Winter Haven Homes with Florida Architectural style

4 Beds ⋅ 3 Baths ⋅ Willowbrook North SubDv. ⋅ 33881 Zip Code

Under Construction. This Castaway floorplan is available in farmhouse exterior designs. The inviting front porch opens to a gracious foyer with 2 adjacent secondary bedrooms and a full bathroom. The well-appointed island kitchen is open to the cafe area and spacious family room 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. A 3rd secondary bedroom, full bathroom and conveniently located laundry room complete the Castaway plan.

823 Andrew Street, Winter Haven

$286,000

3 Beds ⋅ 2 Baths ⋅ Villamar SubDv. ⋅ 33884 Zip Code

Under Construction. Brand new, energy-efficient home available by Sep 2026! Configure the flex room in the front of the home to an at home office space or hobby space for the kids. Past the foyer, the open kitchen flows to the dining space, great room and outside patio. Private primary suite offers a spacious area to relax. 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.

3933 Giorgio Drive, Winter Haven

$293,000

4 Beds ⋅ 2 Baths ⋅ Villamar SubDv. ⋅ 33884 Zip Code

Welcome to this like-new, four-bedroom home in the desirable Villamar community! Built in 2024 and offering nearly 2,000 square feet of beautifully designed living space, this inviting home combines modern comfort, thoughtful design, and effortless Florida living. Step inside to discover a light-filled, open-concept floor plan where the kitchen, dining area, and great room flow seamlessly together—perfect for both relaxed everyday living and memorable gatherings. The heart of the home is the spacious kitchen, featuring stone countertops, a large center island with breakfast bar, stainless steel appliances, and a generous walk-in pantry. The desirable split-bedroom layout provides added privacy, while the spacious primary suite offers a walk-in closet and a private bath with dual sinks. Ceramic tile enhances the main living areas, with soft carpeting adding comfort to the bedrooms. Sliding glass doors open to the patio and backyard, creating a wonderful space to enjoy morning coffee, outdoor dining, or Florida’s year-round sunshine. Additional highlights include energy-efficient appliances, windows, insulation, HVAC, lighting, low-flow fixtures, an irrigation system, and an attached two-car garage. Villamar residents enjoy access to a community pool, playground, park, sidewalks, and recreational facilities. With four bedrooms, nearly 2,000 square feet, and the peace of mind that comes with a home that is only two years young, this is a truly special opportunity to settle into a beautiful home and begin making memories of your own.

3785 Giorgio Drive, Winter Haven

$259,900

3 Beds ⋅ 2 Baths ⋅ Lake Daisy Estates SubDv. ⋅ 33884 Zip Code

Professionally remodeled and completely turnkey, this pristine 3-bedroom, 2-bathroom single-story home offers the ultimate in modern, low-maintenance living. Located approximately one mile from Cypress Gardens / LEGOLAND Florida, this property delivers an exceptional location paired with total peace of mind, featuring a brand-new roof, an attached two-car garage, and a private backyard with a convenient storage shed. Inside, the light-filled, open-concept floor plan showcases a spacious living and dining area with soaring vaulted ceilings, updated contemporary light fixtures, and brand-new wood-look luxury vinyl plank flooring that runs seamlessly throughout—completely carpet-free. The centerpiece of the home is the stunning, fully renovated kitchen equipped with premium quartz countertops, brand-new cabinetry, and a modern layout designed for entertaining. Both bathrooms have been completely updated, featuring new vanities, modern matte-black plumbing fixtures, and clean, bright wall tile surrounding the tub/shower combination. Finished with fresh paint inside and out, this high-end, zero-maintenance remodel is entirely move-in ready. Schedule your private showing today.

