Winter Haven Homes For Sale & Real Estate - 921 homes

Remarks: Fresh on the market is this meticulously maintained and professionally updated 2 bedroom 2 bath villa located in the sought after "Enclave" neighborhood in Cypresswood, a gated golf community in SE Winter Haven. The open floor plan features an expansive kitchen with breakfast nook, spacious living/dining room combo, split bedrooms with ample closets, inside laundry area equipped with a washer and dryer, screened lanai and a 2 car garage with garage door opener. Per the owner, recent upgrades include removal of a wall separating the kitchen from the living area thereby creating a true open-concept living area, upgraded matching stainless kitchen appliances, flooring in the kitchen, living room, foyer, hall and 2 bedrooms, New granite counter-tops, sinks and faucets in the kitchen and both bathrooms, new LED lighting, New front entry door, new window treatments and fresh interior paint. This is truly a move-in-ready villa with quality upgrades that set it ahead of the competition. Come and enjoy the Florida Country Club Lifestyle in this low maintenance villa.

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

Listing Agent: Steven Smith, Pa (863-224-2297)

Remarks: Price Improvement. Offered for the first time, this stunning custom-built luxury home in SE Winter Haven in the gated community of Heron Cay. This exquisite Mediterranean style home features 3,640 square feet of living space with 4 bedrooms, plus a large flex room, 3 ½ baths plus a gorgeous pool and outside entertaining area on a lot measuring .61 acres. As you enter through the front double doors with custom decorative iron work and a soaring ceiling of over 21 feet, you are in a magnificent foyer. The living room has the first of two wood/gas fireplaces with views and access to your private pool via the oversized arched glass French doors on either side of the fireplace. The elegant dining room is oversized and perfect for large family gatherings or entertaining and is adjacent to your cook’s dream kitchen. In addition, off the entry foyer is a home office with a massive built in book case and desk with the flexibility to also be a 4th bedroom. The kitchen is a culinary dream with custom cabinetry, granite countertops, a spacious island, a walk-in pantry and upscale stainless appliances including a gas stove and double wall oven. The kitchen overlooks the great room, the breakfast nook and the pool. The great room ceiling beams are another architectural feature, and a second wood/gas fireplace is a focal point of this amazing room. Crown molding, columns, hurricane rated windows, and a neutral color palette are throughout this home. Next to the great room is a large bonus/ flex space with French doors that can be used as a playroom, a library or even a workout space. The oversized primary bedroom has access out to the pool and features a spa type ensuite complete with a soaking tub and dual vanities. Twin oversized, walk-in closets feature built in shelves for keeping everything organized with access being via barn doors with glass panels. The guest rooms on the other side of the house have separate toilet/vanity areas with a shared tub/shower and private hallway. These are the only two rooms with carpet and it is a low pile neutral Berber style. Both guest rooms have oversized, walk in closets and there is a large linen closet in the private hallway. An indoor laundry room with built ins is well-located next to the kitchen and includes a laundry tub. Outdoor entertaining is perfect for celebrations in the screened lanai with your heated pool and outdoor kitchen! It is also a tranquil space to enjoy your friends and family as the pool features both a fountain and an area for plants. A pool bathroom is off the covered lanai and features a shower making an after swim shower really convenient. All of this beauty is set on professionally landscaped grounds with a whole house natural gas generator (2023) fed from the street and hurricane rated windows. The attached 3 car garage is oversized and features 3 separate garage doors and a driveway complete with a paver turnaround area for easy access in and out of the home. The home features a tile roof and many exterior trim details including landscape lighting only found in a custom, luxury home like this. The irrigation system is from this home’s private well. Built by the original owners and meticulously maintained showing pride of ownership throughout. This home has a low HOA that includes cable tv and Wi-Fi and is convenient to shopping, doctors, hospitals and local state colleges. Centrally located for an easy commute to Orlando or Tampa. Enjoy the virtual tour via the link.

