Refine Search
Sort by
215 S Lake Howard Drive, Winter Haven
$419,000
3 Beds ⋅ 2 Baths ⋅ Linger & Nichols Sub/Winter H SubDv. ⋅ 33880 Zip Code
LAKEFRONT OPPORTUNITY ON LAKE HOWARD! Enjoy the Winter Haven waterfront lifestyle at 215 S Lake Howard Drive. This 3-bedroom (with bonus room off bedroom- possibly and office overlooking the lake), 2-bath home includes lakefront property directly across Lake Howard Drive from the residence, providing access to beautiful Lake Howard along with a private dock and covered boat area. The home has recently been refreshed and is ready for its next chapter, featuring fresh interior paint including painted ceilings, new carpet and padding, professional cleaning, and professionally steam-cleaned tile. The floor plan offers comfortable living spaces, a single-car garage, and a large screened rear patio overlooking the spacious, fenced backyard. Home is directly wired for connection of a generator during power outage. Across the street, your lakefront area provides the opportunity to enjoy boating, fishing, and everything that makes living on Lake Howard so special. Keep your boat conveniently at the dock and head out on the water to enjoy the Central Florida lake lifestyle. The home offers a great foundation for a buyer looking for waterfront access while still having the opportunity to make additional improvements and personalize the property. With some added love and updating, this could become a wonderful full-time residence, seasonal Florida home, or lake retreat. Conveniently located near downtown Winter Haven, shopping, dining, medical facilities, and area attractions, this property combines an established location with one of Winter Haven's most desirable amenities—access to Lake Howard right across the street. Bring your vision, your boat, and your love of the water and discover the possibilities at 215 S Lake Howard Drive!

215 S Lake Howard Drive, Winter Haven

948 Summer Glen Drive, Winter Haven
$259,990
3 Beds ⋅ 2 Baths ⋅ Coventry Cove Ph Ii SubDv. ⋅ 33880 Zip Code
WELCOME TO 948 SUMMER GLEN DRIVE! Discover a wonderful opportunity to own this well-maintained 3-bedroom, 2-bath single-family home in the Coventry Cove community of Winter Haven. Built in 2019 and offering approximately 1,690 square feet of living space, this home combines a modern layout, comfortable living areas, and plenty of room to make it your own. Step inside to a bright, open-concept floor plan where the kitchen and main living areas flow together, creating an inviting space for everyday living and entertaining. The kitchen features stainless-steel appliances, ample workspace, and convenient access to the dining and living areas. The thoughtfully designed split-bedroom layout provides separation between the primary bedroom and additional bedrooms, while two full bathrooms provide added functionality. Outside, enjoy the covered rear porch and a generous 7,688-square-foot lot, offering additional outdoor space to relax, entertain, garden, or create the backyard setup you’ve been envisioning. An attached 2-car garage provides convenient parking and additional storage. Located in an established Winter Haven community with a low HOA fee, this home offers convenient access to shopping, dining, recreation, and major roadways, making it easy to enjoy everything Central Florida has. Best of all, the property is vacant and ready to show, giving buyers the opportunity to tour at their convenience. With a newer 2019 construction date, spacious interior, modern kitchen, covered outdoor living space, 2-car garage, and convenient Winter Haven location, this home deserves a closer look. Schedule your private showing today and come experience 948 Summer Glen Drive for yourself!

948 Summer Glen Drive, Winter Haven

751 Grove Street, Winter Haven
$329,999
4 Beds ⋅ 2 Baths ⋅ Inman Grvs Ph 2 SubDv. ⋅ 33881 Zip Code
Welcome to this beautiful 2023-built home in Winter Haven, offering 4 bedrooms, 2 bathrooms, approximately 1,867 square feet of living space, a two-car garage, and a fenced yard. Designed for comfortable modern living, this home features tile flooring throughout the main living areas and carpet in the bedrooms. The open-concept kitchen is perfect for everyday living and entertaining, featuring a large kitchen island, pantry, dining area, and all appliances included. Additional features include a whole-home water filtration system and solar panels that may be transferred to the buyer, subject to applicable terms and buyer qualification. Conveniently located near shopping, dining, medical facilities, and everyday essentials, with easy access to Cypress Creek Plaza, Polk State College, Winter Haven Hospital, and the Winter Haven station. Enjoy being close to LEGOLAND® Florida Resort and PEPPA PIG Theme Park, while Walt Disney World® Resort and the greater Orlando area are approximately 45 minutes away, depending on traffic and destination. This home is ready for its next owner. Schedule your private showing today!

751 Grove Street, Winter Haven

113 Avenue C  Se, Winter Haven
$319,900
4 Beds ⋅ 2 Baths ⋅ Haven Terrace SubDv. ⋅ 33880 Zip Code
SINGLE-FAMILY HOME WITH DETACHED IN-LAW SUITE, RENTAL INCOME & NO HOA! This unique Winter Haven property features a 3-BEDROOM, 1-BATH MAIN HOME plus a separate 1-BEDROOM, 1-BATH DETACHED IN-LAW SUITE, ideal for MULTIGENERATIONAL LIVING, extended family, guests, or ADDITIONAL RENTAL INCOME. The main home is currently operated as a SHORT-TERM RENTAL and is being sold FULLY FURNISHED, with furniture included in the sale price, offering a TURNKEY opportunity for a new owner or a MOVE-IN-READY PRIMARY RESIDENCE. The detached suite has its own PRIVATE ENTRANCE, SEPARATE ADDRESS, PARKING, and SEPARATE UTILITIES currently paid by the tenant, and is generating $1,095/MONTH in rental income while maintaining privacy between both living spaces. Major improvements include NEWER ROOFS completed within approximately the last two years, UPDATED PLUMBING, and CENTRAL A/C for both living spaces. Located just minutes from DOWNTOWN WINTER HAVEN with convenient access to restaurants, shopping, entertainment, and the continued GROWTH AND DEVELOPMENT happening throughout the area. Live in the main home while collecting rental income, continue utilizing the main home as a SHORT-TERM RENTAL, or accommodate extended family—the property offers exceptional FLEXIBILITY for a variety of living arrangements and income opportunities, subject to applicable local regulations. NO HOA!

