Winter Haven Homes with Florida Architectural style

2 Beds ⋅ 2 Baths ⋅ Traditions Ph 02 SubDv. ⋅ 33884 Zip Code

UPGRADED HOME IN THE GATED RESORT-STYLE COMMUNITY OF TRADITIONS: Meticulously maintained and thoughtfully upgraded 2 bedroom, 2 bath home with a versatile den that can easily serve as a 3rd bedroom, located in the desirable Traditions at Lake Ruby community. Enjoy comfortable living and an active lifestyle in this gated 55+ community in Winter Haven. This beautifully maintained home features extensive improvements, generous outdoor living space and transferable home warranty until April of 2030. The open floor plan brings the great room and kitchen together for easy everyday living and entertaining. New laminate flooring adds warmth, while the kitchen features quartz countertops, an island with seating and pendant lighting, stainless steel appliances including a double oven with air-frying and microwave capabilities and a closet pantry. An adjoining dinette provides a casual dining spot, while the formal dining room offers an inviting setting for intimate dinners and holiday gatherings. The spacious primary suite features a tray ceiling, a walk-in closet with custom built-ins and an ensuite bath with a quartz countertop, dual sinks, a handicap accessible walk-in shower and a private water closet. The comfortably sized secondary bedroom is conveniently situated near the guest bathroom, which features a new walk-in shower. An interior laundry room with storage cabinets adds everyday convenience. Three sets of sliding doors create a natural connection to the expansive covered and screened lanai. Finished with paver flooring, this generous outdoor space offers room for relaxing, dining and hosting larger gatherings. A separate paver patio just outside the enclosure provides a convenient grilling area, while refreshed tropical landscaping enhances the setting. Enjoy added peace of mind in Florida with a new roof installed in 2024 and a 2024 Generac 24kW whole-house generator with a transferable warranty and powered by a 500-gallon buried propane tank capable of providing up to three weeks of backup power eliminating much of the stress and uncertainty associated with unexpected power outages, whether short-term or extended. Additional significant improvements made in 2023/2024 include new interior and exterior paint, new laminate flooring and a Puragain water purification system with reverse osmosis in the kitchen. The two-car garage features screen doors, epoxy flooring, a 240-volt connection for electric vehicle charging and attic stairs. Additional features include surround sound, an ADT security system, an irrigation system with a separate irrigation meter, rain gutters, a paver driveway and walkway and more. The monthly maintenance fee of $485 includes lawn care, bush and hedge trimming, exterior home painting, cable TV, internet, trash removal and access to the clubhouse and community amenities. Just a short walk from the home, the lakefront clubhouse offers a heated pool and spa, fitness center, ballroom, library, dance studio, arts and crafts studio and a computer room. Outdoor amenities include shuffleboard, basketball, tennis and bocce ball, along with a community boat ramp, dock and dog park. A new Publix located just outside the community gate makes everyday errands especially convenient, with dining and medical facilities only minutes away. Centrally located between Tampa and Orlando, this thoughtfully improved home offers an inviting opportunity to enjoy the maintenance-free lifestyle of Traditions at Lake Ruby.

4043 Bedford Avenue, Winter Haven

$1,750,000

4 Beds ⋅ 4 Baths ⋅ Country Club Acres SubDv. ⋅ 33881 Zip Code

11 ACRE POOL HOME WITH GUEST HOUSE AND BARN!!! Just minutes from downtown Winter Haven, on a quiet cul-de-sac, behind a gated private tree-lined drive sits the modern farmhouse of your dreams. From the 3500Sqft 4BR/4BA main house to the 1300Sqft 2BR/2BA guest house, the updates and upgrades are breathtaking. The main house has been fully renovated and NEVER LIVED IN!!! Be the first to enjoy the gorgeous open kitchen, the exquisite custom baths, the beautiful floors, the remarkable finishes, and the unparalleled views from the new windows looking out over the pastures, private pond, and pines! Multiple porches, patios, and sitting areas adorn the main house and guest house alike. The newly resurfaced pool features a waterfall and bubblers and sits under a NEW enclosure with NEW pavers and NEW pool equipment. Just a short walk from the main house is the guest house with endless potential uses: guest quarters, office, business, income production, in-law suite and the list goes on. It features a full kitchen, laundry/utility space, and more. The pole barn is a useful addition to your 900SqFt garage/barn with 900SqFt of fully floored storage up top. All this sits on 10.98 stunning acres of magical Florida beauty with access to shopping, dining, Legoland, medical, and more. Mere moments from the Country Club of Winter Haven, everything is at your fingertips but you feel like you are miles away. A true blend of land, luxury and location that can’t be denied. Schedule your showing now to tour this exquisite Florida masterpiece and turn this dream into your reality…

