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855 Killearn Boulevard, Winter Haven
$251,300
3 Beds ⋅ 2 Baths ⋅ O6441818 MLS
Charm and curb appeal abound for this Winter Haven home! Step inside the inviting foyer and into the well-appointed living room, positioned at the center of the home. The kitchen boasts stainless steel appliances, hard surface countertops, and ample storage. This ranch style floorplan is rounded out by the bonus room, the primary suite, and two secondary bedrooms. Come and see for yourself the possibilities that this home has to offer!

855 Killearn Boulevard, Winter Haven

Listing courtesy of EVERYSTATE INC.. 501-725-1234
3541 Raleigh Drive, Winter Haven
$345,000
3 Beds ⋅ 3 Baths ⋅ P4939900 MLS
Discover exceptional Florida living in this fabulous Eco Smart 3-bedroom, 3-bath home with a den, ideally situated in the premier gated active-adult community of Traditions at Lake Ruby. Designed with comfort, efficiency, and entertaining in mind, this beautifully appointed home offers an impressive array of upgrades and thoughtful features. The desirable split-bedroom floor plan provides privacy and versatility, including a spacious Junior Bedroom Suite with its own ensuite bath—perfect for visiting family or guests. The well-equipped kitchen is a chef’s delight, featuring a center island with pendant lighting, fingerprint-resistant stainless-steel appliance package, recessed lighting, and 42-inch white upper cabinetry enhanced with crown molding, soft-close hinges, and brush nickel hardware. A generous walk-in pantry provides additional storage, while the pull-out cabinet organizers keep everyday items conveniently within reach. The spacious Living Room features wood laminate flooring and triple glass sliding doors that open to the extended lanai, seamlessly blending indoor and outdoor living. The open-concept design also incorporates a dedicated Dining Room and cheerful breakfast nook, providing plenty of space for family gatherings and entertaining. The generously sized Primary Bedroom Suite is enhanced with laminate flooring and dual walk-in closets featuring deluxe closet organizer systems. The luxurious Primary Bath offers a handicapped-accessible tiled shower with glass enclosure, comfort-height vanity with dual sinks, and linen closet for additional storage. Outdoor entertaining is effortless in the oversized screened lanai, featuring decorative stamped-concrete flooring, retractable solar screens and a built-in buffet and BBQ Grill—perfect for enjoying Florida’s year-round outdoor lifestyle. Additional amenities include a versatile Den/Office, Laundry Room with cabinetry, washer and dryer, ceiling fans with remote controls, and extensive storage throughout. Energy-efficient features include solar panels with a monthly solar expense of approximately $209, a 15-SEER HVAC system, AO Smith hybrid water heater, Low-E windows, radiant heat barrier, and architectural shingle roof installed in 2026. A stone facade, decorative stone curbing, and paved driveway add to the home’s impressive curb appeal. Additional upgrades include smart-lock entry, whole-house generator, retractable garage screen, keyless garage entry pad, and a two-car garage equipped with three overhead storage racks, workbench with matching cabinetry, and an overhead solar skylight. Traditions at Lake Ruby offers an exceptional active-adult lifestyle with an impressive selection of amenities and planned community activities. Residents enjoy a lakefront clubhouse, dock and boat ramp, heated swimming pool and spa, ballroom, billiards, meeting room, library, computer room, craft room, dog park, tennis courts, basketball court, bocce, shuffleboard, fitness center, aerobics studio, and so much more. Conveniently located near shopping, medical facilities, and major transportation routes, Traditions at Lake Ruby offers the perfect combination of resort-style amenities, energy-efficient living, and everyday convenience. HOME CAN BE PURCHASED FURNISHED

3541 Raleigh Drive, Winter Haven

Listing courtesy of CENTURY 21 MYERS REALTY LAKE WALES. 863-676-4448
101 Sandburg Lane, Winter Haven
$295,000
4 Beds ⋅ 2 Baths ⋅ L4964941 MLS
Welcome to this beautifully maintained 4-bedroom, 2-bathroom home situated on a spacious, fully fenced corner lot! Offering the perfect blend of comfort, functionality, and outdoor space, this property is ready to welcome its next owner. Inside, you'll find newer luxury vinyl plank flooring throughout the comfortable layout, with added mini-split AC systems in the primary bedroom and 4th bedroom. The 2021 roof provides valuable peace of mind, while the large 24x20 metal building offers exceptional versatility for storage, hobbies, a workshop, or recreational equipment. Enjoy the Florida lifestyle with plenty of room for pets, entertaining, and outdoor activities. With its flexible living space, oversized metal building, and important updates, this home offers an excellent opportunity to make it your own. Come see what 101 Sandburg Ln has to offer!

