Holmes Beach, FL Homes for Sale with Pool

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  /38

  $1,600,000

  $150K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,713 Sq Ft

  207 Peacock Ln, Holmes Beach, FL 34217

  This completely updated Anna Maria Island 3 bedroom 2.5 Bathroom pool home is situated on a cul-de-sac, and features hurricane-rated windows, metal roof, concrete block construction and garage. Property is in a Weekly rental zone with a successful rental history, making this BEAUTIFUL BEACH HOME a perfect investment property, or family get away. Just 3 short blocks to the white sandy beaches of

  Lindsey Haymond KELLER WILLIAMS ON THE WATER

  207 Peacock Ln, Holmes Beach, FL 34217
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  /73

  $6,900,000

  $700K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 3,325 Sq Ft

  95 52nd St, Holmes Beach, FL 34217

  Views abound in this exquisite beachfront retreat in the heart of Anna Maria Island. This 3-bedroom, 3.5-bath Coastal West Indies–inspired residence showcases exceptional craftsmanship, including custom millwork, solid oak flooring, vaulted ceilings, designer draperies, and Roman shades throughout. An open-concept floor plan fills the home with natural light, while expansive windows and glass

  Reid Murphy DEVELOPERS REALTY LBK, INC

  95 52nd St, Holmes Beach, FL 34217
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  /28

  $1,200,000

  $150K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,516 Sq Ft

  5300 Gulf Dr Unit 105, Holmes Beach, FL 34217

  Never miss a sunset with the view from this beachfront GEM! A true 3 Bedroom, 2 Full Bathroom with 1,516 square feet, including an indoor Laundry Room. One of only 6 units of this size in the building. The Master Suite boasts a panoramic beach view, walk in closet and en-suit bath, while the 2 remaining bedrooms have large closets and comfortable natural lighting. The split floor plan ensures

  Jennifer Sekel BEACH HOUSE REAL ESTATE LLC

  5300 Gulf Dr Unit 105, Holmes Beach, FL 34217
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  /65

  $2,950,000

  • 4 Beds
  • 3.5 Baths
  • 2,040 Sq Ft

  117 81st St, Holmes Beach, FL 34217

  Welcome to 117 81st Street in Holmes Beach, a custom-designed coastal retreat steps to the beach that has been completely renovated inside and out, offering the perfect blend of modern luxury and effortless island living. This beautifully updated 4-bedroom, 3.5-bath home is being sold turnkey furnished, making it move-in ready or immediately available as a high-performing rental investment. The

  Matthew Huffman COLDWELL BANKER REALTY

  117 81st St, Holmes Beach, FL 34217
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  /92

  $2,100,000

  $100K PRICE DROP

  • 5 Beds
  • 5 Baths
  • 2,320 Sq Ft

  201 54th St, Holmes Beach, FL 34217

  This exceptional turnkey 5-bedroom, 5-bath duplex on Anna Maria Island offers a rare investment opportunity just moments from the white-sand beaches of the Gulf of Mexico, as well as the island’s charming shops and top-rated dining. Comprised of two beautifully renovated cottages—a 3BR/3BA and a 2BR/2BA, all en-suite—this unique property is connected by a solid 8-inch concrete block wall for

  Ana Chirino CHIRINO REAL ESTATE

  201 54th St, Holmes Beach, FL 34217
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  /61

  $3,500,000

  $150K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 3,274 Sq Ft

  227 S Harbor Dr, Holmes Beach, FL 34217

  Experience elevated coastal living in this brand-new, designer-finished 4BR/4.5BA luxury home located just a 5-minute walk to the pristine beaches of Anna Maria Island. Thoughtfully crafted with high-end finishes and a bright, open-concept layout, this residence blends modern elegance with relaxed island charm. Currently utilized as a successful short term vacation rental with proven rental

  Leslie Wells LESLIE WELLS REALTY, INC.