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

Listing Agent: Susan Mayrant (863-255-2715)

Remarks: Under contract-accepting backup offers. Welcome to 960 Wedgewood Dr SE, a one-owner, mid century ranch home offering over 2,300 square feet of living space with original vintage character, ideally situated on a spacious ¼+ acre cul-de-sac lot with no HOA. This 3-bedroom, 2-bath residence offers a functional and inviting layout with formal living and dining rooms, with the dining room offering flexibility as a potential 4th bedroom thanks to its walk-in closet. The large formal living room provides ample space to host many guests and creates the perfect setting for intimate gatherings and conversation while the comfortable family room features a brick wood-burning fireplace surrounded by built-in shelving and cabinetry, creating a warm and welcoming focal point. The kitchen is generously sized with wood cabinetry, abundant counter space, ample storage, and a closet pantry—ready to serve as the heart of the home. The primary suite includes an en-suite bath with an updated walk-in shower and a spacious walk-in closet. Two additional bedrooms provide plenty of space for family or guests. A secondary bath with a tub is conveniently located by the bedrooms and the hallway features two linen closets, offering great storage throughout the home. A front bonus room creates a welcoming entry and is perfect for a piano or flex space. Additional highlights include a screened rear lanai ideal for morning coffee or entertaining, a charming covered front porch, a fenced backyard, and a storage shed with built-in shelving. The home is equipped with two A/C units plus a mini-split in the primary bedroom, allowing you to keep the home extra cool during Florida’s summer months. The oversized two-car garage offers built-in shelving, a storage closet, washer and dryer, and attic access via pull-down stairs for additional storage. Additional features include rain gutters, a separate irrigation water meter, and a location on a dead-end road with minimal traffic, offering added privacy and quiet enjoyment. Major updates have already been completed, including a new electrical panel and breakers (2024), partial re-plumbing (2021), roof (2016) with 50-year shingles, A/C units (2015 & 2018), and a natural gas water heater (2016). With new flooring and cosmetic updates, this home offers the perfect opportunity to create a charming and beautiful space to enjoy for years to come. Conveniently located just minutes from Publix, restaurants, schools, medical facilities, and LEGOLAND Florida Resort, with easy access to both Tampa and Orlando, offering quick trips to world-class theme parks and Florida’s east and west coast beaches. Located on a highly sought-after street, this is a rare opportunity to purchase a well-built home with great bones, space, and location—ready for its next chapter.

Listing is courtesy of: THE STONES REAL ESTATE FIRM (863-412-2080)

Listing Agent: Deanna Stone (863-412-2080)

Remarks: Under contract-accepting backup offers. BEAT NEW CONSTRUCTION COSTS! Seller offering up to $7,000 toward closing costs, prepaid expenses, or interest rate buydown; helping reduce your cash to close and monthly payment. Move-in ready with NO CDD!This beautifully updated 3-bedroom, 2-bathroom home with a bonus room is ideally located just minutes from LEGOLAND Florida, as well as shopping, restaurants, hospitals, and major attractions. Whether you're looking for a primary residence, vacation home, or investment opportunity, this property delivers comfort, space, and modern upgrades. Step inside to a bright, interior featuring new ceramic tile flooring throughout the entire home (absolutely NO carpet), offering easy maintenance and a clean, modern look. The homehas been freshly painted and thoughtfully updated to feel truly move-in ready. The renovated kitchen features new cabinetry, granite countertops, stainless steel appliances, a spacious pantry, and a breakfast nook perfect for casual meals. For hosting and special occasions, enjoy a formal dining room that adds both function and elegance.The spacious primary suite is a true retreat, offering a beautifully appointed en-suite bathroom with double sinks (ideal for busy mornings), granite countertops, an enclosed shower, and a relaxing garden tub.Both bathrooms have been upgraded with new cabinets and granite countertops, adding a cohesive and modern finish throughout the home. A versatile bonus room provides the perfect space for a home office, playroom, gym, or guest area. For added convenience, the laundry room is located inside the home.Step outside to the screened lanai, overlooking a generous lot being an ideal setting for weekend BBQs, family gatherings, or simpl enjoying Florida?s indoor-outdoor lifestyle.This home combines modern upgrades, flexible living spaces, and an unbeatable location near LEGOLAND Florida. With both roof & HVAC replaced in 2024 there is reassurance of major system being warranted - A must-see property!

