Homes For Sale in Winter Haven 33884 - 317 homes

Remarks: Welcome to 523 Little Lake Court — a spacious 3-bedroom, 2-bath home on a generous lot in the heart of Winter Haven. Step through elegant double front doors with decorative glass and an arched transom into soaring vaulted ceilings that flow throughout the main living areas. The open layout features beautiful hardwood floors in the formal living and dining rooms, a large family room with a cozy fireplace and dramatic arched windows, and a kitchen with wihte cabinetry, a center island, and breakfast bar. The master suite has vaulted ceilings, a freestanding fireplace, French doors to the backyard, and an en-suite bath with a soaking tub, walk-in shower, and dual vanity beneath a stunning arched window. Additional highlights include an interior laundry room, an attached two-car garage, and a large fully fenced backyard with mature trees and a storage shed. Conveniently located just minutes from Little Lake with easy access to shopping, dining, and everything Winter Haven has to do.

Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)

Listing Agent: Steven Koleno (804-656-5007)

Remarks: IMPRESSIVE HOME IN GREAT LOCATION! Move-In-Ready— This home has a wonderful design of open concept living, formal dining room, split bedroom plan and screen lanai overlooking a wooded area giving a peaceful setting without rear neighbors. A welcoming foyer leads to the formal dining room and a step down into the lovely living room featuring a cathedral ceiling, fireplace, built-in entertainment center and sliding glass doors that give view and access to the relaxing lanai highlighting an inground spa. The living room links to the dinette with lanai access and a breakfast bar joining the kitchen. This appealing kitchen has elegant cabinetry accented with upper cabinets of frosted glass doors, pantry storage, decorative tile backsplash, dark stone counters and stainless appliances including a gas range. The home’s design has a contemporary flair that is prominent within the owners’ en suite. Privately situated, this spacious bedroom not only has a walk-in closet and French doors to the lanai, but its unique design delivers an elaborate, elevated and open bathroom featuring a sunken marble bathtub, tile & glass surroundings, lengthy dual sink vanity, shower stall and water closet. The opposite side of the home houses a full bathroom and two lovely bedrooms, one with French doors accessing the lanai. The home is outfitted with an abundance of good-looking ceiling fans and attractive floor coverings including the brick decking on the lanai with the in-ground hot tub! Additional elements that make this a fabulous home include the brand New Roof, New Water Heater, New A/C, large driveway for extra parking, peaceful backyard and lovely gated community. This is a great location offering convenience to all shopping, dining, entertainment, schools and medical around Winter Haven. Call to arrange your appointment today, don’t miss out on this opportunity!

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

Listing Agent: Erin Floyd (863-412-2286)

Remarks: Impeccably maintained home in the sought-after Traditions 55+ community in Winter Haven! This spacious 2-bedroom, 2-bath home with a dedicated office/den offers over 1,500 square feet of open-concept living space, designed for both comfort and functionality. The home features new flooring throughout, upgraded countertops, 36-inch kitchen cabinets, and modern lighting fixtures, creating a bright and inviting kitchen and living area perfect for everyday living or entertaining. Both bathrooms have been tastefully upgraded, and additional improvements include a new water heater and recently replaced AC coil for added efficiency and peace of mind. The home was freshly painted inside and out in 2023, giving it a clean, modern feel throughout. Step outside to enjoy the new screened-in porch, ideal for relaxing mornings or evening gatherings while overlooking the newly installed sod that enhances the home’s curb appeal. The extended driveway provides additional parking and convenience, and the home is handicap accessible, offering added functionality and ease of living. Residents of Traditions enjoy resort-style amenities, including community boat ramp access, fishing, dock, and private water access, along with a community pool and recreational facilities. The HOA includes cable TV, internet, exterior, grounds maintenance, pool maintenance, recreational facilities, and security, making this a truly low-maintenance lifestyle. Located just minutes from shopping, dining, and major roadways, this move-in ready home combines modern updates, accessibility, and the vibrant lifestyle of one of Winter Haven’s most desirable active adult communities.

