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
1565 ROYAL FERN Lane Fleming Island, FL Welcome to this beautifully maintained all brick home nestled in the highly sought-after g...	4 beds \| 2 baths \| 2,331 sq.ft.	$495,000	Airbnb cash on cash: 3.07% Traditional cash on cash: 2.99% Airbnb Rental Income: $3257 Traditional Rental Income: $2487 Airbnb ROI: 3.07% Traditional ROI: 2.99%
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.	$469,000	Airbnb cash on cash: 2.7% Traditional cash on cash: 2.63% Airbnb Rental Income: $2916 Traditional Rental Income: $2210 Airbnb ROI: 2.7% Traditional ROI: 2.63%
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: 3.01% Traditional cash on cash: 3.86% Airbnb Rental Income: $3257 Traditional Rental Income: $2954 Airbnb ROI: 3.01% 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.	$576,000	Airbnb cash on cash: 2.32% Traditional cash on cash: 3.03% Airbnb Rental Income: $3257 Traditional Rental Income: $2908 Airbnb ROI: 2.32% Traditional ROI: 3.03%
1207 STERN Way Fleming Island, FL JUST LISTED in Harbor Island community of Fleming Island! BUYER INCENTIVE: SELLER PAYING u...	4 beds \| 2 baths \| 1,764 sq.ft.	$309,900	Airbnb cash on cash: 5.81% Traditional cash on cash: 5.12% Airbnb Rental Income: $3257 Traditional Rental Income: $2326 Airbnb ROI: 5.81% Traditional ROI: 5.12%
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.	$379,000	Airbnb cash on cash: 3.85% Traditional cash on cash: 3.33% Airbnb Rental Income: $2916 Traditional Rental Income: $2054 Airbnb ROI: 3.85% Traditional ROI: 3.33%
132 MALLEY COVE Lane Fleming Island, FL Custom-built, ADA-friendly home in the heart of Fleming Island with no HOA or CDD fees. Qu...	4 beds \| 4 baths \| 4,184 sq.ft.	$1,100,000	Airbnb cash on cash: 0.6% Traditional cash on cash: 1.96% Airbnb Rental Income: $3257 Traditional Rental Income: $3922 Airbnb ROI: 0.6% Traditional ROI: 1.96%
4966 HARVEY GRANT Road Fleming Island, FL This home sits on over an acre in a quiet, established neighborhood directly across from t...	3 beds \| 2 baths \| 2,116 sq.ft.	$399,999	Airbnb cash on cash: 3.84% Traditional cash on cash: 3.69% Airbnb Rental Income: $2916 Traditional Rental Income: $2185 Airbnb ROI: 3.84% Traditional ROI: 3.69%
2746 Archer Street Fleming Island, FL Welcome to this well-maintained 4-bedroom, 2-bath home tucked in a quiet cul-de-sac. Updat...	4 beds \| 2 baths \| 1,799 sq.ft.	$375,000	Airbnb cash on cash: 5.15% Traditional cash on cash: 4.17% Airbnb Rental Income: $3257 Traditional Rental Income: $2180 Airbnb ROI: 5.15% Traditional ROI: 4.17%
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: 3.46% Traditional cash on cash: 3.83% Airbnb Rental Income: $3257 Traditional Rental Income: $2678 Airbnb ROI: 3.46% Traditional ROI: 3.83%
1477 GREENWAY Place Fleming Island, FL Massive Price Reduction! Great 3 Bedroom 2 bath home in Fleming Island Plantation! Roof re...	3 beds \| 2 baths \| 1,922 sq.ft.	$325,000	Airbnb cash on cash: 3.98% Traditional cash on cash: 3.56% Airbnb Rental Income: $2916 Traditional Rental Income: $2113 Airbnb ROI: 3.98% Traditional ROI: 3.56%
1798 COVINGTON Lane Fleming Island, FL Looking for space, style, and unbeatable outdoor living? This must-see home in Fleming Isl...	4 beds \| 2 baths \| 3,119 sq.ft.	$480,000	Airbnb cash on cash: 3.32% Traditional cash on cash: 3.27% Airbnb Rental Income: $3257 Traditional Rental Income: $2502 Airbnb ROI: 3.32% Traditional ROI: 3.27%
2918 GRANDE OAKS Way Fleming Island, FL OPEN HOUSE - October 11, 12pm to 3pm!! Your private Florida resort awaits in Margaret's Wa...	5 beds \| 4 baths \| 2,922 sq.ft.	$680,000	Airbnb cash on cash: 4.46% Traditional cash on cash: 4.85% Airbnb Rental Income: $5355 Traditional Rental Income: $4525 Airbnb ROI: 4.46% Traditional ROI: 4.85%