Listing is courtesy of: EASY REALTY (321-895-4636)

Listing Agent: Greg Owen

Remarks: A stunning home featuring three spacious bedrooms and two bathrooms with a desirable split bedroom plan. Built in 2021, this residence offers a generous 2,200 square feet under roof, seamlessly blending an open floor layout with the latest technology for exceptional value in one incredible package. Enjoy the convenience of a smart home with automated lighting, climate control, and advanced security access, all designed to bring comfort and efficiency right to your fingertips. The architectural roof is less than a year old, and the energy-efficient construction ensures lower utility costs and sustainable living. This property also includes a water softener, washer, and dryer, all of which stay with the home for added value. If buyers need assistance with closing costs, the seller is open to considering support, making this an even more attractive opportunity. Seller will leave Living room, dining room furniture, big screen tv in master, if buyer desires.

Listing is courtesy of: BROKER’S REALTY AND CONSULTING (863-557-3265)

Listing Agent: Patty Clemons (863-557-3265)

Remarks: FIXER-UPPER OR INVESTORS. Priced accordingly. 2 Bedroom 1 bath- Excellent for rental property. Attached carport and large back yard. NO HOA! Located close to schools, churches, and shopping. Cash offers only with buyer paying title insurance and doc stamps.

Listing is courtesy of: CENTURY 21 WATSON & MYERS REALTY (863-324-1000)

Listing Agent: Sharon Watson (863-557-4800)

Remarks: Welcome to paradise, in this 2/2 with a enclosed front porch, to watch the beautiful Florida sunsets. The gated 55 plus community offers many amenities such as tennis, fishing pier, two heated pools, shuffle board, miniature golf, bocce ball, two club houses, fishing pier, plus many planned activities.

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

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

Remarks: This property is zoned for a duplex and features a large backyard, offering excellent potential for investors. The home is being sold as-is and will be delivered with all items currently inside. Located in a great family-friendly neighborhood, with a new Publix plaza opening nearby adding even more value and convenience to the area.

Listing is courtesy of: FLATFEE.COM (954-965-3990)

Listing Agent: Cliff Glansen

Remarks: Welcome to this stunning 3-bedroom + den pool home in a desirable gated community in Winter Haven—where space, style, and Florida living come together beautifully! Designed with a highly sought-after split-bedroom floor plan, this home offers both privacy and functionality. The luxurious primary suite is a true retreat, featuring elegant tray ceilings, dual walk-in closets, and a spa-inspired ensuite bath with dual vanities, a private water closet, a relaxing garden tub, and a separate walk-in shower. At the heart of the home, the gourmet kitchen impresses with granite countertops, stainless steel appliances, and a huge walk-in pantry, providing both style and ample storage. The versatile den/formal living room offers flexibility—perfect for a home office, media room, or additional living space. Step outside to your screened-in outdoor oasis, complete with a sparkling inground pool and an expansive lanai—ideal for entertaining, relaxing, or enjoying sunny Florida days. The fully fenced backyard offers plenty of room for a garden, pets, or play. With its premium features, flexible layout, and resort-style outdoor space, this home is a true standout. Don’t miss your chance—schedule your private showing today and make this Winter Haven pool home yours!

Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)

Listing Agent: Jeff Jones (205-902-3584)

Remarks: **Location, Location, Location! Seller offering $10,000 toward buyer closing costs, prepaid items, or interest rate buy-down with acceptable offer!** Beautifully maintained 3-bedroom, 2-bath home situated on an expansive oversized corner lot in desirable Southeast Winter Haven with **no city taxes — county taxes only**. Major updates have already been completed, including a **2024 A/C**, **2019 roof**, **new drain field**, and recent **septic inspection/pump-out** for added peace of mind. Inside, you'll find luxury laminate flooring throughout the main living areas with ceramic tile in wet areas, creating a clean and modern feel. Enjoy outdoor living in the private rear courtyard shaded by mature landscaping and beautiful trees, plus a stunning oak tree that enhances the curb appeal of this spacious corner homesite. A rare bonus is the **704 sq. ft. detached garage/workshop**, offering endless possibilities for storage, hobbies, vehicles, or workspace. Conveniently located near shopping, dining, schools, **only 2.1 miles from LEGOLAND Florida Resort**, close to Chain of Lakes access, near Freedom Boat Club, and just minutes from the new Chain of Lakes Baseball Complex. Don’t miss this opportunity!

