Winter Haven Homes For Sale & Real Estate - 1038 homes

Remarks: Under contract-accepting backup offers. Welcome to 5457 Hogan Lane, Winter Haven, FL, a stunning home with lake views and a SPOOL (8x16) in Lake Ashton, an Exclusive 55 Plus community with Resort Style Amenities & Planned Activities! The CDD Debt has been PAID IN FULL on this home. This Ashton Floor plan home with an oversize garage(30x23) features a double car entry & separate single car entry. It has amazing curb appeal with flower bed retaining walls and additional pavers. This 4 bedroom / 2 Bath home is positioned on an oversized lot with no rear neighbors; this property offers an exceptional level of privacy and space and amazing water views. Designed with a thoughtful layout and a luxurious blend of upgrades, this home is both elegant and highly functional. The gourmet kitchen features SS appliances, Vented range with applique & induction cook top, expansive cabinetry, granite counter tops, under cabinet lighting, single level breakfast bar, recessed lighting for ambiance and accent. It opens seamlessly into a spacious family room with trey ceiling, creating the perfect space for entertaining, while a large formal dining room provides an ideal setting for gatherings and celebrations. Offering an abundance of natural light, this upgraded home features: upgraded Casement Windows, Plantation Shutters, Triple Sliders that stack into a pocket in the LR, Engineered hardwood flooring, front entry with double doors and screened enclosure, an epoxy garage floor, whole house surge protector, whole house water treatment equipment (Culligan), Crown Moulding, 250 gallon Propane tank that services the Spool, newer carpet in 2 bedrooms, utility sink in the laundry/flex room, Magic Chef wine cooler in the flex room, silhouette and slider shades, Rheem Platinum 50 Gallon Heat Pump Electric Water Heater, Roof Replacement (2023), newer garage door openers, LG French Door Refrigerator (2024), complete lanai paver resetting, Home Exterior painted (2024), complete lanai rescreen (2024), resealed all pavers (2024) 2 Pumps and Motor Replacement for the SPOOL ( 2025) and Master Temp 400,000 BTU Gas Heater for Spool (2025). These upgrades enhance the home's upscale architectural appeal. Additional living spaces include an oversized Bedroom 2 and Guest Bath. The laundry/flex room has a generous amount of shelving & counter top space, ideal for crafts & storage needs. The generously sized Primary suite with walk in closets serves as a peaceful retreat with a luxurious En-suite bathroom. The Primary Suite has Engineered Hardwood floors, French Doors that lead to the Outdoor Living area and Trey Ceiling. The Primary Bath features a large soaking tub, His and Her Vanities, Oversized Walk In Shower and separate Water Closet. A cozy eat-in kitchen nook offers the perfect spot for casual meals. The screened lanai with lake view is a true highlight—complete with a SPOOL, perfect for relaxing in the Florida sunshine. The oversized lot not only enhances curb appeal but also provides rare privacy in community living. Located in Lake Ashton, residents enjoy a vibrant, resort-style lifestyle with access to a 36-hole private golf course, two community clubhouses, resort-style swimming pools, tennis and pickleball courts, fitness centers, a bowling alley, movie theater, ballroom, craft and game rooms, an on-site Pro Shop and bar, and a calendar full of clubs and social events. The community is golf cart-friendly, making it easy to explore and enjoy everything it has to offer.

Listing is courtesy of: LAKE ASHTON REALTY INC. (863-221-5970)

Listing Agent: Lori Raath (863-409-6899)

