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441 San Jose Drive, Winter Haven
$254,900
2 Beds ⋅ 2 Baths ⋅ L4965434 MLS
Welcome to 441 San Jose Drive, featuring a NEW ROOF installed in 2026 and located in the highly sought after Orchid Springs community of Winter Haven. This spacious 2 bedroom, 2 bathroom patio home sits on an oversized lot and offers a thoughtfully designed floorplan with generous living spaces and wonderful indoor and outdoor flow. The expansive kitchen opens to the large family room and dining area, creating an inviting space for everyday living and entertaining, while a separate living room and breakfast nook provide additional room to spread out. The spacious primary suite is privately positioned at the rear of the home and features an ensuite bathroom and walk in closet, while the second bedroom and full bathroom are located on the opposite side of the home. The home features a combination of tile and carpet flooring throughout. Step outside to enjoy both a charming courtyard and a large screened porch, offering multiple spaces to relax and enjoy the oversized lot. A wooded area along one side of the property is visible from the kitchen and adds a peaceful, secluded feel to the home. Additional features include a 2 car garage and gas water heater. Conveniently located in Winter Haven, this home is close to shopping, dining, medical facilities, recreation, and everyday conveniences. With its spacious floorplan, oversized lot, multiple outdoor living spaces, NEW ROOF, and desirable Orchid Springs location, 441 San Jose Drive is ready to welcome its next owner.

441 San Jose Drive, Winter Haven

5661 Struthers Court, Winter Haven
$319,990
4 Beds ⋅ 2 Baths ⋅ A4708119 MLS
RARE DUPLEX OPPORTUNITY – PERFECT FOR INVESTORS OR HOUSE HACKING! Excellent opportunity to own a CBS duplex featuring two 2-bedroom, 1-bath units situated on approximately 0.22 acres, ideal for a buy-and-hold investor or an owner-occupant looking to offset their monthly mortgage with rental income. One unit is currently rented while the other is vacant, providing flexibility for immediate occupancy or the opportunity to place your own tenant. The property is in good working and living condition and features attractive curb appeal, open kitchens, spacious living areas, and generously sized bedrooms. Major improvements include a NEW ROOF installed in 2025 and A/C systems from 2025 and 2017, helping reduce concerns over major capital improvements. With one unit already producing income and the second available for occupancy or rental, this property offers multiple possibilities for both investors and owner-occupants. Live in one side and rent the other to help offset your mortgage or operate both units as a long-term rental investment. Duplex inventory at this price point is extremely limited. Don’t miss the opportunity to secure a versatile income-producing property with major updates already completed.

5661 Struthers Court, Winter Haven

3304 Costello Circle, Winter Haven
$284,900
3 Beds ⋅ 2 Baths ⋅ L4965165 MLS
Better than New and Move in ready! A screened porch for morning coffee, a fully fenced backyard, and a kitchen finished with white cabinetry and quartz countertops—3304 Costello Circle brings together the features that make a house comfortable to come home to. Set in Winter Haven’s Villamar community, this single-story block home was built in 2023 and offers three bedrooms, two full bathrooms, 1,553 square feet of living space, and an attached two-car garage. Inside, luxury vinyl plank flooring extends throughout the home, with no carpet to maintain. The open-concept living and dining areas keep the main gathering space connected to the kitchen, making it easy to prepare a meal while spending time with guests. White cabinets, quartz countertops, and ample workspace give the kitchen a clean, coordinated finish. The split-bedroom floor plan places the primary suite apart from the secondary bedrooms. The primary bedroom includes a generous walk-in closet and its own en suite bathroom. Two additional bedrooms share a hallway bathroom and provide space for guests, hobbies, or a home office. The second bedroom also includes a walk-in closet, adding storage beyond the primary suite. Indoor laundry keeps everyday tasks conveniently inside. Continue to the screened porch, where there is a welcoming spot to sip morning coffee or settle in for a quiet evening. The fully fenced backyard extends the outdoor living space with room to enjoy the sunshine, garden, or spend time with pets. Beyond your own backyard, Villamar offers a community swimming pool, cabana, shaded poolside seating, and playground in a lakeside setting along Crystal Lake. For those who enjoy fishing, a neighborhood fishing pond is located just five doors down, adding another opportunity to enjoy the outdoors close to home. Shopping, dining, LEGOLAND Florida, and connections to US-27, US-17, and Highway 60 add to the location’s convenience. Come explore the layout, finishes, and outdoor spaces that make this Winter Haven home stand out.

