Homes For Sale in Winter Haven 33884 - 438 homes

Remarks: Welcome to this beautifully updated Cassidy-built 4-bedroom, 3-bath pool home in the highly desirable Terranova community of Winter Haven. Pride of ownership is evident throughout this move-in ready residence, where nearly every major component has been updated since 2022. The stunning kitchen was completely renovated with new cabinetry, tile backsplash, Cambria countertops, new sinks, updated fixtures, and all new appliances. Matching Cambria Quartz Kitchen & Master bathroom countertops, guest bathrooms and laundry room, complemented by updated faucets, sinks, and lighting throughout the home. Additional improvements include a new roof (11/2022), new A/C system (2023), new water heater (2024), new bedroom carpeting (2022), new blinds throughout (2022), complete interior and exterior painting (2022), plywood attic flooring for added storage (2023), new garage cabinets, laundry room cabinets, and additional cabinetry in the primary and pool bathrooms. Outdoor living is equally impressive with a screened and heated saltwater pool that underwent extensive remodeling in 2022, including an exposed aggregate finish, new ANSI-certified main drain covers, updated fittings and lighting, a new pool pump (2022), a new pool heater (2023), and a new screen enclosure (2022). Porcelain tile flooring enhances the main living areas, while the open floor plan, high ceilings, and spacious layout make this home perfect for everyday living and entertaining. One of the home's standout features is the private fourth bedroom and third bathroom, which are separated by a sliding door, creating an ideal in-law suite, guest retreat, or private space for multi-generational living. Private gated entrance to Chain of Lakes Elementary for neighborhood access only. Conveniently located near shopping, restaurants, medical facilities, LEGOLAND, and Winter Haven's Chain of Lakes, this exceptional property offers the peace of mind that comes from knowing the expensive updates have already been completed. Don't miss the opportunity to own one of Terranova's finest homes.

Listing is courtesy of: CROSBY & ASSOCIATES, INC. (863-293-5600)

Listing Agent: Kimberly Davis (850-625-8855)

Remarks: HUGE PRICE REDUCTION! Spacious 2,336 SF pool home in the gated, tranquil Overlook Estates. This 4BR/2BA floorplan features a split-bedroom layout and generous living space including an eat-in kitchen, 17x18 vaulted family room, 10x16 dining room with bay window, and a large foyer. The master suite includes a dressing alcove and walk-in closet; an adjacent bedroom makes an ideal office or nursery. High-traffic areas feature tile flooring; sliding glass doors in three rooms recess into the wall and open to a 31x50 pool deck — perfect for indoor/outdoor living. Additional highlights: 95x130 lot, terraced front walkway, 7x8 laundry with cabinetry and utility sink, 22x23 garage with built-in storage, tankless water heater, and leaf filter gutter guards. Ready for your finishing touches!

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

Listing Agent: Amy Reynolds (863-412-2279)

Remarks: Under Construction. The first floor of the stunning Edison two-story home is host to an open-concept layout that combines the kitchen with the living and dining areas, and an outdoor patio is easily reached off the main living space. Upstairs, five bedrooms surround a versatile loft, including the luxe owner’s suite, complete with a generous walk-in closet and en-suite bathroom. Villa Mar is a masterplan community of new single-family homes. Near Historic downtown Winter Haven. There are lots of shops, restaurants, bike paths, and easy access to nearby highways. Close to Legoland and Bok Tower Gardens. The much anticipated “Villar Mar” community is what you have been looking for. A safe small town feel with convenience.

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

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

Remarks: Under Construction. Open flow sets the tone for this elegant new Crestone II two-story townhome. There are a total of three bedrooms. The first level features a spacious and flexible open-concept layout shared between the kitchen, dining room and family room, maximizing the interior living space. Two secondary bedrooms and a lavish owner’s suite featuring a full bathroom comprise the second floor. Serenity at Peace Creek Reserve is a masterplan community of new townhomes with a beautiful natural creek. Winter Haven is the chain of lakes city, with over 26 linked together by a canal. There are lots of shops, restaurants, and bike paths. Peace Creek Reserve is what you have been looking for. A safe small town feel with convenience, the perfect place to raise a family.

