Refine Search
Map
Sort by
$370,000
5 Beds ⋅ 4 Baths ⋅ Royal Hills SubDv. ⋅ 33881 Zip Code
Discover exceptional living in this spacious 5-bedroom, 4-bath Winter Haven beauty—an ideal blend of style, comfort, and modern convenience. Step inside to an inviting open-concept kitchen with a center island, perfect for entertaining and everyday living. Elegant arched doorways add architectural charm throughout, creating a warm and welcoming flow. Enjoy year-round relaxation in the enclosed patio, offering the perfect spot for morning coffee or evening unwinding. A 2-car garage provides ample storage, while the fully fenced backyard delivers privacy and space for outdoor fun. Homes with this much versatility and character don’t stay on the market long—claim this Winter Haven gem before it’s gone.

5604 Royal Hills Drive, Winter Haven
$849,900
5 Beds ⋅ 4 Baths ⋅ N/A SubDv. ⋅ 33884 Zip Code
Welcome to a truly special waterfront property in Winter Haven, set on 1.28 private acres with water on both sides. Located on Lake Link with Lake Otis directly across the street, the two lakes form a connected two-lake chain offering boating, fishing and plenty of opportunities to enjoy life on the water. Enjoy beautiful lake views from both sides of the home and spectacular sunsets over Lake Otis from the front. A circular driveway welcomes you to this spacious 5-bedroom, 3.5-bath home with over 4,100 square feet of living space. The thoughtfully designed floor plan is filled with natural light and features the primary suite and one additional bedroom on the main level, along with a great room, kitchen and dining area, and a flexible room that could be used as an office or den. Upstairs, three additional bedrooms and a full bath provide plenty of space for family and guests, and the upstairs has been freshly painted. The oversized kitchen is perfect for everyday living and entertaining, offering tons of cabinetry, abundant countertop space and built-in double ovens. The home also offers exceptional storage throughout, providing plenty of room for everything. The outdoor living area features a screened enclosure with an oversized pool overlooking Lake Link, along with a convenient half bath for poolside guests. The backyard is exceptionally private, surrounded by tall bamboo, mature landscaping and fruit trees that create a beautiful natural setting while preserving the gorgeous waterfront views. An oversized dock, replaced in 2020, and a private boat ramp provide convenient access to Lake Link. Recent updates include a new roof in 2024 and one of the two AC systems replaced in 2024. An attached workshop off the laundry room provides additional functional space with direct access to the side yard. The oversized 3-car garage offers plenty of room for vehicles, watercraft and storage. Opportunities like this are truly rare. With 1.26 acres, waterfront on both sides, direct access to Lake Link and Lake Otis, and a spacious home with so much to offer, this property provides an incredible foundation for its next owner. Move in, make it your own, and bring your vision to life in a setting that is truly one of a kind.

25 Lakewood Causeway, Winter Haven
$424,999
5 Beds ⋅ 4 Baths ⋅ Buckeye Rdg SubDv. ⋅ 33881 Zip Code
Well maintained 5 Bedroom Home For Sale on a Huge Corner Lot with no Rear Neighbors! Long Driveway to park a lot of cars plus an extended oversized garage! Low HOA! Open Concept Living. Vinyl plank and tile flooring. Downstairs primary bedroom plus downstairs den/study area. Huge upstairs loft plus 4 additional bedrooms, 1 bedroom with an en-suite bathroom perfect for a young adult or teenager needing their own bathroom. Very private lot with a lot of fruit trees already planted. Perfect for someone who loves to garden! Located just mins from Downtown Winter Haven and with convenient access to I-4, this makes a great option for anyone! Schedule a tour today!

4162 Roberta Drive, Winter Haven
$649,900
3 Beds ⋅ 4 Baths ⋅ Lake Winterset Acres SubDv. ⋅ 33884 Zip Code
This home extrudes the luxury vibe from the moment you approach it with its distinctive roof w/ a blue metal barrel tile appearance and circular driveway. Large manicured 1+ acre lot and oak trees. No HOA and is located behind Legoland. Overlooking Lake Winterset on the famous Winter Haven Chain of Lakes. Lots of room to spread out in over 3000 sq ft of a/c living space. The split floor plan has 3 bedroom and 3 1/2 baths. A large corner gas stone custom fireplace is the living area focal point. A front door 2-car carport covers your guests as they enter through the double doors into the formal foyer. A dedicated built-out office is just inside. A triple sliding glass door opens to the 30' wide covered lanai and to the back yard. Plenty of room for a pool. Full irrigation with a dedicated well. Large 37x11 studio provides extra air conditioned flex space. Additional bonus is the oversized 2-car garage AND a 12' tall 11'x37' RV/boat garage and both are air conditioned and with a polyaspartic floor coating. Separate attached outside storage room for lawn equipment.

