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 that perfectly blends small-town charm with modern convenience. Known for its stunning lakes, Winter Haven is often referred to as the "Chain of Lakes City," boasting over 50 lakes that offer residents and visitors alike a plethora of recreational activities. From fishing and boating to picnicking by the water’s edge, the natural beauty of Winter Haven is truly captivating.

Winter Haven is not just about its picturesque landscapes; it’s also home to a vibrant community and a rich cultural scene. The city hosts numerous festivals throughout the year, including the popular Winter Haven Music Festival, where locals and visitors gather to enjoy live performances and delicious food. For those who appreciate history, the historic downtown area features charming boutiques, delightful eateries, and the iconic Polk Theatre, which showcases a variety of performances and films.

For those considering a move, Winter Haven offers a diverse range of homes for sale, catering to various lifestyles and budgets. Whether you’re looking for a cozy family home, a modern condo with lake views, or a spacious estate with ample outdoor space, you’ll find an array of options that fit your needs. The real estate market here is thriving, making it an ideal time to explore the opportunities that Winter Haven has to offer.

Discover the magic of Winter Haven, where community spirit meets scenic beauty, and find your dream home in this delightful Florida city!

Newest Winter Haven Homes for Sale

3 Beds ⋅ 1 Baths ⋅ West Cannon Heights SubDv. ⋅ 33881 Zip Code

Virtually Staged. Completely renovated from top to bottom, this home offers the feel of new construction at a fraction of the price! Featuring 3 bedrooms plus a spacious family room that can easily serve as a 4th bedroom, home office, playroom, or media room, this property offers flexibility to fit your lifestyle. Every major component has been updated, including the roof, windows, A/C, water heater, kitchen, bathroom, plumbing, electrical, paint, and more, giving you peace of mind for years to come. Step outside to enjoy the oversized backyard with plenty of space for entertaining, pets, gardening, or future additions. No HOA means more freedom and fewer monthly expenses. Conveniently located near shopping, restaurants, schools, and major highways, this move-in-ready home is an excellent opportunity for first-time buyers or investors looking to add a low-maintenance property to their portfolio. Schedule your private showing today!

1207 32nd Street Nw, Winter Haven

5 Beds ⋅ 3 Baths ⋅ Villamar Phase 7 SubDv. ⋅ 33884 Zip Code

The Robie is a two-story floorplan featured in Villamar in Winter Haven, Florida. With 2 exteriors to choose from, the Robie is sure to turn heads. Inside this inviting 5-bedroom, 3-bathroom home, you’ll find 2,447 square feet of comfortable living. This impressive all concrete block construction, two-story plan features a versatile floorplan to fit your needs. A spacious open-concept first floor which includes a well-appointed kitchen with sleek stainless-steel appliances overlooking the living and dining area. Just off the living room you will find the singular downstairs bedroom and full bathroom. As you move upstairs you are greeted with a spacious living and foyer space to utilize for work or play. The primary bedroom one is located just off the loft space and features a spacious walk-in closet as well as ensuite bathroom with double vanity and all the space you need to get ready in the morning. Three additional bedrooms share a second upstairs bathroom and linen closet for extra storage. Your laundry room is located on the second floor as well as extra storage closets. Like all homes in Villamar, the Robie includes smart home technology, which allows you to control your home anytime with your smart device while near or away. *Photos are of similar model but not that of the exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability, and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

5568 Taverna Loop, Winter Haven

3 Beds ⋅ 2 Baths ⋅ Inwood SubDv. ⋅ 33881 Zip Code

Move right in and enjoy this charming 3-bedroom, 2-bathroom concrete block home in a convenient Winter Haven location with NO HOA! Featuring easy-care tile flooring throughout, this home offers both style and low-maintenance living. The kitchen is equipped with rich hardwood cabinets, stainless steel appliances, and plenty of storage, making it as functional as it is inviting. An indoor laundry room adds extra convenience to your daily routine. The spacious primary suite features a beautifully tiled step-in shower, while the guest bathroom offers a tiled tub/shower combination. Step outside to a large, fully fenced backyard with endless possibilities for entertaining, gardening, pets, or simply relaxing outdoors. A covered carport provides sheltered parking and additional storage space. Located just minutes from Havendale Boulevard, you'll have quick access to shopping, restaurants, schools, healthcare, and everyday conveniences. Spend weekends exploring Winter Haven's famous Chain of Lakes, known for its boating, fishing, waterfront parks, and scenic beauty. Commuters and travelers will appreciate the easy drive to both Tampa and Orlando, providing access to major employers, international airports, world-renowned attractions, sporting events, and endless entertainment options. Whether you're searching for your first home, looking to downsize, or adding to your investment portfolio, this property is one you won't want to miss!

