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$725,000
5 Beds ⋅ 3 Baths ⋅ Waterford Oaks SubDv. ⋅ 33884 Zip Code
Welcome to Waterford Oaks, where timeless architectural details and upgraded finishes set this home apart. Beautifully manicured landscaping and a paver driveway lead to an impressive 5-bedroom, 3-bath pool home with nearly 3,000 square feet of living space and an oversized 3-car garage. Decorative glass double entry doors open to a beautifully detailed interior featuring soaring ceilings, extensive crown molding, substantial millwork, architectural columns and arches, plantation shutters and elegant formal living and dining spaces. Thoughtful details continue throughout the home, creating a level of character and craftsmanship rarely found in newer construction. A versatile fifth bedroom at the front of the home also provides an ideal private office or den. At the center of the home, the kitchen combines function with elevated finishes, including granite countertops, rich wood cabinetry, upgraded KitchenAid appliances, a large breakfast bar and walk-in pantry. The kitchen flows into the spacious family room, where recessed lighting and expansive views toward the pool create a comfortable yet refined gathering space. A three-way split bedroom plan provides exceptional privacy. The primary suite is privately positioned in its own wing and features a spacious bath with dual granite-topped vanities, a soaking tub, separate walk-in shower and generous storage. On the opposite side of the home, a separate bedroom and adjacent full bath create an excellent option for guests or in-law accommodations, while two additional bedrooms and another full bath occupy their own private wing. The home's attention to detail carries outdoors to an expansive covered lanai and screened pool, creating a true extension of the living space with room for outdoor dining, entertaining and relaxing year-round. Mature landscaping adds privacy to the backyard setting. Located within gated Waterford Oaks, residents also enjoy community boat ramp and dock access to Lake Winterset and the Winter Haven Chain of Lakes. The combination of architectural detailing, upgraded finishes, a flexible three-way split floor plan, private pool, oversized 3-car garage and Chain of Lakes access makes this a distinctive opportunity in Winter Haven.

9504 Waterford Oaks Boulevard, Winter Haven
$359,000
3 Beds ⋅ 2 Baths ⋅ Lake Dexter Moorings SubDv. ⋅ 33884 Zip Code
Virtually Staged. WATERFRONT LIVING ON BEAUTIFUL LAKE DEXTER-PRIVATE DOCK - OVERSIZED CORNER LOT -Newly Remodeled -Bring the boat and start enjoying the Florida waterfront lifestyle! This beautifully updated 3 Bedroom 2 Bath plus separate Dining Room/Office Lake Dexter canal home offers your own 15 X 25 private dock with electric and water, giving you easy access to boating, fishing and days on the lake. All right from your backyard. Inside, the spacious split-bedroom floor plan features an oversized living room with a fireplace and triple sliding doors opening to the screened lanai and spa. The kitchen had been remodeled with new quarts countertops, new abundant cabinetry, breakfast bar, additional counter space & beverage/wine cooler perfect for entertaining! The formal dining room can easily be converted into a large office/den with built-in oak bookshelves provides the perfect space for working from home or additional flex space. The newly renovated private primary suite offers dual walk-in closets, an updated bath and triple sliders providing direct access to the lanai, spa and outdoors! The guest bathroom has also been beautifully improved. Large inside laundry with plenty of pantry storage is great for organization. Outside, enjoy the huge lot partially fenced in from the waterfront dock! NEWER HVAC and DUCTWORK! NEW SPA PUMP & FILTER! The community also offers an additional boat ramp and community pool to enjoy when you come back in and want to cool off! If waterfront living, boating, fishing and plenty of space are on your wish list, this Lake Dexter home deserves a closer look! You will love living here!

