Winter Haven Homes For Sale & Real Estate - 978 homes

Remarks: Move-in Ready! Welcome to the Residences at Winter Haven, a premier new single-family community designed for those who value both quality and connection. Set within this inviting neighborhood, the Crystal River Gen Suite floor plan brings a versatile elegance to everyday living. The open layout is anchored by a stunning gourmet kitchen featuring a waterfall island, while a private Gen Suite offers ultimate flexibility and independence with its own entrance, bath, and kitchenette. It’s a lovely modern space that’s ready for you to make it your own.

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

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

Remarks: Welcome to 2235 Lakeridge Estates, your opportunity to enjoy the Florida lifestyle in one of Winter Haven's growing and desirable communities near scenic Lake Hartridge and the Beautiful Winter Haven Chain of Lakes. An exceptional opportunity to own a beautifully designed home in the heart of Winter Haven. Nestled within the desirable Lakeridge Estates community near scenic Lake Hartridge, this well-maintained 3-bedroom, 2-bathroom residence offers nearly 1,893 square feet of thoughtfully designed living space, blending comfort, functionality, and Florida lifestyle appeal. From the moment you arrive, you’re greeted by a welcoming entry that opens into a bright, open-concept floor plan featuring vaulted ceilings and a seamless flow between the living and dining areas—perfect for both everyday living and entertaining. The spacious kitchen is a standout, complete with stainless steel appliances, ample cabinetry, a center island, and a pantry, making it as practical as it is stylish. The split-bedroom layout offers privacy and comfort, with a generously sized primary suite featuring a walk-in closet and an en-suite bath with dual features designed for relaxation. Two additional bedrooms provide flexibility for guests, family, or a home office. Step outside to one of this home’s most desirable features—a spacious backyard, ideal for outdoor gatherings, pets, or creating your own private oasis. The covered rear porch extends your living space outdoors, capturing the essence of Florida indoor-outdoor living. Location is key, and this home delivers. You’re just minutes from everyday conveniences including shopping destinations, along with casual dining options. Beyond daily conveniences, Winter Haven is known for its vibrant charm and attractions. Enjoy weekends exploring the nearby Chain of Lakes, or take a short drive to world-renowned destinations like LEGOLAND Florida Resort, a major area highlight for entertainment and recreation. The revitalized downtown district offers local boutiques, dining, and community events, adding to the area’s growing appeal. Whether you’re a first-time buyer, growing household, or investor, 2235 Lakeridge Drive presents a compelling blend of space, location, and lifestyle—an inviting place to call home in one of Central Florida’s most steadily growing markets.

Listing is courtesy of: LA ROSA REALTY CENTRAL FLORIDA LLC (407-861-8009)

Listing Agent: Maria Elena Fernandez (407-704-0732)

Remarks: Under Construction. The Ponte Vedra floor plan at Willowbrook North offers spacious two-story living with 5 bedrooms, 3 full baths, and approximately 2,371 square feet of thoughtfully designed space. This open-concept home features a modern kitchen overlooking the great room and dining area, a spacious primary suite, flexible living areas, and available options. Located near Lake Fannie and adjacent to Willowbrook Golf Club, Willowbrook North offers scenic surroundings with convenient access to shopping, dining, parks, downtown Winter Haven, and major commuter routes to Orlando and Tampa. Buyers will also enjoy energy-efficient features and modern interior finishes.

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

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

Remarks: Under Construction. New construction home with 2227 square feet on two-story including 4 bedrooms with loft, 3.5 baths, and an open living area. Enjoy an open kitchen with Quartz countertops, Samsung stainless steel appliances, a walk-in pantry, and a spacious island, fully open to the dining café and gathering room. The living area, laundry room, and baths include luxury wood vinyl plank flooring, with stain-resistant carpet in the bedrooms. Your owner's suite is complete with a walk-in wardrobe and a private en-suite bath with dual vanities, and a tiled shower. Bedrooms 2 and 3 share a jack-and-Jill bathroom. Plus, enjoy a covered lanai, 2-car garage, custom-fit window blinds, architectural shingles, energy-efficient insulation and windows, and a full builder warranty. “Please note, virtual tour/photos showcases the home layout; colors and design options in actual home for sale may differ. Furnishings and decor do not convey."

