Real Estate Investment Properties for Sale in Anna Maria, FL

Looking for investment property in Anna Maria, FL with high ROI ?

Explore a variety of short-term homes & houses in Anna Maria, FL. Invest wisely with VRBO & Anna Maria, FL Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Single Family Homes for Sale in Anna Maria, FL

Search for Single Family Residential for Sale in Anna Maria, Florida. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 47 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
329 TARPON STREET ANNA MARIA, FL Experience the charm of Anna Maria Island with this NEWLY COMPLETED CONSTRUCTION. This lux...	4 beds \| 5 baths \| 3,751 sq.ft.	$5,800,000	Airbnb cash on cash: -0.78% Traditional cash on cash: 0.13% Airbnb Rental Income: $3476 Traditional Rental Income: $7593 Airbnb ROI: -0.78% Traditional ROI: 0.13%
313 MAGNOLIA AVENUE ANNA MARIA, FL Welcome to your dream getaway on Anna Maria Island! THIS HOME HAS A BRAND NEW ROOF! Nestle...	3 beds \| 2 baths \| 1,424 sq.ft.	$1,675,000	Airbnb cash on cash: -0.55% Traditional cash on cash: -0.66% Airbnb Rental Income: $3306 Traditional Rental Income: $2383 Airbnb ROI: -0.55% Traditional ROI: -0.66%
527 MAGNOLIA AVENUE ANNA MARIA, FL Tucked away along a tranquil canal in the heart of Anna Maria, this exceptional 3-bedroom,...	3 beds \| 2 baths \| 1,924 sq.ft.	$2,195,000	Airbnb cash on cash: -0.84% Traditional cash on cash: -0.45% Airbnb Rental Income: $3306 Traditional Rental Income: $3362 Airbnb ROI: -0.84% Traditional ROI: -0.45%
785 JACARANDA ROAD ANNA MARIA, FL OHHHH THE UPDATES!! BRAND NEW KITCHEN and flooring...and updates galore! There is so to ...	3 beds \| 3 baths \| 1,500 sq.ft.	$1,999,900	Airbnb cash on cash: -0.85% Traditional cash on cash: -0.71% Airbnb Rental Income: $3306 Traditional Rental Income: $2832 Airbnb ROI: -0.85% Traditional ROI: -0.71%
113 MAPLE AVENUE ANNA MARIA, FL THIS INCREDIBLE CUSTOM BUILT ESTATE IS JUST FIVE HOUSES FROM THE GULF AND NESTLED ON ONE O...	5 beds \| 5 baths \| 2,680 sq.ft.	$3,690,000	Airbnb cash on cash: -1.59% Traditional cash on cash: -0.56% Airbnb Rental Income: $3130 Traditional Rental Income: $5965 Airbnb ROI: -1.59% Traditional ROI: -0.56%
222 WILLOW AVENUE ANNA MARIA, FL Welcome to SeaLuxe, where luxury meets the beach! Located on one of the most desirable str...	4 beds \| 6 baths \| 3,265 sq.ft.	$4,995,000	Airbnb cash on cash: -1.45% Traditional cash on cash: -0.06% Airbnb Rental Income: $3476 Traditional Rental Income: $9145 Airbnb ROI: -1.45% Traditional ROI: -0.06%
120 WHITE AVENUE ANNA MARIA, FL Nestled on Anna Maria Islandâs most famous street, this beautifully renovated coastal re...	5 beds \| 4 baths \| 2,763 sq.ft.	$3,497,500	Airbnb cash on cash: -1.67% Traditional cash on cash: -1.06% Airbnb Rental Income: $3130 Traditional Rental Income: $4407 Airbnb ROI: -1.67% Traditional ROI: -1.06%
704 GLADIOLUS STREET ANNA MARIA, FL You are just a short walk to Beach and Bay from this quality constructed 4 bed/3 bath pool...	4 beds \| 3 baths \| 2,415 sq.ft.	$2,995,000	Airbnb cash on cash: -1.2% Traditional cash on cash: -0.87% Airbnb Rental Income: $3476 Traditional Rental Income: $3609 Airbnb ROI: -1.2% Traditional ROI: -0.87%
733 HOLLY ROAD ANNA MARIA, FL ***Welcome to Summer Breeze â a rare island gem on Anna Maria Islandâs coveted North E...	5 beds \| 4 baths \| 2,838 sq.ft.	$2,500,000	Airbnb cash on cash: -0.99% Traditional cash on cash: -0.31% Airbnb Rental Income: $3130 Traditional Rental Income: $3997 Airbnb ROI: -0.99% Traditional ROI: -0.31%