1475 Grand Cayman Circle, Winter Haven
$399,900
4 Beds ⋅ 3 Baths ⋅ Winterset Gardens 1st Add SubDv. ⋅ 33884 Zip Code
Virtually Staged. Welcome to 6604 Winterset Gardens Road, where MOVE-IN-READY living meets the ultimate Winter Haven lake lifestyle! Located directly across from a private boat ramp with access to LAKE WINTERSET and the WINTER HAVEN CHAIN OF LAKES, this beautifully updated 4-bedroom, 2.5-bath home offers an impressive 2,459 square feet of heated living space and a generous 3,777 square feet under roof, complete with a THREE-CAR GARAGE and spacious SCREENED-IN BACK PORCH. From the moment you arrive, you’ll appreciate the fresh exterior paint, gutters, solar system, and oversized three-car garage. Step inside to a freshly painted interior featuring NEW LUXURY VINYL PLANK FLOORING throughout, NEW LIGHTING, soaring CATHEDRAL-STYLE CEILINGS, and a spacious floor plan designed for both everyday living and entertaining. The welcoming entry opens to a separate living area with space for a HOME OFFICE, along with a FORMAL DINING ROOM. Continue into the heart of the home where the beautifully UPDATED KITCHEN features NEW CABINETRY with soft-close doors and drawers, SOLID-SURFACE COUNTERTOPS, BRAND-NEW DARK STAINLESS-STEEL APPLIANCES, a spacious breakfast bar, and an abundance of cabinet and countertop space. The PRIMARY BEDROOM is a TRUE EN SUITE RETREAT with generous space, its own dedicated MINI-SPLIT A/C system, and SLIDING GLASS DOORS opening directly to the screened patio—perfect for enjoying Florida's indoor-outdoor lifestyle. The additional bedrooms offer excellent storage, including WALK-IN CLOSETS, while the INDOOR LAUNDRY ROOM provides additional cabinetry for everyday organization. Comfort is covered with multiple A/C systems, including a 2023 system, a NEW 2026 system, plus the dedicated mini-split serving the primary suite. Additional features include, SOLAR, a freshly painted garage floor, and a THREE-CAR GARAGE offering plenty of room for vehicles, storage, recreational equipment, or your lake toys. Out back, the LARGE SCREENED-IN PORCH expands the living space and creates the perfect setting for morning coffee, weekend gatherings, or relaxing after a day on the water. And for boating and outdoor enthusiasts, the location is hard to beat. With the BOAT RAMP DIRECTLY ACROSS THE STREET, you can enjoy LAKE WINTERSET and the WINTER HAVEN CHAIN OF LAKES for BOATING, FISHING, WATER SPORTS, and the Central Florida lake lifestyle Winter Haven is famous for. With 4 BEDROOMS, 2.5 BATHS, 2,459 SQ FT OF HEATED LIVING SPACE, 3,777 SQ FT UNDER ROOF, an UPDATED KITCHEN, LUXURY VINYL PLANK FLOORING, THREE-CAR GARAGE, SCREENED PORCH, SOLAR, MULTIPLE A/C SYSTEMS, and LAKE WINTERSET/CHAIN OF LAKES ACCESS just steps from your front door, this home delivers the space, updates, storage, and lifestyle today's buyers are searching for. Schedule your private showing and experience 6604 Winterset Gardens Road for yourself!

6604 Winterset Gardens Road, Winter Haven
$258,000
2 Beds ⋅ 2 Baths ⋅ Fla Highlands Co Sub SubDv. ⋅ 33884 Zip Code
This beautifully decorated, impeccably maintained two-bedroom, two-bathroom home sits on a spacious corner lot with a view of the canal across the street. Stepping inside, an inviting and bright layout unfolds into a large living room that flows seamlessly into the dining area. To the left, a well-appointed guest bedroom sits adjacent to a full bath, while the primary suite offers a generous walk-in closet and a spacious ensuite bathroom with a dedicated linen closet. To the right of the dining area, the kitchen features room for an eat-in table and leads through a full-size utility room into a attached one-car garage. Out back, a massive 14x28 screened lanai opens up to a private backyard oasis filled with lush flowers, shrubs, trees, an updated white vinyl privacy fence (2024), pavers installed in the area to the right side of the home (2025), and fresh mulch (2026). Additional recent upgrades include a new Carrier A/C unit (2023) and front gutters & downspouts (2025). Located just down the road from this home is Lake Ned's 73-acre lake with a park—complete with a boat launch, fishing, playground, and pavilions. Anglers will love fishing for largemouth bass, bluegill, black crappie (specks), redear sunfish, blue tilapia, nile tilapia, carp, catfish, bowfin, gar and chain pickerel. For more convenience there is nearby shopping, gas stations, churches, grocery stores and restaurants. This aggressively priced home offers an exceptional lifestyle. Note: Washer, dryer, kitchen refrigerator, dining room light fixture, and the outdoor front shed do not convey.

