Winter Haven Single Family Homes For Sale - 778 homes

Remarks: BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. Feel at home with the Magenta, a single-story home with 3 bedrooms, 2 bathrooms, and a 2-car garage. This layout is a true gem, seamlessly blending modern comfort with Florida charm. Open concept living dazzles with luxury vinyl plank flooring throughout the main living areas. The kitchen, featuring quartz countertops, new stainless-steel appliances and ample storage overlooks the dining and living area. A dreamy, covered lanai, accessible through sliding glass doors, invites you to take full advantage of the Florida climate. The owner’s suite boasts double vanities, a walk-in shower and a substantial walk-in closet, while the additional bedrooms and full bathroom are located off the kitchen for added privacy. With a brand-new washer and dryer conveniently located off the foyer, a smart thermostat with voice control to maintain energy efficient living, and professionally curated landscaping, the Magenta is designed to make every day extraordinary. Just off US-27 with quick access to I-17, Villa Mar puts you close to local hotspots, and everything that makes Central Florida shine. Discover Winter Haven’s Chain of Lakes, explore the historic downtown district, or enjoy a fun-filled day with the family at LEGOLAND® Florida Resort. At Villa Mar, you’ll enjoy a fresh approach to relaxed living, with everyday essentials and local favorites right around the corner. Images shown are for illustrative purposes only and may differ from actual home. Completion date subject to change. Contact or make an appointment for more details on interest rates.

Listing is courtesy of: CASA FRESCA REALTY (813-343-4383)

Listing Agent: Michael Human (813-343-4383)

Remarks: Under Construction. BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. Feel at home with the Magenta, a single-story home with 3 bedrooms, 2 bathrooms, and a 2-car garage. This layout is a true gem, seamlessly blending modern comfort with Florida charm. Open concept living dazzles with luxury vinyl plank flooring throughout the main living areas. The kitchen, featuring quartz countertops, new stainless-steel appliances and ample storage overlooks the dining and living area. A dreamy, covered lanai, accessible through sliding glass doors, invites you to take full advantage of the Florida climate. The owner’s suite boasts double vanities, a walk-in shower and a substantial walk-in closet, while the additional bedrooms and full bathroom are located off the kitchen for added privacy. With a laundry room located off the foyer, a smart thermostat with voice control to maintain energy efficient living, and professionally curated landscaping, the Magenta is designed to make every day extraordinary. Just off US-27 with quick access to I-17, Villa Mar puts you close to local hotspots, and everything that makes Central Florida shine. Discover Winter Haven’s Chain of Lakes, explore the historic downtown district, or enjoy a fun-filled day with the family at LEGOLAND® Florida Resort. At Villa Mar, you’ll enjoy a fresh approach to relaxed living, with everyday essentials and local favorites right around the corner. Images shown are for illustrative purposes only and may differ from actual home. Completion date subject to change. Images shown are for illustrative purposes only and may differ from actual home. Completion date subject to change.

Listing is courtesy of: CASA FRESCA REALTY (813-343-4383)

Listing Agent: Michael Human (813-343-4383)

Remarks: Under Construction. Indigo BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. Check out the Indigo, a spacious two-story, 5-bedroom, 3-bathroom, 2-car garage home perfect for growing families or hosting guests. Enter the impressive foyer with soaring ceilings that creates an immediate sense of openness. From the foyer, the home effortlessly flows into the main living areas and kitchen. With quartz countertops throughout, stainless-steel appliances and a smart thermostat for energy efficient climate control, the Indigo brings all the things that matter together. The downstairs guest suite and bathroom are tucked away for added seclusion, while the open concept living space is perfect for entertaining. Upstairs, you'll find a generously sized recreation space, ideal for family time or unwinding. The owner's suite is a true sanctuary, featuring a walk-in shower, double vanities, and a spacious walk-in closet. A laundry room with a new washer and dryer is just off the owner’s suite, conveniently located near the 3 additional bedrooms and full bathroom. The Indigo is as functional as it is stylish, providing the perfect balance of comfort and modern living. Close to it all, Villa Mar places you near the natural beauty of the Winter Haven Chain of Lakes, the charm of downtown Winter Haven, and family fun at LEGOLAND® Florida Resort. Back at home, residents enjoy community amenities including a pool, dog park, playground, and walking trails.  Images shown are for illustrative purposes only and may differ from actual home. Completion date subject to change. Contact or make an appointment for more details on interest rates.

