Homes For Sale in Winter Haven 33881 - 346 homes

Remarks: Fully renovated 3BR/2BA home with an open space perfect for office or extra space located in Winter Haven NO HOA! New Roof, New AC, New Water Heater, New Flooring, New Kitchen Cabinets, updated bathrooms cabinets, and modern finishes throughout. Turn-key and move-in ready with a spacious yard and great location. Huge fenced backyard with banana trees Plus, NO HOA — enjoy more freedom and lower monthly costs Don’t miss it!

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

Listing Agent: Karina Turcios (407-346-7606)

Remarks: Under Construction. Brand-new 3-bedroom, 2.5-bath two-story townhome with garage in Winter Haven, FL. The open-concept main level features a spacious living area, flex space, powder room, and private covered lanai. The professionally designed kitchen includes a breakfast bar, 36-inch soft-close birch cabinets, premium laminate countertops, walk-in pantry, and Samsung stainless steel appliances. Upstairs, the owner’s suite offers a walk-in closet and en-suite bath with dual vanities and a tiled shower, while two additional bedrooms share a dual-vanity hall bath. Features include luxury vinyl plank flooring in main areas and baths, stain-resistant carpet in bedrooms, LED lighting, built-in pest control, and energy-efficient construction with Low-E windows, R-30 insulation, and a programmable thermostat. Move-in ready and easy to maintain.

Listing is courtesy of: CAMBRIDGE REALTY OF CENTRAL FL (863-797-4999)

Listing Agent: George Lindsey, Iii (863-797-4999)

Remarks: EXCELLENT INVESTMENT OPPORTUNITY IN THE HEART OF WINTER HAVEN! LOCATED AT 601 AVE U NE, THIS PROPERTY OFFERS INCREDIBLE POTENTIAL FOR RENTAL INCOME OR FUTURE DEVELOPMENT. WITH A SPACIOUS LOT AND SOLID STRUCTURE, IT'S PERFECT FOR INVESTORS LOOKING TO RENOVATE, RENT, OR FLIP. CONVENIENTLY SITUATED NEAR DOWNTOWN WINTER HAVEN, SCHOOLS, SHOPPING, AND MEDICAL FACILITIES, THIS LOCATION IS IDEAL FOR LONG-TERM TENANTS OR RESALE VALUE. BENEATH THE EXISTING CARPETING, YOU WILL FIND WELL-PRESERVED HARDWOOD FLOORING READY TO BE DISCOVERED AND ENJOYED. DO NOT MISS YOUR CHANCE TO OWN A PIECE OF RAPIDLY GROWING WINTER HAVEN-OPPORTUNITIES LIKE THIS DO NOT LAST LONG!

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

Listing Agent: Brian Reeves (877-366-2213)

Remarks: Come see this gorgeous 4-Bedroom Home in the beautiful community of Lucerne Park Reserve, Winter Haven, FL – a beautifully designed 4-bedroom, 2.5-bathroom home located in the amazing Lucerne Park Reserve community. Located in a prime corner lot, this home provides you a modern design, spacious living, and an incredible community that is perfect for families who are looking for comfort. Key Features: Spacious & Functional Layout: This is a designed 2,340 sq. ft. home with an open-concept living space, perfect for entertaining. It is located in a big Corner Lot with a Huge Fenced Backyard. It is perfect for you if you need some extra privacy or space for outdoor activities, pets, and even to build a pool! In addition, the property has an Air-Conditioned 2-Car Garage and some Extra Driveway Parking. In the second floor you will find the Loft that would be perfect for entertainment. You cannot miss the incredible Master Suite with a custom walk-in closet, designed for ultimate storage and organization. The property offers a beautifully upgraded open kitchen with a big island, perfect for family gatherings and entertaining guests. One of the most important features is that you will enjoy a Brand-New AC Unit. The property is Located in Winter Haven, Lucerne Park Reserve that is a peaceful, family-friendly community with beautiful surroundings, great amenities, and easy access to major attractions. The community is just Minutes away from LEGOLAND Florida Resort. You will get a close Access to the Winter Haven Chain of Lakes. The community is in an amazing location that is close to Downtown Winter Haven where you can Enjoy boutique shopping, fine dining, and cultural venues like The Ritz Theatre and Theatre Winter Haven. You will get into the major highways in just a few minutes with Easy access to Orlando, Tampa, and other major cities for work or entertainment. Don't miss the opportunity to see this beautiful corner lot property before it is gone! You can be the next owner and live in the after sought community of Lucerne Park Reserve! Come see it today!!

