Winter Haven Homes For Sale & Real Estate - 805 homes

Remarks: Under Construction. Welcome to Ashton Covey in Winter Haven! Discover the ultimate Florida lifestyle in this stunning community. Perfectly situated just off US Highway 27, your new home offers seamless access to work, outdoor recreation, shopping, dining, and more. Imagine being less than 15 minutes from Downtown Winter Haven, where charming local shops and restaurants await your exploration. Plus, you're just 5 miles from public lake access at Lake Daisy, ideal for a day of boating, paddle boarding, and enjoying the water. The Panama single-family home is what you always pictured for yourself. Step in from your 2-car garage or front porch and pass the first of 4 spacious bedrooms and a full bath with double vanity. In your dining area, prepare to be wowed. This space is highlighted by a gourmet kitchen with a large island overlooking your lanai and a great room where friends and family will gather. Your luxurious owner’s suite includes a double vanity owner’s bath and a huge walk-in closet. Your second-story bonus room is the perfect space for a home office, playroom or guest suite. You can have it all with the Panama. All Ryan Homes now include WIFI-enabled garage opener and Ecobee thermostat. **Closing cost assistance is available with use of Builder’s affiliated lender**. DISCLAIMER: Prices, financing, promotion, and offers subject to change without notice. Offer valid on new sales only. See Community Sales and Marketing Representative for details. Promotions cannot be combined with any other offer. All uploaded photos are stock photos of this floor plan. Actual home may differ from photos.

Listing is courtesy of: MALTBIE REALTY GROUP (813-819-5255)

Listing Agent: Bill Maltbie (813-819-5255)

Remarks: Located in the highly sought-after gated golf community of Cypresswood in Winter Haven, this beautiful 4-bedroom, 3-bathroom home offers over 2,800 square feet of spacious living when pool room footage is added. The offering includes a private pool, and a 9x9 pool house complete with a half bath, perfect for guests, poolside entertaining, or an additional flex space. Inside, the home boasts a formal living room and an open-concept family room, dining area, and kitchen, creating a bright and inviting atmosphere ideal for both everyday living and hosting. Also features granite countertops, resurfaced garage, private office, freshly painted interior, paver driveway, and so much more. Enjoy the comfort, privacy, security, and lifestyle that come with living in one of Winter Haven’s premier golf communities.

Listing is courtesy of: LBJ REALTY AND ASSOCIATES LLC (863-206-1552)

Listing Agent: Lovett Johnson (863-206-1552)

Remarks: POOL Home on Pond in TERRANOVA! Located in desirable southeast Winter Haven, this home has it all! Large areas overlooking screened pool and pond frontage and views! Enjoy the security of a gated community close to schools, shopping, churches and LEGOLAND! Call for your private showing today!

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

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

Remarks: Welcome to this well-maintained 3 bedroom, 2 bath home located on a quiet, established street. The Spacious eat in kitchen features tile flooring and a new refrigerator, perfect for everyday living and entertaining. The living room has new vinyl flooring and newly painted, creating a bright and inviting space, while the large family room offers plenty of room to relax or gather. This home also offers a spacious indoor laundry room, a one car garage and whole -house hurricane shutters that are easy to install, providing added piece of mind. Enjoy outdoor living on the screened-in back porch overlooking a fully fenced yard. Conveniently located close to shopping, dining, Polk State College and entertainment. This home combines comfort, functionality and an excellent location.

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

Listing Agent: Carina Lees (540-616-7997)

Remarks: Under contract-accepting backup offers. BEAUTIFUL , RENOVATED 2BEDS, 2 BATHS , OPEN CONCEPT , LAMINATED FLOORS, QUARTZ KITCHEN COUNTER TOPS, NEW KITCHE, NEW BATHROOMS. ENCLOSED PORCH, OVERSIZE LOT. PARTIALLY FENCED, NEW ROOF,NEW AC. READY TO MOVE IN. CLOSE TO SCHOOLS, HOSPITALS, LEGO LAND, MAJOR HWYS NO HOA.

