Anna Maria Homes with Historic Architectural style

Anna Maria Homes with Historic Architectural style

Welcome to Anna Maria, Florida, a hidden gem nestled on the stunning Gulf Coast. Known for its charming, laid-back atmosphere, Anna Maria is a quaint island city that offers residents and visitors a unique blend of natural beauty and rich history. With its pristine white sandy beaches, crystal-clear waters, and lush tropical landscapes, it’s no wonder that this picturesque locale has become a beloved destination for those seeking a peaceful coastal retreat.

One of the most enchanting features of Anna Maria is its collection of historic architectural homes. These residences, often adorned with classic coastal designs and vibrant colors, reflect the rich history and cultural heritage of the area. From charming bungalows to stately beach houses, each home tells a story of the past, showcasing the craftsmanship and artistry of bygone eras. Many of these historic homes have been lovingly restored, offering modern amenities while preserving their original character and charm.

Living in Anna Maria means embracing a lifestyle that celebrates both relaxation and adventure. Enjoy leisurely strolls along the beach, explore the local shops and eateries, or take part in water activities such as kayaking, paddleboarding, and fishing. The community is tight-knit, with friendly neighbors who share a love for the island's natural beauty and vibrant culture.

Whether you’re drawn to the allure of historic architecture or the serene coastal lifestyle, Anna Maria offers a unique opportunity to experience the best of Florida living. Discover your dream home amidst the charm and history of this enchanting island city.

Newest Anna Maria Homes with Historic Architectural style

$569,000
4 Beds ⋅ 2 Baths ⋅ Old West Tampa SubDv. ⋅ 33607 Zip Code
History with a modern touch! Built in 1918 with 1,980 sqft, this 4BR/2BA two-story bungalow in Old West Tampa has been restored to a standard this urban community rarely sees. HVAC 2024, with nearly every interior finish in this house touched in 2023 - the kitchen and its stainless appliances, both bathroom remodels, electrical, plumbing, the tankless water heater, and paint inside and out. The windows were replaced in 2021. Floodzone X, fully fenced yard with extended paver driveway with gated alley access. The foundation was permanently stabilized in 2022 under a 25-year transferable warranty. Termite protection through Chet's through March 2027. Inside, the ceilings are high, and the plan reads open and spacious - living, dining, and kitchen share one continuous space, so light carries from the front of the house to the back. The kitchen anchors it, with a center island and stainless appliances. On the first floor you’ll find two bedrooms and two full bathrooms. A front bedroom sits just off the dining room and works equally well as a home office and offers its own split AC system so that the room's temperature sets independently of the rest of the house. The owner's suite is on the first floor with a newly expanded bathroom that the current owners enlarged during the renovation rather than settling for what the original footprint allowed. A second updated bathroom is at the back of the house and serves the two upstairs bedrooms and guests. Upstairs, both bedrooms measure over 12 feet wide, each with its own closet and windows. Out back, the yard is fully fenced and finished with custom pavers, two pergolas, and an extended driveway with gates to the alley - room to park several vehicles and privacy on every side—a private and shaded oasis. Schedule your showing and bring your inspector. A 1918 bungalow with its foundation warranted for another twenty-one years, its systems replaced, and Zone X on the current FEMA panel is a rare combination in this pocket of Tampa! Located so close to Armature Works, the new Publix grovery store on Boulevard, and the Riverwalk extension as well as quick access to 275.

2126 W Beach Street, Tampa
$609,000
3 Beds ⋅ 3 Baths ⋅ St Petersburg Investment Co Sub SubDv. ⋅ 33713 Zip Code
Step into 1920’s storybook charm combined with high-end modern living in coveted Historic Kenwood! Dressed in a cheerful shade of powder pink, this historic main bungalow and its detached ADU have both recently undergone considerable renovations including brand-new roofing, fresh paint, and updated electrical systems offering peace of mind for the next lucky owner. Inside the main house, soft blonde flooring and elegant gold accents amplify the abundant natural light flooding every room. The rare open-concept floor plan seamlessly bridges vintage character with a modern layout, anchored by a dramatic stone fireplace. The chef’s kitchen features gas cooking, custom cabinetry, and a charming apron-front sink. The living space and front sun room are bright, airy, and designed for effortless entertaining. The detached ADU with its soaring ceilings, full bathroom, efficiency kitchenette and flexible loft space offers incredible versatility, perfect for private guest quarters or a serene home office. Enjoy historic St. Pete charm, modern convenience, incredible flexibility and an enviable location all in one iconic property. Schedule your tour today!

