Winter Haven Homes For Sale & Real Estate - 1041 homes

Remarks: Welcome to this charming 3 bedroom, 1 bath home ideally located in the heart of Winter Haven, just minutes from shopping, dining, and schools. From the moment you arrive, you’ll be greeted by a lush, established front garden, perfect for those who enjoy outdoor living or gardening. The home features a covered front porch, ideal for relaxing mornings or unwinding in the evenings, along with a convenient one-car carport. Inside, you’ll find a warm and inviting living space highlighted by durable wood-look tile flooring that flows seamlessly throughout the main areas. The kitchen and dining room combination offers a functional layout with plenty of room for everyday living and entertaining. Tucked away at the rear of the home, the spacious primary bedroom provides added privacy and a generously sized closet. Two additional bedrooms offer flexibility for guests, a home office, or hobby space. The full bathroom includes a single-sink vanity and a tiled tub/shower combo. Additional features include an exterior storage/laundry room located under the carport with washer and dryer hookups. Whether you're a first-time homebuyer, investor, or looking to downsize, this home offers great potential and opportunity. Schedule your private showing today!

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

Listing Agent: Casandra Vann (863-546-5446)

Remarks: Under contract-accepting backup offers. Beautifully maintained 3-bedroom, 2-bath home located in the desirable Savanna Pointe community in Winter Haven. This property features a great layout perfect for comfortable living and entertaining. updated with a newer HVAC from 2023 and a newer 2024 water heater , stainless steel dishwasher, stainless steel range, and new interior paint! The home offers a spacious living area, a functional kitchen, and a generously sized primary suite with a private bath. Enjoy a peaceful backyard with no rear neighbors, providing added privacy. Seller will replace the roof prior to closing . Conveniently located near shopping, dining, and major roadways, this home is a great opportunity in a growing area. Don’t miss out on this one!

Listing is courtesy of: OAK AVENUE REAL ESTATE LLC (407-720-5000)

Listing Agent: Vivian Ortiz (863-514-7641)

Remarks: BACK ON THE MARKET DUE TO BUYER'S FINANCING FALLING THROUGH. This property appraised at $263,000, well above asking price! You'll definitely want to check out this beautiful, like-new property! The zero entry resort style community pool and playground overlooks one of the many beautiful lakes in Winter Haven. Villamar is a wonderful community close to a top rated Elementary School. Enjoy the privacy of this lot, as it does not have rear neighbors, but instead overlooks a quaint pond and conservatory area! Make sure to schedule your showing today!

Listing is courtesy of: VALOR REALTY SERVICES LLC (407-668-2448)

Listing Agent: Marian Benson (954-205-3075)

Remarks: Welcome to the affordable lifestyle of living in a Villa within a golf course community. Upon entering the front of the home you will notice a courtyard area on the left and right side of the entrance, which opens up additional outside entertaining space. Once inside the home you will notice it has recently been refreshed with new interior painting throughout, all new flooring, and new stove and dishwasher. As you enter, you will find the open and bright kitchen with all Stainless Steel appliances on the immediate right hand side of entryway. The dining room is open to the living room and it will handle a large dinning room set for company dinning. The living room opens to a slight step down into a less formal family room area which overlooks the lush setting of the tropical, backyard landscaping, a beauty to enjoy from your rear windows. The community clubhouse, restaurant and swimming pool are just a few steps away. The tennis courts and pickle ball courts are currently being resurfaced.

Listing is courtesy of: XCELLENCE (866-595-6025)

Listing Agent: Della Landfear (863-698-8057)

Remarks: Under contract-accepting backup offers. Top-floor condo with INCREDIBLE lake views in the desirable 55+ community of Imperial Harbours on Lake Howard! This three-bedroom, two-bath condo offers tons of potential and is ready for your personal touches and a little TLC. The kitchen features a convenient pass-through window overlooking the dining and living areas, creating an open and functional layout. The spacious primary suite includes an en suite bathroom and walk-in closet, while bedrooms two and three share a second full bath. A small bonus room overlooks the lake and would make a great office, sitting room, or hobby space. This beautifully maintained waterfront community offers maintenance-free living with access to a private dock and fishing pier on the famous Chain of Lakes. Amenities include a community pool and cabana, shuffleboard courts, extra storage, covered parking, and elevator access. Association dues cover cable, internet, water, sewer, trash, exterior maintenance, and grounds care. Conveniently located near downtown Winter Haven, shopping, dining, and medical facilities. Call today to schedule your private showing!