229 WILLOW AVENUE ANNA MARIA, FL Here is your chance to own a 5 bed/4.5 bath custom waterfront residence on one of the most...	5 beds \| 5 baths \| 3,250 sq.ft.	$6,375,000	Airbnb cash on cash: -1.69% Traditional cash on cash: -0.85% Airbnb Rental Income: $3130 Traditional Rental Income: $7388 Airbnb ROI: -1.69% Traditional ROI: -0.85%
212 OAK AVENUE ANNA MARIA, FL STUNNING RENOVATED 5 BEDROOM POOL HOME ON A DEEP WATER CANAL ONLY STEPS FROM THE BEACH!!! ...	5 beds \| 5 baths \| 3,844 sq.ft.	$3,950,000	Airbnb cash on cash: -1.24% Traditional cash on cash: -0.3% Airbnb Rental Income: $3130 Traditional Rental Income: $5840 Airbnb ROI: -1.24% Traditional ROI: -0.3%
401 N SHORE DRIVE ANNA MARIA, FL Stunning Fully Remodeled 3-Bedroom Home with Pool & Spa â Prime North End Location. Welc...	3 beds \| 2 baths \| 1,680 sq.ft.	$2,200,000	Airbnb cash on cash: -0.78% Traditional cash on cash: -0.64% Airbnb Rental Income: $3306 Traditional Rental Income: $2846 Airbnb ROI: -0.78% Traditional ROI: -0.64%
709 GLADIOLUS STREET ANNA MARIA, FL Great opportunity for investors and homeowners to start over and design to your very own t...	4 beds \| 3 baths \| 1,933 sq.ft.	$1,595,000	Airbnb cash on cash: -0.14% Traditional cash on cash: 0.58% Airbnb Rental Income: $3476 Traditional Rental Income: $3777 Airbnb ROI: -0.14% Traditional ROI: 0.58%
893 N SHORE DRIVE ANNA MARIA, FL One or more photo(s) has been virtually staged. One or more photos have been virtually sta...	4 beds \| 3 baths \| 2,933 sq.ft.	$3,990,000	Airbnb cash on cash: -0.68% Traditional cash on cash: -0.01% Airbnb Rental Income: $3476 Traditional Rental Income: $5167 Airbnb ROI: -0.68% Traditional ROI: -0.01%
771 JACARANDA ROAD ANNA MARIA, FL An easy 5-minute walk to the Gulf on the coveted north end of Anna Maria Island, Limelight...	3 beds \| 2 baths \| 1,447 sq.ft.	$1,799,000	Airbnb cash on cash: -0.77% Traditional cash on cash: -1.1% Airbnb Rental Income: $3306 Traditional Rental Income: $2024 Airbnb ROI: -0.77% Traditional ROI: -1.1%
513 BAYVIEW PLACE ANNA MARIA, FL This Bayview Palace is a One of a kind, thereâs nothing quite like this on Anna Maria Is...	4 beds \| 6 baths \| 3,464 sq.ft.	$3,999,000	Airbnb cash on cash: -0.73% Traditional cash on cash: 1.31% Airbnb Rental Income: $3476 Traditional Rental Income: $10270 Airbnb ROI: -0.73% Traditional ROI: 1.31%
412 ALAMANDA ROAD ANNA MARIA, FL This stunning and private retreat is perfect for those who enjoy indoor/outdoor living, fl...	2 beds \| 2 baths \| 1,168 sq.ft.	$1,650,000	Airbnb cash on cash: -0.97% Traditional cash on cash: -0.44% Airbnb Rental Income: $2055 Traditional Rental Income: $2344 Airbnb ROI: -0.97% Traditional ROI: -0.44%
112 MAPLE AVENUE ANNA MARIA, FL STUNNING NEW CONSTRUCTION HOME WEST OF GULF DRIVE! WELCOME TO THIS AMAZING FULLY FURNISHED...	5 beds \| 5 baths \| 2,545 sq.ft.	$4,965,000	Airbnb cash on cash: -0.78% Traditional cash on cash: -0.11% Airbnb Rental Income: $3130 Traditional Rental Income: $5495 Airbnb ROI: -0.78% Traditional ROI: -0.11%
113 PALMETTO AVENUE ANNA MARIA, FL Under Construction. Welcome to 113 Palmetto Avenue, an architectural showcase by Eason Bui...	4 beds \| 5 baths \| 2,220 sq.ft.	$5,500,000	Airbnb cash on cash: -0.78% Traditional cash on cash: -0.27% Airbnb Rental Income: $3476 Traditional Rental Income: $5335 Airbnb ROI: -0.78% Traditional ROI: -0.27%
