Homes For Sale in Winter Haven 33884 - 329 homes

Remarks: Owner motivated and ready to negotiate — WOW! This BEAUTIFUL 1361SF 2BR/2BA FIRST-FLOOR condo in Orchid Springs offers stunning lagoon/pond views! Located in the 55+ Granada Building, where at least one occupant must be 55+. IMMEDIATELY AVAILABLE and MOVE-IN READY! Step into an open, airy floor plan with tile throughout, creating a bright and spacious feel. The dining area, living room, and bonus room flow seamlessly together, all overlooking the tranquil lagoon. As an end unit, the living room and bedrooms enjoy extra windows with peaceful courtyard views. The primary bedroom features a walk-in closet plus an additional hallway closet, providing excellent storage. Both bathrooms are well-appointed, with one offering a custom vanity and a tub/shower combo. Additional highlights include assigned parking directly in front of the unit. Perfect for year-round living or a seasonal retreat in a serene, well-maintained community.

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

Listing Agent: Sharon Gastelbondo (863-800-4655)

Remarks: Live the lake life you've been dreaming of in this beautifully maintained 3-bedroom, 2-bath home in Winter Haven! Perfectly positioned for those who love being on the water, this property offers lake access with use of two community docks ideal for boating, fishing, or catching stunning Florida sunsets. Step inside to find a bright, comfortable layout enhanced by new windows that fill the home with natural light. Major updates have already been taken care of, including a newer roof, HVAC system, water heater, new garage door giving buyers peace of mind and true move-in-ready convenience. The easy access to the docks makes it simple to embrace an active, outdoor lifestyle without the high price of direct waterfront. Located just minutes from LEGOLAND Florida Resort, shopping, dining, and entertainment, this home offers the perfect balance of adventure and convenience. Whether you're a boating enthusiast, weekend adventurer, or simply someone who loves being near the water, this property delivers the lifestyle -- not just the home.

Listing is courtesy of: RELENTLESS REAL ESTATE CO. (321-302-0763)

Listing Agent: Scott Loveridge (321-302-0763)

Remarks: Don’t miss the opportunity to own a home in the exclusive gated community of Wyndham, featuring manned security, fewer than 45 homes, and beautifully tree-lined streets shaded by mature oak trees. Situated on a private .69-acre lot, this exceptional one-story estate offers both privacy and space in one of the area’s most desirable neighborhoods. Expanded to 3,974 square feet, this beautifully updated home now offers 5 bedrooms and 3 bathrooms, including a 448-square-foot addition completed in July 2024 with two bedrooms and a full bathroom, making it ideal for guests, multi-generational living, or flexible space. Inside, the home showcases hardwood-style flooring throughout most of the living areas, with LVP and ceramic tile in the remaining spaces. The layout features a spacious formal dining room and a formal living room with a wood-burning fireplace overlooking the private enclosed pool area, creating a warm and inviting setting. The spacious kitchen is a chef’s dream, offering abundant cabinet and counter space, a mini wine and beverage refrigerator, and new appliances including a Bosch dishwasher and Frigidaire refrigerator, microwave, and range. Charming bay windows surround the breakfast nook, creating a bright and inviting space for casual dining. The kitchen flows seamlessly into the main living areas, providing open sightlines that make the space perfect for entertaining while enjoying abundant natural light. The private primary suite is located on its own wing of the home and features a separate sitting area, two walk-in closets, and a spa-like ensuite bathroom with a soaking tub, oversized shower, and dual vanities. This bedroom also features French doors leading directly to the pool area. The four additional bedrooms are generously sized, with two full bathrooms thoughtfully positioned for convenience and functionality for family and guests. Step outside to enjoy the fully enclosed saltwater pool and outdoor entertaining area, perfect for relaxing or hosting family and friends. Recent upgrades include a new roof (2023), a new AC system, a whole-house water softener, a kitchen filtration system, and the two-bedroom, one-bath addition (July 2024.) Additional highlights include a central vacuum system, pest control with a termite bond, a 3-car garage with built-in storage, a bonus room ideal for an office, gym, or playroom, and a mudroom conveniently located just off the garage for everyday organization. Residents of Wyndham enjoy community amenities including tennis and pickleball courts, as well as a playground, all within a short distance. Conveniently located near Highway 27, the home is less than an hour from Walt Disney World and approximately 1.5 hours from both Orlando International Airport (MCO) and Tampa International Airport (TPA). With shopping, dining, and everyday conveniences nearby, Winter Haven offers an exceptional quality of life with endless opportunities for recreation, adventure, and relaxation. Don't miss out on your new dream home and schedule your private showing today!

