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
747 PRUITT DRIVE 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: 4.95% Traditional cash on cash: 2.71% Airbnb Rental Income: $5163 Traditional Rental Income: $2817 Airbnb ROI: 4.95% Traditional ROI: 2.71%
14000 MIRAMAR AVENUE Madeira Beach, FL Rare 4 Bedroom and 2 Bedroom Duplex just 3 blocks from the beach! Live in one and rent ou...	6 beds \| N/A baths \| 2,196 sq.ft.	$849,900	Airbnb cash on cash: 3% Traditional cash on cash: 1.11% Airbnb Rental Income: $5163 Traditional Rental Income: $2618 Airbnb ROI: 3% Traditional ROI: 1.11%
353 144TH AVENUE Madeira Beach, FL This prime waterfront property presents a rare chance for those seeking Gulf Coast living....	3 beds \| 2 baths \| 1,516 sq.ft.	$800,000	Airbnb cash on cash: 3.61% Traditional cash on cash: 2.27% Airbnb Rental Income: $5163 Traditional Rental Income: $3114 Airbnb ROI: 3.61% Traditional ROI: 2.27%
575 CRYSTAL DRIVE Madeira Beach, FL Pre-Construction. To be built. This is a rare and unique opportunity to own a stunning new...	4 beds \| 5 baths \| 4,501 sq.ft.	$3,975,000	Airbnb cash on cash: 0.19% Traditional cash on cash: 0.33% Airbnb Rental Income: $7152 Traditional Rental Income: $6299 Airbnb ROI: 0.19% Traditional ROI: 0.33%
13235 GULF BOULEVARD #303 Madeira Beach, FL Under contract-accepting backup offers. MADEIRA BEACH .....WATERFRONT CONDO!!!! STEPS T...	2 beds \| 2 baths \| 734 sq.ft.	$529,000	Airbnb cash on cash: 3.67% Traditional cash on cash: 2.05% Airbnb Rental Income: $3787 Traditional Rental Income: $2166 Airbnb ROI: 3.67% Traditional ROI: 2.05%
533 LILLIAN DRIVE Madeira Beach, FL Make Every Day Feel Like a Vacation in Your Own Waterfront Paradise Retreat! This MOVE IN ...	4 beds \| 3 baths \| 1,986 sq.ft.	$1,245,000	Airbnb cash on cash: 2.84% Traditional cash on cash: 1.56% Airbnb Rental Income: $7152 Traditional Rental Income: $4291 Airbnb ROI: 2.84% Traditional ROI: 1.56%
14900 GULF BOULEVARD #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: 1.09% Traditional cash on cash: 0.13% Airbnb Rental Income: $3787 Traditional Rental Income: $2316 Airbnb ROI: 1.09% Traditional ROI: 0.13%
13235 GULF BOULEVARD #207 Madeira Beach, FL Under contract-accepting backup offers. Welcome to your slice of paradise in Madeira Beach...	2 beds \| 1 baths \| 768 sq.ft.	$485,000	Airbnb cash on cash: 4.03% Traditional cash on cash: 2.66% Airbnb Rental Income: $3787 Traditional Rental Income: $2347 Airbnb ROI: 4.03% Traditional ROI: 2.66%
14111 W PARSLEY DRIVE 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.	$489,900	Airbnb cash on cash: 9.5% Traditional cash on cash: 2.36% Airbnb Rental Income: $7152 Traditional Rental Income: $2497 Airbnb ROI: 9.5% Traditional ROI: 2.36%
15400 GULF BOULEVARD #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: 2.4% Traditional cash on cash: 1.86% Airbnb Rental Income: $3787 Traditional Rental Income: $2618 Airbnb ROI: 2.4% Traditional ROI: 1.86%
