Timbertiderealty.com Search Results

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.

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

$44,990

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)

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

$319,090

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.

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

$335,000

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.

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

$290,000

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.

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

$230,000

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.

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

$349,900

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.

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

$339,999

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.

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

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.

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

$660,000

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 !!

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

$330,000

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!

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

$140,000

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!

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

$299,990

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.

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

$129,900

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.

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

$79,500

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.

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

$225,000

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:)

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

$1,100,000

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.

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

$298,000

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.

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

$40,000

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.

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

$318,000

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!

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

$305,000

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!

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

$76,000

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!

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.

$245,000

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!

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

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.

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

$215,000

Welcome to 6364 Lolly Bay Loop NE, a beautifully updated Winter Haven home offering comfort, value, and a convenient Central Florida lifestyle. This property features a **2023 roof, remodeled bathrooms, and new flooring**, giving buyers important major updates and a fresh, move-in-ready feel. Located in a peaceful residential setting, this home offers the opportunity to enjoy the relaxed Winter Haven lifestyle while remaining within convenient driving distance of Orlando and other Central Florida destinations. With access to major highways, nearby shopping, dining, outdoor recreation, and Winter Haven’s many lakes, this location offers the best of both convenience and tranquility. Whether you're looking for a primary residence, a place to settle down, or a home that offers more value for your money, this property is a great opportunity to make Central Florida living your own. Schedule your private showing today and come see all that this home has to offer!

2 Beds ⋅ 2 Baths ⋅ O6441156 MLS

Welcome to 6364 Lolly Bay Loop NE, a beautifully updated Winter Haven home offering comfort, value, and a convenient Central Florida lifestyle. This property features a **2023 roof, remodeled bathrooms, and new flooring**, giving buyers important major updates and a fresh, move-in-ready feel. Located in a peaceful residential setting, this home offers the opportunity to enjoy the relaxed Winter Haven lifestyle while remaining within convenient driving distance of Orlando and other Central Florida destinations. With access to major highways, nearby shopping, dining, outdoor recreation, and Winter Haven’s many lakes, this location offers the best of both convenience and tranquility. Whether you're looking for a primary residence, a place to settle down, or a home that offers more value for your money, this property is a great opportunity to make Central Florida living your own. Schedule your private showing today and come see all that this home has to offer!

6364 Lolly Bay Loop Ne, Winter Haven

Listing courtesy of EXP REALTY LLC. 407-706-5000

$244,000

BEAUTIFUL VILLA READY TO MOVE IN! A brand-new HVAC system (June 2026), along with new insulation throughout the attic. Features include cathedral ceilings, elegant detailed trimwork with decorative corner blocks throughout, new flooring, plantation shutters on the windows, and three sets of French doors. The upgraded kitchen features stainless steel appliances, double ovens, and a built-in pantry with pull-out shelves. A utility closet provides additional storage, and the interior laundry room includes a full-size washer and dryer. The primary bathroom features dual showers and two vanities with wood cabinetry, while the second bathroom includes a jetted bathtub and wood cabinet vanity. Both bathrooms also feature skylights. Golf course frontage and two outdoor patio areas, with one overlooking the 8th fairway, plus a second patio with concrete privacy walls. HOA fee includes roof replacement when needed, so you never have to worry about roof expenses. Cypresswood Country Club community offers golf, a Jr. Olympic-size pool, tennis courts, pickleball courts, a restaurant and bar, social events, live music three nights a week, and lush, well-maintained surroundings. Come take a look at this one!

