Homes For Sale in Winter Haven 33884 - 419 homes

Remarks: One or more photo(s) has been virtually staged. SEE THIS QUICKLY! This 3BR/2BA mfg home located in SE Winter Haven is in a NO HOA neighborhood with lake access, has a NEW ROOF in 2023, NEW HVAC 2024, and it has been REPIPED. This is an open floor plan with large bedrooms that all have walk in closets, vaulted ceilings, an inside laundry with included LG front load washer and dryer, a spacious kitchen, separate dining room and a huge great room! Accessibility improvements have been made with the remodeled master bathroom including a large shower, along with a comfort height toilet and grab bars which are in both bathrooms. Outside there is an access ramp, a carport for covered parking, two utility buildings and a fenced backyard. There is a good sized porch with plenty of room for a grill and to enjoy relaxing. Located on a cul-de-sac there is no thru traffic. SE Winter Haven is close to LEGOLAND, Highway 27, shopping, dining, medical, schools and more.

Listing is courtesy of: QUINN & COMPANY REALTORS, LLC (863-412-2287)

Listing Agent: Susan Rohlfing (863-557-7059)

Remarks: Welcome to 1033 Sawgrass Dr, where modern comfort meets thoughtful upgrades in this beautifully maintained 3-bedroom, 2-bath home. Designed with everyday living in mind, this home features an open-concept layout filled with natural light, creating a bright and inviting space perfect for both relaxing and entertaining. The kitchen offers quality finishes and a clean, contemporary feel, seamlessly connecting to the main living area. Elegant crown molding adds a refined touch, while plantation shutters provide both style and function throughout the home. The primary suite offers a spacious retreat, complete with a large walk-in closet for ample storage. Outside, the widened driveway adds extra convenience and functionality—an upgrade you’ll appreciate daily. Located in the highly sought-after Lake Ashton community, residents enjoy access to an impressive array of amenities designed for an active and social lifestyle. From two 18-hole golf courses to expansive clubhouses, fitness centers, indoor and outdoor pools, and courts for tennis, pickleball, bocce, and more, there’s always something to do. Additional features include a bowling alley, movie theater, arts and crafts spaces, pet areas, and a full calendar of community events. Positioned in Central Florida with convenient access to both Tampa and Orlando, this property offers the perfect balance of comfort, convenience, and lifestyle.

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

Listing Agent: Veronica Bard (863-670-7526)

Remarks: This spacious 2-bedroom condo features 2 full baths and sits nestled in the back upper corner of the Barcelona building of Orchid Springs! It is NOT a 55+ community, so families and young folks are welcome! This gorgeous condo could be your very own Florida home or investment property. Enjoy stunning views from three sides, with plenty of natural light and air flow only available on end units. Recent upgrades including non-popcorn ceilings, an acoustic ceiling in the kitchen, neutral vinyl plank flooring throughout, and neutral monochromatic ZERO VOC paint. No mismatched floorings or walls, no plastic kitchen ceilings, no carpeting, no outdated popcorn ceilings, and no bedrooms carved out of living room space commonly found in condos. There is an updated full-sized kitchen, not just a galley, that boasts 17 cabinets, 10 drawers & a pantry. It has a spacious great room/dining area, and large primary bedroom easily can handle a king size bed with a full en suite bath & a spacious walk-in closet with hardwood shelves and rods, ready for customization for your personal wardrobe needs! The second bedroom is ample and ready to use for your family member, roommate, or a home office . The stairway is just outside the door, with assigned parking below. And importantly, there is almost zero foot traffic from delivery people or other residents passing in front of this unit since it is the only one on the back side of the stairs in its own little corner! This additional privacy is rare and priceless! You will enjoy walking the ample, lush grounds of Orchid Springs while not having to do outdoor chores in the Florida heat. One small monthly HOA/Management fee (unchanged from 2025) of $312.69 is one of the lowest in this area, and makes this an affordable housing opportunity. The fee covers the building exterior, grounds maintenance, parking lot, laundry & mailroom, common gas water heaters, tree care, water, sewer, trash disposal, gas for heating/cooking if desired, exterior pest control, capital accounts, etc. Of special note is that the electricity SMART meter bank is located in a different building on the first floor, not in this unit, so there is lesser than normal radiation found on a tri-field meter. Also, 5 HOA commercial hot water heaters are in a lower floor common room to serve all of Barcelona, so one less appliance for the homeowner to buy and maintain! Same with the common area HOA laundry facility- no personal washers or dryers to buy or maintain. This unit is around the corner from Legoland, conveniently situated between Orlando & Tampa. Southeast Winter Haven is surrounded by its famous Chain-O-Lakes known for boating, fishing and waterski shows available for you to enjoy! IMPORTANT NOTE: the Barcelona Building and this condominium unit are NOT subject to the statutory engineering inspections and repairs that many high rise condos 3+ stories tall are, thus eliminating the potential associated astronomical, unanticipated assessments that may occur as a result.