Remarks: Welcome to this spacious 3-bedroom, 2-bath home with a dedicated office/flex room in the Oak Preserve neighborhood of Winter Haven. Offering a popular split-bedroom floor plan, generously sized rooms, an open-concept layout, and attached two-car garage, this home provides the space and flexibility today's buyers are looking for. The kitchen serves as the heart of the home, featuring abundant cabinet and counter space, two pantries, a breakfast bar, and a large dining nook with room for a full-sized table and chairs. The kitchen flows seamlessly into the living room and formal dining area, creating an ideal setup for entertaining guests, hosting holidays, or simply enjoying everyday life. The private primary suite offers a spacious retreat with a large walk-in closet and an ensuite bath featuring dual sinks, a soaking tub, and a separate shower. Two additional bedrooms and a generously sized office/den provide plenty of room for family, guests, remote work, hobbies, or a playroom. Outside, the fenced backyard offers privacy and space to enjoy the Florida lifestyle. A standout feature of the property is the detached 10' x 20' workshop complete with electricity and its own mini-split air conditioning system. Whether you need a workshop, home gym, studio, storage space, or a place to pursue your hobbies, this versatile building provides endless functionality. The home has been well maintained, and the sellers plan to install a new roof prior to closing, providing added value and peace of mind for the future owner. The yard is ready for a fresh landscaping vision, creating an opportunity to personalize the outdoor space and enhance the home's curb appeal. Conveniently located near shopping, dining, medical facilities, schools, and major roadways, this Winter Haven home combines a functional floor plan, flexible living spaces, a fenced yard, detached workshop, and an excellent location. If you've been searching for a move-in ready home with space to spread out and room to make it your own, this property deserves a closer look.

Listing is courtesy of: REMAX EXPERTS (863-802-5262)

Listing Agent: Lindsey Haubner (863-640-1181)

Remarks: Discover lakeside living at its finest in this spacious 4-bedroom, 2-bath home located in the highly desirable 55+ community of Golf & Lake Estates in Winter Haven. Here, you own both the home and the land—a rare find in this area. Perfectly positioned with Lake Henry as your backyard, this home offers stunning water views from the large living area, where expansive windows fill the space with natural light and frame the peaceful scenery. This well-maintained community features outstanding amenities, including a marina, pool, spa, clubhouse, and a storage lot for RVs or boats. Whether you love fishing, boating, or simply relaxing by the water, this property provides the ideal setting. Enjoy the serenity of lakeside living with the convenience of an active, friendly neighborhood. Don’t miss the chance to call this beautiful lakefront property home!

Listing is courtesy of: GREEN STAR REALTY, INC. (813-598-6841)

Listing Agent: Samantha Conley (813-300-7753)

Remarks: New lake house listing, two houses one price. Must see property with no HOA. Chain of lakes property on Lake Mirror with generator and whole house water system. Main house has beautiful kitchen, big living/dining combo. Kitchen has extra-large refrigerator, island, wall tile, and entry to garage. Large living room has fireplace, storage, and muti doors to sunroom. Primary bedroom has walk in closet, ensuite bathroom, and doors to sunroom. Sunroom faces lake has storage and hurricane windows. Laundry room has washer, dryer, and storage. Covered back porch overlooks pineapple garden. Separate cottage comes fully furnished and has full bath, kitchen, pantry and closet. Cottage overlooks banana and avocado trees. Covered dock overlooks lake with a swing for relaxation. All information is deemed reliable but not guaranteed. Buyer must verify all information and measurements. No seller financing.

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

Listing Agent: Kimberly Saddler (863-221-0604)

Remarks: Honey, stop the car! This home truly has it all. Featuring 5 bedrooms, 4 full baths, a spacious loft, and a 3-car garage, this property offers room for everyone. Your 68,132 sq. ft. homesite (1.56 acres) is a little piece of heaven—flat, open space with no rear neighbor, perfect for privacy and endless possibilities. Inside, you’ll find an entertainer’s paradise: a double oven, a kitchen sink plus an additional prep sink in the island, two corner pantries, and over 3,000 sq. ft. of living space to spread out and enjoy. Outside, there’s ample parking for guests and a charming front porch where you can relax and watch the clouds go by.

Listing is courtesy of: FUTURE HOME REALTY INC (813-855-4982)

Listing Agent: Paul Shearn (407-713-2127)

Remarks: Welcome 55+ or investors! This well-maintained one-bedroom, one-bathroom condo with an additional bonus room is the perfect place to retire and take it easy, or a fantastic addition to your investment portfolio. Located in the heart of Winter Haven, this home is just a mile from Legoland, shopping, and dining. The community also features a sparkling pool for you to relax and enjoy year-round. Don't miss out on this prime opportunity!