3304 Costello Circle, Winter Haven

1321 Oakmont Drive, Winter Haven
$409,000
3 Beds ⋅ 2 Baths ⋅ P4940018 MLS
** CDD Debt Balance PAID IN FULL, saving you thousands! ** Enjoy temperature-controlled, therapeutic sunshine year-round in the NEW four-season SUNROOM, looking out at your own private sanctuary of palms and other native trees and plants! With plenty of room to entertain family and friends, this 2022 St. Marks home is located within walking distance of the Health & Fitness Center, and offers a spacious and private Master Suite, two Guest Bedrooms, and a Guest Bath with shower/tub combination. The abundant wood-like tiled living space includes a Foyer, Living Room, Formal Dining, Den, and glass-enclosed Sunroom (accessed via the triple-sliders in the Living Room and the double-sliders in the Dinette). The large Kitchen offers granite countertops, soft close drawers, stainless steel appliances, tiled backsplash, step-up Breakfast Bar with pendant lights, and abundant countertops for food prep and display. The Dinette area, which is adjacent to the Kitchen, is also accessible from the Sunroom and the Den. The generous laundry room includes washer and dryer, and shelves for extra storage. The two-car Garage with designated Golf Cart Entry also offers storage space, as does the partially-floored Attic, accessed from the garage via a new pull-down ladder. An automatic screen (Skeeter Beater) has been added in the Garage for air circulation. New landscaping surrounds the house, including lush privacy landscaping in the back! ADDITIONAL UPGRADES: Separate Irrigation Meter (Saving you Money!), Whole House Gutter System, Storm Door on the front door, new window dressings throughout the home, six-filter Reverse Osmosis Water System, and new cabinet and drawer hardware in the Kitchen and Bathrooms. Lake Ashton has (2) clubhouses, (2) Golf Courses, Planned Activities and Resort Style Amenities. Residents enjoy 2 Swimming Pools (one Indoor & one Outdoor), Movie Theater, Bowling Lanes, Card, Craft and Billiard Rooms, Fitness Rooms, Media Rooms, Indoor Racquetball, Indoor 1/2 Court Basketball, Pickle Ball Courts, Tennis Courts, Shuffleboard Courts, Eagles Nest (an Eatery), a Pro Shop and MORE! Lake Ashton is a beautiful 55 Plus Community in Florida closely located to Shopping, Restaurants, Entertainment and Medical Facilities. MAKE AN APPOINTMENT TODAY TOUR THIS BEAUTIFUL HOME.