113 Avenue C Se, Winter Haven

255 Haines Boulevard, Winter Haven
$275,000
4 Beds ⋅ 2 Baths ⋅ Lakes At Lucerne Park Ph 02 SubDv. ⋅ 33881 Zip Code
Perfect for a family purchasing their first home! This four-bedroom, two-bath home offers comfortable Florida living with a functional layout and great outdoor space. One of the standout features is the private, fully fenced backyard, along with a screened-in back patio and covered lanai that create the perfect setting for relaxing, entertaining, or enjoying your morning coffee. Luxury vinyl plank (LVP) flooring runs throughout all bedrooms and main living areas, creating a clean, updated, and easy-to-maintain look, while the bathrooms feature tile flooring. All appliances convey with the home, including the washer, dryer, refrigerator, stove, and garbage disposal, making this home even more move-in ready. The combination of the screened patio, covered lanai, and fenced yard provides an excellent extension of the home’s living space and added privacy. Conveniently located in Winter Haven with access to shopping, dining, entertainment, and major roadways, this home offers a great combination of indoor comfort, outdoor living, and everyday convenience. Schedule your private showing today and see everything this home has to offer!

255 Haines Boulevard, Winter Haven

824 Vienna Drive, Winter Haven
$258,000
3 Beds ⋅ 2 Baths ⋅ Villamar Ph 1 SubDv. ⋅ 33884 Zip Code
Welcome to 824 Vienna Dr, a beautiful Well sought out community 3-bedroom, 2-bathroom home located in the desirable Villamar Phase 1 community of Winter Haven! Built in 2021, this well-maintained home offers approximately 1,402 square feet of comfortable living space with a spacious open-concept design that makes everyday living and entertaining effortless. Step inside to a bright and inviting living area that flows naturally into the dining space and kitchen, creating a comfortable gathering place for family and friends. The primary suite offers a private retreat with its own bathroom, while two additional bedrooms provide plenty of space for family, guests, a home office, or hobbies. A 2-car attached garage adds convenience and valuable storage space. One of the standout features of this property is the larger lot, giving you more room to enjoy the outdoors and create the backyard you've always wanted. The possibilities are endless from adding a pool or playground to creating an outdoor entertaining area, garden, fire-pit space, or your own private backyard oasis, subject to applicable HOA and local requirements. Community itself has a playground, park, and large resort style pool. Located in Villamar Phase 1, you'll enjoy a welcoming community atmosphere with convenient access to shopping, dining, schools, parks, major roadways, and everything Winter Haven has to display. Whether you're looking for your first home, a place to grow your family, or a newer property with room to make it your own, 824 Vienna Dr is an opportunity you won't want to miss. Schedule your private showing today!

824 Vienna Drive, Winter Haven

2824 San Marco Way, Winter Haven
$272,800
3 Beds ⋅ 2 Baths ⋅ Villamar Ph 6 & Ph 6d SubDv. ⋅ 33884 Zip Code
Short Sale. Discover modern Florida living in Villamar, a desirable Winter Haven community with peaceful pond views and convenient access to Central Florida attractions. Built in 2024, this single-story 3-bedroom, 2-bath home offers an open-concept layout with spacious living areas, an oversized island, granite countertops, stainless steel appliances, and a pantry. The private primary suite features an ensuite bath, while two additional bedrooms offer flexibility for guests, a home office, or hobbies. Sliding doors open to a relaxing backyard overlooking the pond. Enjoy community amenities including a pool, clubhouse, and playground. Ideally located near US-27 and I-4, with shopping, dining, schools, LEGOLAND Florida Resort, the Winter Haven Chain of Lakes, and Downtown Winter Haven nearby. A wonderful opportunity to make a newer home your own. Short sale.

2824 San Marco Way, Winter Haven

900 Lake Martha Drive Ne, Winter Haven
$420,000
4 Beds ⋅ 4 Baths ⋅ Hutchinson Add SubDv. ⋅ 33881 Zip Code
Welcome to 900 Lake Martha Drive NE, a truly unique lakefront property offering exceptional space, flexibility, and endless possibilities! The property extends across the street to Lake Martha, providing direct lake frontage and wonderful opportunities to enjoy the waterfront. Information provided by the City, the lakefront portion may be divided from the main homesite, creating even more possibilities for the property. The main portion of the home features three bedrooms and two bathrooms, spacious living and dining areas, and a large bonus room currently used as a pool and game room. This flexible space could also serve as a family room, home office, gym, or additional entertainment area. Located on the opposite side of the home, the private in-law suite offers separation from the main living area, its own entrance, and a full bathroom. Above the two-car garage is an expansive room with a full bathroom and space for a kitchenette. This versatile area could become a movie room, game room, additional primary suite, guest quarters, or a second in-law suite. The garage also includes an additional shower—perfect for rinsing off after boating, fishing, yardwork, or a day by the lake. Enjoy Florida living from the screened front and rear porches. The fenced side yard is already improved with crushed gravel, providing convenient parking for a boat, RV, trailer, or other recreational vehicles. With direct lake frontage, multiple living areas, flexible bonus spaces, and the potential to separate the waterfront portion, this property offers outstanding possibilities for multigenerational living, extended-family accommodations, guest quarters, or potential short- or long-term rental use. Bring your ideas and discover everything this one-of-a-kind Lake Martha property has to offer!

