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4807 Plumwood Street, Winter Haven
$110,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code
Move right into this furnished home located in Oakwood Estates, a 55+ community. The carpet throughout the home is in excellent condition. The rooms are very spacious and inviting. The home has been very well maintained. The dishwasher was installed in 2018, the washer and dryer 2020, and the refrigerator in 2024. Enjoy the bonus room on the front of the home or sit and watch the world go by on the comfortable lanai. Oakwood Estates offers many activities and amenities. If you are looking for exercise, you can join in with the pool or indoor aerobics. Chair Yoga is offered twice a week, or play some pool volleyball. The tennis court has recently been refinished and there is a pickle ball group that meets three times a week. During the winter months, there are several exciting dances as well as many activities. If food is your thing, Oakwood offers potluck dinners, ice cream socials, and weekly coffee and donuts. If you are looking for full time or just part time, this is your opportunity to move into a wonderful community, conveniently priced.

4807 Plumwood Street, Winter Haven

2820 Traditions Boulevard S, Winter Haven
$309,900
3 Beds ⋅ 2 Baths ⋅ Traditions Ph 01 SubDv. ⋅ 33884 Zip Code
Welcome to 2820 Traditions Blvd S, located in the desirable 55+ gated community of Traditions at Lake Ruby in Winter Haven. This well-maintained Augusta model offers 3 bedrooms, 2 bathrooms, a spacious 2-car garage, and a peaceful pond-front setting. This home is perfect for Florida living! The open and comfortable floor plan provides beautiful pond views from the kitchen, dining area, living room, primary suite, and enclosed patio, allowing you to enjoy the tranquil Florida surroundings throughout the home. The kitchen offers ample cabinetry and workspace, while the spacious living areas create an inviting environment for both everyday living and entertaining. The split bedroom layout provides privacy for owners and guests alike. The enclosed patio is a wonderful space to relax, enjoy your morning coffee, or unwind while taking in the water views. Just outside your door, enjoy all that Traditions at Lake Ruby community provides, including a clubhouse, resort-style amenities, pool, fitness facilities, and recreational opportunities designed for an active adult lifestyle. Conveniently located in Winter Haven with easy access to shopping, dining, medical facilities, golf, and Central Florida attractions. Whether you are looking for a full-time residence or a seasonal retreat, this home offers comfort, convenience, and the opportunity to enjoy the relaxed lifestyle of Traditions at Lake Ruby.

2820 Traditions Boulevard S, Winter Haven

3158 Beauchamp Court, Winter Haven
$484,900
4 Beds ⋅ 3 Baths ⋅ Cypresswood Plantations SubDv. ⋅ 33884 Zip Code
Located on a quiet cut-de-sac in the desirable Plantations part of the guard gated golfing community of Cypresswood Golf & Country Club, this 4BR/3BA beauty w/ more than 2500 sq ft has upgrades galore & is just what you've been looking for! The home has a fantastic open floor plan w/ split bedrooms, volume ceilings, crown molding, double pane windows, plantation shutters, arched entryways, & super stylish hickory scraped wood looking tile throughout! The lovely formal dining room w/ it's arched entrances flows nicely just off the foyer, while another arch entry leads straight ahead into the spacious great room w/ a tray ceiling & French doors leading to the inviting Florida room. The large eat-in-kitchen features beautiful custom maple cabinets w/ pull-outs, new quartz countertops & tile backsplash, a breakfast bar, soft accent lighting over the cabinets & it comes equipped w/ all of the upgraded appliances including a new stainless steel refrigerator, microwave & gas range, as well as a new kitchen sink & faucet! The quaint breakfast nook has a beautiful picture window that provides lots of natural light while you're enjoying the serene backyard views. The primary suite is huge & features a cozy sitting area w/ French doors leading to the Florida rm & there's an ornate barn door entrance leading into the primary bathroom complete w/ a garden tub, nicely tiled step-in shower, double sink vanity w/ quartz countertop & a walk-in closet. The 2nd & 3rd BR's are situated on the other side of the living areas for added privacy & they have a Jack-n-Jill bath between them that has a double sink vanity w/ quartz countertop as well as a tub & shower combo. The 4th BR is located just down the hall from the Primary bedroom making it a nice option for a nursery/small child's room or an office. It would also be a nice guest room w/ the 3rd bathroom conveniently located right beside it w/ quartz countertop & a step-in shower w/ a nice glass enclosure. The large Florida rm has lots of windows overlooking the landscaped back yard & it even has a wet bar complete w/ mini fridge, a wine fridge & of course ...quartz countertops making it the perfect spot for entertaining. Additional features include an inside laundry room, a double car garage, fairly new C/H/A, a whole house gas generator, a water softner/purificiation system, central vac, & there's even a fire pit in the back yard on this 1/3+ acre property tucked away in Cypresswood Golf & Country Club, with lots of community amenities including a 24 hour manned gated entrance, a community pool for you to enjoy & not have to maintain, plus there's pickleball courts, tennis courts, a large clubhouse w/ fitness center, restaurant, pro shop & surrounded by the lovely golf course! Close to shopping, restaurants, medical, the new Publix, Legoland & more & Conveniently located in the heart of Central Florida between Orlando & Tamps and not far from all of the major attractions. All measurements are approximate and all info should be confirmed by buyers.

