Winter Haven FL Real Estate & Homes for Sale

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Beds:
3
Baths:
2.00
Sq.Ft.:
1,214
Status:
Active
MLS#:
R11078833
Type:
Single Family
Subdivision:
EAGLE HEIGHTS
Lot size:
0.14 Acres
Year built:
1996
A broker reciprocity listing Courtesy: Keller Williams Realty/P B 561-656-2929
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ADDITIONAL INFORMATION

Turnkey Airbnb Investment - $290,000 $6,000+ Monthly IncomeLooking for a high-performing short-term rental with strong returns? This turnkey Airbnb property is generating over $6,000 per month in rental income and is fully set up for immediate operation.Whether you're a seasoned investor or just entering the short-term rental market, this property offers a hassle-free investment with professional management available at just 15%--making it easy to earn passive income from day one.Note: Furniture and furnishings are not included in the sale price but are negotiable.Don't miss this chance to own a cash-flowing rental in a high-demand market--skip the setup stress and step into a proven income stream.

Beds:
4
Baths:
2.00
Sq.Ft.:
1,564
Status:
Active
MLS#:
O6296983
Type:
Single Family
Subdivision:
Villamar Ph 5
Lot size:
0.1 Acres
Year built:
2025
A broker reciprocity listing Courtesy: NEW HOME STAR FLORIDA LLC 407-803-4083
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ADDITIONAL INFORMATION

Welcome to The Ventura – a beautifully designed home that combines modern comfort with premium finishes, located in the desirable Villamar community. This thoughtfully crafted split floor plan offers both privacy and functionality, with a welcoming foyer that leads to three secondary bedrooms and a full bathroom—creating an ideal space for guests or flexible use. The heart of the home is the open-concept kitchen and great room, perfect for entertaining and everyday living. The kitchen features elegant quartz countertops, soft-close cabinetry, a spacious island, and a stainless steel side-by-side refrigerator, seamlessly blending style and convenience. The great room is bathed in natural light, providing a warm and inviting atmosphere, enhanced by 4 LED lights that add brightness and ambiance to the space. At the rear of the home, the owner’s suite offers a private retreat with a large walk-in closet and a luxurious en-suite bath. This tranquil space includes quartz countertops and a ceramic tile shower with a glass enclosure, creating a spa-like experience right at home. Throughout the home, you'll find ceramic tile flooring in the main areas, while the bedrooms are cozy with carpet. The well-appointed laundry room includes upper cabinets for extra storage and comes with a washer and dryer, making daily chores more convenient. Smart Home features are included for your convenience, with a Ring Video Doorbell, a Smart Thermostat, a Keyless Entry Smart Door Lock, and DEAKO switches to enhance your living experience. The exterior is equally impressive, with beautifully landscaped grounds and an irrigation system that enhances the home’s curb appeal while minimizing maintenance. As a resident of Villamar, you’ll have access to a range of resort-style amenities, including a swimming pool with a lap lane, an expansive pool deck with shaded seating, a clubhouse, a playground and park area, a dog park, green spaces, ponds, wetlands, and walking paths. The community is also home to waterfront and conservation homesites, offering tranquility and natural beauty. This home comes with a full builder warranty, ensuring peace of mind for years to come. Whether you’re unwinding inside or enjoying the vibrant surroundings, The Ventura delivers the perfect combination of comfort, convenience, and elegance.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,680
Status:
Active
MLS#:
O6296969
Type:
Single Family
Subdivision:
Villamar Ph 5
Lot size:
0.1 Acres
Year built:
2025
A broker reciprocity listing Courtesy: NEW HOME STAR FLORIDA LLC 407-803-4083
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ADDITIONAL INFORMATION

Pre-Construction. To be built. Discover The Vista – a perfectly crafted single-story home in the sought-after Villamar community, where modern style, smart features, and effortless comfort come together. This beautifully designed residence features three bedrooms, two full bathrooms, and a spacious open-concept layout that’s ideal for both everyday living and entertaining. With upgraded ceramic tile throughout the main areas and cozy carpeting in the bedrooms, the Vista offers a stylish yet practical interior from the moment you step inside. At the heart of the home, the kitchen impresses with quartz countertops, soft-close cabinetry with upgraded crown molding, a chic tile backsplash, and a stainless steel side-by-side refrigerator. The oversized island provides the perfect spot for casual meals or gathering with guests, all flowing seamlessly into the dining space and expansive great room. Tucked away for privacy, the owner’s suite features a generous walk-in closet and a sleek en-suite bathroom complete with dual vanities and a beautifully tiled shower with glass enclosure. Two additional bedrooms are located at the front of the home, with easy access to a full bath and a linen closet. The dedicated laundry room—complete with a washer and dryer—adds convenience to your daily routine. Enjoy peace of mind with smart home technology, including a Ring Video Doorbell, Smart Thermostat, Keyless Entry Smart Door Lock, and DEAKO Smart Switches, putting control and security at your fingertips. Outside, this home shines with lush landscaping, a full irrigation system, and a two-car garage—all backed by a full builder warranty. Located in Villamar, one of the area’s premier communities, residents enjoy exceptional amenities: a resort-style swimming pool with lap lane, expansive pool deck with shaded seating, a stylish clubhouse, playground and park area, dog park, walking paths, green spaces, tranquil ponds, wetlands, and waterfront and conservation homesites. The Vista isn’t just a home—it’s a lifestyle. Move-in ready and filled with features that matter most, this home is the perfect blend of function, beauty, and peace of mind. Schedule your private showing today!