2241 Winterset Road, Winter Haven
$269,900
3 Beds ⋅ 2 Baths ⋅ Idylwild Heights SubDv. ⋅ 33881 Zip Code
WELCOME TO 2802 SUNSET DRIVE NW IN WINTER HAVEN! NO HOA AND A SPACIOUS LOT. THIS INVITING 3-BEDROOM, 2-BATHROOM HOME OFFERS A WONDERFUL OPPORTUNITY FOR BUYERS LOOKING FOR COMFORT, FUNCTIONALITY, AND A GREAT LOCATION. THE SPACIOUS LAYOUT PROVIDES PLENTY OF ROOM FOR EVERYDAY LIVING AND ENTERTAINING, WITH WELL-APPOINTED BEDROOMS AND TWO FULL BATHROOMS. ENJOY THE FLORIDA LIFESTYLE FROM THIS SPACIOUS LANAI, CONVENIENTLY SITUATED NEAR SHOPPING, DINING, BOAT RAMPS, PARKS, AND AREA ATTRACTIONS. WHETHER YOU ARE A FIRST-TIME BUYER LOOKING FOR A FAMILY HOME OR SEEKING AN INVESTMENT OPPORTUNITY, THIS PROPERTY IS LOCATED ON A DEAD-END STREET. NO HOA AND A PRIME LOCATION, THIS HOME COMBINES COMFORT, CONVENIENCE, AND VALUE. THE SELLERS ARE OFFERING A GENEROUS $10,000 CREDIT TO BE APPLIED TOWARD THE BUYER'S PREPAID EXPENSES AND CLOSING COSTS. THIS INCENTIVE PROVIDES ADDED FLEXIBILITY AND CAN HELP REDUCE OUT-OF-POCKET EXPENSES AT CLOSING, MAKING HOMEOWNERSHIP EVEN MORE ATTAINABLE. SCHEDULE YOUR PRIVATE SHOWING TODAY.

2802 Sunset Drive Nw, Winter Haven
$295,000
4 Beds ⋅ 3 Baths ⋅ Dundee Station SubDv. ⋅ 33881 Zip Code
Priced to Sell! Just installed brand new flooring in the living room and kitchen on the first floor! Carpet was newly installed in 2025. Two story Single Family Home in beautiful DUNDEE STATION community in Winter Haven. This 4 bedroom/2.5 bathroom home features a great open floor plan. As you enter, you are greeted with a spacious living, dining and kitchen area. The kitchen features stainless steel appliances, granite counter tops, breakfast bar/island and large pantry. Half bath is conveniently located next to the living room. Laminate floor on the 1st floor in the common areas and carpet on the 2nd floor. All bedrooms are on the second floor. Nice size master bedroom comes with large walk-in closet. Master Bath has a garden tub, separate walk-in shower, and dual vanity sinks. No washer and dryer. LOW HOA Fee! Close to historic downtown, schools, LEGOLAND/Cypress Gardens Theme Park and shopping. THE PROPERTY IS GREAT FOR PRIMARY USE or INVESTMENT.

1370 Salisbury Drive, Winter Haven
$819,900
4 Beds ⋅ 3 Baths ⋅ Waterford Oaks SubDv. ⋅ 33884 Zip Code
Welcome to 9469 Waterford Oaks Drive, a beautifully maintained and spacious custom built home offering an exceptional combination of comfort, privacy, upgrades, and Florida living in the highly desirable, gated community of Waterford Oaks! A pavered, circular driveway provides an impressive approach to the home with plenty of space for vehicles and guests. Inside, the home features soaring ceilings, elegant archways, crown molding, custom built-ins, a beautiful fireplace, and generous living spaces throughout. The grand primary suite is a true private retreat, featuring two walk-in closets and an expansive primary bath with dual vanity areas, extensive cabinetry, and a large walk-in shower. A dedicated home office with custom built-in cabinetry and bookshelves provides an ideal work-from-home space. Upstairs offers even more flexibility with a large second living room/loft, spacious bedroom, and full bathroom—perfect for guests, family, or a private secondary living area. Outside, enjoy a private screened pool and hot tub/spa with a new spa heater, surrounded by an expansive pool deck with plenty of room for multiple outdoor seating and dining areas. The covered lanai features a high-end built-in outdoor grilling system with a direct gas connection, creating an exceptional space for entertaining year-round. Recent improvements include a new roof, new exterior paint, new hot tub/spa heater, full app-controlled pool automation system, Tesla charger installed in the garage, and multiple filtered-water systems throughout the home. A community boat ramp and dock on Lake Winterset on the Winter Haven Chain of Lakes is just a short distance away. With its spacious floor plan, grand primary suite, private upstairs living area, home office, fireplace, pool and spa, expansive outdoor entertaining space, and extensive recent upgrades, 9469 Waterford Oaks Drive is move-in ready and designed to enjoy the Florida lifestyle.

9469 Waterford Oaks Drive, Winter Haven
$324,900
4 Beds ⋅ 2 Baths ⋅ Royal Hills SubDv. ⋅ 33881 Zip Code
WELCOME TO THIS WELL-KEPT PROPERTY WITH LOW HOA FEE. THIS IS A SPLIT PLAN FOUR BEDROOM/TWO BATH HOME. THE PROPERTY HAS A LIVING, DINING AND FAMILY ROOM. THE EAT-IN KITCHEN IS LIGHT AND BRIGHT. THERE IS AN INSIDE LAUNDRY ROOM. THE BEDROOMS ARE NICELY SIZED. VAULTED AND CATHEDRAL CEILINGS ALONG WITH NUMEROUS PLANT SHELVES ADD CHARACTER TO THIS HOME. THERE IS A SCREENED PORCH OFF THE FAMILY ROOM THAT LOOKS OUT AT THE TOTALLY FENCED BACK YARD. THIS HOME IS CENTRALLY LOCATED AND CLOSE TO SHOPPING, I-4, HWY 27 AND BETWEEN TAMPA AND ORLANDO. PRICED TO SELL.

