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 65 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
6215 LEEWARD Court Fleming Island, FL Run don't walk! Move in ready Fleming Island Home perfectly situated to capture Sunsets at...	3 beds \| 3 baths \| 1,699 sq.ft.	$355,400	Airbnb cash on cash: 6.94% Traditional cash on cash: 4.2% Airbnb Rental Income: $4122 Traditional Rental Income: $2332 Airbnb ROI: 6.94% Traditional ROI: 4.2%
1968 WESTEND Place Fleming Island, FL Don't miss this Fleming Island Plantation pool home featuring 4 spacious bedrooms, 3.5 bat...	4 beds \| 4 baths \| 2,481 sq.ft.	$500,000	Airbnb cash on cash: 6.15% Traditional cash on cash: 4.29% Airbnb Rental Income: $5275 Traditional Rental Income: $3334 Airbnb ROI: 6.15% Traditional ROI: 4.29%
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.	$499,999	Airbnb cash on cash: 6.42% Traditional cash on cash: 5.59% Airbnb Rental Income: $5275 Traditional Rental Income: $3820 Airbnb ROI: 6.42% Traditional ROI: 5.59%
514 LOS PALMAS Drive Fleming Island, FL Nestled in the heart of sought-after Fleming Island, this beautiful 4-bedroom, 2.5-bath ho...	4 beds \| 3 baths \| 2,156 sq.ft.	$475,000	Airbnb cash on cash: 6.99% Traditional cash on cash: 2.81% Airbnb Rental Income: $5275 Traditional Rental Income: $2346 Airbnb ROI: 6.99% Traditional ROI: 2.81%
2390 STOCKTON Drive Fleming Island, FL This home has been meticulously upgraded with high-end finishes and thoughtful improvement...	4 beds \| 3 baths \| 2,720 sq.ft.	$785,000	Airbnb cash on cash: 3.89% Traditional cash on cash: 2.9% Airbnb Rental Income: $5275 Traditional Rental Income: $3481 Airbnb ROI: 3.89% Traditional ROI: 2.9%
2358 BRIDGETTE Way Fleming Island, FL Massive price adjustment due to seller purchasing another home!! 1.3 acre meticulously mai...	3 beds \| 3 baths \| 3,653 sq.ft.	$1,149,000	Airbnb cash on cash: 0.75% Traditional cash on cash: 1% Airbnb Rental Income: $4122 Traditional Rental Income: $3505 Airbnb ROI: 0.75% Traditional ROI: 1%
1798 COVINGTON Lane Fleming Island, FL Looking for plenty of space inside and out with exceptional value? This Fleming Island Pla...	3 beds \| 2 baths \| 2,591 sq.ft.	$400,000	Airbnb cash on cash: 6.04% Traditional cash on cash: 4% Airbnb Rental Income: $4122 Traditional Rental Income: $2478 Airbnb ROI: 6.04% Traditional ROI: 4%
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: 6.14% Traditional cash on cash: 3.58% Airbnb Rental Income: $4122 Traditional Rental Income: $2292 Airbnb ROI: 6.14% Traditional ROI: 3.58%
2470 COUNTRY SIDE Drive Fleming Island, FL OPEN HOUSE 5/16 11 TO 1. Located in Eagle Creek at Eagle Harbor, this spacious 4-bedroom h...	4 beds \| 4 baths \| 3,136 sq.ft.	$575,000	Airbnb cash on cash: 5.09% Traditional cash on cash: 3.77% Airbnb Rental Income: $5275 Traditional Rental Income: $3496 Airbnb ROI: 5.09% Traditional ROI: 3.77%
1472 MARSH RABBIT Way Fleming Island, FL Nestled on a quiet cul-de-sac in gated Pace Island, this contemporary home offers peaceful...	3 beds \| 2 baths \| 1,777 sq.ft.	$399,500	Airbnb cash on cash: 6.9% Traditional cash on cash: 4.92% Airbnb Rental Income: $4122 Traditional Rental Income: $2508 Airbnb ROI: 6.9% Traditional ROI: 4.92%
2408 STOCKTON Drive Fleming Island, FL Split floor plan w/ 2 PRIMARY SUITES, dedicated office w/ large closet (potential 5th bedr...	4 beds \| 4 baths \| 3,006 sq.ft.	$850,000	Airbnb cash on cash: 2.82% Traditional cash on cash: 3.25% Airbnb Rental Income: $5275 Traditional Rental Income: $4546 Airbnb ROI: 2.82% Traditional ROI: 3.25%
1916 VISTA LAKES Drive Fleming Island, FL Open House Saturday May 23rd 11:00-2:00 This immaculate Eagle Harbor 4 bedroom, 3 bath...	4 beds \| 3 baths \| 2,536 sq.ft.	$574,000	Airbnb cash on cash: 5.48% Traditional cash on cash: 2.65% Airbnb Rental Income: $5275 Traditional Rental Income: $2686 Airbnb ROI: 5.48% Traditional ROI: 2.65%
1819 SENTRY OAK Court Fleming Island, FL Welcome to the desirable gated community of Margarets Walk. This beautiful well maintained...	4 beds \| 3 baths \| 2,170 sq.ft.	$479,000	Airbnb cash on cash: 6.32% Traditional cash on cash: 2.86% Airbnb Rental Income: $5275 Traditional Rental Income: $2659 Airbnb ROI: 6.32% Traditional ROI: 2.86%
1908 FOX GLOVE Lane Fleming Island, FL Located within the gated Pace Island community in Fleming Island, this beautifully maintai...	4 beds \| 3 baths \| 2,489 sq.ft.	$645,000	Airbnb cash on cash: 4.4% Traditional cash on cash: 1.86% Airbnb Rental Income: $5275 Traditional Rental Income: $2673 Airbnb ROI: 4.4% Traditional ROI: 1.86%
