Real Estate Investment Properties for Sale in Madeira Beach, FL

Looking for investment property in Madeira Beach, FL with high ROI ?

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
14103 E Parsley Dr Madeira Beach, FL Discover your dream retreat in this stunning waterfront home, complete with an exquisite i...	3 beds \| 2 baths \| 1,433 sq.ft.	$935,000	Airbnb cash on cash: -0.48% Traditional cash on cash: 3.89% Airbnb Rental Income: $1729 Traditional Rental Income: $5055 Airbnb ROI: -0.48% Traditional ROI: 3.89%
551 Crystal Dr Madeira Beach, FL 551 Crystal Dr, Madeira Beach, FL 33708 \| Single Family Residential	3 beds \| 3 baths \| 2,436 sq.ft.	$1,299,000	Airbnb cash on cash: -0.92% Traditional cash on cash: 1.06% Airbnb Rental Income: $1729 Traditional Rental Income: $3651 Airbnb ROI: -0.92% Traditional ROI: 1.06%
356 144th Ave Madeira Beach, FL New Roof on its way New Paint inside and out. Beautifully maintained home. Wood flooring t...	N/A beds \| N/A baths \| 756 sq.ft.	$349,900	Airbnb cash on cash: 4.3% Traditional cash on cash: 3.04% Airbnb Rental Income: $2714 Traditional Rental Income: $1660 Airbnb ROI: 4.3% Traditional ROI: 3.04%
352 144th Ave Madeira Beach, FL Newer Roof New Paint inside and out Block home. Beautifully maintained home with oversized...	3 beds \| 2 baths \| 1,232 sq.ft.	$750,000	Airbnb cash on cash: 0.26% Traditional cash on cash: 2.05% Airbnb Rental Income: $1729 Traditional Rental Income: $2500 Airbnb ROI: 0.26% Traditional ROI: 2.05%
50 137th Avenue Cir Madeira Beach, FL Exceptional waterfront opportunity in the heart of Madeira Beach. Just steps from Gulf Bou...	1 beds \| 1 baths \| 753 sq.ft.	$424,900	Airbnb cash on cash: -1.08% Traditional cash on cash: 4.12% Airbnb Rental Income: $1077 Traditional Rental Income: $2779 Airbnb ROI: -1.08% Traditional ROI: 4.12%
747 Pruitt Dr Madeira Beach, FL One or more photo(s) has been virtually staged. Welcome to your dream coastal retreat in M...	3 beds \| 2 baths \| 1,664 sq.ft.	$539,900	Airbnb cash on cash: 0.15% Traditional cash on cash: 4.66% Airbnb Rental Income: $1729 Traditional Rental Income: $3527 Airbnb ROI: 0.15% Traditional ROI: 4.66%
14117 Palm St Madeira Beach, FL Under contract-accepting backup offers. Beautiful Beach Bungalow! Immaculate home located ...	2 beds \| 1 baths \| 936 sq.ft.	$300,000	Airbnb cash on cash: 1.09% Traditional cash on cash: 6.05% Airbnb Rental Income: $1562 Traditional Rental Income: $2515 Airbnb ROI: 1.09% Traditional ROI: 6.05%
14900 Gulf Blvd #410 Madeira Beach, FL Welcome to paradise! Enjoy sunsets and coastal breezes! This beautifully updated 2-bedroo...	2 beds \| 2 baths \| 1,100 sq.ft.	$729,900	Airbnb cash on cash: -2.22% Traditional cash on cash: 1.23% Airbnb Rental Income: $1562 Traditional Rental Income: $3457 Airbnb ROI: -2.22% Traditional ROI: 1.23%
13235 Gulf Blvd #315 Madeira Beach, FL MOTIVATED SELLER!! DAILY RENTALS ALLOWED â INCOME PRODUCING â NEW 2025 METAL ROOF â ...	2 beds \| 2 baths \| 973 sq.ft.	$615,000	Airbnb cash on cash: -1.51% Traditional cash on cash: 2.23% Airbnb Rental Income: $1562 Traditional Rental Income: $3259 Airbnb ROI: -1.51% Traditional ROI: 2.23%
179 Medallion Blvd #H Madeira Beach, FL YOUR FLORIDA ESCAPEÂ AND YOUR SMARTEST INVESTMENT YET!Â A Waterfront CONDO at Madeira Beac...	1 beds \| 1 baths \| 755 sq.ft.	$369,000	Airbnb cash on cash: -3.19% Traditional cash on cash: 2.42% Airbnb Rental Income: $1077 Traditional Rental Income: $2651 Airbnb ROI: -3.19% Traditional ROI: 2.42%
