Winter Haven Single Family Homes For Sale - 749 homes

Remarks: ~2/2 Winter Haven residence Offered for Sale~ Great opportunity for a first-time home buyer or an investor! This adorable 2/2 property features 1396 square feet of living area, a split plan, two bonus rooms which could be used as bedrooms, vaulted ceilings, primary bedroom with walk-in closet and en-suite bath, wood burning fireplace, large, screened patio and a one car garage. Roof and A/C are less than 5 years old and water heater is newer. Convenient to fishing, dining, shopping, and medical/educational facilities. Monthly HOA fee covers grounds maintenance, streetlights and community pool care.

Listing is courtesy of: HOUSE OF GLASS REAL ESTATE PM (863-940-3756)

Listing Agent: Andrea Muzzy (863-430-1733)

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: One or more photo(s) has been virtually staged. Located in the desirable Hamilton Pointe community, this beautifully maintained 4-bedroom, 2.5-bath, 3,114 sf pool home built in 1992, sits on a half-acre lot with no rear neighbors offering peaceful views of a protected conservation area and ultimate backyard privacy. Features include a spacious kitchen with eat-in area and French doors to the lanai, a grand family room with 13’ ceilings, crown molding, and a striking coral tile fireplace. The split floor plan offers a large master suite with garden tub, walk-in shower, dual vanities, and lanai access, with one bedroom perfect for an office space. Two bedrooms are on the other side of the home with another full bath and laundry room. Enjoy mature landscaping, a refreshing screened-in pool (resurfaced approx. 3 years ago, new sand filter 2 years ago, rescreened 1 year ago), and numerous updates—new roof (2019), Hybrid electric heat pump water heater that is in the garage (2021), gutters/screens (2020), exterior paint (2019) and whole house was re-piped (2021) . Convenient to downtown Winter Haven, Hwy 27, LEGOLAND, golf, shopping, and airports. A Satisfactory 4-Point Inspection has been done.

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

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

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: FLORIDA LIVING AT ITS BEST! Pool home + oversized lot + NO HOA + Chain of Lakes access just minutes from LEGOLAND Florida Resort! This fully updated 4-bedroom, 3-bath home in SE Winter Haven offers the lifestyle buyers are chasing with TWO master suites, a HUGE FENCED BACK YARD, heated pool, and room to bring the boat, jet skis, golf cart, and all the toys. Inside you’ll find a designer-style interior featuring luxury vinyl flooring, oversized living spaces, and a stunning chef’s kitchen with quartz countertops, custom soft-close cabinetry, stainless steel appliances, and a premium Ruvati workstation sink. The oversized primary suite feels like a private retreat with tray ceilings, spa-inspired bathroom, soaking tub, dual vanities, walk-in shower, and spacious walk-in closet. A second private ensuite is perfect for guests, multigenerational living, or an in-law suite. Step outside to your screened lanai overlooking the heated inground pool and massive backyard — ideal for entertaining, relaxing, and enjoying year-round Florida sunshine. The pool is equipped with a top-of-the-line Raypak pool heater, making it easy to enjoy swimming year-round! MAJOR UPGRADES INCLUDE: New roof (2019), whole-house replumb (2019), AC handler (2019), water heater (2019), remodeled kitchen (2021), luxury vinyl flooring (2021), top-of-the-line Raypak pool heater (2022), variable-speed pool pump (2024), irrigation system (2024), and guest bathroom remodel (2025). Located less than 2 minutes from the Lake Summit boat ramp with access to 20+ connected lakes, waterfront dining, skiing, and fishing, this home is the perfect mix of luxury, freedom, and Florida lifestyle

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

Listing Agent: Christina Loesch (347-977-0962)

Remarks: Come see 2953 Whispering Trails Dr, a residence showcasing recent fresh interior paint and fresh exterior paint for a clean, cohesive appearance. The kitchen is equipped with all stainless steel appliances, and the primary bathroom provides practical double sinks. Outside, a welcoming patio leads to a fully fenced in backyard. This move-in ready property blends comfort and recent updates seamlessly. Included 100-Day Home Warranty with buyer activation

