Winter Haven Homes For Sale & Real Estate - 982 homes

Remarks: Welcome Home To This Spacious 3-Bedroom, 2-Bathroom Residence Featuring An Open-Concept Floor Plan Built For Florida Living. Recently Refurbished With Fresh Interior And Exterior Paint And Luxury Vinyl Flooring Throughout, Modern Custom Kitchen Cabinets With Granite Counter Tops. This Home Is Move-In Ready From Day One. The Expansive Living/Dining Room Combo Flows Into A Well-Appointed Kitchen, Anchored By A Dramatic Full Brick Fireplace Wall That Adds Warmth And Character You Rarely Find At This Price Point. A Utility Room Is Conveniently Located Between The Kitchen And Garage, Perfect For Daily Function. The Primary Suite Is A True Retreat, Positioned With Direct Access To A Dedicated Office/Nursery Flex Space And A True Interior Florida Room Filled With Windows And Natural Light, Creating A Connected Rear Wing That Adapts To However You Live. Two Additional Bedrooms Share A Full Secondary Bath, And The Attached 2-Car Garage With Concrete Side Patio Rounds Out A Home Built For Real Life. The Home; Situated Just Steps From The Amenities Of Cypress Landing On Lake Dexter — A Peaceful Lakeside Community Offering Pickleball And Tennis Courts, Boat Storage, A Private Boat Ramp, Dock, Community Pool, And Clubhouse. Located Just 1.8 Mile From Legoland Florida, Nestled Between Orlando And Tampa With Easy Access To Theme Parks And Beaches, And Just Minutes From 5 Star Rated Dining And Shopping In Downtown Winter Haven And Other Nearby Cities.

Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)

Listing Agent: Patrick Thurmond (863-450-8847)

Remarks: Rent-to-Own Opportunity! Experience easy Florida living with serene lake views right from the front of this charming home. Bright and welcoming, the home is filled with natural light and features a comfortable, functional layout designed for both everyday living and effortless entertaining. The thoughtfully planned interior offers low-maintenance living without sacrificing comfort or style. A standout feature is the fully fenced yard, providing privacy and versatility—perfect for pets, outdoor gatherings, gardening, or creating your own personal retreat. Combined with the tranquil water views, the outdoor space offers a peaceful and inviting setting. Ideal for first-time buyers, downsizers, seasonal residents, or investors, this property blends charm, flexibility, and scenic surroundings—along with a unique path to ownership in one of Central Florida’s most desirable areas.

Listing is courtesy of: IAD FLORIDA LLC (407-720-0020)

Listing Agent: Catherine Torres (863-632-4177)

Remarks: Under Construction. Under Construction. Welcome to the Residences at Winter Haven, a new single-family community designed for those who value both quality and connection. The Key West floor plan offers a functional, open-concept design that prioritizes modern convenience and high-end finishes. The layout includes a dedicated formal dining room and a kitchen anchored by a full waterfall countertop island. This 3-bedroom, 2-bathroom residence is equipped with a smart home package and a dedicated laundry room. The estimated completion date is at the end of June.

Listing is courtesy of: KELLER WILLIAMS REALTY AT THE LAKES (407-566-1800)

Listing Agent: Rodrigo Gomes De Almeida (407-837-8173)

Remarks: Under Construction. Under Construction. Welcome to the Residences at Winter Haven, a new single-family community designed for those who value both quality and connection. This Key West model floor plan features a functional 4-bedroom, open-concept layout centered around a kitchen with a full waterfall countertop island. The home includes a covered lanai for outdoor living, a dedicated laundry room, and a smart home package.The estimated completion date is at the end of June.

Listing is courtesy of: KELLER WILLIAMS REALTY AT THE LAKES (407-566-1800)

Listing Agent: Rodrigo Gomes De Almeida (407-837-8173)

Remarks: BACK ON THE MARKET! PRICE CHANGE – NO HOA & PRICED TO SELL! Opportunity meets value in this 3-bedroom, 2-bath home located in a well-established Winter Haven neighborhood. Positioned on a spacious, fully fenced corner lot, this property offers exceptional outdoor space and includes an above-ground pool, perfect for cooling off on hot Florida days, entertaining guests, or enjoying your own private backyard retreat. Inside, you’ll find a functional, comfortable layout with great natural light and flexible living space. This home presents an excellent opportunity for buyers looking to add personal style, build equity, or secure a solid investment property in a growing area. Whether you’re a first-time buyer, downsizing, or expanding your investment portfolio, this home offers strong potential, location convenience, and everyday livability. Ideally located near shopping, dining, Downtown Winter Haven, and the Polk Parkway, with easy access to both Orlando and Tampa for commuting or weekend travel. If you’re looking for space, flexibility, and long-term value with NO HOA restrictions, this is one you don’t want to miss. Schedule your private showing today and explore the possibilities.

