Winter Haven Homes For Sale & Real Estate - 995 homes

Remarks: Step inside this well-designed single-family home offering comfort, functionality, and a layout that truly makes sense. You’re welcomed by a screened front porch and a beautifully landscaped front yard, setting the tone before you even walk through the door. Inside, you’ll find engineered wood flooring throughout the main living areas with ceramic tile in both bathrooms. The living and dining rooms flow together in one open space, creating an easy layout for everyday living or entertaining. At the heart of the home sits the open kitchen, featuring granite countertops and a central location that keeps you connected to everything happening in the home. The split bedroom floorplan provides privacy, and the spacious primary suite includes a garden tub for unwinding at the end of the day. Enjoy added convenience with an inside laundry room located just off the kitchen as you enter from the two-car garage. The backyard has been thoughtfully designed with low-maintenance rock landscaping instead of grass and is framed by a vinyl privacy fence along both sides and across the back. Additional highlights include high ceilings, approximately 1,716 heated square feet, and about 2,400 square feet under roof—giving you plenty of room to spread out. A comfortable, well-kept home with smart updates and a layout that works for today’s lifestyle—this one is ready for its next chapter.

Listing is courtesy of: CRAIG BURKE REAL ESTATE GROUP, LLC (863-899-5010)

Listing Agent: Julie Sutphin (407-414-4024)

Remarks: Light and bright 2/2/1 in The Verandah's at Lake Reeves. The Verandahs offers a community pool and fishing dock on Lake Reeves. The low HOA fee includes ground maintenance, basic cable and internet, exterior painting and more. Easy access to shopping, Legoland, chain of lakes. Light and bright, move in ready. Dual master bedroom set up. Den/office off of main living area. Vaulted ceilings, large kitchen, open living plan.

Listing is courtesy of: FLATFEE.COM (954-965-3990)

Listing Agent: Cliff Glansen

Remarks: RESORT-STYLE FLORIDA LIVING IN HIGHLY DESIRED LAKE ASHTON! Welcome to your own slice of paradise, where comfort meets connection in one of Central Florida’s most sought-after 55+ communities. This beautifully maintained home offers an easygoing, laid-back lifestyle with soaring ceilings that create an open, breezy feel the moment you walk in—perfect for relaxing or entertaining. At the heart of the home is a fully enclosed and expanded Florida Room, complete with dedicated AC vents, giving you year-round comfort whether you’re enjoying a quiet morning coffee or hosting friends after a day on the course. Thoughtful design continues throughout, including extra-tall closets that provide impressive storage space—keeping everything organized without sacrificing style. BIG-TICKET UPDATE: Enjoy peace of mind with a brand new roof installed on 4/6/2026—a major upgrade already taken care of, with the rest of the home in excellent condition. LIVE THE RESORT LIFE EVERY DAY: Step outside and experience everything that makes Lake Ashton so special: • Health & Wellness: State-of-the-art fitness center, indoor walking track, sauna, plus multiple heated indoor & outdoor pools and spas. • Endless Recreation: Private movie theater, bowling alley, billiards room, and a grand ballroom with live entertainment. • Championship Sports: Two 18-hole golf courses, along with pickleball, tennis, and bocce ball courts. • Dining & Social Scene: Golf cart to the Eagles Nest restaurant, explore 100+ social clubs, or enjoy direct access to Lake Ashton via the community boat ramp. • Peace of Mind: 24-hour manned security and a golf-cart-friendly community. Whether you’re looking for a full-time residence or the perfect seasonal escape, this home delivers the best of Florida living—relaxed, social, and full of opportunity. Homes in this highly desired community don’t last long. Contact your realtor today to schedule your private showing!

Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (863-701-2350)

Listing Agent: Wes Fleming (863-666-4136)

Remarks: Under contract-accepting backup offers. Welcome home to this beautifully renovated 2-bedroom, 1.5-bath condo nestled in a peaceful 55+ community in the heart of Winter Haven. Completely move-in ready, this charming residence has been thoughtfully upgraded from top to bottom with over $50,000 in modern improvements designed for comfort, style, and easy living. Step inside to discover brand-new luxury vinyl plank flooring, a stunning fully remodeled kitchen featuring new appliances and sleek finishes, beautifully refreshed bathrooms, fresh interior and exterior paint, and a brand-new roof completed in 2025. Energy efficiency meets peace of mind with new double-pane windows backed by a lifetime warranty, new gutters, a recently serviced AC unit, and the added convenience of a covered carport. Imagine hosting friends in your stylish kitchen, savoring quiet mornings with coffee in the sun-filled living space, or enjoying relaxing afternoons in your private backyard — perfect for gardening, unwinding, or spending time with your furry companion. Perfectly positioned near everyday conveniences like Walmart and Publix, plus local shops and dining, this location truly puts everything within reach. Spend weekends exploring nearby favorites such as LEGOLAND Florida Resort, the historic Cypress Gardens, or enjoying craft brews at Port 27 Brewery. Outdoor enthusiasts will appreciate close proximity to scenic parks, golf courses, and the beautiful Winter Haven Chain of Lakes — ideal for waterfront dining, boating, and year-round recreation. Plus, exciting day trips and fine dining await within easy driving distance of Orlando and Tampa. Whether you’re searching for a seasonal retreat or a full-time residence, this home delivers the perfect blend of low-maintenance living, modern upgrades, and Central Florida charm. Schedule your private showing today and discover resort-style living at its finest!

Listing is courtesy of: CENTURY 21 MYERS REALTY (863-875-5656)

Listing Agent: Tony Acosta (863-224-5956)

Remarks: Under contract-accepting backup offers. Situated in the desirable gated community of Terranova, this wonderful 3-bedroom, 2-bath pool home with a den offers the perfect blend of comfort, luxury, and energy efficiency. Enjoy low utility costs thanks to the fully paid solar system, providing long-term savings and sustainability. Upon arrival, you are welcomed by a charming covered entry accented by a leaded-glass front door and an arched transom window that fills the foyer with natural light. The spacious great room features hand-scraped engineered wood flooring and a large sliding glass door that seamlessly blends indoor and outdoor living while offering picturesque views of the patio and pool area. The well-appointed kitchen showcases white cabinetry with brushed nickel hardware, beautifully complemented by a glass tile backsplash. The upgraded stainless steel appliance package includes a gas range, while the granite-topped breakfast bar with pendant lighting provides additional seating and serves as a natural gathering space. A formal dining room is conveniently located nearby, making entertaining effortless. The primary bedroom suite offers a walk-in closet and a cozy sitting niche, ideal for relaxing while enjoying tranquil views of the pool. The primary bathroom is thoughtfully designed with dual sinks, a linen closet, a walk-in shower, a private water closet, and a luxurious garden tub. Step outside to your own private outdoor oasis. The lagoon-style pool with a cascading waterfall creates a serene ambiance, while the covered patio provides shade from the Florida sun and convenient access to the guest bathroom—perfect for poolside gatherings. The fully fenced backyard offers privacy and features both avocado and citrus trees. Additional features include: ,Den/office, Laundry room with washer and dryer, Solid surface flooring throughout, Water heater (2020), Architectural shingle roof (2020), 18 SEER Carrier HVAC system with heat pump (2020) and warranty, In-wall pest control system, Pull-down attic stairs, Irrigation well, Smart lock entry, Child safety fence for the pool, Exterior carriage lighting, Oversized driveway, Two-car garage with door opener and keyless entry pad. This exceptional home is conveniently located in a picturesque gated community near schools, shopping, restaurants, and Legoland, offering the perfect combination of luxury, convenience, and energy efficiency.

