Between $300,000 - $400,000 Winter Haven FL Real Estate, Homes, Condos for Sale

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

Beautiful Single Level, 2 Car Garage Home with Open Concept Living and 4 Bedrooms! The Baker plan is in Farmhouse exterior design. Adjacent the foyer you'll find 3 secondary bedrooms and a full bathroom. The well-appointed island kitchen overlooks the spacious family room and adjoining cafe with access to the covered lanai. The primary suite boasts an en suite bathroom with dual sink vanity, shower, private water closet, and large walk-in closet.

815 Andrew Street, Winter Haven

$364,999

5 Beds ⋅ 3 Baths ⋅ Villa Mar SubDv. ⋅ 33884 Zip Code

Under Construction. Indigo BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. Check out the Indigo, a spacious two-story, 5-bedroom, 3-bathroom, 2-car garage home perfect for growing families or hosting guests. Enter the impressive foyer with soaring ceilings that creates an immediate sense of openness. From the foyer, the home effortlessly flows into the main living areas and kitchen. With quartz countertops throughout, stainless-steel appliances and a smart thermostat for energy efficient climate control, the Indigo brings all the things that matter together. The downstairs guest suite and bathroom are tucked away for added seclusion, while the open concept living space is perfect for entertaining. Upstairs, you'll find a generously sized recreation space, ideal for family time or unwinding. The owner's suite is a true sanctuary, featuring a walk-in shower, double vanities, and a spacious walk-in closet. A laundry room with a new washer and dryer is just off the owner’s suite, conveniently located near the 3 additional bedrooms and full bathroom. The Indigo is as functional as it is stylish, providing the perfect balance of comfort and modern living. Close to it all, Villa Mar places you near the natural beauty of the Winter Haven Chain of Lakes, the charm of downtown Winter Haven, and family fun at LEGOLAND® Florida Resort. Back at home, residents enjoy community amenities including a pool, dog park, playground, and walking trails. Images shown are for illustrative purposes only and may differ from actual home. Completion date subject to change. Contact or make an appointment for more details on interest rates.

5441 San Pietro Drive, Winter Haven

$300,000

3 Beds ⋅ 2 Baths ⋅ Kensington View SubDv. ⋅ 33880 Zip Code

Virtually Staged. Welcome to this beautiful, move-in-ready home offering comfort, style, and easy maintenance! Step inside to a bright and inviting layout featuring no carpet throughout the home, making everyday living and upkeep a breeze. The kitchen is equipped with updated appliances and provides a functional space for preparing meals and entertaining family and friends. Step outside to the screened-in back porch, the perfect place to relax and enjoy the Florida weather while overlooking the backyard. Whether you're enjoying your morning coffee, unwinding after a long day, or hosting guests, this outdoor space adds even more room to enjoy the home. Conveniently located in Winter Haven with access to shopping, dining, schools, and major roadways, this home is ready for its next owner. Schedule your showing today and see everything this property has to offer!

477 Kensington View Drive, Winter Haven

$370,000

4 Beds ⋅ 3 Baths ⋅ Overlook Estates East SubDv. ⋅ 33884 Zip Code

HOME SWEET HOME! This sweet 4 bedroom 3 bath home is ready for its next happy homeowner. Located in a small gated community in SE Winter Haven this one has the perfect combination of location, and comfort. Check out the homey kitchen with granite countertops and wood cabinets. The corner pantry can hold all your treats for those football weekend get togethers. The rooms have large windows offering abundant natural light, and space for everyone. The ideal 3 way split bedroom plan offers form, and function. The spacious yard offers peace, and privacy with a PVC-fenced back yard, and extra storage in a charming 10x12 planters shed. The 2025 architectural shingle roof, 2017 AC dual zone AC system, and Generac generator have you covered in all Florida weather. Check out this sweet property today. Step inside, fall in love. Make it yours!

754 Santa Maria Dr, Winter Haven

$399,900

4 Beds ⋅ 3 Baths ⋅ 33880 Zip Code

Freedom and flexibility await in this amazing 4 bedroom, 3 bathroom ranch-style POOL home, featuring beautiful updates, a floor plan ideal for multi-generational needs, and a detached garage offering plenty of room to store your boats, ATV's, Jet Skis or hot rods! Situated on a .6-acre cul-de-sac lot right across the street from Eagle Lake with NO HOA, here you are tucked away from it all, with space to enjoy your own private piece of paradise. Crisp landscaping, a covered front entry and an extended driveway make a nice first impression. It is clear from its tasteful updates and excellent condition that this home has been lovingly maintained. You will appreciate the attractive finishes, knockdown ceilings (no popcorn!), stylish fixtures and solid flooring throughout. The layout offers options and space, with formal and informal living areas, a separate formal dining room and triple split bedrooms, including two with en-suite bathrooms. An updated primary suite provides a peaceful retreat, with a spacious bedroom, walk-in closet, and a gorgeous bathroom including a jetted tub, dual sinks, and a walk-in shower. The second en-suite at the back of the home is a wonderful space for guests or live-in loved ones of all generations, with a bedroom including a Murphy Bed, a refreshed bathroom, and convenient access to the pool. There are also two additional bedrooms and a guest bathroom down a hallway, providing separation from the rest of the home. The remodeled kitchen is stunning, with white soft-close cabinetry, stainless steel appliances, closet pantry, quartz countertops, and a breakfast bar with seating. A window from the kitchen sink overlooks the remodeled pool area. The pool was recently resurfaced, with a new pump and salt system, a screen enclosure and a large, covered paver lanai - perfect for relaxation and entertaining. Green space is ample in the back yard, with room and hookups to park up to a 45-foot RV, and a private air-conditioned shed for a workshop, gardening or hobbies. The incredible 30x40x14 garage, however, is the highlight of this area, with two 12 foot roll up doors, concrete floors, side walk-in door and 1 window. Just imagine what you could do in this space! Solar panels (2023) provide efficiency in this home, while other key system updates include water heater (2024), well pump (2026), driveway (2024), A/C (2022), and Culligan water system (2023). The best part about this home, though, is that it is a FUN place to live! You really can make this space all your own, enjoying your time inside and out, with easy access to the water and all that Central Florida living has to offer! **LOCATED IN A USDA ELIGIBLE AREA**

5014 Sunrise Drive, Winter Haven

$379,000

4 Beds ⋅ 2 Baths ⋅ West Winter Haven SubDv. ⋅ 33880 Zip Code

Step into a piece of Winter Haven history—beautifully reimagined for modern living. Just moments from Lake Howard, this exceptional 1925 residence offers the character and craftsmanship today's luxury buyers crave, paired with a complete top-to-bottom transformation. Original refinished 101 year old hardwood floors and two sets of original French doors provide a timeless connection to the home's past, while the rest has been thoughtfully rebuilt with today's lifestyle in mind. The custom kitchen, elegant architectural details, crown molding, tray ceilings, and spacious living areas create a home that feels both sophisticated and inviting. The private primary suite is a true retreat, featuring his-and-hers walk-in closets and a spa-inspired ensuite with a two-person tiled shower, garden tub, and generous vanity space. Two additional bedrooms upstairs add flexibility for guests, family, or a private home office. With approximately 2,011 heated square feet, 4 bedrooms, 2 baths, a dedicated laundry room, fully fenced backyard, and no HOA, this is a rare opportunity to own something with genuine character—not another cookie-cutter home. Bring your boat and water toys and enjoy the freedom and lifestyle that come with living near Winter Haven's beautiful Chain of Lakes. For buyers who appreciate history, character, and modern luxury, this is a home that simply must be experienced in person.

2112 Avenue C Sw, Winter Haven

$399,999

3 Beds ⋅ 3 Baths ⋅ Ruby Lake Ph 06 SubDv. ⋅ 33884 Zip Code

Under contract-accepting backup offers. Virtually Staged. Welcome to this beautifully remodeled 3-bedroom, 3-bath home with a private office that can easily serve as a 4th bedroom. Located in the Desirable Ruby Lake gated community in Winter Haven, this move-in-ready home offers a great combination of modern updates, spacious living, mature landscaping, and a peaceful lake view. Inside, you'll find soaring 10-foot ceilings, crown molding, and porcelain tile flooring throughout the entire home. The fully remodeled kitchen features granite countertops, stainless steel appliances, updated cabinetry, and plenty of space for cooking and entertaining. The primary bathroom has also been completely renovated with modern finishes, giving the home a fresh, updated feel. Step outside to the fully screened back patio and enjoy relaxing or entertaining while overlooking the lake and mature landscaping. The home has been freshly painted inside and out, and the garage features a clean, durable epoxy-coated floor. A private well provides irrigation for the landscaping, helping reduce monthly water expenses. Conveniently located near LEGOLAND Florida Resort, Winter Haven's famous Chain of Lakes, shopping, dining, schools, and local attractions, this home offers the comfort of an established neighborhood with the updates and finishes of a newly remodeled property. With 3 bedrooms, 3 full bathrooms, a flexible office/4th bedroom, beautiful lake views, and extensive renovations throughout, this Winter Haven home is ready for its next owner! Schedule your private showing today!

