Winter Haven Homes For Sale & Real Estate - 1041 homes

Remarks: Discover the perfect blend of style, comfort, and peace of mind in this beautifully updated 3-bedroom, 2-bath home that’s ready for you to move right in. Thoughtfully refreshed with fresh interior and exterior paint, this home offers a bright, welcoming atmosphere from the moment you arrive. The heart of the home is the stunning kitchen, featuring gorgeous granite countertops, sleek stainless steel appliances, and ample cabinet and counter space—perfect for preparing family meals, entertaining guests, or enjoying your morning coffee. The open and functional layout creates a warm, inviting flow that’s ideal for both everyday living and special gatherings. Enjoy the confidence that comes with major recent upgrades, including a brand-new roof and new energy-efficient A/C system, providing comfort and peace of mind for years to come. Retreat to the spacious primary suite, while two additional bedrooms allows for flexibility for family, guests, a home office, or hobby space. Every room has been thoughtfully refreshed, making this home truly move-in ready. Step outside and fall in love with the oversized backyard—just under a quarter acre—offering endless possibilities. Whether you envision weekend barbecues, kids play area, a flourishing garden, or simply relaxing under the Florida sunshine, this outdoor space is ready to bring your vision to life. The bonus storage shed provides valuable extra space for lawn equipment, tools, seasonal décor, or even your favorite DIY projects. Conveniently located near shopping, restaurants, schools, parks, and major roadways, this home combines everyday convenience with the charm of a quiet neighborhood. Whether you’re a first-time homebuyer, growing family, downsizing, or searching for a fantastic investment opportunity, this exceptional property checks all the boxes. Don’t miss your chance to own this beautifully updated Winter Haven gem. Schedule your private showing today and experience everything 362 Holly Ridge Road has for you!

Listing is courtesy of: MILLSHIRE REALTY (863-815-8000)

Listing Agent: Katrina Asher (863-934-0575)

Remarks: Enjoy peaceful lakeside living at 207 Winter Ridge Blvd! This 2-bedroom, 2-bath condo is ready to move into. The home features an enclosed Florida room, primary bedroom with walk in closet, open floor plan, and stunning lake views. The community features a pool, clubhouse, shuffleboard, and a lot more. Call, text, or email for your private showing. *Agents, please read MLS remarks.*

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

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

Remarks: New - New - New! This 3 bedroom 2 bath features a beautiful lake view and has been completely remodeled. Updates include a new HVAC system, new metal roof, new kitchen with granite counters, new bathrooms, new flooring, and new septic system. No HOA means you can store your boat.

Listing is courtesy of: ALLSTATE REALTY SERVICES (863-965-0207)

Listing Agent: Dwight Head (863-965-0207)

Remarks: Lakefront living with a proper sunset! Down a private road with no HOA (because your house shouldn't come with a rule book). This renovated home offers direct frontage 80' on Lake Pansy and a bonus 80' of canal frontage across the street. The property provides excellent water access and endless sunset views. Outside is where this home really shows off with amenities including a heated saltwater pool / lap pool with markers on the bottom, lighting and water features, added style with a surfboard outdoor shower, screened in with panoramic panels because this view deserves center stage. The outdoor summer kitchen is outfitted with a refrigerator, table top ice chest, bar area, and a grill supplied by a 99-gallon propane tank, making it well-suited for entertaining all year round. The lanai is glassed in with cedar tongue and groove ceiling and motorized retractable sunshade, while enhanced landscape lighting and mature palm trees set the tropical tone. Additional exterior upgrades include a composite dock, fenced in yard, seamless gutters with leaf filters, and recently replaced garage and front entry doors. Inside, the vibe continues with an electric fireplace with customizable lighting (because ambiance matters). Live-edge floating shelves with integrated lighting adds a designer touch. Double-pane replacement windows, custom drapes, California Closets, luxury vinyl and ceramic tile throughout, laundry closet for added convenience. The kitchen brings the function and the flair with an island, generous storage, new cabinetry, quartz countertops, a natural gas range with hood ventilation, along with a built in microwave, electric oven, and refrigerator/freezer. Culligan water treatment. The roof and HVAC system are approximately 10 years old. Additional features include epoxy garage floor, LRE foundation improvements, and well-fed irrigation. Prewired generator hook-up installed in garage. The boat ramp is located on the west side of lake Pansy. Conveniently Located 20 minutes from Lego Land, 7 minutes from Publix Super Market, 5 minutes to Home Depot, 3 minutes to the nearest boat ramp to access the Winter Haven Chain of Lakes. This is a rare opportunity to own a turnkey lakefront property with endless sunsets, extensive upgrades, and no HOA restrictions.

