Winter Haven / Cypress Gardens Homes under $500,000

Winter Haven / Cypress Gardens Homes under $500,000

Welcome to Winter Haven, Florida, a vibrant city nestled in the heart of Polk County, known for its picturesque lakes and rich history. Often referred to as the "Chain of Lakes," Winter Haven boasts more than 50 sparkling lakes, making it a paradise for boating, fishing, and outdoor enthusiasts. This charming city is not only famous for its natural beauty but also for its family-friendly atmosphere and a warm community spirit.

Cypress Gardens, a historic gem located within Winter Haven, enchants visitors with its lush gardens and thrilling water ski shows. This area is a delightful blend of nostalgia and modern attractions, providing residents with a unique lifestyle that celebrates both leisure and adventure. With year-round sunshine and a plethora of recreational activities, Winter Haven is an ideal place for families, retirees, and young professionals alike.

For those seeking affordable housing options, Winter Haven offers a variety of charming homes under $500,000. Whether you’re looking for a cozy single-family home, a modern townhouse, or a delightful waterfront property, you’ll find an array of choices that cater to diverse tastes and lifestyles. Many of these homes feature spacious yards, updated interiors, and proximity to schools, parks, and shopping centers, making it easy to enjoy everything this beautiful city has to offer.

Discover the perfect blend of affordability and quality living in Winter Haven. With its welcoming community, abundant outdoor activities, and homes that fit your budget, this is the place where you can truly thrive. Come and experience the magic of Winter Haven today!

Newest Winter Haven / Cypress Gardens Homes under $500,000

no property photo
$259,000
3 Beds ⋅ 2 Baths ⋅ TB8557853 MLS ⋅ Meritage Homes BLDG.
Brand new, energy-efficient home available by Dec 2026! Open floor plan with a lot of flexibility. Retreat to your primary suite that is conveniently situated in the back of the home for plenty of privacy and offers a huge walk-in closet and bathroom with dual sink vanity and standalone shower. 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.

3988 Giorgio Drive, Winter Haven
525 Vittorio Drive, Winter Haven
$316,900
4 Beds ⋅ 2 Baths ⋅ L4965984 MLS
New construction home with 2005 square feet on one-story including 3 bedrooms plus a den, 2 baths, and an open living area. Enjoy an open kitchen with Silestone countertops, Samsung stainless steel appliances, a walk-in pantry, and a spacious island, fully open to the dining café and gathering room. The living area, laundry room, and baths include luxury wood vinyl plank flooring, with stain-resistant carpet in the bedrooms. Your owner's suite is complete with a walk-in wardrobe and a private en-suite bath with dual vanities, a tiled shower, and a closeted toilet. Plus, enjoy a covered lanai, 2-car garage, custom-fit window blinds, architectural shingles, energy-efficient insulation and windows, and a full builder warranty. ***Please note - Virtual Tour showcases the home layout; colors and design options in actual home for sale may differ. Furnishings and décor do not convey!

525 Vittorio Drive, Winter Haven
100 El Camino Drive Unit 208, Winter Haven
$139,900
1 Beds ⋅ 1 Baths ⋅ O6451540 MLS ⋅ 100 BLDG.
OWNER MOTIVATED Beautiful Condo, Tastefully remodeled, completely updated in 2023. All new appliances, granite counter tops, remote controlled fans, Kitchen and bathroom new cabinets. Come enjoy Florida Living or just retire in style or enjoy it as your Winter Getaway. A small Bonus space may be used as a second sleeping quarters for additional guests. Conveniently located near shopping centers, restaurants, hospitals, churches and more. HOA fees cover your cable, internet, water, sewer, trash pick up and natural gas. Exclusive Carport. Seller will assist you with closing costs or interest rate buy down if needed.