343 REX PLACE #G Madeira Beach, FL Looking for a GREAT INVESTMENT PROPERTY, SECOND HOME OR A MORE PERMANENT PLACE to hang you...	2 beds \| 2 baths \| 1,040 sq.ft.	$365,000	Airbnb cash on cash: 2.35% Traditional cash on cash: -0.51% Airbnb Rental Income: $3787 Traditional Rental Income: $1985 Airbnb ROI: 2.35% Traditional ROI: -0.51%
14950 GULF BOULEVARD #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: 0.37% Traditional cash on cash: 0.09% Airbnb Rental Income: $3787 Traditional Rental Income: $2628 Airbnb ROI: 0.37% Traditional ROI: 0.09%
12924 Gulf Boulevard #502 Madeira Beach, FL Whether you're looking for a dream vacation retreat or a high-performing income property, ...	1 beds \| 1 baths \| 865 sq.ft.	$749,000	Airbnb cash on cash: 0.08% Traditional cash on cash: 0.22% Airbnb Rental Income: $2253 Traditional Rental Income: $1789 Airbnb ROI: 0.08% Traditional ROI: 0.22%
425 150TH AVENUE #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.	$968,000	Airbnb cash on cash: 2.2% Traditional cash on cash: 1.38% Airbnb Rental Income: $5163 Traditional Rental Income: $3382 Airbnb ROI: 2.2% Traditional ROI: 1.38%
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: 8.55% Traditional cash on cash: 2.49% Airbnb Rental Income: $5163 Traditional Rental Income: $1926 Airbnb ROI: 8.55% Traditional ROI: 2.49%
14225 PALM STREET #3 Madeira Beach, FL Step inside to this completely remodeled Madeira Beach condo and experience modern coastal...	1 beds \| 1 baths \| 500 sq.ft.	$249,900	Airbnb cash on cash: 3.43% Traditional cash on cash: 2.08% Airbnb Rental Income: $2253 Traditional Rental Income: $1371 Airbnb ROI: 3.43% Traditional ROI: 2.08%
811 BAY POINT DRIVE Madeira Beach, FL Under contract-accepting backup offers. Incredible expanded WATER VIEW IN MADEIRA BEACH ...	3 beds \| 2 baths \| 2,062 sq.ft.	$650,000	Airbnb cash on cash: 3.16% Traditional cash on cash: 1.53% Airbnb Rental Income: $5163 Traditional Rental Income: $3125 Airbnb ROI: 3.16% Traditional ROI: 1.53%
14146 GULF BOULEVARD #3A Madeira Beach, FL *FRACTIONAL OWNERSHIP* Owner is selling 50% ownership. ----> https://vimeo.com/1085300...	2 beds \| 2 baths \| 1,415 sq.ft.	$565,000	Airbnb cash on cash: -0.2% Traditional cash on cash: -0.52% Airbnb Rental Income: $3787 Traditional Rental Income: $2803 Airbnb ROI: -0.2% Traditional ROI: -0.52%
517 JOHNS PASS AVENUE Madeira Beach, FL Imagine waking each morning to the shimmer of wide-open Intracoastal waters, sunlight pour...	3 beds \| 2 baths \| 2,342 sq.ft.	$1,750,000	Airbnb cash on cash: 0.45% Traditional cash on cash: 0.61% Airbnb Rental Income: $5163 Traditional Rental Income: $4376 Airbnb ROI: 0.45% Traditional ROI: 0.61%
249 BOCA CIEGA DRIVE Madeira Beach, FL Back on market, financing fell through. Owner financing now available! Excellent investm...	3 beds \| 3 baths \| 2,160 sq.ft.	$1,200,000	Airbnb cash on cash: 1.46% Traditional cash on cash: 1.43% Airbnb Rental Income: $5163 Traditional Rental Income: $4086 Airbnb ROI: 1.46% Traditional ROI: 1.43%
197 148TH AVENUE 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.	$435,000	Airbnb cash on cash: 4.33% Traditional cash on cash: 2.18% Airbnb Rental Income: $3787 Traditional Rental Income: $2094 Airbnb ROI: 4.33% Traditional ROI: 2.18%