3158 Beauchamp Court, Winter Haven

4 Enclave Drive, Winter Haven
$240,000
3 Beds ⋅ 2 Baths ⋅ Cypresswood Enclave Ph 01 SubDv. ⋅ 33884 Zip Code
THIS HOUSE QUALIFIES FOR $0 DOWN!!! Welcome to 4 Enclaves Dr., Winter Haven, FL—an exceptional opportunity to own a beautifully maintained home in one of Winter Haven's desirable gated golf course communities. Perfectly situated on a corner lot at the end of a quiet cul-de-sac, this immaculate residence offers privacy with a private entrance, curb appeal, and a peaceful setting. HOA covers all outside maintenance, including the roof. From the moment you arrive, you'll appreciate the home's pristine condition and inviting exterior, complete with a 2-car garage and spacious yard. Inside, the home has been meticulously cared for, making it truly move-in ready. Unwind year-round on the screened-in porch, the perfect place to enjoy your morning coffee, entertain guests, or relax while taking in the Florida breeze. Beyond the home, you'll enjoy the lifestyle that makes Winter Haven so desirable. The community offers the security and exclusivity of gated living along with the beauty of a golf course setting. Just minutes away, you'll find LEGOLAND® Florida Resort, the charming shops and restaurants of Downtown Winter Haven, the area's famous Chain of Lakes for boating, fishing, and waterfront recreation, as well as nearby Bok Tower Gardens and an easy drive to both Orlando and Tampa for world-class entertainment, shopping, and airports. Strategically located by US27. If you've been searching for a home that combines an outstanding location, immaculate condition, and an exceptional Florida lifestyle, 4 Enclaves Dr. is ready to welcome you home. Schedule your private showing today!

4 Enclave Drive, Winter Haven

315 Lanceolate Drive, Winter Haven
$469,000
3 Beds ⋅ 2 Baths ⋅ Village/Spirit Lake Ph 01 SubDv. ⋅ 33880 Zip Code
Homes in The Village at Spirit Lake don’t come up for sale very often, and this one has a lot to offer. 315 Lanceolate Drive is a 3-bedroom, 2-bath pool home with two additional air-conditioned rooms in the converted garage, giving you plenty of flexibility for additional bedrooms, home offices, a gym, playroom, or extra storage. Inside, the home has been thoughtfully updated with a completely renovated kitchen, remodeled bathrooms, and comfortable living spaces that feel fresh and move-in ready. The second bathroom offers direct access to the pool area, making it especially convenient for everyday Florida living. Out back, you’ll find a screened lanai overlooking the saltwater pool and a fully fenced backyard with plenty of room to relax, entertain, or enjoy the sunshine. If you have a boat, this home makes that easy too. The extended driveway provides room for boat parking, and residents have access to the community’s private boat ramp on Spirit Lake. The gated Village at Spirit Lake also offers a clubhouse, new playground, pickleball courts, and basketball court, all with a reasonable HOA. Located in unincorporated Polk County with county taxes only, the home is just minutes from the Polk Parkway with convenient access to Winter Haven, Lakeland, shopping, dining, schools, and LEGOLAND Florida Resort. Saltwater pool, room for the boat, access to the lake, and a home that’s already been beautifully updated. There’s a reason homes in this neighborhood don’t change hands very often.

315 Lanceolate Drive, Winter Haven

1776 6th Street Nw Unit 807, Winter Haven
$162,000
2 Beds ⋅ 2 Baths ⋅ Lakeridge Condo SubDv. ⋅ 33881 Zip Code
NEW LISTING IN CENTRAL FLORIDA. CONDO IN 55+ Gated Community. This condominium provides 1.347 SF of living area 2 bedrooms, 2 baths, Bonus room with views of Spring Lake & is located in the beautiful City of Winter Haven. Lakeridge Condominiums offers a maintenance free lifestyle with heated pool, tennis, shuffleboard, community room, gated secured entrances and covered assigned parking space. Water, sewer, cable, internet, trash removal and use of recreational facilities are included in the monthly fee. This well appointed move in ready condo has a large bright kitchen with lots of cabinets, great counter space, appliances and pantry closet. The kitchen overlooks the great room that also adjoins the additional bonus area and storage closet. The primary bedroom has a walk in closet & bathroom with a walk in shower. Beautiful views of Spring Lake can be enjoyed from the Primary bedroom & living areas. Washer/Dryer are included. Convenient to shopping, groceries & restaurants. Extra assigned storage bin on same floor. Lakeridge Condominiums is an age restricted, well maintained & well managed community.

1776 6th Street Nw Unit 807, Winter Haven

41 Greenfield Court, Winter Haven
$350,000
3 Beds ⋅ 2 Baths ⋅ Cypresswood SubDv. ⋅ 33884 Zip Code
Premier Location overlooking the pond and the golf course. This traditional 3 bedroom 2 bath estate home offers split bedrooms, formal living and dining areas, large family room, master suite with dual vanities and dual closets, oversized garage with a shower and a screen enclosed pool. From the pool deck, enjoy watching the varied species of birds that pass by or land for a stroll/swim in the back yard or pond. Cranes, Herons, Ibis, Ducks, etc. Recent updates include a roof, windows, water treatment system, AC including ducts and insulation, kitchen sink, disposal, bathroom faucets and toilet, rebuilt pool pump and filter system, driveaway resurfacing and garage floor embellishment as well as solar panels.

