Winter Haven FL Real Estate, Homes with Pool for Sale

4 Beds ⋅ 3 Baths ⋅ Country Club Estates SubDv. ⋅ 33881 Zip Code

Under contract-accepting backup offers. UNDER CONTRACT — ACTIVELY ACCEPTING BACKUP OFFERS - Welcome home! Nestled on a spacious 0.22-acre lot, one of the largest in the community, this meticulously maintained property offers serene, unobstructed views of a private horse rescue farm. Step outside into your ultimate backyard oasis, where a south-facing private in-ground pool awaits to treat you to gorgeous Florida sunsets. The pool features a modern salt system, a 2-foot waterfall, an in-pool cleaner, a safety no-bottom drain, and an automatic remote-controlled screen that provides direct sun protection, keeping your living space cooler and more energy-efficient. The fully fenced yard (featuring PVC fencing and 3 gates) is a gardener's delight, complete with a mature avocado tree and a variety of other fruit trees. Inside and out, this home has been extensively upgraded for modern comfort and peace of mind. Key updates include a brand-new asphalt roof (10/24), an updated kitchen featuring quartz countertops, a new garbage disposal (10/24), and a GE refrigerator (4/1/24). Natural light pours through newer Reese windows in the living and dining rooms (10/24), complemented by a stylish Reese front entry door with convenient push-button access (10/24). Energy efficiency and low overhead are major highlights, anchored by 29 Sunrun solar panels, an A/C system with a UV light addition, and recent servicing (6/26) ensuring exceptionally low utility bills. Impeccably clean and in fantastic condition, this turnkey gem is ready for its next owner! Schedule your tour today!

4735 Summerfield Circle, Winter Haven

$194,900

3 Beds ⋅ 2 Baths ⋅ Orchid Springs Village SubDv. ⋅ 33884 Zip Code

A MUST SEE! Beautifully renovated first-floor unit located in the well-kept 55+ Granada Building in Orchid Springs! PARK right in front of the door! The designated parking spot is right in front of #104! This spacious condo spans over 1,500 square feet of living space, featuring an open floor plan with 3 bedrooms and 2 bathrooms. Updates include a new modernized kitchen and bathrooms, stunning granite countertops, new stainless steel appliances, gorgeous luxury vinyl flooring throughout, and a freshly painted tan interior radiating classic warmth and timeless style. The laundry closet offers maximum convenience, complete with a washer and dryer. The monthly HOA fee includes the use of the clubhouse and community pool, gas, water, trash, cable, internet, pest control, and exterior & grounds maintenance. Designed for ultimate relaxation, the Florida room boasts lovely views of the lagoon. Don't miss your chance to transition into effortless comfort with low-maintenance living in a peaceful setting. Call us today!

100 El Camino Dr Unit 104, Winter Haven

$150,000

2 Beds ⋅ 2 Baths ⋅ Village Park SubDv. ⋅ 33880 Zip Code

Welcome to easy, affordable Florida living! This well-maintained 2-bedroom, 2-bath manufactured home is nestled in Village Park, a desirable 55+ community in Winter Haven and offers the perfect blend of comfort, convenience, and an active lifestyle. With a low HOA and NO LOT FEES, you'll enjoy affordable, low-maintenance living. Inside, you'll find a bright and inviting floor plan featuring a spacious living room, a designated dining area, and a functional kitchen complete with a breakfast bar—perfect for casual meals or entertaining guests. The primary suite serves as a private retreat with a walk-in closet and an en suite bathroom. One of the home's standout features is the generously sized screened-in porch overlooking the peaceful community pond, providing the perfect place to enjoy your morning coffee or unwind while taking in the tranquil water views. Situated at the end of a quiet street with no through traffic, this home offers added privacy and a serene setting. A covered carport provides convenient parking. Residents of this welcoming 55+ community have access to fantastic amenities, including a sparkling community pool, clubhouse, shuffleboard courts, and a full calendar of social activities designed to keep you active and connected with your neighbors. Conveniently located just minutes from shopping, restaurants, medical facilities, parks, and everyday conveniences, this move-in-ready home is vacant and easy to show. Whether you're looking for a full-time residence or the perfect Florida getaway, this charming home offers the relaxed lifestyle you've been searching for.

489 Village Circle Sw, Winter Haven

$399,990

4 Beds ⋅ 3 Baths ⋅ Willowbrook North SubDv. ⋅ 33881 Zip Code

Under Construction. Ready in October 2026! CASTAWAY MULTI-GEN: Beautiful 1 Level, 2 Car Garage Home with Open Concept Living and 3 Bedrooms! Featuring a Private Retreat: these thoughtfully designed homes provide flexibility without added monthly costs. Designed for flexibility, the Castaway Retreat offers the ideal solution without added monthly costs. This thoughtfully designed multi-gen layout includes a private retreat with its own kitchenette, living area, bedroom, and full bath, plus both interior access to the main home and a private exterior entrance. An optional washer/dryer hookup adds even more convenience.

819 Andrew Street, Winter Haven

$270,000

3 Beds ⋅ 2 Baths ⋅ Tranquil Oaks SubDv. ⋅ 33880 Zip Code

Welcome to your own private Florida retreat! This beautifully maintained 3-bedroom, 2-bath home is nestled beneath majestic oak trees in an established Winter Haven neighborhood, offering timeless curb appeal and a warm, inviting atmosphere. Inside, you'll find a functional floor plan filled with natural light, creating comfortable living spaces for both everyday life and entertaining. The thoughtful layout offers the perfect blend of openness and privacy. Step outside and discover the true centerpiece of the home—a sparkling saltwater pool surrounded by a screened lanai, allowing you to enjoy Florida's outdoor lifestyle year-round with added comfort and protection. Whether you're sipping your morning coffee, hosting family and friends, or unwinding after a long day, this backyard oasis is designed for relaxation. Conveniently located near Winter Haven's Chain of Lakes, downtown shopping and dining, parks, schools, medical facilities, and LEGOLAND Florida Resort, this home offers the perfect combination of tranquility and convenience. Don't miss your opportunity to own this move-in-ready pool home in one of Winter Haven's most desirable locations. Schedule your private showing today!

1557 N Lake Shipp Drive Sw, Winter Haven

$325,990

5 Beds ⋅ 3 Baths ⋅ Villamar Phase 7 SubDv. ⋅ 33884 Zip Code

The Robie is a two-story floorplan featured in Villamar in Winter Haven, Florida. With 2 exteriors to choose from, the Robie is sure to turn heads. Inside this inviting 5-bedroom, 3-bathroom home, you’ll find 2,447 square feet of comfortable living. This impressive all concrete block construction, two-story plan features a versatile floorplan to fit your needs. A spacious open-concept first floor which includes a well-appointed kitchen with sleek stainless-steel appliances overlooking the living and dining area. Just off the living room you will find the singular downstairs bedroom and full bathroom. As you move upstairs you are greeted with a spacious living and foyer space to utilize for work or play. The primary bedroom one is located just off the loft space and features a spacious walk-in closet as well as ensuite bathroom with double vanity and all the space you need to get ready in the morning. Three additional bedrooms share a second upstairs bathroom and linen closet for extra storage. Your laundry room is located on the second floor as well as extra storage closets. Like all homes in Villamar, the Robie includes smart home technology, which allows you to control your home anytime with your smart device while near or away. *Photos are of similar model but not that of the exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability, and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

5568 Taverna Loop, Winter Haven

$399,900

4 Beds ⋅ 2 Baths ⋅ Summer Haven Shores SubDv. ⋅ 33884 Zip Code

Virtually Staged. Beautiful 1-story home featuring 4 bedrooms, 2 bathrooms, and a 2-car garage with a spacious layout designed for comfortable living. The welcoming living room is highlighted by a cozy fireplace, while the kitchen and bathrooms have been refreshed with new countertops. Fresh interior paint throughout gives the home a bright, updated feel. Step outside to the screened lanai and private pool, offering the perfect space for relaxing or entertaining year-round. Conveniently located near LEGOLAND Florida Resort, Chain of Lakes, shopping, dining, and major roadways, this home offers both comfort and convenience. This is a fantastic opportunity to add your personal touches and make it your own. One or more photos may have been virtually staged, AI-generated, or digitally enhanced to illustrate the property's potential.

