Winter Haven Homes for Sale

Winter Haven Homes for Sale

Winter Haven, located in Polk County, Florida, is a charming city that offers a perfect blend of natural beauty and modern amenities. With a population of over 40,000 residents, Winter Haven is known for its warm climate, friendly community, and abundance of recreational activities.

One of the highlights of Winter Haven is its stunning chain of lakes, which includes over 50 interconnected lakes. These lakes provide residents with endless opportunities for boating, fishing, and water sports. In fact, Winter Haven is often referred to as the "Chain of Lakes City." The city is also home to the famous Cypress Gardens, a historic botanical garden that offers beautiful landscapes, wildlife, and thrilling water ski shows.

When it comes to real estate, Winter Haven offers a diverse range of homes for sale to suit every lifestyle and budget. From charming bungalows and historic homes to modern condos and spacious family residences, there is something for everyone in Winter Haven. The city boasts a mix of established neighborhoods and new developments, providing a variety of options for homebuyers.

The real estate market in Winter Haven is thriving, with a steady demand for properties. Whether you are looking for a waterfront home with stunning lake views or a cozy house nestled in a quiet neighborhood, Winter Haven has it all. With affordable prices and a low cost of living, Winter Haven is an attractive destination for those looking to settle down or invest in real estate.

In conclusion, Winter Haven, Florida, offers a vibrant community, breathtaking natural beauty, and a wide range of homes for sale. With its desirable location and affordable real estate options, Winter Haven is a city worth considering for those seeking a place to call home.

Newest Winter Haven Homes for Sale

2434 Edwin Street Ne, Winter Haven
$100,000
3 Beds ⋅ 1 Baths ⋅ Smart Sub SubDv. ⋅ 33881 Zip Code
NVESTOR OPPORTUNITY! Bring your vision and transform this property into its full potential. This home is ready for a complete renovation and offers an opportunity for an investor, rehabber, or buyer looking for a project. Property is being sold AS-IS. No appliances are included. Buyer and buyer’s agent are responsible for verifying all property information, measurements, condition, utilities, and intended use. Cash only. Schedule your showing and explore the possibilities! Property must be physically seen before submitting offers.

2434 Edwin Street Ne, Winter Haven
1085 Brenton Manor Drive, Winter Haven
$275,000
3 Beds ⋅ 2 Baths ⋅ Brenton Manor SubDv. ⋅ 33881 Zip Code
Virtually Staged. Welcome to this beautifully maintained 3-bedroom, 2-bathroom single-story home in a highly desirable Winter Haven community with low HOA fees! Built in 2015, this property features complete ceramic tile flooring throughout, a new roof installed in 2024, Paid Off Solar Panels and a fully fenced backyard for added privacy. The open living area highlights a custom 3D feature wall with a fireplace, creating a cozy and stylish focal point. Complete with a 2-car garage and all appliances included, this home offers modern comfort and key upgrades. Located in the vibrant Chain of Lakes region near boating and outdoor recreation, plus just 20 minutes from LEGOLAND Florida Resort and 30 miles from Walt Disney World. Schedule your showing today!

1085 Brenton Manor Drive, Winter Haven
5007 Abigail Drive, Winter Haven
$299,990
4 Beds ⋅ 2 Baths ⋅ Willowbrook North SubDv. ⋅ 33881 Zip Code
Virtually Staged. Under Construction. Welcome to the Bradley, the perfect combination of comfort, style, and functionality. This inviting single-story floor plan features 4 bedrooms, 2 bathrooms, and a 2-car garage, with an open-concept layout that's ideal for everyday living and entertaining. Tile flooring extends throughout the main living areas, creating a seamless and durable finish, while the spacious great room flows effortlessly into the dining area and kitchen.

5007 Abigail Drive, Winter Haven
3947 Cypress Landing W, Winter Haven
$309,000
3 Beds ⋅ 2 Baths ⋅ Cypress Landing Ph 01 SubDv. ⋅ 33884 Zip Code
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
718 Eagle Landing Boulevard, Winter Haven
$339,998
4 Beds ⋅ 3 Baths ⋅ Eagle Landing Phase Ii SubDv. ⋅ 33880 Zip Code
Welcome to 718 Eagle Landing Boulevard, a stunning, nearly new 4-bedroom, 2.5-bathroom home that perfectly blends modern style, comfort, and peaceful surroundings! Built just three years ago and barely lived in, this beautiful home has recently undergone fantastic upgrades, including brand-new luxury vinyl flooring throughout all bedrooms and the staircase, with absolutely NO CARPET anywhere in the home! Situated on one of the most desirable lots in the community, this home enjoys a beautiful, wide-open wooded backdrop with NO REAR NEIGHBORS, offering a rare sense of privacy and tranquility. Tucked away toward the quiet rear of the neighborhood, its peaceful setting makes it feel like your own private retreat. Step inside and immediately appreciate the sleek, modern interior, inviting living spaces, and abundance of natural light that fills the home. The thoughtfully designed layout offers four generously sized bedrooms, 2.5 bathrooms, and a spacious garage, providing plenty of room for comfortable everyday living. The oversized primary suite is a true highlight, featuring an exceptionally spacious bedroom, a generous walk-in closet, and an additional storage or closet area for even more convenience. Located in beautiful Winter Haven, famously known as the Chain of Lakes City, this home places you in one of Central Florida's most charming destinations, celebrated for its picturesque lakes, outdoor recreation, and relaxed Florida lifestyle. Enjoy convenient access to Chain of Lakes Park, a recreational destination near Lake Lulu offering sports facilities, open green spaces, and opportunities to enjoy the outdoors. Just a short drive away, discover the excitement of LEGOLAND Florida Resort and the new SEA LIFE Florida Aquarium, along with a wonderful variety of shopping, dining, and entertainment options. Whether you're drawn to lakeside adventures, outdoor activities, or local attractions, Winter Haven offers something for everyone! With its fresh upgrades, contemporary finishes, exceptional lot, and barely lived-in condition, this home offers the look and feel of new construction without the wait! Whether you're enjoying the bright, welcoming interior or the peaceful wooded views out back, every detail makes this property a wonderful place to call home. Homes with this combination of privacy, location, condition, and modern upgrades are hard to find! Don't miss your opportunity to make this exceptional home yours. Schedule your private showing today!