171 MEDALLION BOULEVARD #H Madeira Beach, FL AFFORDABLE WATERFRONT, WATERVIEW CONDO WITH BOAT SLIP IN MADEIRA BEACH NEWLY UPDATED. Amaz...	1 beds \| 2 baths \| 755 sq.ft.	$450,000	Airbnb cash on cash: 1.82% Traditional cash on cash: 2.83% Airbnb Rental Income: $2253 Traditional Rental Income: $2118 Airbnb ROI: 1.82% Traditional ROI: 2.83%
14141 GULF BOULEVARD #5 Madeira Beach, FL This beach cottage was renovated in 2025 and is zoned for daily rentals with easy beach ac...	1 beds \| 1 baths \| 392 sq.ft.	$319,000	Airbnb cash on cash: 3.28% Traditional cash on cash: 1.38% Airbnb Rental Income: $2253 Traditional Rental Income: $1120 Airbnb ROI: 3.28% Traditional ROI: 1.38%
14050 W PARSLEY DRIVE Madeira Beach, FL Under contract-accepting backup offers. Back on market because buyer could not move forwar...	3 beds \| 2 baths \| 1,094 sq.ft.	$585,000	Airbnb cash on cash: 4.65% Traditional cash on cash: 1.93% Airbnb Rental Income: $5163 Traditional Rental Income: $2624 Airbnb ROI: 4.65% Traditional ROI: 1.93%
326 129TH AVENUE E Madeira Beach, FL Iconic Waterfront Living in the Heart of Johnâs Pass. Experience the pinnacle of coastal...	5 beds \| 5 baths \| 3,586 sq.ft.	$3,149,000	Airbnb cash on cash: 0.79% Traditional cash on cash: 0.81% Airbnb Rental Income: $7951 Traditional Rental Income: $6487 Airbnb ROI: 0.79% Traditional ROI: 0.81%
13720 GULF BOULEVARD #305 Madeira Beach, FL Under contract-accepting backup offers. Welcome to your slice of paradise at Villa Madeira...	3 beds \| 2 baths \| 1,130 sq.ft.	$850,000	Airbnb cash on cash: 2.48% Traditional cash on cash: 2.96% Airbnb Rental Income: $5163 Traditional Rental Income: $4490 Airbnb ROI: 2.48% Traditional ROI: 2.96%
403 NORMANDY ROAD Madeira Beach, FL One or more photo(s) has been virtually staged. Short Sale. Live the Island Life in Style ...	3 beds \| 2 baths \| 1,826 sq.ft.	$899,000	Airbnb cash on cash: 2.27% Traditional cash on cash: 1.8% Airbnb Rental Income: $5163 Traditional Rental Income: $3720 Airbnb ROI: 2.27% Traditional ROI: 1.8%
14300 GULF BOULEVARD #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: -0.34% Traditional cash on cash: -0.93% Airbnb Rental Income: $3787 Traditional Rental Income: $2447 Airbnb ROI: -0.34% Traditional ROI: -0.93%
171 MEDALLION BOULEVARD #F Madeira Beach, FL Purchase this condominium and enjoy the Florida lifestyle at its finest. This property is ...	1 beds \| 2 baths \| 755 sq.ft.	$364,900	Airbnb cash on cash: 2.74% Traditional cash on cash: 4.77% Airbnb Rental Income: $2253 Traditional Rental Income: $2386 Airbnb ROI: 2.74% Traditional ROI: 4.77%
15316 GULF BOULEVARD #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: 1.2% Traditional cash on cash: 0.1% Airbnb Rental Income: $5163 Traditional Rental Income: $2616 Airbnb ROI: 1.2% Traditional ROI: 0.1%
14048 GULF BOULEVARD #402 Madeira Beach, FL Under Construction. GULF FRONT - UNDER CONSTRUCTION. Spectacular new building on Madeira ...	2 beds \| 3 baths \| 1,791 sq.ft.	$2,779,000	Airbnb cash on cash: -1.22% Traditional cash on cash: -1.2% Airbnb Rental Income: $3787 Traditional Rental Income: $2999 Airbnb ROI: -1.22% Traditional ROI: -1.2%
