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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

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

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

1921 Manor Circle Se, Winter Haven
$1,295,000
3 Beds ⋅ 3 Baths ⋅ Laha-Wa Manor SubDv. ⋅ 33880 Zip Code
Imagine waking each day to breath-taking lake views, swaying palms, spectacular sunsets, and the tranquil beauty of Lake Lulu. Quietly positioned on one of the most desirable lakes within Winter Haven's renowned Chain of Lakes, this beautifully maintained and thoughtfully updated single-story residence enjoys a private setting on 0.45-acre lot, surrounded by mature landscaping and established tropical gardens. Designed for both comfortable everyday living and exceptional entertaining, the home offers spacious, versatile accommodation with stunning lake views from the moment you enter through the front door. The flowing floor plan seamlessly connects the formal living and dining areas, with 50-inch SAMSUNG TV & rich wood flooring to the family room, kitchen, breakfast nook, and outdoor living spaces, creating an inviting atmosphere throughout. At the heart of the home is a well-appointed gourmet kitchen featuring a large center island, breakfast bar, premium stainless-steel appliances, updated Kitchen-aid double ovens with air fryer, microwave, French-door refrigerator, and dishwasher. Custom cabinetry includes soft-close drawers, pull-out shelving, glass display cabinets, wine storage, pantry space, and appliance garage. Beautiful non-slip tile flooring extends throughout the main living areas. Adjacent to the kitchen, the breakfast nook offers direct access to the pool area through sliding glass doors, while the spacious family room features a stunning Travertine fireplace, built-in SAMSUNG 50-inch television, neutral finishes, and expansive 12-foot sliding glass doors that open directly to the screened resort-style swimming pool & paved Lanai (1485sq,ft ) The laundry room is equipped with custom cabinetry, generous storage, a large linen closet, and includes a front load washer and dryer. A conveniently located half bath provides direct access to the pool and outdoor entertainment area. The fourth bedroom is currently configured as a home office. NEW (AUGUST 2026) ARCHITECTURAL SHINGLE ROOF on home, boathouse and storage shed. Owned security system. Phone, internet, and Wi-Fi connectivity throughout the home. Extensive custom cabinetry and storage solutions. Walk-in closet system in the primary suite. Landscaped with irrigation and lighting. Circular paved driveway with courtyard entrance and carriage lighting. Attached 2 car garage has staircase to large, walk-up attic for extra storage. 106ft frontage on Lake Lulu with a private dock, boathouse with lift. Direct access to Winter Haven's Chain of Lakes for boating, fishing, and water recreation. Convenient location with easy access to downtown Winter Haven, shopping, dining, LEGOLAND, Highway 27, Interstate 4. Tampa and Orlando Airports.

1921 Manor Circle Se, Winter Haven

37 Lake Eloise Lane, Winter Haven
$515,000
3 Beds ⋅ 2 Baths ⋅ Harbour Estates SubDv. ⋅ 33884 Zip Code
Located in the desirable, tree-lined community of Harbour Estates, this custom-built 3-bedroom, 2-bath pool home offers expansive living spaces, and an exceptional outdoor lifestyle. Situated on an impressive .57-acre corner lot at the end of a quiet cul-de-sac, this property provides privacy, space and convenience in a highly sought-after location. Upon arrival, a grand courtyard welcomes you to sit and enjoy the beautifully landscaped grounds. A lovely leaded-glass front door with transom window opens into the inviting foyer, creating an elegant first impression. The generously sized Living Room features a striking stone fireplace, tray ceiling and strategically placed floor outlets that allow for flexible furniture placement. Three sets of glass sliding doors overlook the patio and pool area, bringing the outdoors in and creating a seamless connection between the interior and exterior living spaces. The eat-in Kitchen showcases a timeless black-and-white design, featuring crisp white cabinetry accented with crown molding and designer brushed-nickel hardware. Sleek black granite countertops beautifully complement the tile backsplash, while the kitchen sink is strategically positioned beneath a picture-frame window offering wonderful views of the pool. The upgraded stainless-steel appliance package includes a convection range, while recessed lighting illuminates the space. A cabinet pantry provides additional storage and a convenient coffee bar with a USB outlet adds both functionality and convenience to the kitchen. The charming breakfast nook provides the perfect spot for casual dining. The formal Dining Room features classic chair-rail molding and flows effortlessly into the kitchen, making it ideal for entertaining. The spacious 16' x 23' Primary Bedroom Suite features a beautiful coved ceiling and plenty of room for a comfortable sitting area. Additional features include wall-to-wall carpeting, a safe, and 2 closets, one of which is a walk-in closet. The luxurious Primary Bath offers dual comfort-height vanities with granite countertops, linen closet and walk-in shower with glass enclosure. A bidet and comfort-height toilet are located within the private water closet. A convenient access door leads directly to the patio. Two spacious Guest Bedrooms share a lavishly appointed Guest Bathroom featuring an oversized vanity, luxurious soaking tub accented by a decorative tile surround and a separate walk-in shower with glass enclosure. Outdoor living is truly exceptional in the fully fenced and meticulously landscaped backyard. A sparkling saltwater pool, surrounded by an expansive patio, provides the perfect setting for relaxing or entertaining family and friends. Distant views of Little Lake Eloise add to the tranquil setting. Additional features include a Laundry Room w/ cabinetry, washer & dryer, double-pane Pella fiberglass windows, glass storm door, water softener system, 2024 water heater, security system, stone-accent facade, 2023 architectural shingle roof, well for irrigation, freshly painted exterior, gutters, exterior lights, & 220-volt wiring in the oversized 3 car garage. The garage also features a garage door opener & provides abundant space for vehicles, storage or recreational equipment. Ideally situated in the picturesque community of Harbour Estates, this exceptional home offers the perfect blend of space, comfort, privacy, and convenience, just minutes from shopping, restaurants and LEGOLAND Resort.