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

Listing Agent: Karel Cain (863-287-0196)

Remarks: Welcome to this beautifully maintained two-bedroom, two-bathroom townhome with a versatile flex space, perfectly situated in one of Winter Haven's most desirable communities. As you step inside, you’ll be greeted by soaring 16-foot ceilings, an open floor plan filled with natural light, and tasteful finishes that create an inviting atmosphere. Just off the entry, a spacious guest bedroom with an attached full bath offers comfort and privacy, while the primary suite is tucked away at the back of the home, complete with serene views and an oversized 12’ x 5’ walk-in closet. A set of double pocket doors leads to the flexible bonus room, ideal as a third bedroom, home office, den, or even a formal dining room to fit your lifestyle. The kitchen and living areas flow seamlessly together, making entertaining easy and everyday living a joy. Step outside to enjoy the well-kept community, where a sparkling pool overlooks the lake, and a private fishing pier adds to the charm of the neighborhood. The HOA takes care of exterior building and roof maintenance, landscaping, cable, and internet, allowing for truly low-maintenance living. With recent updates including exterior paint in 2025, new appliances in 2021, plus the roof, HVAC, water heater, and bedroom flooring replaced in 2018, this home offers peace of mind and modern comfort. Conveniently located near world-class attractions, shopping, and dining, this townhome is the perfect blend of comfort, convenience, and lifestyle. Don’t miss the opportunity to make this exceptional property your new home in Central Florida.

Listing is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)

Listing Agent: Nancy Lezotte (407-907-7671)

Remarks: Under contract-accepting backup offers. Looking to move to Florida. Don't miss out on this very well maintained home. Step into the nice sized lanai on the side of the home. Follow into the open living room/dining room/kitchen area. The home features 2 bedrooms and one bath. The living area flooring has been replaced recently. The AC is less than two years old and the roof was replaced in 2014 and repaired after Hurricane Milton in 2024. Doves Rest, a 55+ community offers many amenities and activities. The gate add extra security during the evening hours.

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

Listing Agent: Kathy Devor (573-450-1679)

Remarks: Welcome to 2813 Wingfoot Court — now one of the best values in Cypresswood Golf & Country Club! Perfectly positioned along the 8th fairway inside this guard-gated golf community, this beautifully maintained 2-bedroom, 2-bath villa offers peaceful views and effortless Florida living—now at an exceptional new price. Being sold fully furnished and truly turnkey, this home is ready for immediate enjoyment—just bring your suitcase. Inside, you’ll find a professionally designed interior with vaulted ceilings that create a bright, open feel throughout the main living spaces. The kitchen includes updated appliances, including a newer stove and microwave, while most windows have been upgraded for improved efficiency and style. A tankless hot water heater adds modern convenience and energy savings. The spacious primary suite features a walk-in closet and private bath, while the guest bedroom also offers a walk-in closet and easy access to a second full bath—perfect for hosting family and friends. One of the home’s standout features is the inviting Florida room, ideal for morning coffee or relaxing after a day on the course. Step outside to the stained and stamped patio overlooking the fairway, creating a perfect space for entertaining or unwinding. Major updates include a roof (2019) and A/C (2018), providing added peace of mind. Residents enjoy access to community amenities including a pool, tennis courts, clubhouse, and on-site restaurant—all just minutes from shopping, dining, and major roadways. Now aggressively priced—don’t miss this opportunity to own in Cypresswood at one of the most attractive price points in the community.

