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4629 Palmetto Drive, Winter Haven
$305,000
3 Beds ⋅ 2 Baths ⋅ TB8548042 MLS
Discover the opportunity to own a home in a convenient Central Florida location, surrounded by attractions, recreation, shopping, dining, and everyday conveniences. Enjoy easy access to LEGOLAND® Florida Resort, approximately 25 minutes away, as well as LEGOLAND Water Park and PEPPA PIG Theme Park. Winter Haven is also known for its beautiful Chain of Lakes, offering opportunities for boating, fishing, water activities, and enjoying Florida's outdoors. The area provides convenient access to local parks, restaurants, shopping, entertainment, and downtown Winter Haven. Its Central Florida location also makes it an excellent base for enjoying many of the region's popular attractions while maintaining a more relaxed residential lifestyle. Whether you're looking for a primary residence, a second home, a vacation property, or an investment opportunity, this property offers the chance to enjoy the best of Winter Haven and Central Florida living. Schedule your private showing today!

4629 Palmetto Drive, Winter Haven

Listing courtesy of MIRANDA LANDA REALTY GROUP LLC. 727-554-8198
1029 Hook Lane, Winter Haven
$76,000
2 Beds ⋅ 2 Baths ⋅ 11975643 MLS
Welcome to this charming and beautifully furnished 2-bedroom, 2-bath home in the desirable Swiss Golf & Tennis community in Winter Haven. Offering approximately 1,352 square feet of living space, this well-maintained home combines comfortable living with Florida charm and plenty of updates. Step inside to a bright and inviting interior featuring vinyl flooring throughout the main living areas and bedrooms. The spacious living room provides a comfortable gathering space and flows naturally toward the dining and kitchen areas. The cheerful kitchen offers abundant white cabinetry, generous counter space, stainless-steel appliances and a double sink. The home features two comfortable bedrooms, including a spacious primary bedroom with plenty of room for furnishings and a relaxing sitting/work area. Both bathrooms have been nicely maintained, and the primary bath features a double-sink vanity and an updated shower. One of the home's standout features is the 12' x 16' Florida room, adding approximately 192 square feet of additional living space. This versatile room is on the home's HVAC system, making it a wonderful space to relax, entertain, enjoy hobbies, or simply take in the Florida lifestyle. You'll also appreciate the inside laundry area, making everyday living convenient. Numerous important updates add peace of mind, including a 2023 central HVAC system and a 2023 shingle roof rated for 160-mph winds. The kitchen appliances have also been updated, including a newer refrigerator and dishwasher. The home also features updated plumbing/piping and double-pane windows in the living room. Outside, the home offers a welcoming covered entry and a large carport/driveway area, along with mature landscaping and colorful plantings that give the property wonderful curb appeal. The 2026 monthly lot lease is $632.05, which includes all the amenities of Swiss Golf and Tennis and Hidden Golf Club. Swiss Golf & Tennis is located on beautiful Lake Henry with opportunities to fish, go boating & enjoy the gorgeous sunsets. It is a very active 55+ Golf gated community. There are 2 clubhouses, 2 pools with Hot tubs, Fitness Room, Billiards Room, Library, Pro Shop for the 18-hole golf course, tennis court, and an onsite Restaurant and Pub with so much more! All listing information is considered reliable and appropriate by Sun Resales, Inc., but not guaranteed. Measurements are approximate. The buyer is responsible for verifying all current lot rent, fees, pass-on costs, community rules, regulations, and pet policies directly with the park manager. Sun Resales, Inc. is not responsible for quoting these terms. 1029 Hook Lane, Winter Haven, FL 33881 Out of town? No problem! We offer virtual showings and can complete all paperwork remotely for your convenience. Contact Cindy Minnick with Sun Resales today to schedule your personal or virtual tour!

1029 Hook Lane, Winter Haven

Listing courtesy of Cindy Minnick with Sun Resales, Inc.
1306 15th Street Sw, Winter Haven
$245,000
3 Beds ⋅ 2 Baths ⋅ TB8547534 MLS
3BR/2BA Beauty Near Downtown Winter Haven — Fully Updated Kitchen! Move right into this beautifully updated 3-bedroom, 2-bathroom home just minutes from downtown Winter Haven. The kitchen has been completely renovated with brand-new cabinetry, a stylish island, and gleaming granite countertops — a true showstopper for anyone who loves to cook or entertain. Ceramic tile flooring flows throughout the entire home for a clean, cohesive, low-maintenance feel. Enjoy an unbeatable location within walking distance of both Lake Shipp and Lake Howard — perfect for morning walks, fishing, or simply soaking in that classic Central Florida lake life. Downtown Winter Haven's shops, restaurants, and community events are just a short drive away. This home comes move-in ready with the refrigerator, stove, microwave, dishwasher, washer, and dryer all included. Major systems have been well maintained. No HOA means no extra fees and no added restrictions. Homes like this in this location don't sit on the market long — schedule your showing today!