408 Coleman Drive, Winter Haven

$749,000

3 Beds ⋅ 4 Baths ⋅ Cypresswood Palma Ceia SubDv. ⋅ 33884 Zip Code

Meticulously maintained and beautifully remodeled, this exceptional Palma Ceia residence in Cypresswood offers pond frontage, three private en-suite bedrooms, a dedicated office, a heated swimming pool, and incredible golf course views. The pavered driveway and walkways, manicured flower gardens, and a 2022 black metal roof set the stage for the impressive interior. Elevated ceilings, crown molding, waterproof Pergo flooring, stone counters, and plantation shutters are just a few of the home’s stunning features. At the heart of the home is a spacious great room featuring a natural gas fireplace with shiplap façade. Triple sliding glass doors, with new screens, create a seamless indoor-outdoor flow to the covered lanai and pool area while showcasing the outdoor views. The updated kitchen features quartz counters, an island with a prep sink and filtered water, a Kohler workstation sink, breakfast bar, stainless appliances, double ovens, gas range, Bosch dishwasher, and a spacious dinette overlooking the pool. A private office provides the perfect setting for working from home. Designed to give everyone their own space, the home offers three bedrooms with en-suite bathrooms. The primary suite includes pool access, a tray ceiling, two walk-in closets with built-in shelving, and a gorgeous remodeled bathroom featuring a six-foot freestanding soaking tub, glass-enclosed walk-in shower, dual vanities, and a water closet. The second bedroom includes an equally impressive en-suite bath with custom tile flooring, a granite counter, tub, and separate walk-in shower. Located at the rear of the home, the third en-suite bedroom is ideal for visiting guests and can be closed off with a pocket door for added privacy. Its bathroom offers a granite counter with dual sinks, a tub and shower combo, and a linen closet. An additional linen closet is located in the guest-wing hallway. The interior laundry room provides a closet pantry, storage closet, and convenient half bathroom. Florida living takes center stage outdoors with a screen-enclosed heated pool, expansive covered lanai, and a separate screened area for sunning. The peaceful setting overlooks the pond and third hole of the golf course, where a variety of birds and wildlife can be enjoyed daily. Meticulously designed gardens, window planter boxes and a pavered sitting area near the pond—ideal for a fire pit—complete this private outdoor oasis. The two-car garage features an epoxy floor, utility sink, storage closets, and overhead storage racks. Additional improvements and features include a 2026 installed gas water heater, a 26-gauge standing seam metal roof (2022) with a 40-year warranty, dual-zone air conditioning (2020), irrigation on separate meter, plantation shutters throughout, remote-controlled lanai lighting, pool safety fence, Ring cameras, rain gutters, and more. Located within the guarded Cypresswood community, this remarkable home combines thoughtful updates, exceptional care, abundant privacy, and a truly beautiful golf course and waterfront setting. Cypresswood Golf & Country Club features an 18-hole championship golf course, driving range, pro shop, jr. olympic pool, tennis & pickleball courts, an event venue, a sports pub and more. Located just minutes from shopping, medical facilities and downtown Winter Haven. Centrally located between Tampa and Orlando with easy commutes to airports and beaches. Come see what this magnificent home and community in Central FL has to offer!

4040 Palma Ceia Circle, Winter Haven

$360,000

4 Beds ⋅ 3 Baths ⋅ Villamar SubDv. ⋅ 33884 Zip Code

Under Construction. Brand new, energy-efficient home available by Aug 2026! An open floorplan that makes entertaining easy in the open kitchen, dining, and great room that flow to the patio. The primary suite is tucked in the rear of the home offering plenty of privacy and features a spacious walk-in closet and shower. Visit Villamar and explore new single-family homes for sale in Winter Haven, FL. Residents will have access to two resort-style amenity centers featuring a clubhouse, pool, and playground. Winter Haven is known for its beautiful chain of lakes with lakeside restaurants and its award-winning community theater. Nearby attractions include Legoland Florida and Peppa Pig Theme Park. A brand-new model and new phase are coming soon. Each of our homes is built with innovative, energy-efficient features designed to help you enjoy more savings, better health, real comfort and peace of mind.

3757 Giorgio Drive, Winter Haven

$270,000

3 Beds ⋅ 2 Baths ⋅ Villamar SubDv. ⋅ 33884 Zip Code

Under Construction. Brand new, energy-efficient home available by Aug 2026! Prepare dinner while catching up on the days events from this homes chef-inspired kitchen which overlooks a great room and dining area. Well appointed primary suite provides a restful retreat at the end of the day and has a spacious walk-in closet. Visit Villamar and explore new single-family homes for sale in Winter Haven, FL. Residents will have access to two resort-style amenity centers featuring a clubhouse, pool, and playground. Winter Haven is known for its beautiful chain of lakes with lakeside restaurants and its award-winning community theater. Nearby attractions include Legoland Florida and Peppa Pig Theme Park. A brand-new model and new phase are coming soon. Each of our homes is built with innovative, energy-efficient features designed to help you enjoy more savings, better health, real comfort and peace of mind.

3968 Giorgio Drive, Winter Haven

$619,000

5 Beds ⋅ 3 Baths ⋅ Hidden Creek SubDv. ⋅ 33880 Zip Code

Virtually Staged. Welcome to this stunning 5-bedroom, 3-bathroom pool residence located in the highly sought-after, gated Hidden Creek community of Winter Haven. Perfectly positioned just minutes from the Polk Parkway and LEGOLAND Florida Resort, and conveniently situated between Lakeland and Winter Haven, this home offers an ideal blend of comfort and unbeatable accessibility. Inside, you will find soaring ceilings, a smart split-floor plan, a dedicated office or bonus room, a large den, and a 2-car garage that delivers ultimate flexibility for modern living, complemented by brand-new carpet replaced in 2025. The beautiful kitchen features granite countertops and a convenient walk-in pantry, while the primary suite serves as a true private retreat featuring a deep soaking tub, separate walk-in shower, dual sinks, a vanity, and a massive walk-in closet. Situated on a generous 0.35-acre lot, the property offers rare privacy, as the home backs up to a preserve with peaceful natural views. The absolute crown jewel of the home is the expansive, screen-enclosed lanai and sparkling saltwater heated pool with a heated spa, creating an exceptional resort-style outdoor living space masterfully designed for effortless entertaining, relaxing weekend lounging, or simply enjoying the tranquil Florida breeze in total privacy. Schedule your private showing today and discover a rare gem in Winter Haven! NO CDD!

1020 Lena Run Court, Winter Haven

$165,000

2 Beds ⋅ 2 Baths ⋅ Eagle Pond Condo SubDv. ⋅ 33884 Zip Code

Welcome to maintenance-free living nestled in the thriving community of Cypresswood Golf and Country Club that offers an unparalleled lifestyle and peace of mind with a 24-hour guard at the gated entrance, perfect for year-round living or a worry-free seasonal getaway. This second-floor condo boasts a world of comfort and convenience with 10' high ceilings, tons of storage in generously-sized walk-in closets that both bedrooms offer as well as additional linen storage in the hallway and primary bedroom that will keep your space organized and clutter-free effortlessly. Dive into relaxation and fun at the community pool or host gatherings, socialize with neighbors, or simply unwind in the inviting communal spaces of the clubhouse. The on-site restaurant offers convenient and flavorful dining options, perfect after a tennis or pickleball match on the community's courts or day of golf on Cypresswood's 18-hole championship course. The low monthly HOA fee includes all exterior maintenance, landscaping, pest control, trash collection, and the pool and tennis amenities. Residents also enjoy a discount on daily golf and annual memberships! Minutes from Highway 27 and the I-4 corridor, Winter Haven's very own Legoland Florida Resort, the Polk Parkway, and in the center of a thriving community with many convenient grocery, restaurant, shopping, and commuting options. Schedule your private showing today, and make this lovely condominium yours.

1105 Eagle Pond Drive Unit 1105, Winter Haven

$319,990

4 Beds ⋅ 3 Baths ⋅ Willowbrook North SubDv. ⋅ 33881 Zip Code

Virtually Staged. Under Construction. Under Construction Sample Images: Ready by August 2026. No rear neighbors! 4 Bedrooms and 2 Baths!! The Poinciana is a spacious 2,110 Sq. Ft. floor plan, open concept, with a spacious covered lanai perfect for relaxation and/or entertaining. Sizable great room and two big his and hers walking closets in the master suite. Nice upgrades included like 42" cabinets, stone counters in the kitchen and all bathrooms, tile in wet and common areas, 9'4" ceiling height, and a lot more. One of our most popular floor plan that will fit any family needs.

1052 Luke Avenue, Winter Haven

$274,990

3 Beds ⋅ 2 Baths ⋅ Willowbrook North SubDv. ⋅ 33881 Zip Code

Virtually Staged. Under Construction. Under construction. Sample Images Ready by August 2026 No rear neighbors! The Auburndale is just the perfect home that feels bigger than 1,407 Sq. Ft. Is an open concept floor plan. Nice-sized kitchen and a spacious master bedroom. Nice upgrades include stone counters in the kitchen and in all bathroom counters, tile in wet and common areas, 9'4" ceiling height, and a lot more.

