Winter Haven Homes For Sale & Real Estate - 803 homes

Remarks: NEW PRICE, JUST REDUCED!!! IMMACULATE GROUND FLOOR EAGLE POND CONDO located in desirable Cypresswood Golf & Country Club!!! Don’t miss your chance to own this charming 2-bedroom, 2-bathroom ground-floor condo in the highly sought-after, gated Cypresswood Golf & Country Club community. Perfectly maintained, this move-in-ready home features an open-concept living area, walk-in closets, interior laundry, and serene pond views. The spacious master bedroom includes an en-suite bathroom, while both bedrooms boast generous walk-in closets. Enjoy added storage with linen closets in both the master and hallway, plus an extra storage closet outside. The well-equipped kitchen boasts abundant cabinetry, ample counter space, a breakfast bar, pantry, and an inviting eat-in dining area. Relax on your private patio!! Ideal for seasonal living, rental income, or year-round comfort. Cypresswood's amenities include 24-hour gated/guarded security, an 18-hole championship golf course, junior Olympic-sized pool, walking trails, clubhouse, tennis courts, and restaurant. Just minutes from Highway 27, I-4, LEGOLAND, and a variety of dining, shopping, and entertainment options. Hurry and schedule a showing today!

Listing is courtesy of: THE K TEAM REAL ESTATE SERVICES LLC (863-604-1601)

Listing Agent: Cathy Kluytenaar (863-604-6220)

Remarks: Imagine coming home to peaceful cul-de-sac living, easy-care tile floors, and a refreshed kitchen ready for everyday life — welcome to your next chapter! Step inside to the living room featuring a decorative fireplace seamlessly flowing into the dedicated dining area. The kitchen has been tastefully refreshed within the past year with newer cabinetry, countertops, and appliances, creating a functional space for everyday cooking and entertaining. Sliding glass doors leading to the 17x8 screened-in lanai — perfect for enjoying Florida evenings. Just outside, an additional open concrete slab provides the ideal grilling or outdoor seating area. The primary bedroom features two closets and a private en-suite bath complete with a tub/shower combination and extended vanity. A long foyer off the garage leads to the second bedroom and guest bath. The third bedroom, located off the living room with French doors, provides flexible space ideal for a home office, den, or additional bedroom. Additional highlights include washer/dryer hookup in the garage and a convenient location just off Recker Highway with quick access to the Polk Parkway, making commutes to Lakeland, Tampa, or Orlando a breeze. Whether you're a first-time buyer, downsizing, or investing — this one checks the boxes for location, layout, and value! **Roof April of 2016, A/C 2016, Water Heater 2020**

Listing is courtesy of: STAR REALTY OF WINTER HAVEN (863-299-7827)

Listing Agent: Carlee Marchetti (863-258-3338)

Remarks: Welcome home to this inviting upstairs condo located in the peaceful Lake Buckeye Condo community, where tranquil lake views and relaxed living come together. Step inside to find laminate and ceramic tile flooring throughout, offering both durability and easy maintenance. The open living and dining area is light and welcoming, seamlessly extending to a private 3x7 balcony, the perfect place to enjoy your morning coffee or unwind at the end of the day. Just beyond, the well-appointed kitchen comes complete with all appliances, granite countertops, and an adjacent utility room with washer/dryer hookups and extra cabinet storage. The split-bedroom floor plan provides excellent privacy. The primary suite features a walk-in closet and a private en-suite bathroom with a walk-in tile shower, while the second bedroom is conveniently located near the hall bath, ideal for guests or a home office. Residents enjoy access to community amenities, including a sparkling pool overlooking beautiful Lake Buckeye and community docks, perfect for lakeside relaxation and peaceful views. This condo offers a wonderful blend of comfort, convenience, and serene surroundings—an opportunity you won’t want to miss!

Listing is courtesy of: STAR REALTY OF WINTER HAVEN (863-299-7827)

Listing Agent: Carlee Marchetti (863-258-3338)

Remarks: PRICE IMPROVEMENT! Welcome to this super spacious 3-bedroom, 2-bath home located in Lucerne Park Reserve in Winter Haven. Built in 2020, this home offers a modern split floorplan that provides privacy and functionality, perfect for everyday living or entertaining. The open layout creates a bright and airy feel throughout, with generous room sizes and excellent flow. Furniture is negotiable, making this a flexible move-in-ready opportunity for buyers. Enjoy outdoor living with a screened-in patio/lanai overlooking a fully fenced backyard—ideal for pets, play, or relaxing in privacy. Situated in a well-maintained community featuring a pool, playground, and clubhouse, this home offers both comfort and convenience. Enjoy the benefits of newer construction paired with desirable neighborhood amenities, all just minutes from shopping, dining, and major roadways. A great opportunity to own a nearly new home in a fantastic Winter Haven location.

