Winter Haven Homes For Sale & Real Estate - 981 homes

Remarks: **Multiple offers received. Best offers by 2pm 5/14** This 4 bedroom, 2 bath pool home brings the space you need with a personality that actually makes you feel something the second you walk in. It is bright, it is open, and it has just enough bold style to keep things interesting without trying too hard. Inside, the open layout is filled with natural light and designed for how you really live. The upgraded flooring keeps everything feeling fresh and pulled together, while the pops of color and unique touches give the home a vibe you will not find in a basic, cookie cutter house. The kitchen is right where it should be, open to everything. You have updated appliances, including a newer refrigerator, and a layout that makes it easy to cook, host, laugh, and still be part of the conversation. Whether it is a casual night in or a full house of friends, this space just works. And then we get to the backyard, because yes, she is the moment. A fully screened in pool area gives you your own private escape. Think slow weekends, evening swims, maybe a little music playing in the background. And with solar heating, you are not just looking at it, you are actually using it all year long. The big ticket items are already handled too. Newer AC and water heater, both about a year and a half old, so you can skip the stress and go straight to enjoying your new home. Location wise, you are minutes from LEGOLAND, close to the Chain of Lakes, and a quick drive into downtown Winter Haven. So you are connected to everything without giving up your own space. If you have been waiting for something that feels a little more fun, a little more expressive, and a lot less boring, this one is absolutely worth seeing in person. Trust me, you are going to feel it the second you walk in.

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

Listing Agent: Jen Lay (863-370-1793)

Remarks: This expansive two-story Columbus has a well-designed layout, featuring a first floor dedicated to shared living and entertaining. The open concept design seamlessly connects the kitchen, dining room and family room, with a patio extending the interior space outdoors. Upstairs, a spacious loft separates the three secondary bedrooms from the serene owner's suite. Completing the home is a convenient two-car garage. 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: Welcome to 287 Inman Blvd—where modern comfort meets effortless Florida living in the heart of Winter Haven. This beautifully maintained home truly feels like new, offering the peace of mind of recent construction with thoughtful upgrades already in place. In addition to the home’s like-new condition and thoughtful upgrades, qualified buyers may also have the rare opportunity to assume the seller’s existing 5.125% mortgage — potentially creating estimated monthly savings of more than $250 compared to many current market interest rates. From the moment you step inside, you’ll notice a clean, contemporary design paired with warm, inviting spaces. The open-concept layout flows seamlessly, making it perfect for both everyday living and entertaining. The kitchen is a standout feature, enhanced with a stylish backsplash on the island and throughout, complemented by upgraded light fixtures that add a polished, custom feel. The home also features low-maintenance quartz countertops as well as stainless steel appliances. This home has already been elevated beyond builder-grade with valuable improvements, including solar panels for energy efficiency, a vinyl privacy fence for added outdoor enjoyment, and upgraded ceiling fans and lighting throughout. Tile flooring in the wet areas offers durability and easy maintenance, while cozy carpeting in the bedrooms creates a comfortable retreat at the end of the day. Step outside and enjoy a backyard space that’s ready for relaxing evenings, pets, or gatherings—fully enclosed for privacy and convenience. Location is where this home truly shines. Situated just about one and a half miles from the soon-to-open Publix shopping plaza, you’ll have everyday essentials right around the corner. Plus, you’re only minutes from downtown Winter Haven, known for its charming local shops, dining, and access to the Chain of Lakes lifestyle. Commuters will appreciate the quick access to US-27, making travel to surrounding areas simple and efficient. If you’ve been searching for a move-in-ready home with upgrades already done, modern finishes, and a prime location, this is one you don’t want to miss.

Listing is courtesy of: RE/MAX HERITAGE PROFESSIONALS (863-256-2188)

Listing Agent: Chris Loschiavo (863-280-2201)

Remarks: Under contract-accepting backup offers. Welcome to this spacious and well-maintained four-bedroom, two-bathroom home offering comfort, functionality, and a great layout for everyday living. The open and inviting floor plan features a generous living area that flows seamlessly into the kitchen and dining space, making it ideal for both entertaining and family gatherings. The kitchen offers ample cabinetry, plenty of counter space, and a convenient layout for cooking and hosting. The split-bedroom design provides added privacy, with a spacious primary suite featuring an en-suite bathroom, while the additional bedrooms are well-sized and versatile for guests, family, or a home office. Enjoy outdoor living with a backyard that offers room to relax, play, or entertain. This home also includes a two-car garage, providing additional storage and convenience. Conveniently located near shopping, dining, schools, and major roadways, this property is perfect as a primary residence, second home, or investment opportunity. Don’t miss your chance to own this wonderful home — schedule your private showing today!

Listing is courtesy of: STACEY TOWNS REALTY LLC (863-422-1585)

Listing Agent: Stacey Towns Friend (863-557-3034)

Remarks: Under contract-accepting backup offers. Short Sale. Welcome to your 5 bedroom 3 bathroom home located conveniently in Winter Haven with easy access to dining, shopping, and major roadways. This home features tile flooring throughout the living areas and an open floor plan making it perfect for entertaining. There is a separate living room at the front of the home which could make the perfect office or library. The large kitchen provides a large island, granite countertops, updated lighting, tiled backsplash, stainless steel appliances, and a closet pantry. The large family room is adjacent to the kitchen. You’ll also find sliding doors to your outdoor patio and backyard. One of the 5 bedrooms is located downstairs with its own bathroom, the perfect spot for guests. The primary bedroom is upstairs and features an en-suite with a stand up shower, dual sink vanity and 2 walk in closets! The remaining bedrooms provide plenty of space and share the main hall bathroom with a dual sink vanity and tub/shower combo. This home checks all the boxes! Schedule your private showing today!

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

Listing Agent: Casandra Vann (863-546-5446)

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: 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: 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: 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. 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: 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)

Remarks: Under Construction. This expansive two-story Columbus has a well-designed layout, featuring a first floor dedicated to shared living and entertaining. The open concept design seamlessly connects the kitchen, dining room and family room, with a patio extending the interior space outdoors. Upstairs, a spacious loft separates the three secondary bedrooms from the serene owner's suite. Completing the home is a convenient two-car garage. 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: Another Great Listing. Gated Community, Like New. Open floor plan. minutes from downtown Winter Haven. Low HOA, you’ll enjoy neighborhood security and amenities without the extra cost. Commuters will love the quick access to Hwy 27, providing an easy drive to area beaches, Orlando’s theme parks, and more. Price To Sell.

Listing is courtesy of: XCELLENCE REALTY INC. (866-595-6025)

Listing Agent: Paul Jacques (561-441-9695)