Winter Haven Homes For Sale & Real Estate - 1023 homes

Remarks: Welcome to this beautifully refreshed 3-bedroom, 2-bath pool home in Winter Haven with NO HOA! Situated on a spacious lot in the established Stately Oaks community, this move-in ready property offers comfort, flexibility, and the Florida lifestyle buyers are looking for. Inside, you’ll find bright updated living spaces with fresh finishes, abundant natural light, and a functional layout designed for everyday living and entertaining. The kitchen features clean modern updates, ample cabinetry, and flows seamlessly into the main gathering areas. Step outside to your private backyard retreat featuring a sparkling pool, covered outdoor space, and plenty of room to relax, entertain, and enjoy year-round outdoor living. The oversized driveway offers additional parking and convenience. Additional features include public water and public sewer connections and no HOA restrictions. Conveniently located near shopping, dining, schools, recreation, and major roadways with easy access throughout Central Florida. Schedule your private showing today!

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

Listing Agent: Chelsey Palmowski (863-326-2279)

Remarks: Unlock Incredible Income Potential in Winter Haven! This unique property at 1101 28th St NW is the ultimate value-add or "house-hack" opportunity you’ve been waiting for! While public records show a 2/1, the property features a spacious 3-bedroom, 2-bathroom layout, completely optimized with a separate, income-producing apartment unit that is currently rented. Whether you are looking to offset your mortgage by living in one side and renting the other, accommodating multi-generational living, or adding an asset to your portfolio, this property delivers. Sold AS-IS—bring your vision and capitalize on this rare find today!

Listing is courtesy of: OUTLET REALTY (407-353-5518)

Listing Agent: Yulimar Machado (407-485-1239)

Remarks: FLORIDA LIVING AT IT'S BEST!!! Don't miss out on this end unit, spacious 2 bedroom 2 bath townhome in a gated community. This unit is conveniently located right across the street from the clubhouse, pool, tennis courts and golf course!! Great for just starting out or ready to retire. Great Florida Room for relaxing when the weather is nice. Close to shopping and LegoLand!!

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

Listing Agent: Rhonda Chastain (863-698-9801)

Remarks: Welcome to 3060 Royal St, a beautiful 2023-built home located in the desirable Southeast Winter Haven area near the Chain of Lakes. This 4-bedroom, 2-bath home offers a comfortable open layout, modern finishes, and a 2-car garage. One of the standout features of this property is its canal location, with the canal connecting Lake Winterset and Lake Eloise, creating the perfect backdrop to enjoy the Winter Haven Chain of Lakes lifestyle. Situated on a desirable corner lot, this home also features a curved paver driveway, professional landscaping, and great curb appeal from the moment you arrive. Inside, the kitchen features granite countertops, stainless steel appliances, a center island with breakfast bar, and plenty of cabinet and counter space. Sliding glass doors bring in natural light and lead to the lanai, perfect for relaxing, or entertaining. Additional features include an irrigation system, indoor laundry closet, ceiling fans with lights, 2-inch faux wood blinds, and smart Wi-Fi enabled garage door opener and thermostat. Conveniently located near shopping, dining, schools, Legoland, and area lakes, this home is a great opportunity for buyers looking for comfort, newer construction, and a special waterfront setting in one of Winter Haven’s most loved areas.

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

Listing Agent: Mabel Vassallo (863-604-0499)

Remarks: Schedule your showing before it’s gone!! Check out this beautiful custom home. It sits on a big corner lot and it is the newest house in the neighborhood. Some of the items this home comes with include 9’4 ceilings, 8ft doors, open floor concept, crown molding, St. Augustine grass, irrigation system, insulation injected into the block, custom stone back wall in the living room, ceramic tile, granite counter tops, custom closets, a range hood, real wood cabinets, a back patio pergola, gutters,LED lighting throughout the home and so much more!! So schedule your showing to see this beauty before its to late.

Listing is courtesy of: FREEDOM PROPERTY AGENT LLC (407-530-4600)

Listing Agent: Santiago Arroyo (863-307-5212)

Remarks: Like-new 2022-built home on a desirable corner lot in the heart of 33884, located in a community loaded with amenities! This beautifully maintained 3-bedroom, 2-bath home offers modern living with an open, functional layout and split floorplan. A standout feature is the upgraded enclosed patio/all-seasons room, complete with windows and screens—perfect for relaxing year-round, entertaining guests, or enjoying Florida living without the bugs. The home shows like new and offers peace of mind with newer construction, while the community amenities add incredible value and lifestyle appeal. Conveniently located near shopping, dining, and everything Winter Haven has to offer. Move-in ready and priced to sell—don’t miss this one!