Listing is courtesy of: CREEGAN GROUP (407-622-1111)

Listing Agent: Nathan Mercado (407-353-8612)

Remarks: Under contract-accepting backup offers. Discover the perfect blend of country living and modern convenience with this well-maintained property set on over 5 acres. This spacious home offers 3 bedrooms plus a dedicated office, 2 full baths, a welcoming living room, formal dining room, and a bright kitchen with a breakfast nook. Step outside to your own private retreat featuring a screened pool, ideal for relaxing or entertaining. Equestrian enthusiasts will appreciate the horse barn along with fenced and cross-fenced pastures, providing plenty of space for animals. The property combines privacy and wide-open views with easy access to city amenities, shopping, and schools. With its well-cared-for condition and versatile layout, this home is move-in ready and waiting for you to enjoy the best of both worlds—peaceful country living just minutes from town.

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

Listing Agent: Steve Lockhart (863-289-9801)

Remarks: Charming residence in Winter Haven featuring 3 bedrooms and 2 bathrooms. This home has a spacious living area with abundant natural light, a modern kitchen with ample storage, and a serene backyard appropriate for relaxation. Located in a peaceful neighborhood with convenient access to local amenities, this property provides a welcoming atmosphere and comfortable living. Don't miss this opportunity to be part of the vibrant Winter Haven community. Key Features: *Kitchen: Newly remodeled kitchen with soft close upgraded cabinets and new appliances. Features: Fully furnished home with washer and dryer included; new bathrooms with upgrade tiles. Vinyl fence for pets and privacy. *Water softner system included

Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)

Listing Agent: Steven Koleno (804-656-5007)

Remarks: Welcome to 22 Lake Link in Winter Haven, where space, lifestyle, and location come together in one exceptional opportunity. Situated on a large corner lot, this 4-bedroom, 2-bathroom home with a 2-car garage offers the perfect combination of comfort, functionality, and Florida living. Step inside to a bright and open floor plan designed for modern living and entertaining. The spacious layout flows seamlessly from the living and dining areas to the kitchen, creating the perfect environment for hosting family and friends. Enjoy your mornings on the front balcony and unwind in the evenings on the screened-in patio, overlooking your huge fenced-in backyard—ideal for pets, gatherings, or even adding a pool. Additional highlights include a durable metal roof for long-term value and a large driveway with plenty of space for multiple vehicles, guests, or recreational toys. This home is perfectly positioned to give you access to everything that makes Central Florida one of the most desirable places to live. Convenient access to major highways including Interstate 4, US Route 27, and Florida State Road 540 for easy commuting to Orlando, Tampa, and beyond. Just a short drive to world-famous attractions like Walt Disney World, Universal Orlando Resort, and LEGOLAND Florida Resort. Enjoy weekend trips to Florida’s beautiful beaches including Clearwater & St. Pete Beach (west coast) and Cocoa Beach (east coast). Living in Winter Haven means you’re close to a growing scene of local favorites and everyday conveniences such as, Coffee spots like Richard's Fine Coffees and Starbucks. Popular dining options including Harborside, Tanners Lakeside Restaurant & Bar, Aria and Azteca D'Oro. Shopping and entertainment nearby at Winter Haven Central Park and Eagle Ridge Mall. Minutes from Lake Link and the Chain of Lakes of Winter Haven, Florida.

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

Listing Agent: Omar Andreasen (407-883-2989)

