Winter Haven Single Family Homes For Sale - 773 homes

Remarks: Under Construction. Introducing the Harper floorplan at Villamar, where every square foot is put to use with sophistication and comfort. Inside this 4 bedroom, 2 bathroom home, you’ll find 1,665 square feet of comfortable living. This meticulously designed residence combines modern convenience with timeless elegance, showcasing granite and tile floors throughout. As you step inside, you are greeted by an inviting foyer that leads you into the heart of the home. The open-concept layout seamlessly connects the living room, dining area, and kitchen, creating a perfect space for entertaining family and friends. The spacious living room features abundant natural light, thanks to large windows that provide picturesque views of the surrounding landscape. With ample room for seating, it's an ideal spot for relaxation and gatherings. The chef's kitchen is a true highlight, boasting granite countertops, sleek stainless steel appliances, and an oversized island with a breakfast bar. Whether you're preparing a casual meal or hosting a formal dinner, this kitchen is well-equipped to meet your culinary needs. The four generously sized bedrooms offer flexibility for various lifestyles. The primary suite is a tranquil retreat, featuring a private ensuite bathroom with dual sinks, a separate shower, and a walk-in closet. The remaining three bedrooms share one well-appointed bathroom, making morning routines a breeze. Like all homes in Villamar, the Harper includes all concrete block and also smart home technology, which allows you to control your home anytime with your smart device while near or away. Whether you're seeking a peaceful family retreat or a stylish place to call your own, this home is sure to meet your every need. Contact us today and find your home at Villamar. *Photos are of similar model but not that of the exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability, and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

Listing is courtesy of: DR HORTON REALTY OF CENTRAL FLORIDA LLC (407-250-7299)

Listing Agent: Paul King (407-519-3940)

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: Spacious 4-Bedroom, 3-Bath Pool Home in the admired Lakewood Community. Nestled on an oversized lot with mature trees, this remodeled tri-level home offers a perfect blend of modern luxury and comfort. With a spacious layout, a private pool, and an abundance of natural light, this home is designed for both relaxation and entertaining. As you enter, you’ll immediately notice the bright and airy atmosphere created by large windows that allow natural light to flood the home. The home features stunning luxury vinyl plank flooring and a beautiful brick fireplace, adding warmth and character to the space. The kitchen is of good size and boasting sleek countertops, new modern appliances, and ample cabinet space. Enjoy casual meals in the eat-in kitchen or step outside to the screened-in porch, an ideal spot for dining al fresco or simply relaxing while overlooking the expansive backyard and pool. Come add your personal touches and make this house your beautiful home!

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

Listing Agent: Michelle Armbruster (863-521-6879)

Remarks: Under contract-accepting backup offers. Under Contract. Winter Haven Single Family Residential home, 3B/1ba offers a well landscaped Corner Lot. The Interior accommodates Electric AC & natural gas heat. This home still boasts original well maintained kitchen cabinets, eat-in kitchen & gas oven appliances. The Exterior features are Concrete Block Detached storage/workshop 20x14’, covered carport 20x12’, exterior lighting,pvc plumbing, irrigation well/pump, pole barn for RV parking 28x20’, carport, brand new hot water heater, enclosed concrete outside laundry room. This home offers updated plumbing and abundant parking. Pride of Ownership. A must see!

Listing is courtesy of: WATSON & WATSON INC REALTORS (863-294-4149)

Listing Agent: Wendy Gibbs (863-557-5249)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Newly renovated 2 bedroom, 2 bathroom home with all the major updates already done for you — new roof, new floors ,new AC, and new water heater. This is a boater and fisher’s dream property located on beautiful Lake Dexter, Enjoy boating, water skiing, and freshwater fishing right from your backyard playground. The community offers a dock with boat slips available on a first-come, first-served basis, perfect for boats up to 24 feet. Residents also enjoy a clubhouse, pickleball courts, and tennis courts, making it easy to enjoy the Florida lifestyle. Whether you're looking for a full-time residence or a weekend lake retreat, this home offers the perfect mix of updates, amenities, and waterfront living.