Listing is courtesy of: CASA FRESCA REALTY (813-343-4383)

Listing Agent: Michael Human (813-343-4383)

Remarks: This move-in ready 3-bedroom Winter Haven pool home offers a fantastic combination of comfort, upgrades, and true Florida living on an oversized lot with no HOA. The home features a brand-new roof, new HVAC system and thermostat, new water heater, new pool pump and chlorinator, new laundry units, new exterior front doors, and an expanded driveway with ample parking. Inside, you’ll find a functional layout with generous living space and fresh improvements throughout. The private in-ground pool creates a relaxing backyard setting, while the large lot provides room for outdoor entertaining, storage, or future additions. Located minutes from the Winter Haven Chain of Lakes, Gene’s Lakeside Marina, LEGOLAND Florida Resort, golf courses, shopping, dining, and local parks, this property sits in one of Central Florida’s most desirable and fast-growing areas. With major updates already completed and convenient access to boating, recreation, and upcoming community development, this home is an excellent opportunity for first-time buyers, families, or investors.

Listing is courtesy of: THE URBAN GROUP, INC. (954-522-6226)

Listing Agent: Ashlee Morrell (941-740-9134)

Remarks: Welcome to 1000 Lena Run Ct — a thoughtfully designed 4-bed, 3-bath pool home offering space, privacy, and timeless appeal. The moment you step inside, you’ll notice the attention to detail, soaring ceilings, and a smart split floor plan that truly makes sense. With an additional office or bonus room and a three-car garage, this home delivers flexibility for modern living. Perfectly positioned on nearly half an acre in one of Winter Haven’s most desirable gated communities Hidden Creek, it offers rare privacy with no rear neighbors, peaceful natural views, and regular visits from local wildlife — including bald eagles and turkeys. The layout is ideal for families, multigenerational living, or anyone seeking extra space. The screen-enclosed pool area creates a true Florida retreat — perfect for relaxing, entertaining, or enjoying year-round outdoor living. The primary suite is a haven of comfort, featuring a soaking tub and walk-in shower designed for unwinding after a long day. Located just minutes from the Polk Parkway, this home provides easy access to Lakeland and Winter Haven’s top-rated dining, shopping, medical facilities, and attractions — including Legoland, Chain of Lakes recreation, and other local favorites. Move-in ready and beautifully maintained, this property blends convenience with a tucked-away feel — a rare opportunity to own a private pool home in a sought-after Winter Haven community.

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

Listing Agent: Sarah Garner (863-303-4665)