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

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

Remarks: HUGE PRICE ADJUSTMENT — MOTIVATED SELLER! Welcome to this beautifully, open-concept Sebastian model FULLY FURNISHED and TURNKEY, allowing you to settle in and start enjoying the Lake Ashton lifestyle from day one. Grand, high ceilings immediately draw your eyes to the serene 17th-hole golf view, offering a peaceful backdrop perfect for relaxed living. The living room is anchored by a stunning wood entertainment center with glass display, complemented by plush leather recliners ideal for unwinding or hosting friends. Recessed lighting, neutral tones, and crown molding create a warm, inviting ambiance throughout the home. This home features tile flooring throughout the main living areas, thoughtfully selected furnishings in every room, and a second bedroom equipped with a medical bed for guests or caregiving needs. The gourmet kitchen includes 42" wood cabinetry with crown molding, granite countertops, a stylish backsplash, pendant lighting, Whirlpool stainless steel appliances, and under- and over-cabinet lighting. A washer and dryer are also included for easy, everyday living. The primary suite offers a peaceful retreat with a walk-in closet, dual granite vanities, and a walk-in shower with a corner seat. Triple sliders open to an extended screened veranda, perfect for morning coffee, evening breezes, or simply enjoying the tranquil golf course setting. The Garage is equipped with storage, a golf cart, a leisure bike, and a garage privacy screen, making it easy to embrace the active lifestyle of Lake Ashton. Just unpack and begin enjoying the community, offering two gated entrances with 24/7 guard service and access to two clubhouses featuring a grand ballroom, movie theater, bowling lanes, and on-site dining at Charm City and Eagle Nest. Stay active with amenities including indoor and outdoor pools, fitness centers, racquetball, tennis, pickleball, bocce, shuffleboard, and more.

Listing is courtesy of: LAKE ASHTON REALTY INC. (863-221-5970)

Listing Agent: Candra Alston (407-257-5204)

Remarks: 2-Bedroom, 2-Bathroom Mobile Home in a 55+ Community of ORANGE MANOR WEST-NO LOT RENT!-This spacious 1,352 sq. ft. double wide mobile home located in a 55+ community that offers a wealth of amenities for an active lifestyle. BRAND NEW A/C! The living room features sliding glass doors that open to a front enclosed Florida room, perfect for enjoying the view of your front yard. The kitchen comes fully equipped with all appliances and a separate dining room for your meals. The main bedroom boasts an en-suite bathroom and a walk-in closet. The second bedroom is adjacent to a recently updated bathroom. Inside laundry room with additional storage, washer, and dryer included. A long carport that can accommodate two cars, with a garage door leading to extra storage space. Roof: Installed in 2017. Community Amenities: Pool, Clubhouse with billiards and library,Putt-putt golf, Bocce ball and horseshoe fields, Shuffleboard and Basketball court. Please note, this park does not allow pets. Don’t miss out on this wonderful opportunity! Call now for more details.

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

Listing Agent: Kelley Blackburn (813-478-0023)

Remarks: Charming 3-Bedroom, 2-Bathroom Home in Squires Grove – Move-In Ready! Welcome to this beautifully maintained 3-bedroom, 2-bathroom home located in the desirable Squires Grove subdivision. This move-in ready property offers modern updates and thoughtful features that make it the perfect place to call home. Step inside to find brand new commercial-grade waterproof laminate flooring throughout, adding both durability and style. The spacious living room is perfect for relaxing or entertaining, while the kitchen includes a cozy eating area ideal for casual family meals. Enjoy Florida living at its best with a screened-in back patio, complete with lighting and tile flooring—a great spot for morning coffee or evening gatherings. The patio opens up to a beautiful back yard, offering added peace and privacy. BRAND NEW A/C system installed in March 2025, ensuring comfort year-round. Conveniently located near schools, shopping centers, and parks. Don’t miss this opportunity !

Listing is courtesy of: REMAX EXPERTS (863-802-5262)

Listing Agent: Tony Fridovich (863-698-4267)

Remarks: Whether you are looking for your first home or first rental property, this condominium is a must see! Ideally located off of Overlook Drive in Winter Haven, minutes form Legoland, downtown Winter Haven, and the Chain of Lakes. This unit features an updated kitchen with an upgraded stainless steel gas stove, stainless steel dish washer, and a one-year-old refrigerator. Additionally, there are newer dual pane windows, tile throughout the living area, and vinyl plank floors in the bedrooms! The air conditioner is only two years old and has a warranty that expires in 2033 and the washer/dryer is only one year old. The interior walls were just painted and this unit is ready for a new owner or tenant! This is one of the nicest units in the complex! Call today to schedule a showing!

