Homes For Sale in Winter Haven 33880 - 210 homes

Remarks: Charming 3-Bedroom, 2-Bathroom Home in Squires Grove – Move-In Ready! Welcome to this beautifully maintained 3-bedroom, 2-bathroom home located in the desirable Squires Grove subdivision. This move-in ready property offers modern updates and thoughtful features that make it the perfect place to call home. Step inside to find brand new commercial-grade waterproof laminate flooring throughout, adding both durability and style. The spacious living room is perfect for relaxing or entertaining, while the kitchen includes a cozy eating area ideal for casual family meals. Enjoy Florida living at its best with a screened-in back patio, complete with lighting and tile flooring—a great spot for morning coffee or evening gatherings. The patio opens up to a beautiful back yard, offering added peace and privacy. BRAND NEW A/C system installed in March 2025, ensuring comfort year-round. Conveniently located near schools, shopping centers, and parks. Don’t miss this opportunity !

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

Listing Agent: Tony Fridovich (863-698-4267)

Remarks: Move In Ready 3BR/2BA + Home Office + Dining / Flex Room and Large Screened Lanai. The Interior Features an Open Floor Plan, High Ceilings, Spacious Bedrooms, New & Updated Lighting & Fans, Fresh Interior Paint, Brand New Carpet in BR's and more! The Large Kitchen Offers a Spacious Breakfast Cafe Overlooking the Lanai & Backyard, Newer Countertops, Tiled Backsplash and New Dishwasher. The Master Suite Offers a Huge Walk-In Closet, Soaking Tub, Double Vanities and Walk-In Shower. The Exterior Offers a Fully Privacy Fence, Large Backyard and Newer Storage Shed. Please Note the Property Link extends another 14' beyond the rear fence. This Gated Community is conveniently located in Winter Haven close to Publix Shopping, Walmart, Restaurants and Legoland. Enjoy all that Winter Haven has to offer - Multiple Lakes for fishing & boating, Nature Trails, Golf Courses and more. Located One Hour from both Tampa and Orlando International Airports, Lakeland Linder Airport now offering domestic flights too.

Listing is courtesy of: SHAWN R MCDONALD REALTYGRP INC (863-287-0213)

Listing Agent: Shawn Mcdonald (863-287-0213)

Remarks: Located in the heart of downtown Winter Haven, FL, this versatile R-3 zoned property presents an excellent opportunity for homeowners, investors, or those seeking future development potential! This charming residence features 2 bedrooms and 1 full bathroom, offering a functional layout with comfortable living spaces. The home includes a spacious kitchen with ample cabinetry and room for dining, perfect for everyday living or rental use. A dedicated utility room adds convenience and extra storage space. Connected to city water and sewer, this property provides reliable infrastructure and ease of maintenance. The R-3 zoning allows for a variety of potential uses (buyer to verify with city) making this a flexible investment in a growing and desirable downtown location. Enjoy close proximity to local shops, dining, parks, and all that Winter Haven has to offer, including its renowned chain of lakes! Whether you're looking for a primary residence, rental property, or future development opportunity - this property checks all the boxes!

Listing is courtesy of: RE/MAX REALTY PLUS (863-385-0077)

Listing Agent: Emily Jones (863-446-3246)

Remarks: This is a beautiful condo located in the heart of Downtown Winter Haven, FL. The sunsets over Lake Howard are unbelievably gorgeous and can be enjoyed sitting on either patio overlooking the waterfront. This is an end unit that comes with 2 covered parking spaces located directly underneath the space. A must see.