440 22nd Street N, St Petersburg
$350,000
3 Beds ⋅ 2 Baths ⋅ Macon SubDv. ⋅ 33523 Zip Code
Move in Ready charming turn of the century home with lots of character and history. Located in the old train station town of Trilby, it is close to the Withlacoochee trail for hiking and biking. The cute post office is right down the street. Located minutes off of I-75 , and 5-8 minutes from downtown Dade City, This gem of a find is in the country, but has a great location near Tampa, Ocala, and Orlando, and destinations like the beaches and the theme parks. With 1800 square feet, 3 bedrooms, and two full baths, a newly remodeled kitchen, laundry area, and new CHA mini split system, all on 1/2 Acre of level land, a small workshop and carport/patio pavilion, and dog kennel or chicken coop, this is a real find . The property is fenced with field fencing for privacy or pets.

37315 Trilby Road, Dade City
$169,999
2 Beds ⋅ 2 Baths ⋅ On Top Of The World SubDv. ⋅ 33763 Zip Code
Welcome to On Top of the World, one of Clearwater's most sought-after 55+ communities! This beautifully maintained 2-bedroom, 2-bathroom condo is perfectly positioned to enjoy peaceful golf course views from the front windows while being just a short stroll from the community pool and recreation center. Inside, you'll find a bright, open great room with new laminate flooring, elegant wainscoting, and charming Tiffany-style lighting that adds warmth and character. The updated kitchen features white cabinetry, granite countertops, new stainless steel appliances, including a stove and refrigerator, a modern tile backsplash, updated wiring, and plenty of cabinet space, making it both stylish and functional. For added peace of mind, the HVAC system and water heater are approximately three years old. The oversized primary suite offers a relaxing retreat with an updated en-suite bathroom featuring a beautiful step-in shower. A spacious secondary bedroom is conveniently located near the full guest bath, providing comfort and privacy for family or visitors. One of the highlights of this home is the expansive 25-foot enclosed Florida room—the perfect place to enjoy your morning coffee, entertain guests, or simply relax year-round. Living in On Top of the World means enjoying an incredible array of amenities, including golf course views, fitness centers, swimming pools, tennis and pickleball courts, shuffleboard, a dog park, hobby clubs, and countless social activities. Your monthly condo fee also includes water, sewer, trash, cable, and exterior maintenance, making for truly carefree living. Conveniently located near shopping, restaurants, medical facilities, and entertainment, you're also just a short drive from award-winning Clearwater Beach, where you can enjoy breathtaking sunsets, white sand beaches, and everything Florida's Gulf Coast has to offer. Whether you're looking for a full-time residence or a seasonal retreat, this move-in-ready condo offers the perfect combination of comfort, convenience, and an active Florida lifestyle.

2416 World Parkway Boulevard Unit 26, Clearwater
$450,000
2 Beds ⋅ 2 Baths ⋅ Oak Ridge 4 SubDv. ⋅ 33713 Zip Code
Check out this totally renovated home newly listed and ready for you to move in. Great location in Saint Pete! Inside has a modern kitchen, nice warm vinyl flooring, all new appliances included, and updated electrical in 2018. Also added in 2018 was a complete solar system, set up to feed power back to the power company when not fully being used by the owner. another item to really help with cost, is the new AC system installed in 2024, and roof in 2016. Outside, enjoy a secluded backyard with lots of room to make it your own, maybe even add a deck and outdoor fire pit. The garage has a new full bath, laundry hook ups, and would make a great space for an extra ADU or in-laws suite. The site also includes a one car carport, an extra parking in the driveway for three more vehicles, as well as street parking. Pictures have been virtually staged, to help the new owner with vision and new design ideas. Call to set up a showing today :-)

