Winter Haven Homes with Florida Architectural style

Winter Haven Homes with Florida Architectural style

Welcome to Winter Haven, a charming city located in Polk County, Florida. Known for its beautiful lakes and warm climate, Winter Haven is a popular destination for those seeking a relaxed lifestyle with a touch of Southern charm.

One of the unique features of Winter Haven is its abundance of homes with true Florida architectural style. These homes often feature key elements such as stucco exteriors, tile roofs, and spacious lanais perfect for enjoying the sunny weather. The design of these homes is inspired by the local environment, with an emphasis on bright and airy spaces that seamlessly blend indoor and outdoor living.

Whether you're looking for a cozy bungalow or a spacious estate, Winter Haven offers a variety of homes that showcase the best of Florida architecture. Imagine waking up to the sun streaming through your windows and enjoying a cup of coffee on your private patio as you take in the peaceful surroundings.

If you're ready to make Winter Haven your home, let us help you find the perfect property that embodies the true essence of Florida living. Contact us today to start your search for a home that not only meets your needs but also captures the unique spirit of Winter Haven.

Newest Winter Haven Homes with Florida Architectural style

3 Beds ⋅ 4 Baths ⋅ Lake Winterset Acres SubDv. ⋅ 33884 Zip Code

This home extrudes the luxury vibe from the moment you approach it with its distinctive roof w/ a blue metal barrel tile appearance and circular driveway. Large manicured 1+ acre lot and oak trees. No HOA and is located behind Legoland. Overlooking Lake Winterset on the famous Winter Haven Chain of Lakes. Lots of room to spread out in over 3000 sq ft of a/c living space. The split floor plan has 3 bedroom and 3 1/2 baths. A large corner gas stone custom fireplace is the living area focal point. A front door 2-car carport covers your guests as they enter through the double doors into the formal foyer. A dedicated built-out office is just inside. A triple sliding glass door opens to the 30' wide covered lanai and to the back yard. Plenty of room for a pool. Full irrigation with a dedicated well. Large 37x11 studio provides extra air conditioned flex space. Additional bonus is the oversized 2-car garage AND a 12' tall 11'x37' RV/boat garage and both are air conditioned and with a polyaspartic floor coating. Separate attached outside storage room for lawn equipment.

2241 Winterset Road, Winter Haven

4 Beds ⋅ 3 Baths ⋅ Magnolia Shores SubDv. ⋅ 33881 Zip Code

Welcome to your own private lakefront retreat on 1.23 acres along Lake Hamilton with NO HOA! This stunning 4-bedroom, 3-bath home offers an exceptional combination of luxury, entertaining space, and the ultimate Florida waterfront lifestyle. Bring your boat and jet skis and enjoy the convenience of a private dock featuring an electric covered boat lift and built-in fishing bench. The outdoor living space is truly spectacular! Step through the French doors to a sparkling saltwater PebbleTec pool featuring iridescent tile, fiber-optic lighting, a swim-up bar, fountains, and a roof-line waterfall. The propane-heated pool is surrounded by an expansive travertine deck, while the nearby gas fire pit with custom-cushioned seating creates the perfect setting for evening gatherings. Propane-connected tiki torches add a tropical ambiance, and a hidden sump pump provides worry-free drainage after storms. Entertaining is effortless with the outdoor kitchen, complete with a new grill and refrigerated drawers. The fenced backyard extends halfway to the lake, providing plenty of room for pets to play. Professional Florida-native landscaping, enhances the lush, resort-like setting. Inside, the beautifully designed chef's kitchen features quartz countertops, a copper farmhouse sink, paneled refrigerator, trash compactor, and spacious butler's pantry with a full-size refrigerator and abundant storage. The open floor plan includes a dedicated buffet area with dual wine refrigerators adjacent to the dining space—perfect for hosting family and friends. Nine-foot ceilings, crown molding, porcelain tile, shiplap accents, custom lighting, and a central vacuum system add comfort and sophistication throughout. The luxurious primary suite offers direct access to the pool deck, with a convenient open-air shower just outside. The ensuite features dual vanities and a walk-in shower with dual shower heads. The expansive walk-in closet includes a center island, custom shelving, heated towel rack, and an extra-large Liberty Safe. The home underwent a complete rebuild in 2017, so all features are 2017 or newer. Recent improvements include a new roof (2025), new pool pump (2025), a new 12x24 storage shed (2025) and new irrigation system (2025). The irrigation water comes from the lake so it doesn’t affect your water bill. Additional features include a split-bedroom floor plan, with two guest bedrooms sharing a Jack-and-Jill bath; hurricane shutters; a whole-home Generac generator; and TVs in every room, including the back porch. The spacious 3-car garage features tiled flooring, storage, a workshop, and an industrial ice maker. A pavered circular driveway provides ample parking, plus an additional parking pad with room for an RV. From the custom interior and exterior lighting to the custom painting, bamboo chair rail, and travertine exterior accents, every detail has been thoughtfully designed. The home is also pre-wired for ADT security at the front and rear doors and garage service door. Boating, fishing, entertaining, relaxing, and resort-style living—all in one exceptional Lake Hamilton property with no HOA!

