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
1815 ROYAL FERN Lane Fleming Island, FL Welcome to this inviting 4-bedroom, 2-bath home offering 2,080 sq. ft. of comfortable livi...	4 beds \| 2 baths \| 2,080 sq.ft.	$459,000	Airbnb cash on cash: -0.53% Traditional cash on cash: 3.43% Airbnb Rental Income: $1147 Traditional Rental Income: $2468 Airbnb ROI: -0.53% Traditional ROI: 3.43%
1000 FLEMING Street Fleming Island, FL Welcome to 1000 Fleming Street, Fleming Island, FL! Located in a highly sought-after A-rat...	3 beds \| 2 baths \| 1,200 sq.ft.	$295,000	Airbnb cash on cash: 0.49% Traditional cash on cash: 3.87% Airbnb Rental Income: $1196 Traditional Rental Income: $1745 Airbnb ROI: 0.49% Traditional ROI: 3.87%
1940 BLUEBONNET Way Fleming Island, FL Welcome to Pace Island! Beautiful Home in Gated Community! Come visit this stunning 3-bedr...	3 beds \| 2 baths \| 1,954 sq.ft.	$449,000	Airbnb cash on cash: -0.55% Traditional cash on cash: 2.79% Airbnb Rental Income: $1196 Traditional Rental Income: $2210 Airbnb ROI: -0.55% Traditional ROI: 2.79%
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: -0.48% Traditional cash on cash: 3.86% Airbnb Rental Income: $1147 Traditional Rental Income: $2954 Airbnb ROI: -0.48% 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 \| N/A baths \| 2,855 sq.ft.	$566,000	Airbnb cash on cash: -0.94% Traditional cash on cash: 3.11% Airbnb Rental Income: $1147 Traditional Rental Income: $2908 Airbnb ROI: -0.94% Traditional ROI: 3.11%
2171 TRAILWOOD Drive Fleming Island, FL Welcome home to this beautifully upgraded 3 bedroom, 2 bath gem in the highly sought-after...	3 beds \| 2 baths \| 1,726 sq.ft.	$375,000	Airbnb cash on cash: -0.17% Traditional cash on cash: 3.37% Airbnb Rental Income: $1196 Traditional Rental Income: $2054 Airbnb ROI: -0.17% Traditional ROI: 3.37%
762 HIBERNIA FOREST Drive Fleming Island, FL UNDER CONTRACT BUT SELLER ACCEPTING BACK UP OFFERS !! CLOSING DEC 5th 2025,,,LARGE . 40 Ac...	3 beds \| 2 baths \| 1,586 sq.ft.	$399,900	Airbnb cash on cash: 0.02% Traditional cash on cash: 3.76% Airbnb Rental Income: $1196 Traditional Rental Income: $2209 Airbnb ROI: 0.02% Traditional ROI: 3.76%
4966 HARVEY GRANT Road Fleming Island, FL BACK ON MARKET NO FAULT OF SELLER! This home sits on over an acre in a quiet, established ...	3 beds \| 2 baths \| 2,116 sq.ft.	$399,999	Airbnb cash on cash: 0.02% Traditional cash on cash: 3.69% Airbnb Rental Income: $1196 Traditional Rental Income: $2185 Airbnb ROI: 0.02% Traditional ROI: 3.69%
932 CLAY Street Fleming Island, FL Welcome to this beautifully maintained 3400+ square foot home located in the heart of high...	3 beds \| 4 baths \| 3,438 sq.ft.	$695,000	Airbnb cash on cash: -0.65% Traditional cash on cash: 3.32% Airbnb Rental Income: $1196 Traditional Rental Income: $3379 Airbnb ROI: -0.65% Traditional ROI: 3.32%
2549 WHISPERING PINES Drive Fleming Island, FL Stunning pool home on the coveted 9th hole in Fleming Island Plantation! Step inside to a ...	4 beds \| 2 baths \| 2,451 sq.ft.	$575,000	Airbnb cash on cash: -1.15% Traditional cash on cash: 1.54% Airbnb Rental Income: $1147 Traditional Rental Income: $2212 Airbnb ROI: -1.15% Traditional ROI: 1.54%
