Winter Haven Homes For Sale & Real Estate - 1038 homes

Remarks: Virtually Staged. Welcome to 23 Casarena Ct in Winter Haven, located in the gated lakefront community of Casarena on the Lakes on Lake Cannon, part of Winter Haven's Chain of Lakes. This spacious 2BR/2.5BA townhome that 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 a breakfast bar and a convenient half bathroom. 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 & hardwood flooring, spacious bedrooms, a two-car garage with freshly painted floor & 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 & 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: Experience resort-style living in the highly sought-after gated 55+ golf community of Lake Ashton, offering 24-hour security and an incredible amenity-rich lifestyle. Residents enjoy access to championship golf courses, multiple clubhouses, indoor and outdoor pools, fitness centers, tennis and pickleball courts, bowling, movie theater, restaurant and lounge areas, walking and biking paths, lake access, and a vibrant social atmosphere that makes Lake Ashton one of Central Florida’s premier active adult communities. This beautifully upgraded Ashton floor plan offers approximately 2,606 square feet of living space with 3 bedrooms, 2 full bathrooms, a den, flex room, and a spacious 2-car plus golf cart garage with room for up to 2 golf carts. Inside, you’ll find soaring cathedral ceilings, tray ceiling accents, crown molding, recessed lighting, updated fixtures, and a seamless blend of laminate flooring and ceramic tile throughout. The gourmet kitchen features granite countertops, solid wood 42-inch cabinetry with crown molding, stainless steel appliances including a Bosch dishwasher and double convection ovens, along with abundant prep and storage space. Designed for both comfort and efficiency, the home includes a FULLY PAID OFF SOLAR PANEL SYSTEM with transferable warranty, whole-house generator, enhanced landscaping, updated irrigation system, abundant storage, and negotiable furnishings for a potential move-in-ready opportunity. The spacious primary suite offers custom closets, soaking tub, oversized walk-in shower, and private sauna. Enjoy Florida living year-round from the oversized screened lanai complete with remote-control privacy shades, outdoor kitchen with stainless steel grill, kegerator, wine fridge, barbecue area, and an impressive Veranda 10-person hybrid swim spa. The SELLER IS ALSO INCLUDING THE GOLF CART WITH THE SALE, making it even easier to enjoy everything the Lake Ashton lifestyle has to offer.

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. Make and Offer! Welcome to Garden Grove Oaks, a desirable 55+ community in Winter Haven! This charming move in ready 2-bedroom, 2-bath home offers comfort, convenience, and low-maintenance living in a beautifully maintained setting. The property features a full-yard irrigation system and beautifully landscaped grounds, along with the convenience of an inside laundry room. The sub-floor has been completely redone and Luxury Vinyl Plank has been installed. The primary bathroom has dual sinks with a walk in shower. There is a seperate storage shed for your convenience. Enclosed lanai/Florida room with a side air conditioner. One car covered carport and ample parking on the driveway. The low HOA of just $65 monthly includes access to a heated community pool, clubhouse, shuffleboard courts, and a full calendar of planned activities, plus scenic community walkways. Winter Haven offers an abundance of nearby amenities including restaurants, gyms, shopping, churches, hospitals, and medical facilities, as well as entertainment at the movie theater, the historic Ritz Theatre, and Theatre Winter Haven. LEGOLAND is just down the street, and Highway 27 is easily accessible. Enjoy the area’s many lakes for fishing, boating, or watching stunning sunsets. Orlando and Tampa attractions are approximately an hour away, making this an ideal location for both relaxation and adventure. Own your home and land and enjoy nearly maintenance-free living in this welcoming community.

