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5780 Lakeside Landings Boulevard, Winter Haven
$290,000
4 Beds ⋅ 3 Baths ⋅ Lakeside Landings Ph 01 SubDv. ⋅ 33881 Zip Code
Enjoy peaceful pond views, spacious living, and desirable community amenities in this 4-bedroom, 2.5-bathroom, two-story home in Winter Haven! Built in 2016, this 2,526-square-foot home offers plenty of room to spread out and enjoy comfortable everyday living. Step outside and take in the pond view from the backyard, providing a relaxing backdrop to unwind at the end of the day. Major updates include a roof replacement in late 2023 and exterior paint completed shortly afterward. The A/C has also been recently serviced for added peace of mind. Located in an established community of Lakeside Landings featuring sidewalks, a neighborhood pool, and a playground, there are plenty of opportunities to enjoy the outdoors. Conveniently situated near Lake Fannie, with easy access to I-4, shopping, dining, and other everyday conveniences, this home puts you within reach of all that Winter Haven and Central Florida have to offer. Don't miss the opportunity to make this spacious home your own!

5780 Lakeside Landings Boulevard, Winter Haven

9457 Waterford Oaks Drive, Winter Haven
$710,000
3 Beds ⋅ 3 Baths ⋅ Waterford Oaks SubDv. ⋅ 33884 Zip Code
Welcome to this beautiful 3-bedroom, 3-bath pool home located in the gated community of Waterford Oaks! Offering over 3,200 square feet of living space, this well-maintained home has so much to offer, including a new roof installed in October 2022, solar panels for energy efficiency, and a spacious 3-car garage. As you enter through the double front doors, you’ll immediately appreciate the high ceilings, open floor plan, and beautiful architectural details throughout. The home features a formal dining area, a separate office, and a spacious living room that opens to the kitchen, making it perfect for everyday living and entertaining. The kitchen offers granite countertops, stainless steel KitchenAid appliances, a gas range, center island with prep sink, breakfast bar, walk-in pantry, and plenty of cabinet space. The spacious primary suite features French doors leading to the pool area, two walk-in closets, and a private bath complete with dual vanities, a jetted tub, and a separate walk-in shower. Two additional bedrooms are located on the opposite side of the home, offering privacy for family and guests, along with a Jack-and-Jill bathroom. Step outside and enjoy your own private backyard retreat! The screened pool area features a beautiful waterfall, heated spa, two covered lanais, an outdoor grilling area, and a convenient pool bath. Whether you’re entertaining friends or simply relaxing at home, this outdoor space is sure to be a favorite. Additional features include a tankless water heater, plantation shutters, app-controlled irrigation, exterior lighting, a central vacuum system, and beautifully maintained landscaping. Waterford Oaks is a gated community offering residents access to a private boat ramp on Lake Winterset, part of the Winter Haven Chain of Lakes. Enjoy boating, fishing, and all that lakefront living has to offer without the maintenance of owning waterfront property. This home offers a wonderful combination of space, comfort, and Florida living. Schedule your private showing today

9457 Waterford Oaks Drive, Winter Haven

3937 Giorgio Drive, Winter Haven
$344,720
4 Beds ⋅ 2 Baths ⋅ Villamar SubDv. ⋅ 33884 Zip Code
Brand new, energy-efficient home available by Oct 2026! Prepare dinner while catching up on the days events from this home's open kitchen which overlooks a spacious great room and dining area. Retreat to your primary suite that is conveniently situated in the back of the home for plenty of privacy. Visit Villamar and explore new single-family homes for sale in Winter Haven, FL. Residents will have access to two resort-style amenity centers featuring a clubhouse, pool, and playground. Winter Haven is known for its beautiful chain of lakes with lakeside restaurants and its award-winning community theater. Nearby attractions include Legoland Florida and Peppa Pig Theme Park. A brand-new model and new phase are coming soon. Each of our homes is built with innovative, energy-efficient features designed to help you enjoy more savings, better health, real comfort and peace of mind.

3937 Giorgio Drive, Winter Haven

1151 Carefree Cove Drive, Winter Haven
$399,000
3 Beds ⋅ 2 Baths ⋅ Carefree Cove SubDv. ⋅ 33881 Zip Code
Looking for a peaceful lakefront pool home or well appointed Airbnb property? This beautiful 3-bedroom, 2-bath home sits on Lake Conine in Winter Haven’s northern Chain of Lakes, with easy access to the Chain of Lakes Trail. The home has been completely renovated to include a brand new roof, A/C, luxury vinyl plank flooring, interior / exterior paint, water heater, and much more! The kitchen features tons of solid wood cabinets, all new stainless steel appliances, and granite countertops. It includes both a breakfast area and a picturesque cutout with a view of the pool area and lakefront! The laundry room is also built into the kitchen area and includes a unique custom built porthole window that provides both natural light and views to the Florida room and beyond. The kitchen flows into a large enclosed porch (Florida room) with tons of potential! It could be used as a second living room space, dining room, and even space for a game room or office area! The Florida room includes additional cabinets and a bar area with a granite countertop. From the Florida room you can access the screened open porch where you can enjoy a stunning lake view. The primary bedroom features an en suite bathroom with jetted tub/shower, new vanity & fixtures, as well as a large closet. The 2nd bedroom also includes a large closet. The garage has been converted into a 3rd oversized bedroom with a very large closet and shiplap feature wall. Both bathrooms have been fully renovated with gorgeous subway tile in the showers, new ceramic tile floors and vanities with solid surfaces. Outside the house has been completely repainted including newly painted concrete from the front to the back of the property. The home features a newly screened pool cage, a brand new pool liner, with a multi-colored LED pool light. There is a carport and large outdoor storage closet out front, and also a second driveway to park an extra vehicle or boat. The newly painted boathouse, which includes a roll-up door, is wired with electricity and could also function as a workshop. It features new lights, a new side door, and new wood stairs. The boathouse / workshop is approximately 10x20 feet and has tons of room for all your toys! There is no HOA to hassle with! The property includes its own large dock and a concrete slab along the beach area for launching your own boat. Most furnishings in listing are available for separate purchase. As a potential Airbnb, the unit currently sleeps 8, but could be configured to sleep more. Come see this beautiful renovated home today!