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

Listing Agent: Corinna Weaver (863-258-2901)

Remarks: IMPRESSIVE HOME IN GREAT LOCATION! Move-In-Ready— This home has a wonderful design of open concept living, formal dining room, split bedroom plan and screen lanai overlooking a wooded area giving a peaceful setting without rear neighbors. A welcoming foyer leads to the formal dining room and a step down into the lovely living room featuring a cathedral ceiling, fireplace, built-in entertainment center and sliding glass doors that give view and access to the relaxing lanai highlighting an inground spa. The living room links to the dinette with lanai access and a breakfast bar joining the kitchen. This appealing kitchen has elegant cabinetry accented with upper cabinets of frosted glass doors, pantry storage, decorative tile backsplash, dark stone counters and stainless appliances including a gas range. The home’s design has a contemporary flair that is prominent within the owners’ en suite. Privately situated, this spacious bedroom not only has a walk-in closet and French doors to the lanai, but its unique design delivers an elaborate, elevated and open bathroom featuring a sunken marble bathtub, tile & glass surroundings, lengthy dual sink vanity, shower stall and water closet. The opposite side of the home houses a full bathroom and two lovely bedrooms, one with French doors accessing the lanai. The home is outfitted with an abundance of good-looking ceiling fans and attractive floor coverings including the brick decking on the lanai with the in-ground hot tub! Additional elements that make this a fabulous home include the brand New Roof, New Water Heater, New A/C, large driveway for extra parking, peaceful backyard and lovely gated community. This is a great location offering convenience to all shopping, dining, entertainment, schools and medical around Winter Haven. Call to arrange your appointment today, don’t miss out on this opportunity!

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

Listing Agent: Amanda Plowden (863-224-7088)

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

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

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

Remarks: SIGNIFICANT PRICE IMPROVEMENT | LOWERED 26,000.00 BEAUTIFUL GATED GOLF COURSE COMMUNITY An exceptional opportunity to own a beautiful 3brm/2.5 bath home nestled on the 4th hole of the highly sought-after Lake Bess Country Club and Golf Course in Winter Haven. As you step inside, you are welcomed by a charming foyer featuring 10-ft ceilings that create an open and airy ambiance throughout the home. The living room, enhanced by a cozy gas fireplace, provides a perfect setting for those cool winter evenings in Florida. This space effortlessly connects to a spacious breakfast nook, both of which open onto a large lanai that offers tranquil views of the golf course, framed by majestic oak trees draped in moss-ideal for an evening glass of wine. Through French doors off the living room, you will find a stunning study\office equipped with built -in wood shelving with additional storage, perfect for work or leisure. The layout thoughtfully includes two generous sized bedrooms and a full bath on this side of the home. At the heart of the house, the well-appointed kitchen is a dream for any cook. It boasts ample space, views of the golf course, and a breakfast nook for casual dining. A bar area allows friends and family to gather and socialize while meals are being prepared. For more formal occasions, the designated dining room offers an elegant setting. The primary suite is an impressive retreat, featuring a tray ceiling, his and hers walk-in closets, and a spacious bathroom equipped with a large shower and vanity. A private water closet and a hidden washer and dryer behind closet doors add to the convenience of this remarkable space. The home also includes an oversized 2-car garage, perfect for tools and a work table. As part of this vibrant community, you'll enjoy access to the clubhouse, community pool and golf course. This hidden gem offers easy access to Legoland, Highway 27, and I-4, making it a prime location for both relaxation and adventure. The purchase price also includes 1 of 49 shares to the golf club which includes 2 free memberships and unlimited Golfing, enhancing the value of this exceptional property. I invite you to discover this property and envision the lifestyle that awaits you at Lake Bess Country Club. Please let me know if you would like to schedule a viewing or if you have any questions.

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

Listing Agent: Christina Ashley (941-780-0291)

Remarks: One or more photo(s) has been virtually staged. Under Construction. This two-story Georgia will definitely be on your mind… This beauty highlights a modern open layout, seamlessly integrating a first-floor kitchen with a central island, a dining room and a welcoming family room with patio access. On the same level is a private owner's suite with an attached bathroom. Situated upstairs is a versatile loft for additional shared living space and four secondary bedrooms to provide restful retreats to family members and guests alike. Villa Mar is a masterplan community of new single-family homes. Near Historic downtown Winter Haven. There are lots of shops, restaurants, bike paths, and easy access to nearby highways. Close to Legoland and Bok Tower Gardens. The much anticipated “Villar Mar” community is what you have been looking for. A safe small town feel with convenience.

Listing is courtesy of: LENNAR REALTY (800-229-0611)

Listing Agent: Ben Goldstein (407-310-7677)

Remarks: Welcome to your slice of true Florida lake life—where every day feels like a getaway. This 3-bedroom, 2-bath home is tucked inside a waterfront community designed for living, not just residing. Start your mornings with a quick launch from the private boat ramp, spend your afternoons cruising Lake Dexter, or enjoy a friendly match on the tennis courts. There’s even private boat parking, so your next day on the water is always effortless. When it’s time to unwind, head to the community pool or relax at the clubhouse overlooking the water—perfect for catching those signature Florida sunsets. Located just minutes from LEGOLAND Florida Resort, plus a wide variety of local restaurants and shopping, you’re right in the heart of everything—so close to LEGOLAND that you can sometimes enjoy their fireworks lighting up the night sky. This isn’t just a home—it’s the kind of place where memories are made and the pace of life finally feels just right.

