Winter Haven Homes For Sale & Real Estate - 805 homes

Remarks: Under contract-accepting backup offers. Discover the perfect blend of modern living and convenience in this brand new 3-bedroom, 2-bathroom home located in the heart of Winter Haven, just minutes from the serene shores of Lake Hartridge. Best of all, there’s NO HOA to worry about! As you step inside, you’ll be greeted by a bright and airy open floor plan that flows seamlessly throughout the home. The luxury vinyl plank flooring adds both elegance and durability, making it a great choice for busy households. The heart of the home is undoubtedly the beautiful kitchen, which features stainless-steel appliances, quartz countertops, and plenty of cabinetry to store all your cooking essentials. The kitchen design allows for easy interaction with guests in the spacious living room, ensuring you never miss a moment while entertaining. Retreat to the primary bedroom, a sanctuary designed for relaxation. This inviting space comes complete with a generous walk-in closet and a luxurious ensuite bathroom, featuring dual sinks and a modern walk-in shower—providing a perfect spot to unwind after a long day. The two additional bedrooms are thoughtfully designed with equal sizing and each boasts a walk-in closet, ideal for family members or guests. The second bathroom, conveniently located near the entrance of the home, includes a shower and tub combination, offering both comfort and functionality. Situated in the heart of WinterHaven, this home places you in close proximity to a variety of retailers, restaurants, and shops, ensuring you have everything you need right at your fingertips. Plus, the adjacent home is also available for sale and currently under construction, offering a unique investment opportunity. Don’t miss your chance to own this exceptional new home in Winter Haven—schedule a tour today and envision the possibilities!

Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (863-701-2350)

Listing Agent: John Hubbert, Jr (863-243-4024)

Remarks: Priced to Sell! Fully furnished! Excellent opportunity in the desirable 55+ community of Garden Grove Oaks where you own your land and enjoy low HOA fees. Located at 6133 Grand Oaks Dr SE in Winter Haven, this home offers a great layout with spacious living and dining areas and plenty of natural light. The kitchen provides ample cabinet and counter space, and the primary bedroom includes a private en-suite bath. A second bedroom and bath provide space for guests or a home office. Enjoy relaxing on the screened porch overlooking the peaceful community setting.This home is being sold AS-IS and offers a fantastic opportunity for buyers looking to update and add their own personal touches. Garden Grove Oaks is a well-maintained community conveniently located near shopping, dining, medical facilities, and Winter Haven’s Chain of Lakes with easy access to major highways to Orlando and Tampa.Great value and priced for a quick sale — don’t miss this opportunity!

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

Listing Agent: Anita Lowe (863-269-6461)

Remarks: This home is a MUST SEE? You will find many updates in this home from the beautiful granite counters in the kitchen and new kitchen cabinets to the remodeled bathrooms. All flooring is either ceramic or vinyl flooring. The Singled roof is approximately 11 years old and the ac was installed in 2025. The water heater was installed in 2024. This home will be sold mostly furnished. If that isn't enough, from the carport area there is a beautiful view of the lake and lakeside amenities. Oakwood Estates is a very active 55+ community offering many amenities including two pools, two clubhouses, miniature golf, tennis courts, shuffleboard and more. You can be as busy as you want, or just sit back and enjoy peaceful Florida living. Visit the Oakwood website for more info on the community and to see the governing docs. https://www.oakwoodmhp.com/

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

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

Remarks: ***Invvestor Special*** Welcome to this 2 bedroom 1 bath home. It is in need of some work but not out of range for the right do it your self investor. It is situated on .6 acres of land with room on the back of the lot for a garden, chickens or storage building. This property is located in Winter Haven and is close to everything you need.