111 CEDAR AVENUE ANNA MARIA, FL AMAZING HOME "BLUE CRUSH" ONLY 4 HOUSES TO THE BEACH!!! LOCATIONS LIKE THIS ARE RARELY AVA...	3 beds \| 3 baths \| 2,263 sq.ft.	$3,895,000	Airbnb cash on cash: -1.21% Traditional cash on cash: -1.11% Airbnb Rental Income: $3306 Traditional Rental Income: $2935 Airbnb ROI: -1.21% Traditional ROI: -1.11%
103 SUNSET LANE ANNA MARIA, FL Tucked away at the end of a quiet cul-de-sac in Sunset Cove, this elevated beach home is a...	3 beds \| 3 baths \| 2,800 sq.ft.	$2,695,000	Airbnb cash on cash: -0.45% Traditional cash on cash: 0.12% Airbnb Rental Income: $3306 Traditional Rental Income: $3991 Airbnb ROI: -0.45% Traditional ROI: 0.12%
519 VILLA ROSA WAY ANNA MARIA, FL This stunning property, situated on the premier private street of Anna Maria, was designed...	4 beds \| 5 baths \| 3,385 sq.ft.	$5,000,000	Airbnb cash on cash: -0.93% Traditional cash on cash: 0.12% Airbnb Rental Income: $3476 Traditional Rental Income: $7544 Airbnb ROI: -0.93% Traditional ROI: 0.12%
136 CRESCENT DR ANNA MARIA, FL Anna Maria Island charming remodeled coastal cottage. Now is the time for new owners to m...	2 beds \| 2 baths \| 1,068 sq.ft.	$1,249,000	Airbnb cash on cash: -1.09% Traditional cash on cash: -0.56% Airbnb Rental Income: $2055 Traditional Rental Income: $2141 Airbnb ROI: -1.09% Traditional ROI: -0.56%
527 BAYVIEW PLACE ANNA MARIA, FL Discover the potential of this two-bedroom, two-bathroom home situated on a generous 6,500...	2 beds \| 2 baths \| 1,246 sq.ft.	$1,100,000	Airbnb cash on cash: 0.06% Traditional cash on cash: 0.77% Airbnb Rental Income: $2055 Traditional Rental Income: $2253 Airbnb ROI: 0.06% Traditional ROI: 0.77%
510 MAGNOLIA AVENUE ANNA MARIA, FL Welcome to Aloha Beaches. This home is a successful active rental in the city of Anna Mari...	4 beds \| 3 baths \| 2,225 sq.ft.	$2,995,000	Airbnb cash on cash: -0.99% Traditional cash on cash: 0.12% Airbnb Rental Income: $3476 Traditional Rental Income: $5806 Airbnb ROI: -0.99% Traditional ROI: 0.12%
110 SPRING AVENUE ANNA MARIA, FL Welcome to this exceptional beach retreat, an exquisite 5-bedroom, 4.5-bath luxury coastal...	5 beds \| 5 baths \| 2,925 sq.ft.	$3,000,000	Airbnb cash on cash: -1.37% Traditional cash on cash: -0.18% Airbnb Rental Income: $3130 Traditional Rental Income: $5723 Airbnb ROI: -1.37% Traditional ROI: -0.18%
159 CRESCENT DRIVE ANNA MARIA, FL Location, location, Location. Welcome to Tropical Paradise. What more can you ask for in t...	4 beds \| 3 baths \| 2,567 sq.ft.	$2,995,000	Airbnb cash on cash: -0.99% Traditional cash on cash: -0.65% Airbnb Rental Income: $3476 Traditional Rental Income: $3646 Airbnb ROI: -0.99% Traditional ROI: -0.65%
912 N SHORE DRIVE ANNA MARIA, FL Gorgeous recently renovated 2-bedroom, 2-bathroom cottage is perfectly situated on the nor...	2 beds \| 2 baths \| 1,332 sq.ft.	$1,195,000	Airbnb cash on cash: -0.85% Traditional cash on cash: -0.03% Airbnb Rental Income: $2055 Traditional Rental Income: $2430 Airbnb ROI: -0.85% Traditional ROI: -0.03%
519 SOUTH DRIVE ANNA MARIA, FL âAnna Maria Oasisâ is a Bimini Bay Coastal Classic, perfectly positioned on the covete...	3 beds \| 2 baths \| 2,131 sq.ft.	$1,779,000	Airbnb cash on cash: -1% Traditional cash on cash: -0.65% Airbnb Rental Income: $3306 Traditional Rental Income: $3141 Airbnb ROI: -1% Traditional ROI: -0.65%
154 CRESCENT DRIVE ANNA MARIA, FL Location! Location! Location! TRY BEFORE YOU BUY!!** Come Visitâ¦Fall in Love with luxur...	3 beds \| 3 baths \| 1,421 sq.ft.	$1,995,000	Airbnb cash on cash: -0.46% Traditional cash on cash: -0.42% Airbnb Rental Income: $3306 Traditional Rental Income: $2642 Airbnb ROI: -0.46% Traditional ROI: -0.42%