41 Greenfield Court, Winter Haven

1 Enclave Drive, Winter Haven
$220,000
3 Beds ⋅ 2 Baths ⋅ Cypresswood Enclave Ph 01 SubDv. ⋅ 33884 Zip Code
Opportunity Knocks! Build sweat equity in this 3 bedroom 2 bathroom villa that is ready for some cosmetic updates. Make this home your own with fresh paint, new flooring and anything else you might desire. The unit is currently in habitable condition so you can live there and work at your own pace. Priced well below market value to allow room for cosmetic upgrades. The country club amenities include access to the clubhouse with bar and grill, jr. Olympic swimming pool and brand new tennis and pickleball courts. The championship 18 hole golf course is open to the public. As an added bonus, Publix just opened a brand new location just a mile down the road which is sure to attract other popular businesses.

1 Enclave Drive, Winter Haven

6235 Knotty Pine Drive Se, Winter Haven
$155,000
2 Beds ⋅ 2 Baths ⋅ Garden Grove Oaks SubDv. ⋅ 33884 Zip Code
CUTE AND COZY 2 BR/2 BA HOME IN GARDEN GROVE OAKS 55+ COMMUNITY! This one-owner home is in one of Winter Haven's most sought-after 55+ communities where you own your land, and the HOA is low at $65/month. You will not be bored living here...activities include dances, birthday and anniversary celebrations, water aerobics, card games, shuffleboard, billiards and more. The community has its own clubhouse, pool and spa, and optional secured RV/boat parking. You will find 6235 Knotty Pine Dr on a quiet cul-de-sac with little traffic.  The bright, open, and spacious floor plan features 1080 sq ft of living area, plus a Florida room, perfect for your morning coffee, relaxing and entertaining.  Inside laundry room located in the hall bathroom. Notable upgrades include NEW ROOF in 2023, NEW A/C in 2025, and a FULL HOUSE GENERATOR. With some cosmetic updates, you can add your final touches to make this home yours!  This home has been professionally cleaned and pressure washed in August 2026. The community is clean, and pride of ownership is displayed throughout. Florida living at a price you can afford with no lot rent. Conveniently located just a few minutes from Hwy 27, shopping, medical facilities, and restaurants.Schedule your private viewing today!

6235 Knotty Pine Drive Se, Winter Haven

1814 Sandhill Lane, Winter Haven
$462,000
4 Beds ⋅ 3 Baths ⋅ Cypresswood SubDv. ⋅ 33884 Zip Code
Here is your opportunity to own an immaculate home in the sought after community of Cypresswood Golf and Country Club. Consistently voted the Number 1 Golf Course in the area. This vibrant community has it all. Aside from the fantastic course right out your door, enjoy everything else it has to offer. A wonderful restaurant and Club House where they host live music 3 nights a week and top notch food offerings. An Olympic size pool that was just recently redone along with newly redone tennis courts and pickle ball courts. There is even a fitness center. Take a drive in your golf cart in the evenings and enjoy the natural elements and animals that Central Florida is famous for. Bald Eagles, wild turkey, Sand Cranes are just some of the sights you are likely to see on your ride. Then, come home to your beautifully maintained home that allows for easy entertaining, or peaceful times out on the back screened in patio where you can watch golfers and animals alike. The combination kitchen and family room is second to none. Stainless steel appliances including a new dishwasher for the experienced chef or novice. You can't help enjoying cooking in this home. Second bedroom with it's own ensuite full bath, and two other bedrooms that share a Jack and Jill full bath. You will find storage gallore everywhere you look. Peaceful yard offers privacy and views for days. Come and tour this home today, and you will know that you have found The One!

1814 Sandhill Lane, Winter Haven

1061 Sawgrass Drive, Winter Haven
$449,900
3 Beds ⋅ 2 Baths ⋅ Lake Ashton West Ph 2 South SubDv. ⋅ 33884 Zip Code
WELCOME to the lifestyle you've been dreaming of in the premier 55+ community of Lake Ashton! This Stunning Designer residence offers the perfect blend of elegance, comfort, and resort-style living with 3 spacious bedrooms, 2 beautifully appointed baths, plus a private den/office in a desirable split-bedroom floor plan. The heart of the home is the spectacular open-concept kitchen, featuring upgraded all-wood raised-panel cabinetry, gleaming granite countertops, stainless steel appliances, abundant storage, and a large breakfast bar overlooking the expansive living and dining areas. Gorgeous tile flooring flows throughout the main living spaces, while plush carpeting adds warmth and comfort to the bedrooms. Natural light fills every room through an abundance of windows, creating a bright and inviting atmosphere. Step through the sliding glass doors onto the screened veranda, where you can relax with your morning coffee or evening cocktail while enjoying peaceful pond views and Florida's beautiful sunsets. The luxurious owner's suite is a private retreat featuring an incredible spa-inspired bath with dual granite vanities, upgraded wood cabinetry, and a spectacular walk-through fully tiled shower designed for both beauty and convenience. Enjoy the pocket doors throughout the house. This house has so many Designer Upgrades, its difficult to list all of them. Life at Lake Ashton is second to none, offering two private golf courses, three pristine natural lakes, two magnificent clubhouses, indoor and outdoor resort-style swimming pools (including a relaxing hot tub), two state-of-the-art fitness centers, racquetball, basketball, tennis, pickleball, scenic walking trails winding throughout the golf course, and the convenience of a golf cart-friendly community. Enjoy dining at the restaurant overlooking the golf course, meet friends for endless social activities and entertainment, and experience the vibrant, active lifestyle you've always imagined. This home has solar panels that will save on your electric bills for years to come. Don't miss this exceptional opportunity to own one of Lake Ashton's most BEAUTIFUL DESIGNER HOMES. Schedule your private showing today and be the first to call this extraordinary residence HOME!