37 Lake Eloise Lane, Winter Haven

7002 Summit Circle, Winter Haven
$340,000
3 Beds ⋅ 2 Baths ⋅ Summit East Ph 02 SubDv. ⋅ 33884 Zip Code
Beautifully maintained 3-bedroom, 2-bath pool home in a quiet Winter Haven community with a low HOA of $260/year. This home offers extensive upgrades, modern finishes, and a bright, open layout designed for comfortable living. Major improvements include a new roof (2020), new AC (2020), tankless water heater (2021), updated windows (2018), Culligan water system (2016), and a new pool pump and filter (2025). The kitchen features granite countertops, stainless steel appliances, a breakfast bar, and excellent natural light. The bathrooms also include granite counters, updated fixtures, and a large tub in the primary suite. Paradise Walk in tub (2020) in second bathroom. Enjoy Florida living with a saltwater fiberglass pool, screened enclosure, covered patio, fenced yard and irrigation system. Interior highlights include multiple flex spaces, neutral paint, updated ceiling fans, clean flooring, and move-in ready condition. Located close to shopping, dining, medical facilities, Legoland, and major highways, this home offers strong value with thoughtful upgrades and excellent maintenance. Schedule your private showing today.

7002 Summit Circle, Winter Haven

2 Casarena Court, Winter Haven
$309,900
3 Beds ⋅ 3 Baths ⋅ Casarena On Lakes SubDv. ⋅ 33881 Zip Code
Welcome to 2 Casarena Ct, a truly unique opportunity in a private gated Winter Haven community. One of only three 3-bedroom with 3 full bathroom residences in the community, this spacious home is ideally positioned to capture beautiful views of Lake Cannon, part of Winter Haven’s renowned Chain of Lakes. Step inside to an inviting open-concept floor plan featuring an expansive living and dining area highlighted by a striking fireplace, creating a warm focal point for both everyday living and entertaining. The thoughtfully designed layout includes two generous primary suites, providing exceptional privacy and flexibility for owners, guests, extended family, or seasonal visitors. Each primary offers spacious living accommodations, with the balcony primary offering double vanity and a sauna in the shower, the while the additional ensuite bedroom and bath provide even more versatility. The updated kitchen features granite countertops, stainless steel appliances, ample cabinetry, and convenient access to the main living and dining spaces. Enjoy Florida living from multiple outdoor areas, including a private balcony overlooking the community pool with views toward Lake Cannon, as well as a private Florida room at the rear of the home—perfect for morning coffee, reading, relaxing, or enjoying the Florida sunshine year-round. Additional features include two HVAC systems, with one replaced approximately six months ago, tankless water heater, natural gas connection, a whole-home generator for added peace of mind, and a two-car garage. A unique private paver parking space provides additional dedicated parking beyond the garage—an exceptional feature for condo living. Residents enjoy the benefits of a private gated community along with lawn care, access to the community pool, and lake access to Lake Cannon and the Chain of Lakes with boat slips that are first come first serve. The combination of water views, spacious living areas, multiple private suites, outdoor living spaces, garage parking, and community amenities makes this property an excellent option for buyers seeking the convenience of low-maintenance living without sacrificing space, privacy, or comfort. Whether you're looking for a full-time residence, seasonal Florida retreat, or spacious lock-and-leave lifestyle, 2 Casarena Ct offers a rare combination of privacy, lakefront community living, and exceptional interior space in the heart of Winter Haven.

2 Casarena Court, Winter Haven

9513 Waterford Oaks Boulevard, Winter Haven
$725,000
5 Beds ⋅ 4 Baths ⋅ Waterford Oaks SubDv. ⋅ 33884 Zip Code
HUGE $25,000 PRICE DROP! Welcome to an exceptional 5-bedroom, 3.5 bathroom estate in the highly desirable gated community of Waterford Oaks in Winter Haven, This home offers a 2023 ROOF; NEW EXTERIOR PAINT; and a ONE YEAR HOME WARRANTY offered by the seller, along with lake access, resort-style outdoor living, flexible living spaces, and exceptional parking. A standout feature is community access to LAKE WINTERSET and the Winter Haven Chain of Lakes. A community boat ramp and dock on Lake Winterset are just a short distance away, offering convenient access for boating, fishing, and water recreation. Situated on a beautifully landscaped corner lot, the property features mature landscaping and elegant architectural details. The property offers exceptional parking with an elegant CIRCULAR DRIVEWAY and a separate SIDE ENTRY DRIVEWAY leading to the three-car garage, providing abundant space for guests, vehicles, and recreational equipment. Inside, the spacious floor plan showcases original hardwood floors, high ceilings, multiple tray ceilings, crown molding, custom built-ins, recessed lighting, and abundant natural light. The living room features custom built-in shelving surrounding an electric fireplace, while the adjoining family room offers a custom entertainment center, built-in shelving, and large windows overlooking the screened outdoor living area. The gourmet kitchen is a true centerpiece of the home, featuring custom wood cabinetry, GRANITE COUNTERTOPS, a substantial CENTER ISLAND with prep sink, built-in appliances, gas range with decorative backsplash and pot-filler faucet, abundant counter space, and generous storage. The kitchen overlooks the pool area and connects easily to the entertaining spaces. A spacious BUTLER'S CHAMBER provides additional cabinetry, workspace, storage, and a convenient laundry area. The luxurious primary suite offers a private retreat with a tray ceiling, accent lighting, large windows, plush carpeting, and a walk-in closet. The en-suite bathroom features dual vanities, tile flooring, a deep soaking tub beneath an arched window, and a spacious walk-in shower. One additional bedroom is currently used as a dedicated pool table/billiards room, offering flexibility as a recreation space or bedroom. Upstairs, an expansive TV room or potential mother-in-law suite provides additional privacy and versatility with a microwave, refrigerator, sink, 1/2 bathroom, and walk-in closet currently used as a small office. The outdoor living space is truly one of the home's major highlights, featuring a screened-in lanai, large pool with a swim-out area, OUTDOOR KITCHEN, barbecue area with NEW BARBECUE GRILL, and spacious brick-paver pool deck. The pool enclosure was rescreened last year, creating an inviting setting for swimming, dining, relaxing, and entertaining. Additional highlights include two tankless water heaters, with one serving the primary bedroom and the other serving the remainder of the home; a private well supplying irrigation for the property and adjacent vacant land which is also available for purchase. Conveniently located near shopping, dining, major roadways, local lakes, LEGOLAND Florida, and other Central Florida attractions, this distinctive estate combines Lake Winterset access, a resort-style saltwater pool, outdoor kitchen, gourmet kitchen, three-car side-entry garage, exceptional parking, multiple entertainment spaces, flexible upstairs living, and significant recent improvements.