116 HAMMOCK ROAD ANNA MARIA, FL Discover Mia Bella â a rare canal-front estate on Anna Maria Islandâs coveted North En...	4 beds \| 4 baths \| 2,013 sq.ft.	$2,495,000	Airbnb cash on cash: -0.53% Traditional cash on cash: 0.39% Airbnb Rental Income: $3476 Traditional Rental Income: $4821 Airbnb ROI: -0.53% Traditional ROI: 0.39%
115 LOS CEDROS DRIVE ANNA MARIA, FL Located on the highly sought-after North End of Anna Maria Island, 115 Los Cedrosâknown ...	4 beds \| 4 baths \| 2,203 sq.ft.	$2,495,000	Airbnb cash on cash: -0.91% Traditional cash on cash: -0.18% Airbnb Rental Income: $3476 Traditional Rental Income: $4387 Airbnb ROI: -0.91% Traditional ROI: -0.18%
115 N BAY BOULEVARD ANNA MARIA, FL Welcome to this stunning show stopping property on the North End of Anna Maria Island!Â Â ...	3 beds \| 4 baths \| 3,548 sq.ft.	$4,395,000	Airbnb cash on cash: -1.02% Traditional cash on cash: -0.61% Airbnb Rental Income: $3306 Traditional Rental Income: $4217 Airbnb ROI: -1.02% Traditional ROI: -0.61%
57 N SHORE DRIVE ANNA MARIA, FL 57 North Shore Drive: The Art of Island Living Discover the perfect balance of classic An...	3 beds \| 3 baths \| 1,240 sq.ft.	$2,095,900	Airbnb cash on cash: -0.75% Traditional cash on cash: -0.7% Airbnb Rental Income: $3306 Traditional Rental Income: $2653 Airbnb ROI: -0.75% Traditional ROI: -0.7%
150 CRESCENT DRIVE ANNA MARIA, FL Ease into Island Life at Crescent Palms. If youâve been dreaming of that perfect, easy-...	3 beds \| 2 baths \| 1,765 sq.ft.	$1,995,000	Airbnb cash on cash: -0.42% Traditional cash on cash: -0.05% Airbnb Rental Income: $3306 Traditional Rental Income: $3249 Airbnb ROI: -0.42% Traditional ROI: -0.05%
801 N SHORE DRIVE ANNA MARIA, FL Rising gracefully on the sugar-white sands of Bean Point, The Golden Dolphin is a timeless...	3 beds \| 4 baths \| 4,728 sq.ft.	$10,950,000	Airbnb cash on cash: -1.34% Traditional cash on cash: -1.19% Airbnb Rental Income: $3306 Traditional Rental Income: $4094 Airbnb ROI: -1.34% Traditional ROI: -1.19%
413 POINSETTIA ROAD ANNA MARIA, FL Back on the Market!!!! Take another look at 413 Poinsettia Rd. Once you walk through the d...	2 beds \| 2 baths \| 1,677 sq.ft.	$1,950,000	Airbnb cash on cash: -1.15% Traditional cash on cash: -0.35% Airbnb Rental Income: $2055 Traditional Rental Income: $2973 Airbnb ROI: -1.15% Traditional ROI: -0.35%
50 N SHORE DRIVE ANNA MARIA, FL An exceptional opportunity to experience true island living where waterfront boating and b...	4 beds \| 5 baths \| 3,055 sq.ft.	$4,850,000	Airbnb cash on cash: -1.33% Traditional cash on cash: -0.39% Airbnb Rental Income: $3476 Traditional Rental Income: $6935 Airbnb ROI: -1.33% Traditional ROI: -0.39%
870 N SHORE DRIVE ANNA MARIA, FL LOCATION!!!! North Shore Drive, one of the most popular streets in Anna Maria! This is a g...	4 beds \| 5 baths \| 2,091 sq.ft.	$3,895,000	Airbnb cash on cash: -1.22% Traditional cash on cash: -0.74% Airbnb Rental Income: $3476 Traditional Rental Income: $4428 Airbnb ROI: -1.22% Traditional ROI: -0.74%
612 FERN STREET ANNA MARIA, FL Wake up every day in true island paradise at Anna Maria Chateau! Ideally positioned at the...	3 beds \| 2 baths \| 1,472 sq.ft.	$1,825,000	Airbnb cash on cash: -1.02% Traditional cash on cash: -0.96% Airbnb Rental Income: $3306 Traditional Rental Income: $2671 Airbnb ROI: -1.02% Traditional ROI: -0.96%

