Winter Haven Homes For Sale & Real Estate - 716 homes

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome to this beautifully maintained 4 bedroom, 3 bathroom pool home featuring a 3-car garage and situated on over half an acre. This expansive property offers a massive driveway, providing exceptional space for a boat, RV, or simply added privacy between neighbors—an increasingly rare find. Step inside to an inviting layout enhanced by luxury vinyl plank flooring and tile throughout. The home features a spacious front sitting room and an open-concept design that seamlessly connects the main living areas. At the heart of the home is the upgraded kitchen, complete with granite countertops, stainless-steel appliances, ample cabinetry, generous counter space, and a large island overlooking the bright and open living room—ideal for gatherings and everyday living. The primary suite offers a peaceful retreat with an ensuite bathroom featuring dual vanities, a garden tub, walk-in shower, and a walk-in closet. French doors from the primary bedroom lead directly to the screened-in patio, creating a private connection to the outdoor oasis. The additional bedrooms are located on the opposite side of the home, equal in size and conveniently positioned near two full guest bathrooms. Step outside to enjoy true Florida living on your large screened-in pavered patio overlooking the inground pool, perfect for entertaining family and friends. The property also includes a storage shed for added convenience. Recent upgrades include interior and exterior paint (2026), a new metal roof (2025), and new pool screens, offering peace of mind and move-in readiness. Located near a variety of restaurants, retailers, and everyday conveniences, this home combines space, privacy, and modern comfort in a highly desirable setting.

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

Listing Agent: John Hubbert, Jr (863-243-4024)

Remarks: Short Sale. Don’t miss the opportunity to own this one-of-a-kind, 3-bedroom, 2-bathroom, 2-car garage custom home. Upon arriving at the property, you are greeted by an oversized lot and mature trees in a quiet, well-established neighborhood. Inside, the home offers an open and split floor plan, cathedral ceilings, and an indoor/outdoor pool that flows from the back patio into the living room, adding a unique feature to this property—perfect for entertaining and allowing you to take a dip in any weather. On the left side of the home are two spacious bedrooms with large closets and a shared bathroom featuring a single vanity and a shower/tub combo. Moving to the right side of the house, you’ll find the master suite, loft, and kitchen. The master suite offers ample space and direct access to the pool area. The en-suite bathroom includes a garden tub and walk-in shower. The loft overlooks the living room and pool area and also contains two large storage spaces on either side, making storage accessible while serving as a great spot to watch a show and unwind. The kitchen features tile countertops and a small bar for additional seating. Right out back, the pool is enclosed in a full-screen cage with a large deck. The yard also boasts a shed for storage and plenty of space for activities. This home has so much to offer. Don’t wait—schedule your private showing today!

Listing is courtesy of: LPT REALTY LLC (386-388-7877)

Listing Agent: Trent Shackelford (941-518-7875)

Remarks: OWN YOUR LAND! This home is located in Garden Grove Oaks, a community close to everything! A Clubhouse, pool, shuffleboard courts, and screened in hot tub to enjoy in the friendly 55+ community. An open front porch to enjoy the beautiful weather is enhanced by the front yard garden under the mighty oak! (Tree has been maintained/trimmed regularly) Light and bright, with laminate flooring throughout. The floor plan is open with the living room and dining room upon entering. The kitchen provides space for a bistro table, has a pantry, and great cabinet space. New Ceiling fans, faucets, regularly maintained AC, with 25 yr shingles from 2015. Inside laundry also has a utility sink! Both bedrooms are well sized and have walk-in closets. Primary bedroom has an en suite bathroom. Average total utilities are $150/month...water, sewer, electric! The owner has provided a copy of their 4-Point report just done in March for their insurance company. No grey pipe!

Listing is courtesy of: GOOD COMPANY REALTY INC. (863-585-9610)

Listing Agent: Sanda Andrews (863-585-9610)

Remarks: Here is Central Florida's retirement living at its best. Master planned community with most exterior maintenance included for easy living and full resort-like amenities. Well maintained and on-site managed lakefront community clubhouse for and active lifestyle. Very well maintained home priced below others and close to the side entrance gate for easy access. No rear neighbors provides for a more serene atmosphere and the north facing rear screened porch is pleasantly shady and backyard room to be expanded. Move-in ready.