5638 Royal Hills Street, Winter Haven
$75,000
2 Beds ⋅ 2 Baths ⋅ Orange Manor West Coop Inc SubDv. ⋅ 33884 Zip Code
2 Bedroom 2 Bathroom mobile home in highly sought after Orange Manor West. This community offers a welcoming social atmosphere with plenty of activities and amenities to enjoy. Enjoy a Florida lifestyle with clubhouse, swimming pool, shuffleboard, mini golf, horseshoes, billiards, fishing. Located near shopping and restaurants. NO PETS ALLOWED. SERVICE AND EMOTIONAL SUPPORT ANIMALS ARE ALLOWED WITH CERTIFICATION. SELLER WILL CONSIDER PAYING ONE YEAR HOA

187 Sweet Circle, Winter Haven
$330,000
4 Beds ⋅ 3 Baths ⋅ Windridge SubDv. ⋅ 33881 Zip Code
Spacious 4BR/2.5BA home with 2,836 SF in desirable Windridge! Enjoy a screened saltwater pool, spacious fenced backyard, flexible living areas, and parking for up to 8 vehicles (2-car garage + oversized driveway). Major updates include a 2023 roof and 2022 A/C. Low HOA, no CDD, and convenient access to shopping, dining, schools, and major roads. Quick closing available and priced to sell. Act fast; schedule your private showing today!

5888 Windridge Drive, Winter Haven
$158,500
2 Beds ⋅ 2 Baths ⋅ Lucerne Park Fruit Assn SubDv. ⋅ 33881 Zip Code
Welcome to this spacious, meticulously maintained, and thoughtfully updated double-wide manufactured home on owned land in the highly sought-after 55+ lakefront community of Lake ’n Golf Estates in Winter Haven. Offering a versatile floor plan with multiple living areas, this home beautifully blends modern updates with the relaxed comfort of Florida living. The chef’s kitchen was fully renovated just three years ago and features new countertops, stainless steel appliances, and refreshed cabinetry. The wonderful dining room includes updated built-in cabinetry. Other major improvements include a full carport replacement three years ago, a new AC unit installed in 2020, a main roof replaced approximately three years ago, and a front Florida room whose roof was replaced about nine years ago. Inside you’ll find updated flooring throughout, a convenient indoor laundry room, a front Florida room with central air and heat, and an additional side Florida room with a wall AC unit—perfect for relaxing or entertaining. A spacious double workshop provides plenty of storage, hobby space, or room to park a golf cart. This home comes partially furnished (only furniture not included is master bedroom matching set and TV in living room). Lake ’n Golf Estates offers wonderful amenities including a pool and spa, shuffleboard courts, clubhouse, community lake access, and boat dock. Conveniently located near Highway 27 with easy access to shopping, restaurants, and medical facilities, the community also features impressively, OWN YOUR LAND AND SAVE THOUSANDS PER YEAR, HOA fees of just $550 per year and Move-in ready and packed with value, this home is a must-see—schedule your private showing today!

6703 Canterbury Drive Ne, Winter Haven
$239,900
3 Beds ⋅ 2 Baths ⋅ Winterset 03 A Condo Ph 01 SubDv. ⋅ 33884 Zip Code
3 bedroom, 2 bath ground-floor end-unit condo home with gorgeous views of Lake Winterset and a private 1 car garage—the perfect combination in one of Winter Haven’s most desirable gated communities. Welcome to 701 Magnolia Place, a spacious lakeview residence designed for easy single-level living with approximately 1,180 square feet, durable luxury vinyl plank flooring, and a comfortable, open layout. The living room is anchored by a fireplace and flows naturally into the dining area, creating an inviting space for everyday living and entertaining. The kitchen features white cabinetry, soft close drawers, newer stainless steel appliances, generous counter space, and an adjoining breakfast nook. The primary suite is spacious, measuring approximately 11x16, with lake views, a private bath with walk-in shower, generous closet space and direct access to the back patio. Two additional bedrooms provide flexibility for guests, a home office, hobby room, or den—a combination that makes this 3-bedroom floor plan especially hard to find in Winterset. A second full bath with tub and shower combo completes the interior. Step outside to the private screened porch, where wide-open green space and beautiful Lake Winterset views create the perfect place to enjoy your morning coffee, unwind at the end of the day, and watch sunsets you truly have to see to believe. As an end unit, the home enjoys an added sense of openness and privacy, while the attached one-car garage provides valuable parking and storage. Beyond the residence, the community of Winterset delivers on the Florida lifestyle. Residents have access to a heated lakefront swimming pool and spa, clubhouse, tennis and pickleball courts, shuffleboard, and a private boat ramp with direct access to the Winter Haven Chain of Lakes—opening the door to boating, fishing, water skiing, sunset cruises, and waterfront dining. Shopping, restaurants, medical facilities, LEGOLAND Florida Resort, and downtown Winter Haven are all just minutes away, while convenient routes toward Tampa and Orlando make the location equally appealing for everyday living and weekend adventures. Ground-floor living, an end-unit location, three bedrooms, private garage, screened porch, Chain of Lakes access, resort-style amenities, and gorgeous Lake Winterset views—701 Magnolia Place offers a combination that is difficult to find.