3004 Avenue S Nw, Winter Haven

3 Beds ⋅ 2 Baths ⋅ Fla Highlands Co Sub SubDv. ⋅ 33884 Zip Code

Welcome to this beautifully renovated 3-bedroom, 2-bathroom home in the desirable Cypress Gardens area of Winter Haven, where every detail has been thoughtfully updated and topped off with a New Roof (2026) for lasting peace of mind. Step inside to an inviting open floor plan anchored by a stunning vaulted ceiling with rich exposed wood beams, a true architectural centerpiece that carries warmth and character throughout the main living space. Luxury vinyl plank flooring flows seamlessly from room to room, offering both beauty and durability. The kitchen is nothing short of a showpiece, featuring a hand-painted blue and white tile backsplash, sleek white shaker cabinetry, quartz countertops, and high-end stainless steel appliances. Whether you're preparing a quiet meal or entertaining guests, this kitchen delivers both style and function in equal measure. Both bathrooms have been beautifully renovated with designer tile flooring and tiled showers, warm wood vanities, matte black fixtures, and elegant round mirrors, a spa-like retreat within your own home. Step out back to a fully fenced yard framed by mature trees for added privacy, plus a covered, screened porch, the perfect spot to unwind. And just beyond it, a bonus room offers flexible space for a home office, playroom, gym, or guest retreat, a rare and valuable addition to a home in this price range. With a 2-car garage, an unbeatable location near shopping, dining, and major roadways, and a renovation that leaves nothing to be desired, this home is truly move-in ready. Schedule your private showing today, this one will not last.

205 Whitman Road, Winter Haven

3 Beds ⋅ 2 Baths ⋅ Winter Haven Heights SubDv. ⋅ 33881 Zip Code

Beautiful 2024-built home offering exceptional value! No HOA! Welcome to this beautifully built 3-bedroom, 2-bath home offering 1,560 square feet of thoughtfully designed living space. The open-concept floor plan features tile flooring throughout, a spacious living and dining area, and a modern kitchen with granite countertops, ample cabinetry, and stainless steel appliances including a cooktop, dishwasher, and refrigerator. The split-bedroom layout provides privacy, while the primary suite offers a walk-in closet and private bath. Situated on a spacious 0.17 acre lot with a two-car garage, this home is conveniently located near downtown Winter Haven, Legoland, hospitals, shopping, restaurants, schools, and major highways with easy access to Orlando and Tampa. Built in 2024 and move-in ready, this is an excellent opportunity for homeowners and investors alike. Schedule your private showing today! With proper permits, the backyard offers the potential to build an in-law suite or guest house

319 Avenue A Ne, Winter Haven

4 Beds ⋅ 2 Baths ⋅ Summer Haven Shores SubDv. ⋅ 33884 Zip Code

Virtually Staged. Beautiful 1-story home featuring 4 bedrooms, 2 bathrooms, and a 2-car garage with a spacious layout designed for comfortable living. The welcoming living room is highlighted by a cozy fireplace, while the kitchen and bathrooms have been refreshed with new countertops. Fresh interior paint throughout gives the home a bright, updated feel. Step outside to the screened lanai and private pool, offering the perfect space for relaxing or entertaining year-round. Conveniently located near LEGOLAND Florida Resort, Chain of Lakes, shopping, dining, and major roadways, this home offers both comfort and convenience. This is a fantastic opportunity to add your personal touches and make it your own. One or more photos may have been virtually staged, AI-generated, or digitally enhanced to illustrate the property's potential.

