Winter Haven Homes For Sale & Real Estate - 983 homes

Remarks: Under contract-accepting backup offers. Welcome home to this beautifully maintained three-bedroom two-bathroom gem offering comfort, charm, and everyday functionality! Situated on a spacious lot with a large front yard, this home features a warm and inviting exterior with great curb appeal and plenty of room to enjoy outdoor living. Step inside to find a bright and open layout with multiple living spaces, perfect for both relaxing and entertaining. The updated kitchen showcases crisp cabinetry, ample counter space, and a cozy, modern feel that flows seamlessly into the dining and living areas. The home offers generously sized bedrooms filled with natural light, along with well-appointed bathrooms designed for both style and convenience. A dedicated laundry space and flexible bonus areas provide extra functionality for today’s lifestyle, whether you need a home office, playroom, or hobby space. Enjoy Florida living with a large backyard, ideal for gatherings, pets, or simply unwinding at the end of the day. With a spacious driveway and additional storage options, this home checks all the boxes. Conveniently located near shopping, dining, and major roadways, this one is move in ready and waiting for its next owner!

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

Listing Agent: Jamie Baker (863-258-2244)

Remarks: Short Sale. Welcome to your dream home with low HOA fees and no CDD! This 4-bedroom, 2-bathroom home is nestled in the sought-after gated community of Lake Deer. With 1,946 square feet of heated and cooled living space, it's ideal for a growing family! The thoughtful split floor plan ensures privacy and comfort for everyone. The kitchen opens up to a spacious great room with sliding glass doors leading to a charming covered lanai and a private, fenced backyard. Residents can enjoy fishing from the private community dock or spending time at the play area! Conveniently located near shops, restaurants, and I-4. Schedule your private showing today!

Listing is courtesy of: FLORIDA REALTY MARKETPLACE (863-877-1915)

Listing Agent: Jeri Anarumo (863-877-1915)

Remarks: Under contract-accepting backup offers. Reduced $20k!! Move In Ready 4BR/3BA + Flex Space Featuring a Large 41'x17' Screened Patio. This Lovely Home Offers an Open Floor Plan, Vaulted Ceilings, Large Family Room, Corian Countertops in the Kitchen, Updated Lighting, Large Walk In Closet in Master Suite, LVP & Tile Flooring, Double Pane Windows, Privacy Fence and more! One off the Best Features are the Newly Installed Solar Panels. Cool Your Home as much as you want and Enjoy No More Electric Bills, only a Small Hook Up Fee to TECO for around $16 per month. Additional Updates Include: New Roof Approximately 5 - 6 Years Old, New AC System '24. New Washer & Dryer! Solar Panels are Leased, Monthly Payment is $189 / month. Avg. Electric Bills without Solar would be $400. Experience a Vibrant Downtown Winter Haven, Golf, Numerous Lakes, Outdoor Trails, Shopping and More!

Listing is courtesy of: SHAWN R MCDONALD REALTYGRP INC (863-287-0213)

Listing Agent: Shawn Mcdonald (863-287-0213)

Remarks: Honey, stop the car! This is the one you’ve been waiting for. This beautifully maintained 4-bedroom, 2-bathroom home sits on a spacious 0.45-acre fenced lot, offering the space, privacy, and outdoor lifestyle today’s buyers are searching for. Enjoy the soon-to-be easy access to Avalon and Disney via Sawgrass Rd extension. Step inside and you’re welcomed by a spacious foyer that flows into a cozy sitting area and formal dining room—perfect for gathering with family or entertaining guests. The open-concept kitchen features a charming breakfast nook and overlooks the main living area, creating a warm, connected space where everyone can come together. The private primary suite is a true retreat, complete with dual vanities, a relaxing soaking tub, a walk-in shower, and a large walk-in closet. The split floor plan provides privacy for everyone, while soaring high ceilings throughout the home create a bright and airy feel. Step outside and discover what truly sets this property apart—an outdoor entertainer’s dream. The covered paver lanai opens to a massive fenced backyard with endless possibilities for entertaining, gardening, play, or simply enjoying peaceful Florida evenings. Additional highlights include: New roof installed in 2021 Covered paver lanai perfect for outdoor gatherings Large private backyard with storage shed Two-car garage Interior laundry room Move-in ready condition in a quiet, established neighborhood Homes with this much space, privacy, and charm don’t come around often. Don’t miss your chance—schedule your private showing today before someone else calls it home.

