Real Estate Investment Properties for Sale in Summerland Key, FL

Looking for investment property in Summerland Key, FL with high ROI ?

Explore a variety of short-term homes & houses in Summerland Key, FL. Invest wisely with VRBO & Summerland Key, 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 Summerland Key, FL

Search for Single Family Residential for Sale in Summerland Key, 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 19 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
556 E Caribbean Drive Summerland Key, FL The sea writes the script at this 3 bed, 3 bath oceanfront retreat on the most highly soug...	3 beds \| 3 baths \| 2,167 sq.ft.	$2,499,000	Airbnb cash on cash: 0.05% Traditional cash on cash: 0.45% Airbnb Rental Income: $4854 Traditional Rental Income: $4785 Airbnb ROI: 0.05% Traditional ROI: 0.45%
466 W Shore Drive Summerland Key, FL Welcome to 466 W Shore Dr in prestigious Summerland Key. This 2 bedroom concrete home is s...	2 beds \| 2 baths \| 1,364 sq.ft.	$1,250,000	Airbnb cash on cash: 2.66% Traditional cash on cash: 1.73% Airbnb Rental Income: $5495 Traditional Rental Income: $3317 Airbnb ROI: 2.66% Traditional ROI: 1.73%
25368 2nd Street Summerland Key, FL Experience the perfect blend of character, durability, and Keys style at this quintessenti...	2 beds \| 2 baths \| 1,392 sq.ft.	$1,595,000	Airbnb cash on cash: 1.3% Traditional cash on cash: 0.68% Airbnb Rental Income: $5495 Traditional Rental Income: $3468 Airbnb ROI: 1.3% Traditional ROI: 0.68%
24931 Overseas Highway Summerland Key, FL Seize this rare opportunity to own a prime working waterfront property with exceptional Hi...	1 beds \| 4 baths \| 1,965 sq.ft.	$895,000	Airbnb cash on cash: 1.52% Traditional cash on cash: 4.2% Airbnb Rental Income: $3458 Traditional Rental Income: $4929 Airbnb ROI: 1.52% Traditional ROI: 4.2%
24347 W Caribbean Drive Summerland Key, FL Welcome to Summerland Key Cove! This beautifully home is perfectly situated on a deep-wate...	3 beds \| 2 baths \| 1,232 sq.ft.	$1,325,000	Airbnb cash on cash: 1.44% Traditional cash on cash: 10.41% Airbnb Rental Income: $4854 Traditional Rental Income: $14911 Airbnb ROI: 1.44% Traditional ROI: 10.41%
948 Gulf Drive Summerland Key, FL Luxury coastal living meets unmatched boating convenience at this fully renovated canal-fr...	3 beds \| 3 baths \| 2,010 sq.ft.	$2,300,000	Airbnb cash on cash: 0.07% Traditional cash on cash: 0.27% Airbnb Rental Income: $4854 Traditional Rental Income: $4283 Airbnb ROI: 0.07% Traditional ROI: 0.27%
1082 Bay Drive Summerland Key, FL Rare Yacht-Ready Waterfront? It doesn't get better than this in the Lower Florida Keys! E...	4 beds \| 3 baths \| 1,440 sq.ft.	$1,900,000	Airbnb cash on cash: 5.11% Traditional cash on cash: -0.06% Airbnb Rental Income: $14473 Traditional Rental Income: $2746 Airbnb ROI: 5.11% Traditional ROI: -0.06%
23941 Henry Street Summerland Key, FL Oceanfront Luxury Retreat with Private Beach, Protected Dockage & Quick Direct Boating Acc...	3 beds \| 2 baths \| 2,232 sq.ft.	$2,985,000	Airbnb cash on cash: 0.13% Traditional cash on cash: 0.14% Airbnb Rental Income: $4854 Traditional Rental Income: $3888 Airbnb ROI: 0.13% Traditional ROI: 0.14%
701 Spanish Main Drive #UNIT 49 Summerland Key, FL ******Nightly Licensed Transient Rental!!!******This amazing, two bedroom / one bathro...	2 beds \| 1 baths \| 806 sq.ft.	$925,000	Airbnb cash on cash: 2.58% Traditional cash on cash: 0.16% Airbnb Rental Income: $5495 Traditional Rental Income: $2305 Airbnb ROI: 2.58% Traditional ROI: 0.16%
860 Lagoon Drive Summerland Key, FL This stately concrete home has all the best of everything on one of the best boating areas...	3 beds \| 3 baths \| 1,797 sq.ft.	$1,950,000	Airbnb cash on cash: 0.49% Traditional cash on cash: 0.23% Airbnb Rental Income: $4854 Traditional Rental Income: $3393 Airbnb ROI: 0.49% Traditional ROI: 0.23%
1147 Flagship Drive Summerland Key, FL Located on the highly desired Flagship Drive in Summerland Cove Isles, this stunning 3 bed...	3 beds \| 2 baths \| 2,058 sq.ft.	$2,650,000	Airbnb cash on cash: 0.01% Traditional cash on cash: 0% Airbnb Rental Income: $4854 Traditional Rental Income: $3818 Airbnb ROI: 0.01% Traditional ROI: 0%
21855 21865 Spain Boulevard Summerland Key, FL Majestically positioned at the end of Spain Blvd, within the Prestigious Cudjoe Acres neig...	3 beds \| 2 baths \| 1,467 sq.ft.	$1,500,000	Airbnb cash on cash: 1.43% Traditional cash on cash: 0.98% Airbnb Rental Income: $4854 Traditional Rental Income: $3225 Airbnb ROI: 1.43% Traditional ROI: 0.98%
701 Spanish Main Drive #UNIT 495 Summerland Key, FL Welcome to this completely remodeled, direct canal front cottage located at 701 Spanish Ma...	2 beds \| 2 baths \| 816 sq.ft.	$625,000	Airbnb cash on cash: 5.46% Traditional cash on cash: 2.37% Airbnb Rental Income: $5495 Traditional Rental Income: $2586 Airbnb ROI: 5.46% Traditional ROI: 2.37%
0 Melody Summerland Key, FL An unparalleled opportunity to own your own private island in the Florida Keys. Melody Key...	3 beds \| 4 baths \| 2,851 sq.ft.	$7,000,000	Airbnb cash on cash: -0.69% Traditional cash on cash: -0.32% Airbnb Rental Income: $4854 Traditional Rental Income: $6267 Airbnb ROI: -0.69% Traditional ROI: -0.32%
755 & 744 Sawyer Drive Summerland Key, FL In prestigious Cudjoe Gardens, this fully renovated Keys retreat feels more like a private...	3 beds \| 2 baths \| 1,851 sq.ft.	$3,750,000	Airbnb cash on cash: -0.07% Traditional cash on cash: 0.23% Airbnb Rental Income: $4854 Traditional Rental Income: $4870 Airbnb ROI: -0.07% Traditional ROI: 0.23%
24840 Park Drive Summerland Key, FL Hard to find a home in a Park like setting with a boat ramp right out the back door! 3 be...	3 beds \| 2 baths \| 1,565 sq.ft.	$999,000	Airbnb cash on cash: 2.51% Traditional cash on cash: 1.78% Airbnb Rental Income: $4854 Traditional Rental Income: $3180 Airbnb ROI: 2.51% Traditional ROI: 1.78%
270 S Airport Drive Summerland Key, FL A rare aviation-and-waterfront opportunity in the private Summerland Key Airport community...	3 beds \| 3 baths \| 1,275 sq.ft.	$1,999,000	Airbnb cash on cash: 0.64% Traditional cash on cash: 0.31% Airbnb Rental Income: $4854 Traditional Rental Income: $3236 Airbnb ROI: 0.64% Traditional ROI: 0.31%
1163 De Lussan Lane Summerland Key, FL Are you dreaming of your own personal paradise? Look no further than this stunning propert...	2 beds \| 2 baths \| 1,344 sq.ft.	$1,800,000	Airbnb cash on cash: 1.54% Traditional cash on cash: 0.86% Airbnb Rental Income: $5495 Traditional Rental Income: $3249 Airbnb ROI: 1.54% Traditional ROI: 0.86%
195 W Shore Drive Summerland Key, FL Welcome to a truly unique aviation property in the heart of Summerland Key! Located at the...	3 beds \| 2 baths \| 1,500 sq.ft.	$925,000	Airbnb cash on cash: 2.69% Traditional cash on cash: 1.92% Airbnb Rental Income: $4854 Traditional Rental Income: $3189 Airbnb ROI: 2.69% Traditional ROI: 1.92%