Listing is courtesy of: SIGNATURE INTERNATIONAL REAL E (561-404-7263)

Listing Agent: Barbi Rodriguez, Llc (352-404-2377)

Remarks: ** Back to market and reviewing multiple offers: submit all offers by Monday 5:00 pm 5/25/26** Spacious 3-bedroom, 2-bathroom home in Winter Haven priced to sell! This fixer-upper is perfect for investors, flippers, FHA 203(k) buyers, or first-time homeowners looking to build instant equity. With 2,182 sq ft of living space on an 8,442 sq ft lot, this property offers plenty of room for cosmetic and structural improvements. Priced well below market, buyers can capitalize on a significant value-add opportunity in a growing neighborhood. Renovate to create your dream home, or take advantage of strong resale and rental potential.

Listing is courtesy of: KELLER WILLIAMS REALTY SMART (863-577-1234)

Listing Agent: Daryl Ash, Ii (863-934-1548)

Remarks: Welcome to this beautifully reimagined 4-bedroom, 2-bathroom pool home, perfectly positioned on a premium corner lot. Thoughtfully updated with a new roof (2021), HVAC (2024), and fresh interior paint throughout—including ceilings and the pool deck—this residence offers effortless, move-in-ready living. Inside, a refined layout unfolds with a formal dining space and a flexible bonus room, ideal for a private office or curated living area. The heart of the home showcases an open-concept design, where the living room flows seamlessly into a sophisticated kitchen and breakfast space, perfect for both intimate gatherings and entertaining. The kitchen is appointed with quartz countertops, high-end appliances, a built-in bar fridge, and a convenient pot filler, blending style with function. A desirable three-way split floor plan ensures privacy and comfort throughout. Outdoors, enjoy a screened-in patio overlooking a sparkling pool, complemented by a generously sized, fully fenced backyard, your own private retreat designed for the Florida lifestyle. Experience the perfect blend of modern upgrades and timeless comfort. Schedule your private showing today!

Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)

Listing Agent: Kevin Asenjo (407-844-5252)

Remarks: RUDUCED PRICE! MOTIVATED SELLERS Charming 4-Bedroom Lakefront Home on Lake Thomas – No HOA Discover the perfect blend of comfortable family living and relaxed lakefront lifestyle in this beautiful 4-bedroom, 2-bath home on Lake Thomas. Offering a spacious layout, generous outdoor space, and scenic water access, this property delivers both everyday functionality and waterfront charm. Step inside to find tile flooring throughout the main living areas and an open-concept design that seamlessly connects the living and dining spaces — ideal for family gatherings and entertaining guests. Ceiling fans throughout the home enhance comfort year-round. Outdoors, enjoy an oversized, level backyard that’s fully fenced — perfect for pets, outdoor dining, gardening, or play. Whether you're relaxing by the water or hosting weekend barbecues, this home offers space and flexibility to fit your lifestyle. Located in Winter Haven, you’ll appreciate convenient access to local amenities, shopping, dining, and recreational opportunities — all without the burden of HOA restrictions. Lake living, space to grow, and freedom to enjoy — this one has it all.

Listing is courtesy of: CENTURY 21 WOLF'S CROSSING REALTY (407-449-0000)

Listing Agent: Lucy Martinez (863-521-4156)

Remarks: Welcome to 292 Krenson Bay Loop, a 2024-built block home located in a gated Winter Haven community with NO CDD! This 4-bedroom, 2-bath home offers 1,820 square feet of living space, a 2-car garage, irrigation system, and a desirable split floor plan designed for comfort and functionality. Inside, you’ll find tile throughout the main living areas and kitchen, with carpet in the bedrooms. The modern kitchen features stainless steel appliances, subway tile backsplash, a large pantry, and an oversized peninsula with bar seating, opening nicely to the breakfast nook and main living area. A formal dining room provides additional space for gatherings or flexible use. The primary suite includes a walk-in closet and private bath with dual sinks, a garden tub, and a separate shower. Enjoy Florida living from the covered lanai, perfect for relaxing outdoors. Located in Winter Haven, this home offers convenient access to local lakes, shopping, dining, medical facilities, and nearby attractions including LEGOLAND Florida Resort. With easy routes to Lakeland, Tampa, and Orlando, this location provides a great balance of Central Florida living and regional convenience.