352 Lake Daisy Circle, Winter Haven

$329,090

4 Beds ⋅ 2 Baths ⋅ Villamar SubDv. ⋅ 33884 Zip Code

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

$336,970

4 Beds ⋅ 2 Baths ⋅ Villamar SubDv. ⋅ 33884 Zip Code

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

$249,900

2 Beds ⋅ 2 Baths ⋅ Cypresswood SubDv. ⋅ 33884 Zip Code

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

$344,990

4 Beds ⋅ 2 Baths ⋅ Willowbrook North SubDv. ⋅ 33881 Zip Code

Under Construction. Ready in December, 2026. 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 ensuite bathroom with dual sink vanity, shower, private water closet, and large walk-in closet. Photos are representative only and not of the actual home. Selections, features, and finishes may vary.

815 Andrew Street, Winter Haven

$385,000

3 Beds ⋅ 2 Baths ⋅ Terranova Ph 01 SubDv. ⋅ 33884 Zip Code

POOL HOME WITH POND VIEW IN GATED TERRANOVA! -NEW AC UNIT DECEMBER 2025--ROOF & HOT WATER HEATER ARE 6 YEARS OLD-- Welcome to this spacious 3-bedroom, 2-bath home offering 2,118 square feet of living space and a relaxing Florida lifestyle in one of southeast Winter Haven’s gated communities. The highlight of the home is the screened-in private pool overlooking the pond, creating a peaceful water-view backdrop for relaxing, entertaining, or enjoying time outdoors. Inside, the split-bedroom floor plan offers multiple living spaces, including a comfortable family room featuring a wood-burning fireplace. The eat-in kitchen provides plenty of space for casual dining and features a decorative backsplash behind the countertops, while the dining area flows naturally into the living room for an open and connected feel. Sliding doors provide access to the covered and screened pool area, where you can enjoy the pond views from your own backyard. The home also features a full bathroom with direct access to the pool area, adding extra convenience for family and guests. Additional features include an inside laundry room, walk-in closet, ceiling fans, attached 2-car garage, and a north-facing front exposure. Terranova is a gated community conveniently located in southeast Winter Haven with easy access to shopping, dining, schools, medical facilities, and area attractions including LEGOLAND Florida. Enjoy the combination of a private pool, water view, spacious interior, and gated-community setting—all in a convenient Winter Haven location. Schedule your private showing today!

543 Terranova Circle, Winter Haven

$533,000

4 Beds ⋅ 2 Baths ⋅ Hamilton Pointe SubDv. ⋅ 33881 Zip Code

Welcome to Winter Haven living, where comfort, thoughtful updates, and an exceptional outdoor setting come together in a home designed to be enjoyed inside and out. Step inside to an impressive oversized great room filled with natural light and finished in a fresh, neutral color palette. Updated tile and soft newer carpeting complement the formal living and dining spaces, creating a warm and inviting interior with plenty of room to gather, entertain, or simply relax. The kitchen features brand-new stainless steel appliances, along with a newer dishwasher, garbage disposal, and kitchen sink. Additional improvements throughout the home include a newer roof and updated tile in both the primary and guest bathrooms, adding to the home's move-in-ready appeal. Outside is where this property truly shines. Situated on a spacious oversized lot, the home offers a fully fenced, private backyard surrounded by mature landscaping, creating your own peaceful Florida retreat. The heated swimming pool is ready for sunny afternoons, evening swims, and weekends spent entertaining family and friends. A newer energy-efficient pool pump adds another valuable update, while the generous patio and pool area extend the home's living space outdoors. Set within a quiet, established neighborhood, the property also enjoys beautiful lake views and peaceful streets ideal for morning walks, bike rides, jogging, or an evening stroll with the dog. Publix, shopping, dining, medical offices, and everyday conveniences are just minutes away. And when you're ready for a day of Central Florida adventure, Walt Disney World is approximately 26 miles away, offering easy access to world-famous attractions while still allowing you to come home to the relaxed pace of Winter Haven. With its private heated pool, oversized lot, fenced backyard, mature landscaping, lake views, brand-new stainless steel appliances, and numerous recent updates, this home delivers the Florida lifestyle you've been looking for. Schedule your private showing and come see it for yourself.