Listing is courtesy of: MEEKS REAL ESTATE LLC (863-604-9287)

Listing Agent: Carla Meeks (863-604-9287)

Remarks: Welcome home to this beautifully designed 4-bedroom, 2.5-bath residence nestled on a desirable corner lot in the heart of Central Florida! From the moment you step inside, you’ll love the bright and open feel, complemented by stylish luxury vinyl plank flooring throughout the main living areas. The spacious kitchen is truly the heart of the home, featuring a large center island perfect for entertaining, meal prep, or gathering with family and friends, along with an oversized walk-in pantry offering an incredible amount of storage. The open-concept layout flows seamlessly into the living and dining spaces, creating an inviting atmosphere for both everyday living and hosting guests. Designed with functionality in mind, this home features a convenient guest half bath, while the secondary bedrooms are connected by a thoughtfully designed Jack-and-Jill bathroom layout. Step outside to enjoy the covered, screened-in lanai and partially fenced backyard, creating a private space to relax and enjoy Florida living. The corner lot adds extra curb appeal and a welcoming presence within the community. Located in a sought-after community with a resort-style pool and fantastic amenities, this home combines comfort, style, and convenience all in one. With easy access to shopping, dining, attractions, and everything Central Florida has to offer, this one checks all the boxes!

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

Listing Agent: Krystal Maddox (863-514-6555)

Remarks: Great investor or first time home buyer opportunity. This house has new windows, a new roof, updated electric panel and an renovated bathroom. The LVP throughout the home with 5-1/4 baseboard. This property has a huge back yard for your family to enjoy. Built in laundry with washer and dryer included. This property is move in ready and won't last long at this price. Schedule your showing today

Listing is courtesy of: XCELLENCE REALTY, INC (866-595-6025)

Listing Agent: Stephen Hubbell (863-559-5666)

Remarks: Welcome home to this beautifully maintained 4-bedroom, 3-bathroom home in the desirable Villa Mar community of Winter Haven! Built just 5 years ago, this spacious home offers nearly 2,000 square feet of thoughtfully designed living space and features fresh interior paint, brand-new carpet in all bedrooms, and a fully equipped kitchen with all appliances included, including the washer and dryer. Enjoy peace of mind with a regularly maintained HVAC system, alarm system, and full irrigation system. The oversized fully fenced backyard is larger than many comparable homes in the community and features gates on both sides, providing plenty of room for pets, play, entertaining, or even a future pool. One of the standout features of this home is the solar system, which will be paid off with a full-price offer, allowing the new owner to enjoy significantly reduced utility costs, with the previous owner averaging approximately $80 per month in electric bills. The newer construction may also offer savings on homeowner's insurance compared to older homes. Villa Mar residents enjoy access to a beautiful resort-style pool, playground, and convenient proximity to shopping, dining, schools, and major roadways. This move-in ready home combines comfort, efficiency, and value in one exceptional package. **Owner is Licensed Realtor**

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

Listing Agent: Krystal Maddox (863-514-6555)

Remarks: Charming and well-maintained and can be your HOME in Winter Haven! This property features a functional open concept floor plan with spacious living areas to entertain the entire family. This property is perfect for starter or investment! Schedule your private showing today. Buyer shall verify all the measurements provided herein.

Listing is courtesy of: HOMES UNLIMITED REAL ESTATE CORP (407-378-5600)

Listing Agent: Waleska Rodriguez Leon (407-929-2734)

Remarks: Welcome to the Spring model in Peach Crossings, a spacious five-bedroom, three-bathroom, two-story home situated on a desirable corner lot with no rear neighbors, offering extra privacy and an open feel. As you step inside, a long and inviting foyer welcomes you into the home. The first floor boasts a bright and open family room, perfect for gathering, along with a modern kitchen featuring a large island, breakfast bar, and brand-new Whirlpool appliances. A guest bedroom and a full bathroom on the main level provide a comfortable space for visitors or a private home office. Upstairs, the master retreat offers plenty of space for a king-sized bed, a dresser, and even a cozy reading nook. The en-suite bathroom includes a dual sink vanity, a linen closet for added organization, and a spacious walk-in closet for all your storage needs. The four additional bedrooms are generously sized, allowing everyone their own private space. These rooms can also be used as a home office, playroom, or hobby room to suit your lifestyle. With three full bathrooms, mornings run smoothly without congestion. A large upstairs laundry room with ample storage and a dedicated closet adds to the home’s convenience. Step outside and enjoy the covered back patio and covered front porch, perfect for relaxing or entertaining outdoors. Located in the highly sought-after Peach Crossings community, this home offers easy access to top-rated Polk County schools, shopping, dining, and local attractions. With all upgrades included, this home is move-in ready! Enjoy exceptional value and lower monthly costs with NO CDD fees in this beautiful communitySchedule your private showing today!