4660 7th Avenue N, St Petersburg
$424,500
3 Beds ⋅ 2 Baths ⋅ Hamners Aloha Acres SubDv. ⋅ 33604 Zip Code
Finding a true 3-bedroom, 2-bath home with a garage in Hampton Terrace is rare—especially at this price. Set on a spacious 61-by-140-foot corner homesite, 1300 E Henry Avenue offers you an unusually attainable opportunity to own in one of Tampa Bay’s most sought-after historic neighborhoods without sacrificing the space and practical features you want. The home includes 3 bedrooms, 2 baths, a 1-car garage, and fenced front, side, and back yards. Priced below nearly every other three-bedroom home currently available in Hampton Terrace, it represents an exceptional value—not only within the neighborhood, but also when compared with homes in surrounding areas that cannot offer the same combination of historic charm, walkability, mature trees, and genuine sense of community. An inviting front porch immediately feels at home in a neighborhood known for friendly conversations, front-yard gatherings, and neighbors who truly know one another. Inside, oversized windows fill the home with natural light, while hardwood flooring and a stone-trimmed wood-burning fireplace bring warmth and character to the generously sized living room. The flexible floorplan easily accommodates everyday living, entertaining, working from home, or hosting overnight guests. Interior laundry adds everyday convenience, and the garage provides secure parking along with valuable space for bicycles, tools, storage, or hobbies. Outside, the prominent corner setting and established landscaping create welcoming curb appeal, while the deep, fully fenced backyard gives you plenty of room to garden, entertain, create a private outdoor retreat, or potentially add a pool. Once you get to know Seminole Heights, it becomes clear that Hampton Terrace stands apart. Its timeless homes, walkable streets, mature tree canopy, active Neighborhood Watch, strong civic involvement, and beloved traditions have created one of Tampa’s most connected and highly regarded communities. Children’s holiday parades, neighborhood gatherings, and events such as “Summer in the Hamptons” bring residents together and create the kind of neighborhood you seek out—and rarely want to leave. At the heart of the community is Lake Roberta, a cherished neighborhood landmark with peaceful water views, a scenic walking path, and a relaxed gathering place that perfectly reflects the Hampton Terrace lifestyle. Popular Seminole Heights restaurants, coffee shops, breweries, parks, and locally owned businesses are also nearby, along with convenient access to Downtown Tampa and many of the city’s major destinations. For additional peace of mind, the property is located in FEMA Flood Zone X, generally considered a lower-risk flood zone where most lenders do not require flood insurance. More than simply a home, 1300 E Henry Avenue is your opportunity to enjoy the location, character, and community of Hampton Terrace at a price point that is becoming increasingly difficult to find.

1300 E Henry Avenue, Tampa
$559,999
3 Beds ⋅ 3 Baths ⋅ Seminole Heights North SubDv. ⋅ 33604 Zip Code
Price Improvement!!! Exquisitely remodeled property located in the desirable area of Tampa. Explore this 1,987 sq. ft. of updated living space. Amenities include primary suite with double walk-in closets, a spa-like bath with a freestanding soaking tub and to top it off, a walk-in shower. The remodeled kitchen offers modern finishes, an array of cabinetry, and new appliances for the chef in the family. Additional amenities, hardwood flooring, enhanced lighting, with a modern layout makes this home ideal for living and entertaining friends and family. Yard area fully fenced for privacy, with a large patio, gazebo, and ample parking for boats or other toys! Centrally located by dining, shopping, and major roadways, this is a turn-key and cozy move-in-ready home with blends of an historic charm, with modern day comforts for all to enjoy. Don’t let this one get away!