101 Sandburg Lane, Winter Haven

Listing courtesy of COLDWELL BANKER REALTY. 863-294-7541
2211 9th Street Ne, Winter Haven
$200,000
3 Beds ⋅ 2 Baths ⋅ P4939797 MLS
Discover the opportunity to make this charming 3-bedroom, 2-bathroom home your own. Located in an established neighborhood with NO HOA. Offering approximately 1,522 square feet of living space. This home provides a comfortable layout with plenty of potential for everyday living, entertaining, or creating space that truly reflects your style. Situated on approximately 0.16 acres, the property has outdoor space for relaxing, gardening, pets, or enjoying Florida's beautiful weather. It also has a fenced in yard and is conveniently located near a newly built recreation center, highly rated magnet schools, local parks, lakes, and public transportation. Whether you're a first-time homebuyer, looking for a family home, or an investor seeking an opportunity in a desirable Central Florida market, 2211 9th St NE will be a perfect fit for you.

2211 9th Street Ne, Winter Haven

Listing courtesy of KELLER WILLIAMS REALTY SMART 1. 863-508-3000
293 Alpine Dr, Winter Haven
$44,990
2 Beds ⋅ 2 Baths ⋅ 11983750 MLS
Discover your retreat in the heart of Central Florida! This **2-bedroom, 2-bathroom** furnished manufactured home is nestled within **Swiss Village**, an active **55+ retirement community** on beautiful **Lake Henry**. Move in with ease - this home comes furnished minus just a few personal items, so you can start enjoying the Florida lifestyle right away. Recent upgrades bring peace of mind, including a **2022 roof** and a **2025 HVAC system**. The water heater was installed around 2012, keeping essentials well-maintained. Swiss Village truly feels like a year-round vacation. Tucked away beneath beautiful mature trees with street lamps lining every road, this community offers an incredible array of amenities. Residents enjoy two sparkling swimming pools, two jacuzzi spas, championship shuffleboard courts, miniature golf, horseshoes, a billiard room, and a large clubhouse buzzing with planned activities. The community is **pet friendly**, and the estimated **lot rent of approximately $630/month** includes trash service and pass-through taxes - outstanding value for everything included. Location is everything, and Swiss Village delivers. You're conveniently close to **Disney**, major sporting venues, excellent shopping, diverse restaurants, and two modern hospitals - all while enjoying the laid-back charm of Winter Haven. **Schedule your showing today** - opportunities like this don't last long! VISIT THE LISTING AGENT'S WEBSITE TO EXPLORE THE VIRTUAL TOUR, THEN ARRANGE A PRIVATE SHOWING IN PERSON. **OUT OF TOWN!?!? NO WORRIES, WE CAN DO VIRTUAL SHOWINGS AND WE ARE ABLE TO DO PAPERWORK REMOTELY. FEEL FREE TO CALL, TEXT, OR EMAIL ME. I LOOK FORWARD TO BEING YOUR RAY OF SUNSHINE AND HELPING YOU CALL YOUR NEW HOUSE A HOME! All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Our company does not and cannot guarantee or warrant the accuracy of this information or the condition of this property. Measurements are approximate. The buyer assumes full responsibility for obtaining all current rates of lot rent, fees, and pass-on costs. Additionally, the buyer is responsible for obtaining all rules, regulations, pet policies, etc., associated with the community, park, or home from the community/park manager. Our company is not responsible for quoting said fees or policies. Financing is available through 3rd party lenders. Please contact the sales agent for additional information. The listing price does not include the buyer's closing cost (sales tax etc)

293 Alpine Dr, Winter Haven

Listing courtesy of Chrissy Walter with Sunset Home Sales
3761 Giorgio Drive, Winter Haven
$319,090
4 Beds ⋅ 2 Baths ⋅ TB8544818 MLS ⋅ Meritage Homes BLDG.
Under Construction. Brand new, energy-efficient home available by Sep 2026! Prepare dinner while catching up on the days events from this home's open kitchen which overlooks a spacious great room and dining area. Retreat to your primary suite that is conveniently situated in the back of the home for plenty of privacy. Visit Villamar and explore new single-family homes for sale in Winter Haven, FL. Residents will have access to two resort-style amenity centers featuring a clubhouse, pool, and playground. Winter Haven is known for its beautiful chain of lakes with lakeside restaurants and its award-winning community theater. Nearby attractions include Legoland Florida and Peppa Pig Theme Park. A brand-new model and new phase are coming soon. Each of our homes is built with innovative, energy-efficient features designed to help you enjoy more savings, better health, real comfort and peace of mind.

3761 Giorgio Drive, Winter Haven

Listing courtesy of MERITAGE HOMES OF FL REALTY. 813-703-8860
3921 Giorgio Drive, Winter Haven
$335,000
4 Beds ⋅ 2 Baths ⋅ TB8544819 MLS ⋅ Meritage Homes BLDG.
Under Construction. Brand new, energy-efficient home available by Sep 2026! Prepare dinner while catching up on the days events from this home's open kitchen which overlooks a spacious great room and dining area. Retreat to your primary suite that is conveniently situated in the back of the home for plenty of privacy. Visit Villamar and explore new single-family homes for sale in Winter Haven, FL. Residents will have access to two resort-style amenity centers featuring a clubhouse, pool, and playground. Winter Haven is known for its beautiful chain of lakes with lakeside restaurants and its award-winning community theater. Nearby attractions include Legoland Florida and Peppa Pig Theme Park. A brand-new model and new phase are coming soon. Each of our homes is built with innovative, energy-efficient features designed to help you enjoy more savings, better health, real comfort and peace of mind.

