Winter Haven Homes For Sale & Real Estate - 972 homes

Remarks: Are you looking for a move-in ready home? Well, you found it! This home is like a new build, only better. It is clean as a whistle, has tasteful lighting and fans, luxury plank vinyl, granite countertops, screened lanai, retractable screens on the garage, epoxy garage floor, pad for a grill outback, only naming a few. This is an open floor plan that is great for either entertaining or hanging out at home by yourselves. The home was built in 2020 so it was designed to be eco friendly which makes it easier on the pocketbook. The master has an ensuite bath and a large walk in closet. The two additional bedrooms are a comfortable size for guests. One of the rooms has 3 windows that bow out which allows in lots of natural light, not to mention the bit of extra floor space it adds. It is a perfect space for a desk should you choose to make this your office. All this plus the fact that it is in one of Florida's premier Active Adult Communities. There are two 24 hr manned entrances, 2 pools & hot tubs, billiard rooms, craft rooms, computer libraries, bowling alley, movie theater, 3 dog parks, golf course, pro shop, dances, entertainment and too many clubs and activities to mention. You can be as active or involved as you like. Live and mingle among folks you may have a lot in common with and many of the same interests.

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Ann Heaton (407-758-1472)

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: Under contract-accepting backup offers. Short Sale. One of the most sought-after floor plans, this 4-bedroom, 2-bathroom home boasts numerous charming features and is set on an oversized lot with no rear neighbors and a serene water view. As you enter, you'll find three spacious bedrooms and a modern bathroom. To the left, the inviting, contemporary kitchen showcases a large pantry offering ample storage space. The open dining area flows seamlessly into the airy living room, creating a perfect space for gatherings. Step outside to your private screened-in patio and enjoy the expansive yard with a tranquil, picturesque view. The luxurious Master Suite features dual sinks and a generous walk-in closet. The kitchen island and open layout are perfect for entertaining. This home comes complete with all major appliances, blinds, and is equipped with Smart Home Technology, including Alexa. Conveniently located near I-4, shopping, and entertainment, and offering access to a community pool. All of this at an unbeatable price in an up-and-coming location!

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III (407-207-0825)

Listing Agent: Krichely Gonzalez Rodriguez (407-953-4377)

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: 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: WATERFRONT! ON THE CANAL TO THE CHAIN OF LAKES!! This townhouse is low-maintenance and offers a tranquil setting right in the middle of town, great location!. Primary bedroom with ensuite and screened-in balcony, one car garage and open concrete patio. The screened patio is perfect for enjoying views of boaters and paddle boarders passing between the lakes. Focusing on recreation, this home is in the perfect spot for a multitude of outdoor activities. Community features include a sparkling pool . Fish from your backyard at the bank of Lake Lulu! This residence is convenient to Great restaurants, medical, shopping, entertainment, and LEGOLAND! Check us out today to see what Florida waterfront living is all about!

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

Listing Agent: Rick Hemenway (863-289-5657)

Remarks: Fully remodeled 2-bedroom, 1-bath home in the heart of Winter Haven. This move-in-ready property features a new roof, updated electrical and plumbing, and modern finishes throughout. Situated on a spacious lot with no HOA, it offers both comfort and flexibility. Conveniently located near major roads, shopping, dining, schools, and just minutes from downtown Winter Haven and LEGOLAND Florida Resort, making it an excellent option for homeowners or investors.

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

Listing Agent: Maria Loayza Jimenez (570-856-6822)

Remarks: One or more photo(s) has been virtually staged. Welcome to your gorgeous new home! This executive style home is located in the highly sought after gated community, Eloise Pointe Estates, and is conveniently located 1/4 mile behind Legoland. Community was originally developed by then Boston Red Sox owner, Buddy Larue when they spring trained in Winter Haven. Upon entering this desirable 4 bedroom 3.5 bathroom home one finds many updates, completely remodeled kitchen and primary bathroom. New cabinetry, granite counter-tops, beautiful tongue and groove wood ceiling in the kitchen, paint (including the pool deck) & LVP flooring throughout. The laundry room is also plumbed for a sink. Upstairs over the garage is the 4th bedroom and full bath or use as a Bonus/Theatre room. Also included is an oversized three car garage, a large lot with some beautiful scrub oak trees on just over a 1/2 an acre & privacy fenced. Screened in 15x30 pool. Another great feature of this home is the low HOA fee of only $1200 for the year and no CDD.