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

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

Remarks: Lake-access living meets modern comfort in this beautifully updated corner-lot home. Welcome to 472 Archaic Drive, originally custom built, this updated 4-bedroom, 3-bath home is situated on a corner lot in one of Winter Haven's most desirable gated communities. With a heated pool, fully fenced yard, oversized garage with tool shed/workshop, and access to outstanding neighborhood amenities, this almost 2,800 sqaure foot home offers the perfect combination of comfort, style, and functionality. You'll appreciate the spacious layout, soaring ceilings, abundant natural light, and thoughtful upgrades throughout. The stunning chef-inspired kitchen serves as the heart of the home, showcasing abundant 42" custom cabinetry, luxury stone countertops, a large center island with additional sink, stainless steel appliances, and a stylish subway tile backsplash, a walk-in pantry, and breakfast nook. Thoughtfully updated with modern finishes and timeless design, this kitchen is perfectly suited for everyday living and entertaining alike. The thoughtfully designed split-bedroom floor plan provides privacy for everyone. The spacious primary suite serves as a true retreat, featuring a luxurious ensuite bath complete with dual vanities, a relaxing soaking tub, a separate walk-in shower, and a private water closet. Generous closet space and a serene atmosphere make this the perfect place to unwind at the end of the day. Two additional bedrooms are well-sized with built in storage window seats, and separated by a unique jack-and-jill bathroom with dual vanities, creating an ideal layout for families and guests. The fourth bedroom with closet makes a great added space to the home. A third full bathroom conveniently provides supplemental access to the backyard oasis where a heated self-cleaning swimming pool, covered lanai, and fully fenced yard create the ultimate setting for year-round entertainment. Residents of this sought-after gated community enjoy access to outstanding amenities including a clubhouse, community pool, playground, private boat ramp, and dock, providing endless opportunities for recreation and enjoyment. Easy access to get to Bartow and the Polk Parkway With a new roof in 2021, this beautifully updated, meticulously maintained, and ideally located home offers the perfect combination of luxury, comfort, and Florida living.

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

Listing Agent: Suzie Rudd (863-508-3000)

Remarks: Under contract-accepting backup offers. Welcome to 1000 Lena Run Ct — a thoughtfully designed 4-bed, 3-bath pool home offering space, privacy, and timeless appeal. The moment you step inside, you’ll notice the attention to detail, soaring ceilings, and a smart split floor plan that truly makes sense. With an additional office or bonus room and a three-car garage, this home delivers flexibility for modern living. Perfectly positioned on nearly half an acre in one of Winter Haven’s most desirable gated communities Hidden Creek, it offers rare privacy with no rear neighbors, peaceful natural views, and regular visits from local wildlife — including bald eagles and turkeys. The layout is ideal for families, multigenerational living, or anyone seeking extra space. The screen-enclosed pool area creates a true Florida retreat — perfect for relaxing, entertaining, or enjoying year-round outdoor living. The primary suite is a haven of comfort, featuring a soaking tub and walk-in shower designed for unwinding after a long day. Located just minutes from the Polk Parkway, this home provides easy access to Lakeland and Winter Haven’s top-rated dining, shopping, medical facilities, and attractions — including Legoland, Chain of Lakes recreation, and other local favorites. Move-in ready and beautifully maintained, this property blends convenience with a tucked-away feel — a rare opportunity to own a private pool home in a sought-after Winter Haven community.