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

Listing Agent: Angela Perkins (863-280-5396)

Remarks: Nestled within the exclusive gated community of Tuscany, a charming neighborhood of just 18 homes in Southeast Winter Haven, this 4 bedroom, 3 bath pool home offers over 3,300 square feet under roof on a private 0.33 acre lot. Designed for both comfortable living and entertaining, the home features a dedicated office, formal dining room, living room, and an impressive 25' x 17' poolside bonus room complete with a custom wall-to-wall hardwood entertainment center, surround sound, upgraded lighting, tile flooring, and ceiling fan. The spacious kitchen showcases abundant Kraft Maid cabinetry, granite countertops, generous workspace, and a sunny breakfast nook overlooking the pool. A thoughtfully designed triple-split bedroom floor plan provides privacy for family and guests, while multiple access points lead to the screened pool and outdoor living areas. The spacious primary suite features a double-sink vanity, garden tub, separate shower, private water closet, and oversized walk-in closet. It also as access to the pool area. Additional highlights include hand-scraped real wood flooring throughout most of the home, including the primary suite, an outdoor summer kitchen with built-in gas grill, sink, and refrigerator, indoor laundry room, oversized two-car garage, expanded driveway with parking for up to eight vehicles, a separate entrance to the bonus room, and mature landscaping with an irrigation system on a dedicated meter. The large private backyard offers plenty of space beyond the screened pool area, creating a peaceful retreat while remaining conveniently located less than a mile from schools and Publix supermarket. Experience this exceptional property like never before with a 3D Interactive Virtual Tour or Virtual Reality featuring a 2D Floor Plan and immersive 3D Dollhouse Model, plus a 360-degree Interactive Aerial Virtual Tour showcasing the entire Tuscany community and panoramic views as far as the eye can see. The home features a stunning collection of modern gold crystal chandeliers throughout, including a 23.6" dimmable LED crystal chandelier with adjustable color temperatures in the hallways and kitchen, an elegant gold crystal flush-mount chandelier in the master bedroom, a large modern crystal LED chandelier that serves as a beautiful focal point in the living room, and a luxurious 40" gold rectangular crystal chandelier with 16 lights above the dining area, creating a cohesive, contemporary design with lighting and timeless elegance throughout the home. Meticulously maintained, this one-of-a-kind pool home is a rare opportunity to own a beautiful property in one of Southeast Winter Haven's most desirable gated communities.

Listing is courtesy of: 3D TEAM REALTY LLC (863-604-3662)

Listing Agent: Jimmy Aguilar (863-604-3662)

Remarks: Under contract-accepting backup offers. HUGE PRICE REDUCTION! Spacious 2,336 SF pool home in the gated, tranquil Overlook Estates. This 4BR/2BA floorplan features a split-bedroom layout and generous living space including an eat-in kitchen, 17x18 vaulted family room, 10x16 dining room with bay window, and a large foyer. The master suite includes a dressing alcove and walk-in closet; an adjacent bedroom makes an ideal office or nursery. High-traffic areas feature tile flooring; sliding glass doors in three rooms recess into the wall and open to a 31x50 pool deck — perfect for indoor/outdoor living. Additional highlights: 95x130 lot, terraced front walkway, 7x8 laundry with cabinetry and utility sink, 22x23 garage with built-in storage, tankless water heater, and leaf filter gutter guards. Ready for your finishing touches!

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

Listing Agent: Amy Reynolds (863-412-2279)

Remarks: Short Sale. This home is located in Villamar Subdivision in Southeast Winter Haven. It was built in 2022, and it features a nice open concept with split bedroom plan, inside laundry room, and an open kitchen with a large island. The home has ceramic tile and wood flooring throughout for ease of living. The kitchen features stainless steel appliances package with granite countertops. Other features of this home include a two-car garage, vinyl fencing, and beautiful landscaping. The community features a community pool and playground to enjoy!

