Winter Haven Homes For Sale & Real Estate - 915 homes

Remarks: Better Than New 2022 Home – Move-In Ready! VA Assumable Mortgage!!! Welcome to this beautifully maintained 3-bedroom, 2-bath home with a 2-car garage, located on a desirable corner lot in the sought-after Villamar community of Winter Haven. Built in 2022, this home offers modern living without the wait for new construction. Step inside to an open and inviting floor plan featuring tile flooring throughout the main living areas, with comfortable bedrooms and a spacious primary suite. The kitchen comes equipped with appliances and flows seamlessly into the living and dining areas, making it perfect for everyday living and entertaining. Enjoy outdoor living in the screened lanai, ideal for relaxing or hosting guests. The home also includes an irrigation system and established landscaping, features often not included in new builds. Located in a community with resort-style amenities including a pool, playground, and sidewalks, and just minutes from shopping, dining, and local schools, this home offers both convenience and lifestyle. Skip the construction wait, this home is vacant and ready for immediate move-in! Don’t miss your opportunity to own a newer home in a growing area at an incredible value. Schedule your private showing today!

Listing is courtesy of: LA ROSA REALTY PRESTIGE (863-940-4850)

Listing Agent: Regina Moran Pa (863-698-0748)

Remarks: Welcome to this beautifully updated home in Winter Haven! This move-in ready property combines classic charm with modern upgrades, featuring stunning high-gloss marble-style porcelain flooring throughout that creates a bright and elegant living space. Enjoy a spacious layout filled with natural light, a well-maintained kitchen with stainless steel appliances, wood cabinetry, and a stylish backsplash — perfect for everyday living. The home also offers a renovated bathroom with modern finishes and a convenient interior laundry area. Step outside to a large, fully fenced backyard, ideal for entertaining, pets, or simply enjoying your own private outdoor space. The covered carport and extended driveway provide ample parking. Located in a quiet, well-established neighborhood, this home is perfect for first-time buyers or investors. Property is being sold AS-IS, presenting a great opportunity for buyers looking for value and flexibility. Schedule your private showing today!

Listing is courtesy of: LA ROSA REALTY PRESTIGE (863-940-4850)

Listing Agent: Gabriel Rivera Gonzalez (407-724-4717)

Remarks: *Sellers very motivated* Welcome home to this beautifully renovated 3-bedroom, 2-bath property with a 2-car garage, perfectly situated on a spacious corner lot in the welcoming Brenton Manor community in Winter Haven. Surrounded by peaceful natural lakes and friendly neighborhood streets, this move-in-ready home offers the ideal setting for your first step into homeownership. Inside, you are greeted by a versatile front room that can easily become your home office, a cozy family space, or a formal dining area—whatever fits your needs. The bright, modern kitchen features white cabinetry, quartz countertops, a stylish backsplash, and a comfortable breakfast nook where you can enjoy your morning coffee. The kitchen opens directly into the main living area, creating a natural flow for everyday living and hosting friends and family. The private primary suite gives you a comfortable retreat with a beautifully updated bathroom and a walk-in closet for convenient storage. With a split floor plan, the two additional bedrooms and second bathroom are tucked away on the opposite side of the home—perfect for children, guests, or a roommate. You’ll appreciate the easy-care luxury vinyl plank flooring throughout, the dedicated laundry room located just off the kitchen, and the attached garage for added convenience. Step outside through the sliding doors to a brand-new screened and covered porch overlooking a fully fenced backyard—ideal for pets, weekend barbecues, or simply relaxing after a long day. This home also includes a low cost energy-efficient solar panels, helping keep utility costs down, along with a low HOA for even more affordability—key advantages for first-time buyers looking to build stability and equity. If you’re ready for a fresh start in a beautifully updated home with modern finishes and smart savings, this one is a must-see. Schedule your private tour today and take the next step toward homeownership.

