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$334,900
3 Beds 2 Baths Lake Ashton West Ph 01 SubDv. 33884 Zip Code
Welcome to resort-style living in the highly sought-after Lake Ashton Golf Club Community! This impeccably maintained home is nestled on a quiet and secluded street, offering the perfect combination of privacy, comfort, and an active Florida lifestyle. From the moment you arrive, you will appreciate the pride of ownership and pristine condition of this beautiful residence. Designed for both everyday living and entertaining, the home offers spacious living areas, abundant natural light, and a floor plan that flows effortlessly throughout. One of the most valuable features of this property is that the CDD bond has been fully paid off, providing significant long-term savings and added value for the new owner. Lake Ashton is one of Central Florida's premier gated 55+ communities, offering an unmatched array of amenities and activities. Residents enjoy access to two private 18-hole championship golf courses, including one of the most challenging and highly regarded courses in the region, making it a favorite among golf enthusiasts. The community also features two expansive clubhouses, a state-of-the-art health and fitness center, resort-style pools, tennis and pickleball courts, bowling lanes, movie theater, ballroom, restaurant and lounge, arts and crafts facilities, numerous social clubs, and a private marina with access to beautiful Lake Ashton. Whether you are looking for an active retirement, a seasonal retreat, or your forever home, this exceptional property offers the perfect opportunity to enjoy the Florida lifestyle at its finest. Schedule your private showing today and discover why so many residents proudly call Lake Ashton home.

5312 Nicklaus Drive, Winter Haven

$90,000
2 Beds 2 Baths Orange Manor West Coop Inc SubDv. 33884 Zip Code
One or more photo(s) has been virtually staged. 2-Bedroom, 2-Bathroom Mobile Home in a 55+ Community of ORANGE MANOR WEST-NO LOT RENT!-This spacious 1,352 sq. ft. double wide mobile home located in a 55+ community that offers a wealth of amenities for an active lifestyle. BRAND NEW A/C! The living room features sliding glass doors that open to a front enclosed Florida room, perfect for enjoying the view of your front yard. The kitchen comes fully equipped with all appliances and a separate dining room for your meals. BRAND NEW REFRIGERATOR AND RANGE. The main bedroom boasts an en-suite bathroom and a walk-in closet. The second bedroom is adjacent to a recently updated bathroom. Inside laundry room with additional storage, washer, and dryer included. A long carport that can accommodate two cars, with a garage door leading to extra storage space. Roof: Installed in 2017. Community Amenities: Pool, Clubhouse with billiards and library,Putt-putt golf, Bocce ball and horseshoe fields, Shuffleboard and Basketball court. Please note, this park does not allow pets. Don’t miss out on this wonderful opportunity! Call now for more details.

134 Lake Hazel Drive, Winter Haven

$309,900
2 Beds 2 Baths Traditions Ph 01 SubDv. 33884 Zip Code
WELCOME TO CAREFREE LIVING WITH THIS WELL-MAINTAINED RESIDENCE WITHIN THE DESIRABLE 55+ GATED, LAKEFRONT COMMUNITY AT "TRADITIONS OF RUBY LAKE". This home is MOVE IN READY and is situated withing very close proximity to the clubhouse and Lake Ruby!!! NEW ROOF and NEW HOT WATER HEATER both installed in 2023. With nearly (1,820 Sqft.) of heated and cooled space, this OPEN-CONCEPT SPLIT PLAN with SOARING CEILINGS will not disappoint. There is plenty of room for the chef in the family with your OVERSIZED KITCHEN that has an ABUNDANCE of cabinetry and GRANITE COUNTERTOPS! The kitchen also has 2 windows, giving you a pleasant view along with plenty of extra natural light. Just off the kitchen sits the great room leading into 2 bedrooms and another room (11 x 10) that would be perfect for an office, craft room, or out of town guests. You'll love the (21 x 9) BONUS ROOM that has its own AC and gives you so much extra cooled living space. As if this wasn't enough, the bonus room also overlooks a (21 x 9) SCREENED, PAVERED PATIO for outside grilling or just relaxing. The large primary en-suite has a WALK-IN-SHOWER WITH BUILT-IN BENCH and GLASS SLIDERS, DUAL SINKS, and OVERSIZED WALK-IN-CLOSET. You have direct access to the bonus room from the primary bedroom. Cleaning is a breeze in this home featuring NO CARPET!!! The clubhouse is beautiful and boasts amazing views beyond the pool of 2 lakes (Ruby and Bess). The clubhouse also features an oversized pool and spa, dock, boat ramp, boat slips, tennis courts, pickle ball, basketball, shuffleboard, ball room, billiards, library, craft room, fitness center, dog park and much more! Golf carts are allowed in the community for ease of navigating. Traditions is centrally located in close proximity to medical, shopping, restaurants, 2 major international airports (Tampa/Orlando) and the up and coming airline Avelo in Lakeland, FL. LEGOLAND, FL is just minutes away!

4130 Bedford Avenue, Winter Haven

$329,900
4 Beds 2 Baths Krenson Bay SubDv. 33881 Zip Code
Welcome to 292 Krenson Bay Loop, a 2024-built block home located in a gated Winter Haven community with NO CDD! This 4-bedroom, 2-bath home offers 1,820 square feet of living space, a 2-car garage, irrigation system, and a desirable split floor plan designed for comfort and functionality. Inside, you’ll find tile throughout the main living areas and kitchen, with carpet in the bedrooms. The modern kitchen features stainless steel appliances, subway tile backsplash, a large pantry, and an oversized peninsula with bar seating, opening nicely to the breakfast nook and main living area. A formal dining room provides additional space for gatherings or flexible use. The primary suite includes a walk-in closet and private bath with dual sinks, a garden tub, and a separate shower. Enjoy Florida living from the covered lanai, perfect for relaxing outdoors. Located in Winter Haven, this home offers convenient access to local lakes, shopping, dining, medical facilities, and nearby attractions including LEGOLAND Florida Resort. With easy routes to Lakeland, Tampa, and Orlando, this location provides a great balance of Central Florida living and regional convenience.