Listing is courtesy of: BROKERS REALTY OF CENTRAL FLOR (863-294-6773)

Listing Agent: Renee Butler (863-294-6773)

Remarks: 6/19/2026 - NO SHOWINGS UNTIL NEXT WEEK due to new flooring install. Fully Remodeled 3 Bed / 3 Bath with No HOA – Move-In Ready in Winter Haven! Welcome to 3420 Avenue T NW — a completely updated 3-bedroom, 3-bathroom home featuring a rare full-bath-for-every-bedroom layout, all-new appliances, and a brand-new 6-foot privacy fence. This home has been renovated with today’s buyer in mind, offering a clean, modern interior with updated flooring, a refreshed kitchen, and a seamless open-concept living space. The kitchen is equipped with brand-new stainless steel appliances and flows easily into the main living areas, making it perfect for both daily living and entertaining. Each bedroom offers direct access to a full bathroom, providing flexibility for families, guests, or multi-use living arrangements — a feature that sets this home apart from typical properties in this range. The fully fenced backyard adds another layer of value, giving you private outdoor space ready for pets, play, or relaxation. If you’re searching for a move-in-ready home with modern updates, functional layout, and strong value, this one checks the boxes.

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

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

Remarks: Location, Location , Location Rare opportunity! Exceptional home with 4 bedrooms, 2 baths, and 2-car attached garage. Open-concept living with quartz kitchen, center island, and ceramic tile floors. Primary suite with walk-in closet and an-suite bath. Features include covered screened lanai, fully fenced yard, gutters, irrigation, and inside laundry. Desirable location, this home won’t last!

Listing is courtesy of: MIHOUSE REALTY LLC (407-286-2690)

Listing Agent: Martha Leighton, Pa (407-223-7767)

Remarks: Discover this must-see Tourmaline home. Included features: an inviting covered entry; an expansive great room; a well-appointed kitchen offering 42" cabinets, quartz countertops, a roomy pantry, a center island and an adjacent dining area; a beautiful primary suite showcasing an immense walk-in closet and a private bath; a convenient laundry; an airy loft; a storage area and a covered patio. This home also offers ceiling fan prewiring in select rooms.

Listing is courtesy of: AXEN REALTY, LLC (480-399-1218)

Listing Agent: Stephanie Morales, Llc (407-399-2055)

Remarks: Discover this stunning Ruby home, ready for quick move-in! Included features: a welcoming covered entry; a smartly planned kitchen boasting white 42" cabinets, a center island, a large walk-in pantry, and an open dining area; an immense great room; a secluded primary suite showcasing a generous walk-in closet and a private bath; three secondary bedrooms; a shared hall bath; a central laundry; and a comfortable covered patio. *Take advantage of special financing on quick move-in homes OR buy a to-be-built home and enjoy up to $20,000 in Flex Funds toward homes that can close in a timely manner! Options may vary by community, and offers are available on select homes on a first-come, first-served basis. Contact builder for more information!

Listing is courtesy of: AXEN REALTY, LLC (480-399-1218)

Listing Agent: Stephanie Morales, Llc (407-399-2055)

Remarks: Under contract-accepting backup offers. Wake up to views of Lake Howard and enjoy maintenance-free Florida living in the peaceful 55+ community of Imperial Harbours. From the bright Florida Room to the lakeside atmosphere and community amenities, this condominium offers the relaxed lifestyle many buyers move to Florida to find. Conveniently located less than 25 feet from the elevator, this furnished 2nd story condominium features a spacious great room, open dining area, and a pass-through window connecting the kitchen to the main living space. Natural light fills the home, highlighting the laminate and tile flooring throughout. The primary bedroom easily accommodates a king-sized bed with room for additional furniture and offers views of the community pool and cabana area. The en-suite bathroom includes a walk-in closet and walk-in shower. The second bedroom is across the hall from the main bathroom and primary bedroom. The Florida Room gives you pool and cabana views with sliding glass door separating it from the Great Room. Imperial Harbours amenities include a community pool and cabana, shuffleboard courts, fishing pier on Lake Howard, extra storage space, and a reserved covered parking spot. Lake Howard is part of Winter Haven’s famous Chain of Lakes, and downtown Winter Haven is located just across the lake for convenient access to shopping, dining, entertainment, and local events. Enjoy low-maintenance living, scenic surroundings, and the comfort of a well-established owner-occupied community with no leasing allowed.

