Winter Haven Homes For Sale & Real Estate - 969 homes

Remarks: Under Construction. The Ponte Vedra floor plan at Willowbrook North offers spacious two-story living with 5 bedrooms, 3 full baths, and approximately 2,371 square feet of thoughtfully designed space. This open-concept home features a modern kitchen overlooking the great room and dining area, a spacious primary suite, flexible living areas, and available options. Located near Lake Fannie and adjacent to Willowbrook Golf Club, Willowbrook North offers scenic surroundings with convenient access to shopping, dining, parks, downtown Winter Haven, and major commuter routes to Orlando and Tampa. Buyers will also enjoy energy-efficient features and modern interior finishes.

Listing is courtesy of: DRB GROUP REALTY, LLC (407-270-2747)

Listing Agent: Adam Schott (407-270-2747)

Remarks: Spacious 4-Bedroom, 3-Bath Pool Home in the admired Lakewood Community. Nestled on an oversized lot with mature trees, this remodeled tri-level home offers a perfect blend of modern luxury and comfort. With a spacious layout, a private pool, and an abundance of natural light, this home is designed for both relaxation and entertaining. As you enter, you’ll immediately notice the bright and airy atmosphere created by large windows that allow natural light to flood the home. The home features stunning luxury vinyl plank flooring and a beautiful brick fireplace, adding warmth and character to the space. The kitchen is of good size and boasting sleek countertops, new modern appliances, and ample cabinet space. Enjoy casual meals in the eat-in kitchen or step outside to the screened-in porch, an ideal spot for dining al fresco or simply relaxing while overlooking the expansive backyard and pool. Come add your personal touches and make this house your beautiful home!

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

Listing Agent: Michelle Armbruster (863-521-6879)

Remarks: Under contract-accepting backup offers. Under Contract. Winter Haven Single Family Residential home, 3B/1ba offers a well landscaped Corner Lot. The Interior accommodates Electric AC & natural gas heat. This home still boasts original well maintained kitchen cabinets, eat-in kitchen & gas oven appliances. The Exterior features are Concrete Block Detached storage/workshop 20x14’, covered carport 20x12’, exterior lighting,pvc plumbing, irrigation well/pump, pole barn for RV parking 28x20’, carport, brand new hot water heater, enclosed concrete outside laundry room. This home offers updated plumbing and abundant parking. Pride of Ownership. A must see!

Listing is courtesy of: WATSON & WATSON INC REALTORS (863-294-4149)

Listing Agent: Wendy Gibbs (863-557-5249)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Newly renovated 2 bedroom, 2 bathroom home with all the major updates already done for you — new roof, new floors ,new AC, and new water heater. This is a boater and fisher’s dream property located on beautiful Lake Dexter, Enjoy boating, water skiing, and freshwater fishing right from your backyard playground. The community offers a dock with boat slips available on a first-come, first-served basis, perfect for boats up to 24 feet. Residents also enjoy a clubhouse, pickleball courts, and tennis courts, making it easy to enjoy the Florida lifestyle. Whether you're looking for a full-time residence or a weekend lake retreat, this home offers the perfect mix of updates, amenities, and waterfront living.

Listing is courtesy of: ELEVE REAL ESTATE LLC (813-562-5002)

Listing Agent: Danielle Davis (813-526-5002)

Remarks: Back on market! Cute as a button, historic charm with some nice updates. From the welcoming front porch to the massive fenced back yard, complete with dog washing station, this is a cozy spot to call home! Love the original hardwood floors, open bright kitchen, and character such as built ins. Roof is less than 10 years old, and the sellers have updated the HVAC including adding a mini split to the main bedroom for those who like it extra cold at night. Plenty of parking and extra storage outside as well...check this one before it gets away!

Listing is courtesy of: HARPER REALTY FL, LLC (863-687-8020)

Listing Agent: Paula Shields (863-581-1498)