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

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

Remarks: Move-in ready and priced to sell, this beautiful 2013-built 3-bedroom, 2-bath home offers 1,865 sq. ft. of comfortable living space and a 2-car garage in a desirable single-entry community. The split floor plan features tile and luxury vinyl plank flooring throughout, a spacious primary suite with walk-in closet, and a well-appointed bath with dual sinks, a garden tub, and separate shower. The kitchen boasts granite countertops, a breakfast bar, and an eat-in dinette. Enjoy the fenced backyard, inside laundry room, ceiling fans throughout, and recent updates including a new roof in 2024, A/C in 2019, and air handler in 2023. Convenient to shopping, schools, and medical facilities.

Listing is courtesy of: REAL ESTATE BROKERS USA, INC. (863-242-6624)

Listing Agent: Debbie Bradbury (863-242-6624)

Remarks: Discover waterfront serenity at 5840 Gray Heron Drive, a beautifully maintained Winter Haven retreat featuring a roof replaced just two years ago and a luxurious master bathroom fully renovated in June 2025. This home boasts stylish flooring updated in 2018 and offers a private backyard sanctuary with breathtaking views of a large pond, perfectly complemented by community amenities including two sparkling neighborhood pools. Conveniently located near local favorites like Port 27 and the world-class family fun of Legoland Florida Resort, this property combines modern peace of mind with a premier Florida lifestyle.

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

Listing Agent: Christopher Warschauer (863-257-6677)

Remarks: Under Construction. This home offers an open floor plan with 9'4" ceilings and lots of natural light. The kitchen features granite countertops a large island, and plenty of storage. The primary suite includes a walk-in closet and private bath, providing a comfortable retreat. Conveniently located near shopping, dining, and Winter Haven's beautiful lakes.

Listing is courtesy of: ASHTON WOODS FLORIDA REALTY LLC (813-918-4491)

Listing Agent: Reed Williams (813-918-4491)

Remarks: NO HOA | NO CDD | Move-in ready! Hi there! - I’m 2519 Avenue E SW, but you can call me home. I’m a new construction block home with 3 bedrooms, 2 bathrooms, and 2,063 sq ft of thoughtfully designed living space — plus a 2-car garage and NO HOA or CDD, giving you more freedom and affordability. I was built with comfort and style in mind. My high ceilings and large windows fill every room with natural light, creating a bright and welcoming atmosphere. My open-concept layout makes it easy to gather, entertain, and enjoy everyday living. My kitchen is one of my favorite features — a beautiful island space with granite countertops, stainless steel appliances, and plenty of cabinet storage, perfect for cooking, hosting, and making memories. When it’s time to unwind, my primary suite offers a peaceful retreat with a spacious bathroom, double vanity, elegant finishes, and a walk-in closet ready for you to make your own. I also have a dedicated laundry room, ceiling fans, and wood flooring throughout for added comfort and convenience. I’m located in a growing area of Winter Haven, just minutes from shopping, dining, parks, and major highways, making everyday living easy and connected. I’m move-in ready and excited to meet my new owners. Come take a look — I think we might be the perfect fi!

Listing is courtesy of: SIVEN PREMIER REAL ESTATE (813-419-7009)

Listing Agent: Fanta Traore (863-282-9602)

Remarks: 2118 Chris Dr is a property that boasts a kitchen equipped with all stainless steel appliances, adding a modern touch to the culinary space. The kitchen island serves as a functional centerpiece, perfect for meal preparation or casual dining. The primary bedroom is a haven of comfort, complete with a walk-in closet that provides ample storage for your wardrobe. With these attributes, this property ensures a comfortable and convenient lifestyle. Included 100-Day Home Warranty with buyer activation

Listing is courtesy of: OPENDOOR BROKERAGE LLC (480-462-5392)

Listing Agent: Karen Albright (480-462-5392)