701 Magnolia Place, Winter Haven
$259,900
3 Beds ⋅ 2 Baths ⋅ Fox Ridge Ph 01 SubDv. ⋅ 33884 Zip Code
Welcome to this move-in ready 3-bedroom, 2-bathroom home in the desirable Fox Ridge neighborhood. This home features a modern open-concept layout that connects your living spaces with a seamless flow. The living area is highlighted by a cozy fireplace, creating a warm and welcoming focal point. The updated kitchen comes beautifully equipped with sleek stainless steel appliances and gorgeous granite countertops. The primary suite offers a private retreat complete with a large walk-in closet and an attached primary bathroom featuring double sinks/vanity. Step outside to enjoy the privacy of a fully fenced backyard. The location is a standout, centrally positioned just minutes away from local shopping, schools, dining options, and the excitement of Legoland. Schedule your private showing today!

3329 Fox Ridge Drive, Winter Haven
$345,000
4 Beds ⋅ 2 Baths ⋅ Lake Lucerne Ii SubDv. ⋅ 33881 Zip Code
Virtually Staged. Newer home with NO CDD and large yard!!! Welcome home to this beautifully maintained 4 bedroom, 2 bath home offering 1,983 square feet of comfortable living space and modern finishes throughout. Built in 2023, this home features a desirable open split-floor plan designed for both everyday living and entertaining. The spacious kitchen boasts granite countertops, large island, stainless steel appliances, and plenty of room to gather with family and friends. The split-bedroom layout provides privacy for the primary suite while keeping the additional bedrooms conveniently accessible. Step outside to enjoy the large yard and relaxing covered lanai—perfect for morning coffee, outdoor dining, or entertaining. Additional highlights include a 2-car garage, new carpet, and no CDD. With its modern construction, spacious layout, and move-in-ready appeal, this home is a must-see!

1425 Engelberg Street, Winter Haven
$310,000
4 Beds ⋅ 2 Baths ⋅ Lake Smart Estates SubDv. ⋅ 33881 Zip Code
3D tour available! Welcome to this spacious 4-bedroom, 2-bath single-family home in the Lake Smart Estates community of Winter Haven. With an open-concept layout and 1,842 square feet of living space, the home offers plenty of room for everyday living and entertaining. Major updates provide added peace of mind, including a new roof in 2026, new A/C in 2024, and brand-new appliances in 2026. The kitchen offers generous cabinet and counter space and opens directly to the main living and dining areas. The primary suite features a walk-in closet and private bathroom with dual sinks and a spacious shower. An interior laundry room and attached two-car garage add everyday convenience. One of the property's biggest highlights is the oversized lot, one of the largest in the community. The expansive backyard provides exceptional outdoor space with plenty of possibilities for entertaining, play areas, gardening, or creating your own Florida outdoor retreat. Lake Smart Estates offers community amenities including a swimming pool, dock, gazebo, and water access. Golf enthusiasts will appreciate having Willowbrook Golf Course just minutes away, a public 18-hole course offering a driving range, putting green, chipping areas, and practice facilities. Conveniently located near US-17, the home provides easy access to Downtown Winter Haven, shopping, restaurants, schools, Polk State College, and everyday services. With four bedrooms, significant recent upgrades, an oversized yard, community amenities, and golf nearby, this move-in-ready home offers an excellent combination of indoor and outdoor space in a convenient Winter Haven location.