400 Bayou Road, Winter Haven
$329,999
4 Beds ⋅ 2 Baths ⋅ Inman Grvs Ph 2 SubDv. ⋅ 33881 Zip Code
Welcome to this beautiful 2023-built home in Winter Haven, offering 4 bedrooms, 2 bathrooms, approximately 1,867 square feet of living space, a two-car garage, and a fenced yard. Designed for comfortable modern living, this home features tile flooring throughout the main living areas and carpet in the bedrooms. The open-concept kitchen is perfect for everyday living and entertaining, featuring a large kitchen island, pantry, dining area, and all appliances included. Additional features include a whole-home water filtration system and solar panels that may be transferred to the buyer, subject to applicable terms and buyer qualification. Conveniently located near shopping, dining, medical facilities, and everyday essentials, with easy access to Cypress Creek Plaza, Polk State College, Winter Haven Hospital, and the Winter Haven station. Enjoy being close to LEGOLAND® Florida Resort and PEPPA PIG Theme Park, while Walt Disney World® Resort and the greater Orlando area are approximately 45 minutes away, depending on traffic and destination. This home is ready for its next owner. Schedule your private showing today!

751 Grove Street, Winter Haven
$220,000
4 Beds ⋅ 2 Baths ⋅ Reddicks Corner SubDv. ⋅ 33884 Zip Code
Virtually Staged. INVESTOR OPPORTUNITY! Discover the potential of this 4-bedroom, 2-bath home in Winter Haven, ideally located near LEGOLAND Florida and Peppa Pig Theme Park. This property offers a great opportunity for investors, renovators, or buyers looking to create value in a sought-after Central Florida location. Conveniently situated near major attractions, shopping, dining, and entertainment, this home provides an excellent opportunity to bring your vision to life. CASH OFFERS ONLY. Schedule your showing today!

545 Reddicks Circle, Winter Haven
$315,000
3 Beds ⋅ 2 Baths ⋅ Lake Elbert Estates SubDv. ⋅ 33881 Zip Code
Welcome to this beautifully remodeled 3-bedroom, 2-bathroom home offering approximately 1,220 square feet of living space on a generous 0.28-acre lot. The home features an updated interior, modern finishes, comfortable living areas, and a functional floor plan. Conveniently located near shopping, dining, recreation, and downtown Winter Haven. Schedule your private showing today and come see everything this move-in-ready home.

Winter Haven
$230,000
2 Beds ⋅ 2 Baths ⋅ Cypresswood Patio Homes SubDv. ⋅ 33884 Zip Code
Enjoy comfortable Florida living in this beautiful partially furnished 2 bedroom, 2 bathroom home located in desirable Cypresswood Golf Community. The home features comfortable living areas including spacious family room and inside laundry. Community amenities include manned guard gate, community swimming pool, clubhouse and onsite pub. New roof October 2026, A/C only two years old.

617 Wexford Court, Winter Haven
$190,000
3 Beds ⋅ 2 Baths ⋅ Whispering Trails Ph 02 SubDv. ⋅ 33884 Zip Code
Short Sale. Block 3-2 block home, needs repairs, but can be a great income producing , down sizing or first time home buyer home. House is in need of repaires,no leaks, floors and painted is needed. Being sold in as is condition.

2796 Whispering Trails Drive, Winter Haven
$179,900
3 Beds ⋅ 1 Baths ⋅ West Cannon Heights SubDv. ⋅ 33881 Zip Code
Virtually Staged. Welcome to this 3-bedroom, 1-bath home in Winter Haven. The single-story home offers a comfortable layout with well-sized bedrooms and inviting living spaces. A one-car carport provides convenient covered parking, while the outdoor space offers room to enjoy the Florida weather. The home will benefit from some minor updates, providing an opportunity to add personal touches and make the property your own. Conveniently located near local schools, shopping, dining, parks, and major roadways.

1210 32nd Street Nw, Winter Haven
$259,900
3 Beds ⋅ 2 Baths ⋅ Villamar SubDv. ⋅ 33884 Zip Code
Brand new, energy-efficient home available by Aug 2026! 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.

3948 Giorgio Drive, Winter Haven
$305,000
4 Beds ⋅ 2 Baths ⋅ St James Xing SubDv. ⋅ 33881 Zip Code
Virtually Staged. Weclome to this move-in ready single story home with a bright, open floor plan and inviting living spaces. The spacious kitchen features granite countertops, stainless steel appliances, and ample cabinet space. Functional vinyl flooring enhances the main living areas, while spacious bedrooms provide comfortable accommodations. An attached two car garage adds convenience to this lovely home. Easy to show!