Listing is courtesy of: OPENDOOR BROKERAGE LLC (480-462-5392)

Listing Agent: Karen Albright (480-462-5392)

Remarks: Come see 1100 Carefree Cove Dr, recently improved with a new roof, fresh exterior paint, and fresh interior paint, presenting a comprehensively refreshed presentation. Partial flooring replacement further updates the interior living spaces, while a fenced in backyard provides practical outdoor areas. This property embodies a fresh approach to comfortable living. Included 100-Day Home Warranty with buyer activation

Listing is courtesy of: OPENDOOR BROKERAGE LLC (480-462-5392)

Listing Agent: Karen Albright (480-462-5392)

Remarks: Fully furnished, move in ready pool home located in a quiet, established Winter Haven neighborhood just minutes from LEGOLAND Florida. Situated in a community known for long term ownership and pride of ownership, this property offers a peaceful setting with exceptional convenience and no HOA. A gated side entrance provides rare RV or boat parking, adding flexibility and value. The interior features updated flooring, a modern kitchen with quartz countertops and stainless steel appliances, and a bright, open floor plan designed for comfortable living. Outdoor living shines with a screened in pool and covered patio, ideal for relaxing or entertaining year round. Offered fully furnished, including TVs, this home is perfect for primary residence, relocation, seasonal use, or investment. Roof will be replaced before closing. Truly turn key—just bring your suitcase and enjoy the Florida lifestyle from day one, 3 miles from LEGOLAND.

Listing is courtesy of: NEXTHOME NORRIS & COMPANY REAL (863-875-5583)

Listing Agent: Michael Norris (863-287-3105)

Remarks: JUST REDUCED !! 4-bedroom, 2-bathroom home, you'll find 1,713 square fee of comfortable living. A Craftsman-style front porch welcomes you into the fully open living area featuring airy volume ceilings and sunny natural lighting. Unwind in your private owner's suite complete with a large walk-in wardrobe and a private en-suite bath with dual vanities, a tiled glass-enclosed shower, private toilet, and a linen closet. This meticulously designed residence combines modern convenience with timeless elegance, showcasing quartz 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 quartz 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 are flexible 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. Priced to Sell !!

Listing is courtesy of: BEACH REALTORS (407-201-6300)

Listing Agent: Rachel Reyes (407-201-6300)

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: WELCOME HOME TO STONEBRIDGE! WHERE COMFORT, STYLE, AND CONVENIENCE COME TOGETHER! Step through the custom gated courtyard and discover this beautifully updated residence that is truly move-in ready. From the moment you enter, you'll be impressed by the gorgeous porcelain tile flooring that flows throughout the main living areas, creating an elegant and welcoming atmosphere. The spacious Great Room serves as the heart of the home, featuring a stunning wood-paneled fireplace that creates a warm focal point for relaxing or entertaining. Newer(2022) Sliding Doors lead to a private covered and screened patio, offering the perfect place to enjoy your morning coffee, unwind after a long day or entertain guests in a peaceful outdoor setting. Adjacent to the Great Room is a dedicated dining area with a convenient pass thru to the kitchen. The beautifully updated kitchen showcases rich cabinetry, granite countertops, stainless steel appliances, and a breakfast nook, perfect for preparing meals and gathering with family and friends. Enjoy the convenience of the sliding doors out to the private courtyard. Retreat to the spacious primary suite, complete with a walk-in closet and an updated ensuite bath featuring a walk-in shower and modern finishes. The guest bedroom offers generous closet space and flexibility for visitors, a home office, or craft room. The beautifully renovated guest bathroom features a striking designer tile accent wall, creating a stylish, space for family and guests. Additional highlights include a NEW ROOF (2024), NEW GUTTERS/DOWNSPOUTS (2026), NEW ELECTRIC PANEL (2024), NEWER WINDOWS AND SLIDERS (2022), updated bathrooms, washer and dryer, one-car garage, neutral décor throughout, and move-in-ready condition. Outside, enjoy both the private courtyard and the covered screened patio, offering multiple outdoor living spaces rarely found at this price point. Residents of Stonebridge enjoy access to a community pool and a convenient location close to shopping, restaurants, churches, medical facilities, and everyday conveniences. Located in the heart of Winter Haven, known as Florida's Chain of Lakes City, residents enjoy boating, fishing, waterfront dining, golf courses, beautiful parks, and year-round recreation. Winter Haven is also home to LEGOLAND Florida Resort and offers convenient access to both Orlando and Tampa, making it an ideal location for full-time residents, seasonal homeowners, or anyone seeking the Florida lifestyle. Hurry, schedule an appointment today to view this fabulous patio home.