3921 Giorgio Drive, Winter Haven

Listing courtesy of MERITAGE HOMES OF FL REALTY. 813-703-8860
4856 Summerfield Circle, Winter Haven
$290,000
4 Beds ⋅ 2 Baths ⋅ O6441991 MLS
Virtually Staged. Welcome to this inviting 4-bedroom, 2-bath home in Country Club Estates, offering a comfortable open layout, beautiful pond views, and a convenient Winter Haven location. With a brand-new roof, this home is ready for its next owner to move in and make it their own. Step inside to a bright, open living and dining area with high ceilings and plenty of natural light. The kitchen overlooks the main living space and features granite countertops, abundant cabinetry, a breakfast bar, and a functional layout that makes everyday living and entertaining easy. The spacious primary suite offers a private retreat with a large walk-in closet and an ensuite bath featuring a granite-topped vanity and tiled walk-in shower. Three additional bedrooms provide plenty of flexibility for family, guests, a home office, or hobby space. One of the home's best features is out back. The screened lanai overlooks the backyard and pond, creating a relaxing place to enjoy your morning coffee, unwind in the evening, or simply take in the peaceful water views. Step outside and enjoy the open backyard with **direct pond frontage and the opportunity to fish right from your own backyard. The location adds even more appeal. A brand-new Publix shopping complex is conveniently located just before the entrance to Country Club Estates, putting groceries and everyday necessities just minutes from home. You're also close to Downtown Winter Haven's restaurants, shopping, entertainment, and the area's Chain of Lakes, while LEGOLAND Florida Resort is just a short drive away. For those looking to enjoy everything Central Florida has to offer, Winter Haven provides convenient access toward Orlando and its world-famous theme parks, while also keeping Tampa, Clearwater Beach, St. Petersburg, and Florida's Gulf Coast within reach for day trips and weekend getaways. With four bedrooms, a brand-new roof, screened lanai, pond frontage, fishing opportunities, a two-car garage, and a highly convenient location, this Country Club Estates home brings together the features buyers are looking for in the Florida lifestyle.

4856 Summerfield Circle, Winter Haven

Listing courtesy of COLDWELL BANKER REALTY. 407-647-1211
625 Avenue B Sw, Winter Haven
$230,000
4 Beds ⋅ 4 Baths ⋅ O6439576 MLS
Investment opportunity in the heart of Winter Haven! This tenant-occupied duplex features two units, each offering one bedroom and one full bathroom, with approximately 1,240 square feet of total living space. Built in 1915, the property also includes a one-car garage and is connected to public water and sewer. Conveniently located near Downtown Winter Haven, shopping, restaurants, schools, medical facilities, and major roadways. Whether you are expanding your rental portfolio or purchasing your first income-producing property, this duplex offers excellent potential in a central location. Schedule your private showing today. Please do not disturb the tenants.

625 Avenue B Sw, Winter Haven

Listing courtesy of REAL BROKER, LLC. 855-450-0442
950 14th Street Ne, Winter Haven
$235,000
2 Beds ⋅ 3 Baths ⋅ L4965094 MLS
Virtually Staged. Price Improvement! Motivated Seller! NO HOA and a great Winter Haven location! Just two blocks from Lake Elbert and its paved walking trail, approximately one mile from Polk State College, and only two miles from Downtown Winter Haven, this quaint 1950s home offers 2 bedrooms, 2.5 baths, and 1,380 square feet of comfortable living space. The recently remodeled kitchen features a subway tile backsplash, stainless steel appliances, and good lighting that opens to spacious living areas, creating an easy, open flow throughout the home. Crown molding throughout adds character, while the retro bathrooms retain their original mid-century tile, with a full bathroom in each bedroom. The enclosed porch creates a light-filled sunroom, offering a wonderful additional space to relax or enjoy your morning coffee. An abundance of windows fills the home with natural light, while the generously sized bedrooms provide comfortable retreats. Outside, you'll find a two-car carport, an enclosed laundry room with a half bath, and a separate storage room. The fenced backyard features a patio area with plenty of possibilities for outdoor enjoyment. The roof, water heater, and A/C were replaced in 2021, and a new drain field was installed and septic pumped in 2019. The home also offers a proven rental history. Great Opportunity for a FHA 203K Loan. Vintage character, thoughtful updates, NO HOA, and a convenient location close to some of Winter Haven's favorite destinations!

