Winter Haven Homes For Sale & Real Estate - 863 homes

Remarks: Under contract-accepting backup offers. Discover the perfect blend of country living and modern convenience with this well-maintained property set on over 5 acres. This spacious home offers 3 bedrooms plus a dedicated office, 2 full baths, a welcoming living room, formal dining room, and a bright kitchen with a breakfast nook. Step outside to your own private retreat featuring a screened pool, ideal for relaxing or entertaining. Equestrian enthusiasts will appreciate the horse barn along with fenced and cross-fenced pastures, providing plenty of space for animals. The property combines privacy and wide-open views with easy access to city amenities, shopping, and schools. With its well-cared-for condition and versatile layout, this home is move-in ready and waiting for you to enjoy the best of both worlds—peaceful country living just minutes from town.

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

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

Remarks: Charming residence in Winter Haven featuring 3 bedrooms and 2 bathrooms. This home has a spacious living area with abundant natural light, a modern kitchen with ample storage, and a serene backyard appropriate for relaxation. Located in a peaceful neighborhood with convenient access to local amenities, this property provides a welcoming atmosphere and comfortable living. Don't miss this opportunity to be part of the vibrant Winter Haven community. Key Features: *Kitchen: Newly remodeled kitchen with soft close upgraded cabinets and new appliances. Features: Fully furnished home with washer and dryer included; new bathrooms with upgrade tiles. Vinyl fence for pets and privacy. *Water softner system included

Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)

Listing Agent: Steven Koleno (804-656-5007)

Remarks: Fall in love with this expansive 5-bedroom, 3-bath, 3-car garage home situated on a quarter-acre of land, where luxury, functionality, and energy efficiency come together. Explore every corner of this stunning property right now through a 3D interactive walkthrough or a full video tour. Designed with an open layout and split bedrooms for privacy, the home feels massive yet efficient. The heart of the home is a wide-open living area and a huge kitchen featuring a gigantic island, 42-inch upper cabinets, a spacious pantry, and top-of-the-line stainless steel appliances. Whether you are relaxing, hosting, or cooking, the home provides boundless space to move and mingle. High-quality finishes are found throughout, including granite countertops in the bathrooms, luxury vinyl plank flooring in the main areas, and premium carpeting in the bedrooms. This isn't just a home; it’s an investment featuring $30,000 in upgrades available for your review! One of the standout benefits of this property is the incredible energy efficiency. Powered by solar panels plus a solar-powered attic fan, the home’s energy costs are cut in half compared to neighboring homes that have much smaller living areas. The solar panel lease is a manageable $180 a month, which keeps the actual electric bill payable to TECO energy as low as $5 to $20 a month. For added convenience, the home also includes a paid security system and a water softener system paired with reverse osmosis in the kitchen. The outdoor space is just as impressive, featuring a large, private backyard on a quarter-acre lot fully enclosed by a vinyl fence. You can enjoy the Florida weather from the comfort of a huge, screened-in lanai, surrounded by custom pavers that wrap seamlessly around the sides and back of the home. The meticulous landscaping is easily maintained by a full irrigation system. Located in a quiet, peaceful community in Polk County, you are perfectly positioned near Highway 27 for an easy drive to Disney and the Orlando Airport. Best of all, there are no CDD fees and a low HOA of only $725 a year. This home is being sold AS IS and is ready for you to move in. Schedule your showing today!

Listing is courtesy of: MAZELG REALTY (863-399-0226)

Listing Agent: Mary Sorrell (765-434-1802)

