Winter Haven Homes For Sale & Real Estate - 1049 homes

Remarks: R E D U C E D ... YOU'LL LOVE THIS MAINTENANCE FREE LIFESTYLE IN DESIREABLE VIENNA SQUARE , LOCATED IN WINTER HAVEN. THIS VILLA IS MOVE IN READY. THIS 2BR-2BA VILLA OFFERS AN OPEN GREAT ROOM DESIGN WITH SPLIT BEDROOMS. THE MASTER ENSUITE HAS WALK IN CLOSET WITH STEP IN SHOWER FOR CONVENIENCE. THE 2ND BEDROOM OFF FRONT ENTRANCE OF HOME HAS AN ADJOINING BATH WITH TUB AND SHOWER. DON'T WAIT, THIS GREAT GATED COMMUNITY HAS CLUBHOUSE, FITNESS CENTER, POOL, TENNIS COURTS AND OFFERS SO MUCH TO YOUR OVER 55 LIFESTYLE. CONVENIENT TO SHOPPING, RESTAURANTS AND ONLY MINUTES TO DOWNTOWN WITH SOMETHING FOR EVERYONE. THIS VILLA HAS AN OPEN FLOOR PLAN WITH HIGH CEILINGS, CEILING FANS, CERAMIC TILE IN THE LIVING AREA AND CARPETING IN THE BEDROOMS. RELAX ON YOUR ENCLOSED LANAI OVERLOOKING THE SERENE ATMOSPHERE OF THE PEACEFUL WOODED AREA BEHIND YOUR UNIT WITH NO REAR NEIGHBORS. THE MONTHLY HOA FEE INCLUDES EXTERIOR PAINT, ROOF, IRRIGATION WATER, LAWN MAINTENANCE AND RECENT ADDITION OF SPECTRUM TV/WIFI SERVICE. THIS VILLA HAS BEEN CLEANED AND READY FOR YOUR MOVE.

Listing is courtesy of: FLORIDA HOME CHOICE REALTY (863-412-2727)

Listing Agent: Glenda Pruitt (863-412-2727)

Remarks: Discover the charm of this delightful 3-bedroom, 2-bath home located in the maintenance-free, 55+ gated community of Traditions at Lake Ruby. Thoughtfully designed for comfort and functionality, this home offers an inviting retreat for relaxed, worry-free living. Upon arrival, you’re welcomed by a spacious covered entrance enhanced with a leaded glass door and transom window. Inside, the eat-in kitchen features 42" maple wood cabinetry, Corian countertops, and a closet pantry for added storage. A breakfast bar and breakfast nook provide ample seating, making the space ideal for both everyday living and entertaining. The spacious great room showcases triple sliding glass doors that open to the oversized screened-in lanai, seamlessly extending the living space outdoors. The open-concept design also includes a formal dining room and formal living room, both accented with high ceilings and decorative niches that add architectural interest. The primary bedroom suite serves as a luxurious retreat, featuring a sitting area with patio access and dual walk-in closets with overhead luggage shelving for premium storage. The en-suite bathroom is well appointed with a comfort-height double-sink vanity, linen closet, seated walk-in shower, private water closet, and a relaxing garden tub. Outdoor enjoyment is effortless on the generously sized screened-in lanai, offering a serene space to unwind and enjoy the Florida lifestyle. Additional amenities include, a Laundry Room with washer, dryer, and utility sink, Honeywell Thermostat & Humidistat, Updated Architectural Shingle Roof 2020, Termite Bond, Paved Driveway & Walk Way, Gutters, Flood lights and Carriage Lighting, and a 2 Car Garage with Garage Door Opener. Residents of Traditions enjoy a plethora of amenities, including a lakefront clubhouse, a dock and boat ramp, a heated swimming pool and spa, a ballroom, billiards, meeting rooms, a library, a computer room, a craft room, a dog park, tennis and pickleball courts, basketball, bocce ball, shuffleboard, a fitness center, an aerobics studio, and much more. With its convenient location near shopping, restaurants, major routes, and Legoland, this home offers an exceptional lifestyle. Monthly HOA fees cover exterior house painting, cable, internet, lawn service, and clubhouse amenities, ensuring a worry-free living experience.