4750 Osprey Way, Winter Haven
$319,900
4 Beds ⋅ 2 Baths ⋅ Haven Terrace SubDv. ⋅ 33880 Zip Code
SINGLE-FAMILY HOME WITH DETACHED IN-LAW SUITE, RENTAL INCOME & NO HOA! This unique Winter Haven property features a 3-BEDROOM, 1-BATH MAIN HOME plus a separate 1-BEDROOM, 1-BATH DETACHED IN-LAW SUITE, ideal for MULTIGENERATIONAL LIVING, extended family, guests, or ADDITIONAL RENTAL INCOME. The main home is currently operated as a SHORT-TERM RENTAL and is being sold FULLY FURNISHED, with furniture included in the sale price, offering a TURNKEY opportunity for a new owner or a MOVE-IN-READY PRIMARY RESIDENCE. The detached suite has its own PRIVATE ENTRANCE, SEPARATE ADDRESS, PARKING, and SEPARATE UTILITIES currently paid by the tenant, and is generating $1,095/MONTH in rental income while maintaining privacy between both living spaces. Major improvements include NEWER ROOFS completed within approximately the last two years, UPDATED PLUMBING, and CENTRAL A/C for both living spaces. Located just minutes from DOWNTOWN WINTER HAVEN with convenient access to restaurants, shopping, entertainment, and the continued GROWTH AND DEVELOPMENT happening throughout the area. Live in the main home while collecting rental income, continue utilizing the main home as a SHORT-TERM RENTAL, or accommodate extended family—the property offers exceptional FLEXIBILITY for a variety of living arrangements and income opportunities, subject to applicable local regulations. NO HOA!

113 Avenue C Se, Winter Haven
$280,000
4 Beds ⋅ 2 Baths ⋅ Lakes At Lucerne Park Ph 02 SubDv. ⋅ 33881 Zip Code
Perfect for a family purchasing their first home! This four-bedroom, two-bath home offers comfortable Florida living with a functional layout and great outdoor space. One of the standout features is the private, fully fenced backyard, along with a screened-in back patio and covered lanai that create the perfect setting for relaxing, entertaining, or enjoying your morning coffee. Luxury vinyl plank (LVP) flooring runs throughout all bedrooms and main living areas, creating a clean, updated, and easy-to-maintain look, while the bathrooms feature tile flooring. All appliances convey with the home, including the washer, dryer, refrigerator, stove, and garbage disposal, making this home even more move-in ready. The combination of the screened patio, covered lanai, and fenced yard provides an excellent extension of the home’s living space and added privacy. Conveniently located in Winter Haven with access to shopping, dining, entertainment, and major roadways, this home offers a great combination of indoor comfort, outdoor living, and everyday convenience. Schedule your private showing today and see everything this home has to offer!

255 Haines Boulevard, Winter Haven
$259,000
3 Beds ⋅ 2 Baths ⋅ Villamar Ph 1 SubDv. ⋅ 33884 Zip Code
Welcome to 824 Vienna Dr, a beautiful Well sought out community 3-bedroom, 2-bathroom home located in the desirable Villamar Phase 1 community of Winter Haven! Built in 2021, this well-maintained home offers approximately 1,402 square feet of comfortable living space with a spacious open-concept design that makes everyday living and entertaining effortless. Step inside to a bright and inviting living area that flows naturally into the dining space and kitchen, creating a comfortable gathering place for family and friends. The primary suite offers a private retreat with its own bathroom, while two additional bedrooms provide plenty of space for family, guests, a home office, or hobbies. A 2-car attached garage adds convenience and valuable storage space. One of the standout features of this property is the larger lot, giving you more room to enjoy the outdoors and create the backyard you've always wanted. The possibilities are endless from adding a pool or playground to creating an outdoor entertaining area, garden, fire-pit space, or your own private backyard oasis, subject to applicable HOA and local requirements. Community itself has a playground, park, and large resort style pool. Located in Villamar Phase 1, you'll enjoy a welcoming community atmosphere with convenient access to shopping, dining, schools, parks, major roadways, and everything Winter Haven has to display. Whether you're looking for your first home, a place to grow your family, or a newer property with room to make it your own, 824 Vienna Dr is an opportunity you won't want to miss. Schedule your private showing today!

