Winter Haven Real Estate

Welcome to Winter Haven, Florida, where stunning real estate opportunities await! Located in Polk County, Winter Haven is a vibrant city known for its beautiful lakes, lush landscapes, and abundant recreational activities. This idyllic locale offers a wide range of real estate options to suit diverse preferences.

Prospective buyers can discover an array of properties, from cozy single-family homes in friendly neighborhoods to luxurious waterfront estates overlooking the serene lakes. With its year-round mild climate and proximity to major attractions, Winter Haven presents an enticing living environment.

Moreover, Winter Haven enjoys easy access to neighboring towns, further enhancing its appeal. Just a short drive away, you'll find the charming communities of Auburndale, Lake Alfred, and Haines City, each offering their own unique character and amenities.

Whether you're seeking a peaceful retreat, a family-friendly community, or an active lifestyle with water sports and golfing, Winter Haven and its neighboring towns provide an abundance of options. Embrace the Florida dream and explore the fantastic real estate opportunities available in Winter Haven today!

Latest Winter Haven Real Estate For Sale

$1,100,000

4 Beds ⋅ 6 Baths ⋅ O6452572 MLS

Discover timeless elegance and waterfront living at 100 Island Way, a distinctive custom estate nestled within the gated community of Orchid Springs. Situated on approximately 1.29 acres of beautifully landscaped grounds overlooking Lake Lewis, this remarkable residence offers 4,179 square feet of living space, 4 bedrooms, 4 full bathrooms, 2 half bathrooms, and a detached artist's studio. Originally built in 1969, this one-of-a-kind home showcases exceptional architectural character, featuring natural coral rock sourced from Coral Gables, rich wood accents, custom built-ins, and thoughtfully designed living spaces. A grand circular driveway and expansive porte-cochère create an impressive entrance, welcoming you into a home filled with warmth, charm, and picturesque garden and lake views. At the heart of the residence is a stunning chef's kitchen, beautifully transformed in 2021 with an approximately $200,000 renovation. Featuring custom solid wood cabinetry, premium quartz countertops, a Wolf gas range, oversized Sub-Zero refrigerator, matching wine refrigerator, and a dedicated coffee and wine bar, this exceptional space is designed for both everyday living and entertaining. Two spacious primary suites, a private home office, and a library area provide comfort and versatility, while distinctive architectural details, including exotic redwood floating vanities, natural wood veneer accents, and custom sliding doors, add character throughout. The detached artist's studio offers additional flexible space, ideal for creative pursuits, a private workspace, or a personal retreat. An unexpected second-floor reading or drafting room, accessible by a spiral staircase, adds to the property's unique charm. Step outside into your own private Florida oasis, where lush tropical gardens, brick-lined courtyards, and expansive verandas create inviting spaces for relaxation and entertaining. Enjoy breathtaking waterfront views and a private dock on Lake Lewis, perfect for fishing, canoeing, or simply unwinding while watching the sunset. Notable improvements include the 2021 kitchen renovation, wood-look ceramic tile flooring installed in 2020, several remodeled bathrooms, four A/C units replaced in 2018, plumbing updates, refreshed exterior paint, and updated dock decking. Blending timeless craftsmanship, modern comforts, and serene waterfront surroundings, 100 Island Way presents a rare opportunity to own a truly distinctive Florida estate. Experience the beauty, privacy, and character of this exceptional property. Schedule your private showing today!

100 Island Way, Winter Haven

Courtesy of PMC OF CENTRAL FLORIDA LLC

$182,900

2 Beds ⋅ 1 Baths ⋅ NS1089559 MLS

Beautifully updated 2-bedroom, 1-bath home featuring a 2-year-old roof, new interior and exterior paint, new flooring throughout, and a remodeled bathroom. The brand new kitchen offers new cabinets and new upgraded stainless steel appliances, creating a clean and functional space. This home includes 728 sq. ft. of living area on an oversized 0.17-acre lot, providing room for outdoor enjoyment. Exterior features include a screened side porch, laundry room, carport, and two backyard sheds for storage or projects. Located near Winter Haven’s Chain of Lakes, shopping, dining, parks, and major roadways. A move-in-ready property with modern updates and convenient access to local amenities. Buyer is responsible for verifying all measurements, square footage, and layout details.

3223 Avenue S Nw, Winter Haven

Courtesy of THE BARNETT GROUP, INC.

