Winter Haven Homes For Sale & Real Estate - 916 homes

Remarks: Under Construction. UNDER CONSTRUCTION:Welcome to the Residences at Winter Haven, a new single-family community focused on high-quality construction and modern design. This Key West model features a spacious three-bedroom, two-bathroom layout, centered around an open-concept living area. The interior is highlighted by premium finishes, including vinyl flooring and kitchen island with a fullwaterfall countertop. Large glass sliders lead out to a covered lanai, extending the living space and emphasizing a bright and functional environment.

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 23 Casarena Ct in Winter Haven, located in the gated lakefront community of Casarena on the Lakes on Lake Cannon, part of the Chain of Lakes. This spacious 2BR/2.5BA townhome offers approximately 2,045 sq ft of living space with vaulted ceilings, abundant natural light, and a functional two-story layout. The main level features an open living area with sliding glass doors leading to a private covered patio, plus a well-appointed kitchen with breakfast bar and a convenient half bath. Upstairs, enjoy a versatile loft/bonus space ideal for a home office or additional living area. Both bedrooms offer ensuite bathrooms, including a primary suite with a private screened balcony. Additional highlights include ceramic tile and hardwood flooring, spacious bedrooms, a two-car garage with freshly painted floor, and multiple outdoor spaces including three patios. Recent updates include the ROOF (Aug 2023). Owner is offering a $5,000 credit towards flooring. Residents enjoy resort style amenities: community pool, tennis courts, boat slip, and dock with direct access to Lake Cannon and the Chain of Lakes, perfect for boating, fishing, and waterfront living. Prime location near shopping, dining, and major roadways. Low-maintenance living in a secure, gated community.

Listing is courtesy of: RE/MAX HERITAGE PROFESSIONALS (863-256-2188)

Listing Agent: Patricia De Graaff, Llc (863-307-0061)

Remarks: Opportunities like this rarely come available in the gated Lakewood community. This beautifully updated lakefront pool home sits on a private one-acre lot and offers breathtaking sunset views across Lake Otis from your own backyard. Spend your evenings relaxing on the dock as the sun sets over the water, launch a kayak from the built-in racks, or enjoy weekends boating right from your covered dock. The backyard is designed for Florida living with a resurfaced pool, spacious screened patio, and incredible water views. Inside, the home offers 5 bedrooms and 3.5 bathrooms, including a highly desirable layout with two primary suites—one upstairs and one downstairs, perfect for guests or multi-generational living. Major updates provide peace of mind, including a new roof, two HVAC systems, new water heater, new flooring, and new carpet. The home also features all new double-pane impact windows and sliding doors, a newly resurfaced and retiled pool, and a new covered dock with kayak storage. The irrigation system pulls directly from the lake, so watering your lawn is never restricted by city water rules. Recent improvements include a re-screened patio, new gutters, new garage door, and a new privacy fence, making this home move-in ready. Imagine ending every day watching the sunset over Lake Otis from your own backyard. Homes like this rarely come on the market—schedule your private showing before it’s gone.

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

Listing Agent: Kelly Fain (863-617-0074)