13 Bogey Drive, Winter Haven

$239,999

3 Beds ⋅ 1 Baths ⋅ Carefree Cove SubDv. ⋅ 33881 Zip Code

MOTIVATED SELLER Welcome to this charming home tucked into the desirable Carefree Cove neighborhood of Winter Haven. This 3 bedroom, 1 bath home is as cute as a button and features a beautiful living space that has been thoughtfully remodeled throughout, offering move-in-ready comfort with none of the guesswork. The front exterior has custom woodwork making a modern statement as soon as you pull up. A long driveway can accommodate multiple vehicles or storage for a boat or RV. Upon stepping inside you'll find brand-new laminate flooring flowing throughout every room, making clean ups and pet care easy peasy as there is NO carpet anywhere in the home. An upfront drop-zone is perfect for slipping on your shoes or storing purses & backpacks. Love to entertain??? Then the large family room will check these boxes! With a beautiful fireplace as a focal point, you'll also have a cafe section perfect for popcorn & snacks with a beverage fridge tucked in the corner. Tons of windows throughout make this a bright and airy home. The kitchen has been upgraded to butcher block countertops that are stunning on the eyes. A large pantry can easily accommodate all the big cases of water, rolls of paper towel & much much more! Just off of the kitchen is a nicely sized dining room. This can hold a large formal table and still have room for a serving buffet or credenza for extra storage. All 3 bedrooms feature new closet sliding doors. Major system upgrades give buyers extra peace of mind, including a brand-new roof and a 4-year-old air conditioning system. The big-ticket items are already taken care of. This home sits on a generous 7,279 sq ft lot with a fully fenced rear yard and a bonus screened patio, perfect for enjoying Florida evenings. Fire up the grill and enjoy BBQing while cozying up to a fire-pit in your rear backyard oasis. Solid block construction and a slab foundation add to the home's durability. Ideally located just off Carefree Cove Drive near the water, this home offers a quiet, established neighborhood feel while remaining close to Winter Haven's shopping, dining, and the area's famous chain of lakes. Whether you're a first-time buyer, downsizer, or investor, this fully updated home is ready for its next chapter. Schedule your showing today!

124 Edgewater Drive, Winter Haven

$340,000

3 Beds ⋅ 2 Baths ⋅ Summit East Ph 02 SubDv. ⋅ 33884 Zip Code

Beautifully maintained 3-bedroom, 2-bath pool home in a quiet Winter Haven community with a low HOA of $260/year. This home offers extensive upgrades, modern finishes, and a bright, open layout designed for comfortable living. Major improvements include a new roof (2020), new AC (2020), tankless water heater (2021), updated windows (2018), Culligan water system (2016), and a new pool pump and filter (2025). The kitchen features granite countertops, stainless steel appliances, a breakfast bar, and excellent natural light. The bathrooms also include granite counters, updated fixtures, and a large tub in the primary suite. Paradise Walk in tub (2020) in second bathroom. Enjoy Florida living with a saltwater fiberglass pool, screened enclosure, covered patio, fenced yard and irrigation system. Interior highlights include multiple flex spaces, neutral paint, updated ceiling fans, clean flooring, and move-in ready condition. Located close to shopping, dining, medical facilities, Legoland, and major highways, this home offers strong value with thoughtful upgrades and excellent maintenance. Schedule your private showing today.

7002 Summit Circle, Winter Haven

$345,190

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

$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

$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

$335,000

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

$245,000

2 Beds ⋅ 2 Baths ⋅ Cypresswood Golf Villa 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

$319,990

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

318 Hamilton Shores Drive Ne, Winter Haven

$524,000

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

Price Reduced!!! 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

Winter Haven Homes with Florida Architectural style

Newest Winter Haven Homes with Florida Architectural style

How much is your home worth?

How much is your home worth?