Winter Haven Real Estate

Winter Haven Real Estate

Welcome to Winter Haven, a charming city located in Polk County, Florida. Known for its beautiful lakes, friendly community, and year-round pleasant weather, Winter Haven is a hidden gem in the heart of the Sunshine State.

Situated in Central Florida, Winter Haven offers a perfect blend of small-town charm and modern amenities. The city is conveniently located just 45 minutes from Orlando and Tampa, making it an ideal place to call home for those seeking a peaceful lifestyle with easy access to big-city attractions.

Winter Haven is renowned for its abundance of freshwater lakes, including the famous Chain of Lakes. With over 50 interconnected lakes, residents and visitors can enjoy a variety of water activities such as boating, fishing, and water skiing. The city's picturesque setting provides a tranquil environment where residents can relax and enjoy the beauty of nature.

In addition to its natural beauty, Winter Haven offers a range of recreational activities and cultural attractions. The city is home to LEGOLAND Florida Resort, a popular theme park that delights both children and adults. The historic downtown area features boutique shops, art galleries, and delicious dining options. The renowned Theatre Winter Haven showcases a variety of performances, including plays, musicals, and concerts.

Winter Haven is also known for its excellent educational institutions, making it an ideal place for families. The city boasts top-rated schools, both public and private, that provide a high-quality education to students of all ages.

Whether you're looking for a peaceful retirement destination, a place to raise a family, or a vacation home, Winter Haven offers a unique blend of natural beauty, recreational opportunities, and a welcoming community. Come and discover the charm of Winter Haven, Florida.

Newest Listings in Winter Haven

4 Beds ⋅ 2 Baths ⋅ Lake Lucerne Ph 5 SubDv. ⋅ 33881 Zip Code

A fantastic opportunity for investors or future homeowners! This beautiful corner-lot home features 4 bedrooms and 2 bathrooms, offering comfort, space, and excellent income potential. It boasts a beautiful, spacious kitchen. The open-concept layout seamlessly connects the living and dining areas, creating the ideal space for entertaining guests or enjoying everyday family life. Sliding glass doors open onto a large backyard—perfect for outdoor activities, gatherings, or simply relaxing. Additional features include a two-car garage, a fully equipped laundry room, and a well-designed floor plan that prioritizes functionality and comfort. Located in the desirable Lake Lucerne community, residents enjoy excellent amenities such as a clubhouse, swimming pools, a playground, and walking paths. The home is close to shops, restaurants, and major roads—including easy access to US-27—making for a convenient commute to Winter Haven, Davenport, and Orlando attractions. Don't miss out on this incredible opportunity!

604 Sarner Pass Way, Winter Haven

3 Beds ⋅ 2 Baths ⋅ Mariana Heights SubDv. ⋅ 33881 Zip Code

Discover the opportunity to own a home in a convenient Central Florida location, surrounded by attractions, recreation, shopping, dining, and everyday conveniences. Enjoy easy access to LEGOLAND® Florida Resort, approximately 25 minutes away, as well as LEGOLAND Water Park and PEPPA PIG Theme Park. Winter Haven is also known for its beautiful Chain of Lakes, offering opportunities for boating, fishing, water activities, and enjoying Florida's outdoors. The area provides convenient access to local parks, restaurants, shopping, entertainment, and downtown Winter Haven. Its Central Florida location also makes it an excellent base for enjoying many of the region's popular attractions while maintaining a more relaxed residential lifestyle. Whether you're looking for a primary residence, a second home, a vacation property, or an investment opportunity, this property offers the chance to enjoy the best of Winter Haven and Central Florida living. Schedule your private showing today!

4629 Palmetto Drive, Winter Haven

3 Beds ⋅ 2 Baths ⋅ Tranquility Park 2nd Rep SubDv. ⋅ 33880 Zip Code

3BR/2BA Beauty Near Downtown Winter Haven — Fully Updated Kitchen! Move right into this beautifully updated 3-bedroom, 2-bathroom home just minutes from downtown Winter Haven. The kitchen has been completely renovated with brand-new cabinetry, a stylish island, and gleaming granite countertops — a true showstopper for anyone who loves to cook or entertain. Ceramic tile flooring flows throughout the entire home for a clean, cohesive, low-maintenance feel. Enjoy an unbeatable location within walking distance of both Lake Shipp and Lake Howard — perfect for morning walks, fishing, or simply soaking in that classic Central Florida lake life. Downtown Winter Haven's shops, restaurants, and community events are just a short drive away. This home comes move-in ready with the refrigerator, stove, microwave, dishwasher, washer, and dryer all included. Major systems have been well maintained. No HOA means no extra fees and no added restrictions. Homes like this in this location don't sit on the market long — schedule your showing today!