900 Lake Martha Drive Ne, Winter Haven

4116 Fishermans Landing, Winter Haven
$237,900
3 Beds ⋅ 2 Baths ⋅ Cypress Landing Ph 01 SubDv. ⋅ 33884 Zip Code
One or more photos have been virtually staged Charming 3/2 in Cypress Landings on Lake Dexter! Welcome home to this adorable 3-bedroom, 2-bath property located in the highly desirable Cypress Landings community on beautiful Lake Dexter. Step inside to an inviting open floor plan featuring cathedral ceilings that make the living space feel bright, airy, and perfect for everyday living or entertaining. The large primary bedroom offers plenty of comfort with its walkin closet and a private ensuite bath complete with a convenient step in shower. Living in Cypress Landings means enjoying a lifestyle full of amenities, including: Community boat ramp, Fishing pier, Clubhouse, Heated pool, Tennis courts. All of this, plus a location that keeps you close to shopping, medical offices, dining, and more. This community does not allow short term rentals, ensuring a peaceful, residential atmosphere. A wonderful opportunity to enjoy lake access, great amenities, and a cozy home in a fantastic Winter Haven neighborhood!

4116 Fishermans Landing, Winter Haven

119 Sunfish Drive, Winter Haven
$409,000
3 Beds ⋅ 3 Baths ⋅ Lake Lucerne Ph 1 SubDv. ⋅ 33881 Zip Code
Discover your own private Florida retreat in this stunning 3-bedroom, 2.5-bathroom pool home, built in 2018 and offering over 2,600 square feet of living space on a spacious, nearly quarter-acre lot in Winter Haven, Florida! Designed for comfort, entertaining, and everyday living, this beautiful two-story residence features an expansive floor plan with a generously sized primary suite, an oversized walk-in closet, and a huge upstairs loft offering endless possibilities for a home office, media room, game room, or additional living area. The heart of the home is the spacious kitchen, featuring elegant quartz countertops, a large center island, abundant cabinetry, and plenty of room for preparing meals and gathering with guests. Step outside into your very own backyard paradise! Enjoy a gorgeous screened-in private swimming pool surrounded by an elegant travertine pool deck, all within a fully fenced backyard offering privacy and plenty of outdoor space. Whether you're hosting weekend gatherings, relaxing poolside, or enjoying Florida's year-round sunshine, this outdoor retreat is designed to impress. Additional highlights include a two-car garage, an extended driveway providing ample parking, and access to a community swimming pool. Located in the desirable Lake Lucerne community, this home offers convenient access to US Highway 27, Interstate 4, shopping, dining, and everyday essentials. Enjoy the attractions of Central Florida, including LEGOLAND Florida Resort, Winter Haven's famous Chain of Lakes, nearby parks, and the restaurants and entertainment of Downtown Winter Haven. The location also provides convenient connections to Haines City, Davenport, and the greater Orlando area. Why settle for an ordinary home when you can enjoy your own private pool, an oversized primary suite, generous living space, and an exceptional Central Florida location? Schedule your private showing today and experience everything this Winter Haven pool home has to offer!

119 Sunfish Drive, Winter Haven

5809 Windridge Drive, Winter Haven
$349,000
4 Beds ⋅ 3 Baths ⋅ Windridge SubDv. ⋅ 33881 Zip Code
Space, a Screened Pool and a location that keeps you connected! This 4-bedroom, 2.5-bath pool home on the north side of Winter Haven offers 2,836 sqft, a first-floor office/den, an upstairs bonus room and a 2-car garage. The HOA is only $350 a year, there's NO CDD, and it's in Flood Zone X. Out back, the screen enclosure covers both the 24x14 in-ground pool and the 38x11 covered lanai with ceiling fans, giving you a shaded spot to dine, relax or entertain any time of year. Past the pool, the backyard has room for pets, gardening or play. Inside, high ceilings and ceiling fans keep things bright and open. The kitchen opens to the family room and has granite counters, a cooking island, dual sinks and two pantries, with a separate dining room nearby. The 13x13 den works well as a home office, playroom or guest space. Upstairs, the bonus room sits at the center of the bedroom hallways and makes a great media room, hangout or second office. The 19x16 primary suite has two walk-in closets and an en suite bath with granite counters, a vanity area, a garden tub, a separate shower, a private toilet room and a linen closet. Three more bedrooms, including a roomy 16x13, share a second full bath with dual sinks. Roof was replaced in 2022 and the downstairs HVAC was replaced in 2026. The washer, dryer, refrigerator, range, dishwasher and microwave all stay, and there's an inside laundry room. Furnishings are negotiable. Quick access to SR 27 puts Haines City, Davenport and I-4 within easy reach for commuting toward Orlando or Tampa.

