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.
Investment Property for Sale in Anna Maria, FL
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
110 OAK Avenue #AANNA MARIA, FLOld Florida Charm - Income-Producing Property! Looking for a true Old Florida beach cottag... |
2 beds | 2 baths | 640 sq.ft. |
$829,000 |
Airbnb cash on cash: 0.98%
|
222 WILLOW AvenueANNA MARIA, FLWelcome to SeaLuxe, where luxury meets the beach! Located on one of the most desirable str... |
4 beds | 6 baths | 3,265 sq.ft. |
$4,800,000 |
Airbnb cash on cash: -0.91%
|
704 GLADIOLUS StreetANNA MARIA, FLPRIME LOCATION, PEEKS OF THE BAY & ROOM FOR THE WHOLE FAMILY! Relish the quiet neighborhoo... |
4 beds | 3 baths | 2,415 sq.ft. |
$2,899,900 |
Airbnb cash on cash: -0.28%
|
229 WILLOW AvenueANNA MARIA, FLHere 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: -1.39%
|
212 OAK AvenueANNA MARIA, FLSTUNNING 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: -0.76%
|
111 CEDAR AvenueANNA MARIA, FLAMAZING 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: -0.9%
|
510 MAGNOLIA AvenueANNA MARIA, FLBack on the market after a very busy summer season. Welcome to Aloha Beaches. This home is... |
4 beds | 3 baths | 2,225 sq.ft. |
$2,985,000 |
Airbnb cash on cash: -0.09%
|
912 N SHORE DriveANNA MARIA, FLGorgeous 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: 0.18%
|
154 CRESCENT DriveANNA MARIA, FLLocation! Location! Location! TRY BEFORE YOU BUY!!** Come Visit...Fall in Love with luxury... |
3 beds | 3 baths | 1,421 sq.ft. |
$1,799,900 |
Airbnb cash on cash: 0.28%
|
801 N SHORE DriveANNA MARIA, FLRising gracefully on the sugar-white sands of Bean Point, The Golden Dolphin is a timeless... |
4 beds | 4 baths | 4,728 sq.ft. |
$8,250,000 |
Airbnb cash on cash: -1.11%
|
413 POINSETTIA RoadANNA MARIA, FLBack on the Market! Take a look at 413 Poinsettia Rd. Once you walk through the door you w... |
2 beds | 2 baths | 1,800 sq.ft. |
$1,499,000 |
Airbnb cash on cash: -0.38%
|
50 N SHORE DriveANNA MARIA, FLAn exceptional opportunity to experience true island living where waterfront boating and b... |
4 beds | 5 baths | 3,055 sq.ft. |
$4,490,000 |
Airbnb cash on cash: -0.76%
|
870 N SHORE DriveANNA MARIA, FLLOCATION!!!! 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: -0.53%
|
103 PALM AvenueANNA MARIA, FLWelcome to 103 Palm Avenue on Anna Maria Island, home to some of the best beaches in Flori... |
4 beds | 4 baths | 2,252 sq.ft. |
$5,450,000 |
Airbnb cash on cash: -0.63%
|
155 CRESCENT DriveANNA MARIA, FLYour private island retreat awaits in this exquisitely renovated coastal cottage, situated... |
3 beds | 2 baths | 1,512 sq.ft. |
$1,900,000 |
Airbnb cash on cash: -0.26%
|
889 N SHORE DriveANNA MARIA, FLThis Bayfront home is calling your name! Perfectly positioned directly on the bay, this 3-... |
3 beds | 3 baths | 2,025 sq.ft. |
$4,200,000 |
Airbnb cash on cash: -1%
|
215 SYCAMORE AvenueANNA MARIA, FLWelcome to a rare offering on the coveted north end of Anna Maria Island - a brand-new coa... |
4 beds | 5 baths | 3,250 sq.ft. |
$5,895,000 |
Airbnb cash on cash: -0.3%
|
228 GLADIOLUS StreetANNA MARIA, FLAnna Maria Island Income-Producing Beach Retreat | 3BR/2BA | Oversized Pool + Spa Exceptio... |