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

Listing Agent: Paul Shearn (407-713-2127)

Remarks: LAKEFRONT LIVING AT IT'S BEST! REFRESHED FIRST FLOOR 2BR-2BA CONDO WITH COVERED PARKING AND BEAUTIFUL VIEWS OF LAKE BUCKEYE. THE FEATURES INCLUDE FRESH INTERIOR PAINT, LUXURY VINYL PLANK FLOORING THROUGHOUT WITH CERAMIC TILE IN THE BATHROOMS, KITCHEN AND FLORIDA ROOM, STAINLESS REFRIGERATOR AND MICROWAVE IN THIS CONVENIENT KITCHEN WITH PANTRY AND PASS THRU EATING COUNTER. THIS OPEN GREAT ROOM DESIGN HAS LIVING AND DINING COMBO. RELAX IN YOUR FLORIDA ROOM OVERLOOKING THE LAKE AND ENJOYING THE SUNRISE WITH YOUR MORNING COFFEE. COMMUNITY OFFERS POOL AND TENNIS COURTS. CONVENIENT LOCATION , WALK TO POLK STATE COLLEGE OR ENJOY THE WALKING TRAIL AROUND LAKE ELBERT ONLY MINUTES AWAY WITH NEARBY DOWNTOWN SHOPPING AND RESTAURANTS.

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

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

Remarks: Welcome to this beautifully maintained home featuring a spacious open floor plan and numerous recent upgrades. The heart of the home boasts brand-new solid wood kitchen cabinets, providing both style and durability for the home chef. Step outside to your private backyard oasis, which comes fully equipped with a pristine above-ground pool, a secure fence encompassing the entire property for ultimate privacy, and a convenient storage shed. Additional premium features include a whole-house water softener system and the added financial benefit of NO CDD fees and a very low HOA. This move-in-ready residence perfectly combines modern interior updates with an outdoor space designed for relaxation and entertainment in the heart of Winter Haven.

Listing is courtesy of: AGENT TRUST REALTY CORPORATION (407-251-0669)

Listing Agent: Luceyda Rodriguez Otero (407-301-8394)

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: What an amazing home just waiting for it's new owner!! The kitchen has been completely updated with new cabinets and flooring. The home offers two additional living spaces. The lanai on the side of the home is vented with the central ac and is included in the total square footage. or you can escape to the front porch which is also vented increasing the square footage by an additional 200 sf bringing the total living area to 1216 sf. The primary bathroom has an updated vanity. The laundry is located behind the side lanai so you don't have to go outside. The air conditioner is brand new in December 2025. This home is located in Oakwood Estates, a 55+ community which offers many amenities and activities. You can stay as busy as you like, or just sit back and enjoy the peaceful community.

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

Listing Agent: Kathy Devor (573-450-1679)

Remarks: Under contract-accepting backup offers. Location, Location, Location! Welcome Home! This beautifully remodeled 3-bedroom, 2-bath block home offers 2,000 sq ft of living space. Situated on a desirable corner lot, this block home blends style, function, and Florida living at its best. Inside, you’ll find updates throughout, including fresh finishes, modern fixtures, Luxury Vinyl Plank, and a bright, open layout perfect for both everyday living and entertaining. The kitchen showcases all wood cabinets with Quartz counter tops and all new Stainless Steel Appliances. The home features a newer roof and a brand-new water heater, giving buyers peace of mind from day one. Enjoy the outdoors year-round with a screened-in pool, ideal for relaxing or hosting gatherings. The fully fenced backyard provides privacy, space for pets or play, and plenty of room to make it your own. This home truly checks all the boxes — updated, spacious, and designed for easy Florida living. A must-see for anyone looking for comfort, style, and value. Conveniently located to down town Winter Haven and Medical, and located between Tampa and Orlando. Schedule your showing today!

