Winter Haven Homes with Sidewalks Community Features

Winter Haven Homes with Sidewalks Community Features

Welcome to Winter Haven, Florida—a charming city nestled in the heart of Polk County that perfectly blends small-town warmth with vibrant community living. Known for its stunning lakes and picturesque landscapes, Winter Haven is often referred to as the "Chain of Lakes City," boasting over 50 sparkling lakes that offer endless opportunities for recreation and relaxation. Whether you enjoy boating, fishing, or simply taking in the serene views, you'll find a perfect spot to unwind in this beautiful locale.

One of the standout features of Winter Haven is its inviting neighborhoods, particularly those with sidewalks that foster a sense of community and connectivity. Homes with sidewalk access not only enhance the aesthetic appeal of the area but also promote an active lifestyle. Imagine morning jogs or evening strolls along tree-lined streets, where neighbors wave hello and children play safely. These communities are designed to encourage outdoor activities, making it easy to enjoy the year-round sunny Florida weather.

In addition to its scenic beauty, Winter Haven offers a rich array of amenities, including parks, shopping centers, and dining options that cater to every palate. The city is also home to the famous LEGOLAND Florida Resort, making it a fantastic destination for families and thrill-seekers alike. With a strong sense of community and a welcoming atmosphere, Winter Haven is not just a place to live; it’s a place to thrive. Come explore the delightful homes with sidewalks that invite you to discover the joys of life in this enchanting city!

Newest Winter Haven Homes with Sidewalks Community Features

1711 Carnostie Road, Winter Haven
$279,000
3 Beds ⋅ 2 Baths ⋅ Villamar SubDv. ⋅ 33884 Zip Code
**MODERN LIVING, QUALITY CONSTRUCTION, AND RESORT-STYLE AMENITIES IN THE HEART OF WINTER HAVEN!** Welcome to 1711 Carnostie Road, an immaculate 2022-built home in the desirable VillaMar community. Offering 3 bedrooms, 2 bathrooms, and 1,415 square feet of thoughtfully designed living space, this home combines the comfort of newer construction with a location that puts some of Central Florida's favorite attractions and outdoor activities within easy reach. Step inside and you'll appreciate the open floor plan, inviting living spaces, and a split-bedroom design that provides privacy without sacrificing functionality. Whether you're purchasing your first home, looking to simplify your lifestyle, or searching for an investment property, this home offers a layout that makes excellent use of every square foot. **BUT IT'S THE DETAILS, BOTH SEEN AND UNSEEN, THAT MAKE THIS HOME EVEN MORE APPEALING!** Built with 16-inch-on-center stud framing, R-38 insulation, architectural roof shingles, and a built-in Taexx pest control tubing system, this home offers thoughtful construction features designed with durability, efficiency, and convenience in mind. Inside, 5¼-inch baseboards add a polished finishing touch throughout. These are the details that may not immediately stand out during a showing but certainly deserve your attention. Beyond the home itself, VillaMar offers a resort-style community swimming pool, playground, sidewalks, and community spaces where you can enjoy the Florida sunshine without the upkeep of a private pool. And the location? That's another reason to take a closer look! Just a short drive from LEGOLAND Florida Resort and Winter Haven's beautiful Chain of Lakes, where boating, fishing, waterfront dining, and outdoor recreation are all part of the local lifestyle. Convenient access to Highway 27 makes shopping, dining, commuting, and exploring Central Florida easy. Whether you're a first-time homebuyer, relocating to the area, looking to downsize, or adding to your investment portfolio, this beautifully maintained home offers quality construction, modern comfort, and a location with plenty to enjoy. WHY WAIT TO BUILD WHEN YOU CAN ENJOY THE BENEFITS OF NEWER CONSTRUCTION TODAY?** Schedule your private showing and discover everything 1711 Carnostie Road has to offer!