1151 Carefree Cove Drive, Winter Haven

6052 Kaley Drive, Winter Haven
$375,000
4 Beds ⋅ 3 Baths ⋅ Sunridge Village East SubDv. ⋅ 33880 Zip Code
Welcome to 6052 Kaley Dr in Sunridge Village! This spacious 4-BEDROOM, 3-FULL-BATH POOL HOME PLUS a dedicated HOME OFFICE/BONUS ROOM offers 2,200 square feet of living space, an impressive outdoor entertaining area, and numerous valuable upgrades! THE SELLERS WILL OFFER $10,000 TOWARDS A RATE BUY DOWN WITH A FULL PRICE OFFER! Located in a desirable NO CDD community with an exceptionally LOW HOA OF JUST $165 PER YEAR, this home offers both space and affordability! THE ROOF, A/C SYSTEM, REMODELED KITCHEN, and INTERIOR PAINTING ALL DONE IN 2019, while additional recent updates provide even more value and appeal. This inviting two-story home features an OPEN FLOOR PLAN with TALL CEILINGS, attractive CROWN MOLDING, and generous living spaces designed for both everyday comfort and entertaining. The beautifully UPDATED ISLAND KITCHEN boasts GRANITE COUNTERTOPS, DOUBLE CLOSET PANTRIES, and STAINLESS STEEL APPLIANCES. The spacious living room features a distinctive SPECIALTY CEILING and FRENCH DOORS opening directly to the covered lanai, creating a wonderful connection between indoor and outdoor living. A separate dining room provides additional space for gatherings, while the convenient inside laundry room includes a washer and dryer. The spacious PRIMARY SUITE features a private EN SUITE BATHROOM with a WALK-IN SHOWER and relaxing GARDEN TUB. Three additional bedrooms provide comfortable accommodations, while the DOWNSTAIRS BONUS ROOM, currently used as a HOME OFFICE, offers incredible flexibility and POTENTIAL TO CONVERT INTO A FULL 5TH BEDROOM! With one of the THREE FULL BATHROOMS conveniently located downstairs, this layout provides excellent options for guests, multigenerational living, or anyone looking for additional living space. SPACIOUS 3 CAR GARAGE! Get the full FLORIDA EXPERIENCE by stepping outside to your own PRIVATE BACKYARD OASIS! The spacious COVERED LANAI features TILE FLOORING and OUTDOOR CEILING FANS, providing the perfect setting for relaxing or entertaining. Beyond the lanai, you'll discover a SCREEN-ENCLOSED IN-GROUND SWIMMING POOL & SPA, complete with an OUTDOOR BAR, BUILT-IN PLANTERS, and a charming TIKI-STYLE COVER OVER THE SPA! The pool area has also benefited from several improvements, including a NEW POOL PUMP in 2023, EPOXY-COATED POOL DECK PAVERS in 2023, and a POOL HEAT EXCHANGER replaced approximately 4.5 years ago. The current owners have also installed VINYL PRIVACY FENCING, creating a FULLY FENCED BACKYARD for additional privacy and enjoyment. Other improvements include a BEAUTIFUL NEW DOUBLE FRONT ENTRY DOOR installed in 2025, adding to the home's curb appeal. Situated on a generous .25-ACRE LOT in Sunridge Village, this property offers an EXCELLENT CENTRAL FLORIDA LOCATION! Enjoy convenient access to the POLK PARKWAY, providing easy connections toward TAMPA and ORLANDO, as well as nearby HIGHWAY 60, offering a direct route west toward TAMPA and east toward VERO BEACH and Florida's Atlantic Coast. Shopping, restaurants, and everything Winter Haven has to offer are also conveniently located nearby. With ALL THE UPDATES, 4 BEDROOMS PLUS A FLEXIBLE DOWNSTAIRS BONUS ROOM, 3 FULL BATHROOMS, FULLY FENCED BACKYARD, and spectacular SCREENED POOL & SPA AREA, this home offers an outstanding combination of space, improvements, and Florida living! Add in the NO CDD and incredibly LOW ANNUAL HOA of just $165, and this is an opportunity you won't want to miss. Schedule your private showing today!

