Homes For Sale in Winter Haven 33884 - 380 homes

Remarks: Under contract-accepting backup offers. It's all about Location! Nestled in between Lake Roy and Lake Summit! Welcome home! The living room and dining area wrap around the kitchen. New Island with breakfast bar that sits 6! The eat in nook area and doors to step out to the screened room and shady backyard, a perfect spot for reading, napping and relaxing. The Primary bedroom is of nice size and the two additional bedrooms are down the hall and have ample closet space. The Inside Utility has access to the side breezeway and the garage. Endless possibilities! Need a seasonal home instead of renting or investment property? This is it! This home's location can’t be beat in the beautiful center of Winter Haven known for the Chain of Lakes for fishing, boating and water sports, Legoland, Shopping, Dining in beautiful Winter Haven. Easy commute to Central Florida Attractions! Call today for more details and showing!

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

Listing Agent: Tina Heim, Pa (863-370-1786)

Remarks: Short Sale. Perfect starter home or investment property! Welcome to this 4-bedroom, 2-bathroom residence located in the desirable Orleans community. Built in 2023, this charming corner-lot home offers an open floor plan with a spacious living area, kitchen, and dinette—all featuring easy-to-maintain tile flooring. A sliding glass door leads to the covered lanai, perfect for relaxing or entertaining. The primary bedroom is privately situated at the back of the home and includes a large walk-in closet and an ensuite bathroom with dual vanities and a separate stand-alone shower. Toward the front of the home, you’ll find three additional bedrooms and a full guest bath, offering plenty of space for family or visitors. Additional highlights include a laundry closet with washer/dryer hookups, a two-car garage, and a spacious backyard thanks to the corner lot. With a low HOA and peace of mind from a newer roof, HVAC, and water heater, this home offers both comfort and value. Conveniently located less than a mile from Legoland Florida Resort, and close to shopping, dining, medical facilities, and hospitals—this property truly has it all.

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

Listing Agent: Veronica Figueroa (407-519-3980)

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

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

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

Remarks: Beautifully Maintained 2 bedroom, 2 bath home with a large 2 car garage, perfectly situated on a corner lot. Nestled in Lake Dexter Moorings with a Low Monthly HOA fee! Enjoy access to the neighborhood amenities - a sparkling community pool, a private boat ramp, and a dock. Freshly painted interior! Spanning just over 2,000 square feet of living space, this home offers a spacious great room, an expansive Florida room, and a bright and airy kitchen with a cozy dinette. Large sliding doors open up to the Florida room, creating a seamless transition, allowing easy access to additional space for your entertainment needs. The primary bedroom is complete with an en suite bathroom featuring dual sinks and a walk-in shower. Step outside to your custom brick paver patio, perfect for savouring your morning coffee, having a weekend BBQ, or simply relaxing after a long day. Don't miss this WONDERFUL home, call today!

Listing is courtesy of: ASSOCIATE REALTY (863-618-4000)

Listing Agent: Chrissi Jasso (863-618-4000)