1711 Carnostie Road, Winter Haven
235 Golf Aire Boulevard, Winter Haven
$300,000
3 Beds ⋅ 3 Baths ⋅ Lake Bess Country Club SubDv. ⋅ 33884 Zip Code
Move-In Perfect Golf Course Home on Nearly 1/3 Acre: Fourth Hole Views, Florida Room & Free Golf! Tee up the Florida lifestyle in this immaculate 3-bedroom, 2-bath home that truly needs nothing! Set on nearly a third of an acre along the 4th hole of Lake Bess Country Club & Golf Course, it enjoys sweeping fairway views while sitting perfectly positioned to stay clear of stray golf balls. Inside, a split-bedroom open plan, high ceilings, and solid surface countertops create a bright, easy flow. The primary suite offers an ensuite bath and two large walk-in closets, and an interior laundry room adds everyday convenience. The Florida room overlooks the course, making it the perfect spot for morning coffee or sunset views. Outside, mature landscaping with a majestic oak and magnolia trees frames the property. The large garage includes a side golf cart door, ready for your daily rounds. *Peace of mind is built in!* The tile roof was professionally inspected and resealed in 2023. Both the indoor air handler and outdoor A/C unit were replaced in 2023, and the hot water heater was replaced in August 2026. Additional updates include new front windows, a new refrigerator, and updated electrical breakers. Tucked past the clubhouse on a quiet dead-end street, it is a peaceful corner of the community. POA dues cover free golf, driving range, putting, pool and clubhouse access, grass cutting, and tree and bush trimming. No rentals allowed. Minutes from Legoland, Hwy 27, and I-4. More time for you to enjoy Florida living!

235 Golf Aire Boulevard, Winter Haven
3941 Giorgio Drive, Winter Haven
$275,000
3 Beds ⋅ 2 Baths ⋅ Villamar SubDv. ⋅ 33884 Zip Code
Under Construction. Brand new, energy-efficient home available by Jan 2027! Open floor plan with a lot of flexibility. Retreat to your primary suite that is conveniently situated in the back of the home for plenty of privacy and offers a huge walk-in closet and bathroom with dual sink vanity and standalone shower. 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.

3941 Giorgio Drive, Winter Haven
4314 Mandolin Boulevard, Winter Haven
$315,000
4 Beds ⋅ 2 Baths ⋅ Mandolin SubDv. ⋅ 33884 Zip Code
NEW EXTERIOR PAINT (2026), NEW WATER HEATER (2026), NEW ROOF (2025) AND SOLAR PANELS TO BE PAID OFF BY THE SELLERS AT CLOSING! Welcome to this spacious 4 bedroom, 2 bath home in the desirable gated community of Mandolin in SE Winter Haven. Situated on a 0.27 acre lot, this home combines valuable improvements, an open floor plan and energy savings, with seller-reported electric bills averaging approximately $20 per month. Elevated ceilings create an airy, welcoming feel throughout the main living spaces. The spacious great room offers easy access to the screened lanai, extending your living space outdoors for relaxing or entertaining. The kitchen features a breakfast bar, closet pantry, a Samsung Bespoke 4 door French door refrigerator, a 2025 microwave hood, along with an adjoining dining area perfect for everyday meals or intimate gatherings. The split bedroom layout provides privacy for the primary suite, which features a tray ceiling, walk-in closet and an ensuite bathroom with dual sinks, a walk-in shower, soaking tub and private water closet. Three additional bedrooms offer ample space and convenient access to the second bathroom, complete with a tub and shower combination. An inside laundry room, fully equipped with a washer and dryer, and a 2 car garage add everyday convenience, while additional features include a water purification and softening system, foyer coat closet, hall linen closet, rain gutters and more. Mandolin offers community sidewalks for evening strolls and a convenient location just minutes from a brand-new Publix, Walmart, schools, dining and medical facilities. Centrally located between Tampa and Orlando, this home also offers easy access to Central Florida’s world-famous theme parks and Florida’s beautiful beaches. Come discover what Central Florida living is all about!

4314 Mandolin Boulevard, Winter Haven
3391 Livingston Way, Winter Haven
$215,000
2 Beds ⋅ 2 Baths ⋅ Traditions Ph 1 SubDv. ⋅ 33884 Zip Code
Welcome to your Florida retreat! This beautifully maintained 2-bedroom, 2-bathroom FURNISHED home offers low-maintenance living in a gated Winter Haven community filled with resort-style amenities! Whether you're searching for a full-time residence or seasonal getaway, this home is ready for you to move right in! Enjoy peace of mind with numerous updates, including a roof approximately 5 years old, NEW A/C February 2026, NEW range 2026, refrigerator approximately 2 years old, microwave 1 year old, and carpeting approximately 5 years old. Spend less time maintaining and more time enjoying Florida! The HOA takes care of exterior painting and front landscaping. Additional included services feature cable TV, internet, grounds maintenance, private roads, community pool, recreational facilities, management, and common area taxes. LOVE THE WATER? Enjoy lake access, community boat ramp, boat slips, dock, fishing, and beautiful waterfront areas! Cruise the neighborhood in your golf cart or enjoy the walking paths and sidewalks. Community amenities include a clubhouse, fitness center, swimming pool, tennis courts, dog park, parks, and gated entry! Conveniently located near shopping, dining, medical facilities, and Central Florida attractions. EXCITING PROPERTY TAX NEWS! With Florida's newly approved Amendment 3, establishing Florida residency by December 31, 2026, may qualify eligible homeowners for expanded homestead tax benefits without the new-resident waiting period! Residency and exemption requirements apply. Why spend another winter wishing you were in Florida? This furnished home offers comfort, convenience, and the Florida lifestyle you've been dreaming of! Schedule your private showing TODAY! Buyer approval and community restrictions apply. Verify HOA benefits, amenity availability, and tax eligibility.