$289,900

3 Beds ⋅ 2 Baths ⋅ L4965743 MLS

Welcome home to Winter Haven gem located in Garden Grove area, It is less than 3 miles to Legoland/Cypress Gardens. The .21 acre lot has plenty of room for a pool and outdoor entertaining or play set. Lots of options. There is NO HOA and NO flood zone requirements. Good condition. Newer appliances. There is a water filtration system attached. Enjoy privacy with a wooded rear view and no backyard neighbors. Inside, the spacious great room features a cozy wood-burning fireplace, perfectly positioned to be enjoyed from both the living area and the kitchen. Newer appliances. The cooktop range/oven has several features for cooking and baking. The flexible floor plan includes three generously sized bedrooms plus a dedicated home office—complete with a closet—making it an easy conversion for a 4th bedroom. Step outside to the large, screened back porch with the wooded view. With quick, convenient access to Cypress Gardens Blvd and major surrounding routes, this home perfectly blends private, peaceful living with everyday convenience. Schedule your tour today!

237 Stevenson Road, Winter Haven

Courtesy of KELLER WILLIAMS REALTY

$975,000

4 Beds ⋅ 3 Baths ⋅ TB8561005 MLS

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

Courtesy of FLAT FEE MLS REALTY

$215,000

3 Beds ⋅ 2 Baths ⋅ A4711107 MLS

GREAT INVESTMENT OPPORTUNITY! Great investment property featuring a very large yard in a nice neighborhood, conveniently located near shopping, restaurants, and other amenities. Property requires updates and improvements, offering excellent potential for investors.

1828 Avenue O Sw, Winter Haven

Courtesy of FLATFEE.COM

$290,000

3 Beds ⋅ 2 Baths ⋅ S5160316 MLS

WELCOME HOME! Discover this beautiful single-family home featuring 3 bedrooms, 2 bathrooms, and 1,720 square feet of living space, built in 2020 and located in Winter Haven! Designed with comfort and functionality in mind, this residence showcases a beautiful open floor plan that seamlessly connects the kitchen, dining, and living areas, creating a spacious and inviting atmosphere perfect for everyday living and entertaining. The modern kitchen features elegant granite countertops, stainless steel appliances, and a functional layout that makes meal preparation and gatherings a pleasure. The spacious primary bedroom provides a comfortable retreat, while two additional bedrooms allow flexibility for guests, a home office, or additional living needs. ONE OF THE PROPERTY'S STANDOUT FEATURES IS THE SOLAR PANEL SYSTEM, WHICH WILL BE PAID IN FULL BY THE SELLER AT CLOSING, allowing the new owner to enjoy the potential benefits of lower electricity bills without assuming the existing solar financing. Step outside to your fully fenced, private backyard, an ideal setting for outdoor gatherings, weekend barbecues, pets, or simply relaxing in the Florida sunshine. The property also features a SPACIOUS 2-CAR GARAGE, providing ample room for parking and additional storage. Conveniently situated near shopping, dining, schools, and major roadways, this home combines the appeal of newer construction with everyday convenience. Whether you're searching for a primary residence or an investment opportunity, this property is an excellent choice. Don't miss this fantastic opportunity! Schedule your private showing today!

188 Black Skimmer Lane, Winter Haven

Courtesy of AMY INTERNATIONAL CORP

$459,900

5 Beds ⋅ 3 Baths ⋅ L4965710 MLS

Welcome to 4407 Mandolin Boulevard in Winter Haven! This well-maintained 5 bedroom, 3 bath home in a gated community offers generous living spaces and a versatile layout. The flooring flows throughout with a ceramic tiled first floor and luxury vinyl second. The spacious kitchen with stainless steel appliances opens to the family room. A seperate front room provides space for a formal living-room or home office, complimented by a seperate formal dining area. A first floor bedroom and full bath add flexibility for guests or live in family members. Upstairs there is an open loft providing additional gathering space alongside three secondary bedrooms and another full bath. The primary suite features a sitting area, dual walk-in closets, and an ensuite bathroom with a garden tub. Enjoy relaxing on the screened rear lanai overlooking the large, fenced, backyard. The roof was replaced just two years ago adding to this home's appeal. Schedule your private showing today!