9513 Waterford Oaks Boulevard, Winter Haven

1776 6th Street Nw Unit 304, Winter Haven
$92,900
2 Beds ⋅ 2 Baths ⋅ Lakeridge Condo SubDv. ⋅ 33881 Zip Code
**THIS CONDO IS PRICE TO SELL !!**CENTRAL FLORIDA 55+ Age GATED CONDOMINIUM COMPLEX WITH LAKE AND CITY VIEW. All new insulated windows throughout. This condominium provides 1,347 sq. ft. of living area & is located in the beautiful "Chain Of Lakes" City of Winter Haven, Fl. Very friendly complex w/ social activities offered if you wish to participate. Monthly association fee includes water, sewer, trash, fiber optic cable & internet, condo reserves, manager and use of recreational facilities. Lakeridge Condominiums offers a maintenance-free lifestyle w/ heated pool, tennis, shuffleboard, community room, gated entrances & covered assigned parking space. The large bright kitchen has plenty of cabinets & great counter space, appliances (dishwasher does not work) & pantry closet. The kitchen overlooks the 26'x14' great room that also adjoins the additional bonus space & storage closet. The 16X14 foot Primary bedroom suite has a walk in closet & bathroom w/ walk-in shower. Beautiful views of Spring Lake can be enjoyed from Primary bedroom & living areas. The 2nd bedroom & bath can be a private guest area or for your personal use for office, hobbies etc. The washer & dryer are included in the sale. Central heat and air conditioning. Convenient proximity to shopping, places of worship, groceries & restaurants. Extra assigned storage bin on same floor. Make this your full time home, winter home or investment property to update. Lakeridge Condominiums is an age-restricted, well-maintained & well-managed community. Sharepoint car charger provided for those with electric cars. Non-smoking property. 1 pet, 20 pounds or under may be approved.

1776 6th Street Nw Unit 304, Winter Haven

1380 S Lake Roy Drive, Winter Haven
$359,000
4 Beds ⋅ 3 Baths ⋅ South Roy Shores Pb 38 Pg 45 SubDv. ⋅ 33884 Zip Code
Virtually Staged. UPDATED POOL HOME WITH NEW BATHROOMS, NEW POOL DECK & BRAND-NEW WATER HEATER! Welcome to this spacious 4-bedroom, 3-bathroom, 2,955-square-foot pool home on a desirable corner lot in Winter Haven, ideally located across from beautiful lakefront homes and close to Winter Haven's renowned Chain of Lakes. Major recent improvements include a BRAND-NEW HOT WATER HEATER installed in October 2026, TWO NEWLY REMODELED BATHROOMS completed in 2025, and a RESURFACED POOL WITH NEW POOL DECK completed in 2022. The roof was also replaced in 2023, providing additional peace of mind for the next owner. Inside, the triple-split bedroom floor plan offers privacy and flexibility, making this home ideal for families, guests, or those who need dedicated spaces for work and hobbies. The oversized family room is designed for entertaining, featuring two sets of sliding glass doors that open directly to the screened and netted pool enclosure and covered patio. The seamless indoor-outdoor flow creates the perfect setting for gatherings, relaxing poolside, or enjoying Florida's year-round lifestyle. A spacious flex room with direct pool and patio access offers endless possibilities as a game room, home office, media room, hobby space, or additional entertainment area. The kitchen features custom-made cabinetry, granite countertops, a custom tile backsplash, and stainless-steel appliances, creating a functional and inviting space for everyday living and entertaining. The primary suite offers a private retreat with a bathroom featuring a garden tub, dual sinks, and a walk-in shower. The two recently remodeled bathrooms add fresh, updated appeal throughout the home. Additional highlights include a LARGE LAUNDRY ROOM with utility sink, drop-down ironing board, and extra shelving, as well as tile and wood flooring throughout the main living areas. Step outside to your own private backyard retreat. The resurfaced pool and NEW POOL DECK, completed in 2022, are surrounded by a screened and netted enclosure with a covered patio, creating an inviting space for swimming, dining, entertaining, and soaking up the Florida sunshine. A welcoming front screened porch, ample covered parking, and two detached storage sheds provide additional convenience and storage. The yard is irrigated by a well with a newer irrigation timer. The HVAC system is approximately 9 years old. While there are still opportunities for cosmetic updates in select areas, the home's generous size, desirable floor plan, significant recent improvements, and fantastic outdoor living spaces provide an excellent foundation for making it your own. Location adds even more appeal. The property is just a short walk to Freedom Boat Club, making it easy to access and explore Winter Haven's famous Chain of Lakes. LEGOLAND Florida is approximately one mile away, offering exceptional convenience for both residents and guests. With its four bedrooms, three bathrooms, private pool, newly remodeled bathrooms, resurfaced pool and new pool deck, new water heater, 2023 roof, flexible living spaces, and prime location near lakes and attractions, this is an exciting opportunity to own a spacious Winter Haven home and enjoy the best of the Florida lifestyle.

