Homes For Sale in Winter Haven 33881 - 281 homes

Remarks: Short Sale. Welcome to this beautifully updated 4-bedroom, 1.5-bath single-family home located in Winter Haven with NO HOA! This solid block construction home offers peace of mind with a new roof and AC installed in 2024. Inside, you’ll find newer flooring throughout along with a recently renovated kitchen and bathrooms, giving the home a fresh, modern feel. The kitchen features quartz countertops, stainless steel appliances, and updated cabinetry, perfect for both everyday living and entertaining. The functional layout includes four spacious bedrooms, a full bathroom, and an additional half bath for added convenience. Enjoy outdoor living in the fully fenced backyard, ideal for pets, gatherings, or simply relaxing in your private space. The home also includes a 1-car garage for storage and parking. Ideally situated near Lake Conine, part of Winter Haven’s famous Chain of Lakes, this property offers easy access to boating, fishing, and outdoor recreation. Conveniently located near major roadways, providing a quick commute to Orlando, Tampa, and world-renowned attractions like Disney. This move-in ready home combines modern updates, a great location, and no HOA restrictions—don’t miss your opportunity to make it yours!

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

Listing Agent: Garrett Robinson (863-838-5210)

Remarks: Welcome to 1097 Sandpiper Loop, a beautifully maintained home situated in an intimate community of fewer than 90 residences. Conveniently positioned just off Country Club Road in Winter Haven, this property offers the best of both worlds—quick access to downtown amenities while enjoying the comfort of spacious quarter-acre lots that provide added breathing room. As you enter, you’re welcomed by attractive luxury vinyl flooring that runs throughout the main living spaces, creating a cohesive and low-maintenance design. The kitchen is thoughtfully designed for both everyday living and entertaining, featuring granite countertops, stainless steel appliances, and a generous walk-in pantry. It flows seamlessly into a flexible dining area that can easily adapt to formal gatherings or casual meals. In addition to the main living areas, the home includes a versatile flex room—perfect for a home office, study, playroom, or additional lounge space. The primary suite offers ample space and comfort, paired with a well-appointed bathroom designed with quality finishes and a relaxing atmosphere. Step outside to enjoy the extended covered and screened patio, providing a peaceful outdoor retreat overlooking a fully enclosed backyard. Numerous upgrades throughout the home enhance both functionality and overall appeal. Don’t miss your chance to own this thoughtfully designed home in a desirable Winter Haven location. Schedule your private showing today.

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

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

Remarks: Short Sale. We are in the process of getting a short sale approved. So expect delays. Welcome to 29 Golfview Circle NE, a beautifully modernized Winter Haven property offering a rare combination of charm, flexibility, and income-producing potential. The main residence features 3 bedrooms and 2 baths with an open, inviting layout that includes spacious living and dining areas, stainless steel appliances, and a comfortable primary suite with a walk-in closet. Enjoy outdoor living from the covered front porch, the screened back patio, and the fully fenced yard. Additional updates— including a 2021 roof and numerous interior improvements—add peace of mind and long-term value. What truly sets this property apart is the detached 1BR/1BA guest house, completed in 2022 and designed as an ideal in-law suite or rental unit. This private space features polished concrete floors, a sleek updated kitchen, a modern bathroom with a large walk-in shower, an oversized closet with washer/dryer hookups, stainless steel appliances, its own fenced yard, and dedicated parking. Together, both structures offer approximately 2,228 sq. ft. of combined living space and 2,573 sq. ft. total under roof. Located on a corner lot directly across from Polk State College, this home delivers outstanding convenience with exceptional versatility—perfect for multigenerational living, additional income, or both. Opportunities like this are hard to find. Come see everything this remarkable property has to offer!

Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)

Listing Agent: Chris Sakamoto (904-200-7535)

Remarks: Welcome home to Lake N Golf Estates, a well loved 55+, no pet community situated on the sparkling shores of Lake Henry in sunny Winter Haven, FL! This beautifully maintained 2005 residence offers 2 bedrooms, 2 bathrooms, plus a dedicated office, and boasts an impressive 2,190 square feet of living space — making it the largest home in the community. Major updates provide peace of mind, including a brand new roof, HVAC system, and carport (2025). Inside, you’ll find a newly redone kitchen that serves as the heart of the home, along with a spacious and functional layout designed for both everyday comfort and entertaining. A brand new washer and dryer are also included. Additional features include an irrigation system to keep the landscaping lush and green, and the home is being sold partially furnished — making your move even easier. Located in a land-owned community with low HOA dues, residents enjoy a relaxed lifestyle in a prime Winter Haven location near shopping, dining, medical facilities, and more. This exceptional home combines size, updates, and value — a rare opportunity in Lake N Golf Estates!

