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.	$445,000	Airbnb cash on cash: -0.52% Traditional cash on cash: 3.57% Airbnb Rental Income: $1147 Traditional Rental Income: $2468 Airbnb ROI: -0.52% Traditional ROI: 3.57%
2020 BELLE GROVE Trace Fleming Island, FL Located in the desirable Thornhill subdivision of Fleming Island Plantation, this spacious...	4 beds \| 3 baths \| 2,366 sq.ft.	$529,900	Airbnb cash on cash: -1.02% Traditional cash on cash: 3.89% Airbnb Rental Income: $1147 Traditional Rental Income: $3201 Airbnb ROI: -1.02% Traditional ROI: 3.89%
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 \| 2 baths \| 2,855 sq.ft.	$556,000	Airbnb cash on cash: -0.94% Traditional cash on cash: 3.18% Airbnb Rental Income: $1147 Traditional Rental Income: $2908 Airbnb ROI: -0.94% Traditional ROI: 3.18%
932 CLAY Street Fleming Island, FL Welcome to this beautifully maintained 3400+ square foot home located in the heart of high...	4 beds \| 4 baths \| 3,438 sq.ft.	$679,500	Airbnb cash on cash: -0.71% Traditional cash on cash: 3.42% Airbnb Rental Income: $1147 Traditional Rental Income: $3379 Airbnb ROI: -0.71% Traditional ROI: 3.42%
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%
1991 WOODLAKE Drive Fleming Island, FL Stunning JA Long custom, all-brick home situated on the 17th fairway in the highly desirab...	4 beds \| 4 baths \| 3,514 sq.ft.	$625,000	Airbnb cash on cash: -0.83% Traditional cash on cash: 5.94% Airbnb Rental Income: $1147 Traditional Rental Income: $4716 Airbnb ROI: -0.83% Traditional ROI: 5.94%
1358 BROOKGREEN Way Fleming Island, FL Discover this beautifully updated and affordable Fleming Island home with an amazing locat...	3 beds \| 2 baths \| 1,666 sq.ft.	$375,000	Airbnb cash on cash: -0.35% Traditional cash on cash: 3.07% Airbnb Rental Income: $1196 Traditional Rental Income: $2013 Airbnb ROI: -0.35% Traditional ROI: 3.07%
2918 GRANDE OAKS Way Fleming Island, FL Discover resort-style living in this gorgeous, move-in-ready 5-bedroom, 4-bath home locate...	5 beds \| 4 baths \| 2,922 sq.ft.	$669,000	Airbnb cash on cash: -0.98% Traditional cash on cash: 4.95% Airbnb Rental Income: $1213 Traditional Rental Income: $4525 Airbnb ROI: -0.98% Traditional ROI: 4.95%
1316 HOLMES LANDING Drive Fleming Island, FL Love where you live-nestled in the desirable Eagle Harbor neighborhood, this beautiful 4-b...	4 beds \| 3 baths \| 2,346 sq.ft.	$490,000	Airbnb cash on cash: -0.51% Traditional cash on cash: 3.49% Airbnb Rental Income: $1147 Traditional Rental Income: $2599 Airbnb ROI: -0.51% Traditional ROI: 3.49%
1589 Calming Water Drive Fleming Island, FL Beautifully upgraded three-bedroom, two-bathroom villa in the highly desirable Lake Ridge ...	3 beds \| 2 baths \| 1,646 sq.ft.	$399,000	Airbnb cash on cash: -0.38% Traditional cash on cash: 2.04% Airbnb Rental Income: $1196 Traditional Rental Income: $1713 Airbnb ROI: -0.38% Traditional ROI: 2.04%
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.	$370,000	Airbnb cash on cash: -0.02% Traditional cash on cash: 5.11% Airbnb Rental Income: $1196 Traditional Rental Income: $2586 Airbnb ROI: -0.02% Traditional ROI: 5.11%
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.	$365,000	Airbnb cash on cash: -0.04% Traditional cash on cash: 3.47% Airbnb Rental Income: $1196 Traditional Rental Income: $2011 Airbnb ROI: -0.04% Traditional ROI: 3.47%
1858 SENTRY OAK Court Fleming Island, FL Discover the perfect blend of luxury, comfort, and resort-style living in this beautifully...	4 beds \| 3 baths \| 2,530 sq.ft.	$559,000	Airbnb cash on cash: -0.69% Traditional cash on cash: 4.31% Airbnb Rental Income: $1147 Traditional Rental Income: $3378 Airbnb ROI: -0.69% Traditional ROI: 4.31%