Remarks: NO LOT RENT! Live the retired life you worked so hard for. Whether you are a snowbird or looking to enjoy full-time residency, Orange Manor West welcomes you. This highly sought-after 55+ gated community in Winter Haven, secondary resident(s) must be 40+. This fully furnished 2-bedroom, 2-bath home offers a functional layout with recent updates including a 2018 roof, 2022 HVAC, 2021 water heater, newer vinyl flooring, and updated appliances. The home features a spacious layout with walk-in closets in both bedrooms, a private primary suite with a step-in shower, and an enclosed Florida room that is perfect for relaxing mornings or unwinding in the evening. Enjoy an active, low-maintenance lifestyle with monthly fees that include cable, internet, and trash, in a community that allows only service and emotional support animals. Residents have access to a wide range of amenities including a community pool, clubhouse, billiards, shuffleboard, horseshoes, mini golf, fishing, lake access, and a full calendar of social activities such as bingo, cards, sports tournaments, quilting, and much more. Additional features include onsite management, 24-hour emergency service, extra storage for boats and recreational vehicles, and boat slips. Located in Southeast Winter Haven, you are just minutes from shopping, dining, and everyday conveniences, with Legoland ad Peppa Pig theme parks nearby for visiting guests. This is a great opportunity to enjoy comfort, convenience, and community all in one place.

Listing is courtesy of: FLORIDA REALTY MARKETPLACE (863-877-1915)

Listing Agent: Jenn Manzella (863-866-0335)

Remarks: Welcome to this beautifully maintained 4-bedroom, 2.5-bath home built in 2018, offering the perfect blend of modern comfort and Florida lifestyle living. From the moment you step inside, you’ll appreciate the open-concept layout, ideal for both everyday living and entertaining. The spacious kitchen flows seamlessly into the living and dining areas, featuring contemporary finishes, ample cabinetry, and plenty of natural light throughout. The living area is enhanced by a stylish built-in electric fireplace, creating a warm and inviting focal point. This thoughtfully designed single-story home features a spacious primary suite with a private bath and walk-in closet, along with three additional bedrooms that offer flexibility for family, guests, or a home office. Step outside and enjoy your private backyard space—perfect for relaxing evenings or weekend gatherings. The garage is equipped with a mini-split air conditioning system, adding comfort and versatility for a workspace, gym, or additional storage. Located in a desirable community with private access to Lake Eloise, part of the renowned Winter Haven Chain of Lakes, you’ll have endless opportunities for boating, fishing, and enjoying the water just minutes from your doorstep. Plus, you’re just 10 minutes from LEGOLAND Florida Resort, making this location perfect for both everyday convenience and fun-filled weekends. Conveniently situated near shopping, dining, and major roadways, this move-in-ready home offers the ideal combination of location, lifestyle, and value. Schedule your private showing today and experience everything this home has to offer!

Listing is courtesy of: CLARK REALTY LLC (863-345-2155)

Listing Agent: Ty Dennis (863-651-8328)

Remarks: Discover the ultimate "Entertainer’s Dream" in the heart of Lake Ashton, Central Florida’s premier 55+ gated community. This residence is meticulously designed for those who love to host, featuring soaring high ceilings that create an immediate sense of grandeur and an open, airy flow throughout the main living areas. These impressive heights extend into the closets, offering massive vertical storage capacity to keep your home guest-ready and clutter-free. The centerpiece for social gatherings is the professionally expanded and fully enclosed Florida Room, which has been seamlessly integrated into the home with dedicated AC vents. This climate-controlled sanctuary provides a vast, versatile space for hosting dinner parties or holiday gatherings in year-round comfort. A Resort Lifestyle Without Equal When you aren't hosting at home, the Lake Ashton lifestyle offers a world-class social calendar and unrivaled amenities across two massive clubhouses: Social & Dining Hubs: Impress guests at the on-site Eagles Nest restaurant, or join one of over 100 active social clubs. Elite Recreation: Enjoy a professional-grade bowling alley, a private cinema, a grand ballroom for live entertainment, and a billiard room. Active Sports: Access two 18-hole championship golf courses, plus dedicated courts for pickleball, tennis, and bocce ball. Health & Wellness: A state-of-the-art Health & Fitness Center featuring an indoor walking track, a full gym, sauna, and multiple heated indoor/outdoor pools and spas. Water Access: Explore the community boat ramp with direct access to Lake Ashton for fishing and boating. Safety & Accessibility: Peace of mind is standard with 24-hour manned security gates and a golf-cart-friendly infrastructure throughout the neighborhood. From the expansive interior spaces to the endless community perks, this home is designed for a life well-lived.

Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (863-701-2350)

Listing Agent: Wes Fleming (863-666-4136)

Remarks: Located in Winter Haven, this 2 bedroom, 2 bathroom double wide mobile home sits on an oversized corner lot! The home offers a functional layout with comfortable living space and enclosed front porch. Both bedrooms have walk-in closets and the primary bedroom also has an en suite. The closed-in carport space offers extra functionality as a bonus room and also has an enclosed laundry room. The large corner lot has a fenced in backyard and also provides a detached workshop with AC unit perfect for storage, hobbies, and so much more! The neighborhood also has a boat ramp to Lake Fox for the boaters and fishing lovers! Conveniently located near shopping, dining, Legoland, and Hwy 27 for commuters, this is a great opportunity for a primary residence or investment property! Schedule a private tour today!

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

Listing Agent: Ashley Helms (863-206-7260)

Remarks: IMPROVED PRICE!! LOCATION, LOCATION!! Gorgeous 3 bed, 2 bath POOL home with idyllic views across pretty pond with water frontage and private wooded island!! Located in the sought after gated, Overlook Estates on a spacious corner lot with mature landscaping. The open-concept living area creates an inviting atmosphere, ideal for both relaxed family gatherings and formal entertaining. Enter into the foyer which is flanked by dining room, living room and an additional study/den. Continue through into the spacious kitchen and family room with sliding doors leading to the covered lanai and screened pool area. Relax with your favorite beverage and enjoy the tranquil views of the pond and wooded island with an abundance of wildlife! The primary suite is to the left of the family room and boasts an atmospheric, cozy, gas fireplace and spacious primary bathroom. To the right of the family room are two further bedrooms and full size bathroom. Overlook Estates is perfectly situated among the Chain of Lakes in Winter Haven, not far from Cypress Gardens Blvd for fast commuting and access to dining, shopping and much more. Do not miss this opportunity to live the Florida lifestyle in this unique home!

Listing is courtesy of: WATSON REALTY CORP. (407-589-1600)

Listing Agent: Sue Webb (407-361-6425)

Remarks: Welcome to this exceptional 4-bedroom, 3-bath pool home located in the highly sought-after gated community of Woodpointe in Winter Haven. Custom built by John Wood, this home was thoughtfully designed for both everyday comfort and entertaining. Upon entering, you are immediately impressed by the tall specialty ceilings and the abundance of natural light throughout. The formal living room offers stunning views of the screened pool area, creating an inviting and elegant first impression. The spacious island kitchen features ample cabinetry and counter space and opens seamlessly to the main living area, allowing for an easy flow between spaces while maintaining beautiful pool views. The living room continues to showcase serene views of the screened pool, enhancing the home’s indoor-outdoor living experience. Large bedrooms provide comfort and privacy, while the well-designed floor plan offers functionality and flexibility for a variety of lifestyles. Step outside to the private backyard oasis where a sparkling pool and peaceful surroundings create the perfect setting for relaxation or entertaining. Nestled within a beautifully maintained gated community known for its prime location, this home offers both exclusivity and convenience, with close proximity to shopping, dining, and major roadways, yet tucked away in a tranquil setting. Major updates include a roof replaced in 02/2021, AC replaced in 2017, and a water heater replaced in 07/2025. Homes in Woodpointe are rarely available, schedule your private showing today and experience the lifestyle this property has to offer.

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

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

Remarks: Multiple offers, kindly asking highest and best by Monday 3/2 at 3pm. Location, updates, and flexibility, all in one. Welcome to this beautifully maintained home in the desirable Garden Grove community of SE Winter Haven, just down the street from Lake Ned and minutes to shopping, restaurants, and easy access to HWY 27. Situated on a spacious .22-acre fully fenced lot, this 2-bedroom, 2-bath + bonus room residence offers warmth and functionality throughout. Fresh interior paint gives the home a clean, move-in-ready feel, while hardwood flooring flows through the main living areas. The kitchen features porcelain tile, a tiled backsplash, stainless steel refrigerator, and all appliances included. Natural light fills the living room, with sliding glass doors leading to a screened lanai, the perfect spot for morning coffee or unwinding in the evening. Part of the one-car garage has been converted into a versatile bonus room with wood flooring and its own split AC/heat unit, ideal for a home office, gym, hobby room, or guest overflow. A Tesla charger remains in place for electric vehicle convenience. Both bathrooms have been partially updated and showcase beautiful accent tile flooring. Step outside to enjoy a fully vinyl-fenced backyard designed for privacy and enjoyment, complete with an open patio, firepit area, and additional storage shed. The covered front porch adds charm and curb appeal. The roof was replaced in 2020 and the AC in 2021. This home offers the ideal combination of comfort, location, and practical upgrades. Schedule your private showing today.