Listing is courtesy of: COLDWELL BANKER REALTY (863-687-2233)

Listing Agent: Laura Villardi (317-402-6277)

Remarks: ENJOY THIS WELL KEPT FURNISHED MANUFACTURED HOME IN GATED 55 AND OVER COMMUNITY. THIS PROPERTY IS IN A CO-OP. THE AIR CONDITIONER 2025, KING AND QUEEN SIZE BEDS WITH MATCHING DRESSERS, SOFA BED, 70 IN TV, LEATHER COUCH AND ROCKING RECLINERS. SUN ROOM HAS TV WITH LARGE BAR WITH STOOLS. LAMINATE FLOORS IN ALL ROOMS EXCEPT BEDROOMS HAVE CARPET. BRING YOUR TOOTHBRUSH, EVERYTHING ELSE IS READY FOR YOU TO MPVE IN. ENJOY SCHEDULED ACTIVITIES COMMUNITY HEATED POOL, LIBRARY, SHUFFLEBOARD, HORSESHOES, BILLIARDS, AND MORE. TRAILER STORAGE AREA AND LAUNDRY. SELF CONTAINED WATER AND SEWER SYSTEM WITH BACKUP GENERATORS. NO PETS EXCEPT SERVICE ANIMALS. NO MOTORCYCLES. THE $11,000 SHARE IS INCLUDED IN SALES PRICE. LAKE HENRY IS AN 810 ACRE PRIVATE LAKE.

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

Listing Agent: Jean Murphy (863-412-8751)

Remarks: Opportunities like this are nearly extinct. Just minutes from Winter Haven Country Club, this remarkable estate offers 10.98 acres of privacy, natural beauty, and flexibility in one of Winter Haven’s most coveted and tightly held locations—where land, space, and convenience rarely coexist. The 3,800 sq ft main residence has been completely remodeled with a refined, modern vision that blends luxury with everyday livability. Designed for both entertaining and comfortable living, the open-concept layout showcases luxury vinyl plank flooring throughout, expansive living areas, and a beautifully upgraded chef’s kitchen that serves as the heart of the home. With 4 bedrooms and 4 full bathrooms, the residence provides generous space for family and guests alike. Outdoors, a private pool invites relaxation while remaining surrounded by peaceful, natural views. Adding exceptional value and versatility, the property includes a 1,300 sq ft detached guest house featuring 2 bedrooms and 2 bathrooms, along with an upgraded kitchen and bath—ideal for extended family, long-term guests, or a private work-from-home or creative space. The land itself is what truly sets this property apart. The nearly 11-acre setting offers a thoughtful balance of open usable acreage, mature landscaping, and a scenic private pond, creating a sense of separation and tranquility that enhances both privacy and lifestyle. Multiple outbuildings, including a barn/garage and lean-to structure, provide ample room for storage, hobbies, equipment, or future expansion. In a market where acreage is disappearing and privacy is priceless, properties offering this scale of land, level of renovation, and proximity to town are exceptionally rare. This is not just a home—it’s a private retreat, a long-term asset, and an opportunity to own something truly irreplaceable.

Listing is courtesy of: THE MARKET REALTY COMPANY (863-999-4643)

Listing Agent: Brock Jennings (863-990-5846)

Remarks: 2021 built beautiful house with 4 beds and 2 baths and inside laundry room and double car garage totaling 2395 Sqft under roof. Centrally located in a very nice, quiet community on a dead-end road. Plenty of open air as there is no neighboring house on one side and back of the house. Open floor plan with Master in one side and other three bedrooms are located on the other side of the house. Stainless appliances are in the kitchen with a large spacious island for meal preparation and breakfast. Master bath with his and her walk-in closet with separate door for the toilet. Double sink and standing shower in the master and tub in the other bath. Tiles in all wet areas and waterproof wood like vinyl flooring throughout the living area and bedrooms floor. Dishwasher (not included with this sale) has power but not hooked up with water (buyer will have to try as is or get their own dishwasher). House is AS IS and buyer to verify as seller never lived on this property.