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

Listing Agent: Sarah Garner (863-303-4665)

Remarks: Stunning BRAND NEW two story home offer 4 bedroom, three bathrooms and loft in the Villamar community. No need to wait and build as this home is move in ready, now. From the moment you step inside, you’re greeted by a spacious foyer that flows effortlessly into the open-concept living areas. The main floor features upgraded tile flooring throughout, creating a clean, cohesive, and inviting space. At the heart of the home, the chef-inspired kitchen is designed to impress, showcasing stainless steel appliances, quartz countertops, and a side-by-side refrigerator. It opens seamlessly to the dining area and great room, making it perfect for both relaxed daily living and entertaining with ease. A convenient fourth bedroom and full bath on this level provide flexibility—ideal for guests or home office. Upstairs, a generous loft offers a versatile space for a media room, play area, or quiet retreat. The thoughtfully placed laundry room—complete with washer and dryer—is conveniently located near the secondary bedrooms. A full bath with a shower/tub combo serves this level with ease. The primary suite is your own private sanctuary, featuring a spa-like en-suite bath and an oversized walk-in closet designed for ultimate comfort and convenience. Enjoy the added benefits of modern Smart Home features, including a Ring Video Doorbell, Smart Thermostat, Keyless Entry Smart Door Lock, and DEAKO Switches—bringing both security and simplicity to your daily life. Head outside to find an open patio to lounge and enjoy the backyard. Take advantage of the community amenities inducing sparkling resort-style pool and playground. Don't miss your chance to make this home yours - reach out today for more details or to arrange a visit.

Listing is courtesy of: RE/MAX ASSURED (800-393-8600)

Listing Agent: Vilmari Caraballo (407-583-9870)

Remarks: Great opportunity to obtain a house at a lower price. The house has new kitchen and new bathroom. No HOA fees. Can be purchase with a low monthly mortgage payment. New AC to be install.

Listing is courtesy of: RODRIGUEZ PROPERTY MANAGEMENT (407-936-4061)

Listing Agent: Ivette Graves (407-936-4061)

Remarks: You won't want to miss this opportunity. This 1344 sf home located in Oakwood Estates, a 55+ community. From the carport walk into the lanai, perfect for entertaining. From there step through the French doors into the open and inviting home with an open and updated kitchen with newer appliances including a cooktop, built in double ovens, built in microwave, and nice sized refrigerator. Past the kitchen you will see the comfortable dining area with built in cabinetry. Then follow through to the spacious living room with more built in cabinets. Returning back through the kitchen you will find the family room area which is open to the kitchen, just perfect for those family and friends get togethers. The main bathroom has been updated with a beautiful shower and updated stool. The guest bedroom is attached to this bath. At the back of the home you will find the primary bedroom complete with two built in closets and a nice sized bathroom attached. The shingled room was installed in 2025 and the air conditioner and water heater were installed in 2021. Oakwood Estates offers many amenities as well as activities. You can join in on the activities or just sit back and watch the world go by.

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

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

Remarks: Welcome to your private Central Florida oasis! This beautifully updated, 3-bedroom, 2-bathroom ranch-style home combines classic mid-century durability with modern, high-end updates. Step inside to an open-concept living and dining area featuring clean, carpet-free flooring and a striking brick, perfect for cozy evenings. The heart of the home is a fully remodeled, bright white kitchen equipped with sleek quartz countertops, premium stainless steel appliances, and a convenient breakfast bar for casual dining. Retreat to the spacious primary suite, which offers private sliding glass door access to your backyard paradise. Outside, Florida living truly shines within a massive, floor-to-ceiling screen enclosure. Host gatherings on the expansive 20x14 covered concrete lanai with updated patio pavers, or cool off in the sparkling, oversized in-ground pool. Complete with a versatile, insulated 2-car garage that can easily double as a bonus family room, a durable roof replaced in 2018, and a fully fenced-in yard with no restrictive HOA fees. Feel free to install a custom firepit so the whole family can hang around and catch up on those cool Florida nights. This Winter Haven gem is ready for you to move right in.