15318 HARBOR DRIVE Madeira Beach, FL Diamond In the Rough. New Fence, New Garage Door. You have a fabulous opportunity to purch...	3 beds \| 2 baths \| 1,564 sq.ft.	$1,500,000	Airbnb cash on cash: 1.13% Traditional cash on cash: 0.46% Airbnb Rental Income: $5163 Traditional Rental Income: $3184 Airbnb ROI: 1.13% Traditional ROI: 0.46%
12924 GULF BOULEVARD #503 Madeira Beach, FL Under contract-accepting backup offers. NEW LOWER PRICE!! Top Floor Condo with Direct Gul...	2 beds \| 2 baths \| 1,030 sq.ft.	$820,000	Airbnb cash on cash: 1.61% Traditional cash on cash: 2.2% Airbnb Rental Income: $3787 Traditional Rental Income: $3420 Airbnb ROI: 1.61% Traditional ROI: 2.2%
14001 GULF BOULEVARD #206 Madeira Beach, FL Welcome home to Madeira Beach, where every day feels like a vacation. RARE GEM ALERT!!! NO...	1 beds \| 2 baths \| 840 sq.ft.	$395,000	Airbnb cash on cash: 0.27% Traditional cash on cash: 2.63% Airbnb Rental Income: $2253 Traditional Rental Income: $2561 Airbnb ROI: 0.27% Traditional ROI: 2.63%
13500 GULF BOULEVARD #602 Madeira Beach, FL DIRECTLY BEACHFRONT. Large private balcony directly overlooking the Gulf. Panoramic views ...	2 beds \| 2 baths \| 1,200 sq.ft.	$860,000	Airbnb cash on cash: 1.42% Traditional cash on cash: 0.87% Airbnb Rental Income: $3787 Traditional Rental Income: $2526 Airbnb ROI: 1.42% Traditional ROI: 0.87%
565 CRYSTAL DRIVE Madeira Beach, FL Step into your Madeira Beach dream home with panoramic Intracoastal views and direct Gulf ...	3 beds \| 3 baths \| 2,253 sq.ft.	$1,449,000	Airbnb cash on cash: 1.36% Traditional cash on cash: 2.83% Airbnb Rental Income: $5163 Traditional Rental Income: $6092 Airbnb ROI: 1.36% Traditional ROI: 2.83%
256 144TH AVENUE Madeira Beach, FL Price Reduction â Motivated Seller Oversized Corner Lot with Multi-Family Zoning in Mad...	3 beds \| N/A baths \| 1,404 sq.ft.	$399,000	Airbnb cash on cash: 7.9% Traditional cash on cash: 1.45% Airbnb Rental Income: $5163 Traditional Rental Income: $1700 Airbnb ROI: 7.9% Traditional ROI: 1.45%
13253 BOCA CIEGA AVENUE Madeira Beach, FL Short Sale. Investor Special. Requires a fair amount of TLC / Rehab. Lower level suffered ...	3 beds \| 3 baths \| 1,990 sq.ft.	$449,000	Airbnb cash on cash: 7.89% Traditional cash on cash: 5.88% Airbnb Rental Income: $5163 Traditional Rental Income: $3269 Airbnb ROI: 7.89% Traditional ROI: 5.88%
14300 GULF BOULEVARD #401 Madeira Beach, FL Under contract-accepting backup offers. Own a Madeira Beach vacation rental condo that pay...	2 beds \| 2 baths \| 1,120 sq.ft.	$799,000	Airbnb cash on cash: 2.28% Traditional cash on cash: 1.3% Airbnb Rental Income: $3787 Traditional Rental Income: $2236 Airbnb ROI: 2.28% Traditional ROI: 1.3%
78 146TH AVENUE E Madeira Beach, FL Price improvement!!! Approved!!!Approved!!! Approved!!! Building redevelopment appro...	2 beds \| N/A baths \| 1,340 sq.ft.	$355,000	Airbnb cash on cash: 6.6% Traditional cash on cash: 4.56% Airbnb Rental Income: $3787 Traditional Rental Income: $2285 Airbnb ROI: 6.6% Traditional ROI: 4.56%

