Homes For Sale in Winter Haven 33884 - 423 homes

Remarks: Pre-Construction. To be built. Welcome to Ashton Covey in Winter Haven! Discover the ultimate Florida lifestyle in this stunning community. Perfectly situated just off US Highway 27, your new home offers seamless access to work, outdoor recreation, shopping, dining, and more. Imagine being less than 15 minutes from Downtown Winter Haven, where charming local shops and restaurants await your exploration. Plus, you're just 5 miles from public lake access at Lake Daisy, ideal for a day of boating, paddle boarding, and enjoying the water. The Lynn Haven single-family home lives up to expectations. Relax on the long front porch. Inside, flex space makes an ideal den, or add doors for a quiet study. The foyer leads to the open family room and gourmet kitchen with island, where favorite meals and memories will be made. Enjoy outdoor living on the extended lanai, and store seasonal items in the 3-car garage. There’s even more to love upstairs with a loft, 3 bedrooms and a full bath. In your deluxe owner’s suite, enjoy beautiful tray ceilings, double vanities and a walk-in closet. You can have it all in The Lynn Haven. All Ryan Homes now include WIFI-enabled garage opener and Ecobee thermostat. **Closing cost assistance is available with use of Builder’s affiliated lender**. DISCLAIMER: Prices, financing, promotion, and offers subject to change without notice. Offer valid on new sales only. See Community Sales and Marketing Representative for details. Promotions cannot be combined with any other offer. All uploaded photos are stock photos of this floor plan. Actual home may differ from photos.

Listing is courtesy of: MALTBIE REALTY GROUP (813-819-5255)

Listing Agent: Bill Maltbie (813-819-5255)

Remarks: Under contract-accepting backup offers. This beautifully updated split floor plan home in the desirable Eloise Woods subdivision offers the perfect blend of comfort, quality upgrades, and incredible outdoor living. Nearly every part of this home has been improved, making it truly move-in ready. Inside, the home features updated flooring throughout, renovated bathrooms, redone ceilings, updated electrical and plumbing, new interior doors and trim, and an updated kitchen with new counters, custom backsplash, stainless appliances, and a large wrap-around bar that makes the kitchen the true heart of the home. The layout flows nicely with a spacious living area and flexible dining space that could also be used as an additional den or sitting room. The primary bedroom includes an en-suite bathroom, walk-in closet, and sliding glass doors that lead directly to the pool area. The secondary bedrooms are generously sized with great closet space, and the guest bathroom offers convenient access to the pool patio—perfect for when family and friends come over to enjoy the backyard. Step outside and you’ll immediately see what makes this home special. The pool area has been extensively upgraded with an extended deck finished with beautiful travertine tile, creating an incredible space for entertaining. Multiple pergolas, a built-in bar area, paver walkways, and private fencing create a backyard that truly feels like your own personal retreat. Additional improvements include updated windows and sliding glass doors with built-in custom blinds, custom closet systems, updated garage with epoxy flooring and storage, new soffit and fascia, gutters with screens, irrigation system, and a new drain field. Major mechanical updates give peace of mind with a full home re-pipe completed in 2014, new A/C and ductwork in 2019, and a brand new roof installed in April 2024. From the interior upgrades to the incredible outdoor entertaining space, this home offers a rare opportunity to own a fully updated property in Eloise Woods where the list of improvements is truly extensive.

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

Listing Agent: Sam Daniels (863-412-8218)

