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$170,000
2 Beds 2 Baths Imperial Villas SubDv. 33880 Zip Code
Under contract-accepting backup offers. MOTIVATIED SELLERS!!! MAINTENCE-FREE LIVING...Located right in the Heart of Winter Haven at Imperial Villas, a 55+ community. This very well maintained 2 Bedroom/ 2 Bathroom Villa that offers a complete update, boasting tasteful renovations throughout. Being sold Fully Furnished! From the kitchen to the bathrooms, flooring to the roof, nearly everything has been thoughtfully upgraded. Step inside to discover new ceramic tile and luxury vinyl flooring that sets a modern tone. The kitchen showcases stainless steel appliances, granite countertops, ample cabinet and countertop space. Retreat to the owner's suite at the back of the villa, offering a beautifully tiled walk-in shower and a generous walk-in closet. Through the great room, step into to enclosed lanai. Updates include: Roof (2020), Electrical Panel (2023), HVAC (2012) & Tankless Hot Water Heater (2018). Residents of this community have access to a refreshing pool, making it perfect for leisurely afternoons. The low HOA fee of $270/month covers water, internet, cable, gas, trash and grounds maintenance, ensuring a hassle-free lifestyle. Conveniently located just a short walk from the picturesque Lake Howard and minutes away from downtown Winter Haven. You'll have easy access to charming shops, delectable restaurants, the historic Ritz Theater, and vibrant events like farmers markets in the park. Don't miss out on the opportunity to make this your new home. Schedule your private showing today and experience the epitome of Florida living!!

345 24th Street Nw Unit 23, Winter Haven

$199,900
2 Beds 2 Baths Buckeye Heights SubDv. 33881 Zip Code
Virtually Staged. A rare opportunity to own one of only six cluster homes positioned along the peaceful shoreline of Lake Buckeye! A charming open courtyard entry welcomes you to the front door, creating a private and inviting approach that sets this home apart. Inside, the living room immediately draws your eye outdoors, featuring double French doors that open to an enclosed lanai and extended open patio overlooking lake views. It’s the perfect space to enjoy morning coffee, evening breezes, or simply take in the calm waterfront setting. The layout flows comfortably from the living area into the wrap-around kitchen and adjoining dining space, where a large window overlooks the courtyard entrance and fills the home with natural light. The primary bedroom suite offers a private retreat with its own en-suite bath featuring a walk-in shower, while the second bedroom sits just steps from the guest bath with tub/shower combination — ideal for guests, family, or flexible use as a home office. Additional highlights include a laundry closet and an oversized 550 sq ft 2-car garage with ample storage, providing both convenience and functionality. For easy lake access, the public boat ramp onto Lake Buckeye is located just 0.1 mile down the road. Homes within The Clusters on Lake Buckeye rarely come to market, making this a special opportunity for buyers seeking a property with character, peaceful surroundings, and direct access to one of Winter Haven’s beautiful lakes. **A/C is 2015, Roof is 2017**

1502 Buckeye Road Ne Unit 4, Winter Haven

$169,000
2 Beds 3 Baths Casa Del Sol Condo Village Ph 02 SubDv. 33881 Zip Code
PRICE REDUCTION!!!! Welcome to Casa Del Sol, a desirable lakefront community on Lake Hartridge with access to the Winter Haven Chain of Lakes. This spacious 2bd/2.5 bath condo offers 1,334 sq. ft. of comfortable living with a smart two-story layout—main living areas downstairs and both bedrooms upstairs. The home incorporates rustic farmhouse design elements throughout, including decorative farmhouse wall paneling that adds warmth, texture, and character to the living spaces. Natural wood furnishings and neutral tones complement the farmhouse aesthetic, blending comfort with timeless style. This bedroom features a relaxed coastal design with soothing blue tones and nautical accents that create a bright, airy retreat. A bold navy accent wall highlights the space, complemented by decorative fishing net wall art and seaside décor. Large windows dressed in sheer navy curtains allow natural light to fill the room, enhancing the breezy coastal vibe. A second bedroom showcases a soft coastal palette with tranquil turquoise walls and light, breezy window treatments. The rustic whitewashed headboard adds a beach-cottage feel while coordinating with the natural textures and pastel bedding. The room’s calming color scheme and light-filled atmosphere create a peaceful, seaside-inspired retreat perfect for guests or family. The bathroom is enhanced with a sliding barn door, a popular farmhouse feature that combines charm with functionality. The door’s rustic wood finish and exposed hardware create a stylish focal point while maximizing space and adding a touch of modern farmhouse appeal. Enjoy low-maintenance living with HOA fees covering city water, sewer/garbage, exterior building maintenance, grounds care, and pool service. Community amenities include a clubhouse, two pools, tennis courts, shuffleboard, and a community dock with direct Lake Hartridge access. A rare bonus in condo living—an attached 2-car garage. Centrally located near major roadways for easy commuting to Lakeland, Auburndale, and the I-4 corridor, yet tucked into a peaceful residential setting close to downtown events, waterfront paths, and local dining. Ideal as a primary residence, seasonal home, or investment property. Opportunities like this don’t last—schedule your private showing today.