274 Ruby Lake Lane, Winter Haven

$325,990

4 Beds ⋅ 2 Baths ⋅ Lake Smart Pointe SubDv. ⋅ 33881 Zip Code

Spacious 4-bedroom home in the beautiful and well-kept Lake Smart Pointe community, offering LOW HOA and NO CDD. This home features an open-concept layout with a kitchen island, Jack & Jill bath, and a private backyard with no rear neighbors and expansive green space behind the property. Nice neighborhood with convenient access to shopping, dining, schools, and major highways. More photos coming soon.

380 Lake Smart Circle, Winter Haven

$350,000

3 Beds ⋅ 2 Baths ⋅ Summerhaven Shores SubDv. ⋅ 33884 Zip Code

**THIS IS THE ONE!!** IMMACULATE SE WINTER HAVEN, FLORIDA HOME LOCATED ON A SHADED CUL-DE-SAC LOT WITH NO HOA. NEW ARCHITECTURAL SHINGLE ROOF INSTALLED 2022, AC-HEAT PUMP SYSTEM UPDATED 2020 and NEW INSULATED WINDOWS THROUGHOUT! The privacy-fenced rear yard has double-wide gates allowing access for storing your boat or RV plus plenty of space for the existing 10 x 16 storage/work shed with power, a large patio & separate fenced area for dog space or a garden! The living room & dining room area are conveniently located adjacent to the spacious, updated custom kitchen featuring granite countertops, stainless steel appliances, a 4-door refrigerator, 10 cabinet drawers, a pull-out trash drawer & center island. The family room features a beautiful brick fireplace with hearth and mantle ...perfect for enjoying & decorating on holidays! Sliding glass exit doors allow access from the family room to the welcoming 18 x 37 covered and screened patio. The primary bedroom has a walk-in closet and includes a remodeled en-suite bathroom with a custom tiled walk-in shower and glass shower door. Bedrooms 2 and 3 are near the remodeled hall bath that features a comfort-height vanity & tub-shower combination. This lovely, well-maintained home is perfect for gatherings & entertaining! A public park with a boat ramp on Lake Ned is less than a mile away! Shopping and restaurants are nearby, plus be sure to check out the brand-new Publix grocery store located on Dundee Road! Easy access to Hwy 27 & I-4, Orlando, Tampa area attractions & both coasts. Measurements are approximate. Info is believed to be accurate but not guaranteed. This one will sell soon, so make your showing appointment today!

216 Shore Loop, Winter Haven

$385,000

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

POOL HOME WITH POND VIEW IN GATED TERRANOVA! -NEW AC UNIT DECEMBER 2025--ROOF & HOT WATER HEATER ARE 6 YEARS OLD-- Welcome to this spacious 3-bedroom, 2-bath home offering 2,118 square feet of living space and a relaxing Florida lifestyle in one of southeast Winter Haven’s gated communities. The highlight of the home is the screened-in private pool overlooking the pond, creating a peaceful water-view backdrop for relaxing, entertaining, or enjoying time outdoors. Inside, the split-bedroom floor plan offers multiple living spaces, including a comfortable family room featuring a wood-burning fireplace. The eat-in kitchen provides plenty of space for casual dining and features a decorative backsplash behind the countertops, while the dining area flows naturally into the living room for an open and connected feel. Sliding doors provide access to the covered and screened pool area, where you can enjoy the pond views from your own backyard. The home also features a full bathroom with direct access to the pool area, adding extra convenience for family and guests. Additional features include an inside laundry room, walk-in closet, ceiling fans, attached 2-car garage, and a north-facing front exposure. Terranova is a gated community conveniently located in southeast Winter Haven with easy access to shopping, dining, schools, medical facilities, and area attractions including LEGOLAND Florida. Enjoy the combination of a private pool, water view, spacious interior, and gated-community setting—all in a convenient Winter Haven location. Schedule your private showing today!

543 Terranova Circle, Winter Haven

$350,000

5 Beds ⋅ 3 Baths ⋅ Pinnacle Point SubDv. ⋅ 33880 Zip Code

Short Sale. This is a SHORT SALE-THIRD PARTY APPROVAL REQUIRED. Spacious and extensively upgraded, this 5-bedroom, 3-bath home offers more than 3,000 square feet of flexible living space in the Pinnacle Point community. The open floor plan features an impressive remodeled kitchen, upgraded flooring, generous living and gathering areas, and plenty of room for a large household, home offices, guests, or multigenerational living. Outside, enjoy a fenced backyard and improved patio area ready for relaxing, entertaining, or weekend cookouts. Built in 2022, the home also includes a two-car garage and convenient access to shopping, dining, medical facilities, and Central Florida attractions. Some interior projects remain unfinished, allowing the next owner to add their personal finishing touches.

1436 Axel Circle, Winter Haven

$316,000

4 Beds ⋅ 3 Baths ⋅ Peace Crk Reserve SubDv. ⋅ 33884 Zip Code

Modern Comfort Meets Natural Serenity – 1228 Tyler Loop, Winter Haven, FL Discover peaceful Florida living in this beautifully maintained 4-bedroom, 3-bath Lennar Next Gen® home in the desirable Peace Creek Reserve community. Built in 2024 and offering approximately 2,100 square feet of thoughtfully designed, single-story living space, this home combines modern comfort, flexible living arrangements, and tranquil natural views. The open-concept main living area features high ceilings, abundant natural light, quartz countertops, stainless-steel appliances, and tile flooring in all wet areas. The smart, spacious layout creates an inviting setting for both everyday living and entertaining. A standout feature is the private Next Gen suite, complete with its own entrance, kitchenette, living room, bedroom, and full bathroom. This flexible space is ideal for extended family, guests, a home office, or a comfortable multigenerational living arrangement. Step outside to a fully fenced backyard overlooking a natural retention basin with protected wetlands beyond. The open rear fencing preserves the peaceful view, where Sandhill cranes, water birds, turtles, and other native wildlife can often be seen. With no immediate rear neighbor, the outdoor space offers an added sense of openness and connection to nature. The two-car garage features an eye-catching epoxy-coated floor with black, silver, gold, and brown flecks that shimmer in the light—a sleek and practical upgrade that sets this home apart. A six-foot privacy fence with gates on both sides provides additional seclusion while maintaining the panoramic rear view. Peace Creek Reserve offers residents access to a community swimming pool and playground. The home is situated on a quiet, U-shaped street with low traffic and is conveniently located near shopping, dining, schools, Highway 27, and Winter Haven’s celebrated Chain of Lakes. For recreation and entertainment, LEGOLAND® Florida Resort is approximately 15 minutes away, while Walt Disney World is generally less than an hour away, depending on traffic. This location offers an appealing balance of peaceful residential living and convenient access to some of Central Florida’s most popular attractions. Schedule your private tour today and experience the comfort, flexibility, and natural setting this distinctive home has to offer.

1228 Tyler Loop, Winter Haven

$310,990

5 Beds ⋅ 3 Baths ⋅ Villa Mar 40'S SubDv. ⋅ 33884 Zip Code

Under Construction. This two-story Georgia will definitely be on your mind… This beauty highlights a modern open layout, seamlessly integrating a first-floor kitchen with a central island, a dining room and a welcoming family room with patio access. On the same level is a private owner's suite with an attached bathroom. Situated upstairs is a versatile loft for additional shared living space and four secondary bedrooms to provide restful retreats to family members and guests alike. Villa Mar is a masterplan community of new single-family homes. Near Historic downtown Winter Haven. There are lots of shops, restaurants, bike paths, and easy access to nearby highways. Close to Legoland and Bok Tower Gardens. The much anticipated “Villar Mar” community is what you have been looking for. A safe small town feel with convenience.