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

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

Remarks: Under contract-accepting backup offers. Hidden gem with upgrades you won’t expect! First-floor condo for easy access and numerous updates throughout. The kitchen features a new backsplash, new sink and faucet, freshly painted cabinets, and newer appliances, including the refrigerator and dishwasher. A new water heater adds additional peace of mind. Both bathrooms have been updated with new vanities, faucets, and tile backsplashes. Custom wood shelving has been installed throughout the home—no wire shelving—along with custom closet organizers in both bedrooms. The spacious primary bedroom features beautiful plantation shutters. Stylish barn doors enclose the laundry area with a washer and dryer, and the hall closet. Covered parking included. Situated on scenic Lake Howard, part of the famous Winter Haven Chain of Lakes, this community offers boat dock access. Residents also enjoy a sparkling pool, gazebo with grilling area, shuffleboard courts, and a quiet, secure atmosphere. Even better, the HOA covers cable, internet, water, sewer, trash, exterior maintenance, and lawn care—you only pay for electricity. Truly affordable, maintenance-free Florida living.

Listing is courtesy of: VILLAGE REALTY OF WINTER HAVEN (863-299-6767)

Listing Agent: Nancy Cini (727-612-0375)

Remarks: One or more photo(s) has been virtually staged. Welcome to 3228 Country Walk Club Cir in Winter Haven! This spacious two-story home features 5 bedrooms and 3 bathrooms, offering plenty of room for family and entertaining. The home has been updated with fresh interior paint, brand-new carpet and vinyl flooring throughout, and modern lighting fixtures. The kitchen comes equipped with new stainless steel appliances and opens to the dining and living area for a comfortable, functional layout. One bedroom is conveniently located on the first floor, with four additional bedrooms upstairs. The master suite features two walk-in closets and an updated bathroom with dual vanities and a newly tiled walk-in shower. The second upstairs bathroom also includes dual vanities for added convenience. A bonus area upstairs provides flexible space perfect for a playroom, home office, or media room, along with an upstairs laundry room for easy access. Outside, enjoy a large backyard and an attached two-car garage. Schedule your showing today! Some photos in this listing have been virtually staged to help illustrate the property’s potential. No physical changes have been made to the property.

Listing is courtesy of: PALM ISLAND REALTY (813-843-2233)

Listing Agent: James Nagy, Pa (813-843-2233)

Remarks: NEW CONSTRUCTION! This brand-new single-story, two bedroom, two bath Villa is located in Vienna Square, a 55+ gated community in Winter Haven. Live a low maintenance lifestyle with tranquil views from your screened lanai which is accessible from the villa’s open floor plan. This villa features a two car garage, paver driveway, granite counter tops, shaker cabinets, new Whirlpool appliances, Delta fixtures, designer lighting, inside laundry and more. In the owners retreat, there is a walk-in closet and tiled walk-in shower. The guest bathroom has a tub/shower combo. Lawn maintenance and most exterior maintenance are included in the monthly HOA dues, along with Spectrum basic cable/internet, access to the clubhouse, heated pool, fitness center, and more. This new home comes with a structural warranty. Call today!