Listing is courtesy of: COLLANY PROPERTIES (863-295-9886)

Listing Agent: Christopher Collany (863-412-2170)

Remarks: **PRICE IMPROVEMENT** MAINTENCE-FREE LIVING...Located right in the Heart of Winter Haven at Imperial Villas, a 55+ community. This very well maintained 2 Bedroom/ 2 Bathroom Villa that offers a complete update, boasting tasteful renovations throughout. Being sold Fully Furnished! From the kitchen to the bathrooms, flooring to the roof, nearly everything has been thoughtfully upgraded. Step inside to discover new ceramic tile and luxury vinyl flooring that sets a modern tone. The kitchen showcases stainless steel appliances, granite countertops, ample cabinet and countertop space. Retreat to the owner's suite at the back of the villa, offering a beautifully tiled walk-in shower and a generous walk-in closet. Through the great room, step into to enclosed lanai. Updates include: Roof (2020), Electrical Panel (2023), HVAC (2012) & Tankless Hot Water Heater (2018). Residents of this community have access to a refreshing pool, making it perfect for leisurely afternoons. The low HOA fee of $270/month covers water, internet, cable, gas, trash and grounds maintenance, ensuring a hassle-free lifestyle. Conveniently located just a short walk from the picturesque Lake Howard and minutes away from downtown Winter Haven. You'll have easy access to charming shops, delectable restaurants, the historic Ritz Theater, and vibrant events like farmers markets in the park. Don't miss out on the opportunity to make this your new home. Schedule your private showing today and experience the epitome of Florida living!!

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

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

Remarks: You will fall in love with this home from the time you walk through the front door. Has so much to offer, Has rear screen porch and backs up to drainage ditch. Roof is less than a year old and C/H/A is approximately two years. All main furniture will stay. Located in a 55 plus co op with low maintenance fees. Community is gated and has two club houses, two heated pools, Tennis,fishing pier plus much more. This home want last.

Listing is courtesy of: SOUTHERN BELLE REALTY (863-299-7800)

Listing Agent: Reta Stead (863-299-7800)

Remarks: Welcome to your move in ready home in Oakwood Estates, a gated community designed for those aged 55 and older. This beautifully maintained 2-bedroom, 2-bathroom manufactured home comes fully furnished and is being sold as-is, allowing you to move in comfortably without additional expenses. The double panes windows add thermal efficiency, and the 2014 shingle roof is in great condition . Features Include: - Two spacious bedrooms (split bedroom ) and bathrooms - Two attached screened-in porches, perfect for enjoying the Florida sunshine - Utility shed for additional storage (houses washer/dryer) - Parking space for two vehicles - Access to community amenities, including swimming, shuffleboard, fishing pier, and tennis Location: Conveniently located close to shopping centers and restaurants, everything you need is just a short drive away. Enjoy a vibrant community lifestyle with various social activities and events right at your doorstep. This section is a “No Dog” area but other inside pets are acceptable (cat, bird, fish)

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

Listing Agent: Andi Gamble (954-235-7723)

Remarks: Open and spacious living area is the best way to describe this home. The home features two living areas plus the lanai for additional space. The primary bedroom is large offering two built in closets and a spacious bathroom. The guest bedroom has the bath attached, perfect for visiting guests. The kitchen has an updated island perfect for entertaining. The laundry is located inside the home. Move right into this home, perfect for full time living and spacious for entertaining all the visitors you may have. The TPO roof was installed in 2022 and the ac is 10 years old. Oakwood Estates is a 55+ communities with lots of amenities including two clubhouses, two pools, miniature golf, shuffleboard, tennis courts, and much more. There are activities every day. You can join in or just sit back and enjoy the peaceful community.

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

Listing Agent: Kathy Devor (573-450-1679)

Remarks: One or more photo(s) has been virtually staged. SELLER IS MOTIVATED!!! RENTAL POTENTIAL!!! NO HOA!!! 20 MINUTES AWAY FROM LEGOLAND!!! NEW FLOORING INSTALLED IN FEBRUARY 2026!!!! NEW ROOF INSTALLED IN 2022!!! This 3-bedroom, 2-bathroom home offers the perfect combination of comfort, functionality, and location. The property features a screened-in back porch overlooking a private, fully fenced backyard — ideal for relaxing or entertaining. Enjoy your own private pool with both shallow and deep areas, perfect for family fun or hosting guests. The backyard also includes an area of synthetic grass and a basketball hoop, creating a versatile outdoor space for all ages. A standout feature of this home is the spacious storage shed, thoughtfully divided into two areas. One half is fully set up as an office, complete with a wooden desk, chair, wall-mounted whiteboard, and air conditioning — perfect for working from home. The other half offers additional storage space. The home was extensively updated, with a new roof installed in 2022, along with renovations completed the same year. The flooring was replaced in February 2026, giving the home a fresh, modern feel. High-quality, newer appliances add both style and functionality to the kitchen. Conveniently located just 20 minutes from LEGOLAND Florida Resort and about one hour from Tampa and the beautiful beaches of Florida’s west coast. You’re also just minutes away from Publix, McDonald's, restaurants, and everyday conveniences. The seller is highly motivated and welcomes offers — don’t miss this opportunity!

