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 59 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.	$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%
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%
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%
1895 OSPREY BLUFF Boulevard Fleming Island, FL HIGH AND DRY!! Welcome to 1895 Osprey Bluff, quietly tucked away on Swimming Pen Creek, wh...	3 beds \| 2 baths \| 2,424 sq.ft.	$775,000	Airbnb cash on cash: -0.64% Traditional cash on cash: 1.49% Airbnb Rental Income: $1196 Traditional Rental Income: $2347 Airbnb ROI: -0.64% Traditional ROI: 1.49%
2287 EAGLE PERCH Place Fleming Island, FL Welcome to your Dream Home!!! A blend of elegance and modern luxury nestled in the heart o...	4 beds \| 4 baths \| 2,592 sq.ft.	$539,900	Airbnb cash on cash: -1.28% Traditional cash on cash: 3.59% Airbnb Rental Income: $1147 Traditional Rental Income: $3224 Airbnb ROI: -1.28% Traditional ROI: 3.59%
1628 MISTY LAKE Drive Fleming Island, FL Seller is open to entertaining offers! Three bedrooms plus office in desirable Eagle Harbo...	3 beds \| 3 baths \| 2,263 sq.ft.	$450,000	Airbnb cash on cash: -0.78% Traditional cash on cash: 3.97% Airbnb Rental Income: $1196 Traditional Rental Income: $2812 Airbnb ROI: -0.78% Traditional ROI: 3.97%

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.

$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%