5809 Windridge Drive, Winter Haven

9513 Waterford Oaks Boulevard, Winter Haven
$725,000
5 Beds ⋅ 4 Baths ⋅ Waterford Oaks SubDv. ⋅ 33884 Zip Code
HUGE $25,000 PRICE DROP! Welcome to an exceptional 5-bedroom, 3.5 bathroom estate in the highly desirable gated community of Waterford Oaks in Winter Haven, This home offers a 2023 ROOF; NEW EXTERIOR PAINT; and a ONE YEAR HOME WARRANTY offered by the seller, along with lake access, resort-style outdoor living, flexible living spaces, and exceptional parking. A standout feature is community access to LAKE WINTERSET and the Winter Haven Chain of Lakes. A community boat ramp and dock on Lake Winterset are just a short distance away, offering convenient access for boating, fishing, and water recreation. Situated on a beautifully landscaped corner lot, the property features mature landscaping and elegant architectural details. The property offers exceptional parking with an elegant CIRCULAR DRIVEWAY and a separate SIDE ENTRY DRIVEWAY leading to the three-car garage, providing abundant space for guests, vehicles, and recreational equipment. Inside, the spacious floor plan showcases original hardwood floors, high ceilings, multiple tray ceilings, crown molding, custom built-ins, recessed lighting, and abundant natural light. The living room features custom built-in shelving surrounding an electric fireplace, while the adjoining family room offers a custom entertainment center, built-in shelving, and large windows overlooking the screened outdoor living area. The gourmet kitchen is a true centerpiece of the home, featuring custom wood cabinetry, GRANITE COUNTERTOPS, a substantial CENTER ISLAND with prep sink, built-in appliances, gas range with decorative backsplash and pot-filler faucet, abundant counter space, and generous storage. The kitchen overlooks the pool area and connects easily to the entertaining spaces. A spacious BUTLER'S CHAMBER provides additional cabinetry, workspace, storage, and a convenient laundry area. The luxurious primary suite offers a private retreat with a tray ceiling, accent lighting, large windows, plush carpeting, and a walk-in closet. The en-suite bathroom features dual vanities, tile flooring, a deep soaking tub beneath an arched window, and a spacious walk-in shower. One additional bedroom is currently used as a dedicated pool table/billiards room, offering flexibility as a recreation space or bedroom. Upstairs, an expansive TV room or potential mother-in-law suite provides additional privacy and versatility with a microwave, refrigerator, sink, 1/2 bathroom, and walk-in closet currently used as a small office. The outdoor living space is truly one of the home's major highlights, featuring a screened-in lanai, large pool with a swim-out area, OUTDOOR KITCHEN, barbecue area with NEW BARBECUE GRILL, and spacious brick-paver pool deck. The pool enclosure was rescreened last year, creating an inviting setting for swimming, dining, relaxing, and entertaining. Additional highlights include two tankless water heaters, with one serving the primary bedroom and the other serving the remainder of the home; a private well supplying irrigation for the property and adjacent vacant land which is also available for purchase. Conveniently located near shopping, dining, major roadways, local lakes, LEGOLAND Florida, and other Central Florida attractions, this distinctive estate combines Lake Winterset access, a resort-style saltwater pool, outdoor kitchen, gourmet kitchen, three-car side-entry garage, exceptional parking, multiple entertainment spaces, flexible upstairs living, and significant recent improvements.

9513 Waterford Oaks Boulevard, Winter Haven

3785 Giorgio Drive, Winter Haven
$293,000
4 Beds ⋅ 2 Baths ⋅ Villamar SubDv. ⋅ 33884 Zip Code
Welcome to this like-new, four-bedroom home in the desirable Villamar community! Built in 2024 and offering nearly 2,000 square feet of beautifully designed living space, this inviting home combines modern comfort, thoughtful design, and effortless Florida living. Step inside to discover a light-filled, open-concept floor plan where the kitchen, dining area, and great room flow seamlessly together—perfect for both relaxed everyday living and memorable gatherings. The heart of the home is the spacious kitchen, featuring stone countertops, a large center island with breakfast bar, stainless steel appliances, and a generous walk-in pantry. The desirable split-bedroom layout provides added privacy, while the spacious primary suite offers a walk-in closet and a private bath with dual sinks. Ceramic tile enhances the main living areas, with soft carpeting adding comfort to the bedrooms. Sliding glass doors open to the patio and backyard, creating a wonderful space to enjoy morning coffee, outdoor dining, or Florida’s year-round sunshine. Additional highlights include energy-efficient appliances, windows, insulation, HVAC, lighting, low-flow fixtures, an irrigation system, and an attached two-car garage. Villamar residents enjoy access to a community pool, playground, park, sidewalks, and recreational facilities. With four bedrooms, nearly 2,000 square feet, and the peace of mind that comes with a home that is only two years young, this is a truly special opportunity to settle into a beautiful home and begin making memories of your own.

3785 Giorgio Drive, Winter Haven

464 Fish Hawk Drive, Winter Haven
$449,489
6 Beds ⋅ 5 Baths ⋅ Hart Lake Cove Ph 02 SubDv. ⋅ 33884 Zip Code
"Looking for a large home at a reasonable price? This spacious 6-bedroom home in Hart Lake Cove could be the one for you! Freshly painted with new carpet throughout most of the home, this property offers an impressive amount of living space and flexibility. The first floor features a living room, family room, dining area, eat-in kitchen, half bath, and a generously sized bedroom with its own private bathroom—ideal for guests, extended family, or a private home office. The spacious kitchen offers plenty of room to cook and entertain and features a center island and stainless steel appliances. Upstairs, you’ll find a large loft, five additional bedrooms, and three bathrooms, providing plenty of room for everyone. The loft offers even more flexible space for a game room, media area, study space, or second family room. Outside, enjoy a large fenced backyard with plenty of room for outdoor activities, pets, entertaining, or simply relaxing. A 3-car garage provides excellent parking and additional storage space. With 6 bedrooms, multiple living areas, a large loft, 4.5 bathrooms, a 3-car garage, and a spacious fenced backyard, this home offers the room and versatility that can be difficult to find at this price point. Upgrades over the years include new roof installed in 2021; new electric water heater in 2022; new heat pump systems in 2019; exterior freshly painted in 2021; new gutters added in 2020. Whether you need space for a large household, extended family, guests, or multiple home offices, this Hart Lake Cove home has plenty to offer. Schedule your private showing today!"

