Winter Haven Homes For Sale & Real Estate - 934 homes

Remarks: Improved Price!! All new window in the building...Price improvement...Seller ready to sell! Beautifully maintained 55+ condominium located in Lake Ridge Winter Haven. This is a gated community offering a tranquil living space. Conveniently located near hospitals, restaurants, shopping, entertainment and so much more. This home offers everything you need to live a true Floridian lifestyle. Amenities include heated pool ALL year around, tennis court, shuffleboard, pickle ball, car washing area, outdoor grills, community room, and covered guest parking for your family to enjoy when they visit. The community offers community events so boredom is not an option. So much opportunity to socialize and create amazing memories. This specific unit offers a relaxing airy and bright Florida room to sit back and enjoy your coffee. Association will be putting in new windows and fresh exterior paint this summer. The assessment is PAID in FULL so you can affordable live in style. Monthly association covers water, sewer, trash, fiber optics cable, internet, prime HD package, condo reserves, and maintenance. This is truly a hidden gem waiting for its new owner! Whether you are looking for a winter retreat or a forever home, this condominium offers you your own piece of paradise. Check it out before its gone! Schedule your showing TODAY!

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

Listing Agent: Brenda Brooks (863-370-9667)

Remarks: Under contract-accepting backup offers. Price Improvement — Exceptional Value! Beautifully renovated home tucked away in a quiet, no-HOA community and situated on a spacious corner lot offering added yard space and great curb appeal. This move-in ready property features an open-concept layout with modern finishes, abundant natural light, and fresh updates throughout. The spacious primary suite includes a private bath, and the updated kitchen showcases stylish finishes and appliances ready for everyday living. Laundry hook-ups included for convenience. Well-priced and eligible buyers may qualify for financing programs that assist with closing costs — ask for details.

Listing is courtesy of: LA ROSA REALTY CW PROPERTIES L (407-910-2168)

Listing Agent: Daryle Henry, Jr. (863-651-4792)

Remarks: Welcome to this beautifully reimagined 4-bedroom, 2-bathroom pool home, perfectly positioned on a premium corner lot. Thoughtfully updated with a new roof (2021), HVAC (2024), and fresh interior paint throughout—including ceilings and the pool deck—this residence offers effortless, move-in-ready living. Inside, a refined layout unfolds with a formal dining space and a flexible bonus room, ideal for a private office or curated living area. The heart of the home showcases an open-concept design, where the living room flows seamlessly into a sophisticated kitchen and breakfast space, perfect for both intimate gatherings and entertaining. The kitchen is appointed with quartz countertops, high-end appliances, a built-in bar fridge, and a convenient pot filler, blending style with function. A desirable three-way split floor plan ensures privacy and comfort throughout. Outdoors, enjoy a screened-in patio overlooking a sparkling pool, complemented by a generously sized, fully fenced backyard, your own private retreat designed for the Florida lifestyle. Experience the perfect blend of modern upgrades and timeless comfort. Schedule your private showing today!

Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)

Listing Agent: Kevin Asenjo (407-844-5252)

Remarks: PRICE REDUCTION!!! Bring your buyers. Great opportunity at new price.... Welcome to 740 Squires Grove Dr. This beautiful 5 bedroom, 3 bath residence offers the space you've looking for, filled with natural light and and large fenced backyard ideal for gatherings, pets or relaxing outdoors. Well located near shopping, dining, hospitals, major highways, and just minutes from LEGOLAND. Book your showing today!.

Listing is courtesy of: NORTHGROUP REAL ESTATE, INC (561-222-1850)

Listing Agent: Lulis Batista (407-969-2098)

Remarks: Welcome to your move in ready dream home! Built in 2023 and still sparkling like new, this 3 bedroom , 2 bath beauty comes with an attached 1 car garage, sits at the at the end of of a peaceful dead end street in the highly sought after unincorporated Winter Haven-offering the perfect blend of privacy and convenience. Step inside to an open, light filled floor plan where every detail shines. The heart of the home is a chef's kitchen featuring gorgeous granite countertops, with a large breakfast bar perfect for morning coffee or cold afternoon cocktails and casual dinners with friends and family. Featuring ample cabinetry and spacious pantry make cooking a real joy. Out back escape to your own lush green tropical oasis - shaded by mature trees and lush greens complete with a handy storage shed for your tools and toys. Back yard would be great for having barbecue and making memories.