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Pedro Santiago (407-259-9513)

Remarks: Ready Now! Introducing Villa Mar in Winter Haven, Florida. Master-planned amenities including a pool with cabana that is walking distance from your home, a playground, and shaded seating area. Highway 27, less than 10 minutes away, has everything you are looking for. Grocery stores, movie theaters, shopping centers, golf courses, restaurants, and so much more. The Glen Ridge single-family home is your key to great living. An open floor plan makes entertaining a breeze. Play a game in the family room or gather round the dining room table for a delicious meal, home cooked in the gorgeous gourmet kitchen with large island and walk-in pantry. The 2-car garage offers convenient extra storage. Upstairs, 2 bedrooms and a full bath give guests plenty of privacy. Make the most of your loft by using it as a second living space or media center. Your luxury owner’s suite includes dual walk-in closets and double vanities. You’re going to love The Glen Ridge. All Ryan Homes now include WIFI-enabled garage opener and Ecobee thermostat. **Closing cost assistance is available with use of Builder’s affiliated lender**. DISCLAIMER: Prices, financing, promotion, and offers subject to change without notice. Offer valid on new sales only. See Community Sales and Marketing Representative for details. Promotions cannot be combined with any other offer. All uploaded photos are stock photos of this floor plan. Actual home may differ from photos.

Listing is courtesy of: MALTBIE REALTY GROUP (813-819-5255)

Listing Agent: Bill Maltbie (813-819-5255)

Remarks: Welcome to this charming and well-maintained home in the heart of Winter Haven! Situated on a spacious lot, this property offers a perfect blend of comfort and functionality with an open-concept layout, abundant natural light, and inviting living spaces. The kitchen features ample cabinetry and flows seamlessly into the main living area, making it ideal for both everyday living and entertaining. Enjoy a generously sized backyard with plenty of room for outdoor activities, gardening, or relaxing in your own private space. Conveniently located near shopping, dining, schools, and major roadways, this home provides both tranquility and accessibility. A fantastic opportunity for homeowners or investors alike—schedule your showing today!

Listing is courtesy of: KELLER WILLIAMS SUBURBAN TAMPA (813-684-9500)

Listing Agent: Bridd Bone (727-798-1918)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. WATERFRONT CUSTOM St. John floor plan with CDD bond debt PAID IN FULL! Recent Upgrades: Kinetico whole-house water softener, refrigerator (2025), New roof (2024), AC, dishwasher, stove, additional screened room with pavers, and upgraded landscaping (2022). Experience Florida living at its finest in this beautifully upgraded 3-bedroom + den, 2-bath home, complete with an enclosed Florida room and extended screened lanai. From the moment you arrive, you’ll notice the attention to detail: custom stacked stone accents, a power screen on the garage door, golf cart garage entrance, upgraded landscaping, a front paver patio, screened entry, and elegant beveled double glass doors. Inside, round columns frame the dining area, while raised stone archways lead to the kitchen and breakfast nook. The great room features coffered ceilings with recessed lighting, a ceiling fan, and double crown molding that flows throughout the home. The kitchen boasts a bank of drawers, 42" raised-panel custom cabinets with crown molding, stainless steel appliances, a large prep island with extra storage, granite countertops, pendant lighting, and a breakfast bar. Wake up to serene views from your primary bedroom, complete with sliding doors to the lanai. The en-suite bath features two walk-in closets, a walk-in shower, double vanities, a soaking tub, and a linen closet. Enjoy two clubhouses, two 18-hole golf courses, bowling, a movie theatre, craft & card rooms, billiards, pickleball, tennis, bocce, and so much more.

Listing is courtesy of: A+ REALTY LLC (863-293-1141)

Listing Agent: Emily Muscarella (863-978-7180)

Remarks: Short Sale. "SHORT SALE!! Seller accepting CASH ONLY!! APPROVED SHORT SALE PRICE BY LIEN HOLDER. Needs TLC. This midcentury POOL home has much potential. It features 3 bedrooms and 3 baths. It has a formal living room area, an office area and a large dining/family room for family gatherings. The fireplace has been converted to gas. Pool enclosure can be developed to be an amazing outdoor space. There is NO HOA, NO CDD and NO FLOOD ZONE is this well-established neighborhood. Located close to popular restaurants, shopping centers, and Legoland Florida Resort & Park, banks and lakes. It is tucked away, yet close to it ALL.

