Winter Haven Homes For Sale & Real Estate - 983 homes

Remarks: Under Construction. 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!

Listing is courtesy of: NEW HOME STAR FLORIDA LLC (407-803-4083)

Listing Agent: Charles Pennant (407-305-4317)

Remarks: Welcome to Garden Grove Oaks – a friendly, active 55+ community in beautiful Winter Haven and you OWN THE LAND! This well-maintained 2-bedroom, 2-bathroom manufactured home with a bonus office/den and Florida room offers the perfect blend of comfort, functionality, and easy Florida living. Step inside and you’ll immediately appreciate the bright, open layout, featuring a spacious living area ideal for relaxing or entertaining. The kitchen provides ample storage and prep space, while the adjoining dining area creates a natural flow for everyday living. Outside, you’ll enjoy a low-maintenance yard, covered parking, and plenty of room for outdoor seating. Garden Grove Oaks residents love the clubhouse, community pool & hot tub, social activities, and peaceful setting, all while being close to shopping, dining, medical facilities, and the best of Winter Haven. Whether you’re seeking a seasonal retreat or a year-round home, this charming property is move-in ready and waiting for you!

Listing is courtesy of: DREAM REALTY GROUP (863-450-7973)

Listing Agent: Nicole Castro (863-547-5647)

Remarks: Price Reduced $10,000... Welcome Home! To this beautiful 2-bedroom, 2-bath home in the sought-after 55+ Garden Grove Oaks community features land ownership and a low $65/month HOA. Located in a private cul-de-sac with ample parking, it offers an open floor plan, new roof 2025 (with a 20-year transferable warranty), new gutters 2025 new A/C and all new duct work 2024, new flooring, new carpet in the bedrooms 2025 and the kitchen has updated countertops (granite and butcher block), upgraded appliances. Community amenities include a clubhouse, heated pool, spa, shuffleboard, and organized activities. Minutes from Hwy 27, shopping, and dining. Contact me for a private showing.

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

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

Remarks: This is a must see charming oasis located behind the secure gates of Lake Ashton, you don’t want to miss this opportunity of becoming an homeowner in this Exclusive 55+ community in Florida, comes with a upgraded custom13’6 x 28’ saltwater pool with propane heater and expanded screened enclosure that measures 44’ x 24’ tankless propane water heater, and gas hookup for an outdoor kitchen in Lake Ashton! If you are seeking a stunning 2-bedroom, 2-bath property this is the one it sits on the Lake Ashton West golf course and this environment for Living certified Green home features several builder upgrades PLUS extensive builder and owner upgrades Inside, you’ll find tile flooring throughout (no carpet), upgraded kitchen cabinetry with roll-out shelving, Calcatta Silestone countertops with beveled edge; custom kitchen pantry cabinet with roll-outs; under-cabinet lighting, custom closets in both bedrooms and laundry room plus a custom pantry storage. Additional features include custom closets, updated bathrooms with a walk-in shower and glass doors, remote-controlled blinds, upgraded lighting and fans, epoxy garage flooring, and enhanced landscaping Located in Lake Ashton, a premier 55+ community offering two 18-hole golf courses, a 26,000 + sq ft Health and Fitness Center, pickleball courts , a bowling alley, a restaurant and much more, activities are abundant in this exceptional community . Don’t miss this very special pool home. Schedule your showing today.

Listing is courtesy of: LA ROSA REALTY CENTRAL FLORIDA LLC (407-861-8009)

Listing Agent: Samuel Williams (863-528-0930)

Remarks: New construction home with 2005 square feet on one-story including 3 bedrooms plus a den, 2 baths, and an open living area. Enjoy an open kitchen with Silestone countertops, Samsung stainless steel appliances, a walk-in pantry, and a spacious island, fully open to the dining café and gathering room. The living area, laundry room, and baths include luxury wood vinyl plank flooring, with stain-resistant carpet in the bedrooms. Your owner's suite is complete with a walk-in wardrobe and a private en-suite bath with dual vanities, a tiled shower, and a closeted toilet. Plus, enjoy a covered lanai, 2-car garage, custom-fit window blinds, architectural shingles, energy-efficient insulation and windows, and a full builder warranty. ***Please note - Virtual Tour showcases the home layout; colors and design options in actual home for sale may differ. Furnishings and décor do not convey!