6052 Kaley Drive, Winter Haven

1010 Edgewater Drive, Winter Haven
$795,000
4 Beds ⋅ 3 Baths ⋅ Lake Eloise Estates SubDv. ⋅ 33884 Zip Code
FULLY REMODELED WATERFRONT HOME,PRIVATE POOL and BOAT DOCK WITH LIFT and NO HOA! Enjoy the best of Florida living in this beautifully remodeled 4-bedroom, 3-bathroom waterfront home in Winter Haven, offering modern finishes, a desirable split floor plan, and exceptional indoor-outdoor living. The inviting interior features stylish tile flooring, recessed lighting, and a stunning living room highlighted by a custom stacked-stone electric fireplace with a rustic wood mantle. The beautifully updated kitchen is a standout, featuring sleek solid-surface countertops, contemporary white shaker cabinetry, stainless steel appliances, and a HUGE STACKED-STONE CENTER ISLAND with breakfast bar, providing abundant workspace, seating, and the perfect gathering spot for family and guests. The split floorplan offers added privacy, while the spacious primary suite features sliding glass door access to the patio and an updated ensuite bathroom with a double-sink vanity and frameless glass walk-in shower. Additional highlights include NEW ROOF INSTALLED IN 2023, REMODELED KITCHEN AND BATHROOMS, french door, and TWO LAUNDRY AREAS—one conveniently located in the interior laundry room and another in the garage for added flexibility. The home also features NEW PLUMBING AND ELECTRICAL IN 2023, city water, and irrigation. Step outside to your private backyard oasis featuring a sparkling in-ground pool with a NEW POOL SURFACE AND NEW SCREEN ENCLOSURE, BOTH UPDATED IN 2023, an expansive paver patio, and a HUGE COVERED LANAI with a pine-paneled ceiling, outdoor TV, and stone accents, creating an ideal space for entertaining, relaxing, and enjoying the Florida sunshine. Waterfront enthusiasts will love the PRIVATE COVERED BOAT DOCK WITH BOAT LIFT on the canal leading to LAKE ELOISE, offering access to Winter Haven's renowned Chain of Lakes for boating, fishing, and watersports. With NO HOA, enjoy greater freedom and flexibility to accommodate your boat, trailer, and recreational equipment. Conveniently located near shopping, dining, parks, and everyday essentials, with access to Winter Haven's attractions and major Central Florida destinations, this move-in-ready property combines extensive updates, versatile living spaces, and an exceptional waterfront lifestyle. Enjoy your own private pool, spacious covered lanai, and boating access to Lake Eloise—all with NO HOA!

1010 Edgewater Drive, Winter Haven

3115 Captain Jax Way, Winter Haven
$201,790
3 Beds ⋅ 3 Baths ⋅ Serenity At Peace Creek Th SubDv. ⋅ 33884 Zip Code
Under Construction. This new two-story townhome offers ample space to live and grow with a total of three bedrooms. The first level features a spacious and flexible open-concept layout shared between the kitchen, dining room and family room, maximizing the interior living space. Two secondary bedrooms and a lavish owner’s suite featuring a full bathroom comprise the second floor. Serenity at Peace Creek Reserve is a masterplan community of new townhomes with a beautiful natural creek. Winter Haven is the chain of lakes city, with over 26 linked together by a canal. There are lots of shops, restaurants, and bike paths. Peace Creek Reserve is what you have been looking for. A safe small town feel with convenience, the perfect place to raise a family.

3115 Captain Jax Way, Winter Haven

1606 Eagle Pond Drive, Winter Haven
$155,000
2 Beds ⋅ 2 Baths ⋅ Eagle Pond Condo SubDv. ⋅ 33884 Zip Code
Step into an inviting opportunity and a genuine deal at this price in the desirable Cypresswood Golf & Country Club. Whether you’re seeking a comfortable full-time residence, a relaxing winter retreat, or a place to embrace an active Florida lifestyle, this second-floor 2-bedroom/2-bathroom condo delivers warmth, convenience, and a true sense of community.Enjoy the privacy of an upper-level location with a practical, easy-flow layout designed for comfortable living, plus a convenient storage room for extra belongings. Maintenance-free ownership means the HOA handles exterior and ground maintenance, community pool access, 24-hour security, common-area upkeep, trash service, exterior pest control, and private road maintenance—so you can simply enjoy your home.The convenient location, a short drive to Legoland Florida Resorts, and offers easy access to Hwy 27, making shopping, dining, medical facilities, and everyday errands quick and simple while still keeping you nestled in a peaceful community setting. Residents are welcomed into a lifestyle filled with amenities: a championship 18-hole golf course, on-site restaurant & clubhouse for dining & events, sparkling community swimming pool, tennis courts & pickleball courts, and fitness center. Perfectly positioned for those who value both relaxed living and an active community atmosphere, this condo offers exceptional value and an immediate sense of belonging in one of Winter Haven’s most appealing settings. Schedule your private showing today and experience the lifestyle for yourself. All buyers must provided a pre-approval letter or proof of funds. Buyers are responsible for verifying the accuracy of all information.

1606 Eagle Pond Drive, Winter Haven

3083 Captain Jax Way, Winter Haven
$201,190
3 Beds ⋅ 3 Baths ⋅ Serenity At Peace Creek Th SubDv. ⋅ 33884 Zip Code
Under Construction. Open flow sets the tone for this elegant new Crestone II two-story townhome. There are a total of three bedrooms. The first level features a spacious and flexible open-concept layout shared between the kitchen, dining room and family room, maximizing the interior living space. Two secondary bedrooms and a lavish owner’s suite featuring a full bathroom comprise the second floor. Serenity at Peace Creek Reserve is a masterplan community of new townhomes with a beautiful natural creek. Winter Haven is the chain of lakes city, with over 26 linked together by a canal. There are lots of shops, restaurants, and bike paths. Peace Creek Reserve is what you have been looking for. A safe small town feel with convenience, the perfect place to raise a family.

