Winter Haven Single Family Homes For Sale - 750 homes

Remarks: This move-in ready 3-bedroom Winter Haven pool home offers a fantastic combination of comfort, upgrades, and true Florida living on an oversized lot with no HOA. The home features a brand-new roof, new HVAC system and thermostat, new water heater, new pool pump and chlorinator, new laundry units, new exterior front doors, and an expanded driveway with ample parking. Inside, you’ll find a functional layout with generous living space and fresh improvements throughout. The private in-ground pool creates a relaxing backyard setting, while the large lot provides room for outdoor entertaining, storage, or future additions. Located minutes from the Winter Haven Chain of Lakes, Gene’s Lakeside Marina, LEGOLAND Florida Resort, golf courses, shopping, dining, and local parks, this property sits in one of Central Florida’s most desirable and fast-growing areas. With major updates already completed and convenient access to boating, recreation, and upcoming community development, this home is an excellent opportunity for first-time buyers, families, or investors.

Listing is courtesy of: THE URBAN GROUP, INC. (954-522-6226)

Listing Agent: Ashlee Morrell (941-740-9134)

Remarks: HIGE Price Drops!! Sellers Motivated!! Bring us an offer!! Turn Key House on the North Chain of Lakes. 2023 Roof, 2022 POOL! Welcome to this pristine, beautifully maintained home in the quiet and highly desirable Island Lakes community—where there’s no through traffic and peaceful living comes naturally. This property features a newer roof put on in 2023, a newer in-ground pool put in 2022, and a large backyard shed, offering the perfect blend of comfort, storage, and outdoor enjoyment. Step outside and you’ll fall in love with the vinyl-planked dock that gives you direct access to the Chain of Lakes, making it ideal for boating, fishing, and sunset cruises. Whether you prefer relaxing in the screened-in outdoor area or lounging by the sparkling pool, this home is designed for anyone who loves outdoor living. Inside, the home is in immaculate condition. It offers three bedrooms, including a spacious master suite complete with a walk-in tub for easy washing and added convenience. Every room feels well cared for, move-in ready, and prepared for its next owner to enjoy. This stunning property truly has it all—comfort, water access, serenity, and style. It’s ready and waiting for the next buyer who wants to fully embrace lakeside living.

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

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

Remarks: This expansive property is a true diamond in the rough, perfectly positioned for the savvy investor looking for a great return on a "buy and hold" scenario or a strategic value-add project. Boasting a generous 0.41-acre lot, this property is designed for versatility. With a massive layout featuring 6 bedrooms and 4 bathrooms, the home offers the unique potential for 3 or even 4 separate doors (units), making it an ideal candidate for a multi-generational living setup or a high-performing rental portfolio addition. Only 12 minutes away from LEGOLAND!

Listing is courtesy of: MARZUCCO REAL ESTATE (813-679-1365)

Listing Agent: Clarisa Moody (813-446-2003)

Remarks: Already appraised for the listing price, this home is a great opportunity for massive savings every month on utility bills. Current owners typical electric bill in heat of summer is approx. $16 Solar panels WILL be PAID IN FULL by Sellers at closing. 4 BR/2.5 BA w/NEW ROOF 2025, NEW AC 2024. Durable porcelain wood plank-look floors throughout. Stone, wood burning fireplace in great room. Very private, screened 32 x 16 HEATED pool with large covered seating area, cabana bath, outdoor shower and and roomy storage. Well established, small gated community convenient to shopping, downtown WH, chain-of-lakes recreation. Easy going HOA. Pet friendly! Safe concrete block/stucco construction and NO CDD. Don't miss this opportunity to protect yourself from future electric rate hikes. It's move in ready!

Listing is courtesy of: PROPERTY MANAGEMENT OF POLK (863-259-4600)

Listing Agent: Julie Phillips (561-906-1118)