3695 Julius Estates Boulevard, Winter Haven
$1,250,000
5 Beds ⋅ 4 Baths ⋅ Interlaken Add SubDv. ⋅ 33881 Zip Code
Welcome to this extraordinary custom-built lakefront residence offering an unparalleled lifestyle on the renowned Winter Haven Chain of Lakes. Built-By-Waters in 2024, this award-winning property earned the Polk County Parade of Homes coveted “Home of the Year” award while sweeping all five subcategories for Best Exterior, Best Floor Plan, Best Kitchen, Best Master Bath, and Best Overall Quality. Elevated above the shoreline with sweeping southern views across Lake Howard, the home was thoughtfully designed to embrace its waterfront setting while delivering refined luxury and effortless everyday living. Stately iron doors welcome you inside to soaring ceilings, sophisticated lighting, open-concept living, and expansive windows and glass doors that blur the boundaries between indoors and out. The main living area features a custom beam ceiling and a mesmerizing 6-foot-wide Napoleon fireplace, creating the perfect balance of comfort and refinement. The spectacular kitchen combines striking design with exceptional functionality, anchored by an oversized quartz island and complemented by an Italian-designed Bertazzoni gas range, stainless appliances, sleek flat-front cabinetry, wine cooler, and concealed walk-in pantry—all flowing seamlessly into the dining area. The primary suite features two custom-organized walk-in closets and a spa-inspired bath with quartz countertops, large walk-in shower, and luxurious soaking tub positioned beside the window to enjoy lake and sunset views. Four additional bedrooms provide plenty of space and versatility, complemented by beautifully finished baths all with custom tile work, seamless glass enclosures, and quartz countertops. One larger bedroom currently serves as a second living area and could easily become a secondary primary suite, golf simulator room, wellness studio, or sophisticated whiskey lounge. Outdoor living is equally impressive with a full summer kitchen featuring granite counters, gas grill, power burner, refrigerator, and sink. The fully fenced and beautifully landscaped backyard offers privacy and the perfect canvas for a custom pool and outdoor retreat. Continue toward the lake, where an impressive two-story private dock features two covered boat slips, a storage room, electric and water, and an upper observation deck offering sweeping views across Lake Howard and a front-row seat to some of Central Florida’s most spectacular sunsets. The Winter Haven Chain of Lakes is not your average lakefront lifestyle. Spend your days exploring 20 canal-connected lakes, boating, skiing, fishing, or cruising through enchanting tree-canopied canals and cypress-lined shorelines. Boat to waterfront restaurants for dinner, live music, or a cold drink, gather friends for an afternoon on the water, watch painted sunsets from the lake, or experience spectacular fireworks from your boat. Just minutes from downtown Winter Haven, the property offers convenient access to dining, shopping, entertainment, and medical facilities. Additional features include a 26kW generator, tankless Rinnai water heaters, two A/C systems (2024/2025), landscape and soffit lighting, double-pane windows, irrigation well, and so much more. Meticulously crafted to capture every advantage of its remarkable setting, 1307 N Lake Howard Dr is more than a luxury home—it is a statement of refined lakefront living. (SEE VIRTUAL TOUR LINK)

1307 N Lake Howard Drive, Winter Haven
$139,900
2 Beds ⋅ 2 Baths ⋅ Winter Ridge Condo SubDv. ⋅ 33881 Zip Code
MUST SEE! Discover the perfect blend of comfort, convenience, and Florida lifestyle in this beautifully maintained 2-bedroom, 2-bathroom unit in the desirable Winter Ridge Condominium Community. Featuring new laminate flooring throughout the living areas and bedrooms, fresh paint, updated baseboards, and A/C, this move-in-ready home offers a clean, modern feel with no carpet. The open-concept layout is thoughtfully designed to maximize every square foot, creating a spacious and inviting atmosphere for everyday living or entertaining. The property also includes two dedicated parking spaces, providing added convenience for residents and guests. Enjoy resort-style community amenities including a heated pool, clubhouse, chain-of-lakes access, boat dock, and boat slips, making it easy to embrace the best of Central Florida living. The HOA includes exterior and grounds maintenance as well as trash service, helping simplify ownership and enhance the property's appeal for both homeowners and investors. Conveniently located just minutes from downtown amenities, Legoland, shopping, dining, and entertainment, this property offers an excellent opportunity for a primary residence, second home, or income-producing investment. Seller or private financing available with an easy and fast approval process and just 20% down! Don't miss this exceptional opportunity schedule your showing today before it's gone!

244 Winter Ridge Boulevard Unit 244, Winter Haven
$244,900
3 Beds ⋅ 2 Baths ⋅ Queens Cove Ph 03b SubDv. ⋅ 33880 Zip Code
Welcome to this inviting 3-bedroom, 2-bathroom home located in the Queens Cove neighborhood. This home features a functional floorplan that creates a seamless flow for relaxing and entertaining. The kitchen is functional and stylish, boasting durable countertops and sleek appliances. For added privacy, the primary bedroom is complete with its own attached primary bathroom. Ideally located just minutes from the Polk Parkway, shopping, and grocery stores, and only 20 minutes from the attractions at LEGOLAND, this home offers everything you need for easy, everyday living. Schedule your private showing today!

3735 Imperial Drive, Winter Haven
$430,000
3 Beds ⋅ 2 Baths ⋅ Overlook Estates SubDv. ⋅ 33884 Zip Code
Welcome to the beautiful neighborhood of Overlook Estates. This 3 bedroom 2 bath + bonus room is waiting for its new owner/s to make it their own. This home is completely vacant which makes it that much easier to envision your own life here. When you first arrive you will notice the beautiful curb appeal this home offers. Upon entering you will be greeted by the stunning entrance. This home is bright and spacious with high ceilings and beautiful wood beams giving it character right off the bat. The kitchen was completely remodeled in 2022. It has floor to ceiling cabinets giving you plenty of space for storage. Use the large island with a built in cook top or move it over to a more formal dining room. Either way this home is the perfect place for entertaining. You can access the lanai/salt water pool from the primary bedroom, kitchen, living room, and even the full guest bath. The open floor plan allows for friends and family to gather while still having plenty of space to spread out. The primary bedroom with ensuite bath and walk in closet as well as that access to the lanai. The primary bathroom has a walk in shower, garden tub, dual vanity and also includes a walk in closet as well as a linen closet. The two additional bedrooms as well as a full bath are located on the opposite side of the house. A fourth room allows for the perfect office space or even a room to host your guests. This home has been wonderfully updated while still holding onto its charm and character. Schedule your showing today!

