Winter Haven Homes For Sale & Real Estate - 704 homes

Remarks: Welcome to 287 Inman Blvd—where modern comfort meets effortless Florida living in the heart of Winter Haven. This beautifully maintained home truly feels like new, offering the peace of mind of recent construction with thoughtful upgrades already in place. From the moment you step inside, you’ll notice a clean, contemporary design paired with warm, inviting spaces. The open-concept layout flows seamlessly, making it perfect for both everyday living and entertaining. The kitchen is a standout feature, enhanced with a stylish backsplash on the island and throughout, complemented by upgraded light fixtures that add a polished, custom feel. The home also features low-maintenance quartz countertops as well as stainless steel appliances. This home has already been elevated beyond builder-grade with valuable improvements, including solar panels for energy efficiency, a vinyl privacy fence for added outdoor enjoyment, and upgraded ceiling fans and lighting throughout. Tile flooring in the wet areas offers durability and easy maintenance, while cozy carpeting in the bedrooms creates a comfortable retreat at the end of the day. Step outside and enjoy a backyard space that’s ready for relaxing evenings, pets, or gatherings—fully enclosed for privacy and convenience. Location is where this home truly shines. Situated just about one and a half miles from the soon-to-open Publix shopping plaza, you’ll have everyday essentials right around the corner. Plus, you’re only minutes from downtown Winter Haven, known for its charming local shops, dining, and access to the Chain of Lakes lifestyle. Commuters will appreciate the quick access to US-27, making travel to surrounding areas simple and efficient. If you’ve been searching for a move-in-ready home with upgrades already done, modern finishes, and a prime location, this is one you don’t want to miss.

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

Listing Agent: Chris Loschiavo (863-280-2201)

Remarks: One or more photo(s) has been virtually staged. Welcome to this charming 3-bedroom, 3-bath home located in one of Winter Haven’s most established and sought-after neighborhoods. Situated on a spacious 0.26-acre lot, this property offers timeless character, mature surroundings, and a location rich in local history. A standout feature of the home is the private suite with its own entrance and full bathroom, ideal for guests, extended family, or a flexible work-from-home space. The layout provides both privacy and functionality, making it a rare find in this area. Recent updates include a newer roof (approx. 1 year old), updated electrical, a new water heater, and a newer A/C unit (2018), offering peace of mind on major systems. Enjoy the unique setting with nearby views of Lake Elbert to the north and Lake Otis to the south, surrounded by well-established homes and nearby lakefront properties. The home offers great bones and classic charm, presenting an excellent opportunity for buyers to update and personalize while investing in a premier location. Conveniently located near downtown Winter Haven, shopping, dining, and more.

Listing is courtesy of: REAL BROKER, LLC (855-450-0442)

Listing Agent: Dave Westphal (863-287-3302)

Remarks: Welcome to this fully upgraded 4-bedroom, 2.5 bath Winter Haven home! This home offers modern living, featuring new flooring, appliances, new windows with pull-out panes for easy access and cleaning along with new Plantation Shutters on all windows! You will also enjoy the stylish bathroom/kitchen renovations featuring in the kitchen beautiful backsplash and new pantry door, new tile in guest bath and new shower in primary bathroom! Centrally located near Legoland, shopping, and all your medical facilities, the property includes a new fenced back yard and new storage shed, HOA/City approved. Sellers are highly motivated!

Listing is courtesy of: STACEY TOWNS REALTY LLC (863-422-1585)

Listing Agent: Cathy Stripling (863-422-1585)

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

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

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

Remarks: Perfect BLOCK home for the first time home buyer, investor or seasonal owner - and a prime investment property for consideration as well. Located in a wonderful mature neighborhood zoned as a MIXED USE area; so there is potential to convert this Residential home into an Office or a Business! Offering quick access to every amenity imaginable and close to the Heart of Winter Haven. Currently a 2 bedroom home with a bonus room, could be 3 or 4 bedrooms with conversion of the bonus room and/or the garage. The large lot is between 1/4 & 1/2 Acre size with a fenced backyard. Roofing and electrical was recently updated. A great piece of real estate with lots of opportunity!

