Winter Haven Real Estate

Winter Haven Real Estate

Welcome to Winter Haven, Florida – a hidden gem nestled in the heart of Polk County, where charm meets opportunity! Known for its picturesque lakes and vibrant community, Winter Haven is the ideal place for those seeking a blend of relaxation and adventure.

With over 50 sparkling lakes, Winter Haven is often referred to as the "Chain of Lakes," making it a paradise for water enthusiasts. Whether you enjoy fishing, boating, or simply basking in the sun, these serene waters offer endless recreational opportunities. The city is also home to the popular LEGOLAND Florida Resort, attracting families and thrill-seekers from all over the state.

Winter Haven boasts a rich history that dates back to the late 1800s, reflected in its beautiful historic downtown area, where charming boutiques, local eateries, and vibrant art galleries beckon visitors and residents alike. The annual events, like the Winter Haven Water Ski Show and the Blueberry Festival, bring the community together, celebrating the unique culture and spirit of this delightful city.

In addition to its recreational and cultural offerings, Winter Haven is conveniently located between Orlando and Tampa, providing easy access to major highways, shopping centers, and airport hubs. This strategic location makes it an attractive option for commuters and those looking to enjoy the best of Central Florida living.

With a warm climate, friendly neighborhoods, and a variety of housing options, Winter Haven is not just a place to live; it’s a place to thrive. Come discover why this charming city is the perfect backdrop for your next chapter!

Newest Listings in Winter Haven

3 Beds ⋅ 2 Baths ⋅ S5155533 MLS

IMMACULATE FULLY REMODELED AND COZY 3 Bedroom AND 2 bathroom house. This home can be used as your primary residence or as investment Rental property. This lovely home has tons of curb appeal with easy to maintain landscaping. House was just painted inside and outside, New water heater, New ceiling, New bathrooms, New flooring, New light fixtures, Roof was replaced in 2022, New Garage door and Garage door opener, New Split system A/C, New outlets and switches and much much more! Kitchen was fully updates with new Wood cabinets and Quartz countertop. This wonderful home is completely ready to Move IN!!

Winter Haven

3 Beds ⋅ 2 Baths ⋅ P4939647 MLS

CUSTOM BUILT HOME WITH HEATED POOL IN LAKE MARIAM HILLS!!! This 3BR/2BA residence is situated on a quiet cul-de-sac in established and gated Lake Mariam Hills. Custom features are found throughout the split floorplan with its open and spacious feel. Large archways, columns, towering vaulted ceilings, custom accent windows, French doors and more are examples of the home's craftmanship and attention to detail. The kitchen is spacious, with a breakfast bar, an eat-in area, custom cabinetry, ample counter space and a great pool view. There are also formal living and dining areas, a comfortable living space with French doors opening onto the covered lanai, pool and screen enclosed patio!!! The pool is salt water, has a lovely water feature and feels secluded behind the mature landscaping and privacy fence. The Master Suite is a great place to relax and offers a custom tile shower and a separate garden tub, dual sinks, large walk-in closet, linen closet and French doors opening to the pool area. Many more features include a whole house generator, an oversize two car garage, extended driveway for additional parking, lush, mature landscaping, architectural shingle roof, in-wall pest defense, some tinted windows for efficiency, upgraded insulation and more. A gorgeous custom pool home in one of Winter Haven's most established gated communities, call today to see this exceptional home!

102 Hillside Court, Winter Haven

3 Beds ⋅ 2 Baths ⋅ L4964392 MLS

6.36 ACRES, NO HOA, GATED ENTRY & 3-CAR GARAGE/WORKSHOP! Enjoy country living without sacrificing convenience! This spacious 3-bedroom, 2-bath home with a flex/bonus room sits on 6.36 acres with NO HOA, offering privacy, freedom and room to spread out. Inside, LVP flooring flows throughout the bright, open-concept floor plan. The oversized living room opens to the updated kitchen and dining area, creating an inviting space for everyday living and entertaining. The kitchen features an abundance of cabinetry and counter space. The spacious primary suite offers a comfortable retreat, while generously sized guest bedrooms provide excellent storage, including walk-in closets. The laundry area includes the washer and dryer, and the home also features a tankless water heater and whole-house water treatment system. Outside, a keypad-entry gate provides added privacy, while the expansive screened patio is perfect for relaxing or entertaining. The impressive 24x32 3-car garage/workshop offers plenty of room for vehicles, recreational equipment, storage or your dream workshop. ROOF REPLACED 2022 Conveniently located near the Polk Parkway between Winter Haven and Lakeland, with easy access to shopping, dining and everyday necessities. Come experience the space, freedom and possibilities this property offers!

