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6773 Brentwood Drive Ne, Winter Haven
$139,900
2 Beds ⋅ 2 Baths ⋅ Lake N Golf Estates SubDv. ⋅ 33881 Zip Code
Your new Florida home is waiting for you. This home has many updates and improvements. The shingled roof was installed in December 2024 and the HVAC is 6 years old. A new vapor barrier has been installed. There are new plywood subfloors and luxury vinyl plank in the living room, dining room, hall, and both bathrooms. There is no carpet in this home. The kitchen is perfect for preparing all those special meals. The living room is open and spacious. The front Florida room is perfect for your morning coffee. Lake n Golf Estates, a 55+ community, offers many amenities including a pool, shuffleboard, and clubhouse. Join in the activities or just sit back and enjoy the peaceful community.

6773 Brentwood Drive Ne, Winter Haven
125 Lake Hazel Drive, Winter Haven
$100,000
2 Beds ⋅ 2 Baths ⋅ Orange Manor West Coop Inc SubDv. ⋅ 33884 Zip Code
Under contract-accepting backup offers. NO LOT RENT! Live the retired life you worked so hard for. Whether you are a snowbird or looking to enjoy full-time residency, Orange Manor West welcomes you. This highly sought-after 55+ gated community in Winter Haven, secondary resident(s) must be 40+. This fully furnished 2-bedroom, 2-bath home offers a functional layout with recent updates including a 2018 roof, 2022 HVAC, 2021 water heater, newer vinyl flooring, and updated appliances. The home features a spacious layout with walk-in closets in both bedrooms, a private primary suite with a step-in shower, and an enclosed Florida room that is perfect for relaxing mornings or unwinding in the evening. Enjoy an active, low-maintenance lifestyle with monthly fees that include cable, internet, and trash, in a community that allows only service and emotional support animals. Residents have access to a wide range of amenities including a community pool, clubhouse, billiards, shuffleboard, horseshoes, mini golf, fishing, lake access, and a full calendar of social activities such as bingo, cards, sports tournaments, quilting, and much more. Additional features include onsite management, 24-hour emergency service, extra storage for boats and recreational vehicles, and boat slips. Located in Southeast Winter Haven, you are just minutes from shopping, dining, and everyday conveniences, with Legoland ad Peppa Pig theme parks nearby for visiting guests. This is a great opportunity to enjoy comfort, convenience, and community all in one place.

125 Lake Hazel Drive, Winter Haven
6450 Hollyberry Lane Ne, Winter Haven
$151,000
2 Beds ⋅ 2 Baths ⋅ Brookhaven Village SubDv. ⋅ 33881 Zip Code
Virtually Staged. Short Sale. HUGE $37,000 PRICE DROP! Welcome to 6450 Hollyberry Lane in Brookhaven Village—a highly sought-after 55+ community where you own your land, making this a rare opportunity! This beautifully updated, move-in ready home features new luxury vinyl flooring (2025) and a bright, open layout perfect for everyday living and entertaining. The upgraded kitchen offers butcher block countertops, slide-out metal racks for added storage, and a brand-new dishwasher. Washer and dryer are included. Both bathrooms have been beautifully remodeled with modern finishes. Major updates include a new roof (Dec 2024), new HVAC system (2025) with ductwork and air handler, new windows (2025), and all-new screening, including the lanai with vinyl windows—perfect for enjoying Florida living year-round. The home is also fully replumbed with updated anchors and straps, including a vapor barrier that was installed about 4 years ago. The home also includes a great storage shed/workshop—ideal for hobbies or extra storage. Enjoy a super low HOA with access to a community pool and clubhouse, all in the heart of Winter Haven near shopping, dining, and lakes. Fully updated + land ownership + prime 55+ community—this one stands out. Schedule your showing today!