4407 Mandolin Boulevard, Winter Haven

Courtesy of THE MARKET REALTY COMPANY

$197,000

3 Beds ⋅ 1 Baths ⋅ L4966084 MLS

Lovely Winter Haven Home featuring a 3 bedroom, 1 bath, 1,144 square feet of inviting living space with NO HOA! Perfect for first time home buyers, retiree's or anyone just looking to downsize. Situated on .14 acres near the heart of Winter Haven and Lake Alfred. Step inside to a spacious, open living room that flows into the large kitchen and adjoining dining area, providing plenty of room for everyday living and entertaining. Three bedrooms and a full bathroom are located toward the rear of the home. Outside the property offers room to enjoy the outdoors, while a storage shed provides convenient space for tools, equipment and all your extras. An A/C replacement in 2021 adds to the home's appeal. Set in a quiet neighborhood, this property offers a peaceful setting with convenient access to shopping, medical facilities, dining and entertainment. Schedule your showing today and discover the possibilities.

881 5th Street, Winter Haven

Courtesy of LPT REALTY, LLC

$333,140

4 Beds ⋅ 3 Baths ⋅ O6453123 MLS

Under Construction. Beautiful 2 Level, 2 Car Garage Home with Open Concept Living and 4 Bedrooms! The inviting front porch opens to a gracious foyer with 2 adjacent secondary bedrooms and a full bathroom. The spacious family room is open to the dining area and adjacent kitchen. The primary suite boasts an en suite bathroom with dual sink vanity, shower, private water closet, and large walk-in closet. The 2nd level offers a spacious loft and 2 secondary bedrooms each with walk-in closets and a full bathroom.

824 Andrew Street, Winter Haven

Courtesy of DRB GROUP REALTY, LLC

376 Lake Eloise Pointe Drive, Winter Haven

$290,000

4 Beds ⋅ 2 Baths ⋅ TB8561956 MLS

Check out this freshly painted 4 bedroom, 2 bath, 2 car garage with a huge lot! High ceilings, open floor plan and split floor plan, huge primary suite with walk in closet. Ready for you to move in and drop your bags- new permitted roof. Guaranteed to pass a 4 point!

376 Lake Eloise Pointe Drive, Winter Haven

Courtesy of JAY ALAN REAL ESTATE

$310,000

3 Beds ⋅ 2 Baths ⋅ B4902406 MLS

Welcome to this beautifully maintained 3-bedroom, 2-bathroom home nestled in a the quiet East Summit neighborhood. Thoughtfully updated and move-in ready, this property offers both comfort and style with a spacious, well-designed layout. The private primary suite features a generous bathroom complete with a relaxing soaking tub, separate walk-in shower, and dual vanity sinks. Throughout the home, you'll find attractive tile flooring that creates a seamless and modern feel. The kitchen is well-equipped with quality appliances and provides plenty of space for cooking and entertaining. Recent improvements add even more value and peace of mind, including a new roof installed in 2025, fresh interior paint, a freshly painted garage, a brand-new bathroom sink, updated light fixtures, and new AC vents throughout the home. Step outside to enjoy the fully fenced backyard, offering the perfect space for pets, outdoor gatherings, gardening, or simply unwinding in your own private retreat. Conveniently located near LEGOLAND Florida Resort, shopping, dining, schools, and major roadways, this home combines a peaceful residential setting with easy access to all that Winter Haven has. Don't miss this opportunity to own a beautifully updated home in one of Winter Haven's desirable, quiet neighborhoods. Schedule your private showing today!

7123 Summit Drive, Winter Haven

Courtesy of HOGAN & ASSOCIATES REAL ESTATE FIRM

$190,000

3 Beds ⋅ 2 Baths ⋅ TB8561823 MLS

Calling all real estate investors, flippers, and buy-and-hold landlords! This 3-bedroom, 2-bathroom single-family property offers approximately 1,630 square feet of living space.

2502 Sunset Shores, Winter Haven

Courtesy of PREMIER REALTY

$110,000

2 Beds ⋅ 1 Baths ⋅ O6451914 MLS

Short Sale. INVESTOR SPECIAL! Discover the potential of this cute home in beautiful Winter Haven! Located at 3393 Avenue J NW, this property offers an opportunity for buyers with vision to add their personal touch and bring out its charm. Known as the “Chain of Lakes City,” Winter Haven offers scenic lakes, boating, fishing, and outdoor recreation. Enjoy the area’s local restaurants, shops, parks, and vibrant downtown, along with popular attractions such as LEGOLAND Florida Resort. Explore the possibilities and make this your next project! This is a short sale and is subject to lender approval.