1571 SHELTER COVE Drive Fleming Island, FL Charming, move-in ready home in the heart of Fleming Island's Eagle Harbor! This beautiful...	4 beds \| 2 baths \| 1,995 sq.ft.	$440,000	Airbnb cash on cash: -0.81% Traditional cash on cash: 3.83% Airbnb Rental Income: $1147 Traditional Rental Income: $2678 Airbnb ROI: -0.81% Traditional ROI: 3.83%
1479 SCARLETT Way Fleming Island, FL Welcome to 1479 Scarlet Way-an elegant, beautifully updated 4BR/3BA home in coveted Hibern...	4 beds \| 3 baths \| 3,392 sq.ft.	$850,000	Airbnb cash on cash: -0.93% Traditional cash on cash: 2.68% Airbnb Rental Income: $1147 Traditional Rental Income: $3623 Airbnb ROI: -0.93% Traditional ROI: 2.68%
627 MARTINIQUE Court Fleming Island, FL Move in just in time to create your Christmas memories in your new charming Fleming Island...	4 beds \| 2 baths \| 1,706 sq.ft.	$345,900	Airbnb cash on cash: -0.31% Traditional cash on cash: 3.98% Airbnb Rental Income: $1147 Traditional Rental Income: $2160 Airbnb ROI: -0.31% Traditional ROI: 3.98%
1734 COVINGTON Lane Fleming Island, FL Welcome to this well-maintained home featuring beautiful hand-scraped wood floors, detaile...	4 beds \| 2 baths \| 2,301 sq.ft.	$455,000	Airbnb cash on cash: -0.64% Traditional cash on cash: 3.14% Airbnb Rental Income: $1147 Traditional Rental Income: $2376 Airbnb ROI: -0.64% Traditional ROI: 3.14%
1798 COVINGTON Lane Fleming Island, FL Looking for space, style, and outdoor living that truly stands out? This beautifully maint...	4 beds \| 2 baths \| 3,119 sq.ft.	$480,000	Airbnb cash on cash: -0.59% Traditional cash on cash: 3.27% Airbnb Rental Income: $1147 Traditional Rental Income: $2502 Airbnb ROI: -0.59% Traditional ROI: 3.27%
1837 WESTON Circle Fleming Island, FL This light and airy open-concept floor plan is filled with natural light especially w/ rec...	3 beds \| 2 baths \| 1,904 sq.ft.	$385,000	Airbnb cash on cash: -0.05% Traditional cash on cash: 4.87% Airbnb Rental Income: $1196 Traditional Rental Income: $2586 Airbnb ROI: -0.05% Traditional ROI: 4.87%
410 LUCYS Lane Fleming Island, FL Welcome to the perfect blend of comfort, updates, and outdoor living! This beautifully mai...	3 beds \| 2 baths \| 1,610 sq.ft.	$370,000	Airbnb cash on cash: -0.05% Traditional cash on cash: 2.98% Airbnb Rental Income: $1196 Traditional Rental Income: $1860 Airbnb ROI: -0.05% Traditional ROI: 2.98%
1601 MAJESTIC VIEW Lane Fleming Island, FL AVAILABLE NOW! 2.75% Assumable VA Mortgage Dreams do come true with this corner lot ho...	4 beds \| 2 baths \| 2,532 sq.ft.	$430,000	Airbnb cash on cash: -0.87% Traditional cash on cash: 3.69% Airbnb Rental Income: $1147 Traditional Rental Income: $2605 Airbnb ROI: -0.87% Traditional ROI: 3.69%
2263 KEATON CHASE Drive Fleming Island, FL Beautiful home in the highly desirable Eagle Harbor community. Located in a premier golf c...	3 beds \| 2 baths \| 2,118 sq.ft.	$479,000	Airbnb cash on cash: -0.76% Traditional cash on cash: 3.39% Airbnb Rental Income: $1196 Traditional Rental Income: $2669 Airbnb ROI: -0.76% Traditional ROI: 3.39%
2639 SOPHIA Court Fleming Island, FL Pool home, cul-de-sac street, low HOA, and NO CDD fees! This home checks all the boxes on ...	4 beds \| 2 baths \| 2,242 sq.ft.	$499,900	Airbnb cash on cash: -0.59% Traditional cash on cash: 3.74% Airbnb Rental Income: $1147 Traditional Rental Income: $2794 Airbnb ROI: -0.59% Traditional ROI: 3.74%