1380 S Lake Roy Drive, Winter Haven

1776 6th Street Nw Unit 308, Winter Haven
$144,900
2 Beds ⋅ 2 Baths ⋅ Lakeridge Condo SubDv. ⋅ 33881 Zip Code
**LARGE 2 BEDROOM - 2 BATH CONDO - NEW LISTING IN CENTRAL FLORIDA**- AGE 55+, GATED COMMUNITY (however, a slightly younger age may be approved). This up-to-date condo provides 1,347 sq. ft. of living area & is located in the beautiful "Chain Of Lakes" City of Winter Haven, Florida. NEW ENERGY-EFFICIENT WINDOWS THROUGHOUT. The monthly fee INCLUDES: water, sewer, trash, fiber optic cable package with Choice HD, digital video recorder & fiber optic internet w/ 1 gig speed, & use of recreational facilities. Lakeridge Condominiums offers a maintenance-free lifestyle w/ heated pool, tennis, shuffleboard, community room, gated secured entrances, covered assigned parking space, social events & activities. This well-appointed, move-in-ready condo has a large, bright kitchen w/ lots of cabinets, a tile backsplash, flush-mount LED ceiling lighting, plenty of counter space, all appliances & a pantry closet. The kitchen overlooks the 26'x14' great room that also adjoins the additional FL/bonus area & storage closet. The 16' x 14 ' primary bedroom easily accommodates a king-size bed & has a walk-in closet with a decorative barn door. The beautiful remodeled primary bathroom has an extra-wide door for easy direct access & includes a walk-in shower with a large format designer wall tile, & a comfort-height vanity with a vessel sink. The 2nd bedroom is convenient to the hall bath, which has a tub/shower combination & comfort-height vanity. The WASHER & DRYER are included in the sale. The Flooring throughout is either wood-look luxury vinyl or tile, NO CARPETING. Custom window shades are in place and are included in the sale. An extra assigned storage bin is located on the same floor. Enjoy beautiful views of Spring Lake and the evening sunsets from most rooms. Shopping, medical, hospital, places of worship, groceries, restaurants & bus line are very close by. COVERED ASSIGNED PARKING SPACE. SharePoint electric car charger on site for owners! Measurements are approximate. Information is believed to be accurate but not guaranteed. NON-SMOKING COMPLEX THAT IS WELL MAINTAINED & MANAGED. FURNITURE IS NEGOTIABLE. Make this your full-time or winter home!

1776 6th Street Nw Unit 308, Winter Haven

405 Valley Court, Winter Haven
$455,000
4 Beds ⋅ 2 Baths ⋅ Lake Mariam Hills SubDv. ⋅ 33884 Zip Code
You must see this stunning 4 bedroom, 2 bathroom, pool home located in the gated community of Lake Miriam Hills. This east Winter Haven home boasts a split floor plan, nearly 2,500 sqft of living space, french doors , a formal dining space, a family room and living room, a wood burning fireplace, an open kitchen with granite counter tops and stainless appliances, high ceilings, wood laminate floors in common areas, carpeted bedrooms, a two car garage, and an inside laundry room. The large master suite includes a huge walk-in closet, a gorgeous master bathroom, a soaking tub, a dual sink vanity, and a walk-in shower. The guest bathroom has pool access and a shower/tub combo. The saltwater pool and patio area features covered seating, plenty of shade, and generous deck space around the large pool. Recent repairs include a new roof in 2023, a new septic drainfield in 2022, a new AC in 2022, and a new hot water heater in 2023. Enjoy relaxing and entertaining on the huge pie-shaped lot with shade trees, mature landscaping, and playground equipment all nuzzled back into a quiet cul-de-sac. The community offers private access and a boat ramp to beautiful Lake Mariam. The home is conveniently located to Lego Land, several shopping centers, grocery stores, restaurants, medical centers, and schools. Don’t miss out. Set up your showing today.

405 Valley Court, Winter Haven

1776 6th Street Nw Unit 409, Winter Haven
$114,900
2 Beds ⋅ 2 Baths ⋅ Lakeridge Condo SubDv. ⋅ 33881 Zip Code
Virtually Staged. Virtually staged bedroom. CENTRAL FLORIDA LAKE VIEW CONDO- THIS IS THE ONLY GATED 55+ CONDOMINIUM COMPLEX IN WINTER HAVEN. (Slightly younger buyer could possibly get approved.) NEW ENERGY-EFFICIENT WINDOWS IN THIS IMMACULATE, MOVE-IN READY 2 BEDROOM 2 BATH CONDO. WATER HEATER is 2025 & CENTRAL AIR CONDITIONER is a 2020. The kitchen is larger than most condo kitchens & the unit has a total of 1,347 sq. ft. of living area. MONTHLY FEE INCLUDES-WATER, SEWER, CABLE, FIBER OPTIC INTERNET, TRASH REMOVAL, CONDO RESERVES & use of recreational facilities- HEATED POOL, tennis, shuffleboard, community room, gated entrances & covered assigned parking space. All appliances & washer/dryer are included. The 26'x14' great room adjoins the additional FL/bonus room with large storage closet. The 16X14 foot master bedroom easily accommodates a king-size bed & has a walk-in closet & en-suite bathroom with walk-in shower. The 2nd bedroom includes a space-saving drop-down Murphy bed. The 2nd bathroom has a tub/shower combination. The linen closet is near the washer & dryer for convenience. Lakeridge is close to shopping, places of worship, groceries, restaurants, medical offices & hospital. Extra assigned storage on the same floor. Social activities available, if you wish to participate. Lakeridge is well-maintained, well-managed & passed inspections & studies with flying colors. Electric car charger on site for owners use. YOU ONLY HAVE TO PAY FOR YOUR ELECTRICITY HERE, AS EVERYTHING ELSE IS INCLUDED IN THE MONTHLY FEE. ONE SMALL PET MAY BE APPROVED. NON SMOKING PROPERTY. Quick Closing is available. Information believed to be accurate but not guaranteed. Measurements are approximate.