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

Listing Agent: Eileen Belanger (863-221-0229)

Remarks: Fresh on the market is this meticulously maintained and professionally updated 2 bedroom 2 bath villa located in the sought after "Enclave" neighborhood in Cypresswood, a gated golf community in SE Winter Haven. The open floor plan features an expansive kitchen with breakfast nook, spacious living/dining room combo, split bedrooms with ample closets, inside laundry area equipped with a washer and dryer, screened lanai and a 2 car garage with garage door opener. Per the owner, recent upgrades include removal of a wall separating the kitchen from the living area thereby creating a true open-concept living area, upgraded matching stainless kitchen appliances, flooring in the kitchen, living room, foyer, hall and 2 bedrooms, New granite counter-tops, sinks and faucets in the kitchen and both bathrooms, new LED lighting, New front entry door, new window treatments and fresh interior paint. This is truly a move-in-ready villa with quality upgrades that set it ahead of the competition. Come and enjoy the Florida Country Club Lifestyle in this low maintenance villa.

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

Listing Agent: Steven Smith, Pa (863-224-2297)

Remarks: One or more photo(s) has been virtually staged. Welcome to 6450 Hollyberry Lane in Brookhaven Village—a highly sought-after 55+ community where you own your land, making this a rare opportunity! This beautifully updated, move-in ready home features new luxury vinyl flooring (2025) and a bright, open layout perfect for everyday living and entertaining. The upgraded kitchen offers butcher block countertops, slide-out metal racks for added storage, and a brand-new dishwasher. Washer and dryer are included. Both bathrooms have been beautifully remodeled with modern finishes. Major updates include a new roof (Dec 2024), new HVAC system (2025) with ductwork and air handler, new windows (2025), and all-new screening, including the lanai with vinyl windows—perfect for enjoying Florida living year-round. The home is also fully replumbed with updated anchors and straps, including a vapor barrier that was installed about 4 years ago. The home also includes a great storage shed/workshop—ideal for hobbies or extra storage. Enjoy a super low HOA with access to a community pool and clubhouse, all in the heart of Winter Haven near shopping, dining, and lakes. Fully updated + land ownership + prime 55+ community—this one stands out. Schedule your showing today!

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

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

Remarks: Under Construction. BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. Feel at home with the Magenta, a single-story home with 3 bedrooms, 2 bathrooms, and a 2-car garage. This layout is a true gem, seamlessly blending modern comfort with Florida charm. Open concept living dazzles with luxury vinyl plank flooring throughout the main living areas. The kitchen, featuring quartz countertops, new stainless-steel appliances and ample storage overlooks the dining and living area. A dreamy, covered lanai, accessible through sliding glass doors, invites you to take full advantage of the Florida climate. The owner’s suite boasts double vanities, a walk-in shower and a substantial walk-in closet, while the additional bedrooms and full bathroom are located off the kitchen for added privacy. With a laundry room located off the foyer, a smart thermostat with voice control to maintain energy efficient living, and professionally curated landscaping, the Magenta is designed to make every day extraordinary. Our model home is located at 5512 Taverna Loop, Winter Haven, FL 33884. Take I-4 W to exit 55 for US 27-S. Continue on US 27-S then turn right onto Thompson Nursery Road. Continue straight on Eloise Loop Road then turn left onto Rialto Road. Continue straight and our model homes will be on your right. Images shown are for illustrative purposes only and may differ from actual home. Completion date subject to change.