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

Listing Agent: Kelly Hansell (863-557-1784)

Remarks: Welcome To Hartridge Hills!! This Gorgeous Gated Community is one of Polk County's Hidden Treasures. An established and well maintained community of charming custom homes, each one uniquely it's own. Nestled between Lake Pansy and Lake Hartridge, this community offers boat lovers their own private boat ramp with access to the Chain of Lakes. This community also has been home to many pilots over the years and is conveniently located beside the Winter Haven Airport and only minutes to Publix and all major medical facilities making this community a perfect location. Situated on a corner lot, this well built home by Ernie White is a split plan offering 3 bedrooms & 2 baths plus a den or office space. The dining room, living area and bedrooms have new luxury vinyl. There is High ceilings throughout, crown molding, updated granite in the kitchen and bathrooms. The roof was replaced in 2017. HOA fee's include lawn care and the irrigation system is on a small well, saving you money on your water bill! Grab your favorite beverage & Relax and Enjoy the water views on your enclosed back lanai. Come check out this beautiful property, You'll love being a part of this quaint community!!

Listing is courtesy of: PREMIER HOMES AND REAL ESTATE (863-937-8942)

Listing Agent: Christy Smith (863-409-8709)

Remarks: Welcome to SPRING LAKE TOWERS, a premier 55+ community in Winter Haven, Florida offering a relaxed lakefront lifestyle with this well-maintained 2-bedroom, 2-bath condo featuring an open floor plan with stunning lake views, a 12' x 22' great room connected to the kitchen via convenient pass-through, spacious 12' x 18' Primary suite with private bathroom and walk-in closet, 10' x 13' second bedroom adjacent to guest bathroom with tub/shower, and a versatile 7' x 23' Florida room perfect for home office, hobbies, or relaxation. The all-inclusive condo fee covers cable TV, internet, water, sewer, trash removal, building maintenance (exterior, roof, insurance), reserve funds, common area upkeep, on-site management, and access to all community amenities including swimming pool, exercise room, recreation room with kitchen, library, game area, shuffleboard, laundry facilities, and active social calendar with enhanced security features. Situated on the "Chain of Lakes" for fishing, boating, and water activities with boat slips available for a reasonable fee (verify with management), this property boasts a rare assigned covered parking space in close proximity to the unit and is adjacent to Northgate shopping plaza featuring Publix, restaurants, and services, minutes from medical facilities, Winter Haven Hospital, places of worship, and downtown. No pets or smoking permitted. This perfect full-time residence or seasonal retreat (measurements approximate, information believed accurate but not guaranteed).

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Kevin Tison (863-206-5755)

Remarks: Welcome to this well-maintained 2-bedroom, 2-bath home located in the desirable community of Oakwood Estates in Winter Haven. This home offers a peaceful, well-kept neighborhood with a welcoming atmosphere and a beautiful lake view to enjoy. Recent updates include new kitchen and bathroom flooring, new windows, and new interior and exterior doors, along with a roof that is approximately 5 years old, offering added value and peace of mind. No lot rent—ownership includes the land, with only a low monthly HOA fee. Oakwood Estates is a gated 55+ community offering resort-style amenities including clubhouses, heated pools, fitness center, shuffleboard, tennis courts, and a full calendar of activities. Conveniently located near shopping, dining, medical facilities, and major roadways. Schedule your private showing today and experience easy living in this vibrant community.