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

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

Remarks: Virtually Staged. Welcome to easy Florida living in the sought-after Orchid Springs 55+ community! This beautifully maintained 2-bedroom, 2-bath condominium is located in the desirable San Miguel Building and offers a peaceful second-floor setting with lovely views of the lush, landscaped grounds below. Step inside to find a spacious and comfortable floor plan designed for both everyday living and entertaining. The bright Florida room provides the perfect spot to enjoy your morning coffee, read a book, or simply relax while taking in the serene garden views. The primary suite offers a private retreat featuring an oversized walk-in closet and an updated bathroom with modern finishes, creating a comfortable and inviting space to start and end each day. One of the biggest advantages of this home is the exceptional value offered through the monthly HOA fee, which includes gas, water, sewer, trash, community pool, clubhouse, amenities, exterior maintenance, and grounds maintenance—allowing you to spend more time enjoying life and less time worrying about upkeep. Ideally located at 400 El Camino Drive, Unit 202, you’ll enjoy convenient access to shopping, dining, medical facilities, downtown Winter Haven, and the area’s many lakes and recreational opportunities. Whether you’re looking for a year-round residence, a winter getaway, or a low-maintenance lifestyle, this inviting condo offers the perfect combination of comfort, convenience, and affordability in one of Winter Haven’s most established 55+ communities. Come discover why so many residents love calling Orchid Springs home!

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

Listing Agent: Jessica Willaford (863-662-8549)

Remarks: Under Construction. Brand new, energy-efficient home available by Jul 2026! Configure the flex room in the front of the home to an at home office space or hobby space. Past the foyer, the open kitchen flows to the dining space, great room and outside patio. Private primary suite offers a spacious area to relax. Visit Villamar and explore new single-family homes for sale in Winter Haven, FL. Residents will have access to two resort-style amenity centers featuring a clubhouse, pool, and playground. Winter Haven is known for its beautiful chain of lakes with lakeside restaurants and its award-winning community theater. Nearby attractions include Legoland Florida and Peppa Pig Theme Park. A brand-new model and new phase are coming soon. Each of our homes is built with innovative, energy-efficient features designed to help you enjoy more savings, better health, real comfort and peace of mind.

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

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

Remarks: Welcome 55+ or investors! This well-maintained one-bedroom, one-bathroom condo with an additional bonus room is the perfect place to retire and take it easy, or a fantastic addition to your investment portfolio. Located in the heart of Winter Haven, this home is just a mile from Legoland, shopping, and dining. The community also features a sparkling pool for you to relax and enjoy year-round. Don't miss out on this prime opportunity!

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

Listing Agent: Angela Perkins (863-280-5396)

Remarks: This sprawling two-story luxury pool residence showcases exceptional craftsmanship and timeless elegance, enhanced by extensive upgrades throughout and a Generac home generator. From the moment you enter, you'll be captivated by soaring tray and cathedral ceilings, rich crown molding, and refined architectural details that create an atmosphere of sophistication and grandeur. Designed to inspire culinary excellence, the chef’s kitchen is appointed with a professional-grade gas cooktop, custom solid wood cabinetry, a hidden walk-in pantry, farmhouse sink, and a picturesque window framing serene views of Lake Winterset. A convenient built-in workstation, located near the spacious laundry room and oversized three-car garage, provides added functionality for everyday living. The sumptuous primary suite serves as a private retreat, featuring beautiful custom built-ins, dual vanities, a chandelier-accented soaking tub, an expansive walk-in shower, and generous his-and-her custom closets. A tranquil sitting area offers the perfect space for reading and relaxation, while French doors provide direct access to the poolside lanai. Created for effortless entertaining, the grand great room seamlessly connects indoor and outdoor living through pocketing sliding glass doors that open to a spectacular pavered lanai complete with a summer kitchen, sparkling pool, and elegant water feature. Two additional en-suite bedrooms with walk-in closets are conveniently located on the main level, while a well-appointed powder bath serves guests. The upper level offers a private guest or in-law retreat featuring a spacious en-suite bedroom, full bath, media room, and a sizable studio or flex space overlooking the tranquil waters of Lake Winterset. Elegant formal living and dining rooms provide the perfect backdrop for memorable gatherings, enhanced by exquisite finishes and statement lighting. A distinguished library or executive home office, adorned with rich burled wood cabinetry and custom doors, delivers both privacy and sophistication.Situated on an oversized corner homesite, this exceptional residence is enveloped by lush, mature landscaping that creates a sense of privacy and exclusivity. Combining luxurious amenities, breathtaking lake views, and thoughtfully designed living spaces, this remarkable estate offers an unparalleled lifestyle in a truly spectacular setting.