Beds:
2
Baths:
2.00
Sq.Ft.:
1,385
Status:
Active
MLS#:
S5124391
Type:
Other
Subdivision:
Traditions Ph 2a
Lot size:
0.07 Acres
Year built:
2018
A broker reciprocity listing Courtesy: JASON MITCHELL REAL ESTATE FLO 754-307-0607
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ADDITIONAL INFORMATION

**Price Improvement** Welcome home to comfort, quality, and tranquility! This move-in ready, beautifully maintained villa sits on a premium waterfront lot, offering peaceful views and a serene ambience. Enjoy quiet mornings and relaxing evenings from the covered, screened lanai overlooking the picturesque setting—your own private outdoor retreat. Inside, you’ll immediately appreciate the warm, inviting finishes, including gray quartz countertops, sleek stainless steel appliances, and tiled floors throughout the main living areas and baths. Crown molding and 9-ft. ceilings elevate the space, while smart-home features—Honeywell thermostat, WiFi-controlled garage door opener, smart lock, and whole-home surge protector—provide modern convenience and peace of mind. The spacious primary suite offers a restful escape with a walk-in closet featuring motion-activated lighting and a luxurious en suite bath with double vanity and walk-in tiled shower. A flexible bonus room is perfect for a home office, craft room, or guest space. This gently lived-in home shows like new, with thoughtful touches such as a dedicated laundry room (washer & dryer included), overhead garage storage, and a freshly painted exterior (2024). Located in a vibrant 55+ gated community, the HOA covers an impressive list of services—including roof maintenance/repairs, exterior paint every 5 years, cable, internet, termite protection, lawn maintenance and fertilization (including shrubs and trees), irrigation repairs, and exterior home insurance. The HOA-provided exterior insurance can significantly lower your personal homeowner’s insurance costs. Enjoy a rich array of amenities: two heated community pools for year round enjoyment, hot tub, sauna, fitness center, tennis and pickleball court, basketball court, billiards, library, dog park, walking trails, a community boat ramp with access to Lake Ruby, and a spacious ballroom ideal for gatherings and events. NO CDD! This villa offers more than a home—it offers a lifestyle. Come see why this community is the perfect place to relax, connect, and enjoy everyday living.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,221
Status:
Active
MLS#:
L4951980
Type:
Single Family
Subdivision:
Thornhill Oaks
Lot size:
0.28 Acres
Year built:
2024
A broker reciprocity listing Courtesy: REMAX EXPERTS 863-802-5262
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ADDITIONAL INFORMATION

***BELOW MARKET VALUE*** New Construction 3 Bedrooms 2 Baths built by the best builder in the area WCM Construction! This home is built with high quality kitchen and bathroom cabinetry, Level 3 Granite counters throughout kitchen and baths, high end appliances, beautiful wood grain tile throughout the entire home - no carpet or wood. Built with perfection, yet affordably priced! Check out the complete walk-thru video or better yet, call for an appointment to see this beauty in person!

Beds:
3
Baths:
3.00
Sq.Ft.:
1,334
Status:
Active
MLS#:
TB8368412
Type:
Condo
Subdivision:
Casa Del Sol Condo Village Ph 02
Year built:
1976
A broker reciprocity listing Courtesy: HOMECOIN.COM 888-400-2513
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ADDITIONAL INFORMATION

This desirable and low-maintenance condo is a spacious 1,334 sq ft unit, featuring 3 bedrooms, 2 1/2 bathrooms, an attached 2-car garage, a gated front lanai, a private screened-in balcony off the master bedroom, and a 25-foot screened back porch with insulated roof. Located in Casa del Sol, one of Winter Haven's premier and original condominium communities, is ideally located with easy access to Interstate-4, Hwy 17/92, Polk Parkway, and major routes leading to Tampa and Orlando theme parks and near Winter Haven Regional Airport. You have two entries through the double-car garage. In either direction, you'll find a versatile room that could serve as a formal dining area or be used as a sitting room, with sliding glass doors opening to your private, fenced, and gated lanai. The kitchen is equipped with granite countertops, stainless steel appliances (dishwasher, refrigerator, oven/cooktop), ample cabinetry, a large pantry and an attached laundry room with cabinets and extra storage closet. THE UNIT HAS BEEN REPLUMBED. At the rear of the first floor is a spacious living/dining area with crown molding throughout and two sliding glass doors leading to a screened-in back patio that overlooks the green space. This area also includes a convenient half bath with a vessel sink. Upstairs, the owner's suite offers a screened-in balcony, a oversized built-in granite vanity with storage, and a step-in closet. The ensuite bathroom features your jacuzzi bathtub. The two guest bedrooms share a full bathroom with a bathtub. The upstairs flooring has been newly replaced and is pet and smoke free. The Casa del Sol community offers two pools, a tennis court, and clubhouse with a brand new dock where you can leave a boat for the day. Enjoy the Florida sunshine by relaxing at the larger pool with a splash pool, which overlooks Lake Hartridge on the Winter Haven Chain of Lakes. For a smaller setting, you have a second pool option. If you are planning a gathering, the lake area pool has a designated area with a sink, washrooms, and picnic tables and chairs which is perfect for the day, or the clubhouse has a kitchen, bathrooms, and plenty of seating. Both can be reserved only with a small deposit which will be returned once you clean up after yourself.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,603
Status:
Active
MLS#:
P4934266
Type:
Single Family
Subdivision:
Island Lakes
Lot size:
0.4 Acres
Year built:
2006
A broker reciprocity listing Courtesy: KELLER WILLIAMS REALTY SMART 1 863-508-3000
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ADDITIONAL INFORMATION

**$40K PRICE REDUCTION!!** Lakefront Living on the Chain of Lakes! Welcome to 4099 Island Lakes Dr, a stunning 3 bed, 2 bath block home offering breathtaking waterfront views and direct access to the Chain of Lakes. Nestled in a peaceful setting, this home is perfect for those who love boating, fishing, or simply enjoying serene lakefront sunsets. Step inside to a spacious and inviting layout with plenty of natural light. The living area flows effortlessly into the kitchen and dining space, making it ideal for entertaining. The primary suite offers beautiful lake views, a private bath, and ample closet space. Outside, enjoy a freshly landscaped yard with new sod, providing lush curb appeal and a perfect outdoor space for relaxation or gatherings. With direct lake access, you can launch your boat or kayak right from your backyard and explore the scenic waterways. Don’t miss this rare opportunity to own a lakefront home in a prime location. Whether you're looking for a full-time residence or a vacation retreat, this home has it all. Call today to schedule your private tour and start living the lakefront lifestyle!