Listing is courtesy of: LA ROSA REALTY PRESTIGE (863-940-4850)

Listing Agent: Jody Pagan (863-604-2367)

Remarks: Immaculate and updated pool home ideally located in SE Winter Haven just two blocks from Chain of Lakes access. This well-cared for pool residence features a sleek modern appearance with comfortable living spaces and an impressive level of quality updates found throughout. Interior features 4 bedrooms (two master suites), 3 bathrooms, formal dining room and an absolutely stunning kitchen. New luxury vinyl plank flooring flows through the main living areas including the spacious great room with relaxing views of the private backyard oasis. The home's large dining room is perfectly sized for entertaining or spending quality time with family. Amazing kitchen is truly a chef's dream with custom soft-close cabinetry, elegant quartz counters, stainless appliances and a top-of-line Ruvati Workstation Sink with accessories. It's easy to unwind in the oversized 20x18 master suite with its tray ceiling, walk-in closet and a spa-like master bath with barn door entry, marble topped vanity, dual sinks, soaking tub and a tiled walk-in shower. Remaining 3 bedrooms are all generously sized, one of which has an en-suite bathroom and could easily function as the home's second master/in-law suite. Inside laundry has plenty of room for a full size washer and dryer as well as extra space for storage. Stepping outside reveals an extended 33' long covered and screened lanai with tranquil views of the open-air and a 30x15 inground pool! A huge fully-fenced backyard and a SmithBuilt storage shed with electric for storing lawn equipment and pool toys or a workshop. There is NO HOA so feel free to bring your boat! Less than a 2 min walk from the Lake Summit boat ramp for easy access to the Winter Haven Chain of Lakes where you can enjoy fishing, skiing or boating any of the 20+ canal-connected lakes or stop for a bite to eat at one of the local lakeside restaurants. Extensive list of recent updates include: whole house replumbed in 2019, new roof in 2019, new AC handler in 2019, master bath remodeled 2019, new water heater 2019, kitchen remodeled 2021, new luxury vinyl plank flooring 2021, new variable speed pool pump 2024, pool heater 2022, back and front yard irrigation 2024, guest bathroom remodeled 2025! Close to Legoland, medical facilities, grocery stores, dining, shopping and conveniently located between Tampa and Orlando. Wonderful established neighborhood close to everything. Come see this one today!

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

Listing Agent: Christina Loesch (347-977-0962)

Remarks: Income-producing duplex in Winter Haven with both units in place and performing. Each side offers 2 bedrooms, 2 bathrooms, and approximately 1,175 square feet with layouts that are easy to maintain and consistently appealing to long-term tenants. Positioned on a cul-de-sac, the setting is more private while still keeping quick access to everyday conveniences, shopping, dining, and major roadways. Both units are leased at $1,195 per month, with lease terms secured through early 2027—creating immediate income with no vacancy concerns. Do not disturb tenants.

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

Listing Agent: Kristin Kellin (863-409-5649)

Remarks: Short Sale. Step into one of the largest units at the vibrant 55+ community of Imperial Harbor in Winter Haven! This spacious 3-bedroom, 2-bath condo also features a bonus room. With three comfortable bedrooms, there’s ample space for guests, a home office, or crafting area. Enjoy an active lifestyle with shuffleboard courts, a well-equipped gym, and a billiard room. The heated pool ensures year-round relaxation, and a private community dock on Lake Howard is ideal for boating and fishing enthusiasts. Association dues cover water, basic cable, and internet, and also include access to dock your own boat. Located in the heart of Winter Haven, Imperial Harbor offers a serene and friendly community atmosphere, close to shopping, dining, recreational activities, and medical facilities. Act quickly because a property like this will not last long.

Listing is courtesy of: REALTY COOPERATIVE (800-704-6411)

Listing Agent: Tony Giglio (513-505-5222)

