Anna Maria Homes with Key West Architectural style

Anna Maria Homes with Key West Architectural style

Welcome to Anna Maria, Florida, a hidden gem nestled along the Gulf Coast that embodies the essence of island living. Known for its pristine beaches, charming boutiques, and vibrant local culture, Anna Maria offers a picturesque backdrop for those seeking a serene lifestyle infused with coastal charm. This quaint city is renowned for its laid-back atmosphere, where the sound of gentle waves and the scent of saltwater create a perfect sanctuary for relaxation.

One of the standout features of Anna Maria is its stunning homes, particularly those designed in the Key West architectural style. These homes are characterized by their vibrant colors, metal roofs, and spacious porches, seamlessly blending with the tropical surroundings. The Key West style captures the essence of coastal living, featuring open floor plans that invite natural light and breezes, as well as inviting outdoor spaces perfect for entertaining or enjoying a sunset with family and friends.

In Anna Maria, you’ll find a variety of Key West-style homes, each with its unique charm and appeal. Many properties boast modern amenities while retaining the classic coastal aesthetics that define this architectural style. Imagine waking up in a beautifully designed home, sipping coffee on your porch, and taking in the breathtaking views of the Gulf of Mexico.

Whether you’re looking for a vacation retreat or a permanent residence, Anna Maria offers a lifestyle that is both enchanting and enriching. Experience the magic of island living and discover your dream home in this idyllic coastal paradise.

Newest Anna Maria Homes with Key West Architectural style

2511 Dolly Bay Drive Unit 104, Palm Harbor
$291,700
2 Beds ⋅ 2 Baths ⋅ Dolly Bay A Village On Lake Tarpon SubDv. ⋅ 34684 Zip Code
MOVE-IN READY | UPDATED | 1,611 SQ. FT. | LAKE TARPON WATERFRONT COMMUNITY! Welcome to Dolly Bay, one of Palm Harbor’s hidden waterfront gems! This spacious 2-bedroom, 2-bath condo offers 1,611 sq. ft. PLUS an enclosed lanai overlooking a serene tropical nature setting. Thoughtfully remodeled and well maintained, this home is move-in ready and offered furnished (optional) for the seller’s convenience. Inside, enjoy a spacious layout with NO CARPET, abundant storage, a large galley kitchen with NEW refrigerator, WET BAR, indoor laundry and pantry/storage area. The enclosed lanai features DOUBLE-PANE INTERIOR SLIDERS and HURRICANE-RATED WINDOWS throughout—creating a peaceful space to enjoy the beautiful nature views. The oversized primary suite features TWO WALK-IN CLOSETS, an ensuite bath with a large ROUND JACUZZI TUB and separate linen closet. The generously sized second bedroom, full hall bath and foyer closet provide even more space and storage. Major improvements include NEW HVAC, NEW HOT WATER HEATER, NEW REFRIGERATOR, NEW METAL ROOF (2024), popcorn ceilings removed, hurricane-rated lanai windows, double-pane interior sliders and numerous additional updates. With just 84 residences, Dolly Bay offers a charming, neighborly atmosphere surrounded by mature trees, tranquil ponds, scenic boardwalks and Florida wildlife—all with DIRECT ACCESS TO LAKE TARPON, one of Pinellas County’s premier freshwater lakes for boating, fishing, kayaking and paddleboarding. Community amenities include a HEATED LAKEFRONT POOL, clubhouse, tennis courts, waterfront boardwalk, fishing dock, fish-cleaning station, community fire pit, picnic area with BBQ grills and private Lake Tarpon access. BOAT SLIPS are available first-come, first-served (currently $1,000/year), with KAYAK STORAGE currently available for $100/year. One assigned parking space plus ample guest parking. Conveniently located near John Chesnut Sr. Park, Pinellas Trail, Gulf beaches, shopping, dining, golf, healthcare and both St. Pete-Clearwater and Tampa International Airports. Imagine boating across Lake Tarpon for lunch or dinner at Tarpon Turtle, fishing at sunrise, kayaking peaceful waters or relaxing around the community fire pit. Ideal as a PRIMARY RESIDENCE, SEASONAL RETREAT or INVESTMENT OPPORTUNITY. It’s more than a home—it’s the Florida waterfront lifestyle. WELCOME TO DOLLY BAY!