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

Listing Agent: Mohammad Iqbal (813-494-8864)

Remarks: WELCOME HOME TO THIS MOVE IN READY LAKEFRONT CONDO. 2BEDROOM - 2 BATH WITH 1252 SQ FT OF LIVING AREA , PLUS A FLORIDA ROOM OVERLOOKING LAKE BUCKEYE. THIS CONDO UNIT HAS STORAGE THROUGHOUT, GREAT STORAGE CLOSET OFF THE FLORIDA ROOM, ALSO INSIDE UTILITY WITH WASHER/DRYER HOOKUPS AND THE PRIMARY BEDROOM HAS A WALK IN CLOSET. YOU HAVE THE PRIVACY OF THIS UPSTAIRS UNIT WITH A BEAUTIFUL VIEW, NEW CARPET & INTERIOR PAINT,. IT ALSO FEATURES CONVENIENT COVERED PARKING AND COMMUNITY POOL & TENNIS. LOCATED NEAR POLK STATE COLLEGE , YOU CAN ENJOY A WALK AROUND NEARBY LAKE ELBERT OR DRIVE JUST MINUTES TO DOWNTOWN WINTER HAVEN FOR SHOPPING, RESTAURANTS AND COMMUNITY EVENTS. DON'T MISS OUT ON THIS LAKEFRONT VIEW OF LAKE BUCKEYE .

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. Motivated Seller!! *Welcome to this spacious Move-in-ready 4 bedroom, 2.5 bathroom home tucked away in the heart of Royal Hills, Winter Haven. The Home has recent upgrades including freshly painted Exterior in 2025, Roof 2024. The entire upper level has been revitalized with well-maintained carpeting while the ground floor showcases ceramic tile throughout. The kitchen contains Sleek granite countertops for that touch of sophistication,Stainless-steel appliances along with bright light fixtures.The home also has a BONUS Room on the ground level - perfect for a Home office or Media Room and a HUGE Fenced backyard. Conveniently situated near US-27, this property offers quick access to interstate travel and shopping centers. Don't let the opportunity slip by to make this beautiful house your next family home

Listing is courtesy of: MILLENNIUM REALTY CENTER LLC (407-843-8996)

Listing Agent: Phabie Terzier (407-692-7452)

Remarks: It's a renovated 4-bedroom block home beauty in upscale neighborhood. No HOA. Park your trailers or vehicles in back yard or side yard with gate. Boat ramp in neighborhood. New Roof, new windows, new doors, new hot water heater, new insulation, new electric and new air conditioner 2024. The kitchen has gold handles, refrigerator/ coffee maker combo, and a farmhouse sink. Wood floors are refinished 2025. Kitchen and bathrooms are totally renovated 2024. If you like drawers, this kitchen has a few 36" and 30." HUGE master bedroom runs from the back of the house to the front of the house, plenty of relaxing space, and a fireplace. This is a split plan house with 4 bedrooms,2 living rooms, and all bathrooms have double sinks. Tropical pineapple garden is in front of the front porch and trees have been trimmed. The back shed has a metal roof and can be used as a workshop; she shed or transformed for mother-in-law or rental. Large back porch has new concrete steps, a renovated laundry room and lake view. ZAP CAP from TECO, surge voltage protection. Parks, trails, splash pads, grocery, movies, pharmacy, public boat ramps are all nearby, Access to I-4 or the Polk parkway is easy. Winter Haven is a diverse city which offers lots of things to do such as, dinner cruises, walking parks, farm markets, LEGOLAND park and water parks, Circle B gator park, walking trails, skateboard park, water skiing and free water-skiing shows. All information is deemed reliable but not guaranteed. Buyer must verify all information and measurements. No seller financing.

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

Listing Agent: Kimberly Saddler (863-221-0604)

Remarks: Welcome to this well-maintained 3 bedroom, 2 bath home located on a quiet, established street. The Spacious eat in kitchen features tile flooring and a new refrigerator, perfect for everyday living and entertaining. The living room has new vinyl flooring and newly painted, creating a bright and inviting space, while the large family room offers plenty of room to relax or gather. This home also offers a spacious indoor laundry room, a one car garage and whole -house hurricane shutters that are easy to install, providing added piece of mind. Enjoy outdoor living on the screened-in back porch overlooking a fully fenced yard. Conveniently located close to shopping, dining, Polk State College and entertainment. This home combines comfort, functionality and an excellent location.

Listing is courtesy of: COLDWELL BANKER REALTY (863-687-2233)

Listing Agent: Carina Lees (540-616-7997)

Remarks: Welcome to this well-maintained 3-bedroom, 2-bathroom home on a desirable corner lot and offers a 2-car garage along with a fully fenced backyard. Inside, tile flooring highlights the high-traffic areas, while wood laminate flooring runs through the living room and bedrooms. The kitchen features a stainless sink, refrigerator, and stove. Step outside to enjoy a screened back porch and a paver patio—perfect for relaxing or entertaining. Major updates include a new central A/C installed in 2016 and a new roof completed in 2021. Conveniently located close to Polk State College, shopping, and plenty of restaurants. Legoland is just minutes away!