100 El Camino Drive Unit 208, Winter Haven
517 Vittorio Drive, Winter Haven
$289,900
3 Beds ⋅ 3 Baths ⋅ L4965970 MLS
New construction home with 1568 square feet on two-story including 3 bedrooms with loft, 2.5 baths, and an open living area. Enjoy an open kitchen, Silestone countertops, Samsung stainless steel appliances, a walk-in pantry, and a spacious island, fully open to the dining café and gathering room. The living area, laundry room, and baths include luxury wood vinyl plank flooring, with stain-resistant carpet in the bedrooms. Your owner's suite is complete with a walk-in wardrobe and a private en-suite bath with dual vanities, and a tiled shower. Bedrooms 2 and 3 share a bathroom. Plus, 2-car garage, custom-fit window blinds, architectural shingles, energy-efficient insulation and windows, and a full builder warranty. “Please note, virtual tour/photos showcases the home layout; colors and design options in actual home for sale may differ. Furnishings and décor do not

517 Vittorio Drive, Winter Haven
4490 Rapallo Avenue, Winter Haven
$259,900
3 Beds ⋅ 2 Baths ⋅ L4965968 MLS
New construction home with 1358 square feet on one-story including 3 bedrooms, 2 baths, and an open living area. Enjoy an open kitchen with Quartz countertops, Samsung stainless steel appliances, pantry, and a raised bar, fully open to the gathering room. The living area, laundry room, and baths include luxury wood vinyl plank flooring, with stain-resistant carpet in the bedrooms. Your owner's suite is complete with a private en-suite bath, a tiled shower. Plus, enjoy a covered lanai, 1-car garage, custom-fit window blinds, architectural shingles, energy-efficient insulation and windows, and a full builder warranty. Please note, virtual tour/photos showcases the home layout; colors and design options in actual home for sale may differ. Furnishings and decor do not convey."

4490 Rapallo Avenue, Winter Haven
3947 Cypress Landing W, Winter Haven
$309,000
3 Beds ⋅ 2 Baths ⋅ TB8559476 MLS
BEAUTIFUL 3-BEDROOM, 2-BATH HOME IN CYPRESS LANDING ON LAKE DEXTER! Welcome to this beautifully maintained 3-bedroom, 2-bathroom home with a 2-car garage, located in the desirable Cypress Landing community on Lake Dexter in Winter Haven! Featuring extensive recent updates, spacious living areas, and fantastic community amenities, this home offers the perfect blend of comfort, convenience, and Florida living. Extensive Recent Updates! Major improvements include a new roof and updated in 2022, along with numerous renovations completed this year. Updates include a renovated kitchen with new countertops, new bathroom vanities, updated flooring, new lighting and fans, plumbing fixtures, fresh paint and texture, new interior doors, updated trim, new electrical improvements and pluming, and new appliances, including a range, microwave, and dishwasher. A new DECA drainage system was also recently installed in the rear of the home. Upon entering, you are welcomed by an extended foyer that opens into a spacious living area. The generously sized primary suite offers sliding glass doors leading to the lanai, along with an attached primary bathroom featuring a walk-in shower and walk-in closet. Additional highlights include an impressive 26' x 11' sunroom overlooking the backyard—an ideal space for relaxing, entertaining, or enjoying your morning coffee. Enjoy the Cypress Landing Lifestyle! Community amenities include pickleball and tennis courts, a heated swimming pool, a clubhouse, a private boat ramp with water access, and a variety of social clubs and activities for residents to enjoy. Conveniently situated in the heart of Winter Haven, this home offers easy access to shopping, restaurants, entertainment, and local social events, with convenient commutes to Lakeland, Orlando, and Kissimmee. With its extensive updates, spacious floor plan, inviting living spaces, and desirable lake community amenities, this home is a wonderful opportunity to enjoy the best of Winter Haven living!

3947 Cypress Landing W, Winter Haven
593 Terranova Circle, Winter Haven
$359,000
3 Beds ⋅ 2 Baths ⋅ O6450720 MLS
Welcome to this beautifully maintained 3-bedroom, 2-bath home in the desirable gated community of Terranova! Featuring an open floor plan, vaulted ceilings, and a private screened and heated pool, this home offers comfortable Florida living. Enjoy attractive landscaping with Naval orange and Clementine trees, a screened front porch, energy-efficient Pella windows, and a spacious living room with built-in shelving. The kitchen features ample counter space, appliances, and a breakfast bar overlooking the living area. A separate breakfast nook offers flexible space for dining or a home office. The split-bedroom floor plan provides privacy, with two guest bedrooms and a full bath on one side and a spacious primary suite on the other. The primary suite features dual vanities, a garden tub, a separate shower, and a walk-in closet with custom shelving. The fully fenced backyard features an enclosed lanai, heated screened pool, spacious pool deck, and storage shed. Recent updates include a 2017 roof, upgraded A/C (2014), replaced flooring, upgraded front door, French doors, new garage door opener, and brand-new pool screens. Additional features include a 2-car garage, washer and dryer, and select furnishings, including Sleep Number beds, recliners, and outdoor furniture. Meticulously maintained and ready to enjoy, this Terranova home is a must-see!

