Homes for Sale Near Winter Haven Senior in Winter Haven - 139 homes

Remarks: This move-in-ready 3-bedroom, 2-bathroom home is located in the desirable Planters Walk neighborhood. The interior features a functional open-concept layout where the kitchen overlooks the main living areas, creating an inviting flow for daily living and entertaining. The updated kitchen is equipped with sleek granite countertops and stainless steel appliances. The primary suite serves as a private retreat, complete with a dedicated primary bathroom and a large walk-in closet. Practical features include an attached 2-car garage, a separate laundry room, and a combination of carpet and tile flooring throughout.

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

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

Remarks: Under contract-accepting backup offers. This Beautiful 4-bedroom,3-bath home with additional office offers the perfect blend of style and comfort. Featuring hardwood floors and tile throughout the main living areas, cozy carpeted bedrooms, and an open floor plan with high ceilings that fill the home with natural light. The kitchen boasts elegant granite countertops, while the renovated master bathroom showcase a huge glass shower, double vanity sinks and solid surface countertops. Step outside to your backyard oasis with a gorgeous Pool and Jacuzzi, complete with stone Pebble Tec finish - perfect for relaxing or entertaining. Outside also includes a well for lawn watering & landscape lighting. Enjoy the added bonus of a community pool and clubhouse. Conveniently located near downtown Winter Haven with easy access to Tampa and Orlando, this home truly has it all. Call today for your private showing!!!

Listing is courtesy of: AGILE GROUP REALTY (813-569-6294)

Listing Agent: Cindy Thornton (863-287-8223)

Remarks: Beautiful 3BR/2BA home in desirable College Grove, just off Lake Elbert with its new walking trail. Prime location (with NO HOA) close to downtown Winter Haven, shopping, hospitals, and Polk State College Open floor plan with separate living, dining, and family room featuring cathedral ceilings and a gas fireplace. Updated kitchen with island, breakfast bar, granite countertops, stainless appliances, recessed lighting, and closet pantry. Split bedroom plan for added privacy. Spacious primary suite with walk-in closet, dual sinks, and tub/shower combo. French doors from primary bedroom, living, and family rooms lead to screened lanai with spa and waterfall—perfect for relaxing or entertaining. New Roof 2021. NEW AC 2020. Additional features include luxury vinyl flooring throughout, walk-in closets in all bedrooms, tankless water heater, and irrigation system. Situated on a .30-acre fenced lot with plenty of room for outdoor activities. Schedule your showing today!

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

Listing Agent: Amy Reynolds (863-412-2279)

Remarks: Short Sale. Welcome to your new home in this peaceful and well-maintained community! This spacious 2-bedroom, 2-bathroom condo offers comfortable, low-maintenance living with all the amenities you need to relax and enjoy life. Step inside to find a bright and open floor plan with generous living space, a well-equipped kitchen, and private bedrooms on opposite sides for added privacy. The primary suite includes a full en-suite bathroom and ample closet space, while the second bedroom is perfect for guests, a home office, or family. Enjoy your morning coffee on the screened in back patio or take a short stroll to the community clubhouse, where you’ll find a sparkling swimming pool, social spaces, and exclusive access to a private fishing area—perfect for outdoor enthusiasts. Nestled in a quiet neighborhood with beautifully landscaped grounds, this condo is ideal for those seeking comfort, convenience, and a touch of nature. Whether you're downsizing, investing, or buying your first home, this property offers a unique blend of tranquility and community living. Don’t miss this opportunity—schedule your private showing today!

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

Listing Agent: Casandra Vann (863-546-5446)

Remarks: Spacious 2,336 SF pool home in the gated, tranquil Overlook Estates. This 4BR/2BA floorplan features a split-bedroom layout and generous living space including an eat-in kitchen, 17x18 vaulted family room, 10x16 dining room with bay window, and a large foyer. The master suite includes a dressing alcove and walk-in closet; an adjacent bedroom makes an ideal office or nursery. High-traffic areas feature tile flooring; sliding glass doors in three rooms recess into the wall and open to a 31x50 pool deck — perfect for indoor/outdoor living. Additional highlights: 95x130 lot, terraced front walkway, 7x8 laundry with cabinetry and utility sink, 22x23 garage with built-in storage. Ready for your finishing touches!