292 Krenson Bay Loop, Winter Haven

$290,000
3 Beds 2 Baths Morningside SubDv. 33884 Zip Code
You will be impressed the moment you walk through the door! It’s so clean, polished and move-in ready! This home is a beautifully maintained 3-bedroom, 2-bath home located in the desirable Morningside neighborhood within the gated Winterset community. This thoughtfully designed split-bedroom floor plan offers both comfort and functionality, featuring a formal living room, formal dining room, and a spacious great room ideal for everyday living and entertaining. There is opportunity for lots of natural light with the storm front door and the garage screening. Both the garage and lanai screenings were replaced in 2024 when exterior paint was completed. The kitchen is conveniently positioned with a nearby laundry closet and flows seamlessly into the main living areas. Two secondary bedrooms share a well-appointed hall bath, providing privacy for family or guests. The primary suite is a true retreat, complete with sliding glass doors leading to the Florida room, dual walk-in closets, and a luxurious en-suite bath featuring a soaking tub, separate shower, and ample space. Enjoy year-round relaxation in the expansive Florida room, perfect for a seating area and dining setup, all overlooking a generously sized backyard. This home has been thoughtfully updated and is move-in ready with new carpet throughout (2026), giving it a fresh, like-new feel. Additional updates include: Refrigerator (2023) Garage door opener (2020) Garbage disposal (December 2023) Exterior paint (September 2024) Water heater (September 2024) HVAC system (2014) Winterset offers resort-style amenities including a gated entrance, community pool, tennis courts, scenic lake views, and a private boat ramp. Conveniently located in SE Winter Haven just off Cypress Gardens Blvd, you’ll enjoy easy access to shopping, dining, and local events. Don’t miss the opportunity to own this exceptional home in one of the area’s most sought-after communities!

142 Morning Glory Circle, Winter Haven

$279,000
3 Beds 2 Baths Richmond Square Ph 02 SubDv. 33884 Zip Code
One or more photo(s) has been virtually staged. Price Improvement – Motivated Seller! Welcome to Winterset, one of Winter Haven's most desirable gated lakefront communities! This beautifully designed 3-bedroom, 2-bath home, built in 2006, offers 1,994 square feet of comfortable living space. Winterset is not a 55+ community, and there is no separate master association fee. A covered, screened front porch welcomes you into a spacious great room that opens to an impressive 550-square-foot screened rear porch with beautiful porcelain tile—perfect for relaxing, entertaining, and enjoying Florida's indoor-outdoor lifestyle. The home features no carpet, with durable laminate flooring installed throughout in 2020. Situated on a rare double lot, this property offers added space, privacy, and flexibility that is hard to find in Winterset. While the additional lot is not buildable, it provides plenty of room to add a pool, expand your outdoor living space, or create a larger circular driveway—giving you options that most homes in the community simply don't have. The split-bedroom floor plan offers privacy, with two secondary bedrooms sharing a hall bath complete with a tub and linen closet. The inside laundry room includes the washer and dryer. Recent improvements include a new water heater (2026) and HVAC (2021). Additional features include a tile roof, brick paver driveway, 2-car garage, and garage screen door for added ventilation and flexible use. Winterset residents enjoy exceptional amenities, including a lakefront clubhouse overlooking Lake Winterset, heated pool and spa, tennis and pickleball courts, shuffleboard, and a private boat ramp with access to Lake Winterset and the renowned Winter Haven Chain of Lakes. HOA fees include grounds maintenance, gated security, and access to all community amenities. Conveniently located near LEGOLAND® Florida, shopping, dining, medical facilities, and with easy access to both Tampa and Orlando, this home offers the perfect combination of comfort, convenience, and Florida living.

3027 Richmond Drive, Winter Haven

$395,000
4 Beds 3 Baths Traditions Ph 02 SubDv. 33884 Zip Code
Welcome to TRADITIONS, an active 55+ gated community located in the heart of the state on Lake Ruby. From swimming laps in the olympic size pool, casting a line at the lake, swinging a pickleball racquet or utilizing the fitness room and scheduled classes, there is plenty to do to stay in shape. If you prefer a more relaxed day, the clubhouse provides plenty of social spaces for card games, crafting, puzzles and reading a book. The community has planned monthly activities, they even plan a yearly community cruise if that's your vibe. You don't need to leave the community to find something to do, however; Disney and Universal Studios are nearby and you can reach either coast in less than two hours. The community is close to shopping (Publix coming soon), medical facilities, Legoland and the quaint downtown area of Winter Haven with boutique shops and local restaurants. This community is truly the ultimate 55+ lifestyle. The monthly dues include: community amenities, Spectrum cable and internet, lawn maintenance, common area maintenance, and exterior paining every 8 years. Now for the house: This is a Kennedy model floorplan, one of the most sought after in this community. It is a SHOW STOPPER from top to bottom and these Sellers have executed great care during their ownership. You will appreciate some of the additions they have made such as the extended rear screened lanai with Coolaroo shades and a motorized hurricane shutter. They also extended a paver BBQ area for those who like to grill. They added overhead storage racks in the garage and if you are an angler you will appreciate the storage system for the fishing poles! They have also added a motorized screen door for the days that you want to tinker in the garage and keep the bugs out. The exterior was just painted in 2025. The lawn is manicured with professional landscape edged flower beds and best of all the grass is maintained by the HOA. Step inside the front door to be instantly impressed with the high ceilings. The space is open enough for great entertaining but also offers space to spread out when needed. Ceramic tile in all the wet areas and living spaces with 5 inch baseboards and crown molding give the feeling of luxury. Recessed lighting, pendant lights as well as good window placement bring good lighting into the space. The kitchen is spectacular. 42 inch upper cabinets, quartz counters, walk in pantry and preparation island make the space functional for the chef and easy to entertain in. There are three dining space choices: formal dining area, breakfast nook and a breakfast bar providing with plenty of seating. The living room flows perfectly from the triple sliding door onto the lanai. The wall mounted TV's convey. The floorplan also offers a triple split bedroom plan. The primary bedroom offers an ensuite and the walk in closet has custom built in shelving. The ensuite has dual sinks, private commode room, linen closet and soaking tub. The walk in shower has no step and has nice glass doors. The 2nd and 3rd bedrooms share a guest bath with dual sinks and the 4th bedroom has a private ensuite. You truly have to see this home to appreciate its flow, style, tidiness and all the features that make this place a HOME! If 55+ living in Florida is what you have been dreaming of, you just found it! Come make some new Traditions!