Listing is courtesy of: LGI REALTY- FLORIDA, LLC (904-449-3938)

Listing Agent: Gayle Van Wagenen (904-449-3938)

Remarks: Welcome to the Spring model in Peach Crossings, a spacious five-bedroom, three-bathroom, two-story home designed for modern living. Conveniently located close to the community playground, this home offers easy access to outdoor fun while maintaining a peaceful setting. As you enter, a long and inviting foyer leads into the heart of the home. The first floor boasts a bright and open family room, perfect for gathering and entertaining. The modern kitchen features a large island, breakfast bar, and brand-new Whirlpool appliances, making meal prep effortless. A guest bedroom and full bathroom on the main level provide a comfortable space for visitors or a private home office. Upstairs, the master suite is a true retreat, offering plenty of space for a king-sized bed, dresser, and a cozy reading nook. The en-suite bathroom includes a dual sink vanity, a linen closet for extra storage, and a spacious walk-in closet to keep everything organized. The four additional bedrooms are generously sized, making them perfect for family members or adaptable spaces like a home office, playroom, or hobby room. With three full bathrooms, mornings are stress-free with plenty of space for everyone. A large upstairs laundry room with ample storage and a dedicated closet adds to the home’s convenience. Outside, the covered back patio and covered front porch provide great spots to relax and enjoy the fresh air. Located in the highly sought-after Peach Crossings community, this home is just minutes from top-rated Polk County schools, shopping, dining, and local attractions. With all upgrades included, this home is move-in ready! Enjoy exceptional value and lower monthly costs with NO CDD fees in this beautiful community Schedule your private tour today!

Listing is courtesy of: LGI REALTY- FLORIDA, LLC (904-449-3938)

Listing Agent: Gayle Van Wagenen (904-449-3938)

Remarks: Welcome to the Summit model in Peach Crossings, a beautiful brand-new home featuring four bedrooms and two bathrooms with an inviting open-concept design. This home boasts high ceilings, enhancing the spacious and airy feel throughout. The master retreat is a true sanctuary, offering a generously sized bedroom that connects to a luxurious en-suite bathroom with a dual sink vanity for added convenience and a step-in shower for a spa-like experience. The kitchen is designed for both function and style, featuring exceptional counter space and brand-new Whirlpool appliances, including a refrigerator, stove, dishwasher, and microwave. A spacious hall closet provides extra storage, keeping everything organized. The family room is the perfect space for cozy movie nights, with ample room for a large sectional and entertainment setup. Whether it’s a movie marathon or a casual night in, this space is designed for relaxation, laughter, and quality time with loved ones. Step outside to the lanai, an ideal spot for enjoying warm Florida evenings with family and friends. The home also features professional front yard landscaping, adding to its curb appeal. Located in the heart of Polk County, Peach Crossings offers the best of lake living with easy access to shopping, dining, and top attractions. Families will love the highly-rated Polk County schools, and the community features a children’s playground and picnic area for added enjoyment. With all upgrades included, this home is move-in ready! Enjoy exceptional value and lower monthly costs with NO CDD fees in this beautiful community. Schedule your showing today!

