Winter Haven Homes For Sale & Real Estate - 863 homes

Remarks: MOVE-IN READY! Welcome to your dream home in the sought-after Willowbrook North community! This stunning Ranch-style, one-story residence offers effortless living with 3 spacious bedrooms, 2 full bathrooms, and a versatile flex space—perfect for a home office, playroom, or additional living area. You'll fall in love with the modern open-concept layout, featuring quartz countertops throughout, soft-close cabinets and drawers, and smart home features designed for comfort and convenience. Enjoy peaceful mornings and relaxing evenings with serene pond views right outside your front door. Built with quality and style in mind, this home is the perfect blend of elegance and functionality—ready for you to move in and make it your own. Don't miss this opportunity to own a beautifully crafted home in a growing, vibrant community!

Listing is courtesy of: DRB GROUP REALTY, LLC (407-270-2747)

Listing Agent: Adam Schott (407-270-2747)

Remarks: Short Sale. Motivated Sellers- well below appraisal price - Price requires bank approval - Located in the growing Villa Mar community, this Cali floor plan offers 1,828 square feet of modern comfort in a location that blends resort-style amenities with everyday convenience. Residents enjoy a sparkling pool with a second on the way, a playground, and a planned dog park, creating an active and welcoming neighborhood lifestyle. Just minutes from Legoland, Highway 27, shopping, schools, medical centers, and dining, this home offers both accessibility and charm. The open kitchen is a chef’s delight with granite countertops, a generous island, upgraded cabinetry, and stainless-steel appliances, all connecting to bright and spacious living and dining areas. The primary suite easily fits a king bed and features a walk-in closet and a large walk-in shower for ultimate comfort. Outside, a covered lanai offers a peaceful water view with no rear neighbors for complete privacy. Schedule your private tour today and discover why Villa Mar is the perfect address for you.

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

Listing Agent: Christian Clay (863-509-7466)

Remarks: Back on Market due to loan denial, Chain of Lakes Frontage on Lake Hartridge Enjoy true waterfront living in this beautifully updated 3-bedroom, 2.5-bath townhome-style condo located directly on Lake Hartridge, part of the renowned Winter Haven Chain of Lakes. Situated in the desirable Casa Del Sol community, this spacious two-story home offers direct lake access and stunning panoramic views. The interior features wood laminate and tile flooring, a formal dining room, updated kitchen with stainless steel appliances and solid surface countertops, and a large living room overlooking the water. Relax in the Florida room or enjoy sunrise and sunset views from your screened lakefront lanai. Upstairs, the generous primary suite includes a walk-in closet, ensuite bath with granite counters, and a private enclosed balcony with breathtaking lake views. Two additional bedrooms, full bath, and upstairs laundry complete the layout. An attached 2-car garage adds convenience. Community amenities include a lakefront recreation area, pool, clubhouse, tennis courts, and private dock. HOA covers water, lawn care, and full access to amenities.Experience maintenance-free living with true Chain of Lakes frontage and endless boating, fishing, and waterfront enjoyment.

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

Listing Agent: Irene Bryan (863-289-6789)

Remarks: One or more photo(s) has been virtually staged. Waterfront view from your porch. Affordability, low-maintenance comfort, & strong rental income potential. Waterfront view from your porch. Discover serene living at this charming 2-bedroom, 2-bathroom condo offering stunning sunset water views from its screened lanai. The home has a functional layout, it includes a combination of living & dining area, a large master suite with a walk-in closet, & a sliding glass door towards your comfortable back porch overlooking the canal water view; the kitchen has sufficient space; & there is a large storage room. Enjoy your Florida lifestyle, this welcoming community with built-in amenities, has direct lakefront access via a community dock for boating, fishing, and water sports on the connected Chain of Lakes. For only $253 a month, HOA covers your home's exterior maintenance. Location is accessible to nearby shopping, hospitals, medical offices, schools, and about an hour drive Tampa or Orlando. To schedule a showing, provide your realtor your pre-approval letter or proof of cash funds. At this price range, this move-in ready condo is your best choice.