6217 Botticella Boulevard, Winter Haven

$335,000

3 Beds ⋅ 2 Baths ⋅ Garden Grove SubDv. ⋅ 33884 Zip Code

Welcome to this beautifully maintained 3-bedroom, 2-bathroom pool home offering comfort, functionality, and peace of mind with numerous recent improvements. From the moment you arrive, you’ll appreciate the inviting curb appeal, long driveway, and convenient side-entry garage. Step inside to a freshly painted interior and a warm, welcoming atmosphere featuring a wood-burning fireplace, perfect for cozy evenings at home. The spacious layout provides comfortable living areas and well-appointed bedrooms, making this home ideal for everyday living and entertaining. Step outside and discover your own private retreat! The resurfaced pool, completed in 2023, is surrounded by a large screened-in lanai, creating an expansive outdoor living space where you can relax, entertain, and enjoy the Florida lifestyle year-round. This home has been thoughtfully updated with numerous major improvements, including a 2023 roof and gutters, 2024 exterior paint, 2026 interior paint, and 2024 attic insulation. The HVAC system and water heater were replaced in 2021, along with the pool pump, providing added efficiency and peace of mind. Solar panels are already in place and will be paid off by the seller at closing, allowing the new homeowner to enjoy the benefits of solar without assuming the existing balance. Best of all, there is NO HOA, giving you greater freedom and flexibility. With a spacious lot, side-entry garage, long driveway, private pool, large screened lanai, and an impressive list of updates, this home is ready to welcome its next owner. Located in Winter Haven with convenient access to several lakes, local shopping, dining, recreation, major roadways and more. Come see all this move-in-ready pool home has to offer!

121 Lowell Road, Winter Haven

$390,000

4 Beds ⋅ 2 Baths ⋅ Eloise Woods East Lake Mariam Unit SubDv. ⋅ 33884 Zip Code

Welcome home to this CLEAN and PRISTINE 4-bedroom, 2-bathroom BLOCK pool home on a large lot with NO HOA! Inside, a great layout, light and bright walls and floors, and updated bathrooms, kitchen and flooring create a welcoming, modern feel. Sleek hurricane-impact windows and sliding doors add style, natural light, and peace of mind, while the roof and HVAC are both under 4 years old. Step outside and discover your own Florida oasis! The OVERSIZED POOL (36'x17') and huge 12' x 25' SCREENED-IN TILED PATIO create an incredible space for entertaining, relaxing, morning coffee, or enjoying beautiful Florida evenings. The spacious lot offers plenty of room to spread out, garden, and play! Solar panels add an energy-conscious bonus and meaningful energy savings. The location is hard to beat! You are just 5 minutes from LEGOLAND, with sparkling lakes nearby for boating and fishing, golf courses, great restaurants, and plenty of Central Florida attractions within easy reach. Solid, stylish, spacious, and wonderfully located-this is a Florida home with room to live, relax, entertain, and make lasting memories. Come check it out TODAY!

437 Broward Terrace, Winter Haven

$395,000

4 Beds ⋅ 3 Baths ⋅ South Roy Shores Pb 38 Pg 45 SubDv. ⋅ 33884 Zip Code

Under contract-accepting backup offers. Spacious 4-Bedroom, 3-Bath Pool Home on a Corner Lot in Winter Haven! Ideally located in a convenient area of Winter Haven and situated across from lakefront homes, this 2,955-square-foot home offers a spacious layout with plenty of room to make it your own. The triple-split bedroom floor plan provides privacy and flexibility, while the oversized family room features two sets of sliding glass doors leading directly to the screened and netted pool enclosure and covered patio, creating an inviting space for entertaining and enjoying Florida's outdoor lifestyle. A versatile flex room adds even more living space and offers direct access to the pool and screened patio, making it ideal as a game room, home office, hobby room, or additional entertainment area. The kitchen is one of the home's standout features, offering custom-made cabinetry, granite countertops, a custom tile backsplash, and stainless-steel appliances. The primary suite includes a private bathroom with a garden tub, dual sinks, and a walk-in shower. Additional interior highlights include a LARGE LAUNDRY ROOM with a utility sink, drop-down ironing board, and extra shelving, along with tile and wood flooring throughout the main living areas. Outside, enjoy the screened-in and NETTED POOL ENCLOSURE with a covered patio, surrounded by a grassy yard area, plus a welcoming front screened porch, ample covered parking, and two detached storage sheds for added convenience. The yard is irrigated by a well with a newer irrigation timer. The ROOF WAS INSTALLED IN 2023, and the HVAC SYSTEM IS APPROXIMATELY 9 YEARS OLD. While some areas of the home could benefit from cosmetic updates and freshening to bring out their full potential, the spacious floor plan, desirable pool setting, established features, and prime location make this an exciting opportunity for a buyer ready to add their personal style. For those who enjoy being on the water, the property is just A SHORT WALK TO FREEDOM BOAT CLUB, offering an easy way to rent boats and explore Winter Haven's renowned Chain of Lakes. The home is also approximately one mile from LEGOLAND Florida, adding to the property's appeal and convenience. With its spacious floor plan, private pool setting, flexible living spaces, and desirable location near the area's lakes and attractions, this Winter Haven home offers a great opportunity to enjoy the Florida lifestyle.

1380 S Lake Roy Dr Drive, Winter Haven

$379,999

4 Beds ⋅ 3 Baths ⋅ Chestnut Crk SubDv. ⋅ 33881 Zip Code

SELLER MOTIVATED – MOVE-IN READY! Discover refined Florida living in the STUNNING SHENANDOAH II MODEL, an impressive SINGLE-STORY RESIDENCE offering 2,034 square feet of thoughtfully designed living space. Featuring 4 SPACIOUS BEDROOMS and 3 FULL BATHROOMS, this BEAUTIFULLY APPOINTED HOME blends ELEGANCE, COMFORT, and FUNCTIONALITY in a versatile layout designed for both everyday living and entertaining. From the moment you arrive, the CHARMING COLUMNED FRONT PORCH creates an inviting first impression. Step inside to a BRIGHT, OPEN-CONCEPT LIVING AREA where the seamless flow between the kitchen, dining, and living spaces creates an ideal setting for entertaining guests or enjoying relaxed evenings at home. The GORGEOUS KITCHEN is designed to impress, featuring PRISTINE SHAKER-STYLE CABINETRY, SAMSUNG STAINLESS STEEL APPLIANCES, a GENEROUS PANTRY, and a CHIC BREAKFAST BAR. The adjoining VERSATILE DINING AREA provides a welcoming space for everything from casual breakfasts to special gatherings. Throughout the main living areas and bathrooms, UPDATED 25-YEAR-LIFE-PROOF WOOD-VINYL FLOORING offers a SLEEK LOOK, while the bedrooms feature PLUSH STAIN-RESISTANT CARPETING for added comfort. These thoughtfully selected finishes combine BEAUTY, DURABILITY, and EVERYDAY PRACTICALITY. The SPACIOUS OWNER’S SUITE provides a peaceful retreat with a STYLISH TRAY CEILING, LARGE WALK-IN WARDROBE, and LUXURIOUS ENSUITE BATHROOM featuring DUAL SINKS and a BEAUTIFULLY TILED SHOWER accented by a GLASS ENCLOSURE. Step outside and embrace OUTDOOR LIVING on the EXPANSIVE COVERED LANAI, an inviting space for morning coffee, evening relaxation, or entertaining. Direct access to the THIRD FULL BATHROOM adds exceptional convenience for guests and outdoor activities. The LARGE BACKYARD provides a generous canvas for creating your own private outdoor retreat, with ample space to envision a future pool or customized outdoor living area, subject to applicable approvals and restrictions. Additional highlights include a 2-CAR GARAGE, ENERGY-EFFICIENT INSULATION, and ARCHITECTURAL SHINGLES, bringing together STYLE, EFFICIENCY, and PRACTICALITY. This EXCEPTIONAL HOME offers an appealing combination of BEAUTIFUL FINISHES, FUNCTIONAL DESIGN, SPACIOUS LIVING, and INDOOR-OUTDOOR COMFORT. If you’ve been waiting for a MOVE-IN READY RESIDENCE with room to personalize and make your own, this SHENANDOAH II MODEL deserves a closer look. WELCOME HOME!

