Courtesy: KELLER WILLIAMS REALTY/P B
561-656-2929
Welcome home to effortless Florida living in the highly sought-after Plantation community of Cypresswood, where space, comfort, and lifestyle come together. Set on an oversized 0.46-acre lot, this beautifully maintained single-story ranch-style home offers privacy, flexibility, and room to breathe—both inside and out. Step inside to a bright, open layout made for gathering and relaxing. The spacious great room with fireplace invites cozy evenings, while a versatile flex space easily adapts as a home office, living room, or quiet retreat. Entertain with ease in the formal dining room, and enjoy everyday moments in the welcoming eat-in kitchen, thoughtfully updated with new cabinetry, countertops, flooring, plumbing, and appliances. A nearby inside laundry room adds everyday convenience. This home has been lovingly updated for peace of mind, including 11 of 13 replaced windows, a new HVAC system, new front and back doors, a new garage door and opener, and a newly fully insulated attic. The roof is approximately 7 years old, and the water heater approximately 2 years old. A spacious 2-car garage offers plenty of room for vehicles, storage, or recreational gear—perfect for this golf-cart-friendly community. Out back, your private oasis awaits. Relax or entertain in the fully screened, oversized saltwater pool, complete with a new pool pump, new pool enclosure screening, and lush privacy hedges that create a serene, secluded escape. It’s the perfect setting for morning swims, weekend gatherings, or peaceful evenings under the Florida sky. Beyond the home, Cypresswood offers a lifestyle few communities can match. Residents enjoy an 18-hole championship golf course, along with a vibrant clubhouse featuring a restaurant—a true social hub where neighbors become friends. Move-in ready and rich with lifestyle appeal, this home is more than a place to live—it’s a place to truly enjoy life.
Courtesy: COLDWELL BANKER REALTY
863-294-7541
This home is a blank slate with lots of room. Over 1400 sf of living space plus the lanai with over 300 sf. Much of the flooring is removed showing the sturdy plywood floors. The kitchen is very functional with lots of storage space. The laundry is conveniently located just off the kitchen. The split bedroom floor plan offers lots of privacy for guests. The guest bedroom is a large area that could incorporate an office space with a full back conveniently located outside of the room. The shingled roof was installed in 2017 and the water heater was installed in December 2025. If that's not enough it is located in the "dog area", so bring those little fur babies and make this home your own. This home is priced to sell quickly. Make your appointment today!!
Courtesy: NUWAVE REALTY
386-473-9765
RANCH style block home on oversized 1/4+ Acre fenced lot (78 ft x 140 ft). This could be a three or four bedroom home if you would want to convert the bonus room into another bedroom or convert the garage into an extra large primary bedroom and bath. The options are endless. Recently painted inside and outside, newer shingle roof, updated electric. Spacious open floor plan with a large living room, entertaining dining room/kitchen combo with lots of beautiful slow-closing cabinets and storage throughout. This property is close to every amenity imaginable and available for immediate possession!
Courtesy: MERITAGE HOMES OF FL REALTY
813-703-8860
One or more photo(s) has been virtually staged. Brand new, energy-efficient home available NOW! Retreat to your primary suite located in the back of the home for plenty of privacy and offers a huge walk-in closet. Visit Villamar and explore new single-family homes for sale in Winter Haven, FL. Residents will have access to two resort-style amenity centers featuring a clubhouse, pool, and playground. Winter Haven is known for its beautiful chain of lakes with lakeside restaurants and its award-winning community theater. Nearby attractions include Legoland Florida and Peppa Pig Theme Park. A brand-new model and new phase are coming soon. Each of our homes is built with innovative, energy-efficient features designed to help you enjoy more savings, better health, real comfort and peace of mind.
Courtesy: MERITAGE HOMES OF FL REALTY
813-703-8860
One or more photo(s) has been virtually staged. Brand new, energy-efficient home available NOW! Retreat to your primary suite located in the back of the home for plenty of privacy and offers a huge walk-in closet. Visit Villamar and explore new single-family homes for sale in Winter Haven, FL. Residents will have access to two resort-style amenity centers featuring a clubhouse, pool, and playground. Winter Haven is known for its beautiful chain of lakes with lakeside restaurants and its award-winning community theater. Nearby attractions include Legoland Florida and Peppa Pig Theme Park. A brand-new model and new phase are coming soon. Each of our homes is built with innovative, energy-efficient features designed to help you enjoy more savings, better health, real comfort and peace of mind.