Listing is courtesy of: LGI REALTY- FLORIDA, LLC (904-449-3938)

Listing Agent: Gayle Van Wagenen (904-449-3938)

Remarks: Welcome home to Peach Crossings, a brand-new community in Winter Haven! This stunning three-bedroom, two-bathroom home is designed for modern living, featuring an open-concept layout and stylish finishes. The kitchen is a chef’s dream, offering plenty of counter space for meal prep and entertaining. It comes fully equipped with Whirlpool appliances, including a refrigerator, stove, dishwasher, and microwave—all included at no extra cost! The granite countertops and sleek cabinetry add a touch of elegance and timeless appeal. This home also features high ceilings, enhancing the open and airy feel throughout the living spaces. Step outside to the covered patio, a perfect spot for relaxing, dining, or enjoying the beautiful Florida weather. This home is also packed with energy-efficient upgrades, including double-pane windows, a programmable thermostat, coach lighting, and a Wi-Fi-enabled garage door opener for added convenience. A mudroom located off the garage provides a dedicated space to store shoes, bags, and coats, keeping your home neat and organized. Plus, it’s conveniently placed next to the laundry room for maximum functionality. Enjoy exceptional value and lower monthly costs with NO CDD fees in this beautiful community! Nestled in Polk County, Peach Crossings offers a perfect blend of serene lake living with easy access to shopping, dining, and top attractions. Families will love the highly-rated Polk County schools, while the community itself features a playground and a picnic area for residents to enjoy. This home is move-in ready with all upgrades included! Schedule your tour today

Listing is courtesy of: LGI REALTY- FLORIDA, LLC (904-449-3938)

Listing Agent: Gayle Van Wagenen (904-449-3938)

Remarks: Welcome to Peach Crossings, a brand-new community in Winter Haven! This beautiful three-bedroom, two-bathroom home is designed with both comfort and style in mind. The kitchen is a true highlight, featuring expansive counter space, perfect for meal prep and entertaining. It comes fully equipped with Whirlpool appliances, including a refrigerator, stove, dishwasher, and microwave—all included at no extra cost! The combination of granite countertops and crisp white cabinetry creates a timeless and elegant look. This home also features high ceilings, enhancing the open and airy feel throughout the living spaces. Enjoy outdoor living on the covered patio, an ideal space for relaxing, dining, or enjoying the Florida weather. This home also comes with energy-efficient features, such as double-pane windows, a programmable thermostat, coach lighting, and a Wi-Fi-enabled garage door opener for modern convenience. A mudroom just off the garage provides a functional space to store shoes, bags, and coats, helping to keep the home organized. Conveniently located next to the laundry room, this area makes everyday tasks easier. Enjoy exceptional value and lower monthly costs with NO CDD fees in this beautiful community located in the heart of Polk County. Peach Crossings offers the perfect balance of peaceful lake living with easy access to shopping, dining, and local attractions. Families will appreciate the top-rated Polk County schools, and the community features a children’s playground and a picnic area for all to enjoy. Don’t miss this opportunity—schedule your showing today!

Listing is courtesy of: LGI REALTY- FLORIDA, LLC (904-449-3938)

Listing Agent: Gayle Van Wagenen (904-449-3938)

Remarks: Best view in the building! Welcome to your dream Florida escape at 700 Mirror Terrace NW, a beautifully updated and well-maintained condo in this lively 55+ Spring Lake Towers Community. This stunning unit boasts unparalleled lakefront views on the Chain of Lakes in Winter Haven, offering breathtaking sunrises and sunsets every day. Step inside and discover a spacious living and dining room. The large primary bedroom has a walk-in closet leading to a sunroom, creating a versatile space for relaxation or hobbies. Newer oversized windows throughout the unit bathe the living area in natural light, further enhancing the spectacular lake views... Live an active lifestyle with sparkling swimming pool directly on the lake well-equipped fitness center, shuffleboard court, recreation room and library. Indoor and Outdoor storage comes with the unit. On-site laundry facilities are available for residents. This condo is perfect for full-time residents seeking a tranquil lakeside retreat or snowbirds desiring an affordable winter getaway. Those seeking a low-maintenance lifestyle with condo fees covering water, sewer, trash, cable, internet, and all exterior maintenance. Additional highlights include a single covered parking spot, a dock for fishing or viewing the water, boat slips available on a first-come, first-served basis. Enjoy planned social events and activities for residents. No pets or smoking allowed. Winter Haven's central location provides easy access to theme parks like Orlando and Tampa Downtown area Grocery stores, shopping, movie theaters, restaurants and medical facilities, making this a prime location. Don't miss this extraordinary opportunity to own a piece of paradise. Escape to the tranquility, luxury, and with expansive water views where every day feels like a vacation.

