Winter Haven Homes For Sale & Real Estate - 863 homes

Remarks: Discover how easy life can feel in this beautifully maintained 2-bedroom, 2-bath villa offering over 1,100 square feet of comfortable, thoughtfully designed living space. With a mostly furnished interior and quick occupancy available, you can step right in and start enjoying it from day one. Located inside the gated CypressWood golf community, this home delivers true resort-style living. Spend your days enjoying the sparkling pool, tennis courts, and scenic golf course surroundings, all while the HOA takes care of lawn maintenance and exterior upkeep so you don’t have to. The location ties it all together. Just minutes from LEGOLAND Florida Resort, shopping, and dining, with quick access to Highway 27 and I-4, you’re perfectly positioned between Orlando and Tampa for work, travel, or a day out. Whether you’re looking for a full-time home or a seasonal escape, this is low-maintenance Florida living done right.

Listing is courtesy of: COMPASS FLORIDA LLC (727-339-7902)

Listing Agent: Darin Dobson (407-947-6773)

Remarks: This 4-bed, 2-bath home offers the peace of mind only a gated community can provide, all with an impressively low HOA. Whether you need room for a growing family, a dedicated home office, or a welcoming guest suite, this versatile layout. Beyond the front door, you are minutes away from top-rated schools, essential medical services, and everyday staples like Publix. Spend your weekends exploring the vibrant dining and nightlife of Downtown Winter Haven or creating memories at nearby Legoland. This is more than just a house; it’s an extraordinary opportunity to secure a lifestyle of comfort and convenience. Don't let this one slip away. Go ahead and schedule your tour today to see why this is the perfect place to call home.

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

Listing Agent: Twanna Dewdney (863-207-1634)

Remarks: 2118 Chris Dr is a property that boasts a kitchen equipped with all stainless steel appliances, adding a modern touch to the culinary space. The kitchen island serves as a functional centerpiece, perfect for meal preparation or casual dining. The primary bedroom is a haven of comfort, complete with a walk-in closet that provides ample storage for your wardrobe. With these attributes, this property ensures a comfortable and convenient lifestyle. 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: Attention investors and those looking for a great deal! Seize a truly unique opportunity to own two homes for the price of one. This property includes a single-family home with 2 bedrooms and 1 bathroom address 215 10th Wahneta St W Winter Haven FL, as well as a single-wide mobile home from 1988 with 2 bedrooms and 1 bathroom address 213 10th Wahneta St W Winter Haven FL 33880. The single-family & Mobile home needs Lot's TLC but has great potential. It could be perfect for someone willing to put in some work or an investor looking to flip or rent it out. Also included on the property is a detached garage offering an extra 480 square feet of storage space. This unique setup offers flexibility depending on your needs. This is truly a rare find at this price point. Don't miss out on this fantastic investment opportunity! Dual Rental Income, Fix-and-Flip Potential, Multi-Generational Living

Listing is courtesy of: J&T PROPERTY SOLUTIONS GROUP LLC (863-440-3603)

Listing Agent: Jennifer Daniell (863-440-3603)

Remarks: Welcome to this charming two-story townhome located in the Casarena gated community in Winter Haven, offering 2 bedrooms and 2.1 bathrooms designed for comfort and flexibility. The inviting main living area features a cozy fireplace, perfect for relaxing or entertaining, while the functional layout flows seamlessly into the dining and kitchen spaces. Upstairs, enjoy your own private second-floor balcony—an ideal spot for morning coffee or unwinding in the evening. Enjoy family gatherings in the large screened in patio that is ready to be converted into your ideal outdoors living space. Additional highlights include a convenient laundry closet in the garage and ample storage throughout. Whether you're a first-time buyer, downsizing, or seeking a low-maintenance lifestyle, this home checks all the boxes—schedule your private showing today and make it yours! This home is being sold in As Is condition. All buyers must view the home before submitting an offer.