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

Listing Agent: Katherine Montana - De Jesus (863-508-3000)

Remarks: No HOA! Tucked behind a private canopy of trees, this beautiful 2 story 4-bedroom, 3-bath home offers peaceful country living on just under 2.5 acres. With plenty of space for vehicles, recreational equipment, and outdoor hobbies, the property provides endless possibilities. An oversized garage offers ample room for storage, a workshop, or hobby space, making this home the perfect blend of privacy, comfort, and functionality.

Listing is courtesy of: S & D REAL ESTATE SERVICE LLC (863-824-7169)

Listing Agent: Dee Newell (863-698-2082)

Remarks: NO CDD Fees • Low HOA • *Lower Taxes • Luxury Heated Pool • Resort-style backyard • Move-In Ready Home. Welcome to this beautifully maintained and gently lived-in upscale home situated on an oversized 70’ wide homesite in a desirable community offering low HOA fees and *lower property taxes. Designed for both comfort and entertaining, this expansive 4-bedroom, 3.5-bath, two-story home has approximately 2,894 sq. ft. of thoughtfully designed living space, including TWO primary suites — one conveniently located on the first floor with a luxury bath and spacious walk-in closet, and a second upstairs primary suite featuring its own full bath and walk-in closet. The first floor also includes a versatile enclosed flex room which can be used as a home office, guest room, or potential 5th bedroom. The second floor has three other bedrooms with walk-in closet and oversized loft about 21'x17'. Step outside into your private resort-style backyard featuring a heated, fully automated full-size pool and spa with premium PebbleTec finish, already prepped for expansion with a concrete footer for future screen enclosure installation, upgraded pavers, large covered lanai, gutters and downspouts for improved drainage, fully fenced yard and extended front porch — creating the perfect Florida outdoor living experience— for entertaining, relaxing, pets, and family gatherings. Inside, the open-concept kitchen is beautifully upgraded with: • premium color cabinets, • oversized island, • stylish backsplash, • single-bowl sink, • granite countertops, • pendant lighting, • and stainless-steel appliances. Additional interior highlights include: • recessed LED lighting throughout, • tile flooring in wet areas, kitchen, hallway, and gathering room, • exterior-vented microwave, • and abundant natural light throughout. This truly move-in-ready home includes: • first-floor family room sofa set with wall-mounted 75” TV, • upstairs loft recliner sofa set with wall-mounted 75” TV, • refrigerator, washer, dryer, and window blinds, • home alarm system, • outdoor security cameras, • video doorbell, • and remote thermostat. Additional peace of mind includes: • transferable Pulte Homes 5/10-year warranty, • and 1 year of complimentary pool maintenance. This home has the perfect blend of luxury, functionality, and convenience in a family-friendly community with a safe small-town feel while remaining close to shopping, dining, everyday amenities and just minutes away from Legoland. READY TO MOVE IN. *Some photos have been virtually rendered.

Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)

Listing Agent: Steven Koleno (804-656-5007)

Remarks: Welcome to the Eagle Landing community in Winter Haven, FL. This well-maintained single-family home is move-in ready and waiting for its new owner(s). The open-floor concept creates a comfortable flow throughout the main living areas, while the split floor plan provides added privacy for the primary bedroom and bath with spacious walk-in closet. The kitchen features stainless steel appliances and granite countertops, offering both style and functionality. Additional conveniences include a laundry room, two car garage and low HOA dues, making this home an affordable and practical choice. Experience the charm of small-town living while enjoying the growth and expansion happening throughout Winter Haven. Conveniently located just minutes from Legoland, shopping, dining, and entertainment, and centrally positioned between Tampa and Orlando for easy travel in either direction. Solar panels will be paid off at closing, providing the new owner with the benefit of low electricity bills. The spacious backyard offers room to relax or entertain.

Listing is courtesy of: CENTURY 21 WATSON & MYERS REALTY (863-324-1000)

Listing Agent: Carla Miro (786-897-4081)

Remarks: Welcome to your slice of LAKEFRONT, LAKE VIEW, POOL HOME paradise on the pristine shores of Lake Mariam in Winter Haven, Florida. This stunning 3-bedroom, 2.5-bathroom home with a versatile BONUS ROOM offers the ultimate Florida lifestyle, complete with direct lake access, a private dock, and breathtaking water views right from your own backyard. Built to last and designed for low maintenance, this home features a durable METAL ROOF and solar panels, offering peace of mind and significant savings on energy costs year after year. Whether you’re sipping morning coffee while watching the sunrise over Lake Mariam or heading out for a day on the water, this property delivers the lakefront living experience you’ve been searching for. Inside, the thoughtfully designed floor plan offers three comfortable bedrooms, two and a half bathrooms, and a spacious bonus room perfect for a home office, media room, guest suite, or playroom. The heart of the home is the beautifully designed kitchen, featuring abundant cabinetry, stainless steel appliances, granite countertops, a center island, breakfast bar seating, glass-front upper cabinets, recessed lighting, and an open layout that flows seamlessly into the main living areas. With its generous workspace and water views from the adjoining living space, this kitchen is ideal for both everyday living and entertaining. The oversized 2-car garage provides ample storage for vehicles, watercraft equipment, and all your lake toys. Step outside and discover what truly sets this property apart: your own private HEATED POOL and SPA, along with an impressive private dock stretching out over the serene waters of Lake Mariam, ideal for boating, fishing, kayaking, or simply soaking in the natural Florida scenery. With direct lake access and one of the longest docks on the water, this is a rare find in today’s market. Located in Winter Haven’s sought-after lake corridor, you’re just minutes from dining, shopping, Legoland Florida, and easy access to I-4 connecting you to both Tampa and Orlando. Schedule your showing today!