Listing is courtesy of: CASA FRESCA REALTY (813-343-4383)

Listing Agent: Michael Human (813-343-4383)

Remarks: Short Sale. Over a half-acre fenced in lot with a 4 bedroom 2 1/2 bath home with an office or den. Large family room with a separate formal dining room. Eat in kitchen with 2 pantry's. New roof in 2017-2018 and a new air conditioner in 2019. Great location minutes from State Road 60 and close to all the dining and theme parks and spring baseball field in Winter Haven.

Listing is courtesy of: BROOKS REALTY GROUP LLC (813-653-7291)

Listing Agent: Erica Ranson (863-934-3510)

Remarks: Welcome to your next chapter in beautiful Winter Haven! This charming home offers the perfect blend of comfort, convenience, and value—an ideal opportunity whether you're a first-time buyer, downsizing, or looking to invest. Step inside to discover a bright and inviting layout designed for everyday living. The home features well-proportioned living spaces filled with natural light, creating a warm and welcoming atmosphere from the moment you walk in. The kitchen offers ample cabinet space and functionality, perfect for both casual meals and entertaining guests. Enjoy relaxing mornings or peaceful evenings in your private outdoor space, with room to personalize and make it your own. Nestled in a desirable location, this property provides easy access to shopping, dining, schools, and major roadways—making your daily commute and errands a breeze. Offered at just $210,000, this is an incredible opportunity to own a home in a growing and sought-after area of Winter Haven. Don’t miss your chance to make this property yours—schedule your private showing today!

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

Listing Agent: Belkis Garcia (407-994-5885)

Remarks: "Welcome to this charming 3-bedroom, 3-full-bath home nestled in the heart of Winter Haven! One of the bedrooms features a private entrance, making it perfect as an IN-LAW SUITE, home office/studio, or an income-producing rental opportunity. The spacious Florida room with screen enclosure is ideal for relaxing and entertaining, while the front screened porch adds extra curb appeal and a cozy outdoor living space. The generous backyard offers endless possibilities, plenty of room to add a pool, create your dream outdoor oasis, or simply enjoy the open space. A storage shed with electricity in the back provides additional convenience and storage. Enjoy pure, clean water throughout the entire home with a whole-house reverse osmosis filtration system. Located on a quiet dead-end street with no through traffic. No HOA, No CDD, low taxes, public water and sewer. Just minutes from Downtown Winter Haven, shopping, restaurants, and the beautiful Winter Haven Chain of Lakes. This home has so much to offer, don't miss this opportunity! Equal Housing Opportunity."

Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)

Listing Agent: Romina Peragine, Pllc (407-288-4595)

Remarks: Located in the desirable Harrington subdivision of Winter Haven, this beautifully single-family home offers the perfect blend of comfort, style, and value. Featuring 3 spacious bedrooms and 1 bathroom, the home showcases a bright open-concept layout ideal for modern living. The kitchen boasts granite countertops, stainless steel appliances, and ample cabinet space. Enjoy durable vinyl plank flooring throughout, generously sized bedrooms, and an abundance of natural light. Step outside to a large backyard, perfect for entertaining or relaxing. Conveniently situated near schools, parks, hospitals, dining, and entertainment. Priced to sell, schedule your showing today!

Listing is courtesy of: PREMIUM PROPERTIES R.E. SERVICE (407-380-2800)

Listing Agent: Hamid Dghirni (407-575-2891)

Remarks: Under contract-accepting backup offers. Under Construction. UNDER CONSTRUCTION:Welcome to the Residences at Winter Haven, a new single-family community focused on high-quality construction and modern design. This Key West model features a spacious three-bedroom, two-bathroom layout, centered around an open-concept living area. The interior is highlighted by premium finishes, including vinyl flooring and kitchen island with a fullwaterfall countertop. Large glass sliders lead out to a covered lanai, extending the living space and emphasizing a bright and functional environment.

