Winter Haven Single Family Homes For Sale - 750 homes

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

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

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

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

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

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

Remarks: Short Sale. Don’t miss the opportunity to own this one-of-a-kind, 3-bedroom, 2-bathroom, 2-car garage custom home. Upon arriving at the property, you are greeted by an oversized lot and mature trees in a quiet, well-established neighborhood. Inside, the home offers an open and split floor plan, cathedral ceilings, and an indoor/outdoor pool that flows from the back patio into the living room, adding a unique feature to this property—perfect for entertaining and allowing you to take a dip in any weather. On the left side of the home are two spacious bedrooms with large closets and a shared bathroom featuring a single vanity and a shower/tub combo. Moving to the right side of the house, you’ll find the master suite, loft, and kitchen. The master suite offers ample space and direct access to the pool area. The en-suite bathroom includes a garden tub and walk-in shower. The loft overlooks the living room and pool area and also contains two large storage spaces on either side, making storage accessible while serving as a great spot to watch a show and unwind. The kitchen features tile countertops and a small bar for additional seating. Right out back, the pool is enclosed in a full-screen cage with a large deck. The yard also boasts a shed for storage and plenty of space for activities. This home has so much to offer. Don’t wait—schedule your private showing today!

Listing is courtesy of: LPT REALTY LLC (386-388-7877)

Listing Agent: Trent Shackelford (941-518-7875)

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

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

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

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

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

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

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

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

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

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

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

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

Remarks: Charming 3-bedroom, 1-bath home with no HOA, offering a great opportunity for investors or first-time buyers alike. Conveniently located in Winter Haven with easy access to shopping, dining, schools, major roadways, and everyday amenities. This property offers plenty of potential and is ideal for those looking to expand their portfolio or create a place to call home.

Listing is courtesy of: JOSEPH WALTER REALTY LLC (248-294-7850)

Listing Agent: Scott Fader (248-294-7850)

Remarks: Spacious Single-Story Block Home with Endless Potential! Nestled in a quiet, established neighborhood close to Polk State College with no HOA, this solid single-story block home immediately catches the eye with its charming blend of stucco and natural multi-colored stone accents. Boasting 1,678 square feet of comfortable living space (2,527 square feet total), the interior features a generously sized layout including three spacious bedrooms and two bathrooms. The primary suite is a true retreat, complete with a walk-in closet for ample storage. At the heart of the home, a large kitchen and dining area provides the perfect setup for family gatherings and entertaining. Step outside onto the oversized 0.26-acre lot, where the backyard offers a private oasis featuring mature, producing fruit trees, a handy detached storage shed, and a solid privacy fence running across the rear property line. Perfectly situated in a desirable community zoned for great local schools, this property has incredible bones and just needs some updating and TLC to truly shine. The seller is highly motivated and ready to see your offers—bring your design ideas and schedule your private showing today to unlock this home's immense potential!

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

Listing Agent: Twanna Dewdney (863-207-1634)

Remarks: Under Construction. The Atwood floor plan features 3 bedrooms, 2 full baths, approximately 1,600 sq. ft., an open-concept design, spacious kitchen island, private primary suite, and thoughtfully designed living spaces that combine comfort, style, and everyday functionality in a growing Central Florida location. Willowbrook North offers modern single-family homes in a boutique Winter Haven community near Lake Fannie and Willowbrook Golf Club, with convenient access to shopping, dining, Downtown Winter Haven, US-27, and I-4.

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

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

Remarks: Don't miss this move-in ready, recently updated 3 bedroom, 2 bathroom block home with a 2-car garage, situated on a spacious 7,370 sq ft lot in Winter Haven. This 1994 built home features a recently remodeled kitchen with quartz countertops, shaker cabinets, stainless steel appliances, luxury vinyl plank flooring, updated bathrooms, and fresh paint throughout! Major components like the roof and A/C have both been updated in recent years, with plenty of life remaining for added peace of mind. The open living room features a shiplapped fire place. Out back, enjoy the newly installed paver patio, perfect for grilling, relaxing, or entertaining in the spacious yard. This is a great value for a well-updated home with both indoor and outdoor space at an affordable price point with a low HOA! FHA and VA friendly! *Some photos have been virtually staged*

Listing is courtesy of: IMPACT REALTY TAMPA BAY (813-321-1200)

Listing Agent: Philip Bach, Pa (786-351-2294)