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

Listing Agent: Julia Ferreira (352-298-7325)

Remarks: Under contract-accepting backup offers. Charming 3-bedroom, 2-bath home located in Winter Haven. This property features granite countertops and ceramic tile flooring throughout. The original carport has been converted into a third bedroom and is currently utilized as a spacious primary suite. Ideal opportunity for first-time homebuyers or investors seeking a potential rental property. Conveniently located near shopping, dining, and local amenities. Ready to move in!

Listing is courtesy of: AGENT GROUP REALTY (843-656-0550)

Listing Agent: John Wiertel (863-289-0447)

Remarks: Welcome to your move-in-ready dream home! This charming 3-bedroom, 2-bathroom split-family residence features a spacious living room serves as the heart of the home, providing a seamless flow into the primary bedroom, which boasts an ensuite bathroom and a walk-in closet for maximum convenience. Just off the living room, you'll find a well-designed kitchen, complete with all major appliances, perfect for meal preparation and entertaining. The adjacent dining room offers direct access to the backyard with no rear neighbors overlooking a ranch, creating an ideal setting for outdoor gatherings or quiet relaxation. For even more living space, family room sits just off the kitchen, providing easy access to the backyard as well, making indoor-outdoor living a breeze. Bedrooms 2 and 3 are thoughtfully tucked away off the family room, sharing a conveniently located full bathroom. The nearby laundry room adds to the home's functional layout, ensuring practicality and ease of living. With its open floor plan and quiet outdoor space, this home is perfect for families seeking both comfort and convenience. Located just minutes from Polk parkway, shopping, grocery stores, and only 20 minutes from LEGOLAND, this home offers everything you need for easy, everyday living. Don't miss your chance to make this beautiful property your own!

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

Listing Agent: Emory Dant, Jr (863-812-7521)

Remarks: Welcome to 2849 Cathy Blvd, Winter Haven, FL 33880—a beautifully designed ranch-style home offering an airy, open-concept layout centered around a spacious great room and a modern kitchen, perfect for both everyday living and entertaining. The kitchen features quartz countertops, stainless steel appliances, and elegant 42" white upper cabinets, while the bathrooms showcase cultured marble finishes for a clean, polished look. The private primary suite includes a generously sized bedroom, a large en-suite bath, and a walk-in closet. Step outside to enjoy the covered screened in patio—ideal for relaxing or hosting gatherings year-round with the privacy of your fenced in yard!. All appliances included, adds to the home’s move-in ready appeal. Conveniently located in Winter Haven, this home offers easy access to shopping, dining, and entertainment, including nearby grocery stores, local restaurants, and parks. Just a short drive to downtown Winter Haven, you can enjoy the Chain of Lakes, outdoor recreation, and community events. With close proximity to major roadways, commuting to Lakeland, Orlando, and surrounding areas is a breeze.

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III (407-207-0825)

Listing Agent: Krichely Gonzalez Rodriguez (407-953-4377)

Remarks: One or more photo(s) has been virtually staged. 943 Summer Glen Dr is a spacious and well-maintained home offering exceptional value in the heart of Winter Haven. This move-in-ready residence features a functional, open floor plan designed for modern living and effortless entertaining. The bright, airy interior flows seamlessly into versatile living spaces, including a comfortable primary suite and additional bedrooms perfect for a growing family or a dedicated home office. Positioned in a quiet, family-oriented community, this property sits just moments from top-rated schools like Lake Shipp Elementary and the renowned Jewett School of the Arts. Residents enjoy immediate access to the Chain of Lakes for premier boating and fishing, as well as the dining and boutiques of historic downtown Winter Haven. Perfectly situated between Orlando and Tampa, this home provides a high-quality lifestyle and significant appreciation potential without the metropolitan price tag. Schedule your private showing today to discover why 943 Summer Glen Dr is the perfect place to start your next chapter!

