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 DRIVE 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%
15208 Gulf Blvd #601 Madeira Beach, FL THE CONDO YOU HAVE BEEN WAITING FOR AT THE BEST PRICE! LIVE THE VACATION LIFESTYLE EVERYD...	4 beds \| 3 baths \| 3,400 sq.ft.	$3,000,000	Airbnb cash on cash: -2.58% Traditional cash on cash: 0.3% Airbnb Rental Income: $785 Traditional Rental Income: $8478 Airbnb ROI: -2.58% Traditional ROI: 0.3%
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.	$658,000	Airbnb cash on cash: 0.44% Traditional cash on cash: 2.47% Airbnb Rental Income: $1729 Traditional Rental Income: $2500 Airbnb ROI: 0.44% Traditional ROI: 2.47%
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%
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.	$699,900	Airbnb cash on cash: -2.27% Traditional cash on cash: 1.32% Airbnb Rental Income: $1562 Traditional Rental Income: $3457 Airbnb ROI: -2.27% Traditional ROI: 1.32%
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.	$1,185,000	Airbnb cash on cash: -0.39% Traditional cash on cash: 4.52% Airbnb Rental Income: $2714 Traditional Rental Income: $7484 Airbnb ROI: -0.39% Traditional ROI: 4.52%
117 140th Ave E Madeira Beach, FL Virtually Staged. * PRICED AT APPRAISED VALUE * TURNKEY ALERT * RARE OPPORTUNITY * OWN FUL...	6 beds \| N/A baths \| 2,806 sq.ft.	$1,291,000	Airbnb cash on cash: -0.34% Traditional cash on cash: 1.21% Airbnb Rental Income: $2714 Traditional Rental Income: $3929 Airbnb ROI: -0.34% Traditional ROI: 1.21%
14013 Marguerite Dr Madeira Beach, FL Virtually Staged. Price reduced to sell! Completely renovated triplex in desirable Madeir...	3 beds \| N/A baths \| 1,516 sq.ft.	$675,000	Airbnb cash on cash: -0.04% Traditional cash on cash: 1.8% Airbnb Rental Income: $1729 Traditional Rental Income: $2409 Airbnb ROI: -0.04% Traditional ROI: 1.8%
14016 E Parsley Dr Madeira Beach, FL Price reduction!!! Close to beach. 5 minute walk. Duplex owned by seller for many years. L...	2 beds \| N/A baths \| 1,008 sq.ft.	$529,000	Airbnb cash on cash: 0.75% Traditional cash on cash: 0.67% Airbnb Rental Income: $1729 Traditional Rental Income: $1212 Airbnb ROI: 0.75% Traditional ROI: 0.67%
410 140TH AVENUE E Madeira Beach, FL Under contract-accepting backup offers. ELEVATED WATERFRONT LIVING \| POOL \| PRIVATE DOCK \|...	3 beds \| 4 baths \| 3,564 sq.ft.	$1,495,000	Airbnb cash on cash: -0.98% Traditional cash on cash: 2.49% Airbnb Rental Income: $1729 Traditional Rental Income: $6076 Airbnb ROI: -0.98% Traditional ROI: 2.49%
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.	$549,999	Airbnb cash on cash: -2.04% Traditional cash on cash: 3.39% Airbnb Rental Income: $1562 Traditional Rental Income: $3902 Airbnb ROI: -2.04% Traditional ROI: 3.39%
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 Virtually Staged. PRICED TO SELL. Seller is offering exceptional buyer incentives includin...	3 beds \| 2 baths \| 1,399 sq.ft.	$499,900	Airbnb cash on cash: 0.58% Traditional cash on cash: 4.48% Airbnb Rental Income: $1729 Traditional Rental Income: $3073 Airbnb ROI: 0.58% Traditional ROI: 4.48%
230 Medallion Blvd #E Madeira Beach, FL NO FLOOD INSURANCE NEEDED. Beautifully-updated in 2018 this 2/1 in the highly sought-afte...	2 beds \| 1 baths \| 750 sq.ft.	$349,900	Airbnb cash on cash: -1.47% Traditional cash on cash: -0.01% Airbnb Rental Income: $1562 Traditional Rental Income: $1592 Airbnb ROI: -1.47% Traditional ROI: -0.01%
337 Rex Pl #A Madeira Beach, FL One or more photo(s) has been virtually staged. INVESTOR & SNOWBIRD PARADISE WITH FULLY FU...	2 beds \| 2 baths \| 1,090 sq.ft.	$429,900	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 #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%
547 Johns Pass Ave Madeira Beach, FL WELCOME TO 547 JOHNS PASS AVENUE A RARE OPEN WATER ESTATE FEATURING TWO PRIMARY SUITES, BR...	4 beds \| 3 baths \| 3,481 sq.ft.	$2,495,000	Airbnb cash on cash: -1.42% Traditional cash on cash: 0.37% Airbnb Rental Income: $785 Traditional Rental Income: $4609 Airbnb ROI: -1.42% Traditional ROI: 0.37%
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%
503 Johns Pass Ave Madeira Beach, FL STUNNING WATERFRONT residence in the exclusive Crystal Island enclave of Madeira Beach â...	4 beds \| 3 baths \| 3,072 sq.ft.	$2,699,000	Airbnb cash on cash: -1.86% Traditional cash on cash: -0.28% Airbnb Rental Income: $785 Traditional Rental Income: $4425 Airbnb ROI: -1.86% Traditional ROI: -0.28%
480 S Bayshore Dr Madeira Beach, FL Virtually Staged. Experience the ULTIMATE coastal lifestyle in this LUXURIOUS beach bungal...	2 beds \| 2 baths \| 1,332 sq.ft.	$549,900	Airbnb cash on cash: 0.23% Traditional cash on cash: 3% Airbnb Rental Income: $1562 Traditional Rental Income: $2539 Airbnb ROI: 0.23% Traditional ROI: 3%
14181 E PARSLEY DRIVE 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.	$499,900	Airbnb cash on cash: 0.18% Traditional cash on cash: 4% Airbnb Rental Income: $1562 Traditional Rental Income: $2899 Airbnb ROI: 0.18% Traditional ROI: 4%
516 Crystal Dr Madeira Beach, FL Welcome to 516 Crystal Dr, a beautiful single-family POOL home! This fully updated 3-bedro...	3 beds \| 2 baths \| 2,091 sq.ft.	$950,000	Airbnb cash on cash: -1.25% Traditional cash on cash: 3.87% Airbnb Rental Income: $1729 Traditional Rental Income: $5783 Airbnb ROI: -1.25% Traditional ROI: 3.87%
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.	$879,000	Airbnb cash on cash: -0.91% Traditional cash on cash: 0.7% Airbnb Rental Income: $1562 Traditional Rental Income: $2425 Airbnb ROI: -0.91% Traditional ROI: 0.7%
30 LYNN WAY Madeira Beach, FL Under contract-accepting backup offers. Charming duplex that features a completely finishe...	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%
230 Medallion Blvd #D Madeira Beach, FL LOCATION, LOCATION, LOCATION!!! Check out this POOLSIDE, 2 bedroom/1bth GROUND FLOOR unit...	2 beds \| 1 baths \| 750 sq.ft.	$466,000	Airbnb cash on cash: -1.42% Traditional cash on cash: -0.04% Airbnb Rental Income: $1562 Traditional Rental Income: $1717 Airbnb ROI: -1.42% Traditional ROI: -0.04%
119 147th Ave E Madeira Beach, FL Virtually Staged. AMAZING PRICE AND LOCATION! Discover an exceptional investment opportuni...	2 beds \| N/A baths \| 1,264 sq.ft.	$499,999	Airbnb cash on cash: 0.25% Traditional cash on cash: 4.03% Airbnb Rental Income: $1562 Traditional Rental Income: $2883 Airbnb ROI: 0.25% Traditional ROI: 4.03%
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.	$569,000	Airbnb cash on cash: 0.4% Traditional cash on cash: 4.03% Airbnb Rental Income: $1729 Traditional Rental Income: $3178 Airbnb ROI: 0.4% Traditional ROI: 4.03%
583 Crystal Dr Madeira Beach, FL Where Open Water Views Meet Privacy Positioned at the very end of the road with protect...	4 beds \| 4 baths \| 3,614 sq.ft.	$2,849,000	Airbnb cash on cash: -1.53% Traditional cash on cash: 1.95% Airbnb Rental Income: $785 Traditional Rental Income: $9669 Airbnb ROI: -1.53% Traditional ROI: 1.95%
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%