Listing is courtesy of: MAZELG REALTY (863-399-0226)

Listing Agent: Lienyvette Grimaldo (863-399-0226)

Remarks: This move-in ready 3-bedroom Winter Haven pool home offers a fantastic combination of comfort, upgrades, and true Florida living on an oversized lot with no HOA. The home features a brand-new roof, new HVAC system and thermostat, new water heater, new pool pump and chlorinator, new laundry units, new exterior front doors, and an expanded driveway with ample parking. Inside, you’ll find a functional layout with generous living space and fresh improvements throughout. The private in-ground pool creates a relaxing backyard setting, while the large lot provides room for outdoor entertaining, storage, or future additions. Located minutes from the Winter Haven Chain of Lakes, Gene’s Lakeside Marina, LEGOLAND Florida Resort, golf courses, shopping, dining, and local parks, this property sits in one of Central Florida’s most desirable and fast-growing areas. With major updates already completed and convenient access to boating, recreation, and upcoming community development, this home is an excellent opportunity for first-time buyers, families, or investors.

Listing is courtesy of: THE URBAN GROUP, INC. (954-522-6226)

Listing Agent: Ashlee Morrell (941-740-9134)

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: Brand new, energy-efficient home available NOW! Open floor plan with a lot of flexibility. Retreat to your primary suite that is conveniently situated in the back of the home for plenty of privacy and offers a huge walk-in closet and bathroom with dual sink vanity and standalone shower. Visit Villamar and explore new single-family homes for sale in Winter Haven, FL. Residents will have access to two resort-style amenity centers featuring a clubhouse, pool, and playground. Winter Haven is known for its beautiful chain of lakes with lakeside restaurants and its award-winning community theater. Nearby attractions include Legoland Florida and Peppa Pig Theme Park. A brand-new model and new phase are coming soon. Each of our homes is built with innovative, energy-efficient features designed to help you enjoy more savings, better health, real comfort and peace of mind.

Listing is courtesy of: MERITAGE HOMES OF FL REALTY (813-703-8860)

Listing Agent: Bryan Sumner (813-336-5895)

Remarks: Welcome to this exceptional 2-bedroom, 2-bathroom patio home nestled within the highly sought after Orchid Springs community. Positioned on an expansive double lot, this residence offers a serene and secluded wooded vista visible from the open kitchen and the generously proportioned screened patio. Noteworthy exteri9or features; Paved drive and walkways, attractive canopies and covered front porch invites you inside to discover a charming home. The kitchen boasts custom pantry space, ample counter area and is thoughtfully designed for hosting guests without compromising meal preparation. Beyond the kitchen, the spacious living room, flex apace is adjacent to a second private patio. The large family room offers expansive sliding doors and windows making the perfect space for relaxation. Leading to a beautiful lanai ideal for sharing a glass of wine or enjoying a barbeque, with its scenic outlook. The dining room is designed for casual or formal entertainment. The master bedroom features an ensuite bath and picturesque views while additional bedrooms and guest bathroom complete the layout. Flooring; Tiled foyer, kitchen and bathrooms with plush carpet in the master bedroom as well as the second bedroom, living and dining rooms. Designed with single level living in mind this Orchid Springs Patio Home offers ease of mobility and low maintenance. Stop outside to the spacious outdoor area enveloped by lush trees providing privacy and a natural ambiance. Additional amenities include a spacious 2 car garage with natural gas water heater & washer & dryer. Conveniently located in SE Winter Haven, this central Florida home provides easy access to downtown, Chain of Lakes boat launches, LegoLand, and major highways. The neighborhood also features a community clubhouse and pool, enhancing the overall Florida lifestyle experience.

Listing is courtesy of: NEXTHOME NORRIS & COMPANY REALTY (863-875-5583)

Listing Agent: Michael Norris (863-287-3105)

Remarks: Welcome to 207 Winter Ridge Blvd – A Serene Lakeside Retreat! This charming end-unit condo is a peaceful lakeview haven. Features; 2 spacious bedrooms, 2 bathrooms, and an open-concept living and dining area that flows effortlessly into an enclosed Florida room—ideal for soaking in breathtaking sunsets over Lake Conine. The kitchen features a built-in desk and a convenient closet pantry, while the master suite boasts a generous walk-in closet. Additional highlights include: Two dedicated parking spaces (one covered), brick paved front patio for outdoor enjoyment, high-end windows and doors, Hurricane shutters for peace of mind, new roof installed in 2024. Located within city limits, this quiet and well-maintained community offers resort-style amenities including a clubhouse, sparkling pool, shuffleboard courts, and access to a community dock and boat slip on Lake Smart. Whether you're fishing off the pier or strolling to nearby shops and restaurants in downtown Winter Haven, you'll love the blend of convenience & charm.

