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.	$999,900	Airbnb cash on cash: -0.52% Traditional cash on cash: 1.59% Airbnb Rental Income: $1729 Traditional Rental Income: $3213 Airbnb ROI: -0.52% Traditional ROI: 1.59%
356 144th Ave Madeira Beach, FL New Roof on its way New Paint inside and out. Beautifully maintained home. Wood flooring t...	2 beds \| 1 baths \| 756 sq.ft.	$375,000	Airbnb cash on cash: 3.95% Traditional cash on cash: 1.06% Airbnb Rental Income: $2714 Traditional Rental Income: $1055 Airbnb ROI: 3.95% Traditional ROI: 1.06%
50 137TH AVENUE CIRCLE Madeira Beach, FL Exceptional waterfront opportunity in the heart of Madeira Beach. Just steps from Gulf Bou...	1 beds \| 1 baths \| 753 sq.ft.	$490,000	Airbnb cash on cash: -1.07% Traditional cash on cash: 1.26% Airbnb Rental Income: $1077 Traditional Rental Income: $1777 Airbnb ROI: -1.07% Traditional ROI: 1.26%
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.	$619,900	Airbnb cash on cash: 0% Traditional cash on cash: 2.71% Airbnb Rental Income: $1729 Traditional Rental Income: $2817 Airbnb ROI: 0% Traditional ROI: 2.71%
14117 Palm St Madeira Beach, FL Under contract-accepting backup offers. Beautiful Beach Bungalow! Immaculate home located ...	2 beds \| 1 baths \| 936 sq.ft.	$360,000	Airbnb cash on cash: 0.75% Traditional cash on cash: 6.72% Airbnb Rental Income: $1562 Traditional Rental Income: $3131 Airbnb ROI: 0.75% Traditional ROI: 6.72%
14000 Miramar Ave Madeira Beach, FL Rare 4 Bedroom and 2 Bedroom Duplex just 3 blocks from the beach! Great for a 1031 exchang...	6 beds \| N/A baths \| 2,196 sq.ft.	$824,900	Airbnb cash on cash: -0.5% Traditional cash on cash: 1.46% Airbnb Rental Income: $1562 Traditional Rental Income: $2618 Airbnb ROI: -0.5% Traditional ROI: 1.46%
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.	$618,000	Airbnb cash on cash: -1.5% Traditional cash on cash: 1.94% Airbnb Rental Income: $1562 Traditional Rental Income: $3098 Airbnb ROI: -1.5% Traditional ROI: 1.94%
575 Crystal Dr Madeira Beach, FL Pre-Construction. To be built. This is a rare and unique opportunity to own a stunning new...	4 beds \| 4 baths \| 4,501 sq.ft.	$3,975,000	Airbnb cash on cash: -1.25% Traditional cash on cash: 0.33% Airbnb Rental Income: $785 Traditional Rental Income: $6299 Airbnb ROI: -1.25% Traditional ROI: 0.33%
245 145TH AVENUE E Madeira Beach, FL Great Investment Opportunity for the right buyer! This duplex property sits on 104x70 fo...	N/A beds \| N/A baths \| 1,415 sq.ft.	$485,000	Airbnb cash on cash: -1.8% Traditional cash on cash: 0.85% Airbnb Rental Income: $785 Traditional Rental Income: $1671 Airbnb ROI: -1.8% Traditional ROI: 0.85%
14906 N Bayshore Dr Madeira Beach, FL Under contract-accepting backup offers. Prime Investment Opportunity in Madeira Beach â ...	3 beds \| N/A baths \| 1,399 sq.ft.	$379,900	Airbnb cash on cash: -1.42% Traditional cash on cash: 3.59% Airbnb Rental Income: $785 Traditional Rental Income: $2248 Airbnb ROI: -1.42% Traditional ROI: 3.59%
