Homes for Sale Near Winter Haven Senior in Winter Haven - 155 homes

Remarks: Income-producing duplex in Winter Haven with both units in place and performing. Each side offers 2 bedrooms, 2 bathrooms, and approximately 1,175 square feet with layouts that are easy to maintain and consistently appealing to long-term tenants. Positioned on a cul-de-sac, the setting is more private while still keeping quick access to everyday conveniences, shopping, dining, and major roadways. Both units are leased at $1,195 per month, with lease terms secured through early 2027—creating immediate income with no vacancy concerns. Do not disturb tenants.

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

Listing Agent: Kristin Kellin (863-409-5649)

Remarks: Seller motivated. Welcome to your home in Winter Haven—just minutes from Legoland, shopping, medical facilities, and Highway 27 for easy commuting! Originally a 3-bedroom, 2-bath layout, this home has been converted into a spacious 5-bedroom, 2-bath residence, offering incredible versatility for growing families, multigenerational living, or those needing extra space for a home office or hobby rooms. It will need some TLC due to tenant being in property. With five true bedrooms, everyone in the family can have their own retreat while still enjoying generous shared living spaces. Outside, you’ll find a property ideally situated for convenience—whether you’re heading to Legoland for weekend fun, accessing everyday amenities just minutes away, or commuting via Highway 27. This home offers the perfect blend of location, and space in one of Winter Haven’s most desirable areas.

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

Listing Agent: Brandy Duncan (863-585-6849)

Remarks: ***PRICE REDUCTION*** Refined luxury meets modern efficiency in this stunning 4-bedroom, 3-bath home located in the private gated community of Hampton Cove, tucked away on a peaceful cul-de-sac, accented by elegant brick exterior detailing. Designed for both sophistication and comfort, this meticulously upgraded home offers timeless finishes, flexible living spaces, and exceptional energy efficiency. Inside, luxury vinyl plank flooring flows throughout, complemented by granite countertops in every space. The chef-inspired kitchen is beautifully appointed with stainless steel appliances, rich granite surfaces, a designer backsplash, deep drawer storage, and soft-close cabinetry, a breakfast bar, and a sunlit dinette-creating a space that is as functional as it is striking. A dedicated dining room provides the perfect setting for hosting and formal gatherings. The primary suite serves as a serene retreat, featuring a private sitting area and a spa-style en-suite bath with a soaking tub and walk-in shower. Bedrooms two, three, and four are generously sized, offering comfort and flexibility for family, guests, or additional work-from-home needs. Both guest bathrooms are thoughtfully designed with walk-in showers, offering elevated comfort for family and guests alike. A versatile flex room allows effortless customization—ideal for a private office, fitness studio, or creative space. Outdoors, the expansive fenced backyard provides abundant room for a resort-style pool, with a strategically located bathroom perfectly suited for future pool access. This home is enhanced with top-tier systems and energy-conscious upgrades, including: • Lennox 19.5 SEER high-efficiency A/C (2018) with damper system and four thermostats • Fully paid solar panels • 16kW whole-home Generac generator powered by natural gas • Hybrid water heater (2018) • Roof, A/C, and water heater replaced in 2018 • Energy Recovery Ventilator (ERV) in the garage for improved air quality and humidity balance • Double-pane windows throughout • Backyard fencing added in 2023 • Washer and dryer (2025) included. This exceptional home delivers luxury, resilience, and efficiency in one elegant package—an opportunity rarely found.

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

Listing Agent: Jessica Willaford (863-662-8549)

Remarks: INVESTORS! Take a look at this 1914 Crafstman Bungalow style home! This opportunity is located in the heart of the Winter Haven Heights Historic Residential District that was added to the National Register of Historic Places in 2000! Just 200 feet to the Kiwanis Park on the shores of Lake Martha! Spacious rooms with high ceilings waiting for your imagination are renovation! New Roof 2024! Call for your private showing today!

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

Listing Agent: Steve Lockhart (863-289-9801)

Remarks: Welcome to this beautiful 4-bedroom, 2.5-bath home that perfectly blends comfort and charm. Major updates have already been completed, including a new roof installed in May 2025, foundation work completed in November 2024, a new sliding door added in November 2024, and the main floor has recently been updated. Step inside to find spacious living areas, ideal for both everyday living and entertaining. The real showstopper is the dream backyard—an outdoor oasis featuring a stunning pool and an incredible farm-style barn that offers endless possibilities, from hobbies to storage or even a unique entertaining space. This property truly has it all—space, style, and a one-of-a-kind backyard retreat you won’t want to miss! Property is being sold As-Is. The property also features a brand-new barn shed and solar panels, offering added value and efficiency for the next owner.