Listing is courtesy of: RED BIRD REALTY (850-201-8810)

Listing Agent: Lisa Kleine (863-660-6787)

Remarks: Welcome to Cypresswood Golf & Country Club, a gated and guard-gated community offering resort-style living in a beautiful golf course setting. This well-maintained 3-bedroom, 2-bathroom home is ideally situated at the end of a quiet cul-de-sac, providing one of the most desirable locations on the street. Inside, you'll find a spacious open-concept floor plan designed for comfortable living and entertaining. The large kitchen features stainless steel appliances, abundant cabinetry, and a center island that serves as the heart of the home. The living and dining areas flow seamlessly to the expansive fully screened lanai, creating the perfect indoor-outdoor living space. The private primary suite offers direct access to the lanai, a massive walk-in closet, and an oversized walk-in shower complete with a built-in bench. Two additional bedrooms and a second full bath provide plenty of room for family and guests. Residents of Cypresswood Golf & Country Club enjoy access to exceptional community amenities, including a clubhouse, community pool, tennis courts, and beautifully maintained grounds. Don't miss this opportunity to enjoy Florida living at its finest in one of the area's most sought-after communities.

Listing is courtesy of: GOLD HEART REALTY LLC (863-224-2419)

Listing Agent: Lori Roberts (863-224-2419)

Remarks: Come see 2953 Whispering Trails Dr, a residence showcasing recent fresh interior paint and fresh exterior paint for a clean, cohesive appearance. The kitchen is equipped with all stainless steel appliances, and the primary bathroom provides practical double sinks. Outside, a welcoming patio leads to a fully fenced in backyard. This move-in ready property blends comfort and recent updates seamlessly. Included 100-Day Home Warranty with buyer activation

Listing is courtesy of: OPENDOOR BROKERAGE LLC (480-462-5392)

Listing Agent: Karen Albright (480-462-5392)

Remarks: HUGE $45,000 PRICE DROP! Welcome to one of the largest homes in the desirable Harmony Lake Eloise community! This spacious 5-bedroom, 3-bathroom residence offers a versatile and thoughtfully designed layout perfect for modern living. A generously sized flex room—currently used as a dining area—can easily be converted into a 6th bedroom, home office, or bonus space to suit your needs. The spacious kitchen is a true centerpiece, featuring quartz countertops, beautiful cabinetry, recessed lighting, stainless steel appliances, a large kitchen island, and a walk-in pantry. The interior paint throughout the home offers a soft, inviting color palette that’s easy on the eyes. The first floor showcases beautiful tile flooring throughout, along with a large bedroom and full bathroom—ideal for guests or multigenerational living. You’ll also find an additional sitting area or playroom, providing even more functional living space. Upstairs, all bedrooms are upgraded with luxury vinyl flooring, offering both style and durability. The conveniently located upstairs laundry room adds everyday ease. The expansive primary suite boasts his-and-her closets, dual vanities, and a walk-in shower —your own private retreat. With tons of storage throughout and one of the largest floor plans in the community, this home combines space, comfort, and flexibility. Enjoy a low monthly HOA fee and access to a beautiful community pool. Ideally located just minutes from Lake Eloise, Legoland Florida Resort, shopping, dining, schools, and major roadways, with easy access to Orlando, Tampa, and Walt Disney World. This is a must-see property in Winter Haven!