950 14th Street Ne, Winter Haven

Listing courtesy of REMAX EXPERTS. adockery@remax.net
3247 Nightfall Rd., Winter Haven
$2,050
3 Beds ⋅ 2 Baths ⋅ 11983488 MLS
Stunning new home ready for move-in. When you walk into the house, you will have 2 bedrooms with access to sharing bathroom #2. The laundry room is also near the entrance, and it comes fully stocked with a full-size washer & dryer. Open floor plan with Kitchen, living area, and dining space. The kitchen includes a dishwasher, refrigerator, Microwave, and Range. Ample space to add additional furnishings that fit your lifestyle. You will enjoy the walk-in pantry closet with lots of extra storage. The primary bedroom also has a separate walk-in closet and the primary bathroom. All countertops are granite, and the house continues to have that new-built feel. Open patio perfect for growing, entertaining, playing, and enjoying the Florida sunny weather. The house has a garage ample enough for 2 vehicles. Just 3 miles to Hwy 27. About 5 miles from the new Crossroads Village Center. The location is perfect, with so much you can enjoy in Haines City and Winter Haven. Come see this gem before it is gone.

3247 Nightfall Rd., Winter Haven

Listing courtesy of Zoraya Colon with Elite Realty Agency, LLC
456 Adriel Avenue, Winter Haven
$349,900
4 Beds ⋅ 2 Baths ⋅ S5157711 MLS
Welcome to 456 Adriel Ave, where newer construction meets the space to actually spread out. Built in 2022, this thoughtfully designed 4-bedroom, 2-bath home offers approximately 1,874 square feet of living space on an impressive approximately half-acre homesite—a combination that can be hard to find among newer homes in Central Florida.Step inside to a bright, inviting floor plan designed for everyday living and easy entertaining. The kitchen serves as the heart of the home with dark cabinetry, light marble countertops, stainless steel appliances, generous prep space and a large peninsula that naturally connects the kitchen with the main living area. Just beyond, the living room adds personality with a distinctive tiled feature wall and fireplace, creating a comfortable gathering space with a modern touch.With four true bedrooms, the layout provides the flexibility today's buyers are looking for—whether that means additional bedrooms, a guest space, home office, hobby room or simply room to grow. The home's newer construction provides the clean, contemporary feel buyers want without the wait of building from scratch.But the story continues outside.The expansive fenced backyard offers the kind of room that changes how you live at home. There is space for pets, play, gardening, entertaining and creating your own outdoor retreat, along with an existing pergola/garden area that adds character to the setting. Whether you're enjoying a quiet Florida evening, hosting friends for a backyard cookout or simply appreciating the extra privacy and breathing room, this is outdoor space designed to be used—not just looked at.And then there is the location. Living in Winter Haven means enjoying a community known for its lakes and outdoor lifestyle, including the famed Chain of Lakes, along with boating, fishing and waterfront recreation. Downtown Winter Haven brings local restaurants, shops and community events together, while nearby shopping, dining and entertainment make everyday errands convenient. LEGOLAND Florida Resort and the area's many parks and recreational opportunities add even more to the Central Florida lifestyle.456 Adriel Ave isn't simply another newer home—it offers four bedrooms, modern living and the kind of homesite that gives you room to make the property your own. For added piece of mind, the fire station is only 5 minutes away. Newer home. Huge yard. Room to live.

456 Adriel Avenue, Winter Haven

Listing courtesy of RE/MAX HERITAGE PROFESSIONALS. 863-256-2188
6183 Grey Heron Drive, Winter Haven
$339,999
5 Beds ⋅ 4 Baths ⋅ L4965104 MLS
More than a home, this property offers the flexible space, storage, and energy-saving features today’s buyers are searching for! A standout bonus area provides incredible versatility with its own living space, closet, bathroom, and private rear entrance, making it ideal for multigenerational living, guests, a home office, or additional bonus rooms. Another bedroom features its own en suite bathroom for added comfort and privacy. Inside, enjoy granite countertops, upgraded lighting, ceiling fans throughout, and an abundance of closets and storage space. The dedicated laundry room includes cabinet storage, while a staircase in the garage provides convenient access to the attic for even more storage. Solar panels help keep monthly energy costs extremely low, even during Florida’s hottest months. Outside, the extended paver driveway offers additional parking and attractive curb appeal. The community features two swimming pools, a playground, and a walking trail. Enjoy a convenient Winter Haven location just minutes from Port 27 and the Chain of Lakes for easy lake access, as well as Downtown Winter Haven’s shopping, dining, and entertainment. The home is also approximately five minutes from Highway 27, providing easy travel to Orlando and surrounding areas, and is conveniently located near LEGOLAND Florida. This spacious and versatile home is ready for its next owner! This home is also available for rent! For rental details and lease information, please see MLS #L4965531.

6183 Grey Heron Drive, Winter Haven

Listing courtesy of TFP FLORIDA REALTY LLC. 863-337-9667
1100 Martinique Drive Unit 203, Winter Haven
$104,900
2 Beds ⋅ 1 Baths ⋅ L4964839 MLS ⋅ C BLDG.
Available for immediate occupancy, this lovely condo is updated and features low maintenance lifestyle with superb location. Located close to golf, fishing and water sports, close to LegoLand and shopping. The location is private and off the beaten path, ideal for a starter home or winter retreat. Upon entering the unit, you will note the fresh interior, open living area, and updated kitchen featuring stainless appliances with gas range and all new cabinetry and butcher block countertops. The community features laundry facilities and private mailboxes for security. Designated parking spaces for each unit. Close to LegoLane and Highway 27 for ease of commutes to all things Central Florida including golf, water sports, theme parks, and much more.