Remarks: Under contract-accepting backup offers. POOL HOME ON AN OVERSIZED CORNER LOT WITH A SCREENED LANAI, DETACHED SHE SHED/MAN CAVE, AND A FULLY FENCED BACKYARD! Tucked beneath mature shade trees in Winter Haven's established High Point community, this well-maintained home offers the space, flexibility, and outdoor living opportunities that many buyers have been searching for. From the inviting covered front porch to the multiple outdoor gathering areas, every part of this property is designed to be enjoyed. Step inside to a bright and welcoming interior where natural light fills the living spaces and creates a comfortable atmosphere throughout. The living room serves as the heart of the home and flows effortlessly into the dining area and kitchen, creating a layout that feels connected and functional for both everyday living and entertaining. The kitchen features ample cabinetry, generous countertop space, stainless steel appliances, breakfast bar seating, and easy access to the home's outdoor living areas. The home offers three comfortable bedrooms, each providing flexibility for family, guests, hobbies, or a home office. The centrally located bathroom features a dual-sink vanity with ample storage and countertop space. An indoor laundry room adds everyday convenience, and an additional flexible room currently used for storage offers opportunities for future use based on your needs. One of the home's standout features is the expansive screened lanai stretching across the rear of the property. This impressive outdoor living space creates the perfect setting for morning coffee, outdoor dining, game days, or relaxing evenings while enjoying Florida's beautiful weather. Beyond the lanai, the fully fenced backyard offers multiple areas to gather, entertain, and unwind. The above-ground pool creates a refreshing backyard retreat surrounded by mature landscaping and outdoor living spaces. A detached 12x20 she shed/man cave provides exceptional flexibility and can easily be utilized as a hobby room, creative studio, fitness space, game room, workshop, or private retreat. The property also features two separate carports, providing covered parking and additional space for vehicles, equipment, projects, and everyday convenience. The oversized corner lot offers additional outdoor space and versatility rarely found in many homes of this size. Whether you're hosting family gatherings, working on hobbies, gardening, relaxing by the pool, or simply enjoying the shade of the mature trees, this property provides room to live, work, and play. Conveniently located near shopping, dining, parks, schools, medical facilities, Winter Haven's renowned Chain of Lakes, Legoland Florida Resort, downtown Winter Haven, and major roadways connecting throughout Central Florida, this home offers convenient access to everyday essentials and local recreation. If you've been searching for a property that offers more than just a house—a place with room to gather, relax, create, and enjoy the Florida lifestyle—this home is ready to welcome its next owner.

Listing is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)

Listing Agent: Simi Lakhani (407-408-7393)

Remarks: New - New - New! This 3 bedroom 2 bath features a beautiful lake view and has been completely remodeled. Updates include a new HVAC system, new metal roof, new kitchen with granite counters, new bathrooms, new flooring, and new septic system. No HOA means you can store your boat. Can be purchased together with 73 High Street to make a family compound or have an income producing property. (MLS P4937859)

Listing is courtesy of: ALLSTATE REALTY SERVICES (863-965-0207)

Listing Agent: Dwight Head (863-965-0207)

Remarks: Welcome to this beautifully maintained newer home in the desirable Squires Grove community of Winter Haven! Built in 2022, this spacious 3-bedroom, 2-bath residence offers an open-concept layout with a bright living and dining area—perfect for entertaining. The modern kitchen features ample cabinetry, sleek appliances, and a large island overlooking the main living space. A split-bedroom floor plan provides privacy, with a generous primary suite including a walk-in closet and en-suite bath. Enjoy outdoor living in the private backyard with room to relax or host gatherings. Additional highlights include a 2-car garage, indoor laundry, and energy-efficient construction. Conveniently located near shopping, dining, schools, and major roadways, this home offers comfort, style, and convenience in one of Winter Haven’s growing communities.

Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)

Listing Agent: Danielle Williams (813-297-8258)

Remarks: Under Construction. This two-story Georgia will definitely be on your mind… This beauty highlights a modern open layout, seamlessly integrating a first-floor kitchen with a central island, a dining room and a welcoming family room with patio access. On the same level is a private owner's suite with an attached bathroom. Situated upstairs is a versatile loft for additional shared living space and four secondary bedrooms to provide restful retreats to family members and guests alike. 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 FULLY renovated, beautiful and large 3Bed 2bath home in Winter Haven!! Property has been fully renovated to 2026 standards in and out. Fresh pain in and out. Brand new 6" baseboards throughout the home. Crown molding throughout the main living space. Brand new water resistant LVP tile. Pool has been repainted. Walls have been refreshed and smoothened out. Popcorn ceiling through the main home has been sanded down and smoothened. Garage has been given a fresh coating of pain and the floors smoothened. Both Florida rooms have been renovated as well. Roof (2020) A/C (2020) New Water-heater installed (2026) Stainless Steel Samsung Dishwasher (2026) Stainless Steel Samsung Fridge (2026) Stainless Steel Whirlpool Electric Range (2026) Stainless Steel Broan-NuTone Range Hood (2026). Solar Panels are fully owned. Full 3D property walk-through video available upon request. PLEASE NOTE - I AM NOT AVAILABLE ON THE SABBATH/SATURDAYS