1040 Luke Avenue, Winter Haven

$289,990

4 Beds ⋅ 2 Baths ⋅ Willowbrook North SubDv. ⋅ 33881 Zip Code

Virtually Staged. Under Construction. Under construction. Sample Image Ready by August 2026 No rear neighbors! The Bradley looks and feels bigger than 1,625 Sq. Ft. Is an open concept floor plan: spacious master bathroom, dual vanity, and a nice-sized closet. Nice upgrades include stone counters in the kitchen and in all bathroom counters, tile in wet and common areas, 9'4" ceiling height and a lot more.

296 Meredith Boulevard, Winter Haven

$115,000

2 Beds ⋅ 2 Baths ⋅ Orange Manor West Coop Inc SubDv. ⋅ 33884 Zip Code

Become a share holder in this highly sought after 55+ gated community. If you are looking for the perfect retirement home, this one is for you! Located in Orange Manor West, it is one of the most popular 55+ communities in Winter Haven and surrounding area with many amenities. Pool, shuffle board, putt putt, horse shoes, crochet, bingo, lake access and much more. Legoland is around one mile away which is great for visiting family. This is a 1368 Square ft. 2 bedroom 2 bath 1984 with an attached enclosed Florida room and an enclosed carport with ac. The king size master bedroom has a walk-in closet and a private bathroom with a tub shower. It has an inside utility room with washer & dryer. The monthly maintenance fee is $279.00 a month which includes cable, internet, trash pickup, and amenities. This house is fully furnished and ready to move in. This is also a pet free community. While it is a great winter home get away, it can also be a year round retirement home. Come see it today. This one won't last long. All measurements are approximate and should be verified by the buyer.

113 Lake Hazel Drive, Winter Haven

$425,000

4 Beds ⋅ 3 Baths ⋅ Sun Rdg Village East SubDv. ⋅ 33880 Zip Code

Welcome to this well-maintained Winter Haven pool home, offering over 2,400 sqft of living space on a corner lot. This 4-bedroom, 2.5-bathroom home includes a 3-car garage, wood floors in the kitchen, foyer, and dining room, and spacious rooms with generous closet space. Upstairs, a cozy loft provides the perfect spot to unwind. Step outside to a screened and in-ground pool and spa, surrounded by a large, fenced backyard—ideal for privacy and outdoor enjoyment. The property also includes a rear parking pad with its own side entry, perfect for storing a boat or trailer. If you're looking for an affordable, move-in ready pool home with room to grow—or a strong investment opportunity—this is one you don’t want to miss. The seller is motivated, so schedule your showing today.

5009 Strada Drive, Winter Haven

$287,990

3 Beds ⋅ 2 Baths ⋅ Villamar Phase 6 And Phase 6d SubDv. ⋅ 33884 Zip Code

Under Construction. The Aria is one of our one-story floorplans featured in Villamar in Winter Haven, Florida. With multiple exteriors to choose from, the Aria is a popular home. Inside this 3-bedroom, 2-bathroom home, you’ll find 1,672 square feet of comfortable living. This all-concrete block constructed, one-story layout optimizes living space with an open concept kitchen overlooking the living area, dining room, and covered lanai. Entertaining is a breeze, as this popular single-family home features a living and dining in the heart of the home, with covered lanai just steps away in your backyard. The spacious kitchen features stainless steel appliances, a convenient island, and walk-in pantry with ample storage. In every bedroom you’ll have carpeted floors and a closet in each room. Whether these rooms become bedrooms, office spaces, or other bonus rooms, there is sure to be comfort. The primary bedroom located in the rear of the home has its own attached bathroom that features a walk-in closet and all the space you need to get ready in the morning. Sharing a sink isn’t a worry with the double vanity. Two additional bedrooms share a second bathroom. This home also features a nice laundry room space with privacy doors and a two-car garage for parking or storage. Like all homes in Villamar, the Aria includes smart home technology, which allows you to control your home anytime with your smart device while near or away. *Photos are of similar model but not that of the exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability, and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

4040 Giorgio, Winter Haven

$324,490

4 Beds ⋅ 2 Baths ⋅ Villamar Phase 6 And Phase 6d SubDv. ⋅ 33884 Zip Code

Under Construction. Introducing the Cali floorplan at Villamar, in Winter Haven, Florida, where every square foot is put to use with sophistication and comfort. Inside this 4-bedroom, 2-bathroom home, you’ll find 1,828 square feet of comfortable living. This meticulously designed residence combines modern convenience with timeless elegance, showcasing quartz counters and tile floors throughout. As you step inside, you are greeted by an inviting foyer that leads you into the heart of the home. The open-concept layout seamlessly connects the living room, dining area, and kitchen, creating a perfect space for entertaining family and friends. The spacious living room features abundant natural light, thanks to large windows that provide picturesque views of the surrounding landscape. With ample room for seating, it's an ideal spot for relaxation and gatherings. The kitchen is a true highlight, including quartz countertops, sleek stainless-steel appliances, a walk-in pantry and an oversized island with a breakfast bar. Whether you're preparing a casual meal or hosting a formal dinner, this kitchen is well-equipped to meet your culinary needs. The four generously sized bedrooms provide flexibility for various lifestyles. The primary suite located in the rear of the home is a tranquil retreat, featuring a private ensuite bathroom with dual sinks, a separate shower, and a walk-in closet. The remaining three bedrooms share one well-appointed bathroom, making morning routines a breeze. Laundry won't be a chore with its dedicated space convenient to all bedrooms. Like all homes in Villamar, the Cali includes smart home technology, which allows you to control your home anytime with your smart device while near or away. Whether you're seeking a peaceful family retreat or a stylish place to call your own, this home is sure to meet your every need. Contact us today and find your home at Villamar. *Photos are of similar model but not that of the exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability, and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

3748 Giorgio Drive, Winter Haven

$288,990

4 Beds ⋅ 2 Baths ⋅ Willowbrook South SubDv. ⋅ 33881 Zip Code

Under Construction. The Freeport II floor plan at Willowbrook South offers the perfect blend of comfort, functionality, and modern design. Built with durable all-concrete block construction, this one-story home maximizes living space with a bright, open-concept layout that’s ideal for everyday living and entertaining. As you enter through the foyer, you’ll find two spacious guest bedrooms and a full guest bath with a modern vanity. A convenient linen closet is positioned between the bathroom and bedrooms for easy storage. Further down the hallway, a third bedroom offers flexibility for a home office or guest space, alongside a private laundry area and direct access to the two-car garage. The heart of the home features a well-appointed kitchen with stainless steel appliances, overlooking the dining area, great room, and covered patio perfect for gatherings and family time. Tucked at the rear of the home, the primary bedroom offers a peaceful retreat with a walk-in closet and a spa-inspired bathroom featuring a double vanity sink and a spacious shower. Every home in Willowbrook South comes equipped with the Home Is Connected Smart Home Technology package, allowing you to control locks, thermostat, and more right from your smartphone whether you’re home or away. With its thoughtful design and modern features, the Freeport makes owning a new home in Winter Haven, FL both easy and enjoyable. *Photos are of similar model but not that of the exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability, and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

2778 Adeline Avenue, Winter Haven

$298,990

5 Beds ⋅ 2 Baths ⋅ Willowbrook South SubDv. ⋅ 33881 Zip Code

Under Construction. Welcome to the Dundee, one of our one-story floorplans available in the beautiful community of Willowbrook South in Winter Haven, Florida. Choose between three thoughtfully designed exterior styles. This spacious 5-bedroom, 2-bathroom home offers 1,708 square feet of modern, comfortable living. Step inside to an inviting open-concept layout where the kitchen, living, and dining areas flow seamlessly together perfect for both everyday living and entertaining guests. The gourmet kitchen is the heart of the home, featuring sleek stainless-steel appliances, quartz countertops, and contemporary cabinetry that combine style with functionality. Overlooking the dining and living room, the kitchen ensures you’re always connected to the action. Luxury finishes are found throughout, with luxury vinyl plank flooring in the main living areas, primary suite, bathrooms, laundry room, and foyer. Bedrooms 2–5 include soft carpet and roomy closets, offering comfort and flexibility to use as bedrooms, office space, or creative bonus rooms. The private primary suite is designed for relaxation, with a walk-in closet and an en-suite bathroom that includes a toilet and shower for added privacy. This move-in ready home in Willowbrook South, Florida offers the perfect balance of style, comfort, and convenience. *Photos are of similar model but not that of the exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability, and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

2774 Adeline Avenue, Winter Haven

$165,000

2 Beds ⋅ 2 Baths ⋅ Cypresswood Tennis Villas SubDv. ⋅ 33884 Zip Code

Virtually Staged. Welcome to effortless Florida living in the highly sought-after gated Cypress Wood Golf & Country Club! Perfectly positioned on the beautifully maintained 10th hole, this 2-bedroom, 2-bath villa offers over 1,100 square feet of comfortable living with no close rear neighbors—just breathtaking views of lush fairways, mature oak trees, and Florida wildlife. Inside, you’ll find a bright, open floor plan complete with a spacious Florida room, the perfect place to enjoy your morning coffee or unwind while taking in the peaceful golf course scenery. Offered fully furnished with quick occupancy available, this home is truly move-in ready. Beyond the entrance, experience the exceptional lifestyle that makes Cypress Wood one of Central Florida’s most desirable golf communities. Enter through a 24-hour guard gate and enjoy a scenic drive along beautifully landscaped, tree-lined streets surrounded by meticulously maintained grounds and natural beauty. Residents have access to outstanding amenities including an 18-hole championship golf course, clubhouse, restaurant, community pool, tennis courts, pickleball courts, and a vibrant social atmosphere. The HOA provides lawn maintenance and exterior upkeep, allowing you to spend more time enjoying everything this resort-style community has to offer. Conveniently located just minutes from LEGOLAND Florida Resort, shopping, dining, and everyday conveniences, with easy access to Highway 27 and I-4, offering an easy commute to both Orlando and Tampa. Whether you’re searching for a full-time residence, winter retreat, or investment opportunity, this villa offers the perfect blend of comfort, convenience, and carefree Florida living. Schedule your private showing today !