Listing is courtesy of: NORKIS & CO REALTY (407-506-7070)

Listing Agent: Daisy Perez (407-951-4218)

Remarks: Welcome to this stunning 4-bedroom, 3-bath split floor plan home with tile flooring throughout. The open kitchen features a breakfast bar, brand-new stainless steel appliances, and plenty of storage. You’ll love the formal living room and a dedicated laundry room. Sliders from both the master suite and living room lead to a peaceful lanai. The master bath boasts dual sinks, a garden tub, and a separate shower. Plus, one of the bathrooms conveniently opens to the lanai. The lanai floor and garage floor was recently painted for that added style. The home is located in Winter Haven in between Orlando and Tampa close to all of the amenities you would need. Don’t miss this gem!

Listing is courtesy of: HARPER REALTY FL, LLC (863-687-8020)

Listing Agent: Annie Wood (321-229-1913)

Remarks: One or more photo(s) has been virtually staged. One or more photos have been virtually staged. Charming 1920s home for sale in Winter Haven, offering a rare blend of historic character and functional living space in a highly desirable Central Florida location. This move-in ready home welcomes you with a bright tiled foyer, featuring a spacious coat closet and direct access to a front bedroom, ideal for a home office, guest room, or flex space. The main living and dining areas showcase original hardwood flooring and provide an open, inviting layout perfect for both everyday living and entertaining. The kitchen comes fully equipped with refrigerator, range, microwave, and dishwasher, delivering convenience and efficiency for modern living. This split-bedroom floor plan enhances privacy, with the primary suite positioned separately from the secondary bedroom. Just outside the primary bedroom, a versatile bonus area offers flexibility for a home office, nursery, gym, or creative workspace. A rear Florida room adds valuable additional living space and provides direct access to the driveway, creating an ideal setting for relaxing, entertaining, or enjoying Florida’s indoor-outdoor lifestyle. Situated on an R-3 zoned property, this home presents potential opportunities for investors, developers, or buyers seeking flexibility. Buyers are encouraged to verify all zoning and future use possibilities with the City of Winter Haven. Located near shopping, dining, parks, and the renowned Chain of Lakes, this property offers convenient access to boating, recreation, and everything that makes Winter Haven real estate so desirable. Schedule your showing today and explore the potential of this unique Florida home.

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

Listing Agent: Michael Hochadel (863-604-0018)

Remarks: Located in the highly sought-after gated community of Lakewood, this beautifully maintained home offers 4 bedrooms and 3.5 bathrooms, set on a lush, manicured lot with mature trees and attractive landscaping. Inside, you’ll find rich wood flooring throughout the spacious living and dining areas, as well as the kitchen and family room—perfect for both everyday living and entertaining. A standout feature is the expansive 480 sq ft detached game room, included in the total living area, complete with a full bathroom and generous closet space—ideal for conversion into a private guest house, in-law suite, or home office. The primary suite boasts a recently renovated en-suite bathroom and direct access to the large screened lanai and pool area, creating a relaxing retreat. Major updates include a roof replacement in 2017. This exceptional property offers space, flexibility, and charm—don’t miss your opportunity to make it yours!

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

Listing Agent: Steve Lockhart (863-289-9801)

Remarks: One or more photo(s) has been virtually staged. Welcome to this stunning Floorplan, located in the highly sought-after community of Willowbrook near a beautiful Golf Course in Winter Haven, FL. This spacious 4-bedroom, 3-bath home offers 2110 sq feet of living space and provides excellent curb appeal in its elevation. Inside, you will find gorgeous White cabinets complemented by sleek quartz countertops in the kitchen, creating a modern, bright atmosphere. Tile flooring runs throughout the wet and common areas, offering durability and easy maintenance. The open layout is perfect for family gatherings and entertaining guests.

Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)

Listing Agent: Cindy Sapp (352-516-2843)

Remarks: This expansive property is a true diamond in the rough, perfectly positioned for the savvy investor looking for a great return on a "buy and hold" scenario or a strategic value-add project. Boasting a generous 0.41-acre lot, this property is designed for versatility. With a massive layout featuring 6 bedrooms and 4 bathrooms, the home offers the unique potential for 3 or even 4 separate doors (units), making it an ideal candidate for a multi-generational living setup or a high-performing rental portfolio addition. Only 12 minutes away from LEGOLAND!