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

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

Remarks: Located in the 55+ community of Brookhaven Village, this fee-simple manufactured home offers 1,620 square feet of living space with a functional layout and recent updates. Built in 1990, the home features 2 bedrooms and 2 bathrooms, with vinyl and carpet flooring throughout. The interior includes a spacious living and dining area, an interior laundry closet, and ample storage. An attached storage room provides additional space and may be suitable for use as a workshop, hobby area, or general storage. The home also features a covered and screened porch, offering a comfortable space to enjoy the outdoors. Recent improvements include a roof replaced in 2023 and an HVAC system replaced in 2022. The home may be conveyed fully furnished, providing a convenient option for buyers. Brookhaven Village offers community amenities including a clubhouse, pool, shuffleboard courts, and organized social activities. The HOA fee is $34 per month, and the community enforces age restrictions in accordance with its 55+ designation. Conveniently located in Winter Haven with access to shopping, dining, and local amenities, this property offers an opportunity for low-maintenance living in an established adult community.

Listing is courtesy of: COLDWELL BANKER REALTY (863-687-2233)

Listing Agent: Daniel Mcfee (863-273-6324)

Remarks: Welcome to this beautifully updated home in Winter Haven! This move-in ready property combines classic charm with modern upgrades, featuring stunning high-gloss marble-style porcelain flooring throughout that creates a bright and elegant living space. Enjoy a spacious layout filled with natural light, a well-maintained kitchen with stainless steel appliances, wood cabinetry, and a stylish backsplash — perfect for everyday living. The home also offers a renovated bathroom with modern finishes and a convenient interior laundry area. Step outside to a large, fully fenced backyard, ideal for entertaining, pets, or simply enjoying your own private outdoor space. The covered carport and extended driveway provide ample parking. Located in a quiet, well-established neighborhood, this home is perfect for first-time buyers or investors. Property is being sold AS-IS, presenting a great opportunity for buyers looking for value and flexibility. Schedule your private showing today!

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

Listing Agent: Gabriel Rivera Gonzalez (407-724-4717)

Remarks: Ready Now! Introducing Villa Mar in Winter Haven, Florida. Master-planned amenities including a pool with cabana that is walking distance from your home, a playground, and shaded seating area. Highway 27, less than 10 minutes away, has everything you are looking for. Grocery stores, movie theaters, shopping centers, golf courses, restaurants, and so much more. The Glen Ridge single-family home is your key to great living. An open floor plan makes entertaining a breeze. Play a game in the family room or gather round the dining room table for a delicious meal, home cooked in the gorgeous gourmet kitchen with large island and walk-in pantry. The 2-car garage offers convenient extra storage. Upstairs, 2 bedrooms and a full bath give guests plenty of privacy. Make the most of your loft by using it as a second living space or media center. Your luxury owner’s suite includes dual walk-in closets and double vanities. You’re going to love The Glen Ridge. 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: Short Sale. Step into one of the largest units at the vibrant 55+ community of Imperial Harbor in Winter Haven! This spacious 3-bedroom, 2-bath condo also features a bonus room. With three comfortable bedrooms, there’s ample space for guests, a home office, or crafting area. Enjoy an active lifestyle with shuffleboard courts, a well-equipped gym, and a billiard room. The heated pool ensures year-round relaxation, and a private community dock on Lake Howard is ideal for boating and fishing enthusiasts. Association dues cover water, basic cable, and internet, and also include access to dock your own boat. Located in the heart of Winter Haven, Imperial Harbor offers a serene and friendly community atmosphere, close to shopping, dining, recreational activities, and medical facilities. Act quickly because a property like this will not last long.

