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%
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%
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.	$449,000	Airbnb cash on cash: -1.08% Traditional cash on cash: 3.85% Airbnb Rental Income: $1077 Traditional Rental Income: $2779 Airbnb ROI: -1.08% Traditional ROI: 3.85%
329 MEDALLION BOULEVARD #B Madeira Beach, FL Under contract-accepting backup offers. Live the ultimate Madeira Beach waterfront lifesty...	2 beds \| 2 baths \| 915 sq.ft.	$479,900	Airbnb cash on cash: -2.18% Traditional cash on cash: 1.83% Airbnb Rental Income: $1562 Traditional Rental Income: $2914 Airbnb ROI: -2.18% Traditional ROI: 1.83%
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.	$549,900	Airbnb cash on cash: 0.13% Traditional cash on cash: 4.56% Airbnb Rental Income: $1729 Traditional Rental Income: $3527 Airbnb ROI: 0.13% Traditional ROI: 4.56%
15400 Gulf Blvd #402 Madeira Beach, FL ATTENTION BUYERS: Seller is willing to consider any & all Buyers' requests that are includ...	2 beds \| 2 baths \| 1,190 sq.ft.	$839,000	Airbnb cash on cash: -2.44% Traditional cash on cash: -0.89% Airbnb Rental Income: $1562 Traditional Rental Income: $2330 Airbnb ROI: -2.44% Traditional ROI: -0.89%
14117 Palm St Madeira Beach, FL Under contract-accepting backup offers. Beautiful Beach Bungalow! Immaculate home located ...	2 beds \| 1 baths \| 936 sq.ft.	$320,000	Airbnb cash on cash: 0.96% Traditional cash on cash: 5.62% Airbnb Rental Income: $1562 Traditional Rental Income: $2515 Airbnb ROI: 0.96% Traditional ROI: 5.62%
13630 Gulf Blvd #200C Madeira Beach, FL Huge Price Reduction! EXPERIENCE THE PINNACLE OF LUXURY GULF FRONT LIVING IN BELLARTE. Thi...	3 beds \| 3 baths \| 3,186 sq.ft.	$3,230,000	Airbnb cash on cash: -1.96% Traditional cash on cash: -0.2% Airbnb Rental Income: $1729 Traditional Rental Income: $6531 Airbnb ROI: -1.96% Traditional ROI: -0.2%
15316 GULF BOULEVARD #402 Madeira Beach, FL Under contract-accepting backup offers. MOTIVATED SELLER - THE BEACH IS CALLING!!! Elevat...	3 beds \| 2 baths \| 1,265 sq.ft.	$899,000	Airbnb cash on cash: -2.58% Traditional cash on cash: 0.85% Airbnb Rental Income: $1729 Traditional Rental Income: $4129 Airbnb ROI: -2.58% Traditional ROI: 0.85%
14900 Gulf Blvd #410 Madeira Beach, FL Welcome to paradise! This beautifully updated 2-bedroom, 2-bathroom condo is perfectly pos...	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 BOULEVARD #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%
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%
117 140th Ave E Madeira Beach, FL One or more photo(s) has been virtually staged. * INVESTORS ALERT * RARE OPPORTUNITY * Own...	6 beds \| N/A baths \| 2,806 sq.ft.	$1,347,000	Airbnb cash on cash: -1.02% Traditional cash on cash: 1.12% Airbnb Rental Income: $1729 Traditional Rental Income: $3929 Airbnb ROI: -1.02% Traditional ROI: 1.12%
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 RARE DEEDED BOAT SLIP WITH 10,000LB BOAT LIFT This condominium offers approximately 1,270 ...	2 beds \| 2 baths \| 1,270 sq.ft.	$584,999	Airbnb cash on cash: -1.97% Traditional cash on cash: 3.13% Airbnb Rental Income: $1562 Traditional Rental Income: $3902 Airbnb ROI: -1.97% Traditional ROI: 3.13%
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.	$1,324,999	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%
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%
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.	$529,900	Airbnb cash on cash: 0.11% Traditional cash on cash: 3.72% Airbnb Rental Income: $1562 Traditional Rental Income: $2899 Airbnb ROI: 0.11% Traditional ROI: 3.72%
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.	$995,000	Airbnb cash on cash: -1.24% Traditional cash on cash: 3.65% Airbnb Rental Income: $1729 Traditional Rental Income: $5783 Airbnb ROI: -1.24% Traditional ROI: 3.65%
15400 Gulf Blvd #505 Madeira Beach, FL Enjoy breathtaking waterviews from this beautiful 5th floor corner unit! Spectacular sunse...	2 beds \| 2 baths \| 1,120 sq.ft.	$805,000	Airbnb cash on cash: -2.09% Traditional cash on cash: 0.04% Airbnb Rental Income: $1562 Traditional Rental Income: $2708 Airbnb ROI: -2.09% Traditional ROI: 0.04%
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: 5.45% Airbnb Rental Income: $1729 Traditional Rental Income: $3571 Airbnb ROI: 0.5% Traditional ROI: 5.45%
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.	$425,000	Airbnb cash on cash: -2.35% Traditional cash on cash: 0.67% Airbnb Rental Income: $1562 Traditional Rental Income: $2315 Airbnb ROI: -2.35% Traditional ROI: 0.67%
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.	$575,000	Airbnb cash on cash: 0.09% Traditional cash on cash: 3.38% Airbnb Rental Income: $1562 Traditional Rental Income: $2883 Airbnb ROI: 0.09% Traditional ROI: 3.38%
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%
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%
13135 4th St E Madeira Beach, FL Walk to the Beautiful Gulf of Mexico Beach! Great opportunity for 1031 Exchange. These 3 ...	N/A beds \| N/A baths \| 793 sq.ft.	$275,000	Airbnb cash on cash: 4.53% Traditional cash on cash: 3.74% Airbnb Rental Income: $2714 Traditional Rental Income: $1867 Airbnb ROI: 4.53% Traditional ROI: 3.74%
15316 Gulf Blvd #404 Madeira Beach, FL Indulge in refined beachfront living in Madeira Beach, where the soothing cadence of the G...	3 beds \| 2 baths \| 1,625 sq.ft.	$1,200,000	Airbnb cash on cash: -2.61% Traditional cash on cash: 0.3% Airbnb Rental Income: $1729 Traditional Rental Income: $4500 Airbnb ROI: -2.61% Traditional ROI: 0.3%
54 154th Ave #54 Madeira Beach, FL Under contract-accepting backup offers. Airbnb and short-term rental! Welcome to paradise!...	2 beds \| 1 baths \| 720 sq.ft.	$1,400,000	Airbnb cash on cash: -1.16% Traditional cash on cash: -0.4% Airbnb Rental Income: $1562 Traditional Rental Income: $2109 Airbnb ROI: -1.16% Traditional ROI: -0.4%
52 154th Ave #52 Madeira Beach, FL Greeat 2 bedroom unit only 189 steps to the Gulf of Mexico. Needs TLC but ideal location,...	2 beds \| 1 baths \| 720 sq.ft.	$1,400,000	Airbnb cash on cash: -0.94% Traditional cash on cash: -0.55% Airbnb Rental Income: $1562 Traditional Rental Income: $1616 Airbnb ROI: -0.94% Traditional ROI: -0.55%
401 150TH AVENUE #223 Madeira Beach, FL LOW CONDO FEE! Only $692/month including EVERYTHING except Electricity (even Cable, Net, a...	2 beds \| 2 baths \| 1,125 sq.ft.	$399,400	Airbnb cash on cash: -2.16% Traditional cash on cash: 0.2% Airbnb Rental Income: $1562 Traditional Rental Income: $1994 Airbnb ROI: -2.16% Traditional ROI: 0.2%
14555 N Bayshore Dr Madeira Beach, FL This is the kind of property some wait onâ¦ then regret when itâs gone. Solid block co...	2 beds \| 1 baths \| 1,277 sq.ft.	$587,999	Airbnb cash on cash: -0.18% Traditional cash on cash: 4.44% Airbnb Rental Income: $1562 Traditional Rental Income: $3652 Airbnb ROI: -0.18% Traditional ROI: 4.44%

