Winter Haven Homes For Sale & Real Estate - 913 homes

Remarks: With expanded living areas and versatile spaces, this home offers a comfortable and practical Florida lifestyle in a well-established Winter Haven community. New flooring and fresh interior paint provide a clean, neutral foundation ready for its next owner. Tucked toward the back of the community and accessed by charming, canopy tree-lined roads, the setting offers a peaceful, neighborhood feel ideal for evening walks or bike rides. The enclosed Florida room adds valuable square footage and serves as a flexible extension of the main living area, perfect for everyday living or casual entertaining. A fully enclosed and roofed former atrium creates a unique bonus space that can be enjoyed year-round, offering additional flexibility for hobbies, relaxation, or storage. The fenced backyard provides a private outdoor retreat and features resident koi fish, adding a tranquil touch. The home is equipped with a whole-house generator, offering dependable peace of mind. Residents also enjoy access to the community clubhouse and amenities. Conveniently located near shopping, dining, medical facilities, and major roadways, this property combines comfort, function, and location within a charming, established neighborhood.

Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)

Listing Agent: J. Michael Nolen, Jr (863-294-7541)

Remarks: Open and spacious living area is the best way to describe this home. The home features two living areas plus the lanai for additional space. The primary bedroom is large offering two built in closets and a spacious bathroom. The guest bedroom has the bath attached, perfect for visiting guests. The kitchen has an updated island perfect for entertaining. The laundry is located inside the home. Move right into this home, perfect for full time living and spacious for entertaining all the visitors you may have. The TPO roof was installed in 2022 and the ac is 10 years old. Oakwood Estates is a 55+ communities with lots of amenities including two clubhouses, two pools, miniature golf, shuffleboard, tennis courts, and much more. There are activities every day. You can join in or just sit back and enjoy the peaceful community.

Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)

Listing Agent: Kathy Devor (573-450-1679)

Remarks: A delightful ground-floor 1-bedroom, 1-bath condo that embodies comfortable, low-maintenance Florida living. Step inside to a well-sized living room that invites relaxed gatherings and everyday comfort. The kitchen features a gas stove, ideal for home-cooked meals, and both the A/C and water heater are newer, giving you added peace of mind. This home’s HOA covers exterior maintenance, so you can enjoy more time living and less time on chores. As a resident, you’ll also love the community pool, perfect for refreshing dips on warm Florida afternoons. And to make this condo truly move-in ready, the seller is offering a flooring credit — a great opportunity to personalize the space to your taste. Location highlights: Winter Haven is known for its welcoming community and vibrant lifestyle. Enjoy scenic outdoor living with access to the Chain of Lakes lifestyle, where boating, paddleboarding, fishing, and unforgettable sunsets are part of everyday life. The nearby Chain of Lakes Trail offers miles of paved paths perfect for walking, biking, or jogging. Legoland is just up the road!

Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (863-701-2350)

Listing Agent: Andrew Fearn (863-812-1755)

Remarks: Welcome to this beautifully renovated 3-bedroom, 2-bath family home tucked away on a quiet street. Set on a spacious .39-acre fenced lot, this property offers both privacy and room to roam — perfect for families, pets, or anyone who loves the outdoors. Step inside to find fresh new flooring, a completely updated kitchen with new appliances, and modern interior and exterior paint that give the home a crisp, inviting feel. The family room with a cozy fireplace creates a warm gathering space, while the large screened porch provides the ideal spot to relax and enjoy year-round. With a new roof and new A/C, this home blends comfort and peace of mind with modern updates. Move-in ready and full of charm — come see it for yourself!

Listing is courtesy of: KLINE REAL ESTATE SERVICES (863-287-0204)

Listing Agent: Donna Sealy (863-206-5328)

Remarks: Welcome to the inviting 55+ community of Garden Grove Oaks in Winter Haven, FL. This charming manufactured home offers comfortable living in a peaceful, amenity-rich neighborhood perfect for active adults. Inside, you’ll find a bright, open layout with a spacious living area ideal for relaxing or hosting company. Brand-new flooring has just been installed, giving the home a fresh, updated feel. The kitchen offers plenty of cabinetry, solid counter space, and a cozy dining nook. The primary bedroom provides a comfortable retreat with great storage, and the additional bedroom works well for guests, hobbies, or a home office. Enjoy Florida living year-round in the screened porch — perfect for morning coffee or evening breezes. You’ll also appreciate the covered parking, exterior storage, and easy-care landscaping. The property sits high and dry, even during heavy storms, giving you added peace of mind. The community also provides live security in the evenings, offering an extra layer of comfort and safety. Garden Grove Oaks is known for its friendly atmosphere and strong amenities: a clubhouse, pool, shuffleboard courts, and regular community activities that keep you active and connected. With shopping, dining, medical facilities, and Winter Haven attractions just minutes away, this home delivers comfort and convenience in a truly sought-after 55+ community. Don’t miss your chance to make this your next Florida home.

Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)

Listing Agent: Don Jerue (863-259-9550)

Remarks: The property you are inquiring about is located in Winter Haven, FL, in the Mandolin area of Polk County. This is a just like designer home in the SE gated community of Mandolin. This is the beautiful model with divided bedrooms, supersized main suite and a fabulous floor plan for entertaining. The kitchen is the vocal point with conversation and dining all flowing together for a warm family friendly environment. Roof and hot water 1 year old, oak cabinetry, two-car garage, and priced ??? Tell us what you think to be in a 33884 gated community at this price!!! Call, text, or email to see this property! *Agents, please read MLS remarks.*

Listing is courtesy of: BROKERS REALTY OF CENTRAL FLOR (863-294-6773)

Listing Agent: Renee Butler (863-294-6773)

Remarks: Located in the highly desirable 55+ maintenance-free gated community of Traditions on Lake Ruby, this wonderful 2-bedroom, 2-bathroom home offers charm, functionality, and an exceptional lifestyle. Upon arrival, you’re greeted by a welcoming Screened-in front porch decked out with tile flooring. Inside, the open-concept floor plan features a spacious living room with vaulted ceilings, Laminate wood flooring, a decorative planter shelf, and triple glass sliding doors leading to the Florida room. The eat-in kitchen showcases an arched entryway, maple wood cabinetry, and corian countertops. Functional upgrades include a stainless steel double bowl sink with a gooseneck faucet, a closet pantry and Upgraded Refrigertor. A charming breakfast nook is ideal for casual dining, while the formal dining area—enhanced with sliding glass doors that open to the fenced yard—seamlessly blends indoor and outdoor living. Solid surface flooring throughout the main living areas ensures style and easy maintenance. The primary bedroom suite features Laminate Wood flooring, a walk-in closet, and views of the backyard. Its ensuite bath includes a maple wood vanity, and a walk-in shower with a glass enclosure. Outdoor enjoyment awaits with a fully fenced yard—perfect for relaxation or entertaining. Additional highlights include a Florida room with tile flooring, Laundry Room, with utility sink, washer & dryer, irrigation system, architectural shingle roof (2020), Water Filtration system, water heater (2023), gutters, generator outlet, solar powered attic vent fan, pull down attic stairs, a 2-car garage with door opener and keyless entry pad, plus a paved driveway and walkway. Traditions at Ruby Lake offers an exceptional array of amenities: a lakefront clubhouse, dock and boat ramp, heated swimming pool and spa, ballroom, billiards, meeting rooms, library, computer room, craft room, dog park, tennis and pickleball courts, basketball, bocce, shuffleboard, fitness center, aerobics studio, and more. The monthly HOA fee covers exterior house painting, cable, internet, front-yard lawn service, and access to clubhouse amenities. . Conveniently located near shopping, restaurants, LegoLand and major routes, this home offers an exceptional and carefree lifestyle.

Listing is courtesy of: CENTURY 21 MYERS REALTY LAKE WALES (863-676-4448)

Listing Agent: Eileen Belanger (863-221-0229)

Remarks: PEACEFUL WATERFRONT Living! Many Beautiful Features & Oversized Living Areas Great for Entertaining! 3.2 Miles to Legoland! Formal Living & Dining Rooms, Family Room, and BONUS Room Upstairs (great for crafts, reading, or toys). Primary Suite offers sitting area & plenty of closet space. So much Extra Space that you could have a roommate helping pay the mortgage. Beautiful Kitchen Featuring Extra Space with Cooking Island & LARGE WALK-IN PANTRY! Eat-in Space OVERLOOKING THE WATER! Enjoy Living in the Waterski Capital of the World Featuring the Chain of Lakes! All sizes are approximate. You will love this home!!