1630 HIGHLAND VIEW Court Fleming Island, FL PAID OFF CDD BOND!WORLD CLASS AMENITIES!** No need to look any further! This immaculat...	4 beds \| 3 baths \| 2,031 sq.ft.	$445,000	Airbnb cash on cash: 4.03% Traditional cash on cash: 4.25% Airbnb Rental Income: $3257 Traditional Rental Income: $2614 Airbnb ROI: 4.03% Traditional ROI: 4.25%
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.	$395,000	Airbnb cash on cash: 3.79% Traditional cash on cash: 4.72% Airbnb Rental Income: $2916 Traditional Rental Income: $2586 Airbnb ROI: 3.79% Traditional ROI: 4.72%
1601 MAJESTIC VIEW Lane Fleming Island, FL 2.7% Assumable VA Mortgage Dreams do come true with this corner lot home in the sought...	4 beds \| N/A baths \| 2,532 sq.ft.	$450,000	Airbnb cash on cash: 3.3% Traditional cash on cash: 3.49% Airbnb Rental Income: $3257 Traditional Rental Income: $2605 Airbnb ROI: 3.3% Traditional ROI: 3.49%
1683 WATERS EDGE Drive Fleming Island, FL Nestled in the desirable community of Fleming Island, this beautifully maintained 4-bedroo...	4 beds \| N/A baths \| 2,566 sq.ft.	$665,000	Airbnb cash on cash: 1.47% Traditional cash on cash: 2.52% Airbnb Rental Income: $3257 Traditional Rental Income: $3175 Airbnb ROI: 1.47% 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.	$604,999	Airbnb cash on cash: 1.83% Traditional cash on cash: 2.45% Airbnb Rental Income: $3257 Traditional Rental Income: $2876 Airbnb ROI: 1.83% Traditional ROI: 2.45%
1500 CALMING WATER Drive unit: 2406 #2406 Fleming Island, FL Beautiful End Unit in this gated community is being offered as MOVE IN READY! Just Freshly...	3 beds \| N/A baths \| 1,817 sq.ft.	$269,900	Airbnb cash on cash: 4.6% Traditional cash on cash: 3.47% Airbnb Rental Income: $2916 Traditional Rental Income: $1955 Airbnb ROI: 4.6% Traditional ROI: 3.47%
1896 CHATHAM VILLAGE Drive Fleming Island, FL Beautifully Updated Chatham Village builders model home in highly desired Fleming Island P...	3 beds \| 3 baths \| 2,686 sq.ft.	$489,000	Airbnb cash on cash: 2.44% Traditional cash on cash: 2.83% Airbnb Rental Income: $2916 Traditional Rental Income: $2418 Airbnb ROI: 2.44% Traditional ROI: 2.83%
975 FLOYD Street Fleming Island, FL Fabulous, solid built, Fleming Island brick pool home on a DOUBLE LOT is now availale. Roo...	3 beds \| 2 baths \| 2,159 sq.ft.	$459,000	Airbnb cash on cash: 2.81% Traditional cash on cash: 3.17% Airbnb Rental Income: $2916 Traditional Rental Income: $2395 Airbnb ROI: 2.81% Traditional ROI: 3.17%
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: 4.32% Traditional cash on cash: 3.71% Airbnb Rental Income: $3257 Traditional Rental Income: $2298 Airbnb ROI: 4.32% 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: -0.71% Traditional cash on cash: -0.65% Airbnb Rental Income: $3257 Traditional Rental Income: $2648 Airbnb ROI: -0.71% Traditional ROI: -0.65%
1421 WOODLAND VIEW Drive Fleming Island, FL Included 100-Day Home Warranty with buyer activation.Welcome to your dream home! This prop...	4 beds \| 2 baths \| 1,927 sq.ft.	$340,000	Airbnb cash on cash: 5.29% Traditional cash on cash: 4.7% Airbnb Rental Income: $3257 Traditional Rental Income: $2337 Airbnb ROI: 5.29% Traditional ROI: 4.7%
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: 5.42% Traditional cash on cash: 4.11% Airbnb Rental Income: $2916 Traditional Rental Income: $1902 Airbnb ROI: 5.42% 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.	$409,900	Airbnb cash on cash: 8.79% Traditional cash on cash: 5.35% Airbnb Rental Income: $5355 Traditional Rental Income: $2954 Airbnb ROI: 8.79% Traditional ROI: 5.35%
