Winter Haven Single Family Homes For Sale - 792 homes

Remarks: Virtually Staged. Welcome to a place where everyday life feels like a getaway. Set along the peaceful shores of Lake Jessie, part of Winter Haven’s renowned Chain of Lakes, this lakefront retreat is more than just a home, it’s a lifestyle defined by water, sunshine, & unforgettable experiences. Start your mornings with breathtaking sunrises shimmering across the lake, coffee in hand from your private dock or patio. Spend your days exactly how you choose, cruising the Chain of Lakes by boat, casting a line in some of Central Florida’s best freshwater fishing, or enjoying world-class watersports like skiing, wakeboarding, and paddleboarding right from your backyard. With nearby slalom courses & open water, this is truly a paradise for water enthusiasts. Lake Jessie is especially cherished for its tranquil atmosphere, offering a rare sense of calm while still being full of life. One of its most unique features is the seaplane activity, where you can watch planes gracefully land and take off across the water, an experience that never gets old and adds to the charm of lakeside living. Nature lovers will also appreciate the frequent sightings of all kinds of birds and other beautiful wildlife. The home itself offers a thoughtfully designed single-story layout with over 1,800 square feet, featuring 3 bedrooms and 3 bathrooms. An open-concept living space is filled with natural light and showcases stunning lake views, while a split-bedroom design provides comfort and privacy. A private in-law suite with its own entrance adds flexibility for guests, multi-generational living, or additional income potential. This residence offers plenty of parking space with it's oversized driveway & an additional carport providing covered parking as well. The home has been updated with modern finishes and includes a metal roof installed in 2019. This home would make a perfect full time residence, investment property or second home. Beyond the water, the location is just as appealing. You’re right around the corner from a brand new Publix store and minutes from the heart of Winter Haven, where you’ll find charming local restaurants, shops, parks, and community events. Legoland Florida Resort is just a short drive away and there is convenient access to both Tampa and Orlando, so world-class attractions, dining, and entertainment are always within reach. Whether you're seeking adventure, relaxation, or a smart investment, this Lake Jessie property delivers it all, offering the rare opportunity to live, play, and unwind in one of Florida’s most iconic lakefront settings. Book your showing today!

Listing is courtesy of: RE/MAX HERITAGE PROFESSIONALS (863-256-2188)

Listing Agent: Patricia De Graaff, Llc (863-307-0061)

Remarks: Beautifully maintained, highly upgraded home in a quiet, conveniently located community. From the moment you arrive, you’ll notice the strong curb appeal with manicured landscaping and a spacious screened front entry welcoming you inside. Step through the front door to find high ceilings and a wide hallway that opens into a bright, inviting great room. The open-concept kitchen flows seamlessly into the living and dining areas, featuring a large island perfect for entertaining, an upgraded deep sink, modern lighting, and plenty of cabinet and counter space. The private primary suite is thoughtfully separated from the other bedrooms, offering a peaceful retreat with a walk-in shower and dual vanities in the en-suite bathroom. Three additional bedrooms are located on the opposite side of the home, sharing a full hall bath, with a centrally located indoor laundry room for added convenience. Enjoy outdoor living on the backyard lanai—perfect for relaxing or hosting weekend barbecues. MUST SEE!

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

Listing Agent: David Cepeda (561-214-4879)

Remarks: Virtually Staged. Wonderful opportunity to live in a Florida lifestyle property with two (2) ($1800 total) income-producing studio apartments on your property that are currently leased. Additionally the Airbnb potential would provide an even larger income stream since it's located only one mile from Legoland and the famous Winter Haven Chain of Lakes. This is a unique opportunity and is located on an oversized fenced corner double lot and only a 1/2 mile to Legoland. Another benefit is the bonus room could also be turned into a 4th bedroom. Plenty of paved parking for at least 10 cars. Corner lot will also allow for a detached garage to be built. No need to worry about skyrocketing electric bills as this home also has electric solar panels which are fully paid off and provide electric bill relief. Also on the property is a lovely sparkling 15' x 30' screened pool to provide escapes & privacy. There are many taste-full updates already done, including remodeled kitchen & bathrooms, new LVP throughout, newer windows, large storage shed, a hot tub, triple car wide concrete driveway & a portable back-up generator hook-up. Move-in ready and no HOA. This could also be a great place for a multigenerational living, short term rental or Airbnb.