3640 Crump Road, Winter Haven

4 Beds ⋅ 3 Baths ⋅ Windridge SubDv. ⋅ 33881 Zip Code

Spacious 4BR/2.5BA home with 2,836 SF in desirable Windridge! Enjoy a screened saltwater pool, spacious fenced backyard, flexible living areas, and parking for up to 8 vehicles (2-car garage + oversized driveway). Major updates include a 2023 roof and 2022 A/C. Low HOA, no CDD, and convenient access to shopping, dining, schools, and major roads. Quick closing available and priced to sell. Act fast; schedule your private showing today!

5888 Windridge Drive, Winter Haven

4 Beds ⋅ 2 Baths ⋅ Lake Smart Estates SubDv. ⋅ 33881 Zip Code

3D tour available! Welcome to this spacious 4-bedroom, 2-bath single-family home in the Lake Smart Estates community of Winter Haven. With an open-concept layout and 1,842 square feet of living space, the home offers plenty of room for everyday living and entertaining. Major updates provide added peace of mind, including a new roof in 2026, new A/C in 2024, and brand-new appliances in 2026. The kitchen offers generous cabinet and counter space and opens directly to the main living and dining areas. The primary suite features a walk-in closet and private bathroom with dual sinks and a spacious shower. An interior laundry room and attached two-car garage add everyday convenience. One of the property's biggest highlights is the oversized lot, one of the largest in the community. The expansive backyard provides exceptional outdoor space with plenty of possibilities for entertaining, play areas, gardening, or creating your own Florida outdoor retreat. Lake Smart Estates offers community amenities including a swimming pool, dock, gazebo, and water access. Golf enthusiasts will appreciate having Willowbrook Golf Course just minutes away, a public 18-hole course offering a driving range, putting green, chipping areas, and practice facilities. Conveniently located near US-17, the home provides easy access to Downtown Winter Haven, shopping, restaurants, schools, Polk State College, and everyday services. With four bedrooms, significant recent upgrades, an oversized yard, community amenities, and golf nearby, this move-in-ready home offers an excellent combination of indoor and outdoor space in a convenient Winter Haven location.

3695 Julius Estates Boulevard, Winter Haven

3 Beds ⋅ 2 Baths ⋅ Saxon Myers Rep Ph 2 SubDv. ⋅ 33881 Zip Code

Affordable pool home with NO HOA in the heart of Winter Haven! Welcome to 133 Rebecca Drive NE, a move-in-ready 3 bedroom, 2 bath home offering a private screened saltwater pool, important updates, comfortable living spaces, and an impressive combination of features and value. If you've been searching for an affordable Central Florida home where you can enjoy the Florida pool lifestyle right in your own backyard, this one deserves a closer look. Inside, the spacious main living area features attractive porcelain tile flooring, a vaulted ceiling, and a gas fireplace, creating a comfortable gathering space for everyday living and entertaining. The adjoining dining area provides direct access to the pool and outdoor living area, while the kitchen features clean white cabinetry, beautiful granite countertops, plenty of storage, and a full suite of included appliances. The desirable split-bedroom layout includes two comfortably sized guest bedrooms and a spacious primary suite with an en-suite bath and generously sized walk-in closet. Both bathrooms have been updated, including a beautifully renovated primary bath with a custom walk-in shower. Step outside and imagine weekends filled with pool time, grilling on the back deck, entertaining friends and family, and enjoying the Florida sunshine. The large screened outdoor living area features a private saltwater pool, plenty of deck space for lounging, dining, and grilling, plus a covered area where you can relax in the shade. Start the morning with coffee by the pool, spend a sunny afternoon in the water, then fire up the grill for dinner and enjoy a warm Florida evening at home. This is the kind of outdoor space that makes it easy to enjoy everything the Florida lifestyle is all about. Beyond the pool enclosure, the fully fenced backyard provides additional usable yard space with plenty of potential for landscaping, a vegetable garden, or your own collection of Florida fruit trees. An included storage shed provides convenient space for lawn and gardening equipment while keeping the two-car garage free for vehicles and additional storage. Major improvements include a NEW A/C system in 2025, all new double-pane windows and sliding glass door in 2021, a 2017 roof, newer front door, rain gutters and low utility bills. Best of all, there is NO HOA! Located in the heart of Winter Haven, you're convenient to downtown Winter Haven, Polk State College, shopping, dining, medical facilities, and recreation. Winter Haven's central location between Tampa and Orlando also puts theme parks, international airports, beaches, professional sports, and some of Central Florida's best entertainment within reach.