Remarks: **RECENTLY REDUCED AND PRICED TO SELL** Welcome to this spacious 3 bedroom, 3 bath townhouse located in the private, gated, lakefront community of Casarena on the Lakes. Situated on the Winter Haven Chain of Lakes with a desirable south-facing view of Lake Cannon, this home offers the rare opportunity to enjoy both sunrise and sunset views right from your own space. Three-bedroom properties in this community are seldom available. This would make a PERFECT winter retreat! Boasting over 2,300 square feet of living space, the home provides plenty of room to live comfortably. The second level features two primary suites. One includes a private balcony with beautiful lake views, perfect for morning coffee or winding down in the evening. That same suite also offers an oversized walk-in shower with a built-in steam sauna, creating a relaxing, spa-like retreat at home. The third bedroom is located on the main level and works perfectly for guests or a home office. The kitchen has been thoughtfully updated with high-end stainless steel appliances, granite countertops, and solid wood cabinetry. It opens to the dining area and main living space, which are separated by a striking stone fireplace, making the layout ideal for both everyday living and entertaining. Parking is a standout feature with a two-car garage PLUS an additional parking space, providing room for three vehicles. Community amenities include a pool, tennis court, and a newly rebuilt composite dock with boat slips available on a first-come basis. Leave your boat in the water so you’re always ready for early-morning fishing, evening cruises, or a spur-of-the-moment dinner at one of the Chain’s waterfront restaurants. Additional updates to this home include two new A/C units, a WHOLE-HOUSE GENERATOR, and a tankless water heater, offering comfort and peace of mind year-round. This home delivers space, thoughtful upgrades, and true lakefront living in a secure, well-kept community.

Listing is courtesy of: BERRY REALTY & APPRAISAL SERVICES PA (863-224-6857)

Listing Agent: Kylie Berry (863-224-6857)

Remarks: Welcome to your dream oasis—a stunning craftsman-style 3-bedroom, 2-bath saltwater pool home nestled on just over a quarter acre. This charming property features a large front porch, perfect for relaxing with your morning coffee or enjoying beautiful sunsets. Step inside to find a warm and inviting interior with classic crown molding throughout. The formal dining room offers an elegant space for entertaining, and it can easily double as a home office or flexible bonus room to suit your needs. A cozy dinette off the kitchen provides an additional casual setting for family meals. The backyard is a true retreat, boasting a huge fenced area that provides privacy and security. Dive into the sparkling pool, or unwind on the screened back porch, where you can enjoy the tranquility of your outdoor space. This stunning home also includes a 2-car carport, a long driveway for additional parking, and convenient boat parking—ideal for those who love life on the water. Located near the Lake Howard public boat dock, you’ll enjoy easy access to Winter Haven's sought-after chain of lakes. Additional features include a Generac generator for peace of mind, propane tanks for efficient energy use, and a storage shed for all your gardening tools and equipment. This home perfectly combines comfort, style, and functionality in a picturesque setting. Don’t miss your chance to make it yours!

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

Listing Agent: Michelle Howard (863-944-9920)

Remarks: Under contract-accepting backup offers. BEAUTIFUL , RENOVATED 2BEDS, 2 BATHS , OPEN CONCEPT , LAMINATED FLOORS, QUARTZ KITCHEN COUNTER TOPS, NEW KITCHE, NEW BATHROOMS. ENCLOSED PORCH, OVERSIZE LOT. PARTIALLY FENCED, NEW ROOF,NEW AC. READY TO MOVE IN. CLOSE TO SCHOOLS, HOSPITALS, LEGO LAND, MAJOR HWYS NO HOA.

Listing is courtesy of: CENTURY 21 WOLF'S CROSSING REALTY (407-449-0000)

Listing Agent: Lucy Martinez (863-521-4156)

Remarks: Discover this well maintained 2 bedroom, 1 bathroom home offering 1,206 sq ft of comfortable living space. The home features a practical layout with a functional living area and kitchen. The bedrooms are well sized, and the property offers a spacious yard with room to enjoy. Located in a quiet residential neighborhood, this home is easy to show and ready for its next owner!