3890 Bedford Avenue, Winter Haven

$280,000
4 Beds 2 Baths Buckeye Trace SubDv. 33881 Zip Code
PRICE DROP!! Nestled within a secure, gated community with impressively low HOA fees, this beautiful 4-bedroom, 2-bathroom home offers true peace of mind. The highly versatile layout easily adapts to your lifestyle, whether you need extra space for a growing family, a dedicated home office, or a welcoming guest suite. Beyond the front door, you're just minutes from top-rated schools, medical services, and daily conveniences like Publix. Spend your weekends exploring the vibrant dining and nightlife of Downtown Winter Haven or making memories at nearby Legoland. More than just a house, this property is an extraordinary opportunity to secure a lifestyle of comfort and convenience. Schedule your tour today before it slips away!

1646 Tressel Court, Winter Haven

$269,000
3 Beds 2 Baths Buckeye Ridge SubDv. 33880 Zip Code
MOVE-IN READY WITH MODERN UPDATES ON A PRIME CORNER LOT! Built in 2017 and featuring a LOW HOA, this beautifully maintained home offers a desirable open floor plan with a 3-way split bedroom layout, delivering the perfect balance of functionality and privacy. Enjoy peace of mind with NEW luxury vinyl plank flooring (2025) and fresh interior paint (2025), creating a clean, modern, truly turnkey feel throughout. Architectural details like decorative arches add character, while 18x18 tile in all wet areas enhances durability and style. The kitchen showcases 36” espresso cabinetry, generous storage, and all appliances included, making it ideal for both everyday living and entertaining. Additional highlights include window treatments throughout, an inside laundry room with washer and dryer, and abundant storage space. Step outside to your covered lanai, perfect for relaxing year-round. Situated on a spacious corner lot, the property offers added privacy and curb appeal. Conveniently located just minutes from Highway 27 and approximately 15 minutes to I-4, providing easy access to commuting, shopping, and dining. 1711 sq ft | 3 Bedrooms | 2 Bathrooms | 2-Car Garage

4140 Sophia Boulevard, Winter Haven

$469,900
3 Beds 2 Baths Hartridge Hills SubDv. 33881 Zip Code
LAKEFRONT 3 BEDROOM / 2 BATH HOME ~ 2,847 SQ FT ~ WITH PICTURESQUE OPEN WATER VIEWS AND PRIVATE 30 FT DOCK! OWNER FINANCING AVAILABLE. Located directly on Lake Pansy in the gated subdivision of Hartridge Hills, a quaint lakefront community of approximately 60 homes. NEWER ROOF 2022 and NEWER GENERAC GENERATOR 2020. Lot size is 150 X 83 ft directly on Lake Pansy. Additional lot size in records of 2.44 acres includes riparian or water rights into the lake. Beautiful stone working fireplace with vaulted ceiling in the great room. Spacious kitchen with plenty of storage and breakfast area overlooking tranquil water views. With 2,847 sq ft of air-conditioned living space under roof, you have plenty or room for entertaining and extended family. Large windows and sliding glass doors frame panoramic vistas, infusing the space with a sense of tranquility and connection to nature. Attached 2-car garage with large storage room with AC. HOA fees include lawn care, trimming and fertilizer to give you more time to relax. Access to Lake Hartridge and the ‘Chain of Lakes’, a navigable canal system connecting 15 lakes, is obtained from the private community boat ramp and dock. This community is well known and desired by aircraft owners and flying enthusiasts as it is near Gilbert Field-Winter Haven Regional Airport, a city-owned airport that supports over 80,000 flights a year. It is also home to the Jack Brown Seaplane Base renowned as the largest and one of the oldest seaplane training and base operations in the world. Conveniently located between Orlando and Tampa with great attractions, waterfront restaurants, shopping, and some of the best fishing and ski lakes available! Welcome home to endless days of sunshine and relaxation. Please see the interactive 3D virtual tour and floor plan. Virtually staged photos are included.