1100 Martinique Drive Unit 203, Winter Haven

Listing courtesy of FLORIDA REAL ESTATE COMPANY. 863-701-3487
2425 Gerber Dairy Road, Winter Haven
$660,000
2 Beds ⋅ 2 Baths ⋅ P4939858 MLS
Beautiful piece of property with 5.42 Arces of land. This home is a well built block home with a new metal roof that was just installed in June of 2026, new A/C installed. This a 2 bedroom / 2bath with 2 bonus rooms that can be easily converted into bedrooms making it 4 bedrooms. There is also an additional space added to the home with its own entrance that could be converted to a studio apartment to rent out, man cave, or a Lady lair you can make it what suits your needs. This home has a lot of potential and plenty of room to grow. Make an appointment to view and get the flu potential of the home and property. Some photo's have been virtually staged. Motivated Seller's !!

2425 Gerber Dairy Road, Winter Haven

Listing courtesy of KELLER WILLIAMS REALTY SMART 1. 863-508-3000
2639 San Marco Way, Winter Haven
$330,000
5 Beds ⋅ 4 Baths ⋅ L4965075 MLS
Short Sale. ** $17K PRICE REDUCTION as of 10/20/2026!** Short Sale — Third Party Approval Required. Welcome to 2639 San Marco Way, a spacious 5-bedroom, 3.5-bathroom two-story home offering 2,701 square feet of flexible living space in Winter Haven, FL. This short sale opportunity presents an excellent chance to acquire a generously sized home at an improved price point in an established Winter Haven community. The two-story layout provides excellent separation of space, with room for large households, multigenerational living, home offices, or guest accommodations. Five bedrooms and three and a half bathrooms give the kind of flexibility that is increasingly difficult to find at this price point. Conveniently located near shopping, dining, medical facilities, and the beautiful Winter Haven Chain of Lakes, with easy access to US-27 and major routes to both Orlando and Tampa. This is a short sale subject to lender approval. Being sold as-is. Buyer and buyer's agent to verify all information including HOA fees, community details, restrictions, measurements, and permitted uses. A rare opportunity to own a large Winter Haven home — schedule your showing today!

2639 San Marco Way, Winter Haven

Listing courtesy of KELLER WILLIAMS REALTY SMART 1. 863-508-3000
1220 33rd Street Nw, Winter Haven
$140,000
3 Beds ⋅ 1 Baths ⋅ S5157386 MLS
Great opportunity for investors and buyers looking for their next project! This property offers plenty of potential for those ready to bring their vision and creativity to the table. With no HOA, the next owner can enjoy added flexibility without the restrictions of a homeowners association. The property presents an opportunity to renovate, update, and create a space tailored to your goals. Whether you're looking for your next investment, rental property, or renovation project, this one is worth a closer look. The existing property provides a starting point for buyers looking to add value through improvements. Investors will appreciate the flexibility and potential this opportunity offers. Bring your contractor, ideas, and investment strategy and explore the possibilities. With the right vision, this property has the potential to become a valuable addition to your portfolio. Buyers looking for a project with upside potential will want to take a look. The property is conveniently located near everyday amenities and services. Enjoy the freedom of no HOA while planning your next steps. Opportunities like this are ideal for buyers ready to take on a project and make it their own. Don't miss the chance to explore the potential and possibilities this property has to offer. Schedule your showing today!

1220 33rd Street Nw, Winter Haven

Listing courtesy of EXP REALTY LLC. 888-883-8509
2015 Recker Highway, Winter Haven
$309,900
3 Beds ⋅ 2 Baths ⋅ L4965022 MLS
Virtually Staged. Under Construction. BRAND-NEW CONSTRUCTION –Welcome to this beautiful 3-bedroom, 2-bath home featuring 1,322 sq. ft. of living space with an open-concept floor plan. Thekitchen will feature shaker-style cabinetry, granite countertops, and stainless-steel appliances, with luxury vinyl plank flooring throughout the home. The exterior will be accented with stone veneer for added curb appeal. Additional features include an attached garage, covered front entry, and covered rear patio. Estimated completion in approximately 60–75 days. Secure this new construction home nand make it yours before completion! NO HOA, NO CDD! *Photos/renderings are for illustrative purposes only and may depict finishes, landscaping, furnishings, or features not included in the completed home.