870 HIBERNIA FOREST Drive Fleming Island, FL WELCOME TO YOUR OWN SLICE OF PARADISE IN THE HEART OF COVETED FLEMING ISLAND, FL!! This be...	3 beds \| 2 baths \| 1,400 sq.ft.	$354,900	Airbnb cash on cash: 0.15% Traditional cash on cash: 3.41% Airbnb Rental Income: $1196 Traditional Rental Income: $1895 Airbnb ROI: 0.15% Traditional ROI: 3.41%
2480 STONEY GLEN Drive Fleming Island, FL All brick two-story Eagle Harbor home with pond and fairway views! The spacious yard and t...	3 beds \| 4 baths \| 2,876 sq.ft.	$570,000	Airbnb cash on cash: -1.68% Traditional cash on cash: 4.28% Airbnb Rental Income: $1196 Traditional Rental Income: $3981 Airbnb ROI: -1.68% Traditional ROI: 4.28%
2169 ARDEN FOREST Place Fleming Island, FL This rare, single-story, modern pool home in Eagle Nest Preserve offers a thoughtfully des...	4 beds \| 3 baths \| 2,823 sq.ft.	$699,000	Airbnb cash on cash: -1.49% Traditional cash on cash: 2.24% Airbnb Rental Income: $1147 Traditional Rental Income: $3198 Airbnb ROI: -1.49% Traditional ROI: 2.24%
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%
2231 TRAILWOOD Drive Fleming Island, FL Multiple offers received. Please submit offers by 12:00 pm Sunday 1/18/26. This beautifull...	3 beds \| 2 baths \| 1,669 sq.ft.	$400,000	Airbnb cash on cash: -0.72% Traditional cash on cash: 3.1% Airbnb Rental Income: $1196 Traditional Rental Income: $2242 Airbnb ROI: -0.72% Traditional ROI: 3.1%
1279 Pirates Cove Ln Fleming Island, FL Buy This Home & I'll Buy Yours! Buy this home if YOU Are Not Satisfied in 24 Months I'LL B...	4 beds \| 2 baths \| 2,082 sq.ft.	$325,000	Airbnb cash on cash: -0.17% Traditional cash on cash: 4.84% Airbnb Rental Income: $1147 Traditional Rental Income: $2298 Airbnb ROI: -0.17% Traditional ROI: 4.84%
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%
770 HIBERNIA Road Fleming Island, FL SHORT SALE - Incredible Opportunity! Spacious 4-bedroom home with oversized den, 3 full ba...	5 beds \| 3 baths \| 2,900 sq.ft.	$350,000	Airbnb cash on cash: -0.06% Traditional cash on cash: 6.42% Airbnb Rental Income: $1213 Traditional Rental Income: $2954 Airbnb ROI: -0.06% Traditional ROI: 6.42%
328 N RIDGE Drive Fleming Island, FL Welcome to this charming and thoughtfully updated 4-bedroom, 2.5-bath home on a spacious 0...	4 beds \| 2 baths \| 2,276 sq.ft.	$500,000	Airbnb cash on cash: -0.97% Traditional cash on cash: 2.73% Airbnb Rental Income: $1147 Traditional Rental Income: $2500 Airbnb ROI: -0.97% Traditional ROI: 2.73%
2418 SOUTHERN LINKS Drive Fleming Island, FL Situated in the highly sought-after Fleming Island Plantation, this beautifully maintained...	4 beds \| 3 baths \| 2,605 sq.ft.	$510,000	Airbnb cash on cash: -1.38% Traditional cash on cash: 2.6% Airbnb Rental Income: $1147 Traditional Rental Income: $2665 Airbnb ROI: -1.38% Traditional ROI: 2.6%
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.	$1,390,000	Airbnb cash on cash: -1.2% Traditional cash on cash: 0.94% Airbnb Rental Income: $1147 Traditional Rental Income: $3528 Airbnb ROI: -1.2% Traditional ROI: 0.94%
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 your ultimate Florida lifestyle on the water in this remodeled 4 Bed/3 Bath single-s...	4 beds \| 3 baths \| 2,676 sq.ft.	$825,000	Airbnb cash on cash: -0.71% Traditional cash on cash: 2.89% Airbnb Rental Income: $1147 Traditional Rental Income: $3539 Airbnb ROI: -0.71% Traditional ROI: 2.89%