1061 Sawgrass Drive, Winter Haven

3614 Plymouth Drive, Winter Haven
$310,000
3 Beds ⋅ 2 Baths ⋅ Traditions Ph 01 SubDv. ⋅ 33884 Zip Code
Perfectly situated on a premium pond-front homesite in the sought-after 55+ gated community of Traditions at Lake Ruby, this beautifully maintained residence offers the ideal blend of comfort, space, and carefree Florida living. With 3 bedrooms, 2 bathrooms, and 2,109 square feet of thoughtfully designed living space, the open split-bedroom floor plan is perfect for both everyday living and entertaining. From the moment you arrive, the paver driveway, carriage-style lighting, manicured landscaping, and covered entry create impressive curb appeal. Inside, soaring ceilings and solid-surface flooring enhance the bright, open feel of the home. The spacious kitchen overlooks the family room and features 42-inch maple cabinetry with decorative rain-glass accents, Corian countertops, a breakfast bar, closet pantry, and a charming dining nook. Designed for gathering, the expansive family room is framed by triple sliding glass doors that showcase tranquil pond views and seamlessly connect to the oversized Florida room. Whether you're hosting friends or enjoying a quiet morning coffee, this inviting space provides the perfect backdrop, complete with views of the soothing waterfront fountain. The generously sized primary suite is a true retreat, offering its own waterfront sitting area, direct access to the Florida room, dual walk-in closets, and a spacious en-suite bath featuring a comfort-height double vanity, garden tub, seated walk-in shower, linen closet, and private water closet. Two additional bedrooms provide flexibility for guests, hobbies, or a home office, while the interior utility room includes a washer, dryer, and utility sink for added convenience. Additional highlights include a 2021 roof, 2024 HVAC system, 2018 water heater, gutters, security system, and a two-car garage with an additional refrigerator. Life at Traditions at Lake Ruby feels like a year-round vacation. Residents enjoy an impressive collection of resort-style amenities, including a lakefront clubhouse, heated pool and spa, fitness center, ballroom, library, billiards room, craft and meeting rooms, tennis courts, pickleball courts, bocce ball, basketball, shuffleboard, dog park, private dock, boat ramp, and a full calendar of social activities. The HOA provides exceptional value with lawn maintenance, exterior house painting, cable, internet, and full access to community amenities included. Conveniently located near shopping, dining, medical facilities, major highways, and LEGOLAND, this waterfront gem offers the perfect opportunity to enjoy an active, low-maintenance lifestyle in one of Central Florida’s most desirable 55+ communities.

3614 Plymouth Drive, Winter Haven

4146 Sprucewood Street, Winter Haven
$140,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code
You won't want to miss this opportunity. This 1344 sf home located in Oakwood Estates, a 55+ community. From the carport walk into the lanai, perfect for entertaining. From there step through the French doors into the open and inviting home with an open and updated kitchen with newer appliances including a cooktop, built in double ovens, built in microwave, and nice sized refrigerator. Past the kitchen you will see the comfortable dining area with built in cabinetry. Then follow through to the spacious living room with more built in cabinets. Returning back through the kitchen you will find the family room area which is open to the kitchen, just perfect for those family and friends get togethers. The main bathroom has been updated with a beautiful shower and updated stool. The guest bedroom is attached to this bath. At the back of the home you will find the primary bedroom complete with two built in closets and a nice sized bathroom attached. The shingled room was installed in 2025 and the air conditioner and water heater were installed in 2021. Oakwood Estates offers many amenities as well as activities. You can join in on the activities or just sit back and watch the world go by.