Listing is courtesy of: LIVE FLORIDA REALTY (863-868-8905)

Listing Agent: Jenna Henderson (850-524-3843)

Remarks: Owner motivated and ready to negotiate — WOW! This BEAUTIFUL 931 SF 1BR/1BA FIRST-FLOOR condo in Orchid Springs offers stunning lagoon views! Located in the 55+ Granada Building, where at least one occupant must be 55+. IMMEDIATELY AVAILABLE and MOVE-IN READY! Step into an open, airy floor plan with tile throughout, creating a bright and spacious feel. The dining area, living room, and bonus room flow seamlessly together, all overlooking the tranquil lagoon. As an end unit, the living room and bedroom enjoy extra windows with peaceful courtyard views. The bedroom features a walk-in closet plus an additional hallway closet, providing excellent storage. The bathroom includes a custom vanity and a tub/shower combo. A washer and dryer are included, offering added convenience. Additional highlights include assigned parking directly in front of the unit. Perfect for year-round living or a seasonal retreat in a serene, well-maintained community.

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

Listing Agent: Sharon Gastelbondo (863-800-4655)

Remarks: Price Improvement. Offered for the first time, this stunning custom-built luxury home in SE Winter Haven in the gated community of Heron Cay. This exquisite Mediterranean style home features 3,640 square feet of living space with 4 bedrooms, plus a large flex room, 3 ½ baths plus a gorgeous pool and outside entertaining area on a lot measuring .61 acres. As you enter through the front double doors with custom decorative iron work and a soaring ceiling of over 21 feet, you are in a magnificent foyer. The living room has the first of two wood/gas fireplaces with views and access to your private pool via the oversized arched glass French doors on either side of the fireplace. The elegant dining room is oversized and perfect for large family gatherings or entertaining and is adjacent to your cook’s dream kitchen. In addition, off the entry foyer is a home office with a massive built in book case and desk with the flexibility to also be a 4th bedroom. The kitchen is a culinary dream with custom cabinetry, granite countertops, a spacious island, a walk-in pantry and upscale stainless appliances including a gas stove and double wall oven. The kitchen overlooks the great room, the breakfast nook and the pool. The great room ceiling beams are another architectural feature, and a second wood/gas fireplace is a focal point of this amazing room. Crown molding, columns, hurricane rated windows, and a neutral color palette are throughout this home. Next to the great room is a large bonus/ flex space with French doors that can be used as a playroom, a library or even a workout space. The oversized primary bedroom has access out to the pool and features a spa type ensuite complete with a soaking tub and dual vanities. Twin oversized, walk-in closets feature built in shelves for keeping everything organized with access being via barn doors with glass panels. The guest rooms on the other side of the house have separate toilet/vanity areas with a shared tub/shower and private hallway. These are the only two rooms with carpet and it is a low pile neutral Berber style. Both guest rooms have oversized, walk in closets and there is a large linen closet in the private hallway. An indoor laundry room with built ins is well-located next to the kitchen and includes a laundry tub. Outdoor entertaining is perfect for celebrations in the screened lanai with your heated pool and outdoor kitchen! It is also a tranquil space to enjoy your friends and family as the pool features both a fountain and an area for plants. A pool bathroom is off the covered lanai and features a shower making an after swim shower really convenient. All of this beauty is set on professionally landscaped grounds with a whole house natural gas generator (2023) fed from the street and hurricane rated windows. The attached 3 car garage is oversized and features 3 separate garage doors and a driveway complete with a paver turnaround area for easy access in and out of the home. The home features a tile roof and many exterior trim details including landscape lighting only found in a custom, luxury home like this. The irrigation system is from this home’s private well. Built by the original owners and meticulously maintained showing pride of ownership throughout. This home has a low HOA that includes cable tv and Wi-Fi and is convenient to shopping, doctors, hospitals and local state colleges. Centrally located for an easy commute to Orlando or Tampa. Enjoy the virtual tour via the link.