Listing is courtesy of: KLINE REAL ESTATE SERVICES (863-287-0204)

Listing Agent: Scott Kline (863-287-0204)

Remarks: Under contract-accepting backup offers. Virtually Staged. PRICE IMPROVEMENT with a $10,000 drop! Get your appointment to see this beautifully maintained 2-bedroom, 2-bath home with a 2-car garage offers the perfect blend of comfort, smart updates, and lifestyle perks. There’s something about 4454 Glenns Landing that feels like home before you even step inside. Maybe it’s the quiet charm of the neighborhood — families out walking at sunset, riding bikes, neighbors waving as they pass. Maybe it’s knowing you’re not just buying a house…you’re stepping into a true community. Inside, enjoy the natural light through new windows installed in 2021 and the roof was also replaced in 2020, giving you peace of mind and eliminating two major expenses right from the start. The kitchen has a quaint eat-in area as well as great counter space for food prep and stainless steel appliances. The seamless flow between the living room and dining area creates a spacious feel while keeping everything connected — perfect for entertaining guests, hosting family dinners, or simply enjoying a cozy night at home. The primary suite is a relaxing retreat, featuring a spacious walk-in closet and a private bath with solid surface countertops that add both durability and elegance. The secondary bathroom also showcases matching solid surface countertops, creating a cohesive and polished feel throughout. One of the home’s best surprises, the fully enclosed porch with its own air vent, seamlessly adding extra square footage of living space. Whether you envision a sunroom, home office, reading nook, or second living area, this flexible space gives you room to live the way you want. Step outside your front door and enjoy a neighborhood designed for connection. Residents enjoy access to: a clubhouse with a sparkling pool, a fishing pier and dock, boat slips available on a first-come, first-serve basis, a vibrant social club that plans activities year-round.

Listing is courtesy of: CENTURY 21 MYERS REALTY (863-875-5656)

Listing Agent: Tisha Talbot (863-236-7610)

Remarks: Beautiful single-family home offering 4 bedrooms and 2 bathrooms with approximately 2,012 square feet of heated living space. This spacious residence features high ceilings and a functional layout designed for comfortable living and entertaining. The kitchen includes space for a breakfast table and flows seamlessly into a separate dining room, while an additional family room provides the perfect setting for gatherings. Conveniently located near Cypresswood Golf & Country Club, East Central Park, and Rotary Park, offering access to outdoor recreation, including skating, softball, and picnic areas. The property also provides easy access to U.S. Highway 27, with shopping, dining, and everyday conveniences just minutes away, including Publix and Walmart. The owner is currently in the process of updating the home, including new flooring and additional improvements, all of which will be completed before closing.

Listing is courtesy of: REALTY OF AMERICA (321-732-5369)

Listing Agent: Cisco Romero (407-922-6375)

Remarks: This 4/2 home has a renovated interior showcasing modern upgrades throughout. The home features stunning new 36" x 24" porcelain tile flooring, offering a sleek, contemporary look with durability and easy maintenance. Move-in ready and designed for comfortable, stylish living. Dual access bedroom and bath provides the bedroom with private ensuite access while allowing the bathroom to serve as a main or guest bathroom from the hall, featuring two doors to maximize access and functionality. Large kitchen with island and lots of cabinet space and large pantry. Sliding doors leading to covered screened in porch with additional concreted tiled patio area that leads to a large backyard. Seller will consider contributing toward buyer’s closing costs.

Listing is courtesy of: EASY REALTY (321-895-4636)

Listing Agent: Greg Owen (321-360-4434)

Remarks: HUGE PRICE REDUCTION! Looking to buy a home in Winter Haven Florida? Welcome to 551 Lake Smart Blvd, a stunning move in ready residence featuring a brand new roof replaced in 2025. This beautiful home features 4 bedrooms, 2 bathrooms, and 1936 square feet of open concept living space. Imagine relocating to central Florida and stepping into a bright, airy floor plan where natural light fills the generous living spaces and connects seamlessly to a modern kitchen. Picture yourself enjoying a spacious yard or hosting gatherings in a versatile layout designed for effortless living. Remote workers and commuters will love the strategic location along the I-4 corridor, offering a quiet retreat with easy access to both Tampa and Orlando. Only 2 miles away from the premier Willowbrook Golf Course. To make your move even smoother, the seller is offering a $5000 dollar contribution toward buyer closing costs alongside a 1 year home warranty. This property delivers affordable modern comfort just minutes from dining, shopping, and major roadways. It is incredibly easy to tour, schedule your private showing today.