Remarks: One or more photo(s) has been virtually staged. Welcome to 6450 Hollyberry Lane in Brookhaven Village—a highly sought-after 55+ community where you own your land, making this a rare opportunity! This beautifully updated, move-in ready home features new luxury vinyl flooring (2025) and a bright, open layout perfect for everyday living and entertaining. The upgraded kitchen offers butcher block countertops, slide-out metal racks for added storage, and a brand-new dishwasher. Washer and dryer are included. Both bathrooms have been beautifully remodeled with modern finishes. Major updates include a new roof (Dec 2024), new HVAC system (2025) with ductwork and air handler, new windows (2025), and all-new screening, including the lanai with vinyl windows—perfect for enjoying Florida living year-round. The home is also fully replumbed with updated anchors and straps, including a vapor barrier that was installed about 4 years ago. The home also includes a great storage shed/workshop—ideal for hobbies or extra storage. Enjoy a super low HOA with access to a community pool and clubhouse, all in the heart of Winter Haven near shopping, dining, and lakes. Fully updated + land ownership + prime 55+ community—this one stands out. Schedule your showing today!

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

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

Remarks: IMPROVED PRICE!! LOCATION, LOCATION!! Gorgeous 3 bed, 2 bath POOL home with idyllic views across pretty pond with water frontage and private wooded island!! Located in the sought after gated, Overlook Estates on a spacious corner lot with mature landscaping. The open-concept living area creates an inviting atmosphere, ideal for both relaxed family gatherings and formal entertaining. Enter into the foyer which is flanked by dining room, living room and an additional study/den. Continue through into the spacious kitchen and family room with sliding doors leading to the covered lanai and screened pool area. Relax with your favorite beverage and enjoy the tranquil views of the pond and wooded island with an abundance of wildlife! The primary suite is to the left of the family room and boasts an atmospheric, cozy, gas fireplace and spacious primary bathroom. To the right of the family room are two further bedrooms and full size bathroom. Overlook Estates is perfectly situated among the Chain of Lakes in Winter Haven, not far from Cypress Gardens Blvd for fast commuting and access to dining, shopping and much more. Do not miss this opportunity to live the Florida lifestyle in this unique home!

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

Listing Agent: Sue Webb (407-361-6425)

Remarks: Short Sale. "SHORT SALE!! Seller accepting CASH ONLY!! APPROVED SHORT SALE PRICE BY LIEN HOLDER. Needs TLC. This midcentury POOL home has much potential. It features 3 bedrooms and 3 baths. It has a formal living room area, an office area and a large dining/family room for family gatherings. The fireplace has been converted to gas. Pool enclosure can be developed to be an amazing outdoor space. There is NO HOA, NO CDD and NO FLOOD ZONE is this well-established neighborhood. Located close to popular restaurants, shopping centers, and Legoland Florida Resort & Park, banks and lakes. It is tucked away, yet close to it ALL.

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

Listing Agent: Kelly Hansell (863-557-1784)

Remarks: One or more photo(s) has been virtually staged. SUPER DEAL on a big four bedroom home! Clean, fresh and well maintained home! PLUS, an American Preferred Home Warranty is included! With American Home Warranty, if you ever need to use it, you get to choose your own preferred vendors! Enjoy room for the family and privacy for mom and dad in the spacious split bedroom layout . You are going to like the open-concept living areas, big island kitchen with walk-in kitchen pantry. The large master suite with ensuite bath has a large walk in closet. Plenty of natural light brightens your living spaces from the energy efficient windows. All bedrooms are generously sized. Style and comfort welcome you with brand new beautiful, premium style, extra thick, waterproof luxury vinyl plank flooring in all the living areas. Fresh new carpet in all bedrooms. Pretty ceramic tile in wet areas. ROOF 2024! A fresh coat of premium exterior paint has been done and seals the deal for years to come. MOVE IN READY! Come and see this lovely home in the well-maintained Lakes at Lucerne community today!

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

Listing Agent: Patty Wolfgang (813-389-5226)

Remarks: Another Great Listing brought to you by Paul Jacques, P.A. EveryThing Real Estate. Gated Community, Like New. Open floor plan. minutes from downtown Winter Haven. Low HOA, you’ll enjoy neighborhood security and amenities without the extra cost. Commuters will love the quick access to Hwy 27, providing an easy drive to area beaches, Orlando’s theme parks, and more. Price To Sell.