Listing is courtesy of: KELLER WILLIAMS REALTY SMART (863-577-1234)

Listing Agent: Garrett Robinson (863-838-5210)

Remarks: Under Construction. The main floor of the inviting Ammolite plan offers a private study and versatile flex space, which can be optioned as an additional bedroom and bathroom or a guest suite, complete with living room. You’ll also appreciate a convenient powder room; a nook; a great room and a well-appointed kitchen with a center island, a large pantry and optional additional cabinets. Upstairs, discover an airy loft, a convenient laundry, three secondary bedrooms and a lavish primary suite boasting an expansive walk-in closet and a private bath. This plan also features a patio and a 2-car garage. Make it uniquely your own by adding a bedroom in lieu of the loft, extending one of the secondary bedrooms and opting for an alternate kitchen layout and a covered patio. SAMPLE PHOTOS. Actual homes as constructed may not contain the features and layouts depicted and may vary from image(s). Take advantage of special financing on quick move-in homes OR buy a to-be-built home and enjoy up to $20,000 in Flex Funds toward homes that can close in a timely manner! Options may vary by community, and offers are available on select homes on a first-come, first-served basis. Contact builder for more information!

Listing is courtesy of: AXEN REALTY, LLC (480-399-1218)

Listing Agent: Stephanie Morales, Llc (407-399-2055)

Remarks: Under Construction. The main floor of the inviting Ammolite plan offers a private study and versatile flex space, which can be optioned as an additional bedroom and bathroom or a guest suite, complete with living room. You’ll also appreciate a convenient powder room; a nook; a great room and a well-appointed kitchen with a center island, a large pantry and optional additional cabinets. Upstairs, discover an airy loft, a convenient laundry, three secondary bedrooms and a lavish primary suite boasting an expansive walk-in closet and a private bath. This plan also features a patio and a 2-car garage. Make it uniquely your own by adding a bedroom in lieu of the loft, extending one of the secondary bedrooms and opting for an alternate kitchen layout and a covered patio. SAMPLE PHOTOS. Actual homes as constructed may not contain the features and layouts depicted and may vary from image(s). Take advantage of special financing on quick move-in homes OR buy a to-be-built home and enjoy up to $20,000 in Flex Funds toward homes that can close in a timely manner! Options may vary by community, and offers are available on select homes on a first-come, first-served basis. Contact builder for more information!

Listing is courtesy of: AXEN REALTY, LLC (480-399-1218)

Listing Agent: Stephanie Morales, Llc (407-399-2055)

Remarks: 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.

Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)

Listing Agent: David Small (407-601-8351)

Remarks: Discover this charming first-floor corner unit condo in the highly sought after Orchid Springs community in SE WInter Haven. This 2 bedroom 2 bathroom condo features a desirable split floor plan with an oversized living area perfect for entertaining or relaxing. Both bedrooms boast generous walk-in closets , and offers abundant storage throughout. Enjoy the convenience of a first floor corner location with a covered parking spot. The nice open layout makes every day maintenance free living easy and comfortable. Residents of Orchid Springs love the prime location minutes from shopping,dining, medical facilities, and Legoland, while being centrally situated between Tampa and Orlando for easy access to everything Central Florida has to provide. The HOA takes care of the details including grounds maintenance, water , sewer and gas giving you more time to enjoy the Florida Lifestyle. Whether you are looking for a primary residence or a winter retreat , this first floor corner unit is a fantastic opportunity in a desirable community. Schedule your showing today and make this condo your new home!