2511 Dolly Bay Drive Unit 104, Palm Harbor

10908 Land O Lakes Boulevard, Land O' Lakes
$1,595,000
5 Beds ⋅ 6 Baths ⋅ Highway Lake Ests SubDv. ⋅ 34638 Zip Code
Virtually Staged. CUSTOM LAKEFRONT HOME OFFERED BELOW APPRAISED VALUE! Experience exceptional waterfront living in this one of a kind home on beautiful Green Lake, a boating and ski lake in Land O Lakes. Set on approximately half an acre with NO HOA and NO CDD, this distinctive property pairs custom design with inviting spaces for entertaining, relaxing, and enjoying life on the water. Five bedrooms and five and a half bathrooms provide generous accommodations, with a private bathroom for every bedroom. An oversized second primary bedroom on the ground floor features its own PRIVATE ENTRANCE, offering added flexibility for guests or extended family. A STUDIO APARTMENT with a separate private entrance creates additional space for multigenerational living or a private retreat, while the bonus media room is ideal for movie nights. The home makes it easy to envision your next chapter, whether as a primary residence or a lakefront getaway. A custom circular driveway creates a memorable arrival, and the outdoor living spaces make an equally lasting impression. Gather around the outdoor kitchen, unwind beside the fire pit, or enjoy the lake views from the expansive custom covered deck. Multiple electric fireplaces inside and outside add warmth and ambiance to spaces designed for year round enjoyment. Spend your days boating, skiing, or simply taking in the peaceful waterfront setting from your own backyard. For buyers seeking even more space, the adjacent approximately half acre lakefront lot (MLS: TB8356791) is available for purchase, presenting an opportunity to expand your waterfront footprint to approximately one acre. Located near the US 41 and SR 52 corridor, this property combines lakefront living with convenient access to the area's growing selection of shopping, dining, and amenities. Custom character, direct lakefront living, and the freedom of no HOA or CDD make this an exceptional opportunity. Schedule your private showing and experience what makes this Green Lake home so special.