247 S Lake Pansy Drive, Winter Haven

$110,000
2 Beds 2 Baths Oakwood Estates SubDv. 33880 Zip Code
Check this out!! The home has new vinyl plank and new carpet in the bedrooms and a new roof in 2025. Enjoy the nice sized living room with relaxing cool blue paint and chair rail. Additionally there is a built in for additional storage and display area for your trinkets. The kitchen offers a nice flooring, with upgraded countertops and lots of cabinets and storage. The hall bathroom has been upgraded with vinyl plank and a custom shower. The primary bathroom offers nice space and a walk in closet. All the floors have plywood subfloors with vinyl plank or carpet. The back porch on the home has been framed in and divided into two office spaces. The walls at the back of the house are freestanding and can be easily removed revealing the glass behind them. Step out the back door onto a covered porch area allowing access to the shed that houses the washer and dryer. Oakwood Estates, a 55+ community, offers many activities and amenities. You can be as active as you would like or just sit back and watch the world go by. The Seller is a smoker inside the home. Please beware if you have smoke allergies.

4173 Rolling Oaks Drive, Winter Haven

$429,500
4 Beds 4 Baths Valhalla SubDv. 33884 Zip Code
DONT MISS THIS RARE LAKEVIEW OPPORTUNITY IN DESIRABLE VALHALLA GATED COMMUNITY. THIS 2 STORY TOWNHOME OFFERS OVER 2700 LIVING AREA WITH STUNNING VIEWS OF LAKE ELOISE. THIS HOME FEATURES 4BR/3.5BA WHICH INCLUDES A DOWNSTAIRS PRIMARY SUITE AND A SECONDARY UPSTARS PRIMARY. THIS CUSTOM JOHN TOUCHTON BUILT HOME BOASTS OF STUNNING QUALITIES THROUGHOUT. THE KITCHEN HAS PORCELAIN TILE FLOORING, MODERN MID-CENTURY OAK CABINETRY, STAINLESS APPLIANCES AND A CONVENIENT COFFEE BAR. ANDERSEN THERMAL PANE WINDOWS WITH SOLAR SHADES PROVIDE ENERGY EFFICIENCY AND ABUNDANCE OF NATURAL LIGHT THROUGHOUT. OVERSIZED 2 CAR GARAGE ALSO HAS A WORKSHOP. ENJOY YOUR RESORT STYLE AMENITIES WITH THE CLUBHOUSE, POOL, TENNIS AND YES , "PICKLEBALL". ONLY MINUTES TO DOWNTOWN WINTER HAVEN FOR RESTAURANTS, SHOPPING AND COMMUNITY EVENTS. EASY ACCESS TO HWY 27 TO I-4 ACCESS TO ORLANDO/DISNEY OR TAMPA. YOU'LL LOVE LIVING IN "THE CENTER OF THE STATE" ... FLORIDA LIVING AT ITS BEST!

139 Woden Way, Winter Haven

$579,900
3 Beds 2 Baths Lake Ashton West Ph 01 SubDv. 33884 Zip Code
DON"T SCROLL PAST THIS BEAUTIFUL DESIGNER HOME in the PREMIER Active 55+ Community in LAKE ASHTON. You will LOVE THE EXPANSIVE WATER VIEW OVER THE LAKE in the back. You can see the LAKE easily from the extended Screen Veranda, LOOKING TOWARDS THE CLUBHOUSE and OVER THE GOLF COURSE with FRONTAGE ON the 2ND GREEN of the WEST COURSE...and the SUNSETS are GORGEOUS. This amazing DESIGNER CUSTOM BUILT HOME has everything you are looking for..... From the Beautiful Front Door, the Amazing Stone Accent on the front corners of the house, Gutters on the Front, Side and Back of the home and the Enclosed Screened Entrance ... To the exceptional entrance with High Ceilings, and offering Coffered and Tray Ceilings in the Great Room and Master Bedroom. When you enter this amazing HOME, you will be awed by the Beautiful Designer Features that this home offers, that gives it an elegance that you will admire and enjoy for years to come. ... A Huge benefit in choosing this home is that "You" are going to save thousands on this property because the CDD DEBT IS COMPLETELY PAID IN FULL! The OPEN FLOOR PLAN sets the stage for seamless living combined with elegance. This HOME IS MOVE-IN READY. Some of the many designer upgrades in this home include: Large 20" Diagonal Tile throughout the home in most rooms with excellent upgraded carpeting in the bedrooms, the Gourmet Kitchen with Stainless Steel Appliances, which is open to the Great Room, has 42" All Wood Cherry Cabinets w/ crown molding "bump up and out cabinets, high end Tile Backsplash ( 2022) New Range (2022) Dishwasher (2023) Stainless Steel Refrigerator, Custom Pendant lights over the Kitchen Bar that looks into the GREAT ROOM, and beautiful Granite that completes the designers influence. The Exterior of the house has been Painted in 2025. This floor plan allows easy access to the extended Veranda through the 3 Sliding glass doors which opens from the Great Room into the Large SCREENED Veranda (14 X 34). The View looks over the Golf Course and Lake in the back. The Expanded Den creates a comfortable reading or gathering room for friends and family. The Master Bedroom boasts of a Tray Ceiling and sliders with Silhouette Vertical Blinds that lead to the Expanded Veranda. Throughout the house you will enjoy Designer Ceiling Fans, Window Tinting, Vertical Cellular Blinds at the Kitchen and Great Room Sliders, also Designer upgrades in the bathrooms that compliment the Master Bathroom Suite. Other important upgrades are the NEW ROOF in JULY 2025, Newer Water Heater in 2020, and the A/C is only 6 years old. The 2 car + Golf Cart garage with the added MOTORIZED SCREEN on the garage door along with the added protection with the insulated Garage Doors. Also, the large garage adds additional storage and leads into the inside laundry giving added room for the Washer and Dryer and Walk in Pantry. You will enjoy the Active Lifestyle present in Lake Ashton that sets this community apart from other communities in the Central Florida area. 2 Large Clubhouses, 3 Natural Lakes, 2 Private Golf Courses, Bowing Alley, Movie Theater, Tennis, Pickleball, Basketball court indoor, 2 Pools, 1 indoor and 1 outdoor Pool with Hot Tubs, Sauna, 2 Fitness Centers, Cards, Crafts, Entertainment, Fishing, Boating and close to stores, shopping, and lots or Restaurants. Call today for your private tour and see how much this Active Lifestyle Community will add to your health and enjoyment during these Golden Years.