Listing is courtesy of: REALTY COOPERATIVE (800-704-6411)

Listing Agent: Tony Giglio (513-505-5222)

Remarks: Charming and inviting, this 3-bed, 2-bath home sits in a lovely Winter Haven community with a very low HOA. Built in 2015, it offers a modern design, a comfortable one-level layout, a 2-car garage, and all appliances included. Tucked into the vibrant Chain of Lakes region, you’re surrounded by peaceful views, leafy lakes, and plenty of outdoor fun from boat cruises to paddle boarding. And when it’s time for entertainment, you couldn’t be better located: you’re just 20 minutes from LEGOLAND Florida Resort, and only about 30 miles from Walt Disney World, making magical Orlando day trips effortless.

Listing is courtesy of: MARZUCCO REAL ESTATE (813-679-1365)

Listing Agent: Clarisa Moody (813-446-2003)

Remarks: Seller motivated. Welcome to your home in Winter Haven—just minutes from Legoland, shopping, medical facilities, and Highway 27 for easy commuting! Originally a 3-bedroom, 2-bath layout, this home has been converted into a spacious 5-bedroom, 2-bath residence, offering incredible versatility for growing families, multigenerational living, or those needing extra space for a home office or hobby rooms. It will need some TLC due to tenant being in property. With five true bedrooms, everyone in the family can have their own retreat while still enjoying generous shared living spaces. Outside, you’ll find a property ideally situated for convenience—whether you’re heading to Legoland for weekend fun, accessing everyday amenities just minutes away, or commuting via Highway 27. This home offers the perfect blend of location, and space in one of Winter Haven’s most desirable areas.

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

Listing Agent: Brandy Duncan (863-585-6849)

Remarks: Under contract-accepting backup offers. Welcome to the Serendipity floor plan — where comfort meets style! This stunning three-bedroom, den, two-bathroom home offers the perfect blend of modern design and everyday convenience. Step inside to find a bright, open-concept layout featuring high vaulted ceilings, a spacious great room, a beautifully appointed kitchen with a large island and walk-in pantry, and a cozy dining area ideal for gatherings. The owner’s suite provides a peaceful retreat with dual walk-in closets and a luxurious en-suite bath. The flexible den is perfect for a home office, guest space, or hobby room, offering versatility to fit your lifestyle. Enjoy year-round outdoor living in the beautiful enclosed lanai overlooking the fully fenced backyard—perfect for relaxing or entertaining in privacy. Located in a highly desirable area, this home offers convenient access to top-rated schools, shopping, dining, parks, and houses of worship. Designed for both elegance and functionality, the Serendipity truly lives up to its name—a happy discovery of the place you’ll love to call home.

Listing is courtesy of: CORCORAN CONNECT LLC (407-953-9118)

Listing Agent: Kelly Martinez (407-864-8965)

Remarks: One or more photo(s) has been virtually staged. Welcome to this beautiful home in peace creek reserve! this thoughtfully designed single-story residence offers 4 bedrooms and 2.5 bathrooms, combining comfort and functionality. The open-concept floor plan seamlessly connects the family room, dining area, and kitchen—complete with a central island—creating the perfect space for everyday living and entertaining. Located in the desirable peace creek reserve community, residents enjoy a serene setting surrounded by nature, including a picturesque creek. situated in winter haven—known as the chain of lakes city with over 26 connected lakes—this area offers a variety of shopping, dining, and outdoor activities such as biking and water recreation. Peace creek reserve provides the perfect balance of a peaceful, small-town atmosphere with everyday convenience—an ideal place to call home.

Listing is courtesy of: GLASSTONE GROUP INC (321-988-4663)

Listing Agent: Barbara Cunha De Freitas (617-458-0838)

Remarks: Under Construction. 2-story new construction townhome with 1,604 square feet, 3 bedrooms, and a covered lanai, located in the brand-new Harbor of Lake Henry community. Downstairs, enjoy an open layout(optional first floor layout with den)and a gourmet kitchen with, shaker-style wood cabinets, Samsung stainless steel appliances, including a pantry. The spacious gathering room opens to your covered lanai. The entire lower level and upstairs baths are finished with luxury vinyl plank flooring, with stain-resistant carpet in the bedrooms. Upstairs, you'll find three spacious bedrooms including your owner's suite complete with a walk-in wardrobe, linen closet, and a private en-suite bath with dual vanities and a tiled shower. Additional features for your convenience include a half bath downstairs, upstairs hall bath for the secondary bedrooms, energy-efficient insulation and windows, and a full builder warranty.