318 Hamilton Shores Drive Ne, Winter Haven

$649,900

3 Beds ⋅ 4 Baths ⋅ Lake Winterset Acres SubDv. ⋅ 33884 Zip Code

This home extrudes the luxury vibe from the moment you approach it with its distinctive roof w/ a blue metal barrel tile appearance and circular driveway. Large manicured 1+ acre lot and oak trees. No HOA and is located behind Legoland. Overlooking Lake Winterset on the famous Winter Haven Chain of Lakes. Lots of room to spread out in over 3000 sq ft of a/c living space. The split floor plan has 3 bedroom and 3 1/2 baths. A large corner gas stone custom fireplace is the living area focal point. A front door 2-car carport covers your guests as they enter through the double doors into the formal foyer. A dedicated built-out office is just inside. A triple sliding glass door opens to the 30' wide covered lanai and to the back yard. Plenty of room for a pool. Full irrigation with a dedicated well. Large 37x11 studio provides extra air conditioned flex space. Additional bonus is the oversized 2-car garage AND a 12' tall 11'x37' RV/boat garage and both are air conditioned and with a polyaspartic floor coating. Separate attached outside storage room for lawn equipment.

2241 Winterset Road, Winter Haven

$1,399,900

4 Beds ⋅ 3 Baths ⋅ Magnolia Shores SubDv. ⋅ 33881 Zip Code

Welcome to your own private lakefront retreat on 1.23 acres along Lake Hamilton with NO HOA! This stunning 4-bedroom, 3-bath home offers an exceptional combination of luxury, entertaining space, and the ultimate Florida waterfront lifestyle. Bring your boat and jet skis and enjoy the convenience of a private dock featuring an electric covered boat lift and built-in fishing bench. The outdoor living space is truly spectacular! Step through the French doors to a sparkling saltwater PebbleTec pool featuring iridescent tile, fiber-optic lighting, a swim-up bar, fountains, and a roof-line waterfall. The propane-heated pool is surrounded by an expansive travertine deck, while the nearby gas fire pit with custom-cushioned seating creates the perfect setting for evening gatherings. Propane-connected tiki torches add a tropical ambiance, and a hidden sump pump provides worry-free drainage after storms. Entertaining is effortless with the outdoor kitchen, complete with a new grill and refrigerated drawers. The fenced backyard extends halfway to the lake, providing plenty of room for pets to play. Professional Florida-native landscaping, enhances the lush, resort-like setting. Inside, the beautifully designed chef's kitchen features quartz countertops, a copper farmhouse sink, paneled refrigerator, trash compactor, and spacious butler's pantry with a full-size refrigerator and abundant storage. The open floor plan includes a dedicated buffet area with dual wine refrigerators adjacent to the dining space—perfect for hosting family and friends. Nine-foot ceilings, crown molding, porcelain tile, shiplap accents, custom lighting, and a central vacuum system add comfort and sophistication throughout. The luxurious primary suite offers direct access to the pool deck, with a convenient open-air shower just outside. The ensuite features dual vanities and a walk-in shower with dual shower heads. The expansive walk-in closet includes a center island, custom shelving, heated towel rack, and an extra-large Liberty Safe. The home underwent a complete rebuild in 2017, so all features are 2017 or newer. Recent improvements include a new roof (2025), new pool pump (2025), a new 12x24 storage shed (2025) and new irrigation system (2025). The irrigation water comes from the lake so it doesn’t affect your water bill. Additional features include a split-bedroom floor plan, with two guest bedrooms sharing a Jack-and-Jill bath; hurricane shutters; a whole-home Generac generator; and TVs in every room, including the back porch. The spacious 3-car garage features tiled flooring, storage, a workshop, and an industrial ice maker. A pavered circular driveway provides ample parking, plus an additional parking pad with room for an RV. From the custom interior and exterior lighting to the custom painting, bamboo chair rail, and travertine exterior accents, every detail has been thoughtfully designed. The home is also pre-wired for ADT security at the front and rear doors and garage service door. Boating, fishing, entertaining, relaxing, and resort-style living—all in one exceptional Lake Hamilton property with no HOA!

3640 Crump Road, Winter Haven

Winter Haven Homes with Florida Architectural style

Newest Winter Haven Homes with Florida Architectural style