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

Listing Agent: Olivia Boggs (863-232-8234)

Remarks: Virtually Staged. Welcome to this updated 4-bedroom, 2-bath home offering 1,750 square feet of bright, open living space in the desirable Queens Cove community of Winter Haven. Step inside to discover vaulted ceilings, abundant natural light, and an open-concept floor plan designed for comfortable everyday living and effortless entertaining. Luxury vinyl plank flooring flows throughout the house, while the spacious kitchen features granite countertops, white cabinetry, stainless steel appliances, extensive counter space, a breakfast bar, and a seamless connection to the living and dining areas. The split-bedroom layout provides added privacy, with a generous primary suite offering a walk-in closet and an en-suite bath. Three additional bedrooms provide flexibility for family, guests, or a home office. Sliding glass doors lead to the backyard with plenty of space to create your own outdoor oasis, add a pool, or simply enjoy Florida living. Additional highlights include a two-car garage, an inside laundry area, and a roof replaced in 2018 and new HVAC in 2022. Conveniently located just minutes from Legoland Florida Resort, shopping, restaurants, schools, medical facilities, and major roadways including the Polk Parkway and US-27, this home offers easy access to both Tampa and Orlando while enjoying the charm of Winter Haven's renowned Chain of Lakes. Whether you're searching for your primary residence, a second home, or an investment property, this move-in-ready home offers exceptional value in a convenient Central Florida location.

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

Listing Agent: Cindy Greco (813-240-8300)

Remarks: Introducing the Denham at Harmony at Lake Eloise, in Winter Haven, Florida. A stunning 2,336 square foot, single-story home featuring 4 bedrooms, 3 bathrooms, and a spacious 3-car garage. As you step inside a grand foyer draws you in, leading you through a thoughtfully designed layout where every detail shines. Bedrooms 2, and 3, and 4 branch off from the foyer, creating a private wing for family and guests. Moving into the heart of the home, an expansive open concept living space invites you to unwind or entertain with ease. Find luxurious quartz countertops, luxury vinyl plank flooring, and top of the line stainless steel appliances, all crafted for both elegance and functionality.

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

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

Remarks: This villa has recently had upgrades added and the seller is offering $7,000 AT CLOSING TOWARD CLOSING COSTS OR ADDITIONAL UPGRADES. New HVAC system, new kitchen cabinets, new appliances, new flooring, and even new drywall. This beautiful home is located directly on golf course frontage and has newer metal roof. You will be living in a community with a manned guard gate and your villa is only a short walk to the clubhouse, restaurant, and pool. Don't miss out on this one, call to view today. Flood zone area is deemed to be correct but must be verified by buyer/buyer broker.

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

Listing Agent: Darlene Bice (863-293-1141)

Remarks: Every Detail Has Been Thoughtfully Designed. Every Upgrade Has Been Thoughtfully Completed. Welcome to a home where quality craftsmanship, modern style, and everyday comfort come together effortlessly. Nestled on a beautifully landscaped nearly half-acre homesite overlooking peaceful Garden Lake, this impeccably maintained 3-bedroom, 2-bath residence offers the perfect balance of privacy, sophistication, and smart-home convenience. A natural privacy hedge of mature hibiscus surrounds the backyard, creating a tranquil setting that is increasingly difficult to find. From the screened front entry to the spacious screened lanai, every space has been designed to embrace Florida living while showcasing the exceptional care invested throughout the home. Inside, the open-concept floor plan is warm, inviting, and filled with natural light. Smart-home technology allows you to control the lighting, electric fireplace, and garage door opener with ease, while tasteful finishes and thoughtful updates create a contemporary feel that is as functional as it is beautiful. The completely updated kitchen serves as the heart of the home, featuring granite countertops, a farmhouse sink, elegant 42-inch upper cabinetry, redesigned lower cabinetry, recessed lighting, stainless steel appliances, and a generous workspace. The open layout is ideal for entertaining while maintaining a warm, inviting atmosphere for everyday living. The attention to detail continues throughout with beautiful flooring, updated lighting, refreshed bathrooms with granite countertops and modern fixtures, energy-efficient Low-E replacement windows, and countless improvements that reflect exceptional ownership. Outdoor living is equally impressive. Relax year round on the newly screened lanai with its attractive epoxy floor and premium UV-protective screening provides the perfect place to relax while enjoying peaceful views of Garden Lake. This private outdoor retreat is sure to become a favorite gathering place. Significant improvements—including a Bryant HVAC system, water heater, energy-efficient Low-E windows, updated exterior paint, smart garage door opener, and numerous additional upgrades—offer the peace of mind every buyer is looking for. Completing the home is a long-lasting clay tile roof that adds timeless character and enhances the home’s exceptional curb appeal. Located within the highly sought-after gated community of Winterset, residents enjoy exceptional amenities including a heated pool and spa, clubhouse, tennis courts, beautifully maintained grounds, private boat ramp and dock on Lake Winterset, and access to the renowned Winter Haven Chain of Lakes—all with a low HOA. Thoughtfully updated. Beautifully maintained. Perfectly positioned. A home that feels brand new—without the wait.