3083 Captain Jax Way, Winter Haven

4462 Emerald Palms Lane, Winter Haven
$975,000
4 Beds ⋅ 3 Baths ⋅ Emerald Palms SubDv. ⋅ 33884 Zip Code
Luxury Living in Emerald Palms – Southeast Winter Haven Welcome to an exceptional custom-built residence in Emerald Palms, one of Southeast Winter Haven’s desirable gated communities. Situated on an expansive 0.41-acre homesite, this beautiful four-bedroom, three-bath home has been used primarily as a private vacation retreat and occupied sparingly. This Arthur Rutenberg designed home is an exceptionally well-maintained property that offers the look and feel of a nearly new home, with quality craftsmanship, elegant finishes, and outstanding indoor-outdoor living. The home’s impressive exterior features a concrete tile roof, attractive modern architecture, and beautifully maintained landscaping that creates an inviting first impression. Step inside to a spacious entry foyer highlighted by designer lighting and decorative inlay tile, leading into an open-concept living area designed for both comfortable everyday living and entertaining. Soaring ceilings with double tray details, oversized porcelain tile flooring, and an expansive wall of sliding glass doors fill the great room with natural light while providing picturesque views of the pool and lanai. At the heart of the home, the gourmet kitchen combines style and functionality with a large center island, granite countertops, upgraded cabinetry, premium stainless-steel appliances, and a walk-in pantry. The adjoining dining and living areas create a natural gathering space for family, friends, and special occasions. The generously sized primary suite offers a peaceful escape, featuring tray ceilings, abundant natural light, and an oversized walk-in closet. Its luxurious en-suite bathroom includes dual granite vanities, a jetted soaking tub, a separate walk-in shower, and a private water closet. The additional bedrooms are thoughtfully arranged in a split-bedroom floor plan to provide privacy and flexibility. Each offers comfortable living space and ample closet storage, while one guest bedroom features its own private en-suite bathroom. The fourth bedroom provides exceptional versatility and can easily serve as a game room, media room, hobby space, or secondary living area. An extraordinary outdoor living experience awaits. The custom heated pool and spa, representing an investment of more than $120,000, serves as the centerpiece of the expansive screened lanai. Features include integrated self-cleaning systems, decorative tile accents, deck jets, therapeutic spa jets, and a full-length sitting shelf with jets. Upgraded pavers and linear drainage contribute to the attractive, finished appearance of the outdoor entertaining space. The fully equipped outdoor kitchen is designed for serious entertaining, featuring a premium Lynx gas grill, side burner, beverage cooler, granite countertops, and stainless-steel range hood. Prepare meals, entertain guests, or enjoy game day while relaxing beside the pool. Under the covered lanai, a contemporary outdoor gas fireplace with a striking black-stone surround and TV mount creates an inviting setting for relaxing evenings throughout the year. Additional premium features and upgrades include: • Whole house 22KW Generac Guardian standby generator • Irrigation well for cost-effective landscape watering • Tankless Rinnai water heater • Multiple zoned air-conditioning systems • Salt-filtered pool system • Oversized side-entry three-car garage with durable epoxy flooring Oversized side-entry three car garage with durable stained concrete.

4462 Emerald Palms Lane, Winter Haven

3047 Captain Jax Way, Winter Haven
$201,190
3 Beds ⋅ 3 Baths ⋅ Serenity At Peace Creek Th SubDv. ⋅ 33884 Zip Code
Under Construction. This new two-story townhome offers ample space to live and grow with a total of three bedrooms. The first level features a spacious and flexible open-concept layout shared between the kitchen, dining room and family room, maximizing the interior living space. Two secondary bedrooms and a lavish owner’s suite featuring a full bathroom comprise the second floor. Serenity at Peace Creek Reserve is a masterplan community of new townhomes with a beautiful natural creek. Winter Haven is the chain of lakes city, with over 26 linked together by a canal. There are lots of shops, restaurants, and bike paths. Peace Creek Reserve is what you have been looking for. A safe small town feel with convenience, the perfect place to raise a family.

3047 Captain Jax Way, Winter Haven

3952 Giorgio Drive, Winter Haven
$285,000
3 Beds ⋅ 2 Baths ⋅ Villamar SubDv. ⋅ 33884 Zip Code
Under Construction. Brand new, energy-efficient home available by Nov 2026! Configure the flex room in the front of the home to an at home office space or hobby space for the kids. Past the foyer, the open kitchen flows to the dining space, great room and outside patio. Private primary suite offers a spacious area to relax. Visit Villamar and explore new single-family homes for sale in Winter Haven, FL. Residents will have access to two resort-style amenity centers featuring a clubhouse, pool, and playground. Winter Haven is known for its beautiful chain of lakes with lakeside restaurants and its award-winning community theater. Nearby attractions include Legoland Florida and Peppa Pig Theme Park. A brand-new model and new phase are coming soon. Each of our homes is built with innovative, energy-efficient features designed to help you enjoy more savings, better health, real comfort and peace of mind.

