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 |
|---|---|---|---|
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: -1.16%
|
704 GLADIOLUS STREETANNA MARIA, FLPRICE CHANGE! You are just a short walk to Beach and Bay from this quality constructed 4 b... |
4 beds | 3 baths | 2,415 sq.ft. |
$2,945,000 |
Airbnb cash on cash: -0.7%
|
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: -1.9%
|
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: -1.57%
|
401 N SHORE DRIVEANNA MARIA, FLStunning 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: -0.27%
|
893 N SHORE DRIVEANNA MARIA, FLOne or more photo(s) has been virtually staged. If you're looking for exceptional value on... |
4 beds | 3 baths | 2,933 sq.ft. |
$2,950,000 |
Airbnb cash on cash: -0.06%
|
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: -0.92%
|
103 SUNSET LANEANNA MARIA, FLA premier setting defines this offering. Tucked at the end of a quiet cul-de-sac in Sunset... |
3 beds | 3 baths | 2,800 sq.ft. |
$2,395,000 |
Airbnb cash on cash: 0.08%
|
519 VILLA ROSA WAYANNA MARIA, FLThis 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: -0.63%
|
136 CRESCENT DRANNA MARIA, FLThe Beach Is Calling!!! Best priced Anna Maria City move in ready single family home with ... |
2 beds | 2 baths | 1,068 sq.ft. |
$1,149,999 |
Airbnb cash on cash: -0.19%
|
510 MAGNOLIA AVENUEANNA MARIA, FLWelcome 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: -0.5%
|
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: 0.03%
|
154 CRESCENT DRIVEANNA MARIA, FLLocation! Location! Location! TRY BEFORE YOU BUY!!** Come Visitâ¦Fall in Love with luxur... |
3 beds | 3 baths | 1,421 sq.ft. |
$1,799,900 |
Airbnb cash on cash: 0.22%
|
115 LOS CEDROS DRIVEANNA MARIA, FLLocated on the highly sought-after North End of Anna Maria Island, 115 Los Cedrosâknown ... |
4 beds | 4 baths | 2,203 sq.ft. |
$2,290,000 |
Airbnb cash on cash: -0.25%
|
115 N BAY BOULEVARDANNA MARIA, FLWelcome to this stunning show stopping property on the North End of Anna Maria Island!  ... |
3 beds | 4 baths | 3,548 sq.ft. |
$4,150,000 |
Airbnb cash on cash: -0.75%
|
150 CRESCENT DRIVEANNA MARIA, FLEase into Island Life at Crescent Palms. If youâve been dreaming of that perfect, easy-... |
3 beds | 2 baths | 1,765 sq.ft. |
$1,790,000 |
Airbnb cash on cash: 0.27%
|
801 N SHORE DRIVEANNA MARIA, FLRising gracefully on the sugar-white sands of Bean Point, The Golden Dolphin is a timeless... |
3 beds | 4 baths | 4,728 sq.ft. |
$8,250,000 |
Airbnb cash on cash: -1.32%
|
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. |
$1,595,000 |
Airbnb cash on cash: -0.54%
|
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. |
$4,650,000 |
Airbnb cash on cash: -1.02%
|
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: -0.83%
|
110 OAK AVENUE #AANNA MARIA, FLOld Florida Charm â Income-Producing Property! Looking for a true Old Florida beach cott... |
2 beds | 2 baths | 640 sq.ft. |
$839,000 |
Airbnb cash on cash: 0.74%
|
120 MAPLE AVENUEANNA MARIA, FLPrime Beachside Retreat â Steps to the Sand on Anna Maria Island! Discover coastal livi... |
3 beds | 2 baths | 1,506 sq.ft. |
$1,475,000 |
Airbnb cash on cash: 0.42%
|
102 TUNA STREETANNA MARIA, FLFinding a lot of this scale on one of Anna Mariaâs most quiet and secluded streets is an... |
3 beds | 3 baths | 1,926 sq.ft. |
$6,750,000 |
Airbnb cash on cash: -1.29%
|