Listing is courtesy of: ALLSTATE REALTY SERVICES (863-965-0207)

Listing Agent: Rosalia Abreu (954-854-3694)

Remarks: Under Construction. New construction home with 2005 square feet on one-story including 3 bedrooms plus a den, 2 baths, and an open living area. Enjoy an open kitchen with Silestone countertops, Samsung stainless steel appliances, a walk-in pantry, and a spacious island, fully open to the dining café and gathering room. The living area, laundry room, and baths include luxury wood vinyl plank flooring, with stain-resistant carpet in the bedrooms. Your owner's suite is complete with a walk-in wardrobe and a private en-suite bath with dual vanities, a tiled shower, and a closeted toilet. Plus, enjoy a covered lanai, 2-car garage, custom-fit window blinds, architectural shingles, energy-efficient insulation and windows, and a full builder warranty. ***Please note - Virtual Tour showcases the home layout; colors and design options in actual home for sale may differ. Furnishings and décor do not convey!

Listing is courtesy of: CAMBRIDGE REALTY OF CENTRAL FL (863-797-4999)

Listing Agent: George Lindsey, Iii (863-797-4999)

Remarks: Stunning 2 story 3 bath Spanish home with attention to details. This home has been renovated, roof was complete in 2019, painted inside and out in 2020, new A/C in 2023, electric and plumbing and the sprinkler system in 2023. Upon entering into the family room, you will immediately notice the vaulted beam ceilng along with the 20foot high fireplace. There are built-ins and bookcases throughout the home. Walking up into the kitchen, there is granite throughout and stainless steel appliances, along with a breakfast nook. There is a beautiful flooring throughout the home. On the first floor, there is another sitting room,along with a bedroom and a additional renovated full bath. On the second floor, it provides the laundry room and two more bedrooms and two full bathrooms that have been tastefully renovated. Going outside, there is convered area where you can relax and the property is completely fenced in. Another great feature is a detached studio that has been

Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)

Listing Agent: Joni Reiter (863-287-8274)

Remarks: Ready for immediate move-in, the three bedroom, two bathroom home welcomes you with a perfect blend of style, comfort, and modern living. Thoughtfully designed with an open-concept layout filled with natural light, creating an inviting space for both relaxing and entertaining. At the heart of the home, the spacious great room flows seamlessly into the dining area and kitchen. The gourmet kitchen is sure to impress, showcasing stainless steel appliances, breakfast bar for a casual meal, pantry and plenty of prep space—ideal for everyday living and hosting alike. Beautiful ceramic tile flooring extends through the main living areas, while the bedrooms offer plush carpeting for added comfort. The primary bedroom serves as a peaceful retreat, complete with a generous walk-in closet and en-suite bath featuring dual vanities and a shower with a bench. Two additional bedrooms provide flexibility for guests, or a home office, each offering ample closet space and convenient access to a full bath. A dedicated laundry room with washer and dryer, along with a two-car garage, adds everyday convenience. Step outside to the covered patio to enjoy your backyard. Enjoy the amenities offered in the community with a resort style pool, playground and dog park. Experience the perfect blend of style, convenience, and community living at VillaMar. Come experience a home where comfort, functionality, and beauty come together effortlessly.

Listing is courtesy of: RE/MAX ASSURED (800-393-8600)

Listing Agent: Vilmari Caraballo (407-583-9870)

Remarks: Pre-Construction. To be built. Discover a home where modern comfort meets effortless style in the beautiful VillaMar community of Winter Haven. Surrounded by scenic lake views and resort-style amenities, this is more than a place to live—it’s a place to truly enjoy life. The Ventura floor plan offers up to 1,562 square feet of thoughtfully designed living space with 4 bedrooms and 2 bathrooms. At the heart of the home, the open-concept layout creates a bright and welcoming atmosphere. The beautifully designed kitchen features a large island with quartz countertops—perfect for gathering, entertaining, or enjoying everyday meals. It flows seamlessly into the spacious great room, where natural light pours in through upgraded windows, creating a warm and airy feel throughout. Your private primary suite, located at the rear of the home, offers a peaceful retreat. Enjoy a spacious walk-in closet, dual sinks, and a walk-in shower designed for both relaxation and ease. There are three other bedrooms and a full bath are tucked away at the front of the home, creating a private and functional space. Built with today’s lifestyle in mind, The Ventura includes smart home features such as a Ring Video Doorbell, Smart Thermostat, Keyless Entry Door Lock, and customizable DEAKO light switches—giving you control and peace of mind at your fingertips. Enjoy the amenities offered in the community with a resort style pool, playground and dog park. Experience the perfect blend of style, convenience, and community living at VillaMar. Your future home is waiting—make The Ventura your own and start creating lasting memories.