Listing is courtesy of: CLARK REALTY LLC (863-345-2155)

Listing Agent: Steven Perkins (863-797-7276)

Remarks: Move In Ready 3BR/2BA + Home Office + Dining / Flex Room and Large Screened Lanai. The Interior Features an Open Floor Plan, High Ceilings, Spacious Bedrooms, New & Updated Lighting & Fans, Fresh Interior Paint, Brand New Carpet in BR's and more! The Large Kitchen Offers a Spacious Breakfast Cafe Overlooking the Lanai & Backyard, Newer Countertops, Tiled Backsplash and New Dishwasher. The Master Suite Offers a Huge Walk-In Closet, Soaking Tub, Double Vanities and Walk-In Shower. The Exterior Offers a Fully Privacy Fence, Large Backyard and Newer Storage Shed. Please Note the Property Link extends another 14' beyond the rear fence. This Gated Community is conveniently located in Winter Haven close to Publix Shopping, Walmart, Restaurants and Legoland. Enjoy all that Winter Haven has to offer - Multiple Lakes for fishing & boating, Nature Trails, Golf Courses and more. Located One Hour from both Tampa and Orlando International Airports, Lakeland Linder Airport now offering domestic flights too.

Listing is courtesy of: SHAWN R MCDONALD REALTYGRP INC (863-287-0213)

Listing Agent: Shawn Mcdonald (863-287-0213)

Remarks: Located in the heart of downtown Winter Haven, FL, this versatile R-3 zoned property presents an excellent opportunity for homeowners, investors, or those seeking future development potential! This charming residence features 2 bedrooms and 1 full bathroom, offering a functional layout with comfortable living spaces. The home includes a spacious kitchen with ample cabinetry and room for dining, perfect for everyday living or rental use. A dedicated utility room adds convenience and extra storage space. Connected to city water and sewer, this property provides reliable infrastructure and ease of maintenance. The R-3 zoning allows for a variety of potential uses (buyer to verify with city) making this a flexible investment in a growing and desirable downtown location. Enjoy close proximity to local shops, dining, parks, and all that Winter Haven has to offer, including its renowned chain of lakes! Whether you're looking for a primary residence, rental property, or future development opportunity - this property checks all the boxes!

Listing is courtesy of: RE/MAX REALTY PLUS (863-385-0077)

Listing Agent: Emily Jones (863-446-3246)

Remarks: Welcome to this well-maintained 2-bedroom, 2-bath home located in the desirable community of Oakwood Estates in Winter Haven. This home offers a peaceful, well-kept neighborhood with a welcoming atmosphere and a beautiful lake view to enjoy. Recent updates include new kitchen and bathroom flooring, new windows, and new interior and exterior doors, along with a roof that is approximately 5 years old, offering added value and peace of mind. No lot rent—ownership includes the land, with only a low monthly HOA fee. Oakwood Estates is a gated 55+ community offering resort-style amenities including clubhouses, heated pools, fitness center, shuffleboard, tennis courts, and a full calendar of activities. Conveniently located near shopping, dining, medical facilities, and major roadways. Schedule your private showing today and experience easy living in this vibrant community.

Listing is courtesy of: LA ROSA REALTY PRESTIGE (863-940-4850)

Listing Agent: Jody Pagan (863-604-2367)

Remarks: Located in Osprey Pointe on Lake Ned, 3905 Osprey Pointe Cir. is everything you've been looking for in the heart of Central Florida. This 3 bed, 2 bath home was built to last and withstand anything that comes it's way. Using solid poured concrete tilt walls, the house is incredibly strong and comfortable. Offering over 1700 square feet of air conditioned space, you will never feel confined. The family room, kitchen and dining area have soaring vaulted ceilings, while the primary bedroom feels spacious with a beautiful tray ceiling. The kitchen has many upgrades including solid cabinets, granite counter tops and a natural gas range. You'll also have access to the community clubhouse, pool and dock. With a location just minutes from great shopping, restaurants, grocery stores, medical facilities and Legoland! This home is in great shape and has a wonderful location. It will not last long, come see it before it's gone.