Beds:
3
Baths:
2.00
Sq.Ft.:
700
Status:
Active
MLS#:
L4951816
Type:
Manufactured Home
Subdivision:
Fairview Village
Lot size:
0.05 Acres
Year built:
1986
A broker reciprocity listing Courtesy: KELLER WILLIAMS REALTY SMART 863-577-1234
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ADDITIONAL INFORMATION

Do you have dreams of easy mornings on your front porch sipping your perfect cup of coffee with a spectacular view of Lake Henry? Lakeside Village is an active 55+ co-op that features a pool, community center offering community dinners and exciting social activities, shuffleboard courts, a boat slip and fishing on Lake Henry! With 3 bedrooms and 1.5 bathrooms, this home has been meticulously maintained and updated with drywall throughout giving it a cozy feel. The roof was replaced in 2023 along with new interior paint. The exterior was re-painted in 2025 and AC was replaced in 2017. This home is located conveniently in Winter Haven with easy access to dining, shopping, and major roadways. Arriving at the home, you’ll find a covered lake view front porch. Inside, there is LVT flooring throughout, a spacious living room with plenty of natural light and the kitchen/dining area offers plenty of space for entertaining. The private primary bedroom is located at the back of the home and provides an en-suite with shower. The home includes an indoor laundry/storage room and a separate utility room with its own outdoor access. Schedule your private showing today and see all that this home has to offer!

Beds:
5
Baths:
3.00
Sq.Ft.:
3,161
Status:
Active
MLS#:
P4934289
Type:
Single Family
Subdivision:
Hamilton Pointe
Lot size:
0.98 Acres
Year built:
1997
A broker reciprocity listing Courtesy: COLDWELL BANKER REALTY 863-294-7541
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ADDITIONAL INFORMATION

This beautiful home overlooks Lake Hamilton being the largest lake on a chain of three, Lake Hamilton, Middle Lake Hamilton, and Little Lake Hamilton in Winter Haven Florida making Hamilton Pointe a sought out community. The 2 story home presents with a circular drive way leading to the double front door entrance. Upon entering 3161 Square feet of living area, high ceilings with crown molding, 5 bedrooms, 3 bathrooms, and a stunning view of the lake. The foyer has marble tile with the dominant flooring down stairs being wood. On the left the formal dining room is currently being used as an office and on the right side of the foyer is the formal living room. The family room offers welcoming view of the lake which flows into the bonus room. The kitchen has granite countertops, pantry, breakfast bar along with a large dinette with a view of the lake. The Laundry room is on the first floor. The large primary bedroom faces the lake includes a master bath with a garden tub, shower, dual sinks, and a spacious walk in closet. On the second floor there are 3 bedrooms and one bathroom. The side drive way leads to the large attached garage. Inground Irrigation. There is an attached screened lanai with a lake view to enjoy the sunrise. Winter Haven is also known as " The Chain of Lakes City" comprised of 19 interconnected lakes. Great for boating, skiing, and fishing. Winter Haven is conveniently located between Orlando, Tampa, and a growing airport in Lakeland. Legoland is 20 minutes away and Disney World is approximately 45 minutes away. For the Arts, Winter haven has Theatre Winter Haven offering plays and music. Historic Ritz Theatre is now Ritz Reimagined offering bands performing music of the past. Great restaurants and shopping. All room measurements are approximate and should be verified by the buyer.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,050
Status:
Active
MLS#:
TB8360466
Type:
Townhouse
Subdivision:
Wellington Pt 01 Bldgs 01 02 & Wellington Pt 02 B
Lot size:
0.01 Acres
Year built:
1969
A broker reciprocity listing Courtesy: RIVERA & ASSOCIATES REALTY 813-443-5031
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ADDITIONAL INFORMATION

Beautiful property located in a remarkable location! Do not miss out on the opportunity of making this property yours. Discover the perfect blend of comfort and convenience in this beautiful Winter Haven property. Nestled in a peaceful neighborhood, this property offers spacious living areas and a welcoming atmosphere. Enjoy bright living, a well-appointed kitchen, and generously sized bedrooms. Don't miss out- schedule a showing today!

Beds:
4
Baths:
2.00
Sq.Ft.:
1,828
Status:
Active
MLS#:
S5123505
Type:
Single Family
Subdivision:
Lakeside Landings Phase 3
Lot size:
0.13 Acres
Year built:
2020
A broker reciprocity listing Courtesy: KELLER WILLIAMS ADVANTAGE III 407-207-0825
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ADDITIONAL INFORMATION