300 E Idlewild Avenue, Tampa
$369,900
3 Beds ⋅ 2 Baths ⋅ Acreage SubDv. ⋅ 33525 Zip Code
Step into the timeless charm of 13941 13th Street, Dade City, FL 33525, where historic character meets modern comfort. Built in 1930, this beautifully maintained two-story home offers 3 bedrooms, 2 bathrooms, and 1,688 square feet of inviting living space. One of the property's standout features is its oversized 0.27-acre lot—a rare find within Dade City's walkable historic district, where many homes sit on considerably smaller parcels. Enjoy the same charming downtown lifestyle that makes Meridian Avenue and Church Street so desirable, without paying the premium often associated with those signature addresses. Just a short walk or bike ride away, you'll find charming boutiques, local restaurants, coffee shops, parks, a playground with a splash pad, and beloved community events including the Kumquat Festival, Monarch Festival, Christmas Stroll, and more. Homes built in the 1930s are celebrated for their enduring craftsmanship, quality materials, thoughtful floor plans, and architectural character—features that are increasingly difficult to find in newer construction. This home beautifully preserves that timeless appeal while offering today's most desirable updates for comfortable, worry-free living. Inside, natural light fills the inviting living spaces, and the functional floor plan offers warmth, flexibility, and everyday comfort. Updated bathrooms and new kitchen appliances provide modern convenience while complementing the home's original charm. Additional upgrades include a tankless water heater for endless hot water and improved energy efficiency, along with a whole-home generator for added peace of mind during Florida's storm season, RO water system, a detached workshop/storage shed provides valuable flex space for hobbies, a workshop, additional storage, or even a future art studio or home office. The spacious backyard offers endless possibilities for entertaining, gardening, or simply relaxing outdoors. With NO HOA, this property offers the freedom and flexibility that's becoming increasingly difficult to find. Unlike many newer homes with smaller lots and HOA restrictions, this home combines generous outdoor space, historic character, and an unbeatable location. Enjoy convenient access to downtown Dade City's boutiques, restaurants, coffee shops, parks, festivals, the historic drive-in theater, the scenic Hardy Trail, schools, medical facilities, shopping, and major commuter routes—all just minutes from your doorstep. Whether you're searching for a home filled with character, a unique investment opportunity, or simply a place where historic charm and modern conveniences come together, 13941 13th Street offers a rare opportunity to own a piece of Dade City's history while enjoying the lifestyle today's buyers are seeking. Schedule your private showing and experience everything this exceptional property has to offer.

13941 13th Street, Dade City
$475,000
3 Beds ⋅ 2 Baths ⋅ Plant City Heights SubDv. ⋅ 33563 Zip Code
Welcome to this charming 1926 historic home located in the heart of Plant City's sought-after historic district. Offering 3 bedrooms, 2 bathrooms, and 1,781 square feet of living space, this home showcases beautiful original wood floors and a cozy living room with a wood-burning fireplace. The spacious dining room is perfect for gatherings, while the additional rear room provides flexibility as a home office, hobby space, or extra storage. Both bathrooms feature classic clawfoot tubs that complement the home's timeless character. Recent updates include fresh interior and exterior paint, a newer HVAC system, newer water heater, and new kitchen appliances including a refrigerator, range, and dishwasher. Outside, you'll find a detached two-car garage with an automatic door opener and a workshop area for projects and storage. Situated on an oversized 137' x 115' lot shaded by mature trees, this property offers plenty of outdoor space while remaining conveniently located near downtown Plant City. Easy access to Interstate 4 makes commuting to Tampa, Lakeland, and Orlando a breeze. Call today for your personal tour.

907 N Clark Street, Plant City
$699,999
3 Beds ⋅ 2 Baths ⋅ Allendale Terrace Blks A-B-1-2-3-4-5-6 SubDv. ⋅ 33704 Zip Code
Allendale Terrace's cutest house! This high & dry, block constructed bungalow features 2 large bedrooms & 1 bathroom along with an amazing kitchen remodel including ss appliances, refinished oak hardwood floors and a huge screened in porch for entertaining along with a climate controlled 8 x 10' detached office building and a big 12 x 16' storage shed. Home also has Gas appliances (clothes dryer, stove & tankless water heater) along with water softener and deep well & sprinkler system. Main house could be rented for $3200 per month). The In-Law unit includes 1 bedroom & 1 bathroom with kitchenette installed for short- or long-term rental ($1500 - 1800 per month income), or use as housing for an older child, or aging parent. This home sits on a huge 60' x 124' lot with a brick & tree lined street half a block from Allendale Terrace Park. Walking distance to Publix & Aldi's grocery stores, Crunch Fitness, Golden Isle brewery and many other restaurants and businesses nearby. Best neighborhood in Allendale Terrace! Home being sold "as is"