  227 S Harbor Dr, Holmes Beach, FL 34217
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  /38

  $475,000

  • 2 Beds
  • 2 Baths
  • 1,035 Sq Ft

  3601 E Bay Dr Unit 102, Holmes Beach, FL 34217

  Waterfront Sandy Pointe Condominiums. Discover the charm of this secluded community, perfectly situated in one of the most desirable locations on Anna Maria Island. This private unit, positioned at the rear of the complex near the waterfront, offers an ideal blend of comfort and convenience. Featuring two bedrooms with en-suite bathrooms, the layout provides ample space for relaxation and

  Susie Robinson COLDWELL BANKER REALTY

  3601 E Bay Dr Unit 102, Holmes Beach, FL 34217
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  /79

  $1,599,000

  $50K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,777 Sq Ft

  204 75th St, Holmes Beach, FL 34217

  Fantastic Vacation Rental Loved By All GenerationsWelcome to the ultimate island vacation home. Located in a weekly rental zone, it is positioned to be an outstanding income producing property with strong vacation rental history and bookings secured into Summer 2026, making it an exceptional investment opportunity for any buyer.This fully renovated ground level retreat is designed for

  Kathy Harman MICHAEL SAUNDERS & COMPANY

  204 75th St, Holmes Beach, FL 34217
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  /68

  $599,000

  Open Mon 11AM - 1PM $30K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,430 Sq Ft

  4255 Gulf Dr Unit 116, Holmes Beach, FL 34217

  One or more photo(s) has been virtually staged. NEW ROOF! Welcome to this freshly remodeled, elevated 2-bedroom, 2-bathroom end-unit condo with a flex room at Island Village in Holmes Beach. Perfectly located just one block from the pristine sands of Anna Maria Island. This bright and airy condo has been thoughtfully updated, featuring a clean, modern aesthetic. It includes two dedicated parking

  Hannah Hillyard MICHAEL SAUNDERS & COMPANY

  4255 Gulf Dr Unit 116, Holmes Beach, FL 34217
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  /44

  $1,375,000

  • 3 Beds
  • 2.5 Baths
  • 1,602 Sq Ft

  213 75th St, Holmes Beach, FL 34217

  It’s a short walk to the beach to enjoy the beautiful water and sunsets and then back to your turnkey furnished vacation home with a pool that offers seating and a table for the cocktail hour. The courtyard also offers a covered, shady patio with a dining table to enjoy the cool breeze through the palm trees. Totally updated floor plan with a great flow! Close to shops and the free trolley. An

  Kathy Caserta MIKE NORMAN REALTY INC.

  213 75th St, Holmes Beach, FL 34217
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  /49

  $1,399,000

  $51K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,500 Sq Ft

  3604 Gulf Dr Unit A and B, Holmes Beach, FL 34217

  OVER 150K INCOME OVER LAST 12 MONTHS!!! Embrace the pinnacle of island luxury with this impeccably designed, turnkey Holmes Beach duplex—operating as a successful Airbnb and ready for seamless ownership transition. Each side features two spacious bedrooms and one bath, complete with gleaming marble countertops, white shaker cabinetry, elegant, natural-flow tile backsplashes and breathtaking

  Johnny Hopper PREFERRED SHORE LLC

  3604 Gulf Dr Unit A and B, Holmes Beach, FL 34217
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  /59

  $1,835,000

  Open Thu 1AM - 4PM $50K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,692 Sq Ft

  608 Gladstone Ln, Holmes Beach, FL 34217

  Tucked within the exclusive waterfront community of Key Royale on Anna Maria Island, this beautifully renovated canal-front residence offers an exceptional blend of island charm, privacy, and effortless island living. Designed to embrace the Florida lifestyle, the home is centered around a spectacular pool courtyard, where almost every room opens to the expansive outdoor living space, creating a

  Becky Sirigotis COMPASS FLORIDA LLC

  608 Gladstone Ln, Holmes Beach, FL 34217
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  /35

  $925,000

  $75K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,022 Sq Ft

  304 74th St Unit B, Holmes Beach, FL 34217

  ONE OF A KIND - ELEVATED with a PRIVATE POOL & your own garage, this is like single family home living - for under $1m on Anna Maria Island! This 2 bed/2 bath picture perfect, island dream is ideally situated on a quiet corner, just two short blocks from the Gulf Beaches! This UPDATED island sanctuary surrounds you in coastal charm. The luxury vinyl large plank flooring throughout is ideal for

  Erin Leathem ISLAND REAL ESTATE-ANNA MARIA

  304 74th St Unit B, Holmes Beach, FL 34217
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  /16

  $1,200,000

  • 2 Beds
  • 2 Baths
  • 1,008 Sq Ft

  4200 Gulf Dr Unit 205, Holmes Beach, FL 34217

  Gulf Sands is located in a great location on Anna Maria Island. The unit offers a renovated 2-bedroom, 2-bath coastal escape with Gulf views, private balcony, full kitchen with in-unit laundry, a shared heated pool, and direct private beach access, perfect for island living with amenities and proximity to local attractions and dining. New Air Conditioning unit in 2024. All information should be

  Rochelle Bower MIKE NORMAN REALTY INC.