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

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

Remarks: Wake up to peaceful water views in this beautifully maintained villa in Winter Haven. This move in ready home features a bright open floor plan with tile and laminate flooring, an oversized kitchen with plenty of space to cook and gather, and an enclosed patio where you can relax and enjoy the tranquil pond setting. All appliances are included, making your transition effortless. Located in Traditions at Lake Ruby, this sought after 55+ community offers true resort style living with a lakefront clubhouse, heated pool and spa, fitness center, tennis and pickleball courts, dog park, and a full calendar of social events. The HOA covers exterior painting, cable, internet, and lawn care so you can spend more time enjoying life. Conveniently close to shopping, dining, major highways, and Legoland. Furniture available separately.

Listing is courtesy of: LOVELAND PROPERTIES (407-352-8118)

Listing Agent: Cleve Loveland (407-352-8118)

Remarks: Short Sale. Charming, move-in ready 3-bed, 2-bath home in a peaceful Winter Haven community. Features an open living/dining layout, updated kitchen with modern finishes, and spacious bedrooms. Enjoy plenty of natural light, a private backyard perfect for gatherings and outdoor living, and an attached 2-car garage. Well-maintained and thoughtfully updated, this home offers both comfort and convenience. Monthly HOA of just $50 includes community maintenance for worry-free living. Close to shopping, dining, schools, and major roadways for easy commuting. Don’t miss this opportunity to own in a quiet, established neighborhood — schedule your showing today!

Listing is courtesy of: WORLD PROPERTIES GROUP (407-574-5920)

Listing Agent: Mona Cherkaoui (407-947-5736)

Remarks: Exquisitely and completely remodeled residence at 1539 Roselawn, thoughtfully designed to blend modern elegance with everyday comfort. This stunning home showcases high-end finishes throughout, including premium waterproof luxury vinyl flooring that adds both durability and sophistication. The gourmet-inspired kitchen is a true centerpiece, featuring sleek granite countertops, modern cabinetry, and stainless steel appliances that elevate the overall aesthetic and functionality of the space. The home also provides peace of mind with an AC system updated in 2018, ensuring efficient cooling and long-term reliability. Every detail has been carefully selected to create a cohesive and refined living environment. Situated with no HOA restrictions, this property offers exceptional flexibility and freedom, making it ideal for both homeowners and investors. Whether as a primary residence or an income-producing asset, this home represents a rare turnkey opportunity combining style, quality, and value in one package.

Listing is courtesy of: LA ROSA REALTY KISSIMMEE (407-930-3530)

Listing Agent: Ines Morales (863-738-8794)

Remarks: Welcome to this beautifully maintained 3-bedroom, 2-bathroom home offering the perfect blend of comfort, functionality, and style. Step inside to find a bright and inviting floor plan with spacious living areas, abundant natural light, and a warm, welcoming atmosphere throughout. The kitchen features ample cabinet space, and a convenient layout ideal for both everyday living and entertaining with direct access to the back patio. The master bedroom offers a private retreat with an en-suite bathroom and generous closet space that is connected directly to the large laundry room. The additional bedrooms provide flexibility for family, guests, or a home office. Outside, enjoy a spacious, fenced in yard with plenty of room for relaxing, gardening, or hosting gatherings. Conveniently located near Polk State College, Winter Haven schools, and just minutes away from downtown Winter Haven. This home combines peaceful living with everyday convenience. Don’t miss the opportunity to make this move-in-ready home your own!