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

Listing Agent: Ryan Odenweller, Llc (863-271-7882)

Remarks: Welcome to easy Florida lake view living in this beautifully updated 2-bedroom, 2-bath home located in a friendly 55+ no pet community on the shores of sparkling Lake Henry in sunny Winter Haven. Offering 1,456 square feet of comfortable living space, this well-loved home has been thoughtfully improved from top to bottom and is ready for its next owner. Step inside to find a bright and inviting interior featuring all new flooring, updated lighting, and ceiling fans throughout. The completely renovated kitchen is a standout, showcasing soft-close cabinetry with convenient pull-out drawers, providing both style and functionality. Both bathrooms have been tastefully remodeled, offering a fresh, modern feel. Major updates include a new roof, new AC system, new dual-pane double tilt-in windows, new skylights, and a new electrical panel—giving peace of mind for years to come. The guest bedroom comes fully furnished, making it perfect for visiting family or friends. Enjoy year-round relaxation in the Florida room, complete with its own heating and cooling, or step outside to the private backyard patio surrounded by beautiful landscaping and a full irrigation system. Enjoy lake view from both front and rear of this beautiful home! This home offers the perfect blend of comfort, convenience, and low-maintenance living in a welcoming lakefront community. Call today to schedule your private tour!

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

Listing Agent: Laura Villardi (317-402-6277)

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: Under Construction. The first floor of the stunning Edison two-story home is host to an open-concept layout that combines the kitchen with the living and dining areas, and an outdoor patio is easily reached off the main living space. Upstairs, five bedrooms surround a versatile loft, including the luxe owner’s suite, complete with a generous walk-in closet and en-suite bathroom. 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: 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: Located in the highly desirable 55+ community of Lake Point Landing, this charming 2-bedroom, 2-bath waterfront townhome offers direct views of beautiful Lake Smart and access to Winter Haven’s renowned Chain of Lakes. Upon arrival, you’re welcomed by a covered front porch and a glass storm door. Inside, the open-concept floor plan features a spacious living room enhanced by vaulted ceilings, transom windows, and sliding glass doors that showcase stunning lakefront views. The galley-style kitchen features wood laminate flooring, a stainless steel appliance package, and cream-colored cabinetry accented by brushed nickel hardware that perfectly complements the granite countertops. A charming garden window above the sink provides the ideal space for growing fresh herbs. Adjacent to the kitchen is a cozy dining area, perfect for casual meals and entertaining. Space-saving pocket doors lead to the primary bedroom suite, which offers beautiful waterfront views, chair rail molding, laminate wood flooring, and sliding glass doors that open to the screened lanai. The primary en-suite bathroom includes a vanity adorned with granite countertops, a linen closet, and a walk-in shower equipped with safety grab bars. Outdoor living is a true highlight of this home. The screened-in lanai provides breathtaking views of Lake Smart and serves as the perfect setting for relaxing, enjoying your morning coffee, or entertaining guests while taking in the tranquil waterfront scenery. Additional Features Guest bedroom and guest bathroom Washer and dryer included Architectural shingle roof (2023) AC system (2022) with a 10-year transferable warranty Community Amenities Low monthly HOA fees of $345 include: Lakefront community clubhouse Screened-in swimming pool Lawn maintenance Sewer and trash service Boat dock and boat slips available on first come basis Nestled along the shores of Lake Smart, this lovely home offers a peaceful waterfront lifestyle while remaining conveniently close to shopping, restaurants, and Willowbrook Golf Course.

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

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

Remarks: **SELLER IS OFFERING UP TO $2500 TO ASSIST BUYER WITH CLOSING COSTS** Located in Osprey Pointe on Lake Ned, 3905 Osprey Pointe Cir. is everything you've been looking for in the heart of Central Florida. This 3 bed, 2 bath home was built to last and withstand anything that comes it's way. Using solid poured concrete tilt walls, the house is incredibly strong and comfortable. Offering over 1700 square feet of air conditioned space, you will never feel confined. The family room, kitchen and dining area have soaring vaulted ceilings, while the primary bedroom feels spacious with a beautiful tray ceiling. The kitchen has many upgrades including solid cabinets, granite counter tops and a natural gas range. You'll also have access to the community clubhouse, pool and dock. With a location just minutes from great shopping, restaurants, grocery stores, medical facilities and Legoland! This home is in great shape and has a wonderful location. It will not last long, come see it before it's gone.

Listing is courtesy of: STRAIGHT UP REALTY & PM LLC (863-698-7547)

Listing Agent: Cole Bataille (863-698-7547)