533 Lillian Dr Madeira Beach, FL One or more photo(s) has been virtually staged. Make Every Day Feel Like a Vacation in You...	4 beds \| 3 baths \| 1,986 sq.ft.	$1,200,000	Airbnb cash on cash: -1.77% Traditional cash on cash: 1.66% Airbnb Rental Income: $785 Traditional Rental Income: $4291 Airbnb ROI: -1.77% Traditional ROI: 1.66%
14925 1st St E Madeira Beach, FL Breathtaking views of the wide canal from nearly every room in the house. Move in ready. F...	N/A beds \| N/A baths \| 2,742 sq.ft.	$999,000	Airbnb cash on cash: 0.52% Traditional cash on cash: 0.07% Airbnb Rental Income: $2714 Traditional Rental Income: $1653 Airbnb ROI: 0.52% Traditional ROI: 0.07%
14900 Gulf Blvd #304 Madeira Beach, FL Stunning Gulf-Front Condo in the Heart of Madeira Beach. Experience the ultimate beachfron...	2 beds \| 2 baths \| 1,100 sq.ft.	$729,000	Airbnb cash on cash: -2.63% Traditional cash on cash: -0.86% Airbnb Rental Income: $1562 Traditional Rental Income: $2316 Airbnb ROI: -2.63% Traditional ROI: -0.86%
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.	$1,050,000	Airbnb cash on cash: -1.23% Traditional cash on cash: 1.9% Airbnb Rental Income: $1729 Traditional Rental Income: $4312 Airbnb ROI: -1.23% Traditional ROI: 1.9%
14111 W Parsley Dr Madeira Beach, FL Investment Opportunity in Madeira Beach! Cash or Hard Money buyers only, hereâs your ch...	4 beds \| N/A baths \| 1,518 sq.ft.	$474,900	Airbnb cash on cash: -2.11% Traditional cash on cash: 2.46% Airbnb Rental Income: $785 Traditional Rental Income: $2497 Airbnb ROI: -2.11% Traditional ROI: 2.46%
15400 Gulf Blvd #403 Madeira Beach, FL If you are looking for a condo that is in move in condition, this is the one for you! Expe...	2 beds \| 2 baths \| 1,190 sq.ft.	$699,900	Airbnb cash on cash: -2.15% Traditional cash on cash: 0.16% Airbnb Rental Income: $1562 Traditional Rental Income: $2618 Airbnb ROI: -2.15% Traditional ROI: 0.16%
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: $1985 Airbnb ROI: -3.42% Traditional ROI: -0.77%
14950 Gulf Blvd #1206 Madeira Beach, FL Welcome to Ocean Sands in the heart of Madeira Beach! Ride the elevator to the penthouse l...	2 beds \| 2 baths \| 1,225 sq.ft.	$1,295,000	Airbnb cash on cash: -1.89% Traditional cash on cash: -0.63% Airbnb Rental Income: $1562 Traditional Rental Income: $2628 Airbnb ROI: -1.89% Traditional ROI: -0.63%
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.	$459,000	Airbnb cash on cash: -2.25% Traditional cash on cash: -0.96% Airbnb Rental Income: $1562 Traditional Rental Income: $1665 Airbnb ROI: -2.25% Traditional ROI: -0.96%
425 150th Ave #2301 Madeira Beach, FL WATERFRONT LUXURY LIVING \| 3 BEDROOM CONDO WITH BOAT SLIP, LIFT & PRIVATE GARAGE INCOME PR...	3 beds \| 2 baths \| 1,825 sq.ft.	$939,000	Airbnb cash on cash: -2.73% Traditional cash on cash: -0.29% Airbnb Rental Income: $1729 Traditional Rental Income: $3382 Airbnb ROI: -2.73% Traditional ROI: -0.29%
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.	$385,000	Airbnb cash on cash: 0.63% Traditional cash on cash: 2.49% Airbnb Rental Income: $1729 Traditional Rental Income: $1926 Airbnb ROI: 0.63% Traditional ROI: 2.49%