Remarks: Welcome to easy Florida living in the sought-after community of Peace Creek Reserve in Winter Haven! Built in 2024, this beautifully designed 3-bedroom home offers a modern split-bedroom layout, stylish finishes, and comfortable open living spaces perfect for both relaxing and entertaining. Step inside to discover bright and airy living areas with durable tile flooring flowing throughout the main spaces. The stunning kitchen is the heart of the home, featuring sleek stainless steel appliances, a large center island with seating space, abundant cabinetry, and an open design that overlooks both the dining area and spacious living room—making it easy to stay connected while hosting family and friends. Tucked away at the back of the home for added privacy, the primary suite offers a peaceful retreat with a generously sized bedroom, private ensuite bath with dual sink vanity, and a custom walk-in closet designed for organization and convenience. The split floor plan places the additional bedrooms and secondary bath on the opposite side of the home, creating flexibility for guests, family members, or a home office setup. Thoughtfully designed with newer construction benefits in mind, this home offers modern efficiency, low-maintenance living, and the peace of mind that comes with a recently built home. Peace Creek Reserve offers a convenient Winter Haven location close to shopping, dining, parks, lakes, and everyday essentials, while also providing easy access for commuting throughout Central Florida. Enjoy nearby outdoor recreation, local attractions, and all the charm that Winter Haven living has to offer. Whether you are looking for your first home, downsizing, or simply ready for a newer home with modern style and functionality, this one is ready to welcome you home. Schedule your private showing today!

Listing is courtesy of: KELLER WILLIAMS SUBURBAN TAMPA (813-684-9500)

Listing Agent: Tony Baroni (866-863-9005)

Remarks: Welcome to your turn-key Florida retreat! This beautifully reimagined home is a masterclass in modern updates and serene living, nestled within a tranquil, established community. From the moment you arrive, the vibrant curb appeal and crisp, clean lines signal a home that has been maintained with pride. The heart of the residence is an open, sun-drenched kitchen featuring premium stainless-steel appliances, sleek cabinetry, and chic subway tiling—perfect for the culinary enthusiast or the frequent entertainer. With durable wood-look flooring and a versatile, oversized utility suite, this home seamlessly blends style with everyday functionality. Beyond the interior, your private oasis awaits. Relax on the expansive screened-in porch or take advantage of the massive, fully fenced backyard—a rare find that offers limitless potential for a pool, garden, or workshop. The long driveway and integrated carport provide plenty of space for your vehicles and toys, making this the perfect home base for a Central Florida lifestyle. Whether you’re a first-time buyer or a savvy investor looking for a high-quality asset, this property offers an optimistic outlook and incredible value. Opportunity is knocking—book your showing today and claim your piece of paradise!

Listing is courtesy of: MCO REALTY (407-479-8601)

Listing Agent: Vernel Smith (863-224-1942)

Remarks: NO CDD Fees • Low HOA • *Lower Taxes • Move-In Ready • Resort-style backyard • Luxury Heated Pool Home. Welcome to this beautifully maintained and gently lived-in upscale home situated on an oversized 70’ wide homesite in a desirable community offering low HOA fees and *lower property taxes. Designed for both comfort and entertaining, this expansive 4-bedroom, 3.5-bath, two-story home has approximately 2,894 sq. ft. of thoughtfully designed living space, including TWO primary suites — one conveniently located on the first floor with a luxury bath and spacious walk-in closet, and a second upstairs primary suite featuring its own full bath and walk-in closet. The first floor also includes a versatile enclosed flex room which can be used as a home office, guest room, or potential 5th bedroom. The second floor has three other bedrooms with walk-in closet and oversized loft about 21'x17'. Step outside into your private resort-style backyard featuring a heated, fully automated full-size pool and spa with premium PebbleTec finish, already prepped for expansion with a concrete footer for future screen enclosure installation, upgraded pavers, large covered lanai, gutters and downspouts for improved drainage, fully fenced yard and extended front porch — creating the perfect Florida outdoor living experience— for entertaining, relaxing, pets, and family gatherings. Inside, the open-concept kitchen is beautifully upgraded with: • premium color cabinets, • oversized island, • stylish backsplash, • single-bowl sink, • granite countertops, • pendant lighting, • and stainless-steel appliances. Additional interior highlights include: • recessed LED lighting throughout, • tile flooring in wet areas, kitchen, hallway, and gathering room, • exterior-vented microwave, • and abundant natural light throughout. This truly move-in-ready home includes: • first-floor family room sofa set with wall-mounted 75” TV, • upstairs loft recliner sofa set with wall-mounted 75” TV, • refrigerator, washer, dryer, and window blinds, • home alarm system, • outdoor security cameras, • video doorbell, • and remote thermostat. Additional peace of mind includes: • transferable Pulte Homes 5/10-year warranty, • and 1 year of complimentary pool maintenance. This home has the perfect blend of luxury, functionality, and convenience in a family-friendly community with a safe small-town feel while remaining close to shopping, dining, everyday amenities and just minutes away from Legoland. READY TO MOVE IN. *Some photos have been virtually rendered.