1306 15th Street Sw, Winter Haven

Listing courtesy of MARK SPAIN REAL ESTATE. 855-299-7653
1711 Garden Lake Drive Unit 1711, Winter Haven
$159,900
1 Beds ⋅ 1 Baths ⋅ P4939856 MLS ⋅ Winterset Condo BLDG.
Virtually Staged. Welcome to a little slice of Florida paradise in Winterset, a GATED WATERFRONT COMMUNITY nestled along Winter Haven’s famous Chain of Lakes. This charming 1-bedroom, 1-bathroom condominium offers something truly special: a relaxed lakeside lifestyle, resort-style community amenities, and a home filled with unique spaces and thoughtful updates. Inside, the primary bedroom is wonderfully spacious and features a huge walk-in closet and en suite bathroom. But, one of the home's most delightful surprises is the fun overhead loft, creating flexible bonus space that could be the perfect home office, media area, reading nook, hobby space—or simply your own cozy hideaway. And when it comes to storage, you'll have plenty of room for all the things you don't want taking up your living space, thanks to additional interior AND exterior storage. Major updates mean you can settle in with confidence, too. The HVAC SYSTEM and WATER HEATER were both REPLACED in 2024, giving you two important big-ticket improvements already taken care of. Then there's the lifestyle... Step outside and enjoy everything Winterset has to offer. Take advantage of the community dock and lake access on the SE Chain's coveted Lake Winterset, spend a sunny afternoon at the pool and spa, meet friends at the clubhouse, or enjoy a friendly game of tennis or shuffleboard. When you're ready to get out on the water, Winter Haven's interconnected Chain of Lakes offers endless opportunities for boating, fishing, relaxing, and enjoying those beautiful Florida sunsets. The location is another reason to love this home. You're conveniently close to LEGOLAND Florida Resort, restaurants, grocery shopping, medical facilities, and everyday essentials, while downtown Winter Haven and its lakeside dining and local attractions are also just a few minutes away--whether by boat or by car. Whether you're searching for a full-time Florida home, a weekend retreat, a place to escape the cold, or simply a low-maintenance home where there's always something fun to do, this Winterset condo offers an appealing blend of comfort, character, recreation, and location.

1711 Garden Lake Drive Unit 1711, Winter Haven

Listing courtesy of JOHN WOOD REALTY, INC.. 863-324-9663
6364 Lolly Bay Loop Ne, Winter Haven
$215,000
2 Beds ⋅ 2 Baths ⋅ O6441156 MLS
Welcome to 6364 Lolly Bay Loop NE, a beautifully updated Winter Haven home offering comfort, value, and a convenient Central Florida lifestyle. This property features a **2023 roof, remodeled bathrooms, and new flooring**, giving buyers important major updates and a fresh, move-in-ready feel. Located in a peaceful residential setting, this home offers the opportunity to enjoy the relaxed Winter Haven lifestyle while remaining within convenient driving distance of Orlando and other Central Florida destinations. With access to major highways, nearby shopping, dining, outdoor recreation, and Winter Haven’s many lakes, this location offers the best of both convenience and tranquility. Whether you're looking for a primary residence, a place to settle down, or a home that offers more value for your money, this property is a great opportunity to make Central Florida living your own. Schedule your private showing today and come see all that this home has to offer!

6364 Lolly Bay Loop Ne, Winter Haven

Listing courtesy of EXP REALTY LLC. 407-706-5000
2801 Wingfoot Court, Winter Haven
$245,000
2 Beds ⋅ 2 Baths ⋅ P4939773 MLS
BEAUTIFUL VILLA READY TO MOVE IN! A brand-new HVAC system (June 2026), along with new insulation throughout the attic. Features include cathedral ceilings, elegant detailed trimwork with decorative corner blocks throughout, new flooring, plantation shutters on the windows, and three sets of French doors. The upgraded kitchen features stainless steel appliances, double ovens, and a built-in pantry with pull-out shelves. A utility closet provides additional storage, and the interior laundry room includes a full-size washer and dryer. The primary bathroom features dual showers and two vanities with wood cabinetry, while the second bathroom includes a jetted bathtub and wood cabinet vanity. Both bathrooms also feature skylights. Golf course frontage and two outdoor patio areas, with one overlooking the 8th fairway, plus a second patio with concrete privacy walls. HOA fee includes roof replacement when needed, so you never have to worry about roof expenses. Cypresswood Country Club community offers golf, a Jr. Olympic-size pool, tennis courts, pickleball courts, a restaurant and bar, social events, live music three nights a week, and lush, well-maintained surroundings. Come take a look at this one!