Courtesy: MERITAGE HOMES OF FL REALTY
813-703-8860
One or more photo(s) has been virtually staged. Brand new, energy-efficient home available NOW! Open floor plan with a lot of flexibility. Retreat to your primary suite that is conveniently situated in the back of the home for plenty of privacy and offers a huge walk-in closet and bathroom with dual sink vanity and standalone shower. 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.
Courtesy: TINA MARIE LLC
407-448-5388
COZY 2 BED 2 BATH CONDO, 1 STORY. NICELY MAINTAINED. CONDO HAS 2 WALK-IN CLOSETS, A LARGE COVERED PATIO. NATURAL SUNLIGHT IN ALL ROOMS MAKES THE UNIT PLEASANT AND CHEERFUL. ESTABLISHED ON A CORNER LOT GIVING YOU MORE OUTDOOR SPACE. HOA FEE IS $253 A MONTH.
Courtesy: CHARLES RUTENBERG REALTY ORLANDO
407-622-2122
Remodeled and ready for your family. 3 bedrooms, 2 bathrooms home on lovely lot. Freshly painted, new laminate flooring, stainless steel appliances and more.
Courtesy: JACK KELLER INC
727-586-1497
Welcome to Sawgrass Drive, a better-than-new home in the highly sought-after Lake Ashton 55+ golf community, where resort-style living meets thoughtful luxury. This meticulously upgraded residence offers comfort, style, and over $70,000 in premium enhancements, making it truly move-in ready. Step inside to discover a bright, open layout with elegant finishes and custom touches throughout. The home features: ?? Extensive landscaping with premium river rock in front and back ?? Plantation shutters on all windows and remote-controlled shades on sliding glass doors ?? A custom oak barn door at the guest entrance ?? Designer chandelier and pendant lighting in the primary suite ?? Two wine refrigerators for entertaining in style ?? Large-capacity water softener and four-stage drinking water filtration system under the kitchen sink ?? Exterior stone façade added in 2024 for timeless curb appeal ??? Garage upgrades including a screen and two overhead storage racks ?? Additional outdoor outlets and an in-wall TV outlet for seamless living ?? Driveway pavers sealed in July 2025 ?? Screened-in lanai and front entrance for year-round enjoyment Lake Ashton offers a vibrant lifestyle with two championship golf courses, clubhouses, pools, tennis and pickleball courts, fitness centers, bowling alley, movie theater, and a full calendar of social events and activities. Whether you're seeking a seasonal retreat or a full-time residence, this home delivers unmatched value, comfort, and community. Schedule your private showing today and experience the Lake Ashton lifestyle for yourself!
Courtesy: LIVE FLORIDA REALTY
863-868-8905
Welcome to this beautifully updated 4-bedroom, 2-bath lakefront residence on the renowned *Chain of Lakes*, showcasing picturesque views of Lake Jessie and the rare benefit of no HOA! Set on a generous .44-acre lot in a quiet neighborhood, this home offers the perfect balance of privacy, comfort, and upscale waterfront living. The light-filled interior features neutral tones throughout, 12mm 24-hour water-resistant laminate flooring in the main living areas, ceramic tile in the primary suite, an updated primary bathroom, and plush carpeting in the secondary bedrooms. One bedroom has been thoughtfully converted into a charming library with custom shelving designed for easy removal if desired. Significant improvements provide peace of mind, including a metal roof (11/2019), double-pane insulated windows, new septic system and drain field (2021), and a new AC unit with air handler (2023). Enjoy prime outdoor living with a private fenced in backyard retreat featuring a new dock and boathouse (2021), expansive patio space including a separate screened-in patio, and a paver fire pit perfect for entertaining while enjoying tranquil lake views and watching the Sea planes! Don't miss out on the best of Florida waterfront living and schedule your showing today!