Listing is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)

Listing Agent: Victoria Bollea (813-230-4529)

Remarks: MOTIVATED SELLERS Welcome to this beautifully maintained 3-bedroom, 2-bathroom home offering the perfect blend of comfort, functionality, and style. New roof 2022. Renovated bathrooms. Step inside to find a bright and inviting floor plan with spacious living areas, abundant natural light, and a warm, welcoming atmosphere throughout. The kitchen features ample cabinet space, and a convenient layout ideal for both everyday living and entertaining with direct access to the back patio. The master bedroom offers a private retreat with an en-suite bathroom and generous closet space that is connected directly to the large laundry room. The additional bedrooms provide flexibility for family, guests, or a home office. Outside, enjoy a spacious, fenced in yard with plenty of room for relaxing, gardening, or hosting gatherings. Conveniently located near Polk State College, Winter Haven schools, and just minutes away from downtown Winter Haven. This home combines peaceful living with everyday convenience. Perfect opportunity for first time homebuyers or rental property! Don’t miss the opportunity to make this move-in-ready home your own!

Listing is courtesy of: FLAT FEE MLS REALTY (813-642-6030)

Listing Agent: Stephen Hachey (813-642-6030)

Remarks: Welcome to this beautifully maintained 3-bedroom, 2-bath home offering the perfect blend of comfort, functionality, and outdoor living. Step inside to a spacious living and dining room combination, highlighted by a wood-burning fireplace, creating a warm and inviting focal point for the home. The updated kitchen features stainless steel appliances, stylish cabinetry, and a convenient breakfast bar perfect for casual dining or entertaining. The private primary suite offers a relaxing retreat with a walk-in closet and en-suite bathroom complete with a walk-in shower. Two additional guest bedrooms and a well-appointed hall bath with tub/shower combo provide ample space for family or visitors. Outdoor living truly shines with a screened lanai featuring a hot tub, overlooking the expansive fenced backyard designed for entertaining. Enjoy the above-ground pool with a wooden stairway deck, cozy fire pit area, and additional storage shed. All creating the ideal setting for gatherings or peaceful evenings at home. Additional highlights include a spacious two-car side-entry garage with laundry area, plus bonus office/workshop/storage space, as well as a one-car carport perfect for boat or camper parking. SOLAR power helps keep utility costs low, adding efficiency to this exceptional property! Conveniently located just steps from Lake Summit Public Boat Ramp and minutes from Cypress Gardens Boulevard, this home offers easy access to recreation, shopping, dining, and more. A rare opportunity to enjoy space, convenience, and lifestyle all in one remarkable property.

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

Listing Agent: Ginger Quirk (863-430-5111)

Remarks: Welcome to 504 Manilla Ln, Winter Haven, FL! This 3-bedroom, 2-bath manufactured home sits on a fully fenced and gated 0.5-acre lot, offering privacy, space, and plenty of potential. The property features chain-link fencing around the front yard with vinyl fencing along the rear of the property, creating a secure and private outdoor space. Inside, you'll find a desirable split-bedroom floor plan with a spacious primary suite, comfortable living room, dedicated dining area, breakfast nook, pantry, and interior laundry room. The kitchen includes a dishwasher, and a range will convey with the sale but is not currently installed. One of the standout features is the oversized screened front porch spanning nearly the entire length of the home—an ideal space to relax, entertain, or enjoy Florida's beautiful weather year-round. The property also includes 2- 10x20 outdoor storage buildings, large enough to accommodate a small vehicle, workshop space, or additional storage needs. Conveniently located near Winter Haven's popular attractions, including LEGOLAND® Florida Resort, the Chain of Lakes, parks, shopping, dining, and entertainment. Enjoy easy access to outdoor recreation and all that Central Florida has to offer. Property is being sold as-is.