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

Listing Agent: Laurie Nock (937-218-0031)

Remarks: Under contract-accepting backup offers. Short Sale. A beautifully maintained 3 bedroom, 2 bath home built in 2021, with 1,727 square feet of thoughtfully designed living space. Located in the desirable Lucerne Park Reserve community, this home combines modern finishes, an open layout, and everyday convenience. Step inside to discover a bright, open-concept floor plan featuring tile and luxury vinyl plank flooring throughout, and high ceilings that create a spacious, inviting atmosphere. The stylish kitchen is the heart of the home, complete with stainless steel appliances, a large center island, generous pantry, and plenty of counter space perfect for entertaining or everyday living.The private primary suite offers a relaxing retreat with a walk-in closet and an en-suite bathroom featuring dual vanities. A split-bedroom floor plan provides privacy for family members or guests, while the indoor laundry room adds everyday convenience. Enjoy Florida living from the covered rear porch overlooking a peaceful greenbelt, providing added privacy with no rear neighbors. The home also includes a 2-car attached garage, irrigation system, and attractive landscaping. Residents of Lucerne Park Reserve enjoy community amenities including a pool, playground, sidewalks, and streetlights. Conveniently located just minutes from Highway 27, shopping, dining, and approximately 20 minutes from Legoland Florida, this home offers easy access to everything Central Florida has to enjoy.

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

Listing Agent: Kate Wilson (352-816-0397)

Remarks: NEW PRICE!! 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: Step into timeless elegance with this stunning Mediterranean-style estate in the heart of Winter Haven. Offering over 4,100 square feet of living space, this one-of-a-kind property features a private casita, private pool, and endless possibilities for multi-generational living, guest accommodations, or a home office. Recent updates include a new roof and new AC, giving buyers peace of mind while preserving the home's unique character and charm. Enjoy spacious living areas, beautiful architectural details, and plenty of room for entertaining both indoors and outdoors. With no HOA, ample parking for boats, RVs, and recreational vehicles, and a prime location near Winter Haven's famous Chain of Lakes, this property combines flexibility, privacy, and convenience. Whether you're looking for a family retreat, a home with income potential, or a distinctive property that stands out from the ordinary, this exceptional residence is a must-see. Schedule your private tour today and discover everything this remarkable home has to offer!

Listing is courtesy of: META ONE REALTY GROUP LLC (407-223-3678)

Listing Agent: Aline Oliveira (407-300-7123)

Remarks: Welcome home to this beautifully upgraded 4-bedroom, 2.5-bath home featuring a spacious open-concept floor plan designed for comfortable living and entertaining. The primary suite is conveniently located on the first floor and offers a luxurious, upgraded bathroom along with a custom walk-in closet complete with built-in shelving—truly a dream closet with plenty of organized storage. Upstairs, you'll find three additional bedrooms, a full bathroom, and a versatile loft that's perfect for game nights, a media room, or a cozy space to relax and watch movies. Step outside to a fully fenced backyard that provides privacy and plenty of room for outdoor entertaining, pets, or play. Why wait for new construction when this home already has the upgrades done for you? Move in and start enjoying all the thoughtful enhancements without the added time and expense.