Listing is courtesy of: STRAIGHT UP REALTY & PM LLC (863-698-7547)

Listing Agent: Cole Bataille (863-698-7547)

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: Midcentury-vibed house. This property has approximately 1,559 square feet of living space on a lot of approximately 0.28 acres, with three bedrooms, one full bathroom and an en-suite half bathroom. Hardwood-style vinyl flooring and stone fireplace creates a warm and inviting tone. Large windows allow for an tons of soft, natural light to fill the rooms, enhancing the open layout and creating a peaceful setting. The separate dining room area provides space for hosting a dinner or game night. The retro vibe flows throughout the house and fits-in with the established neighborhood. An efficient kitchen features a window overlooking the backyard and makes it convenient to have BBQs and fun playtime out back. The backyard has it's own storage shed and is large enough to have a pet, playground or maybe even a pool. The primary bedroom and two additional bedrooms are on opposite sides for privacy and quiet. The vintage-styled bathrooms add a unique charm to the home. The pink tile sequence makes it fun to get ready for the day. Just steps from the college, the property is conveniently located near the college ballfields, offering easy access to recreational activities. A walking trail nearby provides opportunities for exercise, and the home is situated close to the town, allowing for quick and easy access to local shopping. The garage features a work bench and shelves, providing storage and workspace. The property's proximity to the lake allows for enjoyable walks or leisure activities on the water.

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

Listing Agent: Maria Deary (863-241-8361)

Remarks: Welcome to this well-maintained 3-bedroom, 2-bathroom home on a desirable corner lot and offers a 2-car garage along with a fully fenced backyard. Inside, tile flooring highlights the high-traffic areas, while wood laminate flooring runs through the living room and bedrooms. The kitchen features a stainless sink, refrigerator, and stove. Step outside to enjoy a screened back porch and a paver patio—perfect for relaxing or entertaining. Major updates include a new central A/C installed in 2016 and a new roof completed in 2021. Conveniently located close to Polk State College, shopping, and plenty of restaurants. Legoland is just minutes away!

Listing is courtesy of: CENTURY 21 MYERS REALTY LAKE WALES (863-676-4448)

Listing Agent: Austin Henry (863-605-3451)

Remarks: **PRICE IMPROVEMENT** MAINTENCE-FREE LIVING...Located right in the Heart of Winter Haven at Imperial Villas, a 55+ community. This very well maintained 2 Bedroom/ 2 Bathroom Villa that offers a complete update, boasting tasteful renovations throughout. Being sold Fully Furnished! From the kitchen to the bathrooms, flooring to the roof, nearly everything has been thoughtfully upgraded. Step inside to discover new ceramic tile and luxury vinyl flooring that sets a modern tone. The kitchen showcases stainless steel appliances, granite countertops, ample cabinet and countertop space. Retreat to the owner's suite at the back of the villa, offering a beautifully tiled walk-in shower and a generous walk-in closet. Through the great room, step into to enclosed lanai. Updates include: Roof (2020), Electrical Panel (2023), HVAC (2012) & Tankless Hot Water Heater (2018). Residents of this community have access to a refreshing pool, making it perfect for leisurely afternoons. The low HOA fee of $270/month covers water, internet, cable, gas, trash and grounds maintenance, ensuring a hassle-free lifestyle. Conveniently located just a short walk from the picturesque Lake Howard and minutes away from downtown Winter Haven. You'll have easy access to charming shops, delectable restaurants, the historic Ritz Theater, and vibrant events like farmers markets in the park. Don't miss out on the opportunity to make this your new home. Schedule your private showing today and experience the epitome of Florida living!!