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

Listing Agent: Juan Garcia (352-467-4043)

Remarks: Charming 2 bedroom, 2.5 bath townhouse offering an ideal blend of style and convenience. Spacious main level features a beautiful kitchen with gas stove, granite counters and matching granite backsplash, plus a convenient half bath. Upstairs includes 2 bedrooms and two full baths, with a relaxing soaking tub in the primary bathroom. HOA covers grounds maintenance; plenty of nearby shopping and the Advent Health Sports Center is nearby. A lovely option for first-time homeowners or an attractive investment property. Virtual tour has floor plan for upstairs and downstairs.

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

Listing Agent: Janet Lynn (407-314-6198)

Remarks: Under contract-accepting backup offers. Don’t miss your chance to own this fully rented quadplex offering immediate cash flow. All four units are currently occupied with month-to-month tenancies paying $1200 per month, giving a new owner flexibility to increase rents to market value or renovate units for added equity and higher returns. Each unit features: 2 Bedrooms / 1 Bathroom, spacious living and dining room combination, dedicated laundry room with washer/dryer hookups, gas stoves and hot water heaters. The roof is only 5 years old. Whether you’re looking to expand your portfolio or secure a strong income-producing property, this quadplex checks all the boxes with built-in upside potential.

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

Listing Agent: Harold Baker (863-604-6272)

Remarks: Welcome to this beautifully renovated lakefront retreat on Thomas Lake in Winter Haven! This stunning two-story home combines modern upgrades with warm character and breathtaking water views. Currently, the 3rd bedroom is set up as a loft, offering breathtaking lake views and including a closet. Step inside to tall vaulted ceilings creating an open, airy layout filled with natural light. The home features all-new flooring throughout and a completely updated kitchen showcasing stainless steel appliances, quartz countertops, brand-new cabinetry, and closet pantry – providing plenty of storage and room to cook or entertain. A cozy fireplace with a raised hearth and wood accents adds charm and a welcoming focal point to the living space. This home also features beautifully updated bathrooms and walk-in closets. The home also includes a new electric water heater and newer A/C (2022) for added efficiency and peace of mind. Outside, you’ll find a newer roof (2022), fresh exterior paint, an attached 1-car garage with driveway, and plenty of space to enjoy the outdoors. Relax or entertain on the large rear patio, or unwind on the private, enclosed back porches on both floors, each offering gorgeous, tranquil lake views. This move-in-ready lakefront gem blends modern updates, comfort and scenic surroundings, making it a rare opportunity you won’t want to miss!

Listing is courtesy of: PORCHLIGHT HOMES LLC (863-529-3369)

Listing Agent: Angie Reynolds (863-838-1090)

Remarks: Discover the perfect blend of modern living and convenience in this brand new 3-bedroom, 2-bathroom home located in the heart of Winter Haven, just minutes from the serene shores of Lake Hartridge. Best of all, there’s NO HOA to worry about! As you step inside, you’ll be greeted by a bright and airy open floor plan that flows seamlessly throughout the home. The luxury vinyl plank flooring adds both elegance and durability, making it a great choice for busy households. The heart of the home is undoubtedly the beautiful kitchen, which features stainless-steel appliances, quartz countertops, and plenty of cabinetry to store all your cooking essentials. The kitchen design allows for easy interaction with guests in the spacious living room, ensuring you never miss a moment while entertaining. Retreat to the primary bedroom, a sanctuary designed for relaxation. This inviting space comes complete with a generous walk-in closet and a luxurious ensuite bathroom, featuring dual sinks and a modern walk-in shower—providing a perfect spot to unwind after a long day. The two additional bedrooms are thoughtfully designed with equal sizing and each boasts a walk-in closet, ideal for family members or guests. The second bathroom, conveniently located near the entrance of the home, includes a shower and tub combination, offering both comfort and functionality. Situated in the heart of WinterHaven, this home places you in close proximity to a variety of retailers, restaurants, and shops, ensuring you have everything you need right at your fingertips. Plus, the adjacent home is also available for sale and currently under construction, offering a unique investment opportunity. Don’t miss your chance to own this exceptional new home in Winter Haven—schedule a tour today and envision the possibilities!

Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (863-701-2350)

Listing Agent: John Hubbert, Jr (863-243-4024)

Remarks: Welcome to this beautifully maintained 3BR/2BA + den home in the desirable gated community of Mandolin in South East Winter Haven! Offering over 2,000 sq ft, this move-in-ready home features a bright open floor plan, vaulted ceilings, and a spacious great room with a striking reclaimed wood accent wall. The kitchen is designed for both everyday living and entertaining, showcasing cherry cabinetry, stainless steel appliances, a breakfast bar, and a cozy nook, plus a formal dining area for gatherings. The split-bedroom layout provides privacy, with a generous primary suite featuring dual walk-in closets, dual vanities, a garden tub, and separate shower. A versatile den makes the perfect home office or flex space. Enjoy peace of mind with a newer roof (2022) and water heater (2025), along with updated flooring and fresh interior paint. Step outside to a screened lanai overlooking a large fully fenced backyard—ideal for relaxing or entertaining. Situated on a .26-acre lot with mature landscaping and irrigation, this home also includes a 2-car garage and excellent curb appeal. Conveniently located near shopping, dining, major highways, and local attractions like Legoland, this home offers the perfect combination of privacy, convenience, and Florida living at its best.

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

Listing Agent: Suzie Rudd (863-287-7861)

Remarks: Short Sale. Requires a some TLC & Refresh. Pool Home.

Listing is courtesy of: WESTBAY REAL ESTATE (813-833-2045)

Listing Agent: Randy Patrick (813-833-2045)

Remarks: Welcome to this well-maintained home located in the heart of Winter Haven! This property is in great condition and offers a comfortable, move-in ready opportunity for homeowners or investors alike. The home features a fully fenced yard, perfect for pets, outdoor gatherings, or added privacy. Enjoy a functional layout with plenty of natural light and a welcoming atmosphere throughout. Conveniently located near shopping, dining, schools, and major roadways, this property provides both comfort and accessibility. Whether you’re looking for a primary residence or an investment opportunity, this home is a must-see!

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

Listing Agent: Carmen Montes (863-242-3698)

Remarks: Under Construction. Turquesa BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. The Turquesa is the ultimate family haven, a two-story home featuring 4 bedrooms, 2.5 bathrooms and a private 2-car garage. This home offers an open concept living space designed for both relaxation and entertainment. The half bathroom off the foyer ensures every guest feels at home while the extended foyer opens to the main living and dining area. Featuring luxury vinyl plank flooring and convenient indoor-outdoor living with a lanai through sliding glass doors, it’s a haven of comfort and style perfect for gatherings. The kitchen includes stunning quartz countertops and sleek stainless-steel appliances. Enjoy the spacious upstairs recreation room and the convenience of a laundry room just steps away from the bedrooms. Did we mention the brand-new washer and dryer? The owner's suite is a secluded retreat with oversized his-and-her walk-in closets, dual vanity and a walk-in shower. Completing this expansive home is the smart thermostat with voice control and professionally designed landscaping, this is truly the epitome of family-friendly luxury! Close to it all, Villa Mar places you near the natural beauty of the Winter Haven Chain of Lakes, the charm of downtown Winter Haven, and family fun at LEGOLAND® Florida Resort. Back at home, residents enjoy community amenities including a pool, dog park, playground, and walking trails.  Images shown are for illustrative purposes only and may differ from actual home. Completion date subject to change. Contact or make an appointment for more details on interest rates.

Listing is courtesy of: CASA FRESCA REALTY (813-343-4383)

Listing Agent: Michael Human (813-343-4383)

Remarks: WELCOME HOME to this beautifully updated 3-bedroom, 2-bath residence located in the pristine gated community of Cypresswood! From the moment you enter the neighborhood, you’ll feel the charm of this private, resort-style community nestled in the heart of Polk County—just minutes from US Hwy 27, providing easy access to all that Central Florida has to offer. Step through the front door into a grand foyer with soaring ceilings that opens to a spacious, light-filled living room—perfect for entertaining guests or enjoying quiet evenings at home. The kitchen is designed to impress, featuring beautiful cabinetry, abundant pantry space, and brand-new stainless steel appliances that elevate both style and functionality. Just off the kitchen, the oversized laundry room offers even more storage along with a convenient laundry sink. On the opposite side, a charming breakfast nook overlooks the large backyard—ideal for morning coffee or casual dining. The generously sized primary suite is a true retreat, complete with an expansive walk-in closet, dual vanities, a walk-in shower, and private access to the screened lanai—perfect for enjoying Florida evenings. Bedrooms two and three both feature double closets, providing plenty of storage space for family or guests. Major updates give you peace of mind for years to come, including the roof (2021), new A/C (2024), gas water heater 2021, new stainless appliances. This move-in-ready gem offers comfort, style, and thoughtful upgrades in one of the area’s most desirable golf communities which include an 18 hole champion designed course, pro shop, wellness center, Pub/restaurant, clubhouse, swimming pool and more! Don’t miss your opportunity to make it yours—schedule your private showing today!