665 Broadmoor Circle, Winter Haven

$339,640

4 Beds ⋅ 3 Baths ⋅ Willowbrook North SubDv. ⋅ 33881 Zip Code

Under Construction. Ready in October 2026! Beautiful 2 Level, 2 Car Garage Home with Open Concept Living and 4 Bedrooms! This Jupiter plan is Traditional elevation. The inviting front porch opens to a gracious foyer with the Primary suite on the first floor; it boasts an en suite bathroom with dual sink vanity, shower, private water closet, and large walk-in closet. The spacious family room is open to the dining area and adjacent kitchen. The 2nd level offers a spacious loft and 3 secondary bedrooms each with walk-in closets and a full bathroom.

349 Meredith Boulevard, Winter Haven

$356,315

4 Beds ⋅ 3 Baths ⋅ Willowbrook North SubDv. ⋅ 33881 Zip Code

Under Construction. Ready in October 2026! Beautiful 2 Level, 2 Car Garage Home with Open Concept Living, Loft and 4 Bedrooms! This Naples is in Coastal Elevation. The inviting front porch opens to a gracious foyer with adjacent powder room. The well-appointed, island kitchen is open to the adjoining cafe and spacious family room. The primary suite boasts an en suite bathroom with dual sink vanity, shower, private water closet, and large walk-in closet. The 2nd level offers a spacious loft, 3 secondary bedrooms, each with walk-in closets, a full bathroom and a convenient laundry room.

816 Andrew Street, Winter Haven

$129,500

2 Beds ⋅ 1 Baths ⋅ Orchid Spgs Vill 300 Barcelona SubDv. ⋅ 33884 Zip Code

Virtually Staged. Nestled within the peaceful and highly desirable Orchid Springs Village, this beautifully renovated ground-floor condominium offers the perfect blend of modern style, low-maintenance living, and an unbeatable Winter Haven location. Designed with comfort and functionality in mind, the bright open floor plan seamlessly connects the living and dining areas, creating an inviting space filled with abundant natural light. Beautiful luxury vinyl plank flooring flows throughout the home, while the updated kitchen showcases crisp white cabinetry, stainless steel appliances, and a desirable gas range—combining timeless style with everyday functionality. The spacious bedroom offers a relaxing retreat with generous closet space, while the beautifully remodeled bathroom features an updated vanity and a sleek glass-enclosed tiled shower with tub. Just beyond the main living area, a versatile FLEX ROOM provides the perfect space for a home office, reading nook, hobby room, fitness area, or additional sitting room to suit your lifestyle. Beyond the flex space, the ENCLOSED SUNROOM is surrounded by expansive windows that overlook the lush, manicured grounds, creating a peaceful setting to enjoy your morning coffee, unwind with a good book, or simply relax while taking in the tranquil views, with direct access to the outdoor green space. Residents of Orchid Springs Village enjoy a carefree lifestyle with exceptional community amenities, including a sparkling swimming pool, clubhouse, scenic walking paths, convenient laundry facilities, assigned covered carport parking, and beautifully maintained landscaping. The monthly condominium fee provides outstanding value by covering water, sewer, trash, natural gas, exterior maintenance, and recreational facilities, allowing for truly stress-free ownership. Perfectly positioned in the heart of Winter Haven, this move-in-ready condo is just minutes from Winter Haven Hospital, shopping centers, local restaurants, golf courses, and the vibrant downtown district. Outdoor enthusiasts will appreciate the proximity to Lake Shipp Park and Lake Hartridge Nature Park, while the world-famous LEGOLAND® Florida Resort and Winter Haven's renowned Chain of Lakes are just a short drive away. With easy access to US-27 and the Polk Parkway, commuting to Orlando, Tampa, and surrounding Central Florida destinations is effortless. Whether you're searching for a full-time residence, seasonal retreat, or investment opportunity, this beautifully updated condo offers the ideal combination of comfort, convenience, and resort-style living.

1100 Martinique Drive Unit 106, Winter Haven

$329,990

4 Beds ⋅ 2 Baths ⋅ Harmony On Lake Eloise SubDv. ⋅ 33884 Zip Code

Under Construction. Introducing the Cali floorplan at Harmony at Lake Eloise, in Winter Haven, Florida, where every square foot is put to use with sophistication and comfort. Inside this 4-bedroom, 2-bathroom home, you’ll find 1,828 square feet of comfortable living. This meticulously designed residence combines modern convenience with timeless elegance, showcasing quartz counters and luxury vinyl plank floors throughout. As you step inside, you are greeted by an inviting foyer that leads you into the heart of the home. The open-concept layout seamlessly connects the living room, dining area, and kitchen, creating a perfect space for entertaining family and friends. The spacious living room features abundant natural light, thanks to large windows that provide picturesque views of the surrounding landscape. With ample room for seating, it's an ideal spot for relaxation and gatherings. The kitchen is a true highlight, including quartz countertops, sleek stainless-steel appliances, a walk-in pantry and an oversized island with a breakfast bar. Whether you're preparing a casual meal or hosting a formal dinner, this kitchen is well-equipped to meet your culinary needs. The four generously sized bedrooms offer flexibility for various lifestyles. The primary suite located in the rear of the home is a tranquil retreat, featuring a private ensuite bathroom with dual sinks, a separate shower, and a walk-in closet. The remaining three bedrooms share one well-appointed bathroom, making morning routines a breeze. Laundry won't be a chore with its dedicated space convenient to all bedrooms. Like all homes in Harmony at Lake Eloise, the Cali includes smart home technology, which allows you to control your home anytime with your smart device while near or away. Whether you're seeking a peaceful family retreat or a stylish place to call your own, this home is sure to meet your every need. Contact us today and find your home at Harmony at Lake Eloise. *Photos are of similar model but not that of the exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability, and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

1765 Hummingbird Road, Winter Haven

$274,900

3 Beds ⋅ 2 Baths ⋅ Harmony On Lake Eloise SubDv. ⋅ 33884 Zip Code

Under Construction. Discover the Downing 2 floorplan at Harmony at Lake Eloise in Winter Haven, featuring 1,302 square feet, three bedrooms and two bathrooms, this home prioritizes efficient living without sacrificing an ounce of warmth. Step inside and be greeted by a thoughtfully arranged space, designed to maximize both comfort and flow. (Luxury vinyl) flooring guides you through the home, setting the stage for everyday living. The heart of the Downing is its open concept living area, where the living room and kitchen merge seamlessly, fostering connection and ease. This central space, bathed in natural light, is perfect for cozy evenings or casual gatherings. The kitchen, a model of efficiency, is equipped with modern appliances and well-organized storage, making meal preparation a breeze. Each of the three bedrooms provides a tranquil escape, with the primary suite offering a private bathroom for added convenience. The second bathroom, strategically located, serves the remaining bedrooms with ease. Like every home built in Harmony at Lake Eloise, the Downing 2 is built with all concrete block construction and integrated smart home technology. This allows you to effortlessly manage your home's systems, from lighting to temperature, all from the palm of your hand, whether you're relaxing inside or out and about. The Downing 2 floorplan is ideal for those seeking a streamlined, comfortable lifestyle. It's a place where thoughtful design meets modern convenience, creating a true sense of home. Experience the blend of simplicity and sophistication at Harmony at Lake Eloise. Contact us today and find your home at Harmony at Lake Eloise. *Photos are of similar model but not that of the exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability, and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