13304 Gulf Blvd Madeira Beach, FL LOCATION,LOCATION,LOCATION! One of a kind Florida Beach cottage just steps to the beautifu...	N/A beds \| N/A baths \| 1,070 sq.ft.	$650,000	Airbnb cash on cash: 1.78% Traditional cash on cash: 0.37% Airbnb Rental Income: $2714 Traditional Rental Income: $1220 Airbnb ROI: 1.78% Traditional ROI: 0.37%
15305 1st St E #202 Madeira Beach, FL Pre Construction. To be built. Welcome to Madeira Del Mar â new construction residences ...	3 beds \| 3 baths \| 1,425 sq.ft.	$695,000	Airbnb cash on cash: -1.64% Traditional cash on cash: 1.98% Airbnb Rental Income: $1729 Traditional Rental Income: $3603 Airbnb ROI: -1.64% Traditional ROI: 1.98%
575 Crystal Dr Madeira Beach, FL Pre-Construction. To be built. This is a rare and unique opportunity to own a stunning new...	N/A beds \| N/A baths \| 4,501 sq.ft.	$1,195,000	Airbnb cash on cash: -0.4% Traditional cash on cash: 4.47% Airbnb Rental Income: $2714 Traditional Rental Income: $7484 Airbnb ROI: -0.4% Traditional ROI: 4.47%
117 140th Ave E Madeira Beach, FL One or more photo(s) has been virtually staged. * TURNKEY ALERT * RARE OPPORTUNITY * Own f...	6 beds \| N/A baths \| 2,806 sq.ft.	$1,291,000	Airbnb cash on cash: -0.36% Traditional cash on cash: 1.12% Airbnb Rental Income: $2714 Traditional Rental Income: $3929 Airbnb ROI: -0.36% Traditional ROI: 1.12%
14013 Marguerite Dr Madeira Beach, FL One or more photo(s) has been virtually staged. Newly renovated triplex in desirable Madei...	3 beds \| N/A baths \| 1,516 sq.ft.	$700,000	Airbnb cash on cash: -0.08% Traditional cash on cash: 1.7% Airbnb Rental Income: $1729 Traditional Rental Income: $2409 Airbnb ROI: -0.08% Traditional ROI: 1.7%
410 140th Ave E Madeira Beach, FL ELEVATED WATERFRONT LIVING \| POOL \| PRIVATE DOCK \| NEW ADDITION \| MODERN UPDATES Welcome t...	3 beds \| 3 baths \| 3,564 sq.ft.	$1,695,000	Airbnb cash on cash: -0.99% Traditional cash on cash: 2.08% Airbnb Rental Income: $1729 Traditional Rental Income: $6076 Airbnb ROI: -0.99% Traditional ROI: 2.08%
401 150th Ave #245 Madeira Beach, FL $10,000.PRICE IMPROVEMENT !!! RARE DEEDED BOAT SLIP WITH 10,000LB BOAT LIFT This condomini...	2 beds \| 2 baths \| 1,270 sq.ft.	$569,999	Airbnb cash on cash: -2% Traditional cash on cash: 3.24% Airbnb Rental Income: $1562 Traditional Rental Income: $3902 Airbnb ROI: -2% Traditional ROI: 3.24%
15316 Gulf Blvd #801 Madeira Beach, FL Welcome to elevated Gulf-front living at Madeira Towers. Perched on the 8th floor and posi...	3 beds \| 2 baths \| 1,625 sq.ft.	$1,324,997	Airbnb cash on cash: -2.04% Traditional cash on cash: 0.66% Airbnb Rental Income: $1729 Traditional Rental Income: $4570 Airbnb ROI: -2.04% Traditional ROI: 0.66%
14906 N Bayshore Dr Madeira Beach, FL One or more photo(s) has been virtually staged. LISTED UNDER APPRAISED VALUE ($577K). SEE ...	3 beds \| 2 baths \| 1,399 sq.ft.	$569,900	Airbnb cash on cash: 0.39% Traditional cash on cash: 3.81% Airbnb Rental Income: $1729 Traditional Rental Income: $3073 Airbnb ROI: 0.39% Traditional ROI: 3.81%
337 Rex Pl #A Madeira Beach, FL One or more photo(s) has been virtually staged. Discover Paradise in Madeira Beach: Fully ...	2 beds \| 2 baths \| 1,090 sq.ft.	$439,000	Airbnb cash on cash: -3.09% Traditional cash on cash: 0.05% Airbnb Rental Income: $1562 Traditional Rental Income: $2402 Airbnb ROI: -3.09% Traditional ROI: 0.05%