Listing is courtesy of: NUWAVE REALTY (386-473-9765)

Listing Agent: Penny Miller (386-473-9765)

Remarks: Discover the best of retirement living in Brookhaven, a welcoming 55+ community! This partially furnished and well-maintained home sits on a desirable lot with OWNED LAND, offering a peaceful and private retreat.Featuring 1,596 sq. ft. of living space, this home boasts a spacious open-concept layout with 2 bedrooms and 2 bathrooms. Recent updates include a new shingle roof (2024), new A/C unit (2025), and hot water heater (2023). The kitchen offers ample counter space and cabinetry, perfect for everyday living and entertaining.Enjoy plenty of storage throughout, along with sliding doors that lead to the porch—ideal for relaxing or hosting guests. The guest bedroom and bathroom are generously sized, while the oversized primary suite features a private ensuite bath complete with a double-sink vanity, garden tub, and walk-in shower.The laundry area is conveniently located in the spacious workshop and includes a washer, dryer, and utility sink. This home also features two porches—one screened and one enclosed—providing additional living space to enjoy year-round.Surrounded by mature landscaping, the property offers both charm and tranquility. Additional perks include an irrigation system and lawn maintenance already paid through February. This home has recently had a 4-point inspection.Brookhaven residents enjoy fantastic amenities including a pool, clubhouse, and shuffleboard—all with a low HOA fee of just $34 per month. Conveniently located near Hwy 27, shopping, medical facilities, and restaurants, you’re also just about an hour from Disney and 1.5–2 hours from both Florida coasts.Don’t miss your opportunity to own this beautiful home at 6561 Chinaberry Dr NE — schedule your private showing today!

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

Listing Agent: Corinna Weaver (863-258-2901)

Remarks: OPPORTUNITY KNOCKS ON THIS SPACIOUS & AFFORDABLE 3 Bedroom/2 Bath Home in the heart of SE Winter Haven located in Lake Daisy Estates is ready for you & your family!!! NO HOA or CDD in this established neighborhood that is within 3 miles of LEGOLAND and close to multiple restaurants, shopping, & parks. The natural light fills each room of the home. Open floor plan with split bedrooms. You'll love the large open backyard that is fully fenced. Newer roof (2023). Schedule a tour today!!!

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

Listing Agent: Cheryl Brewer (863-224-0045)

Remarks: Under Construction. New construction home with 2587 square feet two-story including 4 bedrooms with loft, 3.5 baths, and an open living area. Enjoy an open kitchen with Quartz countertops, Samsung steel appliances, a walk-in pantry, and a spacious island, fully open to the dining café and gathering room. The living area, laundry room, and baths include luxury wood vinyl plank flooring, with stain-resistant carpet in the bedrooms. Your owner's suite is complete with a walk-in wardrobe and a private en-suite bath with dual vanities, and a tiled shower. Bedrooms 3 and 4 share a jack-and-Jill bathroom. Plus, enjoy a 2-car garage, custom-fit window blinds, architectural shingles, energy-efficient insulation and windows, and a full builder warranty. “Please note, virtual tour/photos showcases the home layout; colors and design options in actual home for sale may differ. Furnishings and décor do not convey."

Listing is courtesy of: CAMBRIDGE REALTY OF CENTRAL FL (863-797-4999)

Listing Agent: George Lindsey, Iii (863-797-4999)

Remarks: Under contract-accepting backup offers. Buyer defaulted, check out this great value. The property you are inquiring about is located in Winter Haven, FL, in the Orchid Springs area of East Polk County. This is a 2nd-floor unit in Orchid Springs that is ready to move into NOW! The home has fresh paint throughout and brand new carpet. This is a one-bedroom, open floor plan with most of all utilities bundled in the HOA fees - to include - community pool, gas, exterior maintenance, maintenance grounds, water, sewer, trash. It has an approximate of 1,078 square feet of living, a dedicated parking space, and a common laundry area. Great with overlooking the preserve of nature's own form and the extremely quiet area of the Orchid Springs compound. Text, call, or email for viewing. *Agents, please read MLS remarks.*