Listing is courtesy of: ORCHARD BROKERAGE, LLC (844-515-9880)

Listing Agent: Kristie Scammell (702-234-0837)

Remarks: Priced to Sell — Bring Your Vision (and Your Toolbelt) Opportunity is knocking at 2500 21st St NW, #50 in Winter Haven, and it’s asking for someone ready to turn sweat into serious equity. This lake view property is priced well below its true value for the location and community the kind of deal that rewards buyers who see potential where others see a to-do list. Location is everything here: you’re right across the street from the community pool and clubhouse, and the community even features its own dock lakeside living at your doorstep. Step inside and you’ll find durable tile throughout the downstairs, with laminate flooring running up the steps and across the entire upstairs no carpet to worry about. The upstairs master bedroom comes with its own private balcony view of the lake from the balcony, the perfect spot to take in the surroundings. The kitchen shines with stainless steel appliances, solid countertops, and cabinets in great working condition. Yes, she needs some TLC: a little cleaning, a fresh coat of paint, and a new AC unit. But here’s the good part we already have an estimate from a reputable local company ready to install the unit with a warranty. The heavy lifting on the hardest fix is already scoped out for you. The home is vacant and virtually staged, so you can walk in with a blank canvas and picture your own finishing touches (furniture shown is virtual). Homes with this kind of upside, in this location, at this price, don’t sit long. If you’ve been waiting for the chance to build instant equity in a lakeside community steps from the pool, clubhouse, and dock this is it. Bring your imagination, roll up your sleeves, and make it your own. The community offers two pools (one is adult only), shuffleboard, tennis court, clubhouse and dock. Priced to sell. Move fast.

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

Listing Agent: Jason Prieto (877-366-2213)

Remarks: Welcome to your dream home, a charming 2-bedroom, 2-bath retreat with a versatile bonus room that can be used as a 3rd bedroom or a separate home office featuring its own private exterior entrance! This inviting home has been thoughtfully refreshed and is move-in ready, offering fresh interior paint, a new smart thermostat, recent tree removal, and a brand-new shingle roof (03/24) for peace of mind! Inside, you’ll find a spacious kitchen with a breakfast bar that opens to a bright living room, ideal for everyday living and entertaining. The large dining room or secondary family room is conveniently located next to the kitchen and provides plenty of space for gatherings. Relax in the cozy Florida room, featuring warm wood walls and ceilings and an abundance of windows where you can enjoy views of Lake Elbert! Outside you will find your large paver patio, perfect for entertaining or unwinding, and enjoy the privacy of a newly built fully fenced backyard. Additional updates include a new AC (2022), blown attic insulation (2022), water heater (2019), all kitchen appliances (2021), and Exterior Front Porch paint along with a new front door (2025). Conveniently located just minutes from Downtown Winter Haven, Polk State College, HWY 27, and medical facilities, this home blends comfort, flexibility, and an excellent location. Schedule your showing today!

Listing is courtesy of: LIVE FLORIDA REALTY (863-868-8905)

Listing Agent: Jenna Henderson (850-524-3843)

Remarks: Under contract-accepting backup offers. Welcome to your own private backyard retreat in the heart of Winter Haven! This beautifully maintained 3-bedroom, 2-bath pool home sits on a spacious .31-acre lot with NO HOA and offers the perfect blend of comfort, convenience, and Florida living. The true showstopper is the incredible approximately *983-square-foot covered lanai*, creating an expansive outdoor living space rarely found in homes of this size. Perfect for entertaining, relaxing, outdoor dining, or even a home gym, this massive covered retreat overlooks the sports-style pool, oversized fenced backyard, custom playground, firepit, raised irrigated garden beds, and turf-and-tile entertaining area. Best of all, enjoy spectacular *LEGOLAND fireworks* views right from your own backyard. Inside, you'll find a bright and inviting floor plan with generous living spaces, comfortable bedrooms, and a well-appointed kitchen that flows seamlessly into the living and dining areas. Recent updates provide peace of mind, including a New Roof (2023), New Covered Lanai (2023), whole-home re-plumbing (2024), reverse osmosis system in the kitchen (2024), stainless steel dishwasher (2021), gas water heater (2021), irrigation system for yard (2023), updated light fixtures throughout, Ring security system with automatic flood lights, and added recessed lighting in the living room and kitchen. The outdoor space was thoughtfully enhanced in 2024 with stained fencing, rocked and irrigated landscape borders, a fully sealed playground, and beautifully designed gathering spaces that make this property ideal for everyday living and entertaining alike. Conveniently located just minutes from Downtown Winter Haven, LEGOLAND Florida Resort, major hospitals, shopping, dining, and everyday conveniences, this move-in-ready home offers the perfect combination of location, lifestyle, and value. Don't miss this rare opportunity to own a beautifully updated pool home with an extraordinary outdoor living experience. Schedule your private showing today!