159 Medallion Blvd #E Madeira Beach, FL Bring your toothbrush to this cute 2nd floor condo. No worries here on flooding. If you ...	1 beds \| 1 baths \| 430 sq.ft.	$265,000	Airbnb cash on cash: -1.99% Traditional cash on cash: 3.29% Airbnb Rental Income: $1077 Traditional Rental Income: $2028 Airbnb ROI: -1.99% Traditional ROI: 3.29%
159 Medallion Blvd #F Madeira Beach, FL This furnished one-bedroom condo on the second floor sits inside a gated waterfront commun...	1 beds \| 1 baths \| 430 sq.ft.	$325,000	Airbnb cash on cash: -1.59% Traditional cash on cash: 1.14% Airbnb Rental Income: $1077 Traditional Rental Income: $1542 Airbnb ROI: -1.59% Traditional ROI: 1.14%
14900 Gulf Blvd #304 Madeira Beach, FL Stunning Gulf-front condo in the heart of Madeira Beach Surfside South building being offe...	2 beds \| 2 baths \| 1,100 sq.ft.	$659,900	Airbnb cash on cash: -2.8% Traditional cash on cash: -0.09% Airbnb Rental Income: $1562 Traditional Rental Income: $2784 Airbnb ROI: -2.8% Traditional ROI: -0.09%
14181 E Parsley Dr Madeira Beach, FL MOVE-IN READY! This beautiful BEACH HOME situated in a Corner Lot features 2/2 with Garage...	2 beds \| 2 baths \| 1,400 sq.ft.	$494,900	Airbnb cash on cash: 0.19% Traditional cash on cash: 4.05% Airbnb Rental Income: $1562 Traditional Rental Income: $2899 Airbnb ROI: 0.19% Traditional ROI: 4.05%
516 Crystal Dr Madeira Beach, FL Welcome to 516 Crystal Dr! This fully updated 3-bedroom, 2-bathroom property offers nearly...	3 beds \| 2 baths \| 2,091 sq.ft.	$980,000	Airbnb cash on cash: -1.25% Traditional cash on cash: 3.72% Airbnb Rental Income: $1729 Traditional Rental Income: $5783 Airbnb ROI: -1.25% Traditional ROI: 3.72%
713 Pruitt Dr Madeira Beach, FL BEAUTIFULLY UPDATED BEACHSIDE RETREAT..Just steps from the breathtaking sands of Madeira B...	3 beds \| 2 baths \| 1,442 sq.ft.	$500,000	Airbnb cash on cash: 0.5% Traditional cash on cash: 5.46% Airbnb Rental Income: $1729 Traditional Rental Income: $3571 Airbnb ROI: 0.5% Traditional ROI: 5.46%
343 Rex Pl #G Madeira Beach, FL Looking for an INVESTMENT PROPERTY, SECOND HOME OR A MORE PERMANENT PLACE to hang your fli...	2 beds \| 1 baths \| 1,040 sq.ft.	$350,000	Airbnb cash on cash: -3.42% Traditional cash on cash: 0.77% Airbnb Rental Income: $1562 Traditional Rental Income: $2490 Airbnb ROI: -3.42% Traditional ROI: 0.77%
12924 Gulf Blvd #502 Madeira Beach, FL Wake up to the sound of waves, salty Gulf breezes, and uninterrupted blue horizonsâthis ...	1 beds \| 1 baths \| 865 sq.ft.	$749,000	Airbnb cash on cash: -2.52% Traditional cash on cash: 0.03% Airbnb Rental Income: $1077 Traditional Rental Income: $2487 Airbnb ROI: -2.52% Traditional ROI: 0.03%
449 S Bayshore Dr Madeira Beach, FL 449 S Bayshore Dr, Madeira Beach, FL 33708 \| Other	N/A beds \| N/A baths \| 1,245 sq.ft.	$895,000	Airbnb cash on cash: 0.49% Traditional cash on cash: 0.73% Airbnb Rental Income: $2714 Traditional Rental Income: $2269 Airbnb ROI: 0.49% Traditional ROI: 0.73%
15000 Gulf Blvd #1108 Madeira Beach, FL Take in amazing views, experience the most incredible sunsets, and sleep to the sound of t...	2 beds \| 2 baths \| 1,225 sq.ft.	$930,000	Airbnb cash on cash: -1.23% Traditional cash on cash: 0.57% Airbnb Rental Income: $1562 Traditional Rental Income: $2672 Airbnb ROI: -1.23% Traditional ROI: 0.57%