2015 Recker Highway, Winter Haven

Listing courtesy of TRIBUTE REALTY LLC. 863-450-2910
464 Terranova Street, Winter Haven
$359,900
3 Beds ⋅ 2 Baths ⋅ TB8548427 MLS
Welcome home to this stunning 3-bedroom, 2-bathroom residence tucked into the sought-after, gated community of Terranova. From the moment you step inside, an open floor plan invites you through sun-filled living spaces accented by elegant crown moulding and custom built-ins. The chef-inspired kitchen anchors the home with generous counter space and a breakfast bar — perfect for casual mornings or entertaining guests. Plantation shutters throughout add a touch of timeless charm while offering privacy and light control in every room. Step outside to a spacious backyard, a blank canvas ready for weekend barbecues, a play area, or the pool of your dreams. Beyond your front door, Terranova's gated setting offers peace of mind just minutes from shopping, dining, and medical facilities — the perfect blend of tranquility and convenience. Don't miss this one — call today to schedule your private showing!

464 Terranova Street, Winter Haven

Listing courtesy of KELLER WILLIAMS TAMPA CENTRAL. 813-865-0700
606 Pavare Court Unit 606, Winter Haven
$129,900
2 Beds ⋅ 2 Baths ⋅ L4965031 MLS ⋅ Bay BLDG.
2 Bedroom/2 Bathroom downstairs Condo in Orchid Springs. Laminate flooring throughout. Kitchen with gas stove, stackable washer/dryer, and pass thru window to Dining area. Primary Bedroom has a walk in closet. Close to shopping, Legoland, and minutes to HWY 27. Call today for an appointment to view.

606 Pavare Court Unit 606, Winter Haven

Listing courtesy of LOCKHART & ASSOCIATES INC. 863-293-1234
97 Parson Drive, Winter Haven
$79,500
2 Beds ⋅ 2 Baths ⋅ G5117624 MLS
Become a share holder in this highly sought after 55+ gated community. If you are looking for the perfect retirement home, this one is for you! Peace-of-mind upgrades: Brand new roof installed March 2026, passed four-point inspection, and a four-year-old heat pump. Located in Orange Manor West, it is one of the most popular 55+ communities in Winter Haven and surrounding area with many amenities. Pool, shuffle board, putt putt, horse shoes, crochet, bingo, lake access and much more. Legoland is around one mile away which is great for visiting family. This is a 989 Square ft. 2 bedroom 2 bath 1984 Homes of Merit with an enclosed front facing Florida Room. The king size master bedroom has a walk-in closet and a private bathroom with a tub shower. The guest bedroom also has a walk-in closet. Affordable living with the monthly maintenance fee is $279.00 a month which includes cable, internet, trash pickup, and amenities. This house is fully furnished and ready to move in. This is also a pet free community. While it is a great winter home get away, it can also be a year round retirement home. Come see it today. This one won't last long. All measurements are approximate and should be verified by the buyer. The owner is offing a $1,674.00 discount off of the listing price towards the monthly dues for a full price contract.

97 Parson Drive, Winter Haven

Listing courtesy of MOSAIC SERVICES LLC. 352-414-5339
3344 Timberline Road W, Winter Haven
$225,000
2 Beds ⋅ 2 Baths ⋅ W7889482 MLS
This 2-bedroom, 1½-bath concrete-block home is located in Winter Haven. NO HOA, NO CDD, NON-FLOOD ZONE PER COUNTY RECORDS, UNDERGROUND POWER LINES AND A 2026 AC! The home features 22-foot vaulted ceilings throughout the living room, kitchen, family room and dining room. An attached oversized 1-car garage provides additional parking and storage space. Conveniently located near shopping, dining and major roadways. We welcome FHA, VA, conventional, and cash buyers. Only 1 Lucky Buyer gets to call this Home:)

3344 Timberline Road W, Winter Haven

Listing courtesy of KELLER WILLIAMS REALTY- PALM HARBOR. 727-772-0772
4401 Chambliss Road, Winter Haven
$1,100,000
3 Beds ⋅ 2 Baths ⋅ L4964769 MLS
Welcome to your slice of heaven in Winter Haven! Situated on just over 6.5 acres you will find this charming 3/2/2 Cassidy custom pool home surrounded by green meadows and mature oak trees. 4401 Chambliss Rd. offers space, freedom, and a lifestyle you simply won’t find inside typical neighborhoods. This expansive homestead provides room for horses, chickens, gardens, equipment, and future additions, all thanks to the no-HOA flexibility that lets you live the way you choose. There is a refreshing pool perfect for Florida summers and is surrounded by mature trees and wide-open land that create exceptional privacy. A large pond sits quietly among huge cypress trees on the property, adding a peaceful backdrop without dominating the landscape. Acreage of this size is almost unheard of in Winter Haven, making this a standout opportunity for anyone seeking space, seclusion, and the freedom to have a true country retreat while staying close to town conveniences. Updates include: HVAC 2018, Roof 2024, Water Heater 2018. 2 large sheds and large RV/Boat shed.