2801 Wingfoot Court, Winter Haven

Listing courtesy of VILLAGE REALTY OF WINTER HAVEN. 863-299-6767
707 Dolly Ben Court, Winter Haven
$225,000
3 Beds ⋅ 1 Baths ⋅ P4939828 MLS
NEW PRICE ON THIS ADORABLE & AFFORDABLE 3 BEDROOM CBS HOME WITH RECENT UPGRADES IS SITUATED ON A LARGE LOT AND NO HOA!!! The recent upgrades include new interior paint, new kitchen renovation with new appliances & granite countertops, new hot water heater, new light fixtures, new bifold doors, new window, new toilet, fixtures and vanity in the bathroom & more!!! Features include tile flooring throughout, kitchen has wood cabinets, granite countertops and all appliances. You'll enjoy the large, fenced back yard, one-car garage with extra room for storage. Centrally located in Winter Haven, the home is located at the end of a dead-end street for low traffic. Hurry & call today - make this home your own!!

707 Dolly Ben Court, Winter Haven

Listing courtesy of THE K TEAM REAL ESTATE SERVICES LLC. 863-604-1601
212 Majestic Gardens Lane, Winter Haven
$279,000
3 Beds ⋅ 2 Baths ⋅ TB8547254 MLS
Welcome home to this beautifully refreshed 3-bedroom, 2-bathroom home offering a comfortable layout, fresh updates, and an expansive backyard with plenty of possibilities. Step inside to discover all-new flooring and fresh interior paint, creating a bright, clean, and inviting atmosphere throughout the home. The spacious living areas provide a versatile setting for both everyday living and entertaining, with plenty of natural light adding to the welcoming feel. The well-designed floor plan offers three comfortable bedrooms and two full bathrooms, providing plenty of space for a variety of needs. The attached two-car garage adds valuable parking, storage, and everyday convenience. Outside, the sprawling backyard is one of the home's standout features, offering abundant space to entertain, garden, enjoy outdoor activities, or create your own private retreat. Whether you envision a large outdoor gathering area, garden space, play area, or simply room to relax and enjoy the outdoors, the possibilities are plentiful. With fresh interior updates, a functional layout, generous living space, an attached two-car garage, and an expansive backyard, this home is ready for its next chapter. Come see all that this refreshed home has to offer and schedule your showing today!

212 Majestic Gardens Lane, Winter Haven

Listing courtesy of EXP REALTY LLC. 888-883-8509
3831 Gaines Drive, Winter Haven
$765,000
3 Beds ⋅ 2 Baths ⋅ O6441050 MLS
Virtually Staged. Welcome to 3831 Gaines Dr, where beautifully updated interiors, exceptional outdoor living, and the best of the Winter Haven lifestyle come together. Situated on an impressive half-acre-plus homesite in the established Gaines Cove area, this immaculate 3-bedroom plus dedicated office home offers the space, privacy, and character that can be difficult to find. The location is a standout. Enjoy being just minutes from the Winter Haven Chain of Lakes, with multiple nearby options for boat ramps and lake access, making it easy to spend your days boating, fishing, skiing, or exploring Winter Haven’s interconnected lakes. LEGOLAND Florida Resort is also just minutes away, along with shopping, dining, and the everyday conveniences of the Cypress Gardens area. Inside, an inviting open floor plan welcomes you with spacious living areas designed for both everyday comfort and entertaining. Architectural details, abundant natural light, plantation shutters, and a fireplace with built-ins add warmth and character throughout. The beautifully updated kitchen features brand-new appliances and flows seamlessly into the main living area, while updated bathrooms and thoughtful improvements throughout create a polished, move-in-ready feel. A dedicated office with French doors provides the perfect space for working from home, studying, or additional flex space. The upgrades go well beyond what you immediately see. The home features a Kinetico water filtration system, allergen air filtration system, and a Tesla charging station, adding modern convenience and functionality to an already impressive property. Step outside and discover what truly sets this home apart. The expansive screened outdoor living area creates your own private Florida backyard retreat, centered around a heated saltwater pool with plenty of space for relaxing and entertaining. The substantial covered lanai features an impressive outdoor kitchen with built-in grill, vent hood, sink, and refrigeration, complemented by generous outdoor dining and seating areas. Remote-controlled power sun shades on the rear lanai provide added shade, privacy, and comfort at the touch of a button, making this incredible space even more enjoyable throughout the day. And unlike many pool homes, the backyard doesn't end at the screened enclosure. Beyond the pool is an expansive fenced yard with abundant usable green space, mature trees, and beautifully maintained landscaping. The combination of a large homesite, resort-style pool area, covered outdoor living, and substantial backyard creates a wonderful sense of openness and privacy. Curb appeal is equally impressive, with a large paver driveway, expansive front lawn, mature landscaping, and welcoming covered front porch creating a memorable first impression. Spend the morning boating on the Chain of Lakes, the afternoon relaxing in your heated saltwater pool, cook dinner in your outdoor kitchen, and finish the evening unwinding on the lanai. With LEGOLAND just minutes away and shopping, dining, recreation, and multiple lake-access options nearby, 3831 Gaines Dr offers more than a beautifully updated home—it offers the Winter Haven lifestyle.