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

Listing Agent: Harold Baker (863-604-6272)

Remarks: Under contract-accepting backup offers. Turn-Key Furnished Home in Lakefront 55+ Community Welcome to easy Florida living in the peaceful 55+ lakefront community of Lake Henry. This fully furnished 2-bedroom, 2-bath home is truly move-in ready, offering comfort, convenience, and a relaxed lifestyle just steps from the water. Inside, you'll find a bright and inviting layout with a spacious living area, functional kitchen, and dining space perfect for everyday living or hosting guests. The home includes all furnishings, making it an ideal option for seasonal residents, snowbirds, or anyone looking for a turnkey Florida retreat. Additional features include: • Covered carport parking • Utility/laundry room with extra storage • Spacious primary suite with private bath • Comfortable guest bedroom and second full bath • Low-maintenance living Residents enjoy access to community amenities including a community pool, social activities, and a private dock on Lake Henry, perfect for fishing, relaxing sunsets, and enjoying Florida's beautiful outdoors. Located in the heart of Winter Haven, you're just minutes from shopping, dining, golf courses, and medical facilities. Whether you're looking for a full-time residence, seasonal getaway, or low-maintenance retirement lifestyle, this furnished home offers incredible value in a welcoming community. Schedule your private showing today and experience the relaxed Florida lifestyle this home has to offer.

Listing is courtesy of: KELLER WILLIAMS RLTY NEW TAMPA (813-994-4422)

Listing Agent: Mario Paniagua Ovando (813-953-6003)

Remarks: Welcome to Winter Haven Harbor condos a 55+ community. This two bedroom one bath condo is an end unit and it is on the first floor, very close to your parking spot. The home has Nice laminate flooring throughout. The Dining room is next to kitchen, a little open concept area. The master bedroom has a nice size walk in closet. The home also boasts new energy efficient windows. The community features a massive heated pool, clubhouse with exercise room, kitchen, pool table, shuffleboard, and a grilling area with a nice area to entertain friends and family. This community also features a car washing area. Public bus transportation-Citrus connection available right out front. Buyer approval required. You are walking distance from shopping, Hospital and other medical centers. Centrally located between Tampa and Orlando. Schedule your appointment to view this home and make it yours today.

Listing is courtesy of: HARPER REALTY FL, LLC (863-687-8020)

Listing Agent: Annie Wood (321-229-1913)

Remarks: Welcome to this beautiful 3-bedroom, 2-bathroom home in the heart of Winter Haven! Featuring a desirable open floor plan, this home offers comfortable living with plenty of space to relax and entertain. The modern kitchen is highlighted by granite countertops, ample cabinetry, large island, and a seamless flow into the main living area, making it perfect for gatherings. Just off the entrance, you’ll find a versatile flex space that can easily serve as a home office, dining room, or playroom to suit your needs. The spacious primary suite is a true retreat, complete with a large bedroom and dual master closets, offering plenty of storage. Two additional bedrooms and a second full bathroom provide comfortable accommodations for family or guests. Step outside from the large sliding doors to enjoy the fenced-in backyard, ideal for pets, outdoor activities, or relaxing evenings. Located in a great neighborhood in the heart of Winter Haven, this home is conveniently close to shopping, restaurants, and local schools, offering both comfort and convenience. Don’t miss the opportunity to make this wonderful home yours!

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Bethany Jack (606-584-0518)

Remarks: Discover your serene retreat at Winter Haven Harbour Condos—a charming 55+ community featuring this delightful third-floor, two-bedroom, one-and-a-half-bath residence. Recently refreshed 3 years ago with a brand-new roof, fresh paint, and plush new carpeting in both bedrooms and the living space, this home is move-in ready. The kitchen is bright and functional, with plenty of cabinetry that extends into the dining area and ceramic tile flows seamlessly through the kitchen and baths. Enjoy a screened front porch, perfect for morning coffee. The community offers a large heated pool, a clubhouse, shuffleboard, and a grilling area—ideal for gatherings. Conveniently located near shopping, medical centers, and with easy access to both Tampa and Orlando, this is a rare opportunity. Schedule your private tour today!