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

There are 187 investment properties available for sale in Madeira-beach.

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

The ROI for Short-Term is higher than the Long-Term in Madeira-beach with average rental income of $N/A.

Your search for investment property begins and ends here

Investment Property for Sale in Madeira Beach, FL

14103 E PARSLEY DRIVE

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%

15208 Gulf Blvd #601

Madeira Beach, FL

4 beds | 3 baths | 3,400 sq.ft.

$3,000,000

Airbnb cash on cash: -2.58%

Traditional cash on cash: 0.3%

Airbnb Rental Income: $785

Traditional Rental Income: $8478

Airbnb ROI: -2.58%

Traditional ROI: 0.3%

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.

$658,000

Airbnb cash on cash: 0.44%

Traditional cash on cash: 2.47%

Airbnb Rental Income: $1729

Traditional Rental Income: $2500

Airbnb ROI: 0.44%

Traditional ROI: 2.47%

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%

14900 Gulf Blvd #410

Madeira Beach, FL

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

$699,900

Airbnb cash on cash: -2.27%

Traditional cash on cash: 1.32%

Airbnb Rental Income: $1562

Traditional Rental Income: $3457

Airbnb ROI: -2.27%

Traditional ROI: 1.32%

13235 Gulf Blvd #315

Madeira Beach, FL

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%