280 Santa Rosa Drive, Winter Haven
$299,990
4 Beds ⋅ 2 Baths ⋅ Royal Hills SubDv. ⋅ 33881 Zip Code
Welcome to this well-located single-family home situated in Winter Haven, offering a comfortable layout and enjoyable outdoor space. This home features 4 bedrooms and 2 bathrooms with a practical floor plan that supports everyday living, along with a 2-car garage and a large driveway and backyard. The property also includes a Newer Shingle Roof (2026), Newer A/C (2025) and newer LVP flooring (2026). Inside, the living area offers two living room areas with high ceilings, one at the entrance and another one by the kitchen, creating a welcoming space that makes it easy to stay connected whether you’re relaxing at home or entertaining guests. The bedrooms are nicely sized, and the primary suite provides added comfort with a walk-in closet and a private bathroom that features both a bathtub and a separate shower. The second full bathroom add convenience and functionality for the household. Whether you’re searching for a place to make your own or an investment opportunity, this home is worth a look. Schedule your showing today.

5641 Royal Hills Drive, Winter Haven
$178,500
2 Beds ⋅ 2 Baths ⋅ Winterset 02 A Condo Ph 01 SubDv. ⋅ 33884 Zip Code
Welcome to resort-style living in the heart of Winter Haven! This charming 2-bedroom, 2-bath condo/Townhouse offers the perfect combination of comfort, convenience, and an incredible community lifestyle. Located inside a desirable gated community, residents enjoy an impressive selection of amenities including a sparkling community pool, clubhouse, boat ramp with access to Lake Winterset and the Chain of Lakes, tennis and pickleball courts, and more. The location is hard to beat! Just minutes from LEGOLAND Florida, approximately 5 minutes from US Highway 27, and conveniently close to grocery stores, shopping, dining, and some of Winter Haven's hidden-gem local restaurants. Whether you're looking for a full-time residence, a Florida getaway, or a low-maintenance home in a vibrant community, this property offers an exceptional opportunity. Come experience the relaxed Florida lifestyle, recreational amenities, and convenient location that make this community such a special place to call home. Schedule your private showing today!

2007 Garden Lake Drive Unit 2007, Winter Haven
$425,000
4 Beds ⋅ 3 Baths ⋅ Cypresswood SubDv. ⋅ 33884 Zip Code
ON THE GOLF COURSE IN THE BEAUTIFUL & GATED COMMUNITY OF CYPRESSWOOD GOLF & COUNTRY CLUB!!! Recently remodeled, open, spacious & ready to move in! Enjoy the Cypresswood Country Club lifestyle, including an active clubhouse, junior Olympic size pool, pickle ball courts, tennis, golf and a great restaurant with bar! When you're not enjoying all of the amenities, take a walk or ride your bike on the quiet, tree-lined streets throughout the community! This is a one-of-a-kind, two-story classic home on an extra-large lot, so plenty of room for a swimming pool!!! No rear neighbors, just Florida nature and golf in your backyard! Great place for socializing, family gathering and just lots of relaxing! You can park a dozen cars in your driveway and room to park your fishing boat or up to 6 cars in your garage! The oversized garages come complete with a "golf cart" garage in the rear of the home. Freshly remodeled by Bill Reed Construction, the updates include a freshly painted & neutral color scheme and luxury vinyl flooring throughout. You'll enjoy the golf-course views in the updated kitchen with granite tops and GE appliances. The open & bright kitchen nook area has sliding glass doors, and the family room is adjacent as well as a spacious dining room with lots of windows to enjoy! There is a separate living room with glass sliding doors to the oversized screened lanai and features a brick wood-burning fireplace creating a cozy area with lots of "flex" space. Room for all with 4 bedrooms and the primary suite boasts a walk-in closet, built-ins, dual sinks and a modern barn door. Three of the bedrooms are on the second floor. Mature landscaping and shade trees make perfect areas for enjoying the outdoor beauty and watching golf. Cypresswood is just minutes to Highway 27, great shopping, medical and the new Publix. Right in the heart of Central Florida with a "Chain of Lakes" for boating, fishing and a great "foodie" scene in the charming downtown district. This property has so much for your family to enjoy!!! Call today to schedule your private tour!

300 Greenfield Road, Winter Haven
$269,900
3 Beds ⋅ 2 Baths ⋅ Planters Walk SubDv. ⋅ 33884 Zip Code
THIS WELL-KEPT HOME LOCATED ON A CUL-DE-SAC HAS A HUGE (ONE THIRD ACRE) LOT. THIS IS A SPLIT BEDROOM PLAN WITH THREE BEDROOMS AND TWO BATHS. KITCHEN AND BOTH BATHS HAVE BEEN UPDATED. THE PRIMARY BEDROOM HAS AN UPDATED EN SUITE WITH WALK-IN CLOSET. THE GREAT ROOM IS LARGE AND HAS A VAULTED CEILING. THERE IS AN EAT-IN AREA IN THE KITCHEN AS WELL AS A DINING ROOM LOCATED OFF THE GREAT ROOM. TWO NICELY-SIZED BEDROOMS AND SECOND BATH ARE LOCATED ON OTHER SIDE OF THE GREAT ROOM. DOUBLE PANE WINDOWS HELP WITH UTILITY COSTS. THE REAR SCREENED PORCH OVERLOOKS THE REAR YARD WHERE YOU WILL FIND A HUGE ABOVE-GROUND POOL FOR ENJOYING YEAR ROUND AS THERE IS A SEPARATE SOLAR PANEL FOR HEATING THE POOL. THIS PROPERTY IS CENTRALLY LOCATED AND CLOSE TO SHOPPING, LEGOLAND, TAMPA AND ORLANDO AND EQUAL DISTANCE TO BOTH EAST AND WEST COAST BEACHES.