Listing is courtesy of: INFINITE REAL ESTATE POWERED BY ILIST (321-689-8731)

Listing Agent: Michelle Keohane (850-866-5905)

Remarks: BEAUTIFUL SE POOL HOME LOCATED ON A QUIET CUL-DE-SAC IN DESIRABLE HARBOR ESTATES. SITUATED ON A SPACIOUS WOODED LOT OF OVER 1/2 ACRE. THIS PROPERTY OFFERS PRIVACY, MATURE LANDSCAPING AND PLENTY OF OUTDOOR LIVING SPACE FOR ENTERTAINING OR FOR THOSE FAMILY GATHERINGS. THIS HOME FEATURES 4BR PLUS A PRIVATE GUEST BEDROOM AND BATH, IDEAL FOR GUESTS, MULTI GENERATIONAL LIVING OR FLEXIBLE HOME OFFICE SPACE. ENJOY THIS 38X10 LANAI OVERLOOKING THE SCREEN ENCLOSED POOL, PERFECT FOR ENTERTAINING AND RELAXING YEAR ROUND. LARGE ENTRY FOYER WITH FORMAL LIVING ROOM WITH FIREPLACE, PLANTATION SHUTTERS THROUGHOUT. FORMAL DINING ROOM FOR THOSE FAMILY DINNERS. LARGE OPEN KITCHEN WITH ABUNDANCE OF CABINETS, LARGE CENTER ISLAND WITH GRANITE COUNTERTOPS AND STAINLESS APPLIANCES, A CHEF'S DELIGHT. 20 X 16 FAMILY ROOM WITH FULL STORAGE WALL. SPACIOUS PRIMARY BEDROOM HAS MASTER BATH WITH DOUBLE VANITIES AND STEP IN SHOWER. WALK IN CLOSET WITH ORGANIZER SHELVING. DON'T NEED TO FORGET ... THE OVERSIZED SIDE ENTRY GARAGE HAS A MINI SPLIT AC UNIT AND HAS PREVIOUSLY COOLED THE SPACE FOR AN ART STUDIO, SO MANY POSSIBILITIES. THIS HOME IS CONVENIENTLY LOCATED NEAR SHOPPING, DOWNTOWN EVENTS, RESTAURANTS AND NEAR AREA LAKES ON OUR FAMOUS WINTER HAVEN CHAIN OF LAKES. THIS IS A RARE OPPORTUNITY TO OWN A HOME IN ONE OF OUR SE WINTER HAVEN'S MOST ESTABLISHED COMMUNITIES. PLEASE NOTE: ADDITIONAL PHOTOS TO FOLLOW

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

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

Remarks: LOOKING FOR THAT AMAZING HOME? Discover it in this fully renovated 3-bedroom, 2-bathroom beauty featuring a NEW roof (2025), NEW A/C unit (2026), NEW water heater (2025), and NEW electrical service panel (2026)—perfectly positioned just opposite Jewett Middle Academy. Enjoy your morning coffee on the radiant front porch before stepping into a bright and welcoming interior where the living room and kitchen greet you the moment you enter. The home is complemented by new vinyl flooring throughout and a cozy rug in the primary closet. The kitchen shines with a fresh, modern update, showcasing brand-new appliances, new cabinetry, and sleek quartz countertops. Whether you’re hosting guests or enjoying a quiet evening, the living room serves as the perfect centerpiece for everyday living. The primary suite offers a serene escape, highlighted by a fully remodeled ensuite bathroom and a spacious walk-in closet. The Fenced backyard is perfect for gatherings and outdoor enjoyment, with the added convenience of being close to shopping, schools, dining, and Winter Haven Hospital. Don’t miss this opportunity to own your happy place. Schedule your showing today

Listing is courtesy of: SUNSHINE LIFE REALTY LLC (321-229-0627)

Listing Agent: Sarita Khan (407-385-2077)

Remarks: Ready to be impressed, this move-in ready 4-bedroom, 2-bathroom home at 4263 Stafford Dr is perfectly situated in Winter Haven, FL, with easy access to shopping, restaurants, major roads, and so much more. Step inside and you'll immediately notice the high ceilings and open floor plan that make this 2,234 square foot home feel even bigger than it already is. Hard flooring runs throughout the entire house, giving it a clean and modern look that's super easy to maintain. The family room is a real standout with a cozy fireplace that's perfect for those cooler Florida evenings when you just want to kick back and relax. The split bedroom layout gives you plenty of privacy, with the primary bedroom tucked away on one side and the additional bedrooms on the other. It's a great setup for families or anyone who likes their own space. Now let's talk about the backyard because this is where it gets really good. The screened-in back porch opens up to your very own pool and hot tub. Imagine coming home after a long day and just diving right in. Whether you're hosting friends on the weekend or enjoying a quiet evening under the stars, this outdoor space is going to be your favorite spot. Homes like this one in such a convenient Winter Haven location don't sit on the market for long. Come take a look before someone else scoops it up!