Listing is courtesy of: ELEVE REAL ESTATE LLC (813-562-5002)

Listing Agent: Danielle Davis (813-526-5002)

Remarks: Back on market! Cute as a button, historic charm with some nice updates. From the welcoming front porch to the massive fenced back yard, complete with dog washing station, this is a cozy spot to call home! Love the original hardwood floors, open bright kitchen, and character such as built ins. Roof is less than 10 years old, and the sellers have updated the HVAC including adding a mini split to the main bedroom for those who like it extra cold at night. Plenty of parking and extra storage outside as well...check this one before it gets away!

Listing is courtesy of: HARPER REALTY FL, LLC (863-687-8020)

Listing Agent: Paula Shields (863-581-1498)

Remarks: Under contract-accepting backup offers. Step inside through the large enclosed foyer—perfect as a welcoming entryway, mudroom, or additional sitting space. The home features a comfortable living room and a well-appointed kitchen with a separate dining area, ideal for everyday living and entertaining. A bonus back room provides flexibility and can easily be used as a home office, hobby room, or additional living space. Enjoy outdoor living on the covered back porch overlooking a fully fenced yard—perfect for pets, gatherings, or simply relaxing in your own private oasis. The property is a true gem for those who love fresh fruit, featuring numerous mature trees including mango, avocado, peach, lemon, and other citrus varieties. Additional highlights include two large storage sheds with electricity already in place, offering excellent space for a workshop, storage, or creative projects. There is also a full RV hookup with electric, water, and septic—perfect for travelers or accommodating guests. This property offers a rare combination of comfort, utility, and outdoor enjoyment. Don’t miss this opportunity to own a home with so much to offer!

Listing is courtesy of: LAND SOUTH REALTY, LLC (863-937-8867)

Listing Agent: Ron Denney (863-660-3919)

Remarks: NO HOA! This 2 bedroom, 1 bathroom property has an eat-in kitchen with granite countertops & dining space, and a separate living room for gathering. There is luxury vinyl plank (LVP) floors throughout the home and the bathroom has been newly tiled. The home has UV double-insulated windows, 8x10 shed with finished interior, electricity & wall A/C unit, and a spacious fenced backyard with vehicle gate. Seller updates include screen-enclosed front entry, landscape & sod, bathroom tile, crown molding, living room ceiling fan, LVP & baseboards, and finished shed. This home sweet home is tucked away approximately a half mile to Havendale Blvd which leads to groceries, restaurants and connecting highways/roads for commutes. A brand new Publix will soon be opening right next to this neighborhood! Bring your watercraft because you're approximately one mile to a public boat ramp for Lake Jessie which is known for its fishing, aviation activity (including seaplanes!), and is part of Winter Haven's famous Chain of Lakes.

Listing is courtesy of: REDFIN CORPORATION (407-708-9747)

Listing Agent: Juan Castro (407-808-5353)

Remarks: Back on market buyers financing fell through. Welcome home! Your forever home is located near downtown Winter Haven and just a short distance from Polk State College. Completely remodeled in 2021 with a New Roof, New A/C, New Water Heater, New Electrical system, new windows new kitchen (Quartz Countertops), new appliances, new floors (Vinyl). This home has a huge, oversized corner lot and with summer around the corner, this will be the place for all the summer BBQ's.

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

Listing Agent: Cliff Glansen

Remarks: This 2-bedroom, 2-bathroom home features a private, screened-in backyard pool. Enjoy nearly non-existent electric bills thanks to a fully paid-off SolarEdge solar system, complemented by a whole-house 22 kW Generac generator with a 250-gallon propane tank, hurricane-rated windows, a 5-year-old architectural shingle roof, and a Rinnai tankless water heater. The spacious interior boasts a large galley kitchen with stainless steel appliances and a gas stove, a convenient indoor laundry room with extra storage, a 2-car garage, and a versatile 16x12 climate-controlled Florida room. This property has been an Airbnb and can be purchased fully furnished, making it a turnkey investment or a move-in-ready retreat!

Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)

Listing Agent: Steven Koleno (804-656-5007)

Remarks: Move-in ready and priced to sell! Located in a quiet, neighborhood with a low HOA of just $200 annually, this beautifully updated 3-bedroom, 2-bath home offers exceptional value, major system updates, and endless potential on a spacious quarter-acre lot. Step inside to discover an inviting open-concept layout where the living room, dining area, and kitchen flow seamlessly together, creating the perfect space for both everyday living and entertaining. The updated kitchen features modern cabinetry, updated fixtures, appliances, and a center island that serves as the heart of the home. Luxury vinyl plank flooring throughout provides a clean, cohesive look and easy maintenance. Designed with privacy in mind, the split-bedroom floor plan offers a spacious primary suite separated from the guest bedrooms. Every bedroom features a walk-in closet, providing ample storage throughout the home. A large Florida room adds valuable additional living space and connects the home’s interior, making it ideal for a home office, playroom, gym, media room, or second living area. Outdoor living is where this property truly shines. Situated on approximately a quarter-acre lot, the expansive backyard offers plenty of room to create your dream outdoor oasis, including space for a future pool. Enjoy peaceful views with acreage behind the property, providing added privacy and a more open feel than many neighboring homes. The 16x16 screened patio with a concrete slab is perfect for relaxing, entertaining guests, or enjoying Florida evenings year-round. Major updates provide peace of mind, including a 2021 roof and 2021 A/C system. Originally constructed with a tile roof design, the home was built to support the additional structural load, contributing to its durability and long-term appeal. Additional highlights include a two-car garage, vinyl privacy fencing, updated appliances, modern fixtures, and thoughtful improvements throughout. Offering a rare combination of location, lot size, recent updates, low HOA fees, and future potential, this property presents an outstanding opportunity in one of the area’s most desirable neighborhoods. Whether you’re looking for a move-in-ready home, additional space to grow, or a property with room to personalize over time, this home checks all the boxes. Seller is motivated. Schedule your private showing today and discover everything this exceptional property has in store.

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Emily Ward (863-632-1865)

Remarks: Under contract-accepting backup offers. Short Sale. ***SHORT SALE*Discover Your Dream Home at Lakeside Landing! Welcome to this immaculate home in the picturesque community of Lakeside Landing! This property offers the ultimate in modern living, combining comfort, style, and functionality. It's move-in ready and equipped with smart home technology, energy-efficient windows, and SOLAR PANELS to help you save on energy costs. Plus, enjoy the privacy of having no rear neighbors and a fully fenced large yard. Recent Upgrades and Features Flooring: Experience the elegance of luxury vinyl flooring throughout the home, with upgraded plush carpeting in the primary bedroom. The bathrooms boast stylish tile flooring. Bathroom Updates: Enjoy the convenience of brand-new toilets and an updated guest bathroom that features a new vanity and mirror. Kitchen Enhancements :Crown molding on kitchen cabinets Added cabinet hardware, Stunning new backsplash, Farm-style door leading to the pantry New wooden pantry shelves Additional Interior Features: Ceiling fans in both the primary bedroom and living area Neutral color scheme with fresh, whole-house interior paint Outdoor Living Relax and unwind on your screened-in porch while overlooking your spacious, fenced yard. It's the perfect spot for enjoying a morning coffee or evening gatherings with friends and family. Community Amenities Lakeside Landing offers a variety of community features to enhance your lifestyle, including: Resort-style pool: Dive into relaxation and enjoy the sun by the pool. Ideal Location Convenience is at your doorstep with easy access to major highways like 27 and I-4. Nearby attractions include Legoland, Disney World, and Universal Studios, making this home an ideal location for entertainment enthusiasts. Additionally, Posner Park is just around the corner for all your shopping needs. Don't miss the opportunity to make this like-new, energy-efficient home yours. Come check it out and experience the best of Lakeside Landing living!*CDD INCLUDED IN TAXES . OWNER MOTIVATED

Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)

Listing Agent: Brenda Anglada (407-493-3464)