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

Listing Agent: Mabel Vassallo (863-604-0499)

Remarks: Cute as a button. Great starter home or investment property. Large corner lot. Featuring NEW ROOF, NEW SEPTIC, NEW ELECTRICAL PANELS. This three bedrooms one & one half bathroom has a new modern eat in kitchen and laminate floors. Open spacious living and dining room. Covered front porch. Why rent just buy. Adjoining vacant lot is not included in the sale and has been removed from the legal description. Lot maybe purchased separately.

Listing is courtesy of: CAPITAL REALTY GROUP FLORIDA (407-447-7253)

Listing Agent: Angela Chapman (407-447-7253)

Remarks: Under contract-accepting backup offers. *****BELOW APPRAISAL VALUE***EASY TO SHOW +++ LUXURY AND REMODELED MOVE-IN READY POOL HEATED HOME IN EAGLE LANDING! Welcome to this stunning, fully upgraded corner-lot residence located in the highly desirable Eagle Landing community—just minutes from LEGOLAND and ideally situated between Tampa and Orlando. Built in 2023, this beautifully enhanced home offers the perfect blend of modern design, comfort, and resort-style living. The open-concept floor plan creates a bright and spacious atmosphere, ideal for both everyday living and entertaining. The chef-inspired fully remodeled kitchen features brand-new cabinetry and elegant granite countertops, seamlessly flowing into the main living areas for a clean, modern feel. Both bathrooms have been completely remodeled with stylish tile finishes and granite vanities, adding a touch of luxury throughout the home. Step outside to your private backyard oasis, featuring a 16' x 22' saltwater pool, lights with a heater for year-round enjoyment, a relaxing spa/hot tub, and a fully screened enclosure. The outdoor space is finished with beautiful pavers and a fully fenced yard, perfect for entertaining or simply relaxing in privacy. Additional highlights include: ?? 2023 construction ?? Fully remodeled kitchen with new cabinets & granite countertops ?? Smart home technology to control your home & pool ?? Saltwater pool (16’ x 22’) with heater + spa/hot tub/ heated ?? Screen enclosure + pavered outdoor living space ?? Fully vinil fenced backyard for privacy and entertainment. ? New front entry door with decorative glass and upgraded hardware. ? Block-on-block construction for durability and peace of mind. ? Architectural shingles and modern stucco exterior for lasting curb appeal. ? Spacious corner lot offering extra privacy and outdoor space. This home featuring modern, nearly new furniture throughout—making it truly turnkey. The only exception is the primary bedroom set, which includes a king-size bed. With its prime location, luxury upgrades, and resort-style amenities, this property is perfect as a primary residence, vacation home, or investment opportunity. ?? Eagle Landing – Winter Haven, Florida ?? Schedule your private showing today before it’s gone!

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

Listing Agent: Ingrid Reyes (863-838-6863)

Remarks: This is the ONE! Great location centrally located in Winter Haven. Needing an attached Mother N Law suite with a separate entrance or want an Air BNB. This is the perfect set up. Seller is offering buyer incentive towards closing cost of $4000.00. This can be considered as a duplex, since the units are entirely separate. Main home has had total renovations. New trusses, installation, windows, doors, roof, floors, kitchen, baths, sheetrock & tankless water heater. Open plan with dining/kitchen combo. Kitchen features stainless steel appliances, granite counter tops, range, refrig, dishwasher and pantry. Enjoy your spacious front covered porch in the shade. This home features porcelain tile & wood laminate throughout and offers plenty of off street parking spaces. How many vehicles you can park depends on the size of your vehicles. There is space to park an RV. The attached Mother N Law suite or Air BNB has a private entrance. It is attached to the main home but there is not an entrance between the 2 homes. The 2nd home is new construction and features an open floor plan with porcelain tile & wood laminate flooring. This home features a full size kitchen with stainless steel appliances, granite counter tops, range, refrig, dishwasher and double sinks. The living area if open to the kitchen & dining area. The home features 2 bedroom and 2 baths. One bath has a tiled walk-in shower, the other bath has a tub/shower combo & both have granite vanity tops. This home features a large “Recreation or Flex Room.” Each home has it's own HVAC unit with separate meters.