Listing is courtesy of: CENTURY 21 MYERS REALTY LAKE WALES (863-676-4448)

Listing Agent: Eileen Belanger (863-221-0229)

Remarks: Welcome to your slice of true Florida lake life—where every day feels like a getaway. This 3-bedroom, 2-bath home is tucked inside a waterfront community designed for living, not just residing. Start your mornings with a quick launch from the private boat ramp, spend your afternoons cruising Lake Dexter, or enjoy a friendly match on the tennis courts. There’s even private boat parking, so your next day on the water is always effortless. When it’s time to unwind, head to the community pool or relax at the clubhouse overlooking the water—perfect for catching those signature Florida sunsets. Located just minutes from LEGOLAND Florida Resort, plus a wide variety of local restaurants and shopping, you’re right in the heart of everything—so close to LEGOLAND that you can sometimes enjoy their fireworks lighting up the night sky. This isn’t just a home—it’s the kind of place where memories are made and the pace of life finally feels just right.

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Kevin Tison (863-206-5755)

Remarks: This home offers, 9"4' ceilings and 8' doors, 42' cabinets, white quartz counter tops in kitchen, ceramic tile throughout the wet and main living areas of the home, all bedrooms, family room, and covered lanai are prewired for ceiling fans, secondary bedroom with its own bathroom. 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. 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. This upscale new Summit two-story townhome provides ample space to live and grow with a total of three bedrooms. The first level features a spacious and flexible open-concept layout shared between the kitchen and family room, maximizing the interior living space. Two secondary bedrooms and a lavish owner’s suite featuring a full bathroom comprise the second floor. Serenity at Peace Creek Reserve is a masterplan community of new townhomes with a beautiful natural creek. Winter Haven is the chain of lakes city, with over 26 linked together by a canal. There are lots of shops, restaurants, and bike paths. Peace Creek Reserve is what you have been looking for. A safe small town feel with convenience, the perfect place to raise a family.

Listing is courtesy of: LENNAR REALTY (800-229-0611)

Listing Agent: Ben Goldstein (407-310-7677)

Remarks: Welcome to 802 Marcia Loop, a LAKEFRONT property located in southeast Winter Haven! The property includes an area on Lake Ruby right across the street! The lake is visible from the living room, kitchen, dining room, as well as the primary bedroom! Enjoy the amazing view of Lake Ruby while relaxing on the back patio, which is accessible from the living room and primary bedroom! This home is equipped with a solar panels. BONUS: SOLAR PANELS WILL NOW BE PAID OFF AT CLOSING! This will allow the buyer to benefit from the energy savings from day one! With 3 bedrooms, 2 bathrooms and over 1,500 square feet of living area this home provides ample space. This home sits on just over 1/4 acre, which is the largest lot in the community! Windows and sliding doors were replaced in 2024! Recent kitchen upgrades include: countertops, backsplash and appliances in 2024. The home is also equipped with water filtration, reverse osmosis and an ADT security system. Lake Ruby connects via canal with Lake Bess, providing more area to explore while fishing, boating, etc. Lake Ruby is a 259 acre lake and the access to Lake Bess offers enjoyment of another 146 acres of water. Both lakes have slalom courses and ramps, fitting for the “Water Ski Capital of the World”. Skiing is allowed on Lake Ruby so build a dock and bring a boat in! The laundry room provides a space to complete that chore within the comfort of your home. Winter Haven is centrally located which provides easy access to many parts of the state. The theme parks and airports of Orlando and Tampa are approximately one hour drives in their respective directions. LegoLand, Publix, Wal-Mart and the AdventHealth ER are all within 5 minutes of this home! Buyer and buyer’s agent are responsible for verifying information. Schedule your showing today!