Short Sale. One of the most sought-after floor plans, this 4-bedroom, 2-bathroom home boasts numerous charming features and is set on an oversized lot with no rear neighbors and a serene water view. As you enter, you'll find three spacious bedrooms and a modern bathroom. To the left, the inviting, contemporary kitchen showcases a large pantry offering ample storage space. The open dining area flows seamlessly into the airy living room, creating a perfect space for gatherings. Step outside to your private screened-in patio and enjoy the expansive yard with a tranquil, picturesque view. The luxurious Master Suite features dual sinks and a generous walk-in closet. The kitchen island and open layout are perfect for entertaining. This home comes complete with all major appliances, blinds, and is equipped with Smart Home Technology, including Alexa. Conveniently located near I-4, shopping, and entertainment, and offering access to a community pool. All of this at an unbeatable price in an up-and-coming location!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,226
Status:
Active
MLS#:
S5123247
Type:
Condo
Subdivision:
Imperial Harboursphases 01 & 02
Lot size:
0.01 Acres
Year built:
1973
A broker reciprocity listing Courtesy: LPT REALTY, LLC 877-366-2213
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ADDITIONAL INFORMATION

Welcome to 333 Lake Howard Drive, where comfort, convenience, and a vibrant 55+ lifestyle come together in the heart of Winter Haven’s charming lakefront community. Nestled within the desirable Imperial Harbours 55+ community, this spacious and sunlit 3-bedroom, 2-bathroom corner-unit condo that oversees the pool offers the ideal space for those seeking a relaxed, maintenance-free lifestyle. From the moment you walk in, you’ll feel the warmth and tranquility of this thoughtfully designed home. Spacious Living and Dining Area: Enjoy an open-concept layout perfect for hosting family and friends. Light-Filled Corner Unit Large windows allow natural light to pour in, creating an inviting and bright ambiance. The Private Master Suite Features an en-suite bathroom and a walk-in closet for all your storage needs. Versatile Bonus Space: Perfect for a home office, hobby room, or cozy reading nook. In-Unit Laundry A dedicated laundry closet with a washer and dryer for added convenience. Updated Kitchen With ample counter and cabinet space. Living here means having access to exceptional amenities that enhance your lifestyle: Lakefront Serenity: Enjoy lake frontage on scenic Lake Howard on the Chain of Lakes, complete with a private dock and fishing pier. Take in the stunning sunsets, go for a stroll, or enjoy a day on the water. Heated Pool and Spa: Relax year-round in the community’s heated swimming pool. Clubhouse and Billiards Room: Socialize with neighbors or host your next get-together. Shuffleboard Courts and Gazebo: Perfect for fun, fitness, and friendly competition. Covered Parking and Elevator Access: Ease and convenience with designated parking and easy building access. Located just minutes from downtown Winter Haven, this community offers easy access to local shopping, dining, entertainment, and healthcare facilities. Whether you enjoy morning walks by the lake, engaging in community events, or relaxing poolside, Imperial Harbours is designed for active seniors who want to make the most of their golden years. About Winter Haven – THE CHAIN OF LAKES CITY When you live here, you’re not just getting a home—you’re becoming part of the charm and history that makes Winter Haven one of Florida’s most beloved cities. Famous Chain of Lakes: Winter Haven is home to over 50 interconnected lakes, perfect for boating, fishing, kayaking, or simply enjoying a sunset cruise. You can hop on a boat and explore miles of waterways that connect lakes, parks, and restaurants. Vibrant Community: With weekly farmers markets, art festivals, live music, and local eateries, Winter Haven offers small-town charm with plenty of big-time fun. Close to Attractions: Situated between Tampa and Orlando, you’re just a short drive from LEGOLAND Florida Resort, world-class theme parks, and some of Florida’s best beaches. Imagine starting your mornings with coffee on your private balcony, enjoying a stroll along the lake, or spending afternoons by the heated pool with friends. Whether you’re looking to relax, stay active, or build new connections, this condo is the perfect place to make the most of your golden years. Don’t miss this opportunity to live in Winter Haven’s thriving 55+ lakefront community. Schedule a private tour today and discover why so many call Imperial Harbours home!

Beds:
2
Baths:
2.00
Sq.Ft.:
1,319
Status:
Active
MLS#:
P4934140
Type:
Single Family
Subdivision:
Lake Ashton West Ph 01
Lot size:
0.14 Acres
Year built:
2006
A broker reciprocity listing Courtesy: A+ REALTY LLC 863-293-1141
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ADDITIONAL INFORMATION

Pride of ownership is evident in this well-maintained "snowbird" owned Caribbean floor plan home. The curb appeal comes from the quality landscaping, which includes tasteful plantings, palms, and a paver walk and drive. All the landscaping is "watered" by an automatic irrigation system. The home has many special features and recent upgrades that frees up the new owners. The roof was replaced in 2023. The water heater was replaced in January 2025. The air conditioning system was totally replaced in 2022. New flooring was installed in 2021. The entire interior was repainted in 2021. The primary bath was remodeled in 2022. It just doesn't get any better. Walking up the wide paver walk to the front door, the screened and covered front entry provides both an additional area to enjoy the great Florida weather while also adding a layer of security. The screened front entry also makes cross ventilation a breeze. Upon entering, one notices that the welcoming foyer gets great natural light from the sidelights on the front door. Also evident is that this most efficient floor plan makes this home seem much larger than its stated square footage. The living room is the central focal point of this home. The north wing holds the guest and primary bedroom suites. The south wing has the garage, kitchen, and dining room. The living room has a designer rotating double fan with light. The triple slider at the end of the living room opens to the covered and screened lanai. The lanai has a ceiling fan with light and ceramic tile flooring. Just outside the lanai is a large paver open patio that looks out to an ample backyard bordered by a privacy hedge. Having options for enjoying the outdoors is always a plus. The kitchen features high quality stainless steel appliance, granite counter tops, crown molding on wood cabinetry, a snack bar, and a closet pantry. Also in the kitchen is the laundry closet. The washer and dryer stay for the new owners. Adjacent to the kitchen is the dining room which has plenty of space for your dining room furniture. Having both a dining room and a snack bar gives options for dining. The dining room also has a double slider that opens to the covered and screened lanai. The attached 2 car garage is accessed from the kitchen and features an opener and painted floor. The guest suite is at the front of the home and can be isolated from the rest of the home by using the handy pocket door. The large guest bedroom has a ceiling fan with light and a large reach-in closet. The short hallway from the bedroom holds the linen closet and the guest bath. The guest bath has a combination tub and shower with a glass shower door and ceramic tile surround. The wood vanity has a granite counter top. The primary suite is at the rear of the home and features a large bedroom with enough space for your bedroom furniture. The primary bedroom has a ceiling fan with light and a large window area. There is also a hallway that connects it to the primary bath. This hallway is home to 2 walk-in closets. The primary bath was remodeled 2022 and features a wood vanity with a granite counter top with 2 sinks, an elongated stool, stall shower with ceramic tile surround, a corner seat and glass shower door. This is the perfect home at a great price which gives the owner access to all of Lake Ashton's many amenities and outstanding resort style living lifestyle. Why not enjoy the good life. Some of the furnishing are available in the ready to move-in, must see home.