106 Saint Kitts Circle, Winter Haven
$140,000
2 Beds ⋅ 2 Baths ⋅ Imperial Villas SubDv. ⋅ 33880 Zip Code
Welcome to easy Florida living in desirable Imperial Villas! This well maintained 2 bedroom, 2 bath villa offers a bright, open layout with a comfortable flow. Roof Replaced 2020. The spacious primary suite includes a walkin closet and private bath, and the screened lanai is perfect for morning coffee or relaxing in the evening. Enjoy the heated community pool and a low maintenance lifestyle, with the HOA covering water, sewer, trash, and exterior maintenance. Conveniently located near Lake Howard, shopping, dining, and downtown Winter Haven, this home blends comfort and convenience. Schedule your private showing today.

345 24th Street Nw Unit 1, Winter Haven
$369,900
3 Beds ⋅ 2 Baths ⋅ Hartridge Hills SubDv. ⋅ 33881 Zip Code
Move-In Ready Custom Home in a Gated Community Near the Airport Ideally located for aviation professionals seeking convenient access to the airport or for families looking for a safe, gated community, this beautifully updated custom home offers the perfect blend of comfort, style, and convenience. Built in 1988, this spacious home features an open floor plan with soaring ceilings, stunning exposed wood beams, solid wood doors, and matching wood baseboards that create warmth and character throughout. The split-bedroom layout provides privacy, while the attached two-car garage adds everyday convenience. The recently remodeled interior showcases numerous upgrades, including luxury vinyl plank flooring, fresh interior paint, and updated lighting throughout. The beautifully renovated kitchen features custom wood cabinetry, granite countertops, and a full suite of matching Whirlpool appliances. Both bathrooms have been tastefully updated with new wood vanities, Delta fixtures, Kohler toilets, and stylish tile finishes. The primary bedroom offers the comfort of new carpeting, and the home features smooth ceilings throughout—no popcorn ceilings. Additional highlights include generous laundry room storage, fresh exterior paint, and numerous major improvements for peace of mind. A new roof was installed in March 2026, along with new double-insulated windows, new irrigation, and professional landscaping. Every major update has been completed—simply move in and enjoy. The HOA fee is just $150 per month and includes lawn mowing and fertilization, making it easy to maintain a beautiful yard year-round.

218 Lake Hartridge Drive Nw, Winter Haven
$259,000
3 Beds ⋅ 2 Baths ⋅ Forest Ridge SubDv. ⋅ 33881 Zip Code
Welcome to this beautifully maintained 3-bedroom, 2-bath home in Forest Ridge, offering a great floor plan that feels bright and spacious! The split-bedroom layout provides privacy and flexibility, while the inviting kitchen features an eat-in area and breakfast bar, making it perfect for everyday living and entertaining. A separate laundry room adds convenience, and the home also features ceiling fans throughout. Step outside to the screened lanai overlooking a large, private, fully fenced backyard—an ideal space for relaxing, entertaining, or enjoying the outdoors. The home also features a new roof installed in 2025 and custom-fitted hurricane shutters for each window, designed for easy installation when needed for storm protection. Enjoy the best of both worlds in Forest Ridge—a quiet neighborhood setting with convenient access to Highway 27 and I-4. Shopping, dining, schools, and the many attractions of Central Florida are all within easy reach. Add in the spacious layout and large private backyard, and you have a home that offers both comfort and convenience. This home is move in ready and waiting for the new owner.

5621 Forest Ridge Drive, Winter Haven
$299,000
3 Beds ⋅ 2 Baths ⋅ Saxon Myers Rep Ph 2 SubDv. ⋅ 33881 Zip Code
Affordable pool home with NO HOA in the heart of Winter Haven! Welcome to 133 Rebecca Drive NE, a move-in-ready 3 bedroom, 2 bath home offering a private screened saltwater pool, important updates, comfortable living spaces, and an impressive combination of features and value. If you've been searching for an affordable Central Florida home where you can enjoy the Florida pool lifestyle right in your own backyard, this one deserves a closer look. Inside, the spacious main living area features attractive porcelain tile flooring, a vaulted ceiling, and a gas fireplace, creating a comfortable gathering space for everyday living and entertaining. The adjoining dining area provides direct access to the pool and outdoor living area, while the kitchen features clean white cabinetry, beautiful granite countertops, plenty of storage, and a full suite of included appliances. The desirable split-bedroom layout includes two comfortably sized guest bedrooms and a spacious primary suite with an en-suite bath and generously sized walk-in closet. Both bathrooms have been updated, including a beautifully renovated primary bath with a custom walk-in shower. Step outside and imagine weekends filled with pool time, grilling on the back deck, entertaining friends and family, and enjoying the Florida sunshine. The large screened outdoor living area features a private saltwater pool, plenty of deck space for lounging, dining, and grilling, plus a covered area where you can relax in the shade. Start the morning with coffee by the pool, spend a sunny afternoon in the water, then fire up the grill for dinner and enjoy a warm Florida evening at home. This is the kind of outdoor space that makes it easy to enjoy everything the Florida lifestyle is all about. Beyond the pool enclosure, the fully fenced backyard provides additional usable yard space with plenty of potential for landscaping, a vegetable garden, or your own collection of Florida fruit trees. An included storage shed provides convenient space for lawn and gardening equipment while keeping the two-car garage free for vehicles and additional storage. Major improvements include a NEW A/C system in 2025, all new double-pane windows and sliding glass door in 2021, a 2017 roof, newer front door, rain gutters and low utility bills. Best of all, there is NO HOA! Located in the heart of Winter Haven, you're convenient to downtown Winter Haven, Polk State College, shopping, dining, medical facilities, and recreation. Winter Haven's central location between Tampa and Orlando also puts theme parks, international airports, beaches, professional sports, and some of Central Florida's best entertainment within reach.