Listing is courtesy of: KELLER WILLIAMS REALTY AT THE LAKES (407-566-1800)

Listing Agent: Stacey Vazquez (407-874-5751)

Remarks: UPDATED condo. NEW Bathroom Vanity & fresh Paint throughout. Price Improvement & Great opportunity to add your personal style to this 2 bedroom 2 full bath condo in Park Lake. Located on the 2nd floor close to the elevator with tremendous rental returns. Luxury Vinyl flooring in main living area & primary bedroom. Gas range & Water Heater. Ceiling fans throughout...Roof 2021...Washer/Dryer included with private laundry closet. NEW Dishwasher & Gas Stove just installed. NEW 5T 14 Seer AC just installed. Wet Bar...Terrific view from the back of the newly renovated baseball complex. Walking distance to restaurants & NEWLY RENOVATED BASEBALL COMPLEX. View of Lake Lulu with lake access for fishing off the dock. Primary bedroom offers a walk-in closet & natural light. This building offers an elevator & stairs as well as 1 dedicated parking space. Priced to sell & Perfect for Snowbird or Investor!

Listing is courtesy of: FOLIO REALTY LLC (407-917-0241)

Listing Agent: Dora Siler (407-493-4959)

Remarks: Stop looking now!This well kept home is waiting just for you. A nice 3/2 with tile and laminate thorough. This home offers a beautiful back yard with a deck for a peaceful retreat for enjoyment of the lake. Schedule your showing now.

Listing is courtesy of: PROPERTY WAREHOUSES OF AMERICA (321-234-2683)

Listing Agent: Louis Vincent (321-436-9220)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Nearly 5 acres of fenced and cross-fenced land offering privacy and room to spread out. This 3-bedroom, 2 bath split plan home features an open living and dining area filled with natural light and a large, screened lanai overlooking the property. The private primary suite includes a walk-in closet, granite counters, soaking tub, and separate shower. Two additional bedrooms share a hall bath, and there is an indoor laundry for convenience. Outside you’ll find a 2-car carport and detached garage/workshop, plus plenty of space for animals, gardens, or outdoor projects. This corner lot property gives you the freedom of country living while still being just minutes from shopping, dining, and major roadways.

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

Listing Agent: Melissa Ramirez (813-956-1071)

Remarks: Under contract-accepting backup offers. Pack your bags and move right into this beautiful home. The kitchen was remodeled three years ago. The side porch/lanai adds approximately 200 sf of living space (included in total sf) and is vented with central air. The home features beautiful built ins in the dining area as well as the 2nd bedroom. The primary bathroom has an updated shower and vanity. The shingled roof is 11 years old and the ac is 12 years old. The home comes furnished. Walk through the new sliding door to the front porch which features tinted windows and Berber carpet. This home is located in the Dog area where you can have two pets up to 20lb each. Enjoy Oakwood Estates, a peaceful 55+ community offering many amenities and activities, or just sit on the front porch and watch the world go by. This home is located in the area of Oakwood Estates that allows dogs. There is a 2 pet limit of up to 20 lbs.

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

Listing Agent: Kathy Devor (573-450-1679)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Discover comfortable, low-maintenance living in this inviting 2 bedroom, 2 bath villa located in a small 55+ community in Winter Haven. This well-designed home features vaulted ceilings, great natural light, and a spacious split bedroom layout, giving you and your guests plenty of privacy. Both bedrooms offer generous proportions and walk-in closets, and the primary suite includes a convenient step-in shower.The living room opens to a 12x12 covered patio through sliding glass doors, creating an easy indoor-outdoor flow for relaxing or enjoying fresh air. The one-car garage includes an electric roll-down screen, perfect for ventilation while keeping the space shaded and tidy. Additional highlights include a whole-house water treatment and softener, plus a new roof in 2024 for added peace of mind.The low HOA covers exterior paint, building and roof maintenance, irrigation system repairs, the community wall, and road upkeep, making day-to-day living simple and stress free.This community offers a convenient location near the bus line, medical offices, hospitals, shopping, and dining. You are also close to Winter Haven’s vibrant downtown filled with boutiques, restaurants, and year-round events, along with the city’s beautiful Chain of Lakes known for boating, fishing, and waterfront dining. Ideal for full-time residents or seasonal buyers looking for comfort, convenience, and a welcoming 55+ setting.