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

Listing Agent: Susan Mayrant (863-255-2715)

Remarks: Located in Winter Haven, this 2 bedroom, 2 bathroom double wide mobile home sits on an oversized corner lot! The home offers a functional layout with comfortable living space and enclosed front porch. Both bedrooms have walk-in closets and the primary bedroom also has an en suite. The closed-in carport space offers extra functionality as a bonus room and also has an enclosed laundry room. The large corner lot has a fenced in backyard and also provides a detached workshop with AC unit perfect for storage, hobbies, and so much more! The neighborhood also has a boat ramp to Lake Fox for the boaters and fishing lovers! Conveniently located near shopping, dining, Legoland, and Hwy 27 for commuters, this is a great opportunity for a primary residence or investment property! Schedule a private tour today!

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

Listing Agent: Ashley Helms (863-206-7260)

Remarks: Welcome to the Summit model in Peach Crossings, a beautiful brand-new home featuring four bedrooms and two bathrooms with an inviting open-concept design. This home boasts high ceilings, enhancing the spacious and airy feel throughout. The master retreat is a true sanctuary, offering a generously sized bedroom that connects to a luxurious en-suite bathroom with a dual sink vanity for added convenience and a step-in shower for a spa-like experience. The kitchen is designed for both function and style, featuring exceptional counter space and brand-new Whirlpool appliances, including a refrigerator, stove, dishwasher, and microwave. A spacious hall closet provides extra storage, keeping everything organized. The family room is the perfect space for cozy movie nights, with ample room for a large sectional and entertainment setup. Whether it’s a movie marathon or a casual night in, this space is designed for relaxation, laughter, and quality time with loved ones. Step outside to the lanai, with no rear neighbors, an ideal spot for enjoying warm Florida evenings with family and friends. The home also features professional front yard landscaping, adding to its curb appeal. This home is Located in the heart of Polk County, Peach Crossings offers the best of lake living with easy access to shopping, dining, and top attractions. Families will love the highly-rated Polk County schools, and the community features a playground and picnic area for added enjoyment. With all upgrades included, this home is move-in ready! Schedule your showing today!

Listing is courtesy of: LGI REALTY- FLORIDA, LLC (904-449-3938)

Listing Agent: Gayle Van Wagenen (904-449-3938)

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

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

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

Remarks: 2118 Chris Dr is a property that boasts a kitchen equipped with all stainless steel appliances, adding a modern touch to the culinary space. The kitchen island serves as a functional centerpiece, perfect for meal preparation or casual dining. The primary bedroom is a haven of comfort, complete with a walk-in closet that provides ample storage for your wardrobe. With these attributes, this property ensures a comfortable and convenient lifestyle. 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: One or more photo(s) has been virtually staged. Welcome to your gorgeous new home! This executive style home is located in the highly sought after gated community, Eloise Pointe Estates, and is conveniently located 1/4 mile behind Legoland. Community was originally developed by then Boston Red Sox owner, Buddy Larue when they spring trained in Winter Haven. Upon entering this desirable 4 bedroom 3.5 bathroom home one finds many updates, completely remodeled kitchen and primary bathroom. New cabinetry, granite counter-tops, beautiful tongue and groove wood ceiling in the kitchen, paint (including the pool deck) & LVP flooring throughout. The laundry room is also plumbed for a sink. Upstairs over the garage is the 4th bedroom and full bath or use as a Bonus/Theatre room. Also included is an oversized three car garage, a large lot with some beautiful scrub oak trees on just over a 1/2 an acre & privacy fenced. Screened in 15x30 pool. Another great feature of this home is the low HOA fee of only $1200 for the year and no CDD.