Listing is courtesy of: CARDINAL REALTY GROUP, LLC. (305-910-2902)

Listing Agent: Meir Tenenbaum (305-721-7408)

Remarks: Let's make a deal!! Bring them an OFFER!! Turn Key House on the North Chain of Lakes. 2023 Roof, 2022 POOL! Welcome to this pristine, beautifully maintained home in the quiet and highly desirable Island Lakes community—where there’s no through traffic and peaceful living comes naturally. Gorgeous real hardwood floors, stand up tub for the later years, huge shed and a low HOA fee. Step outside and you’ll fall in love with the vinyl-planked dock that gives you direct access to the Chain of Lakes, making it ideal for boating, fishing, and sunset cruises. Whether you prefer relaxing in the screened-in outdoor area or lounging by the sparkling pool, this home is designed for anyone who loves outdoor living. Inside, the home is in immaculate condition. It offers three bedrooms, including a spacious master suite complete with a walk-in tub for easy washing and added convenience. Every room feels well cared for, move-in ready, and prepared for its next owner to enjoy. This stunning property truly has it all—comfort, water access, serenity, and style. It’s ready and waiting for the next buyer who wants to fully embrace lakeside living.

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

Listing Agent: Keith St. Onge (863-651-1397)

Remarks: Charming & Renovated Single Family Home With NO HOA & Great Investment Potential! Welcome to this cozy 3 Bed, 1 Bath residence that features a seamless open floor plan, with a bright living room and dining room combo that flows into the modern kitchen. The interior has been thoughtfully updated with luxury vinyl and tile flooring throughout, providing a stylish and easy-to-clean environment. The private backyard is spacious and perfect for outdoor gardening or relaxing. Located just 5 miles from LEGOLAND Florida, this property offers excellent access to major highways, hospitals, lakes, and all of Central Florida's top attractions. The home is "rental-ready" and has strong income potential as a short-term or long-term rental. Schedule a private tour and make this beautiful home your new residence or add to your income producing profolio... Matterport 3D tour is available that provide virtual 3D tour & room measurements.

Listing is courtesy of: KN PREMIER REALTY, INC (407-668-8888)

Listing Agent: Guanhua Zhang (407-668-8888)