4401 Chambliss Road, Winter Haven

Listing courtesy of FLORIDA REAL ESTATE COMPANY. 863-701-3487
405 Avenue M Ne, Winter Haven
$298,000
O6441459 MLS
Investors, look no further! This fully renovated, block duplex in Winter Haven offers immediate cash flow with zero deferred maintenance. Both 1-bedroom, 1-bathroom units are fully occupied on 1-year leases generating income with tenants paying their own separate electric. Extensively updated in 2024, the property features a brand-new roof with a transferable 10-year workmanship warranty and 15-year unlimited wind rating, new mini-split A/C systems, and new tankless water heaters. Additional 2024 upgrades include interior and exterior paint, luxury vinyl plank flooring, remodeled bathrooms, updated kitchens with newer stainless steel appliances, modern light fixtures, ceiling fans, and closet organizers. Residents enjoy exceptional private amenities, including individual front porches, private driveways, personal outdoor storage units, and a shared rear laundry room equipped with a complimentary washer and dryer. The property is wrapped by a fully fenced yard with fresh 2024 landscaping.

405 Avenue M Ne, Winter Haven

Listing courtesy of LIFESTYLE INTERNATIONAL REALTY. 305-809-8085
71 Joppa Drive, Winter Haven
$40,000
2 Beds ⋅ 2 Baths ⋅ 11974087 MLS
Welcome to 71 Joppa Drive, a 2-bedroom, 2-full bath manufactured home in Orange Manor West Cooperative, a 55+ community offering a relaxed and active Florida lifestyle. Enjoy community amenities including a pool, clubhouse, shuffleboard, mini golf, fishing, boating, and social activities. Conveniently located near LEGOLAND, shopping, restaurants, lakes, and everything Winter Haven has to offer! Priced at just $42,500! A great opportunity to enjoy affordable Central Florida living.

71 Joppa Drive, Winter Haven

Listing courtesy of Patty Nee with Town and Country Mobile Homes Sales
604 Sarner Pass Way, Winter Haven
$318,000
4 Beds ⋅ 2 Baths ⋅ S5157377 MLS
A fantastic opportunity for investors or future homeowners! This beautiful corner-lot home features 4 bedrooms and 2 bathrooms, offering comfort, space, and excellent income potential. It boasts a beautiful, spacious kitchen. The open-concept layout seamlessly connects the living and dining areas, creating the ideal space for entertaining guests or enjoying everyday family life. Sliding glass doors open onto a large backyard—perfect for outdoor activities, gatherings, or simply relaxing. Additional features include a two-car garage, a fully equipped laundry room, and a well-designed floor plan that prioritizes functionality and comfort. Located in the desirable Lake Lucerne community, residents enjoy excellent amenities such as a clubhouse, swimming pools, a playground, and walking paths. The home is close to shops, restaurants, and major roads—including easy access to US-27—making for a convenient commute to Winter Haven, Davenport, and Orlando attractions. Don't miss out on this incredible opportunity!

604 Sarner Pass Way, Winter Haven

Listing courtesy of LPT REALTY, LLC. 877-366-2213
4629 Palmetto Drive, Winter Haven
$305,000
3 Beds ⋅ 2 Baths ⋅ TB8548042 MLS
Discover the opportunity to own a home in a convenient Central Florida location, surrounded by attractions, recreation, shopping, dining, and everyday conveniences. Enjoy easy access to LEGOLAND® Florida Resort, approximately 25 minutes away, as well as LEGOLAND Water Park and PEPPA PIG Theme Park. Winter Haven is also known for its beautiful Chain of Lakes, offering opportunities for boating, fishing, water activities, and enjoying Florida's outdoors. The area provides convenient access to local parks, restaurants, shopping, entertainment, and downtown Winter Haven. Its Central Florida location also makes it an excellent base for enjoying many of the region's popular attractions while maintaining a more relaxed residential lifestyle. Whether you're looking for a primary residence, a second home, a vacation property, or an investment opportunity, this property offers the chance to enjoy the best of Winter Haven and Central Florida living. Schedule your private showing today!