2 Beds ⋅ 2 Baths ⋅ P4939773 MLS

BEAUTIFUL VILLA READY TO MOVE IN! A brand-new HVAC system (June 2026), along with new insulation throughout the attic. Features include cathedral ceilings, elegant detailed trimwork with decorative corner blocks throughout, new flooring, plantation shutters on the windows, and three sets of French doors. The upgraded kitchen features stainless steel appliances, double ovens, and a built-in pantry with pull-out shelves. A utility closet provides additional storage, and the interior laundry room includes a full-size washer and dryer. The primary bathroom features dual showers and two vanities with wood cabinetry, while the second bathroom includes a jetted bathtub and wood cabinet vanity. Both bathrooms also feature skylights. Golf course frontage and two outdoor patio areas, with one overlooking the 8th fairway, plus a second patio with concrete privacy walls. HOA fee includes roof replacement when needed, so you never have to worry about roof expenses. Cypresswood Country Club community offers golf, a Jr. Olympic-size pool, tennis courts, pickleball courts, a restaurant and bar, social events, live music three nights a week, and lush, well-maintained surroundings. Come take a look at this one!

2801 Wingfoot Court, Winter Haven

Listing courtesy of VILLAGE REALTY OF WINTER HAVEN. 863-299-6767

$225,000

NEW PRICE ON THIS ADORABLE & AFFORDABLE 3 BEDROOM CBS HOME WITH RECENT UPGRADES IS SITUATED ON A LARGE LOT AND NO HOA!!! The recent upgrades include new interior paint, new kitchen renovation with new appliances & granite countertops, new hot water heater, new light fixtures, new bifold doors, new window, new toilet, fixtures and vanity in the bathroom & more!!! Features include tile flooring throughout, kitchen has wood cabinets, granite countertops and all appliances. You'll enjoy the large, fenced back yard, one-car garage with extra room for storage. Centrally located in Winter Haven, the home is located at the end of a dead-end street for low traffic. Hurry & call today - make this home your own!!

3 Beds ⋅ 1 Baths ⋅ P4939828 MLS

NEW PRICE ON THIS ADORABLE & AFFORDABLE 3 BEDROOM CBS HOME WITH RECENT UPGRADES IS SITUATED ON A LARGE LOT AND NO HOA!!! The recent upgrades include new interior paint, new kitchen renovation with new appliances & granite countertops, new hot water heater, new light fixtures, new bifold doors, new window, new toilet, fixtures and vanity in the bathroom & more!!! Features include tile flooring throughout, kitchen has wood cabinets, granite countertops and all appliances. You'll enjoy the large, fenced back yard, one-car garage with extra room for storage. Centrally located in Winter Haven, the home is located at the end of a dead-end street for low traffic. Hurry & call today - make this home your own!!

707 Dolly Ben Court, Winter Haven

Listing courtesy of THE K TEAM REAL ESTATE SERVICES LLC. 863-604-1601

$274,000

Welcome home to this beautifully refreshed 3-bedroom, 2-bathroom home offering a comfortable layout, fresh updates, and an expansive backyard with plenty of possibilities. Step inside to discover all-new flooring and fresh interior paint, creating a bright, clean, and inviting atmosphere throughout the home. The spacious living areas provide a versatile setting for both everyday living and entertaining, with plenty of natural light adding to the welcoming feel. The well-designed floor plan offers three comfortable bedrooms and two full bathrooms, providing plenty of space for a variety of needs. The attached two-car garage adds valuable parking, storage, and everyday convenience. Outside, the sprawling backyard is one of the home's standout features, offering abundant space to entertain, garden, enjoy outdoor activities, or create your own private retreat. Whether you envision a large outdoor gathering area, garden space, play area, or simply room to relax and enjoy the outdoors, the possibilities are plentiful. With fresh interior updates, a functional layout, generous living space, an attached two-car garage, and an expansive backyard, this home is ready for its next chapter. Come see all that this refreshed home has to offer and schedule your showing today!

3 Beds ⋅ 2 Baths ⋅ TB8547254 MLS

Welcome home to this beautifully refreshed 3-bedroom, 2-bathroom home offering a comfortable layout, fresh updates, and an expansive backyard with plenty of possibilities. Step inside to discover all-new flooring and fresh interior paint, creating a bright, clean, and inviting atmosphere throughout the home. The spacious living areas provide a versatile setting for both everyday living and entertaining, with plenty of natural light adding to the welcoming feel. The well-designed floor plan offers three comfortable bedrooms and two full bathrooms, providing plenty of space for a variety of needs. The attached two-car garage adds valuable parking, storage, and everyday convenience. Outside, the sprawling backyard is one of the home's standout features, offering abundant space to entertain, garden, enjoy outdoor activities, or create your own private retreat. Whether you envision a large outdoor gathering area, garden space, play area, or simply room to relax and enjoy the outdoors, the possibilities are plentiful. With fresh interior updates, a functional layout, generous living space, an attached two-car garage, and an expansive backyard, this home is ready for its next chapter. Come see all that this refreshed home has to offer and schedule your showing today!