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

Listing Agent: Carlos Carreno Ledezma (407-580-2914)

Remarks: Looking for a peaceful lakefront pool home or well appointed AibBnB property? This beautiful 3-bedroom, 2-bath home sits on Lake Connie in Winter Haven’s northern Chain of Lakes and has been completely renovated to include a brand new roof, 4-ton A/C, luxury vinyl plank flooring, interior / exterior paint, and new water heater all installed in 2025. The interior living area includes new fixtures, new front and rear sliding glass doors. The kitchen features tons of solid wood cabinets, all new stainless steel appliances, and granite countertops. It includes both a breakfast area and a picturesque cutout with a stunning view of the pool area and lakefront! The laundry room is also built into the kitchen area and includes a unique custom built porthole window that provides both natural light and views to the Florida room and beyond. The kitchen flows into a large enclosed porch (Florida room) with tons of potential! It can include a second living room space, dining room, and even space for a game room or office area! The Florida room includes additional cabinets and a bar area with a granite countertop. From the Florida room you can access the screened open porch where you can enjoy views of boats cruising the lake, skiers cutting through the water, and bald eagles, ospreys, and herons scooping up fish! The primary bedroom features an en suite bathroom with jetted tub/shower, new vanity & fixtures, as well as a large closet. The 2nd bedroom also includes new ceiling fan and a large closet. The garage has been converted into the 3rd bedroom which is oversized with a very large closet and shiplap feature wall. Both bathrooms have been fully renovated with gorgeous subway tile in the showers, new ceramic tile floors and vanities with solid surfaces, as well a new toilets, and exhaust fans. Outside the house has been completely repainted including newly painted concrete from the front to the back of the property. The home features new screen in the pool cage, a brand new pool liner, with new multi-color LED pool light, as well as new light and fan fixtures on the back porch. There is a carport and large outdoor storage closet out front, and also a second driveway to park an extra vehicle or boat. The boathouse, which includes a roll-up door has also been newly painted is wired with electricity and could also function as a workshop. It features new lights, a new side door. The boathouse / workshop is approximately 10x20 feet and has tons of room for all your toys! The property includes its own large dock and a concrete slab along the beach area for launching your own boat. Furnishings in listing are available for separate purchase. As a potential AirBnB, the unit currently sleeps 7 including the pull out couch in the living room, but could potentially sleep 10 with the addition of a second bed in the 3rd bedroom and a second pull out couch in the enclosed porch area.

Listing is courtesy of: HOMECOIN.COM (888-400-2513)

Listing Agent: Jonathan Minerick (888-400-2513)

Remarks: Welcome to your dream lakefront retreat on picturesque Lake Rochelle, part of Winter Haven’s famous Chain O’ Lakes! This beautiful two-story, 4-bedroom, 2.5-bath home combines comfort, style, and Florida living at its finest. Step inside to a bright and spacious living room featuring stunning cathedral ceilings and breathtaking lake views. The kitchen offers ample counter space, a large pantry, and an inviting layout perfect for entertaining or family gatherings. The master bedroom is on the first floor with a walk-in closet and a stunning view to the lake. Upstairs loft area with 3 additional bedrooms and a jack-and-jill bathroom. Convenience meets functionality with a downstairs laundry room, two-car garage, and long driveway providing plenty of parking. The exterior has been freshly painted, giving the home a crisp, updated look that complements its serene waterfront setting. Enjoy mornings with coffee by the lake and evenings watching sunsets reflected on the water. Located just minutes from LEGOLAND, 30 minutes from Disney, and only two hours from both Florida coasts, you’ll have endless recreation and adventure at your doorstep. This lakefront gem blends natural beauty, modern comfort, and an unbeatable location — the perfect place to call home in the heart of Winter Haven, FL. Use Showtime feature to schedule your viewing.