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

Listing Agent: Christopher Howard (888-668-8283)

Remarks: This 2 story home features 4 bedrooms, 2.5 baths, a foyer/den, and a huge backyard. No CDD. The home was built in 2021 and is conveniently located to Orlando, Tampa, and just a few minutes away from Lego Land Resort. Eagles Landing is a community in Winter Haven, Florida. Since purchasing the home in 2023, the following improvements and upgrades have been completed. Flooring, Removed all existing carpet throughout the home and Installed new laminate flooring. Interior Updates, Fresh interior paint completed throughout the entire home, Installed California shutters throughout the house, Bathroom Renovations, Renovated two bathrooms. Upgraded both bathrooms with modern walk-in showers. Kitchen Upgraded kitchen countertops, professionally painted kitchen cabinets. Garage / Installed EV charger in the garage. Installed water softener system. The home has been well maintained and thoughtfully upgraded to provide a modern, clean, and move-in-ready living space.

Listing is courtesy of: AMERICAN IDEAL HOMES, LLC (407-908-8020)

Listing Agent: Bernard Scarpa (407-572-3022)

Remarks: This beautifully updated 4-bedroom, 2-bath home offers the perfect blend of modern comfort and classic Florida living. Located directly across from the Lake Hartridge boat ramp and Lake Hartridge Nature Park, you’ll enjoy instant access to the Winter Haven Chain of Lakes—one of Central Florida’s most desirable waterways for boating, fishing, and recreation. Inside, every detail has been refreshed, featuring new finishes, an updated kitchen and baths, modern flooring, and stylish fixtures throughout. All windows and doors have been replaced, offering enhanced energy efficiency, comfort, and peace of mind. The open-concept layout creates a warm, welcoming flow, ideal for entertaining or relaxing after a day on the water. Outside, the spacious yard provides plenty of room to park your boats or outdoor toys, and the property includes its own private well for irrigation, keeping your lawn lush and green year-round. With its unbeatable location and move-in ready condition, this home is perfect for anyone looking to embrace the lake lifestyle without sacrificing comfort or convenience.

Listing is courtesy of: REAL FLORIDA REALTY LLC (863-399-1804)

Listing Agent: Stetson Russell (863-399-1804)

Remarks: Under contract-accepting backup offers. PRICE REDUCTION!! Welcome to the lakefront community of Edgewater Manor! Come see this awesome custom built 2017 4 bed 3 bath corner lot (1/3 ac.) home with fenced backyard! Located just off Cypress Gardens Blvd., this bright, open floorplan includes combo living and dining area, an office, and a spacious kitchen with white wood cabinets and grey granite counter tops, stainless steel appliances, gas stove, and eat-in area. There is a large family room off the kitchen, crown molding throughout the home, vinyl fencing, and much more, including: gas tankless WH, vinyl planking floor everywhere but bedrooms, plantation shutters, double pane low E windows, a screened lanai. There is even a plug for an electric car built into garage wall, and a shallow well for lawn irrigation. Plus, close to Legoland, restaurants, shopping, and the chain of lakes. A great find!

Listing is courtesy of: STORMS REALTY (813-293-4652)

Listing Agent: Steve Storms (813-293-4652)

Remarks: LOOKING FOR THAT AMAZING HOME? Discover it in this fully renovated 3-bedroom, 2-bathroom beauty featuring a NEW roof (2025), NEW A/C unit (2026), NEW water heater (2025), and NEW electrical service panel (2026)—perfectly positioned just opposite Jewett Middle Academy. Enjoy your morning coffee on the radiant front porch before stepping into a bright and welcoming interior where the living room and kitchen greet you the moment you enter. The home is complemented by new vinyl flooring throughout and a cozy rug in the primary closet. The kitchen shines with a fresh, modern update, showcasing brand-new appliances, new cabinetry, and sleek quartz countertops. Whether you’re hosting guests or enjoying a quiet evening, the living room serves as the perfect centerpiece for everyday living. The primary suite offers a serene escape, highlighted by a fully remodeled ensuite bathroom and a spacious walk-in closet. The Fenced backyard is perfect for gatherings and outdoor enjoyment, with the added convenience of being close to shopping, schools, dining, and Winter Haven Hospital. Don’t miss this opportunity to own your happy place. Schedule your showing today