Beds:
4
Baths:
2.00
Sq.Ft.:
1,532
Status:
Active
MLS#:
L4951690
Type:
Single Family
Subdivision:
West Cannon Heights
Lot size:
0.21 Acres
Year built:
1963
A broker reciprocity listing Courtesy: COLDWELL BANKER REALTY 863-294-7541
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ADDITIONAL INFORMATION

FOR SALE - LEASE WITH OPTION TO BUY PROGRAM AVAILABLE - 4 BEDROOM/2 BATH - Single Family Home-Freshly painted cement block home that features four nice sized bedrooms, a massive Family Room, and an upgraded kitchen. The Guest Bathroom has newer tile in the tub and shower. It also has newer light fixtures and a newer mirror. The floorplan is a split bedroom design with newer laminate flooring. The backyard is large and is partially fenced. The residents who live in this neighborhood find it hard to move as many of them have lived here for 50 years or more! No HOA! No CDD! Just a lovely home in the center of Winter Haven. If you like skiing, Winter Haven is the Ski Capital of the World! Downtown Winter Haven has about a dozen restaurants plus activities for the family every month. These activities include arts and crafts, farmers' markets, music, games, and more. The Winter Haven Public Library offers not only books but movies, family activities and a "kiddie corner". Winter Haven has 26 buildings registered with the U.S. National Register of Historic Places. DISNEYWORLD and the Orlando attractions are 45 minutes away. You just can't beat it...an active community with parks, lakes, theatres, and restaurants. Just come to Winter Haven...it's the home of LEGOLAND!

Beds:
2
Baths:
2.00
Sq.Ft.:
1,035
Status:
Active
MLS#:
P4934214
Type:
Manufactured Home
Subdivision:
Oakwood Estates
Lot size:
0.09 Acres
Year built:
1983
A broker reciprocity listing Courtesy: COLDWELL BANKER REALTY 863-294-7541
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ADDITIONAL INFORMATION

Move right into this beautifully remodeled home. The open living area features an awesome kitchen with all a huge bar/work space. This home is perfect for entertaining, or just sit out on the open front porch and watch the world go by. There is no carpeting in this home, it is a vinyl plank throughout the home. The windows are a double pane insulated window adding to the energy efficiency of the home. The stackable washer and dryer is located in the guest bedroom closet. The side porch offers lots of room for storage, plus there is a shed out back. The shingled roof was installed in 2024 and the air conditioner was installed in 2020. There is also a water softener. The home comes furnished with what you see in the home as you are viewing it. Oakwood Estates, a 55+ community, offers many amenities such as shuffleboard, 2 pools and 2 clubhouses, tennis courts, miniature golf and much, much more.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,682
Status:
Active
MLS#:
S5123194
Type:
Other
Subdivision:
Cypresswood Golf Villas
Lot size:
0.05 Acres
Year built:
1990
A broker reciprocity listing Courtesy: HAPPY DAYS REALTY LLC 407-507-3272
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ADDITIONAL INFORMATION

GOLF COURSE HOME! WELCOME TO THIS AWESOME GOLF VILLA WITH A FAIRWAY VIEW OF THE 8TH HOLE. WELL MAINTAINED HOME. ALL APPLIANCES REMAIN. TANKLESS WATER HEATER. FRESH PAINT. GENEROUS SIZED ROOMS, BEAUTIFUL SUNROOM/FAMILY ROOM WITH OUTDOOR PATIO OVERLOOKS GOLF. FRONT COURTYARD IS PRIVATE AND INVITING. YOUR OWN COVERED PARKING, CARPORT KEEPS CAR PROTECTED. PRIVATE ENTRANCE. GUARD GATED COMMUNITY, LOW HOA. COMMUNITY POOL, TENNIS AND GOLF. GOLF CART COMMUNITY. CLUBHOUSE ACTIVITIES. MUSIC, CORN HOLE, TRIVIA, RESTAURANT ONSITE. CLOSE TO GREAT SHOPPING, RESTAURANTS, POST OFFICE. SELLER HAS ESTABLISHED FLOWER GARDEN ATTRACTS BUTTERFLIES. NON SMOKING HOME. CLEAN AND MOVE IN READY. WONDERFUL END UNIT WITHIN A PRIVATE ENCLAVE OF VILLAS, NOT A THROUGH STREET. WINTER HAVEN IS BUSTLING WITH EVENTS, FARMERS MARKET AND LOVELY TOWN CENTER, FOUNTAINS, PARKS AND CHAIN OF LAKES FOR THE BOATING LIFE. EASY DRIVE TO THEME PARKS, LEGO LAND, DISNEY, UNIVERSAL. HOA REPLACES ROOFS EVERY 10 YEARS, PAINTS EXTERIORS AND MAINTAINS OUTDOORS LAWN,SHRUBS AND PEST CONTROL. THIS HOME IS NOT TO BE MISSED. ONE OF THE BEST LOCATIONS IN ALL WINTER HAVEN! POLK COUNTY #1 PLACE TO LIVE IN FLORIDA! CENTRAL LOCATION, EAST/WEST COAST BEACHES HOUR DRIVE. COME ENJOY EASY MAINTENANCE LIFESTYLE. BEST LOCATION IN CYPRESSWOOD, NOT A THRU STREET.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,344
Status:
Active
MLS#:
R4909059
Type:
Single Family
Subdivision:
Lake Elbert Heights Unit 02 02 Rep
Lot size:
0.32 Acres
Year built:
1958
A broker reciprocity listing Courtesy: MILLSHIRE REALTY 863-815-8000
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ADDITIONAL INFORMATION