1069 Sandpiper Loop, Winter Haven

$335,000

3 Beds ⋅ 2 Baths ⋅ Lake Thomas Woods Seventh Add SubDv. ⋅ 33880 Zip Code

Location is key for this 3-bedroom/2-bath home! With ease of access to the Polk Parkway and access to all of Central Florida. This 2,116 sq.ft. home features an open floor plan and split bedroom that offer great options for the family. This home has ceramic tiles in the living areas and carpet in the bedrooms, formal dining areas, inside utility room, and a large bonus room off the living area. The home sits on a cul-de-sac, has a two-car garage, and paved driveway. Call, text, or email to see it today!

1505 Lake Thomas Loop, Winter Haven

$314,999

4 Beds ⋅ 2 Baths ⋅ Seasons At Annabelle Estates SubDv. ⋅ 33884 Zip Code

The single-story Ruby plan was designed for entertaining, offering a generous great room, an open dining area and a relaxing covered patio. You’ll also appreciate an impressive kitchen with a center island and a walk-in pantry, as well as a lavish primary suite with a private bath and an immense walk-in closet. This home will be built with either two secondary bedrooms and a study or three secondary bedrooms. A shared bath, a convenient laundry room and a 2-car garage complete this beautiful Seasons™ Collection home. Special financing rates and closing cost assistance may be available. Options may vary by community and offers are available on select homes only. Contact builder for more information!

5315 Mickey Avenue, Winter Haven

$309,900

4 Beds ⋅ 3 Baths ⋅ Peace Crk Reserve SubDv. ⋅ 33884 Zip Code

Virtually Staged. Welcome to Florida Paradise in Winter Haven - a massive Chain of Lakes Area famous for the Legoland fun and outdoor activities! PRICED TO SELL! Almost Brand New Spacious 4 Bedroom / 2.5 Bathroom Home with a Community Pool and a Playground Access. Built in 2024 this Bright Modern house with an Open and Airy living/dining space combo concept is perfectly located in a nice neighborhood right across from the elementary school. Property Features include Modern Kitchen with Quartz Countertops equipped with Stainless Steel Appliances - stove, microwave, dishwasher, refrigerator/freezer, as well as a Laundry Area with Washer and Dryer included located on the second floor. Four Spacious Bedrooms with 2 Bathrooms are located upstairs; half a bathroom is located downstairs for your convenience. The Primary Suite comes with a Spacious Walk-In Closet, a beautifully Tiled Walk-In Shower and Dual Vanities. Three additional bedrooms and another full bathroom with a tub comfortably accommodate family and guests. Private Fenced Backyard with a Patio provides a peaceful outdoor retreat - perfect for after school hang outs, relaxing and entertaining. Community Amenities include a well-maintained Community Pool — perfect for warm Florida days and a Playground ideal for outdoor activities, walks and neighborly interaction. Convenient Location: just minutes away from major highways, this location provides an easy access to surrounding areas of Winter Haven and nearby towns. Shops, schools, pharmacies, parks and dining are all within short walking or driving distance. There are also Beautiful Lakes and Green Parks nearby for outdoor recreation. Ideal for a Primary Residence or a Long-Term Rental. This home is the perfect choice for a peaceful comfortable and convenient lifestyle in a fast-growing area. Schedule your private showing today for a chance to own this beautiful home in a desirable location!

1334 Diego Terrace, Winter Haven

$319,000

4 Beds ⋅ 2 Baths ⋅ Lakes At Lucerne Park Ph 02 SubDv. ⋅ 33881 Zip Code

Welcome to your next home in Winter Haven! This beautifully designed 4-bedroom, 2-bathroom home offers a highly sought-after layout with spacious bedrooms, walk-in closets, and plenty of room to spread out. Whether you’re looking for space for a home office, or a comfortable guest suite, this floor plan delivers the flexibility everyone is looking for! The open and functional design makes everyday living and entertaining a breeze, while the generous primary suite provides the perfect place to unwind at the end of the day. And those walk-in closets? Yes, please! Storage is something you won’t have to compromise on here. Location is the icing on the cake! Enjoy easy access to everything Winter Haven has to offer, including LEGOLAND Florida, Chain of Lakes, downtown Winter Haven, shopping, dining, parks, and major roadways for an easy commute. Whether you’re spending the afternoon on the water, enjoying dinner downtown, or heading out for a day of adventure, you’re never far from it. This is the kind of home that checks the boxes buyers have been waiting for—come see it for yourself before it’s gone!

609 Lucerne Boulevard, Winter Haven

$379,000

4 Beds ⋅ 2 Baths ⋅ Reflections East Add SubDv. ⋅ 33884 Zip Code

FOR SALE - 4 Bedroom, 2 Bathroom Beautiful Home in One of Winter Haven's Most Desirable Areas Don't miss this wonderful opportunity to own a beautifully maintained 4-bedroom, 2-bathroom home in a prime Winter Haven location. This charming home comes complete with all kitchen appliances, including a dishwasher, disposal, microwave, range, refrigerator, and washer/dryer. Recently painted and lovingly cared for, the home is move-in ready. One of its standout features is the enormous fourth bedroom, measuring an impressive 26' x 17', offering endless possibilities as a primary suite, game room, home office, or family room. The roof to the house was replaced in 2017. The roof to the rear porch was installed 3 years ago. The roof to the addition was installed in 2023. The hot water heater is from 2017. The air conditioner was replaced in 2023. Conveniently located near shopping, restaurants, schools, places of worship, and LEGOLAND, this home combines comfort, space, and an unbeatable location. Schedule your showing today!

817 Reflections Loop E, Winter Haven

$349,000

4 Beds ⋅ 2 Baths ⋅ Van Duyne Shores SubDv. ⋅ 33881 Zip Code

It's a completely renovated 4-bedroom beauty. No HOA. Park your trailers or vehicles in back yard or side yard with gate. New Roof, new windows, new doors, new hot water heater, new insulation, new electric and new air conditioner 2024. The kitchen has gold handles, refrigerator/ coffee maker combo, and a farmhouse sink. Wood floors are refinished 2025. Kitchen and bathrooms are totally renovated 2024. If you like drawers, this kitchen has a few. HUGE master bedroom runs from the back of the house to the front of the house, plenty of relaxing space, and a fireplace. This is a split plan house with 4 bedrooms, and all bathrooms have double sinks. Tropical pineapple garden is in front of the front porch and trees have been trimmed. The back shed has a metal roof and can be used as a workshop; she shed or transformed for mother-in-law or rental. Large back porch has new concrete steps, a renovated laundry room and lake view. ZAP CAP from TECO, surge voltage protection. Parks, trails, splash pads, grocery, movies, pharmacy, public boat ramps are available. Winter Haven is a diverse city which offers lots of things to do such as, dinner cruises, walking parks, farm markets, LEGOLAND park and water parks, Circle B nature park, walking trails, skateboard park, water skiing and free water-skiing shows. All information is deemed reliable but not guaranteed. Buyer must verify all information and measurements. No seller financing.

1919 19th Street Nw, Winter Haven

$335,924

4 Beds ⋅ 2 Baths ⋅ Crescent Pointe SubDv. ⋅ 33884 Zip Code

Crescent Pointe is a brand new community located in Winter Haven, FL, conveniently situated off State Rd 653 and boasting easy access to a range of nearby attractions. For residents who enjoy outdoor activities, the Winter Haven Chain of Lakes is nearby. It offers opportunities for boating, fishing, and other recreational activities. The community is also close to the bustling downtown area, where residents can explore local shops, dining venues, and family events. With NO CDD and low HOA, Crescent Pointe is an ideal place to call home in Winter Haven.