3952 Giorgio Drive, Winter Haven

725 Heritage Drive Ne, Winter Haven
$560,000
4 Beds ⋅ 3 Baths ⋅ Hamilton Pointe SubDv. ⋅ 33881 Zip Code
BEAUTIFUL HAMILTON POINTE POOL HOME! Welcome to this 4-bedroom, 2.5-bath pool home sits on a half-acre lot with no rear neighbors, offering 3,114 square feet of living space and peaceful conservation views. Inside, you’ll find a spacious kitchen with an eat-in area, a large living room with 13-foot ceilings, crown molding, a coral tile fireplace, and French doors opening to the screened pool and lanai. The split-bedroom layout features a primary suite with lanai access, dual vanities, a garden tub, separate walk-in shower, and ample closet space. Three additional bedrooms and a flexible office provide room for a variety of needs. The formal dining room also offers access to the pool area, creating an easy flow for entertaining. Outside, the oversized screened lanai and pool offer plenty of space to relax and enjoy Florida living. Notable improvements include a 2019 roof and exterior paint, 2020 gutters and screens, a 2021 hybrid water heater and whole-house repipe, plus a resurfaced pool, new sand filter, and refreshed pool screening. Conveniently located near downtown Winter Haven, Highway 27, LEGOLAND, golf courses, shopping, dining, and area airports.

725 Heritage Drive Ne, Winter Haven

4925 Cypress Gardens Road Unit 97, Winter Haven
$180,000
2 Beds ⋅ 2 Baths ⋅ Doves Rest Add SubDv. ⋅ 33884 Zip Code
Welcome to this meticulously maintained 2-bedroom, 2-bathroom double-wide mobile home located in a 55+ co-op community. The home features brand-new vinyl plank flooring in the main living area and a newly remodeled kitchen, giving the interior a fresh, updated feel. Outside, a long attached carport provides ample covered parking, while an attached storage shed offers additional space for tools and equipment. The community offers a variety of amenities and activities, including a heated swimming pool, shuffleboard courts, a pickleball court, a basketball court, an exercise room, a woodshop, a dog park, and a pond. With plenty of opportunities for recreation, hobbies, and socializing, this community offers an active lifestyle with something for everyone. Furniture is negotiable and may be included if desired by the buyer.

4925 Cypress Gardens Road Unit 97, Winter Haven

888 Twin Oaks Lane, Winter Haven
$2,000,000
5 Beds ⋅ 5 Baths ⋅ Twelve Oaks Estates SubDv. ⋅ 33880 Zip Code
Welcome to 888 Twin Oaks Lane, where striking custom architecture, luxury features, four acres of privacy, and resort-style outdoor living come together in prestigious, gated Twelve Oaks Estates. Built by respected custom builder Alan Ulch on a quiet cul-de-sac, this distinctive residence offers 4,565 square feet of heated living space with five bedrooms, four full bathrooms, one half bathroom, and a versatile bonus room. A dramatic two-story foyer and living room showcase soaring 22-foot ceilings, an architectural catwalk, and custom shiplap detailing. Abundant windows fill the home with natural light and frame peaceful property views, complemented by engineered wood flooring, oversized doorways, plantation shutters, and custom window treatments with motorized shades. The chef-inspired kitchen pairs premium Bosch and Thermador appliances with Misterio quartz countertops, floor-to-ceiling cabinetry, a custom range hood, and floating shelves. A built-in coffee maker, Ice-O-Matic nugget ice machine, and separate wine and beverage refrigeration elevate everyday living and entertaining. Two oversized sinks, concealed small-appliance closets, deep island drawers, and an expansive walk-in pantry provide exceptional storage and functionality. The main-level primary suite offers direct pool access and a spa-like bathroom with an oversized soaking tub, floor-to-ceiling tiled shower, dual vanities, dedicated makeup area, and two expansive walk-in closets with custom shelving. A separate main-level mother-in-law suite welcomes extended family or guests. Oversized secondary bedrooms with walk-in closets, an office nook, and a spacious bonus room offer flexibility for work and recreation. The oversized laundry and mudroom feature abundant counter space, a utility sink, laundry chute, barn door, and dedicated pet-washing station. Expansive covered porches with elegant pavers and wood-planked ceilings invite you to enjoy the peaceful setting. Relax on the twin-size bed swing and enjoy the nature. Expansive sliding glass doors connect the interior to an oversized custom heated saltwater pool with a sun shelf, integrated spa, wraparound seating bench, and beautiful lighting. An outdoor shower and plumbing provisions for a future outdoor kitchen enhance this private retreat. Beautiful acreage framed by horse fencing provides room to gather, play, and explore. Quality construction and modern conveniences include Hardie board siding, metal roofing over the porches, whole-home spray foam insulation, a Generac whole-house generator, Culligan water treatment system, three tankless water heaters, two central air-conditioning systems plus a mini-split, and an integrated residential fire sprinkler system. An oversized driveway provides ample parking. With controlled gated access and paved community roads, Twelve Oaks Estates offers a peaceful home base convenient to Winter Haven, Lakeland, Auburndale, and Bartow, with shopping, dining, downtown entertainment, parks, lakes, and boating nearby. Polk Parkway connections to I-4 put Tampa, Orlando, both international airports, and attractions including LEGOLAND Florida, Walt Disney World, Universal Orlando, and Busch Gardens Tampa Bay within reach. Grand spaces for gathering. Quiet places to retreat. Four private acres to call your own. 888 Twin Oaks Lane brings together custom craftsmanship, luxury finishes, resort-style outdoor living, and everyday comfort for an exceptional expression of private estate living.