Listing is courtesy of: HARPER REALTY FL, LLC (863-687-8020)

Listing Agent: Annie Wood (321-229-1913)

Remarks: Welcome to your one bedroom one bath 55+ condo located on the FIRST floor. The kitchen features an abundance of cabinetry. Primary bedroom offers 2 built in closets. Front porch area is entirely screened. The community features a massive heated pool, clubhouse with exercise room, kitchen, pool table, shuffleboard, and a grilling area with a nice area to entertain friends and family. This community also features a car washing area. Possible Owner Financing Available. Please Inquire with listing agent. Public bus transportation-Citrus connection available right out front. Buyer approval required. You are walking distance from shopping, Hospital and other medical centers. Centrally located between Tampa and Orlando. Schedule your appointment to view this home and make it yours today.

Listing is courtesy of: HARPER REALTY FL, LLC (863-687-8020)

Listing Agent: Annie Wood (321-229-1913)

Remarks: "OWNER WILL CREDIT UP TO $15,000 FOR THE COST OF ROOF REPLACEMENT AT CLOSING" FOR SALE: Attractive 3-Bedroom, 2-Bathroom Single-Family Home in Winter Haven! Discover your dream home in Osprey Pointe, where comfort meets style. This home is designed for modern living and entertaining. An open floor plan connects the eat-in kitchen and breakfast bar seamlessly to the living and dining areas, perfect for gatherings. Equipped kitchen with an eat-in area and a breakfast bar, ready for family meals and casual dining. Luxurious Master Suite: Retreat to your sanctuary featuring an elegant tray ceiling, a generous walk-in closet, double vanities in the primary bathroom, and a large glass shower stall. Enjoy the Florida lifestyle on your covered and screened rear porch. A paver driveway and an attached 2-car garage add to the curb appeal. The home includes inside laundry with washer and dryer hook-ups. Tiled common areas and bathrooms offer easy maintenance, while plush carpet in the bedrooms provides comfort. Exceptional Community Amenities: Live like you're on vacation every day! Enjoy access to a community clubhouse and a sparkling pool. Plus, take advantage of the private waterfront dock on beautiful Lake Ned for fishing and recreational activities. Lawncare included in HOA. Don't miss this opportunity to own a piece of paradise in Winter Haven. Schedule your showing today!

Listing is courtesy of: FLORIDA REALTY RESULTS LLC (407-498-3838)

Listing Agent: Debbie Browning (407-908-9060)

Remarks: Welcome to the luxurious 55+ golf course community of Lake Ashton! The home is the Biscayne floor plan, consisting of 3 bedrooms and 2 baths and a 2 car garage. The home and garage are accessible with electronic entry for ease. This home has been a winter retreat and only lived in a few months per year. Beautifully installed ceramic tile throughout and carpet in the bedrooms with 9' ceilings create such volume to the space. This home has stainless appliances and solid countertops to compliment the solid wood cabinetry giving it overall elegant feel and spaciousness. The breakfast nook looks into the main living space as well as out to the pond and nature preserve through one of the two 8' sliders giving perfect tranquility to peaceful mornings. No backyard neighbors!! Expansive primary bedroom with soaking tub and dual walk in closets make for the perfect retreat. Home is fully furnished with golf cart in the garage and all items are negotiable with purchase. Come see all that the Lake Ashton community has to offer.

Listing is courtesy of: KEYS TO THE BAY REAL ESTATE (813-965-1057)

Listing Agent: Nicholas Costello (813-965-1057)

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 contract-accepting backup offers. Welcome to this beautifully updated and immaculately maintained home that truly stands out. This 3-bedroom, 2-full-bath residence reflects the sellers’ meticulous care and pride of ownership throughout, offering peace of mind with a roof that’s only 8 years old. Step inside to find tile flooring throughout the ENTIRE HOUSE, all accented by crown molding throughout the entire home. The updated kitchen features Corian countertops, stainless steel appliances, ample cabinetry, and a functional layout perfect for everyday living and entertaining. Both bathrooms have been tastefully renovated with granite countertops and modern finishes. Enjoy Florida living at its best with a screened lanai overlooking a huge, fully fenced backyard, ideal for gatherings, pets, or relaxing in privacy. The outdoor space also includes a concrete barbecue area, making it perfect for entertaining. Additional features include a screened garage door and a charming front porch that enhances the home’s curb appeal. Ideally located close to shopping, dining, and everyday conveniences, with easy access to Orlando, this move-in-ready home offers the perfect combination of comfort, updates, and location. A must-see!