Short Sale. Quaint 3/2 home perfect for 1st time homebuyers or could be a great rental property. Contract is contingent upon third party bank approval. Centrally located to major highways and shopping.

Beds:
5
Baths:
3.00
Sq.Ft.:
2,244
Status:
Active
MLS#:
TB8364963
Type:
Single Family
Subdivision:
Peach Crossings
Lot size:
0.1 Acres
Year built:
2025
A broker reciprocity listing Courtesy: LGI REALTY- FLORIDA, LLC 904-449-3938
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ADDITIONAL INFORMATION

Welcome to the Spring model in Peach Crossings, a spacious five-bedroom, three-bathroom, two-story home situated on a desirable corner lot with no rear neighbors, offering extra privacy and an open feel. As you step inside, a long and inviting foyer welcomes you into the home. The first floor boasts a bright and open family room, perfect for gathering, along with a modern kitchen featuring a large island, breakfast bar, and brand-new Whirlpool appliances. A guest bedroom and a full bathroom on the main level provide a comfortable space for visitors or a private home office. Upstairs, the master retreat offers plenty of space for a king-sized bed, a dresser, and even a cozy reading nook. The en-suite bathroom includes a dual sink vanity, a linen closet for added organization, and a spacious walk-in closet for all your storage needs. The four additional bedrooms are generously sized, allowing everyone their own private space. These rooms can also be used as a home office, playroom, or hobby room to suit your lifestyle. With three full bathrooms, mornings run smoothly without congestion. A large upstairs laundry room with ample storage and a dedicated closet adds to the home’s convenience. Step outside and enjoy the covered back patio and covered front porch, perfect for relaxing or entertaining outdoors. Located in the highly sought-after Peach Crossings community, this home offers easy access to top-rated Polk County schools, shopping, dining, and local attractions. With all upgrades included, this home is move-in ready! Schedule your private showing today!

Beds:
4
Baths:
2.00
Sq.Ft.:
1,863
Status:
Active
MLS#:
TB8364835
Type:
Single Family
Subdivision:
Peach Crossings
Lot size:
0.1 Acres
Year built:
2025
A broker reciprocity listing Courtesy: LGI REALTY- FLORIDA, LLC 904-449-3938
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ADDITIONAL INFORMATION

Welcome to the Summit model in Peach Crossings, a stunning brand-new home offering four bedrooms and two bathrooms with a spacious open-concept design. Featuring high ceilings, this home is bright and airy, providing a welcoming atmosphere throughout. The master suite is a true retreat, offering a large bedroom that leads into a luxurious en-suite bathroom with a dual sink vanity and a step-in shower for a spa-like experience. The kitchen is both functional and stylish, with exceptional counter space and brand-new Whirlpool appliances, including a refrigerator, stove, dishwasher, and microwave. A spacious hall closet adds extra storage, keeping everything organized. The family room is perfect for movie nights, providing plenty of space for a comfortable sectional and a large entertainment setup. Whether it’s a movie marathon or a quiet evening, this room is designed for relaxation and family fun. Step outside to the lanai, a great place to enjoy the warm Florida evenings with family and friends. The home also features professional front yard landscaping, adding to its curb appeal. Located just a short walk from the children’s playground, this home is perfect for families. In addition to being close to shopping, dining, and local attractions, the community offers access to top-rated Polk County schools and a picnic area for residents to enjoy. With all upgrades included, this home is ready for you to move in! Schedule your showing today!

Beds:
4
Baths:
2.00
Sq.Ft.:
1,863
Status:
Active
MLS#:
TB8364813
Type:
Single Family
Subdivision:
Peach Crossings
Lot size:
0.1 Acres
Year built:
2025
A broker reciprocity listing Courtesy: LGI REALTY- FLORIDA, LLC 904-449-3938
View additional info

ADDITIONAL INFORMATION

Welcome to the Summit model in Peach Crossings, a beautiful brand-new home featuring four bedrooms and two bathrooms with an inviting open-concept design. This home boasts high ceilings, enhancing the spacious and airy feel throughout. The master retreat is a true sanctuary, offering a generously sized bedroom that connects to a luxurious en-suite bathroom with a dual sink vanity for added convenience and a step-in shower for a spa-like experience. The kitchen is designed for both function and style, featuring exceptional counter space and brand-new Whirlpool appliances, including a refrigerator, stove, dishwasher, and microwave. A spacious hall closet provides extra storage, keeping everything organized. The family room is the perfect space for cozy movie nights, with ample room for a large sectional and entertainment setup. Whether it’s a movie marathon or a casual night in, this space is designed for relaxation, laughter, and quality time with loved ones. Step outside to the lanai, with no rear neighbors, an ideal spot for enjoying warm Florida evenings with family and friends. The home also features professional front yard landscaping, adding to its curb appeal. This home is Located in the heart of Polk County, Peach Crossings offers the best of lake living with easy access to shopping, dining, and top attractions. Families will love the highly-rated Polk County schools, and the community features a children’s playground and picnic area for added enjoyment. With all upgrades included, this home is move-in ready! Schedule your showing today!