2500 21st Street Nw Unit 23, Winter Haven

$119,000
2 Beds 2 Baths Carefree Rv Country Club SubDv. 33884 Zip Code
Welcome to Carefree Country Club - one of Winter Haven't best kept secrets! Tucked away off of Cypress Gardens Boulevard, when you approach the GATED community, you know you're entering a really special place. Driving through, you're encompassed by the community's 9-hole golf course. Continuing on, you'll pass a stunning two-story clubhouse, plus all of the amenities (large thermal heated swimming pool; bocce ball courts; tennis and pickle ball courts; boat docks and boat launch). And finally, you'll pass by Lake Bess, which the community has over 3,000 private feet of shoreline on! This home sits just a few homes up from the lake, and there is no need to worry about flooding, as the home pitches down toward the lake! Believe it or not, this is actually a single wide home with a large addition! Entering through the sliding glass doors, you'll find yourself in the open living space, where the kitchen, dining area, and living room flow together. You get great views of the lake through the windows as well! The original structure also has a guest bathroom (with a shower / tub combo) and guest bedroom. The addition has the primary suite, with a nice sized closet, and ensuite bathroom with a walk-in shower. In here you will also find the washer. Out back is a storage shed that can fit a golf cart (as you will see one currently in there), as well as the dryer. The home was re-piped, so no need to worry about polybutylene (grey) pipes! The monthly fees include the following: lawn care; internet access in the clubhouse and golf center; garbage disposal and recycling; all of the amenities! This is a great home in a great community; schedule your showing today!

9705 Lake Bess Road Unit 715, Winter Haven

$174,900
2 Beds 2 Baths Lake Howard Terrace SubDv. 33880 Zip Code
Beautifully Renovated Waterfront Condo in the Heart of Downtown Winter Haven Experience lakeside living in this fully remodeled end-unit condo located in the heart of Downtown Winter Haven, Florida. Every detail has been thoughtfully updated, creating a modern, move-in-ready home that combines style, comfort, and convenience. Enjoy breathtaking sunsets over Lake Howard from the expansive private waterfront patio—perfect for relaxing with your morning coffee or unwinding at the end of the day while taking in the spectacular views. This highly desirable end unit offers added privacy, abundant natural light, and includes two covered parking spaces conveniently located directly beneath the residence for easy access. The building exterior and grounds are exceptionally well maintained and have undergone significant improvements over the past 18 months, including complete building concrete remediation and exterior painting, roof resealing, resurfacing of all exterior walkways, parking lot resealing, and extensive landscaping enhancements. These major capital improvements provide both lasting value and peace of mind. Just steps from downtown's restaurants, shopping, entertainment, parks, and the Chain of Lakes, this exceptional waterfront property offers the very best of Florida living. A rare opportunity—this stunning waterfront condo is truly a must-see!

208 Lake Howard Drive Nw Unit 104, Winter Haven

$180,000
2 Beds 2 Baths Garden Grove Oaks SubDv. 33884 Zip Code
Seller's Motivated! Price just reduced! Welcome to 6086 Southern Oaks Drive SE, a beautifully updated and well- maintained, move in ready manufactured home located in the highly sought after 55+ community of Garden Grove Oaks where you OWN your Land and enjoy low HOA fees in a peaceful, well-maintained neighborhood. This home features two generously sized bedrooms and two full bathrooms. The primary suite boasts a private en-suite bath. Step into the living space filled with natural light featuring spacious living and dining areas ideal for entertaining or family gatherings. The kitchen has been updated and equipped with updated appliances (refrigerator and dishwasher are still under warranty), ample counter space and plenty of storage. Exterior doors have been replaced with wood doors. Roof was installed in 2018 A/C 2007. Laminate flooring throughout. The home has a shed and screened porch adding an additional 224 sq ft of space for storage or relaxing on the back screen porch. Enjoy community amenities, friendly neighbors and the convenience of being just minutes from local shopping, dining, medical facilities, and Winter Haven's world-famous Chain of Lakes. With access to major highways, commuting to nearby cities like Orlando or Tampa is a breeze. Don't miss the opportunity to make this beautifully maintained home in Garden Grove Oaks your new home! Schedule your private showing today and experience this property for yourself.

