Winter Haven Homes For Sale & Real Estate - 1034 homes

Remarks: Welcome to Cypresswood Golf & Country Club, a gated and guard-gated community offering resort-style living in a beautiful golf course setting. This well-maintained 3-bedroom, 2-bathroom home is ideally situated at the end of a quiet cul-de-sac, providing one of the most desirable locations on the street. Inside, you'll find a spacious open-concept floor plan designed for comfortable living and entertaining. The large kitchen features stainless steel appliances, abundant cabinetry, and a center island that serves as the heart of the home. The living and dining areas flow seamlessly to the expansive fully screened lanai, creating the perfect indoor-outdoor living space. The private primary suite offers direct access to the lanai, a massive walk-in closet, and an oversized walk-in shower complete with a built-in bench. Two additional bedrooms and a second full bath provide plenty of room for family and guests. Residents of Cypresswood Golf & Country Club enjoy access to exceptional community amenities, including a clubhouse, community pool, tennis courts, and beautifully maintained grounds. Don't miss this opportunity to enjoy Florida living at its finest in one of the area's most sought-after communities.

Listing is courtesy of: GOLD HEART REALTY LLC (863-224-2419)

Listing Agent: Lori Roberts (863-224-2419)

Remarks: Virtually Staged. Don't miss this charming 1-story home featuring 3 bedrooms, 1 bathroom, and a 1-car carport. The functional floor plan offers comfortable living spaces with plenty of natural light and room for everyday living. The kitchen provides ample cabinet and counter space, while the bedrooms offer flexibility for family, guests, or a home office. Enjoy the spacious yard with plenty of room for outdoor activities, gardening, or entertaining. Conveniently designed for easy living, this property presents a great opportunity to make it your own. One or more photo(s) has been virtually staged, AI generated, or rendered.

Listing is courtesy of: MAINSTAY BROKERAGE LLC (800-583-2914)

Listing Agent: Raquel Littlejohn (470-279-6333)

Remarks: Come see 2953 Whispering Trails Dr, a residence showcasing recent fresh interior paint and fresh exterior paint for a clean, cohesive appearance. The kitchen is equipped with all stainless steel appliances, and the primary bathroom provides practical double sinks. Outside, a welcoming patio leads to a fully fenced in backyard. This move-in ready property blends comfort and recent updates seamlessly. Included 100-Day Home Warranty with buyer activation

Listing is courtesy of: OPENDOOR BROKERAGE LLC (480-462-5392)

Listing Agent: Karen Albright (480-462-5392)

Remarks: Come see 1100 Carefree Cove Dr, recently improved with a new roof, fresh exterior paint, and fresh interior paint, presenting a comprehensively refreshed presentation. Partial flooring replacement further updates the interior living spaces, while a fenced in backyard provides practical outdoor areas. This property embodies a fresh approach to comfortable living. Included 100-Day Home Warranty with buyer activation

Listing is courtesy of: OPENDOOR BROKERAGE LLC (480-462-5392)

Listing Agent: Karen Albright (480-462-5392)

Remarks: Under contract-accepting backup offers. Winter Haven home near Chain of Lakes featuring 5 bedrooms, 3 bathrooms, and 2 flexible bonus rooms offering exceptional convenience and a lifestyle close to everything Central Florida buyers love. This move in ready property provides effortless access to major commuter routes, grocery stores, shopping, dining, scenic walking trails, LEGOLAND Florida Resort, and Florida’s beautiful beaches just about 90 minutes away. Step into your own private outdoor sanctuary designed for both relaxation and entertainment. The caged saltwater pool includes a 6×10 sun shelf perfect for in water lounging along with a 3 to 6 foot depth range ideal for both play and leisurely floating. Enjoy the luxury of a heated spa with priority Jacuzzi jet action creating the perfect setting for evening unwinding, stress relief, muscle relaxation, or hosting friends for cozy nights under the stars. The spacious gazebo offers a shaded retreat for outdoor dining, socializing, or simply enjoying the Florida breeze. Practical upgrades elevate this property as it is equipped to support a home generator, has a warrantied water softener for supreme taste, two 5-ft gates that create a wide 10-ft entry to the backyard and a on-site shed adding valuable extra storage keeping everything tidy and easy to access. Inside, the home feels bright, modern, and truly move in ready. The open concept layout creates an inviting flow throughout, and the generous kitchen is perfectly suited for gatherings, meal prep, and everyday connection. With its flexible floor plan, this home easily accommodates large families, multi generational living, or hosting guests with comfort and privacy. A standout property offering both lifestyle and practicality. This home is a must see!