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

Listing Agent: Amy Reynolds (863-412-2279)

Remarks: Beautiful two-story single-family home built in 2023. Featuring a modern and functional design, this home offers 5 bedrooms and 3 full bathrooms, spread across 2,284 square feet of living space. The ground floor includes a spacious living room, a kitchen equipped with modern appliances (refrigerator, washer, dryer, dishwasher, and more), and a bedroom with a full bathroom, ideal for guests or as an office. The second level features the remaining bedrooms, including the master suite, which is equipped with a walk-in closet. Interior finishes feature ceramic and carpet flooring, thermal windows with blinds, and a central electric HVAC system. The property includes an attached two-car garage and sits on a 5,500-square-foot lot. Located in the Canton Park community, with low HOA fee and not CDD. This home represents an excellent opportunity for those seeking comfort and style in a prime location close to Tampa, Orlando and Lakeland. More pictures coming soon.

Listing is courtesy of: LA ROSA REALTY ORLANDO LLC (407-288-8201)

Listing Agent: Brigida Lopez (321-945-3989)

Remarks: Welcome to Garden Grove Oaks – a friendly, active 55+ community in beautiful Winter Haven and you OWN THE LAND! This well-maintained 2-bedroom, 2-bathroom manufactured home with a bonus office/den and Florida room offers the perfect blend of comfort, functionality, and easy Florida living. Step inside and you’ll immediately appreciate the bright, open layout, featuring a spacious living area ideal for relaxing or entertaining. The kitchen provides ample storage and prep space, while the adjoining dining area creates a natural flow for everyday living. Outside, you’ll enjoy a low-maintenance yard, covered parking, and plenty of room for outdoor seating. Garden Grove Oaks residents love the clubhouse, community pool & hot tub, social activities, and peaceful setting, all while being close to shopping, dining, medical facilities, and the best of Winter Haven. Whether you’re seeking a seasonal retreat or a year-round home, this charming property is move-in ready and waiting for you!

Listing is courtesy of: DREAM REALTY GROUP (863-450-7973)

Listing Agent: Nicole Castro (863-547-5647)

Remarks: Welcome home to this charming 3-bedroom, 2-bath residence nestled on a spacious lot in the heart of Winter Haven. Offering nearly 1,300 square feet of comfortable living space, this well-maintained home features a functional layout with a kitchen and family room combination, ceiling fans throughout, and plenty of natural light. Step outside to your private backyard oasis complete with an in-ground pool—perfect for relaxing, entertaining, or enjoying Florida’s sunshine year-round. A one-car garage adds convenience, while the absence of HOA fees provides flexibility and freedom. Ideally located near schools, shopping, dining, and major roadways, this home is a wonderful opportunity for homeowners or investors alike. NEW ROOF 2020, NEW AC 2022. Don’t miss your chance to make this inviting Winter Haven property your own!

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

Listing Agent: Melissa Mottern (863-860-1808)

Remarks: ALMOST BRAND NEW!! Check out this CHARMING 3 bedroom, 2 bath manufactured home perfectly situated within a fully fenced-in yard! Step inside to find an Open Floor Plan featuring a cozy living room that flows seamlessly into the dining area and kitchen, creating a warm and inviting space. Split Bedroom Plan with the primary bedroom located just off the kitchen, boasting its own bathroom and a walk-in closet! The separate laundry area provides added convenience - even the washer and dryer are included! Enjoy the front covered porch with side screens while having your morning coffee or just to relax after a long day! Additionally, includes a shed, which is great for your storage needs. Don’t miss your chance to see this delightful home — call today to schedule your appointment!

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

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

Remarks: PRIME LOCATION!! Prime Investment Opportunity with Commercial Zoning! Located in the Historic Pughsville neighborhood of Winter Haven. This property offers incredible versatility. Currently a cozy 2-bedroom, 1-bath residential wood framed home, the lot is zoned commercial, opening the door for various business uses. The property features a spacious, fenced-in yard with the added benefit of No HOA and No CDD fees. Ideally situated near Legoland, hospitals, shopping centers, hotels, and Walmart. Don't miss this unique opportunity—make an offer today!

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

Listing Agent: Twanna Dewdney (863-207-1634)

Remarks: Motivated Sellers! Welcome home to this immaculate 4 bedroom / 2 bathroom / 2 car garage home in Winter Haven! Shows like a model! GREAT OPEN FLOORPLAN with lots of living space, this home was BUILT IN 2024 and has plenty of features throughout. The home has tiled flooring throughout the main living areas and a huge great room, perfect for entertaining! The kitchen features a spacious center island, granite countertops, stainless steel appliances, tiled backsplash, and plenty of cabinetry space. There are 4 spacious bedrooms. The owner's suite boasts an en suite bathroom with dual sinks. The backyard is generously sized and is FULLY FENCED! Other features back here include a screened patio and a shed. Lots of upgrades!