5268 Pebble Beach Boulevard, Winter Haven

$120,000
2 Beds 2 Baths Oakwood Estates SubDv. 33880 Zip Code
Check out this well maintained home located in Oakwood Estates, a 55+ community, located in Sunny central Florida. The home features a very open and inviting kitchen, perfect for entertaining. The cooktop and built in oven have been updated. Step into the primary bedroom to find plenty of space for a king size bed, then step into the remodeled and updated primary bathroom. The split bedroom floor plan offers privacy to guests with a bathroom conveniently located outside the door. All the flooring is a laminate with no carpeting in the home. Enjoy the peaceful screened side porch. The home is located on a corner lot with a Florida room giving views of both streets, a great place for your morning coffee. The double pane windows and window AC offers additional living space when guests arrive. Oakwood Estates offers many amenities and activities. You can be as busy as you would like or enjoy the peaceful community and watch the world go by.

4155 Sprucewood Street, Winter Haven

$100,000
2 Beds 2 Baths Orange Manor West Coop Inc SubDv. 33884 Zip Code
NO LOT RENT! Live the retired life you worked so hard for. Whether you are a snowbird or looking to enjoy full-time residency, Orange Manor West welcomes you. This highly sought-after 55+ gated community in Winter Haven, secondary resident(s) must be 40+. This fully furnished 2-bedroom, 2-bath home offers a functional layout with recent updates including a 2018 roof, 2022 HVAC, 2021 water heater, newer vinyl flooring, and updated appliances. The home features a spacious layout with walk-in closets in both bedrooms, a private primary suite with a step-in shower, and an enclosed Florida room that is perfect for relaxing mornings or unwinding in the evening. Enjoy an active, low-maintenance lifestyle with monthly fees that include cable, internet, and trash, in a community that allows only service and emotional support animals. Residents have access to a wide range of amenities including a community pool, clubhouse, billiards, shuffleboard, horseshoes, mini golf, fishing, lake access, and a full calendar of social activities such as bingo, cards, sports tournaments, quilting, and much more. Additional features include onsite management, 24-hour emergency service, extra storage for boats and recreational vehicles, and boat slips. Located in Southeast Winter Haven, you are just minutes from shopping, dining, and everyday conveniences, with Legoland ad Peppa Pig theme parks nearby for visiting guests. This is a great opportunity to enjoy comfort, convenience, and community all in one place.

125 Lake Hazel Drive, Winter Haven

$599,900
3 Beds 2 Baths Lake Ashton West Ph 01 SubDv. 33884 Zip Code
Welcome to the next exciting chapter of your life in Lake Ashton, Central Florida’s premier 55+ active-adult community, where this immaculately maintained three-bedroom, two-bath home with a den offers exceptional comfort and elegance, including a beautiful primary suite with its own relaxing sitting room and a sparkling 7½' x 36' bromine pool awaiting your enjoyment. From the striking stone front elevation and bronze screened front entry to the expansive 51' x 13' bronze screened veranda, this home impresses at every turn. Perfectly positioned on a large pond with a nature preserve beyond, it provides delightful sunrise views and frequent sightings of the abundant wildlife that makes Lake Ashton so special. Step inside through the elegant double glass doors and immediately notice the clean, crisp, and welcoming feel that creates the ideal setting for both relaxed everyday living and gracious entertaining. The interior showcases stunning terraced crown molding, coffered ceilings in both the living room and primary bedroom, and five solar tubes that fill the home with abundant natural light. The kitchen is beautifully appointed with gorgeous cabinetry featuring two glass-front cabinets, a wine rack, and rich black granite countertops, complemented by a large walk-in pantry offering generous storage space. Both bathrooms include walk-in showers and granite counters, adding style and convenience. One of the home’s most remarkable highlights is the expansive screened enclosure with pool at the rear of the property, where the views of the pond, wildlife, and nature preserve are among the finest along Hogan Lane. Additional peace of mind comes from an updated air conditioning system and a roof that is only three years old. Residents of Lake Ashton enjoy unmatched amenities including two championship 18-hole golf courses, a 26,000-square-foot clubhouse, a state-of-the-art health and fitness center, theater, pickleball courts, bowling alley, and so much more, creating an active and fulfilling lifestyle. This exceptional property offers the perfect blend of comfort, convenience, and community—schedule your private showing today and experience the very best of Florida living.

5365 Hogan Lane, Winter Haven

$125,000
2 Beds 2 Baths Oakwood Estates SubDv. 33880 Zip Code
This home is a MUST SEE? You will find many updates in this home from the beautiful granite counters in the kitchen and new kitchen cabinets to the remodeled bathrooms. All flooring is either ceramic or vinyl flooring. The Singled roof is approximately 11 years old and the ac was installed in 2025. The water heater was installed in 2024. This home will be sold mostly furnished. If that isn't enough, from the carport area there is a beautiful view of the lake and lakeside amenities. Oakwood Estates is a very active 55+ community offering many amenities including two pools, two clubhouses, miniature golf, tennis courts, shuffleboard and more. You can be as busy as you want, or just sit back and enjoy peaceful Florida living. Visit the Oakwood website for more info on the community and to see the governing docs.