Courtesy: LIVE FLORIDA REALTY
863-868-8905
Welcome to your dream home, a charming 2-bedroom, 2-bath retreat with a versatile bonus room that can be used as a 3rd bedroom or a separate home office featuring its own private exterior entrance! This inviting home has been thoughtfully refreshed and is move-in ready, offering fresh interior paint, a new smart thermostat, recent tree removal, and a brand-new shingle roof (03/24) for peace of mind! Inside, you’ll find a spacious kitchen with a breakfast bar that opens to a bright living room, ideal for everyday living and entertaining. The large dining room or secondary family room is conveniently located next to the kitchen and provides plenty of space for gatherings. Relax in the cozy Florida room, featuring warm wood walls and ceilings and an abundance of windows where you can enjoy views of Lake Elbert! Outside you will find your large paver patio, perfect for entertaining or unwinding, and enjoy the privacy of a newly built fully fenced backyard. Additional updates include a new AC (2022), blown attic insulation (2022), water heater (2019), all kitchen appliances (2021), and Exterior Front Porch paint along with a new front door (2025). Conveniently located just minutes from Downtown Winter Haven, Polk State College, HWY 27, and medical facilities, this home blends comfort, flexibility, and an excellent location. Schedule your showing today!
Courtesy: FLORIDA REAL ESTATE COMPANY
863-701-3487
Custom Design abounds in this beautiful single family residence located steps away from lovely Lake Howard in Winter Haven. This 4/4 pool home built in 2013, located in a NO HOA, NO CDD, no restriction community, steps away from the park/playground, walking trails, and the water sports of Winter Haven's chain of lakes, minutes from golfing, eateries in the downtown area, shopping, and Spring Training Baseball! Step inside and be welcomed by the living area, spacious and well appointed with durable, custom stained floors, and lots of natural light that infiltrate the space. A designated dining area for gathering around your table leads towards the custom kitchen equipped with double oven, Bosch induction cooktop, granite countertops, and a breakfast bar for on-the-go eats. The large built in pantry provides storage you long for! The family room is perfect for lounging, gaming, or movie watching a it is separate from the private living area. Laundry located adjacent to the family room is ideal for shoe removal prior to entering the residence when you enter from the garage. There's a gardener's bath located between the garage and the pool, and this will make the house manager HAPPY! The central vacuum system will add to the ease of managing floors! The heated saltwater pool is completely fenced, offering peace of mind. On to the private retreat of the owner's suite, a well appointed space welcomes you to relax. With soaring ceilings, makeup vanity, bathroom with jetted soaking tub, and spacious closets, the function for your everyday needs are exceeded. But wait! There's MORE! Step outside to your private covered patio, that leads to a peaceful garden area for quiet coffee time, or tea sipping at the end of the day. Accessory bedrooms and bathrooms are located on a separate hallway, and with 3 other rooms, the possibilities are endless. Outdoors, you will find parking for big toys, so bring your boat! The outdoor space is well utilized and you won't be hindered by any HOA rules! Added bonus - RV hookup. Irrigation system. Vanity area in bathroom is also plumbed if you would desire to add a sink.Security system ready for you to activate your own service. Don't delay, homes like this aren't available every day! Call to schedule your private tour today!