Listing is courtesy of: HOMEXPRESS REALTY, INC. (813-641-2500)

Listing Agent: Luciene Sarubbi (813-641-2500)

Remarks: Welcome to 523 Little Lake Court — a spacious 3-bedroom, 2-bath home on a generous lot in the heart of Winter Haven. Step through elegant double front doors with decorative glass and an arched transom into soaring vaulted ceilings that flow throughout the main living areas. The open layout features beautiful hardwood floors in the formal living and dining rooms, a large family room with a cozy fireplace and dramatic arched windows, and a kitchen with wihte cabinetry, a center island, and breakfast bar. The master suite has vaulted ceilings, a freestanding fireplace, French doors to the backyard, and an en-suite bath with a soaking tub, walk-in shower, and dual vanity beneath a stunning arched window. Additional highlights include an interior laundry room, an attached two-car garage, and a large fully fenced backyard with mature trees and a storage shed. Conveniently located just minutes from Little Lake with easy access to shopping, dining, and everything Winter Haven has to do.

Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)

Listing Agent: Steven Koleno (804-656-5007)

Remarks: Under contract-accepting backup offers. Beautifully renovated solid concrete block home featuring 3 bedrooms and 2 bathrooms, ideally located within walking distance to the Happy Valley Trail in a highly desirable neighborhood with breathtaking water views of Lake Conine. Situated on an oversized 0.31-acre corner lot, this property offers exceptional space, privacy, and endless possibilities for outdoor living and future enhancements — with NO HOA. Upon entry, you are welcomed into a bright and open-concept floor plan that seamlessly connects the living, dining, and kitchen areas, creating the perfect space for everyday living and entertaining. The modern updated kitchen showcases stylish finishes and ample cabinetry for all your cooking needs. The home also includes a dedicated laundry room that provides additional storage, along with an exterior utility room for extra convenience. The property features a covered carport with an extended concrete driveway, allowing parking for multiple vehicles. The spacious backyard includes an unfinished structure that can easily be converted into a garage, workshop, storage area, or even an Additional Dwelling Unit (ADU), offering a great opportunity to add value and customize the space to your vision. With its large corner lot, stunning lake views, move-in-ready renovations, and no HOA restrictions, this home is a rare opportunity offering comfort, versatility, and long-term potential.

Listing is courtesy of: CAISSA REALTY INVESTMENT INC (407-364-3056)

Listing Agent: Thay Barrera Troya (689-278-5059)

Remarks: One or more photo(s) has been virtually staged. Seller is offering $5,000 towards the buyers closing costs and prepaids! Completed in 2020 and ready for immediate occupancy, this property blends modern construction with thoughtful recent upgrades. Notable features include a brand-new roof installed in 2023, fully paid solar panels, a freshly painted interior, and professionally serviced and cleaned air ducts, all contributing to energy efficiency and average utility costs of approximately $85–$100 a month. The home is equipped with smart home technology and constructed with concrete block on both the first and second floors, offering added durability and peace of mind. Inside, the kitchen opens naturally to the main living spaces, creating an inviting layout for everyday living and entertaining. A future flooring update provides an easy opportunity to personalize the space. Bedrooms are generously sized, with the primary suite located upstairs, and a fully fenced backyard enhances privacy and functionality. Ideally positioned within the community, the home is just a short walk to the mailbox, pool, and playground, with convenient access to shopping, dining, grocery stores, major roadways, just a short drive to LEGOLAND® and less then one hour from Walt Disney World.