5230 Thornhill Road, Winter Haven

5 Beds ⋅ 4 Baths ⋅ O6435590 MLS

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

5604 Royal Hills Drive, Winter Haven

5 Beds ⋅ 4 Baths ⋅ O6435502 MLS

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

25 Lakewood Causeway, Winter Haven

3 Beds ⋅ 2 Baths ⋅ L4964346 MLS

Built in 2023 and situated on 1.59 acres, this 3 bedroom, 2 bath home offers something increasingly hard to find in Winter Haven: a newer home with land, flexibility and NO HOA. Nearly 200 feet of street visibility along Hwy 540 creates a unique opportunity for a small business owner who understands the value of exposure. Imagine the visibility your brand could capture simply by parking your wrapped work vehicle along the road frontage while coming home to your own private retreat. Inside, the split floor plan offers an open and functional layout centered around a spacious kitchen with quartz countertops, a large island and plenty of room for gathering. A newly added statement fireplace wall gives the living area a custom finished feel. The home also features a whole home water filtration system and a dedicated internet line from the provider, ideal for working from home, streaming and staying connected. Large covered front and back porches extend the living space outdoors, while the side entry garage adds to the home's beautiful curb appeal and keeps the front elevation clean and inviting. With 1.59 acres and no HOA, there is plenty of room for boats, RVs, additional vehicles, outdoor toys, trailers or work equipment. The expansive property also offers space to explore future possibilities such as a guest house, mother in law suite or additional dwelling, subject to applicable zoning and permitting. Conveniently located with easy access to major roadways, this property combines accessibility with the freedom and breathing room of acreage. Whether you're looking for space for your family, your toys, your work equipment or simply a little more freedom, 795 Crosstower Drive offers possibilities you won't find in a typical neighborhood.

795 Crosstower Drive, Winter Haven

5 Beds ⋅ 4 Baths ⋅ O6435392 MLS

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

4162 Roberta Drive, Winter Haven

2 Beds ⋅ 2 Baths ⋅ P4939656 MLS

UPDATED 2 BEDROOM 2 BATH HOME WITH POND VIEW Welcome to the beautifully updated home in active 55+ community of Orange Manor West. This home offers peaceful views of neighborhood pond. Modern upgrades throughout this home offers comfortable Florida living. The thoughtful updated interior provides a fresh, modern feel, while the scenic pond view adds a tranquil backdrop. Orange Manor West is an active community with a variety of activities and social opportunities. NO PETS. ONLY SERVICE AND EMOTIONAL ANIMALS.

86 Parson Drive, Winter Haven

3 Beds ⋅ 4 Baths ⋅ B4902341 MLS

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

2241 Winterset Road, Winter Haven

4 Beds ⋅ 3 Baths ⋅ L4964316 MLS

Welcome to your own private lakefront retreat on 1.23 acres along Lake Hamilton with NO HOA! This stunning 4-bedroom, 3-bath home offers an exceptional combination of luxury, entertaining space, and the ultimate Florida waterfront lifestyle. Bring your boat and jet skis and enjoy the convenience of a private dock featuring an electric covered boat lift and built-in fishing bench. The outdoor living space is truly spectacular! Step through the French doors to a sparkling saltwater PebbleTec pool featuring iridescent tile, fiber-optic lighting, a swim-up bar, fountains, and a roof-line waterfall. The propane-heated pool is surrounded by an expansive travertine deck, while the nearby gas fire pit with custom-cushioned seating creates the perfect setting for evening gatherings. Propane-connected tiki torches add a tropical ambiance, and a hidden sump pump provides worry-free drainage after storms. Entertaining is effortless with the outdoor kitchen, complete with a new grill and refrigerated drawers. The fenced backyard extends halfway to the lake, providing plenty of room for pets to play. Professional Florida-native landscaping, enhances the lush, resort-like setting. Inside, the beautifully designed chef's kitchen features quartz countertops, a copper farmhouse sink, paneled refrigerator, trash compactor, and spacious butler's pantry with a full-size refrigerator and abundant storage. The open floor plan includes a dedicated buffet area with dual wine refrigerators adjacent to the dining space—perfect for hosting family and friends. Nine-foot ceilings, crown molding, porcelain tile, shiplap accents, custom lighting, and a central vacuum system add comfort and sophistication throughout. The luxurious primary suite offers direct access to the pool deck, with a convenient open-air shower just outside. The ensuite features dual vanities and a walk-in shower with dual shower heads. The expansive walk-in closet includes a center island, custom shelving, heated towel rack, and an extra-large Liberty Safe. The home underwent a complete rebuild in 2017, so all features are 2017 or newer. Recent improvements include a new roof (2025), new pool pump (2025), a new 12x24 storage shed (2025) and new irrigation system (2025). The irrigation water comes from the lake so it doesn’t affect your water bill. Additional features include a split-bedroom floor plan, with two guest bedrooms sharing a Jack-and-Jill bath; hurricane shutters; a whole-home Generac generator; and TVs in every room, including the back porch. The spacious 3-car garage features tiled flooring, storage, a workshop, and an industrial ice maker. A pavered circular driveway provides ample parking, plus an additional parking pad with room for an RV. From the custom interior and exterior lighting to the custom painting, bamboo chair rail, and travertine exterior accents, every detail has been thoughtfully designed. The home is also pre-wired for ADT security at the front and rear doors and garage service door. Boating, fishing, entertaining, relaxing, and resort-style living—all in one exceptional Lake Hamilton property with no HOA!

3640 Crump Road, Winter Haven

3 Beds ⋅ 2 Baths ⋅ S5155622 MLS

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

2802 Sunset Drive Nw, Winter Haven

4 Beds ⋅ 2 Baths ⋅ O6435475 MLS

Virtually Staged. This Winter Haven one-story home offers a two-car garage. Included 100-Day Home Warranty with buyer activation

313 Terranova Boulevard, Winter Haven

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