4918 Rosewood Street, Winter Haven

$384,900
3 Beds 2 Baths Lake Ashton West Ph 2 South SubDv. 33884 Zip Code
Are you looking for a move-in ready home? Well, you found it! This home is like a new build, only better. It is clean as a whistle, has tasteful lighting and fans, luxury plank vinyl, granite countertops, screened lanai, retractable screens on the garage, epoxy garage floor, pad for a grill outback, only naming a few. This is an open floor plan that is great for either entertaining or hanging out at home by yourselves. The home was built in 2020 so it was designed to be eco friendly which makes it easier on the pocketbook. The master has an ensuite bath and a large walk in closet. The two additional bedrooms are a comfortable size for guests. One of the rooms has 3 windows that bow out which allows in lots of natural light, not to mention the bit of extra floor space it adds. It is a perfect space for a desk should you choose to make this your office. All this plus the fact that it is in one of Florida's premier Active Adult Communities. There are two 24 hr manned entrances, 2 pools & hot tubs, billiard rooms, craft rooms, computer libraries, bowling alley, movie theater, 3 dog parks, golf course, pro shop, dances, entertainment and too many clubs and activities to mention. You can be as active or involved as you like. Live and mingle among folks you may have a lot in common with and many of the same interests.

1347 Oakmont Drive, Winter Haven

$399,900
3 Beds 2 Baths Ruby Lake Ph 01 SubDv. 33884 Zip Code
Welcome to your dream home in the gated community of Ruby Lake! This beautifully designed 3-bedroom, 2-bath Cassidy “Ox” floor plan perfectly balances elegance and everyday comfort. Step inside to discover a spacious layout featuring formal living and dining rooms, along with a generous family room—ideal for both entertaining and relaxed living. The updated kitchen is truly the heart of the home, showcasing sleek quartz countertops, a breakfast bar, closet pantry, and durable tile flooring. Retreat to the impressive primary suite, offering a large 17x15 bedroom, walk-in closet, and a spa-like en suite bath complete with soaking tub, walk-in shower, and dual vanities. Thoughtfully designed, the secondary bedroom and bath are handicap accessible with widened doorways for added ease. Enjoy Florida living year-round on the expansive 10x38 screened lanai—perfect for gatherings or quiet evenings. Additional highlights include an interior laundry room with sink, surround sound throughout, plantation shelving with ambient lighting, ceiling fans, irrigation system with separate meter, and a 2-car garage with a high-profile door. Conveniently located near shopping, dining, medical facilities, schools, and Legoland, with easy access to Tampa and Orlando—this exceptional home truly has it all. Don’t miss your opportunity to make it yours!

357 Ruby Lake Loop, Winter Haven

$258,500
2 Beds 2 Baths Vienna Square Ph 2c SubDv. 33884 Zip Code
BETTER THAN NEW!!! Why wait to build when you can move into this HIGHLY UPGRADED, MAINTENANCE FREE villa in the 55+ GATED COMMUNITY of Vienna Square, centrally located in Winter Haven, FL. Before entering this beautiful residence, you will notice the BRICK PAVERED driveway/walkway leading through the MATURE LANDSCAPE and CUSTOM LIGHTING to the front SCREENED LANAI. Walk right into this very OPEN FLOORPLAN with HIGH CEILINGS and SPLIT BEDROOM CONCEPT. The kitchen is a CHEF'S DREAM, featuring UPGRADED STAINLESS APPLIANCES, IMPRESSIVE WINE FRIG., and BREAKFAST BAR. The CASCADING WATERFALL EDGE QUARTZ COUNTERTOPS add a MODERN, ELEGANT and LUXURIOUS focal point to this AMAZING KITCHEN!!! The adjoining great room is very spacious and overlooks the rear SCREENED LANAI with a view of the pond. The primary en-suite will not disappoint which also features QUARTZ COUNTERTOPS and an UPGRADED WALK-IN SHOWER with GLASS DOOR. CUSTOM PLANTATION SHUTTERS in the kitchen and bedrooms ensure you have the privacy you deserve! Don't forget about the second bathroom that has also been UPGRADED with QUARTZ COUNTERTOPS as well. This residence is truly TURN-KEY and one of the most WELL KEPT, ONE-OWNER homes you'll find anywhere. The reasonable monthly HOA dues include: ROOF REPLACEMENT, EXTERIOR PAINTING, YARD MAINTENANCE, LAWN IRRIGATION, and INTERNET/TV PACKAGE! Enjoy the other amenities including, but not limited to: pool/hot tub, tennis/pickle ball, gym, craft room, billiard room, movie room, and large meeting room with remodeled kitchen area. This wonderful property is in close proximity to medical, restaurants, shopping, worship, and LEGOLAND, FL. Winter Haven is well-known for it's beautifully interconnected lakes and being centrally located between the Tampa International and Orlando International Airports.