Courtesy: RE/MAX HERITAGE PROFESSIONALS
863-256-2188
Welcome to this extremely well maintained and thoughtfully upgraded home located in the highly desirable, gated 55+ community of Traditions. From the moment you arrive, the stamped concrete entry and covered, screened front porch create a warm and inviting welcome to this amazing home. Step inside the grand foyer and be immediately impressed by the stunning vaulted ceilings, upgraded tile flooring and open and airy layout. This spacious home offers 2 bedrooms, 2 full bathrooms, and a versatile flex room/office that can easily function as a third bedroom and features custom-built-in shelving with granite shelves, making it both stylish and functional. To the left of the foyer, you’ll find the flex room, followed by the spacious dining area. From the foyer you walk straight into the large living room and kitchen, perfect for entertaining or everyday living. There is crown molding, adding to the home’s upscale feel. The chef’s kitchen is a true standout, featuring beautiful quartz countertops, a large kitchen island, plenty of cabinet space, a walk-in pantry, designated breakfast nook and upgraded “Slate Line” GE appliances, offering both style and performance. The primary bedroom provides elegant tray ceilings and an ensuite large primary bathroom with oversized impressive fully tiled walk-in shower and double vanity with quartz finished counters. The primary suite has a large walk-in closet as well. Down the hallway there is an additional spacious guest bedroom and guest bathroom with a shower/tub and vanity with quartz counter as well. Enjoy Florida living year-round on the extended paved screened in and partially covered back porch, ideal for relaxing or hosting guests. This back porch is directly accessible through sliding doors from the living room breakfast nook and primary bedroom. Additional upgrades include the fully paved driveway and a garage with epoxy flooring, extra cabinetry, and overhead storage. Washer and dryer are located inside the separate laundry room and included. Some of the furniture can be purchased for additional convenience. This home truly reflects pride of ownership with meticulous care throughout. Traditions is offering an exceptional retirement lifestyle with a grand lakefront clubhouse featuring a library, fitness center, card room, billiards, resort-style pool and jacuzzi, tennis courts, fishing pier, water access and a wide variety of activities and social events. Move-in ready and loaded with upgrades, this is Florida living at its finest.
Courtesy: CHAIN OF LAKES REALTY INC
863-287-4679
LUXURY CONDO plus LOCATION, LOCATION, LOCATION! Located in the Lake Buckeye waterfront condominium complex. Nestled on Lake Buckeye and under shady oak trees. Just minutes from Polk State College, Baycare hospital, BRAND NEW Elbert Elementary School, & the BRAND NEW Lake Elbert walking/biking trail. Winter Haven is the "Chain Of Lakes City" featuring over 100 area lakes and ideally located in Central Florida. You will also be just 5 minutes from the revitalized downtown area where you can take advantage of Winter Haven's trendy restaurants, shops & events. Luxury updates to this condo include nearly everything! A/C unit, Window Treamments, Luxury Vinyl throughout,. The all new Kitchen, includes wood cabinetry, tile backsplash granite counters & a full stainless appliance package. Baths also have new cabinetry, granite, new fixtures, wall tile & lighting. The laundry area has a Whirlpool washer & dryer. There's plenty of natural light here and a balcony with views of the shady courtyard, pool & lake. Don't miss your opportunity to move into this BETTER THAN NEW 2 bedroom, 2 full bath condo!!
Courtesy: CORCORAN PREMIER REALTY
407-965-1155
Nearly new 3BR/2BA home built in 2022, located in a gated community with water views and access to the Lake Rochelle boat ramp. Vaulted ceilings and an open-concept living, dining, and kitchen layout with split bedroom floor plan. Kitchen features granite countertops, 42" cabinets, soft under-cabinet lighting, and breakfast bar. Primary suite includes double vanity, tiled shower, and oversized walk-in closet. Separate den/office with French doors plus additional nook near kitchen suitable for desk or reading area. Covered patio with peaceful water views. Whole-home water filtration system. Extended driveway with parking for 6+ vehicles and additional garage storage. Cul-de-sac lot. Community amenities include public dock, playground, and lake access for kayaking and boating. Low HOA. Convenient to downtown Winter Haven and Central Florida attractions.
Courtesy: DALTON WADE INC
888-668-8283
*** Photo's coming soon*** Pet lovers will appreciate this purr-fectly appointed residence generously sized backyard, ideal for pets, entertaining, or simply enjoying your own private outdoor retreat. Nestled on a quiet cul-de-sac in sought-after southeast Winter Haven, this home offers privacy, charm, and convenience. This stunning two-story home offers four spacious bedrooms and two-and-a-half bathrooms, blending comfort and sophistication throughout. The thoughtfully designed interior showcases gorgeous granite countertops, rich dark cabinetry, and elegant tile flooring, creating a refined yet welcoming atmosphere. A truly exceptional property—schedule your private showing today.