Remarks: Welcome to this exceptional lakefront property at 3050 Crump Rd in Winter Haven, offering space, versatility, and direct access to the lifestyle Central Florida is known for. Situated on approximately 1.08 acres along Lake Hamilton, this residence combines a thoughtfully updated main home with a private guest studio, outdoor living, and boating amenities. The main home features three bedrooms and two bathrooms with an open and functional layout. A bonus room with built in entertainment cabinetry and surround sound opens through double sliding doors to the pool deck, creating seamless indoor-outdoor living. The living room showcases beautiful wood beams, a wood burning brick fireplace, and triple sliding glass doors overlooking the pool and lake. Tile flooring runs throughout the main living areas, with wood flooring in the bedrooms. The kitchen is designed for everyday living and entertaining, featuring granite countertops, updated cabinetry with pullouts, a large island, built in desk space, wine refrigerator, stainless steel appliances, and a built-in oven/microwave combination. A separate guest studio apartment adds flexibility, complete with a kitchenette and triple sliding glass doors leading directly to the pool area. This space is ideal for guests, extended household needs, or flexible use. Outdoor features include a screened pool with new heater and an 8-foot depth, a spa that conveys, and a gas fireplace on the patio with underground piping in place (propane tank has been removed, but can easily be replaced by the new homeowner). The pool screen was recently replaced. The property includes a private boat dock and lift, allowing easy access to Lake Hamilton and nearby lakefront restaurants by water. Additional highlights include fruit trees in the front yard, RV parking for up to 31 feet with additional storage space, and a metal roof. Practical upgrades and systems include a new air conditioning system installed July 2024 with annual maintenance, water softener, well for irrigation, public water for the home, an inside laundry room, and a 2-car garage. The hot water heater was installed in 2011. Septic service was last completed June 2023. Solar panels are leased at $381.75 per month, with an average Duke Energy bill of approximately $30 per month. Televisions in the main living areas convey, excluding bedrooms. This lakefront retreat offers privacy, functionality, and a connection to the water, all set along beautiful winding roads in a peaceful Winter Haven setting.

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

Listing Agent: Lisa Matheny (863-412-6633)

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

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

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

Remarks: Rare opportunity to own a spacious two-story home in the highly sought-after Villamar community—homes like this don’t last long. Designed with an open-concept layout perfect for today’s lifestyle, this home offers a seamless flow from the kitchen—featuring quartz countertops, modern appliances, refrigerator, and breakfast nook—into a large, inviting great room ideal for entertaining. Upstairs, retreat to a private primary suite with walk-in closet and en-suite bath complete with dual vanity and tiled shower, along with three additional bedrooms, a full bath, and the convenience of second-floor laundry with washer and dryer included. Enjoy modern living with built-in smart-home features including a Ring Video Doorbell, smart thermostat, keyless entry, and DEAKO switches. Located in Villamar, residents enjoy access to resort-style amenities including a pool, clubhouse, playground, dog park, scenic walking paths, ponds, and lush green spaces. Additional highlights include professional landscaping, a covered entry porch, architectural shingles, and a builder warranty for added peace of mind.

Listing is courtesy of: UNITED REALTY GROUP INC (954-450-2000)

Listing Agent: Keisha Weir (754-204-5431)

Remarks: Welcome Home to Queens Cove! This stunning 4 bedroom, 2 bathroom home is located in the highly desirable community of Queens Cove in Winter Haven. NO CDD and low HOA. Minutes from Legoland, hospitals, shopping centers and mayor highways. Don't miss your opportunity to own an affordable home in the heart of Winter Haven. Schedule your showing today!

Listing is courtesy of: CAISSA REALTY INVESTMENT INC (407-364-3056)

Listing Agent: Harrison Perez Collazo (787-365-8967)

Remarks: This move-in ready 3-bedroom Winter Haven pool home offers a fantastic combination of comfort, upgrades, and true Florida living on an oversized lot with no HOA. The home features a brand-new roof, new HVAC system and thermostat, new water heater, new pool pump and chlorinator, new laundry units, new exterior front doors, and an expanded driveway with ample parking. Inside, you’ll find a functional layout with generous living space and fresh improvements throughout. The private in-ground pool creates a relaxing backyard setting, while the large lot provides room for outdoor entertaining, storage, or future additions. Located minutes from the Winter Haven Chain of Lakes, Gene’s Lakeside Marina, LEGOLAND Florida Resort, golf courses, shopping, dining, and local parks, this property sits in one of Central Florida’s most desirable and fast-growing areas. With major updates already completed and convenient access to boating, recreation, and upcoming community development, this home is an excellent opportunity for first-time buyers, families, or investors.