Listing is courtesy of: FLAT FEE MLS REALTY (813-642-6030)

Listing Agent: Stephen Hachey (813-642-6030)

Remarks: Recently refreshed home in Central Florida featuring luxury vinyl flooring, fresh interior paint, redesigned kitchen and bathrooms, a spacious backyard, and a single-car garage. This property offers a great opportunity for those looking to transition toward homeownership with flexible options available. Conveniently located and ideal for buyers looking for space, updates, and long-term potential. Contact for additional details and showing availability.

Listing is courtesy of: LOKATION (954-545-5583)

Listing Agent: Chad Lindsey (863-660-7837)

Remarks: Move-in ready and fully remodeled from top to bottom, this 4-bedroom, 1-bathroom home at 1055 30th Street NW in Winter Haven is a true turnkey opportunity. Brand new roof (2026), brand new AC (2026), brand new windows (2026), new plumbing, and a new water heater mean all the big-ticket items are already handled — just bring your furniture and move right in. Inside, you'll find all new vinyl flooring throughout, a beautifully updated kitchen, and a flexible bonus room that can easily serve as a 4th bedroom, home office, playroom, or guest bedroom — whatever fits your lifestyle. Tucked into a quiet Winter Haven neighborhood with quick access to Highway 17, US-27, and Legoland, you're minutes from shopping, dining, and some of Polk County's best lakes.

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

Listing Agent: Philips Joseph (813-955-1966)

Remarks: Welcome to this stunning 5-bedroom, 3-bath home located in the Jace Landing community of Winter Haven. Built in 2021, this modern two-story residence provides nearly 2,700 square feet of living space designed for comfort, flexibility, and contemporary living. The open-concept layout features a bright and spacious great room, modern finishes, and a large kitchen with stainless steel appliances, ample cabinetry, and an oversized island perfect for family gatherings and entertaining. The first floor also includes a versatile flex room or optional sixth bedroom and a full bathroom, making it ideal for guests, a home office, or multi-generational living. Upstairs, the primary suite provides a private retreat with a large walk-in closet and an ensuite bath featuring dual vanities and a walk-in shower. Four additional bedrooms and a convenient upstairs laundry room create plenty of space for the whole family. This home is built with durable block construction on both levels and includes smart-home technology with Alexa integration and energy-efficient systems throughout. Outside, enjoy the covered patio and spacious backyard — perfect for relaxing or hosting outdoor get-togethers. Conveniently located just minutes from downtown Winter Haven, Legoland, shopping, dining, and with easy access to I-4, this home combines modern comfort with everyday convenience. Don’t miss your chance to own this move-in-ready home in one of Winter Haven’s most desirable communities.

Listing is courtesy of: DALTON WADE INC (888-668-8283)

Listing Agent: Andres Ramirez (863-845-3310)

Remarks: Move-in Ready.  The house is very light, with plantation shutters on all windows and 6 sets of French doors.  No carpet.  Floor plan is exceptional, and it’s a true one story.  Open floor plan. 4 bedrooms or 3 and an office.  Ceiling heights and finishes are amazing, including a 14 foot ceiling in the formal living room, dining room and covered lanai, vaulted ceiling in the kitchen and family room, and a coffered ceiling in the game room.  Double iron front door.  The family room and game room share a dual sided fireplace with beautiful surrounds.  The wet bar is strategically placed between the family room, kitchen and game room. The kitchen has Thermador appliances, granite countertops, desk, tall built in book shelf, wine rack, and 3 pantries. The laundry room has a large farmhouse sink, cabinets to the ceiling, granite countertop, and a built in ironing board.   The master bedroom is very large, with his and her closets, and hers is large and 3 tiered.  The en-suite master bath was updated in 2020 and has a standalone tub with tub filler, a shower with jets, double sinks, vanity and granite countertops. The outside space is equally beautiful, with a 1/2 acre lot, a screened pool, a separate screened patio, several large trees, and a very long privacy hedge.  Updates:  The flooring in the house was all replaced in 2020.  All surfaces were painted in 2020.  The game room, fireplace and screened patio were added in 2021.  The roof was replaced in 2023 and the house was fully repiped in 2024.  The Skidmore neighborhood is very friendly, and it sits on Lake Eloise, across from Lego Land.  Enjoy Lego Land fireworks from the front of the house and beautiful sunsets over the pool in the back.