10908 Land O Lakes Boulevard, Land O' Lakes

6244 Spoonbill Drive, New Port Richey
$725,000
5 Beds ⋅ 4 Baths ⋅ Gulf Harbors Sea Forest SubDv. ⋅ 34652 Zip Code
WATERFRONT OPPORTUNITY WITH 3,500+ SF, 2 PRIMARY SUITES, HEATED POOL & GULF ACCESS! BOAT OWNER? THIS IS YOUR CHANCE TO ACTUALLY USE THAT BOAT! MOTIVATED SELLER! Welcome to 6244 Spoonbill Drive—a NEVER-FLOODED, elevated waterfront home with 50FT seawall of water frontage! This is an incredible combination of space, flexibility, and Florida lifestyle. Situated on a coveted cul-de-sac/corner-edge lot with canal access toward the Gulf of Mexico, this property gives you the rare opportunity to have the boat, pool, entertaining space, and room for everyone—all in one place. With 5 bedrooms, 4 baths, 3,500+ SF, TWO PRIMARY SUITES, multiple living areas, and an exceptionally versatile floor plan, this home is perfectly suited for multigenerational living. The entire first floor creates an incredible IN-LAW SUITE/guest suite opportunity, complete with its own entrance, living spaces, bedroom, full bath, and direct access to the pool. Use it as a private retreat, guest quarters, media area, or extended-family living space—the flexibility is exceptional. The downstairs den also features a true wood-burning fireplace, adding warmth and character rarely found in today's homes. Upstairs, the main living level welcomes you with abundant natural light, an expansive great room, beautiful water views, and a spacious kitchen featuring custom cabinetry, extensive drawers and storage, stainless steel appliances, granite countertops, and an oversized island built for gathering. The primary suite overlooks the water and offers a generous bathroom, large walk-in closet, and crown molding, while the second primary suite downstairs provides its own private retreat. Crown molding continues through the common areas, adding an elegant finishing detail throughout the home. Storage is abundant, with oversized closets, linen closets, huge garage, cabinetry, and flexible spaces throughout. Step outside and the lifestyle gets even better. The backyard features a heated pool, multiple entertaining areas, gazebo/ pergola, outdoor dining, fire pit, fenced side yard, seawall, and floating dock—ready for pool parties, BBQs, music, sunset cocktails, and unforgettable gatherings. Take the boat out through the canal toward the Gulf, launch your kayak or paddleboard, or simply enjoy the dolphins, manatees, birds, and sunsets from your own backyard. This is the Florida dream—with the space to actually live it. The home has been exceptionally cared for and features a 2017 roof, 2022 AC, newer water heater, updated flooring throughout both levels, full paver driveway and sidewalk, professionally maintained AC, extensive storage, oversized closets, and a large custom kitchen. The bones are fantastic, the floor plan is incredibly versatile, and the cosmetic details offer an opportunity to personalize the home and create something truly special. Select virtually renovated bathroom images are included to help buyers envision the possibilities; no structural changes are represented. Gulf Harbors residents can enjoy the community clubhouse, pool, pickleball/tennis amenities and the option to join the private Gulf Harbors Beach Club. MOTIVATED SELLER + A HOME WITH THIS MUCH SPACE, WATERFRONT, POOL, BOATING ACCESS, AND MULTIGENERATIONAL POTENTIAL = A RARE OPPORTUNITY, ESPECIALLY IN THIS COMMUNITY AND PRICE POINT. Bring your vision, bring your boat, and make this Gulf Coast retreat your own!

6244 Spoonbill Drive, New Port Richey

5050 Coquina Key Drive Se, St Petersburg
$430,000
2 Beds ⋅ 2 Baths ⋅ Waterside At Coquina Key South SubDv. ⋅ 33705 Zip Code
IMAGINE WAKING UP, OPENING THE BLINDS, AND TAKING IN EXPANSIVE, UNOBSTRUCTED VIEWS OF TAMPA BAY. Welcome to 5050 Coquina Key Dr SE, a beautifully updated two-level waterfront townhome where the water becomes part of your everyday surroundings. Inside, hurricane-rated windows frame the views, while the updated kitchen features custom cabinetry, granite countertops, stainless steel appliances, a wine refrigerator, and a spacious island. Step outside onto the large paver patio surrounded by lush landscaping and enjoy the waterfront setting just steps from your door. Launch a kayak or paddleboard, relax by the nearby community pool, or simply enjoy the views of Tampa Bay. Whether used as a primary or seasonal residence, this property offers the opportunity to enjoy Florida waterfront living while remaining just minutes from Downtown St. Petersburg. At the current listing price, SELLER IS OFFERING TO PAY THE RECENTLY APPROVED $25,730.64 SPECIAL ASSESSMENT AT CLOSING, subject to the terms of an accepted contract. If financed through the association's stated payment schedule rather than paid in full, the assessment is approximately $714.74 per month for 36 months, in addition to the regular HOA assessment. Buyers and buyers' agents should independently verify the assessment amount, payment schedule, HOA fees, and all association information directly with the association and applicable documents. The gated waterfront community offers 24-hour guarded access, a community pool, fitness center, yacht club and clubhouse facilities, tennis, pickleball and basketball courts, shuffleboard, playground, walking areas, boat-slip opportunities, and access to Tampa Bay for boating, kayaking, and paddleboarding. This isn't just about living near the water. It's about waking up to it