Listing is courtesy of: KELLER WILLIAMS REALTY AT THE LAKES (407-566-1800)

Listing Agent: Rodrigo Gomes De Almeida (407-837-8173)

Remarks: Welcome to the next exciting chapter of your life in Lake Ashton, Central Florida’s premier 55+ active-adult community, where this immaculately maintained 3-bedroom, 2-bath home awaits. From the stone on the front elevation and bronze screened front entry to the 32’ x 18’ bronze screened veranda, the home impresses in every way. It is situated on a quiet cul-de-sac with views of a large pond and golf course in the distance. Step inside and you’ll immediately notice how clean, crisp, and welcoming the home feels, offering the perfect setting for both comfortable, relaxed living and gracious entertaining. Tasteful 18” x 18” tile flooring provides a uniform flow throughout the house. Plantation shutters adorn all windows. Six interior and 2 exterior veranda fans (total of 8 fans) are remote controlled, high-end Minka ceiling fans. The living room is accented by a coffered ceiling. The kitchen is highlighted by maple cabinets in Toffee color, and feature rollout trays, a corner lazy-susan, refrigerator cabinet and bump ups and bump outs. Identical cabinets and granite counters are found in both baths. The chef’s kitchen appliances are fingerprint resistant stainless steel. A large walk-in pantry offers ample storage space off the kitchen. Multiple pocket doors afford smooth flow room to room. The granite kitchen counters are accented with pendant lighting above the island. Identical cabinets with granite counter and desk/work area are located in the laundry room. Tranquil views from the living room, kitchen and expanded veranda are stunning. The master bath provides dual vanities, one with makeup station, and a spacious, glass-enclosed shower with custom fixtures. The garage features parking for two vehicles and a separate golf cart garage. In addition to the Green Home features built into the house, extra insulation was blown in the attic, providing added energy savings. Plus, the CDD DEBT IS PAID IN FULL on this property, saving you over $10,000! With so many outstanding features, this property must be seen in person to be appreciated. Beyond your doorstep, Lake Ashton’s unmatched amenities invite you to enjoy two championship 18-hole golf courses, a 26,000-square-foot clubhouse, a state-of-the-art health and fitness center, theater, pickleball courts, bowling alley, on-site restaurant, and so much more, ensuring an active and fulfilling lifestyle. This special property is the perfect blend of comfort, convenience, and community—schedule your private showing today and experience the very best of Florida living.

Listing is courtesy of: GLOBAL LIFESTYLE LLC (727-455-2709)

Listing Agent: Brad Kirwan (863-280-0390)

Remarks: Welcome to this refined sanctuary where timeless elegance meets Florida’s tranquil landscape. On a premium golf-adjacent lot within the guarded, gated community, 2964 Plantation Road blends gracious scale, luminous living and multi-generational flexibility in one seamless layout. Upon arrival, you are greeted by mature landscaping, a circular drive and side-entry access to a three-car garage, with stunning views of golf course fairways and water views. Enter inside to discover over 3,600 square feet of thoughtfully designed space. Formal living and dining rooms flow with grace and purpose, while a custom wet bar offers effortless entertaining. The split floor plan is crafted for privacy and connection. The primary suite is complete with dual vanities, walk-in closets, a garden tub, separate shower and private pool access. On opposite wing rests an en-suite bedroom, complete with full bath and independent access. Ideal for multigenerational living, guest privacy or an upscale in-law suite. Two additional bedrooms share a dual bath, while a half bath serves daily living or poolside use. Gourmet gathering begins in the kitchen, including a center island with gas range, generous counter space and views out toward the lanai. The breakfast nook offers a comfortable space for everyday dining, complemented by a nearby utility room and a flexible bonus room. Going outside, this home’s soul lives in its outdoor realm. A pool and spa, and a summer kitchen complete with built-in grill, sink and prep station, invite all-day alfresco living. A covered lanai frames those golf and pond vistas beautifully, offering shade and breeze for lounging or entertaining. Cypresswood is a full-amenity, guard-gated community with an 18-hole golf course, clubhouse with restaurant and lounge, tennis and pickleball, fitness/wellness center, and social programming. A $10,000 seller concession and one-year home warranty.

Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY (407-480-5014)

Listing Agent: Audrey Christman (516-547-5343)

Remarks: HUGE PRICE DROP! Welcome to this 2-bedroom, 1.5-bath condo in the desirable 55+ community of Winter Haven Harbour Apartments! This beautifully updated unit is modern, stylish, and completely move-in ready. Inside, the condo has been freshly painted and features luxury vinyl plank flooring in living areas and tile in kitchen and baths. Both bathrooms have been fully redone with modern finishes. The main bath features granite countertops and a stand-up shower with a built-in seat for added comfort and accessibility. The updated kitchen offers ample cabinetry, storage, and beautiful Granite counter tops. Important updates include a 2021 water heater and all new storm windows installed last year. An additional bonus is the private storage closet located next to the elevator; approximately 4x6 feet with floor-to-ceiling space. This active 55+ community offers a welcoming community center complete with a fitness center, library, and pool table. Outside near the heated pool, you’ll find a beautiful friendship garden with seating and a fire pit — the perfect spot to relax or gather with neighbors. Residents also enjoy pickleball courts, shuffleboard, and a grilling area ideal for social events and sunny Florida afternoons. Conveniently located near shopping, dining, medical facilities, and positioned between Tampa and Orlando. If you’re looking for updated, modern living in a vibrant and friendly 55+ community, this top-floor gem checks all the boxes. Schedule your private showing today!

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

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

Remarks: "OWNER WILL CREDIT UP TO $15,000 FOR THE COST OF ROOF REPLACEMENT AT CLOSING" FOR SALE: Attractive 3-Bedroom, 2-Bathroom Single-Family Home in Winter Haven! Discover your dream home in Osprey Pointe, where comfort meets style. This home is designed for modern living and entertaining. An open floor plan connects the eat-in kitchen and breakfast bar seamlessly to the living and dining areas, perfect for gatherings. Equipped kitchen with an eat-in area and a breakfast bar, ready for family meals and casual dining. Luxurious Master Suite: Retreat to your sanctuary featuring an elegant tray ceiling, a generous walk-in closet, double vanities in the primary bathroom, and a large glass shower stall. Enjoy the Florida lifestyle on your covered and screened rear porch. A paver driveway and an attached 2-car garage add to the curb appeal. The home includes inside laundry with washer and dryer hook-ups. Tiled common areas and bathrooms offer easy maintenance, while plush carpet in the bedrooms provides comfort. Exceptional Community Amenities: Live like you're on vacation every day! Enjoy access to a community clubhouse and a sparkling pool. Plus, take advantage of the private waterfront dock on beautiful Lake Ned for fishing and recreational activities. Lawncare included in HOA. Don't miss this opportunity to own a piece of paradise in Winter Haven. Schedule your showing today!

Listing is courtesy of: FLORIDA REALTY RESULTS LLC (407-498-3838)

Listing Agent: Debbie Browning (407-908-9060)

Remarks: Welcome to Fairview Village, an active 55+ gated waterfront community in Winter Haven. This charming 2-bedroom home offers peaceful canal and lake views, with private access to the water between Lake Hamilton and Lake Henry—perfect for boating and fishing. The community features a 99-year land lease and a low HOA fee of just $90 per month, which includes water and sewer. Residents enjoy a heated swimming pool with nearby restrooms and changing facilities, well-kept shuffleboard courts, coin laundry, and secure RV/boat storage available for an additional fee. The clubhouse serves as the heart of the community, hosting a full calendar of events such as breakfasts, dinners, bingo, cards, billiards, ping pong, dances, shuffleboard, horseshoes, and more. Please note that this is a no-pet community. Fairview Village offers an inviting, active lifestyle with beautiful waterfront surroundings.

