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.

Single Family Homes for Sale in Fleming Island, FL

Search for Single Family Residential for Sale in Fleming Island, Florida. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 75 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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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%
884 LIVE OAK Lane Fleming Island, FL Charming home in Hibernia Oaks! Nestled in the heart of the desirable Hibernia Oaks neighb...	3 beds \| 2 baths \| 1,572 sq.ft.	$385,000	Airbnb cash on cash: -0.06% Traditional cash on cash: 3.98% Airbnb Rental Income: $1196 Traditional Rental Income: $2264 Airbnb ROI: -0.06% Traditional ROI: 3.98%

Your search for investment property begins and ends here

Single Family Homes 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%