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

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

Remarks: Under contract-accepting backup offers. Welcome home to this fabulous 3 bedroom, 3 bath water front pool home nestled in the desirable Bridgewater community. The home is located on the infamous "WINTER HAVEN CHAIN OF LAKES" on the canal between lake Eloise and the cleanest spring fed lake on the chain, LAKE WINTERSET. BRIDGEWATER IS AN ESTABLISHED COMMUNITY OF 22 CUSTOM BUILT HOMES. With access to a private community boat ramp, and newly renovated COMPOSITE dock for your boating and fishing pleasure. Lake Winterset often offers a SLALOM COURSE for the water skiing enthusiast. This fabulous brick home will have a BRAND NEW REROOF with ARCHITECTURAL SHINGLES, peel and stick UNDERLAYMENT installed over the next two weeks for the new owners peace of mind. The new roof will have a ten year transferable warranty to the new owner. As you enter this amazing home you'll be greeted by the grand foyer with vaulted ceilings, and an amazing view of the wood burning brick fireplace in the sunken great room with wooden floors, BLENDING RETRO CHARM WITH MODERN COZY FUNCTIONALITY. There are two sets of French doors exiting to the outdoor kitchen pool area from the great room with amazing views. As you turn to the right, you step inside the amazing study with wooden floors which can easily be transformed into a formal sitting room. Boasting over 2,369 square foot of living space there is plenty of room in this oversized kitchen and dining area to entertain your guest and sliding doors to exit to the pool area. The custom made plantation shutters in the dining area, convey with the home. The large primary bedroom has its own sliding doors that exit to the fully enclosed screen pool and outdoor kitchen area and TWO LARGE WALK IN CLOSETS. The primary bathroom has dual vanity sinks and a large garden jet tub with separate walk in shower stall. Enjoy cooking and entertaining in your fully screened in lanai with an outdoor kitchen area while taking in the sights and sounds of nature on this freshwater canal, AND CASCADING WATERFALL FROM THE SPA INTO THE HEATED POOL. The community of Bridgewater has its own PRIVATE BOAT RAMP LAUNCH and newly renovated dock for unlimited usage to its residents that wish to boat or fish just a few feet from their front door. The home is equipped with two air condition units one replaced 2 YEARS AGO and the other 5 YEARS AGO. Both front loader, washer and dryer convey inside this large indoor laundry room. The two car garage door was insulated for more energy efficient climate control. The home is located just 2.3 MILES FROM THE GATES OF LEGOLAND and just 2.5 MILES FROM SHOPS RESTARUANTS AND MEDICAL FACILITIES making this location ideal. Schedule your viewing today.

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

Listing Agent: Eric Sigismondi, Llc (863-651-9257)

Remarks: PRICE REDUCTION!! Welcome to the lakefront community of Edgewater Manor! Come see this awesome custom built 2017 4 bed 3 bath corner lot (1/3 ac.) home with fenced backyard! Located just off Cypress Gardens Blvd., this bright, open floorplan includes combo living and dining area, an office, and a spacious kitchen with white wood cabinets and grey granite counter tops, stainless steel appliances, gas stove, and eat-in area. There is a large family room off the kitchen, crown molding throughout the home, vinyl fencing, and much more, including: gas tankless WH, vinyl planking floor everywhere but bedrooms, plantation shutters, double pane low E windows, a screened lanai. There is even a plug for an electric car built into garage wall, and a shallow well for lawn irrigation. Plus, close to Legoland, restaurants, shopping, and the chain of lakes. A great find!

Listing is courtesy of: STORMS REALTY (813-293-4652)

Listing Agent: Steve Storms (813-293-4652)

Remarks: Welcome to refined Florida living in the serene, gated, 55+ community of Preserve at Lakeside Landings. This community designed with enjoying your Florida lifestyle, is home to 44 residences, 2 pools, a playground, and sidewalks to keep you active. HOA includes lawn maintenance which allows you to relax in your stunning new home! Thoughtfully designed with a triple-split floorplan, this residence offers exceptional privacy and versatility—ideal for multi-generational living. Manicured tropical landscaping and pristine sidewalks lead you inside, where the first split features two guest bedrooms and a shared bathroom. Continuing into the main corridor, you’ll find the third bedroom or office along with the conveniently located laundry room.The home then opens into a bright, airy living space with 9-foot ceilings and tile flooring. An elegant dining area overlooks the pool, while the beautifully appointed kitchen showcases solid wood cabinetry, granite countertops, stainless steel appliances, and a generous island perfect for entertaining. The primary suite serves as a peaceful retreat with updated flooring, a walk-in closet, and a spa-inspired bath complete with dual sinks, granite, and a glass walk-in shower. Outdoors, the property transforms into a true tropical sanctuary. A stunning saltwater pool with a cascading waterfall is framed by lush landscaping that is home to several citrus trees. This secluded, spa-like atmosphere is ideal for relaxation or entertaining. With a tranquil natural backdrop and effortless indoor-outdoor flow, this home blends elegance, comfort, and resort-style appeal. Fresh interior paint, an immaculate garage, energy-efficient insulation, and lawn care included in the HOA make this home truly move-in ready—offering a lifestyle of ease, beauty, and authentic Florida living. Upgrades include kitchen appliances 2025, new disposal, Pentair salt system is 4 years old. Pool deck was sealed one year ago. Don't hesitate, opportunities like this are rare, so make your appointment today!

Listing is courtesy of: FLORIDA REAL ESTATE COMPANY (863-701-3487)

Listing Agent: Cyleste Goodson (863-701-3487)