14200 E Parsley Dr Madeira Beach, FL GREAT INVESTMENT! ONLY $250K/unit!!! Highly desired rentals! Terrific beach neighborhood...	5 beds \| N/A baths \| 1,822 sq.ft.	$499,950	Airbnb cash on cash: -0.11% Traditional cash on cash: 2.47% Airbnb Rental Income: $1729 Traditional Rental Income: $2457 Airbnb ROI: -0.11% Traditional ROI: 2.47%
14146 Gulf Blvd #3A Madeira Beach, FL *FRACTIONAL OWNERSHIP* Owner is selling 50% ownership. ----> https://vimeo.com/1085300...	2 beds \| 2 baths \| 1,415 sq.ft.	$529,900	Airbnb cash on cash: -3.9% Traditional cash on cash: -0.48% Airbnb Rental Income: $1562 Traditional Rental Income: $2803 Airbnb ROI: -3.9% Traditional ROI: -0.48%
231 E Madeira Ave Madeira Beach, FL Experience the ultimate coastal lifestyle in this beautifully updated waterfront home in M...	3 beds \| 2 baths \| 1,105 sq.ft.	$895,000	Airbnb cash on cash: -0.38% Traditional cash on cash: 1.44% Airbnb Rental Income: $1729 Traditional Rental Income: $2766 Airbnb ROI: -0.38% Traditional ROI: 1.44%
197 148th Ave E Madeira Beach, FL Short Sale. Incredible opportunity to build your dream home or investment property in a gr...	2 beds \| 1 baths \| 1,250 sq.ft.	$335,000	Airbnb cash on cash: 0% Traditional cash on cash: 3.12% Airbnb Rental Income: $1562 Traditional Rental Income: $2094 Airbnb ROI: 0% Traditional ROI: 3.12%
171 Medallion Blvd #H Madeira Beach, FL DEEDED BOAT SLIP!!!!! AFFORDABLE WATERFRONT, WATERVIEW CONDO IN MADEIRA BEACH NEWLY UPDATE...	1 beds \| 1 baths \| 755 sq.ft.	$495,999	Airbnb cash on cash: -2.58% Traditional cash on cash: 0.45% Airbnb Rental Income: $1077 Traditional Rental Income: $2118 Airbnb ROI: -2.58% Traditional ROI: 0.45%
244 145TH AVENUE E Madeira Beach, FL An extraordinary opportunity to finish the transformation of a true Madeira Beach waterfro...	3 beds \| 3 baths \| 1,654 sq.ft.	$750,000	Airbnb cash on cash: -0.59% Traditional cash on cash: 1.85% Airbnb Rental Income: $1729 Traditional Rental Income: $2953 Airbnb ROI: -0.59% Traditional ROI: 1.85%
15316 Gulf Blvd #301 Madeira Beach, FL Imagine waking each day to the breathtaking panorama of the Gulf of America (formerly Gulf...	3 beds \| 2 baths \| 1,625 sq.ft.	$1,200,000	Airbnb cash on cash: -2.73% Traditional cash on cash: -1.18% Airbnb Rental Income: $1729 Traditional Rental Income: $2974 Airbnb ROI: -2.73% Traditional ROI: -1.18%
14607 N Bayshore Dr Madeira Beach, FL Wide open water view of the intercoastal waterway and Boca Ciega Bay is in your backyard. ...	N/A beds \| N/A baths \| 1,570 sq.ft.	$875,000	Airbnb cash on cash: 0.96% Traditional cash on cash: 0.61% Airbnb Rental Income: $2714 Traditional Rental Income: $1790 Airbnb ROI: 0.96% Traditional ROI: 0.61%
215 Medallion Blvd #G Madeira Beach, FL Very spacious 1 BR/1.5 BA townhome in Madeira Beach. One of a kind view in Madeira Beach Y...	1 beds \| 1 baths \| 755 sq.ft.	$495,999	Airbnb cash on cash: -2.57% Traditional cash on cash: -0.44% Airbnb Rental Income: $1077 Traditional Rental Income: $1699 Airbnb ROI: -2.57% Traditional ROI: -0.44%
14300 Gulf Blvd #104 Madeira Beach, FL Income-Producing Gulf-Front Opportunity! Welcome to Kima Condos, an exclusive 30-unit, wel...	2 beds \| 2 baths \| 1,120 sq.ft.	$950,000	Airbnb cash on cash: -2.44% Traditional cash on cash: -0.93% Airbnb Rental Income: $1562 Traditional Rental Income: $2447 Airbnb ROI: -2.44% Traditional ROI: -0.93%