Real Estate investment in Madeira-beach, FL

There are 133 properties for sale in the city of Madeira Beach . The median list price in Madeira Beach is $659,500 and the average price per square foot is $425. In October 2025, the average monthly cash on cash return in Madeira Beach is 1.00%. The average monthly rental income in Madeira Beach is $2,386.

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

There are 133 investment properties available for sale in Madeira-beach.

In 2025, 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 $3,787.

Your search for investment property begins and ends here

Investment Property for Sale in Madeira Beach, FL

747 PRUITT DRIVE

Madeira Beach, FL

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

$619,900

Airbnb cash on cash: 4.95%

Traditional cash on cash: 2.71%

Airbnb Rental Income: $5163

Traditional Rental Income: $2817

Airbnb ROI: 4.95%

Traditional ROI: 2.71%

14000 MIRAMAR AVENUE

Madeira Beach, FL

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

$849,900

Airbnb cash on cash: 3%

Traditional cash on cash: 1.11%

Airbnb Rental Income: $5163

Traditional Rental Income: $2618

Airbnb ROI: 3%

Traditional ROI: 1.11%

353 144TH AVENUE

Madeira Beach, FL

3 beds | 2 baths | 1,516 sq.ft.

$800,000

Airbnb cash on cash: 3.61%

Traditional cash on cash: 2.27%

Airbnb Rental Income: $5163

Traditional Rental Income: $3114

Airbnb ROI: 3.61%

Traditional ROI: 2.27%

575 CRYSTAL DRIVE

Madeira Beach, FL

4 beds | 5 baths | 4,501 sq.ft.

$3,975,000

Airbnb cash on cash: 0.19%

Traditional cash on cash: 0.33%

Airbnb Rental Income: $7152

Traditional Rental Income: $6299

Airbnb ROI: 0.19%

Traditional ROI: 0.33%

13235 GULF BOULEVARD #303

Madeira Beach, FL

2 beds | 2 baths | 734 sq.ft.

$529,000

Airbnb cash on cash: 3.67%

Traditional cash on cash: 2.05%

Airbnb Rental Income: $3787

Traditional Rental Income: $2166

Airbnb ROI: 3.67%

Traditional ROI: 2.05%

533 LILLIAN DRIVE

Madeira Beach, FL

4 beds | 3 baths | 1,986 sq.ft.

$1,245,000

Airbnb cash on cash: 2.84%

Traditional cash on cash: 1.56%

Airbnb Rental Income: $7152

Traditional Rental Income: $4291

Airbnb ROI: 2.84%

Traditional ROI: 1.56%

14900 GULF BOULEVARD #304

Madeira Beach, FL

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

$729,000

Airbnb cash on cash: 1.09%

Traditional cash on cash: 0.13%

Airbnb Rental Income: $3787

Traditional Rental Income: $2316

Airbnb ROI: 1.09%

Traditional ROI: 0.13%

13235 GULF BOULEVARD #207

Madeira Beach, FL

2 beds | 1 baths | 768 sq.ft.

$485,000

Airbnb cash on cash: 4.03%

Traditional cash on cash: 2.66%

Airbnb Rental Income: $3787

Traditional Rental Income: $2347

Airbnb ROI: 4.03%