5050 Coquina Key Drive Se, St Petersburg

103 Royal Court, Safety Harbor
$1,500,000
4 Beds ⋅ 4 Baths ⋅ Philippe Pointe SubDv. ⋅ 34695 Zip Code
Nestled on a premier corner cul-de-sac lot within Safety Harbor’s highly coveted Philippe Pointe neighborhood, the elevated Key West-style retreat at 103 Royal Ct stands as a masterclass in sophisticated coastal living. Expertly manicured grounds frame this grand estate, where a permanent natural buffer ensures absolute privacy, and panoramic views of Old Tampa Bay stretch across the horizon. Every morning here begins with a brilliant sunrise dancing across the water, while evenings showcase the distant, glistening lights of the Tampa skyline. The journey inside begins through custom leaded glass front doors that open up to a grand, sun-drenched main level where formal and casual spaces flow seamlessly together. To the left, an expansive dining room sets an elegant stage for hosting, while straight ahead, the open family room anchors the heart of the home. Steps away, a bright, efficient chef’s kitchen serves as a natural gathering point, complete with a cozy breakfast nook and a casual snack bar. Glass doors transition the indoor living out onto a sweeping wrap-around deck, inviting you to dine alfresco against the backdrop of the bay. This level is rounded out by a quiet sunroom and office that accesses an independent open balcony, alongside two spacious bedrooms and a versatile bonus room. The entire third floor is dedicated to a spectacular, private master oasis designed around its breathtaking environment. Massive windows wrap around the suite to capture the best waterfront vistas imaginable, allowing you to wake up to the sight of the bay from every angle before stepping out onto a private balcony. Custom decor elevates the tranquility of this top-level retreat, which features an adjoining spa-like bath and deep walk-in closets. Down on the ground level, multi-generational living or guest hosting is made effortless by a private fourth bedroom suite equipped with its own full bath. This level walks straight out to a screen-enclosed backyard resort, highlighted by a pristine pool and spillover spa. A covered lanai features year-round entertaining, situated next to a massive 3-car garage with oversized bays and built-in workshop space. Meticulously maintained with robust full stucco construction, a custom paver driveway, and a durable new roof, this remarkable property sits just steps from the historic trails of Philippe Park and minutes from the vibrant boutique shopping, cafes, and local festivals of downtown Safety Harbor. ROOF = 2025 / HVAC = 4 UNITS: 2011, 2018, 2019, 2025 / WATER HEATER = 2017

103 Royal Court, Safety Harbor

7957 2nd Avenue S, St Petersburg
$2,999,000
3 Beds ⋅ 4 Baths ⋅ South Cswy Isle 2nd Add SubDv. ⋅ 33707 Zip Code
Virtually Staged. JUST COMPLETED—2026 ELEVATED WATERFRONT LIVING IN SOUTH CAUSEWAY ISLE/YACHT CLUB ESTATES! From the moment you arrive, this distinctive waterfront residence makes an impression with its elevated design and custom hand-applied natural seashell exterior finish. Offering approximately 2,878 SF of heated and cooled living space with 3 bedrooms, 2 full baths and 1 half bath on the main living level, plus a separate den/office/bonus room that could be used as a 4th bedroom, the home provides exceptional flexibility. A striking custom-built stairway creates the transition to the elevated main living level and immediately showcases the home's craftsmanship. Combining natural wood with iron, stainless-steel supports and horizontal wire railings, the open architectural design makes the stairwell a feature of the residence rather than simply a passage between floors. Ascend to the main living level, where the home opens into a bright, expansive floor plan with kitchen, dining and living areas flowing together and drawing your attention toward the water. The kitchen features a large island, white cabinetry, quartz countertops and KitchenAid Signature Series stainless-steel appliances. LVP flooring continues throughout the living areas for a clean, contemporary coastal feel. The waterfront primary suite features a private balcony, large walk-in closet and luxurious bath with dual vanities, private toilet area and an oversized walk-in shower with marble walls. Additional bedrooms and baths provide comfortable accommodations for family and guests, while bathrooms on the main living level feature heated bidets. Moving toward the rear of the living space, this is where the home truly becomes about the Florida waterfront lifestyle. Step onto the expansive waterside deck, where stainless-steel posts and horizontal cable railings preserve the views. Below, an in-ground saltwater pool overlooks the water, while the private dock and two boat lifts with approximately 16,000-lb and 10,000-lb capacities put boating right outside your back door. Spend the day on the water, return for a swim and finish the evening watching the sunset from your backyard. The approximately 2,160 SF garage/lower level features a 5-car garage capable of accommodating up to 6 vehicles, epoxy flooring, an 8,000-lb automobile lift and separate half bath. A full-view glass rear garage door on the waterside provides convenient access for kayaks, paddleboards and other waterfront gear. Behind the finishes is substantial construction, including an engineered foundation with 33 pilings, engineered floor and roof trusses, PGT impact-resistant windows, impact-rated exterior doors, a 5V-crimp metal roof, engineered flood vents and breakaway construction. Located in South Causeway Isle/Yacht Club Estates, enjoy direct boating access to Boca Ciega Bay and the Gulf, world-famous beaches nearby and Downtown St. Petersburg approximately 20 minutes away for dining, museums, entertainment and professional sports. This is more than a waterfront home—it's an opportunity to live the boating, water and sunset lifestyle that makes this part of St. Petersburg so special. All dimensions are estimates and need to be verified by the buyer.