Remarks: BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. Feel at home with the Magenta, a single-story home with 3 bedrooms, 2 bathrooms, and a 2-car garage. This layout is a true gem, seamlessly blending modern comfort with Florida charm. Open concept living dazzles with luxury vinyl plank flooring throughout the main living areas. The kitchen, featuring quartz countertops, new stainless-steel appliances and ample storage overlooks the dining and living area. A dreamy, covered lanai, accessible through sliding glass doors, invites you to take full advantage of the Florida climate. The owner’s suite boasts double vanities, a walk-in shower and a substantial walk-in closet, while the additional bedrooms and full bathroom are located off the kitchen for added privacy. With a brand-new washer and dryer conveniently located off the foyer, a smart thermostat with voice control to maintain energy efficient living, and professionally curated landscaping, the Magenta is designed to make every day extraordinary. Just off US-27 with quick access to I-17, Villa Mar puts you close to local hotspots, and everything that makes Central Florida shine. Discover Winter Haven’s Chain of Lakes, explore the historic downtown district, or enjoy a fun-filled day with the family at LEGOLAND® Florida Resort. At Villa Mar, you’ll enjoy a fresh approach to relaxed living, with everyday essentials and local favorites right around the corner. 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 to this beautifully maintained residence located in the lakefront community of Traditions, one of Winter Haven’s premier 55+ gated communities known for its vibrant lifestyle and exceptional amenities. Fully upgraded with a brand new HVAC system and water heater installed (both in March 2026), an updated roof (November 2023), updated kitchen appliances (2024), refreshed landscaping (2026), newer irrigation controller and bidet (2025), fresh interior paint (December 2025) and exterior paint (2024). This thoughtfully designed 2 bedroom, 2 bathroom home also includes a versatile office that can easily serve as a third bedroom, along with a spacious family room that provides additional living space for relaxing or entertaining. As you arrive, you’re welcomed by a covered and screened front entry. Inside, the open concept floor plan is enhanced by vaulted ceilings and a stylish blend of luxury vinyl flooring in the main living areas and ceramic tile in the kitchen, bathrooms and laundry room, creating both elegance and easy maintenance. The eat in kitchen is bright and inviting, featuring a closet pantry, stainless steel appliances that are just two years old and a comfortable dining space ideal for everyday meals. An interior laundry room is conveniently located just off the kitchen and provides direct access to the two car garage. Sliding glass doors from the living room lead to a screen enclosed patio, offering the perfect spot to unwind, entertain guests, or simply enjoy Florida’s beautiful year round weather. The primary suite serves as a relaxing retreat, highlighted by a tray ceiling, walk in closet and an ensuite bathroom with a double sink vanity and step-in shower. Outside, the property is beautifully framed by mature landscaping, with an attached two car garage, brick paved driveway and walkway that enhance the home’s inviting curb appeal. Residents of Traditions enjoy a true resort style lifestyle, featuring a lakefront clubhouse with a library, fitness center, card room, and billiards, as well as a resort style pool, hot tub and sauna. Additional amenities include tennis and shuffleboard courts, a dog park, a boat ramp and a dock overlooking Ruby Lake, providing endless opportunities for relaxation and recreation. The $484 monthly HOA fee covers lawn care (including bush/tree trimming and mulch replacement), exterior painting, cable, and internet. Ideally located near shopping, dining, and medical facilities with Publix opening soon just down the street, this home offers the perfect combination of comfort, convenience, and an active community lifestyle.

Listing is courtesy of: RE/MAX HERITAGE PROFESSIONALS (863-256-2188)

Listing Agent: Patricia De Graaff, Llc (863-307-0061)

Remarks: Welcome home to Peach Crossings, a brand-new community in Winter Haven! This stunning three-bedroom, two-bathroom home is designed for modern living, featuring an open-concept layout and stylish finishes. The kitchen is a chef’s dream, offering plenty of counter space for meal prep and entertaining. It comes fully equipped with Whirlpool appliances, including a refrigerator, stove, dishwasher, and microwave—all included at no extra cost! The granite countertops and sleek cabinetry add a touch of elegance and timeless appeal. This home also features high ceilings, enhancing the open and airy feel throughout the living spaces. Step outside to the covered patio, a perfect spot for relaxing, dining, or enjoying the beautiful Florida weather. This home is also packed with energy-efficient upgrades, including double-pane windows, a programmable thermostat, coach lighting, and a Wi-Fi-enabled garage door opener for added convenience. A mudroom located off the garage provides a dedicated space to store shoes, bags, and coats, keeping your home neat and organized. Plus, it’s conveniently placed next to the laundry room for maximum functionality. Nestled in Polk County, Peach Crossings offers a perfect blend of serene lake living with easy access to shopping, dining, and top attractions. Families will love the highly-rated Polk County schools, while the community itself features a playground and a picnic area for residents to enjoy. This home is move-in ready with all upgrades included! Schedule your tour today

Listing is courtesy of: LGI REALTY- FLORIDA, LLC (904-449-3938)

Listing Agent: Gayle Van Wagenen (904-449-3938)

Remarks: Under contract-accepting backup offers. Impeccably maintained home in the sought-after Traditions 55+ community in Winter Haven! This spacious 2-bedroom, 2-bath home with a dedicated office/den offers over 1,500 square feet of open-concept living space, designed for both comfort and functionality. The home features new flooring throughout, upgraded countertops, 36-inch kitchen cabinets, and modern lighting fixtures, creating a bright and inviting kitchen and living area perfect for everyday living or entertaining. Both bathrooms have been tastefully upgraded, and additional improvements include a new water heater and recently replaced AC coil for added efficiency and peace of mind. The home was freshly painted inside and out in 2023, giving it a clean, modern feel throughout. Step outside to enjoy the new screened-in porch, ideal for relaxing mornings or evening gatherings while overlooking the newly installed sod that enhances the home’s curb appeal. The extended driveway provides additional parking and convenience, and the home is handicap accessible, offering added functionality and ease of living. Residents of Traditions enjoy resort-style amenities, including community boat ramp access, fishing, dock, and private water access, along with a community pool and recreational facilities. The HOA includes cable TV, internet, exterior, grounds maintenance, pool maintenance, recreational facilities, and security, making this a truly low-maintenance lifestyle. Located just minutes from shopping, dining, and major roadways, this move-in ready home combines modern updates, accessibility, and the vibrant lifestyle of one of Winter Haven’s most desirable active adult communities.