Listing is courtesy of: ADVANTAGE REALTY 1 (863-386-1111)

Listing Agent: Sharon Jones Pa (850-341-9216)

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: PRICE DROP! SELLER OFFERS $15,000 CREDIT TOWARD CLOSING COSTS OR UPGRADES, BUYER’S CHOICE PRIOR TO CLOSING! Welcome to this charming 3-bedroom, 2-bathroom home in Winter Haven, offering an open and functional layout perfect for everyday living and entertaining. This solid single-family residence features approximately 1,449 sq. ft. of comfortable living space, including a cozy living/dining combination and a well-appointed kitchen. The property boasts significant recent upgrades, including: - Roof: Installed in 2021 - HVAC: Brand new A/C system, ducts, and air handler installed one year ago - Water Heater: Only 3 months old - Flooring: Brand new tile throughout the entire home Outside, you will find a large fenced backyard providing ample room for gardening, play, or weekend grilling. Ideally located on a quiet residential street, this home is just minutes from shopping, dining, major highways, local attractions, and Legoland. With no HOA, this home is an excellent opportunity for first-time buyers, those looking to downsize, or investors seeking value and convenience. Don’t miss out on this Winter Haven gem!

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

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

Remarks: Pack your bags and move right into this fully furnished home. This home has many updates!! Although the bedrooms have updated carpets there is nice wood laminate flooring throughout the main living areas with plywood subfloor. The baths and front porch area have updated tile flooring. The kitchen has newer appliances, a beautiful mosaic backsplash and updated counter tops. All the windows are updated with double pane, thermal, tilt in windows. The updated entry door has blinds between the half glass that you can open for the light or close for privacy. Both bathrooms have updated vanities. Enjoy the updated and modern light fixtures. You get all this, plus the golf cart with new batteries is included in the sale of the home. The HVAC was installed in July 2023. The roof is a roof over adding extra insulation value to the home. Oakwood Estates is an active 55+ communities offering many amenities as well as activities. You can be as busy as you would like or just sit back and enjoy the peacefulness of the community.

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

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

Remarks: Step inside this well-designed single-family home offering comfort, functionality, and a layout that truly makes sense. You’re welcomed by a screened front porch and a beautifully landscaped front yard, setting the tone before you even walk through the door. Inside, you’ll find engineered wood flooring throughout the main living areas with ceramic tile in both bathrooms. The living and dining rooms flow together in one open space, creating an easy layout for everyday living or entertaining. At the heart of the home sits the open kitchen, featuring granite countertops and a central location that keeps you connected to everything happening in the home. The split bedroom floorplan provides privacy, and the spacious primary suite includes a garden tub for unwinding at the end of the day. Enjoy added convenience with an inside laundry room located just off the kitchen as you enter from the two-car garage. The backyard has been thoughtfully designed with low-maintenance rock landscaping instead of grass and is framed by a vinyl privacy fence along both sides and across the back. Additional highlights include high ceilings, approximately 1,716 heated square feet, and about 2,400 square feet under roof—giving you plenty of room to spread out. A comfortable, well-kept home with smart updates and a layout that works for today’s lifestyle—this one is ready for its next chapter.

Listing is courtesy of: CRAIG BURKE REAL ESTATE GROUP, LLC (863-899-5010)

Listing Agent: Julie Sutphin (407-414-4024)

Remarks: Short Sale. Great opportunity to own this spacious home! Please note this is a short sale and purchase is subject to lender/bank approval. Property is being sold strictly in As-Is condition, and buyer is responsible for all municipal inspections. Bring your vision and custom touches to make this home your own! Opportunity meets value in this 3-bedroom, 2-bath home located in a well-established Winter Haven neighborhood. NO HOA. Positioned on a spacious, fully fenced corner lot, this property offers exceptional outdoor space and includes an above-ground pool, perfect for cooling off on hot Florida days, entertaining guests, or enjoying your own private backyard retreat. Inside, you’ll find a functional, comfortable layout with great natural light and flexible living space. This home presents an excellent opportunity for buyers looking to add personal style, build equity, or secure a solid investment property in a growing area. Whether you’re a first-time buyer, downsizing, or expanding your investment portfolio, this home offers strong potential, location convenience, and everyday livability. Ideally located near shopping, dining, Downtown Winter Haven, and the Polk Parkway, with easy access to both Orlando and Tampa for commuting or weekend travel. If you’re looking for space, flexibility, and long-term value with NO HOA restrictions, this is one you don’t want to miss. Schedule your private showing today and explore the possibilities.

Listing is courtesy of: SIGNATURE INTERNATIONAL REAL E (561-404-7263)

Listing Agent: Barbi Rodriguez, Llc (352-404-2377)

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)