6450 Hollyberry Lane Ne, Winter Haven
321 Orange Blossom Drive, Winter Haven
$199,950
2 Beds ⋅ 3 Baths ⋅ Waters Edge Unit 01 A Rep SubDv. ⋅ 33880 Zip Code
Whether you're a first-time buyer, downsizing, or investing, this canal-front townhome is an opportunity you don't want to miss. Enjoy access to Winter Haven's Chain of Lakes at a fraction of typical waterfront prices. This home features an open layout with modern finishes, ideal for everyday living and entertaining. A private lanai and second-story balcony overlook the canal, which connects to Lake Lulu, Lake Roy, Lake Eloise, and the 15 interconnected lakes of the Southern Chain of Winter Haven's Famous Chain of Lakes spanning over 9,000 acres of waterways. Or take some time for yourself to relax at the community pool on the banks of Lake Lulu. This townhome is centrally located near shopping, dining, and major roadways, offering convenient access to all things Winter Haven. Schedule your showing today.

321 Orange Blossom Drive, Winter Haven
220 King Road, Winter Haven
$114,900
2 Beds ⋅ 1 Baths ⋅ 33880 Zip Code
***Investor Special*** Welcome to this 2 bedroom 1 bath home. It is in need of some work but not out of range for the right do it your self investor. It is situated on .6 acres of land with room on the back of the lot for a garden, chickens or storage building. This property is located in Winter Haven and is close to everything you need.

220 King Road, Winter Haven
607 Country Lane Ne Unit 607, Winter Haven
$142,500
2 Beds ⋅ 2 Baths ⋅ Country Lake Condo Ph 01 SubDv. ⋅ 33881 Zip Code
R E D U C ED AND WELCOME HOME TO THIS MOVE IN READY LAKEFRONT CONDO. 2BEDROOM - 2 BATH WITH 1252 SQ FT OF LIVING AREA , PLUS A FLORIDA ROOM OVERLOOKING LAKE BUCKEYE. THIS CONDO UNIT HAS STORAGE THROUGHOUT, GREAT STORAGE CLOSET OFF THE FLORIDA ROOM, ALSO INSIDE UTILITY WITH WASHER/DRYER HOOKUPS AND THE PRIMARY BEDROOM HAS A WALK IN CLOSET. YOU HAVE THE PRIVACY OF THIS UPSTAIRS UNIT WITH A BEAUTIFUL VIEW, NEW CARPET & INTERIOR PAINT,. IT ALSO FEATURES CONVENIENT COVERED PARKING AND COMMUNITY POOL & TENNIS. LOCATED NEAR POLK STATE COLLEGE , YOU CAN ENJOY A WALK AROUND NEARBY LAKE ELBERT OR DRIVE JUST MINUTES TO DOWNTOWN WINTER HAVEN FOR SHOPPING, RESTAURANTS AND COMMUNITY EVENTS. DON'T MISS OUT ON THIS LAKEFRONT VIEW OF LAKE BUCKEYE .

607 Country Lane Ne Unit 607, Winter Haven
4918 Rosewood Street, Winter Haven
$125,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code
This home is a MUST SEE? You will find many updates in this home from the beautiful granite counters in the kitchen and new kitchen cabinets to the remodeled bathrooms. All flooring is either ceramic or vinyl flooring. The Singled roof is approximately 11 years old and the ac was installed in 2025. The water heater was installed in 2024. A new refrigerator was installed in Sept 2026. This home will be sold mostly furnished. If that isn't enough, from the carport area there is a beautiful view of the lake and lakeside amenities. Oakwood Estates is a very active 55+ community offering many amenities including two pools, two clubhouses, miniature golf, tennis courts, shuffleboard and more. You can be as busy as you want, or just sit back and enjoy peaceful Florida living. Visit the Oakwood website for more info on the community and to see the governing docs.

4918 Rosewood Street, Winter Haven
121 Bates Avenue Se, Winter Haven
$179,000
2 Beds ⋅ 1 Baths ⋅ Haven Terrace SubDv. ⋅ 33880 Zip Code
Located in the heart of downtown Winter Haven, FL, this versatile R-3 zoned property presents an excellent opportunity for homeowners, investors, or those seeking future development potential! This charming residence features 2 bedrooms and 1 full bathroom, offering a functional layout with comfortable living spaces. The home includes a spacious kitchen with ample cabinetry and room for dining, perfect for everyday living or rental use. A dedicated utility room adds convenience and extra storage space. Connected to city water and sewer, this property provides reliable infrastructure and ease of maintenance. The R-3 zoning allows for a variety of potential uses (buyer to verify with city) making this a flexible investment in a growing and desirable downtown location. Enjoy close proximity to local shops, dining, parks, and all that Winter Haven has to offer, including its renowned chain of lakes! Whether you're looking for a primary residence, rental property, or future development opportunity - this property checks all the boxes!