Listing is courtesy of: CENTURY 21 WATSON & MYERS REALTY (863-324-1000)

Listing Agent: John Calhoun (863-528-7973)

Remarks: Located in the desirable Harrington subdivision of Winter Haven, this beautifully single-family home offers the perfect blend of comfort, style, and value. Featuring 3 spacious bedrooms and 1 bathroom, the home showcases a bright open-concept layout ideal for modern living. The kitchen boasts granite countertops, stainless steel appliances, and ample cabinet space. Enjoy durable vinyl plank flooring throughout, generously sized bedrooms, and an abundance of natural light. Step outside to a large backyard, perfect for entertaining or relaxing. Conveniently situated near schools, parks, hospitals, dining, and entertainment. Priced to sell, schedule your showing today!

Listing is courtesy of: PREMIUM PROPERTIES R.E. SERVICE (407-380-2800)

Listing Agent: Hamid Dghirni (407-575-2891)

Remarks: One or more photo(s) has been virtually staged. Welcome to this thoughtfully designed single-story home in a growing Winter Haven community, where modern comfort meets everyday convenience. Positioned on a corner lot with clean curb appeal and a fully fenced backyard, this property offers both functionality and a polished presentation from the moment you arrive. Inside, the home opens to a bright, open-concept living space anchored by durable tile flooring and enhanced by natural light. The living room flows seamlessly into the kitchen and dining area, creating an ideal layout for both daily living and entertaining. A large center island provides additional seating and workspace, complemented by white cabinetry, sleek countertops, and stainless steel appliances for a clean, contemporary look. The layout is designed with efficiency and comfort in mind, offering a practical flow between living spaces and private areas. Finishes throughout the home reflect a well-maintained, move-in-ready condition, with neutral tones that allow for easy personalization. Step outside to a fully fenced backyard featuring a paved patio area—perfect for outdoor dining, relaxing, or creating your own backyard retreat. The yard offers a balance of usable green space and lowmaintenance design, with room to enhance further if desired. Additional features include a two-car garage, modern fixtures, and solar panels visible on the roof, which may contribute to energy efficiency. Beyond the home itself, the community offers amenities such as a resort-style pool with lounge seating, providing a convenient option for recreation without the upkeep. The neighborhood is designed with sidewalks and a cohesive feel, contributing to an organized and accessible environment. Located in Winter Haven, this property benefits from proximity to everyday essentials including grocery stores, retail centers, restaurants, and healthcare services. The area is also known for its chain of lakes, parks, and outdoor recreation opportunities. Major roadways nearby allow for convenient travel to Lakeland, Orlando, and surrounding Central Florida employment hubs. This home presents a strong combination of modern living, outdoor space, and community amenities in a well-connected location.

Listing is courtesy of: NEXTHOME MY WAY (407-544-4545)

Listing Agent: Angel Pabon (407-544-4545)

Remarks: Private tri-level pool home on a quiet dead-end street—just minutes from the Winter Haven Chain of Lakes and LEGOLAND® Florida Resort. This 4-bedroom, 3.5-bath home is designed for flexibility, privacy, and real Florida living. Situated at the end of a street with no drive-by traffic, this property offers a peaceful setting that’s hard to come by—perfect for those who value space and quiet. One of the biggest advantages here is the tri-level layout, featuring a separate downstairs bedroom and full bathroom—ideal for guests, multi-generational living, or even a private office setup with its own space away from the main living areas. Out back, you’ll find a screen-enclosed pool and expansive patio, built for year-round enjoyment and entertaining. The large, fully fenced yard adds another layer of privacy and gives you room to spread out without feeling boxed in. And here’s where this one separates itself—there’s plenty of room for RV or boat parking with coverage, making it a rare find for buyers needing space for larger vehicles or recreational toys. Inside, the home offers a comfortable flow with multiple living areas, a spacious primary suite, and well-sized secondary bedrooms—giving everyone their own space while still feeling connected. Highlights: 4 Bedrooms | 3.5 Bathrooms Tri-level layout with private downstairs bedroom & full bath Dead-end street – no through traffic Screen-enclosed pool with large outdoor living area Fully fenced yard with strong privacy Covered parking for RV, boat, or extra vehicles Close to Chain of Lakes, boat ramps, and LEGOLAND® If you’re looking for a home that offers privacy, flexibility, and outdoor living—while still being close to everything—this one delivers. Call for your very own private showing today!