1574 COUNTRY WALK Drive Fleming Island, FL Set along the award-winning Eagle Harbor golf course in Fleming Island & minutes from Jack...	5 beds \| 4 baths \| 2,912 sq.ft.	$775,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.74% Airbnb Rental Income: $null Traditional Rental Income: $3148 Airbnb ROI: N/A Traditional ROI: 1.74%
1631 SETON FAMILY Walk Fleming Island, FL Distinctive 1-story residence in Fleming Estates (NOT a CDD community), built by Riverside...	4 beds \| 3 baths \| 2,918 sq.ft.	$769,500	Airbnb cash on cash: 3.34% Traditional cash on cash: 1.35% Airbnb Rental Income: $5275 Traditional Rental Income: $2776 Airbnb ROI: 3.34% Traditional ROI: 1.35%
413 RIVER BIRCH Lane Fleming Island, FL OPEN HOUSE SATURDAY 12 PM - 3 PM Welcome to this charming custom brick home in Christoph...	3 beds \| 3 baths \| 3,123 sq.ft.	$787,000	Airbnb cash on cash: 2.34% Traditional cash on cash: 3.25% Airbnb Rental Income: $4122 Traditional Rental Income: $3911 Airbnb ROI: 2.34% Traditional ROI: 3.25%
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.	$750,000	Airbnb cash on cash: 4.24% Traditional cash on cash: 4.1% Airbnb Rental Income: $5275 Traditional Rental Income: $4109 Airbnb ROI: 4.24% Traditional ROI: 4.1%
1576 LINKSIDE Drive Fleming Island, FL Whole house Generator year round, newer roof, comfort,Luxurious Upgrades in Fleming Island...	4 beds \| 3 baths \| 2,373 sq.ft.	$600,000	Airbnb cash on cash: 5.12% Traditional cash on cash: 2.86% Airbnb Rental Income: $5275 Traditional Rental Income: $2937 Airbnb ROI: 5.12% Traditional ROI: 2.86%
182 MALLEY COVE Lane Fleming Island, FL NO HOA OR CDDOPEN CONCEPTNEWLY REMODELED Welcome home to this stunning retreat, wh...	5 beds \| 4 baths \| 3,316 sq.ft.	$775,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.56% Airbnb Rental Income: $null Traditional Rental Income: $3848 Airbnb ROI: N/A Traditional ROI: 3.56%
1862 SENTRY OAK Court Fleming Island, FL POOL HOME with 3 CAR GARAGE in the sought-after Margaret's Walk community. Step inside to ...	4 beds \| 3 baths \| 2,272 sq.ft.	$485,000	Airbnb cash on cash: 6.93% Traditional cash on cash: 6.52% Airbnb Rental Income: $5275 Traditional Rental Income: $4021 Airbnb ROI: 6.93% Traditional ROI: 6.52%
170 N RIDGE Drive Fleming Island, FL Rare riverfront opportunity with almost an acre of land in Fleming Island. This 5BR, appro...	5 beds \| 3 baths \| 4,005 sq.ft.	$1,263,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.05% Airbnb Rental Income: $null Traditional Rental Income: $3263 Airbnb ROI: N/A Traditional ROI: 1.05%
1850 WATERBURY Lane Fleming Island, FL NEW PRICE AND OPEN SAT 4/18 AND SUN 4/19 FROM 1-3! Welcome to 1850 Waterbury Lane, a beaut...	4 beds \| 3 baths \| 2,345 sq.ft.	$874,999	Airbnb cash on cash: 2.85% Traditional cash on cash: 1.72% Airbnb Rental Income: $5275 Traditional Rental Income: $3291 Airbnb ROI: 2.85% Traditional ROI: 1.72%
397 FLEMING Drive Fleming Island, FL New Roof on Home and Back Porch installed on 4/13/2026! Welcome home to this beautiful...	3 beds \| 2 baths \| 1,674 sq.ft.	$439,000	Airbnb cash on cash: 6.26% Traditional cash on cash: 4.96% Airbnb Rental Income: $4122 Traditional Rental Income: $2712 Airbnb ROI: 6.26% Traditional ROI: 4.96%
2012 ARDEN FOREST Place Fleming Island, FL Located in Eagle Nest Preserve at Eagle Harbor, this 4-bedroom, 3-bath home built in 2018 ...	4 beds \| 3 baths \| 2,341 sq.ft.	$529,999	Airbnb cash on cash: 6.29% Traditional cash on cash: 5.1% Airbnb Rental Income: $5275 Traditional Rental Income: $3617 Airbnb ROI: 6.29% Traditional ROI: 5.1%
2408 GOLDEN BELL Lane Fleming Island, FL Investors, discover the potential this home holds with just a touch of TLC. Located on a q...	5 beds \| 3 baths \| 3,696 sq.ft.	$550,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.28% Airbnb Rental Income: $null Traditional Rental Income: $3860 Airbnb ROI: N/A Traditional ROI: 5.28%
2076 BELLE GROVE Terrace Fleming Island, FL Nestled in the serene charm of Fleming Island, Florida, this remarkable residence presents...	5 beds \| 3 baths \| 3,573 sq.ft.	$495,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.73% Airbnb Rental Income: $null Traditional Rental Income: $3252 Airbnb ROI: N/A Traditional ROI: 3.73%