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

Listing Agent: Kevin Tison (863-206-5755)

Remarks: The property you are viewing is comprised of four individual parcels all being sold together. Also see MLS B4901531. This property has two parcels with single family homes on it , two vacant parcels, and easement parcel. The two single family homes are both concrete block built, 2 bedrooms and 1 bath room The entire sale parcel is almost 1 acre. These parcels are zoned RL 3 but have the potential to have a future land use zoning change. The corner lot sits across from a commercial store. Located on the corner of Eagle Lake Loop and Rifle Range road this area is rapidly growing with both residential and commercial opportunities. Property location has great opportunities for potential land use change based on surrounding parcels.

Listing is courtesy of: CRAIG BURKE REAL ESTATE GROUP, LLC (863-899-5010)

Listing Agent: Craig Burke (863-899-5010)

Remarks: Under contract-accepting backup offers. Sellers say sell sell sell!! Welcome to 115 Lake Mariam Way in Winter Haven, FL, located in the highly desirable Lake Mariam Hills community. This updated 4-bedroom, 2-bath single-family home offers a functional layout ideal for comfortable everyday living, entertaining, or remote work. Homeowners have paid attention to detail! Residents enjoy private community boat ramp access to Lake Mariam, making this an excellent lake-access home in Winter Haven for boating, fishing, and enjoying the Florida lifestyle. Homes for sale in Lake Mariam Hills are rarely available, adding to the strong demand for this neighborhood. Known for its quiet streets, pride of ownership, and established setting, Lake Mariam Hills is one of Winter Haven’s most sought-after residential communities. Whether you are searching for a primary residence, lake-access property, or a solid Florida real estate investment, this home offers exceptional value. Offered at $364900.00 Schedule your private showing today—opportunities in this neighborhood do not last.

Listing is courtesy of: FAITH AND FAMILY REALTY LLC (863-712-1991)

Listing Agent: Lynn Arthur (336-596-5547)

Remarks: Welcome to this stunning 4-bedroom, 2-bathroom home located in the desirable community of Winter Haven. Situated on a quiet street in a well-maintained neighborhood, this modern residence offers a perfect blend of comfort, style, and functionality. The open-concept floor plan features a spacious living area with high ceilings, abundant natural light, and elegant finishes throughout. The gourmet kitchen boasts granite countertops, stainless steel appliances, a large island with breakfast bar seating, and ample cabinet space—ideal for both everyday living and entertaining. The primary suite includes a walk-in closet and a luxurious en-suite bathroom with dual vanities and a glass-enclosed shower. Three additional bedrooms provide plenty of space for family, guests, or a home office. The split-bedroom layout ensures privacy and convenience. Step outside to a covered lanai overlooking a beautifully landscaped backyard—perfect for relaxing or hosting gatherings. The property also includes a two-car garage, a laundry room, and energy-efficient features.

Listing is courtesy of: RE/MAX REALTY UNLIMITED (813-684-0016)

Listing Agent: Trevor Skeens (813-531-3713)

Remarks: Under contract-accepting backup offers. Short Sale. CLOSE IN 60 DAYS OR LESS! QUICK and easy HECM Short Sale on this well loved, one owner 2 bedroom 2 bath home. The charming kitchen has a breakfast nook with bay window, breakfast bar, generous countertops, and cabinet space. The bright, and open great room as well as both bedrooms have recently updated Luxury Vinyl Plank floors for easy care. You'll be snug, and secure during storm season with electric hurricane shutters, and a 2020 Generac generator. The roof was replaced in 2024, and a new hot water tank installed in 2024.This home is conveniently located within 10 minutes of restaurants, banks, shopping and Legoland. Vienna Square offers a low maintenance lifestyle, in a welcoming setting. The reasonable monthly fee includes all community amenities, lawn mowing, and a Spectrum Internet/Cable/TV package. Residents enjoy access to the community pool, fitness center, billiards, movie theater, tennis and pickleball courts, and an active social calendar. Step inside, fall in love. Make it yours!