15302 Harbor Dr Madeira Beach, FL LIVE THE MADEIRA BEACH DREAM â WALK TO THE BEACH, BOAT FROM YOUR BACKYARD! Just 5 min...	2 beds \| 2 baths \| 1,980 sq.ft.	$949,000	Airbnb cash on cash: -1.17% Traditional cash on cash: 1.26% Airbnb Rental Income: $1562 Traditional Rental Income: $3259 Airbnb ROI: -1.17% Traditional ROI: 1.26%
10830 Navajo Dr Madeira Beach, FL Outstanding Lakefront Mixed-Use Property \| Zoned General Office/Residential: An exceptiona...	4 beds \| 3 baths \| 7,040 sq.ft.	$1,950,000	Airbnb cash on cash: -0.89% Traditional cash on cash: 0.09% Airbnb Rental Income: $2373 Traditional Rental Income: $3571 Airbnb ROI: -0.89% Traditional ROI: 0.09%
165 Medallion Blvd #C Madeira Beach, FL Waterfront Living For The Astute Buyer! Presenting as a wonderful opportunity for savvy pr...	1 beds \| 1 baths \| 430 sq.ft.	$350,000	Airbnb cash on cash: -1.85% Traditional cash on cash: 2.16% Airbnb Rental Income: $1077 Traditional Rental Income: $2027 Airbnb ROI: -1.85% Traditional ROI: 2.16%
14150 N Bayshore Dr Madeira Beach, FL Welcome to your 2/1 dream home, a completely furnished and updated tropical oasis just a f...	N/A beds \| N/A baths \| 700 sq.ft.	$275,000	Airbnb cash on cash: 6.4% Traditional cash on cash: 5.41% Airbnb Rental Income: $2714 Traditional Rental Income: $1817 Airbnb ROI: 6.4% Traditional ROI: 5.41%
175 133rd Ave E Madeira Beach, FL Welcome to an exceptional investment opportunity in one of Madeira Beachâs most desirabl...	4 beds \| N/A baths \| 1,790 sq.ft.	$699,999	Airbnb cash on cash: 1.23% Traditional cash on cash: 2.79% Airbnb Rental Income: $2714 Traditional Rental Income: $3095 Airbnb ROI: 1.23% Traditional ROI: 2.79%
171 Medallion Blvd #F Madeira Beach, FL Purchase this condominium and enjoy the Florida lifestyle at its finest. This property is ...	1 beds \| 1 baths \| 755 sq.ft.	$364,900	Airbnb cash on cash: -2.72% Traditional cash on cash: 2.18% Airbnb Rental Income: $1077 Traditional Rental Income: $2386 Airbnb ROI: -2.72% Traditional ROI: 2.18%
315 Medallion Blvd #E Madeira Beach, FL High & Dry 2nd Floor Beach Oasis â No Flooding Worries! Community Passes Milestone Inspe...	2 beds \| 2 baths \| 1,040 sq.ft.	$549,000	Airbnb cash on cash: -2.62% Traditional cash on cash: 0.92% Airbnb Rental Income: $1562 Traditional Rental Income: $2931 Airbnb ROI: -2.62% Traditional ROI: 0.92%
15316 Gulf Blvd #604 Madeira Beach, FL Incredible opportunity to enjoy your own piece of paradise. Your corner unit, 6th floor, ...	3 beds \| 2 baths \| 1,625 sq.ft.	$1,460,300	Airbnb cash on cash: -1.85% Traditional cash on cash: -0.85% Airbnb Rental Income: $1729 Traditional Rental Income: $2616 Airbnb ROI: -1.85% Traditional ROI: -0.85%
14184 W Parsley Dr Madeira Beach, FL Under contract-accepting backup offers. Imagine stepping into your dream beach cottage, op...	2 beds \| 1 baths \| 827 sq.ft.	$599,000	Airbnb cash on cash: -0.69% Traditional cash on cash: 1.65% Airbnb Rental Income: $1562 Traditional Rental Income: $2425 Airbnb ROI: -0.69% Traditional ROI: 1.65%

