Homes For Sale in Winter Haven 33881 - 289 homes

Remarks: Short Sale. SHORT SALE OPPORTUNITY PRICED TO SELL! This is a great opportunity to walk into equity in a newer home. Needs some minor TLC. Lucerne Park Reserve is located in historic Winter Haven only one mile from US-27 providing easy access to major employment centers. The home is located closely to town centers with plenty of restaurant and retail options. Meritage Home is Known for their energy efficient features. Low HOA of $200/year includes community pool and park

Listing is courtesy of: FOUNDATION REALTY GROUP (813-729-6000)

Listing Agent: Dana Cates (813-729-6000)

Remarks: Welcome to 2213 Rose Blvd in Winter Haven—a beautifully maintained and like-new 4 bedroom, 2 bath home offering over 1850 square feet of comfortable living within the Buckeye Ridge community. Perfectly positioned on a corner lot, this home showcases outstanding curb appeal and evident pride of ownership, enhanced by a freshly painted exterior accents, well cared for landscaping, decorative gable vents and carriage-style garage hardware for a custom look. A thoughtfully designed split-bedroom layout with open-concept living at its core, offering a seamless flow for everyday living and entertaining while maintaining privacy with a well-separated primary suite and generously sized secondary bedrooms. Tile flooring leads from the foyer into the great room and kitchen area, where brand-new wood laminate flooring and roomy dimensions provide an ideal level of easy living. The kitchen features an abundance of cabinetry and counter space, breakfast bar/center island, a walk-in pantry and included appliances. Dining space sits just off the kitchen with tranquil backyard views. The triple split-bedroom layout provides privacy and flexibility, highlighted by a generously sized primary suite with brand-new carpeting, a walk-in closet, and an en-suite bath complete with dual vanities, walk-in shower, large linen closet and private water closet. All guest bedrooms also have brand new carpeting and are spacious with easy access to the full guest bath. Step outside to your private outdoor oasis—featuring a screened patio that opens to a fully fenced backyard with vinyl fencing and irrigation system with timer to keep the yard green and lush—perfect for relaxing or hosting gatherings year-round. Additional notable features include an inside laundry room, double-pane windows, two-car garage, warranties on the new flooring, both gas and battery generator connections and a transfer switch for added peace of mind. Location is everything, and this home delivers—just minutes from vibrant downtown Winter Haven, Polk State College, medical facilities, shopping, restaurants as well as multiple golf courses and lakes to fully enjoy the Central Florida lifestyle. Centrally located between Orlando and Tampa, Winter Haven offers the perfect balance of small-town charm with convenient access to major roadways, shopping, dining, and world-class attractions. Homes in this condition with an ideal combination of upgrades and location are hard to find—schedule your private showing today!

Listing is courtesy of: THE STONES REAL ESTATE FIRM (863-412-2080)

Listing Agent: Michael Stone (863-412-9733)

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 beautiful 4-bedroom, 2-bathroom home located in the desirable Julius Estates community of Winter Haven! This well-maintained home offers a spacious and functional layout perfect for comfortable living and entertaining. Major updates provide peace of mind, including a NEW roof, NEW AC system, and NEW water heater. The home features a bright and open living area, generously sized bedrooms, and a private primary suite designed for relaxation. Enjoy the wonderful community amenities, including a pool and a lakefront dock on Lake Julius with access to the scenic Winter Haven Chain of Lakes perfect for boating, fishing, and enjoying Florida living at its finest. Conveniently located near shopping, dining, schools, and major roadways, this home offers both comfort and convenience. Don’t miss this opportunity to own a move-in ready home in a sought-after community. Schedule your private showing today!