1683 WATERS EDGE Drive Fleming Island, FL Nestled in the desirable community of Fleming Island, this beautifully maintained 4-bedroo...	4 beds \| 2 baths \| 2,566 sq.ft.	$665,000	Airbnb cash on cash: -1.36% Traditional cash on cash: 2.52% Airbnb Rental Income: $1147 Traditional Rental Income: $3175 Airbnb ROI: -1.36% Traditional ROI: 2.52%
1806 ROYAL FERN Lane Fleming Island, FL Experience Florida living in this fully renovated 4-bedroom, 2-bath brick home in the excl...	4 beds \| 2 baths \| 2,424 sq.ft.	$599,000	Airbnb cash on cash: -1.29% Traditional cash on cash: 2.48% Airbnb Rental Income: $1147 Traditional Rental Income: $2876 Airbnb ROI: -1.29% Traditional ROI: 2.48%
1279 PIRATES COVE Lane Fleming Island, FL Welcome to 1279 Pirates Cove Ln in Fleming Island's popular Harbor Island community - a be...	4 beds \| 2 baths \| 2,082 sq.ft.	$399,500	Airbnb cash on cash: -0.38% Traditional cash on cash: 3.71% Airbnb Rental Income: $1147 Traditional Rental Income: $2298 Airbnb ROI: -0.38% Traditional ROI: 3.71%
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: -1.56% Traditional cash on cash: -0.65% Airbnb Rental Income: $1147 Traditional Rental Income: $2648 Airbnb ROI: -1.56% Traditional ROI: -0.65%
1884 LAKE FOREST Lane Fleming Island, FL Short sale opportunity - NO SUB-TO** Price reduced! Exceptional opportunity to put you...	3 beds \| 2 baths \| 1,476 sq.ft.	$275,000	Airbnb cash on cash: -0.11% Traditional cash on cash: 4.11% Airbnb Rental Income: $1196 Traditional Rental Income: $1902 Airbnb ROI: -0.11% Traditional ROI: 4.11%
328 N RIDGE Drive Fleming Island, FL Welcome to this beautifully appointed 4-bedroom, 2.5-bath home set on a generous 0.52-acre...	4 beds \| 2 baths \| 2,276 sq.ft.	$515,000	Airbnb cash on cash: -0.94% Traditional cash on cash: 2.66% Airbnb Rental Income: $1147 Traditional Rental Income: $2500 Airbnb ROI: -0.94% Traditional ROI: 2.66%
560 MAJESTIC WOOD Drive Fleming Island, FL *Seller is offering $5k in Buyer concessions towards buyer's closing costs on offers accep...	4 beds \| 2 baths \| 2,049 sq.ft.	$363,000	Airbnb cash on cash: 0.25% Traditional cash on cash: 5.23% Airbnb Rental Income: $1147 Traditional Rental Income: $2464 Airbnb ROI: 0.25% Traditional ROI: 5.23%
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.	$690,000	Airbnb cash on cash: -0.14% Traditional cash on cash: 2.94% Airbnb Rental Income: $1147 Traditional Rental Income: $2748 Airbnb ROI: -0.14% Traditional ROI: 2.94%
1634 DOCKSIDE Drive Fleming Island, FL This ALL brick 5 bedroom 3.5 bath home with views of the pond is perfect for you! Complete...	5 beds \| N/A baths \| 2,572 sq.ft.	$518,000	Airbnb cash on cash: -0.86% Traditional cash on cash: 5.49% Airbnb Rental Income: $1213 Traditional Rental Income: $3899 Airbnb ROI: -0.86% Traditional ROI: 5.49%
2176 AUTUMN COVE Circle Fleming Island, FL *The Seller is willing to negotiate a new roof!!* Your dreams come true with this incr...	4 beds \| N/A baths \| 2,753 sq.ft.	$525,000	Airbnb cash on cash: -1.34% Traditional cash on cash: 3.83% Airbnb Rental Income: $1147 Traditional Rental Income: $3302 Airbnb ROI: -1.34% Traditional ROI: 3.83%
