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

$415,000
3 Beds 3 Baths Bahia Beach Twnhms Ph 2 SubDv. 33570 Zip Code
Welcome to your own slice of paradise in the sought-after Little Harbor waterfront community! This beautifully updated 3-bedroom, 3-bath corner-unit townhome offers the perfect combination of coastal charm, privacy, and an effortless Florida lifestyle. Designed to embrace true Florida living, this home features three private outdoor spaces, including a serene balcony off the primary suite overlooking the canal, a second private balcony off the upstairs secondary bedrooms that provides additional space to enjoy the spectacular natural surroundings, and a spacious balcony off the dining and living area that creates a seamless indoor-outdoor flow. The rear of the home overlooks the canal and a protected preserve, offering a peaceful tropical backdrop where you can regularly enjoy sightings of manatees, dolphins, native birds, and other Florida wildlife. Filled with abundant natural light, this tastefully updated home showcases a timeless neutral color palette, granite countertops throughout, and a spacious open-concept living area designed for both comfort and entertaining. The stunning primary suite features a luxurious pebble stone, rain-head super shower, creating a spa-like retreat. A newer washer and dryer add everyday convenience, and all appliances throughout the home have been updated, including a recently installed 3-ton HVAC system for enhanced comfort and efficiency. The oversized garage—large enough to function as a one-and-a-half-car garage—provides exceptional storage for beach gear, bicycles, and boating essentials. Beyond your doorstep, Little Harbor offers a true resort-style waterfront lifestyle. Residents enjoy access to a marina, waterfront restaurants, multiple pools, a fitness center, tennis and pickleball courts, and private beach access, all set against some of the most spectacular sunsets over Tampa Bay. Whether you enjoy boating, fishing, kayaking, paddleboarding, or simply relaxing by the water, every day here feels like a vacation. Ideally located in Ruskin, Florida, this home offers exceptional regional connectivity. You are just a short drive to MacDill Air Force Base, as well as other key military and defense installations throughout the Tampa Bay area, including Coast Guard facilities. Travel is convenient with both Tampa International Airport and St. Pete–Clearwater International Airport within easy reach. You are also close to the vibrant downtown districts of Tampa, St. Petersburg, and Sarasota. For beach lovers, the location is unmatched. Enjoy quick access to the world-renowned Gulf Coast beaches, including Anna Maria Island, Siesta Key, and Clearwater Beach, consistently ranked among the best beaches in the world. From white sand shores to crystal-clear waters, the best of Florida’s coastline is right at your fingertips. While Little Harbor does not feature a dedicated dog park within the community, it remains a pet-friendly waterfront neighborhood, with walking areas throughout and nearby public parks in Ruskin offering designated dog parks and additional pet-friendly outdoor spaces. Whether you are searching for a primary residence, vacation getaway, or income-producing investment, this exceptional property offers strong rental potential, an unbeatable location, and the coastal lifestyle you’ve been dreaming of. Don’t miss your opportunity to own one of Little Harbor’s desirable corner-unit townhomes, where comfort, nature, and resort-style living come together beautifully.

3228 Mangrove Point Drive, Ruskin

$3,300,000
4 Beds 4 Baths Westwind A Sub SubDv. 33785 Zip Code
Rare opportunity to own a beautifully maintained, elevated Key West–style Gulf-front pool home in the exclusive gated community of Westwinds. This solid block and cement board 4BR/3.5BA home offers 2,964 sq ft heated living space with direct Gulf views, private beach access, and an open floor plan showcasing cathedral ceilings, arched entryways, and upgrades throughout. The gourmet kitchen features custom wood cabinetry, granite counters, a wine fridge, and stainless gas appliances. The primary suite boasts French doors to a Gulf-view terrace, dual walk-in closets, and a spa-style bath with Jacuzzi tub. A first-level in-law suite with a private bath and entry adds versatility, perfect for guests, a nanny, or generational living. Enjoy a private heated saltwater pool with new child safety fence. Hurricane-rated windows and doors, plus elevated HVAC/pool equipment, speak to the home's safety and security. Per the seller, the home remained completely dry through the 2024 hurricane season (X Flood Zone). Recent updates include 3 newer HVAC units, a fire sprinkler system redone in 2025, a new water heater and refrigerator, a new pool pump, an updated panel surge protector, fresh interior paint, and polished travertine floors. Oversized 2 car garage includes 14 foot ceilings and additional storage space. Sold turnkey and fully furnished. A short list of personal items that do not convey is available upon request. HOA covers grounds, exterior, and road maintenance (Only $500/mo). Meticulously maintained. Exceptional quality. History of storm security. Steps to the beach. Schedule your private showing today!