Listing is courtesy of: DGCF REALTY ADVISORS LLC (877-791-9907)

Listing Agent: Austin Schreiber (863-287-8877)

Remarks: Beautifully Maintained Home in Winter Haven! This stunning property shows just like a model home! The owners have kept it immaculately maintained and spotlessly clean. Built in 2023, everything is practically brand new, offering true peace of mind. This 4 bedroom 2.5 bath home has an Open-Concept Living area, Kitchen and Dinning that are perfect for everyday living and entertaining. Modern Kitchen: Features up-to-date finishes, including beautiful granite countertops and durable tile flooring. Move-In Ready: All appliances, including the washer and dryer, stay with the home! Brinks home security system for added peace of mind. All bedrooms and laundry including the spacious primary suite, are conveniently located upstairs. The primary bedroom floods with natural light and features a beautiful en-suite bathroom with a walk-in shower and a generous walk-in closet. Situated on a large corner lot, the backyard is completely fenced-in and features a double gate for easy access. The Lanai is ideal for hosting family and friends for a cookout. Best of all, this community has NO CDD and a low HOA fee! Prime Location Located in a highly desirable area of Winter Haven, you'll be just minutes away from the new Target, excellent shopping, dining, and LEGOLAND! Priced to move, Welcome Home!

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

Listing Agent: Rose Cayson (863-559-4360)

Remarks: One or more photo(s) has been virtually staged. Welcome to 718 Eagle Landing Blvd, where privacy, peaceful views, and modern living come together beautifully. Built in 2023 and sitting on one of the most desirable lots in the community, this home offers something that’s becoming harder and harder to find, open green space behind your home instead of another row of back windows. No rear neighbors. No cramped feeling. Just peaceful views and room to breathe. Recently refreshed with fresh interior paint, pressure washing, updated landscaping, and new mulch, this home is completely move-in ready and shows beautifully from the moment you arrive. Inside, natural light pours throughout the open-concept layout, creating a space that feels bright, welcoming, and comfortable all day long. The design is modern without feeling cold, offering the perfect balance of style and everyday livability. The spacious primary suite serves as a relaxing retreat with dual closets and a large walk-in shower, while the additional bedrooms offer flexibility for family, guests, a home office, playroom, or hobby space. But what truly makes this home special is the backyard potential. Whether you dream of adding a pool, building the ultimate outdoor entertaining space, creating a peaceful garden retreat, or simply enjoying wide open views without staring directly into another home, this property gives you the space and flexibility to make it happen. Rear fencing is permitted, giving future owners even more possibilities. Located in a growing area near shopping, dining, the Chain of Lakes, LEGOLAND Florida Resort, and the future SEA LIFE Florida Aquarium, this is a home positioned in an area that continues to grow in popularity and convenience. Homes with this combination of privacy, newer construction, natural light, and backyard potential rarely come available at this price point. Schedule your private showing today before someone else grabs one of the best lots in the community.

Listing is courtesy of: M2M REALTY (407-401-2275)

Listing Agent: Micaela Navarra (407-761-5501)

Remarks: Short Sale. $50,000 PRICE REDUCTION! Welcome to your perfect retreat in this exclusive gated community, where tranquility meets convenience! Enjoy easy access to shopping, dining, and the exciting attractions of Winter Haven, including Legoland Theme Park, all just minutes away. This charming three-bedroom, two-bathroom home features a modern open-concept layout and a split bedroom design for added privacy. You'll love the luxury vinyl flooring throughout the living areas, with cozy carpet in the bedrooms. Step outside to your large, fully fenced backyard—perfect for relaxation without any rear neighbors. Unwind in your spacious screened-in lanai, ideal for enjoying the outdoors year-round! Additional highlights include an 8 x 5 fireproof storage closet in the garage, providing peace of mind for your valuables, as well as a well-maintained irrigation system and beautiful landscaping that enhances the curb appeal. With quick access to the Polk Parkway and Interstate 4, Central Florida adventures are at your fingertips. Don’t miss out on this fantastic opportunity—schedule your showing today!