Listing is courtesy of: LA ROSA REALTY CW PROPERTIES L (407-910-2168)

Listing Agent: Kenneth Gonzalez (407-860-2304)

Remarks: Virtually Staged. Fully renovated home nearing completion! This beautiful property has undergone a complete renovation and is almost finished—just a few minor touches remain. Featuring modern updates throughout, this home offers a fresh, stylish feel and is perfect for buyers looking for move-in ready with final details underway. Don’t miss the opportunity to own a beautifully updated home in Winter Haven!

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

Listing Agent: Stephan Elmera (407-750-1765)

Remarks: Welcome to this 3 bedroom, 2 bathroom home located in the Squires Grove community in Winter Haven — a growing Central Florida market known for its chain of lakes, parks, and convenient access to both Lakeland and Orlando. The home offers 1,616 sq ft with a functional single-story layout featuring a spacious living area, a well-sized kitchen, and a natural flow ideal for everyday living. The split floor plan provides privacy, while the bedrooms offer flexibility for families or guests. Attached garage and comfortable residential setting in an established neighborhood. Roof 2007, AC approximately 10 years old. Solar panels installed and operational (Sunrun lease — transferable to buyer or seller will consider buyout/removal, open to negotiation). HOA $155/quarter. All financing welcome including FHA, VA, and conventional.

Listing is courtesy of: HOUSEWELL.COM REALTY OF FLORIDA LLC (678-699-9206)

Listing Agent: Catherine Nolan (610-314-6896)

Remarks: Under Construction. The first floor of the stunning Edison two-story home is host to an open-concept layout that combines the kitchen with the living and dining areas, and an outdoor patio is easily reached off the main living space. Upstairs, five bedrooms surround a versatile loft, including the luxe owner’s suite, complete with a generous walk-in closet and en-suite bathroom. 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: Wake up to peaceful water views in this beautifully maintained villa in Winter Haven. This move in ready home features a bright open floor plan with tile and laminate flooring, an oversized kitchen with plenty of space to cook and gather, and an enclosed patio where you can relax and enjoy the tranquil pond setting. All appliances are included, making your transition effortless. Located in Traditions at Lake Ruby, this sought after 55+ community offers true resort style living with a lakefront clubhouse, heated pool and spa, fitness center, tennis and pickleball courts, dog park, and a full calendar of social events. The HOA covers exterior painting, cable, internet, and lawn care so you can spend more time enjoying life. Conveniently close to shopping, dining, major highways, and Legoland. Furniture available separately.

Listing is courtesy of: LOVELAND PROPERTIES (407-352-8118)

Listing Agent: Cleve Loveland (407-352-8118)

Remarks: Located in the desirable Gardens of Interlochen, this beautifully renovated and impeccably maintained 3-bedroom, 2-bath residence at 106 Jardin Lane offers thoughtful upgrades, timeless finishes, and a functional open layout designed for both everyday comfort and effortless entertaining. At the heart of the home is a stunning renovated kitchen featuring granite countertops, LG black stainless steel appliances including an induction range, a composite sink highlighted by a striking gold-tone faucet, an eat-in dinette, and a spacious closet pantry. Wood flooring flows throughout the main living areas and bedrooms, complemented by elegant crown molding, plantation shutters, and designer light fixtures that elevate each space. The well-designed floor plan includes a welcoming great room, a dedicated dining room, a split-bedroom layout for added privacy, a built-in bar ideal for entertaining, a laundry closet, screened lanai, and a meticulously maintained side-entry two-car garage. French doors open from the great room to the screened lanai, creating a seamless indoor-outdoor connection and an inviting space to enjoy morning coffee or relax with a good book. The primary suite serves as a true retreat, featuring a tray ceiling, an oversized walk-in closet with custom shelving and drawers, a large linen closet, and a beautifully renovated en-suite bath. The spa-inspired bathroom offers a generous walk-in shower with a bench, handrails, and handheld shower wand, dual vanities with granite countertops and a dedicated makeup area, along with new mirrors, faucets, lighting, and toilet. Both guest bedrooms feature wood flooring, ceiling fans, and closets with overhead storage. The updated guest bath includes a glass enclosed tub, linen storage, a granite topped vanity and pocket-door access to the third bedroom, making it an ideal secondary primary suite or private guest space. The interior laundry closet is equipped with a newer full size Speed Queen washer and dryer, as well as new cabinetry and a hanging rack. The side-entry two-car garage mirrors the care found throughout the home, featuring carpeted flooring, custom built-in cabinetry with countertop workspace, and convenient pull-down attic stairs—perfect for organized storage or hobbies. Set on a generous 0.25-acre lot, the property features an irrigation system with a timer and is shaded by beautiful, mature oak trees that create a peaceful and inviting setting. Lawn care, cable, internet and exterior house painting (every 10 years), are all included in the quarterly HOA fee, providing a low-maintenance lifestyle while the 2019 roof provides added peace of mind. Ideally located just minutes from shopping, dining, and medical facilities, and centrally positioned between Tampa and Orlando, this move-in-ready home offers style, comfort, abundant storage, and an exceptional location in the heart of Winter Haven.