Remarks: Relaxed golf community living inside the gated and guarded Cypresswood Golf & Country Club. Welcome to 460 Pinehurst Ct in Winter Haven, Florida — an updated and spacious 2 bedroom, 2 bath patio home tucked away on a quiet cul-de-sac street with no through traffic. A private walled walkway leads to a charming front porch with sitting area, creating a warm and welcoming approach. Step inside the foyer to discover a clean, updated interior offering more than 1,600 square feet of comfortable living space, highlighted by beautiful new flooring, a freshly painted interior, and a long list of thoughtful improvements. All carpeting has been removed, the outdated popcorn ceilings have been scraped and refinished for a more modern look, and the overgrown landscaping has been cleared away to create a clean, attractive, and easy-to-maintain property. The roof was replaced in 2020 for added peace of mind, and gutters have also been installed for convenience and functionality. The great room design creates a spacious and open feel, accentuated by built-in shelving and large glass sliders that bring in natural light while offering the perfect space to showcase personal décor and seasonal accents. Sliding glass doors open to the enclosed, air-conditioned Florida room, seamlessly expanding the living area and creating an easy indoor-outdoor lifestyle that can be enjoyed year-round. The great room also offers space for formal dining in addition to the casual eat-in area found within the kitchen. The generously sized kitchen features abundant real wood cabinetry, a large breakfast bar, closet pantry, and an inviting dining area ideal for casual meals and everyday living. The primary suite offers comfortable dimensions, a walk-in closet, and an en-suite bath complete with a tiled walk-in shower. The guest bedroom is also nicely sized and features its own walk-in closet along with convenient access to the full guest bathroom with tub and shower. Storage is abundant throughout the home with multiple interior closets, garage storage closets, and a spacious 2-car garage with laundry connections, helping keep everything neatly organized and out of sight. Additional features include an irrigation system and low-maintenance exterior living. Beyond the home, Cypresswood delivers one of Winter Haven’s most enjoyable golf community lifestyles. Residents enjoy access to the 18-hole championship golf course, originally opened in 1969 and designed by award-winning architect Ron Garl. Known for its rolling fairways and mature landscaping, the course also features a pro shop, driving range, putting green, and dedicated short-game practice areas. Just a short stroll from the home, residents can enjoy the recently refurbished junior Olympic-sized swimming pool, tennis courts, pickleball courts, and Wellness Center. The Cypresswood Pub & Restaurant serves as the social heart of the community, offering planned events, a full bar, great food, and live weekend music in a relaxed setting overlooking the golf course. Whether you are searching for a full-time residence, winter retreat, or low-maintenance golf community home, 460 Pinehurst Ct offers an exceptional opportunity to enjoy the Florida lifestyle in one of Winter Haven’s most established gated golf communities.

Listing is courtesy of: THE STONES REAL ESTATE FIRM (863-412-2080)

Listing Agent: Michael Stone (863-412-9733)

Remarks: Under Construction. This BEATIFUL ROBIE Model home has 5 bedrooms, 3 baths & a 2-car garage-2447 SqFt. NEWLY UPGRADED! Large 2-STORY open floor plan with Living & Dining room & Kitchen to entertain & enjoy the company of your guests. One bedroom located in the first floor, W/FULL BATH. Your very spacious master suite located on the 2nd floor with a large walk-closet & a double sink vanity with stall shower. This Home provides Stainless Appliances which include range, hood microwave, refrigerator, dishwasher and much more. We also provide Smart Home Technology which allows you to set the scene and connect to your home with your voice, from your smart phone, or through the smart panel interface. Your Smart Home comes with Alarm app, Echo Dot, Kwikset Smart Front Lock, IQ Panel, SkyBell, Z-Wave Thermostat, and a Z-Wave Light Switch. *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: Under Construction. Let me Introduce you to the Astor this 1593 Sqft. 3 Bedroom 2 Bath home with the Garage in the rear is just to die for. This home provides Luxury Vinyl tile in all the wet areas, Living and Dining Rooms and Quartz Counter tops in the Kitchen and both Bathrooms. The Kitchen includes a Stove, Microwave, Dishwasher and Refrigerator, all Stainless Steel by Whirlpool and also includes a Washer/Dryer. The Astor has an Open Floor plan that allows you to entertain guest even if they are in the living or dining room. Spacious bedrooms and an Owners Suite that can easily fit a King size bed. If you like sitting outside, you have a covered lanai that is perfect for BBQing. And on top of all that it also comes with our Home Smart System. Come by today!

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

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

Remarks: Short Sale. Located in the Villamar community of Winter Haven, this 3-bedroom, 2-bath home built in 2023 offers modern construction with a two-car garage and a functional layout designed for everyday living. The home features open living spaces, well-sized bedrooms, and contemporary finishes typical of newer construction. The property appears to require cosmetic refreshing, presenting an opportunity for buyers to personalize a relatively new home without undertaking a major renovation. With a low HOA of approximately $212 and no flood zone designation, this home offers both affordability and added peace of mind. Conveniently located near shopping, dining, schools, and major roadways throughout Winter Haven and Polk County. Buyers are encouraged to conduct their own inspections to determine condition. Agents: Please review all private remarks prior to scheduling a showing.