Listing is courtesy of: LIVE FLORIDA REALTY (863-868-8905)

Listing Agent: Jenna Henderson (850-524-3843)

Remarks: Under Construction. Under construction. This new construction build sits on almost an acre (.72) and is a comfortable and cozy home with 3 bedrooms, 2 bathrooms and 1,467 square feet of living space. The foyer opens to the spacious dining and great rooms, with raised ceilings throughout the home, and there's convenient access to the outdoor patio from the living space. The kitchen features a large island. The primary bathroom boasts a separate shower and tub, and this home comes equipped with ample storage space including two oversized primary walk-in closets, a pantry in the kitchen, a linen closet and a coat closet. The spacious (413 sq ft) 2-car garage provides additional storage and laundry space. This home is located in a quiet neighborhood off Winter Lake Rd, close to all of the amenities Lakeland or Winter Haven have to offer! With no HOA, there's room for your boat, RV, or other outdoor vehicles. USDA FINANCING AVAILABLE FOR ELIGIBLE BUYERS, WITH NO MONEY DOWN. CALL TODAY FOR MORE DETAILS.

Listing is courtesy of: PORCHLIGHT HOMES LLC (863-529-3369)

Listing Agent: Angie Reynolds (863-838-1090)

Remarks: Under Construction. The Astor is one of our one-story floorplans featured in Harmony at Lake Eloise in Winter Haven, Florida. With 3 exteriors to choose from, the Astor is sure to turn heads. Inside this 3 bedroom, 2 bathroom home, you’ll find 1,565 square feet of comfortable living. This home offers a two-car garage and covered porch in the rear of the home. As you enter, you're greeted with a spacious living area, coat and linen storage closets and dedicated laundry room. The kitchen located in the center of the home features quartz countertops, an island, stainless steel appliances and a pantry. You’ll never be too far from the action with the living and dining area to the immediate left and right. The primary bedroom has an attached bathroom that features a walk-in closet, double sink vanity and all the space you need to get ready in the morning. Every bedroom features carpeted floors and a closet. Whether these rooms become bedrooms, office spaces, or other bonus rooms, there is sure to be comfort. Like all homes in Harmony at Lake Eloise, the Astor 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.*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. Ready in August 2026! 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: Welcome to this beautifully maintained waterfront home on an oversized lot in the desirable Island Lakes community. This contemporary residence combines comfort, functionality, and breathtaking lake views. Step inside to discover an open-concept floor plan with soaring cathedral ceilings, abundant natural light, and a desirable split-bedroom layout. The spacious primary suite has views of the lake and access to the screened in back porch. The ensuite includes a large walk-in closet, dual vanity, soaking tub, shower and private water closet. The comfortable great room flows seamlessly into the kitchen and dining areas, creating the perfect setting for everyday living and entertaining. Secondary bedrooms are generously sized and perfect for family and guests. The true highlight of this property is the direct frontage on Lake Rochelle, part of Winter Haven's renowned Chain of Lakes. Your private dock is perfect for fishing or parking your boat. Enjoy peaceful views and breezes from the screened rear porch overlooking the water. Roof replaced in 2024, all new LVP in the family and dining rooms. Whether you enjoy boating, fishing, water sports, or simply relaxing by the lake, this property offers the Florida lifestyle you've been dreaming of. Pack your bags and move in today!

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

Listing Agent: Amy Moline (407-506-7447)

Remarks: This charming 4-bedroom, 2-bathroom new construction build features an open floor plan and 1,778 square feet of living space, all while sitting on a .73 acre lot. The spacious great room, with high vaulted ceilings is perfect for family movie nights in, with convenient access to the back patio. The large open kitchen caters to family living as well as entertaining with its lengthy seated bar for that delicious morning breakfast, and is located perfectly in between the great room and dining area. The ample primary bedroom is enhanced by its dual-sink vanity bathroom and walk-in closet featuring a linen closet within. Additionally, the spacious garage provides additional storage and leads directly into the home’s designated laundry space. This home is located in a quiet neighborhood off Winter Lake Rd, close to all of the amenities Lakeland or Winter Haven have to offer! With no HOA, there's room for your boat, RV, or other outdoor vehicles. USDA FINANCING AVAILABLE FOR ELIGIBLE BUYERS, WITH NO MONEY DOWN. CALL TODAY FOR MORE DETAILS.

Listing is courtesy of: PORCHLIGHT HOMES LLC (863-529-3369)

Listing Agent: Angie Reynolds (863-838-1090)