Beds:
4
Baths:
2.00
Sq.Ft.:
1,564
Status:
Active
MLS#:
O6290604
Type:
Single Family
Subdivision:
Villamar Ph 5
Lot size:
0.1 Acres
Year built:
2026
A broker reciprocity listing Courtesy: NEW HOME STAR FLORIDA LLC 407-803-4083
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ADDITIONAL INFORMATION

Pre-Construction. To be built. Discover the Ventura in VillaMar – A Thoughtfully Designed Smart Home in Winter Haven Located in the beautiful VillaMar community in Winter Haven, the Ventura offers the perfect blend of modern design, comfort, and convenience. Nestled in a prime location, VillaMar provides stunning lake views and resort-style amenities, making it an ideal place to call home. The Ventura is a stunning new home design offering up to 1,562 square feet of beautifully finished living space, all on a single level. As you step onto the inviting covered patio and into the foyer, you’ll find three secondary bedrooms and a full bath conveniently located away from the great room and master suite, ensuring privacy and functionality. Designed with an open-concept layout, the Ventura creates an airy and spacious ambiance, seamlessly blending style and practicality. The stunning kitchen features a large island with quartz countertops, providing ample space for meal preparation and casual dining. Flowing effortlessly into the great room, this space is enhanced by four LED lights and an upgraded window, allowing natural light to fill the home. Cordless blinds throughout provide a sleek, modern touch while enhancing safety and ease of use. Tucked away at the rear of the home, the spacious private master suite serves as a true retreat, complete with a walk-in closet, dual sinks, and a walk-in shower, offering both comfort and convenience. Built for modern convenience, the Ventura comes equipped with cutting-edge smart home features, including a Ring Video Doorbell, Smart Thermostat, and Keyless Entry Smart Door Lock, allowing you to control security and comfort with ease. DEAKO light switches add customizable lighting options, enhancing your living experience. Throughout the main living areas, durable ceramic tile flooring adds a touch of elegance, while plush carpeting in the bedrooms ensures comfort. Outside, a professionally designed landscape and irrigation system keep your yard looking pristine year-round. The home is also built with architectural shingles, ensuring both durability and curb appeal. The two-car garage offers plenty of room for vehicles, with additional space for a workshop or extra storage. Experience the best of Winter Haven living in VillaMar with the Ventura—a home designed for modern lifestyles and unforgettable memories.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,440
Status:
Active
MLS#:
P4934135
Type:
Manufactured Home
Subdivision:
Oakwood Estates
Lot size:
0.08 Acres
Year built:
1983
A broker reciprocity listing Courtesy: COLDWELL BANKER REALTY 863-294-7541
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ADDITIONAL INFORMATION

Spacious is the best word to describe this home. The home has 1440 sf plus a side porch for additional entertaining space. The home has two living areas and a wonderfully functional kitchen. The primary bedroom and bath allow for lots of space with two closets for his and hers clothes. The main bathroom is directly off the guest bedroom, making it convenient for guests. The hot water heater was replaced in 2024, roof in 2020 and HVAC in 2015. So this home is ready for it's new owners. The windows are a newer double pane for energy efficiency and the sliding patio door is also newer. The furnishings you see when you view the home will remain in the home. Oakwood Estates, a 55+ community, offers many opportunities and amenities. You can be as busy as you want, or just sit back and watch the world go by. Check this home out today!!

Beds:
2
Baths:
2.00
Sq.Ft.:
1,691
Status:
Active
MLS#:
L4950037
Type:
Single Family
Subdivision:
Lake Dexter Moorings
Lot size:
0.14 Acres
Year built:
1990
A broker reciprocity listing Courtesy: COLDWELL BANKER REALTY 863-294-7541
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ADDITIONAL INFORMATION

PRICE REDUCTION!! Discover this stunning lakefront gem on Lake Dexter—a peaceful 166-acre lake in southeast Winter Haven, accessible only through private community ramps. Perfect for fishing, waterskiing, or simply cruising, Lake Dexter has something for everyone. Located in the highly sought-after Lake Dexter Moorings Community, residents enjoy a sparkling community pool and private boat ramp. This beautifully maintained 2BD/2BA home is move-in ready with numerous recent updates, including a new roof (2022), modern water treatment system, and backup generator for peace of mind. The spacious kitchen features gorgeous cabinetry and newer appliances, while the cozy living room invites you to unwind by the fireplace. Step outside to the large, screened patio, perfect for year-round relaxation, and enjoy elegant newer flooring throughout the home. Don’t miss this rare opportunity for lakefront living in one of Winter Haven’s most desirable communities. ?? Call today to schedule your private viewing!

Beds:
2
Baths:
2.00
Sq.Ft.:
826
Status:
Active
MLS#:
O6289336
Type:
Condo
Subdivision:
Park Lake
Lot size:
0.01 Acres
Year built:
1984
A broker reciprocity listing Courtesy: FOLIO REALTY LLC 407-917-0241
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ADDITIONAL INFORMATION

UPDATED condo. NEW Bathroom Vanity & fresh Paint throughout. Price Improvement & Great opportunity to add your personal style to this 2 bedroom 2 full bath condo in Park Lake. Located on the 2nd floor close to the elevator with tremendous rental returns. Luxury Vinyl flooring in main living area & primary bedroom. Gas range & Water Heater. Ceiling fans throughout...Roof 2021...Washer/Dryer included with private laundry closet. NEW Dishwasher & Gas Stove just installed. NEW 5T 14 Seer AC just installed. Wet Bar...Terrific view from the back of the newly renovated baseball complex. Walking distance to restaurants & NEWLY RENOVATED BASEBALL COMPLEX. View of Lake Lulu with lake access for fishing off the dock. Primary bedroom offers a walk-in closet & natural light. This building offers an elevator & stairs as well as 1 dedicated parking space. Priced to sell!