1321 Oakmont Drive, Winter Haven

37 Lake Eloise Lane, Winter Haven
$515,000
3 Beds ⋅ 2 Baths ⋅ P4940000 MLS
Located in the desirable, tree-lined community of Harbour Estates, this custom-built 3-bedroom, 2-bath pool home offers expansive living spaces, and an exceptional outdoor lifestyle. Situated on an impressive .57-acre corner lot at the end of a quiet cul-de-sac, this property provides privacy, space and convenience in a highly sought-after location. Upon arrival, a grand courtyard welcomes you to sit and enjoy the beautifully landscaped grounds. A lovely leaded-glass front door with transom window opens into the inviting foyer, creating an elegant first impression. The generously sized Living Room features a striking stone fireplace, tray ceiling and strategically placed floor outlets that allow for flexible furniture placement. Three sets of glass sliding doors overlook the patio and pool area, bringing the outdoors in and creating a seamless connection between the interior and exterior living spaces. The eat-in Kitchen showcases a timeless black-and-white design, featuring crisp white cabinetry accented with crown molding and designer brushed-nickel hardware. Sleek black granite countertops beautifully complement the tile backsplash, while the kitchen sink is strategically positioned beneath a picture-frame window offering wonderful views of the pool. The upgraded stainless-steel appliance package includes a convection range, while recessed lighting illuminates the space. A cabinet pantry provides additional storage and a convenient coffee bar with a USB outlet adds both functionality and convenience to the kitchen. The charming breakfast nook provides the perfect spot for casual dining. The formal Dining Room features classic chair-rail molding and flows effortlessly into the kitchen, making it ideal for entertaining. The spacious 16' x 23' Primary Bedroom Suite features a beautiful coved ceiling and plenty of room for a comfortable sitting area. Additional features include wall-to-wall carpeting, a safe, and 2 closets, one of which is a walk-in closet. The luxurious Primary Bath offers dual comfort-height vanities with granite countertops, linen closet and walk-in shower with glass enclosure. A bidet and comfort-height toilet are located within the private water closet. A convenient access door leads directly to the patio. Two spacious Guest Bedrooms share a lavishly appointed Guest Bathroom featuring an oversized vanity, luxurious soaking tub accented by a decorative tile surround and a separate walk-in shower with glass enclosure. Outdoor living is truly exceptional in the fully fenced and meticulously landscaped backyard. A sparkling saltwater pool, surrounded by an expansive patio, provides the perfect setting for relaxing or entertaining family and friends. Distant views of Little Lake Eloise add to the tranquil setting. Additional features include a Laundry Room w/ cabinetry, washer & dryer, double-pane Pella fiberglass windows, glass storm door, water softener system, 2024 water heater, security system, stone-accent facade, 2023 architectural shingle roof, well for irrigation, freshly painted exterior, gutters, exterior lights, & 220-volt wiring in the oversized 3 car garage. The garage also features a garage door opener & provides abundant space for vehicles, storage or recreational equipment. Ideally situated in the picturesque community of Harbour Estates, this exceptional home offers the perfect blend of space, comfort, privacy, and convenience, just minutes from shopping, restaurants and LEGOLAND Resort.

37 Lake Eloise Lane, Winter Haven

100 El Camino Drive Unit 301, Winter Haven
$149,900
3 Beds ⋅ 3 Baths ⋅ B4902382 MLS ⋅ Granada Building BLDG.
Welcome to 100 El Camino Drive, Unit 301, a spacious corner-unit condominium located in the established Orchid Springs community of Winter Haven. As one of the larger residences in the building, this home offers an appealing combination of generous living space, privacy, convenience, and low-maintenance Florida living. The thoughtfully designed floor plan provides each bedroom with its own private full bathroom, making the home especially well suited for guests, multi-generational living, or owners who simply appreciate added privacy. As a corner unit, the residence benefits from an enhanced sense of separation and space, while additional storage provides room for seasonal items and everyday necessities. Major improvements include a 2023 Heating system and the home has been replumbed throughout, offering valuable updates for the next owner. Additional conveniences private storage, elevator access, and a designated parking space. Orchid Springs offers a peaceful residential setting highlighted by beautifully maintained grounds and scenic water features, along with access to a private community pool and clubhouse. The monthly association fee provides exceptional convenience by including water, gas, cable, internet, and trash service, helping simplify monthly expenses. Community amenities also include pool and clubhouse access, with association services supporting an easy, low-maintenance lifestyle. The location places you in the heart of everything Winter Haven has to offer. Enjoy convenient access to shopping, dining, medical services, downtown Winter Haven, LEGOLAND® Florida Resort, and the famous Winter Haven Chain of Lakes. Known as the “Chain of Lakes City,” Winter Haven offers abundant opportunities for boating, fishing, kayaking, waterfront dining, and other outdoor recreation while remaining conveniently positioned within Central Florida. Spacious, updated, and packed with included amenities, Unit 301 offers an excellent opportunity to enjoy comfortable condominium living in one of Winter Haven’s most distinctive established communities.