734 37th Avenue N, St Petersburg
$208,000
2 Beds ⋅ 1 Baths ⋅ City Zephyrhills SubDv. ⋅ 33542 Zip Code
Step back in time while embracing endless possibilities with this beautifully maintained historic home in the heart of Downtown Zephyrhills. Built in 1910 and designated as a protected historic property, this charming 2-bedroom, 1-bath residence offers a rare blend of historic character, modern updates, and mixed-use zoning that opens the door to a variety of residential and commercial opportunities. A welcoming screened front porch overlooks the tree-lined streets of downtown, creating the perfect place to enjoy your morning coffee or greet visitors. Inside, you'll find bright, inviting living spaces filled with natural light, original architectural charm, and thoughtful updates. The renovated kitchen features modern cabinetry, solid-surface countertops, stainless steel appliances, and ample storage while maintaining the home's timeless appeal. The home also features a water filtration/ softening system installed about 4 years ago. Situated on a spacious corner lot shaded by mature oak trees, the property includes a detached garage with laundry area, white picket fencing, and plenty of outdoor space. Whether you're looking for a unique primary residence, a live/work opportunity, professional office, boutique retail concept, small café, bed and breakfast, or another creative venture permitted by zoning, this property offers exceptional flexibility in one of Zephyrhills' most recognizable historic districts. Located within a minute of downtown shops, restaurants, community events, government offices, and local attractions, this is a rare opportunity to own a piece of Zephyrhills history while investing in its future. Historic properties with mixed-use zoning and this level of charm rarely become available. Schedule your private showing today and discover the possibilities waiting at this one-of-a-kind downtown gem.

5416 8th Street, Zephyrhills
$1,050,000
3 Beds ⋅ 1 Baths ⋅ St Petersburg Investment Co Sub SubDv. ⋅ 33713 Zip Code
This Historic Kenwood Urban Resort, one of Historic Kenwood's most remarkable lifestyle properties, is ready for it's next chapter. Just one block from vibrant Central Avenue and minutes from downtown St. Petersburg, this fully remodeled and turnkey furnished 1923 bungalow offers a rare combination of historic character, resort-style outdoor living, modern upgrades, and income-producing flexibility. Featured twice on Historic Kenwood's celebrated BungalowFest, this exceptional property blends the architectural charm of Old Florida with the conveniences today's buyers demand. The main residence has been thoughtfully updated with a designer kitchen, luxury flooring, custom window treatments, upgraded appliances, two new commercial-grade gas water heaters, and approximately $40,000 in impact glass windows, providing a significant benefit for coastal Florida living. Structural piers have also been reinforced with a hydraulic stabilization system for added confidence and long-term peace of mind. Beyond the front porch, the property unfolds into a private tropical retreat unlike nearly anything else in Historic Kenwood. The heated saltwater pool with bronze frog fountain serves as the centerpiece of an extraordinary outdoor environment surrounded by lush landscaping, artificial turf, expansive entertaining areas, gazebo seating, outdoor shower, irrigation well, and all-new fencing. Whether hosting friends beneath the pergola, relaxing poolside under the palms, or enjoying a quiet evening on the wraparound porch, every space has been designed to elevate daily living. Adding even more versatility is the licensed detached apartment above the garage. Ideal for rental income, guests, extended stays, a private office, creative studio, or multigenerational living, this valuable addition expands the possibilities far beyond those of a typical bungalow. The location is equally compelling. Enjoy exceptional walkability to Central Avenue's restaurants, cafés, galleries, boutiques, entertainment venues, parks, and public transit while being only minutes from downtown St. Petersburg, waterfront parks, museums, and award-winning cultural attractions. Offered turnkey furnished, this is a rare opportunity to acquire a fully curated property ready for immediate enjoyment as a primary residence, second home, seasonal retreat, or investment property. Seller will provide a one-year home warranty to the buyer for added peace of mind. Properties that combine historic charm, resort-style outdoor living, income potential, extensive upgrades, and a premier Historic Kenwood location rarely become available. More than a home, this is a private urban resort designed for those seeking something truly out of the ordinary.

127 23rd Street N, St Petersburg
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