1776 6th Street Nw Unit 409, Winter Haven

280 Santa Rosa Drive, Winter Haven
$399,500
3 Beds ⋅ 2 Baths ⋅ Overlook Estates SubDv. ⋅ 33884 Zip Code
This property went under contract fast and it's back on the market, no fault of the owner. If you missed it the first time, here's your second chance! 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

2500 21st Street Nw Unit 58, Winter Haven
$150,000
3 Beds ⋅ 3 Baths ⋅ Casa Del Sol Condo Village Ph 02 SubDv. ⋅ 33881 Zip Code
Welcome to this spacious 3-bedroom, 2.5-bath corner condo in the lakefront Casa Del Sol community. This two-story home offers 1,334 square feet, an attached two-car garage, granite countertops, newer appliances, inside laundry, and flexible living and dining areas. Sliding doors open to a private courtyard and screened patio overlooking the pool and putting green. All bedrooms are upstairs, including a primary suite with a walk-in closet and private balcony. Whether you're a first-time buyer, downsizer, or investor, this property delivers an easy, low-maintenance living experience. Community amenities include pools, a clubhouse, a fitness center, and access to Lake Hartridge. Conveniently located near downtown Winter Haven, shopping, dining, and major roadways. Schedule your private showing today!

2500 21st Street Nw Unit 58, Winter Haven

1019 W Lake Eloise Terrace, Winter Haven
$799,000
2 Beds ⋅ 3 Baths ⋅ Lake Eloise Sub SubDv. ⋅ 33884 Zip Code
Major Price Improvement .....Welcome to an exceptional and truly distinctive lakefront estate on Lake Eloise with a private pool, defined by architectural artistry, refined character, and timeless Spanish-Mediterranean elegance. This 2-bedroom, 3-bath residence offers more than 3,700 square feet under roof, providing expansive, thoughtfully designed interiors ideal for both entertaining and serene everyday living. From the moment you enter, you are welcomed by an atmosphere of bespoke craftsmanship and enduring design. Exquisite brick archways, rich warm wood detailing, and three elegant wood-burning fireplaces establish a setting that is both inviting and unmistakably unique. The kitchen continues this elevated architectural story, showcasing custom extensive cabinetry, stone countertops, premium stainless steel appliances, and a dramatic brick-arched passage that serves as a striking focal point. Thoughtfully designed to capture the essence of the Florida lifestyle, the home opens to a private resort-style swimming pool set against a peaceful lakefront backdrop, creating an extraordinary environment for relaxation, refined entertaining, and sweeping waterfront views. Seamless indoor-outdoor transitions enhance the sense of openness throughout, making the residence equally suited as a distinguished full-time home or an exclusive private lakefront retreat. With its authentic Spanish-Mediterranean influence, handcrafted brick detailing, multiple fireplaces, resort-style pool, and premier waterfront location, a rare opportunity to own a residence of true individuality and lasting appeal—one that cannot be replicated. Schedule your private showing and experience the elegance and exclusivity of this remarkable lakefront offering.

1019 W Lake Eloise Terrace, Winter Haven

689 Lake Howard Drive Nw Unit 213, Winter Haven
$145,000
2 Beds ⋅ 2 Baths ⋅ Wellington Pt 01 Bldgs 01 02 & Wellington Pt 02 B SubDv. ⋅ 33880 Zip Code
Virtually Staged. 55 PLUS CONDO FULLY REMODELED: Completely remodeled with high-end finishes, a spotless, move-in-ready interior, and a desirable lakeside setting on the world-famous Winter Haven Chain of Lakes. Welcome to 689 Lake Howard Drive, Unit 213, where thoughtful updates, generous living spaces, and an exceptional waterfront community come together at an attractive price point. Located in The Wellington on the shores of Lake Howard, this impressive 2 bedroom, 2 bath condo feels fresh, modern, and remarkably spacious. The expansive living and dining area features beautiful flooring, crown molding, updated lighting and ceiling fans, and plenty of room for comfortable everyday living and entertaining. Sliding glass doors open to a large enclosed Florida room overlooking the beautifully maintained community grounds, providing even more space to relax and enjoy the Florida lifestyle. The remodeled kitchen is a standout, featuring quartz countertops, abundant white soft-close cabinetry, a farmhouse-style sink, herringbone tile backsplash, under-cabinet lighting, and a complete stainless steel LG appliance package including refrigerator, range, microwave, and dishwasher. Both bathrooms have been beautifully remodeled with quartz-topped vanities and impressive custom tile work. Walk-in showers feature frameless glass enclosures, decorative tile accents, niches, and contemporary finishes. An exceptionally large walk-in closet provides outstanding storage, while an interior laundry closet with included washer and dryer and a large private exterior storage room add everyday convenience. The Wellington offers beautifully landscaped grounds, two pool areas including a heated pool for winter use, clubhouse, shuffleboard, community activities, and a private dock on Lake Howard with access to the Winter Haven Chain of Lakes—perfect for fishing and enjoying life on the water. The condo fee includes basic cable and internet, water, garbage pickup, exterior building maintenance, and grounds maintenance. A private covered parking space is also included. Conveniently located near medical facilities, shopping, restaurants, churches, grocery stores, and charming Downtown Winter Haven. Beautifully remodeled, incredibly spacious, and located in a Chain of Lakes waterfront community—this is 55+ living with the updates already done for you!

