Winter Haven Single Family Homes For Sale - 705 homes

Remarks: Buyer Financing fell through! Their loss is your gain!! Turn key opportunity in the heart of Winter Haven! This 4-bedroom, 2-bath home comes partially furnished, Water filtration system already installed and is ready for its next owner whether you're looking for a primary residence, vacation home, or income producing investment. The home features a spacious, light-filled layout, a functional kitchen, comfortable bedrooms, and a screened in lanai perfect for enjoying Florida evenings. A NEW ROOF installed May 2025 with transferable warranty adds long-term value and peace of mind. Located in a quiet neighborhood just minutes from shopping, dining, lakes, parks, and LEGOLAND, this property offers both lifestyle and convenience in one of Winter Haven’s most desirable areas. With its furnished interior and flexible layout, this home is move-in ready and full of potential for homeowners or investors alike. Schedule your private showing today and see why this property stands out!

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

Listing Agent: Laura Medina Ruiz (863-207-4784)

Remarks: Beautifully updated 4BR/3BA pool home with TWO master suites, NO HOA, and just steps from Chain of Lakes access! This modern, move-in-ready home features luxury vinyl plank flooring, a spacious great room overlooking the private backyard oasis, and a fully remodeled chef’s kitchen with custom soft-close cabinetry, quartz counters, stainless appliances, and a Ruvati workstation sink. The oversized primary suite offers a tray ceiling, walk-in closet, soaking tub, double vanity, and a large tiled shower. A second master/in-law suite creates ideal flexibility for guests or multi-generational living. Enjoy outdoor living on the 33’ screened lanai and the heated 30x15 in-ground pool surrounded by a fully fenced yard and a powered SmithBuilt workshop/shed. Recent updates include: roof (2019), replumbing (2019), AC handler (2019), kitchen remodel (2021), flooring (2021), pool heater (2022), variable-speed pool pump (2024), irrigation (2024), and guest bath remodel (2025). Located less than a 2-minute walk to the Lake Summit boat ramp with full access to the Winter Haven Chain of Lakes—perfect for boating, skiing, and fishing. Close to Legoland, shopping, dining, medical facilities, and convenient to both Tampa and Orlando. Stunning home in a highly desirable SE Winter Haven neighborhood with no HOA and endless possibilities! Seller may offer concessions with acceptable offer!

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

Listing Agent: Christina Loesch (347-977-0962)

Remarks: Welcome to this beautifully maintained 2-bedroom, 2-bathroom, 2-car garage home, lovingly cared for by its original owner. Designed for comfort, simplicity, and low-maintenance living, this residence offers just under 1,200 sq. ft. of well-planned space—ideal for those seeking an easy, relaxed lifestyle. The club house is an amazing place to enjoy the 87 degree pool year round, Boat slips available with private boat launch and pickle and tennis courts available among many more amenities. Inside, you’ll find tile flooring throughout the main living areas for effortless upkeep, along with stone countertops in the kitchen and bathrooms for a clean, modern touch. The spacious primary suite includes a large walk-in closet, providing excellent storage and everyday convenience. The split-bedroom layout offers privacy and flexibility for guests, hobbies, or a home office. One of the standout features is its private setting—you’re not looking directly at a neighboring home, giving you a rare sense of openness and tranquility. Step outside to the beautiful back screened in patio, perfect for soaking up the sun, relaxing with a book, or enjoying quiet evenings outdoors. Located in the highly desired 55+ community of Traditions, you’ll also enjoy exceptional amenities. The impressive community center features a heated pool maintained at a comfortable 87° year-round, with stunning views overlooking Lake Ruby. Residents have access to a private boat launch and boat slips, making lake days easy and enjoyable. Stay active with pickleball courts, a fully equipped workout facility, and a full schedule of social events, activities, and community gatherings happening throughout the year. With its peaceful setting, quality finishes, and resort-style amenities, this home offers the perfect blend of comfort and active living. Don't forget the new Publix being built around the corner for quick and easy grocery shopping.