Listing is courtesy of: THE URBAN GROUP, INC. (954-522-6226)

Listing Agent: Ashlee Morrell (941-740-9134)

Remarks: Big Price Drops and Price to sell. Turn Key House on the North Chain of Lakes. 2023 Roof, 2022 POOL! Welcome to this pristine, beautifully maintained home in the quiet and highly desirable Island Lakes community—where there’s no through traffic and peaceful living comes naturally. This property features a newer roof put on in 2023, a newer in-ground pool put in 2022, and a large backyard shed, offering the perfect blend of comfort, storage, and outdoor enjoyment. Step outside and you’ll fall in love with the vinyl-planked dock that gives you direct access to the Chain of Lakes, making it ideal for boating, fishing, and sunset cruises. Whether you prefer relaxing in the screened-in outdoor area or lounging by the sparkling pool, this home is designed for anyone who loves outdoor living. Inside, the home is in immaculate condition. It offers three bedrooms, including a spacious master suite complete with a walk-in tub for easy washing and added convenience. Every room feels well cared for, move-in ready, and prepared for its next owner to enjoy. This stunning property truly has it all—comfort, water access, serenity, and style. It’s ready and waiting for the next buyer who wants to fully embrace lakeside living.

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

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

Remarks: Spacious single-family home featuring 4 bedrooms and 2.5 bathrooms with approximately 3,160 sq ft of living space, offering a functional and flexible floor plan. The main level includes a private office with French doors, ideal for use as a home office or optional fifth bedroom. Generous interior spaces provide comfortable living and well-sized bedrooms throughout. Conveniently located in Winter Haven, with easy access to major roads, shopping, dining, and everyday conveniences. This property offers an excellent opportunity for buyers seeking space, versatility, and a well-established residential setting.

Listing is courtesy of: LA ROSA REALTY LLC (321-939-3748)

Listing Agent: Maria Chavez (407-866-4682)

Remarks: Investor opportunity meets wide-open space! Situated on 11.8 acres at the end of a quiet dead-end road, this unique property offers privacy, flexibility, and endless potential. Featuring a 4-bedroom, 2-bathroom mobile home, this property is ideal for investors, renovators, or buyers looking to create their own private retreat or family compound. ***SELLER IS MOTIVATED TO SELL*** SELLER IS WILLING TO NEGOTIATE!!!! DO NOT MISS THIS OPPORTUNITY!!! The home is in need of cosmetic updates, but major components have already been addressed, including a roof (3 years old), HVAC (4 years old), and hot water heater (4 years old)—providing a solid foundation for improvements. Inside, you’ll find a functional layout with original kitchen and bathrooms, stainless steel appliances included, carpet in living areas and bedrooms, and vinyl flooring in the kitchen. Washer and dryer hookups are available. This expansive property is perfect for those seeking space to spread out—bring your ATVs, off-road vehicles, boats, or work equipment, or explore the potential for multi-use living. With no HOA and a peaceful, rural setting, this property is well-suited for outdoor enthusiasts or those looking to escape city congestion. Sold AS-IS. Seller will make no repairs. SELLER IS MOTIVATED TO SELL!!! BRING ALL REASONABLE OFFERS!! Don’t miss this rare chance to own acreage with unlimited potential!

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

Listing Agent: Teri Hunter (863-307-1683)

Remarks: Waterfront view home on a large lot in amenity-rich community with clubhouse, pool, shuffleboard and fishing pond. This 2 bedroom 2 bathroom home features a completely remodeled kitchen with stone counter tops, custom pull-out cabinetry, and luxury vinyl plank flooring. New carpet throughout most of home. Glass-enclosed Florida room with A/C overlooks pond and clubhouse. The guest bathroom includes a washer and dryer. Widened driveway, deep carport fits car + golf cart. Shed under a carport with water softener and storage/workshop space. Move-in ready partially furnished and conveniently located near all community amenities. Own your land in this 55+ Community. The roof was replaced in 2009.