1678 Linz Court, Winter Haven

$262,500
2 Beds 2 Baths Traditions Ph 01 SubDv. 33884 Zip Code
Welcome to this beautifully maintained residence located in the lakefront community of Traditions, one of Winter Haven’s premier 55+ gated communities known for its vibrant lifestyle and exceptional amenities. Fully upgraded with a brand-new HVAC system & water heater installed (both in March 2026), an updated roof (November 2023), updated kitchen appliances (2024), refreshed landscaping (2026), newer irrigation controller and bidet (2025), fresh interior paint (December 2025), exterior paint (2024). This thoughtfully designed 2-bedroom, 2 bathroom home also includes a versatile office that can easily serve as a third bedroom, along with a spacious family room that provides additional living space for relaxing or entertaining. As you arrive, you’re welcomed by a covered and screened front entry. Inside, the open concept floor plan is enhanced by vaulted ceilings and a stylish blend of luxury vinyl flooring in the main living areas & ceramic tile in the kitchen, bathrooms and laundry room, creating both elegance and easy maintenance. The eat in kitchen is bright & inviting, featuring a closet pantry, stainless steel appliances that are just two years old and a comfortable dining space ideal for everyday meals. An interior laundry room is conveniently located just off the kitchen and provides direct access to the two car garage. Sliding glass doors from the living room lead to a screen enclosed patio, offering the perfect spot to unwind, entertain guests, or simply enjoy Florida’s beautiful year round weather. The primary suite serves as a relaxing retreat, highlighted by a tray ceiling, walk in closet & an ensuite bathroom with a double sink vanity and step-in shower. Outside, the property is beautifully framed by mature landscaping, with an attached two car garage, brick paved driveway & walkway that enhance the home’s inviting curb appeal. Residents of Traditions enjoy a true resort style lifestyle, featuring a lakefront clubhouse with a library, fitness center, card room, & billiards, as well as a resort style pool, hot tub and sauna. Additional amenities include tennis and shuffleboard courts, a dog park, a boat ramp & a dock overlooking Ruby Lake, providing endless opportunities for relaxation and recreation. The $484 monthly HOA fee covers lawn care (including bush/tree trimming and mulch replacement), exterior painting, cable, and internet. Ideally located near shopping, dining, and medical facilities with Publix opening soon just down the street, this home offers the perfect combination of comfort, convenience, and an active community lifestyle.

4019 Carteret Drive, Winter Haven

$405,900
4 Beds 3 Baths Traditions Ph 01 SubDv. 33884 Zip Code
Seller is willing to offer funds towards Buyer's Closing Costs. Welcome to 4020 Carteret Dr in Winter Haven, a beautifully updated 4-bedroom, 3-bath home located in a desirable 55+ lakefront community with a 3-car garage offering comfort, convenience, and low-maintenance living in the heart of Central Florida. This thoughtfully designed home features stunning lake views, hardwood flooring, an updated kitchen with modern finishes, and stylish upgrades throughout. The spacious layout includes a mother-in-law suite, perfect for visiting family, guests, or additional privacy. Residents enjoy direct water access and a private community boat ramp, providing easy access to Winter Haven’s renowned Chain of Lakes, ideal for boating, fishing, and enjoying Florida’s outdoor lifestyle. The community also offers boat and water toy storage for a small fee, making it convenient to keep your boat or jet skis nearby and ready to use. One of the standout features of this home is the maintenance-free lifestyle. The HOA covers Cable, Internet, Exterior Home Maintenance including landscaping, mulch, and exterior painting, and More, allowing homeowners to enjoy their property without the typical upkeep responsibilities. Located just minutes from Cypress Gardens Boulevard, this home offers quick access to shopping, restaurants, grocery stores, golf courses, parks, and medical facilities. Residents are also close to LEGOLAND Florida Resort, and major roadways including US-27 and the Polk Parkway, making travel to Lakeland, Orlando, and Tampa convenient. If you’re searching for a Lake view home in Winter Haven, a low-maintenance home in a 55+ community, or a property with Ruby Lake access, 4020 Carteret Dr offers the perfect combination of location, lifestyle, and modern comfort in one of Polk County’s most established lake communities. Schedule a showing today!

4020 Carteret Drive, Winter Haven

$299,999
3 Beds 2 Baths Lake Bess Country Club SubDv. 33884 Zip Code
Hurry! Won't last long with this Price Drop! MILLION DOLLAR GOLF COURSE VIEW out your back windows! No back yard neighbors ...JUST the peaceful golf course. BRIGHT & Open Home features Split floor plan with Great Room & Formal Dining together, nice for entertaining. Lovely Kitchen offers Breakfast Nook & CHARMING Built in Shelving. Primary Suite with Tray Ceiling, Walk-in Closet, Dual Sink Vanity, Large Tiled Shower, & Garden Tub with Jets. Crown Molding throughout adds personality! QUALITY Ceiling Fans. FLORIDA ROOM with windows that lock delivers the Most Relaxing GOLF COURSE View. INSIDE Utility. Oversized Garage (28X25) will fit the LARGER VEHICLE, with Golf Cart Garage Door. EXTREMELY WELL MAINTAINED, which means A LOT! New Septic Drainfield installed 7/2026, New Sod, Roof/house/front walk/driveway just pressure washed 2025. A/C & heat pump 2019. Security system and smoke detectors updated in 2019. Lake Bess Country Club INCLUDES 1 of 49 shares to the golf club which = 2 memberships, unlimited Golfing, Driving Range, Putting Green, Community Pool, Clubhouse (conveniently located ACROSS THE STREET), & Lawn Maintenance. YOU WILL LOVE THIS HOME!