Remarks: This dynamically unique home in Winter Haven offers waterfront living, with direct access to the renowned Chain of Lakes. Ideally situated on Lake Cannon, the property delivers stunning water views and a peaceful setting that’s hard to match. Located within a gated, low-maintenance community, this home allows you to enjoy all the perks of ownership without the added upkeep. The community pool and hot tub sits just steps away—offering the feel of a personal pool without the responsibility. Residents also enjoy access to a community dock with first-come, first-served boat slips, making it easy to embrace the lake lifestyle. The property itself features a fenced yard, and a beautiful pergola—perfect for relaxing, entertaining, or enjoying the serene lakefront setting. The garage is equipped with a 2021 split-unit AC system, creating a versatile space ideal for a workshop, gym, or even additional living area. For added peace of mind, the home includes a gas-powered generator that automatically kicks on when needed. Inside, the home is nothing short of impressive—boasting soaring cathedral ceilings, expansive balconies with breathtaking views, and a layout that is both majestic and thoughtfully designed. The primary suite is a true retreat, featuring a private balcony, dual vanities, and a luxurious soaking tub designed for relaxation. Additional office and bonus spaces offers flexibility and can easily be converted into extra bedrooms to fit your needs. Updates include two AC units installed in 2017, along with a durable metal roof added in 2021 and the roof tiles were sealed and coated for an extra long life. Whether you’re looking for a full-time residence, a seasonal getaway, or a place to gather with family and friends, this home delivers a warm, inviting atmosphere with unique architectural character throughout. Enjoy peaceful mornings overlooking the lake, afternoons gardening in your yard, or evenings unwinding on the balcony while taking in the surrounding wildlife. Conveniently located near shopping, grocery stores, and Home Depot, this is more than just a home—it’s a lifestyle. A property like this must be seen in person to truly appreciate the grandeur and exceptional living experience it offers.

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

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

Remarks: This spacious 4-bedroom, 3-bathroom home offers the perfect blend of comfort and functionality. Featuring a large living room, there is plenty of space for relaxing, entertaining guests, or enjoying time with family. The open and inviting layout flows beautifully throughout the home, creating a warm and welcoming atmosphere.Step outside to your own private pool, perfect for enjoying Florida’s sunshine year-round, hosting weekend gatherings, or simply unwinding after a long day. With generous bedroom sizes and three full bathrooms, this home is ideal for families or anyone looking for extra space and convenience.Located in a desirable Winter Haven area, this property combines spacious indoor living with fantastic outdoor amenities, making it a wonderful place to call home.

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

Listing Agent: Marissa Hipp (863-624-4995)

Remarks: Under Construction. Brand new, energy-efficient home available by Jun 2026! Prepare dinner while catching up on the day’s events from this home's chef-inspired kitchen which overlooks a great room. Visit Villamar and explore new single-family homes for sale in Winter Haven, FL. Residents will have access to two resort-style amenity centers featuring a clubhouse, pool, and playground. Winter Haven is known for its beautiful chain of lakes with lakeside restaurants and its award-winning community theater. Nearby attractions include Legoland Florida and Peppa Pig Theme Park. A brand-new model and new phase are coming soon. Each of our homes is built with innovative, energy-efficient features designed to help you enjoy more savings, better health, real comfort and peace of mind.

Listing is courtesy of: MERITAGE HOMES OF FL REALTY (813-703-8860)

Listing Agent: Bryan Sumner (813-336-5895)

Remarks: Under contract-accepting backup offers. Short Sale. BANK APPROVED AT 263K --VACANT---ON A CORNER LOT--delightful home boasting a private vinyl fenced side and backyard. Step inside to find three bedrooms and two bathrooms, where the primary suite offers serene privacy and comfort. The kitchen is a homeowner’s dream with upgraded granite countertops, complemented by stylish brown cabinets. Hard flooring flows throughout most of the home, providing both beauty and durability, while the cozy carpet in one guest bedroom offers a touch of warmth. Freshly painted walls and even the ceiling fan in the family room have just been updated, giving the whole space a fresh, inviting feel. Additionally, a covered lanai provides a perfect spot for relaxation or entertaining. Easy access to the Polk Parkway to Orlando And Tampa,

Listing is courtesy of: PREFERRED RE BROKERS III (407-440-4900)

Listing Agent: Michael Huculak (321-624-0150)

Remarks: Move-in ready and fully remodeled from top to bottom, this 4-bedroom, 1-bathroom home at 1055 30th Street NW in Winter Haven is a true turnkey opportunity. Brand new roof (2026), brand new AC (2026), brand new windows (2026), new plumbing, and a new water heater mean all the big-ticket items are already handled — just bring your furniture and move right in. Inside, you'll find all new vinyl flooring throughout, a beautifully updated kitchen, and a flexible bonus room that can easily serve as a 4th bedroom, home office, playroom, or guest bedroom — whatever fits your lifestyle. Tucked into a quiet Winter Haven neighborhood with quick access to Highway 17, US-27, and Legoland, you're minutes from shopping, dining, and some of Polk County's best lakes.