Listing is courtesy of: LISTED SIMPLY (800-995-5879)

Listing Agent: Sinan Zakaria (800-995-5879)

Remarks: Welcome to 652 Grove St. TWO living spaces for ONE price. This exceptional property in the heart of Winter Haven offers a spacious main home plus a fully independent Mother-in-Law Suite all under the same roof. The primary residence features 3 bedrooms, 2 bathrooms, a dedicated office/flex space, an open-concept layout filled with natural light, and a 2-car garage designed for comfortable everyday living. What truly makes this property stand out is the private annex/guest house, complete with its own separate entrance, 1 bedroom, 1 bathroom, semi-equipped kitchen, and private laundry area, creating the perfect setup for extended family, guests, multi-generational living, or a private retreat space. This rare “home within a home” offers flexibility, privacy, and functionality that is hard to find at this price point. Conveniently located near US-27, shopping, dining, and everyday essentials, this unique property is a must-see to truly appreciate its layout and possibilities. Schedule your private showing today.

Listing is courtesy of: MY REALTY GROUP, LLC. (786-847-7421)

Listing Agent: Lizandra Troisi Passos (321-337-9448)

Remarks: Under contract-accepting backup offers. Turn-Key Furnished Home in Lakefront 55+ Community Welcome to easy Florida living in the peaceful 55+ lakefront community of Lake Henry. This fully furnished 2-bedroom, 2-bath home is truly move-in ready, offering comfort, convenience, and a relaxed lifestyle just steps from the water. Inside, you'll find a bright and inviting layout with a spacious living area, functional kitchen, and dining space perfect for everyday living or hosting guests. The home includes all furnishings, making it an ideal option for seasonal residents, snowbirds, or anyone looking for a turnkey Florida retreat. Additional features include: • Covered carport parking • Utility/laundry room with extra storage • Spacious primary suite with private bath • Comfortable guest bedroom and second full bath • Low-maintenance living Residents enjoy access to community amenities including a community pool, social activities, and a private dock on Lake Henry, perfect for fishing, relaxing sunsets, and enjoying Florida's beautiful outdoors. Located in the heart of Winter Haven, you're just minutes from shopping, dining, golf courses, and medical facilities. Whether you're looking for a full-time residence, seasonal getaway, or low-maintenance retirement lifestyle, this furnished home offers incredible value in a welcoming community. Schedule your private showing today and experience the relaxed Florida lifestyle this home has to offer.

Listing is courtesy of: KELLER WILLIAMS RLTY NEW TAMPA (813-994-4422)

Listing Agent: Mario Paniagua Ovando (813-953-6003)

Remarks: Under contract-accepting backup offers. Welcome Home to Queens Cove! This stunning 4 bedroom, 2 bathroom home is located in the highly desirable community of Queens Cove in Winter Haven. NO CDD and low HOA. Minutes from Legoland, hospitals, shopping centers and mayor highways. Don't miss your opportunity to own an affordable home in the heart of Winter Haven. Schedule your showing today!

Listing is courtesy of: CAISSA REALTY INVESTMENT INC (407-364-3056)

Listing Agent: Harrison Perez Collazo (787-365-8967)

Remarks: Located off the southwest side of Rifle Range Rd in Winter Haven, with easy access to Bartow, this property offers a quiet setting with plenty of potential. The existing mobile home has an approximately six-year-old roof and will benefit from updates, including subfloors and AC. Showings of the home are by appointment with an agent. Two additional structures on site offer added storage or future possibilities. No HOA. Buyers and buyer’s agents should verify all measurements, site details, land use, and tax information.