3831 Gaines Drive, Winter Haven

Listing courtesy of COLDWELL BANKER REALTY. 407-647-1211
507 Short Lane, Winter Haven
$329,000
4 Beds ⋅ 2 Baths ⋅ S5157350 MLS
Beautiful home featuring 4 spacious bedrooms and 2 bathrooms. The fully equipped kitchen boasts beautiful wood cabinetry and granite countertops. Sliding glass doors lead to a covered patio and a private, grassy backyard—perfect for relaxing and enjoying the Florida outdoor lifestyle. The home includes a 2-car garage and a fully equipped laundry room for added convenience. Situated in a desirable community, this property offers comfort, practicality, and excellent investment potential. It is conveniently located near LEGOLAND, Chain of Lakes Park, downtown Winter Haven, shopping centers, restaurants, grocery stores, and medical facilities, with easy access to Highway 27. Winter Haven is also known for its beautiful Chain of Lakes, offering opportunities for boating, fishing, and outdoor recreation. The property is currently leased at $2,000 monthly. A fantastic opportunity for both investors and future homeowners.

507 Short Lane, Winter Haven

Listing courtesy of LPT REALTY, LLC. 877-366-2213
624 Sarner Pass Way, Winter Haven
$299,000
4 Beds ⋅ 2 Baths ⋅ TB8547660 MLS
Welcome home! This beautiful property features a comfortable and functional layout, perfect for everyday living and entertaining. Enjoy spacious living areas, a well-appointed kitchen, and inviting bedrooms with plenty of room to relax. Step outside to the fully fenced backyard, providing added privacy and plenty of space for outdoor activities, pets, or weekend gatherings. The covered lanai is the perfect place to enjoy your morning coffee, unwind after a long day, or simply take in Florida’s beautiful weather year-round. Conveniently located near shopping, dining, schools, and major roadways, this home combines comfort, space, and convenience. Schedule your private showing today!

624 Sarner Pass Way, Winter Haven

Listing courtesy of THE ELITE REALTY EXPERIENCE. 813-493-1297
Brigham Road, Winter Haven
$95,000
L4964455 MLS
Bring your vision to life on this cleared and leveled homesite in a convenient Winter Haven location! Situated on just under half an acre, this property offers a clean slate ready for you to build the home you’ve been dreaming of. With the lot already cleared and leveled, you can spend less time imagining what could be and more time planning what comes next. Enjoy convenient access to Downtown Winter Haven, Lake Alfred, shopping, dining, and major roadways, making travel throughout the area and your daily commute a breeze. Whether you’re ready to build now or looking for the perfect piece of land for the future, this property offers the space, location, and opportunity to make your dream a reality. Your future starts here!

Brigham Road, Winter Haven

Listing courtesy of KELLER WILLIAMS REALTY SMART 1. 863-508-3000
815 Andrew Street, Winter Haven
$319,990
4 Beds ⋅ 2 Baths ⋅ O6438380 MLS ⋅ Na BLDG.
Under Construction. Ready in November, 2026. 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 ensuite bathroom with dual sink vanity, shower, private water closet, and large walk-in closet. Photos are representative only and not of the actual home. Selections, features, and finishes may vary.

815 Andrew Street, Winter Haven

Listing courtesy of DRB GROUP REALTY, LLC. 407-270-2747
177 Geneva Drive, #177 Unit #177, Winter Haven
$42,000
2 Beds ⋅ 2 Baths ⋅ 11973879 MLS
Swiss Village / Lot #177 /2 Bedroom/2 Bath /1,080 Sq.Ft.+ Large Florida Room / $42,000 SELLER MOTIVATED, PRICED TO SELL!!This gorgeous Palm Harbor home is partially furnished and is located on a one-of-a-kind large lot! It is priced to sell and has upgrades such as: New Double-Paned Windows Throughout Large Florida Room that is A/C'd and adds square footage (with new windows) 4" Blinds Throughout Completely Updated Guest Bathroom with Walk-In Shower Luxury Vinyl Plank Flooring Throughout A/C & Roof (only 4 years old) Updated Ceiling Fans & Lighting Custom Backsplash Extra-Long Driveway Patio & Large Shed New Refrigerator & Dishwasher GREAT CURB APPEAL!! Located near the two pools and clubhouse, you are steps away from all of the planned activities and amenities! Let's set up your tour today, so you can see, in person, just how special this affordably priced home and lake-side community really are!!!

