Winter Haven Homes For Sale & Real Estate - 1041 homes

Remarks: Short Sale. This property presents a great opportunity for buyers looking to renovate and add value. With a functional floor plan and generous living areas, it offers a solid starting point for updates and improvements. The layout provides flexibility to reimagine the space to suit your needs and design preferences. Spacious rooms allow for creative customization throughout. The kitchen area offers ample space to redesign and enhance. Bedrooms are well sized and provide potential to create comfortable retreats. There is opportunity to refresh both the interior and exterior to maximize appeal. Outdoor space allows room for landscaping or additional enhancements. Ideal for investors or buyers seeking a renovation project. Schedule your showing today and explore the possibilities.

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

Listing Agent: Cesar Estrada, Pa (321-209-4782)

Remarks: This is a beautiful condo located in the heart of Downtown Winter Haven, FL. The sunsets over Lake Howard are unbelievably gorgeous and can be enjoyed sitting on either patio overlooking the waterfront. This is an end unit that comes with 2 covered parking spaces located directly underneath the space. A must see.

Listing is courtesy of: COLLANY PROPERTIES (863-295-9886)

Listing Agent: Christopher Collany (863-412-2170)

Remarks: One or more photo(s) has been virtually staged. Motivated Seller!! *Welcome to this spacious Move-in-ready 4 bedroom, 2.5 bathroom home tucked away in the heart of Royal Hills, Winter Haven. The Home has recent upgrades including freshly painted Exterior in 2025, Roof 2024. The entire upper level has been revitalized with well-maintained carpeting while the ground floor showcases ceramic tile throughout. The kitchen contains Sleek granite countertops for that touch of sophistication,Stainless-steel appliances along with bright light fixtures.The home also has a BONUS Room on the ground level - perfect for a Home office or Media Room and a HUGE Fenced backyard. Conveniently situated near US-27, this property offers quick access to interstate travel and shopping centers. Don't let the opportunity slip by to make this beautiful house your next family home

Listing is courtesy of: MILLENNIUM REALTY CENTER LLC (407-843-8996)

Listing Agent: Phabie Terzier (407-692-7452)

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: Welcome to this charming 2 bedroom, 2 bathroom home in Orchid Springs, a non–age-restricted community where all ages are welcome, located in SE Winter Haven. Thoughtfully updated, this home features new wood plank tile flooring. The open floor plan is highlighted by a spacious and light-filled great room with vaulted ceilings creating a warm and inviting space ideal for everyday living. Just off the great room is a beautiful atrium to fill with your favorite plants or enjoy the evenings outside in your private sanctuary. The primary suite includes built-in closets, sliding glass door open to the back courtyard and an en-suite bathroom with updated wood plank tile flooring, updated vanity and mirror the secondary bedroom is generously sized and located next to the guest bathroom, which features updated vanity and tile flooring. Additional highlights include a one-car garage with laundry area Outdoors, enjoy a paver patio courtyard ideal for BBQs and entertaining. There are plenty of private outdoor spaces for relaxing there is are front and rear screened porches as well as the outdoor courtyard. Orchid Springs is a well-established community offering a swimming pool and clubhouse, with lawn maintenance and amenities included for a low monthly fee. Conveniently located within minutes of shopping, dining, medical facilities, and LEGOLAND® Florida, and centrally positioned between Tampa and Orlando for easy access to theme parks and international airports. Call today to schedule your private showing.

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

Listing Agent: Anita Lowe (863-269-6461)

Remarks: No HOA, no CDD! Jump in to get a deal! Charming brick home nestled only few min from Downtown Winter Heaven and near Legoland. Luxury upgraded and boast lots of improvements - brand new roof, new luxury vinyl planks floor throughout, new interior and exterior paint, new bathroom and new shower room, new pluming, brand new kitchen cabinets and granite counters, new Stainless Steel appliances, new lights throughout, all new doors and door frames. Brand new landscaping and fence in back yard. Schedule private showing today - close it tomorrow and enjoy your dream home with your family! This is only for you!!!