Listing is courtesy of: HOUWZER INC (267-765-2080)

Listing Agent: Daniel Robinson (904-447-8922)

Remarks: Florida Living at Its Best! Welcome home to this beautifully updated 2-bedroom, 2-bath residence offering the perfect combination of comfort, style, and convenience. From the moment you walk through the door, you'll be impressed by the bright, open floor plan, modern finishes, wood-look flooring, and inviting living spaces designed for everyday living and entertaining. The spacious primary suite serves as a private retreat and features sliding glass doors leading to a screened and covered lanai. A portion of the lanai has been enclosed to create a flexible bonus room—ideal for a home office, reading nook, fitness area, or hobby room. Step outside to your private tiled patio, the perfect place to enjoy your morning coffee, unwind after a long day, or host family and friends. This sought-after community offers amenities rarely found at this price point, including assigned covered parking, a sparkling community pool, and direct access to beautiful Lake Smart with a private boat ramp. Whether you enjoy boating, fishing, kayaking, or simply watching the sunset over the water, you'll love the lifestyle this community provides. Located just minutes from shopping, restaurants, medical facilities, and major roadways, this move-in-ready home offers the convenience buyers are looking for and the Florida lifestyle they dream about. Opportunities like this don't come along often. Schedule your private tour today and discover why this could be the perfect place to call home.

Listing is courtesy of: TRUE FLORIDA REALTY LLC (863-337-9667)

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

Remarks: NOW OFFERING A HOME WARRANTY! Your opportunity to own in the highly sought-after Cypresswood Golf & Country Club just became even more appealing. Welcome to The Tennis Villas, where gated security, resort-style amenities, and maintenance-friendly living come together in one of Central Florida’s premier golf communities. A charming wrought iron gate welcomes you into a private front courtyard patio, creating the perfect space to enjoy morning coffee, entertain guests, or simply relax in privacy. Inside, this well-maintained 2-bedroom, 2-bath villa offers spacious living and dining areas with laminate flooring, an open-concept layout, and thoughtful features designed for comfortable Florida living. The bright kitchen features updates, ceramic tile flooring, and flows seamlessly into the main living space, complete with a wet bar and additional cabinet storage—ideal for entertaining. A bonus Florida room with air conditioning overlooks a peaceful open field and pond, providing tranquil views and additional year-round living space. The primary suite offers direct access to the enclosed lanai through sliding glass doors, creating a relaxing retreat with serene backyard views. Recent improvements include a NEW metal roof for added value and peace of mind. Enjoy truly low-maintenance living with HOA services that include exterior painting, roof maintenance, lawn care, and pest control, allowing you more time to enjoy everything Cypresswood has to offer.Community amenities include:?• 18-hole championship golf course designed by Ron Garl?• Junior Olympic-sized swimming pool?• Lighted tennis courts?• Fitness center and clubhouse with pro shop?• On-site restaurant and event space Whether by golf cart, bicycle, or a short walk, all amenities are conveniently nearby. Ideally located just minutes from Highway 27, I-4, Legoland Florida Resort, the Polk Parkway, shopping, dining, and medical facilities, this villa offers both convenience and lifestyle. Don’t miss your chance to enjoy affordable country club living in a secure, beautifully maintained community. Schedule your private showing today and experience the Cypresswood lifestyle for yourself.

Listing is courtesy of: CROSBY & ASSOCIATES, INC. (863-293-5600)

Listing Agent: Corinna Weaver (863-258-2901)