3328 White Indigo Road, Winter Haven

$350,990

4 Beds ⋅ 3 Baths ⋅ Harmony On Lake Eloise SubDv. ⋅ 33884 Zip Code

Under Construction. Welcome to the Campbell, a stunning four-bedroom, two and a half bathroom home located in the heart of Winter Haven, Florida at our Harmony at Lake Eloise community. A beautiful patio welcomes you to a home that optimizes living space with an open concept kitchen overlooking the living area, dining room, and outdoor lanai. Entertaining is a breeze, as this popular single-family home features a spacious kitchen island, quartz countertops, dining area and a walk-in pantry for extra storage. Ample windows and a set of sliding glass doors allow lighting into the dining area and luxury vinyl plank flooring throughout is stylish and charming. The first floor also features a powder bathroom off the living area for convenience. As we head up to the second floor, we are greeted with bedroom one that features an en-suite bathroom with a double vanity and a spacious walk-in closet providing substantial space for storage. Three additional bedrooms, a full bathroom, and a laundry area are located on the second floor. Like all homes in Harmony at Lake Eloise, the Campbell includes a Home is Connected smart home technology package which allows you to control your home with your smart device while near or away. With its spacious layout and contemporary finishes, the Campbell in Harmony at Lake Eloise provides the perfect blend of style and functionality. *Photos are of similar model but not that of the exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability, and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

1734 Hummingbird Road, Winter Haven

$110,000

2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code

Move right into this furnished home located in Oakwood Estates, a 55+ community. The carpet throughout the home is in excellent condition. The rooms are very spacious and inviting. The home has been very well maintained. The dishwasher was installed in 2018, the washer and dryer 2020, and the refrigerator in 2024. Enjoy the bonus room on the front of the home or sit and watch the world go by on the comfortable lanai. Oakwood Estates offers many activities and amenities. If you are looking for exercise, you can join in with the pool or indoor aerobics. Chair Yoga is offered twice a week, or play some pool volleyball. The tennis court has recently been refinished and there is a pickle ball group that meets three times a week. During the winter months, there are several exciting dances as well as many activities. If food is your thing, Oakwood offers potluck dinners, ice cream socials, and weekly coffee and donuts. If you are looking for full time or just part time, this is your opportunity to move into a wonderful community, conveniently priced.

4807 Plumwood Street, Winter Haven

$164,999

3 Beds ⋅ 2 Baths ⋅ Winter Ridge Condo SubDv. ⋅ 33881 Zip Code

Under contract-accepting backup offers. This well-maintained unit is a corner lot unit with 3bed/2bath. Features: ceramic tiles flooring throughout, a huge living room and a kitchen with the laundry space area. The kitchen comes fully equipped with appliances, including a washer and dryer. Large Florida room with a separate A/C unit, could serve as a 4th bedroom/guest bedroom or play room. Two assigned parking spaces out front, one with aluminum carport. Additional guest parking is available near the unit with proper permit tags. Community for ALL Ages and conveniently located close to dining and stores. Low maintenance living with an HOA that takes care of it and include the home Insurance: covering roof maintenance and exterior building maintenance, landscaped grounds, road maintenance. Facilities: heated pool, clubhouse, shuffleboard and boat slip. Allows 2 pets under 40 pounds. Located just minutes from HWY 27. New roof installed in March 2025 and New water heater in July 2025. Call today and schedule your private tour.

344 Winter Ridge Boulevard Unit 344, Winter Haven

$435,000

3 Beds ⋅ 2 Baths ⋅ Acreage SubDv. ⋅ 33880 Zip Code

Welcome home to peaceful country living! Nestled on nearly 2 acres of beautiful pature land and no HOA. This charming 3-bedroom,2-bath farmhouse-style home offers the perfect blend of rustic character and modern comfort. The roof was installed about 5 years ago and the A/C was installed about 4 years ago. The windows have all been updated. Gather with family and friends in the inviting living room, where a cozy fireplace creates the perfect place to relax on cool evenings. The kitchen has updated appliances, farm-style sink and a large pantry. A versatile bonus room provides endless possibilities as a home office, game room, or guest retreat. Need a dedicated workspace? The property also features a separate office, offering privacy and felxibility for remote work, a home business or a creative studio. Step outside and embrace the country lifestyle. Spend warm Florida days cooling off in the above-ground pool with a 16x20 deck. Enjoy the wide-open views, or bring your horses, live-stock or gardening on the spacious pasture. The 2-car garage provides plenty of room for vehicles, tools and outdoor equipment. There is also a 18X18 storage shed with a air-conditioner. Whether you're sipping coffee on the porch at sunrise or watching th sunset over your own piece of the countryside, this property offers the peaceful farmhouse lifestyle you've dreaming of--all while providing the space and freedom to make it your own.

1755 Beth Lane, Winter Haven

$305,000

3 Beds ⋅ 2 Baths ⋅ Waterside Village SubDv. ⋅ 33880 Zip Code

Virtually Staged. Welcome to Waterside Village, a community of just 48 homes that offers a peaceful setting while keeping you close to everything Winter Haven has. This move-in ready 3-bedroom, 2-bath home offers an open floor plan, spacious kitchen with a large walk-in pantry, and a backyard designed for entertaining. Enjoy the screened-in lanai, pool deck, and above-ground pool with a recently replaced liner, all within a fully fenced yard complete with a storage shed. Conveniently located near shopping, restaurants, grocery stores, and LEGOLAND, you'll love having everything you need just minutes away.

144 Waterside Circle, Winter Haven

$309,900

3 Beds ⋅ 2 Baths ⋅ Traditions Ph 01 SubDv. ⋅ 33884 Zip Code

Welcome to 2820 Traditions Blvd S, located in the desirable 55+ gated community of Traditions at Lake Ruby in Winter Haven. This well-maintained Augusta model offers 3 bedrooms, 2 bathrooms, a spacious 2-car garage, and a peaceful pond-front setting. This home is perfect for Florida living! The open and comfortable floor plan provides beautiful pond views from the kitchen, dining area, living room, primary suite, and enclosed patio, allowing you to enjoy the tranquil Florida surroundings throughout the home. The kitchen offers ample cabinetry and workspace, while the spacious living areas create an inviting environment for both everyday living and entertaining. The split bedroom layout provides privacy for owners and guests alike. The enclosed patio is a wonderful space to relax, enjoy your morning coffee, or unwind while taking in the water views. Just outside your door, enjoy all that Traditions at Lake Ruby community provides, including a clubhouse, resort-style amenities, pool, fitness facilities, and recreational opportunities designed for an active adult lifestyle. Conveniently located in Winter Haven with easy access to shopping, dining, medical facilities, golf, and Central Florida attractions. Whether you are looking for a full-time residence or a seasonal retreat, this home offers comfort, convenience, and the opportunity to enjoy the relaxed lifestyle of Traditions at Lake Ruby.

2820 Traditions Boulevard S, Winter Haven

$530,000

5 Beds ⋅ 4 Baths ⋅ Orleans SubDv. ⋅ 33884 Zip Code

Welcome to 3205 La Salle Street, where resort-style outdoor living, an exceptional floor plan, and modern elegance come together in the highly sought-after Orleans community. Built in 2023 by Ryan Homes, this beautifully upgraded Lynn Haven model offers 5 bedrooms, 4 full bathrooms, and 3,021 square feet of thoughtfully designed living space that perfectly balances everyday comfort with effortless entertaining. Situated on a beautifully landscaped corner lot featuring a paver driveway, lush tropical landscaping, and extra green space beyond the backyard, this property offers a setting rarely found in newer construction. The fully privacy-fenced backyard is your own private retreat, complete with a newly added saltwater pool, expansive covered lanai, and additional green space beyond the pool that enhances both privacy and the feeling of having an even larger backyard—perfect for entertaining, pets, or simply enjoying peaceful Florida evenings. Nestled between Lake Eloise and Lake Winterset within the intimate Orleans community of just 42 homesites, residents enjoy low HOA dues, no CDD fees, and select community canal access to Lake Eloise while being less than two miles from Publix, Starbucks, LEGOLAND, shopping, dining, and everyday conveniences. Inside, abundant natural light, soaring ceilings, and an open-concept design create a welcoming atmosphere from the moment you enter. A spacious flex room off the foyer offers endless possibilities as a formal dining room, home office, playroom, or additional living space. The expansive great room seamlessly connects to the chef-inspired kitchen, complete with quartz countertops, stainless steel appliances, a large center island, abundant cabinetry, and a walk-in pantry, creating the ideal gathering space for family and friends. One of this home's standout features is its exceptionally functional floor plan. The first-floor bedroom and adjacent full bathroom provide the perfect private space for guests or multigenerational living. Upstairs, the luxurious primary suite serves as a true retreat with two walk-in closets and a spa-inspired ensuite featuring dual vanities, a walk-in shower with a Roman-style seat, and a private water closet. A secondary upstairs bedroom enjoys the privacy of its own ensuite bathroom, while two additional generously sized bedrooms share a well-appointed guest bath. Completing the second level is an oversized loft, offering endless flexibility as a media room, game room, second family room, or homework space, along with a conveniently located upstairs laundry room. Better than new, this home has already been enhanced with thousands of dollars in premium upgrades, including a saltwater pool, irrigation well, generator-ready wiring, EV charging system wiring, an Ecobee smart thermostat, WiFi-enabled garage door opener, and energy-efficient construction throughout. The roof, HVAC system, water heater, and major kitchen appliances are all approximately two to three years old, providing added peace of mind for years to come. Offering an exceptional combination of luxury, functionality, outdoor living, and one of Winter Haven's most convenient locations, 3205 La Salle Street is truly better than new and ready to welcome its next owners.