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

Listing Agent: Tony Insua Jr. (863-221-0656)

Remarks: Rare opportunity to own a spacious two-story home in the highly sought-after Villamar community—homes like this don’t last long. Designed with an open-concept layout perfect for today’s lifestyle, this home offers a seamless flow from the kitchen—featuring quartz countertops, modern appliances, refrigerator, and breakfast nook—into a large, inviting great room ideal for entertaining. Upstairs, retreat to a private primary suite with walk-in closet and en-suite bath complete with dual vanity and tiled shower, along with three additional bedrooms, a full bath, and the convenience of second-floor laundry with washer and dryer included. Enjoy modern living with built-in smart-home features including a Ring Video Doorbell, smart thermostat, keyless entry, and DEAKO switches. Located in Villamar, residents enjoy access to resort-style amenities including a pool, clubhouse, playground, dog park, scenic walking paths, ponds, and lush green spaces. Additional highlights include professional landscaping, a covered entry porch, architectural shingles, and a builder warranty for added peace of mind.

Listing is courtesy of: UNITED REALTY GROUP INC (954-450-2000)

Listing Agent: Keisha Weir (754-204-5431)

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: THIS HOME QUALIFIES FOR 0% DOWN !! Welcome to 3025 Silverado Terrace, a desirable 2-bedroom, 2-bath home in the highly sought-after Cypresswood Golf & Country Club community. This gated neighborhood offers 24-hour security and resort-style amenities, including a sparkling pool with poolside service, tennis courts, a clubhouse with dining and entertainment, fitness center, and pro shop. It’s also perfect for walking or biking through beautifully maintained grounds. This home enjoys serene views of the golf course, pond, and stunning sunsets—plus a front-row seat to Legoland’s nightly fireworks. Inside, you’ll find cathedral ceilings, abundant natural light, a split-bedroom layout, and an eat-in kitchen. The laundry room is conveniently located off the kitchen. The screened lanai, featuring new lighting and a ceiling fan, is the perfect spot to enjoy your morning coffee or relax while taking in the wildlife and golf course views. Recent updates include a newer roof (2024), HVAC system, and upgraded electrical, giving you peace of mind. Cypresswood is one of Winter Haven’s most established and picturesque communities, making this home a rare opportunity.

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

Listing Agent: Malak Hassani Benbachir (863-624-7266)

Remarks: LAKEFRONT LIVING WITH NO HOA Welcome to 3334 Fox Ridge Drive — a beautifully maintained 3-bedroom, 3-bath pool home perfectly situated on over half an acre along the shores of Lake Fox in Winter Haven. Enjoy the peace and privacy of a spacious lot with no HOA, while still being just minutes from shopping, dining, and schools. Step inside to find a bright, open layout designed for both comfort and entertaining. The kitchen overlooks the living area and pool, featuring plenty of cabinetry and counter space. Each bedroom offers generous closet storage and natural light, while the primary suite provides serene lake views and a private ensuite bath. Out back, unwind in your screened pool area or relax under the covered lanai—perfect for outdoor gatherings. The expansive backyard slopes gently toward Lake Fox, offering endless possibilities for fishing, paddleboarding, or simply soaking in the view. Additional highlights include:     •    Over ½ acre lot     •    Private lake frontage on Lake Fox     •    Screened-in pool with lanai     •    No HOA or CDD fees     •    Convenient SE Winter Haven location This is a rare opportunity to enjoy lakefront living with freedom and space—schedule your private showing today!

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

Listing Agent: Brandy Waters (863-268-9585)

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: Short Sale. $50,000 PRICE REDUCTION! Welcome to your perfect retreat in this exclusive gated community, where tranquility meets convenience! Enjoy easy access to shopping, dining, and the exciting attractions of Winter Haven, including Legoland Theme Park, all just minutes away. This charming three-bedroom, two-bathroom home features a modern open-concept layout and a split bedroom design for added privacy. You'll love the luxury vinyl flooring throughout the living areas, with cozy carpet in the bedrooms. Step outside to your large, fully fenced backyard—perfect for relaxation without any rear neighbors. Unwind in your spacious screened-in lanai, ideal for enjoying the outdoors year-round! Additional highlights include an 8 x 5 fireproof storage closet in the garage, providing peace of mind for your valuables, as well as a well-maintained irrigation system and beautiful landscaping that enhances the curb appeal. With quick access to the Polk Parkway and Interstate 4, Central Florida adventures are at your fingertips. Don’t miss out on this fantastic opportunity—schedule your showing today!