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

Listing Agent: Marti Sutton (863-206-0563)

Remarks: One or more photo(s) has been virtually staged. Under Construction. The first floor of the stunning Edison two-story home is host to an open-concept layout that combines the kitchen with the living and dining areas, and an outdoor patio is easily reached off the main living space. Upstairs, five bedrooms surround a versatile loft, including the luxe owner’s suite, complete with a generous walk-in closet and en-suite bathroom. Villa Mar is a masterplan community of new single-family homes. Near Historic downtown Winter Haven. There are lots of shops, restaurants, bike paths, and easy access to nearby highways. Close to Legoland and Bok Tower Gardens. The much anticipated “Villar Mar” community is what you have been looking for. A safe small town feel with convenience.

Listing is courtesy of: LENNAR REALTY (800-229-0611)

Listing Agent: Ben Goldstein (407-310-7677)

Remarks: One or more photo(s) has been virtually staged. Under Construction. This expansive two-story Columbus has a well-designed layout, featuring a first floor dedicated to shared living and entertaining. The open concept design seamlessly connects the kitchen, dining room and family room, with a patio extending the interior space outdoors. Upstairs, a spacious loft separates the three secondary bedrooms from the serene owner's suite. Completing the home is a convenient two-car garage. Villa Mar is a masterplan community of new single-family homes. Near Historic downtown Winter Haven. There are lots of shops, restaurants, bike paths, and easy access to nearby highways. Close to Legoland and Bok Tower Gardens. The much anticipated “Villar Mar” community is what you have been looking for. A safe small town feel with convenience.

Listing is courtesy of: LENNAR REALTY (800-229-0611)

Listing Agent: Ben Goldstein (407-310-7677)

Remarks: One or more photo(s) has been virtually staged. This expansive two-story Columbus has a well-designed layout, featuring a first floor dedicated to shared living and entertaining. The open concept design seamlessly connects the kitchen, dining room and family room, with a patio extending the interior space outdoors. Upstairs, a spacious loft separates the three secondary bedrooms from the serene owner's suite. Completing the home is a convenient two-car garage. Villa Mar is a masterplan community of new single-family homes. Near Historic downtown Winter Haven. There are lots of shops, restaurants, bike paths, and easy access to nearby highways. Close to Legoland and Bok Tower Gardens. The much anticipated “Villar Mar” community is what you have been looking for. A safe small town feel with convenience.

Listing is courtesy of: LENNAR REALTY (800-229-0611)

Listing Agent: Ben Goldstein (407-310-7677)

Remarks: Welcome to this beautifully renovated home in Greenfield Village at Cypresswood Golf & Country Club, perfectly situated on a spacious .37-acre lot on the 13th green. This charming 2-bedroom, 2-bathroom residence features a bright and open layout with a large living area plus an additional family room accented by a cozy brick fireplace and floor-to-ceiling wood built-ins. The brand-new kitchen has been thoughtfully updated with stainless steel appliances, quartz countertops, and all new cabinetry, along with a convenient passthrough window to the large glass-enclosed sunroom with A/C, making entertaining effortless while enjoying the view. The interior also features crown molding, new luxury vinyl plank flooring throughout the living areas, and new carpet in the bedrooms. Both bathrooms have been fully updated and include dual sink his-and-her vanities. Additional highlights include a new roof, a formal dining space, a side-entry two-car garage, fresh front landscaping, and a welcoming covered front porch, all combining to create a move-in-ready home in a desirable golf community setting. Cypresswood Golf & Country Club is a gated community with a 24 hour guard that hosts social and recreational events and features an 18-hole championship golf course designed by award-winning designer Ron Garl. In addition to golf, the facilities include a pro shop, wellness center, lounge, dining rooms, swimming pool, tennis courts, and trails. They also offer excellent practice facilities, including a putting green, chipping green and driving range. Golf carts are allowed throughout the community.

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

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

Remarks: This open concept 3-bedroom, 2-bath home is located in the Garden Grove part of Winter Haven. This home features a large living room/kitchen combo, with an updated kitchen with stainless steel appliances, granite countertops, wood cabinets, and a large bar perfect for family dining. The large bonus room has possibilities for many different rooms. The home has luxury vinyl plank throughout, updated bathrooms, double pane windows, and french doors for some of the interior features. Exterior features include A/C in 2024, drain field/septic in 2023, updated electrical panel. Outside also features a deck perfect for bbqing, large, fenced back yard, oversized driveway, and extra space for parking your toys. Oh yeah, and NO HOA! Call today to view! *Agents, please read MLS realtor remarks.*

Listing is courtesy of: BROKERS REALTY OF CENTRAL FLOR (863-294-6773)

Listing Agent: Renee Butler (863-294-6773)