4146 Sprucewood Street, Winter Haven

664 Clubhouse Road, Winter Haven
$229,000
2 Beds ⋅ 2 Baths ⋅ Cypresswood Villas/Green Bldg SubDv. ⋅ 33884 Zip Code
Situated in the desirable golfing community of Cypresswood Golf & Country Club, this lovely 2-bedroom, 2-bath townhome offers comfort, style, and beautiful golf course views. Upon arrival, you'll be welcomed by a charming courtyard adorned with pavers, creating a warm and inviting entrance. A glass storm door and smart lock entry provide both convenience and security. Inside, luxury vinyl plank flooring flows throughout the main living areas, enhancing the home's modern appeal and ease of maintenance. The open-concept floor plan features an updated kitchen with maple wood cabinetry embellished with brushed nickel hardware and soft-close hinges. Corian countertops beautifully complement the tile backsplash, while the custom center island serves as the heart of the home. Additional features include a stainless steel appliance package, recessed lighting, and a closet pantry for ample storage. The adjacent dining area is filled with natural light from an overhead solar tube skylight, creating a bright and cheerful space for meals and gatherings. The spacious living room features a convenient dry bar and oversized sliding glass doors that showcase peaceful views of the golf course. The primary bedroom suite serves as a relaxing retreat, offering dual closets and sliding glass doors leading to the Florida Room. The remodeled en-suite bathroom features a comfort-height vanity with Corian countertops, bronze fixtures, and a walk-in shower with a frameless glass enclosure and safety grab bars. The guest bedroom includes luxury vinyl plank flooring, a custom closet organizer system, and views of the private courtyard. The spacious Florida Room provides the perfect place to relax and unwind while enjoying tranquil golf course views through two oversized sliding glass doors. Additional Features: Laundry room with washer and dryer, Comfort-height toilets, Exterior lighting, Metal roof, Gutters with gutter guards. Conveniently located within walking distance of the community clubhouse, restaurant, pub, swimming pool, and tennis courts, this property offers exceptional accessibility to Cypresswood's amenities. The monthly HOA fee of $320 includes: Exterior painting Roof maintenance Lawn care Additional memberships are available for golf and fitness center access. The picturesque Cypresswood Golf & Country Club features beautifully maintained grounds, a 24-hour manned gated entrance, and a welcoming lifestyle centered around golf, recreation, and community living. This home can be offered turnkey and fully furnished the choice is up to you.

664 Clubhouse Road, Winter Haven

105 Laurel Cove Way Unit 105, Winter Haven
$199,000
2 Beds ⋅ 2 Baths ⋅ Winterset 01 A Condo 02 Amd SubDv. ⋅ 33884 Zip Code
Beautiful lake-view condo in Winterset! This ground-floor 2-bedroom, 2-bath residence offers amazing views of Lake Winterset, part of the renowned Winter Haven Chain of Lakes. The spacious great room features tile flooring, sliding glass doors to the screened porch, and stunning lakefront vistas. Just off the kitchen is a comfortable dining area, creating an inviting space for everyday living and entertaining. The kitchen is beautifully appointed with custom Kraft Maid wood cabinetry, granite countertops, a breakfast bar, and a complete appliance package. The primary bedroom enjoys peaceful lake views and includes plush carpeting with a gel pad, a large 11' X 7' walk-in closet, a ceiling fan, sliding doors to the patio, and an en-suite bath featuring dual sinks, quartz countertops, and an oversized walk-in shower with a seamless glass door. The guest bedroom is generously sized at 13' x 10', offering ample closet space and convenient access to the guest bathroom, which features quartz countertops and tile flooring. The screened porch is the perfect place to relax and enjoy breathtaking lakefront views and spectacular sunsets. Residents enjoy true resort-style living with access to a community clubhouse, pool, spa, shuffleboard courts, tennis & Pickleball courts. The highly desirable location offers close proximity to shopping, dining, schools, medical facilities, and LEGOLAND Florida Resort. Additional features include a private storage room off the patio, inside laundry, a tile roof, air conditioning, 24-hour security, meticulously maintained grounds, assigned parking, and ample guest parking. This is Florida lakefront living at its finest.

105 Laurel Cove Way Unit 105, Winter Haven

4158 Rolling Oaks Drive, Winter Haven
$124,900
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code
Walk right in to this fully furnished home located in Oakwood Estates, a 55+ community. The kitchen is laid out perfect for entertaining and contains a large pantry for storage. The living area is open and spacious with cathedral ceilings to make it feel even more open. The area currently used for a dining area could also be used as a family room or second living area. The primary bedroom can easily accommodate a king sized bed. The walk in closet offers plenty of space for all your clothes. The air conditioner is approximately 4 years old and the roof over offers extra insulation value to the home. Oakwood Estates offers many activities and amenities to keep you as busy as you would like, or just sit back and enjoy the peaceful community.

4158 Rolling Oaks Drive, Winter Haven

4132 Sprucewood Street, Winter Haven
$129,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code
Location! Location! Location! This beautiful fully furnished home in Oakwood Estates is located next to the pool, tennis courts, and smaller clubhouse. Walk into the lanai as you enter the home. Once inside the home you will find a cozy family room and an open and and appealing kitchen just perfect for entertaining. The living room beyond the kitchen is open and spacious. The refrigerator was new in 2025. The guest bedroom opens onto the guest bath giving your overnight guest their own bathroom. The primary bedroom is large enough for a king sized bed, plus lots of closet storage space. The laundry with new washer and dryer is located inside the home. The roof was done in 2019 and the air conditioner in 2024. And if that isn't enough, there is new carpet throughout the home. Oakwood Estates is a 55+ community offering many activities and amenities. You can stay as busy as you would like, or just sit back and watch the world go by.