100 El Camino Drive Unit 301, Winter Haven

6059 Navona Way, Winter Haven
$309,990
4 Beds ⋅ 3 Baths ⋅ O6446013 MLS
Under Construction. Introducing the Crestview floorplan, a unique two-story all block construction home available in Villamar, one of our communities in Winter Haven, Florida. Inside this 4 bedrooms, 3-bathroom home you will find 1,866 square feet of desirable living. As you step through the foyer you are greeted with a well-appointed kitchen that features an island with bar seating, cabinets for storage, quartz countertops and stainless-steel appliances. The kitchen overlooks the dining room, living room and outdoor patio making entertaining guests or enjoying time with family easy. The first floor also features a powder room. Perfect for keeping your privacy during guest visits. The second floor is complete with the primary bedroom, three additional bedrooms, a loft, and the laundry room. The primary bedroom includes its own bathroom with a dual vanity sink, separate shower and spacious walk-in closet. Like all homes in Villamar, the Crestview includes smart home technology, which allows you to control your home anytime with your smart device while near or away. *Photos are of similar model but not that of the exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability, and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

6059 Navona Way, Winter Haven

6055 Navona Way, Winter Haven
$336,990
5 Beds ⋅ 3 Baths ⋅ O6446008 MLS
Under Construction. The Robie is a two-story floorplan featured in Villamar in Winter Haven, Florida. With 2 exteriors to choose from, the Robie is sure to turn heads. Inside this inviting 5-bedroom, 3-bathroom home, you’ll find 2,447 square feet of comfortable living. This impressive all concrete block construction, two-story plan features a versatile floorplan to fit your needs. A spacious open-concept first floor which includes a well-appointed kitchen with sleek stainless-steel appliances overlooking the living and dining area. Just off the living room you will find the singular downstairs bedroom and full bathroom. As you move upstairs you are greeted with a spacious living and foyer space to utilize for work or play. The primary bedroom one is located just off the loft space and features a spacious walk-in closet as well as ensuite bathroom with double vanity and all the space you need to get ready in the morning. Three additional bedrooms share a second upstairs bathroom and linen closet for extra storage. Your laundry room is located on the second floor as well as extra storage closets. Like all homes in Villamar, the Robie includes smart home technology, which allows you to control your home anytime with your smart device while near or away. *Photos are of similar model but not that of the exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability, and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

6055 Navona Way, Winter Haven

2668 Rutledge Court, Winter Haven
$232,000
3 Beds ⋅ 2 Baths ⋅ L4965371 MLS ⋅ 2668 BLDG.
Beautifully Upgraded 1-Story Townhome|Low-Maintenance Florida Living! 2 BR PLUS BONUS ROOM-can be used as 3rd Br/2 Full BA home featuring GORGEOUS wood-plank Italian tile floors with authentic real-wood look, designer selected paint-pallets for a neutral interior to make your own. Upgraded carpet in bedrooms, HUGE Walk-in closet in Master BR, custom light fixtures with dimmer in Dining Room for softer lighting when desired. Stainless steel appliances in kitchen with range above oven and disposal. Separate laundry room with storage closet near kitchen. Enjoy soaring high ceiling with sky light and open floor plan with kitchen/dining room/living room adjacent for an open and airy feel. Upgraded ceiling fan/light combos for cool interior, as well as custom outdoor fan to stay cool on your screened in back porch, overlooking beautiful lined oak trees. The garage is designed for convenience with custom ceiling storage racks to provide organization for tools, recreation equipment, and all your Florida lifestyle essentials, while still being able to park in the garage and your private driveway. The Verandahs amenities include gated community pool & private dock on Lake Reeves. Winter Haven is renowned for its famous Chain of Lakes, making this charming town an ideal location for boating, fishing, and outdoor enthusiasts. Conveniently located within easy reach of the attractions and entertainment of Orlando and Tampa, as well as major international airports, this home offers an appealing combination of tranquillity and accessibility. A wonderful opportunity to enjoy comfort, style, recreation and the best of Central Florida!