108 PELICAN DRIVEANNA MARIA, FLLocated on the north end of Anna Maria, this elevated canal-front home is a true boaterâ... |
4 beds | 2 baths | 1,472 sq.ft. |
$2,149,000 |
Airbnb cash on cash: 0.54%
|
313 HAMMOCK CIRCLEANNA MARIA, FLThis waterfront coastal retreat embodies refined island luxury, offered completely turnkey... |
4 beds | 4 baths | 3,755 sq.ft. |
$3,995,000 |
Airbnb cash on cash: -0.99%
|
111 PALMETTO AVENUEANNA MARIA, FLExperience elevated island living in this exceptional brand-new custom four bedroom four a... |
4 beds | 5 baths | 2,677 sq.ft. |
$5,125,000 |
Airbnb cash on cash: -0.47%
|
403 N BAY BOULEVARDANNA MARIA, FLHAPPY FATHER'S DAY $100,000 PRICE REDUCTION â MOTIVATED SELLER - Luxury Island Home on N... |
4 beds | 3 baths | 2,112 sq.ft. |
$2,299,900 |
Airbnb cash on cash: -0.42%
|
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. |
$6,050,000 |
Airbnb cash on cash: -0.86%
|
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: -0.31%
|
112 CEDAR AVENUEANNA MARIA, FLCompletely remodeled 4-bedroom, 4-bathroom coastal retreat blending the charm of an origin... |
4 beds | 4 baths | 1,800 sq.ft. |
$2,795,000 |
Airbnb cash on cash: -0.01%
|
811 N SHORE DRIVEANNA MARIA, FLExperience one of the most extraordinary waterfront settings on the coveted North End of A... |
5 beds | 8 baths | 5,079 sq.ft. |
$10,950,000 |
Airbnb cash on cash: -1.24%
|
109 TERN DRIVEANNA MARIA, FLLove the beach and love to boat? Delightful waterfront home with direct access to open wa... |
2 beds | 2 baths | 1,223 sq.ft. |
$1,499,000 |
Airbnb cash on cash: -0.45%
|
406 N SHORE DRIVEANNA MARIA, FLUnder Construction. Luxury residence coming soon in the heart of Anna Maria! This 4 bedroo... |
4 beds | 5 baths | 2,999 sq.ft. |
$5,450,000 |
Airbnb cash on cash: -0.34%
|
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. |
$4,500,000 |
Airbnb cash on cash: -1.02%
|
215 SYCAMORE AVENUEANNA MARIA, FLWelcome to a rare offering on the coveted north end of Anna Maria Island â a brand-new c... |
4 beds | 5 baths | 3,250 sq.ft. |
$5,895,000 |
Airbnb cash on cash: -0.51%
|
418 PINE AVENUEANNA MARIA, FLPositioned along the most sought-after stretch of Pine Avenueâknown for its vibrant coas... |
4 beds | 3 baths | 2,804 sq.ft. |
$2,850,000 |
Airbnb cash on cash: -0.42%
|
416 ALAMANDA ROADANNA MARIA, FLLocated just two blocks from Bean Point on the coveted north end of Anna Maria Island, thi... |
4 beds | 5 baths | 3,102 sq.ft. |
$4,095,000 |
Airbnb cash on cash: -1%
|
228 GLADIOLUS STREETANNA MARIA, FLAnna Maria Island Income-Producing Beach Retreat | 3BR/2BA | Oversized Pool + Spa Excepti... |
3 beds | 2 baths | 1,458 sq.ft. |
$1,945,000 |
Airbnb cash on cash: -0.19%
|
513 N BAY BOULEVARDANNA MARIA, FLWelcome to The Beachwood! Discover coastal elegance in this brand-new constructed home wi... |
4 beds | 4 baths | 2,602 sq.ft. |
$4,495,000 |
Airbnb cash on cash: -0.25%
|
112 MAPLE AVENUEANNA MARIA, FLSTUNNING HOME WEST OF GULF DRIVE! WELCOME TO THIS AMAZING FULLY FURNISHED 5 BEDROOM, 4.5 B... |
5 beds | 5 baths | 2,545 sq.ft. |
$4,925,000 |
Airbnb cash on cash: -1.76%
|
Real Estate investment in Anna-maria, FL
There are 58 properties for sale in the city of Anna Maria . The median list price in Anna Maria is $2,123,729 and the average price per square foot is $883. In July 2026, the average monthly cash on cash return in Anna Maria is -1.00%. The average monthly rental income in Anna Maria is $2,914.