Remarks: Welcome to 2436 Edwin St NE, Winter Haven, FL 33881(POLK COUNTY). This beautifully designed 4-bedroom, 2-bathroom brand-new manufactured home offers a spacious, open floor plan ideal for modern living. Designed for the modern lifestyle, the spacious open floor plan is bathed in natural light and features durable, high-end vinyl flooring throughout (no carpet!). The massive living room transitions seamlessly into the dining area and kitchen, creating an ideal layout for entertaining. Need extra space? The separate family room provides the perfect footprint for a home office, media room, or playroom. The heart of the home is a chef-inspired kitchen that checks every box: Brand-new stainless-steel appliances, Oversized central island with breakfast bar seating, Stylish shaker-style cabinets with ample storage. The master suite is a private sanctuary, featuring a massive walk-in closet and a luxurious en-suite bath complete with a modern walk-in shower. Three additional generously sized guest bedrooms and a second full bathroom with a soaking tub ensure plenty of room for family and guests. Home also features Sliding Glass door. Enjoy the peace of country living while staying minutes away from Winter Haven’s Chain of Lakes, shopping, dining, and major Central Florida attractions (LEGOLAND, DISNEY, UNIVERSAL STUDIOS). With a dedicated utility/laundry room and a brand-new energy-efficient build, this home is move-in ready and built to last. Schedule your private tour today and experience the best of Florida living! Schedule your private tour today and experience the best of Florida living!

Listing is courtesy of: J&T PROPERTY SOLUTIONS GROUP LLC (863-440-3603)

Listing Agent: Jennifer Daniell (863-440-3603)

Remarks: Under contract-accepting backup offers. Step inside through the large enclosed foyer—perfect as a welcoming entryway, mudroom, or additional sitting space. The home features a comfortable living room and a well-appointed kitchen with a separate dining area, ideal for everyday living and entertaining. A bonus back room provides flexibility and can easily be used as a home office, hobby room, or additional living space. Enjoy outdoor living on the covered back porch overlooking a fully fenced yard—perfect for pets, gatherings, or simply relaxing in your own private oasis. The property is a true gem for those who love fresh fruit, featuring numerous mature trees including mango, avocado, peach, lemon, and other citrus varieties. Additional highlights include two large storage sheds with electricity already in place, offering excellent space for a workshop, storage, or creative projects. There is also a full RV hookup with electric, water, and septic—perfect for travelers or accommodating guests. This property offers a rare combination of comfort, utility, and outdoor enjoyment. Don’t miss this opportunity to own a home with so much to offer!

Listing is courtesy of: LAND SOUTH REALTY, LLC (863-937-8867)

Listing Agent: Ron Denney (863-660-3919)

Remarks: NO HOA! This 2 bedroom, 1 bathroom property has an eat-in kitchen with granite countertops & dining space, and a separate living room for gathering. There is luxury vinyl plank (LVP) floors throughout the home and the bathroom has been newly tiled. The home has UV double-insulated windows, 8x10 shed with finished interior, electricity & wall A/C unit, and a spacious fenced backyard with vehicle gate. Seller updates include screen-enclosed front entry, landscape & sod, bathroom tile, crown molding, living room ceiling fan, LVP & baseboards, and finished shed. This home sweet home is tucked away approximately a half mile to Havendale Blvd which leads to groceries, restaurants and connecting highways/roads for commutes. A brand new Publix will soon be opening right next to this neighborhood! Bring your watercraft because you're approximately one mile to a public boat ramp for Lake Jessie which is known for its fishing, aviation activity (including seaplanes!), and is part of Winter Haven's famous Chain of Lakes.

Listing is courtesy of: REDFIN CORPORATION (407-708-9747)

Listing Agent: Juan Castro (407-808-5353)

Remarks: Whether you're a first-time buyer, downsizing, or investing, this canal-front townhome is an opportunity you don't want to miss. Enjoy access to Winter Haven's Chain of Lakes at a fraction of typical waterfront prices. This home features an open layout with modern finishes, ideal for everyday living and entertaining. A private lanai and second-story balcony overlook the canal, which connects to Lake Lulu, Lake Roy, Lake Eloise, and the 15 interconnected lakes of the Southern Chain of Winter Haven's Famous Chain of Lakes spanning over 9,000 acres of waterways. Or take some time for yourself to relax at the community pool on the banks of Lake Lulu. This townhome is centrally located near shopping, dining, and major roadways, offering convenient access to all things Winter Haven. Schedule your showing today.

Listing is courtesy of: THE PROPERTY ADVISERS (863-651-5691)

Listing Agent: Jay Scharff, Jr (863-651-5691)

Remarks: Back on market buyers financing fell through. Welcome home! Your forever home is located near downtown Winter Haven and just a short distance from Polk State College. Completely remodeled in 2021 with a New Roof, New A/C, New Water Heater, New Electrical system, new windows new kitchen (Quartz Countertops), new appliances, new floors (Vinyl). This home has a huge, oversized corner lot and with summer around the corner, this will be the place for all the summer BBQ's.