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

Listing Agent: Andrea Friedmann (863-661-6535)

Remarks: Located in a desirable gated community on a oversized corner lot, paved driveway and low HOA fee and convenient access to everything Central Florida has to offer. This spacious and well-maintained home offers flexibility, comfort, and thoughtful upgrades throughout. Step inside to discover a bright and airy floor plan featuring a spacious living room with soaring vaulted ceilings and an open-concept design perfect for both everyday living and entertaining. The kitchen overlooks the main living area, creating a seamless flow, and features solid wood cabinetry, ample counter space, and plenty of storage. The versatile office can easily be converted into a fourth bedroom, providing additional space for family, guests, or a home office. The spacious primary suite is a true retreat, complete with elegant tray ceilings and a luxurious en-suite bathroom featuring dual vanities, a relaxing garden tub, walk-in shower, and a large walk-in closet. Additional highlights include a roof replaced in 2022, two AC units for enhanced comfort and efficiency, a large rear lanai perfect for outdoor relaxation, and a storage shed offering extra space for tools and equipment. Ideally situated in Winter Haven, you'll enjoy easy access to excellent shopping, dining, and entertainment options. Popular destinations include the vibrant downtown Winter Haven district, numerous waterfront restaurants along the Chain of Lakes, and shopping at nearby centers featuring national retailers and local boutiques. Outdoor enthusiasts will appreciate the area's beautiful lakes, parks, boating opportunities, and recreational amenities. Families and visitors alike will enjoy being just a short drive from LEGOLAND Florida Resort, one of Central Florida's premier attractions. Whether you're looking for a growing family home, extra space for remote work, or simply a peaceful gated community lifestyle, this exceptional property offers the perfect combination of location, value, and functionality. Schedule your private showing today!

Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (863-701-2350)

Listing Agent: Andrew Fearn (863-812-1755)

Remarks: HUGE $45,000 PRICE DROP! Welcome to one of the largest homes in the desirable Harmony Lake Eloise community! This spacious 5-bedroom, 3-bathroom residence offers a versatile and thoughtfully designed layout perfect for modern living. A generously sized flex room—currently used as a dining area—can easily be converted into a 6th bedroom, home office, or bonus space to suit your needs. The spacious kitchen is a true centerpiece, featuring quartz countertops, beautiful cabinetry, recessed lighting, stainless steel appliances, a large kitchen island, and a walk-in pantry. The interior paint throughout the home offers a soft, inviting color palette that’s easy on the eyes. The first floor showcases beautiful tile flooring throughout, along with a large bedroom and full bathroom—ideal for guests or multigenerational living. You’ll also find an additional sitting area or playroom, providing even more functional living space. Upstairs, all bedrooms are upgraded with luxury vinyl flooring, offering both style and durability. The conveniently located upstairs laundry room adds everyday ease. The expansive primary suite boasts his-and-her closets, dual vanities, and a walk-in shower —your own private retreat. With tons of storage throughout and one of the largest floor plans in the community, this home combines space, comfort, and flexibility. Enjoy a low monthly HOA fee and access to a beautiful community pool. Ideally located just minutes from Lake Eloise, Legoland Florida Resort, shopping, dining, schools, and major roadways, with easy access to Orlando, Tampa, and Walt Disney World. This is a must-see property in Winter Haven!

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

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

Remarks: Discover this must-see Tourmaline home. Included features: an inviting covered entry; an expansive great room; a well-appointed kitchen offering 42" cabinets, quartz countertops, a roomy pantry, a center island and an adjacent dining area; a beautiful primary suite showcasing an immense walk-in closet and a private bath; a convenient laundry; an airy loft; a storage area and a covered patio. This home also offers ceiling fan prewiring in select rooms.