1306 15th Street Sw, Winter Haven

2 Beds ⋅ 2 Baths ⋅ Brookhaven Village Second Add SubDv. ⋅ 33881 Zip Code

Welcome to 6364 Lolly Bay Loop NE, a beautifully updated Winter Haven home offering comfort, value, and a convenient Central Florida lifestyle. This property features a **2023 roof, remodeled bathrooms, and new flooring**, giving buyers important major updates and a fresh, move-in-ready feel. Located in a peaceful residential setting, this home offers the opportunity to enjoy the relaxed Winter Haven lifestyle while remaining within convenient driving distance of Orlando and other Central Florida destinations. With access to major highways, nearby shopping, dining, outdoor recreation, and Winter Haven’s many lakes, this location offers the best of both convenience and tranquility. Whether you're looking for a primary residence, a place to settle down, or a home that offers more value for your money, this property is a great opportunity to make Central Florida living your own. Schedule your private showing today and come see all that this home has to offer!

6364 Lolly Bay Loop Ne, Winter Haven

2 Beds ⋅ 2 Baths ⋅ Cypresswood SubDv. ⋅ 33884 Zip Code

BEAUTIFUL VILLA READY TO MOVE IN! A brand-new HVAC system (June 2026), along with new insulation throughout the attic. Features include cathedral ceilings, elegant detailed baseboard trim with decorative corner blocks throughout, new flooring, plantation shutters on the windows, and three sets of French doors. The upgraded kitchen features stainless steel appliances, double ovens, and a built-in pantry with pull-out shelves. A utility closet provides additional storage, and the interior laundry room includes a full-size washer and dryer. The primary bathroom features dual showers and two vanities with wood cabinetry, while the second bathroom includes a jetted bathtub and wood cabinet vanity. Golf course frontage and two outdoor patio areas, with one overlooking the 8th fairway, plus a second patio with concrete privacy walls. Cypresswood Country Club community offers golf, a Jr. Olympic-size pool, tennis courts, a restaurant and bar, social events, live music three nights a week, and lush, well-maintained surroundings. Come take a look at this one!

2801 Wingfoot Court, Winter Haven

3 Beds ⋅ 1 Baths ⋅ Beverly Heights SubDv. ⋅ 33880 Zip Code

AFFORDABLE & REFRESHED 3 BEDROOM CBS HOME ON LARGE LOT AND NO HOA!!! Centrally located in Winter Haven, the home is at the end of a dead-end street for low traffic. Features include tile flooring throughout, kitchen has wood cabinets, granite countertops and all appliances. You'll enjoy the large, fenced back yard, one-car garage with extra room for storage. Call today to see!

707 Dolly Ben Court, Winter Haven

3 Beds ⋅ 2 Baths ⋅ Gardens Ph 01 SubDv. ⋅ 33880 Zip Code

Welcome home to this beautifully refreshed 3-bedroom, 2-bathroom home offering a comfortable layout, fresh updates, and an expansive backyard with plenty of possibilities. Step inside to discover all-new flooring and fresh interior paint, creating a bright, clean, and inviting atmosphere throughout the home. The spacious living areas provide a versatile setting for both everyday living and entertaining, with plenty of natural light adding to the welcoming feel. The well-designed floor plan offers three comfortable bedrooms and two full bathrooms, providing plenty of space for a variety of needs. The attached two-car garage adds valuable parking, storage, and everyday convenience. Outside, the sprawling backyard is one of the home's standout features, offering abundant space to entertain, garden, enjoy outdoor activities, or create your own private retreat. Whether you envision a large outdoor gathering area, garden space, play area, or simply room to relax and enjoy the outdoors, the possibilities are plentiful. With fresh interior updates, a functional layout, generous living space, an attached two-car garage, and an expansive backyard, this home is ready for its next chapter. Come see all that this refreshed home has to offer and schedule your showing today!

212 Majestic Gardens Lane, Winter Haven

4 Beds ⋅ 2 Baths ⋅ Lucerne Park SubDv. ⋅ 33881 Zip Code

4 BEDROOM, 2 BATH NEWER HOME WITH AFFORDABLE HOA, NO CDD AND PRICED TO SELL! Welcome to this clean, well-kept 2020 four-bedroom, two-bath home across from Lake Lucerne in Winter Haven. A brick-paver driveway leads to a two-car garage and a bright, open floor plan. The kitchen features a large island, abundant cabinetry, and all appliances included. Living and dining areas flow together for easy everyday living. The home has no carpeting only easy to care for ceramic tile and luxury vinyl flooring and a Split-bedroom layout that places three bedrooms on one side and a spacious primary suite with ensuite bath and walk-in closet on the other. HOA is only $360 per year with NO CDD. Move-in ready in a convenient neighborhood with NO REAR NEIGHBOR, close to town, around the corner from Willowbrook golf course, shopping, medical and local eateries.