Listing is courtesy of: GATAP REALTY (352-978-5459)

Listing Agent: Roberta San Juan (786-256-1139)

Remarks: Calling all investors and house-hackers! Welcome to 1830 2nd St NW, a fantastic multi-family investment opportunity located right in the heart of Winter Haven. This well-maintained duplex features two spacious, mirror-image units, each offering a highly desirable 3-bedroom, 1-bathroom layout perfect for maximizing rental income and attracting long-term tenants! Both units boast bright, open-concept floor plans designed for easy living and low maintenance. Step inside to find durable ceramic tile flooring flowing seamlessly throughout the main living areas and kitchens, paired with crisp, neutral paint that makes the space feel fresh and inviting. The kitchens are fully equipped with rich wood cabinetry, ample counter prep space, white appliances (including dishwashers!), and a convenient breakfast bar/passthrough that overlooks the spacious family room. To top it off, each unit includes its own dedicated in-unit laundry closet with a stackable washer and dryer—a major premium for prospective renters.

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

Listing Agent: John Gomez (321-557-5652)

Remarks: Welcome to this beautifully renovated 3-bedroom, 2-bath home located in the heart of Winter Haven. Thoughtfully updated with modern finishes while maintaining its charm, this spacious property offers flexible living areas and plenty of room to spread out. Recent renovations provide a fresh, move-in-ready feel throughout the home. Previous owners added extra rooms and expanded living spaces, offering versatility for a home office, guest space, or bonus room. Square footage to be confirmed by buyer, as additions may not reflect current public records. Conveniently located near shopping, dining, schools, and all that Winter Haven has to offer, this property is a fantastic opportunity for homeowners or investors alike.

Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)

Listing Agent: Patrick Massey (931-337-1678)

Remarks: Welcome home to this inviting upstairs condo located in the peaceful Lake Buckeye Condo community, where tranquil lake views and relaxed living come together. Step inside to find laminate and ceramic tile flooring throughout, offering both durability and easy maintenance. The open living and dining area is light and welcoming, seamlessly extending to a private 3x7 balcony, the perfect place to enjoy your morning coffee or unwind at the end of the day. Just beyond, the well-appointed kitchen comes complete with all appliances, granite countertops, and an adjacent utility room with washer/dryer hookups and extra cabinet storage. The split-bedroom floor plan provides excellent privacy. The primary suite features a walk-in closet and a private en-suite bathroom with a walk-in tile shower, while the second bedroom is conveniently located near the hall bath, ideal for guests or a home office. Residents enjoy access to community amenities, including a sparkling pool overlooking beautiful Lake Buckeye and community docks, perfect for lakeside relaxation and peaceful views. This condo offers a wonderful blend of comfort, convenience, and serene surroundings—an opportunity you won’t want to miss!

Listing is courtesy of: STAR REALTY OF WINTER HAVEN (863-299-7827)

Listing Agent: Carlee Marchetti (863-258-3338)

Remarks: Opportunities like this are nearly extinct. Just minutes from Winter Haven Country Club, this remarkable estate offers 10.98 acres of privacy, natural beauty, and flexibility in one of Winter Haven’s most coveted and tightly held locations—where land, space, and convenience rarely coexist. The 3,800 sq ft main residence has been completely remodeled with a refined, modern vision that blends luxury with everyday livability. Designed for both entertaining and comfortable living, the open-concept layout showcases luxury vinyl plank flooring throughout, expansive living areas, and a beautifully upgraded chef’s kitchen that serves as the heart of the home. With 4 bedrooms and 4 full bathrooms, the residence provides generous space for family and guests alike. Outdoors, a private pool invites relaxation while remaining surrounded by peaceful, natural views. Adding exceptional value and versatility, the property includes a 1,300 sq ft detached guest house featuring 2 bedrooms and 2 bathrooms, along with an upgraded kitchen and bath—ideal for extended family, long-term guests, or a private work-from-home or creative space. The land itself is what truly sets this property apart. The nearly 11-acre setting offers a thoughtful balance of open usable acreage, mature landscaping, and a scenic private pond, creating a sense of separation and tranquility that enhances both privacy and lifestyle. Multiple outbuildings, including a barn/garage and lean-to structure, provide ample room for storage, hobbies, equipment, or future expansion. In a market where acreage is disappearing and privacy is priceless, properties offering this scale of land, level of renovation, and proximity to town are exceptionally rare. This is not just a home—it’s a private retreat, a long-term asset, and an opportunity to own something truly irreplaceable.

