Homes for Sale Near Winter Haven Senior in Winter Haven - 138 homes

Remarks: Welcome to your dream oasis—a stunning craftsman-style 3-bedroom, 2-bath saltwater pool home nestled on just over a quarter acre. This charming property features a large front porch, perfect for relaxing with your morning coffee or enjoying beautiful sunsets. Step inside to find a warm and inviting interior with classic crown molding throughout. The formal dining room offers an elegant space for entertaining, and it can easily double as a home office or flexible bonus room to suit your needs. A cozy dinette off the kitchen provides an additional casual setting for family meals. The backyard is a true retreat, boasting a huge fenced area that provides privacy and security. Dive into the sparkling pool, or unwind on the screened back porch, where you can enjoy the tranquility of your outdoor space. This stunning home also includes a 2-car carport, a long driveway for additional parking, and convenient boat parking—ideal for those who love life on the water. Located near the Lake Howard public boat dock, you’ll enjoy easy access to Winter Haven's sought-after chain of lakes. Additional features include a Generac generator for peace of mind, propane tanks for efficient energy use, and a storage shed for all your gardening tools and equipment. This home perfectly combines comfort, style, and functionality in a picturesque setting. Don’t miss your chance to make it yours!

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

Listing Agent: Michelle Howard (863-944-9920)

Remarks: Enjoy this clean 2 bedroom, 2 bath villa in the community of Mayfair Place. Step into a spacious great room with soaring ceilings and all ceramic tile floors throughout, offering both style and ease of maintenance. The open kitchen includes plenty of counterspace, gas range/stove, and breakfast bar. The primary suite features sliding glass doors leading to a peaceful back patio, the perfect spot for morning coffee or winding down in the evening. Inside utility room with extra cabinet and counter space, plus an additional storage closet for even more convenience. Just minutes from downtown, this villa provides easy access to local dining, shopping, and medical facilities.

Listing is courtesy of: STAR REALTY OF WINTER HAVEN (863-299-7827)

Listing Agent: Carlee Marchetti (863-258-3338)

Remarks: Welcome to 22 Lake Link in Winter Haven, where space, lifestyle, and location come together in one exceptional opportunity. Situated on a large corner lot, this 4-bedroom, 2-bathroom home with a 2-car garage offers the perfect combination of comfort, functionality, and Florida living. Step inside to a bright and open floor plan designed for modern living and entertaining. The spacious layout flows seamlessly from the living and dining areas to the kitchen, creating the perfect environment for hosting family and friends. Enjoy your mornings on the front balcony and unwind in the evenings on the screened-in patio, overlooking your huge fenced-in backyard—ideal for pets, gatherings, or even adding a pool. Additional highlights include a durable metal roof for long-term value and a large driveway with plenty of space for multiple vehicles, guests, or recreational toys. This home is perfectly positioned to give you access to everything that makes Central Florida one of the most desirable places to live. Convenient access to major highways including Interstate 4, US Route 27, and Florida State Road 540 for easy commuting to Orlando, Tampa, and beyond. Just a short drive to world-famous attractions like Walt Disney World, Universal Orlando Resort, and LEGOLAND Florida Resort. Enjoy weekend trips to Florida’s beautiful beaches including Clearwater & St. Pete Beach (west coast) and Cocoa Beach (east coast). Living in Winter Haven means you’re close to a growing scene of local favorites and everyday conveniences such as, Coffee spots like Richard's Fine Coffees and Starbucks. Popular dining options including Harborside, Tanners Lakeside Restaurant & Bar, Aria and Azteca D'Oro. Shopping and entertainment nearby at Winter Haven Central Park and Eagle Ridge Mall. Minutes from Lake Link and the Chain of Lakes of Winter Haven, Florida.