317 Rex Pl #G Madeira Beach, FL CALLING ALL BOATERS! NEED A HOME FOR YOUR BOAT? SLIP #60 IS WAITING FOR YOU! Not only d...	2 beds \| 1 baths \| 1,040 sq.ft.	$419,000	Airbnb cash on cash: -2.37% Traditional cash on cash: 0.7% Airbnb Rental Income: $1562 Traditional Rental Income: $2315 Airbnb ROI: -2.37% Traditional ROI: 0.7%
13095 Gulf Ln Madeira Beach, FL Turnkey beachside investment opportunity with sought after zoning that allows for nightly ...	2 beds \| 2 baths \| 1,404 sq.ft.	$969,000	Airbnb cash on cash: -0.92% Traditional cash on cash: 0.54% Airbnb Rental Income: $1562 Traditional Rental Income: $2425 Airbnb ROI: -0.92% Traditional ROI: 0.54%
30 Lynn Way Madeira Beach, FL Charming duplex that features a completely finished 1 bed /1 bath apartment on one side an...	N/A beds \| N/A baths \| 1,008 sq.ft.	$310,000	Airbnb cash on cash: 1.05% Traditional cash on cash: 4.26% Airbnb Rental Income: $1562 Traditional Rental Income: $2050 Airbnb ROI: 1.05% Traditional ROI: 4.26%
119 147th Ave E Madeira Beach, FL One or more photo(s) has been virtually staged. Discover an exceptional investment opportu...	4 beds \| N/A baths \| 1,264 sq.ft.	$525,000	Airbnb cash on cash: 0.19% Traditional cash on cash: 3.8% Airbnb Rental Income: $1562 Traditional Rental Income: $2883 Airbnb ROI: 0.19% Traditional ROI: 3.8%
15424 2nd St E Madeira Beach, FL Paradise awaits just two blocks from the beach! Nestled in a sought-after neighborhood beh...	3 beds \| 2 baths \| 1,103 sq.ft.	$575,000	Airbnb cash on cash: 0.39% Traditional cash on cash: 3.98% Airbnb Rental Income: $1729 Traditional Rental Income: $3178 Airbnb ROI: 0.39% Traditional ROI: 3.98%
583 Crystal Dr Madeira Beach, FL Where open water views meet privacy... A lifestyle-driven, wide-open-water estate with res...	4 beds \| 4 baths \| 3,614 sq.ft.	$2,950,000	Airbnb cash on cash: -1.52% Traditional cash on cash: 1.85% Airbnb Rental Income: $785 Traditional Rental Income: $9669 Airbnb ROI: -1.52% Traditional ROI: 1.85%
811 Bay Point Dr Madeira Beach, FL Under contract-accepting backup offers. Incredible expanded WATER VIEW IN MADEIRA BEACH ...	N/A beds \| N/A baths \| 2,062 sq.ft.	$820,000	Airbnb cash on cash: -0.37% Traditional cash on cash: 0.71% Airbnb Rental Income: $2714 Traditional Rental Income: $2899 Airbnb ROI: -0.37% Traditional ROI: 0.71%
4550 COVE CIRCLE #405 Madeira Beach, FL WHAT A VIEW !!!! This studio, in a gated community, has a fantastic view of the Intracoast...	1 beds \| 1 baths \| 530 sq.ft.	$99,900	Airbnb cash on cash: -3.5% Traditional cash on cash: 4.87% Airbnb Rental Income: $1077 Traditional Rental Income: $1522 Airbnb ROI: -3.5% Traditional ROI: 4.87%
14146 Gulf Blvd #3A Madeira Beach, FL Fractional Ownership. *FRACTIONAL OWNERSHIP* Owner is selling 50% ownership. Own a mil...	2 beds \| 2 baths \| 1,415 sq.ft.	$519,000	Airbnb cash on cash: -3.96% Traditional cash on cash: 1.74% Airbnb Rental Income: $1562 Traditional Rental Income: $3878 Airbnb ROI: -3.96% Traditional ROI: 1.74%
14066 Marguerite Dr Madeira Beach, FL MOVE-IN READY! FULLY RENOVATED Beachside Bungalow! Welcome to your dream coastal retreat...	2 beds \| 1 baths \| 885 sq.ft.	$520,000	Airbnb cash on cash: -0.02% Traditional cash on cash: 3.24% Airbnb Rental Income: $1562 Traditional Rental Income: $2694 Airbnb ROI: -0.02% Traditional ROI: 3.24%