3205 La Salle Street, Winter Haven

$255,000

3 Beds ⋅ 2 Baths ⋅ Deer Lake Terrace Sub SubDv. ⋅ 33881 Zip Code

Welcome to this charming 3-Bedroom, 2-bath home in the heart of Winter Haven! This property offers comfortable living with a functional layout, a welcoming front porch, and a private in-ground pool that's perfect for relaxing or entertaining family and friends. Fully fenced yard. Conveniently located near shopping, dining, schools, and major roadways. DONT miss this opportunity - schedule your showing today!

3334 Avenue J Nw, Winter Haven

$292,490

3 Beds ⋅ 2 Baths ⋅ Villamar SubDv. ⋅ 33884 Zip Code

Under Construction. Brand new, energy-efficient home available by Aug 2026! Prepare dinner while catching up on the days events from this homes chef-inspired kitchen which overlooks a great room and dining area. Well appointed primary suite provides a restful retreat at the end of the day and has a spacious walk-in closet. Visit Villamar and explore new single-family homes for sale in Winter Haven, FL. Residents will have access to two resort-style amenity centers featuring a clubhouse, pool, and playground. Winter Haven is known for its beautiful chain of lakes with lakeside restaurants and its award-winning community theater. Nearby attractions include Legoland Florida and Peppa Pig Theme Park. A brand-new model and new phase are coming soon. Each of our homes is built with innovative, energy-efficient features designed to help you enjoy more savings, better health, real comfort and peace of mind.

3940 Giorgio Drive, Winter Haven

$337,000

2 Beds ⋅ 2 Baths ⋅ Lake Dexter Woods Ph Two SubDv. ⋅ 33884 Zip Code

PRESENTING A CHARMING LAKEFRONT RETREAT ON LAKE DEXTER! This beautifully maintained 2-bedroom, 2-bath residence with a 1-car garage offers an exceptional blend of comfort, thoughtful upgrades, and waterfront living. The spacious kitchen flows seamlessly into the open living area, creating an inviting setting for everyday living and entertaining, complete with a modern LED fireplace. Travertine flooring extends throughout most of the home, while the guest bedroom features warm bamboo flooring. Plantation shutters and newer PGT hurricane-impact windows provide added beauty, energy efficiency, and peace of mind. Additional improvements include a three-year-old energy-efficient metal roof, radiant barrier insulation in the attic, an Amarr triple-steel insulated garage door, and low-maintenance composite decking. The primary bedroom offers two custom built-in closets and a comfortable private retreat. Step outside to enjoy the patio, composite deck, private dock, and two boat slips on beautiful Lake Dexter. Whether boating, fishing, kayaking, or simply relaxing while taking in the tranquil lake views, this property provides the perfect opportunity to experience the Florida waterfront lifestyle.

679 Lake Dexter Circle, Winter Haven

$379,900

3 Beds ⋅ 2 Baths ⋅ Lesnick Park SubDv. ⋅ 33880 Zip Code

Imagine the possibilities! Offering approximately 1,890 square feet of finished living area along with an additional 1,622 square feet of permitted functional space, the property provides approximately 3,512 total square feet, under roof, of combined building area. The expansive open living areas provide endless possibilities—whether you're envisioning an oversized primary suite, game room, home office, music studio, fitness space, or the ultimate man cave or she shed. Unlike many homes with fixed layouts, this property's generous footprint invites you to customize the space to fit your lifestyle. Step outside to enjoy your own private retreat featuring a solar-heated 20' x 40' pool, beautiful paver pool deck, spacious fenced backyard, circular driveway, and no HOA—all in an established neighborhood surrounded by beautiful lakefront homes. A unique 3-car garage configuration provides exceptional flexibility. The oversized 23' x 25' two-car garage includes an adjoining workshop or storage area, while the separate single-car garage with a built-in closet sits adjacent to the utility room, making it ideal for hobbies, storage, a home gym, or recreational equipment. If you've been searching for a home with space, versatility, and room to make it your own, this is one you won't want to miss.

906 Avenue M Se, Winter Haven

$265,000

4 Beds ⋅ 2 Baths ⋅ Villamar SubDv. ⋅ 33884 Zip Code

Short Sale. Calling all investors, flippers, and renovation enthusiasts! This 4 bedroom, 2 bathroom home in Winter Haven presents an outstanding opportunity to add value and build equity. With a spacious floor plan and solid footprint, this property is ready for a complete transformation. Whether you're looking for your next fix and flip, rental investment, or renovation project, the possibilities are endless. Conveniently located near shopping, dining, schools, and major roadways, this home offers a desirable location with strong upside potential. Bring your vision, creativity, and contractor, this property is being sold as-is and is priced with repairs in mind. Don't miss your chance to unlock the potential of this Winter Haven investment opportunity!

1973 Carnostie Road, Winter Haven

$125,000

1 Beds ⋅ 1 Baths ⋅ The Haven SubDv. ⋅ 33881 Zip Code

Virtually Staged. Historic charm meets downtown convenience at The Haven. This 1-bedroom, 1-bath condo sits on the 3rd floor of one of Winter Haven's most recognizable former hotels — now reimagined as boutique historic condos just steps from downtown, Lake Howard, restaurants, coffee shops, nightlife, parks, and the popular Saturday Farmers Market. The unit blends vintage character with modern updates: tall ceilings, oversized historic windows, and abundant natural light give the space an airy, elevated feel, with partial views of downtown from the 3rd floor. The kitchen has been fully renovated with granite countertops, brand-new stainless steel appliances, and dual pantry/utility closets — smart, functional storage that's genuinely hard to find in a condo. The primary bedroom comfortably fits a king-sized bed and includes a walk-in closet, while the bathroom has been refreshed with granite counters, a tiled tub surround, and a classic tub/shower combo. Building amenities add real everyday value: secure key-fob entry, elevator access, assigned parking, on-site laundry, additional storage rooms, and a beautifully restored historic lobby that reflects the building's original character. Residents also have access to a private courtyard pool, framed by creeping fig walls, palm trees, and lush landscaping — a peaceful spot to relax or work remotely outdoors. Low-maintenance and move-in ready, this unit suits a range of buyers: first-time homeowners, investors, seasonal residents, or anyone looking for an affordable condo with strong rental potential in a walkable downtown setting. Location is where this property really stands out. You're within walking distance of downtown dining, shopping, entertainment, and lakefront paths along Lake Howard. Winter Haven is home to 50 lakes, including the famous Chain of Lakes, putting boating, fishing, water skiing, and sunset views just minutes away. Everyday essentials are equally close — Publix, Walmart, Aldi, TJ Maxx, and local medical facilities are all nearby, and LEGOLAND Florida Resort is a short drive for weekend fun or extra rental appeal. Affordable, updated, and full of character, this condo at The Haven offers a rare combination: historic charm, modern comfort, and a genuinely walkable downtown lifestyle. Units in this building don't come up often — schedule your showing before this one's gone.

235 6th Street Nw Unit 307, Winter Haven

$409,900

4 Beds ⋅ 3 Baths ⋅ Eloise Woods Lake Roy Unit SubDv. ⋅ 33884 Zip Code

Under contract-accepting backup offers. Located in one of Southeast Winter Haven's most desirable neighborhoods, just minutes from the Chain of Lakes and Lake Summit boat ramp, this beautifully updated 4-bedroom, 3-bath pool home offers nearly 2,500 square feet of living space with **no HOA**. Designed with flexibility in mind, the home features two spacious primary suites, multiple living areas, and a beautifully remodeled kitchen with quartz countertops, soft-close cabinetry, stainless steel appliances, and a workstation sink. Step outside to the screened lanai overlooking the private pool and enjoy the fully fenced backyard - perfect for entertaining, pets, and everyday living. Major updates include a NEW ROOF (2019), HVAC (2019), HOT WATER HEATER (2019), primary bathroom remodel (2019), kitchen remodel (2021), pool heater (2022), pool pump (2024), front and backyard irrigation system (2024), and guest bathroom remodel (2025). Offering quality updates, generous living space, and an exceptional location! Schedule your private showing today!