464 Fish Hawk Drive, Winter Haven

2211 9th Street Ne, Winter Haven
$200,000
3 Beds ⋅ 2 Baths ⋅ Lake Idyll Estates SubDv. ⋅ 33881 Zip Code
Discover the opportunity to make this charming 3-bedroom, 2-bathroom home your own. Located in an established neighborhood with NO HOA. Offering approximately 1,522 square feet of living space. This home provides a comfortable layout with plenty of potential for everyday living, entertaining, or creating space that truly reflects your style. Situated on approximately 0.16 acres, the property has outdoor space for relaxing, gardening, pets, or enjoying Florida's beautiful weather. It also has a fenced in yard and is conveniently located near a newly built recreation center, highly rated magnet schools, local parks, lakes, and public transportation. Whether you're a first-time homebuyer, looking for a family home, or an investor seeking an opportunity in a desirable Central Florida market, 2211 9th St NE will be a perfect fit for you.

2211 9th Street Ne, Winter Haven

3761 Giorgio Drive, Winter Haven
$319,090
4 Beds ⋅ 2 Baths ⋅ Villamar SubDv. ⋅ 33884 Zip Code
Under Construction. Brand new, energy-efficient home available by Sep 2026! Prepare dinner while catching up on the days events from this home's open kitchen which overlooks a spacious great room and dining area. Retreat to your primary suite that is conveniently situated in the back of the home for plenty of privacy. 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.

3761 Giorgio Drive, Winter Haven

3921 Giorgio Drive, Winter Haven
$335,000
4 Beds ⋅ 2 Baths ⋅ Villamar SubDv. ⋅ 33884 Zip Code
Under Construction. Brand new, energy-efficient home available by Sep 2026! Prepare dinner while catching up on the days events from this home's open kitchen which overlooks a spacious great room and dining area. Retreat to your primary suite that is conveniently situated in the back of the home for plenty of privacy. 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.

3921 Giorgio Drive, Winter Haven

4856 Summerfield Circle, Winter Haven
$290,000
4 Beds ⋅ 2 Baths ⋅ Country Club Estates SubDv. ⋅ 33881 Zip Code
Virtually Staged. Welcome to this inviting 4-bedroom, 2-bath home in Country Club Estates, offering a comfortable open layout, beautiful pond views, and a convenient Winter Haven location. With a brand-new roof, this home is ready for its next owner to move in and make it their own. Step inside to a bright, open living and dining area with high ceilings and plenty of natural light. The kitchen overlooks the main living space and features granite countertops, abundant cabinetry, a breakfast bar, and a functional layout that makes everyday living and entertaining easy. The spacious primary suite offers a private retreat with a large walk-in closet and an ensuite bath featuring a granite-topped vanity and tiled walk-in shower. Three additional bedrooms provide plenty of flexibility for family, guests, a home office, or hobby space. One of the home's best features is out back. The screened lanai overlooks the backyard and pond, creating a relaxing place to enjoy your morning coffee, unwind in the evening, or simply take in the peaceful water views. Step outside and enjoy the open backyard with **direct pond frontage and the opportunity to fish right from your own backyard. The location adds even more appeal. A brand-new Publix shopping complex is conveniently located just before the entrance to Country Club Estates, putting groceries and everyday necessities just minutes from home. You're also close to Downtown Winter Haven's restaurants, shopping, entertainment, and the area's Chain of Lakes, while LEGOLAND Florida Resort is just a short drive away. For those looking to enjoy everything Central Florida has to offer, Winter Haven provides convenient access toward Orlando and its world-famous theme parks, while also keeping Tampa, Clearwater Beach, St. Petersburg, and Florida's Gulf Coast within reach for day trips and weekend getaways. With four bedrooms, a brand-new roof, screened lanai, pond frontage, fishing opportunities, a two-car garage, and a highly convenient location, this Country Club Estates home brings together the features buyers are looking for in the Florida lifestyle.

4856 Summerfield Circle, Winter Haven

6183 Grey Heron Drive, Winter Haven
$339,999
5 Beds ⋅ 4 Baths ⋅ Lakeside Landings Ph 01 SubDv. ⋅ 33881 Zip Code
More than a home, this property offers the flexible space, storage, and energy-saving features today’s buyers are searching for! A standout bonus area provides incredible versatility with its own living space, closet, bathroom, and private rear entrance, making it ideal for multigenerational living, guests, a home office, or additional bonus rooms. Another bedroom features its own en suite bathroom for added comfort and privacy. Inside, enjoy granite countertops, upgraded lighting, ceiling fans throughout, and an abundance of closets and storage space. The dedicated laundry room includes cabinet storage, while a staircase in the garage provides convenient access to the attic for even more storage. Solar panels help keep monthly energy costs extremely low, even during Florida’s hottest months. Outside, the extended paver driveway offers additional parking and attractive curb appeal. The community features two swimming pools, a playground, and a walking trail. Enjoy a convenient Winter Haven location just minutes from Port 27 and the Chain of Lakes for easy lake access, as well as Downtown Winter Haven’s shopping, dining, and entertainment. The home is also approximately five minutes from Highway 27, providing easy travel to Orlando and surrounding areas, and is conveniently located near LEGOLAND Florida. This spacious and versatile home is ready for its next owner! This home is also available for rent! For rental details and lease information, please see MLS #L4965531.