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

Listing Agent: Stephanie Florez (407-810-5874)

Remarks: Charming and well-maintained 3 bedroom home located at 3015 Avenue I NW in a quiet, established Winter Haven neighborhood, freshly painted inside and out and ideal for first-time buyers or investors. The home features a bright, open layout with durable flooring throughout, a spacious kitchen with ample cabinet space, an updated roof, central AC, a covered carport, mature landscaping, no HOA, and a large backyard perfect for entertaining, gardening, or future expansion. The septic tank was inspected in December 2025 and is in normal working condition. Living in Winter Haven offers an exceptional lifestyle thanks to its renowned Chain of Lakes, including Lake Howard, Lake Cannon, and Lake Shipp, where residents enjoy boating, fishing, kayaking, and scenic sunsets, along with nearby attractions such as LEGOLAND Florida Resort, parks, and walking trails. The location is highly convenient, with easy access to US-17, US-92, the Polk Parkway (SR-570), and I-4, allowing for a smooth commute to Lakeland in approximately 20–25 minutes and to Orlando in about 45–55 minutes, depending on traffic. A standout advantage is proximity to Lakeland International Airport (LAL), a growing and less congested airport offering easy parking, quick check-in, and expanding domestic flights to major U.S. cities, as well as direct service to Puerto Rico, making travel for work, family, or leisure significantly more convenient. This property perfectly combines comfort, location, connectivity, and lifestyle value in the heart of Central Florida, making it an excellent option for buyers seeking quality and convenience.

Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)

Listing Agent: Omar Rodriguez (321-442-2001)

Remarks: Welcome home to Brenton Manor! This move-in ready 3-bedroom, 2-bathroom split-plan home checks every box — and then some. The open-concept kitchen flows seamlessly into the great room, creating the perfect space for entertaining or relaxing after a long day. Step outside to your private, fully fenced backyard with no rear neighbors — your own Florida oasis. Big-ticket updates have already been done for you: brand-new 2026 HVAC with UV ray lights and professionally cleaned ductwork, 2026 whole-home water softener system, 2025 tankless water heater, 2025 fresh exterior paint, 2025 gutters, and a 2023 roof. Both bathrooms feature updated showers, so all you need to do is move in and enjoy. Nestled in the established Brenton Manor community near US-27 and beautiful Lake Hamilton, this home offers the perfect blend of comfort, convenience, and peace of mind. Conveniently located minutes from I4 offering easy access to major roadways, downtown Orlando, MCO airport, short drive to theme parks, premier shopping, dining and world class health facilities. Schedule your private showing today!

Listing is courtesy of: COLDWELL BANKER REALTY (407-696-8000)

Listing Agent: Cynthia Davis (407-619-2937)

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: Completely remodeled and move-in ready, this stunning 2-bedroom, 2.5-bathroom condo in Casa Del Sol Village offers modern updates and a comfortable layout in the heart of Winter Haven. Every corner has been renovated, featuring new flooring, paint, lighting, kitchen appliances, doors, and beautifully updated bathrooms. The spacious living room and downstairs guest half-bath make entertaining a breeze, while both upstairs bedrooms boast private en-suite bathrooms for added convenience. Enjoy a low-maintenance lifestyle with an attached one-car garage, access to the community pool, and a location close to shops and restaurants—all amidst the beautiful landscapes and lakes that surround this lovely community.

Listing is courtesy of: WF REALTY CORP. (407-994-2900)

Listing Agent: Adriana Sanchez (321-947-4014)

Remarks: Welcome to a home where comfort, convenience, and peace of mind come together in one of Winter Haven’s most desirable and evolving areas. Nestled just minutes from the shores of Lake Howard and the charm of Downtown Winter Haven, this property offers the lifestyle so many are seeking—close to it all, yet tucked away in a quiet, established neighborhood.From the moment you arrive, you’ll appreciate the care and updates that make this home truly move-in ready. Major systems have already been taken care of for you, including a brand-new hot water heater installed in 2026, roof and HVAC systems both replaced in 2018, giving confidence for years to come. Inside all-new windows bring in natural light while improving energy efficiency. The home continues to shine with newer cabinets and updated appliances. The interior tells a story of thoughtful updates and everyday functionality—spaces that feel welcoming whether you’re hosting friends, enjoying a quiet evening, or simply living life comfortably. Every improvement has been made with both style and practicality in mind, allowing you to settle in without the stress of immediate projects.Step outside and you’re just moments away from everything that makes Winter Haven special. Spend your weekends enjoying the Chain of Lakes lifestyle at Lake Howard, take in the growing dining and entertainment scene downtown, or simply enjoy the continued growth and investment happening throughout the area—making this not just a great home, but a smart move for the future.If you’ve been looking for a home that blends updated features, prime location, and long-term value, this one checks all the boxes.