4629 Palmetto Drive, Winter Haven

Listing courtesy of MIRANDA LANDA REALTY GROUP LLC. 727-554-8198
1029 Hook Lane, Winter Haven
$76,000
2 Beds ⋅ 2 Baths ⋅ 11975643 MLS
Welcome to this charming and beautifully furnished 2-bedroom, 2-bath home in the desirable Swiss Golf & Tennis community in Winter Haven. Offering approximately 1,352 square feet of living space, this well-maintained home combines comfortable living with Florida charm and plenty of updates. Step inside to a bright and inviting interior featuring vinyl flooring throughout the main living areas and bedrooms. The spacious living room provides a comfortable gathering space and flows naturally toward the dining and kitchen areas. The cheerful kitchen offers abundant white cabinetry, generous counter space, stainless-steel appliances and a double sink. The home features two comfortable bedrooms, including a spacious primary bedroom with plenty of room for furnishings and a relaxing sitting/work area. Both bathrooms have been nicely maintained, and the primary bath features a double-sink vanity and an updated shower. One of the home's standout features is the 12' x 16' Florida room, adding approximately 192 square feet of additional living space. This versatile room is on the home's HVAC system, making it a wonderful space to relax, entertain, enjoy hobbies, or simply take in the Florida lifestyle. You'll also appreciate the inside laundry area, making everyday living convenient. Numerous important updates add peace of mind, including a 2023 central HVAC system and a 2023 shingle roof rated for 160-mph winds. The kitchen appliances have also been updated, including a newer refrigerator and dishwasher. The home also features updated plumbing/piping and double-pane windows in the living room. Outside, the home offers a welcoming covered entry and a large carport/driveway area, along with mature landscaping and colorful plantings that give the property wonderful curb appeal. The 2026 monthly lot lease is $632.05, which includes all the amenities of Swiss Golf and Tennis and Hidden Golf Club. Swiss Golf & Tennis is located on beautiful Lake Henry with opportunities to fish, go boating & enjoy the gorgeous sunsets. It is a very active 55+ Golf gated community. There are 2 clubhouses, 2 pools with Hot tubs, Fitness Room, Billiards Room, Library, Pro Shop for the 18-hole golf course, tennis court, and an onsite Restaurant and Pub with so much more! All listing information is considered reliable and appropriate by Sun Resales, Inc., but not guaranteed. Measurements are approximate. The buyer is responsible for verifying all current lot rent, fees, pass-on costs, community rules, regulations, and pet policies directly with the park manager. Sun Resales, Inc. is not responsible for quoting these terms. 1029 Hook Lane, Winter Haven, FL 33881 Out of town? No problem! We offer virtual showings and can complete all paperwork remotely for your convenience. Contact Cindy Minnick with Sun Resales today to schedule your personal or virtual tour!

1029 Hook Lane, Winter Haven

Listing courtesy of Cindy Minnick with Sun Resales, Inc.
1306 15th Street Sw, Winter Haven
$245,000
3 Beds ⋅ 2 Baths ⋅ TB8547534 MLS
3BR/2BA Beauty Near Downtown Winter Haven — Fully Updated Kitchen! Move right into this beautifully updated 3-bedroom, 2-bathroom home just minutes from downtown Winter Haven. The kitchen has been completely renovated with brand-new cabinetry, a stylish island, and gleaming granite countertops — a true showstopper for anyone who loves to cook or entertain. Ceramic tile flooring flows throughout the entire home for a clean, cohesive, low-maintenance feel. Enjoy an unbeatable location within walking distance of both Lake Shipp and Lake Howard — perfect for morning walks, fishing, or simply soaking in that classic Central Florida lake life. Downtown Winter Haven's shops, restaurants, and community events are just a short drive away. This home comes move-in ready with the refrigerator, stove, microwave, dishwasher, washer, and dryer all included. Major systems have been well maintained. No HOA means no extra fees and no added restrictions. Homes like this in this location don't sit on the market long — schedule your showing today!

1306 15th Street Sw, Winter Haven

Listing courtesy of MARK SPAIN REAL ESTATE. 855-299-7653
1711 Garden Lake Drive Unit 1711, Winter Haven
$159,900
1 Beds ⋅ 1 Baths ⋅ P4939856 MLS ⋅ Winterset Condo BLDG.
Virtually Staged. Welcome to a little slice of Florida paradise in Winterset, a GATED WATERFRONT COMMUNITY nestled along Winter Haven’s famous Chain of Lakes. This charming 1-bedroom, 1-bathroom condominium offers something truly special: a relaxed lakeside lifestyle, resort-style community amenities, and a home filled with unique spaces and thoughtful updates. Inside, the primary bedroom is wonderfully spacious and features a huge walk-in closet and en suite bathroom. But, one of the home's most delightful surprises is the fun overhead loft, creating flexible bonus space that could be the perfect home office, media area, reading nook, hobby space—or simply your own cozy hideaway. And when it comes to storage, you'll have plenty of room for all the things you don't want taking up your living space, thanks to additional interior AND exterior storage. Major updates mean you can settle in with confidence, too. The HVAC SYSTEM and WATER HEATER were both REPLACED in 2024, giving you two important big-ticket improvements already taken care of. Then there's the lifestyle... Step outside and enjoy everything Winterset has to offer. Take advantage of the community dock and lake access on the SE Chain's coveted Lake Winterset, spend a sunny afternoon at the pool and spa, meet friends at the clubhouse, or enjoy a friendly game of tennis or shuffleboard. When you're ready to get out on the water, Winter Haven's interconnected Chain of Lakes offers endless opportunities for boating, fishing, relaxing, and enjoying those beautiful Florida sunsets. The location is another reason to love this home. You're conveniently close to LEGOLAND Florida Resort, restaurants, grocery shopping, medical facilities, and everyday essentials, while downtown Winter Haven and its lakeside dining and local attractions are also just a few minutes away--whether by boat or by car. Whether you're searching for a full-time Florida home, a weekend retreat, a place to escape the cold, or simply a low-maintenance home where there's always something fun to do, this Winterset condo offers an appealing blend of comfort, character, recreation, and location.

1711 Garden Lake Drive Unit 1711, Winter Haven

Listing courtesy of JOHN WOOD REALTY, INC.. 863-324-9663

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