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

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

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: Under contract-accepting backup offers. Short Sale. Packed with potential! This spacious two-story home, featuring 4 bedrooms, 2.5 baths, and a versatile bonus room needs some repairs, cleaning, and TLC, but that’s where the attractive price comes in! The main floor includes a large great room, white kitchen with granite countertops, front living room/den, laundry, enclosed bonus room and a 3-car garage. The lanai offers a great outdoor entertaining space. Upstairs, the primary suite offers dual sinks, tub and separate shower, and dual walk-in closets, and the other bedrooms. Not in a flood zone and low HOA fees of $165/year ensure long-term low cost of ownership. Trustee Sale, must sell!

Listing is courtesy of: FUTURE HOME REALTY INC (813-855-4982)

Listing Agent: Tanja Cisliek (727-480-4155)

Remarks: UNDER MARKET VALUE!!! Brand NEW AC Fan motor, AC Amp Fuse and AC capacitor installed May 2026. Brand NEW fire/carbon monoxide detector alarms throughout the home. Welcome home to this beautiful 2-bedroom, 2-bathroom golf villa nestled within the beautiful Cypresswood Golf and Country Club in Winter Haven, Florida. Property is steps away from the golf clubhouse!!! Home features a stunning Florida room, ready for relaxation. Dry bar with sink in living room perfect for entertaining your guests. Step out to your outside patio for even more enjoyment. With access to golf, clubhouse, Restaurant, pool and recreational facilities, this home offers a low-maintenance lifestyle in an active and vibrant community. Legoland attraction is approximately 5 miles. Disney World, Orlando and Tampa attractions are within 30-60 minute driving distance. Opportunities like this don’t last long, Just buy and move in!!! CLEAN TITLE WITH NO LIENS. Property being sold AS-IS. ALL interior contents and furniture convey with the property.

Listing is courtesy of: SUCCESS INVESTMENT REALTY (407-304-0490)

Listing Agent: Bill Sprys (407-574-9724)

Remarks: NOW OFFERING A HOME WARRANTY! Your opportunity to own in the highly sought-after Cypresswood Golf & Country Club just became even more appealing. Welcome to The Tennis Villas, where gated security, resort-style amenities, and maintenance-friendly living come together in one of Central Florida’s premier golf communities. A charming wrought iron gate welcomes you into a private front courtyard patio, creating the perfect space to enjoy morning coffee, entertain guests, or simply relax in privacy. Inside, this well-maintained 2-bedroom, 2-bath villa offers spacious living and dining areas with laminate flooring, an open-concept layout, and thoughtful features designed for comfortable Florida living. The bright kitchen features updates, ceramic tile flooring, and flows seamlessly into the main living space, complete with a wet bar and additional cabinet storage—ideal for entertaining. A bonus Florida room with air conditioning overlooks a peaceful open field and pond, providing tranquil views and additional year-round living space. The primary suite offers direct access to the enclosed lanai through sliding glass doors, creating a relaxing retreat with serene backyard views. Recent improvements include a NEW metal roof for added value and peace of mind. Enjoy truly low-maintenance living with HOA services that include exterior painting, roof maintenance, lawn care, and pest control, allowing you more time to enjoy everything Cypresswood has to offer.Community amenities include:?• 18-hole championship golf course designed by Ron Garl?• Junior Olympic-sized swimming pool?• Lighted tennis courts?• Fitness center and clubhouse with pro shop?• On-site restaurant and event space Whether by golf cart, bicycle, or a short walk, all amenities are conveniently nearby. Ideally located just minutes from Highway 27, I-4, Legoland Florida Resort, the Polk Parkway, shopping, dining, and medical facilities, this villa offers both convenience and lifestyle. Don’t miss your chance to enjoy affordable country club living in a secure, beautifully maintained community. Schedule your private showing today and experience the Cypresswood lifestyle for yourself.