Listing is courtesy of: REALTYCITY INC (863-438-6605)

Listing Agent: Jesse Carriedo (863-438-6605)

Remarks: Investor opportunity meets wide-open space! Situated on 11.8 acres at the end of a quiet dead-end road, this unique property offers privacy, flexibility, and endless potential. Featuring a 4-bedroom, 2-bathroom mobile home, this property is ideal for investors, renovators, or buyers looking to create their own private retreat or family compound. The home is in need of cosmetic updates, but major components have already been addressed, including a roof (3 years old), HVAC (4 years old), and hot water heater (4 years old)—providing a solid foundation for improvements. Inside, you’ll find a functional layout with original kitchen and bathrooms, stainless steel appliances included, carpet in living areas and bedrooms, and vinyl flooring in the kitchen. Washer and dryer hookups are available. This expansive property is perfect for those seeking space to spread out—bring your ATVs, off-road vehicles, boats, or work equipment, or explore the potential for multi-use living. With no HOA and a peaceful, rural setting, this property is well-suited for outdoor enthusiasts or those looking to escape city congestion. Sold AS-IS. Seller will make no repairs. Don’t miss this rare chance to own acreage with unlimited potential!

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

Listing Agent: Teri Hunter (863-307-1683)

Remarks: Fixer upper! THIS COULD BE THE ONE. PRIVATE POOL! So many possibilities! Lovely vaulted ceilings, 2 fireplaces, open kitchen, lovely wood accents, mahogany kitchen cabinets, office has a closet and could be converted to a 3rd bedroom 3 car garage/ carport and a separate workshop all on .75 of an acre. roof 10 years old, ac replaced 2019, UVI light 2024

Listing is courtesy of: YELLOWFIN REALTY (813-347-7547)

Listing Agent: Marcia Rains - Nadal, Mrs (813-493-2221)

Remarks: PRICE REDUCTION! MOTIVATED SELLER! With fabulous WATER VIEWS and GOLF COURSE views, this elegant residence offers a perfect tropical retreat. A large pool with a attached spa invites year-round outdoor enjoyment, framed by the beauty of Lake Ashton's natural surroundings. Ideally situated near Lake Wales and Winter Haven this home offers exceptional access to shopping and entertainment; medical facilities and restaurants. The spacious three-bedroom, two-bath layout includes a large den, ideal for a home office or flexible living space. The chef's kitchen features upgraded 42" cabinets, tiled backsplash, granite counter top and breakfast bar all designed for both form and function. The primary suite offers a spa-like escape with double vanities, a walk-in shower, a large soaking tub, separate water closet, and His and Her walk-in closets. Direct access from the PRIMARY SUITE to the outdoor living space is a BONUS. The outdoor living space is covered and screened to enhance the home's entertaining capabilities, creating a seamless flow between indoor and outdoor living. This ST. JOHN floor plan is a split plan home, which is desirable and spacious. Golf enthusiasts will appreciate the separate golf cart entry garage. Additional home features include: Travertine Flooring in the Living Areas (Bedrooms have carpet), Custom Shelving in the Den/Office with Glass Doors, Tray Ceiling in the Primary and Living Room areas, Sliding Glass Doors that Disappear into a Pocket in the Living Room and Beautiful Window Treatments, Floor outlets in the LR and MORE.... IT'S AS MUST SEE!!! Located in Lake Ashton, a 55+ community, residents enjoy access to a resort-style pool, fitness center, pickleball and tennis courts, and planned activities. Lake Ashton offers 2- 18 hole golf courses (Memberships Optional), Restaurant, Pro Shop and Eagles Nest. If you are seeking luxury, security and an active lifestyle, Lake Ashton could be your next home.

Listing is courtesy of: LAKE ASHTON REALTY INC. (863-221-5970)

Listing Agent: Lori Raath (863-409-6899)

Remarks: SHORT SALE!! Welcome to Heather Glen, a gated community in the heart of Winter Haven with an HOA of ONLY $150 A YEAR! This charming 3 bedroom, 2 bathroom home with an attached 2-car garage offers comfort, security, and convenience & ready for a quick close & move in. Featuring neutral gray walls, wood-look tile flooring, and plantation shutters throughout, this open-concept home is filled with natural light and boasts a spacious master suite with walk-in closet and private bath, two additional bedrooms with a guest bath, and a bright kitchen with plenty of counter space, a window over the sink, and a cozy dinette area for your morning coffee. Enjoy the convenience of an interior laundry room, newer roof and A/C unit, and a fully fenced backyard with a separate well for irrigation. Located just minutes from Legoland, Peppa Pig Theme Park, shopping, dining, medical facilities, and downtown Winter Haven, this pristine home is the perfect rental in a sought-after location. Schedule your showing today!