Listing is courtesy of: XCELLENCE REALTY INC. (866-595-6025)

Listing Agent: Paul Jacques (561-441-9695)

Remarks: Under contract-accepting backup offers. Welcome home to this beautiful 2-bedroom, 2-bathroom golf villa nestled within the beautiful Cypresswood Golf and Country Club in Winter Haven, Florida. Property is steps away from the golf clubhouse!!! Home features a stunning Florida room, ready for relaxation. Dry bar with sink in living room perfect for entertaining your guests. Step out to your outside patio for even more enjoyment. With access to golf, clubhouse, Restaurant, pool and recreational facilities, this home offers a low-maintenance lifestyle in an active and vibrant community. Legoland attraction is approximately 5 miles. Disney World, Orlando and Tampa attractions are within 30-60 minute driving distance. Opportunities like this don’t last long, Just buy and move in!!! CLEAN TITLE WITH NO LIENS. Property being sold AS-IS. ALL interior contents and furniture convey with the property.

Listing is courtesy of: SUCCESS INVESTMENT REALTY (407-304-0490)

Listing Agent: Bill Sprys (407-574-9724)

Remarks: SELLER MOTIVATED! | NEW ROOF | NO CDD| GATED COMMUNITY Welcome home to 107 Mandolin Drive, a move-in ready, single-story gem nestled inside the sought-after Mandolin gated community in SE Winter Haven. This beautifully maintained 4-bedroom, 2-bath residence offers the perfect blend of comfort, style, and security, all with No CDD and a low HOA. A brand-new roof tops off a home that has been thoughtfully cared for inside and out. Soaring cathedral ceilings fill the open-concept living area with light and volume, creating an inviting atmosphere from the moment you walk in. The primary suite is a true retreat, featuring a spacious walk-in closet and a private en suite bath with a walk-in shower. A second bedroom also boasts its own walk-in closet, ideal for guests, family members, or a dedicated home office. The eat-in kitchen sits at the heart of the home and is designed for both function and connection, offering ample cabinetry, a breakfast bar, and all major appliances included. It flows seamlessly into the main living space — perfect for everything from weeknight dinners to weekend entertaining. Slide open the doors to your enclosed lanai, an ideal spot for morning coffee, game nights, or unwinding after a long day. The fully fenced backyard offers room to roam, bring your pets, your garden plans, or simply enjoy the open space. Prime location perks: -Minutes to the new Publix Supermarket, Legoland, shopping, dining & medical facilities -Zone for Chain of Lakes Elementary School -Easy access to both Tampa and Orlando. Gated living, modern updates, and an unbeatable SE Winter Haven address, this one checks every box. Schedule your private showing today.

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

Listing Agent: Mabel Vassallo (863-604-0499)

Remarks: One or more photo(s) has been virtually staged. Fully Renovated Gem in the Heart of Winter Haven! Step into this farmhouse charm : 2-bedroom, 2-bathroom home, nestled on a spacious lot in the established Villa Manor neighborhood. NO HOA This move-in-ready residence presents luxury finishes, laminate flooring throughout, a sleek new kitchen with updated cabinets, carrara white quarts countertops, and stainless steel appliances, and a freshly tiled bathroom with contemporary finishes. Fresh interior and exterior paint, and upgraded lighting fixtures. The large backyard offers plenty of space for outdoor living or future expansion. Located minutes from local schools, parks, and downtown Winter Haven’s shops and restaurants, this home is perfect for first-time buyers, downsizers, or investors seeking turnkey potential.