Listing is courtesy of: SUNSHINE LIFE REALTY LLC (321-229-0627)

Listing Agent: Sarita Khan (407-385-2077)

Remarks: The property you are inquiring about is located in Winter Haven, FL, in the Park Lake area of Polk County. This is an amazing opportunity for anyone wanting to be close in one single floor, walkable distance to almost everything, and is ready to move into. This is a 2-bedroom, 2-bath home with 1,224 sq.ft. plus a single-car garage, and has been updated. Text, call, and see it today. *Agents, please MLS remarks.*

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

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

Remarks: Under Construction. This expansive two-story Columbus has a well-designed layout, featuring a first floor dedicated to shared living and entertaining. The open concept design seamlessly connects the kitchen, dining room and family room, with a patio extending the interior space outdoors. Upstairs, a spacious loft separates the three secondary bedrooms from the serene owner's suite. Completing the home is a convenient two-car garage. 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: Under contract-accepting backup offers. Welcome to this beautifully upgraded lakefront home nestled inside a private gated community, offering 2,705 square feet of thoughtfully designed living space. Perfectly positioned on scenic Lake Ruby, which connects to Lake Bess, this west-facing property delivers breathtaking sunset views that can be enjoyed daily from your own backyard. Inside, the home features a stunning, oversized living room with cathedral ceilings and expansive views of the water—creating a bright, open atmosphere that truly feels like the heart of the home. The home boasts sliding glass doors that fully retract, inviting in cool breezes during the milder months. These sliders have been freshly tinted, along with the bath door, for added privacy and energy efficiency. Step outside to your private oasis where the recently remodeled pool and professionally leveled pavers provide a clean, modern look. The screened-in pool area also features a covered patio—perfect for relaxing or enjoying meals outdoors rain or shine. Additional exterior upgrades include 22 all new windows and screens, a lanai screen roof on the west side upper screens, lanai fans, solar exhaust attic fans, dock lights, dock power, and a boat lift motor with decking at the bow. The entire exterior has been enhanced with fresh flowers, and the north path walkway has been updated alongside the pool lite timer. The lanai also includes a separate 220 volt outlet to accommodate a hot tub.Entertaining is effortless with a convenient pool bathroom, allowing guests to shower or refresh without entering the main home—thanks to the new shower diverter in the master and fully upgraded plumbing, including all faucets (3 bathrooms, kitchen, and garage), toilet innards, and a new guest toilet. A cozy wood burning fireplace adds warmth and charm, while the overall condition of the home reflects true pride of ownership—impeccably maintained and move-in ready. Interior finishes include fresh interior paint, crown molding, electronic door locks on all 3 exterior doors, an electronic garage door lock, in-wall medicine cabinets, kitchen backsplash, pantry can closet, anti-skid tiles & garage floor, regrouted all bath wall tiles, and slider rollers & rebalance. Built-in cabinets in the living room have been removed for a more open feel, and the floor in the TV room has been updated. The home also features new smoke detectors throughout.Electrical upgrades are extensive: new lighting in the halls, bath, and garage, washer & dryer, master closet, dock lights, generator outlet, generator cutoff, additional lanai power, dock power, pool lite timer, and more. The HVAC system has been enhanced with an added garage AC split system, blown insulation, solar exhaust attic fans, and an insulated garage door. The garage offers exceptional versatility with its own AC split unit, insulated garage door, garage door springs, electronic garage door lock, and upgraded LED lighting, making it ideal for a workshop, home gym, or additional functional space. Additional thoughtful touches include all outside hose bibs x4, the main drain “Roto Rootered”, pool fill line. The property features lake-fed irrigation, removed lake grass and lake rocks for a clean, polished waterfront appearance. This home combines luxury, comfort, and functionality in a serene waterfront setting—an exceptional opportunity to enjoy Florida living at its finest. You'll also be able to enjoy the fireworks from LegoLand and Disney is only 30 miles away.

