Winter Haven Homes for Sale

Winter Haven Homes for Sale

Welcome to Winter Haven, Florida – a charming city nestled in the heart of Polk County, where the sun shines brightly and the community spirit thrives! Known for its picturesque lakes and vibrant outdoor lifestyle, Winter Haven is a hidden gem that offers a perfect blend of relaxation and recreation. With its rich history and friendly atmosphere, it’s no wonder that families, retirees, and young professionals alike are drawn to this delightful city.

Winter Haven is renowned for its stunning lakes, boasting over 50 bodies of water that provide ample opportunities for fishing, boating, and enjoying scenic waterfront views. The city is home to the famous Legoland Florida Resort, making it a fantastic destination for families seeking fun and adventure. Additionally, the downtown area is filled with quaint shops, delightful eateries, and lively community events, ensuring there’s always something to do.

For those looking to settle down in this idyllic locale, Winter Haven offers a diverse array of homes for sale. From charming single-family residences to modern townhouses and spacious waterfront properties, there’s something to suit every lifestyle and budget. The housing market here is dynamic, with options that cater to first-time buyers, growing families, and retirees seeking tranquility.

With its affordable cost of living, excellent schools, and abundant recreational opportunities, Winter Haven is not just a place to live – it’s a place to thrive. Come discover your dream home in this enchanting city where every day feels like a vacation!

Newest Winter Haven Homes for Sale

$259,900
3 Beds ⋅ 2 Baths ⋅ Fox Ridge Ph 01 SubDv. ⋅ 33884 Zip Code
Welcome to this move-in ready 3-bedroom, 2-bathroom home in the desirable Fox Ridge neighborhood. This home features a modern open-concept layout that connects your living spaces with a seamless flow. The living area is highlighted by a cozy fireplace, creating a warm and welcoming focal point. The updated kitchen comes beautifully equipped with sleek stainless steel appliances and gorgeous granite countertops. The primary suite offers a private retreat complete with a large walk-in closet and an attached primary bathroom featuring double sinks/vanity. Step outside to enjoy the privacy of a fully fenced backyard. The location is a standout, centrally positioned just minutes away from local shopping, schools, dining options, and the excitement of Legoland. Schedule your private showing today!

3329 Fox Ridge Drive, Winter Haven
$345,000
4 Beds ⋅ 2 Baths ⋅ Lake Lucerne Ii SubDv. ⋅ 33881 Zip Code
Virtually Staged. Newer home with NO CDD and large yard!!! Welcome home to this beautifully maintained 4 bedroom, 2 bath home offering 1,983 square feet of comfortable living space and modern finishes throughout. Built in 2023, this home features a desirable open split-floor plan designed for both everyday living and entertaining. The spacious kitchen boasts granite countertops, large island, stainless steel appliances, and plenty of room to gather with family and friends. The split-bedroom layout provides privacy for the primary suite while keeping the additional bedrooms conveniently accessible. Step outside to enjoy the large yard and relaxing covered lanai—perfect for morning coffee, outdoor dining, or entertaining. Additional highlights include a 2-car garage, new carpet, and no CDD. With its modern construction, spacious layout, and move-in-ready appeal, this home is a must-see!