Listing is courtesy of: FLATFEE.COM (954-965-3990)

Listing Agent: Cliff Glansen

Remarks: This 2-bedroom, 2-bathroom home features a private, screened-in backyard pool. Enjoy nearly non-existent electric bills thanks to a fully paid-off SolarEdge solar system, complemented by a whole-house 22 kW Generac generator with a 250-gallon propane tank, hurricane-rated windows, a 5-year-old architectural shingle roof, and a Rinnai tankless water heater. The spacious interior boasts a large galley kitchen with stainless steel appliances and a gas stove, a convenient indoor laundry room with extra storage, a 2-car garage, and a versatile 16x12 climate-controlled Florida room. This property has been an Airbnb and can be purchased fully furnished, making it a turnkey investment or a move-in-ready retreat!

Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)

Listing Agent: Steven Koleno (804-656-5007)

Remarks: Move-in ready and priced to sell! Located in a quiet, neighborhood with a low HOA of just $200 annually, this beautifully updated 3-bedroom, 2-bath home offers exceptional value, major system updates, and endless potential on a spacious quarter-acre lot. Step inside to discover an inviting open-concept layout where the living room, dining area, and kitchen flow seamlessly together, creating the perfect space for both everyday living and entertaining. The updated kitchen features modern cabinetry, updated fixtures, appliances, and a center island that serves as the heart of the home. Luxury vinyl plank flooring throughout provides a clean, cohesive look and easy maintenance. Designed with privacy in mind, the split-bedroom floor plan offers a spacious primary suite separated from the guest bedrooms. Every bedroom features a walk-in closet, providing ample storage throughout the home. A large Florida room adds valuable additional living space and connects the home’s interior, making it ideal for a home office, playroom, gym, media room, or second living area. Outdoor living is where this property truly shines. Situated on approximately a quarter-acre lot, the expansive backyard offers plenty of room to create your dream outdoor oasis, including space for a future pool. Enjoy peaceful views with acreage behind the property, providing added privacy and a more open feel than many neighboring homes. The 16x16 screened patio with a concrete slab is perfect for relaxing, entertaining guests, or enjoying Florida evenings year-round. Major updates provide peace of mind, including a 2021 roof and 2021 A/C system. Originally constructed with a tile roof design, the home was built to support the additional structural load, contributing to its durability and long-term appeal. Additional highlights include a two-car garage, vinyl privacy fencing, updated appliances, modern fixtures, and thoughtful improvements throughout. Offering a rare combination of location, lot size, recent updates, low HOA fees, and future potential, this property presents an outstanding opportunity in one of the area’s most desirable neighborhoods. Whether you’re looking for a move-in-ready home, additional space to grow, or a property with room to personalize over time, this home checks all the boxes. Seller is motivated. Schedule your private showing today and discover everything this exceptional property has in store.

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Emily Ward (863-632-1865)

Remarks: Welcome to 3097 Buckeye Pointe Drive, a fully updated pool home in Winter Haven, Florida, offering the space, flexibility, and upgrades today's buyers are searching for in Polk County. If you've been looking for a move-in ready home with a private pool, screened spa, modern finishes, and no rental restrictions, this property deserves a spot at the top of your list.Located in the established Buckeye Pointe community, this spacious two-story home features 5 bedrooms, 2.5 bathrooms, and more than 2,500 square feet of living space. The versatile floor plan includes a first-floor bedroom, making it ideal for multigenerational living, visiting guests, a private home office, or a fitness room.From the moment you step inside, you'll notice the extensive updates throughout. The entire first floor showcases oversized 24x36 porcelain tile, creating a clean, modern look that is both stylish and easy to maintain. The renovated kitchen serves as the heart of the home with updated cabinetry, a large center island, upgraded lighting, and newer appliances including the refrigerator and dishwasher. Every bathroom has been remodeled, while fresh interior and exterior paint give the home a bright, updated feel throughout.Step outside and enjoy the Florida lifestyle year-round. The screened and heated pool and spa create the perfect setting for relaxing after work, entertaining family and friends, or enjoying weekend gatherings. The vinyl fenced backyard offers privacy, while mature fruit trees provide character and charm that are increasingly difficult to find. Major improvements include a newer 2023 roof and a 2020 water heater, giving buyers added confidence and helping reduce future maintenance concerns. One of the most attractive features of this property is the absence of rental restrictions. Buyers searching for an Airbnb-friendly home in Winter Haven, a Florida vacation home, a second home near Orlando attractions, or an income-producing investment property will appreciate the flexibility this community offers. Conveniently located near shopping, restaurants, medical facilities, schools, and major transportation routes, this home provides easy access to everything Central Florida has to offer. Whether you're commuting to Orlando, exploring nearby lakes, visiting world-famous attractions, or simply enjoying the growing Winter Haven lifestyle, this location puts you close to it all.Buyers frequently searching for "homes with pools in Winter Haven," "5-bedroom homes in Polk County," "updated homes near Orlando," "Airbnb investment properties in Central Florida," "homes with no rental restrictions," or "move-in ready Florida homes with a pool" will find everything they're looking for at 3097 Buckeye Pointe Drive. This is more than just a house. It's a move-in ready Florida lifestyle with room to grow, space to entertain, and the flexibility to fit your future plans.