6086 Southern Oaks Drive Se, Winter Haven

$120,000
3 Beds 3 Baths Orchid Spgs Vill 400 San Miguel SubDv. 33884 Zip Code
Short Sale. Welcome to this beautifully updated mostly furnished end unit condo located on the second floor offering 1,666sf of comfortable living space in the desirable 55+ community of Orchid Springs. Tucked away in a serene setting, this end unit offers exceptional privacy & a peaceful feel while enjoying the security & convenience of community living. Inside you will find updated luxury vinyl flooring, windows, Stainless appliances and blinds, creating a move in ready space with modern touches throughout. The kitchen appliances, washer/dryer & AC were all just replaced in 2024! Wonderful split floor plan which offers 3 bedrooms and 2 full bathrooms, plus a guest half bathroom. There is an extended living room/ enclosed Florida room as well which is adding on to the spacious feel of this great unit. The bedrooms have plenty of storage space. All appliances are included also including the washer/dryer. The extended living space/enclosed Florida room provides the perfect place to relax and enjoy the tranquil surroundings and amazing views. Orchid Springs is a private, well-maintained community featuring a clubhouse and community pool. Located in Winter Haven, right of Overlook Dr. with easy access to shopping, churches, dining and medical facilities, this home offers the perfect blend of comfort, privacy and active 55+ living. Located in Central Florida, about 1 hour from Orlando and Tampa and 1,5 hour to each coast this is the perfect spot for affordable retirement living in the Sunshine State!

400 El Camino Drive Unit 210, Winter Haven

$129,900
2 Beds 2 Baths Lake N Golf Estates SubDv. 33881 Zip Code
Under contract-accepting backup offers. Welcome to Lake ‘N Golf Estates! This well-maintained 2-bedroom, 2-bath double-wide manufactured home is situated on 0.09 acres of land that you own, in one of Winter Haven’s desirable 55+ lakefront communities with direct access to the Lake Henry Chain of Lakes. Offering 1,296 sq ft of heated living space, the home features a spacious open layout, large living room, dedicated dining area, and an eat-in kitchen with ample cabinet storage and pantry. The primary suite includes a walk-in closet and private bath, while the guest bedroom also offers a walk-in closet and convenient access to the second full bathroom. Enjoy Florida living year-round with a bright Florida room, enclosed porch, and additional workshop/storage space—ideal for hobbies or extra storage. The covered carport and extended driveway provide convenient parking, and the home is being offered furnished, making it move-in ready. Community amenities include a clubhouse, community pool, boat slips, and golf-cart-friendly streets. Low annual HOA fee covers common area maintenance, recreational facilities, and pool maintenance. Buyer approval required. Conveniently located near shopping, dining, medical facilities, and Winter Haven’s renowned Chain of Lakes lifestyle. Whether you’re seeking a seasonal retreat or full-time residence, this home offers comfort, convenience, and classic Florida charm.

6644 Princeton Drive Ne, Winter Haven

$185,000
2 Beds 2 Baths Cypresswood Golf Villas Gi-4 SubDv. 33884 Zip Code
Welcome to this spacious and well-maintained villa in Cypresswood Golf & Country Club, offering comfortable living in one of Winter Haven's established gated golf communities. Please note: The professional photos currently showing blue carpet were taken before the recent flooring update. New flooring has now been installed in the living room, dining room, kitchen, hallway, and Florida room. Inside, you'll find an oversized living area filled with natural light, a functional kitchen with ample cabinet space, generously sized bedrooms, and an enclosed Florida room that provides valuable additional living space. The new flooring gives the main living areas a fresh, updated look while maintaining the home's warm and inviting feel. The home has been lovingly cared for over the years and offers a wonderful opportunity for its next owner to move right in or personalize it to their own style over time. The split-bedroom floor plan provides privacy and flexibility, while covered parking and low-maintenance exterior living make everyday life easy and convenient. Residents of Cypresswood enjoy access to golf, tennis, a clubhouse with restaurant, and beautifully maintained grounds, all just minutes from shopping, dining, medical facilities, and major roadways. If you've been searching for space, value, and a relaxed Florida lifestyle in a gated golf community, this home deserves a spot on your must-see list.