177 Geneva Drive, #177 Unit #177, Winter Haven

Listing courtesy of Donna Kendall with CRF Communities
6136 Pebble Beach Boulevard, Winter Haven
$549,999
3 Beds ⋅ 3 Baths ⋅ P4939770 MLS
Virtually Staged. *GOLF COURSE and WATER VIEWS*** Located behind the secure gates of the coveted 55 + community of Lake Ashton, the water views from the covered and screened lanai are superb! Built in 2019, this home offers TWO SUITES, ONE GUEST BEDROOM and THREE BATHS. This split floor plan home offers great curb appeal with a FRESH NEW EXTERIOR COAT OF PAINT, Paver Driveway and Well Maintained Landscape. The lawn is "watered" by an irrigation system. As you enter thru the double glass doors of this home you are greeted by a large open floor plan offering expansive views of the golf course and lake beyond. The water views from this coveted lot location are spectacular! The living room, formal dining area and kitchen flow seamlessly together in this modified ASHTON Floor plan home, making entertaining easy and fun! The spacious Living Room has a tray ceiling, floor outlets, ceiling fan and triple sliders that stack and open to the covered and screened lanai. A formal dining area is located to the left of the front entry and the arched double windows add a touch of class! The Kitchen features 42" wood cabinetry, breakfast bar, pendant lighting, granite countertops, SS appliances (microwave replaced Sept. 2026) and ample counter top space for food prep and food display. The Dinette area is conveniently located off of the kitchen and the double windows provide an abundance of natural light into the home. Double sliders provide access to the lanai from the dinette area. The spacious and oversized Primary Suite with double door entry makes up the right wing of the home. It showcases two large walk-in closets, a separate water closet with window, a linen closet, a large, tiled walk in shower with grab bars and a tiled bench to sit on. The vanity with double sinks compliments the bathroom area. The Primary Suite with trey ceiling and ceiling fans can accommodate a separate sitting area for relaxation or larger bedroom furniture. The 2nd Suite with double door entry is on the left side of the home. It's accessible from the dinette area and from the hallway that leads to the 3rd Bedroom/3 Bath. The 2nd Suite has a private bath and built in closet. The 2nd Suite Bath features a comfort height vanity, walk in shower with glass enclosure, grab bars, foot rest and comfort height toilet. Overnight Guests will enjoy their own bedroom and bath with shower/tub combo and comfort height vanity. The Laundry Room (FLEX ROOM) is spacious and well designed with a wash tub and portable storage units for your personal items. The washer/dryer are included in the sale of this home. The outdoor living space offers a delightful place for entertaining. There are two OPTIONS: You can enjoy the covered portion of the lanai or the extended/uncovered screened lanai with direct views of the golf course and lake. The double car garage is sizeable and there is a separate golf cart entrance. The home also has a WHOLE HOUSE GENERAC- this is a huge bonus! ADDITIONAL IMPROVEMENTS to this home include: NEW INTERIOR PAINT and NEW LUXURY VINYL FLOORING. The community of Lake Ashton is a hidden treasure with an aura of peace and tranquility, and offers 2 golf courses, tennis courts, 2 pools (one indoor and one outdoor) movie theater, bowling lanes, card, craft and billiard rooms, fitness centers, pickleball courts, indoor basketball, indoor racquetball, numerous recreational activities, and restaurants. Make an appointment today to TOUR THIS HOME!

6136 Pebble Beach Boulevard, Winter Haven

Listing courtesy of LAKE ASHTON REALTY INC.. 863-409-6899
1776 6th Street Nw Unit 304, Winter Haven
$92,900
2 Beds ⋅ 2 Baths ⋅ P4939801 MLS ⋅ Lakeridge BLDG.
**THIS CONDO IS PRICE TO SELL !!**CENTRAL FLORIDA 55+ Age GATED CONDOMINIUM COMPLEX WITH LAKE AND CITY VIEW. All new insulated windows throughout. This condominium provides 1,347 sq. ft. of living area & is located in the beautiful "Chain Of Lakes" City of Winter Haven, Fl. Very friendly complex w/ social activities offered if you wish to participate. Monthly association fee includes water, sewer, trash, fiber optic cable & internet, condo reserves, manager and use of recreational facilities. Lakeridge Condominiums offers a maintenance-free lifestyle w/ heated pool, tennis, shuffleboard, community room, gated entrances & covered assigned parking space. The large bright kitchen has plenty of cabinets & great counter space, appliances (dishwasher does not work) & pantry closet. The kitchen overlooks the 26'x14' great room that also adjoins the additional bonus space & storage closet. The 16X14 foot Primary bedroom suite has a walk in closet & bathroom w/ walk-in shower. Beautiful views of Spring Lake can be enjoyed from Primary bedroom & living areas. The 2nd bedroom & bath can be a private guest area or for your personal use for office, hobbies etc. The washer & dryer are included in the sale. Central heat and air conditioning. Convenient proximity to shopping, places of worship, groceries & restaurants. Extra assigned storage bin on same floor. Make this your full time home, winter home or investment property to update. Lakeridge Condominiums is an age-restricted, well-maintained & well-managed community. Sharepoint car charger provided for those with electric cars. Non-smoking property. 1 pet, 20 pounds or under may be approved.