2668 Rutledge Court, Winter Haven

5281 Pebble Beach Boulevard, Winter Haven
$269,900
3 Beds ⋅ 2 Baths ⋅ P4939964 MLS
Begin the next exciting chapter of your life in Lake Ashton, Central Florida’s premier 55+ active-adult community, where this beautifully maintained and tastefully updated 2-bedroom, 2-bath home with den offers the perfect combination of comfort, convenience, and Florida lifestyle living. Ideally situated on a desirable corner lot with a generously sized yard, this inviting home welcomes you with its attractive curb appeal and continues to impress with thoughtful updates and quality features throughout. The kitchen offers 42-inch upper cabinets and solid-surface countertops, while beautiful wood flooring flows through the living room and den, creating a warm and inviting setting for relaxing or entertaining. The bedrooms feature newer carpeting for added comfort, and important major improvements provide exceptional peace of mind, including a new air-conditioning system and electric water heater in 2018, a new roof in 2023, and exterior painting completed last year for a fresh, crisp appearance and added weather durability. The washer & dryer are newer. Best of all, this exceptional home is being sold turnkey, including the furniture, electronics, furnishings, golf cart, and charger, making it possible to move in and immediately begin enjoying the Florida lifestyle without the hassle of furnishing a new home. Adding even more value, the seller is offering a $4,500 credit at closing toward new kitchen appliances. Beyond your front door, Lake Ashton delivers an extraordinary resort-style lifestyle with two 18-hole championship golf courses, a 26,000-square-foot clubhouse, a state-of-the-art health and fitness center, indoor and outdoor swimming pools, pickleball courts, a bowling alley, and an impressive calendar of clubs, activities, social events, and opportunities to make new friends. With its desirable corner-lot setting, spacious yard, numerous updates, turnkey convenience, golf cart, and access to one of Central Florida’s most sought-after active-adult lifestyles, this is a home that deserves to be experienced in person. Schedule your private showing today and discover how enjoyable your next chapter could be at Lake Ashton.

5281 Pebble Beach Boulevard, Winter Haven

7808 Waterview Way, Winter Haven
$115,000
2 Beds ⋅ 2 Baths ⋅ L4965354 MLS ⋅ 7808 BLDG.
Investor Special!! Welcome to resort-style living in the highly sought-after gated waterfront community of Winterset, where convenience meets comfort in this charming 2-bedroom, 2-bathroom 2-story condo. Step inside to discover a spacious living and dining room combo that creates an inviting atmosphere for relaxation and entertaining. The well appointed kitchen features appliances and a convenient breakfast bar, perfect for causal dining or morning coffee. The master bedroom suite features a generous walk-in closet, providing ample storage space. For your convenience, a stackable washer and dryer are included. This professionally managed community boasts a plethora of amenities, including a clubhouse, fishing pier, heated pool, hot tub, and tennis courts—all overlooking the serene Lake Winterset, part of the renowned "Chain of Lakes." Enjoy peace of mind with state-of-the-art security in this well-maintained environment. You’re just minutes away from Lego Land and conveniently located near Disney and other Florida amusement parks, shopping, dining, and more. Alternatively, relish the numerous community offerings, including a fitness center, shuffleboard, and expansive green spaces perfect for walking your family pet. Experience the perfect blend of leisure and lifestyle at Winterset!

7808 Waterview Way, Winter Haven

7002 Summit Circle, Winter Haven
$340,000
3 Beds ⋅ 2 Baths ⋅ TB8552575 MLS
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