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

Listing Agent: Deanna Stone (863-412-2080)

Remarks: Welcome to 1217 Michelangelo Ln., a beautifully updated Wakefield model by Centex Homes located in one of Winter Haven’s most desirable communities — with NO CDD fees and convenient access to shopping, dining, medical facilities, and local attractions! Situated on a premium corner lot, this spacious 4-bedroom, 3.5-bath home offers the perfect blend of style, functionality, and modern updates throughout. From the moment you walk in, you’ll notice the designer touches including updated lighting, modern fixtures, sleek ceramic tile flooring, and tasteful upgrades in every room. The open-concept kitchen features granite countertops, stainless steel appliances, updated faucets and fixtures, beautiful pendant lighting, and abundant cabinet space — perfect for entertaining and everyday living. The spacious primary suite is conveniently located on the main level and includes dual sinks, a relaxing garden tub, separate shower, and an oversized walk-in closet. Also downstairs is a stunning French door office that can easily function as a 5th bedroom, guest room, or flex space if desired. Upstairs, enjoy a large bonus room ideal for a media room, playroom, fitness area, or second living space. The beautifully designed laundry room adds both style and convenience. Step outside to your oversized fenced backyard featuring a white vinyl fence, offering privacy and plenty of room for pets, gatherings, or future outdoor living additions. Additional upgrades include a new water softener system for added comfort and value. Located just minutes from Winter Haven Hospital and close to everything Winter Haven has to offer, this move-in ready home truly checks all the boxes. Don’t miss your opportunity to own this exceptional property!

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

Listing Agent: Susan Brown (863-640-5722)

Remarks: Virtually Staged. Investor Special! Don't miss this opportunity to transform this 3-bedroom, 2-bath block home into something truly special. Featuring a newer roof and AC system, some of the major improvements have already been completed, providing a solid foundation for your renovation plans. Whether you're an investor searching for your next flip, looking to add to your rental portfolio, or a buyer ready to create your dream home, this property offers incredible potential. Situated in a convenient Central Florida location, you'll be close to shopping, dining, major highways, world-famous theme parks, and both the Gulf and Atlantic Coast beaches. Bring your tools, creativity, and vision. This handyman special is ready for its next chapter!

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

Listing Agent: Stephen Novak (863-409-3635)

Remarks: Super nice! Very affordable with NO HOA! This 3 bedroom, 2 full baths home has lots of great features like high ceilings, laminate flooring throughout, great room, kitchen, cute bathrooms and front and back porches.   Quality too, this home has been verified to meet the DOE Challenge Home (US Department of Energy guidelines), verifications are attached in MLS. Certified energy efficiencies that will save you money and universal design for aging in place with wide doors, easy open fixtures, etc.

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

Listing Agent: J. Michael Nolen, Jr (863-294-7541)