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

Listing Agent: Keith St. Onge (863-651-1397)

Remarks: Welcome to a move-in ready villa in the desirable 55+ Oakview community of Winter Haven—now strategically repositioned to reflect today’s market and create immediate opportunity. This well-maintained 2-bedroom, 2-bath home offers 1,220 sq ft of comfortable living with a functional open layout, spacious bedrooms with walk-in closets, and a screened lanai designed for relaxed Florida mornings and evenings. Major updates are already done for you, including a NEW ROOF (2024) and HVAC (2019), giving buyers confidence where it matters most. The kitchen has been refreshed with brand-new appliances, making this a truly easy transition with no extra projects needed. A standout feature is the garage screen system, allowing you to enjoy fresh air and added flexibility during the day—an underrated benefit for Florida living. The HOA covers lawn care and exterior maintenance, supporting a low-maintenance, lock-and-leave lifestyle many buyers are actively seeking. Now repositioned to align with current market conditions—creating one of the most compelling opportunities in Oakview today. With recent activity in the community, buyers are moving quickly when the value makes sense—schedule your showing today.

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

Listing Agent: Vanessa Aybar Badillo (352-557-1682)

Remarks: Back on market buyers financing fell through. Welcome home! Your forever home is located near downtown Winter Haven and just a short distance from Polk State College. Completely remodeled in 2021 with a New Roof, New A/C, New Water Heater, New Electrical system, new windows new kitchen (Quartz Countertops), new appliances, new floors (Vinyl). This home has a huge, oversized corner lot and with summer around the corner, this will be the place for all the summer BBQ's.

Listing is courtesy of: FLATFEE.COM (954-965-3990)

Listing Agent: Cliff Glansen

Remarks: One or more photo(s) has been virtually staged. This spacious 4-bedroom, 3-bath home is located in the desirable 55+ gated community of Traditions at Ruby Lake. Upon entering, you’re greeted by a charming screened-in front porch. The open-concept floor plan features both a formal living room and a great room, with low-maintenance solid surface flooring throughout the main living areas. The great room showcases oversized glass sliding doors that seamlessly blend indoor and outdoor living. The gourmet kitchen offers 42" upper cabinetry with brushed nickel hardware and crown molding trim. The center island is accented with granite countertops and pendant lighting, while the upgraded stainless steel appliance package includes a Bosch dishwasher. Additional conveniences such as pull-out shelving, a closet pantry, and recessed lighting ensure a well-equipped culinary space. A delightful breakfast nook with built-ins and large windows provides beautiful views of the patio, perfect for casual dining. The primary bedroom suite is generously sized, featuring vaulted ceilings and a walk-in closet. The primary bathroom offers a comfort-height vanity with double sinks, a linen closet, water closet, and a handicap-accessible walk-in shower with a glass enclosure. Three spacious guest bedrooms and two additional bathrooms accommodate visitors with ease. Bathroom #3 features a premium walk-in tub with body jets and an overhead shower—designed to promote comfort, safety, and independence. Step outside to your private oasis, where outdoor entertaining is effortless on the paved patio or within the screened lanai. Additional features include: Formal dining room, Laundry room with washer, dryer, utility sink, and cabinetry, Welcoming foyer with transom window, Double-pane Low-E windows, Keyless entry smart lock and Ring doorbell, Irrigation system, Paved walkway and driveway, AO Smith hybrid water heater, Owens Corning architectural shingle roof (2023) with extended warranty, Gutters, water softener system, in-wall pest system and Exterior carriage lighting. The 3-car garage includes smart garage door openers, overhead storage racks, a workbench, remote-controlled ceiling fan, refrigerator, additional electrical outlets, and retractable garage door screens. Traditions at Ruby Lake provides an exceptional array of amenities, including a lakefront clubhouse, dock and boat ramp, heated swimming pool and spa, ballroom, billiards, meeting rooms, library, computer room, craft room, dog park, tennis and pickleball courts, basketball, bocce ball, shuffleboard, fitness center, aerobics studio, and more. Conveniently located near shopping, restaurants, LegoLand and major routes, this home offers an exceptional and carefree lifestyle. The monthly HOA fee covers exterior house painting, cable, internet, lawn service, and access to clubhouse amenities—ensuring a truly worry-free living experience. Golf cart included in the sale!

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

Listing Agent: Eileen Belanger (863-221-0229)

Remarks: Under contract-accepting backup offers. Welcome to this charming three-bedroom, two-bathroom home in the peaceful Biltmore Shores neighborhood, conveniently located away from the busy streets of Winter Haven. Featuring durable hardwood floors throughout and practical tile in the kitchen, this home offers a comfortable and functional living space. The large bonus room provides flexibility for use as a dining area or additional living space, tailored to your needs. Set on an oversized, fully fenced lot, the property includes a detached two-car garage with 100 amps of power and water. Enjoy calming views of Lake Jessie directly across the street and easy access to a public boat ramp just a few blocks away. This home is also conveniently close to shopping, restaurants, and entertainment options, enhancing your lifestyle. Structurally sound, it has withstood many hurricanes with minimal damage, and the new roof installed in 2024 adds to its appeal, making it a great choice for those seeking a reliable and inviting place to call home.

