Winter Haven / Cypress Gardens Homes with Shade Shutter(s) Exterior Features

Winter Haven / Cypress Gardens Homes with Shade Shutter(s) Exterior Features

Welcome to Winter Haven, Florida, a charming city nestled in the heart of Polk County, renowned for its picturesque lakes and vibrant community spirit. Known as the "Chain of Lakes City," Winter Haven boasts a stunning array of waterways, perfect for boating, fishing, and enjoying the tranquil Florida sunshine. Just a stone's throw away, the iconic Cypress Gardens, once a famous botanical garden and theme park, continues to inspire with its lush landscapes and rich history, making it a delightful spot for both residents and visitors alike.

In this idyllic setting, you’ll find homes that reflect the area's unique character, particularly those featuring shade shutters. These charming exterior features not only enhance the aesthetic appeal of your home but also provide a practical solution for Florida's warm climate. Shade shutters offer protection from the sun's intense rays, helping to keep your home cooler and more energy-efficient. They also add a touch of elegance, creating a timeless look that complements the natural beauty surrounding Winter Haven.

Living in Winter Haven means embracing a lifestyle filled with outdoor adventures, community events, and a close-knit atmosphere. Whether you're exploring the scenic walking trails, enjoying local festivals, or relaxing by the lakeside, there’s always something to love about this vibrant city. With homes equipped with shade shutters, you can enjoy the best of both worlds: a stylish residence that offers comfort and protection while allowing you to fully experience the enchanting charm of Winter Haven and Cypress Gardens. Come discover your dream home in this beautiful region today!

Newest Winter Haven / Cypress Gardens Homes with Shade Shutter(s) Exterior Features

6066 Se Southern Oaks Drive, Winter Haven
$126,900
2 Beds ⋅ 2 Baths ⋅ S5159435 MLS
Motivated Seller! Let's make a deal. Welcome to life at Garden Grove Oaks, a quiet 55+ community tucked away in the Southeast Winter Haven/Garden Grove area. Step inside this 2 bed/2 bath home to an open floor plan with a dining area conveniently to the right and the kitchen on your left, which includes a refrigerator, range, microwave, and dishwasher. Cathedral ceilings create an open, spacious feel, leading into the living room. The primary bedroom includes an en-suite bathroom with a step-in shower. Fans throughout the house help keep it cool. Two screened porches (front and side) give you options for enjoying the outdoors. Enjoy a morning coffee on the front screened porch which provides shade and a cool breeze and room for your favorite hobbies. The side porch behind the carport features tile flooring. Behind the side porch is an adjoining storage area with two work benches provides useful space for tools, projects, and hobbies. Laundry hookups are available in an interior closet and on the screened porch behind the carport. The washer and dryer do not convey. Enjoy the newer roof (2024), vinyl siding, a carport, and a long driveway, adding everyday convenience. Plenty of outdoor space with a nice sized backyard and the neighboring lot is vacant and owned by the next-door neighbor. Garden Grove Oaks low community fees offer a nice pool, shuffleboard next to the community lake, completing the setting for relaxed Florida living. Come see how this home fits your next chapter!

6066 Se Southern Oaks Drive, Winter Haven
464 Terranova Street, Winter Haven
$359,900
3 Beds ⋅ 2 Baths ⋅ TB8548427 MLS
Welcome home to this stunning 3-bedroom, 2-bathroom residence tucked into the sought-after, gated community of Terranova. From the moment you step inside, an open floor plan invites you through sun-filled living spaces accented by elegant crown moulding and custom built-ins. The chef-inspired kitchen anchors the home with generous counter space and a breakfast bar — perfect for casual mornings or entertaining guests. Plantation shutters throughout add a touch of timeless charm while offering privacy and light control in every room. Step outside to a spacious backyard, a blank canvas ready for weekend barbecues, a play area, or the pool of your dreams. Beyond your front door, Terranova's gated setting offers peace of mind just minutes from shopping, dining, and medical facilities — the perfect blend of tranquility and convenience. Don't miss this one — call today to schedule your private showing!