Listing is courtesy of: CENTURY 21 MYERS REALTY LAKE WALES (863-676-4448)

Listing Agent: Austin Henry (863-605-3451)

Remarks: Welcome to refined Florida living in the serene, gated, 55+ community of Preserve at Lakeside Landings. This community designed with enjoying your Florida lifestyle, is home to 44 residences, 2 pools, a playground, and sidewalks to keep you active. HOA includes lawn maintenance which allows you to relax in your stunning new home! Thoughtfully designed with a triple-split floorplan, this residence offers exceptional privacy and versatility—ideal for multi-generational living. Manicured tropical landscaping and pristine sidewalks lead you inside, where the first split features two guest bedrooms and a shared bathroom. Continuing into the main corridor, you’ll find the third bedroom or office along with the conveniently located laundry room.The home then opens into a bright, airy living space with 9-foot ceilings and tile flooring. An elegant dining area overlooks the pool, while the beautifully appointed kitchen showcases solid wood cabinetry, granite countertops, stainless steel appliances, and a generous island perfect for entertaining. The primary suite serves as a peaceful retreat with updated flooring, a walk-in closet, and a spa-inspired bath complete with dual sinks, granite, and a glass walk-in shower. Outdoors, the property transforms into a true tropical sanctuary. A stunning saltwater pool with a cascading waterfall is framed by lush landscaping that is home to several citrus trees. This secluded, spa-like atmosphere is ideal for relaxation or entertaining. With a tranquil natural backdrop and effortless indoor-outdoor flow, this home blends elegance, comfort, and resort-style appeal. Fresh interior paint, an immaculate garage, energy-efficient insulation, and lawn care included in the HOA make this home truly move-in ready—offering a lifestyle of ease, beauty, and authentic Florida living. Upgrades include kitchen appliances 2025, new disposal, Pentair salt system is 4 years old. Pool deck was sealed one year ago. Don't hesitate, opportunities like this are rare, so make your appointment today!

Listing is courtesy of: FLORIDA REAL ESTATE COMPANY (863-701-3487)

Listing Agent: Cyleste Goodson (863-701-3487)

Remarks: ** We have received multiple offers and are considering the highest and best offer by Monday, October 13, at 12:00 PM.** Spacious 3-bedroom, 2-bathroom home in Winter Haven priced to sell! This fixer-upper is perfect for investors, flippers, FHA 203(k) buyers, or first-time homeowners looking to build instant equity. With 2,182 sq ft of living space on an 8,442 sq ft lot, this property offers plenty of room for cosmetic and structural improvements. Priced well below market, buyers can capitalize on a significant value-add opportunity in a growing neighborhood. Renovate to create your dream home, or take advantage of strong resale and rental potential.

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

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

Remarks: Experience lakefront living at its best in this 2-story townhouse with 3 bedroom 3 bath on Lake Buckeye, located just minutes from Winter Haven. Christian School. !Enjoy breathtaking panoramic lake views from the living room, master bedroom balcony, . this spacious home is perfect for anyone looking to customize their living space. This property has great potential and features an oversized attached 2-car garage with ample storage space and access to a private lift station. Don't miss out on the chance to make this lakefront gem your own. Investment Only.Tenant Occupied. Lease start on 04/01/2026 & Expire On 03/31/2026. $1950/M.CASH FLOW INVESTMENT. INVESTMENT OLY WITH 20% DOWN. DSCR BUSINESS LOAN.

Listing is courtesy of: KURUVILA REALTY ASSOCIATES LLC (954-530-9477)

Listing Agent: Joe Kuruvila (954-822-7900)

Remarks: Price Reduced. Excellent Investment Opportunity. Zoning MX district. Charming 1910 Colonial Home — Elegantly Renovated in Central Winter Haven. Welcome to timeless charm blended with modern comfort in this beautifully Colonial residence, perfectly situated in the heart of Winter Haven, Florida. Meticulously updated while honoring its historic character, this home offers the ideal blend of classic architectural details and contemporary living. As you approach, you’re greeted by a stately façade showcasing symmetrical Colonial proportions, a welcoming front porch, and original period craftsmanship that has stood the test of time. Current zoning classification is MX (Mixed-Use), which allows a wide range of commercial and residential uses. Typical permitted uses examples are: Professional and medical offices, Assisted living facilities, ALF) / senior care, Group homes and supportive housing, Multifamily residential buildings, Live/work units and mixed commercial-residential developments.

