Winter Haven Homes with Sidewalk Exterior Features

Winter Haven Homes with Sidewalk Exterior Features

Welcome to Winter Haven, Florida – a charming city nestled in the heart of Polk County, known for its picturesque lakes and vibrant community spirit. With over 50 lakes, Winter Haven is often referred to as the "Chain of Lakes" city, where residents enjoy a plethora of outdoor activities, from boating and fishing to leisurely strolls along scenic waterfronts. The city’s rich history is complemented by a thriving arts scene, delightful dining options, and a variety of parks, making it an ideal place for families and individuals alike.

One of the standout features of homes in Winter Haven is their inviting sidewalk exteriors. These charming sidewalks not only enhance the aesthetic appeal of the neighborhoods but also promote a strong sense of community. Picture yourself taking evening walks with your loved ones, greeting friendly neighbors, or enjoying a morning jog along tree-lined streets. The sidewalks encourage an active lifestyle and foster connections among residents, making Winter Haven a welcoming place to call home.

Whether you’re looking for a cozy bungalow or a spacious family home, Winter Haven offers a diverse range of properties that cater to various tastes and budgets. With the added charm of sidewalks, these homes create a perfect backdrop for a vibrant community life. Explore the beauty and warmth of Winter Haven, where every day feels like a vacation, and find your dream home in this delightful city!

Newest Winter Haven Homes with Sidewalk Exterior Features

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$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
325 Majestic Gardens Drive, Winter Haven
$345,000
3 Beds ⋅ 3 Baths ⋅ Gardens Ph 01 SubDv. ⋅ 33880 Zip Code
Welcome to 325 Majestic Gardens Drive nestled in the desirable gated Gardens community of SE Winter Haven! This lovely home is situated on a spacious lot with a fully fenced backyard, various fruit trees, and nice curb appeal. The inviting open floor plan features a spacious eat-in kitchen, breakfast bar, an open living area, and a formal dinning room. The home offers dual primary bedrooms with private baths, an additional bedroom with a hallway bath, and a versatile office currently used as an extra bedroom. Enjoy your morning coffee or weekend barbecues in the back screened patio overlooking the generous backyard. Additional features include a two-car garage, indoor laundry room with utility sink, lawn IRRIGATION system, and a NEW ROOF installed in February 2025! Washer, dryer and select furniture are included. Conveniently located near LEGOLAND, local schools, shopping, dining and medical facilities. Don't miss this wonderful opportunity--schedule your private tour today.

325 Majestic Gardens Drive, Winter Haven
1783 White Elephant Loop, Winter Haven
$364,900
5 Beds ⋅ 3 Baths ⋅ Peach Crossings SubDv. ⋅ 33884 Zip Code
Virtually Staged. ONLY $1,000 DOWN AT SIGNING! BUILDER PAYS THE REMAINING CLOSING COSTS! PLUS, A PROMOTIONAL 4.99% INTEREST RATE FIXED FOR THE FIRST 5 YEARS WITH A 5/1 ARM FOR QUALIFIED BUYERS! BRAND NEW, MOVE IN READY SINGLE FAMILY HOME WITH 5 BEDROOMS AND 3 FULL BATHROOMS! Why wait months to build when you can move right into a beautifully designed new construction home with incredible builder incentives? Welcome to 1783 White Elephant Loop, featuring the spacious Spring floor plan by LGI Homes in the desirable Peach Crossings community. This impressive home offers five generously sized bedrooms, three full bathrooms, and a thoughtfully designed layout that combines modern comfort, functionality, and plenty of room to grow. Step inside to discover bright, inviting living spaces perfect for everyday living and entertaining. With five spacious bedrooms, you'll have endless possibilities for a home office, guest accommodations, playroom, fitness room, or hobby space. The exceptional owner's suite provides a relaxing private retreat with plenty of room for a king sized bed, additional furnishings, and a cozy reading area. The adjoining bathroom features a beautiful dual sink vanity, convenient linen closet, and an impressive walk in closet offering abundant storage and organization. Three full bathrooms provide added convenience for busy households and visiting guests. Enjoy the benefits of brand new construction, modern finishes, and the peace of mind that comes with owning a newly built home. Peach Crossings offers a welcoming community atmosphere with a children's playground and picnic area, along with convenient access to nearby schools, shopping, dining, and everyday essentials. Whether you're looking for additional bedrooms, flexible living spaces, or a beautiful new home without the construction wait, this property checks all the boxes! With builder paid closing costs, incredible promotional financing, five spacious bedrooms, and immediate move in availability, this is an outstanding opportunity to own brand new construction at an exceptional value. Schedule your private showing today! Promotional financing and closing cost incentives are subject to buyer qualification, participating lender requirements, and program availability. The advertised 4.99% interest rate applies to the initial five year fixed rate period of a 5/1 adjustable rate mortgage, after which the rate may adjust.