Listing is courtesy of: RE/MAX HERITAGE PROFESSIONALS (863-256-2188)

Listing Agent: Desiree Carlson (541-743-1985)

Remarks: Welcome to this immaculate dream home at 3831 Gaines Dr! This beautifully updated 3-bedroom + office home features an open floor plan with stunning upgrades throughout, including an updated kitchen, modern bathrooms, and spacious living areas designed for both comfort and entertaining. The gorgeous kitchen is complete with brand-new appliances and flows seamlessly into the main living space, creating the perfect atmosphere for family gatherings and everyday living. Additional upgrades include a Kinetico water filtration system and an allergen air filtration system to help provide cleaner water and improved indoor air quality throughout the home. Step outside to your own private oasis featuring a heated pool, incredible outdoor kitchen, and a perfectly maintained yard that makes outdoor living effortless year-round. This move-in-ready home truly has it all — luxury, comfort, thoughtful upgrades, and plenty of space to live, work, and entertain!

Listing is courtesy of: THE MARKET REALTY COMPANY (863-999-4643)

Listing Agent: Vikki Thielen (863-604-6627)

Remarks: ~2/2 Winter Haven residence Offered for Sale~ Great opportunity for a first-time home buyer or an investor! This adorable 2/2 property features 1396 square feet of living area, a split plan, two bonus rooms which could be used as bedrooms, vaulted ceilings, primary bedroom with walk-in closet and en-suite bath, wood burning fireplace, large, screened patio and a one car garage. Roof and A/C are less than 5 years old and water heater is newer. Convenient to fishing, dining, shopping, and medical/educational facilities. Monthly HOA fee covers grounds maintenance, streetlights and community pool care.

Listing is courtesy of: HOUSE OF GLASS REAL ESTATE PM (863-940-3756)

Listing Agent: Andrea Muzzy (863-430-1733)

Remarks: Under contract-accepting backup offers. Short Sale. ***SHORT SALE*Discover Your Dream Home at Lakeside Landing! Welcome to this immaculate home in the picturesque community of Lakeside Landing! This property offers the ultimate in modern living, combining comfort, style, and functionality. It's move-in ready and equipped with smart home technology, energy-efficient windows, and SOLAR PANELS to help you save on energy costs. Plus, enjoy the privacy of having no rear neighbors and a fully fenced large yard. Recent Upgrades and Features Flooring: Experience the elegance of luxury vinyl flooring throughout the home, with upgraded plush carpeting in the primary bedroom. The bathrooms boast stylish tile flooring. Bathroom Updates: Enjoy the convenience of brand-new toilets and an updated guest bathroom that features a new vanity and mirror. Kitchen Enhancements :Crown molding on kitchen cabinets Added cabinet hardware, Stunning new backsplash, Farm-style door leading to the pantry New wooden pantry shelves Additional Interior Features: Ceiling fans in both the primary bedroom and living area Neutral color scheme with fresh, whole-house interior paint Outdoor Living Relax and unwind on your screened-in porch while overlooking your spacious, fenced yard. It's the perfect spot for enjoying a morning coffee or evening gatherings with friends and family. Community Amenities Lakeside Landing offers a variety of community features to enhance your lifestyle, including: Resort-style pool: Dive into relaxation and enjoy the sun by the pool. Ideal Location Convenience is at your doorstep with easy access to major highways like 27 and I-4. Nearby attractions include Legoland, Disney World, and Universal Studios, making this home an ideal location for entertainment enthusiasts. Additionally, Posner Park is just around the corner for all your shopping needs. Don't miss the opportunity to make this like-new, energy-efficient home yours. Come check it out and experience the best of Lakeside Landing living!*CDD INCLUDED IN TAXES . OWNER MOTIVATED

Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)

Listing Agent: Brenda Anglada (407-493-3464)

Remarks: Completely remodeled and move-in ready, this stunning 2-bedroom, 2.5-bathroom condo in Casa Del Sol Village offers modern updates and a comfortable layout in the heart of Winter Haven. Every corner has been renovated, featuring new flooring, paint, lighting, kitchen appliances, doors, and beautifully updated bathrooms. The spacious living room and downstairs guest half-bath make entertaining a breeze, while both upstairs bedrooms boast private en-suite bathrooms for added convenience. Enjoy a low-maintenance lifestyle with an attached one-car garage, access to the community pool, and a location close to shops and restaurants—all amidst the beautiful landscapes and lakes that surround this lovely community.