121 Bates Avenue Se, Winter Haven
28 Casarena Court, Winter Haven
$135,000
2 Beds ⋅ 3 Baths ⋅ Casarena On Lakes SubDv. ⋅ 33881 Zip Code
Under contract-accepting backup offers. Welcome to this charming two-story townhome located in the Casarena gated community in Winter Haven, offering 2 bedrooms and 2.1 bathrooms designed for comfort and flexibility. The inviting main living area features a cozy fireplace, perfect for relaxing or entertaining, while the functional layout flows seamlessly into the dining and kitchen spaces. Upstairs, enjoy your own private second-floor balcony—an ideal spot for morning coffee or unwinding in the evening. Enjoy family gatherings in the large screened in patio that is ready to be converted into your ideal outdoors living space. Additional highlights include a convenient laundry closet in the garage and ample storage throughout. Whether you're a first-time buyer, downsizing, or seeking a low-maintenance lifestyle, this home checks all the boxes—schedule your private showing today and make it yours! This home is being sold in As Is condition. All buyers must view the home before submitting an offer.

28 Casarena Court, Winter Haven
1678 Linz Court, Winter Haven
$245,000
2 Beds ⋅ 2 Baths ⋅ Vienna Square Ph 2c SubDv. ⋅ 33884 Zip Code
BETTER THAN NEW!!! Why wait to build when you can move into this HIGHLY UPGRADED, MAINTENANCE FREE villa in the 55+ GATED COMMUNITY of Vienna Square, centrally located in Winter Haven, FL. Before entering this beautiful residence, you will notice the BRICK PAVERED driveway/walkway leading through the MATURE LANDSCAPE and CUSTOM LIGHTING to the front SCREENED LANAI. Walk right into this very OPEN FLOORPLAN with HIGH CEILINGS and SPLIT BEDROOM CONCEPT. The kitchen is a CHEF'S DREAM, featuring UPGRADED STAINLESS APPLIANCES, IMPRESSIVE WINE FRIG., and BREAKFAST BAR. The CASCADING WATERFALL EDGE QUARTZ COUNTERTOPS add a MODERN, ELEGANT and LUXURIOUS focal point to this AMAZING KITCHEN!!! The adjoining great room is very spacious and overlooks the rear SCREENED LANAI with a view of the pond. The primary en-suite will not disappoint which also features QUARTZ COUNTERTOPS and an UPGRADED WALK-IN SHOWER with GLASS DOOR. CUSTOM PLANTATION SHUTTERS in the kitchen and bedrooms ensure you have the privacy you deserve! Don't forget about the second bathroom that has also been UPGRADED with QUARTZ COUNTERTOPS as well. This residence is truly TURN-KEY and one of the most WELL KEPT, ONE-OWNER homes you'll find anywhere. The reasonable monthly HOA dues include: ROOF REPLACEMENT, EXTERIOR PAINTING, YARD MAINTENANCE, LAWN IRRIGATION, and INTERNET/TV PACKAGE! Enjoy the other amenities including, but not limited to: pool/hot tub, tennis/pickle ball, gym, craft room, billiard room, movie room, and large meeting room with remodeled kitchen area. This wonderful property is in close proximity to medical, restaurants, shopping, worship, and LEGOLAND, FL. Winter Haven is well-known for it's beautifully interconnected lakes and being centrally located between the Tampa International and Orlando International Airports.