133 Rebecca Drive Ne, Winter Haven

4 Beds ⋅ 3 Baths ⋅ Willowbrook North SubDv. ⋅ 33881 Zip Code

Under Construction. Ready in October 2026! CASTAWAY MULTI-GEN: Beautiful 1 Level, 2 Car Garage Home with Open Concept Living and 3 Bedrooms! Featuring a Private Retreat: these thoughtfully designed homes provide flexibility without added monthly costs. Designed for flexibility, the Castaway Retreat offers the ideal solution without added monthly costs. This thoughtfully designed multi-gen layout includes a private retreat with its own kitchenette, living area, bedroom, and full bath, plus both interior access to the main home and a private exterior entrance. An optional washer/dryer hookup adds even more convenience.

819 Andrew Street, Winter Haven

3 Beds ⋅ 2 Baths ⋅ Eagle Crest SubDv. ⋅ 33881 Zip Code

Welcome to this beautiful 1-owner home at Eagle Crest. Currently the only home for sale in the entire neighborhood. Pride of ownership is apparent and the neighborhood is very well maintained. Wake up in the morning and enjoy your coffee on the covered lanai which overlooks a lush green field of undeveloped acreage behind. This home sits on a premium oversize lot w/ over a quarter of an acre and no rear neighbors. Large luxury primary bathroom and his & hers walk-in closets and large doorless shower w/ 2 heads. Breakfast nook in the home that is 7 x 11 and a formal dining room too. Den or office off of the foyer as you enter the home. Natural gas range for the chef in you. Regular scheduled maintenance has been done on this home with the A/C serviced every 6 months & the garage door opener every year, and it possesses an on-demand natural gas hot water heater. Currently it is the only property up for sale in this desired community. Make an appointment to see this immaculate home and make it yours!

1514 Hamlin Street, Winter Haven

3 Beds ⋅ 2 Baths ⋅ Audubon Place Sub SubDv. ⋅ 33884 Zip Code

Welcome to this beautifully maintained 3-bedroom, 2-bathroom home tucked away on a quiet cul-de-sac in the desirable Audubon Place community of Southeast Winter Haven. Offering exceptional curb appeal with fresh interior and exterior paint, this move-in-ready residence showcases quality craftsmanship and extensive updates, including a NEW ROOF (2023), a BRAND-NEW HVAC system with ALL NEW DUCTWORK (2025), and a REME HALO whole-home air purification system (2025) for enhanced indoor air quality and year-round comfort. Inside, you'll be welcomed by soaring 12-foot ceilings, elegant rounded corner walls, extensive crown molding, detailed architectural arches, and an open-concept floor plan designed to maximize space and natural light. Tray ceilings enhance every bedroom, adding an extra touch of sophistication throughout the home. The chef-inspired kitchen is beautifully appointed with granite countertops, stainless steel appliances, crisp white cabinetry, under-cabinet lighting, and a large walk-in pantry offering abundant storage. The adjoining living area features rich flooring, a tray ceiling, a built-in media alcove, and expansive windows that create a warm and inviting atmosphere. The private primary suite serves as a relaxing retreat with a tray ceiling, spacious walk-in closet, and a luxurious ensuite bathroom featuring granite countertops, a dual-sink vanity, a dedicated makeup station, a soaking tub, and a separate walk-in shower. The additional bedrooms are generously sized, while the oversized laundry room offers exceptional functionality with built-in cabinetry, a utility sink, and included Maytag commercial washer and dryer. Step outside to your own private backyard oasis featuring a beautiful paver lanai, matching paver walkway and 2 car garage with paver driveway and an expansive screened outdoor living space complete with ceiling fans and an included hot tub. The fully fenced backyard is surrounded by mature landscaping, providing the perfect setting for entertaining, relaxing, or enjoying Florida's year-round sunshine. For added value, the drapes and area rugs throughout the home will remain, making your move even easier. Located in a well-maintained community with a low HOA of just $38 per month, residents enjoy peaceful streets, attractive deed restrictions, and a prime location just minutes from shopping, restaurants, the Audubon Sanctuary with scenic walking trails, Garden Grove Elementary School, the Audubon Nature Trail, LEGOLAND Florida Resort, Peppa Pig Theme Park, Downtown Winter Haven, Winter Haven Hospital, and the area's renowned Chain of Lakes. With convenient access to Highway 27 and the Polk Parkway, commuting to both Orlando and Tampa is simple. Beautifully updated, thoughtfully maintained, and truly move-in ready, this exceptional home offers timeless style, modern comfort, and quality upgrades throughout.