689 Lake Howard Drive Nw Unit 213, Winter Haven

4040 Palma Ceia Circle, Winter Haven
$749,000
3 Beds ⋅ 4 Baths ⋅ Cypresswood Palma Ceia SubDv. ⋅ 33884 Zip Code
Meticulously maintained and beautifully remodeled, this exceptional Palma Ceia residence in Cypresswood offers pond frontage, three private en-suite bedrooms, a dedicated office, a heated swimming pool, and incredible golf course views. The pavered driveway and walkways, manicured flower gardens, and a 2022 black metal roof set the stage for the impressive interior. Elevated ceilings, crown molding, waterproof Pergo flooring, stone counters, and plantation shutters are just a few of the home’s stunning features. At the heart of the home is a spacious great room featuring a natural gas fireplace with shiplap façade. Triple sliding glass doors, with new screens, create a seamless indoor-outdoor flow to the covered lanai and pool area while showcasing the outdoor views. The updated kitchen features quartz counters, an island with a prep sink and filtered water, a Kohler workstation sink, breakfast bar, stainless appliances, double ovens, gas range, Bosch dishwasher, and a spacious dinette overlooking the pool. A private office provides the perfect setting for working from home. Designed to give everyone their own space, the home offers three bedrooms with en-suite bathrooms. The primary suite includes pool access, a tray ceiling, two walk-in closets with built-in shelving, and a gorgeous remodeled bathroom featuring a six-foot freestanding soaking tub, glass-enclosed walk-in shower, dual vanities, and a water closet. The second bedroom includes an equally impressive en-suite bath with custom tile flooring, a granite counter, tub, and separate walk-in shower. Located at the rear of the home, the third en-suite bedroom is ideal for visiting guests and can be closed off with a pocket door for added privacy. Its bathroom offers a granite counter with dual sinks, a tub and shower combo, and a linen closet. An additional linen closet is located in the guest-wing hallway. The interior laundry room provides a closet pantry, storage closet, and convenient half bathroom. Florida living takes center stage outdoors with a screen-enclosed heated pool, expansive covered lanai, and a separate screened area for sunning. The peaceful setting overlooks the pond and third hole of the golf course, where a variety of birds and wildlife can be enjoyed daily. Meticulously designed gardens, window planter boxes and a pavered sitting area near the pond—ideal for a fire pit—complete this private outdoor oasis. The two-car garage features an epoxy floor, utility sink, storage closets, and overhead storage racks. Additional improvements and features include a 2026 installed gas water heater, a 26-gauge standing seam metal roof (2022) with a 40-year warranty, dual-zone air conditioning (2020), irrigation on separate meter, plantation shutters throughout, remote-controlled lanai lighting, pool safety fence, Ring cameras, rain gutters, and more. Located within the guarded Cypresswood community, this remarkable home combines thoughtful updates, exceptional care, abundant privacy, and a truly beautiful golf course and waterfront setting. Cypresswood Golf & Country Club features an 18-hole championship golf course, driving range, pro shop, jr. olympic pool, tennis & pickleball courts, an event venue, a sports pub and more. Located just minutes from shopping, medical facilities and downtown Winter Haven. Centrally located between Tampa and Orlando with easy commutes to airports and beaches. Come see what this magnificent home and community in Central FL has to offer!

4040 Palma Ceia Circle, Winter Haven

333 Lake Howard Drive Nw Unit 211B, Winter Haven
$149,900
3 Beds ⋅ 2 Baths ⋅ Imperial Harbours Ph 01 SubDv. ⋅ 33880 Zip Code
Remodeled and updated 2nd floor condo with picturesque views of the pool and lush landscaping. This 3 bedroom unit is ready for immediate occupancy. Recent updates include fresh interior paint, new flooring, new kitchen cabinets and solid surface counters. This established 55 and over community is nestled on the shores of Lake Howard on the famous Chain of Lakes and includes a community boat dock/fishing pier. Additional amenities include a heated pool, gazebo with bathrooms, shuffleboard, activities and secure storage. Located close to the heart of downtown Winter Haven, This condo provides an opportunity to enjoy the Lakefront Florida lifestyle at an affordable price. Monthly fees include water, cable, internet, trash, sewer, exterior maintenance and grounds maintenance making this an attractive opportunity for year round residents or snowbirds. Seller is a licensed Realtor in the State of Illinois.