1678 Linz Court, Winter Haven
1700 6th Street Nw Unit B23, Winter Haven
$125,000
2 Beds ⋅ 2 Baths ⋅ Winter Haven Harbour Apts Condo SubDv. ⋅ 33881 Zip Code
This beautifully maintained **DELUXE UNIT** is move-in ready and offers everything you’ve been searching for—located in a desirable **55+ community**, perfect for comfortable and peaceful living! What sets this unit apart is its **private in-unit laundry room**, a rare and valuable upgrade compared to other units in the community—adding both convenience and functionality. Enjoy improved energy efficiency with newly installed solar window tint on all windows, along with recently added vertical blinds. The plumbing has been upgraded, providing added peace of mind. Inside, you’ll find a stunning built-in bookcase and shelving system, perfect for organization and style. Relax and take in the views from both the screened front and back porches—ideal for morning coffee or evening unwinding. All appliances are included for your convenience: washer, dryer, refrigerator, dishwasher, stove/range, and microwave. The bathroom has been tastefully updated with a new toilet and vanity. Additional features include one assigned covered parking space under the carport and a private 4x8 storage unit located on the same floor. The condo association fee covers water and garbage, adding even more value to this exceptional home.

1700 6th Street Nw Unit B23, Winter Haven
503 Avenue B Nw Unit 503, Winter Haven
$299,999
2 Beds ⋅ 3 Baths ⋅ Haven Place SubDv. ⋅ 33881 Zip Code
Experience refined living in the heart of Downtown Winter Haven with this architecturally significant residence just moments from the city’s vibrant lakeside lifestyle. Perfectly positioned within walking distance of local restaurants, boutiques, parks, and entertainment, this exceptional residence places you at the center of one of Central Florida’s most charming downtown districts. Residents will also enjoy quick access to LEGOLAND® Florida Resort, the renowned Chain of Lakes, and nearby tennis and recreation facilities. Originally designed by celebrated architect Gene Leedy, a pioneer of the Sarasota School of Architecture, this residence showcases the timeless elegance of Florida modernism. Clean architectural lines, open living spaces, and distinctive exposed concrete elements reflect Leedy’s philosophy of blending structural beauty with functional design. Expansive interiors allow natural light to flow throughout the home, creating a seamless connection between indoor comfort and the surrounding Florida landscape. Inside, the thoughtfully designed floor plan offers 2 spacious bedrooms, 2 full bathrooms, and a convenient half bath, with 1,408 square feet of living space that balances openness with privacy. The residence provides a comfortable setting for professionals, couples, or small families seeking both style and convenience in one of Winter Haven’s most desirable walkable locations. With its architectural pedigree, prime downtown setting, and close proximity to the lakes, recreation, and major attractions, 503 Avenue B NW #503 offers a rare opportunity to enjoy living in the heart of Winter Haven.

503 Avenue B Nw Unit 503, Winter Haven
1502 Buckeye Road Ne Unit 4, Winter Haven
$189,900
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
319 Niblick Circle, Winter Haven
$325,000
2 Beds ⋅ 2 Baths ⋅ Gates Lake Region SubDv. ⋅ 33881 Zip Code
Lovely 2 bedroom and 2 bathroom home located in a private gated community of just over 100 homes in Winter Haven, FL. Situated between Tampa and Orlando with easy access to both international airports. Short distance to theme parks, Legoland, Bok Tower Gardens. New Publix grocery store opening soon is a short drive away. New HVAC installed in 2022. Freshly painted interior and exterior. House overlooks a community park which makes a nice setting for relaxing afternoons and visiting with neighbors. Unique lot shape reveals a beautiful, secluded backyard for gardening and plant enthusiasts. Backyard patio area is a great spot to relax and enjoy quiet evenings.

319 Niblick Circle, Winter Haven
9705 Lake Bess Road Unit 715, Winter Haven
$99,900
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
8304 Waterview Way Unit 8304, Winter Haven
$154,900
2 Beds ⋅ 2 Baths ⋅ Garden Villas Condo Ph 01 SubDv. ⋅ 33884 Zip Code
A Cozy Condo nestled in the back corner of the popular community of Winterset. Forgot your key, no problem, you have a coded keyless entry. Your tour begins entering through your covered screened front porch into a Ground level 2 bed/2bath home with an open floor plan. Beautiful Laminate wood flooring accentuates the space. The conveniently centered kitchen boasts a neutral decor with tile backsplash and a newer Stainless side by side fridge. A Nice size Patio is accessed from Livingroom for Barbecuing or just relaxing, enjoying the Florida weather. The split bedroom design offers added privacy to The Master Bedrm with en suite, spacious Walkin closet, Stackable washer/dryer and private screened in patio area which continues to enhance this space. The master bath has separate tub/shower access. The Nest thermostat allows you to monitor and change settings via a phone app. When you Plan your day trips.... You're Only minutes from Lego Land and convenient to Disney & other Florida amusement parks, Beaches, Shopping, Restaurants & More. Or, stay at home, relax and enjoy amenities of the community with Heated Pool, Spa, Tennis, Shuffleboard, Fishing Pier and Clubhouse! Walk the family pet across the street in the expansive green space. All Furniture negotiable!