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: 5.41% Traditional cash on cash: 5.23% Airbnb Rental Income: $3257 Traditional Rental Income: $2464 Airbnb ROI: 5.41% 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.	$710,000	Airbnb cash on cash: 2.5% Traditional cash on cash: 2.83% Airbnb Rental Income: $3257 Traditional Rental Income: $2748 Airbnb ROI: 2.5% Traditional ROI: 2.83%
2176 AUTUMN COVE Circle Fleming Island, FL Your dreams come true with this incredible home located in an exclusive resort style commu...	4 beds \| N/A baths \| 2,753 sq.ft.	$549,900	Airbnb cash on cash: 2.1% Traditional cash on cash: 3.61% Airbnb Rental Income: $3257 Traditional Rental Income: $3302 Airbnb ROI: 2.1% Traditional ROI: 3.61%
234 EVENTIDE Drive Fleming Island, FL MOTIVATED SELLERS! Make an appointment and then make an offer! Located on a quiet street t...	4 beds \| 2 baths \| 2,478 sq.ft.	$514,000	Airbnb cash on cash: 3.33% Traditional cash on cash: 3.58% Airbnb Rental Income: $3257 Traditional Rental Income: $2645 Airbnb ROI: 3.33% Traditional ROI: 3.58%
1875 GREEN SPRINGS Circle unit: B #B Fleming Island, FL Step into your dream lifestyle with this stunning 2-story townhome, perfectly nestled in t...	3 beds \| N/A baths \| 1,664 sq.ft.	$239,000	Airbnb cash on cash: 5.07% Traditional cash on cash: 3.56% Airbnb Rental Income: $2916 Traditional Rental Income: $1899 Airbnb ROI: 5.07% Traditional ROI: 3.56%
149 RIVERWOOD Drive Fleming Island, FL Come see this beautiful 4 bedroom 2.5 bath home on the St. Johns river. The living space i...	4 beds \| N/A baths \| 2,911 sq.ft.	$1,489,000	Airbnb cash on cash: 0.09% Traditional cash on cash: 0.81% Airbnb Rental Income: $3257 Traditional Rental Income: $3528 Airbnb ROI: 0.09% 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: 6.09% Traditional cash on cash: 3.38% Airbnb Rental Income: $5355 Traditional Rental Income: $2884 Airbnb ROI: 6.09% 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.	$865,000	Airbnb cash on cash: 1.46% Traditional cash on cash: 2.72% Airbnb Rental Income: $3257 Traditional Rental Income: $3539 Airbnb ROI: 1.46% Traditional ROI: 2.72%
2518 WILLOW CREEK Drive Fleming Island, FL REDUCED!!!Welcome to this one of a kind, spacious home with many beautiful upgrades throug...	4 beds \| N/A baths \| 2,716 sq.ft.	$575,000	Airbnb cash on cash: 2.32% Traditional cash on cash: 4.67% Airbnb Rental Income: $3257 Traditional Rental Income: $3789 Airbnb ROI: 2.32% Traditional ROI: 4.67%
5640 STARLIGHT Lane Fleming Island, FL Stunning All-Brick Home with Rock Waterfall Pool Near St. Johns River - virtually No HOA r...	3 beds \| N/A baths \| 2,644 sq.ft.	$685,000	Airbnb cash on cash: 1.64% Traditional cash on cash: 2.89% Airbnb Rental Income: $2916 Traditional Rental Income: $3040 Airbnb ROI: 1.64% Traditional ROI: 2.89%
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: 6.43% Traditional cash on cash: 7.36% Airbnb Rental Income: $5355 Traditional Rental Income: $4744 Airbnb ROI: 6.43% 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: 2.46% Traditional cash on cash: 2.83% Airbnb Rental Income: $3257 Traditional Rental Income: $2730 Airbnb ROI: 2.46% Traditional ROI: 2.83%
2012 BELLE GROVE Terrace Fleming Island, FL Buyer's financing fell through, their LOSS is your GAIN! Welcome to Fleming Island Plantat...	4 beds \| N/A baths \| 2,808 sq.ft.	$495,000	Airbnb cash on cash: 2.52% Traditional cash on cash: 5.48% Airbnb Rental Income: $3257 Traditional Rental Income: $3896 Airbnb ROI: 2.52% Traditional ROI: 5.48%
1576 LINKSIDE Drive Fleming Island, FL LUXURY LIFESTYLE WITH LUXURIOUS UPGRADES in Fleming Island WITH A WATER VIEW An exceptiona...	4 beds \| N/A baths \| 2,373 sq.ft.	$699,000	Airbnb cash on cash: 1.72% Traditional cash on cash: 3.13% Airbnb Rental Income: $3257 Traditional Rental Income: $3444 Airbnb ROI: 1.72% Traditional ROI: 3.13%