2270 Firestone Place, Winter Haven

$158,000
2 Beds 2 Baths Garden Grove Oaks SubDv. 33884 Zip Code
PRICE ADJUSTMENT JUST MADE! This beautiful home is back on the market due to buyer financing falling through right before closing – no fault of the seller. The good news? The seller has already completed lender-required repairs, so the home is ready for a smooth closing! Welcome to 6315 Grove Pointe Drive SE, a beautifully maintained manufactured home in the highly sought after 55+ community of Garden Grove Oaks where you OWN your Land and enjoy low HOA fees in a peaceful, well-maintained neighborhood. This home features two generously sized bedrooms and two full bathrooms. The primary suite boasts a walk in closet and private en-suite bath with both a garden tub and separate shower. Step into the open-concept living space filled with natural light featuring spacious living and dining areas ideal for entertaining or family gatherings. The kitchen is equipped with updated appliances, reverse osmosis water purification system, ample counter space and plenty of storage. The home had a new membrane roof installed in 2021 with a gutter and roof maintenance yearly contract. Roof was just inspected 10/2025. Vinyl plank flooring throughout, updated appliances and electric drapes. Enjoy community amenities, friendly neighbors and the convenience of being just minutes from local shopping,dining, medical facilities,and Winter Haven's world-famous Chain of Lakes. With access to major highways,commuting to nearby cities like Orlando or Tampa is a breeze. Don't miss the opportunity to make this beautifully maintained home in Garden Grove Oaks your new home! Schedule your private showing today and experience all this property for yourself.

6315 Grove Pointe Drive Se, Winter Haven

$189,900
3 Beds 2 Baths Brookhaven Village First Add SubDv. 33881 Zip Code
Under contract-accepting backup offers. PRICE IMPROVEMENT! Now offered at an even better value, this beautifully maintained home in Brookhaven’s desirable 55+ community is the perfect opportunity to enjoy comfortable Florida living with owned land and low HOA fees. Located on a corner lot on a quiet dead-end street, this 2005 Homes of Merit double-wide manufactured home offers 1,440 sq. ft. of well-designed living space and comes fully furnished and move-in ready. The spacious open floor plan features 3 bedrooms, 2 bathrooms, an indoor laundry room, and abundant natural light throughout. Elegant tray ceilings enhance the main living area, while sliding glass doors lead to an additional porch overlooking a peaceful neighboring pasture—an ideal place to relax and enjoy the view. The large kitchen is designed for both functionality and entertaining, featuring a center island, ample cabinet and counter space, updated microwave, newer refrigerator (2024), and A/C unit (2024). Recent improvements provide added value and peace of mind, including a new shingle roof and carport (2023), updated siding, reinforced tie-downs, fresh interior paint, and new Parkay Endurance water-resistant laminate flooring. A versatile bonus room with French doors offers flexibility for a home office, hobby room, or third bedroom. The guest bedroom and bath are generously sized, while the oversized primary suite includes a private ensuite bathroom for added comfort and privacy. Additional features include an indoor laundry room with washer and dryer included, a spacious workshop/storage area, and valuable extras such as an 8,000-watt generator (gas or propane) with two propane tanks, mower, trimmer, and power washer. Surrounded by mature landscaping, this property offers both charm and tranquility. Brookhaven residents enjoy amenities including a community pool, clubhouse, and shuffleboard, all with a low HOA fee of just $34 monthly. Conveniently located near Hwy 27, shopping, restaurants, and medical facilities, this home is also approximately one hour from Disney and within easy driving distance to both Florida coasts. Don’t miss your opportunity to own this well-maintained, fully furnished home with owned land in one of Central Florida’s welcoming 55+ communities. Schedule your private showing today.

6346 Bayberry Blvd Ne, Winter Haven

$129,900
2 Beds 2 Baths Garden Grove Oaks SubDv. 33884 Zip Code
NEW PRICE REDUCTION!! Very well kept home on your own lot. No lot rent here! Low HOA of only $65 a month. Garden Grove Oaks is a well-kept and managed over 55 park in a great location in SE Winter Haven. Home has 2 bedrooms and 2 full bathrooms. Kitchen and dining area have tons of cabinets and storage for all your dishes and cookware and includes a closet pantry. There is a wet bar in the dining area with a small sink, open shelves and cabinet storage underneath. The opposite side of the dining room has a built-in china cabinet. Main bedroom is a great size with a walk-in closet and small bathroom with tub and tiled shower. Second bedroom has door opening to nice-sized bathroom with large sink and cabinets and a shower/tub combination. Home has a membrane roof that was installed in spring of 2014. York air conditioner is 8-9 years old. Nice large laundry room has Bosch washer and dryer. Back screened porch is always cool! HOA fee includes use of the clubhouse with many activities planned every month. There is a billiard room, card and game room with library and puzzles to check out, large event area, and great kitchen. Huge heated pool and spa for all residents and their guests. There is a screened-in area with a grill for Bar-B-Q's with family and friends. There is also a shuffleboard court. HOA is an award-winning association. Community is close to a Super Walmart and grocery stores as well as shopping and restaurants. Only minutes to Hwy. 27! Winter Haven is famous for its Chain of Lakes! Where else can you find all of this for only $129,900? Please make an appointment to see this great home today!

6033 Grand Oaks Drive Se, Winter Haven

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