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

Listing Agent: David Small (407-601-8351)

Remarks: Discover this must-see Tourmaline home. Included features: an inviting covered entry; an expansive great room; a well-appointed kitchen offering 42" cabinets, quartz countertops, a roomy pantry, a center island and an adjacent dining area; a beautiful primary suite showcasing an immense walk-in closet and a private bath; a convenient laundry; an airy loft; a storage area and a covered patio. This home also offers ceiling fan prewiring in select rooms.

Listing is courtesy of: AXEN REALTY, LLC (480-399-1218)

Listing Agent: Stephanie Morales, Llc (407-399-2055)

Remarks: Discover this stunning Ruby home, ready for quick move-in! Included features: a welcoming covered entry; a smartly planned kitchen boasting white 42" cabinets, a center island, a large walk-in pantry, and an open dining area; an immense great room; a secluded primary suite showcasing a generous walk-in closet and a private bath; three secondary bedrooms; a shared hall bath; a central laundry; and a comfortable covered patio. *Take advantage of special financing on quick move-in homes OR buy a to-be-built home and enjoy up to $20,000 in Flex Funds toward homes that can close in a timely manner! Options may vary by community, and offers are available on select homes on a first-come, first-served basis. Contact builder for more information!

Listing is courtesy of: AXEN REALTY, LLC (480-399-1218)

Listing Agent: Stephanie Morales, Llc (407-399-2055)

Remarks: Virtually Staged. Short Sale. Welcome home to Villa Mar, a vibrant and growing community in beautiful Winter Haven! Built in 2023 and occupied for just one year, this 5-bedroom, 3-bathroom home offers that “like-new” feel with thoughtful upgrades throughout. As you step inside, you’re greeted by an inviting open-concept layout designed for both comfort and connection. The kitchen shines with stainless steel appliances, an oversized pantry, and cabinets with updated fixtures, all opening to the main living area with NEW laminate flooring—creating a seamless space for gathering and entertaining. A bedroom and full bathroom on the main floor offer ideal flexibility for guests or multi-generational living. Upstairs, you’ll find four additional bedrooms, a loft that’s perfect for a home office or a cozy nook to unwind and recharge, and a conveniently located laundry room. The oversized primary suite features a large walk-in closet and an ensuite bathroom complete with a stand-alone shower, upgraded shower head, and linen closet for added convenience. Step outside to a fully fenced backyard, offering privacy and plenty of space to create your own outdoor retreat—whether that means adding a future pool, garden, or simply enjoying a quiet evening of relaxation. The oversized under-the-stairs storage and two-car garage add even more practicality, while the LOW HOA helps keep ownership easy and affordable. Perfectly situated just off US-27, residents enjoy proximity to dining, shopping, and grocery options, as well as easy access to I-17. Outdoor enthusiasts will love being near the Winter Haven Chain of Lakes, ideal for boating, kayaking, fishing, or simply soaking up the sunshine. Plus, the charming Downtown Winter Haven Historic District is nearby—home to local restaurants, boutiques, and community events like First Fridays, the Wine, Chocolate & Cheese Festival, and so many more! For a weekend of fun with the family and friends, LEGOLAND is only 3.5 miles away! This home beautifully blends modern comfort, functional space, and a convenient location—making it a must-see in the heart of Winter Haven. This is the one you've been waiting on. Schedule a showing today and make it yours!