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.	$649,000	Airbnb cash on cash: -0.98% Traditional cash on cash: 3.44% Airbnb Rental Income: $1147 Traditional Rental Income: $3444 Airbnb ROI: -0.98% Traditional ROI: 3.44%
1912 BLUEBONNET Way Fleming Island, FL Welcome Home! Step into comfort and peace of mind with this beautifully updated home nestl...	3 beds \| 2 baths \| 1,964 sq.ft.	$499,000	Airbnb cash on cash: -0.61% Traditional cash on cash: 2.46% Airbnb Rental Income: $1196 Traditional Rental Income: $2241 Airbnb ROI: -0.61% Traditional ROI: 2.46%
2025 CASTLE POINT Court Fleming Island, FL Located in the gated community of Romeo Point with access to Eagle Harbor amenities with p...	5 beds \| 4 baths \| 3,042 sq.ft.	$645,000	Airbnb cash on cash: -0.62% Traditional cash on cash: 3.9% Airbnb Rental Income: $1213 Traditional Rental Income: $3544 Airbnb ROI: -0.62% Traditional ROI: 3.9%
136 HOLLYWOOD FOREST Drive Fleming Island, FL Major Updates Complete \| All-Brick Ranch \| Cedar Framing \| No HOA Move forward with confid...	3 beds \| 2 baths \| 1,659 sq.ft.	$425,000	Airbnb cash on cash: 0.19% Traditional cash on cash: 3.05% Airbnb Rental Income: $1196 Traditional Rental Income: $1947 Airbnb ROI: 0.19% Traditional ROI: 3.05%
1500 CALMING WATER Drive unit: 5503 #5503 Fleming Island, FL Priced to sell! Motivated Seller! This 3/2.5 bath townhome in highly sought after Lake Rid...	3 beds \| 2 baths \| 1,492 sq.ft.	$222,500	Airbnb cash on cash: 0.61% Traditional cash on cash: 5.65% Airbnb Rental Income: $1196 Traditional Rental Income: $1868 Airbnb ROI: 0.61% Traditional ROI: 5.65%
1608 DOCKSIDE Drive Fleming Island, FL BUYER BONUS $5,000 toward buyer closing costs, rate buy down, you decide, with acceptable ...	4 beds \| 2 baths \| 1,710 sq.ft.	$399,000	Airbnb cash on cash: 0.15% Traditional cash on cash: 4.77% Airbnb Rental Income: $1147 Traditional Rental Income: $2494 Airbnb ROI: 0.15% Traditional ROI: 4.77%
1900 COPPER STONE Drive unit: C #C Fleming Island, FL Discover this charming two-story Eagle Harbor townhome, move-in ready with recent upgrades...	3 beds \| 2 baths \| 2,029 sq.ft.	$315,000	Airbnb cash on cash: 0.24% Traditional cash on cash: 6.1% Airbnb Rental Income: $1196 Traditional Rental Income: $2542 Airbnb ROI: 0.24% Traditional ROI: 6.1%
1860 COPPER STONE Drive unit: C #C Fleming Island, FL NEW FLOORING THROUGHOUT AND NEW INTERIOR PAINT!!! Enjoy low-maintenance living in this two...	3 beds \| 2 baths \| 2,029 sq.ft.	$315,000	Airbnb cash on cash: 0.25% Traditional cash on cash: 5.48% Airbnb Rental Income: $1196 Traditional Rental Income: $2358 Airbnb ROI: 0.25% Traditional ROI: 5.48%
1665 CINNAMON FERN Court Fleming Island, FL Don't miss this beautifully maintained 4-bedroom, 2-bath home, built by Sid Higginbotham, ...	4 beds \| 2 baths \| 2,051 sq.ft.	$425,000	Airbnb cash on cash: -0.58% Traditional cash on cash: 3.42% Airbnb Rental Income: $1147 Traditional Rental Income: $2360 Airbnb ROI: -0.58% Traditional ROI: 3.42%
2111 AUTUMN COVE Circle Fleming Island, FL Impressive executive home with thoughtful floor plan, high-end touches & features througho...	5 beds \| 5 baths \| 4,182 sq.ft.	$725,000	Airbnb cash on cash: -0.97% Traditional cash on cash: 7.5% Airbnb Rental Income: $1213 Traditional Rental Income: $6546 Airbnb ROI: -0.97% Traditional ROI: 7.5%
1727 MARGARETS WALK Road Fleming Island, FL Beautiful move-in ready home in the highly sought after gated community of Margaret's Walk...	3 beds \| 2 baths \| 2,015 sq.ft.	$448,000	Airbnb cash on cash: -0.37% Traditional cash on cash: 3.21% Airbnb Rental Income: $1196 Traditional Rental Income: $2310 Airbnb ROI: -0.37% Traditional ROI: 3.21%