1776 6th Street Nw Unit 304, Winter Haven

Listing courtesy of JUDY B CLEAVES PROPERTIES INC. 863-299-5878
44 Brevard Drive, Winter Haven
$475,000
3 Beds ⋅ 2 Baths ⋅ TB8546901 MLS
* METAL ROOF & AC DONE IN 2024* Welcome home to this spacious 3-bedroom, 2-bath pool home offering 2,269 square feet of living space, with an inviting layout designed for everyday living and entertaining. Topped with a new metal roof, this home combines valuable recent improvements with plenty of character inside and out. Step inside to an open and expansive living area highlighted by exposed wood beams, recessed lighting, and tile flooring throughout much of the main living space. The updated kitchen features luxury cabinetry, quartz countertops, subway tile backsplash, stainless steel appliances, abundant storage, and generous counter space, all flowing naturally into the dining and living areas. An additional bonus/game room offers exceptional flexibility and could serve as a billiards room, home theater, playroom, office, or second family room. The primary suite features a spacious walk-in closet and an updated bathroom with a large dual-sink vanity, modern fixtures, and beautifully tiled walk-in shower. Step outside to your own Florida retreat featuring a private in-ground swimming pool, paver deck, and tropical landscaping. The expansive screened lanai overlooking the pool provides plenty of covered space for outdoor dining, entertaining, or simply relaxing and enjoying the Florida lifestyle year-round. Additional highlights include a dedicated indoor laundry room, generous storage, spacious secondary bedrooms, multiple living areas, and a large backyard. With its new metal roof, updated interior, private pool, screened outdoor living space, bonus room, and 2,269 square feet of living space, this Winter Haven home delivers the space, versatility, and indoor-outdoor lifestyle today's buyers are looking for.

44 Brevard Drive, Winter Haven

Listing courtesy of SCHLEICHER SELECT PROPERTIES. 863-581-2624
679 Avenue L Se, Winter Haven
$182,000
3 Beds ⋅ 1 Baths ⋅ O6440388 MLS
Auction Property. 3-bedroom, 1 bath, 1,080 square foot ranch home sitting on 10,097 square foot lot. Cyprus Gardens, Lego Land and a few Parks near you can recharge your energy. Only a short distance from the Orlando International airport. Make it your own. Jump on this great deal before its gone! All buyers are responsible to confirm City, County, Zoning, Tax, and other records to their satisfaction before bidding. No inspection contingencies in contract. Absolutely no repairs before closing. This property is sold As-Is. This is a REO auction property.

679 Avenue L Se, Winter Haven

Listing courtesy of REALHOME SERVICE & SOLUTIONS INC. 855-882-1314
754 Santa Maria Dr, Winter Haven
$359,000
4 Beds ⋅ 3 Baths ⋅ P4939817 MLS
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

Listing courtesy of CENTURY 21 WATSON & MYERS REALTY. 863-324-1000
913 Turnstone Lane, Winter Haven
$3,000
4 Beds ⋅ 2.5 Baths ⋅ 11971772 MLS
PRIVATE POOL + FLEX SPACE! This two-story Winter Haven home offers 4 bedrooms, 2.5 bathrooms, approximately 2,208 sq. ft. of living space, and a flexible bonus room/office that adds valuable function to the floor plan. The bright interior offers abundant natural light, spacious living areas, and a kitchen with a double pantry providing substantial storage. The bonus room is ideal for a home office, media room, guest space, playroom, workout area, or other flex use, allowing the home to adapt to a variety of needs. Step outside and enjoy one of the home's biggest highlights: a screened private pool area with a whirlpool/jacuzzi, creating a comfortable outdoor retreat for relaxing and enjoying the Florida lifestyle. This home is pet friendly and conveniently located near shopping, dining, major roadways, and LEGOLAND Florida Resort. Please note: the two-car garage is excluded from the lease. Schedule your private showing and discover the space, flexibility, storage, and private-pool lifestyle this rental has to available.

913 Turnstone Lane, Winter Haven

Listing courtesy of Carmen Sousa Erazo with La Rosa Realty Kissimmee
240 Fairway Circle, #240 Unit #240, Winter Haven
$59,900
2 Beds ⋅ 2 Baths ⋅ 11966614 MLS
2 Bed | 2 Bath | 1248 square foot | $59,900 (Swiss Golf and Tennis- Lot 240) NO LOT RENT UNTIL JAN 2027 and One-year FREE golf membership with your purchase! This beautiful and completely renovated home is located in a highly desirable 55+ community. Highlights include: Brand New roof, carport, and AC (2026) -Beautiful open kitchen with brand new appliances and island/bar for eating and entertaining - gorgeous mud room and pantry - All new lighting - All new flooring throughout - Double carport for plenty of parking - Spacious shed with lots of storage space. Fresh landscaping for beautiful curb appeal. You do not want to miss this one! This home gives you access to a relaxed, resort-style lifestyle. Enjoy the beautifully maintained 18-hole golf course. One-year FREE golf membership with your purchase! Unwind at the heated pool and spa overlooking beautiful Lake Henry. The community also features an on-site restaurant and pub. Residents also enjoy a variety of recreational activities including tennis, pickleball, and shuffleboard. Call today to schedule a tour!