212 Majestic Gardens Lane, Winter Haven

Listing courtesy of EXP REALTY LLC. 888-883-8509

$765,000

Virtually Staged. Welcome to 3831 Gaines Dr, where beautifully updated interiors, exceptional outdoor living, and the best of the Winter Haven lifestyle come together. Situated on an impressive half-acre-plus homesite in the established Gaines Cove area, this immaculate 3-bedroom plus dedicated office home offers the space, privacy, and character that can be difficult to find. The location is a standout. Enjoy being just minutes from the Winter Haven Chain of Lakes, with multiple nearby options for boat ramps and lake access, making it easy to spend your days boating, fishing, skiing, or exploring Winter Haven’s interconnected lakes. LEGOLAND Florida Resort is also just minutes away, along with shopping, dining, and the everyday conveniences of the Cypress Gardens area. Inside, an inviting open floor plan welcomes you with spacious living areas designed for both everyday comfort and entertaining. Architectural details, abundant natural light, plantation shutters, and a fireplace with built-ins add warmth and character throughout. The beautifully updated kitchen features brand-new appliances and flows seamlessly into the main living area, while updated bathrooms and thoughtful improvements throughout create a polished, move-in-ready feel. A dedicated office with French doors provides the perfect space for working from home, studying, or additional flex space. The upgrades go well beyond what you immediately see. The home features a Kinetico water filtration system, allergen air filtration system, and a Tesla charging station, adding modern convenience and functionality to an already impressive property. Step outside and discover what truly sets this home apart. The expansive screened outdoor living area creates your own private Florida backyard retreat, centered around a heated saltwater pool with plenty of space for relaxing and entertaining. The substantial covered lanai features an impressive outdoor kitchen with built-in grill, vent hood, sink, and refrigeration, complemented by generous outdoor dining and seating areas. Remote-controlled power sun shades on the rear lanai provide added shade, privacy, and comfort at the touch of a button, making this incredible space even more enjoyable throughout the day. And unlike many pool homes, the backyard doesn't end at the screened enclosure. Beyond the pool is an expansive fenced yard with abundant usable green space, mature trees, and beautifully maintained landscaping. The combination of a large homesite, resort-style pool area, covered outdoor living, and substantial backyard creates a wonderful sense of openness and privacy. Curb appeal is equally impressive, with a large paver driveway, expansive front lawn, mature landscaping, and welcoming covered front porch creating a memorable first impression. Spend the morning boating on the Chain of Lakes, the afternoon relaxing in your heated saltwater pool, cook dinner in your outdoor kitchen, and finish the evening unwinding on the lanai. With LEGOLAND just minutes away and shopping, dining, recreation, and multiple lake-access options nearby, 3831 Gaines Dr offers more than a beautifully updated home—it offers the Winter Haven lifestyle.