Beds:
3
Baths:
3.00
Sq.Ft.:
2,118
Status:
Active
MLS#:
P4934004
Type:
Single Family
Subdivision:
Hanna Sub
Lot size:
0.47 Acres
Year built:
1954
A broker reciprocity listing Courtesy: COLDWELL BANKER REALTY 863-294-7541
View additional info

ADDITIONAL INFORMATION

LAKE FRONT PROPERTY FOR SALE ON THE CHAIN OF LAKES ON LAKE HOWARD!!! This chain of lakes has 20 connecting lakes. If you enjoy water sports, fishing or just time on the water this lake front property may be a perfect fit for you. This Home has a detached Mother In-Law Suite, Fire place, New flooring, New split AC unit and a Updated Bathroom. If there is NO NEED for a Mother In-Law Suite it could be used as a extra bedroom or Bonus room. The Home itself has a nice Lake View from the Living Room. The main Home has 2 Full Bathrooms along with a Half Bath an Oversized Garage with plenty of Storage. The Kitchen has been updated with New cabinets, Granite Countertops, New Paint on Inside and a Updated Guest Bathroom. In Ground Irrigation and Plenty of Yard. All Room measurements are Approximate. This home really could be yours come and see!!!

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Andrea D. Conner, License # BK3437731, Xome Inc., License CQ1043756, [email protected], 844-400-XOME, 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067

All listings featuring the BMLS logo are provided by BeachesMLS, Inc. This information is not verified for authenticity or accuracy and is not guaranteed. Copyright © 2026 BeachesMLS, Inc.


Andrea Conner, License #BK3437731, Xome Inc., License #1043756, [email protected], 844-400-9663, 750 State Hwy 121 Bypass, Suite 100, Lewisville, TX 75067


Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of {{last updated}}. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Properties displayed may be listed or sold by various participants in the MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Copyright 2026, My Florida Regional MLS DBA Stellar MLS.



Winter Haven Real Estate

Winter Haven is located in Florida. Winter Haven, Florida has a population of 48,707. Winter Haven is less family-centric than the surrounding county with 26.09% of the households containing married families with children. The county average for households married with children is 26.62%.

The median household income in Winter Haven, Florida is $50,842. The median household income for the surrounding county is $55,099 compared to the national median of $69,021. The median age of people living in Winter Haven is 41 years.

Winter Haven Weather

The average high temperature in July is 92.5 degrees, with an average low temperature in January of 49.7 degrees. The average rainfall is approximately 51.2 inches per year, with 0 inches of snow per year.

Winter Haven Map

Winter Haven Real Estate Market Conditions

  • Median sales price

    $277,000
    25.4%
    change since last quarter
  • # Active listings

    927
    30-day change

Winter Haven Schools and Demographics

Education near Winter Haven, FL

City County
High School Graduates 88.28 86.36
College Degree - 2 year 10 9.74
College Degree - 4 year 19.99 21.01
Graduate Degree 4.94 5.22
Expenditures per Student 10,984 10,984
Students per Teacher 17.8 17.8

Elementary Schools near Winter Haven, FL

Grades Students P/T Ratio ZIP
Chain of Lakes Elementary School PK - 05 1,077 17.4 33884
Eagle Lake Elementary School PK - 05 473 15.8 33839
Elbert Elementary School PK - 05 638 15.6 33881
Frank E. Brigham Academy KG - 05 527 15.5 33880
Fred G. Garner Elementary School PK - 05 646 13.7 33881
Garden Grove Elementary School PK - 05 562 15.2 33884
Hartridge Academy KG - 05 237 18.2 33881
Highland City Elementary School PK - 05 428 13.8 33846
Inwood Elementary School PK - 05 412 15.3 33880
Jewett School of the Arts PK - 08 738 15.1 33881
John Snively Elementary PK - 05 467 15.6 33880
Lake Shipp Elementary School PK - 05 550 17.2 33880
Pinewood Elementary School PK - 05 678 14.7 33839
Wahneta Elementary School PK - 05 502 16.2 33880
Winter Haven Head Start PK - PK 35 17.5 33881

Middle Schools near Winter Haven, FL

Grades Students P/T Ratio ZIP
Denison Middle School 06 - 08 842 15.9 33880
Jewett Middle Academy Magnet 06 - 08 606 18.4 33881
Westwood Middle School 06 - 08 821 15.5 33881

High Schools near Winter Haven, FL

Grades Students P/T Ratio ZIP
Chain of Lakes Collegiate High School 11 - 12 291 32.3 33881
Lake Region High School 09 - 12 1,892 19.9 33839
New Beginnings High School 07 - 12 382 27.3 33881
Polk State College Collegiate High School 11 - 12 281 40.1 33881
Winter Haven Senior High School 09 - 12 1,953 22.2 33880

Ungraded Schools near Winter Haven, FL

Grades Students P/T Ratio ZIP
Ridge Teen Parent Program 06 - 12 71 33881
Winter Haven Pace 01 - 12 5 33880

Demographics near Winter Haven, FL

City County
Neighborhood Type Suburban
Population 48,707 713,148
Population Density 1,520 397
Median Age 41 40.1
People per Household 2.7 2.8
Median Household Income 50,842 55,099
Average Income per Capita 27,296 27,909

Real estate near Winter Haven