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

Listing Agent: Don Jerue (863-259-9550)

Remarks: One or more photo(s) has been virtually staged. DISCOVER THE SERENE BEAUTY OF THIS STUNNING HOME! GORGEOUS 2-BEDROOM, 2-BATHROOM, 1-CARPORT HOME boasting a SPACIOUS FLOOR PLAN that effortlessly blends functionality with modern style. From the moment you step inside, you’ll be greeted by an OPEN-CONCEPT LIVING AREA filled with NATURAL LIGHT, creating a warm and inviting atmosphere. .This home is LOADED WITH UPGRADES, including: New Roof with better type 30-Year Shingles, NEWER KITCHEN featuring NEW SLEEK STAINLESS STEEL APPLIANCES, Newer HVAC System from 2023, Newer Septic drain field in 2024, Renovated Bathrooms, Fresh Interior & Exterior Paint, New Light Fixtures, Faucets, Toilets, Interior Doors, and Closet Doors. Step outside to enjoy a fenced backyard and A huge screened-in porch that extends your living area, creating the perfect spot for relaxing, dining, or entertaining, .CONVENIENTLY LOCATED near all major highways, shopping, restaurants, and entertainment—this move-in-ready home truly has it all! All measurements are approximate and should be verified by the buyer, Virtual Staging was added to some of the pictures.

Listing is courtesy of: IHOME REALTY FL LLC (407-730-9971)

Listing Agent: Karen Sweat (407-730-9971)

Remarks: Cute as a Button! Charming 1-Bedroom, 1-Bath Condo in the desirable Park Lake community. This bright and inviting home features easy-care laminate flooring throughout, a cozy wood-burning fireplace, and a functional dinette area with a breakfast bar that flows into the dining space. Enjoy lots of Hot Water with the Natural Gas Tankless Hot Water Heater. The convenient stackable washer and dryer are included, making move-in a breeze. Step outside to enjoy your private screened-in porch — perfect for relaxing with your morning coffee or unwinding in the evening. Ideally suited for first-time homebuyers, investors, or anyone seeking low-maintenance living in a prime location, this condo is situated right in the heart of Winter Haven. The Park Lake community offers an abundance of amenities, including a sparkling community pool, direct lake access, clubhouse, fishing pier, exercise room, and more. Located on the shores of beautiful Lake Lulu, Park Lake is conveniently positioned next to the new AdventHealth Field House. You’re also just minutes from LEGOLAND, with quick access to the Disney and Universal entertainment areas. Excellent medical facilities and shopping are nearby as well. All measurements are approximate. Buyers and Buyers’ Agents to verify all listing information. Call today to schedule your private showing!

Listing is courtesy of: LAMOND REALTY INC. (863-875-8910)

Listing Agent: Robert Lamond (863-604-5400)

Remarks: This charming 2-bedroom, 2-bath condo offers the perfect blend of comfort and convenience with a layout designed for effortless living. Enjoy a spacious living area, light-filled interiors, and a private outdoor space perfect for morning coffee or evening wind-downs. Located just minutes from Winter Haven’s famous Chain of Lakes, local dining, shopping, and everyday essentials, this is the ideal spot for year-round living, a seasonal retreat, or a smart investment. Low maintenance. Prime location. Relaxed lifestyle. *This home can be purchased with NO INCOME VERIFICATION*

Listing is courtesy of: ENGEL & VOELKERS LAKELAND (863-412-6633)

Listing Agent: Donna Fiore (904-228-0198)

Remarks: Short Sale. Charming, move-in ready 3-bed, 2-bath home in a peaceful Winter Haven community. Features an open living/dining layout, updated kitchen with modern finishes, and spacious bedrooms. Enjoy plenty of natural light, a private backyard perfect for gatherings and outdoor living, and an attached 2-car garage. Well-maintained and thoughtfully updated, this home offers both comfort and convenience. Monthly HOA of just $50 includes community maintenance for worry-free living. Close to shopping, dining, schools, and major roadways for easy commuting. Don’t miss this opportunity to own in a quiet, established neighborhood — schedule your showing today!