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

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

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: 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: MOVE-IN READY! Step inside this stunning one-story Castaway home feel right at home. As you enter through the front door, a welcoming foyer sets the tone for the open and inviting layout. Two spacious bedrooms are tucked at the front of the home and share a beautifully designed full bathroom, perfect for family or guests. A third bedroom with its own private bath offers comfort and privacy, ideal for visitors or a home office setup. Continue down the hallway and the home opens up into a wide, light-filled living area where the kitchen, dining, and family room seamlessly connect. The kitchen features sleek gray cabinets, quartz countertops, and a large island that overlooks the gathering spaces, making it the heart of the home—perfect for cooking, dining, and entertaining all at once. At the back of the home, the private primary suite provides a peaceful retreat with a spacious bathroom featuring double vanities, a walk-in shower, and a generous walk-in closet. Step outside through the sliding doors to a covered lanai, where you can relax and enjoy Florida’s sunshine year-round. Situated on a desirable corner homesite in Willowbrook North, this beautifully designed home offers modern finishes, an open concept layout, and a lifestyle made for comfort and connection.

Listing is courtesy of: DRB GROUP REALTY, LLC (407-270-2747)

Listing Agent: Adam Schott (407-270-2747)

Remarks: Under contract-accepting backup offers. Beautifully maintained 4-bedroom, 2-bathroom home with a 2-car garage, situated on a spacious corner lot of over a quarter acre in desirable Winter Haven. The primary suite features an en suite bathroom with a walk-in shower, while three additional generously sized bedrooms and a second full bath provide comfortable accommodations for family or guests. The inviting kitchen offers ample space with a breakfast bar and adjacent dining area, perfect for everyday living and entertaining. An inside laundry room adds convenience. Enjoy outdoor living in the fully fenced backyard, complete with plenty of room to relax, play, or entertain, and a perfectly sized patio for gatherings. Ideally located close to shopping, dining, entertainment, medical facilities, and the world-famous Plant City Strawberry Festival

Listing is courtesy of: JT REALTY & ASSOCIATES (352-279-2640)

Listing Agent: Lindsey Funderburk (352-606-9639)

Remarks: Under contract-accepting backup offers. Discover Florida living at its finest in this beautifully maintained single-story pool home located in the desirable Hamilton West community of Winter Haven. Situated on an impressive ¼-acre lot with no rear neighbors, this property offers both privacy and space with approximately 2,000 heated square feet designed for comfortable living and effortless entertaining. This 4-bedroom, 2-bathroom home has been meticulously cared for and thoughtfully updated. Major improvements include a new roof installed in 2020 and HVAC replaced in 2017, giving buyers peace of mind. Inside, the home was freshly painted in 2022 and enhanced with numerous tasteful upgrades including taller baseboards, updated lighting, doorknobs, faucets, showerheads, towel bars, and toilet paper holders. Additional updates include a new garbage disposal (2022), new cabinet and mirror in the guest bathroom, a new ceiling fan in one of the bedrooms, and a wine cooler added to the dry bar area—perfect for entertaining guests. Step outside and experience a backyard designed for making memories. The sparkling pool is enclosed with brand-new screening (2023) and complemented by a fully installed outdoor kitchen (2023) that creates the ultimate space for weekend cookouts and gatherings. Paver sidewalks and portions of the backyard were added in 2023, enhancing both style and functionality, while a white privacy fence installed in 2022 neatly conceals the garbage cans and pool equipment. The interior features honeycomb shades and curtains throughout, with room-darkening shades in the bedrooms for added comfort and relaxation. The lush landscaping has been lovingly expanded by the homeowners with additional foliage and fruit-bearing trees including key lime, lime, lemon, and banana, bringing a touch of Florida’s natural beauty right to your backyard. With its spacious lot, private setting, inviting pool area, and extensive updates, this home is ideal for relaxing evenings, lively gatherings, and enjoying the Florida lifestyle year-round. Located near parks and outdoor recreation, it’s a place where family and friends will always want to visit.