888 Twin Oaks Lane, Winter Haven

273 Mariposa Street, Winter Haven
$285,000
3 Beds ⋅ 2 Baths ⋅ Florida Highland Co SubDv. ⋅ 33884 Zip Code
Welcome to 273 Mariposa St. in the desirable Orchid Springs Patio Homes community in Winter Haven! This beautifully maintained 3-bedroom, 2-bathroom home has undergone MAJOR UPGRADES THROUGHOUT in 2022/2023, offering a wonderful combination of modern improvements, spacious living areas, and Florida charm! The versatile floor plan features a formal living room, dining room, and family room, with luxury vinyl plank flooring throughout much of the home and tile flooring in the family room. The inviting living room features vaulted ceilings accented by beautiful wood beams, adding warmth and character. The FULLY REMODELED KITCHEN is a standout feature, offering gorgeous granite countertops, updated cabinetry, a center island, stylish backsplash, and stainless steel appliances, including built-in ovens, cooktop, microwave, and dishwasher. The dining room is enhanced by classic wainscoting and sliding glass doors that fill the space with natural light and provide easy access to the family room and outdoor living areas. The bathrooms have received attractive updates! The guest bathroom features an updated vanity, toilet, tile, backsplash, and fresh paint. The spacious primary suite offers a private ensuite bathroom and generous closet space. The list of MAJOR IMPROVEMENTS continues with a COMPLETE HOME REPLUMBING, COMPLETE ELECTRICAL REWIRING WITH UPDATED OUTLETS THROUGHOUT, WINDOWS REPLACED with double-pane windows, updated baseboards, interior repainting, updated blinds, and a NEW WATER HEATER installed in September 2024. The home also features a well-maintained Trane A/C system, an attractive METAL ROOF and an attached 2-car garage with built-in storage cabinetry and a replaced garage door opener. Step outside and enjoy Florida living from the SCREEN-ENCLOSED PATIO or the additional open patio featuring a firepit, perfect for relaxing or entertaining! Situated on a desirable .14-acre CORNER LOT, the property showcases beautiful, mature oak and palm trees, along with thoughtfully maintained landscaping. Orchid Springs Patio Homes offers residents access to a COMMUNITY POOL and CLUBHOUSE, providing a wonderful opportunity to enjoy the Florida lifestyle. LOCATION IS ANOTHER GREAT FEATURE! Conveniently situated near restaurants, medical facilities, churches, and shopping, with a NEW PUBLIX just approximately 5 minutes away! The home also offers easy access to HIGHWAY 27 and is just a short drive from LEGOLAND FLORIDA RESORT, making it easy to enjoy everything Central Florida has to offer. With its extensive upgrades, generous living spaces, inviting outdoor areas, and convenient location, this home is a wonderful opportunity to enjoy Florida living. Schedule your private showing today!

273 Mariposa Street, Winter Haven

4446 Glenns Landing, Winter Haven
$279,900
3 Beds ⋅ 2 Baths ⋅ Cypress Landing Ph 03 SubDv. ⋅ 33884 Zip Code
LOCATION! LOCATION! LOCATION! SPRING-FED LAKE DEXTER WITH REMARKABLY CLEAR WATER! Welcome to CYPRESS LANDING, one of Winter Haven’s hidden gems, offering an incredible Florida lake lifestyle! Residents enjoy private community access to beautiful LAKE DEXTER, featuring a PRIVATE BOAT RAMP, BOAT STORAGE OPTIONS, COMMUNITY BOAT DOCK WITH BOAT SLIPS, WATERFRONT SWIMMING POOL, CLUBHOUSE, TENNIS COURTS, AND SCENIC LAKESIDE WALKING PATHS! Boat storage and boat slips are community amenities; availability, fees, and usage requirements are subject to HOA confirmation. Golf carts are also permitted, subject to community guidelines! Located at 4446 GLENNS LANDING, this inviting 3-BEDROOM, 2-BATHROOM HOME features a BRAND-NEW CENTRAL A/C SYSTEM! Inside, you’ll find CERAMIC TILE FLOORING THROUGHOUT, spacious living and dining areas, and a beautiful kitchen featuring GRANITE COUNTERTOPS AND STAINLESS STEEL APPLIANCES! Expansive rear sliding glass doors bring the outdoors in, seamlessly connecting the interior living space to the covered, screened porch and creating an inviting atmosphere for entertaining or simply enjoying Florida living. The primary suite offers a WALK-IN CLOSET AND PRIVATE BATHROOM WITH A WALK-IN SHOWER, while a skylight brings additional natural light into the home. An interior laundry room and attached garage provide everyday convenience. ENJOY FLORIDA LIVING WITH TWO COVERED, SCREENED PORCHES, both featuring ceramic tile flooring! An UPGRADED PAVER DRIVEWAY, lush St. Augustine lawn, mature shade trees, and attractive landscaping add to the home’s curb appeal. JUST MINUTES FROM LEGOLAND FLORIDA RESORT, shopping, dining, entertainment, and Winter Haven’s renowned CHAIN OF LAKES! Enjoy boating, fishing, kayaking, and waterfront recreation right within your community, with additional public boat ramps nearby. SPRING-FED LAKE DEXTER ACCESS, BRAND-NEW CENTRAL A/C, GRANITE COUNTERTOPS, STAINLESS STEEL APPLIANCES, TWO SCREENED PORCHES, AND EXCEPTIONAL COMMUNITY AMENITIES! Experience the benefits of lake community living without the waterfront price tag. SCHEDULE YOUR PRIVATE SHOWING TODAY!