234 EVENTIDE Drive Fleming Island, FL MOTIVATED SELLERS! Home being sold as-is. Located on a quiet street this 4/2 POOL house, w...	4 beds \| 2 baths \| 2,478 sq.ft.	$495,000	Airbnb cash on cash: -0.3% Traditional cash on cash: 3.76% Airbnb Rental Income: $1147 Traditional Rental Income: $2645 Airbnb ROI: -0.3% Traditional ROI: 3.76%
149 RIVERWOOD Drive Fleming Island, FL Waterfront homes of this caliber on Fleming Island are few and far between, making this cu...	4 beds \| 2 baths \| 2,911 sq.ft.	$1,489,000	Airbnb cash on cash: -1.18% Traditional cash on cash: 0.81% Airbnb Rental Income: $1147 Traditional Rental Income: $3528 Airbnb ROI: -1.18% Traditional ROI: 0.81%
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: -0.63% Traditional cash on cash: 3.38% Airbnb Rental Income: $1213 Traditional Rental Income: $2884 Airbnb ROI: -0.63% Traditional ROI: 3.38%
6433 RIVER POINT Drive Fleming Island, FL Enjoy a worry-free life on the water! Completely remodeled 4 Bedroom/3Bath home with 100-f...	4 beds \| 3 baths \| 2,676 sq.ft.	$849,000	Airbnb cash on cash: -0.72% Traditional cash on cash: 2.79% Airbnb Rental Income: $1147 Traditional Rental Income: $3539 Airbnb ROI: -0.72% Traditional ROI: 2.79%
2479 PINEHURST Lane Fleming Island, FL This home is tucked on a quiet cul de sac in Southern Links and offers privacy, comfort, a...	4 beds \| 4 baths \| 2,808 sq.ft.	$529,000	Airbnb cash on cash: -0.62% Traditional cash on cash: 5.91% Airbnb Rental Income: $1147 Traditional Rental Income: $3995 Airbnb ROI: -0.62% Traditional ROI: 5.91%
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: -0.41% Traditional cash on cash: 7.36% Airbnb Rental Income: $1213 Traditional Rental Income: $4744 Airbnb ROI: -0.41% Traditional ROI: 7.36%
7685 RIVER Avenue Fleming Island, FL Welcome to your cutom built concrete block home on Fleming Island! No Cdd or Hoa. This spa...	4 beds \| N/A baths \| 2,507 sq.ft.	$595,000	Airbnb cash on cash: -0.71% Traditional cash on cash: 2.83% Airbnb Rental Income: $1147 Traditional Rental Income: $2730 Airbnb ROI: -0.71% Traditional ROI: 2.83%
2012 BELLE GROVE Terrace Fleming Island, FL You know you've been wanting to make the move to Fleming Island Plantation - now is your c...	4 beds \| 4 baths \| 2,808 sq.ft.	$480,000	Airbnb cash on cash: -1.28% Traditional cash on cash: 5.68% Airbnb Rental Income: $1147 Traditional Rental Income: $3896 Airbnb ROI: -1.28% Traditional ROI: 5.68%
1576 LINKSIDE Drive Fleming Island, FL PRICE REDUCTION Motivated Seller WITH Luxurious Upgrades in Fleming Island WITH A WATER VI...	4 beds \| 2 baths \| 2,373 sq.ft.	$669,000	Airbnb cash on cash: -0.98% Traditional cash on cash: 3.31% Airbnb Rental Income: $1147 Traditional Rental Income: $3444 Airbnb ROI: -0.98% Traditional ROI: 3.31%
1684 SANCTUARY Way Fleming Island, FL Welcome to your better than new luxury townhome that is still under warranty! This 2 year ...	3 beds \| 3 baths \| 1,980 sq.ft.	$378,000	Airbnb cash on cash: -0.17% Traditional cash on cash: 4.77% Airbnb Rental Income: $1196 Traditional Rental Income: $2561 Airbnb ROI: -0.17% Traditional ROI: 4.77%