Listing is courtesy of: CROSBY & ASSOCIATES, INC. (863-293-5600)

Listing Agent: Lorena Alvarez Cordero (863-412-9288)

Remarks: Under Construction. This two-story Georgia will definitely be on your mind… This beauty highlights a modern open layout, seamlessly integrating a first-floor kitchen with a central island, a dining room and a welcoming family room with patio access. On the same level is a private owner's suite with an attached bathroom. Situated upstairs is a versatile loft for additional shared living space and four secondary bedrooms to provide restful retreats to family members and guests alike. Villa Mar is a masterplan community of new single-family homes. Near Historic downtown Winter Haven. There are lots of shops, restaurants, bike paths, and easy access to nearby highways. Close to Legoland and Bok Tower Gardens. The much anticipated “Villar Mar” community is what you have been looking for. A safe small town feel with convenience.

Listing is courtesy of: LENNAR REALTY (800-229-0611)

Listing Agent: Ben Goldstein (407-310-7677)

Remarks: This two-story Georgia will definitely be on your mind… This beauty highlights a modern open layout, seamlessly integrating a first-floor kitchen with a central island, a dining room and a welcoming family room with patio access. On the same level is a private owner's suite with an attached bathroom. Situated upstairs is a versatile loft for additional shared living space and four secondary bedrooms to provide restful retreats to family members and guests alike. Villa Mar is a masterplan community of new single-family homes. Near Historic downtown Winter Haven. There are lots of shops, restaurants, bike paths, and easy access to nearby highways. Close to Legoland and Bok Tower Gardens. The much anticipated “Villar Mar” community is what you have been looking for. A safe small town feel with convenience.

Listing is courtesy of: LENNAR REALTY (800-229-0611)

Listing Agent: Ben Goldstein (407-310-7677)

Remarks: Ground-floor, furnished condo in Sandy Cove, a lakefront community on the beautiful Winter Haven Chain of Lakes. This furnished 2-bedroom, 1-bath unit offers low-maintenance living that’s ideal for full-time residents, seasonal owners, retirees, or anyone seeking a convenient Florida lifestyle. The layout offers comfortable living with a spacious great room featuring laminate flooring, a ceiling fan, and sliding doors leading to the enclosed Florida room. The adjacent dining space is cozy and ideal for entertaining or quiet nights in. The kitchen is complete with quartz countertops, included appliances, and a stackable washer and dryer. The unit also features double-pane windows for improved energy efficiency, comfort, and noise reduction. The primary bedroom is generously sized and features a ceiling fan, walk-in closet, and direct access to the bathroom. The guest bedroom is also comfortably sized with a built-in closet, ceiling fan, and en-suite-style bathroom access. The bathroom has been updated with an upgraded vanity, solid-surface countertop, and walk-in shower. Enjoy outdoor living from the enclosed Florida room with screens and vinyl windows, perfect for relaxing or entertaining year-round. This ground-floor unit is ideally positioned just steps from the community clubhouse, grill area, and heated pool maintained at approximately 85 degrees for year-round enjoyment. Sandy Cove also offers a community dock on Lake Lulu, one of twenty+ lakes on the Winter Haven Chain, providing a peaceful setting to unwind, enjoy waterfront views, and take in beautiful Florida sunsets. Residents enjoy the relaxed lifestyle that makes Winter Haven so desirable, including boating, fishing, lakeside dining, golf courses, walking paths, and year-round community events. Conveniently located near everyday essentials and recreation, the condo is just minutes from Publix Super Markets, CVS Pharmacy, restaurants, banks, medical offices, and Walmart shopping. Nearby public boat access on Lake Summit makes it easy to enjoy the Chain of Lakes lifestyle, while several local golf courses are only a short drive away. The location also provides convenient access to both Orlando and ,making this an excellent choice for easy, low-maintenance Central Florida living.

Listing is courtesy of: THE STONES REAL ESTATE FIRM (863-412-2080)

Listing Agent: Michael Stone (863-412-9733)