8304 Waterview Way Unit 8304, Winter Haven
4239 Cedarwood Street, Winter Haven
$125,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code
Open and spacious living area is the best way to describe this home. The home features two living areas plus the lanai for additional space. The primary bedroom is large offering two built in closets and a spacious bathroom. The guest bedroom has the bath attached, perfect for visiting guests. The kitchen has an updated island perfect for entertaining. The laundry is located inside the home. Move right into this home, perfect for full time living and spacious for entertaining all the visitors you may have. The TPO roof was installed in 2022 and the ac is 10 years old. Oakwood Estates is a 55+ communities with lots of amenities including two clubhouses, two pools, miniature golf, shuffleboard, tennis courts, and much more. There are activities every day. You can join in or just sit back and enjoy the peaceful community.

4239 Cedarwood Street, Winter Haven
3363 Livingston Way, Winter Haven
$235,000
2 Beds ⋅ 2 Baths ⋅ Traditions Phase 1 SubDv. ⋅ 33884 Zip Code
Under contract-accepting backup offers. Beautifully updated cottage-style villa located in a desirable 55+ gated community. This fully remodeled home features ceramic tile flooring throughout, with the exception of the second bedroom. The spacious two-car garage includes a laundry area that can easily be enclosed for additional privacy or functionality. The appliances are approximately four years old and have been gently used. ***Please note that the chandeliers and corner hanging lamps do not convey with the sale.**** Residents of this active retirement community enjoy a wide range of amenities, including fishing, a pool and spa, card room, billiards room, social events, fitness center, cable, internet, front lawn maintenance, irrigation, boat dock access (for an additional fee), and boat slips. Don’t miss this opportunity to own your own piece of Florida paradise!

3363 Livingston Way, Winter Haven
1581 Oakview Circle Se, Winter Haven
$210,000
2 Beds ⋅ 2 Baths ⋅ Oakview SubDv. ⋅ 33880 Zip Code
IMAGINE TRADING COLD WINTERS FOR SUNSHINE, PEACEFUL MORNINGS, AND AN EASIER FLORIDA LIFESTYLE. Welcome to this well-maintained 2-bedroom, 2-bath villa in Oakview, a desirable 55+ community in Winter Haven, where comfort, tranquility, and everyday convenience come together. Start your mornings with coffee on the screened lanai, enjoy the ease of one-level living, and spend less time worrying about exterior upkeep—the HOA covers exterior maintenance and lawn care, helping make homeownership simpler and more predictable. Offering 1,220 square feet, this inviting villa features a NEW ROOF (2024), HVAC (2019), NEW KITCHEN APPLIANCES (2026), spacious walk-in closets, and an attached garage with a screen system. Winter Haven offers the relaxed pace and small-town charm many buyers are searching for, surrounded by beautiful lakes, shopping, dining, medical facilities, and convenient access to Downtown Winter Haven, the Chain of Lakes, Bok Tower Gardens, and Legoland when family comes to visit. Whether you are looking for a seasonal retreat or a comfortable full-time residence, this villa offers an attainable and low-maintenance way to enjoy the Florida lifestyle you have been dreaming about. The sellers are ready for their next chapter and welcome reasonable offers. Schedule your private showing and make this your Florida home this season!