593 Terranova Circle, Winter Haven
221 Mandolin Drive, Winter Haven
$330,000
4 Beds ⋅ 2 Baths ⋅ L4965776 MLS
LIKE NEW!!! Don't miss this 4 bedroom, 2 bath home centrally located in Winter Haven, FL in the GATED COMMUNITY OF MANDOLIN. So many NOTABLE UPDATES in 2026 including: NEW ROOF (TAMKO TITAN SHINGLES), NEW LEVEL 3 GRANITE IN KITCHEN AND BOTH BATHROOMS, NEW SINKS, NEW KOHLER TOILETS, NEW FIXTURES, NEW INTERIOR PAINT, NEW FANS, NEWLY FINISHED GARAGE FLOOR, AND NEWLY LANDSCAPED LAWN! This OPEN CONCEPT, SPLIT PLAN is light and bright and very inviting. The OVERSIZED LOT gives you plenty of room with a length of (125 ft deep and 92 feet in width). This neighborhood is COMPLETELY BUILT OUT and VERY ESTABLISHED. The kitchen features STAINLESS APPLIANCES and is perfect for entertaining guests with it's central location. The back area is COMPLETELY PRIVATE with vinyl fencing for all your friends/family gatherings. Shopping, medical, restaurants, and LEGOLAND, FL are within minutes of this centrally located home with so many updates!!!

221 Mandolin Drive, Winter Haven
241 Volusia Drive, Winter Haven
$339,900
3 Beds ⋅ 2 Baths ⋅ L4965656 MLS
Timeless charm, exceptional living space and an established SE Winter Haven location! Welcome to 241 Volusia Drive, a beautifully maintained, one-owner, 3 bedroom, 2 bath residence offering 2,273 square feet of living area. From its undeniable curb appeal and mature landscaping to its classic traditional architecture, this home makes a wonderful first impression, with the added freedom of no HOA. Providing valuable peace of mind are several significant improvements, including a remodeled guest bath (2024), 5-ton A/C (2022), new roof (2019), tankless water heater (2017), remodeled kitchen, private 4" irrigation deep well for added efficiency. Beyond these thoughtful improvements, the inviting layout is equally impressive. The home opens to an expansive interior with room to comfortably accommodate both everyday living and entertaining. Just off the welcoming front entry, formal living and dining rooms provide inviting settings for holiday celebrations and memorable gatherings with family and friends. A spacious 16' x 27' family room features tile flooring, wraparound sliding windows and an abundance of natural light. With plenty of room for multiple seating arrangements, weekend sports or relaxing evenings, this is truly a space designed to be enjoyed. Convenient access to the backyard allows for an effortless transition between indoor and outdoor enjoyment. The beautifully updated kitchen features custom cabinetry with a rich wood finish, granite counters, a breakfast bar, double ovens, a flat-top range and pull-out cabinet drawers. A pantry offers additional storage, while the eat-in dinette provides a comfortable setting for casual dining. Designed with privacy in mind, the primary suite is thoughtfully separated from the guest bedrooms and features a generously sized walk-in closet and an ensuite bathroom with dual sinks and a tiled walk-in shower. Both guest bedrooms are comfortably sized with ample closet space and convenient access to the beautifully remodeled guest bathroom, updated with attractive tile finishes, a stunning vanity with a quartz counter, updated fixtures, new lighting and mirror. An interior laundry room with built-in ironing board, cabinetry and a utility sink adds everyday convenience. The oversized, side entry two car garage is another standout feature, offering abundant space for vehicles, hobbies and storage, along with built-in cabinetry and attic access. Step outside to discover a lush, fully fenced backyard framed by mature landscaping and majestic Oak trees. The fully fenced backyard offers plenty of room for family, pets and outdoor activities. A concrete patio is the perfect place for grilling or simply enjoying the peaceful surroundings. Additional highlights include double paned windows, crown molding, rain gutters and more. The location is equally appealing! Situated in an established neighborhood, this home enjoys the charm of a traditional Florida community, where mature trees nd spacious yards create a welcoming atmosphere reminiscent of years gone by. Enjoy convenient access to shopping, dining, medical facilities, schools, lakes and recreational opportunities that make Winter Haven such a wonderful place to call home. Lovingly maintained by its original owner, thoughtfully updated and ideally located, 241 Volusia Drive offers the kind of timeless appeal, comfortable living and neighborhood charm that never goes out of style. Schedule your private showing today.