Listing is courtesy of: CENTRAL REALTY GROUP AND PROPERTIES (407-582-9011)

Listing Agent: Raul Briceno (407-715-2550)

Remarks: Under Construction. The Archer II is one of our one-story floorplans features in our Willowbrook South community in Winter Haven, Florida. Take your pick between two sleek exterior options when choosing this floorplan. Inside this 3 bedroom, 2 bathroom home you’ll find 1,328 square feet of comfortable living. The open concept layout allows for seamless movement between spaces making entertaining guests a breeze. It also provides homeowners versatile design options. The kitchen features shaker-style cabinets, quartz countertops, and stainless steel appliances, which are sure to both turn heads and make meal prep easy. You’ll bever be too far from the action with the living and dining area right there. In every bedroom, besides the primary bedroom, you’ll have carpeted floors and a closet in each room. Whether these rooms become bedrooms, office spaces, or other bonus rooms, there is sure to be comfort. The primary bedroom features luxury vinyl plank flooring that will be sure to stand out. It also has its own attached bathroom that features a walk-in closet and all the space you need to get ready in the morning. Sharing a sink isn’t a worry with the double vanity, and you also get additional privacy with a separate door for the toilet and shower. Contact us today and find your home at Willowbrook South. *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. 2-story new construction townhome with 1,604 square feet, 3 bedrooms, and a covered lanai, located in the brand-new Harbor of Lake Henry community. Downstairs, enjoy an open layout and a gourmet kitchen with, shaker-style wood cabinets, Samsung stainless steel appliances, including a pantry. The spacious gathering room opens to your covered lanai. The entire lower level and upstairs baths are finished with luxury vinyl plank flooring, with stain-resistant carpet in the bedrooms. Upstairs, you'll find three spacious bedrooms including your owner's suite complete with a walk-in wardrobe, linen closet, and a private en-suite bath with dual vanities and a tiled shower. Additional features for your convenience include a half bath downstairs, upstairs hall bath for the secondary bedrooms, energy-efficient insulation and windows, and a full builder warranty.

Listing is courtesy of: CAMBRIDGE REALTY OF CENTRAL FL (863-797-4999)

Listing Agent: George Lindsey, Iii (863-797-4999)

Remarks: Welcome to this immaculately maintained 4-bedroom, 3-bathroom home with a spacious 3-car garage, perfectly situated in the highly desirable Country Club area of Northeast Winter Haven. Located within a gated community, this home offers both privacy and peace of mind. Backing up to an 11-acre jurisdictional wetland, the property provides complete rear privacy with a beautiful natural landscape—no rear neighbors, just serene views and tranquil surroundings. Inside, you’ll find a thoughtfully designed split floor plan with upgraded flooring, modern cabinetry, and stylish countertops throughout. The layout offers both functionality and comfort, ideal for those who love to entertain. Step outside to your private screened back porch retreat and fully fenced yard—perfect for relaxing evenings or weekend gatherings while enjoying the quiet, natural backdrop. This home truly combines luxury, privacy, and location—don’t miss the opportunity to make it yours.

Listing is courtesy of: VILLAGE REALTY OF WINTER HAVEN (863-299-6767)

Listing Agent: Joshua Taylor (863-651-5471)

Remarks: MOVE-IN READY Home with lakefront homesite! This stunning Highbourne with Coastal elevation greets you with a charming front porch, perfect for relaxing and enjoying the outdoors. Inside, a versatile flex space offers an ideal area for a formal living room or home office, conveniently connected to the kitchen. Just past the flex room is a thoughtfully placed half bathroom. The heart of the home features an expansive open-concept kitchen, dining, and living area, perfect for entertaining family and friends. The kitchen showcases elegant granite countertops, shaker cabinets, and a spacious layout. Sliding doors off the dining area lead to a covered lanai and an oversized backyard, providing serene views of the woods and lake. Upstairs, the oversized primary suite offers a luxurious primary bathroom with dual vanities, providing a private retreat. Three additional bedrooms and a centrally located laundry room complete the second floor, making the home ideal for families. The first floor is fully tiled, adding a sleek and easy-to-maintain finish throughout the main living areas. This Highbourne quick move-in home at Willowbrook North combines modern design, thoughtful layout, and beautiful natural surroundings, offering the perfect balance of comfort and style.

Listing is courtesy of: DRB GROUP REALTY, LLC (407-270-2747)

Listing Agent: Adam Schott (407-270-2747)