144 Beverly Dr, Winter Haven

$90,500

2 Beds ⋅ 2 Baths ⋅ Orchid Spgs Vill 200 Condo SubDv. ⋅ 33884 Zip Code

Under contract-accepting backup offers. WELCOME TO THE SEVILLE BUILDING IN BEAUTIFUL ORCHID SPRINGS. THIS IS A LARGE (1,378 SQUARE FEET) TWO BEDROOM TWO BATH UNIT LOCATED ON THE THIRD FLOOR. ELEVATORS ARE POSITIONED IN THE CENTER OF THE BUILDING FOR RESIDENTS CONVENIENCE. THIS UNIT HAS BEEN UPGRADED AND IS READY FOR IT'S NEW OWNERS. THIS FLOORPLAN HAS A SPLIT- BEDROOM PLAN. THE RESIDENCE OVERLOOKS A BEAUTIFUL TROPICAL LAGOON. THE ROOF WAS REPLACED IN 2025 AND THE ENTIRE BUILDING IS CURRENTLY BEING PAINTED. THE GALLEY KITCHEN HAS BEEN REDONE AND HAS STAINLESS STEEL APPLIANCES. THE PRIMARY BEDROOM IS SPACIOUS WITH A REMODELED ENSUITE BATH WITH A HUGE WALK-IN CLOSET. THE SECOND BEDROOM HAS ACCESS TO ITS OWN UPDATED BATH ALSO. THE MONTHLY HOA FEE COVERS, GAS, WATER, TRASH, SEWER, CLUBHOUSE & POOL, EXTERIOR MAINTENANCE AND GROUNDS UPKEEP. THIS WELL-KEPT HOME IS PRICED TO SELL.

200 El Camino Drive Unit 311, Winter Haven

$429,000

3 Beds ⋅ 2 Baths ⋅ Winterset Gardens SubDv. ⋅ 33884 Zip Code

Virtually Staged. Rarely does a home this unique come to market! Situated on a spacious .30-acre lot directly across the street from beautiful Lake Winterset, this fully renovated 3-bedroom, 2-bath mid-century modern pool home offers incredible character, modern updates, and NO mandatory HOA or CDD. An optional neighborhood HOA of just $100 per year provides access to the community boat ramp, connecting you to the renowned Winter Haven Chain of 22 Lakes, one of Central Florida's premier destinations for boating, fishing, and watersports. Unlike nearly any other Florida home, this property features an impressive 300+ square foot basement, a rare find that offers endless possibilities as a wine cellar, hobby room, workshop, fitness area, or additional storage. The home's distinctive architectural design is complemented by spectacular views of Lake Winterset from the living and dining rooms, where sliding glass doors open to a charming wraparound front porch—the perfect place to enjoy your morning coffee while taking in the peaceful lake scenery. Upstairs, a spacious bonus room provides flexibility as a potential fourth bedroom, media room, home office, or second living area and includes a private balcony overlooking the front of the property and the lake. The beautifully updated kitchen is designed for both everyday living and entertaining with quartz countertops, a center island, pantry, recessed lighting, tile backsplash, reverse osmosis system, garbage disposal, a window overlooking the screened pool, and a premium 2022 Samsung Bespoke appliance suite. The home's thoughtful split layout places all three spacious bedrooms down a private hallway away from the main living spaces. Wood-look tile flooring flows throughout the main living areas, while luxury vinyl plank flooring extends through the bedrooms, bathrooms, and upstairs bonus room. The spacious primary suite features dual vanities and a beautifully remodeled walk-in shower. Additional conveniences include an indoor laundry closet with the washer and dryer included, and a two-car garage. Step outside to your oversized screened, chlorinated pool complete with a diving board and removable safety fence, creating the perfect backyard retreat for entertaining family and friends year-round. Major improvements provide added peace of mind, including a new roof in 2025, a new pool pump and well pump in 2025, new A/C ductwork and attic insulation in 2025, windows replaced in 2019, A/C replaced in 2019, water heater replaced in 2019, and new appliances installed in 2022. Ideally located just a short drive from Disney, Universal, LEGOLAND, and other Central Florida attractions, this one-of-a-kind home combines timeless mid-century modern architecture, extensive modern updates, a rare basement, beautiful lake views, access to the Winter Haven Chain of Lakes, and a lifestyle that is truly hard to find. Don't miss this rare opportunity to own one of the area's most distinctive homes overlooking beautiful Lake Winterset.

6704 Winterset Gardens Road, Winter Haven

$249,900

3 Beds ⋅ 2 Baths ⋅ Lucerne Park Reserve SubDv. ⋅ 33881 Zip Code

Welcome to 297 Meadowbrook Boulevard, a well-maintained 3-bedroom, 2-bathroom home located in the Lucerne Park Reserve community of Winter Haven. Built in 2020, this single-story residence offers approximately 1,408 square feet of comfortable living space with a functional, open-concept floor plan designed for everyday living and entertaining. The kitchen flows seamlessly into the main living and dining areas, creating an inviting central gathering space. The primary suite features a private bathroom and generous closet space, while two additional bedrooms provide flexibility for guests, a home office, hobbies, or additional living needs. A two-car attached garage offers convenient parking and storage. Residents can enjoy access to community amenities, including a swimming pool and playground. Conveniently situated near shopping, dining, schools, recreation, and major roadways, this property provides easy access to Winter Haven and the surrounding Central Florida area. Schedule your private showing today and explore everything this home has to provide!

297 Meadowbrook Boulevard, Winter Haven

$99,000

2 Beds ⋅ 1 Baths ⋅ Winter Haven Harbour Apts Condo SubDv. ⋅ 33881 Zip Code

Peaceful oasis in a premier 55+ community! This lovely 2 bedroom, 1 bath second-floor condo in Winter Haven Harbour Apartments offers a perfect blend of comfort, functionality, and an active, low-maintenance lifestyle. Inside, you will find a spacious living room that flows effortlessly into a dedicated dining room, and a galley-style kitchen that maximizes counter space and storage, making meal preparation a breeze. Step onto your private balcony, where you can enjoy your morning coffee, read a book, or soak in the serene views. This wonderful active community offers fantastic resort-style perks, including a sparkling heated community pool, an active community center, and shuffleboard courts for fun with friends and neighbors. This home provides the ideal setting for your next chapter. Don't miss out, schedule your appointment today.

1700 6th St Nw Unit C24, Winter Haven

$149,900

2 Beds ⋅ 2 Baths ⋅ Spring Lake Towers SubDv. ⋅ 33881 Zip Code

Enjoy maintenance-free lakefront living in this 2-bedroom, 2-bathroom condominium located in the highly sought-after Spring Lake Towers, a premier 55+ active adult community in the heart of Winter Haven. Updated in 2020, this inviting residence offers BREATHTAKING VIEWS OF SPRING LAKE, part of the scenic Spring Lake Meander, and a bright, open living space that feels like an indoor lanai, where walls of windows create the perfect setting to relax while overlooking the tranquil water. Both the primary bedroom and the second bedroom have direct access to this enclosed lakefront space, creating a seamless connection to the serene waterfront and providing the perfect spot to enjoy your morning coffee, unwind with a book, or simply take in the picturesque views of Spring Lake throughout the day. The updated kitchen is designed for both style and function, featuring soft-close cabinetry, porcelain countertops, recessed lighting, a decorative tile backsplash, a convection oven, and a convenient center island cart. Luxury vinyl flooring flows throughout the main living areas, while the bedrooms offer the comfort of carpet. The spacious primary suite features a walk-in closet and an ensuite bath, while the secondary bathroom has been tastefully updated with a beautifully tiled glass-enclosed shower. The all-inclusive condo fee provides exceptional value, covering cable TV, high-speed internet, water, sewer, trash removal, exterior building maintenance, roof maintenance, building insurance, reserve funds, on-site management, groundskeeping, and assigned covered parking. Residents enjoy an impressive selection of community amenities, including a waterfront in-ground concrete pool, fitness center, recreation room with a full kitchen, library, game area, shuffleboard courts, laundry facilities, private boat docks, and a year-round social calendar. Take advantage of the community's private dock, where boat slips are available on a first-come, first-served basis for a minimal monthly fee, offering convenient access to Spring Lake Meander for boating, fishing, or simply enjoying the peaceful waterfront setting. Ideally located just minutes from historic downtown Winter Haven, the renowned Chain of Lakes, shopping, dining, medical facilities, golf courses, and LEGOLAND® Florida Resort, this waterfront condo offers the perfect blend of low-maintenance living, spectacular views, and an active Florida lifestyle.