Remarks: Under contract-accepting backup offers. PRICE REDUCED!!!WELCOME to this beautiful 4-bedroom, 2-bath home, built in 2018, offering 1,755 sq. ft. of comfortable living space on a spacious 0.24-acre fenced lot. Located in a desirable area close to shopping, dining, and major roads, this home is perfect for those seeking both convenience and a peaceful neighborhood feel. Step inside and you'll love the bright and airy vaulted great room and the open floor plan, ideal for entertaining or everyday family living. The home features laminate & ceramic flooring throughout the main areas with cozy carpet in all bedrooms. The kitchen is a standout with its beautiful cabinetry, handmade extra shelving, all the appliances, tile backsplash, and plenty of counter space for cooking and gathering. Eagle crest is also a natural gas community, enjoying nonstop hot water with a tank less water heater. Additional thoughtful upgrades include ceiling fans in every room, custom made wood door casings and trim, washer and dryer included, and a screened lanai — the perfect spot to unwind and enjoy the outdoors. The fully fenced backyard provides privacy, security, and space for pets or family fun. The 2-car garage includes a convenient garage screen door, sprinkler system and the home also feature gutters for added protection. This home has been lovingly maintained and is truly move-in ready. Don’t miss your opportunity—call today to schedule your private tour! Some of the furniture is available for sale. CALL TODAY FOR A PRIVATE TOUR ON THIS BEAUTIFUL HOME!!!

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

Listing Agent: Gaby Murillo (863-668-1914)

Remarks: Discover this charming three-bedroom, two-bathroom residence in the desirable Savannah Estates, where comfort meets style. This inviting space features laminate flooring throughout, complemented by tile in the bathrooms. The open-concept design showcases a spacious kitchen, complete with ample cabinets, generous counter space, a breakfast bar, and stainless steel appliances, including a gas stove—perfect for culinary enthusiasts. High vaulted ceilings create an airy atmosphere in the combined kitchen, dining, and living areas, while the spacious primary bedroom boasts a large walk-in closet and an en suite bath featuring a relaxing soaker tub and a separate shower. French doors open to a large screened lanai adorned with decorative tile flooring, providing a serene outdoor retreat. The fully fenced backyard, complete with a storage shed, offers plenty of space for outdoor activities, and the convenient two-car garage adds to the home's functionality. Recent upgrades include a new roof in 2022 and a 5 year old AC unit, ensuring peace of mind for years to come. Additionally, the assumable lease on solar panels at $210 per month enhances energy efficiency and sustainability. Don’t miss the opportunity to make this beautiful property your own! Click on the virtual link attached for a full tour!

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

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

Remarks: BEAUTIFUL SE POOL HOME LOCATED ON A QUIET CUL-DE-SAC IN DESIRABLE HARBOR ESTATES. SITUATED ON A SPACIOUS WOODED LOT OF OVER 1/2 ACRE. THIS PROPERTY OFFERS PRIVACY, MATURE LANDSCAPING AND PLENTY OF OUTDOOR LIVING SPACE FOR ENTERTAINING OR FOR THOSE FAMILY GATHERINGS. THIS HOME FEATURES 4BR PLUS A PRIVATE GUEST BEDROOM AND BATH, IDEAL FOR GUESTS, MULTI GENERATIONAL LIVING OR FLEXIBLE HOME OFFICE SPACE. ENJOY THIS 38X10 LANAI OVERLOOKING THE SCREEN ENCLOSED POOL, PERFECT FOR ENTERTAINING AND RELAXING YEAR ROUND. LARGE ENTRY FOYER WITH FORMAL LIVING ROOM WITH FIREPLACE, PLANTATION SHUTTERS THROUGHOUT. FORMAL DINING ROOM FOR THOSE FAMILY DINNERS. LARGE OPEN KITCHEN WITH ABUNDANCE OF CABINETS, LARGE CENTER ISLAND WITH GRANITE COUNTERTOPS AND STAINLESS APPLIANCES, A CHEF'S DELIGHT. 20 X 16 FAMILY ROOM WITH FULL STORAGE WALL. SPACIOUS PRIMARY BEDROOM HAS MASTER BATH WITH DOUBLE VANITIES AND STEP IN SHOWER. WALK IN CLOSET WITH ORGANIZER SHELVING. DON'T NEED TO FORGET ... THE OVERSIZED SIDE ENTRY GARAGE HAS A MINI SPLIT AC UNIT AND HAS PREVIOUSLY COOLED THE SPACE FOR AN ART STUDIO, SO MANY POSSIBILITIES. THIS HOME IS CONVENIENTLY LOCATED NEAR SHOPPING, DOWNTOWN EVENTS, RESTAURANTS AND NEAR AREA LAKES ON OUR FAMOUS WINTER HAVEN CHAIN OF LAKES. THIS IS A RARE OPPORTUNITY TO OWN A HOME IN ONE OF OUR SE WINTER HAVEN'S MOST ESTABLISHED COMMUNITIES.