Listing is courtesy of: KLINE REAL ESTATE SERVICES (863-287-0204)

Listing Agent: Scott Kline (863-287-0204)

Remarks: Impeccably maintained home in the sought-after Traditions 55+ community in Winter Haven! This spacious 2-bedroom, 2-bath home with a dedicated office/den offers over 1,500 square feet of open-concept living space, designed for both comfort and functionality. The home features new flooring throughout, upgraded countertops, 36-inch kitchen cabinets, and modern lighting fixtures, creating a bright and inviting kitchen and living area perfect for everyday living or entertaining. Both bathrooms have been tastefully upgraded, and additional improvements include a new water heater and recently replaced AC coil for added efficiency and peace of mind. The home was freshly painted inside and out in 2023, giving it a clean, modern feel throughout. Step outside to enjoy the new screened-in porch, ideal for relaxing mornings or evening gatherings while overlooking the newly installed sod that enhances the home’s curb appeal. The extended driveway provides additional parking and convenience, and the home is handicap accessible, offering added functionality and ease of living. Residents of Traditions enjoy resort-style amenities, including community boat ramp access, fishing, dock, and private water access, along with a community pool and recreational facilities. The HOA includes cable TV, internet, exterior, grounds maintenance, pool maintenance, recreational facilities, and security, making this a truly low-maintenance lifestyle. Located just minutes from shopping, dining, and major roadways, this move-in ready home combines modern updates, accessibility, and the vibrant lifestyle of one of Winter Haven’s most desirable active adult communities.

Listing is courtesy of: CREEGAN GROUP (407-622-1111)

Listing Agent: Nathan Mercado (407-353-8612)

Remarks: Brand new, energy-efficient home available NOW! Open floor plan creates a unified living space with a large great room that overlooks the kitchen. 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: 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.

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

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

Remarks: Under contract-accepting backup offers. Discover this charming 4-bedroom, 2-bath home with 1,840 sqft of comfortable living space in the highly desirable Ruby Lake neighborhood in Southeast Winter Haven. Located near LEGOLAND®, this home offers both convenience and a great sense of community. Enjoy the generous bedrooms, including a comfortable primary suite, plus a backyard ready for play or entertaining! With a fantastic location near schools, shopping, and parks, everything you need is just minutes away. Don’t miss the chance to make this lovely Ruby Lake home yours—schedule a tour today!

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

Listing Agent: Steve Lockhart (863-289-9801)

Remarks: NO LOT RENT! Live the retired life you worked so hard for. Whether you are a snowbird or looking to enjoy full-time residency, Orange Manor West welcomes you. This highly sought-after 55+ gated community in Winter Haven, secondary resident(s) must be 40+. This fully furnished 2-bedroom, 2-bath home offers a functional layout with recent updates including a 2018 roof, 2022 HVAC, 2021 water heater, newer vinyl flooring, and updated appliances. The home features a spacious layout with walk-in closets in both bedrooms, a private primary suite with a step-in shower, and an enclosed Florida room that is perfect for relaxing mornings or unwinding in the evening. Enjoy an active, low-maintenance lifestyle with monthly fees that include cable, internet, and trash, in a community that allows only service and emotional support animals. Residents have access to a wide range of amenities including a community pool, clubhouse, billiards, shuffleboard, horseshoes, mini golf, fishing, lake access, and a full calendar of social activities such as bingo, cards, sports tournaments, quilting, and much more. Additional features include onsite management, 24-hour emergency service, extra storage for boats and recreational vehicles, and boat slips. Located in Southeast Winter Haven, you are just minutes from shopping, dining, and everyday conveniences, with Legoland ad Peppa Pig theme parks nearby for visiting guests. This is a great opportunity to enjoy comfort, convenience, and community all in one place.