Listing is courtesy of: CREEGAN GROUP (407-622-1111)

Listing Agent: Chris Creegan (407-622-1111)

Remarks: Welcome to the Summit model in Peach Crossings, a beautiful brand-new home featuring four bedrooms and two bathrooms with an inviting open-concept design. This home boasts high ceilings, enhancing the spacious and airy feel throughout. The master retreat is a true sanctuary, offering a generously sized bedroom that connects to a luxurious en-suite bathroom with a dual sink vanity for added convenience and a step-in shower for a spa-like experience. The kitchen is designed for both function and style, featuring exceptional counter space and brand-new Whirlpool appliances, including a refrigerator, stove, dishwasher, and microwave. A spacious hall closet provides extra storage, keeping everything organized. The family room is the perfect space for cozy movie nights, with ample room for a large sectional and entertainment setup. Whether it’s a movie marathon or a casual night in, this space is designed for relaxation, laughter, and quality time with loved ones. Step outside to the lanai, an ideal spot for enjoying warm Florida evenings with family and friends. The home also features professional front yard landscaping, adding to its curb appeal. Located in the heart of Polk County, Peach Crossings offers the best of lake living with easy access to shopping, dining, and top attractions. Families will love the highly-rated Polk County schools, and the community features a children’s playground and picnic area for added enjoyment. With all upgrades included, this home is move-in ready! Schedule your showing today!

Listing is courtesy of: LGI REALTY- FLORIDA, LLC (904-449-3938)

Listing Agent: Gayle Van Wagenen (904-449-3938)

Remarks: Discover this stunning Ruby home, ready for quick move-in! Included features: a welcoming covered entry; a smartly planned kitchen boasting white 42" cabinets, a center island, a large walk-in pantry, and an open dining area; an immense great room; a secluded primary suite showcasing a generous walk-in closet and a private bath; three secondary bedrooms; a shared hall bath; a central laundry; and a comfortable covered patio. *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: Discover this must-see Tarragon home. Included features: an inviting covered entry; an expansive great room; a quiet study; a well-appointed kitchen offering quartz countertops, stainless-steel appliances, 42" cabinets, a walk-in pantry, a center island and an adjacent dining area; a convenient laundry; an impressive primary suite showcasing a spacious walk-in closet and a private bath; a mudroom and an extended covered patio. This could be your dream home! *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: This Azure floor plan offers a welcoming formal entry and hallway. A spacious great room with kitchen is open to dining and family entertainment area that leads to a covered patio. Also included is a great sized primary bedroom with a primary bath and walk-in closet. Included features: 9"4' ceilings and 8' doors, 42' cabinets and white quartz counter tops in kitchen, ceramic tile throughout the wet and main living areas of the home. All bedrooms, family room, and covered lanai are prewired for ceiling fans. *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: New construction home with 2005 square feet on one-story including 3 bedrooms plus a den, 2 baths, and an open living area. Enjoy an open kitchen with Silestone countertops, Samsung stainless steel appliances, a walk-in pantry, and a spacious island, fully open to the dining café and gathering room. The living area, laundry room, and baths include luxury wood vinyl plank flooring, with stain-resistant carpet in the bedrooms. Your owner's suite is complete with a walk-in wardrobe and a private en-suite bath with dual vanities, a tiled shower, and a closeted toilet. Plus, enjoy a covered lanai, 2-car garage, custom-fit window blinds, architectural shingles, energy-efficient insulation and windows, and a full builder warranty. ***Please note - Virtual Tour showcases the home layout; colors and design options in actual home for sale may differ. Furnishings and décor do not convey!

Listing is courtesy of: CAMBRIDGE REALTY OF CENTRAL FL (863-797-4999)

Listing Agent: George Lindsey, Iii (863-797-4999)

Remarks: Better than new! Completely Remodeled! This 3 bedroom 2 bath home has been completely remodeled, to include a new a/c, new water heater, a beautiful new kitchen, new flooring, new lights & fixtures, and new paint, and the roof was replaced in 2023.