Listing is courtesy of: KELLER WILLIAMS REALTY SMART (863-577-1234)

Listing Agent: Jenni Thompson (863-899-5255)

Remarks: Under Construction. Welcome to the Campbell, a stunning four-bedroom, two and a half bathroom home located in the heart of Winter Haven, Florida at our Harmony at Lake Eloise community. A beautiful patio welcomes you to a home that optimizes living space with an open concept kitchen overlooking the living area, dining room, and outdoor lanai. Entertaining is a breeze, as this popular single-family home features a spacious kitchen island, quartz countertops, dining area and a walk-in pantry for extra storage. Ample windows and a set of sliding glass doors allow lighting into the dining area and luxury vinyl plank flooring throughout is stylish and charming. The first floor also features a powder bathroom off the living area for convenience. As we head up to the second floor, we are greeted with bedroom one that features an en-suite bathroom with a double vanity and a spacious walk-in closet providing substantial space for storage. Three additional bedrooms, a full bathroom, and a laundry area are located on the second floor. Like all homes in Harmony at Lake Eloise, the Campbell includes a Home is Connected smart home technology package which allows you to control your home with your smart device while near or away. With its spacious layout and contemporary finishes, the Campbell in Harmony at Lake Eloise provides the perfect blend of style and functionality. *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.*

Listing is courtesy of: DR HORTON REALTY OF CENTRAL FLORIDA LLC (407-250-7299)

Listing Agent: Paul King (407-519-3940)

Remarks: Best-Priced 2BR Villa with Garage in Vienna Square – and it’s a corner! Built 2022 Welcome to one of the best values in Vienna Square—this corner unit is a light-filled 2-bedroom, 2-bath villa with a 2+ car private garage. You’ll have low-maintenance living in one of Winter Haven’s most sought-after 55+ communities. Built in 2022, this home features a bright, open-concept layout with a seamless flow between the living, dining, and kitchen areas—perfect for both everyday living and entertaining. The kitchen offers modern finishes, tons of cabinets, and great sightlines into the main living space. New stainless refrigerator and microwave in December 2025! In-unit laundry closet for convenience! The spacious primary suite includes a private bathroom and 2 generous walk-in closets. The second large bedroom and full bath provide flexibility for guests or a home office. Enjoy your morning coffee or unwind in the evening on the screened lanai, offering a quiet and comfortable outdoor retreat. Refreshed inside and out with most main furniture included. Vienna Square is known for its active, pet-friendly lifestyle and amenities, including a clubhouse, resort-style pool, fitness center, and social activities—all with a convenient location close to shopping, dining, and medical facilities. Association fees include: • Exterior paint • Roof maintenance • Irrigation water • Lawn mowing • Shrub trimming • Spectrum Internet and TV Priced to sell—schedule your showing today. Easy to show for buyer’s agents using ShowingTime.

Listing is courtesy of: FLAT FEE MLS REALTY (813-642-6030)

Listing Agent: Stephen Hachey (813-642-6030)

Remarks: One or more photo(s) has been virtually staged. 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.

Listing is courtesy of: LENNAR REALTY (800-229-0611)

Listing Agent: Ben Goldstein (407-310-7677)

Remarks: Welcome to this well-maintained home located in Winter Haven. This property features several recent upgrades that enhance both style and functionality. The interior showcases all new laminate flooring installed throughout the entire home just six months ago, creating a fresh and cohesive look. The home also features updated lighting fixtures in the dining room and bathrooms, adding a modern touch to the living spaces. Outside, the backyard has been thoughtfully improved with a newly installed fence for added privacy and a spacious paver patio area with a sunshade, perfect for outdoor entertaining, relaxing, or enjoying Florida evenings. Additional exterior upgrades include new sod and landscaping, providing great curb appeal and a welcoming first impression. Residents of the community also enjoy access to a community pool and playground, offering great spaces for relaxation and recreation. This home offers a move-in ready opportunity with tasteful updates both inside and out.