Listing is courtesy of: FLORIDA HOME CHOICE REALTY (863-412-2727)

Listing Agent: Glenda Pruitt (863-412-2727)

Remarks: One or more photo(s) has been virtually staged. Price reduced to $240,000. This newer construction 3-bedroom, 2-bath home offers a compelling opportunity for buyers looking for location, layout flexibility, and upside potential. Built in 2025, the property features an open living area, laminate wood flooring, white cabinetry, stainless steel appliances, and a tankless water heater. The functional floor plan allows for a variety of uses, whether for primary residence, multigenerational living, or investment purposes. Located just minutes from Downtown Winter Haven, the Chain of Lakes, hospitals, shopping, and dining, and with no HOA, this property offers convenience and long-term appeal. Sold as-is.

Listing is courtesy of: KELLER WILLIAMS REALTY SMART (863-577-1234)

Listing Agent: Daryl Ash, Ii (863-934-1548)

Remarks: Welcome Home to this 5 bedroom 3 bath POOL Home on a large corner lot in Winter Haven. Upgrades galore. NEW ROOF, NEW POOL EQUIPMENT, 2 NEW A/C UNITS. The home features luxury vinyl wood flooring throughout. The kitchen has been renovated featuring white wood shaker cabinets, quartz countertops and stainless steel appliances. The bathrooms have been fully renovated as well and feature modern updated finishes. The living room features a large brick fireplace. The large fenced in backyard has a large underground pool just waiting for its new homeowners to spend their afternoons building memories and soaking up the Florida sun. The front of the home features 2 driveways. This home is close to Legoland, Lakes galore and amazing shopping, dining and entertainment.

Listing is courtesy of: ELEVATE REALTY LLC (561-427-3923)

Listing Agent: Laura Auten (561-427-3923)

Remarks: Under contract-accepting backup offers. Welcome to this charming and move-in ready 3-bedroom, 2-bath home located in the established Foxridge community of Winter Haven. Featuring approximately 1,148 square feet of living space, this cozy residence offers a functional split-bedroom floor plan, spacious living area, and plenty of natural light throughout. The kitchen provides ample cabinet space and flows nicely into the dining area, making it perfect for everyday living or entertaining. Situated on a generously sized lot with a private backyard, there’s plenty of room to relax, garden, or enjoy outdoor gatherings. Conveniently located near shopping, dining, schools, and major roadways with easy access to all that Winter Haven has to offer. Whether you're a first-time homebuyer, or looking to downsize, this property is a fantastic opportunity to own an affordable home in Central Florida.

Listing is courtesy of: CITARELLI REALTY GROUP LLC (321-607-3586)

Listing Agent: Benjamin Crane (302-841-8999)

Remarks: This well-maintained 4-bedroom, 3-bathroom pool home is located in the sought-after gated community of Tuscany at Winterset, offering both comfort and style in a prime setting. Inside, you’ll find an inviting layout highlighted by solid surface countertops, elegant tray ceilings, and detailed crown molding that adds a refined touch throughout the living spaces. Major updates provide peace of mind, including new windows (2025), a newer roof (2021), kitchen remodel (2023) and an updated HVAC system (2023). Step outside to enjoy the brick-paved driveway and your own private pool (2020)—perfect for relaxing or entertaining. This home combines thoughtful upgrades, functional features, and a desirable location—an excellent opportunity in one of the area’s most desirable gated communities.

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

Listing Agent: Tony Insua, Jr (863-221-0656)

Remarks: Under contract-accepting backup offers. Welcome to 103 Morning Glory Circle in the highly desirable Morningside at Winterset community in Winter Haven. As you step inside, you’ll be greeted by soaring vaulted ceilings, abundant natural light, neutral paint tones and immense charm. The spacious living room is the heart of the home, featuring a cozy fireplace and custom built-in shelving, creating the perfect space to relax or entertain. The home’s layout flows seamlessly, offering both functionality and style, while the tile roof adds durability and long-term value. New HVAC was installed in 2025 and water heater in 2020 along with all new appliances within the last few years. Step outside to your large screened-in patio, ideal for enjoying Florida’s outdoor lifestyle year-round, whether you’re hosting guests or unwinding in your private retreat. Located in a gated community with low HOA and no CDD, homeowners of Morningside at Winterset enjoy access to resort-style amenities including a community pool, clubhouse, tennis courts, private-community boat ramp, and direct lake access to Lake Winterset, perfect for boating, fishing, and soaking up the Florida sunshine. Conveniently situated near LEGOLAND Florida Resort, the Chain of Lakes, shopping, dining, medical facilities, and major highway access, this home offers the perfect blend of peaceful living and everyday convenience. If you’ve been searching for a home that combines character, community, and location, this one checks all the boxes. Schedule your showing today!