Listing is courtesy of: ALLSTATE REALTY SERVICES (863-965-0207)

Listing Agent: Dwight Head (863-965-0207)

Remarks: This is a very well maintained home which is priced to sell! The property has many upgrades; a new roof in 21, new AC coil in 25, and newer countertops. It is also located close to the side entrance gate for easy access. No rear neighbors provides for a more serene atmosphere and the north facing rear screened porch is pleasantly shady and backyard has room to be expanded. This is truly Central Florida's retirement living at its best. Located in a master planned community with most exterior maintenance included for easy living and full resort-like amenities. The beautifully maintained on-site managed lakefront community clubhouse offers many opportunities for an active lifestyle. This home is move-in ready.

Listing is courtesy of: KLINE REAL ESTATE SERVICES (863-287-0204)

Listing Agent: Scott Kline (863-287-0204)

Remarks: BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. Feel at home with the Magenta, a single-story home with 3 bedrooms, 2 bathrooms, and a 2-car garage. This layout is a true gem, seamlessly blending modern comfort with Florida charm. Open concept living dazzles with luxury vinyl plank flooring throughout the main living areas. The kitchen, featuring quartz countertops, new stainless-steel appliances and ample storage overlooks the dining and living area. A dreamy, covered lanai, accessible through sliding glass doors, invites you to take full advantage of the Florida climate. The owner’s suite boasts double vanities, a walk-in shower and a substantial walk-in closet, while the additional bedrooms and full bathroom are located off the kitchen for added privacy. With a brand-new washer and dryer conveniently located off the foyer, a smart thermostat with voice control to maintain energy efficient living, and professionally curated landscaping, the Magenta is designed to make every day extraordinary. Just off US-27 with quick access to I-17, Villa Mar puts you close to local hotspots, and everything that makes Central Florida shine. Discover Winter Haven’s Chain of Lakes, explore the historic downtown district, or enjoy a fun-filled day with the family at LEGOLAND® Florida Resort. At Villa Mar, you’ll enjoy a fresh approach to relaxed living, with everyday essentials and local favorites right around the corner. 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: Pre-Construction. To be built. Discover the Ventura in VillaMar – A Thoughtfully Designed Smart Home in Winter Haven Located in the beautiful VillaMar community in Winter Haven, the Ventura offers the perfect blend of modern design, comfort, and convenience. Nestled in a prime location, VillaMar provides stunning lake views and resort-style amenities, making it an ideal place to call home. The Ventura is a stunning new home design offering up to 1,562 square feet of beautifully finished living space, all on a single level. As you step onto the inviting covered patio and into the foyer, you’ll find three secondary bedrooms and a full bath conveniently located away from the great room and master suite, ensuring privacy and functionality. Designed with an open-concept layout, the Ventura creates an airy and spacious ambiance, seamlessly blending style and practicality. The stunning kitchen features a large island with quartz countertops, providing ample space for meal preparation and casual dining. Flowing effortlessly into the great room, this space is enhanced by four LED lights and an upgraded window, allowing natural light to fill the home. Cordless blinds throughout provide a sleek, modern touch while enhancing safety and ease of use. Tucked away at the rear of the home, the spacious private master suite serves as a true retreat, complete with a walk-in closet, dual sinks, and a walk-in shower, offering both comfort and convenience. Built for modern convenience, the Ventura comes equipped with cutting-edge smart home features, including a Ring Video Doorbell, Smart Thermostat, and Keyless Entry Smart Door Lock, allowing you to control security and comfort with ease. DEAKO light switches add customizable lighting options, enhancing your living experience. Throughout the main living areas, durable ceramic tile flooring adds a touch of elegance, while plush carpeting in the bedrooms ensures comfort. Outside, a professionally designed landscape and irrigation system keep your yard looking pristine year-round. The home is also built with architectural shingles, ensuring both durability and curb appeal. The two-car garage offers plenty of room for vehicles, with additional space for a workshop or extra storage. Experience the best of Winter Haven living in VillaMar with the Ventura—a home designed for modern lifestyles and unforgettable memories.