6183 Grey Heron Drive, Winter Haven

1711 Garden Lake Drive Unit 1711, Winter Haven
$159,900
1 Beds ⋅ 1 Baths ⋅ Winterset 02 A Condo Ph 01 SubDv. ⋅ 33884 Zip Code
Virtually Staged. Welcome to a little slice of Florida paradise in Winterset, a GATED WATERFRONT COMMUNITY nestled along Winter Haven’s famous Chain of Lakes. This charming 1-bedroom, 1-bathroom condominium offers something truly special: a relaxed lakeside lifestyle, resort-style community amenities, and a home filled with unique spaces and thoughtful updates. Inside, the primary bedroom is wonderfully spacious and features a huge walk-in closet and en suite bathroom. But, one of the home's most delightful surprises is the fun overhead loft, creating flexible bonus space that could be the perfect home office, media area, reading nook, hobby space—or simply your own cozy hideaway. And when it comes to storage, you'll have plenty of room for all the things you don't want taking up your living space, thanks to additional interior AND exterior storage. Major updates mean you can settle in with confidence, too. The HVAC SYSTEM and WATER HEATER were both REPLACED in 2024, giving you two important big-ticket improvements already taken care of. Then there's the lifestyle... Step outside and enjoy everything Winterset has to offer. Take advantage of the community dock and lake access on the SE Chain's coveted Lake Winterset, spend a sunny afternoon at the pool and spa, meet friends at the clubhouse, or enjoy a friendly game of tennis or shuffleboard. When you're ready to get out on the water, Winter Haven's interconnected Chain of Lakes offers endless opportunities for boating, fishing, relaxing, and enjoying those beautiful Florida sunsets. The location is another reason to love this home. You're conveniently close to LEGOLAND Florida Resort, restaurants, grocery shopping, medical facilities, and everyday essentials, while downtown Winter Haven and its lakeside dining and local attractions are also just a few minutes away--whether by boat or by car. Whether you're searching for a full-time Florida home, a weekend retreat, a place to escape the cold, or simply a low-maintenance home where there's always something fun to do, this Winterset condo offers an appealing blend of comfort, character, recreation, and location.

1711 Garden Lake Drive Unit 1711, Winter Haven

2801 Wingfoot Court, Winter Haven
$245,000
2 Beds ⋅ 2 Baths ⋅ Cypresswood Golf Villa SubDv. ⋅ 33884 Zip Code
BEAUTIFUL VILLA READY TO MOVE IN! A brand-new HVAC system (June 2026), along with new insulation throughout the attic. Features include cathedral ceilings, elegant detailed trimwork with decorative corner blocks throughout, new flooring, plantation shutters on the windows, and three sets of French doors. The upgraded kitchen features stainless steel appliances, double ovens, and a built-in pantry with pull-out shelves. A utility closet provides additional storage, and the interior laundry room includes a full-size washer and dryer. The primary bathroom features dual showers and two vanities with wood cabinetry, while the second bathroom includes a jetted bathtub and wood cabinet vanity. Both bathrooms also feature skylights. Golf course frontage and two outdoor patio areas, with one overlooking the 8th fairway, plus a second patio with concrete privacy walls. HOA fee includes roof replacement when needed, so you never have to worry about roof expenses. Cypresswood Country Club community offers golf, a Jr. Olympic-size pool, tennis courts, pickleball courts, a restaurant and bar, social events, live music three nights a week, and lush, well-maintained surroundings. Come take a look at this one!

2801 Wingfoot Court, Winter Haven

507 Short Lane, Winter Haven
$329,000
4 Beds ⋅ 2 Baths ⋅ Inman Grvs Ph 1 SubDv. ⋅ 33881 Zip Code
Beautiful home featuring 4 spacious bedrooms and 2 bathrooms. The fully equipped kitchen boasts beautiful wood cabinetry and granite countertops. Sliding glass doors lead to a covered patio and a private, grassy backyard—perfect for relaxing and enjoying the Florida outdoor lifestyle. The home includes a 2-car garage and a fully equipped laundry room for added convenience. Situated in a desirable community, this property offers comfort, practicality, and excellent investment potential. It is conveniently located near LEGOLAND, Chain of Lakes Park, downtown Winter Haven, shopping centers, restaurants, grocery stores, and medical facilities, with easy access to Highway 27. Winter Haven is also known for its beautiful Chain of Lakes, offering opportunities for boating, fishing, and outdoor recreation. The property is currently leased at $2,000 monthly. A fantastic opportunity for both investors and future homeowners.