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

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

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: Virtually Staged. Short Sale. Welcome home to Villa Mar, a vibrant and growing community in beautiful Winter Haven! Built in 2023 and occupied for just one year, this 5-bedroom, 3-bathroom home offers that “like-new” feel with thoughtful upgrades throughout. As you step inside, you’re greeted by an inviting open-concept layout designed for both comfort and connection. The kitchen shines with stainless steel appliances, an oversized pantry, and cabinets with updated fixtures, all opening to the main living area with NEW laminate flooring—creating a seamless space for gathering and entertaining. A bedroom and full bathroom on the main floor offer ideal flexibility for guests or multi-generational living. Upstairs, you’ll find four additional bedrooms, a loft that’s perfect for a home office or a cozy nook to unwind and recharge, and a conveniently located laundry room. The oversized primary suite features a large walk-in closet and an ensuite bathroom complete with a stand-alone shower, upgraded shower head, and linen closet for added convenience. Step outside to a fully fenced backyard, offering privacy and plenty of space to create your own outdoor retreat—whether that means adding a future pool, garden, or simply enjoying a quiet evening of relaxation. The oversized under-the-stairs storage and two-car garage add even more practicality, while the LOW HOA helps keep ownership easy and affordable. Perfectly situated just off US-27, residents enjoy proximity to dining, shopping, and grocery options, as well as easy access to I-17. Outdoor enthusiasts will love being near the Winter Haven Chain of Lakes, ideal for boating, kayaking, fishing, or simply soaking up the sunshine. Plus, the charming Downtown Winter Haven Historic District is nearby—home to local restaurants, boutiques, and community events like First Fridays, the Wine, Chocolate & Cheese Festival, and so many more! For a weekend of fun with the family and friends, LEGOLAND is only 3.5 miles away! This home beautifully blends modern comfort, functional space, and a convenient location—making it a must-see in the heart of Winter Haven. This is the one you've been waiting on. Schedule a showing today and make it yours!

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

Listing Agent: Brianna Perez Montalvo (407-687-3837)

Remarks: Virtually Staged. Welcome Home!!! 4577 Back Nine Dr. Winter Haven, Fl. features 3 bedrooms and 2 full baths and is located in Lake Ashton, an Exclusive Florida Retirement 55+ community. This home has BRAND NEW EXTERIOR PAINT! The widened, paver driveway offers extra room for parking and the screened entry at the front door is an added bonus. The glass leaded front door with large eye brow window above leads you into a home that is warm, inviting and spacious. The open-concept kitchen showcases granite countertops, stainless steel appliances, Maple cabinets and a Pantry Cabinet with convenient pull-out shelving. You can seamlessly blend indoor and outdoor living by sliding open the living room and dinette area sliding glass doors to the screened, covered lanai with 8" aluminum border base. It's the perfect place for entertaining. The primary bedroom with En-Suite bath has been extended 4 ft. to provide additional living space. It's the perfect getaway and you'll enjoy the EXTRA SPACE in the primary suite. The primary bathroom has ample closet space with His/Her Walk In Closets with Organization System, a large walk in shower with double shower heads, a separate water closet and separate His and Her Vanities. Her vanity has an additional make up area. Guests will appreciate the separate bedrooms and bath behind a pocket door. Additional features include: an automatic screen on the garage door, a separate irrigation meter, 18" diagonal tile in home (Bed 2 and Bed 3 are excluded), crown moulding, New A/C modulator, cabinetry in laundry room, Plantation Shutters in the Bedrooms, Upgraded entry light fixture, surround sound in the living room, additional insulation in the attic, new interior paint in Bedroom 1 and Guest Bathroom, new interior paint in the formal dining and dinette areas. Lake Ashton, a Florida Retirement community, has a Clubhouse with large grand ballroom, Outdoor Community Heated Pool, Tennis Courts, Bocce Ball, Shuffleboard, Fitness Center, Movie Theater, Bowling Lanes, Restaurant (Charm City)and More! The Health and Fitness center has indoor basketball, indoor racquetball, indoor heated pool, pickle ball and tennis courts, media center, card, craft and billiard rooms. There are two golf courses located in Lake Ashton. Memberships are optional and not a requirement to reside in Lake Ashton. Residents enjoy the resort style amenities and activities offered in Lake Ashton, a premier Florida Retirement Community. Don't miss this opportunity to own your piece of paradise. Check out the photo gallery and make your appointment to tour this home.

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

Listing Agent: Lori Raath (863-409-6899)

Remarks: Great investor or first time home buyer opportunity. This house has new windows, a new roof, updated electric panel and an renovated bathroom. The LVP throughout the home with 5-1/4 baseboard. This property has a huge back yard for your family to enjoy. Built in laundry with washer and dryer included. This property is move in ready and won't last long at this price. Schedule your showing today

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

Listing Agent: Stephen Hubbell (863-559-5666)