Real Estate investment in Madeira-beach, FL

There are 154 properties for sale in the city of Madeira Beach . The median list price in Madeira Beach is $770,000 and the average price per square foot is $503. In January 2026, the average monthly cash on cash return in Madeira Beach is N/A%. The average monthly rental income in Madeira Beach is $2,381.

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

There are 154 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 $2,381.

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.

$999,900

Airbnb cash on cash: -0.52%

Traditional cash on cash: 1.59%

Airbnb Rental Income: $1729

Traditional Rental Income: $3213

Airbnb ROI: -0.52%

Traditional ROI: 1.59%

356 144th Ave

Madeira Beach, FL

2 beds | 1 baths | 756 sq.ft.

$375,000

Airbnb cash on cash: 3.95%

Traditional cash on cash: 1.06%

Airbnb Rental Income: $2714

Traditional Rental Income: $1055

Airbnb ROI: 3.95%

Traditional ROI: 1.06%

50 137TH AVENUE CIRCLE

Madeira Beach, FL

1 beds | 1 baths | 753 sq.ft.

$490,000

Airbnb cash on cash: -1.07%

Traditional cash on cash: 1.26%

Airbnb Rental Income: $1077

Traditional Rental Income: $1777

Airbnb ROI: -1.07%

Traditional ROI: 1.26%

747 Pruitt Dr

Madeira Beach, FL

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

$619,900

Airbnb cash on cash: 0%

Traditional cash on cash: 2.71%

Airbnb Rental Income: $1729

Traditional Rental Income: $2817

Airbnb ROI: 0%

Traditional ROI: 2.71%

14117 Palm St

Madeira Beach, FL

2 beds | 1 baths | 936 sq.ft.

$360,000

Airbnb cash on cash: 0.75%

Traditional cash on cash: 6.72%

Airbnb Rental Income: $1562

Traditional Rental Income: $3131

Airbnb ROI: 0.75%

Traditional ROI: 6.72%

14000 Miramar Ave

Madeira Beach, FL

6 beds | N/A baths | 2,196 sq.ft.

$824,900

Airbnb cash on cash: -0.5%

Traditional cash on cash: 1.46%

Airbnb Rental Income: $1562

Traditional Rental Income: $2618

Airbnb ROI: -0.5%

Traditional ROI: 1.46%

13235 GULF BOULEVARD #315

Madeira Beach, FL

2 beds | 2 baths | 973 sq.ft.

$618,000

Airbnb cash on cash: -1.5%

Traditional cash on cash: 1.94%

Airbnb Rental Income: $1562

Traditional Rental Income: $3098

Airbnb ROI: -1.5%

Traditional ROI: 1.94%

575 Crystal Dr

Madeira Beach, FL

4 beds | 4 baths | 4,501 sq.ft.

$3,975,000

Airbnb cash on cash: -1.25%

Traditional cash on cash: 0.33%

Airbnb Rental Income: $785

Traditional Rental Income: $6299

Airbnb ROI: -1.25%