1581 Oakview Circle Se, Winter Haven
194 S Lake Mariam Drive, Winter Haven
$390,000
2 Beds ⋅ 2 Baths ⋅ Valencia Wood Estates First Add SubDv. ⋅ 33884 Zip Code
** $10K PRICE REDUCTION!** Welcome to this beautifully updated home in desirable Southeast Winter Haven, offering space, privacy, and modern upgrades on a generous half-acre lot. Step inside to vaulted ceilings and rich hardwood flooring that create a warm, open feel. The living room features a gas fireplace with mantle detail, adding character and comfort to the main gathering space. The fully renovated kitchen stands out with stainless steel appliances, granite countertops throughout, updated shaker-style cabinetry, and a sleek glass vent hood for a clean, contemporary finish. The layout flows effortlessly into the dining and living areas, making it ideal for both everyday living and entertaining. The enclosed rear patio is fully incorporated into the heated and cooled square footage, providing additional living space in a controlled climate year-round. From here, you overlook the expansive backyard with mature trees and complete privacy — and with no rear neighbors, that view and buffer will never change. The updated bathroom features a spacious walk-in shower with modern tile accents, granite vanity top, and upgraded lighting for a polished, spa-like feel. Outside, the half-acre homesite offers exceptional flexibility. There is ample room for a future pool, garden, or additional structure, along with space for boat or RV parking. A detached shed provides extra storage. The property backs to natural privacy with no rear neighbors ever, creating a peaceful setting that’s hard to find. Located in a one-way-in, one-way-out area of Southeast Winter Haven, the neighborhood offers limited traffic and added privacy while still being conveniently close to everything. With a little effort, this home could easily be converted into a 3-bedroom layout, adding even more value and flexibility for future owners. If you’re looking for updated interiors, privacy, and room to grow — this one checks boxes that most homes simply don’t.

194 S Lake Mariam Drive, Winter Haven
4056 Rolling Oaks Drive, Winter Haven
$114,900
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code
Pack your bags and move right into this fully furnished home. This home has many updates!! Although the bedrooms have updated carpets there is nice wood laminate flooring throughout the main living areas with plywood subfloor. The baths and front porch area have updated tile flooring. The kitchen has newer appliances, a beautiful mosaic backsplash and updated counter tops. All the windows are updated with double pane, thermal, tilt in windows. The updated entry door has blinds between the half glass that you can open for the light or close for privacy. Both bathrooms have updated vanities. Enjoy the updated and modern light fixtures. The HVAC was installed in July 2023. The roof is a roof over adding extra insulation value to the home. Oakwood Estates is an active 55+ communities offering many amenities as well as activities. You can be as busy as you would like or just sit back and enjoy the peacefulness of the community.

4056 Rolling Oaks Drive, Winter Haven
6825 S Lake Henry Drive Ne, Winter Haven
$200,000
2 Beds ⋅ 2 Baths ⋅ Lucerne Park Fruit Assn SubDv. ⋅ 33881 Zip Code
One or more photo(s) has been virtually staged. Enjoy true Florida LAKEFRONT living in this spacious 2-bedroom, 2-bath home offering almost 1800 square feet of heated living space, perfectly positioned on a waterfront lot with your OWN private dock, ideal for relaxing, fishing, or simply taking in the peaceful views of Lake Henry. Inside, the home features a large kitchen with a center island, Stainless Steel appliances including a built-in oven and cooktop, with plenty of cabinet space for storage and functionality. The oversized family room offers some of the most beautiful lake views in the home, creating a bright & welcoming gathering space. French doors lead into the additional Florida room under air and heat, where the panoramic water views continue and provide a perfect year-round retreat. Both bedrooms are generously sized, with the primary suite featuring a large ensuite bathroom complete with a walk-in closet, double sinks, a shower and a garden tub. The guest bathroom has been updated, offering a fresh and modern feel. Additional interior features include an entry foyer, inside laundry room, and ample storage space including a dedicated storage room. Outdoor living is just as impressive, with oversized parking, a carport, a large, screened room, a paved open patio, & an additional storage shed. The combination of covered and open spaces makes it easy to enjoy the Florida lifestyle throughout the year. Major updates include a NEW ROOF IN 2025, updated windows, & updated plumbing for added peace of mind. Additional energy-efficient features include a ROOF-MOUNTED SOLAR WATER HEATING SYSTEM, helping reduce electricity usage and water heating costs. Located in Lake n Golf Estates, a desirable lakefront, LAND-OWNED 55+ no pet community, residents enjoy access to amenities including a pool, spa, clubhouse, shuffleboard, & community boat ramp & dock, with boat slips available subject to availability. Conveniently situated near Hwy 27, medical facilities, shopping, and dining, the community also offers low HOA fees of $550 per year, adding to its overall appeal. Schedule your private showing today!