2718 Gulf Boulevard Unit 2, Indian Rocks Beach

$269,900
1 Beds 1 Baths Waterside At Coquina Key South SubDv. 33705 Zip Code
This 1 bedroom, 1 bath unit comes with a private boat slip! The boat slip is located behind Bldg 60 on Canal #5 and is has electric and water along with a storage box. The unit has upgraded cabinets, granit countertops and sleek stainless steel appliances. Private balcony provides views of the saltwater canal to enjoy while having your morning coffee or savoring a sunset cocktail. The Waterside South community has 24 hour gated entrance with on-site security and is PET FRIENDLY. This waterfront location allows you to stroll along 88 acres of lush, landscaped waterfront and 3 miles of sea paths along Tampa Bay. Enjoy cocktails and dinner at the exclusive, private two story Waterside Yacht Club, which offers full liquor sports bar, nightly specials in the restaurant and gorgeous water views. The Waterside community features two pools, one of which is right on the bay with a hot tub, and there is a fully equipped gym open 24/7. The clubhouse also has saunas, billiards room, library/game room, vending machines, ice machine and laundry facilities. This private yacht club has an elevator and may be booked for private events. Relax and do some fishing from the private Fishing Pier, play tennis under the lights, or opt for Pickleball, basketball, sand volleyball, horseshoes, or shuffleboard. Or take a stroll with your pooch at the on-site dog park with walking paths. Bicycle and Kayak racks are available for use. There are also Garages, Carports, Dry dock storage and Boat slips, accommodating boats up to 32’ , which are available for lease and additional purchase. Waterside South is a short commute from the bustling downtown and waterfront area of St Petersburg with its boutique shopping, dining, numerous museums, and many entertainment venues. Short drive to Fort DeSoto and the beautiful sands of St Petersburg Beach. Easy commute to Tampa and Tampa International Airport to the north and the iconic Skyway Bridge and Sarasota/Bradenton area to the south.

4728 Beach Drive Se Unit B, St Petersburg

$269,700
2 Beds 3 Baths Dolly Bay Vlg On Lake Tarpon Condo SubDv. 34684 Zip Code
COME LIVE THE FLORIDA LAKE LIFESTYLE! Move-In Ready and thoughtfully remodeled, this furnished (optional) 2-bedroom, 2.5-bath, two-story condominium offers dual primary suites, soaring vaulted ceilings, direct access to beautiful 2,534-acre Lake Tarpon, boat slips available on a first-come, first-served basis, kayak storage, a New HVAC (2024), New Metal Roof (2024), New Electrical Panel, a Clean 4-Point Inspection (April 2026), and the added peace of mind of being located in Flood Zone X—all within Dolly Bay, one of Palm Harbor's most charming waterfront communities. With just 84 residences, Dolly Bay offers a warm, neighborly atmosphere surrounded by mature trees, tranquil ponds, scenic boardwalks, abundant Florida wildlife, and direct access to one of Pinellas County's premier freshwater lakes. Stretching nearly 9 miles with approximately 16 miles of shoreline, Lake Tarpon is renowned for exceptional bass fishing, boating, kayaking, paddleboarding, and spectacular sunsets. This spacious 1,633-square-foot residence is filled with natural light and features soaring vaulted ceilings, an open floor plan, inside laundry, abundant storage, a usable attic, and a versatile nook beneath the staircase that's perfect for a home office, reading area, decorative display, or pet retreat. The beautifully remodeled kitchen showcases real wood soft-close cabinetry, granite countertops, stainless steel appliances, a Breakfast Bar, Coffee Station, and abundant cabinetry. Matching granite continues throughout the bathrooms, while elegant wainscoting and a convenient Wet Bar make entertaining effortless. The home is being offered furnished for the seller's convenience, with the option to remove furnishings if preferred by the buyer, making it ideal as a primary residence, seasonal retreat, or investment opportunity. Upstairs, both bedrooms are spacious private suites with their own ensuite bathrooms, offering exceptional privacy for owners and guests. Relax on your screened balcony overlooking the peaceful pond and scenic boardwalk while enjoying the sights and sounds of owls, songbirds, squirrels, and Florida's natural beauty. 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 access to Lake Tarpon. Boat slips are available on a first-come, first-served basis (currently $1,000/year), and kayak storage is available for just $100/year. The home includes one assigned parking space plus ample guest parking and is conveniently located near John Chesnut Sr. Park, the Pinellas Trail, Gulf beaches, shopping, dining, golf courses, top-rated healthcare, St. Pete/Clearwater and Tampa International Airports. Whether your perfect day includes boating across Lake Tarpon to the Tarpon Turtle Waterfront Grill for lunch or dinner, casting a fishing line at sunrise, paddling peaceful waters by kayak, or relaxing around the community fire pit with neighbors, Dolly Bay offers the Florida waterfront lifestyle you've been searching for. It's more than a home... it's the Florida lifestyle. Welcome to Dolly Bay.