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

Listing Agent: Kimberly Davis (850-625-8855)

Remarks: Under contract-accepting backup offers. PRICE REDUCTION! MOTIVATED SELLER! With fabulous WATER VIEWS and GOLF COURSE views, this elegant residence offers a perfect tropical retreat. A large pool with a attached spa invites year-round outdoor enjoyment, framed by the beauty of Lake Ashton's natural surroundings. Ideally situated near Lake Wales and Winter Haven this home offers exceptional access to shopping and entertainment; medical facilities and restaurants. The spacious three-bedroom, two-bath layout includes a large den, ideal for a home office or flexible living space. The chef's kitchen features upgraded 42" cabinets, tiled backsplash, granite counter top and breakfast bar all designed for both form and function. The primary suite offers a spa-like escape with double vanities, a walk-in shower, a large soaking tub, separate water closet, and His and Her walk-in closets. Direct access from the PRIMARY SUITE to the outdoor living space is a BONUS. The outdoor living space is covered and screened to enhance the home's entertaining capabilities, creating a seamless flow between indoor and outdoor living. This ST. JOHN floor plan is a split plan home, which is desirable and spacious. Golf enthusiasts will appreciate the separate golf cart entry garage. Additional home features include: Travertine Flooring in the Living Areas (Bedrooms have carpet), Custom Shelving in the Den/Office with Glass Doors, Tray Ceiling in the Primary and Living Room areas, Sliding Glass Doors that Disappear into a Pocket in the Living Room and Beautiful Window Treatments, Floor outlets in the LR and MORE.... IT'S AS MUST SEE!!! Located in Lake Ashton, a 55+ community, residents enjoy access to a resort-style pool, fitness center, pickleball and tennis courts, and planned activities. Lake Ashton offers 2- 18 hole golf courses (Memberships Optional), Restaurant, Pro Shop and Eagles Nest. If you are seeking luxury, security and an active lifestyle, Lake Ashton could be your next home.

Listing is courtesy of: LAKE ASHTON REALTY INC. (863-221-5970)

Listing Agent: Lori Raath (863-409-6899)

Remarks: Take advantage of this beautiful 3 Bed, 2 Bath home with Stunning Lake View in Winter Haven, FL! Welcome to your dream home, nestled in the heart of Winter Haven, with sunset view from the back porch that will take your breath away. With granite countertops in the kitchen, modern appliances, and a spacious open layout, this home is perfect for families or those seeking comfort and style. The master bedroom features an ensuite bathroom, providing a private retreat, while the other two bedrooms are spacious and bright. Outside, the stunning views of the surrounding landscape make this home truly special. Conveniently located near shops, restaurants, and local attractions, this home offers both tranquility and easy access to the best of Winter Haven. Don’t miss out on this opportunity to own a beautiful home in one of the most desirable areas of Winter Haven! Contact us today to schedule a showing.

Listing is courtesy of: LA ROSA REALTY CW PROPERTIES L (407-910-2168)

Listing Agent: Lidia De Queiroz (321-330-8082)

Remarks: The property you are inquiring about is located in Winter Haven, FL, in the Southeast area of Polk County. This is just a beautiful family home featuring approximately 2,000 square feet living, 4 bedrooms, 3 bathrooms, with practically everything in the home updated since 2018! This is very functional elevated outdoor pool with sun deck space to enjoy and dive right in. There is an additional 13x33 detached garage or workshop all situated on 1/3 acre approximately. This is a NON-HOA community, so your monthly expense is lower and more choices! Also a large screened lanai, fenced backyard, and conveniently located in the SE quadrant. Washer and dryer stay. Tool shed stays. Text, call, or email to see it today! *Realtors, please read MLS remarks.*

Listing is courtesy of: BROKERS REALTY OF CENTRAL FLOR (863-294-6773)

Listing Agent: Renee Butler (863-294-6773)

Remarks: One or more photo(s) has been virtually staged. *BACK ON THE MARKET due to buyer financing, no fault of seller**Welcome home to this beautifully maintained move-in ready 3-bedroom, 2-bathroom home with a screened-in porch located in Winter Haven, Florida. As you step inside, you are greeted by elegant French doors and a stunning bay window that fills the living room with an abundance of natural light. The primary suite is privately located on one side of the home and offers its own en-suite bathroom and walk in closet, creating a peaceful retreat at the end of the day. On the opposite side of the home, you will find two additional bedrooms and a second full bathroom. The kitchen features a practical layout and opens to the dining room, creating a comfortable space for daily living and hosting guests. An interior laundry closet adds convenience and makes household tasks simple and accessible. Step outside to enjoy the spacious screened-in back porch, ideal for relaxing or hosting family gatherings. The fully fenced backyard and additional side patio offers a great space for grilling and spending time with friends and loved ones. A one car garage provides secure parking along with additional storage space. This home is conveniently located in the Whisper Lake Community off Highway 17 with quick access to the Polk Parkway, making commutes to Orlando and Tampa simple and efficient. Located just minutes from LEGOLAND Florida Resort, as well as shopping, dining, and everyday amenities. The 3rd bedroom is currently not fully enclosed, but can easily be completed to create a fully private third bedroom, home office, or flex space. It is currently left open behind the dinning room to create a larger space. This delightful home is ready for you, schedule your private showing today.