Remarks: Under Construction. Under construction. This new construction build sits on almost an acre (.72) and is a comfortable and cozy home with 3 bedrooms, 2 bathrooms and 1,467 square feet of living space. The foyer opens to the spacious dining and great rooms, with raised ceilings throughout the home, and there's convenient access to the outdoor patio from the living space. The kitchen features a large island. The primary bathroom boasts a separate shower and tub, and this home comes equipped with ample storage space including two oversized primary walk-in closets, a pantry in the kitchen, a linen closet and a coat closet. The spacious (413 sq ft) 2-car garage provides additional storage and laundry space. This home is located in a quiet neighborhood off Winter Lake Rd, close to all of the amenities Lakeland or Winter Haven have to offer! With no HOA, there's room for your boat, RV, or other outdoor vehicles. USDA FINANCING AVAILABLE FOR ELIGIBLE BUYERS, WITH NO MONEY DOWN. CALL TODAY FOR MORE DETAILS.

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

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

Remarks: Under Construction. This charming 4-bedroom, 2-bathroom new construction build features an open floor plan and 1,778 square feet of living space, all while sitting on a .73 acre lot. The spacious great room, with high vaulted ceilings is perfect for family movie nights in, with convenient access to the back patio. The large open kitchen caters to family living as well as entertaining with its lengthy seated bar for that delicious morning breakfast, and is located perfectly in between the great room and dining area. The ample primary bedroom is enhanced by its dual-sink vanity bathroom and walk-in closet featuring a linen closet within. Additionally, the spacious garage provides additional storage and leads directly into the home’s designated laundry space. This home is located in a quiet neighborhood off Winter Lake Rd, close to all of the amenities Lakeland or Winter Haven have to offer! With no HOA, there's room for your boat, RV, or other outdoor vehicles. USDA FINANCING AVAILABLE FOR ELIGIBLE BUYERS, WITH NO MONEY DOWN. CALL TODAY FOR MORE DETAILS.

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

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

Remarks: Privacy, space, and freedom — this gated 2.38-acre Winter Haven estate has it all, with no HOA to tell you what to do with it. Tucked well back from the road behind a remote-operated gate, this 4-bedroom, 2-bath home offers 2,125 sq ft of comfortable living surrounded by mature oaks and wide open sky. The split-bedroom floor plan features formal living and dining rooms, a family room that flows into the kitchen, hardwood floors, and a breakfast bar perfect for morning coffee. The owner's suite is a true retreat with French doors to the screened back porch, a spa-style bath with soaking tub and separate shower, and a generous walk-in closet. Outside, a 42-ft covered front porch and 34-ft screened back porch frame the fully fenced acreage — room for your RV, boat, ATVs, a future pool, a garden, and more. New roof (2023), updated AC, well pump, and New water heater 2026, septic pumped this year. Minutes from the Polk Parkway with easy access to Lakeland, Tampa, and Orlando. Back on the market and ready for its new owners.

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

Listing Agent: Kimberly Davis (850-625-8855)

Remarks: Under contract-accepting backup offers. NO LOT RENT. Welcome to your slice of Florida living in Winter Haven! This well-maintained 2-bedroom, 2-bath home offers 1,620 sq ft of comfortable living space and is packed with valuable upgrades, including the ROOF 2023 and 4 ton A/C 2023, Water Heater 2024 or 2025, water softener, reverse osmosis system, and rain gutters with leaf guards for added peace of mind. Step inside to find a spacious floor plan. Relax and unwind in the large screened-in lanai, ideal for enjoying Florida’s beautiful weather year-round. The property also features a large storage shed with air conditioning, giving you plenty of room for tools, hobbies, or seasonal items and an inside laundry with washer and dryer included. Located in the desirable Village Park community for those 55+ years young, residents enjoy an incredibly low HOA fee of just $55 a month, which includes access to a sparkling pool and community amenities. Best of all—you own the land! Limited trailer/RV storage is also available on a first-come basis. Perfectly situated between Tampa and Orlando, this home offers convenient access to world-renowned attractions like LEGOLAND Florida Resort, Walt Disney World, Universal Studios Florida, Busch Gardens Tampa Bay, ZooTampa at Lowry Park, and Seminole Hard Rock Hotel & Casino Tampa. You’re also just minutes from shopping, dining, grocery stores, hospitals, golf courses, nature parks, and Florida’s beautiful beaches. With both Tampa and Orlando international airports within about an hour’s drive, travel is incredibly convenient. Whether you're looking for a full-time residence or a seasonal retreat, this home checks all the boxes. Don’t miss your opportunity to live in Village Park—schedule your private showing today!