408 Coleman Drive, Winter Haven

4 Beds ⋅ 3 Baths ⋅ Ashton Covey SubDv. ⋅ 33884 Zip Code

Pre-Construction. To be built. Welcome to Ashton Covey in Winter Haven! The Lynn Haven single-family home lives up to expectations. Relax on the long front porch. Inside, flex space makes an ideal den, or add doors for a quiet study. The foyer leads to the open family room and gourmet kitchen with island, where favorite meals and memories will be made. Enjoy outdoor living on the lanai, and store seasonal items in the 3-car garage. There’s even more to love upstairs with a loft, 3 bedrooms and a full bath. In your deluxe owner’s suite, enjoy beautiful tray ceilings, double vanities and a walk-in closet. You can have it all in The Lynn Haven. Discover the ultimate Florida lifestyle in this stunning community. Perfectly situated just off US Highway 27, your new home offers seamless access to work, outdoor recreation, shopping, dining, and more. Imagine being less than 15 minutes from Downtown Winter Haven, where charming local shops and restaurants await your exploration. Plus, you're just 5 miles from public lake access at Lake Daisy, ideal for a day of boating, paddle boarding, and enjoying the water. All Ryan Homes now include WIFI-enabled garage opener and Ecobee thermostat. **Closing cost assistance is available with use of Builder’s affiliated lender**. DISCLAIMER: Prices, financing, promotion, and offers subject to change without notice. Offer valid on new sales only. See Community Sales and Marketing Representative for details. Promotions cannot be combined with any other offer. All uploaded photos are stock photos of this floor plan. Actual home may differ from photos.

2232 Labrador Loop, Winter Haven

4 Beds ⋅ 2 Baths ⋅ Ashton Covey SubDv. ⋅ 33884 Zip Code

Pre-Construction. To be built. Welcome to Ashton Covey in Winter Haven! The Panama single-family home is what you always pictured for yourself. Step in from the 2-car garage or front porch and pass the first of 3 spacious bedrooms and a full bath with double vanity. A versatile flex space can be used as an office, a study, or a 4th bedroom. In the dining area, prepare to be wowed. This space is highlighted by a gourmet kitchen with a large island overlooking a lanai and a great room where friends and family will gather. Your luxurious owner’s suite includes a beautiful tray ceiling, a double vanity owner’s bath and a huge walk-in closet. The Panama is pure bliss. Discover the ultimate Florida lifestyle in this stunning community. Perfectly situated just off US Highway 27, your new home offers seamless access to work, outdoor recreation, shopping, dining, and more. Imagine being less than 15 minutes from Downtown Winter Haven, where charming local shops and restaurants await your exploration. Plus, you're just 5 miles from public lake access at Lake Daisy, ideal for a day of boating, paddle boarding, and enjoying the water. All Ryan Homes now include WIFI-enabled garage opener and Ecobee thermostat. **Closing cost assistance is available with use of Builder’s affiliated lender**. DISCLAIMER: Prices, financing, promotion, and offers subject to change without notice. Offer valid on new sales only. See Community Sales and Marketing Representative for details. Promotions cannot be combined with any other offer. All uploaded photos are stock photos of this floor plan. Actual home may differ from photos.

2236 Labrador Loop, Winter Haven

4 Beds ⋅ 2 Baths ⋅ Island Lakes SubDv. ⋅ 33881 Zip Code

CHAIN OF LAKES LAKEFRONT LIVING on Lake Rochelle! Welcome to Island Lakes, where everyday life feels like a vacation. Located on the highly desirable Winter Haven Chain of Lakes, this beautifully updated home offers the ultimate waterfront lifestyle—boating, sunset cruising, and lakefront dining right from your own backyard. This 4-bedroom, 2-bath home is designed for both comfort and entertaining, featuring an open floorplan with stunning lake views from the main living areas. The spacious great room is filled with natural light, showcasing soaring ceilings, plant shelves, and an expansive sliding glass door that seamlessly blends indoor and outdoor living. The updated kitchen is both stylish and functional, complete with new cabinetry, solid surface countertops, stainless steel appliances, a full tile backsplash, breakfast bar, and a cozy eat-in nook—all perfectly positioned to take in the water views. The primary suite has been beautifully renovated, featuring a sliding barn door leading to a spa-like bathroom with a walk-in glass and tile shower, dual vanities with stone countertops, and a large walk-in closet with built-ins and hidden storage. Step outside and experience true Florida living with a huge screened outdoor living space complete with a hot tub, perfect for relaxing evenings or entertaining guests year-round. Beyond that, enjoy your private dock with a covered boat lift and freshwater supply, ready for days on the Chain. A public boat ramp is just minutes away. This home also features $92,000 in solar panels, providing exceptional energy efficiency and long-term savings—keeping utility costs low while supporting a more sustainable lifestyle. Additional features include a fully fenced backyard, beautiful lake views, and a prime location near Hwy 27 and I-4 with easy access to Orlando, Disney, Lakeland, and Tampa. This is more than a home—it’s a true Chain of Lakes lifestyle with comfort, efficiency, and unforgettable views.