  4200 Gulf Dr Unit 205, Holmes Beach, FL 34217
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  /96

  $2,439,000

  • 4 Beds
  • 3.5 Baths
  • 2,634 Sq Ft

  4805 2nd Ave, Holmes Beach, FL 34217

  Anna Maria Island Coastal retreat, located west of Gulf Drive and only two blocks to the beach, offers the perfect blend of luxury, comfort, and investment potential. Featuring four bedrooms and three and half bathrooms and a bonus living area, this home has potential as a primary residence, vacation getaway, or income-producing property. The open concept interior showcases high ceilings, tile

  Karen McCall BEACH HOUSE REAL ESTATE LLC

  4805 2nd Ave, Holmes Beach, FL 34217
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  /28

  $499,900

  $49K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,179 Sq Ft

  600 Manatee Ave Unit 116, Holmes Beach, FL 34217

  OWNER VERY MOTIVATED !! West Bay Cove in Holmes Beach! This fully updated condo is being offered turnkey furnished, making it an ideal vacation getaway, income-producing rental, or full-time home in paradise.PICKLE BALL ! The bright corner layout offers open, inviting living spaces and a peaceful setting overlooking the pool, creating the perfect spot to unwind after a day at the beach.

  Brenda Boyd May BOYD REALTY

  600 Manatee Ave Unit 116, Holmes Beach, FL 34217
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  /31

  $1,699,000

  $100K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 1,900 Sq Ft

  311 63rd St Unit A, Holmes Beach, FL 34217

  Own 2 Vacation / Investment Properties for the price of 1 with this Island Duplex -Live & Vacation in 1 Side / Rent the other with Strong Income Potential . Just a short 8 min. healthy walk to the beaches and downtown Homes Beach. This fully renovated duplex offers two private 2 BR/2BA residences, each with its own private entrance and each with a private heated and cooled pool ideal for renter

  Mel Neely, PA IVP OF FLORIDA INC

  311 63rd St Unit A, Holmes Beach, FL 34217
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  /46

  $1,075,000

  • 3 Beds
  • 2 Baths
  • 1,010 Sq Ft

  5803 de Palmas Ave, Holmes Beach, FL 34217

  Come make your island dream a reality! This updated 3 bed/2 bath coastal charmer is just steps to the sugar sand beach, with a heated, salt water pool with full spa features! Create your own style in this cute cottage, where the hard work has already been done for you! New Luxury Vinyl Plank throughout, fresh paint, new doors, new bathrooms, new cabinetry and new appliances, means nothing left

  Erin Leathem ISLAND REAL ESTATE-ANNA MARIA

  5803 de Palmas Ave, Holmes Beach, FL 34217
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  /40

  $939,000

  $37K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,188 Sq Ft

  5400 Gulf Dr Unit 32, Holmes Beach, FL 34217

  BEACHFRONT PROPERTY.............. OPEN TO SELLER FINANCING........FULLY FURNISHED........... BUILDING NEVER FLOODED.........FULLY RENOVATED.......IMPACT WINDOWS...............BREATHTAKING OCEAN AND BEACH VIEWS..........HOA PAYS EVERYTHING BUT ELECTRIC................ Rarely does a beachfront opportunity like this come along. In a community where properties seldom hit the market, this residence

  Garrett Sedlacek KELLER WILLIAMS ON THE WATER S

  5400 Gulf Dr Unit 32, Holmes Beach, FL 34217
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  /81

  $2,295,000

  $100K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,799 Sq Ft

  624 Dundee Ln, Holmes Beach, FL 34217

  Welcome to Southern Exposure! One of the best things about coming to sunny Florida from the cold North is a home with Southern Exposure so you can bask in the sun by this amazing pool all day long! Tranquil, private waterfront sanctuary — 624 Dundee on Key Royale is an impeccably renovated residence offering modern-luxe living by the water. This refined 3-bedroom, 2-bath pool home blends

  Billi Gartman ANNA MARIA LIFE REAL ESTATE

  624 Dundee Ln, Holmes Beach, FL 34217
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  /79

  $2,499,000

  $201K PRICE DROP

  • 6 Beds
  • 5.5 Baths
  • 2,621 Sq Ft

  6908 Holmes Blvd, Holmes Beach, FL 34217

  Welcome to Sands of Time, a recently updated six-bedroom, four-and-a-half-bathroom coastal retreat located less than two blocks from the white-sand beaches in the heart of Holmes Beach on Anna Maria Island. Thoughtfully designed and professionally decorated, this home blends relaxed beach style with upscale comfort, making it ideal as a primary residence, second home, or high-performing

