Winter Haven Homes For Sale & Real Estate - 857 homes

Remarks: Discover your serene retreat at Winter Haven Harbour Condos—a charming 55+ community featuring this delightful third-floor, two-bedroom, one-and-a-half-bath residence. Recently refreshed 3 years ago with a brand-new roof, fresh paint, and plush new carpeting in both bedrooms and the living space, this home is move-in ready. The kitchen is bright and functional, with plenty of cabinetry that extends into the dining area and ceramic tile flows seamlessly through the kitchen and baths. Enjoy a screened front porch, perfect for morning coffee. The community offers a large heated pool, a clubhouse, shuffleboard, and a grilling area—ideal for gatherings. Conveniently located near shopping, medical centers, and with easy access to both Tampa and Orlando, this is a rare opportunity. Schedule your private tour today!

Listing is courtesy of: HARPER REALTY FL, LLC (863-687-8020)

Listing Agent: Annie Wood (321-229-1913)

Remarks: "OWNER WILL CREDIT UP TO $15,000 FOR THE COST OF ROOF REPLACEMENT AT CLOSING" FOR SALE: Attractive 3-Bedroom, 2-Bathroom Single-Family Home in Winter Haven! Discover your dream home in Osprey Pointe, where comfort meets style. This home is designed for modern living and entertaining. An open floor plan connects the eat-in kitchen and breakfast bar seamlessly to the living and dining areas, perfect for gatherings. Equipped kitchen with an eat-in area and a breakfast bar, ready for family meals and casual dining. Luxurious Master Suite: Retreat to your sanctuary featuring an elegant tray ceiling, a generous walk-in closet, double vanities in the primary bathroom, and a large glass shower stall. Enjoy the Florida lifestyle on your covered and screened rear porch. A paver driveway and an attached 2-car garage add to the curb appeal. The home includes inside laundry with washer and dryer hook-ups. Tiled common areas and bathrooms offer easy maintenance, while plush carpet in the bedrooms provides comfort. Exceptional Community Amenities: Live like you're on vacation every day! Enjoy access to a community clubhouse and a sparkling pool. Plus, take advantage of the private waterfront dock on beautiful Lake Ned for fishing and recreational activities. Lawncare included in HOA. Don't miss this opportunity to own a piece of paradise in Winter Haven. Schedule your showing today!

Listing is courtesy of: FLORIDA REALTY RESULTS LLC (407-498-3838)

Listing Agent: Debbie Browning (407-908-9060)

Remarks: Welcome to the luxurious 55+ golf course community of Lake Ashton! The home is the Biscayne floor plan, consisting of 3 bedrooms and 2 baths and a 2 car garage. The home and garage are accessible with electronic entry for ease. This home has been a winter retreat and only lived in a few months per year. Beautifully installed ceramic tile throughout and carpet in the bedrooms with 9' ceilings create such volume to the space. This home has stainless appliances and solid countertops to compliment the solid wood cabinetry giving it overall elegant feel and spaciousness. The breakfast nook looks into the main living space as well as out to the pond and nature preserve through one of the two 8' sliders giving perfect tranquility to peaceful mornings. No backyard neighbors!! Expansive primary bedroom with soaking tub and dual walk in closets make for the perfect retreat. Home is fully furnished with golf cart in the garage and all items are negotiable with purchase. Come see all that the Lake Ashton community has to offer.

Listing is courtesy of: KEYS TO THE BAY REAL ESTATE (813-965-1057)

Listing Agent: Nicholas Costello (813-965-1057)

Remarks: Under Construction. The main floor of the inviting Ammolite plan offers a private study and versatile flex space, which can be optioned as an additional bedroom and bathroom or a guest suite, complete with living room. You’ll also appreciate a convenient powder room; a nook; a great room and a well-appointed kitchen with a center island, a large pantry, and optional additional cabinets. Upstairs, discover an airy loft, a convenient laundry, three secondary bedrooms, and a lavish primary suite boasting an expansive walk-in closet and a private bath. This plan also features a patio and a 2-car garage. SAMPLE PHOTOS. Actual homes as constructed may not contain the features and layouts depicted and may vary from image(s).*Take advantage of special financing on quick move-in homes OR buy a to-be-built home and enjoy up to $20,000 in Flex Funds toward homes that can close in a timely manner! Options may vary by community, and offers are available on select homes on a first-come, first-served basis. Contact builder for more information!

Listing is courtesy of: AXEN REALTY, LLC (480-399-1218)

Listing Agent: Stephanie Morales, Llc (407-399-2055)

Remarks: Under contract-accepting backup offers. Welcome to this beautifully updated and immaculately maintained home that truly stands out. This 3-bedroom, 2-full-bath residence reflects the sellers’ meticulous care and pride of ownership throughout, offering peace of mind with a roof that’s only 8 years old. Step inside to find tile flooring throughout the ENTIRE HOUSE, all accented by crown molding throughout the entire home. The updated kitchen features Corian countertops, stainless steel appliances, ample cabinetry, and a functional layout perfect for everyday living and entertaining. Both bathrooms have been tastefully renovated with granite countertops and modern finishes. Enjoy Florida living at its best with a screened lanai overlooking a huge, fully fenced backyard, ideal for gatherings, pets, or relaxing in privacy. The outdoor space also includes a concrete barbecue area, making it perfect for entertaining. Additional features include a screened garage door and a charming front porch that enhances the home’s curb appeal. Ideally located close to shopping, dining, and everyday conveniences, with easy access to Orlando, this move-in-ready home offers the perfect combination of comfort, updates, and location. A must-see!

Listing is courtesy of: HOMEXPRESS REALTY, INC. (813-641-2500)

Listing Agent: Luciene Sarubbi (813-641-2500)

Remarks: One or more photo(s) has been virtually staged. Seller is offering $5,000 towards the buyers closing costs and prepaids! Completed in 2020 and ready for immediate occupancy, this property blends modern construction with thoughtful recent upgrades. Notable features include a brand-new roof installed in 2023, fully paid solar panels, a freshly painted interior, and professionally serviced and cleaned air ducts, all contributing to energy efficiency and average utility costs of approximately $85–$100 a month. The home is equipped with smart home technology and constructed with concrete block on both the first and second floors, offering added durability and peace of mind. Inside, the kitchen opens naturally to the main living spaces, creating an inviting layout for everyday living and entertaining. A future flooring update provides an easy opportunity to personalize the space. Bedrooms are generously sized, with the primary suite located upstairs, and a fully fenced backyard enhances privacy and functionality. Ideally positioned within the community, the home is just a short walk to the mailbox, pool, and playground, with convenient access to shopping, dining, grocery stores, major roadways, just a short drive to LEGOLAND® and less then one hour from Walt Disney World.

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)

Listing Agent: Kristin Duncan (407-274-5911)

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)