Your search for investment property begins and ends here

Single Family Homes for Sale in Summerland Key, FL

556 E Caribbean Drive

Summerland Key, FL

3 beds | 3 baths | 2,167 sq.ft.

$2,499,000

Airbnb cash on cash: 0.05%

Traditional cash on cash: 0.45%

Airbnb Rental Income: $4854

Traditional Rental Income: $4785

Airbnb ROI: 0.05%

Traditional ROI: 0.45%

466 W Shore Drive

Summerland Key, FL

2 beds | 2 baths | 1,364 sq.ft.

$1,250,000

Airbnb cash on cash: 2.66%

Traditional cash on cash: 1.73%

Airbnb Rental Income: $5495

Traditional Rental Income: $3317

Airbnb ROI: 2.66%

Traditional ROI: 1.73%

25368 2nd Street

Summerland Key, FL

2 beds | 2 baths | 1,392 sq.ft.

$1,595,000

Airbnb cash on cash: 1.3%

Traditional cash on cash: 0.68%

Airbnb Rental Income: $5495

Traditional Rental Income: $3468

Airbnb ROI: 1.3%

Traditional ROI: 0.68%

24931 Overseas Highway

Summerland Key, FL

1 beds | 4 baths | 1,965 sq.ft.

$895,000

Airbnb cash on cash: 1.52%

Traditional cash on cash: 4.2%

Airbnb Rental Income: $3458

Traditional Rental Income: $4929

Airbnb ROI: 1.52%

Traditional ROI: 4.2%

24347 W Caribbean Drive

Summerland Key, FL

3 beds | 2 baths | 1,232 sq.ft.

$1,325,000

Airbnb cash on cash: 1.44%

Traditional cash on cash: 10.41%

Airbnb Rental Income: $4854

Traditional Rental Income: $14911

Airbnb ROI: 1.44%

Traditional ROI: 10.41%

948 Gulf Drive

Summerland Key, FL

3 beds | 3 baths | 2,010 sq.ft.

$2,300,000

Airbnb cash on cash: 0.07%

Traditional cash on cash: 0.27%

Airbnb Rental Income: $4854

Traditional Rental Income: $4283

Airbnb ROI: 0.07%

Traditional ROI: 0.27%

1082 Bay Drive

Summerland Key, FL

4 beds | 3 baths | 1,440 sq.ft.

$1,900,000

Airbnb cash on cash: 5.11%

Traditional cash on cash: -0.06%

Airbnb Rental Income: $14473

Traditional Rental Income: $2746

Airbnb ROI: 5.11%

Traditional ROI: -0.06%

23941 Henry Street

Summerland Key, FL

3 beds | 2 baths | 2,232 sq.ft.

$2,985,000

Airbnb cash on cash: 0.13%

Traditional cash on cash: 0.14%

Airbnb Rental Income: $4854

Traditional Rental Income: $3888

Airbnb ROI: 0.13%