4446 Glenns Landing, Winter Haven

3084 Captain Jax Way, Winter Haven
$209,990
3 Beds ⋅ 3 Baths ⋅ Serenity At Peace Creek Th SubDv. ⋅ 33884 Zip Code
Under Construction. This new two-story townhome offers ample space to live and grow with a total of three bedrooms. The first level features a spacious and flexible open-concept layout shared between the kitchen and family room, maximizing the interior living space. Two secondary bedrooms and a lavish owner’s suite featuring a full bathroom comprise the second floor. Serenity at Peace Creek Reserve is a masterplan community of new townhomes with a beautiful natural creek. Winter Haven is the chain of lakes city, with over 26 linked together by a canal. There are lots of shops, restaurants, and bike paths. Peace Creek Reserve is what you have been looking for. A safe small town feel with convenience, the perfect place to raise a family.

3084 Captain Jax Way, Winter Haven

3437 Grenville Drive, Winter Haven
$223,000
2 Beds ⋅ 2 Baths ⋅ Traditions Ph 01 SubDv. ⋅ 33884 Zip Code
Discover this 2-bedroom, 2-bath home filled with potential and ready for its next owner. Located in Traditions at Lake Ruby, a maintenance-free, gated 55+ community, this thoughtfully designed home combines comfort, functionality, and style for relaxed Florida living. The kitchen features maple wood cabinetry, an updated microwave, reverse osmosis at the kitchen sink, and a convenient closet pantry. The dining area is highlighted by vaulted ceilings and a decorative arched pass-through to the kitchen, adding character and charm. The open-concept floor plan offers a spacious living room with a decorative planter shelf and triple sliding glass doors leading to the Florida room, where tranquil garden views create a peaceful setting. The primary bedroom suite offers serene backyard views and a walk-in closet. The en-suite primary bathroom is designed for comfort, featuring a comfort-height vanity, tile flooring, and a walk-in shower with a glass door. Enjoy outdoor living even during inclement weather from the Florida room, while the low-maintenance courtyard, enhanced with pavers and Florida-friendly landscaping, provides a private and inviting outdoor retreat. The fenced backyard with mature plantings offers additional outdoor space. Additional features include a laundry pantry with washer and dryer, architectural shingle roof (2020), HVAC system (2017), exterior lighting, water softener system, gutters, a glass entry storm door, and a two-car garage. A paved driveway and walkway further enhance the home's curb appeal. Traditions at Lake Ruby offers an impressive array of amenities, including a lakefront clubhouse, dock and boat ramp, heated swimming pool and spa, ballroom, billiards, meeting rooms, library, computer room, craft room, dog park, tennis and basketball courts, bocce, shuffleboard, fitness center, and aerobics studio. Residents can also enjoy a variety of planned community activities. Monthly HOA fees cover front-yard lawn service, cable tv, internet, exterior house painting, and community clubhouse amenities helping provide a convenient, low-maintenance lifestyle. Ideally located near shopping, restaurants, medical facilities, Legoland, and major routes, this home offers a wonderful combination of comfort, convenience, and vibrant community living.

3437 Grenville Drive, Winter Haven

251 Greenfield Road, Winter Haven
$224,900
2 Beds ⋅ 2 Baths ⋅ Cypresswood SubDv. ⋅ 33884 Zip Code
VACANT AND PRICED TO SELL! NEW ROOF 2025! 2 BED 2 BATH CONCRETE BLOCK STUCCO (CBS) HOME IN GUARD GATED CYPRESSWOOD GOLF AND COUNTRY CLUB, WINTER HAVEN FL 33884. Vacant single story home on a 0.44 acre lot with an attached garage, central air, and no CDD. Roof replaced 2025 and water heater 2017. The home needs some work and is priced for its condition. Seller is open to making repairs needed for FHA or conventional loan approval. Cypresswood is a golf cart friendly golf course community with a 24 hour guard gate, 18 hole championship golf course, clubhouse, community pool, and tennis. Located in Polk County near Legoland Florida, Cypress Gardens, the Chain of Lakes, shopping, dining, US 27, and the I-4 corridor between Orlando and Tampa. FHA, VA, conventional, and cash welcome. Sold as is.