Listing is courtesy of: NEXTHOME NORRIS & COMPANY REALTY (863-875-5583)

Listing Agent: Michael Norris (863-287-3105)

Remarks: *** No CDD fees!!***Welcome to this stunning smart home offering the perfect blend of modern design, space, and functionality. This impressive two-story residence features 5 bedrooms, 3 full bathrooms, and a spacious 3-car garage, making it ideal for growing families or those who love to entertain. Step inside to discover a bright and open floor plan designed for today’s lifestyle. The main living areas flow seamlessly, creating the perfect space for gatherings, while large windows bring in abundant natural light. The modern kitchen serves as the heart of the home, featuring sleek finishes, ample cabinetry, and generous counter space for cooking and entertaining. With five generously sized bedrooms, there’s room for everyone—including a flexible space for guests, a home office, or multi-generational living. The primary suite offers a private retreat with a well-appointed en-suite bathroom and plenty of closet space. This home is equipped with smart home technology, providing convenience, efficiency, and peace of mind at your fingertips.Step outside and enjoy your own private outdoor retreat situated on a generous 0.24-acre lot, offering plenty of space for relaxation, play, or future customization. The covered back patio and screened enclosure create the perfect setting for year-round outdoor living—ideal for morning coffee, evening gatherings, or simply enjoying Florida’s beautiful weather without the bugs. Built in 2023, this home offers the advantages of newer construction without the wait, combining modern features with move-in ready convenience. Don’t miss the opportunity to own this beautifully designed home—schedule your private showing today!

Listing is courtesy of: JASON MITCHELL REAL ESTATE FLO (754-307-0607)

Listing Agent: David Hartigan (407-955-1156)

Remarks: Under contract-accepting backup offers. You'll definitely want to check out this beautiful, like-new property! The zero entry resort style community pool and playground overlooks one of the many beautiful lakes in Winter Haven. Villamar is a wonderful community close to a top rated Elementary School. Enjoy the privacy of this lot, as it does not have rear neighbors, but instead overlooks a quaint pond and conservatory area! Make sure to schedule your showing today!

Listing is courtesy of: VALOR REALTY SERVICES LLC (407-668-2448)

Listing Agent: Marian Benson (954-205-3075)

Remarks: Welcome to 6775 Brentwood Dr NE, located in the desirable no pet community of Lake N Golf Estates, a 55+ lakefront community offering the best of Florida living. This well maintained, mostly furnished home offers 3 bedrooms, 2 bathrooms with a spacious and functional layout, including a Florida room, formal dining room, breakfast nook and a dedicated laundry/storage room, providing plenty of flexibility for everyday living and entertaining. Updated HVAC system (2024) & automated thermostat. Additional exterior features include awnings for added shade and energy efficiency, along with a spacious carport for convenient covered parking. The home already passed the insurance/4-pointe inspection and will come with a one year home warranty at closing. It is situated within an established, beautifully maintained community known for its welcoming atmosphere and convenient access to nearby shopping, dining, medical facilities, and major roadways. Residents of Lake N Golf Estates enjoy fantastic amenities including a clubhouse, heated pool, spa, shuffleboard courts and community boat slip access, perfect for taking full advantage of the scenic lakefront setting. With OWNED land, low maintenance living, this community offers both comfort and peace of mind. Whether you're looking for a seasonal retreat or a fulltime residence, this is a wonderful opportunity to enjoy the Florida lifestyle at its finest. Schedule your private showing today and experience all that Lake N Golf Estates has to offer!

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

Listing Agent: Patricia De Graaff, Llc (863-307-0061)

Remarks: Located in the 55+ community of Brookhaven Village, this fee-simple manufactured home offers 1,620 square feet of living space with a functional layout and recent updates. Built in 1990, the home features 2 bedrooms and 2 bathrooms, with vinyl and carpet flooring throughout. The interior includes a spacious living and dining area, an interior laundry closet, and ample storage. An attached storage room provides additional space and may be suitable for use as a workshop, hobby area, or general storage. The home also features a covered and screened porch, offering a comfortable space to enjoy the outdoors. Recent improvements include a roof replaced in 2023 and an HVAC system replaced in 2022. The home may be conveyed fully furnished, providing a convenient option for buyers. Brookhaven Village offers community amenities including a clubhouse, pool, shuffleboard courts, and organized social activities. The HOA fee is $34 per month, and the community enforces age restrictions in accordance with its 55+ designation. Conveniently located in Winter Haven with access to shopping, dining, and local amenities, this property offers an opportunity for low-maintenance living in an established adult community.