824 Vienna Drive, Winter Haven
$365,190
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
$459,900
5 Beds ⋅ 3 Baths ⋅ East El Otis Park Rep SubDv. ⋅ 33880 Zip Code
NO HOA Lake Front 5 bedroom 3 bath Home in Winter Haven! This beautifully remodeled home enjoys elevated views of Lake Elbert! Inside the home you find Luxury vinyl plank flooring throughout the main living area with brand new carpet for comfort in the bedrooms. The large Kitchen boasts All wood cabinetry with durable quartz countertops and brand new Stainless steel appliance package! Enjoy time outside in the Screened in porch that overlooks the lake or enjoy time in the fenced in back yard that has citrus and star fruit trees! There is workshop or storage room out back as well. All major repairs and updates have been taken care of, including: newer roof, new HVAC, Water heater, windows and doors and this beautiful home is ready for its new owner! Schedule your showing today!

1196 Lake Elbert Drive Se, Winter Haven
$299,000
3 Beds ⋅ 2 Baths ⋅ Planters Walk SubDv. ⋅ 33884 Zip Code
Welcome to the beautifully maintained 3-bedroom, 2-bath home with a bonus room in the desirable Planters Walk community of SE Winter Haven! Offering approximately 1,640 square feet of living space on a spacious 8,712-square-foot lot, this home provides comfortable living with plenty of room to enjoy both indoors and out. Step inside to find beautiful wood flooring flowing through the entrance, living room, and dining area, creating a warm and inviting atmosphere. The family room and kitchen feature easy-care tile flooring, while the kitchen offers stainless steel appliances and granite countertops. Granite countertops are also featured in the other wet areas of the interior, adding both style and functionality. The bonus room provides flexible space that can be used as a home office, den, craft room, playroom, or additional living area. Outside, enjoy your fully fenced backyard featuring a deck and gazebo—perfect for relaxing, entertaining guests, enjoying your morning coffee, or creating your own private outdoor retreat. The roof was recently replaced, providing an added benefit for the next homeowner. Another great feature is the exceptionally low HOA fee, with no CDD fees, helping keep the cost of ownership affordable. Located in SE Winter Haven, Planters Walk offers convenient access to shopping, restaurants, grocery stores, medical facilities, schools, and major roadways. The area is also close to Winter Haven's famous Chain of Lakes and is just a short drive from LEGOLAND Florida Resort, making this a great location for both everyday living and enjoying Central Florida attractions. Winter Haven offers plenty of opportunities for outdoor recreation and entertainment, including parks, trails, lakes, downtown restaurants, local shopping, and community events. Nearby attractions include South Lake Howard Nature Park, Trailhead Park Playground, and the vibrant Downtown Winter Haven area with its restaurants, shops, events, and local markets. Sizes and measurements are estimates and are to be verified by buyer and or buyers agent.

12 Saint Kitts Circle, 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
$450,000
5 Beds ⋅ 3 Baths ⋅ Winterset Gardens 1st Add SubDv. ⋅ 33884 Zip Code
Welcome to 6624 Winterset Gardens Road - this is an ideal home or rental property for those seeking an updated living space with community boat ramp with Chain of Lakes access. This renovated home has 5 bedrooms with 2.5 bathrooms. The renovations include new kitchen cabinets, kitchen appliances and Quartz countertops, fully renovated bathrooms, new flooring, new lighting, new ceiling fans and more. NEW Roof in 2022 and a New Termite bond in 2026! This home also has a newly painted interior/exterior. Winterset Gardens is a highly respected, quaint neighborhood on the shore of Little lake Winterset and offers an optional $100 HOA with a community boat ramp and no deed restrictions allowing direct access to The world renowned Winter Haven Chain of Lakes. 24 canal connected lakes offering great fishing, skiing and leisure boating. Hop on your boat from your neighborhood and go get a bite to eat at several float up bars and restaurants.