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

Listing Agent: Jeavanna Lanza Pa (585-313-3408)

Remarks: Welcome to this beautifully maintained 4-bedroom, 2.5-bath home built in 2018, offering the perfect blend of modern comfort and Florida lifestyle living. From the moment you step inside, you’ll appreciate the open-concept layout, ideal for both everyday living and entertaining. The spacious kitchen flows seamlessly into the living and dining areas, featuring contemporary finishes, ample cabinetry, and plenty of natural light throughout. The living area is enhanced by a stylish built-in electric fireplace, creating a warm and inviting focal point. This thoughtfully designed single-story home features a spacious primary suite with a private bath and walk-in closet, along with three additional bedrooms that offer flexibility for family, guests, or a home office. Step outside and enjoy your private backyard space—perfect for relaxing evenings or weekend gatherings. The garage is equipped with a mini-split air conditioning system, adding comfort and versatility for a workspace, gym, or additional storage. Located in a desirable community with private access to Lake Eloise, part of the renowned Winter Haven Chain of Lakes, you’ll have endless opportunities for boating, fishing, and enjoying the water just minutes from your doorstep. Plus, you’re just 10 minutes from LEGOLAND Florida Resort, making this location perfect for both everyday convenience and fun-filled weekends. Conveniently situated near shopping, dining, and major roadways, this move-in-ready home offers the ideal combination of location, lifestyle, and value. Schedule your private showing today and experience everything this home has to offer!

Listing is courtesy of: CLARK REALTY LLC (863-345-2155)

Listing Agent: Ty Dennis (863-651-8328)

Remarks: Price adjustment! Welcome to Garden Grove Oaks, a desirable 55+ community in Winter Haven! This charming move in ready 2-bedroom, 2-bath home offers comfort, convenience, and low-maintenance living in a beautifully maintained setting. The property features a full-yard irrigation system and beautifully landscaped grounds, along with the convenience of an inside laundry room. The sub-floor has been completely redone and Luxury Vinyl Plank has been installed. The primary bathroom has dual sinks with a walk in shower. There is a seperate storage shed for your convenience. Enclosed lanai/Florida room with a side air conditioner. One car covered carport and ample parking on the driveway. The low HOA of just $65 monthly includes access to a heated community pool, clubhouse, shuffleboard courts, and a full calendar of planned activities, plus scenic community walkways. Winter Haven offers an abundance of nearby amenities including restaurants, gyms, shopping, churches, hospitals, and medical facilities, as well as entertainment at the movie theater, the historic Ritz Theatre, and Theatre Winter Haven. LEGOLAND is just down the street, and Highway 27 is easily accessible. Enjoy the area’s many lakes for fishing, boating, or watching stunning sunsets. Orlando and Tampa attractions are approximately an hour away, making this an ideal location for both relaxation and adventure. Own your home and land and enjoy nearly maintenance-free living in this welcoming community.

Listing is courtesy of: MEEKS REAL ESTATE LLC (863-604-9287)

Listing Agent: Carla Meeks (863-604-9287)

Remarks: Investor Opportunity with Value-Add Potential in Winter Haven! Welcome to 112 Sandburg Ln a 3 bedroom, 2 bathroom block home on a concrete slab offering a solid foundation for investors or renovation buyers seeking a value-add project. The property features durable block construction, a practical floor plan, and ample opportunity for updates to improve functionality and overall appeal. This home is well-suited for a fix-and-flip or long-term rental strategy, with renovation potential that allows the next owner to maximize value. The layout provides flexibility for interior improvements, while the slab foundation and block construction support long-term durability and ease of maintenance. Conveniently located near shopping, dining, schools, and major roadways, the property has strong market appeal once renovated. Whether you're an experienced investor or a buyer looking for a renovation project, this property presents a compelling opportunity in the Winter Haven area. Property requires updates.