Remarks: LOCATION, LOCATION, LOCATION! Best Deal in Harmony on Lake Eloise!!! The Seller has upgraded everything with custom finishes throughout! The seller will also assist with buyer's closing cost. The open, light and bright floor plan is perfect for entertaining with a welcoming kitchen that is the heart of the home & features a solid-surface island large enough to seat six guests. Stainless appliances and a spacious pantry are just a couple of amenities creating the perfect place for "the chef". The spacious primary suite offers a generous walk-in closet, dual sinks and a walk-in shower. The additional bedrooms are of ample size and beautifully positioned to allow privacy for all. Enjoy the Florida lifestyle with two covered patios! Outdoor living on the rear patio is complete with a fabulous porch swing, perfect for cookouts and relaxing. The large backyard is surrounded by beautifully enhanced landscaping in a tropical setting to ensure privacy. This home is one-of-a-kind and feels like a custom-built property, the upgrades include the following: High-end water treatment system, interior and exterior repaint completed, crown molding throughout, French doors, recessed lighting in 3 rooms, ceiling fans, light fixtures, patio swing, custom window treatments, upgraded guest bathroom vanity, framed mirrors, designer hardware for showers and sinks, extensive landscaping and rear irrigation & more! Located between Tampa & Orlando in the master community of "Harmony on Lake Eloise", a premier lakefront community with all of the "amenities" - resort style pool, gazebos and picnic area, sidewalks, scenic walking paths, ponds and designated bicycle access way, just minutes from medical, shopping, downtown area with upscale dining, minutes to boating on the chain of lakes, local schools & LEGOLAND. Harmony is also located in close proximity to the Polk Parkway for easy access to Lakeland, Tampa & Orlando. Call today for an appointment to see all this beautiful home and neighborhood has to enjoy!!!

Listing is courtesy of: THE K TEAM REAL ESTATE SERVICES LLC (863-604-1601)

Listing Agent: Cathy Kluytenaar (863-604-6220)

Remarks: Under Construction. This BEAUTIFUL ALLEX II Model home is located in the quaint town of Winter Haven. Ski capital & home of LEGOLAND. The ALLEX II is3/2/2- 1504 S/F & newly upgraded! This new model has an open floor plan with a spacious DINING room off the kitchen to entertain & enjoy the company of your guests. You will love the split floor plan with beautiful & spacious master suite with walk in closet & ensuite bathroom away from the other 2 bedrooms. Home comes with WHIRLPOOL Stainless Appliances- range, hood microwave, refrigerator & dishwasher. Home also comes with faux wood blinds throughout & has Smart Home Technology which allows you to set the scene & connect to your home with your voice, from your smart phone. *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. Harmony at Lake Eloise presents The Camden, available to build in Winter Haven, FL. This all-concrete block constructed, one-story multi-gen layout offers two homes under one roof. As you enter the foyer you are greeted with two guest bedrooms that share an en suite bathroom with a double vanity. Making your way down the hall you will find a large dining room perfect for the whole family. The well-appointed kitchen overlooks the great room and features an island with bar seating, beautiful granite countertops and stainless steel appliances. Enjoy views of the oversized covered lanai from the café area just off the kitchen. Bedroom one, located at the back of the house for privacy, has an en suite bathroom with a double vanity and two spacious walk-in closets providing ample space for storage. This floorplan offers more than just a spare guest room. It’s two homes — the main home area with a separate suite including living space, bedroom, kitchenette and private entrances with the convenience and safety of a connecting door. Like all homes in Harmony at Lake Eloise, the Camden includes a Home is Connected smart home technology package which allows you to control your home 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: Great investor or first time home buyer opportunity. This house has new windows, a new roof, updated electric panel and an renovated bathroom. The LVP throughout the home with 5-1/4 baseboard. This property has a huge back yard for your family to enjoy. Built in laundry with washer and dryer included. This property is move in ready and won't last long at this price. Schedule your showing today

Listing is courtesy of: XCELLENCE REALTY, INC (866-595-6025)

Listing Agent: Stephen Hubbell (863-559-5666)

Remarks: Lake Views, Space to Spread Out, and Major Updates Already Done! Nestled on over half an acre with fully fenced back yard, this charming home offers a rare combination of privacy, flexibility, and scenic surroundings as it's situated between Lake Elbert and Lake Otis, both visible from the large front yard. Sit on the lovely front porch, relax in the swing out back, or in the oversized screen breezeway with peace of mind from the recent improvements. New roof and electric panel installed in 2023, as well as a newer water heater and ac/heat pump w/10 year warranty. While on public utilities, the home does have a well for irrigation (seller is obeying current water restrictions but hopeful that grass will green back up with rain!). There is NO HOA, and plenty of room to park the toys like boats or an RV. Side entry detached garage offers even more flexibility, as it includes the laundry, storage and a bonus room with full bath, perfect for hobbies, office, or home gym. We haven't even gotten to the home yet, which includes spacious rooms, real wood floors and kitchen cabinets, built ins and some charming features that you won't find in a modern cookie cutter home. It's truly a must see with great natural lighting and that homey feel you can't duplicate. Contact your agent to shedule a showing today!

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

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