Remarks: ? Back on Market – New Price + $10,000 Buyer Incentive! ? Welcome to this move-in ready 4-bedroom, 2-bath home with a 2-car garage, perfectly situated on a rare nearly ½-acre oversized lot in Winter Haven! This home offers the space and updates today’s buyers are looking for — including a brand NEW roof and NEW A/C (2025), giving peace of mind and added value from day one. Step inside to a bright, open layout with updated flooring and plenty of room for both everyday living and entertaining. The spacious kitchen flows seamlessly into the main living area, creating a comfortable and inviting atmosphere. The flexible 4th bedroom with French doors can easily serve as a guest room, home office, or additional living space — tailored to your needs. Outside, the oversized lot is a true standout! Whether you’re dreaming of adding a pool, storing a boat or RV, or creating your own backyard oasis, this property gives you the space to make it happen. ?? Seller is offering $10,000 toward buyer closing costs or interest rate buy-down. Conveniently located near shopping, dining, and major roadways while still offering room to spread out — a rare combination at this price point. Don’t miss your chance to own a home with space, updates, and flexibility — schedule your showing today!

Listing is courtesy of: FREEDOM REALTY (863-289-7004)

Listing Agent: Ike Fountain (863-206-1105)

Remarks: Under Construction. BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. Feel at home with the Magenta, a single-story home with 3 bedrooms, 2 bathrooms, and a 2-car garage. This layout is a true gem, seamlessly blending modern comfort with Florida charm. Open concept living dazzles with luxury vinyl plank flooring throughout the main living areas. The kitchen, featuring quartz countertops, new stainless-steel appliances and ample storage overlooks the dining and living area. A dreamy, covered lanai, accessible through sliding glass doors, invites you to take full advantage of the Florida climate. The owner’s suite boasts double vanities, a walk-in shower and a substantial walk-in closet, while the additional bedrooms and full bathroom are located off the kitchen for added privacy. With a brand-new washer and dryer conveniently located off the foyer, a smart thermostat with voice control to maintain energy efficient living, and professionally curated landscaping, the Magenta is designed to make every day extraordinary. Just off US-27 with quick access to I-17, Villa Mar puts you close to local hotspots, and everything that makes Central Florida shine. Discover Winter Haven’s Chain of Lakes, explore the historic downtown district, or enjoy a fun-filled day with the family at LEGOLAND® Florida Resort. At Villa Mar, you’ll enjoy a fresh approach to relaxed living, with everyday essentials and local favorites right around the corner. Images shown are for illustrative purposes only and may differ from actual home. Completion date subject to change. Contact or make an appointment for more details on interest rates.

Listing is courtesy of: CASA FRESCA REALTY (813-343-4383)

Listing Agent: Michael Human (813-343-4383)

Remarks: One or more photo(s) has been virtually staged. Under Construction. This two-story Georgia will definitely be on your mind… This beauty highlights a modern open layout, seamlessly integrating a first-floor kitchen with a central island, a dining room and a welcoming family room with patio access. On the same level is a private owner's suite with an attached bathroom. Situated upstairs is a versatile loft for additional shared living space and four secondary bedrooms to provide restful retreats to family members and guests alike. 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: Welcome to this beautiful 4-bedroom, 2.5-bath home that perfectly blends comfort and charm. Step inside to find spacious living areas, ideal for both everyday living and entertaining. The real showstopper is the dream backyard—an outdoor oasis featuring a stunning pool and an incredible farm-style barn that offers endless possibilities, from hobbies to storage or even a unique entertaining space. This property truly has it all—space, style, and a one-of-a-kind backyard retreat you won’t want to miss! Property is being sold As-Is. Major updates have already been completed, including a new roof installed in May 2025, foundation work completed in November 2024, and a new sliding door added in November 2024. The property also features a brand-new barn shed and solar panels, offering added value and efficiency for the next owner.

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

Listing Agent: Daisy Perez (407-951-4218)

Remarks: Welcome to this stunning Bradley floorplan, located in the highly sought-after community of Willowbrook near a beautiful golf course in Winter Haven, FL. This spacious 4-bedroom, 2-bath home offers 1598 square feet of living space and provides excellent curb appeal in its elevation. Inside, you'll find gorgeous White cabinets complemented by sleek quartz countertops in the kitchen, creating a modern, bright atmosphere. Tile flooring runs throughout the wet and common areas, offering durability and easy maintenance. The open layout is perfect for family gatherings and entertaining guests.

Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)

Listing Agent: Nancy Pruitt, Pa (352-552-7574)

Remarks: One or more photo(s) has been virtually staged. Welcome to the Mulberry floorplan, located in the highly sought-after community of Willowbrook near a beautiful golf course in Winter Haven, FL. This spacious 4-bedroom, 2.5-bath home offers 1,938 square feet of living space and provides excellent curb appeal in its elevation. Inside, you'll find gorgeous White cabinets complemented by sleek quartz countertops in the kitchen, creating a modern, bright atmosphere. Tile flooring runs throughout the wet and common areas, offering durability and easy maintenance. The open layout is perfect for family gatherings and entertaining guests. This home is ideally situated just minutes from the scenic Port 27 and downtown Winter Haven, making it convenient for shopping, dining, and entertainment. Additionally, it's only a short drive to Highway 27 and about 20 minutes to I-4, providing easy access to nearby cities and attractions. Don’t miss the chance to own this beautiful home in a prime location—schedule your tour today!

Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)

Listing Agent: Nancy Pruitt, Pa (352-552-7574)

Remarks: Located in the new Residences at Winter Haven community, this home features the Everglades model floor plan, designed with an open-concept layout that maximizes natural light and functionality. The home backs directly to the community pond, offering water views and added privacy. Built with double-pane insulated windows and constructed in compliance with the current Florida Building Energy Efficiency Code, the home offers modern efficiency standards. Residences at Winter Haven is a newly developed single-family home community conveniently located near shopping, dining, major roadways, and everyday conveniences. There is a natural ease to this home, from the open layout to the thoughtful finishes. The 8-foot doors and premium flooring flow throughout the main living areas, creating a clean and consistent feel. In the kitchen, the focus is on quality and gathering, highlighted by a large waterfall island and 42” cabinetry with crown molding. It’s a home designed for both quiet mornings and hosting friends, with an open living area that leads out to a covered lanai. It’s a clean, modern space that’s ready for you to make it your own. A model home is available for on-site visits within the community.

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

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

Remarks: One or more photo(s) has been virtually staged. Under Construction. Beautiful Corner Lot!! This expansive two-story Columbus has a well-designed layout, featuring a first floor dedicated to shared living and entertaining. The open concept design seamlessly connects the kitchen, dining room and family room, with a patio extending the interior space outdoors. Upstairs, a spacious loft separates the three secondary bedrooms from the serene owner's suite. Completing the home is a convenient two-car garage. Peace Creek Reserve is a masterplan community of new single-family homes with a beautiful natural creek. Winter Haven is the chain of lakes city, with over 26 linked together by canal. There are lots of shops, restaurants, 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: COMPLETE REMODELING * PRIME LOCATION * HOUSE & INVESTMENT * NEW ROOF 2026 Complete remodeling house6/5 near 4,000 square feet of living area. Short distance from parks as Legoland, restaurants, malls. Great location between Tampa and Orlando. Builders don't build this king of big houses anymore. Brand new fence, new floors, walls and update bathrooms inside, owner invested more than $50,000 on new updates. Price is reduced for a quick sale. Today construction cost is $200 square feet. Get this great deal for a fraction of the original price. All concrete block construction.

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

Listing Agent: Gino Dapello (954-790-0632)

Remarks: ***Price Adjustment*** Gated Community! Welcome to this Beautiful 4BR/3BA Home with Hardwood throughout, with ceramic tile in wet areas, HEATED Inground Swimming Pool with Water Fountain! NEW Roof (2023); Recent A/C, Water Heater, Pool Motor and Hot Water System Replacements; also, Interior and Exterior Recently Painted. New TECO Sensi Smart Digital Thermostat to save you energy and by using the Sensi App you can manage your home's temperature from anywhere. It is nestled in the gated Terranova community, this beautiful home features well-maintained landscaping, extra High Ceilings with crown molding in Foyer, Living Room, Dining Room, Kitchen Nook and Family Room, 4 bedrooms, 3 full bathrooms, with a good size master suite with a walk-in closet, jacuzzi, and shower; Other highlights include a screened-in deck and an oversized lot with a PVC privacy fence. At .29 acres, the backyard is one of the largest in the community, offering significant flexibility for future use. The formal living and dining areas, cozy breakfast nook, and family room are spacious and perfect for gatherings. Additionally, the water well sprinkler system provides year-round savings, particularly during the summer months. Note: "Some Furniture is available for sale".

Listing is courtesy of: DALTON WADE INC (888-668-8283)

Listing Agent: Raquel Hernandez (863-662-0910)

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)