  Don Purvis BEACH HOUSE REAL ESTATE LLC

  6908 Holmes Blvd, Holmes Beach, FL 34217
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  /38

  $5,900,000

  • 10 Beds
  • 8 Baths
  • 4,944 Sq Ft

  102 39th St Unit 2, Holmes Beach, FL 34217

  Welcome to Alamanda Villas and your piece of island paradise. Just steps from the Gulf of Mexico, 8 unit property features a heated outdoor pool, barbecue facilities and umbrella-covered patio areas with wonderful water views. Each 1 bedroom/1 bathroom unit has a fully stocked kitchen with a microwave, refrigerator, coffee maker, oven and stove top. There are many shops, restaurants, and

  Robert Louloudes STARZ REAL ESTATE, LLC

  102 39th St Unit 2, Holmes Beach, FL 34217
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  /51

  $438,900

  $10K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 980 Sq Ft

  3607 E Bay Dr Unit 206, Holmes Beach, FL 34217

  Better than ever and in beautiful condition, this top floor unit is priced below recent similar units for a quick sale. This 2BD/2BA home is ready to live in or rent immediately after purchase. All buildings feature brand-new roofs (2022–2023) following Hurricane Milton. The buildings also received new siding and paint. Community pool is also in very good condition. The private street serving the

  Brad Hodge BAY VISION REALTY INC

  3607 E Bay Dr Unit 206, Holmes Beach, FL 34217
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  /39

  $369,000

  $16K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 888 Sq Ft

  600 Manatee Ave Unit 226, Holmes Beach, FL 34217

  Turnkey Furnished 1-Bed, 1-Bath Condo Steps from the Beach on Anna Maria Island Enjoy island living in this elevated, turnkey 1-bedroom, 1-bath condo just steps from the public beach on Anna Maria Island. Located in the highly desirable Westbay Cove community, this spacious second-floor unit features an open floor plan filled with natural light and a private balcony overlooking the pool and lush

  Elizabeth Blandford SALTY MERMAID REAL ESTATE LLC

  600 Manatee Ave Unit 226, Holmes Beach, FL 34217
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  /47

  $2,699,000

  $100K PRICE DROP

  • 6 Beds
  • 4.5 Baths
  • 2,947 Sq Ft

  130 50th St, Holmes Beach, FL 34217

  Own the sunset and step into a lifestyle buyers dream about—and renters actively seek out. Just moments from the Gulf, this stunning 6-bedroom, 4.5-bath coastal retreat delivers the perfect blend of luxury, comfort, and exceptional income potential.Designed to host and impress, the home lives like a private resort. Outside, guests are drawn to the resort-style pool with a sun shelf, a

  Lisa Tucker BEACH HOUSE REAL ESTATE LLC

  130 50th St, Holmes Beach, FL 34217
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  /47

  $1,799,000

  • 4 Beds
  • 4 Baths
  • 2,037 Sq Ft

  408 71st St, Holmes Beach, FL 34217

  Welcome to paradise at Coco Cay! This beautiful 4 bedroom 4 bathroom home has been completely remodeled top to bottom. Brand new hurricane impact windows and doors, a new roof, kitchen, appliances, bathrooms, flooring, paint, furnishings, and even a new pool! This island oasis is move-in ready and only a few blocks from the world-famous beaches of Anna Maria Island. You will notice coastal décor

  Don Purvis BEACH HOUSE REAL ESTATE LLC

  408 71st St, Holmes Beach, FL 34217
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  /16

  $675,000

  • 2 Beds
  • 2 Baths
  • 1,038 Sq Ft

  5325 Marina Dr Unit 123, Holmes Beach, FL 34217

  Welcome to Waterline Villas & Marina Residences, where modern coastal elegance meets the laid-back charm of Old Florida on Anna Maria Island. Built in 2017, each fully furnished residence offers a stylish and comfortable escape featuring 2 bedrooms, 2 full baths, a fully equipped kitchen, inviting living space, and in-unit washer and dryer. Wake up in a spacious primary suite with a king-sized