Listing is courtesy of: KEYSTONE RESIDENTIAL GROUP LLC (407-556-3249)

Listing Agent: Lisa Bertossa (407-709-1447)

Remarks: Honey, stop the car! This is the one you’ve been waiting for. This beautifully maintained 4-bedroom, 2-bathroom home sits on a spacious 0.45-acre fenced lot, offering the space, privacy, and outdoor lifestyle today’s buyers are searching for. Enjoy the soon-to-be easy access to Avalon and Disney via Sawgrass Rd extension. Step inside and you’re welcomed by a spacious foyer that flows into a cozy sitting area and formal dining room—perfect for gathering with family or entertaining guests. The open-concept kitchen features a charming breakfast nook and overlooks the main living area, creating a warm, connected space where everyone can come together. The private primary suite is a true retreat, complete with dual vanities, a relaxing soaking tub, a walk-in shower, and a large walk-in closet. The split floor plan provides privacy for everyone, while soaring high ceilings throughout the home create a bright and airy feel. Step outside and discover what truly sets this property apart—an outdoor entertainer’s dream. The covered paver lanai opens to a massive fenced backyard with endless possibilities for entertaining, gardening, play, or simply enjoying peaceful Florida evenings. Additional highlights include: New roof installed in 2021 Covered paver lanai perfect for outdoor gatherings Large private backyard with storage shed Two-car garage Interior laundry room Move-in ready condition in a quiet, established neighborhood Homes with this much space, privacy, and charm don’t come around often. Don’t miss your chance—schedule your private showing today before someone else calls it home.

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

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

Remarks: Some homes are built. Others are crafted. Tucked away in a quiet Winter Haven neighborhood, 4599 Reynosa Drive is a rare, cedar-constructed residence that blends artisan craftsmanship with modern efficiency. From the moment you arrive, the home sets itself apart fully fenced with new vinyl fencing, enhanced exterior lighting, and a brand-new Trex front porch designed for relaxed mornings and long evenings. Inside, the warmth is immediate. Cedar wood wraps the interior, creating a natural, timeless atmosphere rarely found in Florida homes. The craftsmanship was completed by a skilled wood artisan, and the attention to detail is felt throughout custom wood features, soaring character, and a layout that feels both grounded and inviting. Tile flooring spans the entire downstairs, while all bathrooms are finished floor-to-ceiling in tile, offering durability and a clean, elevated aesthetic. The home has been thoughtfully upgraded for comfort and longevity, including brand-new hurricane-impact, double-pane windows with architectural tint reflecting up to 90% of heat, a new AC unit, new attic fan, insect-repellent insulation, and a fully sealed roof coated with heat-reflective, hurricane-rated paint. Even in peak summer, electric bills remain impressively low under $150 with no solar required. The kitchen and bathrooms feature newer plumbing, modern appliances (all just a few years old), and a standout stone-wrapped Jacuzzi tub, creating a spa-like retreat within the home. Side sliders bring in natural light and connect indoor living with outdoor space, while the garage includes sensor lighting, Hardie backer walls, full electrical, and AC, making it ideal for a workshop, studio, or flex space. The property is being offered fully furnished, including custom handcrafted wood furnishings (excluding beds and sofas), making it a true turnkey opportunity for a buyer who values character, quality, and immediate livability. Regular termite and pest control servicing adds peace of mind to this cedar-built, naturally insect-resistant home. Centrally located between Orlando and Tampa, with convenient access to major highways, shopping, and daily essentials, this home delivers both lifestyle and location. This is not a cookie-cutter property. This is a home with a story built to last, designed to feel different, and ready for its next chapter.

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

Listing Agent: Jason Prieto (877-366-2213)