditional ROI: 4.46%

762 HIBERNIA FOREST Drive

Fleming Island, FL

3 beds | 2 baths | 1,586 sq.ft.

$439,000

Airbnb cash on cash: 3.34%

Traditional cash on cash: 3.26%

Airbnb Rental Income: $2916

Traditional Rental Income: $2209

Airbnb ROI: 3.34%

Traditional ROI: 3.26%

132 MALLEY COVE Lane

Fleming Island, FL

4 beds | 4 baths | 4,184 sq.ft.

$1,100,000

Airbnb cash on cash: 0.6%

Traditional cash on cash: 1.96%

Airbnb Rental Income: $3257

Traditional Rental Income: $3922

Airbnb ROI: 0.6%

Traditional ROI: 1.96%

4966 HARVEY GRANT Road

Fleming Island, FL

3 beds | 2 baths | 2,116 sq.ft.

$465,000

Airbnb cash on cash: 3.05%

Traditional cash on cash: 2.92%

Airbnb Rental Income: $2916

Traditional Rental Income: $2185

Airbnb ROI: 3.05%

Traditional ROI: 2.92%

2746 Archer Street

Fleming Island, FL

4 beds | 2 baths | 1,799 sq.ft.

$385,000

Airbnb cash on cash: 4.99%

Traditional cash on cash: 4.04%

Airbnb Rental Income: $3257

Traditional Rental Income: $2180

Airbnb ROI: 4.99%