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

Listing Agent: Omar Andreasen (407-883-2989)

Remarks: Welcome to this charming three-bedroom, two-bath home nestled in the desirable Lake Daisy Wood neighborhood. Featuring a practical open concept floor plan with tile throughout, this residence is designed for comfortable living. The inviting living room seamlessly connects to a screened porch lanai through sliding glass doors, providing a perfect view of the spacious, fenced backyard—ideal for gatherings or relaxation. The kitchen boasts a convenient breakfast bar and a separate eating area, while a dedicated laundry room connects the garage to the home for added convenience. The generous primary bedroom offers an en suite bath complete with a tub, separate shower, and a large walk-in closet, with its own sliding glass doors leading to the screened lanai. As an added benefit, with a full-price offer, the seller will pay off the solar system in full. This home combines functionality with a welcoming atmosphere, perfect for everyday living.

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

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

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: One or more photo(s) has been virtually staged. This is a 4 bedroom, 2 bathroom single family home with approximately 2,355 square feet on about 0.34 acres, a 2 car garage, a wood burning fireplace, and a screen enclosed pool and jacuzzi inside a gated community just minutes from Legoland. This home stands out for buyers who want strong square footage, a functional layout, and outdoor features that are already in place. The floor plan gives plenty of room for daily living, guests, or flexible use, and the 2 car garage adds practical storage and parking that matters for long term ownership. The gated setting brings added privacy and neighborhood appeal while keeping the property close to shopping, dining, schools, and the main conveniences that make this part of Winter Haven attractive. Inside, the home gives a buyer a solid starting point with the chance to update key finish areas over time. The kitchen and bathrooms are the main spaces where a future owner may choose to remodel, making this a value add opportunity for someone who wants to improve the home around an already desirable footprint. The wood burning fireplace adds character to the living area and helps give the interior more presence than a basic builder layout. This is the kind of house that works well for a buyer who wants size, location, and lifestyle features first, then the freedom to make design changes at their own pace. The outdoor setup is a major part of the appeal. The screen enclosed pool and jacuzzi create a more complete Florida living experience and give the backyard a true entertaining and relaxation element. The screened enclosure adds usability and helps the pool area feel like an extension of the home rather than just an extra feature. The pool is reported to be working, with the main noted item being a light, and seller will have the pool fully cleaned and ready to go. For buyers searching online for a Winter Haven pool home, a gated community home near Legoland, a house with jacuzzi and screened pool, or a Polk County property with indoor and outdoor living space, this home checks multiple search points that matter. Major system notes also help frame the opportunity clearly. The AC is reported at about 10 years old, the water heater about 2 years old, and the roof about 10 years old, with a prior note that inspection suggested roof replacement due to age and mentioned one small leak in a closet. The septic system was replaced, which is an important update for future maintenance planning. HOA is reported at approximately $550 a year, and rental restrictions are reported as no. For buyers looking for a 4 bedroom 2 bathroom home in Winter Haven, a gated neighborhood property near Legoland, or a Florida home with pool, fireplace, garage, and room to personalize, 215 Santa Rosa Dr presents a strong opportunity. SOME PHOTOS HAVE BEEN VIRTUALLY EDITED.

Listing is courtesy of: SILVER DOOR REALTY LLC (954-993-0696)

Listing Agent: Michelle Paez (954-589-0144)

Remarks: One or more photo(s) has been virtually staged. 4.99% Rate 30-year fixed FHA/VA Act now ! Step into this renovated farmhouse charm : 2-bedroom, 2-bathroom home, nestled on a spacious lot in the established Villa Manor neighborhood. NO HOA This move-in-ready residence presents luxury finishes, laminate flooring throughout, a sleek new kitchen with updated cabinets, carrara white quarts countertops, and stainless steel appliances, and a freshly tiled bathroom with contemporary finishes. Fresh interior and exterior paint, and upgraded lighting fixtures. The large backyard offers plenty of space for outdoor living or future expansion. Located minutes from local schools, parks, and downtown Winter Haven’s shops and restaurants, this home is perfect for first-time buyers, downsizers, or investors seeking turnkey potential.