Real Estate investment in Madeira-beach, FL

There are 202 properties for sale in the city of Madeira Beach . The median list price in Madeira Beach is $790,000 and the average price per square foot is $517. In May 2026, the average monthly cash on cash return in Madeira Beach is 1.00%. The average monthly rental income in Madeira Beach is $2,857.

Madeira-beach, FL Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 202 investment properties available for sale in Madeira-beach.

In 2026, the best neighborhood to buy investment property is Madeira Beach.

The ROI for Long-Term is higher than the Short-Term in Madeira-beach with average rental income of $2,857.

Your search for investment property begins and ends here

Investment Property for Sale in Madeira Beach, FL

14103 E Parsley Dr

Madeira Beach, FL

3 beds | 2 baths | 1,433 sq.ft.

$935,000

Airbnb cash on cash: -0.48%

Traditional cash on cash: 3.89%

Airbnb Rental Income: $1729

Traditional Rental Income: $5055

Airbnb ROI: -0.48%

Traditional ROI: 3.89%

551 Crystal Dr

Madeira Beach, FL

3 beds | 3 baths | 2,436 sq.ft.

$1,299,000

Airbnb cash on cash: -0.92%

Traditional cash on cash: 1.06%

Airbnb Rental Income: $1729

Traditional Rental Income: $3651

Airbnb ROI: -0.92%

Traditional ROI: 1.06%

356 144th Ave

Madeira Beach, FL

N/A beds | N/A baths | 756 sq.ft.

$349,900

Airbnb cash on cash: 4.3%

Traditional cash on cash: 3.04%

Airbnb Rental Income: $2714

Traditional Rental Income: $1660

Airbnb ROI: 4.3%

Traditional ROI: 3.04%

352 144th Ave

Madeira Beach, FL

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

$750,000

Airbnb cash on cash: 0.26%

Traditional cash on cash: 2.05%

Airbnb Rental Income: $1729

Traditional Rental Income: $2500

Airbnb ROI: 0.26%

Traditional ROI: 2.05%

50 137th Avenue Cir

Madeira Beach, FL

1 beds | 1 baths | 753 sq.ft.

$424,900

Airbnb cash on cash: -1.08%

Traditional cash on cash: 4.12%

Airbnb Rental Income: $1077

Traditional Rental Income: $2779

Airbnb ROI: -1.08%

Traditional ROI: 4.12%

747 Pruitt Dr

Madeira Beach, FL

3 beds | 2 baths | 1,664 sq.ft.

$539,900

Airbnb cash on cash: 0.15%

Traditional cash on cash: 4.66%

Airbnb Rental Income: $1729

Traditional Rental Income: $3527

Airbnb ROI: 0.15%

Traditional ROI: 4.66%

14117 Palm St

Madeira Beach, FL

2 beds | 1 baths | 936 sq.ft.

$300,000

Airbnb cash on cash: 1.09%

Traditional cash on cash: 6.05%

Airbnb Rental Income: $1562

Traditional Rental Income: $2515

Airbnb ROI: 1.09%

Traditional ROI: 6.05%

14900 Gulf Blvd #410

Madeira Beach, FL

2 beds | 2 baths | 1,100 sq.ft.

$729,900

Airbnb cash on cash: -2.22%

Traditional cash on cash: 1.23%

Airbnb Rental Income: $1562

Traditional Rental Income: $3457

Airbnb ROI: -2.22%