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

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

Remarks: Back on the market due to buyer financing, property previously appraised at value. Welcome to 106 Lantern Ln in Winter Haven, a comfortable and move in ready 2 bedroom 2 bathroom home with 1,134 square feet of living space. When you step inside, you are welcomed into the living room that opens nicely to the dining area and adjoining kitchen, creating a functional and inviting layout for everyday living. From the dining room, you can step into the Florida room, a great space to relax, enjoy your morning coffee, or use as a flexible bonus area. One of the bathrooms has been recently updated and features a new tiled shower. The home has seen several major updates, including a new HVAC system installed in December 2025, along with a new roof and water heater replaced in 2023, and recently septic pumped this year. Out back, a storage shed provides plenty of room for tools, equipment, or extra storage. From the front yard, you can enjoy peaceful views of Ruby Lake, adding to the home’s charm. Conveniently located just minutes from Legoland Florida, Walmart, Winter Haven Medical Plaza, as well as shopping, dining, and everyday conveniences, this home is ready for its next owner. Schedule your showing today.

Listing is courtesy of: JADE KEY REALTY LLC (407-743-7766)

Listing Agent: Quoc Huynh (407-575-1355)

Remarks: Under contract-accepting backup offers. 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 3 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: Welcome to 8 St. Kitts Circle in Winter Haven—a move-in ready home that checks all the right boxes. Freshly painted and well-maintained, this property offers comfort and peace of mind with a metal roof (2023) and a newer A/C unit (2020). Even better, a brand-new water heater will be installed prior to closing, making this home truly ready for its next owner. Step outside to enjoy the vinyl-fenced rear yard—perfect for pets, play, or relaxing in your own private outdoor space. Enjoy the benefits of low-maintenance living with an incredibly affordable HOA fee of just $95 per year. Whether you're a first-time buyer, downsizing, or adding to your investment portfolio, this home offers a great combination of value, updates, and convenience. Don’t miss your chance to make it yours!

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

Listing Agent: Michelle Smith (863-412-7577)

Remarks: Auction Property. Ranch-style home offering 2 bedrooms and 1.5 bathrooms with a spacious living room and a good-sized yard. Features include a durable metal roof, RV electrical hookups, and a chicken coop. Some updates in the kitchen. Short Sale subject to lender approval.

Listing is courtesy of: JASON MITCHELL REAL ESTATE FLO (754-307-0607)

Listing Agent: David Hartigan (407-955-1156)

Remarks: Short Sale. This property presents a great opportunity for buyers looking to renovate and add value. With a functional floor plan and generous living areas, it offers a solid starting point for updates and improvements. The layout provides flexibility to reimagine the space to suit your needs and design preferences. Spacious rooms allow for creative customization throughout. The kitchen area offers ample space to redesign and enhance. Bedrooms are well sized and provide potential to create comfortable retreats. There is opportunity to refresh both the interior and exterior to maximize appeal. Outdoor space allows room for landscaping or additional enhancements. Ideal for investors or buyers seeking a renovation project. Schedule your showing today and explore the possibilities.

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

Listing Agent: Cesar Estrada, Pa (321-209-4782)

Remarks: Under Construction. BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. Indigo - Check out the Indigo, a spacious two-story, 5-bedroom, 3-bathroom, 2-car garage home perfect for growing families or hosting guests. Enter the impressive foyer with soaring ceilings that creates an immediate sense of openness. From the foyer, the home effortlessly flows into the main living areas and kitchen. With quartz countertops throughout, stainless-steel appliances and a smart thermostat for energy efficient climate control, the Indigo brings all the things that matter together. The downstairs guest suite and bathroom are tucked away for added seclusion, while the open concept living space is perfect for entertaining. Upstairs, you'll find a generously sized recreation space, ideal for family time or unwinding. The owner's suite is a true sanctuary, featuring a walk-in shower, double vanities, and a spacious walk-in closet. A laundry room with a new washer and dryer is just off the owner’s suite, conveniently located near the 3 additional bedrooms and full bathroom. The Indigo is as functional as it is stylish, providing the perfect balance of comfort and modern living. Close to it all, Villa Mar places you near the natural beauty of the Winter Haven Chain of Lakes, the charm of downtown Winter Haven, and family fun at LEGOLAND® Florida Resort. Back at home, residents enjoy community amenities including a pool, dog park, playground, and walking trails. Images shown are for illustrative purposes only and may differ from actual home. Completion date subject to change. Contact or make an appointment for more details on interest rates.

Listing is courtesy of: CASA FRESCA REALTY (813-343-4383)

Listing Agent: Michael Human (813-343-4383)