981 Lunar Lane, Winter Haven

$324,900

4 Beds ⋅ 2 Baths ⋅ Gardens Ph 01 SubDv. ⋅ 33880 Zip Code

Welcome to 418 Majestic Gardens Blvd, Winter Haven, FL 33880, a spacious and move-in-ready 4-bedroom, 2-bath home located within a gated community. Offering a well-designed floor plan with generous living and dining areas, this home provides plenty of space for everyday living, entertaining, or continued use as an investment property. The kitchen features abundant cabinetry, ample counter space and stainless-steel appliances, while the open living areas are enhanced by high ceilings and plenty of natural light. The spacious primary suite includes a large private bath with dual vanities, soaking tub, separate shower and walk-in closet space. Three additional bedrooms provide flexibility for family, guests, a home office or additional accommodations. Step outside to enjoy the screened rear lanai overlooking a fully fenced backyard with plenty of room to relax, garden or entertain. A large concrete pad provides additional outdoor-use possibilities, while approximately 20 producing sugar apple plants create a unique backyard feature for those who enjoy fresh tropical fruit and gardening. Adding to the property's versatility, the home has previously been utilized as an Airbnb/short-term rental and has provided income for the current seller, making it an attractive option for buyers searching for either a primary residence or potential investment property. Conveniently located near Winter Haven shopping, dining, recreation and major roadways, this property combines space, privacy and opportunity. Move-in ready with a flexible floor plan, gated-community setting, screened outdoor living area, fenced yard and established fruit-producing plants—418 Majestic Gardens Blvd is ready for its next owner.

418 Majestic Gardens Blvd, Winter Haven

$314,900

4 Beds ⋅ 2 Baths ⋅ Overlook Estates SubDv. ⋅ 33884 Zip Code

This spacious 4-bedroom, 2-bathroom single-family home offers approximately 2,355 square feet of living space on a generous 0.34-acre lot, providing plenty of room to make it your own. This property offers a great opportunity for buyers looking to customize a home to their style and potentially build equity through improvements. First time home buyer, ask about the possibility of purchasing with an FHA 203(k) renovation loan, which may allow qualified buyers to finance both the purchase of the home and eligible renovations into one mortgage. Whether you're looking for a primary residence or an opportunity for investor to create additional value, this home offers flexibility and potential in a convenient Winter Haven location. Schedule your private showing today and explore the possibilities this property has. FHA 203(k) financing is subject to buyer and property qualification and lender approval.

215 Santa Rosa Drive, Winter Haven

$319,900

4 Beds ⋅ 2 Baths ⋅ Fanning Sub SubDv. ⋅ 33880 Zip Code

INVESTMENT OPPORTUNITY + INCOME-PRODUCING PROPERTY + NO HOA! Welcome to 501 Avenue G SE, Winter Haven, FL 33880, a unique single-family property grandfathered for multi-family use, offering flexibility for INVESTORS, HOUSE HACKERS, MULTI-GENERATIONAL LIVING, or OWNER-OCCUPANTS looking for rental income! Situated on a LARGE LOT, the property is currently configured as TWO SEPARATE LIVING UNITS with PRIVATE ENTRANCES AND SEPARATE YARD AREAS. The front residence features 3 BEDROOMS, 1 BATH, laminate flooring, and a dedicated laundry room, while the rear 1 BEDROOM, 1 BATH unit is currently TENANT OCCUPIED AT $1,220/MONTH by a reliable tenant who pays on time and is happy to discuss extending the lease—providing IMMEDIATE RENTAL INCOME for the next owner. Live in the front while collecting rent from the rear to help OFFSET YOUR MONTHLY MORTGAGE, or add this property to your rental portfolio as an INCOME-PRODUCING ASSET. For buyers looking for VALUE-ADD POTENTIAL, the existing layout provides an opportunity to reconfigure the property by creating a middle studio-style living space and converting the front residence to a 2-bedroom, 1-bath configuration. With NO HOA, separate living areas, existing rental income, a large lot, and additional upside potential, this property offers multiple possibilities for today's savvy buyer. Increase its overall value and rental potential. Property is being sold AS-IS. Whether you're searching for a HOUSE HACK, MULTI-GENERATIONAL HOME, RENTAL PROPERTY, VALUE-ADD INVESTMENT, PASSIVE INCOME OPPORTUNITY, or PRIMARY RESIDENCE WITH ADDITIONAL INCOME, this is one you don't want to miss!

501 Avenue G Se, Winter Haven

$325,000

3 Beds ⋅ 2 Baths ⋅ Martha Heights Pb 9 Pg 39 SubDv. ⋅ 33881 Zip Code

Rare No-HOA Corner Lot with Work, RV, & Boat Parking This 3-bedroom, 2-bath block home sits on a quarter-acre corner lot in Winter Haven with zero HOA restrictions. The fenced yard offers Private area for RV parking, boat parking, and off-street parking beyond the attached 22x13 garage—ideal for trailers, toys, or a backyard workshop—plus raised garden beds already in place, a kennel/chicken coop, and mature oak trees for those who'd rather use the space for animals or growing their own food. Inside, this home offers a living room/dining room combo, a Florida room, and shelving in the guest hallway. The primary suite features a built-in closet and large en-suite bathroom including storage and laundry area. The second full bathroom serves the additional bedrooms. Central air, ceiling fans, and oak wood floor throughout much of the home other than ceramic tile in both bathrooms, and linoleum in the kitchen. The community offers access to a nearby Lake Elbert which has a public boat ramp, dock, allowing fishing and a paved lakeside walking path close by. No HOA. No lease restrictions. No association approval required—a flexible corner lot ready for RVs, boats, gardens, or animals.

845 Avenue F Ne, Winter Haven

$389,000

3 Beds ⋅ 2 Baths ⋅ Lake Mariam Hills Rep SubDv. ⋅ 33884 Zip Code

CUSTOM BUILT HOME WITH HEATED POOL IN LAKE MARIAM HILLS!!! This 3BR/2BA residence is situated on a quiet cul-de-sac in established and gated Lake Mariam Hills. Custom features are found throughout the split floorplan with its open and spacious feel. Large archways, columns, towering vaulted ceilings, custom accent windows, French doors and more are examples of the home's craftmanship and attention to detail. The kitchen is spacious, with a breakfast bar, an eat-in area, custom cabinetry, ample counter space and a great pool view. There are also formal living and dining areas, a comfortable living space with French doors opening onto the covered lanai, pool and screen enclosed patio!!! The pool is salt water, has a lovely water feature and feels secluded behind the mature landscaping and privacy fence. The Master Suite is a great place to relax and offers a custom tile shower and a separate garden tub, dual sinks, large walk-in closet, linen closet and French doors opening to the pool area. Many more features include a whole house generator, an oversize two car garage, extended driveway for additional parking, lush, mature landscaping, architectural shingle roof, in-wall pest defense, some tinted windows for efficiency, upgraded insulation and more. A gorgeous custom pool home in one of Winter Haven's most established gated communities, call today to see this exceptional home!

102 Hillside Court, Winter Haven

$329,900

3 Beds ⋅ 2 Baths ⋅ Southern Gardens Rep SubDv. ⋅ 33880 Zip Code

Under contract-accepting backup offers. 6.36 ACRES, NO HOA, GATED ENTRY & 3-CAR GARAGE/WORKSHOP! Enjoy country living without sacrificing convenience! This spacious 3-bedroom, 2-bath home with a flex/bonus room sits on 6.36 acres with NO HOA, offering privacy, freedom and room to spread out. Inside, LVP flooring flows throughout the bright, open-concept floor plan. The oversized living room opens to the updated kitchen and dining area, creating an inviting space for everyday living and entertaining. The kitchen features an abundance of cabinetry and counter space. The spacious primary suite offers a comfortable retreat, while generously sized guest bedrooms provide excellent storage, including walk-in closets. The laundry area includes the washer and dryer, and the home also features a tankless water heater and whole-house water treatment system. Outside, a keypad-entry gate provides added privacy, while the expansive screened patio is perfect for relaxing or entertaining. The impressive 24x32 3-car garage/workshop offers plenty of room for vehicles, recreational equipment, storage or your dream workshop. ROOF REPLACED 2022 Conveniently located near the Polk Parkway between Winter Haven and Lakeland, with easy access to shopping, dining and everyday necessities. Come experience the space, freedom and possibilities this property offers!

5230 Thornhill Road, Winter Haven

$357,000

5 Beds ⋅ 4 Baths ⋅ Royal Hills SubDv. ⋅ 33881 Zip Code

Discover exceptional living in this spacious 5-bedroom, 4-bath Winter Haven beauty—an ideal blend of style, comfort, and modern convenience. Step inside to an inviting open-concept kitchen with a center island, perfect for entertaining and everyday living. Elegant arched doorways add architectural charm throughout, creating a warm and welcoming flow. Enjoy year-round relaxation in the enclosed patio, offering the perfect spot for morning coffee or evening unwinding. A 2-car garage provides ample storage, while the fully fenced backyard delivers privacy and space for outdoor fun. Homes with this much versatility and character don’t stay on the market long—claim this Winter Haven gem before it’s gone.