Listing is courtesy of: MARZUCCO REAL ESTATE (813-679-1365)

Listing Agent: Clarisa Moody (813-446-2003)

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: Welcome to this beautiful 3-bedroom, 2-bathroom home in the heart of Winter Haven! Featuring a desirable open floor plan, this home offers comfortable living with plenty of space to relax and entertain. The modern kitchen is highlighted by granite countertops, ample cabinetry, large island, and a seamless flow into the main living area, making it perfect for gatherings. Just off the entrance, you’ll find a versatile flex space that can easily serve as a home office, dining room, or playroom to suit your needs. The spacious primary suite is a true retreat, complete with a large bedroom and dual master closets, offering plenty of storage. Two additional bedrooms and a second full bathroom provide comfortable accommodations for family or guests. Step outside from the large sliding doors to enjoy the fenced-in backyard, ideal for pets, outdoor activities, or relaxing evenings. Located in a great neighborhood in the heart of Winter Haven, this home is conveniently close to shopping, restaurants, and local schools, offering both comfort and convenience. Don’t miss the opportunity to make this wonderful home yours!

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

Listing Agent: Bethany Jack (606-584-0518)

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: Short Sale. SHORT SALE OPPORTUNITY – PRICED TO SELL! Welcome to this 2022-built 3-bedroom, 2-bathroom home located in the growing Lucerne Park Reserve community of Winter Haven. This newer construction single-story home features a desirable open-concept floor plan, perfect for comfortable everyday living and easy entertaining. The spacious kitchen overlooks the living and dining areas, creating a bright and inviting central gathering space. The primary suite offers a private bathroom and generous closet space, while two additional bedrooms provide flexibility for guests, family, or a home office. Home includes solar panels, offering potential energy efficiency benefits for the new owner. Conveniently located near shopping, dining, schools, and major highways with easy access to Lakeland, Orlando, and surrounding Central Florida areas. Ideal opportunity for first-time buyers, investors, or anyone looking to add value in a rapidly growing area. Short Sale – subject to lender approval. Property sold as-is. MOTIVATED SELLERS!!!

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

Listing Agent: Mariel Espinal (407-921-5868)

Remarks: One or more photo(s) was virtually staged. Nothing to do but unpack. This 3-bedroom, 2-bathroom home in Deer Lake Terrace delivers true move-in-ready living at one of Winter Haven's most accessible price points. At 1,200 square feet of solid block construction on a 0.15-acre lot, this home checks every box for first-time buyers and investors alike. Step inside to an open, light-filled layout with luxury vinyl plank flooring flowing through every room. The updated kitchen features modern shaker cabinetry, granite countertops, and a full appliance package: dishwasher, disposal, microwave, range, and refrigerator, all included. Both bathrooms were gutted and rebuilt with contemporary tile and fixtures. Central air conditioning keep the home comfortable year-round. The enclosed porch adds over 275 square feet of flexible living space that doesn't disappoint. Use it as a home office, playroom, second living area, or year-round entertaining space. Outside, the fully fenced yard includes a utility building for storage, all on a flat and usable lot connected to public water and sewer. The shingle roof was replaced during the renovation. No HOA. No CDD. No lease restrictions. Zoned R-2, this property is equally suited for a primary residence or income-producing rental with no association approval required. Flood Zone X, no flood insurance required. Deer Lake Terrace is a quiet, established neighborhood in northwest Winter Haven with quick access to US-17, US-92, Polk Parkway, and downtown Winter Haven's restaurants, shopping, and the Chain of Lakes trail system. Legoland Florida and Posner Park are just minutes away.

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

Listing Agent: Nelson Cruz Pa (407-901-9939)

Remarks: Under contract-accepting backup offers. Welcome to this beautiful fully renovated 3-bedroom, 2-bath home offering 1,485 square feet of stylish, move-in-ready living in the heart of Winter Haven, Florida. Every detail has been thoughtfully updated to deliver modern comfort and peace of mind. Enjoy brand-new doors and windows that fill the home with natural light, along with a completely new kitchen featuring contemporary finishes and new appliances—perfect for everyday living and entertaining. Both bathrooms have been fully renovated, offering fresh, modern design and functionality. New flooring throughout ties the home together with a clean, cohesive look. Adding even more value, a brand-new roof has been installed, providing long-term durability and confidence for the next homeowner. AC Replaced in 2020, Whole Home re-pipe with PEX and PVC/CPVC in 2020. Conveniently located near shopping, dining, schools, and Winter Haven’s renowned lakes, this turnkey property blends modern upgrades with Florida charm. Don’t miss the opportunity to own a fully updated home ready for immediate enjoyment.