333 Lake Howard Drive Nw Unit 211B, Winter Haven

328 Hamilton Shores Drive Ne, Winter Haven
$765,000
5 Beds ⋅ 4 Baths ⋅ Hamilton Pointe SubDv. ⋅ 33881 Zip Code
5 BEDROOM, 3.5 BATH HOME WITH 3800+ SQFT OF LIVING: Impressive 5-bedroom home offering over 3,800 square feet of beautifully designed living space, including 3.5 baths, an oversized bonus room, inside storage room, formal living and dining rooms, and a spacious family room—all set on a beautifully landscaped 0.40-acre corner lot in sought-after Hamilton Pointe. This immaculate home offers the perfect blend of quality finishes, versatile spaces, and detailed craftsmanship throughout—making it both impressive and move-in ready. From the moment you arrive, you'll be drawn in by the lush, meticulously maintained landscaping that offers year-round color, texture, and curb appeal. Twin driveways and an oversized side-entry three-car garage provide generous parking and storage, ideal for multi-vehicle households, guests, or recreational toys. Step through the welcoming foyer into a light-filled interior defined by soaring ceilings, elegant crown molding, and custom built-ins that speak to the elevated level of construction found throughout the home. Formal living and dining rooms offer ideal spaces for entertaining, while the expansive first family room features tranquil pool views and flows seamlessly into a chef-inspired kitchen. Here, you’ll find all-wood cherry cabinetry with upgraded 15-inch-deep uppers, granite countertops, newer stainless steel appliances, a breakfast bar, and a walk-in pantry. A cozy, window-lined dinette is perfect for casual meals or morning coffee with views of the sparkling pool. A triple-split bedroom layout ensures privacy and flexibility, making the home suitable for a wide variety of family dynamics. The primary suite is tucked away on its own wing, offering private access to the lanai, a spacious walk-in closet, and a spa-like bath complete with dual vanities, a jetted soaking tub, and a tiled walk-in shower. Four additional bedrooms are generously sized and feature wood flooring, ceiling fans, and ample closet space with extra built-in storage above. The guest bathrooms are tastefully appointed with tile-surround tub and shower combinations, offering comfort and convenience for family or visitors. In addition to the dedicated office, a large rear bonus room serves as the second family/TV room and can easily transform into a game room, media center, craft room, or additional living area. Step outside and unwind in your private backyard retreat, where a screen-enclosed pool deck and covered lanai overlook a solar-heated pool powered by 2020 panels. The lush landscaping and privacy fencing create a resort-like atmosphere perfect for year-round enjoyment. Additional highlights include a 2020 architectural shingle roof, new water heater, energy-efficient tinted windows, Kinetico whole-house water filtration system, irrigation well, newer pool pump, and dual HVAC systems. Located in one of Winter Haven’s most established and well-cared-for communities, Hamilton Pointe is known for its manicured lawns, mature oaks, and true pride of ownership. Residents enjoy easy access to the Winter Haven Chain of Lakes, downtown dining and entertainment, Legoland, and major roadways like the Polk Parkway—placing Orlando, Tampa, beaches, and international airports all within reach. Don’t miss your chance to own this exceptional home that offers space , quality, and lifestyle in one of Central Florida’s most desirable neighborhoods.

328 Hamilton Shores Drive Ne, Winter Haven

250 Brigham Road Nw, Winter Haven
$1,195,000
5 Beds ⋅ 6 Baths ⋅ Na SubDv. ⋅ 33881 Zip Code
Prepare to be captivated by this beautifully updated lakefront estate on Lake Hartridge, perfectly positioned along the highly sought-after Winter Haven Chain of Lakes. Situated on approximately 1.3 acres with an impressive 115 feet of waterfront, this exceptional property offers a rare combination of luxury, privacy, and breathtaking panoramic water views, all tucked away on a peaceful dead-end street. Mature oak trees and lush tropical landscaping create a timeless Old Florida ambiance while blending seamlessly with the home’s fresh, modern updates. A long private driveway welcomes you to the property, leading to an oversized detached two-car garage complete with a private apartment above—ideal for guests, multigenerational living, rental income, or a secluded home office—and a convenient full bathroom below. Inside the main residence, an expansive and thoughtfully designed floor plan features four spacious bedrooms and 4.5 beautifully appointed bathrooms. One bedroom is currently styled as a cozy movie room, creating the perfect entertainment space for relaxing evenings or family gatherings. The luxurious first-floor primary suite serves as a true retreat, offering a spacious sitting area with stunning views overlooking the sparkling screened pool and tranquil lakefront setting. The spa-inspired primary bathroom showcases a soaking tub, oversized walk-in shower, elegant dual vanities, and generous space designed for comfort and relaxation. At the center of the home is the beautifully updated gourmet kitchen, featuring sleek quartz countertops, modern cabinetry, stainless steel appliances, and abundant prep and storage space sure to impress any chef. Elegant porcelain flooring flows throughout the main living areas, while plush carpeting adds warmth and comfort to the bedrooms. Recent upgrades, including a new roof and new AC system, provide peace of mind and enhance the home’s fresh, move-in-ready appeal. Designed to maximize the spectacular lake views, the expansive lanai and private screened-in pool area with an in-ground hot tub create the ultimate outdoor oasis for year-round Florida living. Newly refreshed pool and lanai screening further elevate the experience, seamlessly blending indoor and outdoor entertaining spaces. For boating enthusiasts, the property truly stands out with a private covered dock featuring a metal roof and boat lift, offering direct access to the renowned Winter Haven Chain of Lakes, known for boating, fishing, watersports, and unforgettable sunset cruises. Additional highlights include dedicated RV parking with electrical, water, and sewer hookups, making this property ideal for those seeking adventure without sacrificing luxury and convenience. Located in the heart of Winter Haven, known as the “Chain of Lakes City,” residents enjoy easy access to over 50 interconnected lakes, waterfront dining, boutique shopping, recreational trails, and convenient access to both Tampa and Orlando attractions. This extraordinary lakefront estate perfectly combines modern updates, timeless elegance, and resort-style living—offering a truly rare opportunity to own a one-of-a-kind waterfront retreat.

250 Brigham Road Nw, Winter Haven

355 Ruby Lake Loop, Winter Haven
$463,700
4 Beds ⋅ 3 Baths ⋅ Ruby Lake Sub Ph Ii SubDv. ⋅ 33884 Zip Code
WONDERFUL POOL HOME IN GATED COMMUNITY. Don’t forget to ask about Seller Credits for exterior paint. Located in Ruby Lake subdivision, this spacious home boasts appealing architectural enhancements with high ceilings throughout its 2,648 sq.ft. of living area. The layout features an open concept design with a formal living room, formal dining room, large family room and a split-plan for the 4 bedrooms and 3 full baths. The centrally located kitchen offers plenty of beautiful wood cabinets and granite counter space along with the conveniences of a pantry, breakfast bar and a dinette giving great view of the outdoor living space and pool. The generous family room has sliding glass doors to the lanai & pool and stands open to the dinette and kitchen. The seamless transition between the kitchen, formal living and dining rooms, and the casual living areas is perfect for daily life and when hosting get-togethers. The master en suite features a generous bedroom with sliding glass doors to the lanai, walk-in closet, and the bathroom has dual vanities, a soaking tub, walk-in shower, and water closet. The second bathroom stands convenient to the additional bedrooms and living areas and the third bathroom stands convenient to the pool area. This great Central Florida location is near shopping, schools, medical facilities and restaurants with easy access to both Tampa and Orlando.