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

Listing Agent: Eric Gross (513-907-4271)

Remarks: This home offers, 9"4' ceilings and 8' doors, 42' cabinets, white quartz counter tops in kitchen, ceramic tile throughout the wet and main living areas of the home, all bedrooms, family room, and covered lanai are prewired for ceiling fans, secondary bedroom with its own bathroom. *Take advantage of special financing on quick move-in homes OR buy a to-be-built home and enjoy up to $20,000 in Flex Funds toward homes that can close in a timely manner! Options may vary by community, and offers are available on select homes on a first-come, first-served basis. Contact builder for more information!

Listing is courtesy of: AXEN REALTY, LLC (480-399-1218)

Listing Agent: Stephanie Morales, Llc (407-399-2055)

Remarks: Short Sale. Discover this beautifully designed 2023-built 5-bedroom, 3-bathroom home located in the highly sought-after Villamar community in Winter Haven, Florida. This spacious two-story home offers the perfect blend of modern style, functional living space, and scenic water views. The welcoming foyer opens into a bright and airy open-concept floor plan ideal for both entertaining and everyday living. The chef-inspired kitchen features plentiful gray cabinetry, a large center island, stainless steel appliances, and an oversized pantry, all overlooking the spacious living room for seamless gathering and conversation. A downstairs bedroom and full bathroom provide the perfect setup for guests, multi-generational living, or a home office. Upstairs, you’ll find a versatile loft space that can be used as a second living area, playroom, media room, or workspace. The spacious primary suite offers a large walk-in closet and private en-suite bathroom complete with double vanities and a walk-in shower. Three additional upstairs bedrooms, another full bathroom, and a convenient upstairs laundry room provide plenty of room for everyone. Step outside and enjoy peaceful water views right from your backyard. Located in the growing Villamar community, residents enjoy amenities including a community pool, clubhouse, playground, and low HOA fees. Conveniently situated near US-27 and I-4, this home provides easy access to shopping, dining, medical facilities, and entertainment. Nearby attractions include the LEGOLAND Florida Resort, the Winter Haven Chain of Lakes, and the Downtown Winter Haven Historic District. This is a fantastic opportunity to own a newer construction home with water views in one of Winter Haven’s fastest-growing communities. Short sale opportunity — don’t miss your chance to make this home yours!

Listing is courtesy of: ENGEL & VOELKERS LAKELAND (863-412-6633)

Listing Agent: Emily Lietz (863-266-9961)

Remarks: Situated on just over 5 acres of pastureland shaded by mature oak trees, this property offers the perfect blend of privacy, space, and functionality. Inside, you'll find an inviting 3 bedroom, 2 bathroom split floor plan featuring a newly renovated kitchen complete with a large hidden walk-in pantry. The guest bedrooms are connected by a versatile flex space ideal for a home office, playroom, or just additional living area. Toward the rear of the home, the enclosed porch has been transformed into the perfect movie room or bonus family space. Step outside to enjoy the screened-in heated saltwater pool, great for Florida summers and entertaining. The property also includes a detached suite with its own private entrance and full bathroom, offering excellent flexibility for guests or a private office setup. Additional highlights include a whole-home generator, large storage building, treehouse with window unit, and an additional shed with attached lean-to for equipment or workspace.

Listing is courtesy of: AGENT GROUP REALTY (843-656-0550)

Listing Agent: Stephanie Bombinski (863-877-5520)

Remarks: From the moment you walk through the door, this home welcomes you with space, comfort, and endless possibilities. Located in the sought-after Lakeside Landings community, this beautifully designed 4-bedroom, 2.5-bath home offers over 2,400 square feet of thoughtfully designed living space. Featuring an open and airy floor plan, generous living areas, and plenty of room to entertain, this home is perfect for growing families or anyone who loves extra space. The large primary suite creates the perfect private escape, while the backyard offers room to relax and enjoy Florida living year-round. Conveniently situated near shopping, dining, and everything Winter Haven has to offer, this home truly checks all the boxes!