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

Listing Agent: Greg Staker (407-589-1600)

Remarks: Take a look at this beautifully upgraded 3-bedroom, 2-bathroom home located in the desirable gated community of Sanctuary by the Lake in Winter Haven. Nestled along the shores of Lake Rochelle part of the renowned Chain of Lakes this property offers the perfect blend of comfort, style, and serene lakeside living. Step inside to an inviting open-concept layout featuring a bright and spacious living and dining area with glass sliding doors that overlook a large, fully fenced backyard. With plenty of room to add a pool, the outdoor space is ideal for relaxation and entertaining. A double-car garage provides ample parking and additional storage. The modern kitchen is designed for both functionality and style, boasting stainless steel appliances, rich wood cabinetry, a spacious pantry, and a large island perfect for casual dining and gatherings. The primary suite serves as a private retreat, complete with an oversized walk-in closet and a luxurious en-suite bathroom featuring a walk-in tiled shower. Two additional bedrooms bring comfort and versatility for family, guests, or a home office. Residents of Sanctuary by the Lake enjoy exclusive access to Lake Rochelle for kayaking and water sports, as well as scenic walking trails, private docks, and a playground. All of this comes with low HOA fees and no CDD. Conveniently located near shopping, dining, medical centers, and major attractions including LEGOLAND®, Walt Disney World®, and Universal Studios® this home offers the best of Central Florida living.

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

Listing Agent: Gaby Murillo (863-668-1914)

Remarks: One or more photo(s) has been virtually staged. Welcome to this beautifully maintained 2018-built single-family home located at 1327 Salisbury Drive in Winter Haven. Offering approximately 2,300 square feet of living space, this spacious residence features 5 bedrooms, 3.5 bathrooms, and a two-car garage. The primary suite is conveniently located on the first floor, providing privacy and comfort, while the upstairs bedrooms are carpeted for a warm, cozy feel. The interior has been freshly painted, creating a bright and move-in-ready atmosphere throughout. Enjoy Florida living year-round from the screened-in back patio, perfect for relaxing or entertaining. It is conveniently located just minutes from downtown Winter Haven and close to the area’s picturesque lakes, shopping, dining, and major roadways. This home combines modern construction, generous space, and an excellent location. Schedule your private showing today!

Listing is courtesy of: TAH FLORIDA LLC (844-874-2661)

Listing Agent: Joshua Nogowski (754-234-9626)

Remarks: Move-in ready single-story home with NO HOA! This 3-bedroom, 2-bathroom gem features low-maintenance tile flooring throughout the entire home—no carpet here! The kitchen is stylishly appointed with stainless steel appliances and crisp painted cabinets. Enjoy outdoor privacy in the fully fenced backyard, perfect for relaxing or entertaining. Complete with a 1-car garage. A fantastic opportunity for easy living!

Listing is courtesy of: ENTERA REALTY LLC (888-216-6364)

Listing Agent: Robert Salmons (888-216-6364)

Remarks: One or more photo(s) has been virtually staged. Welcome to 265 Meadowbrook Blvd, Winter Haven, FL 33881—this well-maintained 3-bedroom, 2-bathroom residence features a comfortable and functional layout designed for everyday living and entertaining. The home features an open-concept floor plan with generous living and dining areas filled with natural light, creating an inviting atmosphere throughout. The kitchen provides ample cabinetry and counter space, along with modern appliances, making it both practical and efficient. The primary bedroom includes a private en-suite bathroom and a walk-in closet, while the additional bedrooms provide versatility for guests, a home office, or other needs. Step outside to a spacious backyard with plenty of room for outdoor activities, gardening, or relaxation. Conveniently located with easy access to major roadways, this property is just minutes from shopping and dining options at Posner Park and Eagle Ridge Mall, as well as outdoor recreation at Lake Shipp Park. Enjoy proximity to popular attractions like LEGOLAND Florida Resort and convenient travel via Orlando International Airport. This property presents a great opportunity to own a move-in ready home in a centrally located area close to everyday conveniences, entertainment, and recreation.