6825 S Lake Henry Drive Ne, Winter Haven
447 San Jose Drive, Winter Haven
$224,900
2 Beds ⋅ 2 Baths ⋅ Orchid Springs Patio Homes SubDv. ⋅ 33884 Zip Code
With expanded living areas and versatile spaces, this home offers a comfortable and practical Florida lifestyle in a well-established Winter Haven community. New flooring and fresh interior paint provide a clean, neutral foundation ready for its next owner. New water heater and a current 4-point inspection report is attached in MLS. Tucked toward the back of the community and accessed by charming, canopy tree-lined roads, the setting offers a peaceful, neighborhood feel ideal for evening walks or bike rides. The enclosed Florida room adds valuable square footage and serves as a flexible extension of the main living area, perfect for everyday living or casual entertaining. A fully enclosed and roofed former atrium creates a unique bonus space that can be enjoyed year-round, offering additional flexibility for hobbies, relaxation, or storage. The fenced backyard provides a private outdoor retreat and features resident koi fish, adding a tranquil touch. The home is equipped with a whole-house generator, offering dependable peace of mind. Residents also enjoy access to the community clubhouse and amenities. Conveniently located near shopping, dining, medical facilities, and major roadways, this property combines comfort, function, and location within a charming, established neighborhood.

447 San Jose Drive, Winter Haven
6081 Southern Oaks Drive Se, Winter Haven
$169,500
2 Beds ⋅ 2 Baths ⋅ Garden Grove Oaks SubDv. ⋅ 33884 Zip Code
Welcome to 6081 Southern Oaks 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 an extra-large walk in closet and 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 is equipped with updated appliances, ample counter space and plenty of storage. The home has a beautiful Florida room with new windows. A new roof was installed in 2025. Vinyl plank flooring in main living area. Inside laundry room. 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.

6081 Southern Oaks Drive Se, Winter Haven
345 24th Street Nw Unit 25, Winter Haven
$120,000
2 Beds ⋅ 2 Baths ⋅ Imperial Villas SubDv. ⋅ 33880 Zip Code
Under contract-accepting backup offers. Back on the Market! Buyer financing fell through. Enjoy relaxed, low-maintenance Florida living in the desirable 55+ community of Imperial Villas! This charming 2-bedroom, 2-bath residence offers the comfort and privacy of a home without the burden of extensive exterior upkeep. Inside, updated flooring and tastefully renovated bathrooms create a fresh, welcoming atmosphere that is ready for you to move in and enjoy. The open, comfortable layout extends to a peaceful lanai overlooking the heated community pool—an ideal place to sip your morning coffee, read a favorite book, or unwind at the end of the day. Several important improvements provide added comfort and peace of mind, including a resurfaced roof with a 15-year warranty, a tankless water heater, and an updated electrical system. The affordable HOA fee of just $270 per month includes water, high-speed internet, cable, gas, and complete grounds maintenance—leaving you responsible only for electricity. The home also includes two assigned parking spaces, one conveniently located beneath a carport, along with ample visitor parking for family and friends. Located just a short walk from beautiful Lake Howard, Imperial Villas places you close to shopping, restaurants, medical services, and the many activities and events of downtown Winter Haven. Whether you are ready to downsize, searching for a seasonal Florida retreat, or simply want a comfortable home with fewer maintenance responsibilities, this inviting villa offers the easygoing lifestyle you deserve. The property is also eligible for FHA financing (3.5% down payment) because it is considered a single-family home. Move in, relax, and start enjoying the best of Winter Haven living!