464 Terranova Street, Winter Haven
1380 S Lake Roy Drive, Winter Haven
$374,500
4 Beds ⋅ 3 Baths ⋅ L4962667 MLS
Virtually Staged. UPDATED POOL HOME WITH NEW BATHROOMS, NEW POOL DECK & BRAND-NEW WATER HEATER! Welcome to this spacious 4-bedroom, 3-bathroom, 2,955-square-foot pool home on a desirable corner lot in Winter Haven, ideally located across from beautiful lakefront homes and close to Winter Haven's renowned Chain of Lakes. Major recent improvements include a BRAND-NEW HOT WATER HEATER installed in October 2026, TWO NEWLY REMODELED BATHROOMS completed in 2025, and a RESURFACED POOL WITH NEW POOL DECK completed in 2022. The roof was also replaced in 2023, providing additional peace of mind for the next owner. Inside, the triple-split bedroom floor plan offers privacy and flexibility, making this home ideal for families, guests, or those who need dedicated spaces for work and hobbies. The oversized family room is designed for entertaining, featuring two sets of sliding glass doors that open directly to the screened and netted pool enclosure and covered patio. The seamless indoor-outdoor flow creates the perfect setting for gatherings, relaxing poolside, or enjoying Florida's year-round lifestyle. A spacious flex room with direct pool and patio access offers endless possibilities as a game room, home office, media room, hobby space, or additional entertainment area. The kitchen features custom-made cabinetry, granite countertops, a custom tile backsplash, and stainless-steel appliances, creating a functional and inviting space for everyday living and entertaining. The primary suite offers a private retreat with a bathroom featuring a garden tub, dual sinks, and a walk-in shower. The two recently remodeled bathrooms add fresh, updated appeal throughout the home. Additional highlights include a LARGE LAUNDRY ROOM with utility sink, drop-down ironing board, and extra shelving, as well as tile and wood flooring throughout the main living areas. Step outside to your own private backyard retreat. The resurfaced pool and NEW POOL DECK, completed in 2022, are surrounded by a screened and netted enclosure with a covered patio, creating an inviting space for swimming, dining, entertaining, and soaking up the Florida sunshine. A welcoming front screened porch, ample covered parking, and two detached storage sheds provide additional convenience and storage. The yard is irrigated by a well with a newer irrigation timer. The HVAC system is approximately 9 years old. While there are still opportunities for cosmetic updates in select areas, the home's generous size, desirable floor plan, significant recent improvements, and fantastic outdoor living spaces provide an excellent foundation for making it your own. Location adds even more appeal. The property is just a short walk to Freedom Boat Club, making it easy to access and explore Winter Haven's famous Chain of Lakes. LEGOLAND Florida is approximately one mile away, offering exceptional convenience for both residents and guests. With its four bedrooms, three bathrooms, private pool, newly remodeled bathrooms, resurfaced pool and new pool deck, new water heater, 2023 roof, flexible living spaces, and prime location near lakes and attractions, this is an exciting opportunity to own a spacious Winter Haven home and enjoy the best of the Florida lifestyle.

1380 S Lake Roy Drive, Winter Haven
6114 Grand Oaks Drive Se, Winter Haven
$159,900
2 Beds ⋅ 2 Baths ⋅ L4961323 MLS
Virtually Staged. YOU OWN THE LAND – NO LOT RENT! Welcome to 6114 Grand Oaks Dr SE, a well-maintained 2-bedroom, 2-bath home with 1,288 sq. ft. of living space in the Garden Grove Oaks 55+ active community of Winter Haven. With a pond view, oversized lot, low $65/month HOA, no CDD, and no land lease, this home offers an appealing combination of affordability, comfort, and Florida lifestyle. Step inside to an open, comfortable floor plan with plenty of natural light and a spacious living area. The updated kitchen features granite countertops, luxury vinyl flooring, generous cabinet and counter space, and a pantry designed for practical storage—the deep side of the pantry includes pull-out shelves, making it much easier to reach and organize items stored toward the back. The kitchen opens to the main living area, creating an easy flow for everyday living and entertaining. The primary bedroom is conveniently located on the main level and includes an en-suite bath with walk-in shower and walk-in closet. A second bedroom and full guest bath provide comfortable space for visitors, a home office, hobbies, or additional living needs. The guest bathroom includes space for the inside laundry. The home features ceiling fans, skylights, window treatments, and a combination of luxury vinyl and carpet flooring. Appliances are included, along with the washer and dryer, and the home is being offered partially furnished. Outside, enjoy the water and garden views, covered parking with room for two vehicles plus golf cart parking, and additional storage in the exterior shed. The paved driveway provides extra parking flexibility, while the outdoor living area gives you a place to relax and enjoy Florida's year-round climate. Garden Grove Oaks is an established 55+ community with a clubhouse, community pool and fishing opportunities, with ground and pool maintenance included among the association benefits. And unlike communities where homeowners pay hundreds of dollars each month in lot rent, you own the land here, helping keep ongoing expenses manageable. Conveniently located in Winter Haven, this home combines an updated interior, water view, covered parking, storage, community amenities and land ownership with a low monthly HOA—all at an attractive price point.

6114 Grand Oaks Drive Se, Winter Haven
6315 Grove Pointe Drive Se, Winter Haven
$158,000
2 Beds ⋅ 2 Baths ⋅ P4936981 MLS
READY FOR ITS NEXT OWNER! Welcome to 6315 Grove Pointe Drive SE, located in Garden Grove Oaks, a desirable 55+ community where YOU OWN YOUR LAND and enjoy LOW HOA fees. This well-maintained 2-bedroom, 2-bath home offers a spacious and comfortable floor plan filled with natural light. The open living and dining areas provide plenty of room for everyday living and entertaining, while the kitchen features updated appliances, generous cabinet and counter space, and a reverse osmosis water purification system. The spacious primary suite includes a walk-in closet and private bath with a garden tub and separate shower. Vinyl plank flooring throughout provides easy-care living, and electric drapes add an extra touch of convenience. Several important improvements have already been taken care of, including a membrane roof installed in 2021 and inspected in October 2025. The seller has also completed lender-requested repairs from a previous transaction, making this home ready for its next buyer. Enjoy the relaxed Florida lifestyle in Garden Grove Oaks, a friendly, well-maintained community conveniently located near shopping, restaurants, medical facilities and Winter Haven's beautiful Chain of Lakes. With land ownership, low HOA fees, a spacious floor plan and important improvements already completed, this home offers plenty to appreciate. Schedule your private showing.

6315 Grove Pointe Drive Se, Winter Haven
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