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

Listing Agent: Ashley Lopez (863-585-0585)

Remarks: Under Construction. Discover this stunning brand-new construction 3-bedroom, 2-bath home with an open living space and a convenient 2-car garage, this move-in-ready gem boasts elegant granite countertops in the kitchen for a touch of luxury and everyday functionality. The bright, airy layout offers three spacious bedrooms, two full baths, and a peaceful setting perfect for relaxing or family life—ideal for first-time buyers or those seeking fresh, contemporary Florida living. Minutes from shopping, dining, parks, and the Chain of Lakes, this serene location combines tranquility with easy access to everything Central Florida offers. Don't miss this pristine new build—schedule your private tour today! All measurements and sizes are deemed to be accurate but not guaranteed; any information contained here that is critical to buyers' purchasing decisions must be verified by the buyers. Private financing is available to qualified buyers.

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

Listing Agent: Juan Carrion (863-581-6028)

Remarks: Pre-Construction. To be built. Welcome to Ashton Covey in Winter Haven! Discover the ultimate Florida lifestyle in this stunning community. Perfectly situated just off US Highway 27, your new home offers seamless access to work, outdoor recreation, shopping, dining, and more. Imagine being less than 15 minutes from Downtown Winter Haven, where charming local shops and restaurants await your exploration. Plus, you're just 5 miles from public lake access at Lake Daisy, ideal for a day of boating, paddle boarding, and enjoying the water. The Baymont 2-car garage single-family home has it all, all on one level. A welcoming foyer invites you inside and leads you past 2 spacious bedrooms to a unique flex space, which can be used as a study or an additional bedroom. From there, a large great room is where you’ll make memories with family and friends, and it flows directly into the gourmet kitchen. Set up games or enjoy homemade meals around the large center island. At the end of the day, escape to your main-level owner’s suite with its tray ceiling, walk-in closet and double-vanity bath. This is the next level of great living. 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: Pre-Construction. To be built. Welcome to Ashton Covey in Winter Haven! Discover the ultimate Florida lifestyle in this stunning community. Perfectly situated just off US Highway 27, your new home offers seamless access to work, outdoor recreation, shopping, dining, and more. Imagine being less than 15 minutes from Downtown Winter Haven, where charming local shops and restaurants await your exploration. Plus, you're just 5 miles from public lake access at Lake Daisy, ideal for a day of boating, paddle boarding, and enjoying the water. The Lynn Haven single-family home lives up to expectations. Relax on the long front porch. Inside, flex space makes an ideal den, or add doors for a quiet study. The foyer leads to the open family room and gourmet kitchen with island, where favorite meals and memories will be made. Enjoy outdoor living on the extended lanai, and store seasonal items in the 3-car garage. There’s even more to love upstairs with a loft, 3 bedrooms and a full bath. In your deluxe owner’s suite, enjoy beautiful tray ceilings, double vanities and a walk-in closet. You can have it all in The Lynn Haven. All Ryan Homes now include WIFI-enabled garage opener and Ecobee thermostat. **Closing cost assistance is available with use of Builder’s affiliated lender**. DISCLAIMER: Prices, financing, promotion, and offers subject to change without notice. Offer valid on new sales only. See Community Sales and Marketing Representative for details. Promotions cannot be combined with any other offer. All uploaded photos are stock photos of this floor plan. Actual home may differ from photos.

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

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