Listing is courtesy of: KELLER WILLIAMS LEGACY REALTY (407-855-2222)

Listing Agent: Daniel Araque (321-276-0747)

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: Welcome to 525 Winter Terrace in Winter Haven, an inviting, move-in-ready 2-bedroom, 2-bath, single-level townhouse in a maintenance-free family community with outstanding amenities. Step inside to find ceramic tile throughout the main living areas, spacious bedrooms, and a bright Florida room perfect for relaxing or entertaining. The heart of the home is the completely updated kitchen featuring nice appliances, wood cabinetry, and granite countertops, complemented by neutral interior paint and updated tile. Enjoy even more comfortable living space in the enclosed back room, offering additional air-conditioned square footage. The primary suite has sliding glass doors that lead to your own, private, enclosed porch. Community perks include a clubhouse, solar-heated pool, shuffleboard, and a private boat dock on beautiful Lake Smart. Schedule your showing today because this one won’t last long!

Listing is courtesy of: THE SIMON SIMAAN GROUP (407-558-1396)

Listing Agent: Oralis Perez (407-325-1045)

Remarks: Welcome To Hartridge Hills!! This Gorgeous Gated Community is one of Polk County's Hidden Treasures. An established and well maintained community of charming custom homes, each one uniquely it's own. Nestled between Lake Pansy and Lake Hartridge, this community offers boat lovers their own private boat ramp with access to the Chain of Lakes. This community also has been home to many pilots over the years and is conveniently located beside the Winter Haven Airport and only minutes to Publix and all major medical facilities making this community a perfect location. Situated on a corner lot, this well built home by Ernie White is a split plan offering 3 bedrooms & 2 baths plus a den or office space. The dining room, living area and bedrooms have new luxury vinyl. There is High ceilings throughout, crown molding, updated granite in the kitchen and bathrooms. The roof was replaced in 2017. HOA fee's include lawn care and the irrigation system is on a small well, saving you money on your water bill! Grab your favorite beverage & Relax and Enjoy the water views on your enclosed back lanai. Come check out this beautiful property, You'll love being a part of this quaint community!!

Listing is courtesy of: PREMIER HOMES AND REAL ESTATE (863-937-8942)

Listing Agent: Christy Smith (863-409-8709)

Remarks: One or more photo(s) has been virtually staged. Discover this exceptional investment opportunity in the thriving city of Winter Haven! This spacious and well-maintained 2-bedroom, 1.5-bath apartment offers the perfect blend of comfort, location, and long-term rental potential. Ideal for investors seeking stable returns, this unit comes equipped with all appliances, including an in-unit washer and dryer, providing added convenience and desirability for future tenants. Perfectly situated, the property is only 5 minutes (approx. 3 miles) from the world-renowned Legoland Theme Park, making it highly attractive for families and professionals relocating to the area. You’ll also be just minutes from Port 27, Winter Haven’s newest lifestyle and entertainment destination located on Lake Hamilton, featuring waterfront dining, recreation, and a growing selection of family-friendly activities. Inside, the unit offers a functional layout with comfortable living spaces, natural light, and low-maintenance living—an excellent advantage for landlords. Whether the intended use is long-term leasing or adding a turnkey property to an investment portfolio, this apartment checks all the boxes. Winter Haven continues to experience strong residential growth, fueled by its central location, access to major highways, beautiful chain of lakes, and expanding entertainment and commercial developments. This upward trend makes the area highly appealing for long-term renters and a promising market for investors. Don’t miss the chance to secure a property in one of Central Florida’s most dynamic and fast-growing communities. This is a solid investment you’ll want to add to your portfolio!