4064 Phoenician Way, Winter Haven
$449,900
3 Beds ⋅ 2 Baths ⋅ P4939945 MLS
GOLF COURSE LIVING AT ITS FINEST! Take a look at this absolutely stunning 3 BR + Den / 2 BA St. John floor plan home in the highly desirable Lake Ashton community, a gated 55+ community in Central Florida! Located on an oversized corner lot, with NO BACKYARD NEIGHBORS you’ll enjoy the serene water views that border Hole 13 along Lake Ashton's West Course. This home has mature and well-maintained landscape with Oak Trees and Beautiful Stately Palm trees, all "watered" by a separate irrigation meter. Highlights you'll love about this home: Double French door entry with Custom Tilework & Interior Finishes in the Open and Spacious Living Room with Tray Ceiling, Triple Sliders that separate the Living Room from the Large Screened Lanai; Luxury Kitchen with Granite Countertops, Tile Backsplash, Under and Above Cabinet Lighting, Custom 42" Maple Cabinets with Pullouts, Pendant Lighting on the Breakfast Bar, SS Appliances, Crown Molding, Glass Front on Select Upper Cabinets and a New Wine Fridge. The Walk in Pantry and Dinette Areas are adjacent to the Kitchen. This home features a Luxurious Primary Suite with Trey Ceiling, His/Her Walk-in closets, a Private En-Suite bathroom complete with a Soaking tub, Separate shower with Custom tile and glass enclosure, Separate His/Her Vanities, and a Dedicated Linen closet. The Primary Suite is a serene retreat after a fun day in Lake Ashton. Additional Upgrades Include: Tile on the Diagonal Flooring, Custom Ceiling fans, Designer lighting fixtures, Stately columns at the entry and a formal dining area, Central Vac, Whole House Sound System and Plantation Shutters. Improvements to the home include: New Roof (2025), New Exterior Paint (2025), Coil Replacement on the A/C, New Water Heater (2025). This home is a Split Floor Plan, offering Privacy for the Owner and Overnight Guests. Bedroom 2 and Bedroom 3 have carpet flooring, a Built in Closet, and ceiling fan. Guests will enjoy the spacious Bath with Comfort Height Vanity and Glass Enclosed Shower. Enjoy Reading a Good Book? Escape to the Den- It's a cozy sitting area and has custom Built-In Shelving- the perfect place to display photos, books or your special "Collectibles. The inside laundry room in this home is sizeable and is the passage from the garage into the home. This home offers a 2- Car Garage and Dedicated Golf Cart Entry. Lake Ashton offers Planned Activities like Dances, Entertainment Series, Karaoke, Bingo and Trivia, Day Trips and SO MUCH MORE! Lake Ashton has two Clubhouses. Residents enjoy Indoor/Outdoor Pools, Pickleball Courts, Tennis Courts, 2- 18 Hole Golf Courses (Memberships Optional), Indoor Racquetball, Movie Theater, Bowling Lane, Fitness Centers (2), Eagles Nest (Eatery), Card, Craft and Billiards and MORE! Schedule an Appointment Today!

4064 Phoenician Way, Winter Haven

1631 Linz Court, Winter Haven
$180,500
2 Beds ⋅ 2 Baths ⋅ L4965373 MLS
Maintenance-free Villa in the 55+ gated community of Vienna Square, centrally located in Winter Haven! A brick-paver driveway and walkway lead through mature landscaping to the covered front porch. Inside, the open floor plan features high ceilings, a spacious great room, and a split-bedroom layout. The primary suite offers a large bedroom and en-suite bath, while the second bedroom is conveniently located near the guest bath. The kitchen features a breakfast bar, ample cabinet and counter space, and all appliances, overlooking the Great Room living/dining area with access to the screened lanai through triple Sliding Glass Door. Low monthly HOA fees include roof replacement, exterior painting, lawn maintenance, irrigation, internet/cable TV, and community amenities. Residents enjoy a pool, hot tub, fitness center, tennis/pickleball, billiards, movie room, craft room, recreation room, and more. Conveniently located near shopping, dining, golf, fishing, boating, medical facilities, entertainment, Legoland, Disney, Universal, and both Tampa and Orlando International airports. Vienna Square offers active adult living with the ease, convenience, and peace of mind of low-maintenance living. This is a VA Foreclosure.

1631 Linz Court, Winter Haven

9504 Waterford Oaks Boulevard, Winter Haven
$725,000
5 Beds ⋅ 3 Baths ⋅ TB8533115 MLS
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

1475 Grand Cayman Circle, Winter Haven
$359,000
3 Beds ⋅ 2 Baths ⋅ L4965284 MLS
Virtually Staged. WATERFRONT LIVING ON BEAUTIFUL LAKE DEXTER-PRIVATE DOCK - OVERSIZED CORNER LOT -Newly Remodeled - 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 a 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

400 Bayou Road, Winter Haven
$254,000
2 Beds ⋅ 2 Baths ⋅ G5118252 MLS
**Price Reduction** 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 and trees. 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), tankless hot water heater (2023), flooring in living room & dining room (2024) 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, security system, and the outdoor front shed do not convey.