5604 Royal Hills Drive, Winter Haven

$360,000

4 Beds ⋅ 2 Baths ⋅ Terranova Ph Iv SubDv. ⋅ 33884 Zip Code

Virtually Staged. This Winter Haven one-story home offers a two-car garage. Included 100-Day Home Warranty with buyer activation

313 Terranova Boulevard, Winter Haven

$320,480

3 Beds ⋅ 2 Baths ⋅ Harbor At Lake Henry SubDv. ⋅ 33881 Zip Code

Under Construction. New construction home with 1,545 square feet on one-story including 3 bedrooms, 2 baths, and an open living area. Enjoy an open kitchen with Quartz countertops, Samsung stainless steel appliances, a walk-in pantry, and a spacious island, fully open to the dining café and gathering room. The living area, laundry room, and baths include luxury wood vinyl plank flooring, with stain-resistant carpet in the bedrooms. Your owner's suite is complete with a walk-in wardrobe and a private en-suite bath with dual vanities, a tiled shower, and a closeted toilet. Plus, enjoy a covered lanai, 2-car garage, custom-fit window blinds, architectural shingles, energy-efficient insulation and windows, and a full builder warranty. "Please note, virtual tour/photos showcases the home layout; colors and design options in actual home for sale may differ. Furnishings and décor do not convey.

576 Ituna Circle, Winter Haven

$353,290

4 Beds ⋅ 3 Baths ⋅ Harbor At Lake Henry SubDv. ⋅ 33881 Zip Code

Under Construction. New construction home with 2029 square feet one-story including 4 bedrooms, 2.5 baths, and an open living area. Enjoy an open kitchen with, Quartz countertops, Samsung stainless steel appliances, pantry, and a spacious counter height island, fully open to the dining café and gathering room. The living area, laundry room, and baths include luxury wood vinyl plank flooring, with stain-resistant carpet in the bedrooms. Your owner's suite is complete with a walk-in wardrobe and a private en-suite bath with dual vanities, a tiled shower, and a closeted toilet. Jack-and-Jill Hall bath with an enclosed tub and toilet, accessed from bedrooms 3 and 4. Plus, enjoy a covered lanai, 2-car garage, custom-fit window blinds, architectural shingles, energy-efficient insulation and windows, and a full builder warranty. Please note, virtual tour/photos showcases the home layout; colors and design options in actual home for sale may differ. Furnishings and décor do not convey.

540 Ituna Circle, Winter Haven

$335,560

3 Beds ⋅ 2 Baths ⋅ Harbor At Lake Henry SubDv. ⋅ 33881 Zip Code

New construction home with 2005 square feet on one-story including 3 bedrooms, 2 baths, den, and an open living area. Enjoy an open kitchen with Quartz countertops, Samsung stainless steel appliances, a walk-in pantry, and a spacious island, fully open to the dining café and gathering room. The living area, laundry room, and baths include luxury wood vinyl plank flooring, with stain-resistant carpet in the bedrooms. Your owner's suite is complete with a walk-in wardrobe and a private en-suite bath with dual vanities, a tiled shower, and a closeted toilet. Plus, enjoy a covered lanai, 2-car garage, custom-fit window blinds, architectural shingles, energy-efficient insulation and windows, and a full builder warranty. ***Please note - Virtual Tour/Photos showcases the home layout; colors and design options in actual home for sale may differ. Furnishings and décor do not convey!

432 Ituna Circle, Winter Haven

$330,000

4 Beds ⋅ 3 Baths ⋅ Windridge SubDv. ⋅ 33881 Zip Code

Spacious 4BR/2.5BA home with 2,836 SF in desirable Windridge! Enjoy a screened saltwater pool, spacious fenced backyard, flexible living areas, and parking for up to 8 vehicles (2-car garage + oversized driveway). Major updates include a 2023 roof and 2022 A/C. Low HOA, no CDD, and convenient access to shopping, dining, schools, and major roads. Quick closing available and priced to sell. Act fast; schedule your private showing today!

5888 Windridge Drive, Winter Haven

$345,000

4 Beds ⋅ 2 Baths ⋅ Lake Lucerne Ii SubDv. ⋅ 33881 Zip Code

Virtually Staged. Newer home with NO CDD and large yard!!! Welcome home to this beautifully maintained 4 bedroom, 2 bath home offering 1,983 square feet of comfortable living space and modern finishes throughout. Built in 2023, this home features a desirable open split-floor plan designed for both everyday living and entertaining. The spacious kitchen boasts granite countertops, large island, stainless steel appliances, and plenty of room to gather with family and friends. The split-bedroom layout provides privacy for the primary suite while keeping the additional bedrooms conveniently accessible. Step outside to enjoy the large yard and relaxing covered lanai—perfect for morning coffee, outdoor dining, or entertaining. Additional highlights include a 2-car garage, new carpet, and no CDD. With its modern construction, spacious layout, and move-in-ready appeal, this home is a must-see!

1425 Engelberg Street, Winter Haven

$310,000

4 Beds ⋅ 2 Baths ⋅ Lake Smart Estates SubDv. ⋅ 33881 Zip Code

3D tour available! Welcome to this spacious 4-bedroom, 2-bath single-family home in the Lake Smart Estates community of Winter Haven. With an open-concept layout and 1,842 square feet of living space, the home offers plenty of room for everyday living and entertaining. Major updates provide added peace of mind, including a new roof in 2026, new A/C in 2024, and brand-new appliances in 2026. The kitchen offers generous cabinet and counter space and opens directly to the main living and dining areas. The primary suite features a walk-in closet and private bathroom with dual sinks and a spacious shower. An interior laundry room and attached two-car garage add everyday convenience. One of the property's biggest highlights is the oversized lot, one of the largest in the community. The expansive backyard provides exceptional outdoor space with plenty of possibilities for entertaining, play areas, gardening, or creating your own Florida outdoor retreat. Lake Smart Estates offers community amenities including a swimming pool, dock, gazebo, and water access. Golf enthusiasts will appreciate having Willowbrook Golf Course just minutes away, a public 18-hole course offering a driving range, putting green, chipping areas, and practice facilities. Conveniently located near US-17, the home provides easy access to Downtown Winter Haven, shopping, restaurants, schools, Polk State College, and everyday services. With four bedrooms, significant recent upgrades, an oversized yard, community amenities, and golf nearby, this move-in-ready home offers an excellent combination of indoor and outdoor space in a convenient Winter Haven location.

3695 Julius Estates Boulevard, Winter Haven

$349,900

4 Beds ⋅ 3 Baths ⋅ Eagle Lndg Ph Ii SubDv. ⋅ 33880 Zip Code

!!!!REDUCED PRICE FOR QUICK SELL! SELLER HIGHLY MOTIVATED! BEST VALUE IN EAGLE LANDING! Welcome to this beautiful 2022-built home in the desirable Eagle Landing community of Winter Haven, conveniently located just minutes from LEGOLAND Florida and ideally positioned between Tampa and Orlando. Offering approximately 2,300 square feet of living space, this move-in-ready home features a spacious open-concept floor plan designed for comfortable everyday living and entertaining. The modern kitchen flows seamlessly into the main living areas, creating a bright and inviting space. Enjoy Florida living from the screened-in porch overlooking the private, fully vinyl-fenced backyard. Additional features include durable block construction, architectural shingle roof, modern stucco exterior, and a LOW HOA. Whether you're looking for a primary residence, vacation home, or investment property, this home offers an excellent combination of location, size, condition, and value. Offered at $355,000 with a highly motivated seller. Easy to show—schedule your private showing today!

662 Eagle Landing Boulevard, Winter Haven

$359,900

Asbury Park SubDv. ⋅ 33880 Zip Code

LOCATION! Exceptional opportunity to own a move-in-ready professional office building in the heart of Downtown Winter Haven's business district. Situated on a high-traffic, highly visible city street, this property offers outstanding exposure for businesses seeking a prominent location with excellent accessibility. Recently remodeled from top to bottom, the building features new flooring, new energy-efficient windows, fresh interior and exterior paint, an updated ADA-compliant restroom, a front accessibility ramp providing convenient entry for clients and visitors, and numerous additional improvements making it ready for immediate occupancy. The well-designed floor plan currently offers six private office suites, a welcoming reception/work area, and one ADA-compliant bathroom, providing flexibility for a wide variety of professional users. Ideal for real estate, medical, legal, insurance, title, accounting, financial services, consulting, or other professional office uses, this property is perfectly suited for both owner-users and investors alike. The exterior offers rear parking for approximately 5–8 vehicles, depending on the desired parking configuration, along with excellent street signage opportunities to maximize business visibility. Located in Flood Zone X and positioned just minutes from local government offices, restaurants, shopping, and the rapidly growing Downtown Winter Haven corridor, this property combines convenience, functionality, and long-term investment potential. Whether you're expanding your business, relocating your office, or adding a quality commercial asset to your portfolio, this is a rare opportunity to own a beautifully updated office building in one of Winter Haven's most desirable commercial locations.