Real Estate investment in Madeira-beach, FL

There are 198 properties for sale in the city of Madeira Beach . The median list price in Madeira Beach is $799,000 and the average price per square foot is $541. In April 2026, the average monthly cash on cash return in Madeira Beach is 1.00%. The average monthly rental income in Madeira Beach is $3,001.

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

There are 198 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 $3,001.

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%

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%

50 137th Avenue Cir

Madeira Beach, FL

1 beds | 1 baths | 753 sq.ft.

$449,000

Airbnb cash on cash: -1.08%

Traditional cash on cash: 3.85%

Airbnb Rental Income: $1077

Traditional Rental Income: $2779

Airbnb ROI: -1.08%

Traditional ROI: 3.85%

329 MEDALLION BOULEVARD #B

Madeira Beach, FL

2 beds | 2 baths | 915 sq.ft.

$479,900

Airbnb cash on cash: -2.18%

Traditional cash on cash: 1.83%

Airbnb Rental Income: $1562

Traditional Rental Income: $2914

Airbnb ROI: -2.18%

Traditional ROI: 1.83%

747 Pruitt Dr

Madeira Beach, FL

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

$549,900

Airbnb cash on cash: 0.13%

Traditional cash on cash: 4.56%

Airbnb Rental Income: $1729

Traditional Rental Income: $3527

Airbnb ROI: 0.13%

Traditional ROI: 4.56%

15400 Gulf Blvd #402

Madeira Beach, FL

2 beds | 2 baths | 1,190 sq.ft.

$839,000

Airbnb cash on cash: -2.44%

Traditional cash on cash: -0.89%

Airbnb Rental Income: $1562

Traditional Rental Income: $2330

Airbnb ROI: -2.44%

Traditional ROI: -0.89%

14117 Palm St

Madeira Beach, FL

2 beds | 1 baths | 936 sq.ft.

$320,000

Airbnb cash on cash: 0.96%

Traditional cash on cash: 5.62%

Airbnb Rental Income: $1562

Traditional Rental Income: $2515

Airbnb ROI: 0.96%

Traditional ROI: 5.62%

13630 Gulf Blvd #200C

Madeira Beach, FL

3 beds | 3 baths | 3,186 sq.ft.

$3,230,000

Airbnb cash on cash: -1.96%

Traditional cash on cash: -0.2%

Airbnb Rental Income: $1729

Traditional Rental Income: $6531

Airbnb ROI: -1.96%