507 Short Lane, Winter Haven

1776 6th Street Nw Unit 304, Winter Haven
$92,900
2 Beds ⋅ 2 Baths ⋅ Lakeridge Condo SubDv. ⋅ 33881 Zip Code
**THIS CONDO IS PRICE TO SELL !!**CENTRAL FLORIDA 55+ Age GATED CONDOMINIUM COMPLEX WITH LAKE AND CITY VIEW. All new insulated windows throughout. This condominium provides 1,347 sq. ft. of living area & is located in the beautiful "Chain Of Lakes" City of Winter Haven, Fl. Very friendly complex w/ social activities offered if you wish to participate. Monthly association fee includes water, sewer, trash, fiber optic cable & internet, condo reserves, manager and use of recreational facilities. Lakeridge Condominiums offers a maintenance-free lifestyle w/ heated pool, tennis, shuffleboard, community room, gated entrances & covered assigned parking space. The large bright kitchen has plenty of cabinets & great counter space, appliances (dishwasher does not work) & pantry closet. The kitchen overlooks the 26'x14' great room that also adjoins the additional bonus space & storage closet. The 16X14 foot Primary bedroom suite has a walk in closet & bathroom w/ walk-in shower. Beautiful views of Spring Lake can be enjoyed from Primary bedroom & living areas. The 2nd bedroom & bath can be a private guest area or for your personal use for office, hobbies etc. The washer & dryer are included in the sale. Central heat and air conditioning. Convenient proximity to shopping, places of worship, groceries & restaurants. Extra assigned storage bin on same floor. Make this your full time home, winter home or investment property to update. Lakeridge Condominiums is an age-restricted, well-maintained & well-managed community. Sharepoint car charger provided for those with electric cars. Non-smoking property. 1 pet, 20 pounds or under may be approved.

1776 6th Street Nw Unit 304, Winter Haven

2112 Avenue C  Sw, Winter Haven
$379,000
4 Beds ⋅ 2 Baths ⋅ West Winter Haven SubDv. ⋅ 33880 Zip Code
Step into a piece of Winter Haven history—beautifully reimagined for modern living. Just moments from Lake Howard, this exceptional 1925 residence offers the character and craftsmanship today's luxury buyers crave, paired with a complete top-to-bottom transformation. Original refinished 101 year old hardwood floors and two sets of original French doors provide a timeless connection to the home's past, while the rest has been thoughtfully rebuilt with today's lifestyle in mind. The custom kitchen, elegant architectural details, crown molding, tray ceilings, and spacious living areas create a home that feels both sophisticated and inviting. The private primary suite is a true retreat, featuring his-and-hers walk-in closets and a spa-inspired ensuite with a two-person tiled shower, garden tub, and generous vanity space. Two additional bedrooms upstairs add flexibility for guests, family, or a private home office. With approximately 2,011 heated square feet, 4 bedrooms, 2 baths, a dedicated laundry room, fully fenced backyard, and no HOA, this is a rare opportunity to own something with genuine character—not another cookie-cutter home. Bring your boat and water toys and enjoy the freedom and lifestyle that come with living near Winter Haven's beautiful Chain of Lakes. For buyers who appreciate history, character, and modern luxury, this is a home that simply must be experienced in person.

2112 Avenue C Sw, Winter Haven

333 Lake Howard Drive Nw Unit 204D, Winter Haven
$139,999
3 Beds ⋅ 2 Baths ⋅ Imperial Harboursphases 01 & 02 SubDv. ⋅ 33880 Zip Code
**Welcome to Imperial Harbours, a beautifully maintained 55+ active community surrounded by gorgeous landscaping and offering access to Winter Haven’s Chain of Lakes!** This spacious **3-bedroom, 2-bath second-floor corner condo** offers over 1,226 sq. ft. of comfortable living with an open-concept living/dining area, lovely kitchen with beautiful countertops and abundant cabinetry, plus an enclosed bonus room perfect for an office, sitting area, or hobby space. The generous primary suite features a private bath and large walk-in closet. Enjoy the peace of mind of a **BRAND-NEW A/C**, newer double-pane windows, updated bathroom vanities, fresh interior paint, and an in-unit washer and dryer. Additional features include an exterior storage unit, elevator access, covered assigned parking, guest parking, and community car wash. Enjoy resort-style amenities including a **heated pool, fitness room, billiards, recreation room, shuffleboard, BBQ grills, gazebo, fishing, dock access, and nearby boat ramp.** HOA includes **water, internet, cable, and trash!** Conveniently located near hospitals, restaurants, shopping, and everyday essentials. **Come experience the Florida lifestyle at Imperial Harbours—schedule your private showing today!**