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

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

Remarks: 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: Welcome to 523 Little Lake Court — a spacious 3-bedroom, 2-bath home on a generous lot in the heart of Winter Haven. Step through elegant double front doors with decorative glass and an arched transom into soaring vaulted ceilings that flow throughout the main living areas. The open layout features beautiful hardwood floors in the formal living and dining rooms, a large family room with a cozy fireplace and dramatic arched windows, and a kitchen with wihte cabinetry, a center island, and breakfast bar. The master suite has vaulted ceilings, a freestanding fireplace, French doors to the backyard, and an en-suite bath with a soaking tub, walk-in shower, and dual vanity beneath a stunning arched window. Additional highlights include an interior laundry room, an attached two-car garage, and a large fully fenced backyard with mature trees and a storage shed. Conveniently located just minutes from Little Lake with easy access to shopping, dining, and everything Winter Haven has to do.

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

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

Remarks: Under contract-accepting backup offers. PRICE REDUCTION!!! MOTIVATED SELLER!!! Discover this exceptional income-producing property perfectly situated on a spacious 0.48-acre lot in the heart of Winter Haven. This versatile property features two separate living spaces, one currently rented—providing immediate income and excellent long-term investment potential. The main home which is now vacant and ready for it's new owners or tenants offers 3 bedrooms and 2 bathrooms, including a generous master suite with an en-suite bath. The open and functional layout makes it ideal for families or long-term tenants. Attached to the main residence is a 484 sq. ft. in-law suite currently rented, complete with a full kitchen, bedroom, bathroom, and private entrance. This flexible space can serve as an additional rental unit, private guest quarters, or be seamlessly integrated into the main living area for multi-generational living. This home was recently appraised above the asking price, giving buyers instant equity and outstanding value. Whether you’re an investor seeking steady cash flow or a homeowner looking for flexibility, this property is a rare find. Take advantage of strong rental demand, potential appreciation, and the benefits of owning in one of Florida’s fastest-growing counties, consistently rated among the best places to live. Don’t miss your chance to own this unique multi-unit property—schedule your private showing today!

Listing is courtesy of: BRIGHT REALTY (941-552-6036)

Listing Agent: Jen Victor (941-587-2787)

Remarks: MOVE-IN READY! Welcome to the Flagler floor plan, where timeless charm meets modern luxury. The home’s traditional elevation with a welcoming front porch sets the tone for elegance and comfort. Inside, a versatile flex space off the entry offers the perfect spot for a home office or cozy reading nook. The heart of the home features a chef-inspired kitchen with an oversized quartz island, sleek cabinetry, and abundant counter space, all seamlessly flowing into the dining and living areas. Natural light pours in through sliding glass doors, opening to the backyard and creating the ideal setting for entertaining or everyday living. Two spacious bedrooms, a full bath, and a conveniently placed laundry room are located just off the kitchen, designed with functionality and ease in mind. At the back of the home, the private primary suite feels like a true retreat with elegant tray ceilings, a generous walk-in closet, and a spa-style bathroom with dual vanities and designer finishes. With its open-concept design, luxurious finishes, and thoughtful split-bedroom layout, the Flagler offers the perfect balance of style, comfort, and sophistication an exceptional place to call home.

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

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

Remarks: Under contract-accepting backup offers. !!PRICE ADJUSTMENT!! NOW is your opportunity to own this home. Roof: 2023, HVAC: 2023, Water Heater: New, Electric: Serviced in 2020, Plumbing: Re-piped in 2025. 3/1.5 home in Winter Haven close to downtown (Target is coming!) and near Polk State College. Huge yard! New carpet in every bedroom! Pretty bathrooms! Walk to the lake! Schedule a showing today! This property has approximately 1,559 square feet of living space on a lot of approximately 0.28 acres, with three bedrooms, one full bathroom and an en-suite half bathroom. Hardwood-style vinyl flooring and stone fireplace creates a warm and inviting tone. Large windows allow for an tons of soft, natural light to fill the rooms, enhancing the open layout and creating a peaceful setting. The separate dining room area provides space for hosting a dinner or game night. The retro vibe flows throughout the house and fits-in with the established neighborhood. An efficient kitchen features a window overlooking the backyard and makes it convenient to have BBQs and fun playtime out back. The backyard has it's own storage shed and is large enough to have a pet, playground or maybe even a pool. The primary bedroom and two additional bedrooms are on opposite sides for privacy and quiet. The vintage-styled bathrooms add a unique charm to the home. The pink tile sequence makes it fun to get ready for the day. Just steps from the college, the property is conveniently located near the college ballfields, offering easy access to recreational activities. A walking trail nearby provides opportunities for exercise, and the home is situated close to the town, allowing for quick and easy access to local shopping. The garage features a work bench and shelves, providing storage and workspace. The property's proximity to the lake allows for enjoyable walks or leisure activities on the water.