2599 Dolly Bay Drive Unit 306, Palm Harbor

$2,500,000
4 Beds 5 Baths Greenland Preserve SubDv. 33715 Zip Code
Nestled within the exclusive Greenland Preserve Conservation Area, this exceptional 4-bedroom 3.5-bath residence offers the perfect blend of luxury, privacy, and natural beauty. A gated entrance welcomes you home, where a circular driveway and oversized 3-car garage create an impressive first impression. Designed with soaring ceilings and abundant natural light, the home features an elegant living room with a cozy fireplace, custom built-in shelving, and expansive windows that showcase the tranquil surroundings. The spacious kitchen is thoughtfully designed with a large center island, generous cabinetry, and ample storage, making it ideal for both everyday living and entertaining. The luxurious primary suite is a private retreat, complete with a sitting area, two walk-in closets—including one oversized dressing closet—and a spa-inspired ensuite bath designed for ultimate relaxation. Outdoor living is equally impressive. Two spacious balconies and a lower-level covered patio with a fully equipped outdoor kitchen provide multiple spaces to entertain or unwind. Gather around the custom built fire pit while enjoying peaceful views of the pond and the lush Florida foliage that surrounds the property. Water enthusiasts will appreciate the rare combination of a deeded boat slip with dock at the community marina, as well as a private dock located behind the home. A charming catwalk meanders through the natural landscape, leading directly to your private waterfront access. Offering an unmatched lifestyle in a serene conservation setting, this remarkable home combines elegant design, exceptional outdoor amenities, and convenient boating access in one extraordinary property.

2000 Bayview Drive, Tierra Verde

$1,625,000
4 Beds 4 Baths Oyster Point Sub SubDv. 34683 Zip Code
Every detail of this custom Key West-inspired residence has been thoughtfully designed to embrace the Florida lifestyle while delivering exceptional comfort, craftsmanship, and timeless coastal elegance. Perfectly positioned on a beautifully landscaped 0.26-acre corner homesite within the sought-after Oyster Point community, this 4-bedroom, 3.5-bath residence offers 3,334 square feet of heated living space and 6,344 total square feet across three expansive levels, creating a home that feels both grand and inviting. Natural light pours through the open-concept living spaces, highlighting soaring ceilings, engineered hardwood flooring, crown molding, custom built-ins, and a wood-burning fireplace that creates a warm focal point for gathering. Designed with entertaining in mind, the spacious kitchen features solid wood cabinetry, stone countertops, abundant prep space, and a seamless connection to the dining and living areas, making everyday living as enjoyable as hosting family and friends. The home's outdoor living spaces are equally impressive. Covered wraparound decks capture peaceful views toward Sutherland Bayou, extending the living space outdoors and providing the perfect setting for morning coffee, sunset cocktails, or weekend entertaining. Below, the private saltwater pool is surrounded by mature landscaping, creating a secluded fenced backyard retreat that feels like your own private resort. Occupying its own level, the spacious primary suite offers privacy and tranquility, while three additional bedrooms provide flexibility for guests, family, or a home office. An oversized four-car garage offers exceptional storage for vehicles, golf carts, watercraft, and recreational equipment. Located just minutes from marinas, championship golf, waterfront parks, charming downtown Palm Harbor, Ozona, Dunedin, and the Gulf Coast's award-winning beaches, this exceptional residence combines luxury, space, and an unbeatable coastal lifestyle—all with no HOA fees.

1700 Oyster Point Way, Palm Harbor

$194,900
1 Beds 1 Baths Grand Key A Condo SubDv. 33611 Zip Code
Welcome to Grand Key, a gated Key West-style community in the heart of South Tampa! This beautifully maintained first-floor 1-bedroom, 1-bath condominium offers the perfect combination of comfort, convenience, and investment potential. Inside, you'll find an open and functional floor plan featuring a spacious living and dining area, granite countertops, solid wood cabinetry, a breakfast bar, and a generously sized bedroom with a walk-in closet. The unit also includes a full-size washer and dryer, a private storage closet conveniently located just outside the front door, and a reserved parking space. Best of all, it is being sold fully furnished, making it truly move-in ready. Grand Key offers resort-style amenities, including a sparkling swimming pool, fitness center, indoor basketball court, clubhouse, playground, grilling areas, and beautifully landscaped courtyards. The gated community is professionally managed and meticulously maintained, with beautifully landscaped grounds and common areas. Ideally located in the heart of South Tampa, you'll be just minutes from Hyde Park, Bayshore Boulevard, Downtown Tampa, MacDill Air Force Base, Tampa International Airport, International Plaza, top-rated restaurants, shopping, and major highways. Whether you're looking for a primary residence, a second home, or an investment property, this condo is an excellent opportunity. Grand Key allows 6-month minimum rentals, offering flexibility for both homeowners and investors.