Real Estate investment in Fleming-island, FL

There are 72 properties for sale in the city of Fleming Island . The median list price in Fleming Island is $449,000 and the average price per square foot is $197. In February 2026, the average monthly cash on cash return in Fleming Island is 4.00%. The average monthly rental income in Fleming Island is $2,394.

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

There are 72 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 $1,196.

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.

$445,000

Airbnb cash on cash: -0.52%

Traditional cash on cash: 3.57%

Airbnb Rental Income: $1147

Traditional Rental Income: $2468

Airbnb ROI: -0.52%

Traditional ROI: 3.57%

2020 BELLE GROVE Trace

Fleming Island, FL

4 beds | 3 baths | 2,366 sq.ft.

$529,900

Airbnb cash on cash: -1.02%

Traditional cash on cash: 3.89%

Airbnb Rental Income: $1147

Traditional Rental Income: $3201

Airbnb ROI: -1.02%

Traditional ROI: 3.89%

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 | 2 baths | 2,855 sq.ft.

$556,000

Airbnb cash on cash: -0.94%

Traditional cash on cash: 3.18%

Airbnb Rental Income: $1147

Traditional Rental Income: $2908

Airbnb ROI: -0.94%

Traditional ROI: 3.18%

932 CLAY Street

Fleming Island, FL

4 beds | 4 baths | 3,438 sq.ft.

$679,500

Airbnb cash on cash: -0.71%

Traditional cash on cash: 3.42%

Airbnb Rental Income: $1147

Traditional Rental Income: $3379

Airbnb ROI: -0.71%

Traditional ROI: 3.42%

2549 WHISPERING PINES Drive

Fleming Island, FL

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%

1991 WOODLAKE Drive

Fleming Island, FL

4 beds | 4 baths | 3,514 sq.ft.

$625,000

Airbnb cash on cash: -0.83%

Traditional cash on cash: 5.94%

Airbnb Rental Income: $1147

Traditional Rental Income: $4716

Airbnb ROI: -0.83%

Traditional ROI: 5.94%

1358 BROOKGREEN Way

Fleming Island, FL

3 beds | 2 baths | 1,666 sq.ft.

$375,000

Airbnb cash on cash: -0.35%

Traditional cash on cash: 3.07%

Airbnb Rental Income: $1196

Traditional Rental Income: $2013

Airbnb ROI: -0.35%