3393 Avenue J Nw, Winter Haven

Courtesy of PREFERRED REAL ESTATE BROKERS

$229,900

2 Beds ⋅ 2 Baths ⋅ P4940270 MLS ⋅ Na BLDG.

Enjoy Florida Living in this updated 2BR/2BA home located in the lakefront 55+ community on Lake Hartridge. Only 42 units in Hartridge Harbors condo situated on the beautiful Winter Haven Chain-of-Lakes. Well maintained complex with affordable HOA fees. This home features a 2 car garage, inside laundry, new appliances, Large master suite, and large guest room. Screened and private patio at the rear of the house affords space for outdoor kitchen, spa, or garden area. Location is ideal-close to shopping, restaurants, medical, etc. Community amenities include a clubhouse and pool while offering low maintenance living. Call today for your private showing.

2212 Starboard Unit 2212, Winter Haven

Courtesy of CENTURY 21 WATSON & MYERS REALTY

$149,900

2 Beds ⋅ 2 Baths ⋅ L4965947 MLS

INVESTOR’S DREAM IN SE WINTER HAVEN — This 2 bedroom, 2 bath block home offers a convenient location within walking distance of Publix, Walmart, restaurants and retail shopping. Features include a new roof in 2019, new HVAC in 2018, two remodeled bathrooms and a new water heater in 2025. These valuable improvements are already in place, while still in need of a few additional updates, this home offers an opportunity to make it your own. The open floor plan features a great room, dining room, an eat-in kitchen and a Florida room. The kitchen offers original wood cabinetry, an original built-in oven and a dinette space for casual dining. The dining area allows for a larger gathering for holidays and special occasions. The FL room provides additional flexible space and includes a newly constructed full bathroom with a tiled handicap accessible walk-in shower, along with a laundry space equipped with a stackable washer and dryer and a mini split A/C unit. The FL room can easily be converted into a third en-suite bedroom. There are two bedrooms of ample size and a secondary beautifully remodeled bathroom with a walk-in shower. Situated on a spacious 0.24-acre fenced lot, the property also offers central heart and air, a one-car carport, 2 storage sheds and rain gutters. Bring your vision and explore the potential of this conveniently located home!

1810 4th Court Se, Winter Haven

Courtesy of THE STONES REAL ESTATE FIRM

$250,000

2 Beds ⋅ 2 Baths ⋅ L4966038 MLS

**More PhotosComing** Comfortable, Simple Living in Cypress Landing on Lake Dexter. This 2 Bedroom, 2 Bath Home Has a Vaulted Ceiling Over the Living and Dining Area, and It Makes the Whole Space Feel Open the Minute You Walk In. The Kitchen Has Light-Bright Cabinets, Tile Floors, a Stainless Refrigerator and Dishwasher, a Built In Oven, Cooktop and Microwave, with Sliders Out to the Screened Lanai. The Primary Bedroom Has a Walk In Closet and a Walk In Shower in the Bath. Need More Room? The Enclosed Lanai Gives You Extra Space for a Den, Hobby Room or Home Office. Crown Molding and Ceiling Fans Throughout, a Two Car Attached Garage with Opener and Storage Cabinets, and a Fenced Backyard with Low Maintenance Rock Landscaping. Home Electrical is Generator Ready. The Home Includes Hurricane Shutters - Easy Up And Down Installation. Cypress Landing Offers a Clubhouse, Community Pool, Tennis and Pickleball Courts, Boat Storage, a Private Boat Ramp and a Dock on the Lake. Minutes from Legoland, Shopping and Dining. Schedule Your Showing Today! All Sizes Approximate. Buyer to Verify.

3969 Cypress Landing W, Winter Haven

Courtesy of KELLER WILLIAMS REALTY SMART 1

$320,990

4 Beds ⋅ 2 Baths ⋅ O6452454 MLS

Under Construction. Introducing the Cali floorplan at Willowbrook South, in Winter Haven, Florida, where every square foot is put to use with sophistication and comfort. Inside this 4-bedroom, 2-bathroom home, you’ll find 1,828 square feet of comfortable living. This meticulously designed residence combines modern convenience with timeless elegance, showcasing quartz counters and tile floors throughout. As you step inside, you are greeted by an inviting foyer that leads you into the heart of the home. The open-concept layout seamlessly connects the living room, dining area, and kitchen, creating a perfect space for entertaining family and friends. The spacious living room features abundant natural light, thanks to large windows that provide picturesque views of the surrounding landscape. With ample room for seating, it's an ideal spot for relaxation and gatherings. The kitchen is a true highlight, including granite countertops, sleek stainless-steel appliances, a walk-in pantry and an oversized island with a breakfast bar. Whether you're preparing a casual meal or hosting a formal dinner, this kitchen is well-equipped to meet your culinary needs. The four generously sized bedrooms offer flexibility for various lifestyles. The primary suite located in the rear of the home is a tranquil retreat, featuring a private ensuite bathroom with dual sinks, a separate shower, and a walk-in closet. The remaining three bedrooms share one well-appointed bathroom, making morning routines a breeze. Laundry won't be a chore with its dedicated space convenient to all bedrooms. Like all homes in Willowbrook South, the Cali includes smart home technology, which allows you to control your home anytime with your smart device while near or away. Whether you're seeking a peaceful family retreat or a stylish place to call your own, this home is sure to meet your every need. *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.*