1425 Engelberg Street, Winter Haven
$310,000
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
$1,250,000
5 Beds ⋅ 4 Baths ⋅ Interlaken Add SubDv. ⋅ 33881 Zip Code
Welcome to this extraordinary custom-built lakefront residence offering an unparalleled lifestyle on the renowned Winter Haven Chain of Lakes. Built-By-Waters in 2024, this award-winning property earned the Polk County Parade of Homes coveted “Home of the Year” award while sweeping all five subcategories for Best Exterior, Best Floor Plan, Best Kitchen, Best Master Bath, and Best Overall Quality. Elevated above the shoreline with sweeping southern views across Lake Howard, the home was thoughtfully designed to embrace its waterfront setting while delivering refined luxury and effortless everyday living. Stately iron doors welcome you inside to soaring ceilings, sophisticated lighting, open-concept living, and expansive windows and glass doors that blur the boundaries between indoors and out. The main living area features a custom beam ceiling and a mesmerizing 6-foot-wide Napoleon fireplace, creating the perfect balance of comfort and refinement. The spectacular kitchen combines striking design with exceptional functionality, anchored by an oversized quartz island and complemented by an Italian-designed Bertazzoni gas range, stainless appliances, sleek flat-front cabinetry, wine cooler, and concealed walk-in pantry—all flowing seamlessly into the dining area. The primary suite features two custom-organized walk-in closets and a spa-inspired bath with quartz countertops, large walk-in shower, and luxurious soaking tub positioned beside the window to enjoy lake and sunset views. Four additional bedrooms provide plenty of space and versatility, complemented by beautifully finished baths all with custom tile work, seamless glass enclosures, and quartz countertops. One larger bedroom currently serves as a second living area and could easily become a secondary primary suite, golf simulator room, wellness studio, or sophisticated whiskey lounge. Outdoor living is equally impressive with a full summer kitchen featuring granite counters, gas grill, power burner, refrigerator, and sink. The fully fenced and beautifully landscaped backyard offers privacy and the perfect canvas for a custom pool and outdoor retreat. Continue toward the lake, where an impressive two-story private dock features two covered boat slips, a storage room, electric and water, and an upper observation deck offering sweeping views across Lake Howard and a front-row seat to some of Central Florida’s most spectacular sunsets. The Winter Haven Chain of Lakes is not your average lakefront lifestyle. Spend your days exploring 20 canal-connected lakes, boating, skiing, fishing, or cruising through enchanting tree-canopied canals and cypress-lined shorelines. Boat to waterfront restaurants for dinner, live music, or a cold drink, gather friends for an afternoon on the water, watch painted sunsets from the lake, or experience spectacular fireworks from your boat. Just minutes from downtown Winter Haven, the property offers convenient access to dining, shopping, entertainment, and medical facilities. Additional features include a 26kW generator, tankless Rinnai water heaters, two A/C systems (2024/2025), landscape and soffit lighting, double-pane windows, irrigation well, and so much more. Meticulously crafted to capture every advantage of its remarkable setting, 1307 N Lake Howard Dr is more than a luxury home—it is a statement of refined lakefront living. (SEE VIRTUAL TOUR LINK)

1307 N Lake Howard Drive, Winter Haven
$355,000
4 Beds ⋅ 3 Baths ⋅ Eagle Lndg Ph Ii SubDv. ⋅ 33880 Zip Code
PRICE IMPROVEMENT! SELLER HIGHLY MOTIVATED! BEST VALUE IN EAGLE LANDING! Welcome to this beautiful 2022-built home in the desirable Eagle Landing community of Winter Haven, conveniently located just minutes from LEGOLAND Florida and ideally positioned between Tampa and Orlando. Offering approximately 2,300 square feet of living space, this move-in-ready home features a spacious open-concept floor plan designed for comfortable everyday living and entertaining. The modern kitchen flows seamlessly into the main living areas, creating a bright and inviting space. Enjoy Florida living from the screened-in porch overlooking the private, fully vinyl-fenced backyard. Additional features include durable block construction, architectural shingle roof, modern stucco exterior, and a LOW HOA. Whether you're looking for a primary residence, vacation home, or investment property, this home offers an excellent combination of location, size, condition, and value. Offered at $355,000 with a highly motivated seller. Easy to show—schedule your private showing today!

662 Eagle Landing Boulevard, Winter Haven
$99,900
2 Beds ⋅ 2 Baths ⋅ Kenilworth Park SubDv. ⋅ 33881 Zip Code
CASH ONLY, INVESTORS SPECIAL! This adorable home has so much potential and a wonderful location near Lake Mirror and Lake Cannon in Winter Haven. Built in 1926, features such as wood flooring and a brick fireplace add to the historic charm of this bungalow. Repairs are needed, but this home is priced to sell - allowing for a great investment into a flip, rental or place to call home!

1825 16th Street Nw, Winter Haven
$244,900
3 Beds ⋅ 2 Baths ⋅ Queens Cove Ph 03b SubDv. ⋅ 33880 Zip Code
Welcome to this inviting 3-bedroom, 2-bathroom home located in the Queens Cove neighborhood. This home features a functional floorplan that creates a seamless flow for relaxing and entertaining. The kitchen is functional and stylish, boasting durable countertops and sleek appliances. For added privacy, the primary bedroom is complete with its own attached primary bathroom. Ideally located just minutes from the Polk Parkway, shopping, and grocery stores, and only 20 minutes from the attractions at LEGOLAND, this home offers everything you need for easy, everyday living. Schedule your private showing today!