240 Fairway Circle, #240 Unit #240, Winter Haven

Listing courtesy of Brandi Sappington with CRF Communities
1200 33rd Street Nw, Winter Haven
$269,900
3 Beds ⋅ 2 Baths ⋅ L4964764 MLS
Welcome to this beautifully maintained 3-bedroom, 2-bathroom home in Winter Haven, built in 2023 and offering the feel of a nearly new home without the wait for new construction. The open and inviting layout features durable vinyl flooring throughout, creating a clean and modern look with easy maintenance. Thoughtful upgrades include a black aluminum privacy fence, an expanded two-car driveway, and paver walkway for added curb appeal. Inside, matte black faucets and door hardware throughout the home add a stylish, contemporary touch. The spacious backyard provides plenty of room for outdoor entertaining, pets, gardening, or simply enjoying Florida’s beautiful weather. With no HOA, you’ll have added flexibility and freedom without monthly association fees or restrictions. Conveniently located in Winter Haven, this move-in-ready home combines modern finishes, desirable upgrades, and a low-maintenance lifestyle. Schedule your showing today!

1200 33rd Street Nw, Winter Haven

Listing courtesy of 54 REALTY LLC. 813-435-5411
5325 Snead Drive, Winter Haven
$349,500
3 Beds ⋅ 2 Baths ⋅ TB8546364 MLS
MOTIVATED SELLERS!!! Welcome to one of THE MOST DESIRABLE AND BEAUTIFUL 55+ GATED/GUARD community in Winter Haven, FL! LAKE ASHTON has great amenities for their residents to enjoy every day and feel in PARADISE. An enormous club house were events are held, two pools, dog park, golf course, bowling, movie theater, fitness center, restaurant, and more. There's also a 2nd clubhouse available for residents. This gorgeous well maintained home has MULTIPLE VALUABLE UPGRADES that the future owner would enjoy. Even the floor plan was updated in the KITCHEN making this home UNIQUE in the neighborhood! NEW ROOF was installed in 2024, DISHWASHER FEB 2026, REFRIGETATOR NOV 2025, and WATER HEATER 2021. Also ENJOY the BENEFIT of having WATER SOFTENER, A WATER PURIFIER SYSTEM IN THE KITCHEN and QUARTS COUNTER TOPS. For the outdoor living you have a SPACIOUS TILE FLOORING, SCREENED LANAI WITH FLORIDA GLASS FOR PRIVACY. ONE OF THE BEST FEATURES OF THIS PROPERTY IS THAT IT HAS PAID OFF SOLAR PANELS. WHAT ELSE YOU CAN ASK FOR? This helps with the electric bill cost. COME AND SEE THIS AMAZING HOME THAT WILL MAKE YOU FEEL IN PARADISE!

5325 Snead Drive, Winter Haven

Listing courtesy of LA ROSA REALTY LLC. 321-939-3748
Archaic Drive, Winter Haven
$199,900
TB8546225 MLS
LAST BUILDING LOT ON SPIRIT LAKE IN THE VILLAGES OF SPIRIT LAKE, SO BRING YOUR PLANS AND START ENJOYING THIS GATED COMMUNITY. OFFERING A PRIVATE BOAT LAUNCH, FISHING DOCK PLUS COMMUNITY POOL, CLUBHOUSE, PLAY GROUND, TENNIS, BASKETBALL AND PICKLEBOARD COURTS. EAST ACCESS TO THE POLK PARKWAY SO COMMUTES TO TAMPA OR ORLANDO MAKE IT EASY. OWNER TERMS AVAILABLE IF NEEDED WHILTE GETTING YOUR CONSTRUCTION PLANS TOGETHER.

Archaic Drive, Winter Haven

Listing courtesy of BRIDGMON REALTY. 813-478-3107
2112 Avenue C Sw, Winter Haven
$379,000
4 Beds ⋅ 2 Baths ⋅ P4939766 MLS
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