Listing is courtesy of: COLDWELL BANKER REALTY (863-687-2233)

Listing Agent: Daniel Mcfee (863-273-6324)

Remarks: Welcome to your dream home in the heart of Winter Haven's sought-after Peace Creek Reserve community! This stunning two-story Atlanta Plan offers 4 bedrooms, 2.5 bathrooms, and 1,933 square feet of thoughtfully designed living space that perfectly balances comfort with style. Step inside to discover an open floor plan that flows seamlessly from the great room to the dining area and into a chef's dream kitchen. The heart of the home features a large island perfect for morning coffee or evening entertaining, complemented by gleaming quartz countertops, stainless steel appliances, and a generous pantry that even Mary Poppins would envy. The casual dining area opens to a covered lanai through sliding glass doors, creating an effortless indoor-outdoor living experience. Upstairs, the primary bedroom retreat awaits with a luxurious en-suite bathroom featuring a spacious walk-in shower, dual vanity, and a walk-in closet that could double as a small boutique. Three additional bedrooms, a full bathroom, and a versatile loft provide plenty of space for family, guests, or that home office you've been dreaming about. The convenient second-floor laundry room means no more hauling baskets up and down stairs. Throughout the home, beautiful tile flooring graces the main living areas while cozy carpet warms the bedrooms. Peace Creek Reserve offers the perfect blend of small-town charm and modern convenience, nestled near Winter Haven's famous chain of lakes connected by scenic canals. With abundant shopping, dining, and bike paths nearby, this community delivers everything you've been searching for in your next home.

Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)

Listing Agent: Maritza Saint Hilaire (407-953-6765)

Remarks: One or more photo(s) has been virtually staged. NEW ROOF 2/9/2026 + $45,000 PRICE IMPROVEMENT! Lakefront living on the Chain of Lakes just became an incredible opportunity. Welcome to 4099 Island Lakes Dr — a well-maintained 3 bedroom, 2 bath block home offering breathtaking waterfront views and direct access to the Chain of Lakes. Major updates already handled with a brand new roof installed February 9, 2026, giving buyers peace of mind and potential insurance benefits. Combine that with a significant $40K price reduction, and this property stands out in today’s market. Inside, you’ll find a bright and open layout filled with natural light. The spacious living area flows seamlessly into the kitchen and dining space, ideal for entertaining or relaxing after a day on the water. The primary suite features beautiful lake views, a private bath, and generous closet space. Step outside to freshly installed sod and updated landscaping that enhances curb appeal and creates the perfect setting for outdoor gatherings. With direct lake access, enjoy boating, fishing, kayaking, and stunning sunset views right from your backyard. Whether you're searching for a full-time residence, seasonal escape, or lakefront investment, this Chain of Lakes home offers location, lifestyle, and value. Schedule your private showing today.

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

Listing Agent: Don Jerue (863-259-9550)

Remarks: LOCATION, LOCATION, LOCATION! ONLY MINUTES FROM ATTRACTIONS. THIS HARWICH FLOOR PLAN IS GREAT FOR ENTERTAINING WITH IT'S OPEN FLOOR PLAN. HOME IS WELL EQUIPED WITH SIDE BY SIDE FRIDGE, GLASS TOP RANGE, DISHWAHER, WASHER, DRYER, NEW 2026 ROOF AND MUCH MORE. MASTER SUITE IS VERY SPACIOUS AND MASTER BATH WITH STAND UP SHOWER AND DOUBLE VANITY. LAKESIDE LANDINGS IS A BEAUTIFUL COMMUNITY WITH A LOT OF GREEN SPACE, A NATURE TRAIL AND PARK AT LAKE CONINE, 2 POOLS (FREEFORM AND LAP), LARGE COVERED LANAI AREA WITH SEATING AND RESTROOMS, AND PLAYGROUND. 15 MINUTES TO LEGOLAND. STOP BY AND TAKE A LOOK AT LAKESIDE LANDINGS COMMUNITY.

Listing is courtesy of: KELLER WILLIAMS REALTY PREMIER (305-595-2844)

Listing Agent: Aileen Garciga (786-286-9372)

Remarks: Nestled in the heart of Winter Haven! Welcome to this well-maintained 3-bedroom 2- bath home with a bonus room, perfect for an office room, playroom or guest bedroom. Offering a comfortable layout split floorplan. A spacious kitchen with lots of cabinets and stainless appliances. Master bedroom with double closet, master bath with walk-in shower and two sink vanity. Step outside to a fully fenced backyard ideal for families, pets, or anyone who loves the outdoors. The home is located close to lakes, parks, shopping, and downtown Winter Haven. NO HOA or CDD. Don't miss your chance to own this beautiful gem! Schedule your private tour today.