Listing is courtesy of: LA ROSA REALTY PRESTIGE (863-940-4850)

Listing Agent: Yolanda Floyd (863-577-9369)

Remarks: One or more photo(s) has been virtually staged. Brand new, energy-efficient home available NOW! Retreat to your primary suite located in the back of the home for plenty of privacy and offers a huge walk-in closet. Visit Villamar and explore new single-family homes for sale in Winter Haven, FL. Residents will have access to two resort-style amenity centers featuring a clubhouse, pool, and playground. Winter Haven is known for its beautiful chain of lakes with lakeside restaurants and its award-winning community theater. Nearby attractions include Legoland Florida and Peppa Pig Theme Park. A brand-new model and new phase are coming soon. Each of our homes is built with innovative, energy-efficient features designed to help you enjoy more savings, better health, real comfort and peace of mind.

Listing is courtesy of: MERITAGE HOMES OF FL REALTY (813-703-8860)

Listing Agent: Bryan Sumner (813-336-5895)

Remarks: Welcome to this charming and versatile property located in the heart of Winter Haven! This 2-bedroom, 1-bath home offers comfort, character, and added flexibility with a private in-law suite — perfect for extended family, guests, or potential rental income. The main home features a bright and inviting living space, a functional kitchen, and well-sized bedrooms filled with natural light. Roof and AC units are 2020. The separate in-law suite provides its own private entrance, offering privacy and convenience for multi-generational living or investment opportunities. Situated in an established neighborhood, this property is conveniently located near shopping, dining, schools, and just minutes from the Chain of Lakes. Whether you’re a first-time buyer, investor, or looking for a home with extra space for loved ones, this property is full of potential. Schedule your private showing today!

Listing is courtesy of: BOARDWALK REALTY ASSOCIATES, LLC (800-567-0535)

Listing Agent: Amanda Johnson (310-554-9364)

Remarks: Under Construction. New construction home with 1,486 square feet on one-story including 3 bedrooms, 2 baths, and an open living area. Enjoy an open kitchen with Quartz countertops, Samsung stainless steel appliances, pantry, and a spacious counter height bar, fully open to the dining café and gathering room. The living area, laundry room, and baths include luxury wood vinyl plank flooring, with stain-resistant carpet in the bedrooms. Your owner's suite is complete with a walk-in wardrobe and a private en-suite bath with dual vanities, a tiled shower, and a closeted toilet. Plus, enjoy a covered lanai, 2-car garage, custom-fit window blinds, architectural shingles, energy-efficient insulation and windows, and a full builder warranty. Please note, virtual tour/photos showcases the home layout; colors and design options in actual home for sale may differ. Furnishings and decor do not convey."

Listing is courtesy of: CAMBRIDGE REALTY OF CENTRAL FL (863-797-4999)

Listing Agent: George Lindsey, Iii (863-797-4999)

Remarks: BRAND NEW ROOF INSTALLED NOVEMBER, 2025. Enjoy the Florida Country Club Lifestyle in this 2 bedroom patio home featuring a foyer with wet bar, spacious living room, dining area, kitchen with wood cabinets and converted Florida room, ideal as a den, office or play room. Additional amenities include an expansive master bedroom, 2 car garage with door opener and front courtyard wall. The home is in move-in condition but does have some original features and it's priced accordingly. This is an ideal opportunity to make this home your own with some contemporary updates. The home is currently tenant occupied on a month to month rental but the tenant may be willing to stay on for an investor purchase. Tenant has been there for 3 years.

Listing is courtesy of: LOCKHART & ASSOCIATES INC (863-293-1234)

Listing Agent: Steven Smith, Pa (863-224-2297)

Remarks: One or more photo(s) has been virtually staged. SELLER IS MOTIVATED!!! RENTAL POTENTIAL!!! NO HOA!!! 20 MINUTES AWAY FROM LEGOLAND!!! NEW FLOORING INSTALLED IN FEBRUARY 2026!!!! NEW ROOF INSTALLED IN 2022!!! This 3-bedroom, 2-bathroom home offers the perfect combination of comfort, functionality, and location. The property features a screened-in back porch overlooking a private, fully fenced backyard — ideal for relaxing or entertaining. Enjoy your own private pool with both shallow and deep areas, perfect for family fun or hosting guests. The backyard also includes an area of synthetic grass and a basketball hoop, creating a versatile outdoor space for all ages. A standout feature of this home is the spacious storage shed, thoughtfully divided into two areas. One half is fully set up as an office, complete with a wooden desk, chair, wall-mounted whiteboard, and air conditioning — perfect for working from home. The other half offers additional storage space. The home was extensively updated, with a new roof installed in 2022, along with renovations completed the same year. The flooring was replaced in February 2026, giving the home a fresh, modern feel. High-quality, newer appliances add both style and functionality to the kitchen. Conveniently located just 20 minutes from LEGOLAND Florida Resort and about one hour from Tampa and the beautiful beaches of Florida’s west coast. You’re also just minutes away from Publix, McDonald's, restaurants, and everyday conveniences. The seller is highly motivated and welcomes offers — don’t miss this opportunity!