Listing is courtesy of: THE MARKET REALTY COMPANY (863-999-4643)

Listing Agent: Brock Jennings (863-990-5846)

Remarks: Seller motivated — great opportunity for investors or future homeowners! This beautiful corner lot home features 4 bedrooms and 2 bathrooms, offering comfort, space, and excellent income potential. The spacious kitchen comes fully equipped with all appliances, including a refrigerator, stove, microwave, and dishwasher, making it move-in ready from day one. The open-concept layout seamlessly connects the living and dining areas, creating the perfect space for entertaining guests or enjoying everyday family life. Sliding glass doors lead to a large backyard, ideal for outdoor activities, gatherings, or simply relaxing. Additional highlights include a 2-car garage, an already equipped laundry room, and a well-designed floor plan that offers both functionality and comfort. Located in the desirable Lake Lucerne community, residents enjoy great amenities, including a clubhouse, swimming pools, playground, and sidewalks for walking. Conveniently situated near Lake Alfred Elementary School, Daniel Jenkins Academy, Haines City Senior High School, as well as shopping, restaurants, and major roads with easy access to US-27, making commuting to Winter Haven, Davenport, and Orlando attractions even more convenient. Investor alert: The property is currently tenant-occupied with a lease in place through November 2026, generating $1,950/month in rental income. After the lease term ends, the new owner may choose to renew the lease or have the tenant vacate. Don’t miss this incredible opportunity!

Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)

Listing Agent: Anderson Siqueira, Sr (407-912-4688)

Remarks: Charming Inwood home, located one block to lake Alfred. This 3 bedroom , 2 bathroom is perfect for 1st time home buyer or as an investment property. Its close to school and shopping. The drain field was done approximately 8 mths ago, New kitchen cabinets were put in, also both toilets and vanity, plus a new hot water tank. Please note that the hose will need a new A/C unit., however if the buyer does not want to put in new central air then they can use the window AC units(4). The house does not comes with appliances, there is a refrigerator in the garage that can be used in the kitchen.

Listing is courtesy of: LIBERTY HOME SALES INC (321-256-0500)

Listing Agent: Baijnauth Singh (212-518-7621)

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: One or more photo(s) has been virtually staged. Welcome to 6450 Hollyberry Lane in Brookhaven Village—a highly sought-after 55+ community where you own your land, making this a rare opportunity! This beautifully updated, move-in ready home features new luxury vinyl flooring (2025) and a bright, open layout perfect for everyday living and entertaining. The upgraded kitchen offers butcher block countertops, slide-out metal racks for added storage, and a brand-new dishwasher. Washer and dryer are included. Both bathrooms have been beautifully remodeled with modern finishes. Major updates include a new roof (Dec 2024), new HVAC system (2025) with ductwork and air handler, new windows (2025), and all-new screening, including the lanai with vinyl windows—perfect for enjoying Florida living year-round. The home is also fully replumbed with updated anchors and straps, including a vapor barrier that was installed about 4 years ago. The home also includes a great storage shed/workshop—ideal for hobbies or extra storage. Enjoy a super low HOA with access to a community pool and clubhouse, all in the heart of Winter Haven near shopping, dining, and lakes. Fully updated + land ownership + prime 55+ community—this one stands out. Schedule your showing today!

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

Listing Agent: David Small (407-601-8351)

Remarks: "Welcome to this charming 3-bedroom, 3-full-bath home nestled in the heart of Winter Haven! One of the bedrooms features a private entrance, making it perfect as an IN-LAW SUITE, home office/studio, or an income-producing rental opportunity. The spacious Florida room with screen enclosure is ideal for relaxing and entertaining, while the front screened porch adds extra curb appeal and a cozy outdoor living space. The generous backyard offers endless possibilities, plenty of room to add a pool, create your dream outdoor oasis, or simply enjoy the open space. A storage shed with electricity in the back provides additional convenience and storage. Enjoy pure, clean water throughout the entire home with a whole-house reverse osmosis filtration system. Located on a quiet dead-end street with no through traffic. No HOA, No CDD, low taxes, public water and sewer. Just minutes from Downtown Winter Haven, shopping, restaurants, and the beautiful Winter Haven Chain of Lakes. This home has so much to offer, don't miss this opportunity! Equal Housing Opportunity."

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

Listing Agent: Romina Peragine, Pllc (407-288-4595)

Remarks: Located in the desirable Harrington subdivision of Winter Haven, this beautifully single-family home offers the perfect blend of comfort, style, and value. Featuring 3 spacious bedrooms and 1 bathroom, the home showcases a bright open-concept layout ideal for modern living. The kitchen boasts granite countertops, stainless steel appliances, and ample cabinet space. Enjoy durable vinyl plank flooring throughout, generously sized bedrooms, and an abundance of natural light. Step outside to a large backyard, perfect for entertaining or relaxing. Conveniently situated near schools, parks, hospitals, dining, and entertainment. Priced to sell, schedule your showing today!