Listing is courtesy of: KELLER WILLIAMS LEGACY REALTY (407-855-2222)

Listing Agent: Daniel Araque (321-276-0747)

Remarks: Under contract-accepting backup offers. NEW PRICE! Move-in Ready. This one-story, 4-bedroom, 2-bath home offers 1,851 square feet of well-designed living space and is situated on an oversized corner lot in the VillaMar community. Recent upgrades include a fully vinyl-fenced backyard and a whole-home water filtration system with water softener, providing added comfort and peace of mind. Built in 2023, this Cali floorplan features abundant natural light, granite countertops, ceramic tile flooring throughout the main living areas, carpeted bedrooms, and smart home technology. An inviting foyer opens to a bright open-concept layout that seamlessly connects the living room, dining area, and kitchen—perfect for everyday living and entertaining. The kitchen is equipped with granite countertops, Whirlpool stainless-steel appliances, a walk-in pantry, and an oversized island with breakfast bar, offering ample workspace and storage. The primary suite, privately located at the rear of the home, includes an ensuite bathroom with dual sinks, a separate shower, and two closets—one built-in and one walk-in. Three additional bedrooms share a full bathroom, and a conveniently located laundry room with Samsung washer and dryer adds everyday convenience. The spacious backyard offers plenty of room for outdoor living and is large enough to accommodate a pool. VillaMar residents enjoy community amenities including a pool and playground. Ideally located near Legoland, parks, shopping, and recreational options, with easy access to major highways for a smooth commute. Schedule your private showing today!

Listing is courtesy of: CANVAS REAL ESTATE (954-332-7121)

Listing Agent: Jennifer Ng (305-308-6896)

Remarks: Welcome Home to this 3 bedroom/2 bath updated home. New granite counters in the kitchen, pass-through bar and both baths. Primary bath features a double vanity and walk-in shower, and secondary bath has large tile surround in the tub/shower combo. Kitchen is spacious and airy with a window sink overlooking the backyard. Freshly painted, new 6-panel doors, ceiling fans and lighting fixtures throughout. Laundry room is inside and has ample shelving for storage and pantry space. Tile throughout, so no carpet to maintain. Close to major throughfares, shopping and restaurants.

Listing is courtesy of: POWERS REAL ESTATE SOLUTIONS LLC (904-703-0905)

Listing Agent: Lynne Powers (904-703-0905)

Remarks: Under Construction. Located in the heart of Winter Haven, Willowbrook South puts you close to the area's Chain of Lakes, beautiful parks, and an array of dining and shopping. With top attractions and everyday conveniences just minutes away, your new home here keeps you connected to everything you love. Your new home at Willowbrook South places you right where you want to be. Let me Introduce you to the Archer II this 1328 Sqft. 3 Bedroom 2 Bath home is just to die for. This home provides Luxury Vinyl tile in all the wet areas, Living and Dining Rooms and Quartz Counter tops in the Kitchen and both Bathrooms. The Kitchen includes a Stove, Microwave, Dishwasher and Refrigerator, all Stainless Steel by Whirlpool and also includes a Washer/Dryer. The Archer II has an Open Floor plan that allows you to entertain guest even if they are in the living or dining room. Spacious bedrooms Owners Suite that can easily fit a King size bed. And on top of all that it also comes with our Home Smart System. Come by today!

Listing is courtesy of: DR HORTON REALTY OF CENTRAL FLORIDA LLC (407-250-7299)

Listing Agent: Paul King (407-519-3940)

Remarks: Under Construction. Located in the heart of Winter Haven, Willowbrook South puts you close to the area's Chain of Lakes, beautiful parks, and an array of dining and shopping. With top attractions and everyday conveniences just minutes away, your new home here keeps you connected to everything you love. Your new home at Willowbrook South places you right where you want to be. Let me Introduce you to the Archer II this 1328 Sqft. 3 Bedroom 2 Bath home is just to die for. This home provides Luxury Vinyl tile in all the wet areas, Living and Dining Rooms and Quartz Counter tops in the Kitchen and both Bathrooms. The Kitchen includes a Stove, Microwave, Dishwasher and Refrigerator, all Stainless Steel by Whirlpool and also includes a Washer/Dryer. The Archer II has an Open Floor plan that allows you to entertain guest even if they are in the living or dining room. 2 Spare Bedrooms and an Owners Suite that can easily fit a King size bed. And on top of all that it also comes with our Home Smart System. Come by today! *Photos are of similar model but not that of the exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability, and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

