Winter Haven Real Estate

Winter Haven Real Estate

Welcome to Winter Haven, Florida—a hidden gem nestled in the heart of Polk County. Known for its stunning chain of lakes, vibrant community, and rich history, Winter Haven offers a unique blend of small-town charm and modern amenities. With over 50 lakes, including the famous Lake Eloise, residents and visitors alike enjoy a myriad of outdoor activities, from fishing and boating to picnicking along the picturesque shores.

Winter Haven is not just about its beautiful landscapes; it also boasts a lively downtown area filled with boutique shops, delightful cafes, and a variety of dining options that cater to every palate. The city hosts numerous events throughout the year, including the Winter Haven Music Festival and the annual Blueberry Festival, which foster a strong sense of community and celebrate the local culture.

Families will appreciate the excellent educational opportunities available in Winter Haven, with a range of public and private schools, as well as nearby colleges. The city is also home to the renowned Legoland Florida Resort, making it a popular destination for families seeking fun and adventure.

With a warm climate year-round, Winter Haven is perfect for those who enjoy an active lifestyle. Whether you're exploring the scenic walking trails, playing a round of golf, or simply soaking up the sun by the lake, there’s always something to do.

In Winter Haven, you’ll find a welcoming community that embraces both new residents and visitors. Come discover the charm of Winter Haven, where every day feels like a vacation!

Newest Listings in Winter Haven

$1,200,000
3 Beds ⋅ 2 Baths ⋅ N/A SubDv. ⋅ 33884 Zip Code
Welcome to your slice of heaven in Winter Haven! Situated on just over 6.5 acres you will find this charming 3/2/2 Cassidy custom pool home surrounded by green meadows and mature oak trees. 4401 Chambliss Rd. offers space, freedom, and a lifestyle you simply won’t find inside typical neighborhoods. This expansive homestead provides room for horses, chickens, gardens, equipment, and future additions, all thanks to the no-HOA flexibility that lets you live the way you choose. There is a refreshing pool perfect for Florida summers and is surrounded by mature trees and wide-open land that create exceptional privacy. A large pond sits quietly among huge cypress trees on the property, adding a peaceful backdrop without dominating the landscape. Acreage of this size is almost unheard of in Winter Haven, making this a standout opportunity for anyone seeking space, seclusion, and the freedom to have a true country retreat while staying close to town conveniences. Updates include: HVAC 2018, Roof 2024, Water Heater 2018. 2 large sheds and large RV/Boat shed.

4401 Chambliss Road, Winter Haven
$300,000
Silvercrest Add SubDv. ⋅ 33881 Zip Code
Investors, look no further! This fully renovated, block duplex in Winter Haven offers immediate cash flow with zero deferred maintenance. Both 1-bedroom, 1-bathroom units are fully occupied on 1-year leases generating income with tenants paying their own separate electric. Extensively updated in 2024, the property features a brand-new roof with a transferable 10-year workmanship warranty and 15-year unlimited wind rating, new mini-split A/C systems, and new tankless water heaters. Additional 2024 upgrades include interior and exterior paint, luxury vinyl plank flooring, remodeled bathrooms, updated kitchens with newer stainless steel appliances, modern light fixtures, ceiling fans, and closet organizers. Residents enjoy exceptional private amenities, including individual front porches, private driveways, personal outdoor storage units, and a shared rear laundry room equipped with a complimentary washer and dryer. The property is wrapped by a fully fenced yard with fresh 2024 landscaping.

405 Avenue M Ne, Winter Haven
$165,000
3 Beds ⋅ 2 Baths ⋅ Carefree Cove SubDv. ⋅ 33881 Zip Code
Don't miss your opportunity to own this block home, featuring 3 bedrooms, 1.5 bathrooms plus a bonus room with no HOA. This is a Fannie Mae Homepath property.

1114 Carefree Cove Drive, Winter Haven
$235,000
2 Beds ⋅ 2 Baths ⋅ Cypresswood SubDv. ⋅ 33884 Zip Code
Welcome to The Meadows, a desirable community within Cypresswoods! This well-maintained home offers the perfect combination of comfort, convenience, and beautiful golf course views. Ideally situated along the golf course, you can enjoy your morning coffee while taking in the scenic views of the 13th hole. The home has been thoughtfully maintained and features a 2025 roof and 2023 HVAC system, providing added peace of mind for the next owner. The property also includes an oversized garage with a workbench. Schedule your showing today!

450 Sandestin Drive, Winter Haven
$260,000
3 Beds ⋅ 2 Baths ⋅ West Lake Park SubDv. ⋅ 33880 Zip Code
Welcome to this beautifully updated 3-bedroom, 2-bath home in Winter Haven! The home offers a versatile in-law suite layout with two living areas and private spaces on each side of the home, connected by a brand-new kitchen featuring new cabinets, quartz countertops, and new appliances. The property also features fresh interior and exterior paint, with most of the flooring updated throughout the home, along with a completely remodeled bathroom. Enjoy the added benefit of paid-off solar panels with no solar loan to assume. The spacious, fully fenced backyard offers plenty of room for entertaining, relaxing, gardening, or outdoor activities. A large workshop/storage area can also be used as a 2-car garage, plus there is a carport in the rear for additional parking. With three separate entrances, this home offers exceptional flexibility for extended family, guests, or a variety of living arrangements. Don't miss this opportunity to own a spacious home with numerous updates and unique features—schedule your showing today!

2336 Avenue E Nw, Winter Haven
$338,000
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
$320,000
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
$275,000
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
$215,000
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
$249,900
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. HOA fee includes roof replacement when needed, so you never have to worry about roof expenses. 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
$239,000
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
$289,000
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
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