4132 Sprucewood Street, Winter Haven

419 Greenfield Road, Winter Haven
$334,990
3 Beds ⋅ 2 Baths ⋅ Cypresswood Mdws SubDv. ⋅ 33884 Zip Code
Cypresswood Golf & Country Club welcomes you to 419 Greenfield Drive. This desirable gated golf community has a host of activities and treasures, but by far the most impressive one is this gem and it shows. As you pull up to the extended driveway, low maintenance landscape ushers you into a well appointed home. Once in the front door, sparkling floor tiles guide you through this beautiful 3 bedroom 2 bath split floor plan home. Quartz counters and wall to wall cabinet space give anyone that loves to cook the space they need to store items and create meals while hosting family or company. Right off of the kitchen there is a climate controlled Florida room, with an additional screened-in patio to the rear. When you are ready to retire for the evening, your primary bedroom has plenty of space to stretch out in and keep your belongings in the large walk-in closet. Move right in and leave your worries behind. Not only has the kitchen and flooring been recently upgraded, all your major components have been replaced within the last 5 years - brand new electric panel w/surge protection installed (May 2026), roof (2022) , water heater (2021), A/C (2021). Schedule your private tour and make this home yours for years to come.

419 Greenfield Road, Winter Haven

5312 Nicklaus Drive, Winter Haven
$334,900
3 Beds ⋅ 2 Baths ⋅ Lake Ashton West Ph 01 SubDv. ⋅ 33884 Zip Code
Welcome to resort-style living in the highly sought-after Lake Ashton Golf Club Community! This impeccably maintained home is nestled on a quiet and secluded street, offering the perfect combination of privacy, comfort, and an active Florida lifestyle. From the moment you arrive, you will appreciate the pride of ownership and pristine condition of this beautiful residence. Designed for both everyday living and entertaining, the home offers spacious living areas, abundant natural light, and a floor plan that flows effortlessly throughout. One of the most valuable features of this property is that the CDD bond has been fully paid off, providing significant long-term savings and added value for the new owner. Lake Ashton is one of Central Florida's premier gated 55+ communities, offering an unmatched array of amenities and activities. Residents enjoy access to two private 18-hole championship golf courses, including one of the most challenging and highly regarded courses in the region, making it a favorite among golf enthusiasts. The community also features two expansive clubhouses, a state-of-the-art health and fitness center, resort-style pools, tennis and pickleball courts, bowling lanes, movie theater, ballroom, restaurant and lounge, arts and crafts facilities, numerous social clubs, and a private marina with access to beautiful Lake Ashton. Whether you are looking for an active retirement, a seasonal retreat, or your forever home, this exceptional property offers the perfect opportunity to enjoy the Florida lifestyle at its finest. Schedule your private showing today and discover why so many residents proudly call Lake Ashton home.

5312 Nicklaus Drive, Winter Haven

4130 Bedford Avenue, Winter Haven
$309,900
2 Beds ⋅ 2 Baths ⋅ Traditions Ph 01 SubDv. ⋅ 33884 Zip Code
WELCOME TO CAREFREE LIVING WITH THIS WELL-MAINTAINED RESIDENCE WITHIN THE DESIRABLE 55+ GATED, LAKEFRONT COMMUNITY AT "TRADITIONS OF RUBY LAKE". This home is MOVE IN READY and is situated withing very close proximity to the clubhouse and Lake Ruby!!! NEW ROOF and NEW HOT WATER HEATER both installed in 2023. With nearly (1,820 Sqft.) of heated and cooled space, this OPEN-CONCEPT SPLIT PLAN with SOARING CEILINGS will not disappoint. There is plenty of room for the chef in the family with your OVERSIZED KITCHEN that has an ABUNDANCE of cabinetry and GRANITE COUNTERTOPS! The kitchen also has 2 windows, giving you a pleasant view along with plenty of extra natural light. Just off the kitchen sits the great room leading into 2 bedrooms and another room (11 x 10) that would be perfect for an office, craft room, or out of town guests. You'll love the (21 x 9) BONUS ROOM that has its own AC and gives you so much extra cooled living space. As if this wasn't enough, the bonus room also overlooks a (21 x 9) SCREENED, PAVERED PATIO for outside grilling or just relaxing. The large primary en-suite has a WALK-IN-SHOWER WITH BUILT-IN BENCH and GLASS SLIDERS, DUAL SINKS, and OVERSIZED WALK-IN-CLOSET. You have direct access to the bonus room from the primary bedroom. Cleaning is a breeze in this home featuring NO CARPET!!! The clubhouse is beautiful and boasts amazing views beyond the pool of 2 lakes (Ruby and Bess). The clubhouse also features an oversized pool and spa, dock, boat ramp, boat slips, tennis courts, pickle ball, basketball, shuffleboard, ball room, billiards, library, craft room, fitness center, dog park and much more! Golf carts are allowed in the community for ease of navigating. Traditions is centrally located in close proximity to medical, shopping, restaurants, 2 major international airports (Tampa/Orlando) and the up and coming airline Avelo in Lakeland, FL. LEGOLAND, FL is just minutes away!

