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

$345,690
4 Beds ⋅ 2 Baths ⋅ Willowbrook North SubDv. ⋅ 33881 Zip Code
Beautiful Single Level, 2 Car Garage Home with Open Concept Living and 4 Bedrooms! The Baker plan is in Farmhouse exterior design. Adjacent the foyer you'll find 3 secondary bedrooms and a full bathroom. The well-appointed island kitchen overlooks the spacious family room and adjoining cafe with access to the covered lanai. The primary suite boasts an en suite bathroom with dual sink vanity, shower, private water closet, and large walk-in closet.

815 Andrew Street, Winter Haven
$106,000
2 Beds ⋅ 2 Baths ⋅ Lakeridge Condo SubDv. ⋅ 33881 Zip Code
**THIS CONDO IS PRICE TO SELL !!**CENTRAL FLORIDA 55+ Age GATED CONDOMINIUM COMPLEX WITH LAKE AND CITY VIEW. All new insulated windows throughout. This condominium provides 1,347 sq. ft. of living area & is located in the beautiful "Chain Of Lakes" City of Winter Haven, Fl. Very friendly complex w/ social activities offered if you wish to participate. Monthly association fee includes water, sewer, trash, fiber optic cable & internet, condo reserves, manager and use of recreational facilities. Lakeridge Condominiums offers a maintenance-free lifestyle w/ heated pool, tennis, shuffleboard, community room, gated entrances & covered assigned parking space. The large bright kitchen has plenty of cabinets & great counter space, appliances (dishwasher does not work) & pantry closet. The kitchen overlooks the 26'x14' great room that also adjoins the additional bonus space & storage closet. The 16X14 foot Primary bedroom suite has a walk in closet & bathroom w/ walk-in shower. Beautiful views of Spring Lake can be enjoyed from Primary bedroom & living areas. The 2nd bedroom & bath can be a private guest area or for your personal use for office, hobbies etc. The washer & dryer are included in the sale. Central heat and air conditioning. Convenient proximity to shopping, places of worship, groceries & restaurants. Extra assigned storage bin on same floor. Make this your full time home, winter home or investment property to update. Lakeridge Condominiums is an age-restricted, well-maintained & well-managed community. Sharepoint car charger provided for those with electric cars. Non-smoking property. 1 pet, 20 pounds or under may be approved.

1776 6th Street Nw Unit 304, Winter Haven
$379,000
4 Beds ⋅ 2 Baths ⋅ West Winter Haven SubDv. ⋅ 33880 Zip Code
Step into a piece of Winter Haven history—beautifully reimagined for modern living. Just moments from Lake Howard, this exceptional 1925 residence offers the character and craftsmanship today's luxury buyers crave, paired with a complete top-to-bottom transformation. Original refinished 101 year old hardwood floors and two sets of original French doors provide a timeless connection to the home's past, while the rest has been thoughtfully rebuilt with today's lifestyle in mind. The custom kitchen, elegant architectural details, crown molding, tray ceilings, and spacious living areas create a home that feels both sophisticated and inviting. The private primary suite is a true retreat, featuring his-and-hers walk-in closets and a spa-inspired ensuite with a two-person tiled shower, garden tub, and generous vanity space. Two additional bedrooms upstairs add flexibility for guests, family, or a private home office. With approximately 2,011 heated square feet, 4 bedrooms, 2 baths, a dedicated laundry room, fully fenced backyard, and no HOA, this is a rare opportunity to own something with genuine character—not another cookie-cutter home. Bring your boat and water toys and enjoy the freedom and lifestyle that come with living near Winter Haven's beautiful Chain of Lakes. For buyers who appreciate history, character, and modern luxury, this is a home that simply must be experienced in person.