4123 Island Lakes Drive, Winter Haven

4 Beds ⋅ 3 Baths ⋅ Peace Creek Reserve 50s SubDv. ⋅ 33884 Zip Code

Virtually Staged. WELCOME HOME! FULLY FENCED! Discover this stunning one-story home featuring a full In-Law Suite with its own bedroom, bathroom, kitchenette, laundry, and private entrance, perfect for multigenerational living or guests seeking total privacy. The main home offers 3 spacious bedrooms, 2 full bathrooms, and a versatile flex room ideal for an office, playroom, or potential 4th bedroom. Enjoy quartz countertops, upgraded lighting, stainless steel appliances, and a large island perfect for gatherings. The fenced backyard with covered patio is ideal for relaxing or entertaining. Located in Peace Creek Reserve with access to a community pool, playground, and close to schools, shopping, and dining. Don’t miss this rare opportunity, schedule your showing today!

1172 Tyler Loop, Winter Haven

3 Beds ⋅ 2 Baths ⋅ Ashton Covey SubDv. ⋅ 33884 Zip Code

Pre-Construction. To be built. Welcome to Ashton Covey in Winter Haven! The Baymont 2-car garage single-family home has it all, all on one level. A welcoming foyer invites you inside and leads you past 2 spacious bedrooms to a unique flex space, which can be used as a study or an additional bedroom. From there, a large great room is where you’ll make memories with family and friends, and it flows directly into the gourmet kitchen. Set up games or enjoy homemade meals around the large center island. At the end of the day, escape to your main-level owner’s suite with its tray ceiling, walk-in closet and double-vanity bath. This is the next level of great living. Discover the ultimate Florida lifestyle in this stunning community. Perfectly situated just off US Highway 27, your new home offers seamless access to work, outdoor recreation, shopping, dining, and more. Imagine being less than 15 minutes from Downtown Winter Haven, where charming local shops and restaurants await your exploration. Plus, you're just 5 miles from public lake access at Lake Daisy, ideal for a day of boating, paddle boarding, and enjoying the water. All Ryan Homes now include WIFI-enabled garage opener and Ecobee thermostat. **Closing cost assistance is available with use of Builder’s affiliated lender**. DISCLAIMER: Prices, financing, promotion, and offers subject to change without notice. Offer valid on new sales only. See Community Sales and Marketing Representative for details. Promotions cannot be combined with any other offer. All uploaded photos are stock photos of this floor plan. Actual home may differ from photos.

2252 Labrador Loop, Winter Haven

3 Beds ⋅ 2 Baths ⋅ Ashton Covey SubDv. ⋅ 33884 Zip Code

Pre-Construction. To be built. Welcome to Ashton Covey in Winter Haven! The Adeline single-family home is the next level of great living. Enter through the inviting front porch or attached 2-car garage into the large foyer. Inside, laughter comes from the spacious great room, the heart of your home. The adjoining gourmet kitchen, with large center island and connected dining space, can flow seamlessly outside to an optional lanai. After you’ve relaxed with loved ones, let them retreat to either of 2 bedrooms while you recharge in your main-level owner’s suite with its dual vanity bath and expansive walk-in closet. This is all you’ve wanted, all on one level. Discover the ultimate Florida lifestyle in this stunning community. Perfectly situated just off US Highway 27, your new home offers seamless access to work, outdoor recreation, shopping, dining, and more. Imagine being less than 15 minutes from Downtown Winter Haven, where charming local shops and restaurants await your exploration. Plus, you're just 5 miles from public lake access at Lake Daisy, ideal for a day of boating, paddle boarding, and enjoying the water. All Ryan Homes now include WIFI-enabled garage opener and Ecobee thermostat. **Closing cost assistance is available with use of Builder’s affiliated lender**. DISCLAIMER: Prices, financing, promotion, and offers subject to change without notice. Offer valid on new sales only. See Community Sales and Marketing Representative for details. Promotions cannot be combined with any other offer. All uploaded photos are stock photos of this floor plan. Actual home may differ from photos.

2240 Labrador Loop, Winter Haven

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