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

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

Remarks: Welcome to 233 Temple Cir W, a spacious manufactured home perfectly positioned on a private .60-acre lot in the heart of Winter Haven, offering peaceful surroundings, room to breathe, and the freedom of no HOA restrictions. Set back from the road with no rear neighbors, this property provides a rare sense of privacy while still being conveniently close to everyday amenities. The home features two porches, both front and rear, creating ideal spaces to enjoy Florida’s year-round outdoor lifestyle, whether sipping morning coffee, entertaining guests, or relaxing in the evening breeze. Inside, you’ll find a generously sized 3-bedroom, 2-bathroom floor plan filled with potential. The home is ready for a new owner’s personal touch, making it an excellent opportunity for buyers seeking space, value, and the ability to customize a property to their own style. The expansive lot offers endless possibilities for gardening, outdoor living areas, additional storage, or recreational use, a rarity in today’s market. Located in Winter Haven, one of Central Florida’s fastest-growing communities, residents benefit from a city experiencing significant residential, commercial, and economic expansion. The area has seen steady population growth along with new housing, retail, and infrastructure investments, reinforcing its reputation as a city focused on long-term quality of life and opportunity. Winter Haven’s central location along the I-4 corridor places Tampa and Orlando within easy reach while maintaining a more relaxed pace and affordable lifestyle. The city is widely known for its scenic Chain of Lakes, vibrant downtown district, and family-friendly attractions, including LEGOLAND® Florida Resort, which continues to draw visitors and economic activity to the region. Outdoor enthusiasts enjoy boating, fishing, waterfront parks, and community events that contribute to the area’s welcoming atmosphere. Dining options nearby range from local favorites and downtown cafés to popular waterfront restaurants, while everyday conveniences are just minutes away. Higher education opportunities are easily accessible with Polk State College nearby, along with proximity to Southeastern University and Florida Southern College in neighboring Lakeland, adding educational and cultural depth to the region. Winter Haven’s continued investment in logistics, industry, and job creation, including major developments at the Central Florida Integrated Logistics Park, further strengthens the local economy and supports ongoing growth throughout Polk County.

Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (863-701-2350)

Listing Agent: Andrew Fearn (863-812-1755)

Remarks: BETTER THAN NEW!!! Why wait to build when you can move into this HIGHLY UPGRADED, MAINTENANCE FREE villa in the 55+ GATED COMMUNITY of Vienna Square, centrally located in Winter Haven, FL. Before entering this beautiful residence, you will notice the BRICK PAVERED driveway/walkway leading through the MATURE LANDSCAPE and CUSTOM LIGHTING to the front SCREENED LANAI. Walk right into this very OPEN FLOORPLAN with HIGH CEILINGS and SPLIT BEDROOM CONCEPT. The kitchen is a CHEF'S DREAM, featuring UPGRADED STAINLESS APPLIANCES, IMPRESSIVE WINE FRIG., and BREAKFAST BAR. The CASCADING WATERFALL EDGE QUARTZ COUNTERTOPS add a MODERN, ELEGANT and LUXURIOUS focal point to this AMAZING KITCHEN!!! The adjoining great room is very spacious and overlooks the rear SCREENED LANAI with a view of the pond. The primary en-suite will not disappoint which also features QUARTZ COUNTERTOPS and an UPGRADED WALK-IN SHOWER with GLASS DOOR. CUSTOM PLANTATION SHUTTERS in the kitchen and bedrooms ensure you have the privacy you deserve! Don't forget about the second bathroom that has also been UPGRADED with QUARTZ COUNTERTOPS as well. This residence is truly TURN-KEY and one of the most WELL KEPT, ONE-OWNER homes you'll find anywhere. The reasonable monthly HOA dues include: ROOF REPLACEMENT, EXTERIOR PAINTING, YARD MAINTENANCE, LAWN IRRIGATION, and INTERNET/TV PACKAGE! Enjoy the other amenities including, but not limited to: pool/hot tub, tennis/pickle ball, gym, craft room, billiard room, movie room, and large meeting room with remodeled kitchen area. This wonderful property is in close proximity to medical, restaurants, shopping, worship, and LEGOLAND, FL. Winter Haven is well-known for it's beautifully interconnected lakes and being centrally located between the Tampa International and Orlando International Airports.