Remarks: This Azure floor plan offers a welcoming formal entry and hallway. A spacious great room with kitchen is open to dining and family entertainment area that leads to a covered patio. Also included is a great sized primary bedroom with a primary bath and walk-in closet. Included features: 9"4' ceilings and 8' doors, 42' cabinets and 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. *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: Discover this stunning Ruby home, ready for quick move-in! Included features: a welcoming covered entry; a smartly planned kitchen boasting white 42" cabinets, a center island, a large walk-in pantry, and an open dining area; an immense great room; a secluded primary suite showcasing a generous walk-in closet and a private bath; three secondary bedrooms; a shared hall bath; a central laundry; and a comfortable covered patio. *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: Pre-Construction. To be built. Welcome to Ashton Covey in Winter Haven! Discover the ultimate Florida lifestyle in this stunning community. Perfectly situated just off US Highway 27, your new home offers seamless access to work, outdoor recreation, shopping, dining, and more. Imagine being less than 15 minutes from Downtown Winter Haven, where charming local shops and restaurants await your exploration. Plus, you're just 5 miles from public lake access at Lake Daisy, ideal for a day of boating, paddle boarding, and enjoying the water. The Sandalwood single-family home sets the standard for main level luxury. A convenient family entry welcomes you inside to unmatched space and style. A full bath sits between 2 bedrooms, while a guest suite with full bath is found off the 3-car garage. Use the versatile flex space as a home office. The gourmet kitchen includes a large island overlooking dining space and the family room, ideal for gathering with family and friends. Your luxurious owner’s suite features a double vanity bath and massive walk-in closet, plus private access to the rear lanai. You’ll be stunned by The Sandalwood. All Ryan Homes now include WIFI-enabled garage opener and Ecobee thermostat. **Closing cost assistance is available with use of Builder’s affiliated lender**. DISCLAIMER: Prices, financing, promotion, and offers subject to change without notice. Offer valid on new sales only. See Community Sales and Marketing Representative for details. Promotions cannot be combined with any other offer. All uploaded photos are stock photos of this floor plan. Actual home may differ from photos.

Listing is courtesy of: MALTBIE REALTY GROUP (813-819-5255)

Listing Agent: Bill Maltbie (813-819-5255)

Remarks: Welcome to this charming three-bedroom, two-bath home nestled in the desirable Lake Daisy Wood neighborhood. Featuring a practical open concept floor plan with tile throughout, this residence is designed for comfortable living. The inviting living room seamlessly connects to a screened porch lanai through sliding glass doors, providing a perfect view of the spacious, fenced backyard—ideal for gatherings or relaxation. The kitchen boasts a convenient breakfast bar and a separate eating area, while a dedicated laundry room connects the garage to the home for added convenience. The generous primary bedroom offers an en suite bath complete with a tub, separate shower, and a large walk-in closet, with its own sliding glass doors leading to the screened lanai. As an added benefit, with a full-price offer, the seller will pay off the solar system in full. This home combines functionality with a welcoming atmosphere, perfect for everyday living.

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

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

Remarks: Welcome to this beautifully maintained 3-bedroom, 2-bath home located in the highly sought-after Cypresswood golf community in Winter Haven. Enjoy resort-style living with an 18-hole golf course, 24-hour gated security, clubhouse, community pool, and more. Inside, the renovated kitchen features granite countertops and custom cabinetry. The spacious primary suite offers a large ensuite bath complete with a double vanity and a generous walk-in closet. Additional updates include a roof replaced in July 2022, windows in May 2023, appliances in November 2016, an updated water heater and A/C, a garage screen added in September 2019, and a motorized awning installed in July 2022. This is an exceptional opportunity to own in one of Winter Haven’s premier neighborhoods. The home does come with appliances and washer and dryer.

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

Listing Agent: Melissa Witter (863-206-8744)

Remarks: Welcome to resort-style living in the highly sought-after gated waterfront community of Winterset, where convenience meets comfort in this charming 2-bedroom, 2-bathroom downstairs condo. Step inside to discover a spacious living and dining room combo that creates an inviting atmosphere for relaxation and entertaining. The well appointed kitchen features stainless steel appliances and a convenient breakfast bar, perfect for causal dining or morning coffee. The master bedroom suite features a generous walk-in closet, providing ample storage space. For your convenience, a stackable washer and dryer are included. This professionally managed community boasts a plethora of amenities, including a clubhouse, fishing pier, heated pool, hot tub, and tennis courts—all overlooking the serene Lake Winterset, part of the renowned "Chain of Lakes." Enjoy peace of mind with state-of-the-art security in this well-maintained environment. You’re just minutes away from Lego Land and conveniently located near Disney and other Florida amusement parks, shopping, dining, and more. Alternatively, relish the numerous community offerings, including a fitness center, shuffleboard, and expansive green spaces perfect for walking your family pet. Additionally, most furniture is negotiable, providing a seamless transition into your new home. Experience the perfect blend of leisure and lifestyle at Winterset!