Listing is courtesy of: FLORIDA REALTY MARKETPLACE (863-877-1915)

Listing Agent: Jenn Manzella (863-866-0335)

Remarks: Under Construction. Brand new, energy-efficient home available by Aug 2025! Open floor plan creates a unified living space with a large great room that overlooks the kitchen. 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: 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.

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

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

Remarks: Short Sale. Subject to lender approval. Property has sustained prior storm-related damage with documented mold and interior environmental conditions. Due to these conditions, interior access is limited and not suitable for routine showings. Property is being sold AS-IS and will require substantial remediation, including potential structural and electrical work. Access is restricted to serious, qualified buyers and must be coordinated with the listing agent. Property includes leased solar panels. Buyer to verify terms and assume existing lease. Buyer to verify all measurements, square footage, HOA, and property information.

Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)

Listing Agent: Hien Nguyen (479-926-7079)

Remarks: Welcome to this beautifully maintained residence located in the lakefront community of Traditions, one of Winter Haven’s premier 55+ gated communities known for its vibrant lifestyle and exceptional amenities. This thoughtfully designed 2 bedroom, 2 bathroom home also includes a versatile office that can easily serve as a third bedroom, along with a spacious family room that provides additional living space for relaxing or entertaining. As you arrive, you’re welcomed by a covered and screened front entry. Inside, the open concept floor plan is enhanced by vaulted ceilings and a stylish blend of luxury vinyl flooring in the main living areas and ceramic tile in the kitchen, bathrooms and laundry room, creating both elegance and easy maintenance. The eat in kitchen is bright and inviting, featuring a closet pantry, stainless steel appliances that are just two years old and a comfortable dining space ideal for everyday meals. An interior laundry room is conveniently located just off the kitchen and provides direct access to the two car garage. Sliding glass doors from the living room lead to a screen enclosed patio, offering the perfect spot to unwind, entertain guests, or simply enjoy Florida’s beautiful year round weather. The primary suite serves as a relaxing retreat, highlighted by a tray ceiling, walk in closet and an ensuite bathroom with a double sink vanity and step-in shower. Recent updates provide added peace of mind, including a brand new HVAC system and water heater, installed in March 2026, a new roof (November 2023), updated kitchen appliances (2024), fresh interior paint, and refreshed landscaping (2026). Outside, the property is beautifully framed by mature landscaping, with an attached two car garage, brick paved driveway and walkway that enhance the home’s inviting curb appeal. Residents of Traditions enjoy a true resort style lifestyle, featuring a lakefront clubhouse with a library, fitness center, card room, and billiards, as well as a resort style pool, hot tub and sauna. Additional amenities include tennis and shuffleboard courts, a dog park, a boat ramp and a dock overlooking Ruby Lake, providing endless opportunities for relaxation and recreation. The $484 monthly HOA fee covers lawn care (including bush/tree trimming and mulch replacement), exterior painting, cable, and internet. Ideally located near shopping, dining, and medical facilities with Publix opening soon just down the street, this home offers the perfect combination of comfort, convenience, and an active community lifestyle.

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

Listing Agent: Patricia De Graaff, Llc (863-307-0061)

Remarks: Under contract-accepting backup offers. Short Sale. CLOSE IN 60 DAYS OR LESS! QUICK and easy HECM Short Sale on this well loved, one owner Villa with wooded view. The charming kitchen has upgraded wood cabinets, solid surface counter tops, breakfast bar, and two pantry storage closets. The spacious great room has recently updated Luxury Vinyl Plank floors for easy care. Other recent updates include AC system in 2022, and Roof 3/2026.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. 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!

Listing is courtesy of: CENTURY 21 WATSON & MYERS REALTY (863-324-1000)

Listing Agent: Marti Sutton (863-206-0563)