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

Listing Agent: Brianna Perez Montalvo (407-687-3837)

Remarks: Virtually Staged. Welcome Home!!! 4577 Back Nine Dr. Winter Haven, Fl. features 3 bedrooms and 2 full baths and is located in Lake Ashton, an Exclusive Florida Retirement 55+ community. This home has BRAND NEW EXTERIOR PAINT! The widened, paver driveway offers extra room for parking and the screened entry at the front door is an added bonus. The glass leaded front door with large eye brow window above leads you into a home that is warm, inviting and spacious. The open-concept kitchen showcases granite countertops, stainless steel appliances, Maple cabinets and a Pantry Cabinet with convenient pull-out shelving. You can seamlessly blend indoor and outdoor living by sliding open the living room and dinette area sliding glass doors to the screened, covered lanai with 8" aluminum border base. It's the perfect place for entertaining. The primary bedroom with En-Suite bath has been extended 4 ft. to provide additional living space. It's the perfect getaway and you'll enjoy the EXTRA SPACE in the primary suite. The primary bathroom has ample closet space with His/Her Walk In Closets with Organization System, a large walk in shower with double shower heads, a separate water closet and separate His and Her Vanities. Her vanity has an additional make up area. Guests will appreciate the separate bedrooms and bath behind a pocket door. Additional features include: an automatic screen on the garage door, a separate irrigation meter, 18" diagonal tile in home (Bed 2 and Bed 3 are excluded), crown moulding, New A/C modulator, cabinetry in laundry room, Plantation Shutters in the Bedrooms, Upgraded entry light fixture, surround sound in the living room, additional insulation in the attic, new interior paint in Bedroom 1 and Guest Bathroom, new interior paint in the formal dining and dinette areas. Lake Ashton, a Florida Retirement community, has a Clubhouse with large grand ballroom, Outdoor Community Heated Pool, Tennis Courts, Bocce Ball, Shuffleboard, Fitness Center, Movie Theater, Bowling Lanes, Restaurant (Charm City)and More! The Health and Fitness center has indoor basketball, indoor racquetball, indoor heated pool, pickle ball and tennis courts, media center, card, craft and billiard rooms. There are two golf courses located in Lake Ashton. Memberships are optional and not a requirement to reside in Lake Ashton. Residents enjoy the resort style amenities and activities offered in Lake Ashton, a premier Florida Retirement Community. Don't miss this opportunity to own your piece of paradise. Check out the photo gallery and make your appointment to tour this home.

Listing is courtesy of: LAKE ASHTON REALTY INC. (863-221-5970)

Listing Agent: Lori Raath (863-409-6899)

Remarks: Spacious 2-bedroom, 2-bath upper corner condo in the Barcelona Building of Orchid Springs, an all-ages community. This desirable end unit offers natural light and views from three sides, plus added privacy with minimal foot traffic. Recent updates include luxury vinyl plank flooring throughout, smooth ceilings, and neutral zero-VOC paint. Routine annual A/C maintenance completed in May 2026. The updated kitchen features 17 cabinets, 10 drawers, and a pantry, while the spacious primary suite offers a walk-in closet and en-suite bath. Assigned parking is located just below the unit. The monthly HOA fee of $312.69 covers exterior maintenance, grounds care, water, sewer, trash, gas service, pest control, common laundry facilities, and capital reserves. Conveniently located near LEGOLAND Florida and between Orlando and Tampa, with easy access to Winter Haven's renowned Chain of Lakes.

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

Listing Agent: Melissa Witter (863-206-8744)