241 Volusia Drive, Winter Haven
2470 Salzburg Loop, Winter Haven
$270,000
3 Beds ⋅ 2 Baths ⋅ O6450814 MLS
Virtually Staged. This property is located in one of the best neighborhoods in Winter haven. A new roof will be installed soon.

2470 Salzburg Loop, Winter Haven
260 Greenfield Road, Winter Haven
$349,900
3 Beds ⋅ 2 Baths ⋅ P4940214 MLS
Tucked away on the golf course in the highly sought after Cypresswood Golf and Country Club community of SE Winter Haven with serene pond views and lush natural foliage for privacy, this beautifully maintained single-family pool home offers the perfect blend of comfort, elegance, and resort-style living. A circular drive sets the tone as you arrive, leading into a thoughtfully designed split-bedroom floorplan ideal for both everyday living and hosting guests. The heart of the home features solid wood cabinetry and rich granite surfaces in the kitchen and baths, combining timeless style with durability. The primary suite is a true retreat, complete with an en suite bathroom and a spacious walk-in closet. Guests will appreciate the dedicated pool/guest bathroom, perfectly positioned for indoor-outdoor living. Step outside to the screen-enclosed private POOL deck and take in tranquil views of the golf course and pond—your own private oasis framed by mature landscaping. Whether enjoying a quiet morning coffee or entertaining at sunset, this outdoor space delivers year-round enjoyment. Located within a gated community with 24-hour guard service, residents enjoy access to an impressive array of amenities, including a community pool, tennis, pickleball and basketball courts, a clubhouse with restaurant, pro shop, and a fully equipped fitness center. This is more than a home—it’s a lifestyle.Tucked away on the golf course with serene pond views and lush natural foliage for privacy, this beautifully maintained single-family home offers the perfect blend of comfort, elegance, and resort-style living. A circular drive sets the tone as you arrive, leading into a thoughtfully designed split-bedroom floorplan ideal for both everyday living and hosting guests. The heart of the home features solid wood cabinetry and rich granite surfaces in the kitchen and baths, combining timeless style with durability. The primary suite is a true retreat, complete with an en suite bathroom and a spacious walk-in closet. Guests will appreciate the dedicated pool/guest bathroom, perfectly positioned for indoor-outdoor living. Step outside to the screen-enclosed pool deck and take in tranquil views of the golf course and pond—your own private oasis framed by mature landscaping. Whether enjoying a quiet morning coffee or entertaining at sunset, this outdoor space delivers year-round enjoyment. Located within a gated community with 24-hour guard service, residents enjoy access to an impressive array of amenities, including a community pool, tennis, pickleball and basketball courts, a clubhouse with restaurant, pro shop, and a fully equipped fitness center. This is more than a home—it’s a lifestyle. Whether you’re raising a family, welcoming visiting guests, or enjoying a seasonal escape, this home offers the space, setting, and lifestyle to fit every chapter. The Cypresswood community is minutes from Highway 27 and the I-4 corridor, Winter Haven's very own Legoland Florida Resort, the Polk Parkway, and in the center of a thriving community with many convenient grocery, restaurant, shopping, and commuting options for travel in less than an hour from Disney World and other Orlando attractions, the Orlando International Airport, and the gulf-side beaches of Tampa/St. Pete! Schedule your private showing today, and don't miss the opportunity to make this incredible home yours.

260 Greenfield Road, Winter Haven
100 El Camino Drive Unit 103, Winter Haven
$59,000
1 Beds ⋅ 1 Baths ⋅ L4965857 MLS ⋅ 1 BLDG.
Clean and move in Ready condo on ground floor. This is part of an estate and ready for immediate sale. No probate will be required. The bedroom features and walk in closet. Great location that is great for year round living or a seasonal escape in a very well maintained community.

100 El Camino Drive Unit 103, Winter Haven
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