3391 Livingston Way, Winter Haven
3123 Laurel Oak Ln, Winter Haven
$315,000
4 Beds ⋅ 2 Baths ⋅ Villamar Ph 6 & Ph 6d SubDv. ⋅ 33884 Zip Code
Short Sale. A Must-See! Beautifully designed 4-bedroom, 2-bathroom home with a 2-car garage, presenting 1,983 square feet of living space with a bright and airy open floor plan and high ceilings. Perfect for families or anyone who loves to entertain, this home seamlessly blends style, comfort, and functionality. The kitchen boasts ample counter space, a breakfast bar, stainless steel appliances, solid wood cabinets, and even a pantry. Strategically located just off the kitchen, the laundry room offers additional storage space. Enjoy gorgeous, durable vinyl flooring throughout the main living areas and cozy carpet in the bedrooms for ultimate comfort. The expansive primary bedroom highlights a walk-in closet and en suite bathroom complete with a double vanity and large step-in shower. The welcoming, screened-in front porch and lovely landscaping provide great curb appeal. Step out back through sliding glass doors to a second screened porch overlooking the fenced-in backyard, great for relaxing, weekend gatherings, or enjoying your morning coffee. Located in Villamar! Low annual HOA fee; the amenities include a community pool at the main entrance of the neighborhood on Cunningham Dr., along with a playground. This pristine home is ready to welcome its next owners. Don't miss the opportunity to make this beautiful home yours!

3123 Laurel Oak Ln, Winter Haven
4000 Giorgio Drive, Winter Haven
$325,000
4 Beds ⋅ 3 Baths ⋅ Villamar SubDv. ⋅ 33884 Zip Code
Brand new, energy-efficient home available by Dec 2026! First-floor primary suite ensures everyone has their own private space. Second floor offers a spacious loft that can be used to best fit your family's needs. Enjoy preparing meals with your family in the open kitchen with spacious work island. 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.

4000 Giorgio Drive, Winter Haven
1550 11th Street Ne Unit C5, Winter Haven
$115,000
2 Beds ⋅ 2 Baths ⋅ Lake Buckeye Condo SubDv. ⋅ 33881 Zip Code
This updated unit has 1,148 sq ft of living space, with new flooring, new countertops and plenty of natural light throughout. The kitchen has a large pantry, and the washer and dryer are in the unit. Step out onto the balcony for direct views over Lake Buckeye. Both bedrooms are a good size with large closets, and the primary bedroom has its own private bathroom. Residents can use the community pool. The unit is currently leased at $1,150 a month, and the lease continues after closing, so the buyer takes over an existing tenancy and income from day one. Showings are by appointment only, with notice to the tenant. Information is deemed reliable but not guaranteed. Buyer to verify square footage, lease terms, HOA fees and rules, and all other details.

1550 11th Street Ne Unit C5, Winter Haven
2037 San Marcos Drive Se Unit 325, Winter Haven
$180,000
2 Beds ⋅ 2 Baths ⋅ Park Lake 02 SubDv. ⋅ 33880 Zip Code
Enjoy city convenience Living in this 2-bedroom, 2-bath in Winter Garden Chain of Lakes Condo. Relax on private dock, fish or swim in the community pool. This home blends style with comport. Low maintenance and ready for your personal touch. Easy access from top shopping , dining, and entertainment-- perfect as a week-end getaway, or year round home. Come check and see for the opportunity to own or investment possibilities. Must be sold. Seller may hold first mortgage with a good down payment.