Real Estate investment in Fleming-island, FL

There are 85 properties for sale in the city of Fleming Island . The median list price in Fleming Island is $450,000 and the average price per square foot is $200. In December 2025, the average monthly cash on cash return in Fleming Island is 4.00%. The average monthly rental income in Fleming Island is $2,396.

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

There are 85 investment properties available for sale in Fleming-island.

In 2025, 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 $1,196.

Your search for investment property begins and ends here

Investment Property for Sale in Fleming Island, FL

1815 ROYAL FERN Lane

Fleming Island, FL

4 beds | 2 baths | 2,080 sq.ft.

$459,000

Airbnb cash on cash: -0.53%

Traditional cash on cash: 3.43%

Airbnb Rental Income: $1147

Traditional Rental Income: $2468

Airbnb ROI: -0.53%

Traditional ROI: 3.43%

1000 FLEMING Street

Fleming Island, FL

3 beds | 2 baths | 1,200 sq.ft.

$295,000

Airbnb cash on cash: 0.49%

Traditional cash on cash: 3.87%

Airbnb Rental Income: $1196

Traditional Rental Income: $1745

Airbnb ROI: 0.49%

Traditional ROI: 3.87%

1940 BLUEBONNET Way

Fleming Island, FL

3 beds | 2 baths | 1,954 sq.ft.

$449,000

Airbnb cash on cash: -0.55%

Traditional cash on cash: 2.79%

Airbnb Rental Income: $1196

Traditional Rental Income: $2210

Airbnb ROI: -0.55%

Traditional ROI: 2.79%

1685 PINECREST Drive

Fleming Island, FL

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

$539,000

Airbnb cash on cash: -0.48%

Traditional cash on cash: 3.86%

Airbnb Rental Income: $1147

Traditional Rental Income: $2954

Airbnb ROI: -0.48%

Traditional ROI: 3.86%

2299 S BROOK Drive

Fleming Island, FL

4 beds | N/A baths | 2,855 sq.ft.

$566,000

Airbnb cash on cash: -0.94%

Traditional cash on cash: 3.11%

Airbnb Rental Income: $1147

Traditional Rental Income: $2908

Airbnb ROI: -0.94%

Traditional ROI: 3.11%

2171 TRAILWOOD Drive

Fleming Island, FL

3 beds | 2 baths | 1,726 sq.ft.

$375,000

Airbnb cash on cash: -0.17%

Traditional cash on cash: 3.37%

Airbnb Rental Income: $1196

Traditional Rental Income: $2054

Airbnb ROI: -0.17%

Traditional ROI: 3.37%

762 HIBERNIA FOREST Drive

Fleming Island, FL

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

$399,900

Airbnb cash on cash: 0.02%

Traditional cash on cash: 3.76%

Airbnb Rental Income: $1196

Traditional Rental Income: $2209

Airbnb ROI: 0.02%

Traditional ROI: 3.76%

4966 HARVEY GRANT Road

Fleming Island, FL

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

$399,999

Airbnb cash on cash: 0.02%

Traditional cash on cash: 3.69%

Airbnb Rental Income: $1196

Traditional Rental Income: $2185

Airbnb ROI: 0.02%