4207 S Dale Mabry Highway Unit 6107, Tampa

$769,999
3 Beds 2 Baths Excelsior Sub SubDv. 33603 Zip Code
Welcome to an almost-new Key West–style cottage in the heart of historic Tampa Heights—where timeless charm, modern comfort, and one of Tampa’s most vibrant urban lifestyles come together beautifully. Just moments from Armature Works, the Tampa Riverwalk, neighborhood parks, and nearby public and private schools, this home places you right in the center of everything buyers love about Tampa Heights. Downtown Tampa, Channelside, Water Street, and Ybor City are all less than 10 minutes away, while Tampa International Airport is approximately 20 minutes from your door. From the moment you arrive, the home makes a memorable first impression with its inviting oversized front porch and distinctive arched entry door. Step inside and you’ll immediately notice the craftsmanship, thoughtful design, and attention to detail that make this residence feel truly special. Designed with beauty, efficiency, and everyday comfort in mind, this 3-bedroom, 2-bath home offers an open great room that is ideal for entertaining, relaxing, or gathering at the end of the day. Outside, enjoy Florida evenings around the gas backyard fire bowl, bike along the Riverwalk, or stroll to dinner at Armature Works and take in sunset views over the Hillsborough River. Custom built in 2021, this home offers the ease and confidence of newer construction while capturing the character and charm that makes Tampa Heights so desirable. Furnishings are negotiable if desired, creating a potentially exceptional turnkey opportunity in one of Tampa’s most connected and sought-after neighborhoods.

3016 N Massachusetts Avenue, Tampa

$675,000
4 Beds 3 Baths Donovan W P Sub SubDv. 33782 Zip Code
Welcome to this one-owner custom home, offered for sale for the very first time! Situated on an expansive 18,000-square-foot lot on a quiet dead-end street, this nearly 2,500-square-foot home offers a rare combination of space, flexibility, and an unbeatable central Pinellas County location. Conveniently located between St. Petersburg, Tampa, and the award-winning Gulf beaches, you'll also enjoy easy access to Freedom Lake Park, Helen S. Howarth Community Park, shopping, and dining. Set on an expansive 18,000-square-foot lot, this property offers endless possibilities rarely found in Pinellas County. Whether you're dreaming of a resort-style pool, detached garage, workshop, guest house, or accessory dwelling unit (ADU), there's room to bring your vision to life. With ample access on both sides of the home leading to the backyard, it's an ideal setup for car enthusiasts, contractors needing space for work vehicles and equipment, RV or boat owners, or buyers seeking the flexibility to add a mother-in-law suite or private guest quarters. Inside, the thoughtfully designed floor plan offers generous living spaces with 10-foot ceilings throughout the main level. The first floor features a spacious living room, comfortable family room, formal dining room, well-appointed kitchen, and an oversized primary suite. Beautiful porcelain tile flooring flows throughout the kitchen, hallways, and primary suite, adding both style and durability. Just off the primary bedroom is a flexible bonus room perfect for a home office, nursery, or private sitting room. The primary suite also features an impressive walk-in closet, oversized two-person jetted soaking tub, private water closet, and French doors leading to a private deck overlooking the expansive backyard. A convenient wet bar and nearby half bath provide the perfect setup for future outdoor entertaining or poolside gatherings. Upstairs, you'll find two generously sized bedrooms, a full bathroom, and abundant easily accessible attic storage. Additional highlights include a durable 2018 metal roof, dual-pane windows, an XL Trane air conditioning system, a spacious two-car garage, and an oversized driveway with parking for four or more vehicles. Lovingly maintained by its original owners since it was built, this home presents a rare opportunity to own a property with exceptional space, flexibility, and potential in one of Pinellas County's most convenient locations. Move in and enjoy it as-is, or update it over time to create the home you've always envisioned. Opportunities like this don't come along often—schedule your private showing today and discover the endless possibilities this exceptional property has to offer!