Remarks: Discover affordable luxury and modern Florida living in this beautifully designed brand-new 2025 home located in the growing Peach Crossings community of Winter Haven. Perfectly positioned for first-time homebuyers, growing families, remote professionals, and buyers seeking more space without sacrificing style, this move-in ready 4-bedroom, 2-bath residence offers the ideal combination of comfort, functionality, and value in one of Polk County’s rapidly expanding areas. Built by LGI Homes, the highly sought-after “Summit” floor plan features an open-concept design with soaring ceilings, abundant natural light, and thoughtfully designed living spaces perfect for entertaining and everyday living. The spacious chef-inspired kitchen is equipped with granite countertops, solid wood cabinetry, Whirlpool stainless steel appliances, generous prep space, and seamless flow into the dining and family room area creating the perfect setting for gatherings, holidays, and movie nights at home. The oversized primary suite offers a peaceful retreat with a large walk-in closet and spa-style en-suite bathroom featuring dual vanities, stone countertops, and a step-in shower. Three additional bedrooms provide flexibility for guest rooms, a home office, fitness room, or playroom. Luxury vinyl flooring throughout the main living areas, energy-efficient windows, smart layout design, interior laundry room, and modern finishes add both style and practicality for today’s buyers. Step outside and enjoy covered outdoor living space ideal for relaxing evenings, weekend cookouts, or enjoying Florida’s year-round sunshine. Professionally designed landscaping, irrigation, sidewalks, and attractive curb appeal make this home stand out from the moment you arrive. Located near shopping, dining, medical facilities, parks, and major commuter routes, Peach Crossings offers convenient access to Lakeland, Orlando, and Central Florida attractions while still maintaining a quieter residential atmosphere. Community amenities include playgrounds, parks, picnic areas, and access to highly desired Polk County schools, making this neighborhood especially appealing to families and buyers relocating to Florida. With no CDD fees, low HOA costs, builder warranty coverage, and financing options including FHA, VA, USDA, and Conventional loans, this property presents an exceptional opportunity for buyers looking for affordable new construction in Winter Haven with long-term value and lifestyle appeal.

Listing is courtesy of: WATSON REALTY CORP. (407-589-1600)

Listing Agent: Renee Anthony (407-603-5935)

Remarks: Better then new 2022-built home on a desirable corner lot in the heart of 33884, located in a family-style community loaded with amenities! This beautiful 3-bedroom, 2-bath home offers modern living with an open, functional layout and split floorplan. A standout feature is the upgraded enclosed patio/all-seasons room, complete with windows and screens—perfect for relaxing year-round, entertaining guests, or enjoying Florida living without the bugs. The home shows better then new and offers peace of mind with newer construction, while the community amenities add incredible value and lifestyle appeal. Conveniently located near shopping, dining, schools and everything Winter Haven has to offer. Move-in ready and priced to sell—don’t miss this one!

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

Listing Agent: Katherine Montana - De Jesus (863-508-3000)

Remarks: Under contract-accepting backup offers. Location, Location, Location! Welcome Home! This beautifully remodeled 3-bedroom, 2-bath block home offers 2,000 sq ft of living space. Situated on a desirable corner lot, this block home blends style, function, and Florida living at its best. Inside, you’ll find updates throughout, including fresh finishes, modern fixtures, Luxury Vinyl Plank, and a bright, open layout perfect for both everyday living and entertaining. The kitchen showcases all wood cabinets with Quartz counter tops and all new Stainless Steel Appliances. The home features a newer roof and a brand-new water heater, giving buyers peace of mind from day one. Enjoy the outdoors year-round with a screened-in pool, ideal for relaxing or hosting gatherings. The fully fenced backyard provides privacy, space for pets or play, and plenty of room to make it your own. This home truly checks all the boxes — updated, spacious, and designed for easy Florida living. A must-see for anyone looking for comfort, style, and value. Conveniently located to down town Winter Haven and Medical, and located between Tampa and Orlando. Schedule your showing today!

Listing is courtesy of: DALTON WADE INC (888-668-8283)

Listing Agent: Christopher Howard (888-668-8283)

Remarks: Charming and well-maintained and can be your HOME in Winter Haven! This property features a functional open concept floor plan with spacious living areas to entertain the entire family. This property is perfect for starter or investment! Schedule your private showing today. Buyer shall verify all the measurements provided herein.

Listing is courtesy of: HOMES UNLIMITED REAL ESTATE CORP (407-378-5600)

Listing Agent: Waleska Rodriguez Leon (407-929-2734)