  Penny Walding SARABAY REAL ESTATE INC

  5325 Marina Dr Unit 123, Holmes Beach, FL 34217
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  /92

  $2,349,000

  $426K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,524 Sq Ft

  303 58th St, Holmes Beach, FL 34217

  AMAZING LOCATION • COMPLETELY UPDATED • BRAND NEW POOL • BRAND NEW ROOF • TURN-KEY FURNISHED Casa Bella is a spacious and beautifully updated 4-bedroom, 3-bath home offering more than 2,500 sq ft in the heart of Holmes Beach. Located just steps from shopping and dining and only a 5-MINUTE WALK TO BEACH, this property is situated in one of Anna Maria Island’s most desirable WEEKLY RENTAL ZONES,

  Marlen Ryan PREFERRED SHORE LLC

  303 58th St, Holmes Beach, FL 34217
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  /36

  $259,000

  $56K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 412 Sq Ft

  2601 Gulf Dr N Unit 729, Bradenton Beach, FL 34217

  Welcome to Sandpiper Resort Co-Op, one of Anna Maria Island’s most sought-after 55+ coastal communities—where owning your own piece of paradise is actually within reach. This beautifully updated 2-bedroom, 1-bath coastal retreat is being sold with the share, offering a rare opportunity for true ownership in a waterfront, amenity-rich community without the high monthly fees typically found on the

  Jomarie Alicea PREFERRED SHORE LLC

  2601 Gulf Dr N Unit 729, Bradenton Beach, FL 34217
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  /34

  $299,000

  $96K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 838 Sq Ft

  2601 Gulf Dr N Unit B24, Bradenton Beach, FL 34217

  Welcome to Paradise! Sandpiper Resort Co-op is a vibrant 55+ community located on beautiful Anna Maria Island, offering the perfect blend of coastal relaxation and island convenience. This charming 2-bed, 1-bath coastal retreat sits on one of the larger lots in the community, giving you extra space, privacy, and future potential. Enjoy a quintessential island lifestyle: spend your days at the

  Robyn Hawk DUNCAN REAL ESTATE, INC.

  2601 Gulf Dr N Unit B24, Bradenton Beach, FL 34217
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  /25

  $260,000

  $29K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 320 Sq Ft

  2601 Gulf Dr N Unit 506, Bradenton Beach, FL 34217

  Discover the charm of Anna Maria Island with this delightful one-bedroom, one-bath home located in the highly sought-after Sandpiper Resort Co-Op community. Perfectly situated between the sparkling Gulf of Mexico and the tranquil waters of Sarasota Bay, this residence offers the best of both worlds—a relaxed coastal lifestyle in a friendly, active 55+ neighborhood.Inside, you’ll find a bright

  Greg Brock BROCK REAL ESTATE

  2601 Gulf Dr N Unit 506, Bradenton Beach, FL 34217
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  /68

  $7,500,000

  New Construction

  • 6 Beds
  • 6.5 Baths
  • 6,500 Sq Ft

  107 Maple Ave, Anna Maria, FL 34216

  This turn-key custom built six bedroom six and a half bathroom luxury home on Anna Maria Island is an exceptional beach investment property offering the perfect balance of passive rental income and personal coastal living. Located on one of the most private and prestigious streets on Anna Maria Island just steps from beach access the home offers Gulf of Mexico views and a proven short term rental

  Marisol Horner ARC REALTY GROUP

  107 Maple Ave, Anna Maria, FL 34216
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  /16

  $215,000

  • Land
  • 871 Sq Ft
  • $10,750,000 per Acre

  2601 Gulf Dr N Unit 310, Bradenton Beach, FL 34217

  This rare vacant lot opportunity at the Sandpiper Resort Co-op on Anna Maria Island offers the perfect canvas to build a brand-new coastal retreat in one of the island’s most desirable communities. The lot allows for the placement of a new unit, giving you the unique ability to create a custom residence designed for modern island living, and floor plan drawings for a new unit are already

  Greg Brock BROCK REAL ESTATE

  2601 Gulf Dr N Unit 310, Bradenton Beach, FL 34217
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  /45

  $1,598,000

  $181K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,131 Sq Ft

  519 South Dr, Anna Maria, FL 34216

  “Anna Maria Oasis” is a Bimini Bay Coastal Classic, perfectly positioned on the coveted north end in the City of Anna Maria. With deep-water access directly from your backyard, no bridges to the bay or the Gulf of Mexico, and a 50’ dock with pilings already in place for lift installation, this property is truly a boater’s and fisherman’s paradise.Originally built in 1972, the home was

  Jessica Batten SATO REAL ESTATE INC.

  519 South Dr, Anna Maria, FL 34216

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