2766 Adeline Avenue, Winter Haven

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC

$285,000

3 Beds ⋅ 2 Baths ⋅ TB8559684 MLS ⋅ Meritage Homes BLDG.

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

Courtesy of MERITAGE HOMES OF FL REALTY

$279,000

4 Beds ⋅ 2 Baths ⋅ P4940110 MLS

4 BEDROOM, 2 BATH NEWER HOME WITH AFFORDABLE HOA, NO CDD AND PRICED TO SELL! Welcome to this clean, well-kept 2020 four-bedroom, two-bath home across from Lake Lucerne in Winter Haven. A brick-paver driveway leads to a two-car garage and a bright, open floor plan. The kitchen features a large island, abundant cabinetry, and all appliances included. Living and dining areas flow together for easy everyday living. The home has no carpeting only easy to care for ceramic tile and luxury vinyl flooring and a Split-bedroom layout that places three bedrooms on one side and a spacious primary suite with ensuite bath and walk-in closet on the other. HOA is only $360 a year with NO CDD. Move-in ready in a convenient neighborhood with NO REAR NEIGHBOR, close to town, around the corner from Willowbrook golf course, shopping, medical and local eateries.

1339 Lucerne Loop Road Ne, Winter Haven

Courtesy of BETTER HOMES AND GARDENS REAL ESTATE LIFESTYLES REALTY

$560,000

4 Beds ⋅ 3 Baths ⋅ P4939998 MLS

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

Courtesy of COLDWELL BANKER REALTY

$344,990

4 Beds ⋅ 3 Baths ⋅ O6452648 MLS

Under Construction. Beautiful 2 Level, 2 Car Garage Home with Open Concept Living, Loft and 4 Bedrooms! The inviting front porch opens to a gracious foyer with adjacent powder room. The well-appointed, island kitchen is open to the adjoining cafe and spacious family room. The primary suite boasts an ensuite bathroom with dual sink vanity, shower, private water closet, and large walk-in closet. The 2nd level offers a spacious loft, 3 secondary bedrooms, each with walk-in closets, a full bathroom and a convenient laundry room.

353 Meredith Boulevard, Winter Haven

Courtesy of DRB GROUP REALTY, LLC

$2,000,000

5 Beds ⋅ 5 Baths ⋅ L4966009 MLS

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

Courtesy of COLDWELL BANKER REALTY

$364,990

3 Beds ⋅ 3 Baths ⋅ S5160167 MLS

STYLE, COMFORT, AND SMART LIVING COME TOGETHER IN THIS WINTER HAVEN HOME! Discover this elegant 3-bedroom, 2.5-bath residence in Lake Smart Pointe, where inviting spaces and practical features create an opportunity for first-time buyers and investors alike. An open layout seamlessly connects the kitchen, dining, and living areas—perfect for hosting guests or enjoying a relaxing evening at home. The kitchen’s spacious center island creates a natural gathering place, while the upstairs loft offers flexible space for a home office, media room, or additional lounge. A private primary suite with a walk-in closet and a two-car garage add everyday comfort and convenience. Adding to its appeal, the SOLAR PANELS WILL BE PAID OFF AT CLOSING, offering potential electric-bill savings without assuming the seller’s solar loan. Enjoy Winter Haven’s signature lifestyle with boating and fishing on the Chain of Lakes, local dining, shopping, parks, and downtown entertainment. LEGOLAND Florida Resort offers another way to enjoy the area, while access to US-27 and I-4 connects you to destinations throughout Central Florida. Whether you’re ready to step into homeownership or expand your investment portfolio, this home deserves a closer look. Schedule your private showing today!