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

Listing Agent: Chris Loschiavo (863-280-2201)

Remarks: One or more photo(s) has been virtually staged. 4.99% Rate 30-year fixed FHA/VA Act now ! Step into this renovated farmhouse charm : 2-bedroom, 2-bathroom home, nestled on a spacious lot in the established Villa Manor neighborhood. NO HOA This move-in-ready residence presents luxury finishes, laminate flooring throughout, a sleek new kitchen with updated cabinets, carrara white quarts countertops, and stainless steel appliances, and a freshly tiled bathroom with contemporary finishes. Fresh interior and exterior paint, and upgraded lighting fixtures. The large backyard offers plenty of space for outdoor living or future expansion. Located minutes from local schools, parks, and downtown Winter Haven’s shops and restaurants, this home is perfect for first-time buyers, downsizers, or investors seeking turnkey potential.

Listing is courtesy of: KELLER WILLIAMS LEGACY REALTY (407-855-2222)

Listing Agent: Daniel Araque (321-276-0747)

Remarks: Under contract-accepting backup offers. A stunning home featuring three spacious bedrooms and two bathrooms with a desirable split bedroom plan. Built in 2021, this residence offers a generous 2,200 square feet under roof, seamlessly blending an open floor layout with the latest technology for exceptional value in one incredible package. Enjoy the convenience of a smart home with automated lighting, climate control, and advanced security access, all designed to bring comfort and efficiency right to your fingertips. The architectural roof is less than a year old, and the energy-efficient construction ensures lower utility costs and sustainable living. This property also includes a water softener, washer, and dryer, all of which stay with the home for added value. If buyers need assistance with closing costs, the seller is open to considering support, making this an even more attractive opportunity. Seller will leave Living room, dining room furniture, big screen tv in master, if buyer desires.

Listing is courtesy of: BROKER’S REALTY AND CONSULTING (863-557-3265)

Listing Agent: Patty Clemons (863-557-3265)

Remarks: Buyer Financing fell through! Their loss is your gain!! Turn key opportunity in the heart of Winter Haven! This 4-bedroom, 2-bath home comes partially furnished, Water filtration system already installed and is ready for its next owner whether you're looking for a primary residence, vacation home, or income producing investment. The home features a spacious, light-filled layout, a functional kitchen, comfortable bedrooms, and a screened in lanai perfect for enjoying Florida evenings. A NEW ROOF installed May 2025 with transferable warranty adds long-term value and peace of mind. Located in a quiet neighborhood just minutes from shopping, dining, lakes, parks, and LEGOLAND, this property offers both lifestyle and convenience in one of Winter Haven’s most desirable areas. With its furnished interior and flexible layout, this home is move-in ready and full of potential for homeowners or investors alike. Schedule your private showing today and see why this property stands out!

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

Listing Agent: Laura Medina Ruiz (863-207-4784)

Remarks: ? Back on Market – New Price Welcome to this move-in ready 4-bedroom, 2-bath home with a 2-car garage, perfectly situated on a rare nearly ½-acre oversized lot in Winter Haven! This home offers the space and updates today’s buyers are looking for — including a brand NEW roof and NEW A/C (2025), giving peace of mind and added value from day one. Step inside to a bright, open layout with updated flooring and plenty of room for both everyday living and entertaining. The spacious kitchen flows seamlessly into the main living area, creating a comfortable and inviting atmosphere. The flexible 4th bedroom with French doors can easily serve as a guest room, home office, or additional living space — tailored to your needs. Outside, the oversized lot is a true standout! Whether you’re dreaming of adding a pool, storing a boat or RV, or creating your own backyard oasis, this property gives you the space to make Conveniently located near shopping, dining, and major roadways while still offering room to spread out — a rare combination at this price point. Don’t miss your chance to own a home with space, updates, and flexibility — schedule your showing today!