6624 Winterset Gardens Road, Winter Haven
$315,000
3 Beds ⋅ 2 Baths ⋅ Lake Deer SubDv. ⋅ 33880 Zip Code
Welcome to this beautifully maintained 3-bedroom, 2-bathroom home, built in 2020 and located in the gated Lake Deer community. This move-in-ready residence features a bright, open-concept floor plan that seamlessly connects the living room, dining area, and kitchen—ideal for everyday living and entertaining. The kitchen is the heart of the home, offering granite countertops, stainless steel appliances, ample cabinetry, and a spacious center island with additional seating and workspace. Laminate flooring extends throughout the home, providing a clean, modern appearance with no carpet to maintain. The primary suite includes a private bathroom and walk-in closet, while two additional bedrooms are flexibility for guests, a home office, or a personal fitness space. The home also features an attached two-car garage and a covered rear patio overlooking the generously sized backyard—perfect for relaxing, entertaining, or creating your own outdoor retreat. Residents of Lake Deer enjoy access to a community playground and dock for fishing or taking in the peaceful lake views. Additional benefits include low HOA fees, no CDD, and Flood Zone X. Conveniently located near shopping, dining, schools, and major roadways. Schedule your private showing today!

195 Black Skimmer Lane, Winter Haven
$700,000
3 Beds ⋅ 4 Baths ⋅ Acreage SubDv. ⋅ 33880 Zip Code
Welcome to your own private piece of Florida! This unique property offers nearly 5 acres of space, privacy, and endless possibilities with **NO HOA**. Nestled away from the hustle and bustle, this property provides the room and freedom to enjoy a more private, country-style lifestyle while still being conveniently located near everything Winter Haven has to offer. The property features a spacious 3-bedroom, 2.5 bath home plus a detached shed that is currently being used as a she shed. With nearly 5 acres, there is plenty of room for outdoor activities, pets, gardening, recreational equipment, or simply enjoying the peace and privacy of your surroundings. The Pool area also features an outdoor half bath for convenience! Enjoy easy access to Winter Haven's famous **Chain of Lakes**, offering boating, fishing, kayaking and scenic water activities. You're also conveniently located near **LEGOLAND Florida Resort, Peppa Pig Theme Park, SEA LIFE Florida, downtown Winter Haven, local parks, shopping and dining**. For nature lovers, nearby attractions include scenic lakefront parks and trails, while **Bok Tower Gardens** is just a short drive away in Lake Wales. Winter Haven's central location also provides convenient access to the greater Central Florida area, including Orlando and Tampa. If you've been searching for acreage, privacy, flexibility and no HOA while remaining close to Central Florida attractions, this property offers a rare opportunity to enjoy it all.

281 Gerber Dairy Road, Winter Haven
$349,001
2 Beds ⋅ 2 Baths ⋅ Traditions Ph 02 SubDv. ⋅ 33884 Zip Code
Welcome to Traditions, a premier 55+ maintenance-free gated community, where resort-style living meets everyday comfort and convenience! This wonderful 2-bedroom, 2-bath home with a den offers Eco Smart construction and an exceptional location just steps from the community clubhouse and directly across the street from the boat ramp. A charming screened-in front entry welcomes you into this beautifully appointed home. Step inside to the spacious Great Room, featuring elegant crown molding and porcelain plank flooring. Oversized glass sliding doors provide an abundance of natural light and open seamlessly to the screened-in lanai, creating an effortless flow between indoor and outdoor living. The gourmet kitchen is truly a chef’s delight, showcasing timeless white shaker cabinetry accented with crown molding and brushed-nickel hardware, complemented by a beautiful glass-tile backsplash. The center island features luxurious quartz countertops and pendant lighting, creating both a stylish focal point and functional workspace. A walk-in pantry and stainless-steel appliance package provide additional convenience and storage. The charming breakfast nook offers the perfect spot for casual dining. Designed for entertaining, the open-concept floor plan allows the formal Dining Room to flow naturally into the Great Room. The versatile Den is an inviting retreat with beautiful views overlooking Lake Ruby, making it an ideal home office, reading room, or additional living space. The Primary Bedroom Suite offers a peaceful retreat, featuring a tray ceiling, wall-to-wall carpeting, and a generously sized walk-in closet. The luxurious Primary Bath features a comfort-height vanity with dual sinks, quartz countertops, private water closet, and a handicapped-accessible tiled shower beautifully finished with decorative Listello tile and glass enclosure. Throughout the home, crown molding and graceful arched entryways add architectural detail and timeless elegance. Step outside to the generously sized screened-in lanai, beautifully finished with pavers and offering a peaceful space to relax, entertain, and enjoy the Florida lifestyle. Additional features include a Laundry Room with cabinetry, washer and dryer, keyless smart-lock entry, smart thermostat, double-pane Low-E windows, AO Smith hybrid water heater, screened front entry, exterior carriage lighting, architectural shingle roof, radiant heat barrier, gutters, exterior stone facade, and paved walkway & driveway. The two-car garage features a garage door opener for added convenience. Traditions offers an exceptional active-adult lifestyle with an impressive array of amenities and planned activities. Residents enjoy a lakefront clubhouse, dock and boat ramp, heated swimming pool and spa, ballroom, billiards, meeting room, library, computer room, craft room, dog park, tennis courts, basketball court, bocce, shuffleboard, fitness center, aerobics studio, and so much more. The monthly HOA fee includes lawn service, cable, internet, and exterior house painting, providing added value and making maintenance-free living truly effortless. With its coveted location near the clubhouse and boat ramp, Lake Ruby views, this property offers the perfect combination of resort-style amenities, beautiful surroundings, and everyday convenience.