Listing is courtesy of: YELLOWFIN REALTY (813-347-7547)

Listing Agent: Philips Joseph (813-955-1966)

Remarks: Nestled on a beautifully landscaped and tree shaded lot this well maintained 3 bedroom 2 bathroom home features split bedrooms with ample closets, formal living and dining areas, an expansive family room, breakfast bar in the kitchen and an attached 2 car garage. Additional amenities include an oversized rear screened lanai overlooking a serene kidney-shaped screen-enclosed pool with southerly exposure. Cypresswood Golf & Country Club offers a variety of amenities, including an 18-hole golf course, clubhouse with pro shop and lounge, Jr Olympic swimming pool and a soon-to-be-completed tennis, pickleball and recreation area. Located in close proximity to HWY 27 affords easy access to I-4 and within 1.5 hours of either coast. This ideal location is just a mile down the road from a brand new Publix as well as being conveniently close to shopping, restaurants, and Legoland.

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

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

Remarks: NEW PRICE ADJUSTMENT-Seller is willing to offer 3K towards Buyer's Closing Costs. Welcome to 4020 Carteret Dr in Winter Haven, a beautifully updated 4-bedroom, 3-bath home located in a desirable 55+ lakefront community with a 3-car garage offering comfort, convenience, and low-maintenance living in the heart of Central Florida. This thoughtfully designed home features stunning lake views, hardwood flooring, an updated kitchen with modern finishes, and stylish upgrades throughout. The spacious layout includes a mother-in-law suite, perfect for visiting family, guests, or additional privacy. Residents enjoy direct water access and a private community boat ramp, providing easy access to Winter Haven’s renowned Chain of Lakes, ideal for boating, fishing, and enjoying Florida’s outdoor lifestyle. The community also offers boat and water toy storage for a small fee, making it convenient to keep your boat or jet skis nearby and ready to use. One of the standout features of this home is the maintenance-free lifestyle. The HOA covers Cable, Internet, Exterior Home Maintenance including landscaping, mulch, and exterior painting, and More, allowing homeowners to enjoy their property without the typical upkeep responsibilities. Located just minutes from Cypress Gardens Boulevard, this home offers quick access to shopping, restaurants, grocery stores, golf courses, parks, and medical facilities. Residents are also close to LEGOLAND Florida Resort, and major roadways including US-27 and the Polk Parkway, making travel to Lakeland, Orlando, and Tampa convenient. If you’re searching for a Lake view home in Winter Haven, a low-maintenance home in a 55+ community, or a property with Ruby Lake access, 4020 Carteret Dr offers the perfect combination of location, lifestyle, and modern comfort in one of Polk County’s most established lake communities. Schedule a showing today!

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

Listing Agent: Sofia Lovinsky (407-376-1845)

Remarks: Live the lifestyle you’ve been dreaming about in Lake Ashton, Winter Haven’s premier 55+ gated community. This beautifully cared-for Ashton floor plan offers 3 bedrooms, 2 baths, a den, and 2,512 sq ft of thoughtfully designed space — but it’s the feeling of this home that truly stands out. From the manicured landscaping to the elegant leaded-glass French front doors, every detail reflects pride of ownership. Inside, natural light pours through plantation shutters and a full wall of 8’ sliding glass doors that draw your eye straight to your private backyard retreat. The kitchen is both stylish and welcoming, featuring Seacrest Birch cabinetry with soft-close drawers, designer Silestone countertops, and elevated details that make everyday living feel special. The primary suite is a peaceful escape with custom his-and-her closets and granite makeup vanity. The flexible den space is perfect for hobbies, guests, or a home office. As a certified Green Home by Environments for Living, you’ll enjoy energy efficiency and long-term savings. Step outside and this home truly shines. The oversized screened veranda with custom flooring, a beautifully designed outdoor kitchen, and a heated saltwater pool creates the perfect setting for quiet mornings, sunset swims, or entertaining friends year-round. The extended garage offers room for longer vehicles and even a golf cart, complete with epoxy floors and screened doors. And beyond your front door? Lake Ashton delivers resort-style living with golf, fitness center, clubhouse, pickle ball, tennis, dining, and endless activities — all in a vibrant, active community. This isn’t just a home. It’s the next chapter. Washer and dryer and front flag pole do not convey.Schedule your private showing today — you’re going to love it here.

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

Listing Agent: Anita Lowe (863-269-6461)