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

Listing Agent: Corinna Weaver (863-258-2901)

Remarks: Welcome to 8 The Village Blvd—nestled in a highly desirable gated community in Winter Haven with exclusive access to beautiful Spirit Lake! This well-maintained former model home offers 3 bedrooms, 2 baths, and a 2-car garage, combining comfort, style, and thoughtful upgrades throughout. Step inside to an inviting open floorplan featuring gleaming wood floors, a formal dining area overlooking the spacious front yard, and a stunning magnolia tree that enhances the home’s curb appeal. The kitchen is designed to impress with Corian countertops, upgraded appliances, and abundant cabinet and counter space, flowing seamlessly into a bright breakfast nook with views of the backyard and large screened lanai. The split-bedroom layout provides privacy, with two generously sized guest bedrooms and a full bath (with lanai access) tucked away on one side of the home. The spacious primary suite is located on the opposite side and features sliding glass doors to the lanai, dual walk-in closets, and a luxurious en-suite bath complete with a garden tub, separate shower, and ample counter space. Major updates offer peace of mind, including a new roof (May 2023), upgraded 50-gallon water heater (2021), new garage door opener (2022), upgraded main electrical panel (2024), and a Brinks Home Security System and Goodman AC (2025) with transferable warranty. The 2-car garage includes a Chamberlain opener (2022), built-in shelving, and a pegboard—perfect for organization. Enjoy all the amenities this sought-after gated community has to offer, including a clubhouse, recently refinished pool, tennis and basketball courts, updated exterior lighting, and a freshly painted entrance and clubhouse. Residents also enjoy private access to Spirit Lake via a boat ramp and dock. This move-in-ready home is truly “neat as a pin” and ready for its next owner. Survey and floorplan available—schedule your private showing today!

Listing is courtesy of: HOUWZER INC (267-765-2080)

Listing Agent: Daniel Robinson (904-447-8922)

Remarks: Under contract-accepting backup offers. Come enjoy the beautiful Florida sunsets, In this beautiful, furnished home. You can relax in the enclosed Florida room, Carport is long enough to put two cars in. floors have the beautiful laminate wood flooring, all through out the livingroom,and dining areas. All located in a beautiful gated 55 plus park. Two heated pools, two clubhouses, tennis ,fishing pier, minature golf, shuffle board, plus much more. this home want last, act fast.

Listing is courtesy of: SOUTHERN BELLE REALTY (863-299-7800)

Listing Agent: Reta Stead (863-299-7800)

Remarks: Sitting on Lake Jessie and on a beautiful lot along the Winter Haven Chain of Lakes, this property offers an incredible opportunity to own waterfront living at an affordable price point. Known as the “Chain of Lakes City,” Winter Haven features dozens of interconnected lakes perfect for boating, fishing, watersports, and enjoying the true Florida lifestyle. Whether you’re looking for a full-time residence, seasonal snowbird retreat, or a smart long-term investment opportunity, this home is priced right for someone ready to make a few updates while securing a spot on the highly desirable main Chain of Lakes. Opportunities like this are becoming harder and harder to find. The home includes a metal roof, updated AC system, and updated plumbing, giving you a solid foundation to make it your own. The oversized lot provides plenty of extra driveway space and room to add a large garage or additional storage for boats, trailers, or recreational vehicles. Relax and unwind in the screened-in area while enjoying the peaceful lake breeze and beautiful waterfront surroundings. With endless potential and a low price, this property is a rare chance to create your dream lakefront getaway without breaking the bank.