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

Listing Agent: Michael Cruz Irizarry (407-530-7620)

Remarks: Single story POOL HOME ready for new homeowners! This home sits on just over a QUARTER ACRE LOT. Terranova is a GATED COMMUNITY nestled among the Winter Haven Chain of Lakes. Enjoy the HEATED POOL all year in your backyard Oasis. Screened in patio is great for enjoying the beautiful Florida weather. Fully fenced yard with double door gate so you can pull a small boat inside! ROOF 2022. HVAC 2013. Split floor plan features the primary bedroom and bathroom on one side of the home and three additional bedrooms and a full bath on the other. High ceilings. BRAND NEW PUBLIX GROCERY STORE is being built less than five minutes away! Walking trail within the community to Chain of Lakes Elementary School. Call to schedule your private showing today.

Listing is courtesy of: REAL BROKER, LLC (855-450-0442)

Listing Agent: Ken Pozek (407-813-2773)

Remarks: *** No CDD fees!!***Welcome to this stunning smart home offering the perfect blend of modern design, space, and functionality. This impressive two-story residence features 5 bedrooms, 3 full bathrooms, and a spacious 3-car garage, making it ideal for growing families or those who love to entertain. Step inside to discover a bright and open floor plan designed for today’s lifestyle. The main living areas flow seamlessly, creating the perfect space for gatherings, while large windows bring in abundant natural light. The modern kitchen serves as the heart of the home, featuring sleek finishes, ample cabinetry, and generous counter space for cooking and entertaining. With five generously sized bedrooms, there’s room for everyone—including a flexible space for guests, a home office, or multi-generational living. The primary suite offers a private retreat with a well-appointed en-suite bathroom and plenty of closet space. This home is equipped with smart home technology, providing convenience, efficiency, and peace of mind at your fingertips.Step outside and enjoy your own private outdoor retreat situated on a generous 0.24-acre lot, offering plenty of space for relaxation, play, or future customization. The covered back patio and screened enclosure create the perfect setting for year-round outdoor living—ideal for morning coffee, evening gatherings, or simply enjoying Florida’s beautiful weather without the bugs. Built in 2023, this home offers the advantages of newer construction without the wait, combining modern features with move-in ready convenience. Home is just minutes from Legoland and the sea life aquarium! Don’t miss the opportunity to own this beautifully designed home—schedule your private showing today!

Listing is courtesy of: JASON MITCHELL REAL ESTATE FLO (754-307-0607)

Listing Agent: David Hartigan (407-955-1156)

Remarks: HUGE $15,000 PRICE DROP! Welcome to this completely renovated 4-bedroom, 3-bath POOL home in the highly desirable Idylridge community of Winter Haven. No expense has been spared in transforming this home into a modern, move-in ready masterpiece with high-end upgrades inside and out. Additional highlights include a brand-new roof with new soffit and fascia, two new AC units, new electrical including a 60-amp outdoor generator plug, a three-car carport, and a driveway that fits up to NINE vehicles. Inside, you’ll find a bright, open layout with all-new paint, luxury vinyl plank flooring, and luxury tile in the bathrooms. Each room features modern ceiling fans, and crown molding throughout, creating both comfort and style throughout the home. The stunning kitchen is a chef’s dream, featuring brand-new stainless steel appliances, granite countertops, a large new island, soft-close cabinet drawers, and a new walk-in pantry. A chef’s natural gas stove lets you cook while enjoying views of the pool and backyard, making this space perfect for entertaining or everyday living. The home offers TWO master suites, one with a large walk-in closet, plus two additional bedrooms and three fully updated bathrooms with contemporary fixtures and backlit mirrors for a sleek, contemporary feel. Step outside to your private backyard oasis with a refreshed pool featuring a brand-new liner, new screen enclosure, and new tile surrounding the deck. The large, fully fenced yard includes partially new fencing and three separate entrances with double gates, ideal for vehicles, boats, or recreational equipment. A 17 x 16 block shed on a slab with a brand-new metal roof provides extra storage or workshop space. Conveniently located in Winter Haven, the home is minutes from shopping, dining, parks, and the Chain of Lakes, as well as attractions like LEGOLAND Florida Resort. This fully renovated, move-in ready pool home offers space, style, and unmatched upgrades—inside and out. Don’t miss your opportunity to own a truly exceptional property in one of Winter Haven’s most sought-after neighborhoods.

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

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

Remarks: 2118 Chris Dr is a property that boasts a kitchen equipped with all stainless steel appliances, adding a modern touch to the culinary space. The kitchen island serves as a functional centerpiece, perfect for meal preparation or casual dining. The primary bedroom is a haven of comfort, complete with a walk-in closet that provides ample storage for your wardrobe. With these attributes, this property ensures a comfortable and convenient lifestyle. 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)