334 1st Street S, Winter Haven

$315,000

4 Beds ⋅ 3 Baths ⋅ Jan Phyl Village SubDv. ⋅ 33880 Zip Code

Welcome home to this spacious 4-bedroom, 3-bathroom home offering over 2,000 square feet of comfortable living space on a large corner lot. Designed with both everyday living and entertaining in mind, this home features two bedrooms with private en-suite bathrooms, providing flexibility and privacy for family members or guests. Step outside to the screened lanai, where you can relax and enjoy views of the expansive backyard and in-ground pool—perfect for Florida living and entertaining year-round. The large fenced backyard provides plenty of room for outdoor activities, pets, gardening, or simply enjoying your own private outdoor retreat. With its generous living space, desirable split-bedroom potential, pool, and oversized corner lot, this home offers plenty of room to make it your own. Don’t miss the opportunity to make this spacious pool home your next address!

506 Clayton Circle, Winter Haven

$326,900

4 Beds ⋅ 2 Baths ⋅ Lakeside Landings Ph 01 SubDv. ⋅ 33881 Zip Code

Welcome to your new sanctuary in Lakeside Landings, a 55+ resort style, low maintenance existence awaits!! This isn't just a 4-bedroom, 2-bathroom, 2-car garage house. It is an exclusive VIP pass to resort-style living in a gated community with only 44 other neighbors. Before you even step inside, stop and look up. Are those... yes, those are RAIN GUTTERS and a NEW ROOF!! In Central Florida, tile floors are a plus, and you will not find any carpet here! Step inside and experience the magic of a triple-split floor plan. It is perfect for maximum privacy when you need a break. Even better? The indoor laundry room is centrally located. The open-concept living area features a kitchen with stone countertops and stainless steel appliances, beautiful tile backsplash. But the real showstopper is the view! Breathtaking conservation backdrop sets the stage while local birds put on a daily, free nature documentary. Screened-in and bug-free, sip coffee without swatting mosquitoes! Fenced, lushly landscaped, and fully optimized for your pet safety, the fenced back yard is well maintained for your pet! The owner's suite is an absolute fortress of comfort. It boasts dual closets and a massive walk-in shower. In fact, this bathroom is so huge you might actually mistake it for a ballroom dance floor. Need to escape your paradise? You are right off Highway 27 and I-4, minutes from Legoland and Central Florida attractions. Championship golf courses and world-class fishing. Shopping, restaurants, and places of worship. This home has everything the Florida lifestyle demands. Grab your sunglasses and give me a call before someone else beats you to it!

5852 Marsh Landing Drive, Winter Haven

$399,900

4 Beds ⋅ 4 Baths ⋅ Twin Oaks Add SubDv. ⋅ 33880 Zip Code

This exceptional property offers a rare opportunity to live in one residence while renting the other to help supplement your mortgage payment. Conveniently located near hospitals, medical facilities, colleges, universities, shopping, dining, and major transportation routes, the property combines versatile living arrangements with everyday accessibility. Qualified buyers may be eligible for down payment assistance. Program eligibility, terms, and availability may vary; contact the listing agent for details. The primary residence has been completely renovated, offering a refreshed and inviting atmosphere throughout. Its open-concept design seamlessly connects the kitchen and dining areas, creating an ideal space for everyday living, entertaining and gathering with loved ones. The beautifully updated kitchen features sleek stainless steel appliances, elegant granite countertops, wood laminate, porcelain tile flooring and a functional layout that combines style and convenience. A covered front porch provides a shaded outdoor area for relaxing and enjoying the surroundings. The two residences have separate living areas with no interior access between them, offering added privacy and flexibility. The second residence offers stylish and comfortable living with durable porcelain tile flooring throughout. Its well-appointed kitchen features stainless steel appliances and elegant granite countertops, while the spacious layout includes two bedrooms and two bathrooms-providing flexibility and convenience for residents or tenants. The spacious backyard offers room for outdoor entertaining, gardening, recreation or future personalization. With no homeowners association, extensive renovations, newly constructed, and versatile use options, this property is well-suited for multigenerational living, an owner-occupant seeking rental income, or an investor looking for income-producing potential. Its location near hospitals and colleges adds convenience for healthcare professionals, faculty, medical personnel, and other nearby employees. Virtually staged images are for illustrative purposes only.

207 Avenue E Se, Winter Haven

$350,000

5 Beds ⋅ 3 Baths ⋅ Peace Crk Reserve SubDv. ⋅ 33884 Zip Code

This is a great opportunity to own your dream home located in SE Winter Haven, FL. One of Central Florida’s growing residential markets, known for its family-friendly lifestyle, beautiful lakes, peaceful atmosphere, and strategic location. The property is about one hour from Tampa and Orlando. The home offers a modern and functional design with an open-concept layout, a bright great room that flows into the dining area, and a contemporary kitchen featuring stainless steel appliances, sleek cabinetry, and generous counter space. The laundry room is conveniently located on the first floor, adding everyday comfort and practicality. Upstairs, the home features a versatile loft ideal for a home office, entertainment area, or additional family space. All bedrooms are on the second floor. The private backyard adds lifestyle value for future occupants, offering the perfect space to enjoy Florida’s outdoor living. The seller is motivated and open to considering strong offers, making this property an excellent opportunity for you.

1187 Tyler Loop, Winter Haven

$306,000

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

Why wait to build when you can move right in? This 2023-built, 3-bedroom, 2-bath home in VillaMar Phase 4 offers 1,597 square feet and is ready for its next owner! THE 10-YEAR STRUCTURAL BUILDER WARRANTY IS STILL IN EFFECT, offering added peace of mind for the new owner. The open floor plan connects the kitchen, dining, and living areas, making it easy to entertain, host family and friends, or enjoy a night at home. SMART-HOME features include a central control hub, smart front-door lock, Wi-Fi-enabled thermostat, video doorbell, and connected lighting, allowing you to manage select features right from your smart device. Step outside and enjoy the Florida lifestyle without leaving the neighborhood! VillaMar offers resort-style amenities including a community pool, cabana, and playground, with dog parks nearby. The location puts you just minutes from LEGOLAND Florida and Peppa Pig Theme Park, Publix, Walmart, Eagle Ridge Mall, restaurants and shopping along Cypress Gardens Boulevard, and Downtown Winter Haven. US-27, US-17, and Highway 60 are also nearby, providing access to Lakeland, Orlando, and Tampa. WALT DISNEY WORLD is approximately 35 miles away, making weekend trips to the Orlando attractions an easy option. With an established neighborhood and a 2023-built home that's ready now, you can skip the building process, bring your belongings, and start enjoying VillaMar! All information is deemed reliable but is not guaranteed and should be independently verified.