400 Bayou Road, Winter Haven

1205 Eagle Pond Drive Unit 1205, Winter Haven
$162,000
2 Beds ⋅ 2 Baths ⋅ S5158253 MLS ⋅ 1205 BLDG.
Enjoy the Florida lifestyle in Cypresswood Golf & Country Club! This inviting 2-bedroom, 2-bathroom second-floor condo offers comfortable living in a desirable Winter Haven community. PRICED TO SELL. The home features LVP flooring, a newer water heater, and convenient exterior storage for golf equipment, seasonal items, and more. Cypresswood Golf & Country Club offers an array of amenities, including a 24-hour manned guard gate, an 18-hole championship golf course, tennis, pickleball and basketball courts, community pool, restaurant, clubhouse and more. Whether you're looking for a full-time residence, winter retreat, or a place to enjoy an active Florida lifestyle, this condo offers comfort and convenience in a welcoming community. Conveniently located near US-27, you'll have easy access to restaurants, shopping, entertainment, and everyday conveniences, while still enjoying the relaxed atmosphere of a golf and country club community. Low monthly HOA fee. Schedule your visit TODAY.

1205 Eagle Pond Drive Unit 1205, Winter Haven

824 Vienna Drive, Winter Haven
$258,000
3 Beds ⋅ 2 Baths ⋅ O6443270 MLS
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

1100 Martinique Drive Unit 220, Winter Haven
$149,900
3 Beds ⋅ 2 Baths ⋅ S5158041 MLS ⋅ A BLDG.
Welcome to easy Florida living in the desirable community of Orchid Springs! This beautifully updated second-floor CORNER/END-UNIT condo offers a wonderful sense of privacy along with an abundance of natural light. Featuring a spacious, open split-bedroom floor plan with 3 bedrooms, 2 bathrooms, an enclosed bonus room and a dedicated inside laundry room, this modern-looking unit provides plenty of comfortable & flexible living space. Thoughtful updates and custom touches can be found throughout, including crown molding and stylish finishes. The beautiful kitchen features granite countertops, updated stainless steel appliances and plenty of cabinet and counter space, creating a functional and inviting space for everyday living and entertaining. The spacious primary suite offers a walk-in closet and private ensuite bathroom with a step-in shower and granite countertop. The split-bedroom layout provides added privacy for family or guests, while the enclosed bonus room adds valuable additional living space and can easily serve as a home office, den, hobby room or additional sitting area. Additional conveniences include a full inside laundry room with washer and dryer included, as well as assigned covered parking. Some of the furniture may also be negotiable, making this an excellent option for buyers looking for an easier transition into their new Florida home. One of the many benefits of Orchid Springs is the affordable condo fee, which includes water, gas, sewer, trash, exterior building maintenance and grounds maintenance, providing for a convenient, low-maintenance lifestyle. Residents also enjoy access to the community clubhouse and swimming pool. Ideally located in SE Winter Haven near Highway 27, this condo provides convenient access to shopping, restaurants, medical facilities, LEGOLAND Florida Resort and everyday necessities. Winter Haven's Central Florida location between Tampa and Orlando also makes it convenient for enjoying everything the region has to offer. Whether you are looking for a full-time residence or a seasonal Florida retreat, this beautifully updated corner unit combines privacy, natural light, modern finishes, additional living space and a convenient location. Schedule your private showing today!