Listing is courtesy of: LOCKHART & ASSOCIATES INC (863-293-1234)

Listing Agent: Bobby Desanto (863-604-7466)

Remarks: Under contract-accepting backup offers. The seller is OFFERING UP TO $14,000 toward a NEW ROOF or may apply this contribution toward the BUYER'S CLOSING COSTS, providing added flexibility and value. This spacious 4-bedroom, 3-bath ranch-style home offers an impressive amount of living space (2,178 sqft) filled with natural light and designed for comfort and flexibility. The many windows throughout the home create a bright, welcoming atmosphere, while multiple living areas provide room to spread out and enjoy. The remodeled kitchen features a refrigerator, dishwasher, and range, along with a convenient breakfast bar and adjacent dining area—perfect for everyday living and entertaining. A formal living room greets you at the front entry, and the oversized family room offers exceptional gathering space, complete with a built-in desk and direct access to the screened lanai. The generous primary suite includes a walk-in closet, garden tub, separate shower, and an additional wall A/C unit for added comfort. A desirable mini–master suite with its own private bath provides ideal space for guests, extended family, or a private home office. Built-in cabinetry throughout the home adds both character and abundant storage. Situated on a large corner lot, the expansive yard offers endless possibilities for outdoor living, recreation, or future enhancements. The chain-link fenced backyard provides security and functionality while maintaining an open feel. With no HOA restrictions, you’ll enjoy the freedom to personalize the property to suit your needs. Combining space, natural light, a sizable yard, and the advantage of no HOA, this property delivers comfort, flexibility, and room to grow.

Listing is courtesy of: CENTURY 21 MYERS REALTY LAKE WALES (863-676-4448)

Listing Agent: Michelle Heath (863-528-3123)

Remarks: Winter Haven's premier condominium located directly overlooking the picturesque Lake Spring that is part of the famous 17-lake Winter Haven Chain of Lakes. Be the first to enjoy this beautiful extensively remodeled and upgraded 5th floor corner unit directly off of the elevators. Lots of natural light through the expansive windows looking out to Lake Spring and the pool area. Lots of storage closets and an extra storage locker. Its turn-key & ready to move into. Exquisitely maintained building and has passed the newly required Florida State Milestone Inspection & Reserves Study. Many amenities including a covered assigned parking space, guest parking, boat slips & fishing pier, paver brick pool area, large work-out room, library and community room w/ kitchen. Outdoor grills for your use, shuffle board & patio furniture on the huge pool deck overlooking Lake Spring. Publix shopping center by walking across the side street is a great convenience. Close to downtown No pets or smoking. Owner will consider different leasing and/or purchase & financing options. Short term seasonal or long term lease. Tenants and/or buyers have to be approved and interviewed by the HOA as this is a 98% owner occupied building. Nicest condominium building in Polk County with full-time maintenance and management on-site daily.

Listing is courtesy of: KLINE REAL ESTATE SERVICES (863-287-0204)

Listing Agent: Scott Kline (863-287-0204)

Remarks: One or more photo(s) has been virtually staged. Price Improvement! Charming 1920s home in Winter Haven featuring original hardwood floors, modern updates, and desirable R-3 zoning. Located in one of Central Florida's fastest-growing markets, this move-in-ready property offers flexibility, character, and investment potential. Inside, you'll find a bright foyer, spacious living and dining areas with original hardwood flooring, and a functional kitchen complete with refrigerator, range, microwave, and dishwasher. The split-bedroom layout provides added privacy, while a bonus flex space off the primary bedroom is ideal for a home office, nursery, gym, or hobby room. A large Florida room adds extra living space and offers direct driveway access, perfect for entertaining or relaxing. The R-3 zoning creates opportunities for investors and future development potential (buyers should verify permitted uses with the City of Winter Haven). Conveniently located near downtown Winter Haven, LEGOLAND® Florida Resort, shopping, dining, medical facilities, major highways, and the Chain of Lakes. Now offered at a reduced price—schedule your private showing today!

Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (863-701-2350)

Listing Agent: Michael Hochadel (863-604-0018)

Remarks: Welcome to this beautifully maintained 2023-built home offering the perfect blend of modern design, functionality, and space to grow! Located in a desirable Winter Haven community, this move-in ready residence feels just like new construction without the wait. This spacious home features 4 bedrooms and 2.5 bathrooms, with all bedrooms thoughtfully located upstairs for added privacy and separation from the main living areas. The versatile floor plan is ideal for both everyday living and entertaining, offering a seamless flow throughout the home. The kitchen and living spaces showcase a clean, modern aesthetic, perfect for today’s lifestyle, while large windows bring in plenty of natural light. Whether you're starting a family or need more room to grow, this layout adapts to your needs with ease. Step outside to a huge fully fenced backyard with endless possibilities, create your dream outdoor oasis, add a pool, or design the perfect space for gatherings and play. Conveniently located just minutes from Legoland, shopping, dining, and major roadways, this home combines comfort, location, and value all in one. Don’t miss your opportunity to own a practically new home in one of Winter Haven’s growing areas!

Listing is courtesy of: ORANGE SLICE PROPERTIES (863-632-9765)

Listing Agent: Nellymar Albelo Pllc (407-435-1939)

Remarks: MOVE-IN READY! Welcome to your dream home in the sought-after Willowbrook North community! This stunning Ranch-style, one-story residence offers effortless living with 3 spacious bedrooms, 2 full bathrooms, and a versatile flex space—perfect for a home office, playroom, or additional living area. You'll fall in love with the modern open-concept layout, featuring quartz countertops throughout, soft-close cabinets and drawers, and smart home features designed for comfort and convenience. Enjoy peaceful mornings and relaxing evenings with serene pond views right outside your front door. Built with quality and style in mind, this home is the perfect blend of elegance and functionality—ready for you to move in and make it your own. Don't miss this opportunity to own a beautifully crafted home in a growing, vibrant community!

Listing is courtesy of: DRB GROUP REALTY, LLC (407-270-2747)

Listing Agent: Adam Schott (407-270-2747)

Remarks: Beautiful completely updated condo in the highly desirable gated community of Cypresswood Golf and Country Club. It features tile flooring throughout the whole condo, marble kitchen countertops with an extended breakfast island, matching marble on both bathroom vanities, upgraded lighting fixtures/ceiling fans, interior laundry with washer and dryer, pond view, and so much more. The master bedroom features an en suite bathroom while both bedrooms have a walk-in-closet. Additional linen storage exists in the main bedroom and hallway, plus an additional outside storage closet with shelves. The Cypresswood community features an 18-hole championship golf course designed by Ron Garl, junior Olympic sized community pool, lighted tennis courts, clubhouse with a restaurant, event space and more. Minutes from Hwy 27 and the I-4 corridor, Winter Haven's chain-of-lakes for the water enthusiast, Legoland Fl Park and Resort, Bok Tower gardens, and a brand new Publix shopping center within 2 miles and much more. Centrally located between Orlando and Tampa. Schedule your private showing today.

Listing is courtesy of: COLDWELL BANKER REALTY (727-781-3700)

Listing Agent: Amy Sullivan (863-280-3633)