Listing is courtesy of: GLOBALWIDE REALTY LLC (352-456-9788)

Listing Agent: Ruth Benavides Rivera (352-673-5697)

Remarks: Under contract-accepting backup offers. Experience timeless elegance in this executive Mediterranean-style home, where refined architecture meets luxurious living. Welcome to Heron Cay, an exclusive retreat comprised of just two dozen custom homes tucked away near Lake Eloise. Make your way through the gate and wind around to the cul-de-sac where this exceptional home stands ready to welcome and impress you. Upon entering through the double doors, prepare to be captivated by the grand scale of this home's living spaces and rich textures. Open-concept design flows seamlessly into expansive living and dining areas, highlighted by soaring ceilings, a travertine fireplace, and windows that bathe the home in natural light. The gourmet chef’s kitchen is a true showpiece, featuring premium stainless-steel appliances including a gas range, beautiful cabinetry, a wine refrigerator, an island, and elegant granite countertops—ideal for both everyday living and upscale entertaining. Be sure to take note of the ample storage and rolling ladder in the well appointed butler's pantry, and the custom coffee station. Retreat to the lavish primary suite, complete with a spa-inspired bathroom, walk-in shower, separate steam shower, dual vanities, and an expansive custom closet. The remaining bedrooms are generously sized and thoughtfully designed spaces to ensure comfort for family and visitors alike. Step outside to your own private oasis—lush landscaping, an enclosed pool and patio, and ample space for outdoor dining and relaxation create the ultimate setting for year-round enjoyment. On a practical note, the home is equipped with a 22KW Generac generator, which is sure to provide peace of mind during storm season. Combining Mediterranean charm with executive-level finishes, this extraordinary home offers privacy, prestige, and craftsmanship in one of the area’s most desirable gated communities. Request your private tour today, and ask about the seller's assumable incredible interest rate!

Listing is courtesy of: FATHOM REALTY FL LLC (888-455-6040)

Listing Agent: Misty Mccracken (863-289-0735)

Remarks: Under Construction. This BEAUTIFUL ALLEX II Model home is located in the quaint town of Winter Haven. Ski capital & home of LEGOLAND. The ALLEX II is3/2/2- 1504 S/F & newly upgraded! This new model has an open floor plan with a spacious DINING room off the kitchen to entertain & enjoy the company of your guests. You will love the split floor plan with beautiful & spacious master suite with walk in closet & en suite bathroom away from the other 2 bedrooms. Home comes with WHIRLPOOL Stainless Appliances- range, hood microwave, refrigerator & dishwasher. Home also comes with faux wood blinds throughout & has Smart Home Technology which allows you to set the scene & connect to your home with your voice, from your smart phone.

Listing is courtesy of: DR HORTON REALTY OF CENTRAL FLORIDA LLC (407-250-7299)

Listing Agent: Stephen Cline (407-250-7299)

Remarks: Under contract-accepting backup offers. LAKEFRONT LIVING FOR UNDER $200K, MOTITVATED SELLER!!! Why pay lot rent when you can enjoy the charm and tranquility in this beautifully renovated, Fully Furnished 2 Bedroom/2 Bath 2006 home in Winter Haven! Nestled in the serene, gated 55+ Lakeside Ranch community on Lake Henry. This home is move-in ready and offers a host of modern updates, including New HVAC (2025) and New Roof and All New Windows both replaced in 2024. The home features a spacious living room, a primary bedroom with an ensuite bathroom and walk-in shower, an indoor utility room with laundry and extra storage, and a screened-in porch perfect for relaxing or enjoying breathtaking sunset views. The kitchen is designed for convenience featuring an Island with Breakfast Bar and ample storage. The carport doubles as additional seating or parking space. Lakeside Ranch is a co-op community where the price includes an $11,000 share in the corporation—meaning no lot rent. The LOW MONTHLY HOA Fee that includes Water, Sewer & Garbage. This vibrant community offers an array of amenities, including a clubhouse, heated swimming pool, library, shuffleboard courts, horseshoe area, billiards, a boat launch, and docks on Lake Henry. Residents can also take advantage of scheduled holiday events, arts and crafts classes, exercise programs, card games, and more. For added convenience, the community has a trailer storage area, self-contained water and sewer systems with backup generators. Perfect for year-round residents or snowbirds. Lakeside Ranch Community offers the flexibility to be as active or as relaxed as you desire. With its idyllic location near shopping, dining, and amusement parks, this home offers the best of Florida living. Call today for a private showing and start enjoying the security, serenity, and vibrant lifestyle of this remarkable Lakeside Community!!

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

Listing Agent: Cheryl Brewer (863-224-0045)