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

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

Remarks: 2118 Chris Dr is a property that boasts a kitchen equipped with all stainless steel appliances, adding a modern touch to the culinary space. The kitchen island serves as a functional centerpiece, perfect for meal preparation or casual dining. The primary bedroom is a haven of comfort, complete with a walk-in closet that provides ample storage for your wardrobe. With these attributes, this property ensures a comfortable and convenient lifestyle. Included 100-Day Home Warranty with buyer activation

Listing is courtesy of: OPENDOOR BROKERAGE LLC (480-462-5392)

Listing Agent: Karen Albright (480-462-5392)

Remarks: Short Sale. Lender has provided preliminary net guidance based on a recent appraisal. Offers will be reviewed in accordance with lender and VA guidelines. Buyer is encouraged to submit highest and best offer. Final approval subject to lender review.This is the kind of home that just feels right the moment you pull in. Set on an oversized .29-acre lot with no rear neighbors and peaceful conservation views behind you, this spacious 4-bedroom, 2-bath home offers room to breathe, grow, and truly settle in. Inside, you’ll find more than 2,200 square feet of comfortable living space—plus a converted garage that gives you even more flexibility. Need a fifth bedroom? A home office? A workout room or game space? This home easily adapts to whatever stage of life you’re in. The heart of the home is the open kitchen, breakfast nook, and family room, designed for everyday living and easy entertaining. Large windows over the kitchen sink flood the space with natural light, while ample cabinetry and a charming barn-door pantry add both function and personality. The living room’s feature wall gives the space character, and luxury vinyl flooring throughout keeps things both stylish and practical. Every bedroom has ceiling fans, making the home comfortable year-round. One of the hidden gems here is the oversized laundry room—complete with built-in cabinets and direct access to the backyard—perfect for storage, projects, or keeping life organized. Major updates mean peace of mind: newer windows and sliding glass doors, updated insulation, a replaced sewer line, newer appliances, a 2021 roof, and solar panels installed in 2022. Even better? The solar panels often result in credits from the power company, helping keep monthly utility costs surprisingly low. Step outside and you’ll see where this home really shines. The backyard feels private and inviting, with a large screened porch, fire pit for cozy evenings, and two storage sheds for all your tools and toys. Whether you’re hosting friends, enjoying a quiet morning coffee, or winding down after a long day, there’s space here to enjoy Florida living your way. The wide driveway easily fits four or more vehicles, making gatherings easy. Located in a quiet non-HOA neighborhood, you’ll enjoy the freedom to live how you want—no HOA or CDD fees—while still being close to shopping, dining, schools, and local attractions. And if you love boating or an active outdoor lifestyle, you’ll appreciate the flexibility this neighborhood offers. This home isn’t just about square footage or upgrades—it’s about comfort, flexibility, and the feeling of finally finding the one. Come see it in person and imagine the life you could build here.