Remarks: PRICED BELOW RECENT APPRAISED VALUE OF $795,000 — APPRAISAL AVAILABLE FOR REVIEW! (Real Matterport Tour & Videos in Virtual Tour Links) Rare opportunity to own one of the most desirable waterfront golf course homes in Cypresswood Golf & Country Club. Positioned on a private corner lot overlooking the pond, 4th green, and 5th tee, this extensively updated 5-bedroom, 4.5-bath estate offers nearly 4,200 SQ FT of luxury living with breathtaking views, incredible sunsets, and no rear neighbors. Inside, soaring ceilings, engineered hardwood floors, custom finishes, a gas fireplace, expansive entertaining spaces, and a completely secret hidden room create a one-of-a-kind luxury experience unlike anything else on the market. The chef’s kitchen features stainless LG appliances, propane gas range, custom cabinetry, oversized island, and seamless flow into the family room and entertainer’s wet bar — all designed around the stunning golf and water views. The downstairs owner’s suite offers a private retreat with spa-style bath, oversized closet, and direct pool views, while upstairs features spacious guest suites and a dedicated movie room/loft ideal for entertaining, working from home, or multigenerational living. The screened outdoor living area feels like a private resort with a sparkling pool, newer gas heater, outdoor summer kitchen with gas grill, and peaceful panoramic golf course and waterfront scenery. Major upgrades include new downstairs HVAC (2025), updated engineered hardwood flooring, newer pool equipment and pump, tankless gas water heaters, roof updates and annual inspections, fresh interior paint, and more. Located inside the 24-hour guard-gated Cypresswood Golf & Country Club community featuring championship golf, tennis, pickleball, clubhouse dining, fitness center, and resort-style amenities. Conveniently located near Legoland, Disney, Orlando attractions, top restaurants, shopping, malls, medical facilities, and major highways with easy access to both Tampa and Orlando. Luxury golf properties with this combination of views, privacy, updates, lot positioning, and value rarely become available.

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

Listing Agent: Justino Zoppe (417-848-1383)

Remarks: Welcome to this 2-bedroom, 2-bathroom ground-floor condo in the desirable Lake Buckeye community. This home features a bonus room and includes the washer and dryer for move-in ease. Step inside and enjoy seamless indoor-outdoor living with a cozy open patio off the dining area. The community enhances your lifestyle with amenities such as a sparkling pool, fishing pier, dock all while showcasing tranquil views of Lake Buckeye that make every day feel like a retreat. Ideally located just minutes from Polk State College, Winter Haven Hospital, Bond and Gessler Clinics, and the lively downtown of Winter Haven, you’ll enjoy easy access to dining, breweries, shopping, the farmers market, and seasonal events. Publix and the Diamond plex sports complex are less than 10 minutes away, Legoland Resort is only 15 minutes, and world-class attractions like Walt Disney World and Universal Studios are about an hour’s drive. With leasing permitted and no age restrictions, this property is an excellent choice for both homeowners and investors. Don’t miss your chance to make it yours.

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

Listing Agent: Brian Cox (863-559-3627)

Remarks: Here we go, back to market, Buyer default! The property you are inquiring about is located in Winter Haven, FL, in the Winter Haven Harbour area of Polk County. Now conveniently located is this corner unit with beautiful window views from the third floor, and with recent updates. Two bedrooms, 1 bath, with every square inch utilized for practical purposes. The community is a 55+ and is conveniently located in the heart of convenience. The HOA fees are low by comparison to what is included in the fee. Vacant and ready for occupancy. Text or call for your private viewing. *Agents, please read MLS remarks.*

Listing is courtesy of: BROKERS REALTY OF CENTRAL FLOR (863-294-6773)

Listing Agent: Renee Butler (863-294-6773)

Remarks: Welcome to the Eagle Landing community in Winter Haven, FL. This well-maintained single-family home is move-in ready and waiting for its new owner(s). The open-floor concept creates a comfortable flow throughout the main living areas, while the split floor plan provides added privacy for the primary bedroom and bath with spacious walk-in closet. The kitchen features stainless steel appliances and granite countertops, offering both style and functionality. Additional conveniences include a laundry room, two car garage and low HOA dues, making this home an affordable and practical choice. Experience the charm of small-town living while enjoying the growth and expansion happening throughout Winter Haven. Conveniently located just minutes from Legoland, shopping, dining, and entertainment, and centrally positioned between Tampa and Orlando for easy travel in either direction. Solar panels will be paid off at closing, providing the new owner with the benefit of low electricity bills. The spacious backyard offers room to relax or entertain.

Listing is courtesy of: CENTURY 21 WATSON & MYERS REALTY (863-324-1000)

Listing Agent: Carla Miro (786-897-4081)