7957 2nd Avenue S, St Petersburg

2805 Gulf City Road, Ruskin
$1,800,000
1 Beds ⋅ 1 Baths ⋅ Unplatted SubDv. ⋅ 33570 Zip Code
Experience sweeping views of the Little Manatee River from your own private retreat. This rare and exceptional property features a beautifully remodeled home thoughtfully designed for entertaining, relaxing, and enjoying the picturesque natural surroundings. At the heart of the home, expansive wall-to-wall windows fill the living spaces with natural light while showcasing stunning river views as the ultimate backdrop. The meticulously maintained backyard is a peaceful oasis, complete with lush St. Augustine grass, majestic oak trees, a covered porch, a charming swing, and a private dock—perfect for quiet mornings or relaxing evenings by the river. The spacious travertine pool lanai provides an ideal setting for entertaining large gatherings while still capturing beautiful views of the river. Inside, the well-appointed kitchen features top-of-the-line appliances, upscale finishes, and plenty of space for hosting family and friends. The large primary bedroom offers serene river views and an impressive walk-in closet. A versatile den provides additional flex space that can easily serve as a guest bedroom, home office, media room, or entertainment space. Beyond the main residence, the property offers two additional barns along the meticulously maintained driveway, providing abundant storage and exciting potential for future use. With its exceptional privacy, beautifully updated home, and breathtaking river views, this is a truly rare opportunity to own your own slice of the Little Manatee River.

2805 Gulf City Road, Ruskin

786 59th Avenue Ne, St Petersburg
$739,900
3 Beds ⋅ 3 Baths ⋅ Edgemoor Estates SubDv. ⋅ 33703 Zip Code
Nearly new NE St Petersburg 2 story pool home in Edgemoor Estates subdivision. 3 bedrooms, 2 1/2 bathrooms 2 car garage with large bonus/game room on first floor (884 sq ft +/- 26x34) Perfect for an exercise, craft, hobby, party room or just needed extra storage space. Bring your most discerning detail oriented buyers to this CLEAN non smokers home that is immaculately maintained to a high standard. Never a pet inside since original construction in 2003. For those who entertain and enjoy their backyard, your friends and family will enjoy the inground pool & spa, pebble tec surface and covered BBQ area with an outside sink. Entertain in the lushly landscaped tropical setting. Fully vinyl fenced for privacy. Many new amenities to include new roof (2023) attic(s) are semi finished and insulated, new HVAC (2024) new luxury vinyl plank flooring throughout, modern kitchen with granite countertops and new Frigidaire Stainless Gallery series convection stove & refrigerator (2026). Deep water well for irrigation. Featuring high ceilings, wood burning fireplace and a large 2nd floor screened balcony. Security system is owned. Garage has epoxy coated floors and there is an extra side yard parking pad for a boat or RV. Hurricane modifications include impact windows, reinforced garage door, roof strapping and underground utilities (Electric&Water). Nearby community recreation includes the Mangrove Bay golf course, nature walks in Puryear Park rec center. Worldclass education is offered at Shorecrest Preparatory School or Canterbury School of Fl. Well located for access to downtown St Pete and area bridges. Flood insurance is assumable, current cost is $1600/yr! Show and sell! Wont last.