4075 Bedford Avenue, Winter Haven
$255,000
3 Beds ⋅ 2 Baths ⋅ Saxon Myers Rep Ph 2 SubDv. ⋅ 33881 Zip Code
Welcome to 117 Rebecca Dr NE in Winter Haven! This charming home features a comfortable, spacious layout, inviting living areas, and a convenient location on a quiet residential street. Well-maintained landscaping and welcoming curb appeal make a great first impression. Inside, natural light fills the living spaces, creating a bright and comfortable atmosphere throughout. The functional kitchen provides plenty of space for everyday cooking and entertaining, while the open living and dining areas provide flexibility for a variety of uses. Step outside to enjoy a spacious, fully fenced backyard with plenty of room for outdoor entertaining, recreation, or simply relaxing in the Florida sunshine. The patio provides additional outdoor living space, while the privacy fencing creates a more secluded setting. For added preparedness during Florida's hurricane season and unexpected power outages, an included generator setup is conveniently connected to the home. Conveniently located near shopping, dining, recreation, and other Winter Haven amenities, this home combines comfort with everyday convenience. The home can also be purchased fully furnished and move-in ready, providing an easy transition for use as a primary residence, second home, or investment property. Come see everything 117 Rebecca Dr NE has to enjoy!

117 Rebecca Drive Ne, Winter Haven
$269,000
3 Beds ⋅ 2 Baths ⋅ Kings Pond Sub SubDv. ⋅ 33880 Zip Code
Welcome to this well-maintained 3-bedroom, 2-bath home tucked away on a quiet cul-de-sac. Situated on approximately 0.23 acres, this home features a 2-car garage, vaulted ceilings, upgraded windows, and a bright, comfortable layout. The roof was replaced in November 2021 and the HVAC was replaced in 2022. Interior updates completed in 2024 include new flooring and fresh paint. Master Bedroom has private access to the patio space and an ensuite full bathroom. Enjoy additional living and entertaining space on the screened-in patio with vinyl window coverings.. The property also features an irrigation/sprinkler system. Conveniently located near shopping, dining, schools, and everything the city of Winter Haven provides, this move-in-ready home combines thoughtful updates with a peaceful residential setting. HOA is only $200 annually. Buyer to verify all HOA information, Tax information and Room Dimensions.

224 Crown Court, Winter Haven
$335,000
3 Beds ⋅ 2 Baths ⋅ Estates/Lk Florence SubDv. ⋅ 33884 Zip Code
Great Location!! 3 beds 2 baths, HUGE LOT. This home features porcelain tile in the main living, quartz countertops, stainless steal appliances and much more. Split floor plan with huge master bedroom, on-suite, and large walk in closet. This is the perfect family home close to everything including Legoland. Give us a call today to set up a showing to see this amazing home!

1050 Michelangelo Lane, Winter Haven
$255,000
3 Beds ⋅ 2 Baths ⋅ Eagle Lndg Ph I SubDv. ⋅ 33880 Zip Code
Move right into this lovingly maintained 3-bedroom, 2-bath home with a 2-car garage nestled in Eagle Landing. Low annual HOA fee. Spanning nearly 1,300 square feet of living space, this home features a bright and airy open floor plan that effortlessly connects the living, dining, and kitchen areas. The kitchen showcases beautiful countertops, ample cabinetry, a close pantry, and a functional island. The primary bedroom is complete with a walk-in closet and its own bathroom. The additional bedrooms provide plenty of versatility for family, guests, or a dedicated home office. Enjoy the ease of a dedicated indoor laundry room. Step outside to a rear covered porch overlooking a fully fenced-in backyard, ideal for relaxation, pets, play, and outdoor gatherings. Don't delay; call and schedule your appointment today.