3735 Imperial Drive, Winter Haven
$315,000
4 Beds ⋅ 3 Baths ⋅ Jan Phyl Village SubDv. ⋅ 33880 Zip Code
Welcome home to this spacious 4-bedroom, 3-bathroom home offering over 2,000 square feet of comfortable living space on a large corner lot. Designed with both everyday living and entertaining in mind, this home features two bedrooms with private en-suite bathrooms, providing flexibility and privacy for family members or guests. Step outside to the screened lanai, where you can relax and enjoy views of the expansive backyard and in-ground pool—perfect for Florida living and entertaining year-round. The large fenced backyard provides plenty of room for outdoor activities, pets, gardening, or simply enjoying your own private outdoor retreat. With its generous living space, desirable split-bedroom potential, pool, and oversized corner lot, this home offers plenty of room to make it your own. Don’t miss the opportunity to make this spacious pool home your next address!

506 Clayton Circle, Winter Haven
$279,900
3 Beds ⋅ 3 Baths ⋅ Inwood SubDv. ⋅ 33881 Zip Code
Welcome to this beautiful and versatile home featuring a private detached mother-in-law suite with its own bedroom, bathroom, and full kitchen, perfect for extended family, guests, or additional living space. No HOA. The home offers a comfortable, functional layout with spacious living areas and plenty of room for everyone. The separate suite provides added privacy and flexibility, making this property an excellent choice for multi-generational living.

723 24th Street Nw, Winter Haven
$279,000
3 Beds ⋅ 2 Baths ⋅ 33880 Zip Code
Virtually Staged. "One or more photo(s) was virtually staged." This 3-bedroom, 2-bathroom home offers 1,124 square feet of living space with the added bonus of .94 acres of land and No HOA! Built in 2015, this home features a split-bedroom floor plan, laminate flooring throughout, and an inside utility closet for added convenience. Enjoy the privacy and freedom of nearly an acre where there is plenty of room to spread out, entertain, garden, park your toys, or create the outdoor space you've always wanted. The property also features a carport, screened front porch, private well, and septic system. Vacant and ready for its new owners, this property is a great opportunity for anyone looking for a comfortable home with plenty of land and no HOA restrictions. Don't miss out on this wonderful opportunity to enjoy country living with nearly an acre of land and all the convenience of being close to everything!

214 King Road, Winter Haven
$430,000
3 Beds ⋅ 2 Baths ⋅ Overlook Estates SubDv. ⋅ 33884 Zip Code
Welcome to the beautiful neighborhood of Overlook Estates. This 3 bedroom 2 bath + bonus room is waiting for its new owner/s to make it their own. This home is completely vacant which makes it that much easier to envision your own life here. When you first arrive you will notice the beautiful curb appeal this home offers. Upon entering you will be greeted by the stunning entrance. This home is bright and spacious with high ceilings and beautiful wood beams giving it character right off the bat. The kitchen was completely remodeled in 2022. It has floor to ceiling cabinets giving you plenty of space for storage. Use the large island with a built in cook top or move it over to a more formal dining room. Either way this home is the perfect place for entertaining. You can access the lanai/salt water pool from the primary bedroom, kitchen, living room, and even the full guest bath. The open floor plan allows for friends and family to gather while still having plenty of space to spread out. The primary bedroom with ensuite bath and walk in closet as well as that access to the lanai. The primary bathroom has a walk in shower, garden tub, dual vanity and also includes a walk in closet as well as a linen closet. The two additional bedrooms as well as a full bath are located on the opposite side of the house. A fourth room allows for the perfect office space or even a room to host your guests. This home has been wonderfully updated while still holding onto its charm and character. Schedule your showing today!

280 Santa Rosa Drive, Winter Haven
$299,990
4 Beds ⋅ 2 Baths ⋅ Royal Hills SubDv. ⋅ 33881 Zip Code
Welcome to this well-located single-family home situated in Winter Haven, offering a comfortable layout and enjoyable outdoor space. This home features 4 bedrooms and 2 bathrooms with a practical floor plan that supports everyday living, along with a 2-car garage and a large driveway and backyard. The property also includes a Newer Shingle Roof (2026), Newer A/C (2025) and newer LVP flooring (2026). Inside, the living area offers two living room areas with high ceilings, one at the entrance and another one by the kitchen, creating a welcoming space that makes it easy to stay connected whether you’re relaxing at home or entertaining guests. The bedrooms are nicely sized, and the primary suite provides added comfort with a walk-in closet and a private bathroom that features both a bathtub and a separate shower. The second full bathroom add convenience and functionality for the household. Whether you’re searching for a place to make your own or an investment opportunity, this home is worth a look. Schedule your showing today.

5641 Royal Hills Drive, Winter Haven
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