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

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

Remarks: 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: Welcome to TRADITIONS, an active 55+ gated community located in the heart of the state on Lake Ruby. From swimming laps in the olympic size pool, casting a line at the lake, swinging a pickleball racquet or utilizing the fitness room and scheduled classes, there is plenty to do to stay in shape. If you prefer a more relaxed day, the clubhouse provides plenty of social spaces for card games, crafting, puzzles and reading a book. The community has planned monthly activities, they even plan a yearly community cruise if that's your vibe. You don't need to leave the community to find something to do, however; Disney and Universal Studios are nearby and you can reach either coast in less than two hours. The community is close to shopping (Publix coming soon), medical facilities, Legoland and the quaint downtown area of Winter Haven with boutique shops and local restaurants. This community is truly the ultimate 55+ lifestyle. The monthly dues include: community amenities, Spectrum cable and internet, lawn maintenance, common area maintenance, and exterior paining every 8 years. Now for the house: This is a Kennedy model floorplan, one of the most sought after in this community. It is a SHOW STOPPER from top to bottom and these Sellers have executed great care during their ownership. You will appreciate some of the additions they have made such as the extended rear screened lanai with Coolaroo shades and a motorized hurricane shutter. They also extended a paver BBQ area for those who like to grill. They added overhead storage racks in the garage and if you are an angler you will appreciate the storage system for the fishing poles! They have also added a motorized screen door for the days that you want to tinker in the garage and keep the bugs out. The exterior was just painted in 2025. The lawn is manicured with professional landscape edged flower beds and best of all the grass is maintained by the HOA. Step inside the front door to be instantly impressed with the high ceilings. The space is open enough for great entertaining but also offers space to spread out when needed. Ceramic tile in all the wet areas and living spaces with 5 inch baseboards and crown molding give the feeling of luxury. Recessed lighting, pendant lights as well as good window placement bring good lighting into the space. The kitchen is spectacular. 42 inch upper cabinets, quartz counters, walk in pantry and preparation island make the space functional for the chef and easy to entertain in. There are three dining space choices: formal dining area, breakfast nook and a breakfast bar providing with plenty of seating. The living room flows perfectly from the triple sliding door onto the lanai. The wall mounted TV's convey. The floorplan also offers a triple split bedroom plan. The primary bedroom offers an ensuite and the walk in closet has custom built in shelving. The ensuite has dual sinks, private commode room, linen closet and soaking tub. The walk in shower has no step and has nice glass doors. The 2nd and 3rd bedrooms share a guest bath with dual sinks and the 4th bedroom has a private ensuite. You truly have to see this home to appreciate its flow, style, tidiness and all the features that make this place a HOME! If 55+ living in Florida is what you have been dreaming of, you just found it! Come make some new Traditions!

Listing is courtesy of: DREAM REALTY GROUP (863-450-7973)

Listing Agent: Christie Weeks (863-450-7973)

Remarks: Valhalla - A GATED subdivision with pool, club house and more! 3-bedroom, 2-bath villa home with a connecting property but considered a single family home. This special villa has a functional layout with updated features throughout. A screened entry with leaded glass doors opens to vaulted ceilings and custom architectural touches. The open concept kitchen includes granite countertops, custom cabinetry, a center island with breakfast bar, Bosch dishwasher, stainless oven and range, walk-in pantry, and a passthrough to the living area for open flow. Wood plank flooring runs throughout the main spaces. The living room features large windows and an adjacent flex space for dining, office, or den use. The primary suite includes an ensuite bathroom with slate tile, jacuzzi tub, glass shower, dual sinks, and the laundry room is part of the primary. The guest room features a window seat and recessed lighting. A third room functions well as an office or additional guest space. HOA covers lawn care, water, trash, basic cable, pool, and tennis access.

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

Listing Agent: Karen Myers (863-651-4636)