Listing is courtesy of: NEW HOME STAR FLORIDA LLC (407-803-4083)

Listing Agent: Charles Pennant (407-305-4317)

Remarks: NEW PRICE REDUCTION! OWNER IS VERY MOTIVATED! Welcome to 6107 Grand Oaks Drive on one of the most beautiful locations in Garden Grove Oaks, an active 55+ community where you own the land! NO LOT RENT HERE! This home has a beautiful extra lot included on the left side of the house for total privacy to the west, as well as there are no homes behind the house. This extra lot is worth at least $21,000 according to the tax appraiser. That makes the house asking price only $168,000!! The yards on both lots are beautifully landscaped. This home has everything a homeowner could want: 2 bedrooms, 2 bathrooms, a side air-conditioned enclosed porch and an air-conditioned workshop. Inside is a great kitchen with beautiful cabinets (3 with decorative glass doors) and countertops with ceramic tiled borders. There is a gas range for the chef in the family! There is also a gas water heater and clothes dryer as well as natural gas heating! Great energy efficiency! There is a nice closet pantry with hookups for the washer and dryer if you prefer them to be inside the house. New double paned windows installed in 2017 throughout the home that have a lifetime guarantee! Roof has a vinyl single ply roof over, installed in 2013. It has a lifetime warranty! Air conditioner was replaced in 2006. Master bedroom has a nice walk-in closet, 13' x 4'. Master bathroom has a walk-in shower and many nice cabinets for all your needs. Guest bath has a large linen closet and a tub/shower combination. Family room is very large and opens through French doors to a Florida room that could be used for an extra sleeping area. All window treatments stay with the home as well as some of the furniture. Garden Grove Oaks is in a great area of Winter Haven, home to two Chain of Lakes for the boaters in your life. The lot to the left (west side) of the home is a part of this property. It can be your personal oasis to use as you like! Buyer is able to sell the extra lot if desired. There is a Pergola with a clay wood-burning Chimenea and two gliders for relaxing outdoors. Electricity is available under the Pergola. A beautiful loquat tree graces the lawn on the extra lot. Much of the yard is shaded. There are many options for this extra property. Let your imagination be your guide! Furniture and items still in house and yard (fountain, etc.) are negotiable for new buyer. Garden Grove Oaks has a great clubhouse where many activities are available to residents. The clubhouse includes a billiards room, cards/game room, a large heated pool and spa, and a screen room with a grill and eating area. There are also shuffleboard courts and a small pond with a fountain. This location is only minutes away from Hwy. 27 and many restaurants, shopping and churches. The home has been well loved and the seller is looking for another great homeowner who will love the home also. Please make your appointment to see this wonderful home today!

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

Listing Agent: Peggy Lewellen (863-412-7692)

Remarks: BRAND NEW ROOF- 2026!!! LOOK AT THIS BEAUTIFUL 4 BEDROOM 2 BATH HOME BOASTING 2,503 SqFt. SITUATED ON AN OVERSIZED LOT WITH A VIEW OF LAKE DAISY!!! Enjoy the OPEN FLOOR PLAN with 2 SEPERATE LIVING AREAS, BONUS ROOM and a LARGE WALK-IN-PANTRY. There is plenty of privacy out back for pets with fencing and a concrete slab perfect for grilling area. Notable updates include: Roof-2026, irrigation system-2021, guest bathroom remodel-2022, air handler--2022, garbage disposal-2022, gutter/leaf guard-2023, refrigerator and dishwasher-2023. There is also NO CARPET in this home!!! The (24 acre) Street Audubon Center is located 1 block from this residence and is home to many species of birds with appx. 3 miles of walking trails abutting the shores of 72 acre Lake Ned! This property is also conveniently located within minutes to LEGOLAND, FL, dining, shopping, medical and schools.

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

Listing Agent: Wanda Dicks (863-287-7846)

Remarks: Welcome to this beautifully maintained 3-bedroom, 2-bath home located in the highly sought-after Cypresswood golf community in Winter Haven. Enjoy resort-style living with an 18-hole golf course, 24-hour gated security, clubhouse, community pool, and more. Inside, the renovated kitchen features granite countertops and custom cabinetry. The spacious primary suite offers a large ensuite bath complete with a double vanity and a generous walk-in closet. Additional updates include a roof replaced in July 2022, windows in May 2023, appliances in November 2016, an updated water heater and A/C, a garage screen added in September 2019, and a motorized awning installed in July 2022. This is an exceptional opportunity to own in one of Winter Haven’s premier neighborhoods. The home does come with appliances and washer and dryer.

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

Listing Agent: Melissa Witter (863-206-8744)