Listing is courtesy of: DOWNTOWN REALTY (407-989-8881)

Listing Agent: Mark Rankin (407-989-8881)

Remarks: Fully Renovated! Discover the perfect blend of modern upgrades and timeless charm in this beautifully updated 5-bedroom, 3-bathroom home. Featuring a brand-new kitchen, updated living spaces, new flooring throughout, and completely renovated bathrooms, this property is truly move-in ready. Recent upgrades include a new roof (2024), new electrical panel, new water heater, fresh interior and exterior paint, and all-new lighting and ceiling fans. The kitchen is a standout, showcasing quartz countertops, new cabinetry, stainless steel appliances, and modern finishes. Enjoy the warmth of a cozy wood-burning fireplace or step outside to your private oasis with a resurfaced pool and a spacious, fully fenced backyard—perfect for entertaining or relaxing. Located between Orlando and Tampa with no HOA or CDD, this home offers flexibility, freedom, and excellent investment potential. Conveniently close to major highways, theme parks, shopping, and dining. Short-term rentals are allowed, making this a great opportunity for both homeowners and investors.

Listing is courtesy of: GARCIA REALTY GROUP (407-920-3616)

Listing Agent: Erika Pinto (407-460-4097)

Remarks: Under Construction. Located in the heart of Winter Haven, Willowbrook South puts you close to the area's Chain of Lakes, beautiful parks, and an array of dining and shopping. With top attractions and everyday conveniences just minutes away, your new home here keeps you connected to everything you love. Your new home at Willowbrook South places you right where you want to be. Let me Introduce you to the Archer II this 1328 Sqft. 3 Bedroom 2 Bath home is just to die for. This home provides Luxury Vinyl tile in all the wet areas, Living and Dining Rooms and Quartz Counter tops in the Kitchen and both Bathrooms. The Kitchen includes a Stove, Microwave, Dishwasher and Refrigerator, all Stainless Steel by Whirlpool and also includes a Washer/Dryer. The Archer II has an Open Floor plan that allows you to entertain guest even if they are in the living or dining room. Spacious bedrooms Owners Suite that can easily fit a King size bed. And on top of all that it also comes with our Home Smart System. Come by today! *Photos are of similar model but not that of the exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability, and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

Listing is courtesy of: DR HORTON REALTY OF CENTRAL FLORIDA LLC (407-250-7299)

Listing Agent: Paul King (407-519-3940)

Remarks: Under Construction. The Freeport II floor plan at Willowbrook South offers the perfect blend of comfort, functionality, and modern design. Built with durable all-concrete block construction, this one-story home maximizes living space with a bright, open-concept layout that’s ideal for everyday living and entertaining. As you enter through the foyer, you’ll find two spacious guest bedrooms and a full guest bath with a modern vanity. A convenient linen closet is positioned between the bathroom and bedrooms for easy storage. Further down the hallway, a third bedroom offers flexibility for a home office or guest space, alongside a private laundry area and direct access to the two-car garage. The heart of the home features a well-appointed kitchen with stainless steel appliances, overlooking the dining area, great room, and covered patio perfect for gatherings and family time. Tucked at the rear of the home, the primary bedroom offers a peaceful retreat with a walk-in closet and a spa-inspired bathroom featuring a double vanity sink and a spacious shower. Every home in Willowbrook South comes equipped with the Home Is Connected Smart Home Technology package, allowing you to control locks, thermostat, and more right from your smartphone whether you’re home or away. With its thoughtful design and modern features, the Freeport makes owning a new home in Winter Haven, FL both easy and enjoyable. *Photos are of similar model but not that of the exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability, and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

Listing is courtesy of: DR HORTON REALTY OF CENTRAL FLORIDA LLC (407-250-7299)

Listing Agent: Paul King (407-519-3940)

Remarks: Under Construction. Let me Introduce you to our 5 Bed 2 Bath 1708sqft floor plan the Dundee. This home provides you with Luxury Vinyl Tile in all the wet areas and the living and dining rooms with Quartz Counter Tops in the Kitchen and Bathrooms. The Kitchen provides Stainless Steel Whirlpool Appliances that Including a Stove, Microwave, Refrigerator and Dishwasher, and a Washer and Dryer in the Laundry room. You have 4 Spare Bedrooms and an Owners Suite that can easily fit a King size bed with walk in closet. Beautiful Master bath with two Adult Vanity sinks and Quartz Countertops.

Listing is courtesy of: DR HORTON REALTY OF CENTRAL FLORIDA LLC (407-250-7299)

Listing Agent: Paul King (407-519-3940)