Listing is courtesy of: FREEDOM REALTY (863-289-7004)

Listing Agent: Ike Fountain (863-206-1105)

Remarks: Welcome home to this beautifully renovated 2 bedroom, 2 bathroom residence that truly stands out from the rest. From the moment you step inside, you’ll notice the bright, open living space featuring stylish wood-look flooring, modern lighting, and a layout designed for both comfort and entertaining. The spacious primary suite features sliding glass doors that lead to a screened, covered lanai—now thoughtfully split to create a versatile bonus room, perfect for a home office, hobby space, or relaxing retreat. Step outside to the tiled patio, ideal for morning coffee, evening gatherings, or weekend BBQs. Enjoy low-maintenance living in a community that offers assigned covered parking, a community pool, and direct lake access to Lake Smart with a boat ramp—perfect for fishing, boating, and enjoying the Florida lifestyle. Conveniently located near shopping, dining, and medical facilities, this home offers both comfort and convenience. This move-in-ready unit is a rare find. Schedule your private showing today before it’s gone.

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

Listing Agent: Diana Acosta (914-562-3386)

Remarks: Turnkey quadplex ( 5 units) investment opportunity in Winter Haven This income-producing multifamily property features 4 of 5 units currently leased, delivering strong in-place cash flow with additional upside from one vacant unit. Recent capital improvements include a new metal roof, updated HVAC system, and multiple interior and exterior upgrades completed within the past year, reducing near-term maintenance exposure and supporting long-term returns. The property offers practical unit layouts, established tenancy, and is positioned in a high-demand rental corridor near retail, dining, schools, and major transportation routes. Continued growth and redevelopment throughout Winter Haven reinforce rental demand and long-term appreciation potential. An efficient addition to any rental portfolio, suited for investors pursuing passive income, portfolio expansion, or a structured value-add play. Seller financing terms enhance flexibility and can improve overall income depending on structure. Contact for financials, rent roll, and seller financing details.

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

Listing Agent: Michael Hochadel (863-604-0018)

Remarks: Back on market buyers financing fell through. Welcome home! Your forever home is located near downtown Winter Haven and just a short distance from Polk State College. Completely remodeled in 2021 with a New Roof, New A/C, New Water Heater, New Electrical system, new windows new kitchen (Quartz Countertops), new appliances, new floors (Vinyl). This home has a huge, oversized corner lot and with summer around the corner, this will be the place for all the summer BBQ's.

Listing is courtesy of: FLATFEE.COM (954-965-3990)

Listing Agent: Cliff Glansen

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

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

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

Remarks: Price Reduced. Excellent Investment Opportunity. Zoning MX district. Seller Motivated. Recived $10,000 toward buyers closing cost. Charming 1910 Colonial Home — Elegantly Renovated in Central Winter Haven. Welcome to timeless charm blended with modern comfort in this beautifully Colonial residence, perfectly situated in the heart of Winter Haven, Florida. Meticulously updated while honoring its historic character, this home offers the ideal blend of classic architectural details and contemporary living. As you approach, you’re greeted by a stately façade showcasing symmetrical Colonial proportions, a welcoming front porch, and original period craftsmanship that has stood the test of time. Current zoning classification is MX (Mixed-Use), which allows a wide range of commercial and residential uses. Typical permitted uses examples are: Professional and medical offices, Assisted living facilities, ALF) / senior care, Group homes and supportive housing, Multifamily residential buildings, Live/work units and mixed commercial-residential developments.

Listing is courtesy of: CENTRAL REALTY GROUP AND PROPERTIES (407-582-9011)

Listing Agent: Raul Briceno (407-715-2550)

Remarks: 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: Under contract-accepting backup offers. Accepting Backup Offers. Cash-flowing block duplex in Winter Haven, FL offering immediate income and upside, with (2) 2 bed / 1 bath units currently leased at $1,150/month & $1,200/Mo ($2,350/month total) to long-term tenants, providing stable day-one cash flow. Recent improvements include a brand-new roof (2023), privacy fence, and on-site storage shed with potential for additional income, while rents remain below market, presenting a straightforward opportunity to increase NOI through rent growth. Conveniently located near The Home Depot and major retail corridors, the property benefits from strong tenant demand, making it an attractive low-risk, value-add workforce housing investment in a growing Polk County submarket.

Listing is courtesy of: HANCO & ASSOCIATES (813-833-2185)

Listing Agent: Matthew Greezicki (813-833-2185)