4130 Bedford Avenue, Winter Haven

75 Sunset View Drive Unit 75, Winter Haven
$405,000
2 Beds ⋅ 2 Baths ⋅ Winterset 04 A Condo Ph 01 SubDv. ⋅ 33884 Zip Code
Beautiful lakefront living awaits in the gated community of Winterset! This beautifully maintained 2-bedroom, 2-bathroom condo with an attached one-car garage offers stunning lake views, abundant natural light, and unique architectural details throughout. Inside, you’ll find beautiful cork flooring, specialty tray ceilings, and a cozy library area complete with custom built-in shelving. The spacious enclosed Florida room is a true showstopper, featuring floor-to-ceiling windows overlooking the lake, creating the perfect space to relax and enjoy breathtaking water views year-round. The oversized primary suite offers a spacious layout with dual sinks, a walk-in closet, and a peaceful retreat-like feel. The large custom kitchen is a chef’s dream, complete with a gas stove, ample cabinetry, generous counter space, and plenty of storage for all your culinary needs. Enjoy the beautiful community amenities that include a pool, tennis courts, and the security and privacy of this sought-after gated neighborhood. Conveniently located near Legoland, shopping, dining, and everyday conveniences. This lakefront condo perfectly blends comfort, elegance, and Florida lifestyle living.

75 Sunset View Drive Unit 75, Winter Haven

702 Country Lane Ne Unit 702, Winter Haven
$169,500
2 Beds ⋅ 2 Baths ⋅ Country Lake Condo Ph 01 SubDv. ⋅ 33881 Zip Code
LAKEFRONT LIVING AT IT'S BEST! REFRESHED FIRST FLOOR 2BR-2BA CONDO WITH COVERED PARKING AND BEAUTIFUL VIEWS OF LAKE BUCKEYE. THE FEATURES INCLUDE FRESH INTERIOR PAINT, LUXURY VINYL PLANK FLOORING THROUGHOUT WITH CERAMIC TILE IN THE BATHROOMS, KITCHEN AND FLORIDA ROOM, STAINLESS REFRIGERATOR AND MICROWAVE IN THIS CONVENIENT KITCHEN WITH PANTRY AND PASS THRU EATING COUNTER. THIS OPEN GREAT ROOM DESIGN HAS LIVING AND DINING COMBO. RELAX IN YOUR FLORIDA ROOM OVERLOOKING THE LAKE AND ENJOYING THE SUNRISE WITH YOUR MORNING COFFEE. COMMUNITY OFFERS POOL AND TENNIS COURTS. CONVENIENT LOCATION , WALK TO POLK STATE COLLEGE OR ENJOY THE WALKING TRAIL AROUND LAKE ELBERT ONLY MINUTES AWAY WITH NEARBY DOWNTOWN SHOPPING AND RESTAURANTS.

702 Country Lane Ne Unit 702, Winter Haven

10 Enclave Drive, Winter Haven
$214,900
2 Beds ⋅ 2 Baths ⋅ Cypresswood Enclave Ph 01 SubDv. ⋅ 33884 Zip Code
WELCOME TO THIS CHARMING TOWNHOUSE located in the sought-after Cypresswood Golf & Country Club community in beautiful Winter Haven! This inviting 2 BD / 2 BA home offers comfortable Florida living with a spacious open-concept living and dining room combination, abundant natural light, and a thoughtfully designed layout perfect for both relaxing and entertaining. The kitchen features beautiful granite countertops, handsome cabinetry, and a cozy eat-in space ideal for casual dining. The primary suite is generously sized and includes a custom walk-in closet, dual sink vanity, skylight, and an attractive walk-in shower creating a bright and airy retreat. The guest bedroom also offers a custom closet for added organization and convenience. Additional features include skylights that fill the home with natural light, spacious living areas, and a warm, welcoming atmosphere throughout. Residents of Cypresswood enjoy a gated golf course community with beautifully maintained grounds, scenic surroundings, clubhouse amenities, tennis courts, community pool, restaurant access, and an 18-hole championship golf course, all conveniently located near shopping, dining, medical facilities, and easy access to both Orlando and Tampa. Come experience the peaceful lifestyle and exceptional community setting this lovely townhouse has to offer!

10 Enclave Drive, Winter Haven

1004 Medinah Drive, Winter Haven
$165,000
2 Beds ⋅ 2 Baths ⋅ Cypresswood Tennis Vls SubDv. ⋅ 33884 Zip Code
Don’t miss this incredible opportunity to own a villa in one of Winter Haven’s most sought-after gated golf communities — at an unbeatable price! This 2-bedroom, 2-bathroom villa offers 1,278 sq ft of comfortable Florida living with a peaceful pond view backdrop. The open floor plan flows effortlessly, and the private enclosed Florida room is perfect for year-round entertaining. The generous primary suite features a walk-in shower, and the guest bath includes a tub/shower combo. Why this is a steal: Priced well below comparable properties in the community, Resort-style amenities INCLUDED — 18-hole golf course, tennis, pickleball, pool, fitness center, clubhouse & restaurant, 24-hour manned gate for peace of mind, Pets welcome, Flexible for investors — 6-month minimum lease allowed. Whether you’re looking for your Florida dream home, a seasonal getaway, or a smart rental investment, this property checks every box at a price that won’t last long. Act fast — opportunities like this don’t stay on the market!