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

Listing Agent: Scottie Wilson (305-510-2446)

Remarks: WELCOME TO YOUR NEW HOME! Experience peaceful lakefront living in a charming SE Winter Haven location, just minutes from LEGOLAND Florida Resort and the beautiful Chain of Lakes. This home is perfect for buyers looking to slow down and enjoy the simple things—morning coffee with a water view, evenings by the lake, and weekends spent fishing or unwinding in your own backyard. While the lake is smaller and offers a more quiet setting with no public boat access, that’s part of its charm—less traffic, more tranquility. Situated on a spacious lot with a fenced backyard, there’s plenty of room for pets, gatherings, or creating your own outdoor oasis. Inside, the home offers a solid foundation and a warm, inviting layout, ready for your personal style and updates to truly make it your own. If you’ve been searching for an affordable lakefront lifestyle with room to grow, this is your opportunity to put down roots and create a home that reflects you.

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

Listing Agent: Lamanda Jones (863-557-3627)

Remarks: Enjoy a relaxed, maintenance-free lifestyle in this well-loved 55+ condo overlooking the beautifully maintained grounds of Imperial Harbours and the shores of Lake Howard. From both the bedroom and enclosed Florida room, take in peaceful views of the community pool and landscaped courtyard—an ideal backdrop for quiet mornings or unwinding at the end of the day. Located in Building Two, this second-floor unit offers convenient access via elevator or stairs and provides a comfortable, easygoing layout designed for everyday living. The bright and open great room flows seamlessly into the dining area, creating a welcoming space for both relaxing and entertaining. The primary suite is spacious and features a walk-in closet along with a private en suite bath complete with a step-in shower. The guest bedroom offers flexibility for visitors or additional use, while the kitchen provides ample cabinetry, stainless steel appliances, stone countertops with workspace for everyday needs. Interior features include tile flooring throughout and the convenience of an in-unit stackable washer and dryer. Residents enjoy a variety of amenities, including a lakeside fishing pier, community pool, fitness area, meeting room, assigned covered parking, and extra storage. The condo fee simplifies daily living by covering cable, internet, water, sewer, trash, exterior maintenance, and grounds care. Ideally situated just minutes from shopping, dining, and the charm of downtown Winter Haven, this property offers an easy, enjoyable Florida lifestyle with lake access right at your doorstep.

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

Listing Agent: Deborah Grogan (863-812-5944)

Remarks: Need space? This private gated 2.38-acre Winter Haven property with NO HOA offers room to live, play, and grow—bring your RV, boat, ATV, and all your toys. Set well back from the road behind a remote-operated gated entry, this property delivers the privacy and convenience buyers are actively searching for in Winter Haven and throughout Polk County. The fully fenced acreage gives you the freedom to create the lifestyle you want—whether it’s kids playing football or volleyball, evenings around a fire-pit, playground, space for a future pool, or planting your own fruit trees and garden. Inside, the home features an open floor plan with a desirable split-bedroom layout, offering both functionality and comfort. Enjoy formal living and dining spaces for hosting, plus a spacious family room that flows into the kitchen—perfect for everyday living and gatherings. The kitchen is equipped with abundant cabinetry, hardwood flooring, a breakfast bar overlooking your private backyard. The owner’s suite is a peaceful retreat, featuring French doors leading to the screened back porch, a large walk-in closet, and a spa-style bathroom with soaking tub and separate shower. A flexible fourth bedroom near the primary suite provides the ideal space for a home office, nursery, or hobby room. Step outside and experience true Florida living from your 42’ covered front porch or 34’ screened back porch, surrounded by mature trees and open space. This property offers the perfect balance of cleared land for activities and wooded areas for added privacy. Additional features include: * Remote-operated gate for easy access and security * New roof in 2023 * Side-entry 2-car garage + metal carport * Inside laundry room * Well for irrigation & water softener * High and dry acreage *New AC, Well Pump & Water Heater in 2018 *Septic Pumped 2026 Located just minutes from the Polk Parkway, with convenient access to Lakeland, Tampa, and Orlando, this home combines privacy, land, and accessibility—a rare opportunity in today’s market. If you’ve been searching for a gated acreage property in Winter Haven with no HOA and true outdoor living potential, this one checks all the boxes.

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

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