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

Listing Agent: Kitty Mark (407-491-6857)

Remarks: Move-in ready! Welcome to the Residences at Winter Haven, a premier new single-family community designed for those who value both quality and connection. Set within this inviting neighborhood, the Everglades floor plan brings a natural ease to everyday living, from its open layout to the thoughtful finishes. At the heart of the home is a stunning kitchen featuring a large waterfall island and 42” cabinetry. Designed for hosting, the living area flows effortlessly out to a covered lanai. It’s a clean, modern space ready for you to make your own.

Listing is courtesy of: KELLER WILLIAMS REALTY AT THE LAKES (407-566-1800)

Listing Agent: Rodrigo Gomes De Almeida (407-837-8173)

Remarks: Lakefront living on beautiful Lake Cannon! Wake up every day to sparkling water views and enjoy peaceful sunsets from this charming 2-bedroom, 1-bath waterfront retreat. Perfectly positioned to take advantage of the scenery, the home features a bright and inviting interior with a spacious living area and an oversized picture window that frames the lake like artwork. Natural light pours in, creating a warm and cheerful atmosphere throughout. Outside, enjoy the easy Florida lifestyle with plenty of yard space, covered parking, and direct lakefront access on one of the most desirable lakes in the Winter Haven Chain of Lakes. Whether you love boating, fishing, kayaking, or simply relaxing with your morning coffee while taking in the view, this property delivers. A rare opportunity to own affordable lakefront in Central Florida—ideal as a full-time residence, winter getaway, or investment property. Bring your boat, bring your fishing pole, and start enjoying life on Lake Cannon!

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

Listing Agent: Michele Elchin (863-514-6880)

Remarks: One or more photo(s) has been virtually staged. Welcome to this beautifully maintained 3-bedroom, 2-bathroom home located in the desirable Winter Haven area! This move-in ready property offers a perfect blend of comfort, style, and modern updates throughout. From the moment you step inside, you’ll notice the upgraded accent wall paneling featured in the foyer, dining room, and spacious primary bedroom, adding warmth and custom character to the home. The dining room and foyer have also been enhanced with updated light fixtures that provide a fresh, elegant touch. Pride of ownership is evident throughout, as this home has been exceptionally well maintained and cared for. With inviting living spaces, a functional layout, and tasteful upgrades, this home is ideal for both relaxing and entertaining. Conveniently located near shopping, dining, schools, and major roadways, this property combines comfort and convenience in one attractive package. Don’t miss your opportunity to own this charming Winter Haven home — schedule your private showing today!