Listing is courtesy of: WORLD PROPERTIES GROUP (407-574-5920)

Listing Agent: Mona Cherkaoui (407-947-5736)

Remarks: Welcome to 3108 Buckeye Point Dr — where comfort meets convenience in the heart of Winter Haven. From the moment you arrive, this home invites you in with a layout designed for the way you truly live. With 4 bedrooms and 2 full bath and a brand new A/C system the living spaces feel open yet connected, creating an easy flow for both everyday routines and weekend gatherings. Natural light enhances the home’s warmth, while thoughtful design elements make each space feel intentional and livable. The kitchen serves as the hub of the home, seamlessly connecting to the main living areas — ideal for hosting, relaxing, or simply enjoying a quiet night in. The primary suite offers a private retreat, while additional rooms provide flexibility for guests, work-from-home needs, or hobbies. Step outside and imagine morning coffee, evening unwinding, and effortless Florida living in your own outdoor space. Located in a desirable Winter Haven community, you’ll appreciate the convenience to shopping, dining, medical facilities, schools, and major roadways — all while enjoying the feel of a tucked-away neighborhood setting. Homes that combine layout, location, and livability like this don’t stay available for long. Schedule your private showing and experience 3108 Buckeye Point Dr for yourself.

Listing is courtesy of: KELLER WILLIAMS REALTY SMART (863-577-1234)

Listing Agent: Jp Phillips (863-670-7923)

Remarks: Discover lakeside living at its finest in this spacious 4-bedroom, 2-bath home located in the highly desirable 55+ community of Golf & Lake Estates in Winter Haven. Here, you own both the home and the land—a rare find in this area. Perfectly positioned with Lake Henry as your backyard, this home offers stunning water views from the large living area, where expansive windows fill the space with natural light and frame the peaceful scenery. This well-maintained community features outstanding amenities, including a marina, pool, spa, clubhouse, and a storage lot for RVs or boats. Whether you love fishing, boating, or simply relaxing by the water, this property provides the ideal setting. Enjoy the serenity of lakeside living with the convenience of an active, friendly neighborhood. Don’t miss the chance to call this beautiful lakefront property home!

Listing is courtesy of: GREEN STAR REALTY, INC. (813-598-6841)

Listing Agent: Samantha Conley (813-300-7753)

Remarks: One or more photo(s) has been virtually staged. Short Sale. Welcome to this beautifully maintained 3-bedroom, 2-bath home with a 2-car garage, offering 1,512 square feet of comfortable living space in a desirable gated community in Winter Haven. Built just two years ago, this nearly new home blends modern design with a warm, family-friendly feel. Step inside to find vaulted ceilings and tile flooring throughout the main living areas, creating a bright and open atmosphere. The spacious kitchen features stainless steel appliances, a large island, and ample cabinet space, perfect for everyday living or gathering with friends and family. The split floor plan provides privacy, while the generous primary suite includes double sinks, a garden tub, separate shower, and walk-in closet. Enjoy Florida living outdoors on the covered lanai, with a backyard perfect for relaxing afternoons or weekend playtime. Conveniently located near Downtown Winter Haven, Polk State College, Winter Haven Hospital, shopping, dining, and major attractions like LEGOLAND. For those who love lifestyle and entertainment, the home is also just about 15 minutes from the popular Port 27, a vibrant waterfront destination known for its live music, great food, desserts, and beautiful lake scenery—the perfect place to unwind and enjoy time with family and friends. This move-in ready home offers comfort, style, and location all in one. Schedule your showing today!

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

Listing Agent: Carolina Flores, Llc (954-471-5909)