Listing is courtesy of: DR HORTON REALTY OF CENTRAL FLORIDA LLC (407-250-7299)

Listing Agent: Paul King (407-519-3940)

Remarks: Under Construction. Located in the heart of Winter Haven, Willowbrook South puts you close to the area's Chain of Lakes, beautiful parks, and an array of dining and shopping. With top attractions and everyday conveniences just minutes away, your new home here keeps you connected to everything you love. Your new home at Willowbrook South places you right where you want to be. Now let me Introduce you to the Freeport II this 1498 sqft, 4 Bedroom 2 Bath home is just to die for. This home provides Luxury Vinyl tile in all the wet areas and Great room and Quartz Counter tops in the Kitchen and both Bathrooms. The Kitchen includes a Stove, Microwave, Dishwasher and Refrigerator, all Stainless Steel by Whirlpool and the laundry room also includes a Washer and Dryer. With 2 Spare Bedrooms in the Front one in the Middle and an Owners Suite in the Back. The Owners Suite can easily fit a King size bed and has a large Walk-in closet. It also includes a Home Smart System. Come by today! *Photos are of similar model but not that of the exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability, and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

Listing is courtesy of: DR HORTON REALTY OF CENTRAL FLORIDA LLC (407-250-7299)

Listing Agent: Paul King (407-519-3940)

Remarks: NEW PRICE, JUST REDUCED!!! ON THE GOLF COURSE! CUSTOM BUILT 4 BEDROOM 2.5 BATH POOL HOME IN CYPRESSWOOD GOLF & COUNTRY CLUB'S PLANTATIONS! This beautiful home is on an oversized lot that offers space and privacy with fabulous golf course views & a circular driveway that accommodates ample parking for guests. Step into the foyer that leads to a large, open and bright living area with fireplace and triple sliding glass doors to the lanai. Enjoy the formal dining room with oversized windows & Plantation shutters. The hardwood floors in the main living area are gorgeous. The spacious kitchen with lots of storage has cabinets galore and a long breakfast bar, a dream for busy cooks! Adjacent to the kitchen is a cozy nook for informal dining overlooking the lanai, pool, Jacuzzi & golf course! The expansive primary suite is a true retreat with French doors that open to the lanai and pool area & the en-suite bath is complete with walk-in closets, dual vanities, a jetted bathtub and separate shower. Plenty of room for everyone with the three additional bedrooms, all large rooms with nice closets and privacy for all. The guest room has pool and lanai access through the French doors. Enjoy the golf course views from the screened lanai featuring a sparkling pool & spa. Entertaining is a breeze on the covered lanai with built-ins and TV. This home has been lovingly maintained. New roof in 2020, new hot water heater in 2026, freshly painted interior in 2026, Plantation shutters throughout, utility room with large laundry sink, oversized garage and the whole house generator is included. Cypresswood residents enjoy "the good life" in this golf community that features a 24-hour guarded entrance gate, 18-hole championship golf course, junior Olympic sized community pool, tennis & pickle ball facilities. The clubhouse includes a Pro Shop, bar & restaurant, making it easy to enjoy an active social lifestyle! Biking & walking are relaxing in Cypresswood with Resort style perks in an established & sought-after community that is convenient to shopping, dining, entertainment, medical and in close proximity to LEGOLAND and major highways. Call now to view this exceptional property and make it your own!!

Listing is courtesy of: THE K TEAM REAL ESTATE SERVICES LLC (863-604-1601)

Listing Agent: Cathy Kluytenaar (863-604-6220)