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

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

Remarks: One or more photo(s) has been virtually staged. Under Construction. The first floor of the stunning Edison two-story home is host to an open-concept layout that combines the kitchen with the living and dining areas, and an outdoor patio is easily reached off the main living space. Upstairs, five bedrooms surround a versatile loft, including the luxe owner’s suite, complete with a generous walk-in closet and en-suite bathroom. Villa Mar is a masterplan community of new single-family homes. Near Historic downtown Winter Haven. There are lots of shops, restaurants, bike paths, and easy access to nearby highways. Close to Legoland and Bok Tower Gardens. The much anticipated “Villar Mar” community is what you have been looking for. A safe small town feel with convenience.

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

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

Remarks: Designed for the way you live today, this beautifully updated 3BR/2BA home offers a modern, open floor plan ideal for gathering with family, entertaining friends and great for enjoying relaxed backyard barbecues. Built in 2002, offering just under 1900 square feet of comfortable living space. Topped with a long-lasting, low maintenance tile roof designed for lasting durability, this home is ideally positioned with no direct neighbors-backing up to peaceful green space for added privacy. Thoughtfully updated with numerous recent improvements, providing peace of mind for the next owner. Major upgrades include new HVAC system (2023), hot water heater (2025), new flooring throughout (2025), freshly painted, complemented by new ceiling fans, light fixtures and hardware throughout. While functionality has been enhanced inside recent upgrades outside include irrigation improvements (2023), a garden sump pump (2026) and exterior paint just completed, offering even more value and curb appeal. Enjoy resort-style living in this gated community featuring a heated pool, spa, tennis/pickleball courts and Community Clubhouse. Residents also have access to a private boat ramp and dock-perfect for fishing or taking in breathtaking sunsets on Lake Winterset. Winter Haven is a vibrant and growing lakeside city known for its Chain of Lakes lifestyle, charming downtown with weekend farmers market and ski shows. Winter Haven is also home to attractions like LEGOLAND Florida Resort and Peppa Pig-offering the perfect balance of relaxation, recreation and convenience to Lakeland/Tampa, Orlando, major airports and both coasts. The perfect place to call home!

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

Listing Agent: Laurie Nock (937-218-0031)

Remarks: Short Sale. Welcome to this beautiful Winter Haven home! Villamar This property offers a spacious layout, abundant natural light, and comfortable living areas ideal for everyday living and entertaining. The backyard provides great outdoor potential. Conveniently located near shopping, dining, schools, and major highways. Short Sale opportunity — perfect for buyers looking for value and investment potential.

Listing is courtesy of: MY REALTY GROUP, LLC. (786-847-7421)

Listing Agent: Yoja Mirabal (407-543-7789)

Remarks: Discover this charming home ideally located near Legoland, hospitals, businesses, and schools. With easy access to major roads, this property is situated within a community that offers private access, providing both convenience and security. The home requires new flooring, but with a little help and your personal touch, it has great potential to become a cozy haven. Perfect for first-time buyers or as an income property. Come and make this house your new home!

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

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

Remarks: Welcome to the affordable lifestyle of living in a Villa within a golf course community. Upon entering the front of the home you will notice a courtyard area on the left and right side of the entrance, which opens up additional outside entertaining space. Once inside the home you will notice it has recently been refreshed with new interior painting throughout, all new flooring, and new stove and dishwasher. As you enter, you will find the open and bright kitchen with all Stainless Steel appliances on the immediate right hand side of entryway. The dining room is open to the living room and it will handle a large dinning room set for company dinning. The living room opens to a slight step down into a less formal family room area which overlooks the lush setting of the tropical, backyard landscaping, a beauty to enjoy from your rear windows. The community clubhouse, restaurant and swimming pool are just a few steps away. The tennis courts and pickle ball courts are currently being resurfaced.