1004 Medinah Drive, Winter Haven

3023 Caneel Street, Winter Haven
$235,000
2 Beds ⋅ 2 Baths ⋅ Traditions Ph 2a SubDv. ⋅ 33884 Zip Code
Welcome to the vibrant lifestyle of Traditions, one of Winter Haven’s most desirable gated 55+ communities! Built in 2020, this impeccably maintained villa offers 2 bedrooms, 2 bathrooms, and 1,385 sq. ft. of beautifully designed living space that perfectly blends comfort, elegance, and low-maintenance Florida living. Step inside to an inviting open-concept floor plan filled with natural light, high ceilings, and stylish ceramic tile flooring throughout the main living areas. The spacious living and dining areas are ideal for entertaining guests or simply relaxing in comfort. The modern kitchen is a standout feature, showcasing solid wood cabinetry, granite countertops, stainless steel appliances, and generous prep space for everyday living and special gatherings alike. The spacious primary suite offers a large walk-in closet and a private en-suite bath designed for comfort and convenience. Sliding glass doors lead to a screened-in porch where you can unwind and enjoy Florida’s beautiful weather year-round. Living in Traditions means enjoying an exceptional array of resort-style amenities, including a lakeside heated pool, elegant clubhouse, fitness center, tennis, pickleball, and shuffleboard courts, plus private access to Lake Ruby with a community boat ramp and dock. Even better, the HOA covers exterior maintenance, lawn care, and high-speed internet, allowing you to truly enjoy a carefree lifestyle. Ideally located near shopping, dining, hospitals, and Legoland, this stunning villa offers the perfect opportunity to enjoy the best of Central Florida living. Don’t miss your chance to own a beautiful home in one of Winter Haven’s premier active adult communities!

3023 Caneel Street, Winter Haven

1108 Sawgrass Drive, Winter Haven
$422,999
2 Beds ⋅ 2 Baths ⋅ Lake Ashton West Ph Ii South SubDv. ⋅ 33884 Zip Code
This is a must see charming oasis located behind the secure gates of Lake Ashton, you don’t want to miss this opportunity of becoming an homeowner in this Exclusive 55+ community in Florida, comes with a upgraded custom13’6 x 28’ saltwater pool with propane heater and expanded screened enclosure that measures 44’ x 24’ tankless propane water heater, and gas hookup for an outdoor kitchen in Lake Ashton! If you are seeking a stunning 2-bedroom, 2-bath property this is the one it sits on the Lake Ashton West golf course and this environment for Living certified Green home features several builder upgrades PLUS extensive builder and owner upgrades Inside, you’ll find tile flooring throughout (no carpet), upgraded kitchen cabinetry with roll-out shelving, Calcatta Silestone countertops with beveled edge; custom kitchen pantry cabinet with roll-outs; under-cabinet lighting, custom closets in both bedrooms and laundry room plus a custom pantry storage. Additional features include custom closets, updated bathrooms with a walk-in shower and glass doors, remote-controlled blinds, upgraded lighting and fans, epoxy garage flooring, and enhanced landscaping Located in Lake Ashton, a premier 55+ community offering two 18-hole golf courses, a 26,000 + sq ft Health and Fitness Center, pickleball courts , a bowling alley, a restaurant and much more, activities are abundant in this exceptional community . Don’t miss this very special pool home. Schedule your showing today.

1108 Sawgrass Drive, Winter Haven

142 Morning Glory Circle, Winter Haven
$284,500
3 Beds ⋅ 2 Baths ⋅ Morningside SubDv. ⋅ 33884 Zip Code
You will be impressed the moment you walk through the door! It’s so clean, polished and move-in ready! This home is a beautifully maintained 3-bedroom, 2-bath home located in the desirable Morningside neighborhood within the gated Winterset community. This thoughtfully designed split-bedroom floor plan offers both comfort and functionality, featuring a formal living room, formal dining room, and a spacious great room ideal for everyday living and entertaining. There is opportunity for lots of natural light with the storm front door and the garage screening. Both the garage and lanai screenings were replaced in 2024 when exterior paint was completed. The kitchen is conveniently positioned with a nearby laundry closet and flows seamlessly into the main living areas. Two secondary bedrooms share a well-appointed hall bath, providing privacy for family or guests. The primary suite is a true retreat, complete with sliding glass doors leading to the Florida room, dual walk-in closets, and a luxurious en-suite bath featuring a soaking tub, separate shower, and ample space. Enjoy year-round relaxation in the expansive Florida room, perfect for a seating area and dining setup, all overlooking a generously sized backyard. This home has been thoughtfully updated and is move-in ready with new carpet throughout (2026), giving it a fresh, like-new feel. Additional updates include: Refrigerator (2023) Garage door opener (2020) Garbage disposal (December 2023) Exterior paint (September 2024) Water heater (September 2024) HVAC system (2014) Winterset offers resort-style amenities including a gated entrance, community pool, tennis courts, scenic lake views, and a private boat ramp. Conveniently located in SE Winter Haven just off Cypress Gardens Blvd, you’ll enjoy easy access to shopping, dining, and local events. Don’t miss the opportunity to own this exceptional home in one of the area’s most sought-after communities!

142 Morning Glory Circle, Winter Haven