3 Beds ⋅ 2 Baths ⋅ O6441050 MLS

Virtually Staged. Welcome to 3831 Gaines Dr, where beautifully updated interiors, exceptional outdoor living, and the best of the Winter Haven lifestyle come together. Situated on an impressive half-acre-plus homesite in the established Gaines Cove area, this immaculate 3-bedroom plus dedicated office home offers the space, privacy, and character that can be difficult to find. The location is a standout. Enjoy being just minutes from the Winter Haven Chain of Lakes, with multiple nearby options for boat ramps and lake access, making it easy to spend your days boating, fishing, skiing, or exploring Winter Haven’s interconnected lakes. LEGOLAND Florida Resort is also just minutes away, along with shopping, dining, and the everyday conveniences of the Cypress Gardens area. Inside, an inviting open floor plan welcomes you with spacious living areas designed for both everyday comfort and entertaining. Architectural details, abundant natural light, plantation shutters, and a fireplace with built-ins add warmth and character throughout. The beautifully updated kitchen features brand-new appliances and flows seamlessly into the main living area, while updated bathrooms and thoughtful improvements throughout create a polished, move-in-ready feel. A dedicated office with French doors provides the perfect space for working from home, studying, or additional flex space. The upgrades go well beyond what you immediately see. The home features a Kinetico water filtration system, allergen air filtration system, and a Tesla charging station, adding modern convenience and functionality to an already impressive property. Step outside and discover what truly sets this home apart. The expansive screened outdoor living area creates your own private Florida backyard retreat, centered around a heated saltwater pool with plenty of space for relaxing and entertaining. The substantial covered lanai features an impressive outdoor kitchen with built-in grill, vent hood, sink, and refrigeration, complemented by generous outdoor dining and seating areas. Remote-controlled power sun shades on the rear lanai provide added shade, privacy, and comfort at the touch of a button, making this incredible space even more enjoyable throughout the day. And unlike many pool homes, the backyard doesn't end at the screened enclosure. Beyond the pool is an expansive fenced yard with abundant usable green space, mature trees, and beautifully maintained landscaping. The combination of a large homesite, resort-style pool area, covered outdoor living, and substantial backyard creates a wonderful sense of openness and privacy. Curb appeal is equally impressive, with a large paver driveway, expansive front lawn, mature landscaping, and welcoming covered front porch creating a memorable first impression. Spend the morning boating on the Chain of Lakes, the afternoon relaxing in your heated saltwater pool, cook dinner in your outdoor kitchen, and finish the evening unwinding on the lanai. With LEGOLAND just minutes away and shopping, dining, recreation, and multiple lake-access options nearby, 3831 Gaines Dr offers more than a beautifully updated home—it offers the Winter Haven lifestyle.

3831 Gaines Drive, Winter Haven

Listing courtesy of COLDWELL BANKER REALTY. 407-647-1211

$329,000

Beautiful home featuring 4 spacious bedrooms and 2 bathrooms. The fully equipped kitchen boasts beautiful wood cabinetry and granite countertops. Sliding glass doors lead to a covered patio and a private, grassy backyard—perfect for relaxing and enjoying the Florida outdoor lifestyle. The home includes a 2-car garage and a fully equipped laundry room for added convenience. Situated in a desirable community, this property offers comfort, practicality, and excellent investment potential. It is conveniently located near LEGOLAND, Chain of Lakes Park, downtown Winter Haven, shopping centers, restaurants, grocery stores, and medical facilities, with easy access to Highway 27. Winter Haven is also known for its beautiful Chain of Lakes, offering opportunities for boating, fishing, and outdoor recreation. The property is currently leased at $2,000 monthly. A fantastic opportunity for both investors and future homeowners.

4 Beds ⋅ 2 Baths ⋅ S5157350 MLS

Beautiful home featuring 4 spacious bedrooms and 2 bathrooms. The fully equipped kitchen boasts beautiful wood cabinetry and granite countertops. Sliding glass doors lead to a covered patio and a private, grassy backyard—perfect for relaxing and enjoying the Florida outdoor lifestyle. The home includes a 2-car garage and a fully equipped laundry room for added convenience. Situated in a desirable community, this property offers comfort, practicality, and excellent investment potential. It is conveniently located near LEGOLAND, Chain of Lakes Park, downtown Winter Haven, shopping centers, restaurants, grocery stores, and medical facilities, with easy access to Highway 27. Winter Haven is also known for its beautiful Chain of Lakes, offering opportunities for boating, fishing, and outdoor recreation. The property is currently leased at $2,000 monthly. A fantastic opportunity for both investors and future homeowners.

507 Short Lane, Winter Haven

Listing courtesy of LPT REALTY, LLC. 877-366-2213

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