333 Lake Howard Drive Nw Unit 204D, Winter Haven

1380 S Lake Roy Drive, Winter Haven
$359,000
4 Beds ⋅ 3 Baths ⋅ South Roy Shores Pb 38 Pg 45 SubDv. ⋅ 33884 Zip Code
Virtually Staged. UPDATED POOL HOME WITH NEW BATHROOMS, NEW POOL DECK & BRAND-NEW WATER HEATER! Welcome to this spacious 4-bedroom, 3-bathroom, 2,955-square-foot pool home on a desirable corner lot in Winter Haven, ideally located across from beautiful lakefront homes and close to Winter Haven's renowned Chain of Lakes. Major recent improvements include a BRAND-NEW HOT WATER HEATER installed in October 2026, TWO NEWLY REMODELED BATHROOMS completed in 2025, and a RESURFACED POOL WITH NEW POOL DECK completed in 2022. The roof was also replaced in 2023, providing additional peace of mind for the next owner. Inside, the triple-split bedroom floor plan offers privacy and flexibility, making this home ideal for families, guests, or those who need dedicated spaces for work and hobbies. The oversized family room is designed for entertaining, featuring two sets of sliding glass doors that open directly to the screened and netted pool enclosure and covered patio. The seamless indoor-outdoor flow creates the perfect setting for gatherings, relaxing poolside, or enjoying Florida's year-round lifestyle. A spacious flex room with direct pool and patio access offers endless possibilities as a game room, home office, media room, hobby space, or additional entertainment area. The kitchen features custom-made cabinetry, granite countertops, a custom tile backsplash, and stainless-steel appliances, creating a functional and inviting space for everyday living and entertaining. The primary suite offers a private retreat with a bathroom featuring a garden tub, dual sinks, and a walk-in shower. The two recently remodeled bathrooms add fresh, updated appeal throughout the home. Additional highlights include a LARGE LAUNDRY ROOM with utility sink, drop-down ironing board, and extra shelving, as well as tile and wood flooring throughout the main living areas. Step outside to your own private backyard retreat. The resurfaced pool and NEW POOL DECK, completed in 2022, are surrounded by a screened and netted enclosure with a covered patio, creating an inviting space for swimming, dining, entertaining, and soaking up the Florida sunshine. A welcoming front screened porch, ample covered parking, and two detached storage sheds provide additional convenience and storage. The yard is irrigated by a well with a newer irrigation timer. The HVAC system is approximately 9 years old. While there are still opportunities for cosmetic updates in select areas, the home's generous size, desirable floor plan, significant recent improvements, and fantastic outdoor living spaces provide an excellent foundation for making it your own. Location adds even more appeal. The property is just a short walk to Freedom Boat Club, making it easy to access and explore Winter Haven's famous Chain of Lakes. LEGOLAND Florida is approximately one mile away, offering exceptional convenience for both residents and guests. With its four bedrooms, three bathrooms, private pool, newly remodeled bathrooms, resurfaced pool and new pool deck, new water heater, 2023 roof, flexible living spaces, and prime location near lakes and attractions, this is an exciting opportunity to own a spacious Winter Haven home and enjoy the best of the Florida lifestyle.

1380 S Lake Roy Drive, Winter Haven

1069 Sandpiper Loop, Winter Haven
$364,900
4 Beds ⋅ 3 Baths ⋅ Chestnut Crk SubDv. ⋅ 33881 Zip Code
PRICE REDUCED - ASSUMABLE VA MORTGAGE–IN PLACE - MOVE-IN READY! NEW FLORIDA PROPERTY TAX SAVINGS OPPORTUNITIES!** Florida homeowners have a new reason to celebrate! With the recent passage of **FLORIDA AMENDMENT 3 (PROP 3)**, qualifying homeowners may enjoy significant property tax relief as the expanded homestead exemption increases to **$150,000 IN 2027 AND $250,000 IN 2028 FOR NON-SCHOOL PROPERTY TAXES! Discover refined Florida living in the STUNNING SHENANDOAH II MODEL, an impressive SINGLE-STORY RESIDENCE offering 2,034 square feet of thoughtfully designed living space. Featuring 4 SPACIOUS BEDROOMS and 3 FULL BATHROOMS, this BEAUTIFULLY APPOINTED HOME blends ELEGANCE, COMFORT, and FUNCTIONALITY in a versatile layout designed for both everyday living and entertaining. From the moment you arrive, the CHARMING COLUMNED FRONT PORCH creates an inviting first impression. Step inside to a BRIGHT, OPEN-CONCEPT LIVING AREA where the seamless flow between the kitchen, dining, and living spaces creates an ideal setting for entertaining guests or enjoying relaxed evenings at home. The GORGEOUS KITCHEN is designed to impress, featuring PRISTINE SHAKER-STYLE CABINETRY, SAMSUNG STAINLESS STEEL APPLIANCES, a GENEROUS PANTRY, and a CHIC BREAKFAST BAR. The adjoining VERSATILE DINING AREA provides a welcoming space for everything from casual breakfasts to special gatherings. Throughout the main living areas and bathrooms, UPDATED 25-YEAR-LIFE-PROOF WOOD-VINYL FLOORING offers a SLEEK LOOK, while the bedrooms feature PLUSH STAIN-RESISTANT CARPETING for added comfort. These thoughtfully selected finishes combine BEAUTY, DURABILITY, and EVERYDAY PRACTICALITY. The SPACIOUS OWNER’S SUITE provides a peaceful retreat with a STYLISH TRAY CEILING, LARGE WALK-IN WARDROBE, and LUXURIOUS ENSUITE BATHROOM featuring DUAL SINKS and a BEAUTIFULLY TILED SHOWER accented by a GLASS ENCLOSURE. Step outside and embrace OUTDOOR LIVING on the EXPANSIVE COVERED LANAI, an inviting space for morning coffee, evening relaxation, or entertaining. Direct access to the THIRD FULL BATHROOM adds exceptional convenience for guests and outdoor activities. The LARGE BACKYARD provides a generous canvas for creating your own private outdoor retreat, with ample space to envision a future pool or customized outdoor living area, subject to applicable approvals and restrictions. Additional highlights include a 2-CAR GARAGE, ENERGY-EFFICIENT INSULATION, and ARCHITECTURAL SHINGLES, bringing together STYLE, EFFICIENCY, and PRACTICALITY. This EXCEPTIONAL HOME offers an appealing combination of BEAUTIFUL FINISHES, FUNCTIONAL DESIGN, SPACIOUS LIVING, and INDOOR-OUTDOOR COMFORT. If you’ve been waiting for a MOVE-IN READY RESIDENCE with room to personalize and make your own, this SHENANDOAH II MODEL deserves a closer look. WELCOME HOME!

1069 Sandpiper Loop, Winter Haven

How much is your home worth?

Get instant property value now!