Listing is courtesy of: RIGHT TRACK REALTY (953-437-4747)

Listing Agent: Phyllis Haigler (804-641-9763)

Remarks: Completely remodeled and move-in ready, this stunning 2-bedroom, 2.5-bathroom condo in Casa Del Sol Village offers modern updates and a comfortable layout in the heart of Winter Haven. Every corner has been renovated, featuring new flooring, paint, lighting, kitchen appliances, doors, and beautifully updated bathrooms. The spacious living room and downstairs guest half-bath make entertaining a breeze, while both upstairs bedrooms boast private en-suite bathrooms for added convenience. Enjoy a low-maintenance lifestyle with an attached one-car garage, access to the community pool, and a location close to shops and restaurants—all amidst the beautiful landscapes and lakes that surround this lovely community.

Listing is courtesy of: WF REALTY CORP. (407-994-2900)

Listing Agent: Adriana Sanchez (321-947-4014)

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: MOVE-IN READY! Beautiful 2 Level, Coastal elevation, 2 Car Garage Home with Open Concept Living and 3 Bedrooms! The inviting front porch opens to a gracious foyer that leads you to the open main living space. The family room is open to the dining area and adjacent kitchen. The primary suite boasts an ensuite bathroom with dual sink vanity, shower, private water closet, and large walk-in closet. The second level offers a spacious loft and 2 secondary bedrooms each with walk-in closets and a full bathroom.

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

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

Remarks: Owner motivated and ready to negotiate — WOW! This BEAUTIFUL 1361SF 2BR/2BA FIRST-FLOOR condo in Orchid Springs offers stunning lagoon/pond views! Located in the 55+ Granada Building, where at least one occupant must be 55+. IMMEDIATELY AVAILABLE and MOVE-IN READY! Step into an open, airy floor plan with tile throughout, creating a bright and spacious feel. The dining area, living room, and bonus room flow seamlessly together, all overlooking the tranquil lagoon. As an end unit, the living room and bedrooms enjoy extra windows with peaceful courtyard views. The primary bedroom features a walk-in closet plus an additional hallway closet, providing excellent storage. Both bathrooms are well-appointed, with one offering a custom vanity and a tub/shower combo. Additional highlights include assigned parking directly in front of the unit. Perfect for year-round living or a seasonal retreat in a serene, well-maintained community.

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

Listing Agent: Sharon Gastelbondo (863-800-4655)

Remarks: Owner motivated and ready to negotiate — WOW! This BEAUTIFUL 931 SF 1BR/1BA FIRST-FLOOR condo in Orchid Springs offers stunning lagoon views! Located in the 55+ Granada Building, where at least one occupant must be 55+. IMMEDIATELY AVAILABLE and MOVE-IN READY! Step into an open, airy floor plan with tile throughout, creating a bright and spacious feel. The dining area, living room, and bonus room flow seamlessly together, all overlooking the tranquil lagoon. As an end unit, the living room and bedroom enjoy extra windows with peaceful courtyard views. The bedroom features a walk-in closet plus an additional hallway closet, providing excellent storage. The bathroom includes a custom vanity and a tub/shower combo. A washer and dryer are included, offering added convenience. Additional highlights include assigned parking directly in front of the unit. Perfect for year-round living or a seasonal retreat in a serene, well-maintained community.

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

Listing Agent: Sharon Gastelbondo (863-800-4655)

Remarks: The seller is OFFERING UP TO $14,000 toward a NEW ROOF or may apply this contribution toward the BUYER'S CLOSING COSTS, providing added flexibility and value. This spacious 4-bedroom, 3-bath ranch-style home offers an impressive amount of living space (2,178 sqft) filled with natural light and designed for comfort and flexibility. The many windows throughout the home create a bright, welcoming atmosphere, while multiple living areas provide room to spread out and enjoy. The remodeled kitchen features a refrigerator, dishwasher, and range, along with a convenient breakfast bar and adjacent dining area—perfect for everyday living and entertaining. A formal living room greets you at the front entry, and the oversized family room offers exceptional gathering space, complete with a built-in desk and direct access to the screened lanai. The generous primary suite includes a walk-in closet, garden tub, separate shower, and an additional wall A/C unit for added comfort. A desirable mini–master suite with its own private bath provides ideal space for guests, extended family, or a private home office. Built-in cabinetry throughout the home adds both character and abundant storage. Situated on a large corner lot, the expansive yard offers endless possibilities for outdoor living, recreation, or future enhancements. The chain-link fenced backyard provides security and functionality while maintaining an open feel. With no HOA restrictions, you’ll enjoy the freedom to personalize the property to suit your needs. Combining space, natural light, a sizable yard, and the advantage of no HOA, this property delivers comfort, flexibility, and room to grow.