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Larysa Tsyupenko (407-780-5456)

Remarks: WELCOME TO CAREFREE LIVING WITH THIS WELL-MAINTAINED RESIDENCE WITHIN THE DESIRABLE 55+ GATED, LAKEFRONT COMMUNITY AT "TRADITIONS OF RUBY LAKE". This home is MOVE IN READY and is situated withing very close proximity to the clubhouse and Lake Ruby!!! NEW ROOF and NEW HOT WATER HEATER both installed in 2023. With nearly (1,820 Sqft.) of heated and cooled space, this OPEN-CONCEPT SPLIT PLAN with SOARING CEILINGS will not disappoint. There is plenty of room for the chef in the family with your OVERSIZED KITCHEN that has an ABUNDANCE of cabinetry and GRANITE COUNTERTOPS! The kitchen also has 2 windows, giving you a pleasant view along with plenty of extra natural light. Just off the kitchen sits the great room leading into 2 bedrooms and another room (11 x 10) that would be perfect for an office, craft room, or out of town guests. You'll love the (21 x 9) BONUS ROOM that has its own AC and gives you so much extra cooled living space. As if this wasn't enough, the bonus room also overlooks a (21 x 9) SCREENED, PAVERED PATIO for outside grilling or just relaxing. The large primary en-suite has a WALK-IN-SHOWER WITH BUILT-IN BENCH and GLASS SLIDERS, DUAL SINKS, and OVERSIZED WALK-IN-CLOSET. You have direct access to the bonus room from the primary bedroom. Cleaning is a breeze in this home featuring NO CARPET!!! The clubhouse is beautiful and boasts amazing views beyond the pool of 2 lakes (Ruby and Bess). The clubhouse also features an oversized pool and spa, dock, boat ramp, boat slips, tennis courts, pickle ball, basketball, shuffleboard, ball room, billiards, library, craft room, fitness center, dog park and much more! Golf carts are allowed in the community for ease of navigating. Traditions is centrally located in close proximity to medical, shopping, restaurants, 2 major international airports (Tampa/Orlando) and the up and coming airline Avelo in Lakeland, FL. LEGOLAND, FL is just minutes away!

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

Listing Agent: Bryan Dicks (863-287-7851)

Remarks: PRICE IMPROVEMENT OF $5K MOTIVATED SELLER BEAUTIFUL GATED GOLF COURSE COMMUNITY An exceptional opportunity to own a beautiful 3brm/2.5 bath home nestled on the 4th hole of the highly sought-after Lake Bess Country Club and Golf Course in Winter Haven. As you step inside, you are welcomed by a charming foyer featuring 10-ft ceilings that create an open and airy ambiance throughout the home. The living room, enhanced by a cozy gas fireplace, provides a perfect setting for those cool winter evenings in Florida. This space effortlessly connects to a spacious breakfast nook, both of which open onto a large lanai that offers tranquil views of the golf course, framed by majestic oak trees draped in moss-ideal for an evening glass of wine. Through French doors off the living room, you will find a stunning study\office equipped with built -in wood shelving with additional storage, perfect for work or leisure. The layout thoughtfully includes two generous sized bedrooms and a full bath on this side of the home. At the heart of the house, the well-appointed kitchen is a dream for any cook. It boasts ample space, views of the golf course, and a breakfast nook for casual dining. A bar area allows friends and family to gather and socialize while meals are being prepared. For more formal occasions, the designated dining room offers an elegant setting. The primary suite is an impressive retreat, featuring a tray ceiling, his and hers walk-in closets, and a spacious bathroom equipped with a large shower and vanity. A private water closet and a hidden washer and dryer behind closet doors add to the convenience of this remarkable space. The home also includes an oversized 2-car garage, perfect for tools and a work table. As part of this vibrant community, you'll enjoy access to the clubhouse, community pool and golf course. This hidden gem offers easy access to Legoland, Highway 27, and I-4, making it a prime location for both relaxation and adventure. The purchase price also includes 1 of 49 shares to the golf club which includes 2 free memberships and unlimited Golfing, enhancing the value of this exceptional property. I invite you to discover this property and envision the lifestyle that awaits you at Lake Bess Country Club. Please let me know if you would like to schedule a viewing or if you have any questions.

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

Listing Agent: Christina Ashley (941-780-0291)

Remarks: RUDUCED PRICE! MOTIVATED SELLERS Charming 4-Bedroom Lakefront Home on Lake Thomas – No HOA Discover the perfect blend of comfortable family living and relaxed lakefront lifestyle in this beautiful 4-bedroom, 2-bath home on Lake Thomas. Offering a spacious layout, generous outdoor space, and scenic water access, this property delivers both everyday functionality and waterfront charm. Step inside to find tile flooring throughout the main living areas and an open-concept design that seamlessly connects the living and dining spaces — ideal for family gatherings and entertaining guests. Ceiling fans throughout the home enhance comfort year-round. Outdoors, enjoy an oversized, level backyard that’s fully fenced — perfect for pets, outdoor dining, gardening, or play. Whether you're relaxing by the water or hosting weekend barbecues, this home offers space and flexibility to fit your lifestyle. Located in Winter Haven, you’ll appreciate convenient access to local amenities, shopping, dining, and recreational opportunities — all without the burden of HOA restrictions. Lake living, space to grow, and freedom to enjoy — this one has it all.