1333 Lucerne Loop Road Ne, Winter Haven

3 Beds ⋅ 2 Baths ⋅ Gaines Cove SubDv. ⋅ 33884 Zip Code

Virtually Staged. Welcome to 3831 Gaines Dr, where beautifully updated interiors, exceptional outdoor living, and the best of the Winter Haven lifestyle come together. Situated on an impressive half-acre-plus homesite in the established Gaines Cove area, this immaculate 3-bedroom plus dedicated office home offers the space, privacy, and character that can be difficult to find. The location is a standout. Enjoy being just minutes from the Winter Haven Chain of Lakes, with multiple nearby options for boat ramps and lake access, making it easy to spend your days boating, fishing, skiing, or exploring Winter Haven’s interconnected lakes. LEGOLAND Florida Resort is also just minutes away, along with shopping, dining, and the everyday conveniences of the Cypress Gardens area. Inside, an inviting open floor plan welcomes you with spacious living areas designed for both everyday comfort and entertaining. Architectural details, abundant natural light, plantation shutters, and a fireplace with built-ins add warmth and character throughout. The beautifully updated kitchen features brand-new appliances and flows seamlessly into the main living area, while updated bathrooms and thoughtful improvements throughout create a polished, move-in-ready feel. A dedicated office with French doors provides the perfect space for working from home, studying, or additional flex space. The upgrades go well beyond what you immediately see. The home features a Kinetico water filtration system, allergen air filtration system, and a Tesla charging station, adding modern convenience and functionality to an already impressive property. Step outside and discover what truly sets this home apart. The expansive screened outdoor living area creates your own private Florida backyard retreat, centered around a heated saltwater pool with plenty of space for relaxing and entertaining. The substantial covered lanai features an impressive outdoor kitchen with built-in grill, vent hood, sink, and refrigeration, complemented by generous outdoor dining and seating areas. Remote-controlled power sun shades on the rear lanai provide added shade, privacy, and comfort at the touch of a button, making this incredible space even more enjoyable throughout the day. And unlike many pool homes, the backyard doesn't end at the screened enclosure. Beyond the pool is an expansive fenced yard with abundant usable green space, mature trees, and beautifully maintained landscaping. The combination of a large homesite, resort-style pool area, covered outdoor living, and substantial backyard creates a wonderful sense of openness and privacy. Curb appeal is equally impressive, with a large paver driveway, expansive front lawn, mature landscaping, and welcoming covered front porch creating a memorable first impression. Spend the morning boating on the Chain of Lakes, the afternoon relaxing in your heated saltwater pool, cook dinner in your outdoor kitchen, and finish the evening unwinding on the lanai. With LEGOLAND just minutes away and shopping, dining, recreation, and multiple lake-access options nearby, 3831 Gaines Dr offers more than a beautifully updated home—it offers the Winter Haven lifestyle.

3831 Gaines Drive, Winter Haven

5 Beds ⋅ 3 Baths ⋅ Villa Mar 40'S SubDv. ⋅ 33884 Zip Code

Under Construction. The first floor of the stunning Edison two-story home is host to an open-concept layout that combines the kitchen with the living and dining areas, and an outdoor patio is easily reached off the main living space. Upstairs, five bedrooms surround a versatile loft, including the luxe owner’s suite, complete with a generous walk-in closet and en-suite bathroom. Villa Mar is a masterplan community of new single-family homes. Near Historic downtown Winter Haven. There are lots of shops, restaurants, bike paths, and easy access to nearby highways. Close to Legoland and Bok Tower Gardens. The much anticipated “Villar Mar” community is what you have been looking for. A safe small town feel with convenience.

6260 Botticella Boulevard, Winter Haven

4 Beds ⋅ 2 Baths ⋅ Inman Grvs Ph 1 SubDv. ⋅ 33881 Zip Code

Beautiful home featuring 4 spacious bedrooms and 2 bathrooms. The fully equipped kitchen boasts beautiful wood cabinetry and granite countertops. Sliding glass doors lead to a covered patio and a private, grassy backyard—perfect for relaxing and enjoying the Florida outdoor lifestyle. The home includes a 2-car garage and a fully equipped laundry room for added convenience. Situated in a desirable community, this property offers comfort, practicality, and excellent investment potential. It is conveniently located near LEGOLAND, Chain of Lakes Park, downtown Winter Haven, shopping centers, restaurants, grocery stores, and medical facilities, with easy access to Highway 27. Winter Haven is also known for its beautiful Chain of Lakes, offering opportunities for boating, fishing, and outdoor recreation. The property is currently leased through November 2026 at $2,150 monthly. A fantastic opportunity for both investors and future homeowners.

507 Short Lane, Winter Haven

4 Beds ⋅ 2 Baths ⋅ Lake Lucerne Ph 5 SubDv. ⋅ 33881 Zip Code

Welcome home! This beautiful property features a comfortable and functional layout, perfect for everyday living and entertaining. Enjoy spacious living areas, a well-appointed kitchen, and inviting bedrooms with plenty of room to relax. Step outside to the fully fenced backyard, providing added privacy and plenty of space for outdoor activities, pets, or weekend gatherings. The covered lanai is the perfect place to enjoy your morning coffee, unwind after a long day, or simply take in Florida’s beautiful weather year-round. Conveniently located near shopping, dining, schools, and major roadways, this home combines comfort, space, and convenience. Schedule your private showing today and come see everything this home has!

624 Sarner Pass Way, Winter Haven

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