133 Rebecca Drive Ne, Winter Haven
$198,900
2 Beds ⋅ 2 Baths ⋅ Vienna Square SubDv. ⋅ 33884 Zip Code
Short Sale. CLOSE IN 60 DAYS OR LESS! QUICK and easy HECM Short Sale on this 2 bedroom 2 bath Vienna Square Villa with pond and wooded view. Located next door to the clubhouse! The charming kitchen has upgraded ivory cabinets, and quartz counter tops. The oak floors flow from the kitchen, and great room giving a warm quality finish. The roof was replaced in 2022. Sold strictly AS-IS. No renting for the 1st 2 years of ownership in this charming 55+ community. This home is conveniently located within 10 minutes of restaurants, banks, shopping and Legoland. Vienna Square offers a low-maintenance lifestyle with reasonable fees, in a welcoming setting. Vienna Square is a beautifully maintained, amenity-rich community designed for easy living. Monthly fees include exterior paint, roof replacement, irrigation water, basic yard maintenance, and a Spectrum Internet/TV package. Residents enjoy access to a community pool, fitness center, billiards, movie nights, tennis and pickleball courts, and an active social calendar. Step inside, fall in love. Make it yours!

1307 Innsbruck Ct, Winter Haven
$315,000
4 Beds ⋅ 3 Baths ⋅ Villamar Ph 2 SubDv. ⋅ 33884 Zip Code
Designed around connected gathering spaces and an easy single-story layout, this 1,988-square-foot home offers a comfortable balance of openness and separation throughout. The kitchen sits at the center of the home, where granite counters, a large island with seating, stainless-steel appliances, and a walk-in pantry create a practical workspace while keeping the kitchen connected to the dining area and great room. Sliding glass doors extend the main living space toward the backyard, bringing in natural light and making it easy to move between indoor and outdoor areas. The four-bedroom, three-bath layout provides flexibility without sacrificing privacy, with the primary suite positioned toward the rear of the home and complemented by a walk-in closet and en suite bath with dual sinks and a glass-enclosed shower. Ceramic tile runs through the main living spaces, while carpet adds a softer finish to the bedrooms. An interior laundry room, attached two-car garage, paver driveway, irrigation system, and backyard add to the home’s everyday functionality. Built in 2021 and maintained with its original finishes, the home offers a functional, well-connected layout with room for the next owner to make it their own. Beyond the home, VillaMar offers a community pool, playground, sidewalks, and recreational common areas, giving residents additional ways to enjoy time outside close to home. Its Winter Haven location also keeps shopping, dining, major roadways, and area attractions within convenient reach.

1166 Yumuri Street, Winter Haven
$215,000
2 Beds ⋅ 2 Baths ⋅ Winterset 01 A Condo 02 Amd SubDv. ⋅ 33884 Zip Code
This home can be purchased with NO MONEY DOWN or NO INCOME VERIFICATION! Welcome to Lakefront Living at Its Finest! Experience serene waterside tranquility with breathtaking views of Lake Winterset in this inviting 2-bedroom, 2-bath unit, all at an affordable price. As you step inside, you'll be greeted by soaring ceilings that enhance the open and airy atmosphere. The thoughtfully designed open floor plan seamlessly connects living and dining areas, perfect for both entertaining and relaxation. Both bedrooms offers ample space for comfortable living. The master bedroom also offers a spacious walk-in closet, and sliding glass doors leading to your rear screened porch. Enjoy your morning coffee or unwind in the evenings on the screened porch, where nature's beauty serves as your stunning backdrop. This desirable gated community not only offers a Clubhouse, pool, and spa but also features tennis and pickleball courts, as well as a convenient boat ramp for easy access to the lake. Ideally located near Legoland and in the heart of the Florida Peninsula, with lots of lakes, or just over an hour drive to the Gulf or Atlantic beaches, Tampa & Orlando for airports, shopping, entertainment and more. This home perfectly blends comfort and convenience. Don't miss your chance to embrace the Florida lakefront lifestyle you've always dreamed of!

410 Laurel Cove Way, Winter Haven