588 Lake Smart Boulevard, Winter Haven

Courtesy of CENTURY 21 NEXT LEVEL REALTY

$285,000

3 Beds ⋅ 2 Baths ⋅ S5160128 MLS

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

Courtesy of RE/MAX HERITAGE PROFESSIONALS

$419,900

3 Beds ⋅ 2 Baths ⋅ L4965020 MLS

Beautiful New Construction with Detached Mother-In-Law Suite/ADU! Discover the perfect blend of modern living, privacy, and versatility in this beautiful new-construction property featuring a spacious 3-bedroom, 2-bathroom main home PLUS a detached 1-bedroom, 1-bathroom mother-in-law suite/ADU. The detached residence has its own separate entrance and separate address, offering exceptional flexibility for extended family, guests, a private home office, or potential rental opportunities. The main home welcomes you with a fresh, modern design and an open, versatile layout created for today’s lifestyle. The spacious living areas provide plenty of room to relax, entertain, and personalize the home to fit your needs. The well-appointed kitchen flows naturally into the living and dining areas, creating a comfortable space for everyday living and gatherings. The detached 1-bedroom, 1-bathroom suite provides a living arrangement with added privacy and convenience. Whether you envision a comfortable space for family members, a guest retreat, a dedicated workspace, or an income-producing opportunity, this additional residence adds tremendous value and versatility. With two separate living spaces, separate entrances, and separate addresses, this property is an exceptional opportunity for multi-generational living, hosting guests, or an investment-minded buyer seeking flexibility and additional potential. A unique property offering the space, privacy, and possibilities that are hard to find in new construction!

1855 Avenue P Sw, Winter Haven

Courtesy of COLDWELL BANKER REALTY

$350,000

4 Beds ⋅ 2 Baths ⋅ L4965381 MLS

Welcome to this spacious 4-bedroom, 2-bathroom home nestled in a desirable gated community. Situated on a large lot, this home offers over 2,000 square feet of comfortable living space, providing plenty of room for both everyday living and entertaining. The private owner’s suite offers a relaxing retreat, complete with an ensuite bathroom featuring a separate tub and shower and walk in closets. The open-concept kitchen flows seamlessly into the great room, creating a welcoming space where the cook can stay connected with family and guests. The other bedrooms are spacious and one room can be used as office/den. This home also has a separate formal dining room not seen in newer model homes. This home does have owner owned solar panels ( free and clear ownership) offering instant savings on electricity bills. With generous living areas, a spacious lot, and a thoughtfully designed floor plan, this home offers comfort, privacy, and functionality in a beautiful community setting. This community is located in the USDA zoned area for down payment assists.

1859 Galloway Terrace, Winter Haven

Courtesy of LA ROSA REALTY PRESTIGE

$279,900

3 Beds ⋅ 2 Baths ⋅ L4966012 MLS

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

Courtesy of CENTURY 21 WATSON & MYERS REALTY

$475,000

4 Beds ⋅ 3 Baths ⋅ P4940256 MLS

CYPRESSWOOD MASTERPIECE!!! This breathtaking 4BR/2.5BA residence sits across from a tranquil pond & Cypresswood's sprawling par 5 15th hole. Enjoy the view from your large covered front porch at the end of your quiet cul-de-sac. Offering nearly 2300SqFt of living area and almost 3500SqFt under roof, updates and upgrades are found throughout this gorgeous property. Features include: large downstairs primary suite with fully renovated bath and generous walk-in closet, expansive island in kitchen, under counter, microwave, custom cabinetry, solid surface floors downstairs, granite countertops, upstairs and downstairs laundry hook-up, stainless appliances, pot filler on range, fireplace, downstairs half bath, bonus room upstairs, ample closet space, large screened rear patio, paver fire pit and outdoor patio, mature landscaping, 2 car side load garage, and the list goes on!!! Community features a 24hr Guarded and Gated entrance, golf, pool, tennis, pickleball, clubhouse, restaurant!!! Right off HWY 27 and close to medical, shopping, dining, and Legoland. This property and this community are both wonderful places to call home....

70 Greenfield Court, Winter Haven

Courtesy of THE K TEAM REAL ESTATE SERVICES LLC

$575,000

4 Beds ⋅ 4 Baths ⋅ P4940249 MLS

GORGEOUS SOUTHEAST WINTER HAVEN POOL HOME ON .83 ACRE LAKEFRONT LOT ON RIVER LAKE.

4103 Shoal Green Court, Winter Haven

Courtesy of THE K TEAM REAL ESTATE SERVICES LLC

$223,000

2 Beds ⋅ 2 Baths ⋅ P4940235 MLS

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

Courtesy of CENTURY 21 MYERS REALTY LAKE WALES

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