Listing is courtesy of: PREMIUM PROPERTIES R.E. SERVICE (407-380-2800)

Listing Agent: Hamid Dghirni (407-575-2891)

Remarks: HUGE PRICE DROP! Welcome to this 2-bedroom, 1.5-bath condo in the desirable 55+ community of Winter Haven Harbour Apartments! This beautifully updated unit is modern, stylish, and completely move-in ready. Inside, the condo has been freshly painted and features luxury vinyl plank flooring in living areas and tile in kitchen and baths. Both bathrooms have been fully redone with modern finishes. The main bath features granite countertops and a stand-up shower with a built-in seat for added comfort and accessibility. The updated kitchen offers ample cabinetry, storage, and beautiful Granite counter tops. Important updates include a 2021 water heater and all new storm windows installed last year. An additional bonus is the private storage closet located next to the elevator; approximately 4x6 feet with floor-to-ceiling space. This active 55+ community offers a welcoming community center complete with a fitness center, library, and pool table. Outside near the heated pool, you’ll find a beautiful friendship garden with seating and a fire pit — the perfect spot to relax or gather with neighbors. Residents also enjoy pickleball courts, shuffleboard, and a grilling area ideal for social events and sunny Florida afternoons. Conveniently located near shopping, dining, medical facilities, and positioned between Tampa and Orlando. If you’re looking for updated, modern living in a vibrant and friendly 55+ community, this top-floor gem checks all the boxes. Schedule your private showing today!

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

Listing Agent: David Small (407-601-8351)

Remarks: Welcome to Fairview Village, an active 55+ gated waterfront community in Winter Haven. This charming 2-bedroom home offers peaceful canal and lake views, with private access to the water between Lake Hamilton and Lake Henry—perfect for boating and fishing. The community features a 99-year land lease and a low HOA fee of just $90 per month, which includes water and sewer. Residents enjoy a heated swimming pool with nearby restrooms and changing facilities, well-kept shuffleboard courts, coin laundry, and secure RV/boat storage available for an additional fee. The clubhouse serves as the heart of the community, hosting a full calendar of events such as breakfasts, dinners, bingo, cards, billiards, ping pong, dances, shuffleboard, horseshoes, and more. Please note that this is a no-pet community. Fairview Village offers an inviting, active lifestyle with beautiful waterfront surroundings.

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

Listing Agent: Sandra Perry (978-273-0601)

Remarks: Under contract-accepting backup offers. Welcome to 3108 Buckeye Point Dr — where comfort meets convenience in the heart of Winter Haven. From the moment you arrive, this home invites you in with a layout designed for the way you truly live. With 4 bedrooms and 2 full bath and a brand new A/C system the living spaces feel open yet connected, creating an easy flow for both everyday routines and weekend gatherings. Natural light enhances the home’s warmth, while thoughtful design elements make each space feel intentional and livable. The kitchen serves as the hub of the home, seamlessly connecting to the main living areas — ideal for hosting, relaxing, or simply enjoying a quiet night in. The primary suite offers a private retreat, while additional rooms provide flexibility for guests, work-from-home needs, or hobbies. Step outside and imagine morning coffee, evening unwinding, and effortless Florida living in your own outdoor space. Located in a desirable Winter Haven community, you’ll appreciate the convenience to shopping, dining, medical facilities, schools, and major roadways — all while enjoying the feel of a tucked-away neighborhood setting. Homes that combine layout, location, and livability like this don’t stay available for long. Schedule your private showing and experience 3108 Buckeye Point Dr for yourself.

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

Listing Agent: Jp Phillips (863-670-7923)

Remarks: Spacious single-family home featuring 4 bedrooms and 2.5 bathrooms with approximately 3,160 sq ft of living space, offering a functional and flexible floor plan. The main level includes a private office with French doors, ideal for use as a home office or optional fifth bedroom. Generous interior spaces provide comfortable living and well-sized bedrooms throughout. Conveniently located in Winter Haven, with easy access to major roads, shopping, dining, and everyday conveniences. This property offers an excellent opportunity for buyers seeking space, versatility, and a well-established residential setting.

Listing is courtesy of: LA ROSA REALTY LLC (321-939-3748)

Listing Agent: Maria Chavez (407-866-4682)