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

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

Remarks: Under contract-accepting backup offers. Welcome to this inviting 3 bedroom, 2 bath home in one of Southeast Winter Haven’s desirable neighborhoods. Enjoy a spacious Florida Room surrounded by large glass windows on three sides, flooding the home with natural light and providing a perfect spot to relax or entertain. The cozy living room features a decorative fireplace with built-in bookshelves, creating a warm and welcoming atmosphere. Enjoy a fully fenced backyard, offering privacy and plenty of space for outdoor living, gardening, or pets. Located in a sought-after area, this home combines comfort, character, and convenience—close to schools, shopping, dining, Legoland and all that Winter Haven has to offer. Don’t miss the opportunity to make this beautiful property your own—schedule your showing today!

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

Listing Agent: Steve Lockhart (863-289-9801)

Remarks: Under contract-accepting backup offers. Welcome to 2813 Wingfoot Court — now one of the best values in Cypresswood Golf & Country Club! Perfectly positioned along the 8th fairway inside this guard-gated golf community, this beautifully maintained 2-bedroom, 2-bath villa offers peaceful views and effortless Florida living—now at an exceptional new price. Being sold fully furnished and truly turnkey, this home is ready for immediate enjoyment—just bring your suitcase. Inside, you’ll find a professionally designed interior with vaulted ceilings that create a bright, open feel throughout the main living spaces. The kitchen includes updated appliances, including a newer stove and microwave, while most windows have been upgraded for improved efficiency and style. A tankless hot water heater adds modern convenience and energy savings. The spacious primary suite features a walk-in closet and private bath, while the guest bedroom also offers a walk-in closet and easy access to a second full bath—perfect for hosting family and friends. One of the home’s standout features is the inviting Florida room, ideal for morning coffee or relaxing after a day on the course. Step outside to the stained and stamped patio overlooking the fairway, creating a perfect space for entertaining or unwinding. Major updates include a roof (2019) and A/C (2018), providing added peace of mind. Residents enjoy access to community amenities including a pool, tennis courts, clubhouse, and on-site restaurant—all just minutes from shopping, dining, and major roadways. Now aggressively priced—don’t miss this opportunity to own in Cypresswood at one of the most attractive price points in the community.

Listing is courtesy of: CROSBY & ASSOCIATES, INC. (863-293-5600)

Listing Agent: Corinna Weaver (863-258-2901)

Remarks: MOTIVATED SELLERS...OPPORTUNITY KNOCKS ON THIS SPACIOUS & AFFORDABLE 3 Bedroom/2 Bath Home in the heart of SE Winter Haven located in Lake Daisy Estates is ready for you & your family!!! NO HOA or CDD in this established neighborhood that is within 3 miles of LEGOLAND and close to multiple restaurants, shopping, & parks. The natural light fills each room of the home. Open floor plan with split bedrooms. You'll love the large open backyard that is fully fenced. Newer roof (2023). Schedule a tour today!!!

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

Listing Agent: Cheryl Brewer (863-224-0045)

Remarks: ACCEPTING BACK UP OFFERS!! Ready to be impressed, this move-in ready 4-bedroom, 2-bathroom home at 4263 Stafford Dr is perfectly situated in Winter Haven, FL, with easy access to shopping, restaurants, major roads, and so much more. Step inside and you'll immediately notice the high ceilings and open floor plan that make this 2,234 square foot home feel even bigger than it already is. Hard flooring runs throughout the entire house, giving it a clean and modern look that's super easy to maintain. The family room is a real standout with a cozy fireplace that's perfect for those cooler Florida evenings when you just want to kick back and relax. The split bedroom layout gives you plenty of privacy, with the primary bedroom tucked away on one side and the additional bedrooms on the other. It's a great setup for families or anyone who likes their own space. Now let's talk about the backyard because this is where it gets really good. The screened-in back porch opens up to your very own pool and hot tub. Imagine coming home after a long day and just diving right in. Whether you're hosting friends on the weekend or enjoying a quiet evening under the stars, this outdoor space is going to be your favorite spot. Homes like this one in such a convenient Winter Haven location don't sit on the market for long. Come take a look before someone else scoops it up!

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Scottie Wilson (305-510-2446)