Listing is courtesy of: FIND YOUR PARADISE (352-675-2209)

Listing Agent: Dylan Mcleod (352-675-2209)

Remarks: Virtually Staged. Rare opportunity to own a 5-unit multifamily investment property situated on an oversized lot in the rapidly growing and expanding City of Winter Haven. The property consists of three separate buildings, providing flexibility, privacy, and multiple income streams. Currently, three units are leased with one vacant unit available for immediate occupancy or additional rental income potential , air b n b options as well . Recent renovations and updates completed within the past year include a new metal roof, updated HVAC systems, and numerous interior and exterior improvements, helping minimize deferred maintenance and enhance long-term value. Located near shopping, restaurants, schools, medical facilities, and major roadways, this property is positioned in one of Central Florida's strongest and fastest-growing rental markets. The versatile layout presents numerous possibilities for investors seeking cash flow, portfolio expansion, house-hacking opportunities, or potential short-term rental and Airbnb use, subject to local regulations and buyer verification. With strong income potential, multiple buildings, recent capital improvements, and a prime Winter Haven location near attractions, employment centers, and everyday conveniences, this is a unique opportunity to acquire a well-maintained multifamily asset with both immediate income and future upside.

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

Listing Agent: Michael Hochadel (863-604-0018)

Remarks: Virtually Staged. Fully occupied 5-unit multifamily investment property located minutes from Downtown Winter Haven in a high-demand rental market. Zoned multifamily and currently producing immediate cash flow with all units leased. Strong location near major thoroughfares, retail, and ongoing residential development, including a planned townhome project that is expected to support future rental demand. Opportunity exists for additional income growth through rent optimization. Situated in one of Central Florida's fastest-growing submarkets, this stabilized asset offers current income, long-term appreciation potential, and portfolio expansion opportunities. Contact for rent roll and financial information.

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

Listing Agent: Michael Hochadel (863-604-0018)

Remarks: WELCOME TO THIS CHARMING TOWNHOUSE located in the sought-after Cypresswood Golf & Country Club community in beautiful Winter Haven! This inviting 2 BD / 2 BA home offers comfortable Florida living with a spacious open-concept living and dining room combination, abundant natural light, and a thoughtfully designed layout perfect for both relaxing and entertaining. The kitchen features beautiful granite countertops, handsome cabinetry, and a cozy eat-in space ideal for casual dining. The primary suite is generously sized and includes a custom walk-in closet, dual sink vanity, skylight, and an attractive walk-in shower creating a bright and airy retreat. The guest bedroom also offers a custom closet for added organization and convenience. Additional features include skylights that fill the home with natural light, spacious living areas, and a warm, welcoming atmosphere throughout. Residents of Cypresswood enjoy a gated golf course community with beautifully maintained grounds, scenic surroundings, clubhouse amenities, tennis courts, community pool, restaurant access, and an 18-hole championship golf course, all conveniently located near shopping, dining, medical facilities, and easy access to both Orlando and Tampa. Come experience the peaceful lifestyle and exceptional community setting this lovely townhouse has to offer!

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

Listing Agent: Erin Floyd (863-412-2286)

Remarks: Short Sale. SHORT SALE APPROVED. LIST PRICE APPROVED BY BANK. Amazing opportunity to purchase a 3 bedroom, 2 bath home situated on a spacious ¼ acre lot with NO HOA. Priced to sell and offering exceptional value, this property will not last long. The home features an open floor plan with a spacious living room, kitchen and dining combination, and additional family room space. The primary bedroom is generously sized and includes a private en suite bathroom. A bonus room with exterior access provides flexible space for a home office, game room, or additional living area. Attached oversized 1 car garage. The kitchen includes appliances and a breakfast bar. The covered outdoor area and wood deck have great potential for entertaining, and the fenced backyard with no rear neighbors adds privacy and space. Subject to lender approval. Home does now have some deferred maintenance.

Listing is courtesy of: THE AGENCY FL (407-335-4119)

Listing Agent: Cristina Porretto (407-264-1870)