Listing is courtesy of: BROKERS REALTY OF CENTRAL FLOR (863-294-6773)

Listing Agent: Renee Butler (863-294-6773)

Remarks: Under contract-accepting backup offers. Property is under contract with contingencies and a kick-out clause. Seller will consider backup offers. Lakefront home on the prestigious Chain of Lakes, directly on Lake Eloise, set on 1.87 acres. This three-story estate offers 6 bedrooms, 5.5 bathrooms, and a private in-law suite on the lower level, providing exceptional privacy, generous scale, and a setting designed to embrace the lake. The primary suite is thoughtfully positioned to capture sweeping lake views and serves as a true retreat, featuring a large walk-in closet and a spa-style bath with oversized shower and jacuzzi tub. Additional living spaces flow effortlessly, anchored by a chef’s kitchen with granite countertops, cherry cabinetry, and double ovens, opening to both formal and casual gathering areas ideal for entertaining. Designed for elevated living and hosting, the home includes a private movie room for a true theater experience and a spacious game and gathering room located just off the pool, creating a seamless indoor-outdoor connection. Outdoor living is a focal point of the property, highlighted by a large infinity pool within a screened enclosure overlooking the lake—an ideal setting for entertaining, relaxing, and enjoying sunset views. A private boat dock extends the lakefront lifestyle. Additional highlights include a grand circular driveway, mature shade trees, a four-car garage with space for recreational vehicles, a whole-home Generac system, and low HOA.

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

Listing Agent: Daniela Zoppe (407-808-7350)

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 this stunning Winston floorplan, located in the highly sought-after community of Willowbrook near a beautiful golf course in Winter Haven, FL. This spacious 5-bedroom, 3-bath home offers 2,531 square feet of living space and provides excellent curb appeal in its elevation. Inside, you'll find gorgeous White cabinets complemented by sleek quartz countertops in the kitchen, creating a modern, bright atmosphere. Tile flooring runs throughout the wet and common areas, offering durability and easy maintenance. The open layout is perfect for family gatherings and entertaining guests.

Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)

Listing Agent: Cindy Sapp (352-516-2843)

Remarks: One or more photo(s) has been virtually staged. Welcome to this stunning Dream Finders Poinciana Floorplan, located in the highly sought-after community of Willowbrook near a beautiful Golf Course in Winter Haven, FL. This spacious 4-bedroom, 3-bath home offers 2110 sq feet of living space and provides excellent curb appeal in its elevation. Inside, you will find gorgeous White cabinets complemented by sleek quartz countertops in the kitchen, creating a modern, bright atmosphere. Tile flooring runs throughout the wet and common areas, offering durability and easy maintenance. The open layout is perfect for family gatherings and entertaining guests.

Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)

Listing Agent: Cindy Sapp (352-516-2843)

Remarks: Welcome to this stunning Bradley floorplan, located in the highly sought-after community of Willowbrook near a beautiful golf course in Winter Haven, FL. This spacious 4-bedroom, 2-bath home offers 1598 square feet of living space and provides excellent curb appeal in its elevation. Inside, you'll find gorgeous White cabinets complemented by sleek quartz countertops in the kitchen, creating a modern, bright atmosphere. Tile flooring runs throughout the wet and common areas, offering durability and easy maintenance. The open layout is perfect for family gatherings and entertaining guests.

Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)

Listing Agent: Nancy Pruitt, Pa (352-552-7574)

Remarks: One or more photo(s) has been virtually staged. Welcome to the Mulberry floorplan, located in the highly sought-after community of Willowbrook near a beautiful golf course in Winter Haven, FL. This spacious 4-bedroom, 2.5-bath home offers 1,938 square feet of living space and provides excellent curb appeal in its elevation. Inside, you'll find gorgeous White cabinets complemented by sleek quartz countertops in the kitchen, creating a modern, bright atmosphere. Tile flooring runs throughout the wet and common areas, offering durability and easy maintenance. The open layout is perfect for family gatherings and entertaining guests. This home is ideally situated just minutes from the scenic Port 27 and downtown Winter Haven, making it convenient for shopping, dining, and entertainment. Additionally, it's only a short drive to Highway 27 and about 20 minutes to I-4, providing easy access to nearby cities and attractions. Don’t miss the chance to own this beautiful home in a prime location—schedule your tour today!

Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)

Listing Agent: Nancy Pruitt, Pa (352-552-7574)

Remarks: One or more photo(s) has been virtually staged. Under Construction. This two-story Georgia will definitely be on your mind… This beauty highlights a modern open layout, seamlessly integrating a first-floor kitchen with a central island, a dining room and a welcoming family room with patio access. On the same level is a private owner's suite with an attached bathroom. Situated upstairs is a versatile loft for additional shared living space and four secondary bedrooms to provide restful retreats to family members and guests alike. 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: DON'T MISS THIS 3 BEDROOM 2.5 BATH HOME CENTRALLY LOCATED IN WINTER HAVEN, FL ON AN OVERSIZED (.39 ACRE) LOT WITH NO HOA!!! Featuring nearly 2,000 SqFt. of heated and cooled living space, this 2-owner home was constructed of BLOCK AND BRICK! The OPEN-CONCEPT, SPLIT BEDROOM PLAN, and CENTRALLY LOCATED KITCHEN share both privacy and convenience. There is plenty of natural light in the main living area and especially through the glass sliders leading to the back yard. In the event more privacy is preferred, just hit the remote button for the MOTORIZED BLINDS, which are also INCLUDED IN THE SALE. For those looking for an OVERSIED GARAGE, this one plenty of workspace for several different hobbies. There is no shortage of parking whatsoever on this HUGE CORNER LOT! Opportunity awaits at this lovely residence, which is located in close proximity to LEGOLAND, FL, medical, shopping, dining, schools, and the many freshwater lakes Winter Haven features. Winter Haven is also located between ORANDO INTERNATIONAL and TAMPA INTERNATIONAL AIRPORT, and the most recently added AVELO AIRLINE in LAKELAND, FL!!!

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

Listing Agent: Wanda Dicks (863-287-7846)

Remarks: Lovely 3-bedroom, 2-bath home with a 2-car garage located in the gated golf course community of Lake Bess Country Club in sunny Winter Haven, FL! Perfectly situated on the 9th fairway, this home offers breathtaking golf course views with no rear neighbors—providing both privacy and a serene backdrop. From the moment you arrive, you’ll appreciate the upgraded builder features, including a beautiful tile roof, separate garage entries, and lush, mature landscaping. Just a few doors down from the clubhouse and community pool, the location within the community is ideal. Step inside to cheerful, light-filled interiors with a welcoming open view straight through to the backyard. The thoughtfully designed floor plan includes a formal dining room, a spacious living area with vaulted ceilings, and a separate kitchen dinette complete with a built-in hutch. The screened lanai is the perfect place to enjoy Florida living year-round while taking in the peaceful golf course scenery. The oversized primary suite is privately located and features its own sitting area or study, creating a true retreat. The en suite bathroom offers a soaking tub, separate shower, water closet, and dual sinks in one large vanity, along with a spacious walk-in closet with ample storage. Elegant molding details throughout the home add a touch of sophistication. The kitchen is a chef’s dream, showcasing warm wood cabinetry, tile countertops, a coordinating backsplash, stainless steel appliances, and a built-in wine rack for added charm and functionality. On the opposite side of the home, you’ll find two spacious guest bedrooms and a well-appointed guest bathroom full of character. The indoor laundry room is conveniently located just off the kitchen and leads to the garage, which features a separate single garage door for added convenience. Additional updates include a new HVAC system (2024), and the washer and dryer are included with the sale. Monthly fees cover lawn maintenance (mowing, shrub trimming, fertilization, and weed control), access to the community pool and clubhouse, plus unlimited golf and use of the driving range—offering exceptional value and a true resort-style lifestyle. Conveniently located just minutes from Legoland, the interstate, Tampa and Orlando airports, Disney attractions, shopping, dining, medical facilities, and the Chain of Lakes—perfect for boating, fishing, or simply relaxing. This well loved home offers comfort, convenience, and incredible views—schedule your private showing today!