Listing is courtesy of: WATSON REALTY CORP. (407-589-1600)

Listing Agent: Katie Sweet (863-990-5141)

Remarks: Under contract-accepting backup offers. Welcome home to this beautiful 2-bedroom, 2-bathroom golf villa nestled within the beautiful Cypresswood Golf and Country Club in Winter Haven, Florida. Property is steps away from the golf clubhouse!!! Home features a stunning Florida room, ready for relaxation. Dry bar with sink in living room perfect for entertaining your guests. Step out to your outside patio for even more enjoyment. With access to golf, clubhouse, Restaurant, pool and recreational facilities, this home offers a low-maintenance lifestyle in an active and vibrant community. Legoland attraction is approximately 5 miles. Disney World, Orlando and Tampa attractions are within 30-60 minute driving distance. Opportunities like this don’t last long, Just buy and move in!!! CLEAN TITLE WITH NO LIENS. Property being sold AS-IS. ALL interior contents and furniture convey with the property.

Listing is courtesy of: SUCCESS INVESTMENT REALTY (407-304-0490)

Listing Agent: Bill Sprys (407-574-9724)

Remarks: This open concept 3-bedroom, 2-bath home is located in the Garden Grove part of Winter Haven. This home features a large living room/kitchen combo, with an updated kitchen with stainless steel appliances, granite countertops, wood cabinets, and a large bar perfect for family dining. The large bonus room has possibilities for many different rooms. The home has luxury vinyl plank throughout, updated bathrooms, double pane windows, and french doors for some of the interior features. Exterior features include A/C in 2024, drain field/septic in 2023, updated electrical panel. Outside also features a deck perfect for bbqing, large, fenced back yard, oversized driveway, and extra space for parking your toys. Oh yeah, and NO HOA! Call today to view! *Agents, please read MLS realtor remarks.*

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

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

Remarks: SELLER MOTIVATED! | NEW ROOF | NO CDD| GATED COMMUNITY Welcome home to 107 Mandolin Drive, a move-in ready, single-story gem nestled inside the sought-after Mandolin gated community in SE Winter Haven. This beautifully maintained 4-bedroom, 2-bath residence offers the perfect blend of comfort, style, and security, all with No CDD and a low HOA. A brand-new roof tops off a home that has been thoughtfully cared for inside and out. Soaring cathedral ceilings fill the open-concept living area with light and volume, creating an inviting atmosphere from the moment you walk in. The primary suite is a true retreat, featuring a spacious walk-in closet and a private en suite bath with a walk-in shower. A second bedroom also boasts its own walk-in closet, ideal for guests, family members, or a dedicated home office. The eat-in kitchen sits at the heart of the home and is designed for both function and connection, offering ample cabinetry, a breakfast bar, and all major appliances included. It flows seamlessly into the main living space — perfect for everything from weeknight dinners to weekend entertaining. Slide open the doors to your enclosed lanai, an ideal spot for morning coffee, game nights, or unwinding after a long day. The fully fenced backyard offers room to roam, bring your pets, your garden plans, or simply enjoy the open space. Prime location perks: -Minutes to the new Publix Supermarket, Legoland, shopping, dining & medical facilities -Zone for Chain of Lakes Elementary School -Easy access to both Tampa and Orlando. Gated living, modern updates, and an unbeatable SE Winter Haven address, this one checks every box. Schedule your private showing today.

Listing is courtesy of: CENTURY 21 MYERS REALTY (863-875-5656)

Listing Agent: Mabel Vassallo (863-604-0499)

Remarks: This Azure floor plan offers a welcoming formal entry and hallway. A spacious great room with kitchen is open to dining and family entertainment area that leads to a covered patio. Also included is a great sized primary bedroom with a primary bath and walk-in closet. Included features: 9"4' ceilings and 8' doors, 42' cabinets and white quartz counter tops in kitchen, ceramic tile throughout the wet and main living areas of the home. All bedrooms, family room, and covered lanai are prewired for ceiling fans. *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: Short Sale. Subject to lender approval. Property has sustained prior storm-related damage with documented mold and interior environmental conditions. Due to these conditions, interior access is limited and not suitable for routine showings. Property is being sold AS-IS and will require substantial remediation, including potential structural and electrical work. Access is restricted to serious, qualified buyers and must be coordinated with the listing agent. Property includes leased solar panels. Buyer to verify terms and assume existing lease. Buyer to verify all measurements, square footage, HOA, and property information.

Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)

Listing Agent: Hien Nguyen (479-926-7079)