Remarks: Welcome to 3108 Buckeye Point Dr — where comfort meets convenience in the heart of Winter Haven. From the moment you arrive, this home invites you in with a layout designed for the way you truly live. With 4 bedrooms and 2 full bath and a brand new A/C system the living spaces feel open yet connected, creating an easy flow for both everyday routines and weekend gatherings. Natural light enhances the home’s warmth, while thoughtful design elements make each space feel intentional and livable. The kitchen serves as the hub of the home, seamlessly connecting to the main living areas — ideal for hosting, relaxing, or simply enjoying a quiet night in. The primary suite offers a private retreat, while additional rooms provide flexibility for guests, work-from-home needs, or hobbies. Step outside and imagine morning coffee, evening unwinding, and effortless Florida living in your own outdoor space. Located in a desirable Winter Haven community, you’ll appreciate the convenience to shopping, dining, medical facilities, schools, and major roadways — all while enjoying the feel of a tucked-away neighborhood setting. Homes that combine layout, location, and livability like this don’t stay available for long. Schedule your private showing and experience 3108 Buckeye Point Dr for yourself.

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

Listing Agent: Jp Phillips (863-670-7923)

Remarks: Welcome to 819 Sunset Cove, Winter Haven, FL 33880 – the perfect blend of space, comfort, and VALUE! This spacious 4-bedroom, 2.5-bath home with over 2,200+ SQFT sits on an OVERSIZED .38 ACRE CORNER LOT, offering the ideal setting for a growing family seeking both interior space and outdoor freedom — all for UNDER $300,000. Built in 2006, this home features a 2019 ROOF, 2014 AC, and NO carpet throughout, providing durability and easy maintenance. The expansive 16’ x 24’ PRIMARY SUITE offers a true retreat, while the home also includes a separate formal dining room and a versatile GROUND FLOOR OFFICE/DEN/FLEX ROOM that can serve as a 5th bedroom. Enjoy the benefits of a LOW HOA of just $25/month in a quiet, WELL-KEPT COMMUNITY. Conveniently located just minutes from DOWNTOWN WINTER HAVEN, with easy access to the AdventHealth Fieldhouse & Conference Center, Walmart, Publix, and numerous restaurants, plus quick access to Highway 570 (POLK PARKWAY) connecting you directly to I-4 for commuting to Orlando or Tampa. This is a rare opportunity to own a LARGE-LOT home with exceptional space and location at an affordable price — schedule your showing today!

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

Listing Agent: Nomar Rosa (646-673-3900)

Remarks: Under contract-accepting backup offers. Welcome to your dream villa in a resort-style 55+ community, where at least one resident must be 55 years or older. This beautifully maintained 2-bedroom, 2-bath home offers an open and inviting floor plan designed for comfort and easy living. Step inside to find a spacious living area filled with natural light, a versatile den perfect for a home office, formal dining, or family room, and a cozy sitting area at the kitchen counter ideal for casual meals or entertaining. The upgraded kitchen features quartz countertops, stainless steel appliances, and a breakfast bar, making it a true chef’s delight. The primary suite is a relaxing retreat with a generous walk-in closet, and an ensuite bathroom with dual vanity sinks and a walk-in shower. with upgraded shower doors. A separate laundry room and attached garage add everyday convenience. Enjoy peaceful mornings and evenings on your screened-in lanai. Just steps away, you’ll find the community mailbox, dog park, and outdoor workout area. HOA fees provide exceptional value, covering roof maintenance and repairs, exterior painting every five years, cable, internet, termite control, lawn care, irrigation repairs, and exterior home insurance—helping reduce overall homeowner insurance costs. Residents enjoy access to an impressive array of amenities, including a swimming pool, hot tub, sauna, fitness center, pickleball and basketball courts, shuffleboard, billiard room, library, computer/game room, craft room, aerobic studio, ballroom, and more. The highlight is the private dock and boat ramp with access to beautiful Lake Ruby. Conveniently located just 3 miles from Regal Eagle Ridge Mall, Aldi, Chili’s, Publix, and close to major attractions like Legoland, Peppa Pig Theme Park, and Bok Tower, this home offers both relaxation and accessibility. This exceptional villa delivers the perfect blend of comfort, and convenience. Don’t miss your opportunity to enjoy resort-style living at its finest, schedule your private tour today!

Listing is courtesy of: VESTI LLC (407-749-5489)

Listing Agent: Natalie Rivera (321-800-1485)