Real Estate investment in Fleming-island, FL

There are 83 properties for sale in the city of Fleming Island . The median list price in Fleming Island is $480,000 and the average price per square foot is $201. In October 2025, the average monthly cash on cash return in Fleming Island is 4.00%. The average monthly rental income in Fleming Island is $2,522.

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

There are 83 investment properties available for sale in Fleming-island.

In 2025, the best neighborhood to buy investment property is Fleming Island.

The ROI for Long-Term is higher than the Short-Term in Fleming-island with average rental income of $2,522.

Your search for investment property begins and ends here

Investment Property for Sale in Fleming Island, FL

1565 ROYAL FERN Lane

Fleming Island, FL

4 beds | 2 baths | 2,331 sq.ft.

$495,000

Airbnb cash on cash: 3.07%

Traditional cash on cash: 2.99%

Airbnb Rental Income: $3257

Traditional Rental Income: $2487

Airbnb ROI: 3.07%

Traditional ROI: 2.99%

1940 BLUEBONNET Way

Fleming Island, FL

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

$469,000

Airbnb cash on cash: 2.7%

Traditional cash on cash: 2.63%

Airbnb Rental Income: $2916

Traditional Rental Income: $2210

Airbnb ROI: 2.7%

Traditional ROI: 2.63%

1685 PINECREST Drive

Fleming Island, FL

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

$539,000

Airbnb cash on cash: 3.01%

Traditional cash on cash: 3.86%

Airbnb Rental Income: $3257

Traditional Rental Income: $2954

Airbnb ROI: 3.01%

Traditional ROI: 3.86%

2299 S BROOK Drive

Fleming Island, FL

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

$576,000

Airbnb cash on cash: 2.32%

Traditional cash on cash: 3.03%

Airbnb Rental Income: $3257

Traditional Rental Income: $2908

Airbnb ROI: 2.32%

Traditional ROI: 3.03%

1207 STERN Way

Fleming Island, FL

4 beds | 2 baths | 1,764 sq.ft.

$309,900

Airbnb cash on cash: 5.81%

Traditional cash on cash: 5.12%

Airbnb Rental Income: $3257

Traditional Rental Income: $2326

Airbnb ROI: 5.81%

Traditional ROI: 5.12%

2171 TRAILWOOD Drive

Fleming Island, FL

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

$379,000

Airbnb cash on cash: 3.85%

Traditional cash on cash: 3.33%

Airbnb Rental Income: $2916

Traditional Rental Income: $2054

Airbnb ROI: 3.85%

Traditional ROI: 3.33%

132 MALLEY COVE Lane

Fleming Island, FL

4 beds | 4 baths | 4,184 sq.ft.

$1,100,000

Airbnb cash on cash: 0.6%

Traditional cash on cash: 1.96%

Airbnb Rental Income: $3257

Traditional Rental Income: $3922

Airbnb ROI: 0.6%

Traditional ROI: 1.96%

4966 HARVEY GRANT Road

Fleming Island, FL

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

$399,999

Airbnb cash on cash: 3.84%

Traditional cash on cash: 3.69%

Airbnb Rental Income: $2916

Traditional Rental Income: $2185

Airbnb ROI: 3.84%