Listing courtesy of KELLER WILLIAMS REALTY SMART 1. 863-508-3000
6204 Knotty Pine Drive Se, Winter Haven
$165,000
2 Beds ⋅ 2 Baths ⋅ P4939790 MLS
OWN THE LAND! NO LOT RENT! LOW $65/MONTH HOA! FURNISHED AND EXTENSIVELY UPDATED IN 2026! Discover affordable Florida living in this beautifully renovated 2-bedroom, 2-bath manufactured home situated on a spacious, beautifully landscaped CORNER LOT THAT YOU OWN! Offering exceptional value, this MOVE-IN-READY home comes furnished and features an impressive list of recent improvements, including a NEW ROOF, NEW A/C, UPDATED PLUMBING , NEW FLOORING, FRESH INTERIOR AND EXTERIOR PAINT, NEW WINDOWS AND DOORS, UPDATED LIGHT FIXTURES, RENOVATED BATHROOMS, AND A BEAUTIFULLY UPDATED KITCHEN WITH QUARTZ COUNTERTOPS AND NEW APPLIANCES! Step inside to a bright, welcoming living space with an open layout perfect for relaxing or entertaining. The desirable SPLIT-BEDROOM FLOOR PLAN provides privacy for owners and guests alike. The spacious primary suite features its own updated bathroom with a convenient step-in shower, while the guest bedroom offers easy access to a beautifully refreshed second bathroom with a tub. Both bathrooms feature elegant quartz countertops. Enjoy your morning coffee or unwind in the evenings on the 14' x 8' SCREENED-IN PORCH, offering additional space to enjoy Florida's beautiful weather. A separate laundry room with WASHER AND DRYER INCLUDED, convenient workshop area, and an 18' x 11' CARPORT with an extended driveway add even more functionality and value. The community amenities are equally impressive! Enjoy a welcoming CLUBHOUSE featuring a spacious entertainment room, full kitchen, library, and billiards room. Spend sunny afternoons relaxing by the OVERSIZED SWIMMING POOL overlooking scenic PEACE POND, unwind in the spa, gather with friends in the poolside cookout room, or enjoy a game of shuffleboard. With a LOW HOA OF JUST $65 PER MONTH and NO LOT RENT, you can enjoy the benefits of community living without the expense of leasing your land. FURNISHED, BEAUTIFULLY UPDATED, AND READY FOR IMMEDIATE ENJOYMENT! Whether you're looking for a year-round residence or a seasonal Florida getaway, this home offers comfort, convenience, and exceptional value. Schedule your private showing today and discover everything this wonderful property has to offer! LISTING AGENT IS THE OWNER.

6204 Knotty Pine Drive Se, Winter Haven

Listing courtesy of COLDWELL BANKER REALTY. 863-294-7541
1116 40th Street Nw, Winter Haven
$44,900
3 Beds ⋅ 2 Baths ⋅ R4911936 MLS
Excellent investment property centrally located in Winter Haven,

1116 40th Street Nw, Winter Haven

Listing courtesy of MILLSHIRE REALTY. 863-815-8000
333 Lake Howard Drive Nw Unit 204D, Winter Haven
$139,999
3 Beds ⋅ 2 Baths ⋅ O6437272 MLS ⋅ 1 BLDG.
**Welcome to Imperial Harbours, a beautifully maintained 55+ active community surrounded by gorgeous landscaping and offering access to Winter Haven’s Chain of Lakes!** This spacious **3-bedroom, 2-bath second-floor corner condo** offers over 1,226 sq. ft. of comfortable living with an open-concept living/dining area, lovely kitchen with beautiful countertops and abundant cabinetry, plus an enclosed bonus room perfect for an office, sitting area, or hobby space. The generous primary suite features a private bath and large walk-in closet. Enjoy the peace of mind of a **BRAND-NEW A/C**, newer double-pane windows, updated bathroom vanities, fresh interior paint, and an in-unit washer and dryer. Additional features include an exterior storage unit, elevator access, covered assigned parking, guest parking, and community car wash. Enjoy resort-style amenities including a **heated pool, fitness room, billiards, recreation room, shuffleboard, BBQ grills, gazebo, fishing, dock access, and nearby boat ramp.** HOA includes **water, internet, cable, and trash!** Conveniently located near hospitals, restaurants, shopping, and everyday essentials. **Come experience the Florida lifestyle at Imperial Harbours—schedule your private showing today!**

333 Lake Howard Drive Nw Unit 204D, Winter Haven

Listing courtesy of UNITED REAL ESTATE PREFERRED. 407-243-8840
2215 Starboard Drive Unit 29, Winter Haven
$184,900
2 Beds ⋅ 2 Baths ⋅ B4902354 MLS ⋅ Hartridge Landing BLDG.
Great condo in Hartridge Landings. A premier 55+ small 42 unit custom condominium complex Walking out the front door one can find themselves only a few steps from the clubhouse, pool and the famous Chain of Lakes...Lake Hartridge. 17-lake chain of inter-connected lakes. Boating and fishing enthusiasts paradise! Well maintained. This home comes with several skylights to brighten your day. It also has several custom shelves and engineered closet built-ins. Large totally private rear patio area that's great for entertaining outside and room to add a portable spa. Large double car garage with some storage closets. New TPO roof, re-piped plumbing and a/c system in 2022. Vacant and easy to show.

2215 Starboard Drive Unit 29, Winter Haven

Listing courtesy of KLINE REAL ESTATE SERVICES. 863-287-0204
1020 Cambridge Drive, Winter Haven
$279,900
4 Beds ⋅ 2 Baths ⋅ O6439455 MLS
Virtually Staged. Welcome to this beautiful one-story Freeport floor plan featuring 4 bedrooms, 2 bathrooms, an open-concept kitchen and great room, a private primary suite with a walk-in closet, a patio, and a two-car garage. The home also includes solar panels, offering incredible energy savings even during August, one of the hottest months of the year; the electric bill was under $20! The buyer must assume the existing solar-panel account. Don’t miss this wonderful opportunity to enjoy a comfortable home with significantly lower energy costs!

1020 Cambridge Drive, Winter Haven

Listing courtesy of CAPITAL HOMES INC. 800-642-0668

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