Listing is courtesy of: COLDWELL BANKER REALTY (863-687-2233)

Listing Agent: John Manibusan (863-307-2792)

Remarks: Welcome to this well-maintained 3-bedroom, 2-bathroom home situated on a desirable corner lot in Winter Haven. Conveniently located in the heart of Central Florida, Winter Haven is known for its Chain of Lakes, Legoland, local parks, shopping, dining, and easy access to both Orlando and Tampa. This property offers a functional layout with thoughtful updates throughout. The updated kitchen features quartz countertops, ample dark wood cabinetry, and a convenient breakfast bar. Recent improvements include tile flooring and an upgraded electrical panel, adding both style and peace of mind. The primary bedroom includes a walk-in closet, while the additional bedrooms provide flexibility for a variety of uses. Step outside to enjoy the large screened-in porch, ideal for relaxing or entertaining, all within a fully fenced yard with durable PVC fencing. The irrigation system is controlled by a Hydrawise WiFi system, allowing for easy and efficient lawn maintenance. Additional highlights include a 2-car garage, a circular driveway for added parking and convenience, and a roof replaced in 2018. With no HOA or CDD fees, this property offers added flexibility and fewer restrictions. Located near Winter Haven’s popular Chain of Lakes, as well as nearby shopping, dining, and major roadways, this home provides both comfort and accessibility.

Listing is courtesy of: KELLER WILLIAMS REALTY SMART (863-577-1234)

Listing Agent: Garrett Robinson (863-838-5210)

Remarks: Under contract-accepting backup offers. R E D U C E D - R E D U C E D ... DON'T WAIT TO OWN THIS 2BR-2BA MFG HOME ON THIS LARGE CORNER LOT IN SE COMMUNITY WITH LOW MONTHLY FEES, OWNING YOUR OWN LAND AND GREAT AMENITIES. CLUBHOUSE WITH LARGE ENTERTAINMENT ROOM, FULL KITCHEN, LIBRARY, BILLIARDS ROOM, SPA, OVERSIZED POOL OVERLOOKING WATERFRONT PEACE POND WITH COOKOUT ROOM OFF POOL AREA AND EVEN SHUFFLEBOARD, THIS COMMUNITY OFFERS SO MUCH FOR THEIR RESIDENTS. THE HOME IS MOVE IN READY AND HAS SOME FURNITURE LEFT FOR CONVENIENCE OF THE SELLER. OPEN LIVING ROOM DESIGN WITH SEPARATE DINING ROOM, LARGE KITCHEN HAS EAT IN COUNTER , SPLIT BEDROOM PLAN WITH 2 BATHS. PRIMARY BEDROOM AND BATH HAS STEP IN SHOWER AND GUEST BATH OFF 2ND BR HAS TUB. LAUNDRY ROOM WITH WASHER, DRYER & WORKSHOP WALL OFF THE 14X8 SCREEN ENCLOSED PORCH. 18X11 CARPORT WITH LONG DRIVEWAY WITH PLENTY OF PARKING SPACE FOR VISITING GUESTS. MATURE LANDSCAPING WITH 2 LARGE OAKS ON THIS CORNER LOT.

Listing is courtesy of: FLORIDA HOME CHOICE REALTY (863-412-2727)

Listing Agent: Glenda Pruitt (863-412-2727)