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

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

Remarks: HOME WARRANTY INCLUDED & PRICE IMPROVEMENT! Now offered at an even better value, this beautifully maintained home in Brookhaven’s desirable 55+ community is the perfect opportunity to enjoy comfortable Florida living with owned land and low HOA fees. Located on a corner lot on a quiet dead-end street, this 2005 Homes of Merit double-wide manufactured home offers 1,440 sq. ft. of well-designed living space and comes fully furnished and move-in ready. The spacious open floor plan features 3 bedrooms, 2 bathrooms, an indoor laundry room, and abundant natural light throughout. Elegant tray ceilings enhance the main living area, while sliding glass doors lead to an additional porch overlooking a peaceful neighboring pasture—an ideal place to relax and enjoy the view. The large kitchen is designed for both functionality and entertaining, featuring a center island, ample cabinet and counter space, updated microwave, newer refrigerator (2024), and A/C unit (2024). Recent improvements provide added value and peace of mind, including a new shingle roof and carport (2023), updated siding, reinforced tie-downs, fresh interior paint, and new Parkay Endurance water-resistant laminate flooring. A versatile bonus room with French doors offers flexibility for a home office, hobby room, or third bedroom. The guest bedroom and bath are generously sized, while the oversized primary suite includes a private ensuite bathroom for added comfort and privacy. Additional features include an indoor laundry room with washer and dryer included, a spacious workshop/storage area, and valuable extras such as an 8,000-watt generator (gas or propane) with two propane tanks, mower, trimmer, and power washer. Surrounded by mature landscaping, this property offers both charm and tranquility. Brookhaven residents enjoy amenities including a community pool, clubhouse, and shuffleboard, all with a low HOA fee of just $34 monthly. Conveniently located near Hwy 27, shopping, restaurants, and medical facilities, this home is also approximately one hour from Disney and within easy driving distance to both Florida coasts. Don’t miss your opportunity to own this well-maintained, fully furnished home with owned land in one of Central Florida’s welcoming 55+ communities. Schedule your private showing today.

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

Listing Agent: Corinna Weaver (863-258-2901)

Remarks: One or more photo(s) has been virtually staged. Behind the gates of Winterset, one of Winter Haven’s most sought-after lakefront communities, this 3-bedroom, 2-bath home built in 2006 offers 1,994 SF of comfortable living space. A covered, screened front porch welcomes you into a spacious great room that opens to a 550 SF screened rear porch with beautiful porcelain tile, ideal for indoor-outdoor living. NO Carpeting throughout, durable laminate flooring in 2020 was placed in the entire house. The split floor plan includes secondary bedrooms, sharing a hall bath with tub and linen closet. Inside laundry room includes washer and dryer, new water heater (2026), HVAC is 2021. Additional features include a tile roof with a brick paver driveway, 2-car garage and a garage screen door, offering added ventilation and flexible use of the garage. Situated on a large corner lot, this home provides added space and privacy.. Winterset community amenities include a lakefront clubhouse overlooking Lake Winterset, heated pool and spa, tennis and pickleball courts, shuffleboard, and a private boat ramp with access to Lake Winterset, part of the renowned Winter Haven Chain of Lakes. HOA fees include exterior maintenance, grounds maintenance, security, and access to all community amenities. Conveniently located near LEGOLAND® Florida, shopping, dining, and medical facilities. Centrally positioned between Tampa and Orlando with easy access to theme parks, beaches, and airports, this home offers comfort, natural beauty, and resort-style living in a peaceful, gated community.

Listing is courtesy of: REMAX EXPERTS (863-802-5262)

Listing Agent: Laura Slocumb (863-660-7000)

Remarks: Short Sale. Short Sale. Looking for a nice home with amazing potential and opportunity to gain equity? This one may be IT for you! Welcome to this 3-bedroom, 2-bath move-in ready home located in the peaceful and sought-after SE Winter Haven area! Situated on an OVERSIZED corner lot, this home features a fully fenced backyard, high ceilings, and ceramic tile flooring throughout the main living spaces. You’ll love the screened-in lanai and Private Pool—perfect for relaxing or entertaining year-round. The kitchen boasts custom cabinetry, a cozy dinette with wraparound windows, and direct access to an oversized garage. The spacious master bedroom features a walk-in closet, while the additional bedrooms are ideal for family or guests. This home has AMAZING POTENTIAL and nestled in a quiet, well-kept neighborhood, just minutes from Legoland and all of Central Florida’s top attractions. Call today to schedule your private showing—this home is priced to sell and won’t last long!

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

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