Remarks: Pre-Construction. To be built. Welcome to Ashton Covey in Winter Haven! Discover the ultimate Florida lifestyle in this stunning community. Perfectly situated just off US Highway 27, your new home offers seamless access to work, outdoor recreation, shopping, dining, and more. Imagine being less than 15 minutes from Downtown Winter Haven, where charming local shops and restaurants await your exploration. Plus, you're just 5 miles from public lake access at Lake Daisy, ideal for a day of boating, paddle boarding, and enjoying the water. The Baymont 2-car garage single-family home has it all, all on one level. A welcoming foyer invites you inside and leads you past 2 spacious bedrooms to a unique flex space, which can be used as a study or an additional bedroom. From there, a large great room is where you’ll make memories with family and friends, and it flows directly into the gourmet kitchen. Set up games or enjoy homemade meals around the large center island. At the end of the day, escape to your main-level owner’s suite with its tray ceiling, walk-in closet and double-vanity bath. This is the next level of great living. All Ryan Homes now include WIFI-enabled garage opener and Ecobee thermostat. **Closing cost assistance is available with use of Builder’s affiliated lender**. DISCLAIMER: Prices, financing, promotion, and offers subject to change without notice. Offer valid on new sales only. See Community Sales and Marketing Representative for details. Promotions cannot be combined with any other offer. All uploaded photos are stock photos of this floor plan. Actual home may differ from photos.

Listing is courtesy of: MALTBIE REALTY GROUP (813-819-5255)

Listing Agent: Bill Maltbie (813-819-5255)

Remarks: Pre-Construction. To be built. Welcome to Ashton Covey in Winter Haven! Discover the ultimate Florida lifestyle in this stunning community. Perfectly situated just off US Highway 27, your new home offers seamless access to work, outdoor recreation, shopping, dining, and more. Imagine being less than 15 minutes from Downtown Winter Haven, where charming local shops and restaurants await your exploration. Plus, you're just 5 miles from public lake access at Lake Daisy, ideal for a day of boating, paddle boarding, and enjoying the water. The Lynn Haven single-family home lives up to expectations. Relax on the long front porch. Inside, flex space makes an ideal den, or add doors for a quiet study. The foyer leads to the open family room and gourmet kitchen with island, where favorite meals and memories will be made. Enjoy outdoor living on the extended lanai, and store seasonal items in the 3-car garage. There’s even more to love upstairs with a loft, 3 bedrooms and a full bath. In your deluxe owner’s suite, enjoy beautiful tray ceilings, double vanities and a walk-in closet. You can have it all in The Lynn Haven. All Ryan Homes now include WIFI-enabled garage opener and Ecobee thermostat. **Closing cost assistance is available with use of Builder’s affiliated lender**. DISCLAIMER: Prices, financing, promotion, and offers subject to change without notice. Offer valid on new sales only. See Community Sales and Marketing Representative for details. Promotions cannot be combined with any other offer. All uploaded photos are stock photos of this floor plan. Actual home may differ from photos.

Listing is courtesy of: MALTBIE REALTY GROUP (813-819-5255)

Listing Agent: Bill Maltbie (813-819-5255)

Remarks: Pre-Construction. To be built. Welcome to Ashton Covey in Winter Haven! Discover the ultimate Florida lifestyle in this stunning community. Perfectly situated just off US Highway 27, your new home offers seamless access to work, outdoor recreation, shopping, dining, and more. Imagine being less than 15 minutes from Downtown Winter Haven, where charming local shops and restaurants await your exploration. Plus, you're just 5 miles from public lake access at Lake Daisy, ideal for a day of boating, paddle boarding, and enjoying the water. The Sandalwood single-family home sets the standard for main level luxury. A convenient family entry welcomes you inside to unmatched space and style. A full bath sits between 2 bedrooms, while a guest suite with full bath is found off the 3-car garage. Use the versatile flex space as a home office. The gourmet kitchen includes a large island overlooking dining space and the family room, ideal for gathering with family and friends. Your luxurious owner’s suite features a double vanity bath and massive walk-in closet, plus private access to the rear lanai. You’ll be stunned by The Sandalwood. All Ryan Homes now include WIFI-enabled garage opener and Ecobee thermostat. **Closing cost assistance is available with use of Builder’s affiliated lender**. DISCLAIMER: Prices, financing, promotion, and offers subject to change without notice. Offer valid on new sales only. See Community Sales and Marketing Representative for details. Promotions cannot be combined with any other offer. All uploaded photos are stock photos of this floor plan. Actual home may differ from photos.