Listing is courtesy of: CENTURY 21 WOLF'S CROSSING REALTY (407-449-0000)

Listing Agent: Lucy Martinez (863-521-4156)

Remarks: Welcome to 292 Krenson Bay Loop, a 2024-built block home located in a gated Winter Haven community with NO CDD! This 4-bedroom, 2-bath home offers 1,820 square feet of living space, a 2-car garage, irrigation system, and a desirable split floor plan designed for comfort and functionality. Inside, you’ll find tile throughout the main living areas and kitchen, with carpet in the bedrooms. The modern kitchen features stainless steel appliances, subway tile backsplash, a large pantry, and an oversized peninsula with bar seating, opening nicely to the breakfast nook and main living area. A formal dining room provides additional space for gatherings or flexible use. The primary suite includes a walk-in closet and private bath with dual sinks, a garden tub, and a separate shower. Enjoy Florida living from the covered lanai, perfect for relaxing outdoors. Located in Winter Haven, this home offers convenient access to local lakes, shopping, dining, medical facilities, and nearby attractions including LEGOLAND Florida Resort. With easy routes to Lakeland, Tampa, and Orlando, this location provides a great balance of Central Florida living and regional convenience.

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

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

Remarks: LAKEFRONT COMMUNITY...Welcome home to Lakeside Ranch, a gated 55+ community with NO LOT RENT! This 2 Bedroom/2 Bath home features a large living room that leads to the lovely Florida room.This open concept home has a tastefully renovated kitchen with lots of counterspace and cabinets, a dining room with built-in cabinetry, a large living room with lighted ceiling fan, luxury vinyl plank flooring throughout. Utility shed all offers additional storage space and includes washer and dryer. Sold Furnished or Vacant, your choice. HOA inscludes water, sewer, lawn service and security. The community features a large clubhouse with a variety of scheduled activities and holiday events, library, meeting space, a boat ramp and fishing dock on Lake Henry, trailer storage area, heated swimming pool, shuffleboard, horseshoe area, and a billiards room. Are you ready for an active lifestyle? Or just relax and fish the day away? This is the place for you either way! Live here year-round or escape the cold winters in sunny Florida!

Listing is courtesy of: HOME WISE REALTY GROUP, INC. (407-712-2000)

Listing Agent: Chanmarlie Lim (407-376-1813)

Remarks: Brand new, energy-efficient home available by Oct 2025! Prepare dinner while catching up on the days events from this homes chef-inspired kitchen which overlooks a great room and dining area. Well appointed primary suite provides a restful retreat at the end of the day and has a spacious 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.

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

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

Remarks: Like new 5-bedroom, 3.5-bath home with a functional open layout and abundant natural light. The kitchen overlooks the main living area, making it perfect for entertaining. Upstairs, a versatile loft adds valuable extra living space. With generously sized secondary bedrooms, modern finishes, and a 2-car garage, this home is ready for its next owner. Easy to show!

Listing is courtesy of: SOVEREIGN REAL ESTATE GROUP (305-662-1502)

Listing Agent: William Figueroa (305-662-1502)