813 Eagle Rock Ter, Winter Haven
$460,000
4 Beds ⋅ 4 Baths ⋅ Hutchinson Add SubDv. ⋅ 33881 Zip Code
Welcome to 900 Lake Martha Drive NE, a truly unique lakefront property offering exceptional space, flexibility, and endless possibilities! The property extends across the street to Lake Martha, providing direct lake frontage and wonderful opportunities to enjoy the waterfront. Information provided by the City, the lakefront portion may be divided from the main homesite, creating even more possibilities for the property. The main portion of the home features three bedrooms and two bathrooms, spacious living and dining areas, and a large bonus room currently used as a pool and game room. This flexible space could also serve as a family room, home office, gym, or additional entertainment area. Located on the opposite side of the home, the private in-law suite offers separation from the main living area, its own entrance, and a full bathroom. Above the two-car garage is an expansive room with a full bathroom and space for a kitchenette. This versatile area could become a movie room, game room, additional primary suite, guest quarters, or a second in-law suite. The garage also includes an additional shower—perfect for rinsing off after boating, fishing, yardwork, or a day by the lake. Enjoy Florida living from the screened front and rear porches. The fenced side yard is already improved with crushed gravel, providing convenient parking for a boat, RV, trailer, or other recreational vehicles. With direct lake frontage, multiple living areas, flexible bonus spaces, and the potential to separate the waterfront portion, this property offers outstanding possibilities for multigenerational living, extended-family accommodations, guest quarters, or potential short- or long-term rental use. Bring your ideas and discover everything this one-of-a-kind Lake Martha property has to offer!

900 Lake Martha Drive Ne, Winter Haven
$350,000
4 Beds ⋅ 2 Baths ⋅ Reflections East Add SubDv. ⋅ 33884 Zip Code
More space, more flexibility, and more included! Located near LEGOLAND Florida Resort, this spacious Winter Haven home offers 2,257 square feet of total living area, including a permitted 320-square-foot addition completed in 2021. The interior features a bright main living area with vaulted ceilings, a separate dining space, generously sized bedrooms, an interior laundry room, and a well-equipped kitchen with ample cabinetry and counter space. The refrigerator, range, microwave, dishwasher, washer, and dryer are all included. Step outside to a fenced backyard designed for enjoying the Florida lifestyle. A brand-new permitted covered patio, completed in March 2026, provides an inviting shaded space for relaxing, grilling, or entertaining. The backyard also features mature shade trees and a paver gathering area with a built-in firepit and seating. Additional highlights include a complete HVAC system installed in 2023, a main house roof installed in 2017, a new patio roof installed in 2026, a two-car garage, an included security system, and eight included 360-degree security cameras. Conveniently positioned in Central Florida between Orlando and Tampa, the home provides access to major attractions, shopping, dining, recreation, and everything the Winter Haven area has to provide. With substantial living space, valuable permitted improvements, included appliances, and an outdoor area ready to enjoy, this home delivers features that are increasingly difficult to find at this price point. Schedule your private showing and see how much this property has to give.

817 Reflections Loop E, Winter Haven
$237,900
3 Beds ⋅ 2 Baths ⋅ Cypress Landing Ph 01 SubDv. ⋅ 33884 Zip Code
One or more photos have been virtually staged Charming 3/2 in Cypress Landings on Lake Dexter! Welcome home to this adorable 3-bedroom, 2-bath property located in the highly desirable Cypress Landings community on beautiful Lake Dexter. Step inside to an inviting open floor plan featuring cathedral ceilings that make the living space feel bright, airy, and perfect for everyday living or entertaining. The large primary bedroom offers plenty of comfort with its walkin closet and a private ensuite bath complete with a convenient step in shower. Living in Cypress Landings means enjoying a lifestyle full of amenities, including: Community boat ramp, Fishing pier, Clubhouse, Heated pool, Tennis courts. All of this, plus a location that keeps you close to shopping, medical offices, dining, and more. This community does not allow short term rentals, ensuring a peaceful, residential atmosphere. A wonderful opportunity to enjoy lake access, great amenities, and a cozy home in a fantastic Winter Haven neighborhood!

4116 Fishermans Landing, Winter Haven