Your search for investment property begins and ends here

Single Family Homes for Sale in Fleming Island, FL

6215 LEEWARD Court

Fleming Island, FL

3 beds | 3 baths | 1,699 sq.ft.

$355,400

Airbnb cash on cash: 6.94%

Traditional cash on cash: 4.2%

Airbnb Rental Income: $4122

Traditional Rental Income: $2332

Airbnb ROI: 6.94%

Traditional ROI: 4.2%

1968 WESTEND Place

Fleming Island, FL

4 beds | 4 baths | 2,481 sq.ft.

$500,000

Airbnb cash on cash: 6.15%

Traditional cash on cash: 4.29%

Airbnb Rental Income: $5275

Traditional Rental Income: $3334

Airbnb ROI: 6.15%

Traditional ROI: 4.29%

2299 S BROOK Drive

Fleming Island, FL

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

$499,999

Airbnb cash on cash: 6.42%

Traditional cash on cash: 5.59%

Airbnb Rental Income: $5275

Traditional Rental Income: $3820

Airbnb ROI: 6.42%

Traditional ROI: 5.59%

514 LOS PALMAS Drive

Fleming Island, FL

4 beds | 3 baths | 2,156 sq.ft.

$475,000

Airbnb cash on cash: 6.99%

Traditional cash on cash: 2.81%

Airbnb Rental Income: $5275

Traditional Rental Income: $2346

Airbnb ROI: 6.99%

Traditional ROI: 2.81%

2390 STOCKTON Drive

Fleming Island, FL

4 beds | 3 baths | 2,720 sq.ft.

$785,000

Airbnb cash on cash: 3.89%

Traditional cash on cash: 2.9%

Airbnb Rental Income: $5275

Traditional Rental Income: $3481

Airbnb ROI: 3.89%

Traditional ROI: 2.9%

2358 BRIDGETTE Way

Fleming Island, FL

3 beds | 3 baths | 3,653 sq.ft.

$1,149,000

Airbnb cash on cash: 0.75%

Traditional cash on cash: 1%

Airbnb Rental Income: $4122

Traditional Rental Income: $3505

Airbnb ROI: 0.75%

Traditional ROI: 1%

1798 COVINGTON Lane

Fleming Island, FL

3 beds | 2 baths | 2,591 sq.ft.

$400,000

Airbnb cash on cash: 6.04%

Traditional cash on cash: 4%

Airbnb Rental Income: $4122

Traditional Rental Income: $2478

Airbnb ROI: 6.04%

Traditional ROI: 4%

1589 Calming Water Drive

Fleming Island, FL

3 beds | 2 baths | 1,646 sq.ft.

$399,000

Airbnb cash on cash: 6.14%

Traditional cash on cash: 3.58%

Airbnb Rental Income: $4122

Traditional Rental Income: $2292

Airbnb ROI: 6.14%