700 Mirror Terrace Nw Unit 511, Winter Haven

$409,000

3 Beds ⋅ 2 Baths ⋅ Lake Ashton West Ph I SubDv. ⋅ 33884 Zip Code

Under contract-accepting backup offers. HOME FOR SALE IN LAKE ASHTON! Is 4052 Phoenician Way, Winter Haven, Florida YOUR next address? This 3 Bedroom, 2 Bath home with Golf Cart Entry is located on a large premium lot that abuts to the 13th Fairway of Lake Ashton's West Golf Course. The view from the wrap around covered and screened lanai includes a large pond that borders the 13th Hole with a farm pasture beyond. Home Highlights: CDD Debt Balance Paid in Full; Roof Replaced 2022; Water Heater Replaced 2022; A/C Heat Pump Replaced 2019. This home offers excellent curb appeal with a Widened Drive Way, Poured Curbing, Well Maintained Mature Landscape with Landscape Rock, Quoined Corners, Bay Window on the Front Bedroom, and arched Screened Entry. A paver walkway on the right side of the home connects the access door of the golf cart garage to the rear lanai. The interior of this home is warm and inviting with an Open and Spacious Living area. The Foyer, Dining, LR and Kitchen flow seamlessly together making entertaining a "breeze" in this home. The beautiful Bruce interlocking Engineered natural oak floors and the Plantation Shutters on the Side Lights of the Front Entry Door, Double Sliding Glass Doors in the Living Room, Bedroom 2 and Primary Bedroom accent the interior of this home- adding a touch of class. Crown molding gives definition to the Open Living area. The kitchen upgrades include: Granite counter tops, Maple Cabinets with raised panels, 3 banks of drawers, crown molding and a pantry. The refrigerator, microwave and disposal were replaced in 2026 and the range was replaced in 2023. A breakfast bar/snack bar and Dining areas are perfect for entertaining friends and family. Enter thru the 8' Front entry door with Eyebrow window above. To the left of the foyer are Bedrooms 2 and 3, a Linen Closet in the Hallway and a Guest Bathroom with shower/tub combo, accent window and comfort height vanity. A pocket door provides privacy to the Guest Bedroom area. The EXTENDED Primary Suite is located on the back on the home. It's the perfect place to relax after a long day in the sun. The Primary Suite offers a spacious sitting area and En-Suite with His/Her Walk in Closets, His/Her Separate Vanities, a large corner Soaking tub, a separate water room with a walk in shower with glass doors and linen closet. The laundry room is easily accessible from the garage and kitchen. It has cabinets for storage, a wash tub and the washer/dryer will be included in the sale of the home. The double car garage has hang down storage racks, attic access, storage cabinets, and an access door to the outside. There is a motorized screen on the garage door and a separate entry for the golf cart. The outdoor living space is a destination location in this home. The view is peaceful and the space is cozy with paver floor, ceiling fans and TV hook up. Make an appointment to tour this home today! Lake Ashton is a gated and guarded Florida Active Community with resort style amenities (2 Clubhouses with Movie Theater, Restaurant, Outdoor/Indoor Pools, Fitness Centers and More! Residents enjoy activities like Karaoke, Trivia, Dances, Entertainment Series, Holiday Events and so much more. You can stay busy living the Florida Retirement Dream every single day. For those that love the game of golf, there are (2) 18-Hole Golf Courses, a Pro Shop, Driving Range, Putting Green and the Eagles Nest (Hole 19). Don't wait to tour this home; tour it today!

4052 Phoenician Way, Winter Haven

$274,990

3 Beds ⋅ 2 Baths ⋅ Leisure Shores SubDv. ⋅ 33881 Zip Code

Welcome to this beautifully maintained 3-bedroom, 2-bath home offering approximately 1,627 square feet of comfortable living space in the established Leisure Shores community of Winter Haven. Situated on a spacious 0.22-acre lot, this property is packed with features both inside and out. Step inside to an open floor plan with easy-to-maintain laminate flooring throughout, an updated kitchen featuring granite countertops, newer cabinetry, stainless steel appliances, and plenty of space for everyday living and entertaining. Energy-efficient double-pane windows and an updated sliding glass door help enhance comfort throughout the home. The backyard is designed for enjoying Florida living, complete with a screened lanai, an above-ground pool, a large side deck, and a fully fenced yard that’s perfect for relaxing or hosting family and friends. Need extra space? This property offers multiple detached structures, including a spacious air-conditioned shed that’s ideal for a home office, hobby room, gym, studio, or workshop, plus an additional storage shed for tools and equipment. For those with recreational vehicles or extra toys, you’ll appreciate the dedicated RV parking area with electrical hookup, along with a covered carport for everyday parking. Conveniently located near shopping, dining, schools, and everything Winter Haven has to offer, this home combines comfort, versatility, and outdoor living in one exceptional package. Schedule your private showing today!

2021 Oliver Place, Winter Haven

$498,500

4 Beds ⋅ 3 Baths ⋅ Cypresswood Plantations SubDv. ⋅ 33884 Zip Code

Located on a quiet cut-de-sac in the desirable Plantations part of the guard gated golfing community of Cypresswood Golf & Country Club, this 4BR/3BA beauty w/ more than 2500 sq ft has upgrades galore & is just what you've been looking for! The home has a fantastic open floor plan w/ split bedrooms, volume ceilings, crown molding, double pane windows, plantation shutters, arched entryways, & super stylish hickory scraped wood looking tile throughout! The lovely formal dining room w/ it's arched entrances flows nicely just off the foyer, while another arch entry leads straight ahead into the spacious great room w/ a tray ceiling & French doors leading to the inviting Florida room. The large eat-in-kitchen features beautiful custom maple cabinets w/ pull-outs, new quartz countertops & tile backsplash, a breakfast bar, soft accent lighting over the cabinets & it comes equipped w/ all of the upgraded appliances including a new stainless steel refrigerator, microwave & gas range, as well as a new kitchen sink & faucet! The quaint breakfast nook has a beautiful picture window that provides lots of natural light while you're enjoying the serene backyard views. The primary suite is huge & features a cozy sitting area w/ French doors leading to the Florida rm & there's an ornate barn door entrance leading into the primary bathroom complete w/ a garden tub, nicely tiled step-in shower, double sink vanity w/ quartz countertop & a walk-in closet. The 2nd & 3rd BR's are situated on the other side of the living areas for added privacy & they have a Jack-n-Jill bath between them that has a double sink vanity w/ quartz countertop as well as a tub & shower combo. The 4th BR is located just down the hall from the Primary bedroom making it a nice option for a nursery/small child's room or an office. It would also be a nice guest room w/ the 3rd bathroom conveniently located right beside it w/ quartz countertop & a step-in shower w/ a nice glass enclosure. The large Florida rm has lots of windows overlooking the landscaped back yard & it even has a wet bar complete w/ mini fridge, a wine fridge & of course ...quartz countertops making it the perfect spot for entertaining. Additional features include an inside laundry room, a double car garage, fairly new C/H/A, a whole house gas generator, a water softner/purificiation system, central vac, & there's even a fire pit in the back yard on this 1/3+ acre property tucked away in Cypresswood Golf & Country Club, with lots of community amenities including a 24 hour manned gated entrance, a community pool for you to enjoy & not have to maintain, plus there's pickleball courts, tennis courts, a large clubhouse w/ fitness center, restaurant, pro shop & surrounded by the lovely golf course! Close to shopping, restaurants, medical, the new Publix, Legoland & more & Conveniently located in the heart of Central Florida between Orlando & Tamps and not far from all of the major attractions. All measurements are approximate and all info should be confirmed by buyers.

3158 Beauchamp Court, Winter Haven

$320,000

4 Beds ⋅ 2 Baths ⋅ Mandolin SubDv. ⋅ 33884 Zip Code

Under contract-accepting backup offers. POOL HOME + PAID-OFF SOLAR in the gated Mandolin community! This four-bedroom, two-bath Winter Haven home combines a private pool and raised spa with exceptionally low energy costs—the seller reports recent electric bills of approximately $40 per month. Inside, the single-story layout features vaulted ceilings, abundant natural light and durable hard-surface flooring throughout the main living areas. The kitchen offers granite countertops, rich wood cabinetry, stainless-steel appliances and a breakfast bar overlooking the adjoining dining and living spaces. The primary suite features a generously sized bedroom, walk-in closet and private bath with dual sinks, soaking tub, separate shower and private water closet. Three additional bedrooms provide flexibility for family, guests, a home office or hobby space, and the indoor laundry room adds everyday convenience. Step outside to your own Florida backyard retreat. An expansive paver deck surrounds the in-ground pool and raised spa, while the covered patio provides a shaded area for outdoor dining, relaxing and entertaining. The fenced yard and pool safety fence add additional convenience. PAID-OFF SOLAR PANELS offer another major benefit, with the seller reporting recent electric bills of approximately $40 per month. The home also includes an attached two-car garage and sits on approximately a quarter-acre lot. Conveniently located near LEGOLAND Florida, shopping, dining, medical facilities and major roadways, this home offers a hard-to-find combination of four bedrooms, a private pool and spa, gated community living and significant energy savings. Schedule your private showing today!

233 Mandolin Drive, Winter Haven

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