Your search for investment property begins and ends here

Single Family Homes for Sale in Anna Maria, FL

329 TARPON STREET

ANNA MARIA, FL

4 beds | 5 baths | 3,751 sq.ft.

$5,800,000

Airbnb cash on cash: -0.78%

Traditional cash on cash: 0.13%

Airbnb Rental Income: $3476

Traditional Rental Income: $7593

Airbnb ROI: -0.78%

Traditional ROI: 0.13%

313 MAGNOLIA AVENUE

ANNA MARIA, FL

3 beds | 2 baths | 1,424 sq.ft.

$1,675,000

Airbnb cash on cash: -0.55%

Traditional cash on cash: -0.66%

Airbnb Rental Income: $3306

Traditional Rental Income: $2383

Airbnb ROI: -0.55%

Traditional ROI: -0.66%

527 MAGNOLIA AVENUE

ANNA MARIA, FL

3 beds | 2 baths | 1,924 sq.ft.

$2,195,000

Airbnb cash on cash: -0.84%

Traditional cash on cash: -0.45%

Airbnb Rental Income: $3306

Traditional Rental Income: $3362

Airbnb ROI: -0.84%

Traditional ROI: -0.45%

785 JACARANDA ROAD

ANNA MARIA, FL

3 beds | 3 baths | 1,500 sq.ft.

$1,999,900

Airbnb cash on cash: -0.85%

Traditional cash on cash: -0.71%

Airbnb Rental Income: $3306

Traditional Rental Income: $2832

Airbnb ROI: -0.85%

Traditional ROI: -0.71%

113 MAPLE AVENUE

ANNA MARIA, FL

5 beds | 5 baths | 2,680 sq.ft.

$3,690,000

Airbnb cash on cash: -1.59%

Traditional cash on cash: -0.56%

Airbnb Rental Income: $3130

Traditional Rental Income: $5965

Airbnb ROI: -1.59%

Traditional ROI: -0.56%

222 WILLOW AVENUE

ANNA MARIA, FL

4 beds | 6 baths | 3,265 sq.ft.

$4,995,000

Airbnb cash on cash: -1.45%

Traditional cash on cash: -0.06%

Airbnb Rental Income: $3476

Traditional Rental Income: $9145

Airbnb ROI: -1.45%

Traditional ROI: -0.06%

120 WHITE AVENUE

ANNA MARIA, FL

5 beds | 4 baths | 2,763 sq.ft.

$3,497,500

Airbnb cash on cash: -1.67%

Traditional cash on cash: -1.06%

Airbnb Rental Income: $3130

Traditional Rental Income: $4407

Airbnb ROI: -1.67%

Traditional ROI: -1.06%

704 GLADIOLUS STREET

ANNA MARIA, FL

4 beds | 3 baths | 2,415 sq.ft.

$2,995,000

Airbnb cash on cash: -1.2%

Traditional cash on cash: -0.87%

Airbnb Rental Income: $3476

Traditional Rental Income: $3609

Airbnb ROI: -1.2%