Courtesy: CENTURY 21 WATSON & MYERS REALTY
863-324-1000
EXTRA, EXTRA, EXTRA special homes like this rarely come available - an impeccably maintained, seasonally occupied villa in Vienna Square, thoughtfully enhanced beyond the builder’s base model and ready to enjoy immediately. Located in the desirable 55+ community of Vienna Square, this exceptional home shows better than new. With thoughtful enhancements and numerous upgrades beyond the builder’s base model, this 2023 2 bedroom 2 bath villa offers quality finishes and attention to detail throughout. White plantation shutters on the front windows provide both privacy and style. The kitchen and bathrooms feature white wood cabinetry paired with granite countertops, creating a bright, clean, and timeless look. Additional enhancements throughout the home reflect careful ownership and elevate the overall feel well beyond standard construction. The private, South facing, glass-enclosed Florida room is a standout, offering abundant natural light and a peaceful space to relax year-round - ideal for enjoying morning coffee or quiet afternoons. Tastefully decorated, the home may be offered with optional turnkey furnishings, allowing for a seamless move-in experience with everything already in place. This home is conveniently located within 10 minutes of restaurants, banks, shopping and Legoland. Vienna Square offers a low-maintenance lifestyle with reasonable fees, in a welcoming setting. Homes of this caliber are seldom available. Take the time to see it in person and experience the ease and quality this thoughtfully enhanced villa has to offer. Vienna Square is a beautifully maintained, amenity-rich community designed for easy living. Monthly fees include exterior paint, roof replacement, irrigation water, basic yard maintenance, and a Spectrum Internet/TV package. Residents enjoy access to a community pool, fitness center, billiards, movie nights, tennis and pickleball courts, and an active social calendar. Step inside, fall in love. Make it yours!
Courtesy: GLOBAL LIFESTYLE LLC
727-455-2709
Welcome to a wonderful new chapter in Lake Ashton, Central Florida’s premier fifty-five plus active adult community, where this thoughtfully maintained two bedroom, two bath home offers comfort, style, and peace of mind. Recently refreshed with exterior and interior paint, enhanced energy-saving features include additional attic foil insulation, and surrounded by pristine landscaping, the home immediately makes a welcoming impression with its screened front entry, elegant stone veneer, and newly sealed veneer and pavers. Inside, the living room feels open and inviting beneath a cathedral ceiling and new vinyl plank flooring, while the spacious primary suite and separate guest bedroom and bath provide privacy and relaxation for both owners and visitors. The kitchen is both functional and attractive with solid wood cabinetry and granite countertops, and the generously sized screened veranda creates the perfect setting for quiet mornings, relaxed evenings, or easy entertaining. This home truly shines when experienced in person, and life at Lake Ashton extends far beyond the front door with two championship golf courses, an expansive clubhouse, fitness center, theater, pickleball courts, bowling alley, on-site restaurant, and an array of activities that make every day feel full and rewarding. Blending comfort, convenience, and an exceptional sense of community, this inviting property is ready to welcome you home and offer the very best of Florida living.
Courtesy: LPT REALTY, LLC
877-366-2213
PICTURES COMING SOON! Welcome home to this beautifully updated 3-bedroom, 2-bathroom gem that's perfect for first-time homebuyers or anyone looking for a move-in-ready home. This cute and charming property features a brand new roof, new windows and new water heater. Freshly painted interior and exterior, offering peace of mind and great curb appeal from the moment you arrive. Step inside to discover all new flooring throughout, a completely renovated kitchen with quartz countertops and brand new appliances, and two fully updated bathrooms. Conveniently located just minutes away from major roads, schools, and shopping. Schedule your private showing today.
Courtesy: CENTURY 21 WATSON & MYERS REALTY
863-324-1000
INVESTOR SPECIAL. NO HOA. GOOD RENTAL PROPERTY. NEEDS SOME REPAIRS, BUT PRICED RIGHT. SELLER SAYS THERE WAS A NEW MEMBRANE ON ROOF APPROX 3-4 years ago. Double wide built in 1973. Call for appointment to see.
Courtesy: JASON MITCHELL REAL ESTATE FLO
754-307-0607
Beautiful 3-bedroom, 2-bath ranch home built in 2022 offering modern design and easy one-level living. Open concept layout with spacious living areas, contemporary finishes, and abundant natural light. Well appointed kitchen and comfortable bedroom split for added privacy. Move-in ready and perfect for today's lifestyle.