2112 Avenue C Sw, Winter Haven
$145,000
3 Beds ⋅ 2 Baths ⋅ Imperial Harboursphases 01 & 02 SubDv. ⋅ 33880 Zip Code
**Welcome to Imperial Harbours, a beautifully maintained 55+ active community surrounded by gorgeous landscaping and offering access to Winter Haven’s Chain of Lakes!** This spacious **3-bedroom, 2-bath second-floor corner condo** offers over 1,226 sq. ft. of comfortable living with an open-concept living/dining area, lovely kitchen with beautiful countertops and abundant cabinetry, plus an enclosed bonus room perfect for an office, sitting area, or hobby space. The generous primary suite features a private bath and large walk-in closet. Enjoy the peace of mind of a **BRAND-NEW A/C**, newer double-pane windows, updated bathroom vanities, fresh interior paint, and an in-unit washer and dryer. Additional features include an exterior storage unit, elevator access, covered assigned parking, guest parking, and community car wash. Enjoy resort-style amenities including a **heated pool, fitness room, billiards, recreation room, shuffleboard, BBQ grills, gazebo, fishing, dock access, and nearby boat ramp.** HOA includes **water, internet, cable, and trash!** Conveniently located near hospitals, restaurants, shopping, and everyday essentials. **Come experience the Florida lifestyle at Imperial Harbours—schedule your private showing today!**

333 Lake Howard Drive Nw Unit 204D, Winter Haven
$279,900
4 Beds ⋅ 2 Baths ⋅ Lucerne Park Reserve SubDv. ⋅ 33881 Zip Code
Virtually Staged. Welcome to this beautiful one-story Freeport floor plan featuring 4 bedrooms, 2 bathrooms, an open-concept kitchen and great room, a private primary suite with a walk-in closet, a patio, and a two-car garage. The home also includes solar panels, offering incredible energy savings even during August, one of the hottest months of the year; the electric bill was under $20! The buyer must assume the existing solar-panel account. Don’t miss this wonderful opportunity to enjoy a comfortable home with significantly lower energy costs!

1020 Cambridge Drive, Winter Haven
$379,999
4 Beds ⋅ 3 Baths ⋅ Chestnut Crk SubDv. ⋅ 33881 Zip Code
SELLER MOTIVATED – MOVE-IN READY! Discover refined Florida living in the STUNNING SHENANDOAH II MODEL, an impressive SINGLE-STORY RESIDENCE offering 2,034 square feet of thoughtfully designed living space. Featuring 4 SPACIOUS BEDROOMS and 3 FULL BATHROOMS, this BEAUTIFULLY APPOINTED HOME blends ELEGANCE, COMFORT, and FUNCTIONALITY in a versatile layout designed for both everyday living and entertaining. From the moment you arrive, the CHARMING COLUMNED FRONT PORCH creates an inviting first impression. Step inside to a BRIGHT, OPEN-CONCEPT LIVING AREA where the seamless flow between the kitchen, dining, and living spaces creates an ideal setting for entertaining guests or enjoying relaxed evenings at home. The GORGEOUS KITCHEN is designed to impress, featuring PRISTINE SHAKER-STYLE CABINETRY, SAMSUNG STAINLESS STEEL APPLIANCES, a GENEROUS PANTRY, and a CHIC BREAKFAST BAR. The adjoining VERSATILE DINING AREA provides a welcoming space for everything from casual breakfasts to special gatherings. Throughout the main living areas and bathrooms, UPDATED 25-YEAR-LIFE-PROOF WOOD-VINYL FLOORING offers a SLEEK LOOK, while the bedrooms feature PLUSH STAIN-RESISTANT CARPETING for added comfort. These thoughtfully selected finishes combine BEAUTY, DURABILITY, and EVERYDAY PRACTICALITY. The SPACIOUS OWNER’S SUITE provides a peaceful retreat with a STYLISH TRAY CEILING, LARGE WALK-IN WARDROBE, and LUXURIOUS ENSUITE BATHROOM featuring DUAL SINKS and a BEAUTIFULLY TILED SHOWER accented by a GLASS ENCLOSURE. Step outside and embrace OUTDOOR LIVING on the EXPANSIVE COVERED LANAI, an inviting space for morning coffee, evening relaxation, or entertaining. Direct access to the THIRD FULL BATHROOM adds exceptional convenience for guests and outdoor activities. The LARGE BACKYARD provides a generous canvas for creating your own private outdoor retreat, with ample space to envision a future pool or customized outdoor living area, subject to applicable approvals and restrictions. Additional highlights include a 2-CAR GARAGE, ENERGY-EFFICIENT INSULATION, and ARCHITECTURAL SHINGLES, bringing together STYLE, EFFICIENCY, and PRACTICALITY. This EXCEPTIONAL HOME offers an appealing combination of BEAUTIFUL FINISHES, FUNCTIONAL DESIGN, SPACIOUS LIVING, and INDOOR-OUTDOOR COMFORT. If you’ve been waiting for a MOVE-IN READY RESIDENCE with room to personalize and make your own, this SHENANDOAH II MODEL deserves a closer look. WELCOME HOME!