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

Listing Agent: Matt Everett (231-563-3176)

Remarks: 329 Lake Daisy Loop | NO HOA Welcome to this beautiful 3BR/2BA home in Lake Daisy Estates, offering over 1,500 sq. ft. of comfortable living space on a spacious corner lot—and best of all, NO HOA, giving buyers the freedom they want. This home features a bright formal living and dining area, a spacious kitchen with Frigidaire appliances, and a large family room with vaulted ceilings and a wood-burning fireplace. Sliding doors open to a generous enclosed patio, perfect for relaxing or entertaining. The master suite includes a walk-in closet, jetted tub, separate shower, double sinks, and private access to the patio. Additional highlights include: Marble flooring installed in 2025, New AC (2025), Roof replaced in 2017, Window shades installed in 2025, Indoor laundry room 2-car garage Located just minutes from Legoland (5 min), Walmart (4 min), shopping centers, restaurants, schools, and medical facilities. A fantastic opportunity in a prime location with no HOA—highly attractive for today’s buyers.

Listing is courtesy of: LA ROSA RTY WINTER GARDEN LLC (407-614-5158)

Listing Agent: Jasmin Vargas (407-747-2367)

Remarks: Under Construction. This two-story Georgia will definitely be on your mind… This beauty highlights a modern open layout, seamlessly integrating a first-floor kitchen with a central island, a dining room and a welcoming family room with patio access. On the same level is a private owner's suite with an attached bathroom. Situated upstairs is a versatile loft for additional shared living space and four secondary bedrooms to provide restful retreats to family members and guests alike. Villa Mar is a masterplan community of new single-family homes. Near Historic downtown Winter Haven. There are lots of shops, restaurants, bike paths, and easy access to nearby highways. Close to Legoland and Bok Tower Gardens. The much anticipated “Villar Mar” community is what you have been looking for. A safe small town feel with convenience.

Listing is courtesy of: LENNAR REALTY (800-229-0611)

Listing Agent: Ben Goldstein (407-310-7677)

Remarks: Gated custom home in the Gates of Lake Region! This quiet and highly-desirable neighborhood has the look, feel and privacy of an age-restricted community, but it is open to all ages. This property was constructed as a builder’s model home so it offers numerous upgrades and architectural details that can be found throughout. Located within the quaint, gated community of The Gates of Lake Region and built by Alan Ulch Construction, the home offers nearly 2,500 square feet of spacious living area. Construction includes high-efficiency Ytong concrete block, providing superior sound reduction, enhanced structural performance, and meaningful energy savings. This elegant home features 4 spacious bedrooms (one currently used as an office), 2 full baths, and 1 half bath. Refined interior finishes include crown molding, oversized custom doors, handcrafted double entry doors, custom cabinetry, ceiling fans, a jetted tub in the primary suite, and a generously sized laundry room. Lush landscaping and a covered front entry create a warm and inviting arrival. Inside, the foyer opens to formal living and dining areas highlighted by high ceilings and detailed trim work—creating an inviting setting for both everyday living and entertaining. The well-appointed kitchen offers abundant cabinetry, solid-surface countertops, a closet pantry, and a light-filled breakfast nook overlooking the screened porch and private, brick-walled backyard. The comfortable family room features a granite-faced gas fireplace, adding warmth and ambiance. A split-bedroom layout ensures privacy for the primary suite, which includes a roomy walk-in closet, soaking tub, and tiled walk-in shower. The guest wing features two additional bedrooms with ample closet space and convenient access to the guest bath. Outdoor living is highlighted by a large screened lanai, mature tropical landscaping, and a private brick-walled backyard. Additional features include an oversized two-car garage, natural gas water heater, irrigation system, and an efficient interior laundry room with extra storage. The Gates of Lake Region is a peaceful, well-maintained community known for its scenic ponds, fountains, and quiet streets, located just minutes from the Winter Haven Chain of Lakes, multiple golf courses, the Country Club of Winter Haven, medical facilities, local dining and shopping, and Downtown Winter Haven. A brand-new Publix is planned to open nearby in 2026. Orlando, Tampa, international airports, and both Florida coasts are all an easy drive away. Come discover the charm and convenience of The Gates of Lake Region.

Listing is courtesy of: THE STONES REAL ESTATE FIRM (863-412-2080)

Listing Agent: Michael Stone (863-412-9733)