1015 Robin Lane, Winter Haven

2 Beds ⋅ 1 Baths ⋅ Inwood SubDv. ⋅ 33881 Zip Code

Investor special in the heart of the Inwood neighborhood — solid block construction, new roof (2024), and a location that puts you minutes from everything Winter Haven has to give. This two-bedroom (possibly could be a 3 bedroom), one-bath home sits on a fenced lot with mature shade trees, and the covered, screened front porch gives the place a real homey feel the moment you pull up. Inside you'll find ceramic tile throughout the bedrooms and living areas, ceiling fans in every room, and a converted single-car garage that works well as an additional bedroom or possibly a den, home office, or storage space. The layout is straightforward and functional — living room, eat-in kitchen, two bedrooms with built-in closets, and a full bath with pedestal sink and tiled shower. There's also a linen closet in the hall. A shed out back adds extra storage. And the size of the backyard allows for endless possibilities. The home currently has window AC units but no central air or heat system — a definite opportunity for a buyer to update to their preference and immediately add equity. Dual septic system on site. Water is public. The property is being sold as-is. Convenient to US-17, shopping, dining, Polk State College, the Chain of Lakes trail system, and downtown Winter Haven. No HOA. Great bones, priced to move.

3319 Avenue U Nw, Winter Haven

4 Beds ⋅ 2 Baths ⋅ Berryhill SubDv. ⋅ 33884 Zip Code

Short Sale. Located in Winter Haven, this 4-bedroom, 2-bath home offers approximately 2,460 square feet of living space with a two-car garage, spacious layout, and private pool. The home's generous floor plan provides multiple living areas and ample space for everyday living, entertaining, or accommodating a variety of household needs. Based on available information and photographs, the property appears to be in generally good cosmetic condition. The home offers an opportunity for buyers seeking a larger residence with a functional layout and desirable outdoor living features. The property includes a screened lanai and pool area; however, buyers are encouraged to independently verify the condition and functionality of the pool and all related equipment. Conveniently located near shopping, dining, schools, and other area amenities, this property combines size, location, and potential in today's market. Buyers are encouraged to conduct thorough inspections and verify the condition and functionality of all systems, components, and improvements. Buyers should verify all information. Agents: Please review all private remarks prior to scheduling a s

302 Sterling Drive, Winter Haven

3 Beds ⋅ 2 Baths ⋅ Villamar SubDv. ⋅ 33884 Zip Code

Under Construction. Brand new, energy-efficient home available by Jul 2026! Configure the flex room in the front of the home to an at home office space or hobby space. Past the foyer, the open kitchen flows to the dining space, great room and outside patio. Private primary suite offers a spacious area to relax. Visit Villamar and explore new single-family homes for sale in Winter Haven, FL. Residents will have access to two resort-style amenity centers featuring a clubhouse, pool, and playground. Winter Haven is known for its beautiful chain of lakes with lakeside restaurants and its award-winning community theater. Nearby attractions include Legoland Florida and Peppa Pig Theme Park. A brand-new model and new phase are coming soon. Each of our homes is built with innovative, energy-efficient features designed to help you enjoy more savings, better health, real comfort and peace of mind.

3932 Giorgio Drive, Winter Haven

4 Beds ⋅ 3 Baths ⋅ Villamar Ph 2 SubDv. ⋅ 33884 Zip Code

Welcome home to this beautifully maintained 4-bedroom, 3-bathroom home in the desirable Villa Mar community of Winter Haven! Built just 5 years ago, this spacious home offers nearly 2,000 square feet of thoughtfully designed living space and features fresh interior paint, brand-new carpet in all bedrooms, and a fully equipped kitchen with all appliances included, including the washer and dryer. Enjoy peace of mind with a regularly maintained HVAC system, alarm system, and full irrigation system. The oversized fully fenced backyard is larger than many comparable homes in the community and features gates on both sides, providing plenty of room for pets, play, entertaining, or even a future pool. One of the standout features of this home is the solar system, which will be paid off with a full-price offer, allowing the new owner to enjoy significantly reduced utility costs, with the previous owner averaging approximately $80 per month in electric bills. The newer construction may also offer savings on homeowner's insurance compared to older homes. Villa Mar residents enjoy access to a beautiful resort-style pool, playground, and convenient proximity to shopping, dining, schools, and major roadways. This move-in ready home combines comfort, efficiency, and value in one exceptional package. **Owner is Licensed Realtor**

1355 Benevento Drive, Winter Haven

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