Remarks: Under Construction. Brand new, energy-efficient home available by May 2026! Prepare dinner from this home's open kitchen which overlooks a spacious great room. 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. BEAT NEW CONSTRUCTION COSTS! Seller offering up to $7,000 toward closing costs, prepaid expenses, or interest rate buydown; helping reduce your cash to close and monthly payment. Move-in ready with NO CDD!This beautifully updated 3-bedroom, 2-bathroom home with a bonus room is ideally located just minutes from LEGOLAND Florida, as well as shopping, restaurants, hospitals, and major attractions. Whether you're looking for a primary residence, vacation home, or investment opportunity, this property delivers comfort, space, and modern upgrades. Step inside to a bright, interior featuring new ceramic tile flooring throughout the entire home (absolutely NO carpet), offering easy maintenance and a clean, modern look. The homehas been freshly painted and thoughtfully updated to feel truly move-in ready. The renovated kitchen features new cabinetry, granite countertops, stainless steel appliances, a spacious pantry, and a breakfast nook perfect for casual meals. For hosting and special occasions, enjoy a formal dining room that adds both function and elegance.The spacious primary suite is a true retreat, offering a beautifully appointed en-suite bathroom with double sinks (ideal for busy mornings), granite countertops, an enclosed shower, and a relaxing garden tub.Both bathrooms have been upgraded with new cabinets and granite countertops, adding a cohesive and modern finish throughout the home. A versatile bonus room provides the perfect space for a home office, playroom, gym, or guest area. For added convenience, the laundry room is located inside the home.Step outside to the screened lanai, overlooking a generous lot being an ideal setting for weekend BBQs, family gatherings, or simpl enjoying Florida?s indoor-outdoor lifestyle.This home combines modern upgrades, flexible living spaces, and an unbeatable location near LEGOLAND Florida. With both roof & HVAC replaced in 2024 there is reassurance of major system being warranted - A must-see property!

Listing is courtesy of: EASY REALTY (321-895-4636)

Listing Agent: Greg Owen (321-360-4434)

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: This 3 bedroom 2 bath home is located in an established neighborhood close to the Polk parkway for easy access to Orlando or Tampa. The Kitchen is equipped with stainless steel appliances, wood cabinets, granite counter tops, breakfast bar. There is a fire place and a wet bar in the large living room with beautiful tile & wood flooring throughout the home. The back porch is screened and the entire backyard is beautifully landscaped with mature landscaping, various trees and surrounded with a brick wall. There is also a detached workshop that is completely finished with tile floors and air conditioning. The home features a gas tankless hot water heater and smart lock on the doors.

Listing is courtesy of: THOMAS REALTY (863-412-4253)

Listing Agent: Phillip Thomas (863-412-4253)

Remarks: Short Sale. ***Short sale***Spacious 4-bedroom, 2-bathroom manufactured home with strong bones and endless potential! Featuring a newer AC unit and a roof less than 5 years old, this property is a great opportunity for a savvy buyer ready to bring their vision to life. Whether you're looking to create your forever home or an investment property, this one is worth a look. The primary suite offers a walk-in closet and a luxurious garden tub, perfect for relaxing after a long day. Situated on just under half an acre, there’s ample space for outdoor living, gardening, or future enhancements. Bring your eye for design and turn this home into something truly special!

Listing is courtesy of: CENTURY 21 MYERS REALTY (863-875-5656)

Listing Agent: Tony Acosta (863-224-5956)

Remarks: A Cozy Condo nestled in the back corner of the popular community of Winterset. Forgot your key, no problem, you have a coded keyless entry. Your tour begins entering through your covered screened front porch into a Ground level 2 bed/2bath home with an open floor plan. Beautiful Laminate wood flooring accentuates the space. The conveniently centered kitchen boasts a neutral decor with tile backsplash and a newer Stainless side by side fridge. A Nice size Patio is accessed from Livingroom for Barbecuing or just relaxing, enjoying the Florida weather. The split bedroom design offers added privacy to The Master Bedrm with en suite, spacious Walkin closet, Stackable washer/dryer and private screened in patio area which continues to enhance this space. The master bath has separate tub/shower access. The Nest thermostat allows you to monitor and change settings via a phone app. When you Plan your day trips.... You're Only minutes from Lego Land and convenient to Disney & other Florida amusement parks, Beaches, Shopping, Restaurants & More. Or, stay at home, relax and enjoy amenities of the community with Heated Pool, Spa, Tennis, Shuffleboard, Fishing Pier and Clubhouse! Walk the family pet across the street in the expansive green space. All Furniture negotiable!

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

Listing Agent: Catrina Marshall (813-377-7380)

Remarks: Discover this 3-bed, 2.5-bath pool home in the sought-after Whisper Lake community of Winter Haven. The home features a functional two-story layout with all bedrooms and full baths upstairs, plus a convenient half bath off the kitchen. Interior highlights include wood laminate and tile flooring, crown molding, wainscoting, and thoughtful finishing touches throughout. Step outside to a private backyard retreat complete with an in-ground pool, oversized patio, and vinyl fencing—perfect for relaxing or entertaining. This property offers a great blend of comfort, style, and outdoor living in a peaceful neighborhood setting. Don't delay. Schedule today!!

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

Listing Agent: Andrea Williams Llc (863-605-0408)