Listing is courtesy of: WF REALTY CORP. (407-994-2900)

Listing Agent: Adriana Sanchez (321-947-4014)

Remarks: This dynamically unique home in Winter Haven offers waterfront living, with direct access to the renowned Chain of Lakes. Ideally situated on Lake Cannon, the property delivers stunning water views and a peaceful setting that’s hard to match. Located within a gated, low-maintenance community, this home allows you to enjoy all the perks of ownership without the added upkeep. The community pool and hot tub sits just steps away—offering the feel of a personal pool without the responsibility. Residents also enjoy access to a community dock with first-come, first-served boat slips, making it easy to embrace the lake lifestyle. The property itself features a fenced yard, and a beautiful pergola—perfect for relaxing, entertaining, or enjoying the serene lakefront setting. The garage is equipped with a 2021 split-unit AC system, creating a versatile space ideal for a workshop, gym, or even additional living area. For added peace of mind, the home includes a gas-powered generator that automatically kicks on when needed. Inside, the home is nothing short of impressive—boasting soaring cathedral ceilings, expansive balconies with breathtaking views, and a layout that is both majestic and thoughtfully designed. The primary suite is a true retreat, featuring a private balcony, dual vanities, and a luxurious soaking tub designed for relaxation. Additional office and bonus spaces offers flexibility and can easily be converted into extra bedrooms to fit your needs. Updates include two AC units installed in 2017, along with a durable metal roof added in 2021 and the roof tiles were sealed and coated for an extra long life. Whether you’re looking for a full-time residence, a seasonal getaway, or a place to gather with family and friends, this home delivers a warm, inviting atmosphere with unique architectural character throughout. Enjoy peaceful mornings overlooking the lake, afternoons gardening in your yard, or evenings unwinding on the balcony while taking in the surrounding wildlife. Conveniently located near shopping, grocery stores, and Home Depot, this is more than just a home—it’s a lifestyle. A property like this must be seen in person to truly appreciate the grandeur and exceptional living experience it offers.

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

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

Remarks: One or more photo(s) has been virtually staged. Located in the desirable Hamilton Pointe community, this beautifully maintained 4-bedroom, 2.5-bath, 3,114 sf pool home built in 1992, sits on a half-acre lot with no rear neighbors offering peaceful views of a protected conservation area and ultimate backyard privacy. Features include a spacious kitchen with eat-in area and French doors to the lanai, a grand family room with 13’ ceilings, crown molding, and a striking coral tile fireplace. The split floor plan offers a large master suite with garden tub, walk-in shower, dual vanities, and lanai access, with one bedroom perfect for an office space. Two bedrooms are on the other side of the home with another full bath and laundry room. Enjoy mature landscaping, a refreshing screened-in pool (resurfaced approx. 3 years ago, new sand filter 2 years ago, rescreened 1 year ago), and numerous updates—new roof (2019), Hybrid electric heat pump water heater that is in the garage (2021), gutters/screens (2020), exterior paint (2019) and whole house was re-piped (2021) . Convenient to downtown Winter Haven, Hwy 27, LEGOLAND, golf, shopping, and airports. A Satisfactory 4-Point Inspection has been done.

Listing is courtesy of: REMAX EXPERTS (863-802-5262)

Listing Agent: Laura Slocumb (863-660-7000)

Remarks: This spacious 4-bedroom, 3-bathroom home offers the perfect blend of comfort and functionality. Featuring a large living room, there is plenty of space for relaxing, entertaining guests, or enjoying time with family. The open and inviting layout flows beautifully throughout the home, creating a warm and welcoming atmosphere.Step outside to your own private pool, perfect for enjoying Florida’s sunshine year-round, hosting weekend gatherings, or simply unwinding after a long day. With generous bedroom sizes and three full bathrooms, this home is ideal for families or anyone looking for extra space and convenience.Located in a desirable Winter Haven area, this property combines spacious indoor living with fantastic outdoor amenities, making it a wonderful place to call home.

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

Listing Agent: Marissa Hipp (863-624-4995)