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

Listing Agent: Bryan Dicks (863-287-7851)

Remarks: Welcome to maintenance-free living nestled in the thriving community of Cypresswood Golf and Country Club that offers an unparalleled lifestyle and peace of mind with a 24-hour guard at the gated entrance, perfect for year-round living or a worry-free seasonal getaway. This second-floor condo boasts a world of comfort and convenience with the A/C having been replaced entirely in 2024, giving you one less worry, tons of storage in generously-sized walk-in closets that both bedrooms offer as well as additional linen storage in the hallway and primary bedroom that will keep your space organized and clutter-free effortlessly. Dive into relaxation and fun at the community pool or host gatherings, socialize with neighbors, or simply unwind in the inviting communal spaces of the clubhouse. The on-site restaurant offers convenient and flavorful dining options, perfect after a tennis or pickleball match on the community's courts or day of golf on Cypresswood's 18-hole championship course. The low monthly HOA fee includes all exterior maintenance, landscaping, pest control, trash collection, and the pool and tennis amenities. Residents also enjoy a discount on daily golf and annual memberships! Minutes from Highway 27 and the I-4 corridor, Winter Haven's very own Legoland Florida Resort, the Polk Parkway, and in the center of a thriving community with many convenient grocery, restaurant, shopping, and commuting options. Schedule your private showing today, and make this lovely condominium yours.

Listing is courtesy of: JOHN WOOD REALTY, INC. (863-324-9663)

Listing Agent: Kayly Malinas, Pa (863-258-1426)

Remarks: ***JUST REDUCED*** All Ages Welcome! Immaculately kept patio home in Orchid Springs featuring exceptional wooded and pasture views—truly a buyer’s paradise. The wrap-around driveway offers abundant parking for friends, family, and guests, while the serene surroundings set the tone for this lovely residence. Inside, an open and spacious floorplan makes entertaining effortless. This patio home stands out from others in the community thanks to its fully enclosed additional living area—ideal for a home office, reading room, or creative space. A split floorplan ensures maximum privacy for visitors, with the primary suite tucked at the back of the home and the guest bedroom positioned on the opposite side, separated by two living areas, the kitchen, and the dining room. The primary suite boasts an enormous walk-in closet and an ensuite bathroom with tub/shower combo. Step into your own tropical oasis in the expansive Florida Room, which spans the entire depth of the home and offers unparalleled views of local wildlife. A built-in wet bar adds to the room’s appeal, making it perfect for relaxing evenings or entertaining. Pet owners will appreciate the small fenced area conveniently located just outside. An additional screened-in space—almost as large as the Florida Room—provides yet another area to enjoy the peaceful setting. Schedule your showing today—you’ll be glad you did!