2037 San Marcos Drive Se Unit 325, Winter Haven
5780 Lakeside Landings Boulevard, Winter Haven
$290,000
4 Beds ⋅ 3 Baths ⋅ Lakeside Landings Ph 01 SubDv. ⋅ 33881 Zip Code
Enjoy peaceful pond views and spacious living in this 4-bedroom, 2.5-bathroom, two-story home in Winter Haven! Built in 2016, this 2,526-square-foot home offers plenty of room to spread out and enjoy comfortable everyday living. Major updates include a roof replacement in late 2023 and exterior paint completed shortly afterward. The A/C has also been recently serviced for added peace of mind. Located in an established community of Lakeside Landings featuring sidewalks, a neighborhood pool, and a playground, there are plenty of opportunities to enjoy the outdoors. Conveniently situated near Lake Fannie (part of the Chain of Lakes) off Lucern Park Rd, with easy access to Hwy 27, shopping, dining, and other everyday conveniences, this home puts you within reach of all that Winter Haven and Central Florida have to offer. Don't miss the opportunity to make this spacious home your own!

5780 Lakeside Landings Boulevard, Winter Haven
1606 Eagle Pond Drive, Winter Haven
$155,000
2 Beds ⋅ 2 Baths ⋅ Eagle Pond Condo SubDv. ⋅ 33884 Zip Code
Step into an inviting opportunity and a genuine deal at this price in the desirable Cypresswood Golf & Country Club. Whether you’re seeking a comfortable full-time residence, a relaxing winter retreat, or a place to embrace an active Florida lifestyle, this second-floor 2-bedroom/2-bathroom condo delivers warmth, convenience, and a true sense of community.Enjoy the privacy of an upper-level location with a practical, easy-flow layout designed for comfortable living, plus a convenient storage room for extra belongings. Maintenance-free ownership means the HOA handles exterior and ground maintenance, community pool access, 24-hour security, common-area upkeep, trash service, exterior pest control, and private road maintenance—so you can simply enjoy your home.The convenient location, a short drive to Legoland Florida Resorts, and offers easy access to Hwy 27, making shopping, dining, medical facilities, and everyday errands quick and simple while still keeping you nestled in a peaceful community setting. Residents are welcomed into a lifestyle filled with amenities: a championship 18-hole golf course, on-site restaurant & clubhouse for dining & events, sparkling community swimming pool, tennis courts & pickleball courts, and fitness center. Perfectly positioned for those who value both relaxed living and an active community atmosphere, this condo offers exceptional value and an immediate sense of belonging in one of Winter Haven’s most appealing settings. Schedule your private showing today and experience the lifestyle for yourself. All buyers must provided a pre-approval letter or proof of funds. Buyers are responsible for verifying the accuracy of all information.

1606 Eagle Pond Drive, Winter Haven
188 Black Skimmer Lane, Winter Haven
$285,000
3 Beds ⋅ 2 Baths ⋅ Lake Deer SubDv. ⋅ 33880 Zip Code
WELCOME HOME! Discover this beautiful single-family home featuring 3 bedrooms, 2 bathrooms, and 1,720 square feet of living space, built in 2020 and located in Winter Haven! Designed with comfort and functionality in mind, this residence showcases a beautiful open floor plan that seamlessly connects the kitchen, dining, and living areas, creating a spacious and inviting atmosphere perfect for everyday living and entertaining. The modern kitchen features elegant granite countertops, stainless steel appliances, and a functional layout that makes meal preparation and gatherings a pleasure. The spacious primary bedroom provides a comfortable retreat, while two additional bedrooms allow flexibility for guests, a home office, or additional living needs. ONE OF THE PROPERTY'S STANDOUT FEATURES IS THE SOLAR PANEL SYSTEM, WHICH WILL BE PAID IN FULL BY THE SELLER AT CLOSING, allowing the new owner to enjoy the potential benefits of lower electricity bills without assuming the existing solar financing. Step outside to your fully fenced, private backyard, an ideal setting for outdoor gatherings, weekend barbecues, pets, or simply relaxing in the Florida sunshine. The property also features a SPACIOUS 2-CAR GARAGE, providing ample room for parking and additional storage. Conveniently situated near shopping, dining, schools, and major roadways, this home combines the appeal of newer construction with everyday convenience. Whether you're searching for a primary residence or an investment opportunity, this property is an excellent choice. Don't miss this fantastic opportunity! Schedule your private showing today!

188 Black Skimmer Lane, Winter Haven
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