Listing is courtesy of: SOVEREIGN REAL ESTATE GROUP (305-662-1502)

Listing Agent: William Figueroa (305-662-1502)

Remarks: !!PRICE ADJUSTMENT!! NOW is your opportunity to own this home. Roof: 2023, HVAC: 2023, Water Heater: New, Electric: Serviced in 2020, Plumbing: Re-piped in 2025. 3/1.5 home in Winter Haven close to downtown (Target is coming!) and near Polk State College. Huge yard! New carpet in every bedroom! Pretty bathrooms! Walk to the lake! Schedule a showing today! This property has approximately 1,559 square feet of living space on a lot of approximately 0.28 acres, with three bedrooms, one full bathroom and an en-suite half bathroom. Hardwood-style vinyl flooring and stone fireplace creates a warm and inviting tone. Large windows allow for an tons of soft, natural light to fill the rooms, enhancing the open layout and creating a peaceful setting. The separate dining room area provides space for hosting a dinner or game night. The retro vibe flows throughout the house and fits-in with the established neighborhood. An efficient kitchen features a window overlooking the backyard and makes it convenient to have BBQs and fun playtime out back. The backyard has it's own storage shed and is large enough to have a pet, playground or maybe even a pool. The primary bedroom and two additional bedrooms are on opposite sides for privacy and quiet. The vintage-styled bathrooms add a unique charm to the home. The pink tile sequence makes it fun to get ready for the day. Just steps from the college, the property is conveniently located near the college ballfields, offering easy access to recreational activities. A walking trail nearby provides opportunities for exercise, and the home is situated close to the town, allowing for quick and easy access to local shopping. The garage features a work bench and shelves, providing storage and workspace. The property's proximity to the lake allows for enjoyable walks or leisure activities on the water.

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

Listing Agent: Maria Deary (863-241-8361)

Remarks: Opportunities like this rarely come available in the gated Lakewood community. This beautifully updated lakefront pool home sits on a private one-acre lot and offers breathtaking sunset views across Lake Otis from your own backyard. Spend your evenings relaxing on the dock as the sun sets over the water, launch a kayak from the built-in racks, or enjoy weekends boating right from your covered dock. The backyard is designed for Florida living with a resurfaced pool, spacious screened patio, and incredible water views. Inside, the home offers 5 bedrooms and 3.5 bathrooms, including a highly desirable layout with two primary suites—one upstairs and one downstairs, perfect for guests or multi-generational living. Major updates provide peace of mind, including a new roof, two HVAC systems, new water heater, new flooring, and new carpet. The home also features all new double-pane impact windows and sliding doors, a newly resurfaced and retiled pool, and a new covered dock with kayak storage. The irrigation system pulls directly from the lake, so watering your lawn is never restricted by city water rules. Recent improvements include a re-screened patio, new gutters, new garage door, and a new privacy fence, making this home move-in ready. Imagine ending every day watching the sunset over Lake Otis from your own backyard. Homes like this rarely come on the market—schedule your private showing before it’s gone.

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

Listing Agent: Kelly Fain (863-617-0074)

Remarks: Under contract-accepting backup offers. DON'T MISS THIS 3 BEDROOM 2.5 BATH HOME CENTRALLY LOCATED IN WINTER HAVEN, FL ON AN OVERSIZED (.39 ACRE) LOT WITH NO HOA!!! Featuring nearly 2,000 SqFt. of heated and cooled living space, this 2-owner home was constructed of BLOCK AND BRICK! The OPEN-CONCEPT, SPLIT BEDROOM PLAN, and CENTRALLY LOCATED KITCHEN share both privacy and convenience. There is plenty of natural light in the main living area and especially through the glass sliders leading to the back yard. In the event more privacy is preferred, just hit the remote button for the MOTORIZED BLINDS, which are also INCLUDED IN THE SALE. For those looking for an OVERSIED GARAGE, this one plenty of workspace for several different hobbies. There is no shortage of parking whatsoever on this HUGE CORNER LOT! Opportunity awaits at this lovely residence, which is located in close proximity to LEGOLAND, FL, medical, shopping, dining, schools, and the many freshwater lakes Winter Haven features. Winter Haven is also located between ORANDO INTERNATIONAL and TAMPA INTERNATIONAL AIRPORT, and the most recently added AVELO AIRLINE in LAKELAND, FL!!!

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

Listing Agent: Wanda Dicks (863-287-7846)