Listing is courtesy of: XCELLENCE (866-595-6025)

Listing Agent: Della Landfear (863-698-8057)

Remarks: Welcome to the Enclave at Cypresswood Golf & Country Club. Cypresswood is a Gated community featuring a 24-Hour Guard, 18 Hole Golf Course, Community Pool, Lighted Tennis Courts, Restaurant, and a Pub. This 2 Bedroom Villa is For Sale, FULLY FURNISHED, and Move-In Ready! The owners updated their Home in 2023, just 3 years ago, with Granite Countertops, Stainless Steel Appliances, New Furniture, and the Interior was Freshly Painted. The owners are including the 75 Inch TV with the Entertainment Center in the Living Room. Be sure to take time to enjoy the view from your Screened Porch. There are No Homes behind you, just open pastures, roaming cows, and trees. Very peaceful. The HOA fee also includes the Landscaping, Lawn Maintenance, Exterior Painting, and Roof (replaced in 2023) for your Villa. This Home allows you to relax and enjoy a game of Golf, take a swim in the Olympic Pool, or just enjoy your favorite show on TV. The Home is located close to Shopping (New Publix opening soon), Restaurants, Downtown, and Highway 27 which leads to Interstate 4 for Tampa and Orlando (Disney World). Come see what this home can offer you!

Listing is courtesy of: XCELLENCE REALTY, INC (866-595-6025)

Listing Agent: David Shippey (863-521-4517)

Remarks: Welcome to this beautifully maintained 2-bedroom, 2-bathroom, 2-car garage home, lovingly cared for by its original owner. Designed for comfort, simplicity, and low-maintenance living, this residence offers just under 1,200 sq. ft. of well-planned space—ideal for those seeking an easy, relaxed lifestyle. The club house is an amazing place to enjoy the 87 degree pool year round, Boat slips available with private boat launch and pickle and tennis courts available among many more amenities. Inside, you’ll find tile flooring throughout the main living areas for effortless upkeep, along with stone countertops in the kitchen and bathrooms for a clean, modern touch. The spacious primary suite includes a large walk-in closet, providing excellent storage and everyday convenience. The split-bedroom layout offers privacy and flexibility for guests, hobbies, or a home office. One of the standout features is its private setting—you’re not looking directly at a neighboring home, giving you a rare sense of openness and tranquility. Step outside to the beautiful back screened in patio, perfect for soaking up the sun, relaxing with a book, or enjoying quiet evenings outdoors. Located in the highly desired 55+ community of Traditions, you’ll also enjoy exceptional amenities. The impressive community center features a heated pool maintained at a comfortable 87° year-round, with stunning views overlooking Lake Ruby. Residents have access to a private boat launch and boat slips, making lake days easy and enjoyable. Stay active with pickleball courts, a fully equipped workout facility, and a full schedule of social events, activities, and community gatherings happening throughout the year. With its peaceful setting, quality finishes, and resort-style amenities, this home offers the perfect blend of comfort and active living. Don't forget the new Publix being built around the corner for quick and easy grocery shopping.

Listing is courtesy of: LA ROSA REALTY PRESTIGE (863-940-4850)

Listing Agent: Keith St. Onge (863-651-1397)

Remarks: This two bedroom one and a half bath condo offers comfortable living. The kitchen features stainless steel appliances and an eat-in space. Bedrooms are upstairs with a full bath for privacy. A fenced patio provides outdoor relaxation and the community pool is just steps away. Convenient location near shopping dining and Legoland.

Listing is courtesy of: ORLANDO HOMES & INVESTMENTS (407-467-6515)

Listing Agent: Noel Moenssens (407-467-6515)

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: One or more photo(s) has been virtually staged. Under Construction. Open flow sets the tone for this elegant new Crestone II two-story townhome. There are a total of three bedrooms. The first level features a spacious and flexible open-concept layout shared between the kitchen, dining room 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: One or more photo(s) has been virtually staged. Under Construction. Open flow sets the tone for this elegant new Crestone II two-story townhome. There are a total of three bedrooms. The first level features a spacious and flexible open-concept layout shared between the kitchen, dining room 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: One or more photo(s) has been virtually staged. Under Construction. Open flow sets the tone for this elegant new Crestone II two-story townhome. There are a total of three bedrooms. The first level features a spacious and flexible open-concept layout shared between the kitchen, dining room 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)