786 59th Avenue Ne, St Petersburg

5518 Luminar Pointe Lane, Apollo Beach
$349,490
3 Beds ⋅ 3 Baths ⋅ Mirabay - Townhomes At Compass Pointe SubDv. ⋅ 33572 Zip Code
5518 Luminar Pointe Ln, Apollo Beach, FL 33572 | 3 Bedrooms | 2.5 Bathrooms | Den | 2-Car Garage | Maintenance-Free Living | MiraBay Experience maintenance-free luxury living in MiraBay with this spacious 3-bedroom, 2.5-bath executive townhome with a den and 2-car garage, located in one of Apollo Beach's premier waterfront communities. Offering an impressive combination of space, upscale finishes, abundant storage, and a walkable location near MiraBay's resort-style amenities, this home delivers the Florida lifestyle you've been looking for. Step inside to an inviting open-concept floor plan featuring beautiful travertine flooring throughout the main level, soaring ceilings, crown molding, modern finishes, and an abundance of natural light. Double French doors open to a private den/home office, complete with built-in shelving. Storage is exceptional throughout the home, with walk-in closets in every bedroom, additional den storage, and a convenient closet tucked beneath the stairs. At the heart of the home is the chef's kitchen, featuring 42-inch upper cabinetry with crown molding, granite countertops, tile backsplash, stainless steel appliances including a wine refrigerator, breakfast bar with pendant lighting, and an oversized center island with additional dining space. A custom built-in hutch adds even more storage and character while creating the perfect space for entertaining. Upstairs, the expansive primary suite feels like a private retreat, beginning with its own foyer and opening to a generous bedroom with a separate sitting area. The ensuite bath features a garden soaking tub, oversized walk-in shower, dual-sink vanity with dedicated makeup space, and a large walk-in closet enhanced with California Closet storage. Two generously sized secondary bedrooms share a convenient Jack-and-Jill bathroom, while the upstairs laundry room includes built-in cabinetry and a utility sink. Enjoy Florida's indoor-outdoor lifestyle from the private pavered and fenced patio, perfect for relaxing, grilling, or entertaining. The 2-car garage is complemented by an oversized driveway long enough to accommodate trucks and SUVs, with additional guest parking conveniently located nearby. Enjoy the ease of maintenance-free living, with landscaping maintenance and water included in the HOA. The home is just steps from a neighborhood park and playground overlooking the lagoon and a short walk to the MiraBay clubhouse and community amenities. Located in the sought-after MiraBay community in Apollo Beach, residents enjoy a resort-style waterfront lifestyle with a clubhouse, pools, fitness center, tennis and pickleball courts, basketball, parks, playgrounds, walking trails, and opportunities for kayaking and paddleboarding. Convenient access to shopping, dining, I-75, Tampa, MacDill Air Force Base, and the greater Tampa Bay area makes this an exceptional opportunity for those seeking a luxury townhome in Apollo Beach, maintenance-free home in MiraBay, or resort-style Florida living. Luxury, space, convenience, and the MiraBay lifestyle come together at 5518 Luminar Pointe Ln—schedule your private showing today!

5518 Luminar Pointe Lane, Apollo Beach

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