1783 White Elephant Loop, 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
3403 Julius Estates Boulevard, Winter Haven
$349,000
4 Beds ⋅ 3 Baths ⋅ Lake Smart Estates SubDv. ⋅ 33881 Zip Code
Enjoy comfortable living in this spacious home offering just under 2,400 square feet of living space in a convenient North Winter Haven location. Situated directly across from the community swimming pool, newly replaced AC this home offers easy access to neighborhood amenities, including a fishing pier. The backyard features a peaceful view overlooking a small pond, creating a relaxing setting to enjoy your outdoor space. The thoughtfully designed floor plan features an open and inviting downstairs living area with the living room, kitchen, and family room, while all bedrooms are conveniently located upstairs, providing added privacy. The kitchen is appointed with granite countertops, and the home also features a two-car garage and the added convenience of an upstairs laundry area with washer and dryer included. With quick access to Highway 27, getting around Winter Haven and the surrounding areas is a breeze. Enjoy the combination of spacious living, community amenities, peaceful water views, and a convenient location in this inviting home!

3403 Julius Estates Boulevard, Winter Haven
1803 4th Street Nw, Winter Haven
$125,000
3 Beds ⋅ 2 Baths ⋅ Annie O Maddox Subdivision SubDv. ⋅ 33881 Zip Code
A little retro, a lot of room to make it yours! This single story Winter Haven home pairs vintage details with a flexible layout, featuring 3 bedrooms, 1 full bath, and 1 half bath. A wall of windows brightens the wood paneled front room, where sliding glass doors lead into the living and dining area. The separate front room provides space for a home office, reading nook, or hobby room. A decorative arch opens from the dining area into the kitchen, where upper and lower cabinets, a tiled backsplash, and a double basin sink give you a starting point for a refresh. The full bath features a tub and shower combination with a distinctive vintage tile surround. Outside, a mature shade tree frames the driveway, and the covered carport leads to a screened porch with room for a pair of chairs. Brick accents add character to the exterior, and a separate shed provides storage for tools and outdoor gear. Whether you’re drawn to the original look or already picturing fresh flooring and a new color palette, there’s plenty of room to put your own stamp on this home.

1803 4th Street Nw, Winter Haven
2019 Kapree Court, Winter Haven
$330,000
3 Beds ⋅ 2 Baths ⋅ Winterset North SubDv. ⋅ 33884 Zip Code
Your Florida poolside retreat awaits! Welcome to this inviting 3-BEDROOM, 2-BATH POOL HOME with approximately 1,718 square feet, located on the north side of Lake Winterset in Winter Haven. Thoughtful updates, generous storage, and comfortable indoor and outdoor spaces make this home a standout—including RE-PLUMBING and a NEW GENERATOR that will convey with the sale! Step inside to a spacious living room where VOLUME CEILINGS and a NATURAL STONE WOOD-BURNING FIREPLACE create a welcoming setting for relaxing or gathering with guests. The UPDATED KITCHEN features MAPLE CABINETRY, newer appliances, an island with BREAKFAST BAR seating, and a large WALK-IN PANTRY. The adjoining dining area opens to the pool and patio, making entertaining flow easily outdoors. Enjoy your own backyard getaway with a SWIMMING POOL and a large COVERED, SCREENED PATIO with convenient bathroom access. The FULLY FENCED BACKYARD provides room to enjoy the landscaped setting, while a STORAGE BUILDING keeps outdoor essentials organized. Interlocking STONE PAVERS along the driveway and walkway add curb appeal, complemented by landscape lighting. The primary bathroom features CUSTOM CABINETRY, a solid-surface countertop, and a shower. An approximately 9-BY-13-FOOT INDOOR LAUNDRY ROOM offers a utility sink, built-in cabinets, and ample storage. The TWO-CAR GARAGE adds even more functionality with a workbench, tool storage, and a side exterior door. Additional highlights include DUAL-PANE INSULATED WINDOWS AND DOORS, HURRICANE SHUTTERS, and RADIANT BARRIER INSULATION. Conveniently located near shopping, restaurants, schools, and LEGOLAND, this home brings together practical upgrades and the outdoor lifestyle you love. Schedule your private showing today!