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

Listing Agent: Carolyn Christian, Llc (863-514-6378)

Remarks: Newly Remodeled Mobile home!!! Move-In Ready! Its own lot- no lot rent!! Affordable 4-Bedroom 2-Bath Home on Owned Land! This 1994 manufactured home. Enjoy a spacious, open floor plan featuring a large living room and kitchen, perfect for gatherings or everyday living. All measurements and sizes approximate and not guaranteed, any information contained here-in critical to buyers purchasing decisions, must be verified by the buyers.

Listing is courtesy of: NONA LEGACY POWERED BY LA ROSA (407-270-6841)

Listing Agent: Eric Galban (863-430-8222)

Remarks: Welcome to 255 Haines Boulevard, Winter Haven, Florida! This beautifully maintained home offers the perfect blend of comfort, convenience, and Florida living. Featuring a spacious floor plan with plenty of natural light, this property is ideal for families, first-time homebuyers, or investors alike. The kitchen provides ample cabinet and counter space and flows seamlessly into the living and dining areas, making it perfect for entertaining guests. Step outside and enjoy the generous yard with room for outdoor activities, gardening, or future enhancements. Conveniently located near shopping, dining, schools, medical facilities, and major roadways, this home provides easy access to everything in Winter Haven. Whether you're looking for a primary residence, seasonal home, or investment property, this move-in-ready opportunity is one you won't want to miss. Schedule your private showing today!

Listing is courtesy of: LAND SOUTH REALTY, LLC (863-937-8867)

Listing Agent: Sean Denney (863-602-0424)

Remarks: Spacious 2-bedroom, 2-bath upper corner condo in the Barcelona Building of Orchid Springs, an all-ages community. This desirable end unit offers natural light and views from three sides, plus added privacy with minimal foot traffic. Recent updates include luxury vinyl plank flooring throughout, smooth ceilings, and neutral zero-VOC paint. Routine annual A/C maintenance completed in May 2026. The updated kitchen features 17 cabinets, 10 drawers, and a pantry, while the spacious primary suite offers a walk-in closet and en-suite bath. Assigned parking is located just below the unit. The monthly HOA fee of $312.69 covers exterior maintenance, grounds care, water, sewer, trash, gas service, pest control, common laundry facilities, and capital reserves. Conveniently located near LEGOLAND Florida and between Orlando and Tampa, with easy access to Winter Haven's renowned Chain of Lakes.

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

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

Remarks: Discover affordable luxury and modern Florida living in this beautifully designed brand-new 2025 home located in the growing Peach Crossings community of Winter Haven. Perfectly positioned for first-time homebuyers, growing families, remote professionals, and buyers seeking more space without sacrificing style, this move-in ready 4-bedroom, 2-bath residence offers the ideal combination of comfort, functionality, and value in one of Polk County’s rapidly expanding areas. Built by LGI Homes, the highly sought-after “Summit” floor plan features an open-concept design with soaring ceilings, abundant natural light, and thoughtfully designed living spaces perfect for entertaining and everyday living. The spacious chef-inspired kitchen is equipped with granite countertops, solid wood cabinetry, Whirlpool stainless steel appliances, generous prep space, and seamless flow into the dining and family room area creating the perfect setting for gatherings, holidays, and movie nights at home. The oversized primary suite offers a peaceful retreat with a large walk-in closet and spa-style en-suite bathroom featuring dual vanities, stone countertops, and a step-in shower. Three additional bedrooms provide flexibility for guest rooms, a home office, fitness room, or playroom. Luxury vinyl flooring throughout the main living areas, energy-efficient windows, smart layout design, interior laundry room, and modern finishes add both style and practicality for today’s buyers. Step outside and enjoy covered outdoor living space ideal for relaxing evenings, weekend cookouts, or enjoying Florida’s year-round sunshine. Professionally designed landscaping, irrigation, sidewalks, and attractive curb appeal make this home stand out from the moment you arrive. Located near shopping, dining, medical facilities, parks, and major commuter routes, Peach Crossings offers convenient access to Lakeland, Orlando, and Central Florida attractions while still maintaining a quieter residential atmosphere. Community amenities include playgrounds, parks, picnic areas, and access to highly desired Polk County schools, making this neighborhood especially appealing to families and buyers relocating to Florida. With no CDD fees, low HOA costs, builder warranty coverage, and financing options including FHA, VA, USDA, and Conventional loans, this property presents an exceptional opportunity for buyers looking for affordable new construction in Winter Haven with long-term value and lifestyle appeal.

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

Listing Agent: Renee Anthony (407-603-5935)