Courtesy: VIEWPOINT VALUE REALTY
863-617-7015
This 3 YEAR YOUNG, 4 bedroom, 2 bath single-family home built by DR Horton offers 1,867 square feet of thoughtfully designed living space and a 2-car ATTACHED GARAGE with OPENER. The open floorplan features a seamless kitchen, dining area, and family room combination, ideal for both everyday living and entertaining. The kitchen includes a CENTER ISLAND, GRANITE countertops, DOUBLE SINK, and a WALK-IN PANTRY and is ready for your personal touch with NEEDED APPLIANCES (except for the included dishwasher). Ceramic tile flooring runs throughout the main living areas, with carpet in the bedrooms. The PRIMARY BEDROOM boasts a WALK-IN CLOSET and a spacious EN-SUITE BATHROOM featuring a walk-in SHOWER, DUAL SINKS with GRANITE countertops, and a PRIVATE WATER CLOSET. Three additional bedrooms are serviced by BATHROOM #2, which offers a TUB/SHOWER combination, SINGLE SINK VANITY, and GRANITE countertop. An INSIDE LAUNDRY ROOM with washer/dryer HOOK-UPS adds convenience. Additional features include an IRRIGATION SYSTEM and a COVERED concrete LANAI, accessed through sliding glass doors from the family room. This home combines modern design, functionality, and value in a well-built, nearly new property.
Courtesy: MARK SPAIN REAL ESTATE
855-299-7653
3.63% Rate Assumable FHA with ROAM! this inviting 3-bedroom, 2-bath home located just minutes from downtown Winter Haven and the Chain of Lakes. This property features a bright, open living area with plenty of natural light, a functional kitchen layout, and spacious bedrooms. The large yard offers room for outdoor entertaining, gardening, or future expansion. With a little TLC, this home could truly shine—making it a perfect opportunity for first-time buyers or investors. Conveniently located near shopping, dining, and parks.
Courtesy: BHHS FLORIDA PROPERTIES GROUP
863-701-2350
One or more photo(s) has been virtually staged. Nearly 5 acres of fenced and cross-fenced land offering privacy and room to spread out. This 3-bedroom, 2 bath split plan home features an open living and dining area filled with natural light and a large, screened lanai overlooking the property. The private primary suite includes a walk-in closet, granite counters, soaking tub, and separate shower. Two additional bedrooms share a hall bath, and there is an indoor laundry for convenience. Outside you’ll find a 2-car carport and detached garage/workshop, plus plenty of space for animals, gardens, or outdoor projects. This corner lot property gives you the freedom of country living while still being just minutes from shopping, dining, and major roadways.
Courtesy: MY REALTY GROUP, LLC.
786-847-7421
Welcome to 1804 Emily Drive, Winter Haven, a spacious and beautifully maintained home offering 5 bedrooms, 2.5 bathrooms, and over 2,800 square feet of living space. Designed for comfort and functionality, this home features expansive living areas ideal for large families, multi-generational living, or entertaining guests. Enjoy peace of mind with a NEW ROOF and NEW AC installed in 2023, providing energy efficiency and long-term value. The open and flexible floor plan allows for multiple living and dining options, while the generously sized bedrooms with plenty of space to relax and unwind. Conveniently located just minutes from a newly built Publix, shopping, dining, and everyday essentials, this home combines space, updates, and an unbeatable location. Don’t miss the opportunity to own a move-in ready home in one of Winter Haven’s growing areas. Schedule your private showing today!
Winter Haven is located in Florida. Winter Haven, Florida has a population of 48,707. Winter Haven is less family-centric than the surrounding county with 26.09% of the households containing married families with children. The county average for households married with children is 26.62%.
The median household income in Winter Haven, Florida is $50,842. The median household income for the surrounding county is $55,099 compared to the national median of $69,021. The median age of people living in Winter Haven is 41 years.
The average high temperature in July is 92.5 degrees, with an average low temperature in January of 49.7 degrees. The average rainfall is approximately 51.2 inches per year, with 0 inches of snow per year.