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

Listing Agent: Maria Deary (863-241-8361)

Remarks: The two-story Atlanta Plan has the “WOW-Factor” with four bedrooms, two and a half baths, loft and a two-car garage. This exquisite home offers an open floor plan with great room, dining room, and kitchen with large island. The kitchen features ample counter space, and generous pantry. The casual dining area allows outdoor access to a covered lanai via sliding glass doors. The second floor includes an owner's retreat featuring an owner's bath with large walk-in shower, dual vanity, and spacious walk-in closet. Three additional bedrooms, a bathroom, a spacious loft, and laundry room finish off this beautiful home. This home comes fully equipped with Everything Included Features like new appliances, solid surface countertops throughout and oversized tile flooring in the wet areas. Peace Creek Reserve is a masterplan community of new single-family homes with a beautiful natural creek. Winter Haven is the chain of lakes city, with over 26 linked together by canal. There are lots of shops, restaurants, bike paths. Peace Creek Reserve is what you have been looking for. A safe small town feel with convenience, the perfect place to raise a family.

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

Listing Agent: Omar Andreasen (407-883-2989)

Remarks: Under contract-accepting backup offers. ** RECENT $20K PRICE REDUCTION as of 3/10/2026!!** Corner Lot 3 Bedroom Home in Winter Haven | Granite Kitchen | Fully Fenced Yard | Extra Parking Located at 2017 Misty Morning Dr in Winter Haven, FL 33880, this 3-bedroom, 2-bath home sits on a spacious corner lot with a fully fenced vinyl privacy yard and extended driveway offering additional parking space. The open-concept layout features vaulted ceilings, abundant natural light, and durable tile flooring throughout the main living areas. The kitchen includes granite countertops, stainless steel appliances, ample cabinetry, and a breakfast bar that overlooks the living and dining spaces—ideal for everyday living and entertaining. The split-bedroom floor plan provides separation and privacy, with a comfortable primary suite and well-sized secondary bedrooms. Outside, the large white vinyl fence encloses the backyard, creating a secure space for pets, outdoor gatherings, or future enhancements. The oversized lot provides more yard space than many homes in the area. Additional features include: • 2-car garage • Extended driveway with additional parking pad • Covered front entry • Neutral interior finishes • Move-in ready condition Conveniently located in Winter Haven with easy access to major highways, shopping, dining, and Central Florida commuting routes, this property offers space, privacy, and everyday functionality in the 33880 market.

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

Listing Agent: Don Jerue (863-259-9550)

Remarks: Price reduction! Bring your buyers. Motivated seller brings added opportunity on this inviting four-bedroom, two-bathroom single family home in Winter Haven. Featuring a desirable split floor plan, this home offers privacy comfort, space, and functionality for the primary suite while maintaining an easy, natural flow throughout the main living areas perfect for everyday living and entertaining. The spacious primary suite serves as a relaxing retreat, featuring, a walk-in closet, a soaker tub, and a separate shower. Generously sized secondary bedrooms present flexibility for guests, a home office, or future needs. Enjoy warm and welcoming living spaces that lead to a screened patio, ideal for morning coffee or evening gatherings, all overlooking a fenced backyard that provides privacy and room to enjoy the outdoors. A brand-new roof installed in 2025 adds peace of mind and long-term value. Move-in ready and competitively price. This home is a fantastic opportunity for buyers. Looking for space, comfort, and a great value This home is ready for its next owners. Schedule your showing today and bring your offers. YOUR NEW HOME AWAITS. DOWN PAYMENT ASSISTANCE IS AVAILABLE TO QUALIFIED BUYER(S)

Listing is courtesy of: AUDITH POLEON REALTY (863-709-5643)

Listing Agent: Audith Poleon (863-709-5643)