1069 Sandpiper Loop, Winter Haven
$165,900
2 Beds ⋅ 2 Baths ⋅ Eagle Pond Condo SubDv. ⋅ 33884 Zip Code
Looking for a COUNTRY CLUB LIFESTYLE? Conveniently located in Cypresswood Golf & Country Club, on Dundee Rd near HWY 27. RECENT UPDATES INCLUDE a 2 year old AC unit, and in 2026 brand New hot water heater, countertops throughout, dishwasher, microwave, disposal and kitchen faucet. This SUPER CLEAN 2 bed/2 bath condominium offers an open concept with 10' Ceilings, Crown Molding, 2" Blinds and Ceiling Fans throughout. You will love the spacious kitchen with pantry & lots of counter space. Both bedrooms feature walk in closets. Ample amount of closet space plus an outside storage room & assigned parking. Cypresswood residents enjoy a resort and country club lifestyle! The 18 hole golf course and Clubhouse with chef prepared meals & live music are open to the public. Additional amenities include Brand New tennis & pickleball courts, plus a half Olympic size pool. Located just minutes from trendy downtown Winter Haven, convenient to Hwy 27 & I-4. Close to Legoland, Bok Tower, shopping, dining, hospital and medical facilities. Just 5 minutes to BRAND NEW Publix and ALDI grocery's, 7-11 gas station & McDonalds.

508 Eagle Pond Drive Unit 508, Winter Haven
$233,000
4 Beds ⋅ 2 Baths ⋅ Villamar Ph 4 SubDv. ⋅ 33884 Zip Code
Welcome to Winter Haven's Villamar Community! This home built in 2022 features 4 bedrooms, 2 bathrooms, a 2-car garage and 1707 square feet! At the main entry doorway, step to the left and find tucked away two secondary bedrooms sharing a full bathroom. Continue down the hall and step into the open concept floorplan with kitchen, family and dining room. The handsome kitchen has modern wood cabinets, island, stainless-steel appliances and closet pantry. Sliding doors off the dining room lead out to a patio and spacious backyard. Directly off the family room, find another small hallway with the third secondary bedroom and the Primary Suite - a great set up for a private home office. The primary suite includes walk in closet, dual sinks, and step in shower. Great location close to shopping, restaurants and interstate. It's good to be home! This property may qualify for Seller Financing (Vendee).

2586 San Marco Way, Winter Haven
$865,000
5 Beds ⋅ 3 Baths ⋅ Eloise Woods West Lake Florence SubDv. ⋅ 33884 Zip Code
Set along the shoreline of Lake Florence, this distinctive 0.83-acre waterfront parcel extends 367 feet in depth and includes 87 feet of lake frontage. Lake Florence is an independent 74-acre lake with a county-owned park but no public boat ramp. The property's concrete boat-launching pad, dock, boathouse, and lift provide on-site access for boating, water skiing, paddling, and fishing. The parcel contains two detached residences and is coded as Multiple SFR in Polk County property records. Together, the residences encompass 3,482 square feet of combined heated living space and 5,094 total square feet under roof, divided between a two-bedroom, two-bath primary residence with a flexible studio and a detached two-bedroom, one-bath cottage. The 2,311-square-foot primary residence, built in 1985, includes a spacious primary suite and a second bedroom configured as a den with fireplace and Murphy bed. The studio/flex room has its own side entry and an auxiliary appliance station with an 18-inch dishwasher, refrigerator and freezer drawers, ice maker, and microwave, adding flexibility for entertaining, guest accommodations, or additional living space. The recently updated kitchen features quartz countertops, a substantial island with seating for five, induction cooktop, double ovens, coffee bar, and generous pantry. Expansive sliding glass doors and the dining room's oversized window capture sweeping views of Lake Florence. New luxury vinyl plank flooring extends throughout the main living areas, while fresh interior paint complements the recent updates throughout the primary residence. The HVAC system was replaced in 2020. The primary bath includes a steam shower and refined vanity, while the secondary bath includes an oversized quartz vanity and newly installed Kohler shower. A 30-foot lakefront deck includes a screened area for additional outdoor living space. The detached 1,171-square-foot cottage, originally constructed in 1958, includes two bedrooms, one bath, a comfortable living area, and kitchenette, with crown molding throughout. Set apart from the primary home, it provides flexible separate living or workspace while remaining part of the unified property. A spacious 15-by-14-foot screened porch overlooks the surrounding landscaping. Each residence has its own electric meter and septic system; the primary residence's septic system was replaced in 2020. The homes share a water meter and driveway. Both residences feature concrete-block construction, new roofs, screened outdoor porches, interior laundry areas, and Ecobee thermostats. An additional washer and dryer are located in the cottage's attached garage. Major appliances in both residences convey with the property. The lakefront grounds provide open space for outdoor living and sunrise views across Lake Florence. Parking includes a 2.5-car carport, 1.5-car garage, and additional off-street parking. This uncommon combination of two detached residences, substantial covered area, boating infrastructure, and flexible living space distinguishes the property in Winter Haven.