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)

Listing Agent: Kristin Duncan (407-274-5911)

Remarks: Under contract-accepting backup offers. Discover the perfect blend of country living and modern convenience with this well-maintained property set on over 5 acres. This spacious home offers 3 bedrooms plus a dedicated office, 2 full baths, a welcoming living room, formal dining room, and a bright kitchen with a breakfast nook. Step outside to your own private retreat featuring a screened pool, ideal for relaxing or entertaining. Equestrian enthusiasts will appreciate the horse barn along with fenced and cross-fenced pastures, providing plenty of space for animals. The property combines privacy and wide-open views with easy access to city amenities, shopping, and schools. With its well-cared-for condition and versatile layout, this home is move-in ready and waiting for you to enjoy the best of both worlds—peaceful country living just minutes from town.

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

Listing Agent: Steve Lockhart (863-289-9801)

Remarks: Charming residence in Winter Haven featuring 3 bedrooms and 2 bathrooms. This home has a spacious living area with abundant natural light, a modern kitchen with ample storage, and a serene backyard appropriate for relaxation. Located in a peaceful neighborhood with convenient access to local amenities, this property provides a welcoming atmosphere and comfortable living. Don't miss this opportunity to be part of the vibrant Winter Haven community. Key Features: *Kitchen: Newly remodeled kitchen with soft close upgraded cabinets and new appliances. Features: Fully furnished home with washer and dryer included; new bathrooms with upgrade tiles. Vinyl fence for pets and privacy. *Water softner system included

Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)

Listing Agent: Steven Koleno (804-656-5007)

Remarks: Fall in love with this expansive 5-bedroom, 3-bath, 3-car garage home situated on a quarter-acre of land, where luxury, functionality, and energy efficiency come together. Explore every corner of this stunning property right now through a 3D interactive walkthrough or a full video tour. Designed with an open layout and split bedrooms for privacy, the home feels massive yet efficient. The heart of the home is a wide-open living area and a huge kitchen featuring a gigantic island, 42-inch upper cabinets, a spacious pantry, and top-of-the-line stainless steel appliances. Whether you are relaxing, hosting, or cooking, the home provides boundless space to move and mingle. High-quality finishes are found throughout, including granite countertops in the bathrooms, luxury vinyl plank flooring in the main areas, and premium carpeting in the bedrooms. This isn't just a home; it’s an investment featuring $30,000 in upgrades available for your review! One of the standout benefits of this property is the incredible energy efficiency. Powered by solar panels plus a solar-powered attic fan, the home’s energy costs are cut in half compared to neighboring homes that have much smaller living areas. The solar panel lease is a manageable $180 a month, which keeps the actual electric bill payable to TECO energy as low as $5 to $20 a month. For added convenience, the home also includes a paid security system and a water softener system paired with reverse osmosis in the kitchen. The outdoor space is just as impressive, featuring a large, private backyard on a quarter-acre lot fully enclosed by a vinyl fence. You can enjoy the Florida weather from the comfort of a huge, screened-in lanai, surrounded by custom pavers that wrap seamlessly around the sides and back of the home. The meticulous landscaping is easily maintained by a full irrigation system. Located in a quiet, peaceful community in Polk County, you are perfectly positioned near Highway 27 for an easy drive to Disney and the Orlando Airport. Best of all, there are no CDD fees and a low HOA of only $725 a year. This home is being sold AS IS and is ready for you to move in. Schedule your showing today!

Listing is courtesy of: MAZELG REALTY (863-399-0226)

Listing Agent: Mary Sorrell (765-434-1802)

Remarks: One or more photo(s) has been virtually staged. Welcome to 6450 Hollyberry Lane in Brookhaven Village—a highly sought-after 55+ community where you own your land, making this a rare opportunity! This beautifully updated, move-in ready home features new luxury vinyl flooring (2025) and a bright, open layout perfect for everyday living and entertaining. The upgraded kitchen offers butcher block countertops, slide-out metal racks for added storage, and a brand-new dishwasher. Washer and dryer are included. Both bathrooms have been beautifully remodeled with modern finishes. Major updates include a new roof (Dec 2024), new HVAC system (2025) with ductwork and air handler, new windows (2025), and all-new screening, including the lanai with vinyl windows—perfect for enjoying Florida living year-round. The home is also fully replumbed with updated anchors and straps, including a vapor barrier that was installed about 4 years ago. The home also includes a great storage shed/workshop—ideal for hobbies or extra storage. Enjoy a super low HOA with access to a community pool and clubhouse, all in the heart of Winter Haven near shopping, dining, and lakes. Fully updated + land ownership + prime 55+ community—this one stands out. Schedule your showing today!

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

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