9121 65th Street N, Pinellas Park

$749,900
3 Beds 3 Baths Sunset Hills Rep SubDv. 34689 Zip Code
This KEY WEST STYLE CHARMER captures the essence of relaxed “OLD FLORIDA” living, with SWIMMING POOL, 3 Wood Deck areas, and detached garage/pool House. Thoughtful upgrades include a STUNNING NEW KITCHEN, NEW ROOF 2026 & NEW HVAC 2024. Built above base elevation for LOW flood insurance cost of $682 yearly, experienced no flooding during the hurricanes. Nestled between the scenic Tarpon Springs bayous and 2 GULF BEACHES, this location offers a rare blend of Old Florida charm, coastal beauty, and small-town character that is becoming increasingly difficult to find. You’ll be greeted by a shell driveway and wood stairway leading you up to a relaxing front porch. From the moment you enter custom woodwork, generous living spaces, and an atmosphere that feels both timeless and inviting set the tone. From the moment you step inside, you'll appreciate the bright, open feel accented by bay windows that fill the home with natural light. At the heart of the home lies a stunning NEW CHEF-INSPIRED GOURMET KITCHEN with abundant WHITE SHAKER CABINETRY, gleaming Brazilian QUARTZ COUNTERTOPS, tile backsplash, center island with custom lighting and breakfast bar, and SS appliances. The adjoining eat-in area offers a bay window, creating the perfect spot to enjoy your morning coffee. A convenient powder room is located on the first floor for guests. And an inside utility room offers a convenient exterior door out back. The owner’s suite is a private sanctuary, with a dedicated sitting area featuring a bay window and soaring cupola like ceiling, as well as a ensuite bathroom. The inviting front deck and dual back decks (one screened, one open) create seamless indoor-outdoor living, ideal for enjoying breezes year-round. Open the doors to your private outdoor paradise, where your SPARKLING POOL is surrounded by lush Florida native landscaping, ideal for year-round relaxing and entertaining. The pool was built in 2023. The pool and wood decks create the perfect setting for sunset cocktails, weekend barbecues, or simply enjoying Florida's beautiful weather. Set on a 0.21-acre lot, the property offers exceptional outdoor living area. Beyond the pool area, the backyard offers plenty of room for pets, play, or gardening and is fully fenced for exceptional privacy. Have a boat or RV? No problem! This large lot offers PLENTY OF PARKING SPACE, including a long driveway along the South side of the home, as well as an expansive shell driveway in the front. THE DETACHED GARAGE has been partially converted into living area and can be a POOL HOUSE, in-law suite or Air B&B!! If used as living area the TOTAL SQFT of the home would be *2,650SQFT*. Located just 1 mile to Sunset Beach and Fred Howard Park & Beach, and 2 miles to downtown Tarpon Springs and the famous Sponge Docks, you’ll have endless opportunities to enjoy the charming coastal town of Tarpon Springs - named the best Historic Small Town in the United States. Whether you're into water sports, fishing, marinas, walking and biking trails, parks, waterfront restaurants, boutique shopping, craft breweries, or downtown arts festival, this area has something for everyone to enjoy. This rare combination of Key West charm, Gulf beaches proximity, sparkling pool, and NEW KITCHEN, ROOF & AC makes this home stand out. This is more than just a home—it's an opportunity to enjoy one of Florida's most charming coastal communities.

510 Wideview Avenue, Tarpon Springs

$299,999
2 Beds 2 Baths Mallory Square A Condo SubDv. 33609 Zip Code
Go big—and go home to Mallory Square Unit A8. Featuring the largest floorplan in the entire condominium community, this home offers 994 square feet of beautifully refreshed living space and wears every inch well. Vaulted ceilings soar throughout, creating an open, airy feeling rarely found in condo living, while western exposure fills the interior with warm afternoon sunlight. Luxury vinyl flooring and fresh paint provide a clean, modern backdrop that is ready for its next owner from day one. The spacious primary suite is a true retreat, complete with a walk-in closet and an impressively large primary bathroom. Step outside to your covered private patio and take in the pool view—the perfect setting for morning coffee, an evening cocktail, or a well-earned moment of doing absolutely nothing. The generous layout offers the flexibility and breathing room you have been searching for, all within one of Tampa’s most conveniently located communities. Mallory Square places you just minutes from Downtown Tampa, Hyde Park Village, Bayshore Boulevard, the Westshore Business District, Tampa International Airport, and some of the city’s best dining, shopping, and entertainment. This is more than the largest floorplan at Mallory Square. It is vaulted ceilings, golden-hour light, poolside views, modern finishes, and an unbeatable Tampa location—all coming together in one legendary address. Mallory Square Unit A8. This is the one you were hoping would hit the market.

3002 W Cleveland Street Unit A8, Tampa

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