3 beds | 2 baths | 1,458 sq.ft. |
$1,845,000 |
Airbnb cash on cash: -0.09%
|
513 N BAY BoulevardANNA MARIA, FLWelcome to The Beachwood! Discover coastal elegance in this brand-new constructed home wit... |
4 beds | 4 baths | 2,602 sq.ft. |
$4,495,000 |
Airbnb cash on cash: 0.02%
|
306 PALM AvenueANNA MARIA, FLLOCATION! NEW STEEL ROOF! .19 ACRE LOT! RARE ARTISAN WELL! MOTHER-IN-LAW SUITE! Opportunit... |
3 beds | 3 baths | 1,902 sq.ft. |
$1,525,000 |
Airbnb cash on cash: 1.31%
|
315 SPRING AvenueANNA MARIA, FLSpring Avenue. One of Anna Maria Island's most coveted addresses and this elevated pool ho... |
3 beds | 2 baths | 1,428 sq.ft. |
$2,175,000 |
Airbnb cash on cash: -0.19%
|
317 N BAY BoulevardANNA MARIA, FLFINANCING FELL THROUGH BACK ON THE MARKET!!! Welcome to your dream getaway, an adorable bu... |
3 beds | 3 baths | 2,019 sq.ft. |
$1,595,000 |
Airbnb cash on cash: 0.17%
|
526 SEAGULL WayANNA MARIA, FLDon't miss this Eason Builders Group custom-built pool home located on the desirable north... |
4 beds | 5 baths | 2,707 sq.ft. |
$3,445,000 |
Airbnb cash on cash: -0.67%
|
256 GLADIOLUS StreetANNA MARIA, FLUnparalleled luxury, unmatched value: recently reduced by $400K! Discover the essence of i... |
4 beds | 4 baths | 2,122 sq.ft. |
$3,250,000 |
Airbnb cash on cash: -0.53%
|
703 S BAY BoulevardANNA MARIA, FLExperience Elevated Island Living at 703 S Bay Blvd. Nestled along the tranquil Bimini Bay... |
5 beds | 5 baths | 3,700 sq.ft. |
$8,995,000 |
Airbnb cash on cash: -0.69%
|
504 SPRING AvenueANNA MARIA, FLThis amazing old Florida 1922 cottage is so quaint and cozy, you'll never want to leave! T... |
3 beds | 3 baths | 1,398 sq.ft. |
$1,795,000 |
Airbnb cash on cash: 0.08%
|
159 CRESCENT DriveANNA MARIA, FLBack on the Market!!!!! Welcome to Tropical Paradise. Talk about Location, Location, Locat... |
4 beds | 3 baths | 2,567 sq.ft. |
$2,985,000 |
Airbnb cash on cash: -0.09%
|
524 SPRING AvenueANNA MARIA, FLSet in the heart of Anna Maria, this elevated 3BD/2BA home holds one of the island's most ... |
3 beds | 2 baths | 1,176 sq.ft. |
$1,250,000 |
Airbnb cash on cash: 1.82%
|
113 PALMETTO AvenueANNA MARIA, FLA rare opportunity awaits just steps from the Gulf in this exceptional 2025 coastal reside... |
4 beds | 5 baths | 2,220 sq.ft. |
$5,125,000 |
Airbnb cash on cash: -0.24%
|
505 S BAY BoulevardANNA MARIA, FLGrandfathered to accommodate up to 12 guests-a rare and increasingly valuable advantage on... |
5 beds | 5 baths | 3,202 sq.ft. |
$2,750,000 |
Airbnb cash on cash: -0.7%
|
872 NORTH SHORE DriveANNA MARIA, FLBEAUTIFUL WATER VIEWS. This four-bedroom, two-bath stilt home with a two-car garage offers... |
4 beds | 2 baths | 1,560 sq.ft. |
$1,700,000 |
Airbnb cash on cash: 0.93%
|
109 TERN DriveANNA MARIA, FLLove the beach and love to boat? Delightful waterfront home with direct access to open wat... |
2 beds | 2 baths | 1,223 sq.ft. |
$1,399,000 |
Airbnb cash on cash: -0.28%
|
Real Estate investment in Anna-maria, FL
There are 41 properties for sale in the city of Anna Maria . The median list price in Anna Maria is $1,978,691 and the average price per square foot is $855. In October 2026, the average monthly cash on cash return in Anna Maria is -1.00%. The average monthly rental income in Anna Maria is $2,836.