718 Eagle Landing Boulevard, Winter Haven
1638 Seth Drive, Winter Haven
$408,888
5 Beds ⋅ 3 Baths ⋅ Pinnacle Point SubDv. ⋅ 33880 Zip Code
Room to spread out in Pinnacle Point! Built in 2022, this two-story Winter Haven home offers 5 bedrooms, 3 full bathrooms, and approximately 2,892 square feet of heated living space on a 0.17-acre corner lot. The living room and kitchen are located on the first floor, while the primary bedroom is upstairs. A two-car attached garage provides parking and storage space. With five bedrooms, there’s flexibility for guests, a home office, or hobbies. Enjoy no CDD fees and an HOA fee of $214 per quarter. Located in Central Florida between Tampa and Orlando, Pinnacle Point offers convenient access to shopping, dining, schools, parks, and medical facilities. Nearby LEGOLAND Florida Resort adds another option for recreation, while access to major highways connects you to destinations throughout the region.

1638 Seth Drive, Winter Haven
593 Terranova Circle, Winter Haven
$359,000
3 Beds ⋅ 2 Baths ⋅ Terranova Ph 01a SubDv. ⋅ 33884 Zip Code
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
1096 Carefree Cove Drive, Winter Haven
$199,000
4 Beds ⋅ 2 Baths ⋅ Carefree Cove SubDv. ⋅ 33881 Zip Code
**PRICED TO SELL! 4 BEDROOMS, 2 BATHROOMS, NO HOA, AND MAJOR UPDATES ALREADY COMPLETED! ** Don't miss this fantastic opportunity to own an affordable home in Winter Haven! This spacious 4-bedroom, 2-bathroom home offers plenty of potential with several major improvements already taken care of, including a **NEW ROOF IN 2022, COMPLETE REPIPE IN 2023, AND NEW WINDOWS IN 2023!** While the home could benefit from some cosmetic updating and personal touches, the big-ticket improvements have already been completed, giving the next owner a great head start. Enjoy the freedom of **NO HOA** and a convenient location near shopping, dining, schools, and major roadways. Whether you're a first-time homebuyer looking to build equity, a buyer wanting to make a home their own, or an investor searching for their next opportunity, this property checks all the boxes! **PRICED EXTREMELY COMPETITIVELY TO REFLECT THE COSMETIC UPDATES NEEDED AND SELL QUICKLY!** Opportunities like this don't come around often at this price point. Schedule your showing today and see the potential for yourself!

1096 Carefree Cove Drive, Winter Haven
221 Mandolin Drive, Winter Haven
$330,000
4 Beds ⋅ 2 Baths ⋅ Mandolin SubDv. ⋅ 33884 Zip Code
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 ⋅ Eloise Woods Lake Mariam Unit SubDv. ⋅ 33884 Zip Code
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
2303 Jagger Lane, Winter Haven
$355,000
4 Beds ⋅ 2 Baths ⋅ Sutton Preserve SubDv. ⋅ 33880 Zip Code
Virtually Staged. Move-in ready and built in 2024! This beautifully maintained 4-bedroom, 2-bath home offers nearly 1,900 sq. ft. of thoughtfully designed living space with an open-concept layout and desirable upgrades throughout. The spacious kitchen features quartz countertops, stainless-steel appliances, a large center island, and pantry, opening seamlessly to the living and dining areas. Tile flooring enhances the main living spaces, with carpet in the bedrooms. Additional features include an epoxy-finished garage floor, rain gutters, security cameras that convey, and solar panels. Enjoy Florida living on the enclosed screened lanai, complete with roll-down shades and patio furniture that convey, overlooking a fully fenced backyard. Located just minutes from Lake McLeod and a public boat dock, with convenient access to shopping, dining, schools, and major roadways. No CDD, low HOA fees that include high-speed internet, and a seller-provided one-year home warranty! A wonderful opportunity to own a move-in-ready home with valuable upgrades already in place. Schedule your private showing today!

2303 Jagger Lane, Winter Haven
2470 Salzburg Loop, Winter Haven
$270,000
3 Beds ⋅ 2 Baths ⋅ Vienna Square Ph 01 SubDv. ⋅ 33884 Zip Code
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
Start Your Search

How much is your home worth?

Get instant property value now!