Listing is courtesy of: WATSON REALTY CORP. (407-589-1600)

Listing Agent: Sandra Perry (978-273-0601)

Remarks: Welcome to your new home located directly across the street From Legoland. Home features community pool and tennis court and is ready for a new owner. Located in the central Hub of Winter Haven and close to anything any everything you need. Shopping, restaurants, schools.

Listing is courtesy of: FLORIDA HOMES REALTY & MTG (904-996-9115)

Listing Agent: Matthew Davis (321-848-2004)

Remarks: Under contract-accepting backup offers. Welcome to 3108 Buckeye Point Dr — where comfort meets convenience in the heart of Winter Haven. From the moment you arrive, this home invites you in with a layout designed for the way you truly live. With 4 bedrooms and 2 full bath and a brand new A/C system the living spaces feel open yet connected, creating an easy flow for both everyday routines and weekend gatherings. Natural light enhances the home’s warmth, while thoughtful design elements make each space feel intentional and livable. The kitchen serves as the hub of the home, seamlessly connecting to the main living areas — ideal for hosting, relaxing, or simply enjoying a quiet night in. The primary suite offers a private retreat, while additional rooms provide flexibility for guests, work-from-home needs, or hobbies. Step outside and imagine morning coffee, evening unwinding, and effortless Florida living in your own outdoor space. Located in a desirable Winter Haven community, you’ll appreciate the convenience to shopping, dining, medical facilities, schools, and major roadways — all while enjoying the feel of a tucked-away neighborhood setting. Homes that combine layout, location, and livability like this don’t stay available for long. Schedule your private showing and experience 3108 Buckeye Point Dr for yourself.

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

Listing Agent: Jp Phillips (863-670-7923)

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

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

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

Remarks: Welcome to 6086 Southern Oaks Drive SE, a beautifully updated and well- maintained, move in ready manufactured home located in the highly sought after 55+ community of Garden Grove Oaks where you OWN your Land and enjoy low HOA fees in a peaceful, well-maintained neighborhood. This home features two generously sized bedrooms and two full bathrooms. The primary suite boasts a private en-suite bath. Step into the living space filled with natural light featuring spacious living and dining areas ideal for entertaining or family gatherings. The kitchen has been updated and equipped with updated appliances (refrigerator and dishwasher are still under warranty), ample counter space and plenty of storage. Exterior doors have been replaced with wood doors. Roof was installed in 2018 A/C 2007. Laminate flooring throughout. The home has a shed and screened porch adding an additional 224 sq ft of space for storage or relaxing on the back screen porch. Enjoy community amenities, friendly neighbors and the convenience of being just minutes from local shopping, dining, medical facilities, and Winter Haven's world-famous Chain of Lakes. With access to major highways, commuting to nearby cities like Orlando or Tampa is a breeze. Don't miss the opportunity to make this beautifully maintained home in Garden Grove Oaks your new home! Schedule your private showing today and experience this property for yourself.

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

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

Remarks: Welcome to 6081 Southern Oaks Drive SE, a beautifully maintained manufactured home in the highly sought after 55+ community of Garden Grove Oaks where you OWN your Land and enjoy low HOA fees in a peaceful, well-maintained neighborhood. This home features two generously sized bedrooms and two full bathrooms. The primary suite boasts an extra-large walk in closet and private en-suite bath. Step into the living space filled with natural light featuring spacious living and dining areas ideal for entertaining or family gatherings. The kitchen is equipped with updated appliances, ample counter space and plenty of storage. The home has a beautiful Florida room with new windows. A new roof was installed in 2025. Vinyl plank flooring in main living area. Inside laundry room. Enjoy community amenities, friendly neighbors and the convenience of being just minutes from local shopping, dining, medical facilities, and Winter Haven's world-famous Chain of Lakes. With access to major highways, commuting to nearby cities like Orlando or Tampa is a breeze. Don't miss the opportunity to make this beautifully maintained home in Garden Grove Oaks your new home! Schedule your private showing today and experience this property for yourself.

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

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