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

Listing Agent: Harley Holmes (863-632-6946)

Remarks: LAKEFRONT LIVING WITH NO HOA Welcome to 3334 Fox Ridge Drive — a beautifully maintained 3-bedroom, 3-bath pool home perfectly situated on over half an acre along the shores of Lake Fox in Winter Haven. Enjoy the peace and privacy of a spacious lot with no HOA, while still being just minutes from shopping, dining, and schools. Step inside to find a bright, open layout designed for both comfort and entertaining. The kitchen overlooks the living area and pool, featuring plenty of cabinetry and counter space. Each bedroom offers generous closet storage and natural light, while the primary suite provides serene lake views and a private ensuite bath. Out back, unwind in your screened pool area or relax under the covered lanai—perfect for outdoor gatherings. The expansive backyard slopes gently toward Lake Fox, offering endless possibilities for fishing, paddleboarding, or simply soaking in the view. Additional highlights include:     •    Over ½ acre lot     •    Private lake frontage on Lake Fox     •    Screened-in pool with lanai     •    No HOA or CDD fees     •    Convenient SE Winter Haven location This is a rare opportunity to enjoy lakefront living with freedom and space—schedule your private showing today!

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

Listing Agent: Brandy Waters (863-268-9585)

Remarks: One or more photo(s) has been virtually staged. STUNNING POOL HOME ON OVERSIZED .53-ACRE CUL-DE-SAC LOT WITH NO HOA! Experience the perfect Florida lifestyle in this beautifully updated 4-bedroom, 2.5-bathroom residence. Perfectly positioned at the end of a quiet cul-de-sac, this home offers rare privacy and modern comfort. KEY UPGRADES: Move in with peace of mind featuring a REPLACED ROOF 2021 ,UPDATED AC SYSTEM, PLUMBING systems. The property has been FULLY REPAINTED inside and out for a fresh, contemporary look. INTERIOR ELEGANCE: The functional floor plan includes a formal LIVING ROOM and a spacious FAMILY ROOM centered around a cozy DOUBLE-SIDED WOOD-BURNING FIREPLACE. The kitchen boasts STAINLESS STEEL APPLIANCES, and ALL BATHROOMS HAVE BEEN COMPLETELY REMODELED with stylish finishes. OUTDOOR OASIS: Relax in your private SCREEN-ENCLOSED POOL, ideal for entertaining. The massive .53-acre backyard provides endless room for activities, while the rare 2-CAR GARAGE offers ample space for vehicles and storage. LOCATION HIGHLIGHTS: JUST 5 MINUTES (1.6 MILES) FROM LEGOLAND FLORIDA RESORT! Tucked away in a private cul-de-sac with no through traffic, yet minutes from shopping and dining. READY TO MOVE IN and easy to show. Schedule your private tour today!

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

Listing Agent: Julian Carvajal, Llc (407-454-2632)

Remarks: Paradise Awaits !!!! Lakefront Living at its finest...... This cozy one bedroom hideaway could be your Dream Come True! This home is located on Lake Lucerne just a short drive to downtown Winter Haven, Hwy 27, and loads of amenities including shopping, restaurants, and more. Nestled on almost an acre of gorgeous lake frontage, you can enjoy all your favorite things right at home. The living area is on the second level. It includes a nice family room/dining room combo, primary bedroom, bath and kitchen! Everything you need!! The decking on the lakeside gives the best views around Lake Lucerne. Lake Lucerne is a Private lake covering 40 acres. What an awesome location to kick back, relax and enjoy nature at its best. The lower level is currently a storage and laundry area but there is potential for additional living space with a bit of imagination. There is no shortage of storage....2 sheds will allow you plenty of room for all that "Stuff" that you need to put away. There is also a great air-conditioned "Hobby Shack" for you to DO whatever it is you LOVE TO DO!! The possibilities are limitless!! This is a wonderful property that would be great for rental income or just enjoying the lakefront lifestyle..... NO HOA as an added bonus. Don't miss out on this amazing property.....call today to schedule a private showing.

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

Listing Agent: Eunice Arroyo-Kirchgessner (863-698-9369)

Remarks: BACK ON THE MARKET DUE TO BUYER'S FINANCING FALLING THROUGH. This property appraised at $263,000, well above asking price! You'll definitely want to check out this beautiful, like-new property! The zero entry resort style community pool and playground overlooks one of the many beautiful lakes in Winter Haven. Villamar is a wonderful community close to a top rated Elementary School. Enjoy the privacy of this lot, as it does not have rear neighbors, but instead overlooks a quaint pond and conservatory area! Make sure to schedule your showing today!

Listing is courtesy of: VALOR REALTY SERVICES LLC (407-668-2448)

Listing Agent: Marian Benson (954-205-3075)