Listing is courtesy of: MALTBIE REALTY GROUP (813-819-5255)

Listing Agent: Bill Maltbie (813-819-5255)

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

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

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

Remarks: One or more photo(s) has been virtually staged. Some seller concessions possible. SUPER DEAL on a big four bedroom home! Clean, fresh and well maintained home! PLUS, an American Preferred Home Warranty is included! With American Home Warranty, if you ever need to use it, you get to choose your own preferred vendors! Enjoy room for the family and privacy for mom and dad in the spacious split bedroom layout . You are going to like the open-concept living areas, big island kitchen with walk-in kitchen pantry. The large master suite with ensuite bath has a large walk in closet. Plenty of natural light brightens your living spaces from the energy efficient windows. All bedrooms are generously sized. Style and comfort welcome you with brand new beautiful, premium style, extra thick, waterproof luxury vinyl plank flooring in all the living areas. Fresh new carpet in all bedrooms. Pretty ceramic tile in wet areas. ROOF 2024! A fresh coat of premium exterior paint has been done and seals the deal for years to come. MOVE IN READY! Come and see this lovely home in the well-maintained Lakes at Lucerne community today!

Listing is courtesy of: DALTON WADE INC (888-668-8283)

Listing Agent: Patty Wolfgang (813-389-5226)

Remarks: Virtually Staged. Welcome to this beautifully maintained 3-bedroom, 2-bathroom home located in the desirable Winter Haven area! This move-in ready property offers a perfect blend of comfort, style, and modern updates throughout. From the moment you step inside, you’ll notice the upgraded accent wall paneling featured in the foyer, dining room, and spacious primary bedroom, adding warmth and custom character to the home. The dining room and foyer have also been enhanced with updated light fixtures that provide a fresh, elegant touch. Pride of ownership is evident throughout, as this home has been exceptionally well maintained and cared for. With inviting living spaces, a functional layout, and tasteful upgrades, this home is ideal for both relaxing and entertaining. Conveniently located near shopping, dining, schools, and major roadways, this property combines comfort and convenience in one attractive package. Don’t miss your opportunity to own this charming Winter Haven home — schedule your private showing today!

Listing is courtesy of: DALTON WADE INC (888-668-8283)

Listing Agent: Matt Everett (231-563-3176)

Remarks: NO HOA + POOL HOME + MINUTES TO THE CHAIN OF LAKES! This updated 4-bedroom, 3-bath Winter Haven home delivers the Florida lifestyle buyers are searching for — a heated private pool, oversized fenced backyard, flexible living space, and quick access to the Lake Summit boat ramp and the Winter Haven Chain of Lakes. Bring the boat, jet skis, trailer, golf cart, pets, and weekend plans because this property gives you room to enjoy it all. Inside, the home offers nearly 2,500 sq ft of living space with a bright, open feel, luxury vinyl flooring, oversized living and dining areas, and a beautifully updated kitchen featuring quartz countertops, custom soft-close cabinetry, stainless steel appliances, and a premium Ruvati workstation sink. The layout includes two private ensuite bedrooms, making it ideal for multigenerational living, guests, teenagers, extended family, or a private work-from-home setup. The spacious primary suite feels like its own retreat with tray ceilings, a large walk-in closet, dual vanities, soaking tub, and walk-in shower. Step outside to the screened lanai overlooking the heated inground pool and large backyard — perfect for cookouts, pool days, entertaining, or quiet evenings after a day on the lakes. Boat ramp is only 2 blocks away. Major updates include roof 2019, whole-house replumb 2019, AC handler 2019, water heater 2019, remodeled kitchen 2021, luxury vinyl flooring 2021, Raypak pool heater 2022, variable-speed pool pump 2024, irrigation system 2024, and guest bathroom remodel 2025. Located in desirable SE Winter Haven near Legoland, shopping, dining, medical, schools, and less than 2 minutes from Lake Summit boat ramp with access to the Chain of Lakes for boating, fishing, skiing, and waterfront dining. This is the kind of home that checks the boxes: updated, spacious, no HOA, pool, fenced yard, and close to the water.

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

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