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

Listing Agent: Yuliescar Mendoza (321-402-6564)

Remarks: Welcome to 1805 Emily Drive—where space, comfort, and outdoor living come together to create a home that truly stands apart in today’s market. Nestled in a well-positioned area of Winter Haven, this 4-bedroom, 2.5-bath pool home delivers the flexibility today’s buyers are actively seeking. Step inside and immediately notice the expansive layout designed to adapt to your lifestyle. The main level showcases ceramic rustic tile and luxury vinyl plank flooring, while the staircase and entire upper living areas have also been upgraded with durable, modern luxury vinyl—offering both style and easy maintenance. Upstairs, the oversized primary suite creates a true owner’s retreat, highlighted by soaring cathedral ceilings, a spacious en-suite bath, and the rare advantage of two walk-in closets. Each additional bedroom offers impressive dimensions, providing the kind of space that’s increasingly difficult to find in newer construction. The real showstopper awaits outdoors. Enjoy your own private backyard oasis featuring full vinyl fencing, a generous covered lanai, and a screened pool built for year-round enjoyment. Whether you’re hosting weekend gatherings, creating memorable family moments, or simply unwinding in your own peaceful setting, this outdoor space delivers the Florida lifestyle buyers dream about. This property has been meticulously maintained, reflecting pride of ownership throughout and offering peace of mind for its next owner. Opportunities to secure a move-in-ready pool home with this combination of condition, space, and location are becoming increasingly scarce. Positioned just minutes from major shopping, dining, schools, and commuter routes, this property also presents strong long-term value and investment appeal. This home will not last long in the market. Schedule your private showing today!

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

Listing Agent: Pedro Santiago (407-259-9513)

Remarks: Welcome to this beautifully updated single-story home. This cozy property features modern interiors with high-gloss, marble-style porcelain flooring throughout, creating an elegant and spacious atmosphere. The main living area offers excellent natural light through multiple windows, along with ceiling fans that provide additional comfort. The kitchen includes well-kept wood cabinetry, decorative backsplash, and stainless steel appliances. The bathroom has been renovated with a modern vanity and contemporary finishes. An interior laundry area comes equipped with washer and dryer. Outside, the property features a large yard with mature trees, a covered carport, and an extended driveway. This is a wonderful opportunity to live or invest in a quiet, well-established neighborhood.

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

Listing Agent: Gabriel Rivera Gonzalez (407-724-4717)

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: ***PRICE DECREASE +++ SELLER IS OFFERING $5000 in seller concessions!!! This unique 2-story home in Winter Haven is full of character and charm, located just three houses down from scenic Lake Elbert. Thoughtfully updated while preserving its warm, rustic appeal, this property offers a welcoming atmosphere from the moment you arrive. Outdoor enthusiasts will love the 2.4-mile paved loop trail surrounding Lake Elbert, complete with boardwalks and beautiful landscaping—perfect for morning walks, bike rides, or peaceful evening strolls. The home is in walking distance to Downtown Winter Haven, the public boat ramp and park, and Polk State College’s Winter Haven Fine Arts Building, offering exceptional convenience and lifestyle amenities. Inside, you’ll find live-edge wood countertops, natural wood trim, and an open kitchen overlooking the family and dining rooms. The kitchen features stainless steel appliances, newer cabinets, and a rustic flair originally crafted by an Amish family. The spacious family room includes a large picture windows that frame the beautiful front yard and mature oak tree. The primary bedroom and bathroom are conveniently located downstairs, while the second floor offers two additional bedrooms, a bonus room, a full bathroom, and a loft area with generous storage closets. Both bathrooms have been updated with newer cabinets, newer countertops, and newer tile. Additional interior upgrades include newer luxury vinyl plank flooring, newer windows, newer light fixtures and ceiling fans, and fresh interior paint. The home also features a newer A/C system. Outside, the home offers a covered front porch perfect for evening relaxation, mature landscaping, and a fenced yard on nearly a quarter-acre, with most of the outdoor space located in the front of the home. Ideally situated near Lake Elbert, Downtown Winter Haven, Polk State College, shopping, dining, parks, and medical facilities, this home offers both convenience and character. Schedule your private showing today!

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

Listing Agent: Lisa Ford (863-510-3890)

Remarks: Welcome to this stunning Bradley floorplan, located in the highly sought-after community of Willowbrook near a beautiful golf course in Winter Haven, FL. This spacious 4-bedroom, 2-bath home offers 1598 square feet of living space and provides excellent curb appeal in its elevation. Inside, you'll 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: Nancy Pruitt, Pa (352-552-7574)