Listing is courtesy of: RE/MAX ASSURED (800-393-8600)

Listing Agent: Vilmari Caraballo (407-583-9870)

Remarks: Stunning BRAND NEW two story home offer 4 bedroom, three bathrooms and loft in the Villamar community. No need to wait and build as this home is move in ready, now. From the moment you step inside, you’re greeted by a spacious foyer that flows effortlessly into the open-concept living areas. The main floor features upgraded tile flooring throughout, creating a clean, cohesive, and inviting space. At the heart of the home, the chef-inspired kitchen is designed to impress, showcasing stainless steel appliances, quartz countertops, and a side-by-side refrigerator. It opens seamlessly to the dining area and great room, making it perfect for both relaxed daily living and entertaining with ease. A convenient fourth bedroom and full bath on this level provide flexibility—ideal for guests or home office. Upstairs, a generous loft offers a versatile space for a media room, play area, or quiet retreat. The thoughtfully placed laundry room—complete with washer and dryer—is conveniently located near the secondary bedrooms. A full bath with a shower/tub combo serves this level with ease. The primary suite is your own private sanctuary, featuring a spa-like en-suite bath and an oversized walk-in closet designed for ultimate comfort and convenience. Enjoy the added benefits of modern Smart Home features, including a Ring Video Doorbell, Smart Thermostat, Keyless Entry Smart Door Lock, and DEAKO Switches—bringing both security and simplicity to your daily life. Head outside to find an open patio to lounge and enjoy the backyard. Take advantage of the community amenities inducing sparkling resort-style pool and playground. Don't miss your chance to make this home yours - reach out today for more details or to arrange a visit.

Listing is courtesy of: RE/MAX ASSURED (800-393-8600)

Listing Agent: Vilmari Caraballo (407-583-9870)

Remarks: Situated on nearly half an acre in a quiet cul-de-sac with NO HOA, this 3-bedroom, 2-bath home offers space, flexibility, and room to make it your own. Featuring a functional layout, 1-car garage, and extended driveway with ample parking, this property provides versatility for homeowners, first-time buyers, or those seeking an investment opportunity. Recent updates include a NEW ROOF (2026), NEW INTERIOR & EXTERIOR PAINT (2026), and a newer HVAC system, offering a strong starting point for future personalization. There are currently no rear neighbors immediately behind the property, providing additional separation from surrounding homes. Whether you're searching for a primary residence or investment property, this home presents an opportunity to blend comfortable day-one living with cosmetic updates over time to match your style and needs. This property offers space, flexibility, and everyday convenience with access to shopping, dining, recreation, and the amenities that continue to make Winter Haven a growing Central Florida destination. Schedule your private showing today.

Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)

Listing Agent: Ruben Galindo Vega (863-307-5009)

Remarks: Discover the best of retirement living in Brookhaven, a welcoming 55+ community! This partially furnished and well-maintained home sits on a desirable lot with OWNED LAND, offering a peaceful and private retreat.Featuring 1,596 sq. ft. of living space, this home boasts a spacious open-concept layout with 2 bedrooms and 2 bathrooms. Recent updates include a new shingle roof (2024), new A/C unit (2025), and hot water heater (2023). The kitchen offers ample counter space and cabinetry, perfect for everyday living and entertaining.Enjoy plenty of storage throughout, along with sliding doors that lead to the porch—ideal for relaxing or hosting guests. The guest bedroom and bathroom are generously sized, while the oversized primary suite features a private ensuite bath complete with a double-sink vanity, garden tub, and walk-in shower.The laundry area is conveniently located in the spacious workshop and includes a washer, dryer, and utility sink. This home also features two porches—one screened and one enclosed—providing additional living space to enjoy year-round.Surrounded by mature landscaping, the property offers both charm and tranquility. Additional perks include an irrigation system and lawn maintenance already paid through February. This home has recently had a 4-point inspection.Brookhaven residents enjoy fantastic amenities including a pool, clubhouse, and shuffleboard—all with a low HOA fee of just $34 per month. Conveniently located near Hwy 27, shopping, medical facilities, and restaurants, you’re also just about an hour from Disney and 1.5–2 hours from both Florida coasts.Don’t miss your opportunity to own this beautiful home at 6561 Chinaberry Dr NE — schedule your private showing today!

Listing is courtesy of: CROSBY & ASSOCIATES, INC. (863-293-5600)

Listing Agent: Corinna Weaver (863-258-2901)