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

Listing Agent: Cynthia Cole (863-514-4461)

Remarks: LOVELY FULL-SIZE HOME ON A CORNER LOT. Step inside and you'll find a generous family room ideal for relaxing and gathering, a formal living room with soaring ceilings that create an open and airy feel, and a formal dining room. THE HOUSE HAS MANY UPDATES, INCLUDING BUT NOT LIMITED TO PAINTING AND FLOORING. THE KITCHEN HAS BEEN BEAUTIFULLY RENOVATED, AND THE BATHROOM IS CLEAN AND REFRESHING.. Living here means less work, more play. With a low monthly maintenance fee, you’ll enjoy access to a sparkling community pool and a clubhouse. Orchid Springs is all about tranquility with quick access to local markets, dining, medical facilities, Legoland, and the Winter Haven Chain of Lakes. Don’t miss your chance to own this cheerful, easy-care home in one of Winter Haven’s most loved communities. Schedule your showing today and step into the Florida lifestyle you’ve been WAITING FOR!

Listing is courtesy of: TINA MARIE LLC (407-448-5388)

Listing Agent: Tina Marie (863-332-2612)

Remarks: Discover this must-see Ruby home. Included features: an inviting covered entry; a well-appointed kitchen offering 42" white cabinets, a walk-in pantry and a center island; an elegant dining room; a spacious great room; a lavish primary suite showcasing a generous walk-in closet and a private bath; a laundry and a covered patio. This could be your dream home! *Take advantage of special financing on quick move-in homes OR buy a to-be-built home and enjoy up to $20,000 in Flex Funds toward homes that can close in a timely manner! Options may vary by community, and offers are available on select homes on a first-come, first-served basis. Contact builder for more information!

Listing is courtesy of: AXEN REALTY, LLC (480-399-1218)

Listing Agent: Stephanie Morales, Llc (407-399-2055)

Remarks: This thoughtfully designed Slate home opens with two bedrooms flanking a full hall bath. Beyond the entry, you’ll find an open layout with a dining nook, a great room with access to an inviting covered patio, and a kitchen with a center island, walk-in pantry and abundant cabinetry. The owner’s suite is nearby, offering a generous walk-in closet and a private bath with optional dual sinks, a shower and a separate soaking tub. A laundry room and a fourth bedroom with its own private bath complete the home. *Take advantage of special financing on quick move-in homes OR buy a to-be-built home and enjoy up to $20,000 in Flex Funds toward homes that can close in a timely manner! Options may vary by community, and offers are available on select homes on a first-come, first-served basis. Contact builder for more information!

Listing is courtesy of: AXEN REALTY, LLC (480-399-1218)

Listing Agent: Stephanie Morales, Llc (407-399-2055)

Remarks: An inviting covered entry welcomes guests to this inspired Tarragon home. Pass two bedrooms, a shared bath, a flex room and a laundry on your way to a spacious great room with an adjacent covered patio. The well-appointed kitchen boasts a center island, a walk-in pantry and a dining nook. Showcasing a generous walk-in closet and an attached bath with double sinks. An additional bedroom and bathroom round out this inspired plan. *Take advantage of special financing on quick move-in homes OR buy a to-be-built home and enjoy up to $20,000 in Flex Funds toward homes that can close in a timely manner! Options may vary by community, and offers are available on select homes on a first-come, first-served basis. Contact builder for more information!

Listing is courtesy of: AXEN REALTY, LLC (480-399-1218)

Listing Agent: Stephanie Morales, Llc (407-399-2055)

Remarks: Discover this must-see Tourmaline home. Included features: an inviting covered entry; an expansive great room; a well-appointed kitchen offering 42" cabinets, quartz countertops, a roomy pantry, a center island and an adjacent dining area; a beautiful primary suite showcasing an immense walk-in closet and a private bath; a convenient laundry; an airy loft; a storage area and a covered patio. This home also offers ceiling fan prewiring in select rooms. *Take advantage of special financing on quick move-in homes OR buy a to-be-built home and enjoy up to $20,000 in Flex Funds toward homes that can close in a timely manner! Options may vary by community, and offers are available on select homes on a first-come, first-served basis. Contact builder for more information!

Listing is courtesy of: AXEN REALTY, LLC (480-399-1218)

Listing Agent: Stephanie Morales, Llc (407-399-2055)