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

Listing Agent: Michelle Heath (863-528-3123)

Remarks: Under contract-accepting backup offers. Enclosed Saltwater Pool | Corner Lot | 4 Bedrooms in Winter Haven Welcome to 310 17th St NE in Winter Haven, FL — a charming 4-bedroom, 2.5-bath pool home set on a spacious 0.28-acre corner lot in an established neighborhood. This home offers a blend of character, space, and opportunity for the next owner. Inside, you'll find nearly 1,800 sq ft of living space with a functional layout that includes four bedrooms, 2 full bathrooms and a convenient half bath, offering flexibility for guests, home office space, or everyday living. The kitchen and bathrooms retain their original style, giving buyers the chance to update and personalize over time. Step outside and enjoy the enclosed saltwater pool (installed in 2018), creating a private outdoor space for relaxing or gathering with friends. The fenced backyard and large corner lot provide room to spread out and enjoy outdoor living. Major systems have already been updated, including AC (2020) and water heater (2018). The home also offers 2,267 total square feet under roof, adding additional usable space. Conveniently located near shopping, dining, schools, and major roadways, this property combines the charm of an established Winter Haven neighborhood with everyday convenience.

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

Listing Agent: Jenelle Grabowicz (863-604-0834)

Remarks: Fresh new price — NOW OFFERING A HOME WARRANTY! Your opportunity to own in Cypresswood just got better! Welcome to The Tennis Villas! Nestled in the highly desired Cypresswood Golf & Country Club, this gated community with 24/7 security offers the perfect blend of comfort, convenience, and resort-style living.At the entry, a classic wrought iron gate opens to a private front patio, creating a welcoming first impression and a charming space to enjoy.This 2-bedroom, 2-bath villa features expansive living and dining areas with laminate flooring, a bright kitchen with updates and ceramic tile flooring. An open-concept layout that includes a wet bar with cabinet storage—perfect for entertaining. A bonus Florida room with air conditioning overlooks an open field and pond, providing a peaceful view right from your home.The primary bedroom boasts a sliding glass door leading to the enclosed lanai, filling the space with natural light and offering relaxing backyard views. Recent updates include a NEW metal roof for peace of mind. Plus, the HOA covers exterior paint, roof maintenance, lawn care, and pest control, making this home truly move-in-ready.The Cypresswood community offers incredible amenities:An 18-hole championship golf course designed by Ron Garl, Junior Olympic-sized pool, Lighted tennis courts, Fitness center & clubhouse with pro-shop, On-site restaurant and event space.Whether walking, biking, or taking the golf cart, all amenities are conveniently close by. You’ll also love the location—just minutes from Highway 27, I-4, Legoland Florida Resort, the Polk Parkway, and plenty of shopping and dining options.Don’t miss your chance to enjoy the Florida country club lifestyle in this affordable, stylish villa. Schedule your private showing today!

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

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

Remarks: Clean, clean, clean. Welcome to 356 Sterling Drive — a meticulously maintained 3-bedroom, 2-bath pool home that truly shows like a model. Pride of ownership is evident from the moment you arrive, where outstanding curb appeal showcases fresh exterior paint, hurricane-rated double-pane windows and sliding doors, lush landscaping, and a welcoming front lawn. This move-in ready residence offers extensive recent updates, including a brand-new roof with Heritage Proline Titan XT shingles (2025), refinished pool, new stainless steel appliances (2023), water heater (2023), new double-hung hurricane rate double pane windows (2024), updated bathroom vanities, new interior and exterior paint (2023), upgraded door hardware and electrical faceplates (2023), and more. Inside, an open and airy layout features tile flooring throughout, elevated ceilings, and an inviting great room designed for both relaxed living and entertaining while capturing tranquil views of the screened pool. The eat-in kitchen provides generous workspace, ample cabinetry, newer stainless appliances, and a charming bay-window dinette ideal for everyday dining. A desirable split bedroom plan ensures privacy. The spacious primary suite offers generous closet space and a well-appointed en-suite bath with dual sinks, updated finishes, and a tiled walk-in shower. Secondary bedrooms are nicely sized and provide convenient access to the full guest bath. Outdoor living is where this home truly shines. The screened pool and fully fenced backyard create the perfect setting for enjoying Florida’s year-round lifestyle, offering privacy, space for pets or play, and fruit trees that add beauty and a touch of nature. A two-car garage provides additional storage and everyday convenience. Located in the established Berryhill community of southeast Winter Haven, the home offers convenient access to shopping, dining, schools, medical facilities, and everyday essentials. Winter Haven’s central location between Tampa and Orlando makes commuting and travel easy while still enjoying the relaxed lifestyle the area is known for — including the Chain of Lakes, boating, recreation, and a vibrant community atmosphere. A beautifully updated home, thoughtfully cared for, and ready for its next chapter.

Listing is courtesy of: THE STONES REAL ESTATE FIRM (863-412-2080)

Listing Agent: Michael Stone (863-412-9733)