3927 Palazzo Place, Winter Haven

$331,000

5 Beds ⋅ 3 Baths ⋅ Lucerne Park Reserves SubDv. ⋅ 33881 Zip Code

***Seller has a 2.6 interest rate and is open to creative financing options ***SPACE, VERSATILITY & A FANTASTIC FLOOR PLAN! This spacious 5-bedroom, 3-bath D.R. Horton "Hayden" offering approximately 2,601 square feet of living space in Winter Haven's Lucerne Park Reserve. Step inside and you'll immediately appreciate a floor plan designed for today's lifestyle. Just off the entry is a spacious flex room, currently utilized as a home office, but equally suited for a formal dining room, playroom, study or additional sitting area. Continue into the heart of the home where the open-concept kitchen, dining and family room create one large gathering space perfect for everyday living and entertaining. The kitchen features dark cabinetry, generous counter space, a large center island with breakfast-bar seating, pantry storage and a complete appliance package. Sliding glass doors provide easy access to the backyard and bring natural light into the main living areas. One of the most desirable features of this floor plan is the first-floor secondary bedroom and full bathroom, providing excellent flexibility for overnight guests, extended household needs or an additional private workspace. Upstairs, the home's generous proportions continue with a large loft, creating another flexible living area for a media room, game room, homework area or second family room. The oversized primary suite provides plenty of room for a complete bedroom set plus an additional sitting area. The primary suite is complemented by a private bath and walk-in closet. Built in 2021, the home also features tile in the main traffic areas, carpeted living and bedroom spaces, abundant storage and solar panels for added energy-conscious appeal. Outside, enjoy a backyard with plenty of possibilities for creating your own Florida outdoor living space. Lucerne Park Reserve offers residents a community pool, playground, sidewalks and recreational areas, all while providing convenient access to shopping, dining, entertainment and major Central Florida roadways, including access toward I-4. If you've been looking for a home with five bedrooms, three full bathrooms, a downstairs guest suite, dedicated flex space AND an upstairs loft, this floor plan delivers the versatility that's hard to find. Schedule your private showing and see just how much space this home has to offer!

706 Peyton Brooke Way, Winter Haven

$320,000

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

NEARLY NEW WITHOUT THE WAIT—AND NO HOA! Built in 2024 by premiere builder WCM Construction, and only briefly lived in, this 3-bedroom, 2-bath home offers the benefits of newer construction without having to wait for a home to be built. Situated on an oversized approximately .28-acre lot, the property also features a large fenced backyard, giving you plenty of room for pets, play, entertaining, gardening or simply enjoying your own outdoor space. Inside, the home offers a clean, modern feel with wood-grain tile flooring throughout—no carpet—Level 3 granite countertops in the kitchen and bathrooms, quality cabinetry and upgraded appliances. The open layout makes excellent use of the space while the attached garage provides additional convenience and storage. One of the biggest advantages is what you won't find here—NO HOA, giving you greater flexibility without monthly association dues or community restrictions. Located in southwest Winter Haven, this home offers convenient access to major roadways and makes commuting throughout Polk County easy. Winter Haven, Bartow, Lakeland and surrounding areas are all within easy reach, while shopping, dining, schools and everyday conveniences are just a short drive away. If you've been considering new construction but don't want the added expense, construction timeline or HOA commonly associated with newer homes, 6631 Thornhill Road offers an excellent alternative—a nearly new home, generous fenced yard and no HOA. Schedule your private showing and see why this one deserves a closer look!

6631 Thornhill Road, Winter Haven

$385,000

4 Beds ⋅ 2 Baths ⋅ Hamilton West Ph 02 SubDv. ⋅ 33881 Zip Code

Welcome to **107 Sanderling Drive**, a spacious and inviting **4-bedroom, 2-bathroom single-family home** in the desirable Hamilton West community of Winter Haven. Offering approximately **2,567 square feet of living space**, this one-story home provides plenty of room for comfortable everyday living, entertaining, and creating lasting memories. Step inside to a welcoming floor plan featuring spacious living and dining areas, an eat-in kitchen, vaulted ceilings, crown molding, and a combination of wood and tile flooring. The kitchen offers generous cabinet and counter space and opens toward the breakfast area and family room, creating a great gathering space for family and friends. The split-bedroom layout provides privacy for the primary suite, which features **two walk-in closets, dual sinks, a garden tub, and a separate walk-in shower**. Recent and important property improvements include a **new roof installed in 2024 with architectural shingles**, providing added peace of mind for years to come. The home features an **HVAC system with dual-purpose natural gas heating and cooling**, along with a **natural gas water heater**. A **well irrigation system services the sprinkler system**, helping maintain the landscaping while providing an efficient source for irrigation. Additional features include a **two-car attached garage**, ceiling fans, window treatments, and a spacious **0.26-acre lot** with approximately **11,326 square feet of land**, providing plenty of room to enjoy Florida's outdoor lifestyle. Located in the heart of Winter Haven's famous **Chain of Lakes region**, residents can enjoy boating, fishing, kayaking, water sports, and beautiful waterfront recreation. Nearby **Lake Howard** and the surrounding lakes provide numerous opportunities for outdoor adventures and relaxation. Enjoy the shops, restaurants, entertainment, and community events of **downtown Winter Haven**, or spend the day exploring local parks and nature areas. Family-friendly attractions and activities are also nearby, including **LEGOLAND Florida Resort**, golf courses, walking and biking trails, and numerous recreational facilities throughout the Winter Haven area. Conveniently located with easy access to major roadways, this home provides a great balance of peaceful residential living and proximity to shopping, dining, recreation, medical facilities, and Central Florida attractions. With its spacious floor plan, **2024 architectural shingle roof**, natural gas HVAC and water heater, well irrigation system, and desirable Winter Haven location, **107 Sanderling Drive** is an excellent opportunity to enjoy the Central Florida lifestyle. **Come see all this wonderful home has to offer!**

107 Sanderling Drive, Winter Haven

$305,000

3 Beds ⋅ 2 Baths ⋅ Jan Phyl Village Un #16 SubDv. ⋅ 33880 Zip Code

PRICE IMPROVEMENT! Enjoy Florida living with your own private pool and plenty of space to spread out in this recently remodeled 3-bedroom, 2-bathroom Winter Haven home. Inside, the spacious floor plan offers an open main living area where the family room, dining space, and kitchen flow together, creating a comfortable setting for both everyday living and entertaining. Recent updates throughout give the home a fresh, updated feel, including new flooring throughout. The updated kitchen features brand-new cabinets and countertops, stainless steel appliances, and a large island that provides generous prep space and additional seating. One of the home's standout features is the additional flex room, giving you even more room to make the home work for your lifestyle. Use it as a second living area, game room, home office, playroom, or entertainment space. Sliding glass doors fill the room with natural light and open directly to the covered patio, extending the living space outdoors. The primary bedroom features its own private bathroom and closet, while two additional bedrooms and a second full bathroom provide flexibility for family, guests, or a home office. The neutral interior and open layout make the home feel bright and inviting while offering plenty of possibilities for personalizing each space. Step outside to your own private backyard retreat featuring a remodeled pool with new tile and a freshly painted pool deck, perfect for relaxing, entertaining, or enjoying Florida's beautiful weather. The covered patio extends the living space outdoors and provides a great spot for dining or unwinding by the pool. With plenty of surrounding backyard space, there's room to enjoy sunny afternoons by the water or relax beneath the covered patio. With a recently remodeled interior, updated kitchen, new flooring, remodeled pool, multiple living spaces, a flexible floor plan, and indoor-outdoor living, this Winter Haven home brings together the space and features that make everyday Florida living easy to enjoy.

205 Fern Road, Winter Haven

$365,000

3 Beds ⋅ 2 Baths ⋅ Hartridge Hills SubDv. ⋅ 33881 Zip Code

Move-In Ready Custom Home in a Gated Community Near the Airport Ideally located for aviation professionals seeking convenient access to the airport or for families looking for a safe, gated community, this beautifully updated custom home offers the perfect blend of comfort, style, and convenience. Built in 1988, this spacious home features an open floor plan with soaring ceilings, stunning exposed wood beams, solid wood doors, and matching wood baseboards that create warmth and character throughout. The split-bedroom layout provides privacy, while the attached two-car garage adds everyday convenience. The recently remodeled interior showcases numerous upgrades, including luxury vinyl plank flooring, fresh interior paint, and updated lighting throughout. The beautifully renovated kitchen features custom wood cabinetry, granite countertops, and a full suite of matching Whirlpool appliances. Both bathrooms have been tastefully updated with new wood vanities, Delta fixtures, Kohler toilets, and stylish tile finishes. The primary bedroom offers the comfort of new carpeting, and the home features smooth ceilings throughout—no popcorn ceilings. Additional highlights include generous laundry room storage, fresh exterior paint, and numerous major improvements for peace of mind. A new roof was installed in March 2026, along with new double-insulated windows, new irrigation, and professional landscaping. New water heater and also passed 4-point inspection for insurance purposes. Every major update has been completed—simply move in and enjoy. The HOA fee is just $150 per month and includes lawn mowing and fertilization, making it easy to maintain a beautiful yard year-round.

218 Lake Hartridge Drive Nw, Winter Haven

Browse All Winter Haven FL Between $300K - $400K Properties for Sale

Between $300K - $400K Winter Haven Real Estate