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Julia Ferreira (352-298-7325)

Remarks: Welcome to 1331 34th St NW in Winter Haven, a property offering exceptional potential and versatility This home is ideal for buyers ready to bring their vision and personal updates, offering the opportunity to build instant equity through thoughtful improvements. In addition to the existing layout, the home features a dedicated office space that, with the addition of a closet, could easily function as a third bedroom, providing added flexibility for growing households, guests, or work-from-home needs. The true show-stopping feature is the MASSIVE EXTENDED GARAGE SPACE, OVER 2000SQFT! capable of accommodating up to 12 vehicles. Whether you are a car collector, small business owner, hobbyist, or someone in need of large-scale storage or workshop space, this structure provides flexibility that is rarely found in residential properties. With the right touch, this property can become a highly functional residence paired with unmatched utility space. Beyond the property itself, Winter Haven offers a strong blend of lifestyle, education, and recreation. The area is home to Polk State College’s Winter Haven campus, providing accessible higher education within the city, while larger universities such as Florida Polytechnic University, Southeastern University, Florida Southern College, and Warner University are all located within roughly a 15-mile radius, supporting a strong educational and workforce presence in the region. This proximity to multiple colleges and universities helps support steady housing demand, local employment opportunities, and long-term community growth. Winter Haven is widely known as the “Chain of Lakes City,” featuring dozens of connected lakes that support boating, fishing, kayaking, and waterfront recreation. The city also offers major attractions including LEGOLAND Florida Resort and the Peppa Pig Theme Park, making it a destination for both tourism and family entertainment. Downtown Winter Haven adds to the lifestyle appeal with locally owned boutiques, antique shops, a year-round farmers market, and historic cultural venues that help maintain the city’s small-town charm while still offering modern conveniences. For buyers looking for a property with unique functionality, strong surrounding amenities, and long-term upside potential, 1331 34th St NW represents a rare opportunity. With renovation potential inside and extraordinary garage and workspace capacity outside, this property is ready to be transformed into something truly special while being positioned in one of Polk County’s most lifestyle-rich communities.

Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (863-701-2350)

Listing Agent: Andrew Fearn (863-812-1755)

Remarks: Under contract-accepting backup offers. Short Sale. Welcome to your 3 bedroom 2 bathroom home located conveniently in Winter Haven with easy access to shopping, dining, and major roadways. The roof and AC were replaced in 2023. This home features luxury vinyl plank flooring throughout. The living room is spacious and features vaulted ceilings. The kitchen has been remodeled and features newer cabinets and granite countertops and a closet pantry. The primary bedroom is spacious with a walk in closet and en-suite bathroom. The remaining bedrooms offer plenty of space and share the main hall bathroom featuring a single sink vanity and tub/shower combo. The home also features a large screened in back porch, the perfect spot for entertaining. This home has so much to offer. Schedule your private showing today!

Listing is courtesy of: KELLER WILLIAMS REALTY SMART (863-577-1234)

Listing Agent: Casandra Vann (863-546-5446)

Remarks: Step into comfort and versatility with this beautifully maintained two-story home featuring 4 spacious bedrooms and 3 full bathrooms, perfect for growing families or those who love extra space. Enjoy peace of mind with a brand-new air conditioning system installed in 2025, ensuring year-round comfort. The home offers a well-designed layout with a spacious walk-in pantry, ideal for keeping your kitchen organized and functional. A mix of laminate, tile, and carpet flooring adds both style and practicality throughout the home. Upstairs, you’ll find a convenient laundry closet, making everyday living even easier. The two-car garage has been partially converted, offering flexible space that can be used as needed while still maintaining storage options. Outside, the ample driveway provides plenty of parking for guests and multiple vehicles. This home combines comfort, functionality, and flexibility, ready for you to make it your own!

Listing is courtesy of: GIPSTAR REALTY LLC (954-678-8416)

Listing Agent: Johanna Carmona (954-865-3673)