1100 Martinique Drive Unit 220, Winter Haven

12 Saint Kitts Circle, Winter Haven
$294,000
3 Beds ⋅ 2 Baths ⋅ L4965243 MLS
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

6624 Winterset Gardens Road, Winter Haven
$450,000
5 Beds ⋅ 3 Baths ⋅ O6443972 MLS
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

4075 Bedford Avenue, Winter Haven
$344,900
2 Beds ⋅ 2 Baths ⋅ P4939922 MLS
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

2824 San Marco Way, Winter Haven
$272,800
3 Beds ⋅ 2 Baths ⋅ D6148870 MLS
Discover modern Florida living in Villamar, a desirable Winter Haven community with peaceful pond views and convenient access to Central Florida attractions. Built in 2024, this single-story 3-bedroom, 2-bath home offers an open-concept layout with spacious living areas, an oversized island, granite countertops, stainless steel appliances, and a pantry. The private primary suite features an ensuite bath, while two additional bedrooms offer flexibility for guests, a home office, or hobbies. Sliding doors open to a relaxing backyard overlooking the pond. Enjoy community amenities including a pool, clubhouse, and playground. Ideally located near US-27 and I-4, with shopping, dining, schools, LEGOLAND Florida Resort, the Winter Haven Chain of Lakes, and Downtown Winter Haven nearby. A wonderful opportunity to make a newer home your own. Short sale.

2824 San Marco Way, Winter Haven

5974 Foxhollow Drive, Winter Haven
$169,900
2 Beds ⋅ 2 Baths ⋅ S5158044 MLS
Welcome to this charming 2-bedroom, 1.5-bath manufactured home situated on more than a quarter-acre of owned land with no HOA or lot rent! Located in a quiet, established community, this home offers a spacious, private yard with plenty of room for outdoor entertaining, gardening, pets, or simply enjoying your own peaceful space. The property is comfortable and functional as it stands, while offering an excellent opportunity for someone ready to add a little love, complete a few cosmetic improvements, and make it their own. Recent updates include a remodeled kitchen and septic system, both completed in 2026. The main home features central air conditioning, while the Florida room and detached backyard structure each have mini-split systems. The Florida room provides additional flexible living space, and the separate air-conditioned backyard structure is perfect for a workshop, home office, hobby room, or extra storage. Conveniently located near Cypress Gardens Boulevard, shopping, dining, and LEGOLAND Florida, this property combines privacy, land, flexibility, and value in one unique opportunity.

5974 Foxhollow Drive, Winter Haven

817 Reflections Loop E, Winter Haven
$340,000
4 Beds ⋅ 2 Baths ⋅ L4965212 MLS
** $10K PRICE REDUCTION as of 10/23/2026!!** 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

4116 Fishermans Landing, Winter Haven
$237,900
3 Beds ⋅ 2 Baths ⋅ P4939927 MLS
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

5707 E Lake Fox Drive, Winter Haven
$260,000
4 Beds ⋅ 3 Baths ⋅ P4939940 MLS
Virtually Staged. UPDATED 4-BEDROOM, 3-BATH HOME WITH FLEXIBLE IN-LAW SUITE IN WINTER HAVEN! Welcome home to this nicely updated and versatile 4-bedroom, 3-bathroom property in the heart of Winter Haven! With major components already updated—including the septic drain field (2026), plumbing, AC and duct work (2025) and roof (2023) and updated current FHA tie down compliant!—this home offers a great combination of comfort, flexibility, and functionality. Step inside to a spacious living room and dining room combination, with fresh paint and new flooring throughout. The split-bedroom floor plan provides privacy and features generously sized bedrooms with walk-in closets. The primary suite offers plenty of space and a large ensuite bathroom. One of the home's standout features is the one-bedroom, one-bath in-law/guest suite, complete with a separate entrance and conveniently separated from the main living area by a hallway. This flexible space can accommodate a variety of needs, whether used for extended family, guests, a home office, workshop, craft room, or other personal space. The layout also offers the potential to add a small kitchenette for even greater functionality. Additional updates include updated bathrooms and a convenient indoor laundry area tucked behind the kitchen. Step outside to the spacious backyard, offering plenty of room for entertaining, relaxing, gardening, or enjoying the Florida sunshine. For outdoor enthusiasts, a community boat ramp to Lake Fox is just around the corner. Not in a flood zone and not in an HOA!The home is also conveniently located near schools, shopping, healthcare, and LEGOLAND Florida. With its flexible floor plan, major updates, spacious yard, and desirable location, this home offers plenty of possibilities for a homeowner or investor. Schedule your private showing today and come see all this property has to offer!

5707 E Lake Fox Drive, Winter Haven

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