2019 Kapree Court, Winter Haven
427 W Lake Elbert Dr Ne, Winter Haven
$409,900
3 Beds ⋅ 3 Baths ⋅ Anna Mar SubDv. ⋅ 33881 Zip Code
Lakefront Paradise on Lake Elbert! Enjoy beautiful water views right from your front door! Spanning over 1,900 square feet of living space on a generous 0.52-acre lot, this home features a thoughtful layout to include a welcoming living room, a separate cozy family room, and a formal dining room overlooking the lake. The spacious kitchen boasts solid wood cabinets, beautiful countertops, and stainless steel appliances. The primary bedroom showcases stunning lake views along with its own ensuite bathroom complete with a walk-in shower and double vanity. The expansive fenced backyard offers plenty of room for outdoor entertaining. Don’t miss your chance to own this lakeside retreat—schedule your private tour today!

427 W Lake Elbert Dr Ne, Winter Haven
263 Oleander Street, Winter Haven
$275,000
4 Beds ⋅ 2 Baths ⋅ Lakes/Lucerne Park Ph 3 SubDv. ⋅ 33881 Zip Code
HOME SWEET HOME. Welcome! This well-located home offers 1,682 sq. ft. of living space and a peaceful setting in a newer, established community. One of the property’s standout features is the beautiful water view from the backyard, offering a relaxing backdrop for Florida living. The neighborhood offers a quiet and welcoming atmosphere while still providing convenient access to shopping, dining, everyday services, and major roadways. Whether you’re relaxing at home, enjoying the water view, or heading out to nearby conveniences, this property offers a great combination of comfort, location, and tranquility. See what this Winter Haven home has to offer and make it your own!

263 Oleander Street, 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
1501 N Lake Howard Drive, Winter Haven
$375,000
3 Beds ⋅ 2 Baths ⋅ Interlaken Add SubDv. ⋅ 33881 Zip Code
A rare 1945-lakefront home on Lake Howard along Winter Haven's highly sought-after Chain of Lakes. This central Florida waterfront property offers a 2BR/1BA main home plus a separate 1BR/1BA guesthouse currently used as a rental. The breezeway, (laundry rm), has a doorway from the main house leading into the guesthouse that has been sealed off, but could easily be opened again if a buyer wanted to merge the guesthouse into becoming part of the main home. The historic charm here is truly one of a kind w/ original hardwood floors running through much of the home, arched doorways between the rooms, & even the original front door w/ its antique turn-key doorbell. The living rm is anchored by a wood-burning fireplace w/ deep built-in shelving on each side, while large sweeping windows frame views of Lk Howard. The Florida rm/sun rm features wall-to-wall wrap-around windows, tile floor & a built-in window seat w/ storage, offering panoramic lake views & beautiful sunsets. An ornate stained glass divider leads from the sun rm into the dining rm, which showcases a stunning hand-painted mural of Old Florida lakefront scenery w/ the same blue herons, coots & anhingas you'll see right outside. The bathroom features an arched, tiled walk-in shower w/ a frameless glass enclosure. The spacious kitchen offers tile floors, tile countertops, a gas range, white cabinetry, a pantry & a breakfast-nook area w/ French doors that lead to the separate laundry rm, which features vintage mosaic tile floors & direct access to the brick walkway & the generously sized wrap-around wooden sun deck. The large .35-acre lot offers room for a garden, pool, or a private outdoor retreat. Just behind the main home, the guesthouse has its own charm, w/ a checkerboard woven wood ceiling & painted vintage mosaic tile floors. Its living area has sliders leading to its private covered patio. The guesthouse kitchen includes wood cabinetry, & tile floors while the tiled bathroom offers a step-in shower. The same tenant has called it home for approx. 4 years & rents month-to-month for $800/mo, making it a reliable income-producing property, a private space for guests, or a future extension of the main home. There are 3 carports plus 2 storage rooms. Across the street, your private lakefront features a boat dock w/ electric, newer decking & a boatlift that just needs a motor. This fixer-upper needs some TLC, but w/ this much character & potential on the Chain of Lakes, it is a rare chance to restore a true piece of Winter Haven history. All measurements are approx. & all info should be confirmed by buyer.

1501 N Lake Howard Drive, Winter Haven
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