251 Greenfield Road, Winter Haven

6240 Pinehurst Loop, Winter Haven
$415,000
3 Beds ⋅ 2 Baths ⋅ Lake Ashton West Phase Ii North SubDv. ⋅ 33884 Zip Code
Virtually Staged. Welcome to your dream retirement home located at 6240 Pinehurst Loop Winter Haven, Fl. 33884, designed with 3 Bedrooms and 2 full bathrooms. This delightful Sebastian home in the highly sought after Lake Ashton, a 55 plus community in Central Florida, was BUILT in 2022. It features a spacious living area with Trey Ceiling and abundant Natural light thru the Glass Front Entry Door with Privacy Tint, Triple Sliders in the LR and Double Glass Window in the Dinette area; Plantation Shutters in the Bedrooms, an Upgraded Kitchen with Stainless Steel Appliances, Under Cabinet Lighting, Breakfast Bar, Walk in Pantry, Cabinet Pantry with Pull Out Drawers and Granite countertop. The inviting living and dining areas blend seamlessly together with carpet flooring, while the open-concept layout is beautifully enhanced by tile flooring in the kitchen, laundry, guest bathroom/hall, entry and Primary Suite bath. Two spacious guest bedrooms and a full bath are located near the front entry; a pocket door provides privacy and a Linen Closet provides storage. The guest bath has a comfort height vanity with Granite counter top, and glass block window is above the tiled shower/tub combo. The Primary Suite is a private retreat on the back of the home, complete with a generously sized bathroom with separate comfort height vanities, a tiled corner shower with glass block accent above and a separate walk in closet. Step outside and enjoy the screened and covered lanai that overlooks the seasonal pond, perfect for entertaining. Plumbing was added to the privacy wall at the time of build, should you desire to have a summer kitchen. The laundry room with wash sink is spacious and is accessible from the garage and kitchen. The exterior of the home has been well maintained with landscaped flower beds and the double car garage with separate golf cart entry is a bonus. A water filtration system is located in the garage. Don't miss the opportunity to explore this wonderful property! Lake Ashton is a Florida Retirement Community that offers a Florida Retirement Lifestyle with resort style amenities and activities for 55+ in Florida. The main clubhouse offers a movie theater, bowling lanes, grand ballroom, card, craft and billiards, outdoor temperature controlled swimming pool, Bocce Courts, tennis courts, 1/2 court basketball, shuffleboard courts and MORE. The Health and Fitness Center has a large indoor temperature controlled pool, fitness center, indoor 1/2 court basketball, indoor racquetball, large multi-purpose room, card, craft, billiards, pickle ball courts and tennis courts. 2 -18 hole golf courses are located in Lake Ashton (memberships are optional). Tour this well maintained home today! You'll be glad you did!

6240 Pinehurst Loop, Winter Haven

4235 Cedarwood Street, Winter Haven
$109,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code
Walk right into this beautifully maintained home located in Oakwood Estates, a 55+ community. The metal roof is only 6 years old. The home has newer windows and a new vapor barrier. The lanai has all new windows. The home also has a water filtration system. The furnishings you see will stay with the home. The living and dining room give a very open and inviting feel. The kitchen bar offers additional eating space for when the whole family comes to visit. The ample kitchen cabinetry has been updated. The only carpet remaining in the home is in the guest bedroom, but it is in very good condition. Sit on the front porch or side lanai for your morning coffee. Enjoy the peaceful community or join in to the many activities available year round. The community offers two pools, two clubhouses, shuffleboard, tennis courts, bocci ball, miniature golf, and much, much more. Make your appointment today.

4235 Cedarwood Street, Winter Haven

2746 Adeline Avenue, Winter Haven
$286,490
3 Beds ⋅ 2 Baths ⋅ Willowbrook South SubDv. ⋅ 33881 Zip Code
Under Construction. The Archer II is one of our one-story floorplans features in our Willowbrook South community in Winter Haven, Florida. Take your pick between two sleek exterior options when choosing this floorplan. Inside this 3 bedroom, 2 bathroom home you’ll find 1,328 square feet of comfortable living. The open concept layout allows for seamless movement between spaces making entertaining guests a breeze. It also provides homeowners versatile design options. The kitchen features shaker-style cabinets, quartz countertops, and stainless steel appliances, which are sure to both turn heads and make meal prep easy. You’ll bever be too far from the action with the living and dining area right there. In every bedroom, besides the primary bedroom, you’ll have carpeted floors and a closet in each room. Whether these rooms become bedrooms, office spaces, or other bonus rooms, there is sure to be comfort. The primary bedroom features luxury vinyl plank flooring that will be sure to stand out. It also has its own attached bathroom that features a walk-in closet and all the space you need to get ready in the morning. Sharing a sink isn’t a worry with the double vanity, and you also get additional privacy with a separate door for the toilet and shower. Contact us today and find your home at Willowbrook South. *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.*

2746 Adeline Avenue, Winter Haven

3996 Giorgio Drive, Winter Haven
$280,000
3 Beds ⋅ 2 Baths ⋅ Villamar SubDv. ⋅ 33884 Zip Code
Under Construction. Brand new, energy-efficient home available by Dec 2026! Enjoy open-concept living with a chef-inspired kitchen overlooking the great room and dining area. The spacious primary suite offers a peaceful retreat and includes a large walk-in closet. Visit Villamar and explore new single-family homes for sale in Winter Haven, FL. Residents will have access to two resort-style amenity centers featuring a clubhouse, pool, and playground. Winter Haven is known for its beautiful chain of lakes with lakeside restaurants and its award-winning community theater. Nearby attractions include Legoland Florida and Peppa Pig Theme Park. A brand-new model and new phase are coming soon. Each of our homes is built with innovative, energy-efficient features designed to help you enjoy more savings, better health, real comfort and peace of mind.

3996 Giorgio Drive, Winter Haven

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