355 Ruby Lake Loop, Winter Haven

1108 Sawgrass Drive, Winter Haven
$422,999
2 Beds ⋅ 2 Baths ⋅ Lake Ashton West Ph Ii South SubDv. ⋅ 33884 Zip Code
This is a must see charming oasis located behind the secure gates of Lake Ashton, you don’t want to miss this opportunity of becoming an homeowner in this Exclusive 55+ community in Florida, comes with a upgraded custom13’6 x 28’ saltwater pool with propane heater and expanded screened enclosure that measures 44’ x 24’ tankless propane water heater, and gas hookup for an outdoor kitchen in Lake Ashton! If you are seeking a stunning 2-bedroom, 2-bath property this is the one it sits on the Lake Ashton West golf course and this environment for Living certified Green home features several builder upgrades PLUS extensive builder and owner upgrades Inside, you’ll find tile flooring throughout (no carpet), upgraded kitchen cabinetry with roll-out shelving, Calcatta Silestone countertops with beveled edge; custom kitchen pantry cabinet with roll-outs; under-cabinet lighting, custom closets in both bedrooms and laundry room plus a custom pantry storage. Additional features include custom closets, updated bathrooms with a walk-in shower and glass doors, remote-controlled blinds, upgraded lighting and fans, epoxy garage flooring, and enhanced landscaping Located in Lake Ashton, a premier 55+ community offering two 18-hole golf courses, a 26,000 + sq ft Health and Fitness Center, pickleball courts , a bowling alley, a restaurant and much more, activities are abundant in this exceptional community . Don’t miss this very special pool home. Schedule your showing today.

1108 Sawgrass Drive, Winter Haven

2935 Plantation Road, Winter Haven
$529,900
4 Beds ⋅ 4 Baths ⋅ Cypresswood Plantation SubDv. ⋅ 33884 Zip Code
Highly motivated seller! Bring all reasonable offers. This beautiful property is priced to move and the owner is ready to make a deal. Don't miss this incredible opportunity—schedule your showing today! Located in the highly sought-after gated golf community of Cypresswood in Winter Haven, this beautiful 4-bedroom, 3-bathroom home offers over 2,800 square feet of spacious living when pool room footage is added. The offering includes a private pool, and a 9x9 pool house complete with a half bath, perfect for guests, poolside entertaining, or an additional flex space. Inside, the home boasts a formal living room and an open-concept family room, dining area, and kitchen, creating a bright and inviting atmosphere ideal for both everyday living and hosting. Also features granite countertops, resurfaced garage, private office, freshly painted interior, paver driveway, and so much more. Enjoy the comfort, privacy, security, and lifestyle that come with living in one of Winter Haven’s premier golf communities.

2935 Plantation Road, Winter Haven

649 Broadmoor Circle, Winter Haven
$119,500
2 Beds ⋅ 2 Baths ⋅ Cypresswood Golf Villas SubDv. ⋅ 33884 Zip Code
Welcome home to this beautiful 2-bedroom, 2-bathroom golf villa nestled within the beautiful Cypresswood Golf and Country Club in Winter Haven, Florida. Property is steps away from the golf clubhouse!!! Brand NEW AC Fan motor, AC Amp Fuse and AC capacitor installed May 2026. Brand NEW fire/carbon monoxide detector alarms throughout the home.Home features a stunning Florida room, ready for relaxation. Dry bar with sink in living room perfect for entertaining your guests. Step out to your outside patio for even more enjoyment. With access to golf, clubhouse, Restaurant, pool and recreational facilities, this home offers a low-maintenance lifestyle in an active and vibrant community. Legoland attraction is approximately 5 miles. Disney World, Orlando and Tampa attractions are within 30-60 minute driving distance. Opportunities like this don’t last long, Just buy and move in!!! CLEAN TITLE WITH NO LIENS. Property being sold AS-IS.

649 Broadmoor Circle, Winter Haven

4612 Reynosa Drive Sw, Winter Haven
$305,000
3 Beds ⋅ 2 Baths ⋅ Plaza Sub SubDv. ⋅ 33880 Zip Code
Short Sale. BACK ON THE MARKET WITH A BANK-APPROVED SHORT SALE PRICE! Don’t miss the opportunity to own this one-of-a-kind, 3-bedroom, 2-bathroom, 2-car garage custom home. Upon arriving at the property, you are greeted by an oversized lot and mature trees in a quiet, well-established neighborhood. Inside, the home offers an open and split floor plan, cathedral ceilings, and an indoor/outdoor pool that flows from the back patio into the living room, adding a unique feature to this property—perfect for entertaining and allowing you to take a dip in any weather. On the left side of the home are two spacious bedrooms with large closets and a shared bathroom featuring a single vanity and a shower/tub combo. Moving to the right side of the house, you’ll find the master suite, loft, and kitchen. The master suite offers ample space and direct access to the pool area. The en-suite bathroom includes a garden tub and walk-in shower. The loft overlooks the living room and pool area and also contains two large storage spaces on either side, making storage accessible while serving as a great spot to watch a show and unwind. The kitchen features tile countertops and a small bar for additional seating. Right out back, the pool is enclosed in a full-screen cage with a large deck. The yard also boasts a shed for storage and plenty of space for activities. This home has so much to offer. Don’t wait—schedule your private showing today!

4612 Reynosa Drive Sw, Winter Haven

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