2510 Cypress Gardens Boulevard, Winter Haven
$309,900
4 Beds ⋅ 3 Baths ⋅ Peace Crk Reserve SubDv. ⋅ 33884 Zip Code
Virtually Staged. Welcome to Florida Paradise in Winter Haven - a massive Chain of Lakes Area famous for the Legoland fun and outdoor activities! PRICED TO SELL! Almost Brand New Spacious 4 Bedroom / 2.5 Bathroom Home with a Community Pool and a Playground Access. Built in 2024 this Bright Modern house with an Open and Airy living/dining space combo concept is perfectly located in a nice neighborhood right across from the elementary school. Property Features include Modern Kitchen with Quartz Countertops equipped with Stainless Steel Appliances - stove, microwave, dishwasher, refrigerator/freezer, as well as a Laundry Area with Washer and Dryer included located on the second floor. Four Spacious Bedrooms with 2 Bathrooms are located upstairs; half a bathroom is located downstairs for your convenience. The Primary Suite comes with a Spacious Walk-In Closet, a beautifully Tiled Walk-In Shower and Dual Vanities. Three additional bedrooms and another full bathroom with a tub comfortably accommodate family and guests. Private Fenced Backyard with a Patio provides a peaceful outdoor retreat - perfect for after school hang outs, relaxing and entertaining. Community Amenities include a well-maintained Community Pool — perfect for warm Florida days and a Playground ideal for outdoor activities, walks and neighborly interaction. Convenient Location: just minutes away from major highways, this location provides an easy access to surrounding areas of Winter Haven and nearby towns. Shops, schools, pharmacies, parks and dining are all within short walking or driving distance. There are also Beautiful Lakes and Green Parks nearby for outdoor recreation. Ideal for a Primary Residence or a Long-Term Rental. This home is the perfect choice for a peaceful comfortable and convenient lifestyle in a fast-growing area. Schedule your private showing today for a chance to own this beautiful home in a desirable location!

1334 Diego Terrace, Winter Haven
$275,000
3 Beds ⋅ 2 Baths ⋅ Villamar Ph 2a SubDv. ⋅ 33884 Zip Code
Welcome to 1042 Corso Drive in Winter Haven! This beautiful 4-bedroom, 2-bath home offers a bright, open floor plan with modern finishes and plenty of space for comfortable living. The kitchen features ample cabinetry, modern appliances, and a walk-in pantry, opening to the spacious living and dining areas. The primary suite includes a private bath with dual vanities, soaking tub, and separate shower. Enjoy the Florida lifestyle from the screened-in patio overlooking the backyard. The home also features a 2-car garage and is located in the desirable Villamar community with resort-style amenities, including a community pool and playground. Conveniently located near LEGOLAND, shopping, dining, lakes, and major roadways with easy access to Tampa and Orlando. Schedule your showing today! Motivated seller.

1042 Corso Dr, Winter Haven
$298,080
3 Beds ⋅ 2 Baths ⋅ Crescent Pointe SubDv. ⋅ 33884 Zip Code
Crescent Pointe is a brand new community located in Winter Haven, FL, conveniently situated off State Rd 653 and boasting easy access to a range of nearby attractions. For residents who enjoy outdoor activities, the Winter Haven Chain of Lakes is nearby. It offers opportunities for boating, fishing, and other recreational activities. The community is also close to the bustling downtown area, where residents can explore local shops, dining venues, and family events. With NO CDD and low HOA, Crescent Pointe is an ideal place to call home in Winter Haven.

967 Lunar Lane, Winter Haven
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