345 24th Street Nw Unit 25, Winter Haven
414 Avenue C Avenue Ne, Winter Haven
$214,999
2 Beds ⋅ 2 Baths ⋅ Coker A B Add SubDv. ⋅ 33881 Zip Code
Under contract-accepting backup offers. This 2 BR, 2 BA home is located near Rotary Park and Kiwanis Park, which is on Lake Martha, both public parks. Each park has room for games and family gatherings. Rotary Park has a baseball field with backstop and other outside activity areas. This home is located near schools, the Winter Haven downtown post office, the Winter Haven (Bay Care Hospital) and several doctors offices and medical clinics. The Winter Haven Public Library is also 6+/- blocks to the west of this property. The home has a metal roof which offers a long life and better storm protection than typical asphalt shingles. The windows have been replaced and the central A/C - Heat system has recently been inspected. The home has attic storage, however, a detached storage building, with a high interior ceiling, provides room for lawn equipment or other large items not needed inside the residence. where they are more easily accessed than typical attic space provides. The interior of the home has been extensively renovated with both bathrooms completely remodeled.

414 Avenue C Avenue Ne, Winter Haven
4228 Cedarwood Street, Winter Haven
$118,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code
Under contract-accepting backup offers. Move right into this very well maintained home. This home features some new vinyl flooring and newer windows. The hall bathroom has been upgraded with a new vanity and flooring. The home has had new plumbing installed in 2025 including a new water heater and washing machine. Just pack your bags and move right into this fully furnished home. Oakwood Estates, a 55+ community offers many amenities and activities. You can be as busy and join all the activities or just sit back and enjoy the peaceful community.

4228 Cedarwood Street, Winter Haven
188 Sweet Circle Drive, Winter Haven
$90,500
2 Beds ⋅ 2 Baths ⋅ Orange Manor West Coop Inc SubDv. ⋅ 33884 Zip Code
Become a share holder in this highly sought after 55+ gated community. If you are looking for the perfect retirement home, this one is for you! Located in Orange Manor West, it is one of the most popular 55+ communities in Winter Haven and surrounding area with many amenities. Pool, shuffle board, putt putt, horse shoes, crochet, bingo, lake access and much more. Legoland is around one mile away which is great for visiting family. This is a 1176 Square ft. 2 bedroom 2 bath 1991 mobile home with a front facing enclosed Florida room. The king size master bedroom has a walk-in closet and a private bathroom with step in shower. The monthly maintenance fee is $279.00 a month which includes cable, internet, trash pickup, and amenities. This house is fully furnished and ready to move in. This is also a pet free community. While it is a great winter home get away, it can also be a year round retirement home. Come see it today. This one won't last long. All measurements are approximate and should be verified by the buyer.

188 Sweet Circle Drive, Winter Haven
1700 6th Street Nw Unit C1, Winter Haven
$109,900
2 Beds ⋅ 2 Baths ⋅ Winter Haven Harbour Apts Condo SubDv. ⋅ 33881 Zip Code
Welcome to Winter Haven Harbor condos a 55+ community. This two bedroom one bath condo is an end unit and it is on the first floor, very close to your parking spot. The home has Nice laminate flooring throughout. The Dining room is next to kitchen, a little open concept area. The master bedroom has a nice size walk in closet. The home also boasts new energy efficient windows. The community features a massive heated pool, clubhouse with exercise room, kitchen, pool table, shuffleboard, and a grilling area with a nice area to entertain friends and family. This community also features a car washing area. Public bus transportation-Citrus connection available right out front. Buyer approval required. You are walking distance from shopping, Hospital and other medical centers. Centrally located between Tampa and Orlando. Schedule your appointment to view this home and make it yours today.

1700 6th Street Nw Unit C1, Winter Haven
940 Oleander Drive Se, Winter Haven
$250,000
2 Beds ⋅ 2 Baths ⋅ Cooper Estates SubDv. ⋅ 33880 Zip Code
Auction Property. Ranch-style home offering 2 bedrooms and 1.5 bathrooms with a spacious living room and a good-sized yard. Features include a durable metal roof, RV electrical hookups, and a chicken coop. Some updates in the kitchen. Short Sale subject to lender approval.

940 Oleander Drive Se, Winter Haven

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