221 Golf Aire Boulevard, Winter Haven

$119,000
2 Beds 2 Baths Carefree Rv Country Club SubDv. 33884 Zip Code
Welcome to Carefree Country Club - one of Winter Haven't best kept secrets! Tucked away off of Cypress Gardens Boulevard, when you approach the GATED community, you know you're entering a really special place. Driving through, you're encompassed by the community's 9-hole golf course. Continuing on, you'll pass a stunning two-story clubhouse, plus all of the amenities (large thermal heated swimming pool; bocce ball courts; tennis and pickle ball courts; boat docks and boat launch). And finally, you'll pass by Lake Bess, which the community has over 3,000 private feet of shoreline on! This home sits just a few homes up from the lake, and there is no need to worry about flooding, as the home pitches down toward the lake! Believe it or not, this is actually a single wide home with a large addition! Entering through the sliding glass doors, you'll find yourself in the open living space, where the kitchen, dining area, and living room flow together. You get great views of the lake through the windows as well! The original structure also has a guest bathroom (with a shower / tub combo) and guest bedroom. The addition has the primary suite, with a nice sized closet, and ensuite bathroom with a walk-in shower. In here you will also find the washer. Out back is a storage shed that can fit a golf cart (as you will see one currently in there), as well as the dryer. The home was re-piped, so no need to worry about polybutylene (grey) pipes! The monthly fees include the following: lawn care; internet access in the clubhouse and golf center; garbage disposal and recycling; all of the amenities! This is a great home in a great community; schedule your showing today!

9705 Lake Bess Road Unit 715, Winter Haven

$105,000
Emerald Palms SubDv. 33884 Zip Code
Discover the perfect canvas for your dream home at 4410 Emerald Palms Lane, nestled in the prestigious Emerald Palms subdivision of Winter Haven, Florida. This expansive lot offers a rare opportunity to build a custom residence in a serene, gated community known for its elegant homes and tranquil surroundings. With ample space to accommodate a variety of architectural styles, this lot is ideal for those seeking a peaceful retreat with the convenience of nearby amenities. Emerald Palms is just minutes from Winter Haven’s vibrant downtown, top-rated schools, shopping, dining, LegoLand, and the famous Chain of Lakes. Enjoy the blend of privacy and accessibility, making this lot a prime choice for your future home. Don’t miss the chance to create your own personal oasis in one of Winter Haven’s most sought-after communities!

4410 Emerald Palms Lane, Winter Haven

$128,000
2 Beds 2 Baths Oakwood Estates SubDv. 33880 Zip Code
Open and spacious living area is the best way to describe this home. The home features two living areas plus the lanai for additional space. The primary bedroom is large offering two built in closets and a spacious bathroom. The guest bedroom has the bath attached, perfect for visiting guests. The kitchen has an updated island perfect for entertaining. The laundry is located inside the home. Move right into this home, perfect for full time living and spacious for entertaining all the visitors you may have. The TPO roof was installed in 2022 and the ac is 10 years old. Oakwood Estates is a 55+ communities with lots of amenities including two clubhouses, two pools, miniature golf, shuffleboard, tennis courts, and much more. There are activities every day. You can join in or just sit back and enjoy the peaceful community.

4239 Cedarwood Street, Winter Haven

$337,000
3 Beds 2 Baths Cypresswood Fairway Patio Homes SubDv. 33884 Zip Code
Welcome to this meticulously maintained 3-bedroom, 2-bath pool home located in the highly sought-after 24-hour guard-gated Cypresswood Golf and Country Club community of Winter Haven. Thoughtfully designed with a desirable split-bedroom floorplan, this residence offers both privacy and functionality for everyday living and entertaining. Plus, seller is currently in the process of installing a NEW ROOF! Step inside to find beautiful hardwood and tile flooring throughout, creating a warm yet low-maintenance living environment. The spacious primary suite serves as a private retreat, complete with direct access to the screen-enclosed pool deck — perfect for enjoying your morning coffee or an evening swim under the stars. The heart of the home flows seamlessly into a dedicated dining area, with an exciting bonus room just beyond featuring a fun wet bar — ideal for hosting gatherings, game nights, or creating your own lounge space. Two additional bedrooms are situated on the opposite side of the home, providing comfort and privacy for family or guests. Outdoors, the screened pool deck offers the perfect space for relaxing or entertaining year-round. The garage includes a dedicated workshop area, making it ideal for hobbyists, DIY enthusiasts, or extra storage needs. Beyond the home itself, residents enjoy an exceptional lifestyle within this premier community, featuring a championship 18-hole golf course, community pool, fitness center, clubhouse, on-site restaurant, and pro shop. Exciting new amenities are on the way, including lighted tennis courts, pickleball, and basketball courts — offering something for everyone. Whether you’re raising a family, welcoming visiting guests, or enjoying a seasonal escape, this home offers the space, setting, and lifestyle to fit every chapter. The Cypresswood community is minutes from Highway 27 and the I-4 corridor, Winter Haven's very own Legoland Florida Resort, the Polk Parkway, and in the center of a thriving community with many convenient grocery, restaurant, shopping, and commuting options for travel in less than an hour from Disney World and other Orlando attractions, the Orlando and Tampa International Airports, and the gulf-side beaches of Tampa/St. Pete! This is more than just a home — it’s a lifestyle. Schedule your private showing today!

688 Augusta Road, Winter Haven

$235,000
2 Beds 2 Baths Traditions Phase 1 SubDv. 33884 Zip Code
Beautifully updated cottage-style villa located in a desirable 55+ gated community. This fully remodeled home features ceramic tile flooring throughout, with the exception of the second bedroom. The spacious two-car garage includes a laundry area that can easily be enclosed for additional privacy or functionality. The appliances are approximately four years old and have been gently used. ***Please note that the chandeliers and corner hanging lamps do not convey with the sale.**** Residents of this active retirement community enjoy a wide range of amenities, including fishing, a pool and spa, card room, billiards room, social events, fitness center, cable, internet, front lawn maintenance, irrigation, boat dock access (for an additional fee), and boat slips. Don’t miss this opportunity to own your own piece of Florida paradise!

3363 Livingston Way, Winter Haven