Listing is courtesy of: KELLER WILLIAMS ELITE REALTY (239-949-8338)

Listing Agent: Jonathon, Pa Mcleod (239-357-8938)

Remarks: Welcome to this beautifully updated home in Winter Haven! This move-in ready property combines classic charm with modern upgrades, featuring stunning high-gloss marble-style porcelain flooring throughout that creates a bright and elegant living space. Enjoy a spacious layout filled with natural light, a well-maintained kitchen with stainless steel appliances, wood cabinetry, and a stylish backsplash — perfect for everyday living. The home also offers a renovated bathroom with modern finishes and a convenient interior laundry area. Step outside to a large, fully fenced backyard, ideal for entertaining, pets, or simply enjoying your own private outdoor space. The covered carport and extended driveway provide ample parking. Located in a quiet, well-established neighborhood, this home is perfect for first-time buyers or investors. Property is being sold AS-IS, presenting a great opportunity for buyers looking for value and flexibility. Schedule your private showing today!

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

Listing Agent: Gabriel Rivera Gonzalez (407-724-4717)

Remarks: Welcome to this stunning Bradley floorplan, located in the highly sought-after community of Willowbrook near a beautiful golf course in Winter Haven, FL. This spacious 4-bedroom, 2-bath home offers 1,625 square feet of living space, and provides excellent curb appeal in it's elevation. Inside, you'll find gorgeous White cabinets complemented by sleek quartz countertops in the kitchen, creating a modern, bright atmosphere. Tile flooring runs throughout the wet and common areas, offering durability and easy maintenance. The open layout is perfect for family gatherings and entertaining guests. This home is ideally situated just minutes from the scenic Port 27 and downtown Winter Haven, making it convenient for shopping, dining, and entertainment. Additionally, it's only a short drive to Highway 27 and about 20 minutes to I-4, providing easy access to nearby cities and attractions. Don’t miss the chance to own this beautiful home in a prime location—schedule your tour today!

Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)

Listing Agent: Nancy Pruitt, Pa (352-552-7574)

Remarks: Under Construction. Located in the heart of Winter Haven, Willowbrook South puts you close to the area's Chain of Lakes, beautiful parks, and an array of dining and shopping. With top attractions and everyday conveniences just minutes away, your new home here keeps you connected to everything you love. Your new home at Willowbrook South places you right where you want to be. Let me Introduce you to the Archer II this 1328 Sqft. 3 Bedroom 2 Bath home is just to die for. This home provides Luxury Vinyl tile in all the wet areas, Living and Dining Rooms and Quartz Counter tops in the Kitchen and both Bathrooms. The Kitchen includes a Stove, Microwave, Dishwasher and Refrigerator, all Stainless Steel by Whirlpool and also includes a Washer/Dryer. The Archer II has an Open Floor plan that allows you to entertain guest even if they are in the living or dining room. Spacious bedrooms Owners Suite that can easily fit a King size bed. And on top of all that it also comes with our Home Smart System. Come by today!

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

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

Remarks: Welcome to this beautifully updated 3-bedroom, 1-bath home in Winter Haven! Move-in ready and filled with recent improvements, this property offers comfort, style, and peace of mind. The kitchen was completely updated in May 2025 with new cabinets, granite countertops, and sink, creating a fresh and modern space for everyday living. Major system upgrades include a new roof with warranty (April 2025), new electrical panel with warranty (May 2025), new hot water heater (September 2024), and updated A/C coils and air handler box (January 2024). New flooring installed in October 2025 adds to the home's updated appeal. The living area features a built-in entertainment center with fireplace, added in March 2025, creating a cozy focal point for relaxing or entertaining. Step outside to enjoy the screened back patio, where you'll also find the laundry area for added convenience. Conveniently located near shopping, dining, schools, and major roadways, this well-maintained home is ready for its next owner. Schedule your private showing today!

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

Listing Agent: Tiffany Steck (937-430-9119)