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6308 Pinehurst Loop, Winter Haven
$444,000
3 Beds ⋅ 2 Baths ⋅ Lake Ashton West Ph Ii North SubDv. ⋅ 33884 Zip Code
Welcome to this beautifully upgraded 3-bedroom, 2-bath home offering 2,045 square feet of refined living space in the highly desirable Lake Ashton 55+ golf community—where luxury meets an active, resort-style lifestyle. This thoughtfully designed home features top-notch upgrades throughout, including an additional sliding glass door leading to the back patio, flooding the living space with natural light and creating a seamless indoor-outdoor living experience. The spacious kitchen is a standout, boasting abundant cabinet storage with extended cabinetry along the back wall, perfect for entertaining, organization, and everyday convenience. Smart hybrid water heater and water softener system as well The open and inviting floor plan provides generous living and dining areas, while the private primary suite offers comfort and tranquility. Two additional bedrooms are ideal for guests, hobbies, or a home office. Both bathrooms are well-appointed, and the home’s layout is designed for easy living. Located within Lake Ashton, residents enjoy world-class amenities including championship golf courses, clubhouses, fitness centers, pools, tennis and pickleball courts, planned activities, and a vibrant social calendar. Experience the best of Florida living in this exceptional home—schedule your private showing today and discover everything Lake Ashton has to offer.

6308 Pinehurst Loop, Winter Haven
4577 Back Nine Drive, Winter Haven
$334,800
3 Beds ⋅ 2 Baths ⋅ Lake Ashton West Ph 01 SubDv. ⋅ 33884 Zip Code
Virtually Staged. Welcome Home!!! Recent Price Reduction! 4577 Back Nine Dr. Winter Haven, Fl. features 3 bedrooms and 2 full baths and is located in Lake Ashton, an Exclusive Florida Retirement 55+ community. This home has BRAND NEW EXTERIOR PAINT! The widened, paver driveway offers extra room for parking and the screened entry at the front door is an added bonus. The glass leaded front door with large eye brow window above leads you into a home that is warm, inviting and spacious. The open-concept kitchen showcases granite countertops, stainless steel appliances, Maple cabinets and a Pantry Cabinet with convenient pull-out shelving. You can seamlessly blend indoor and outdoor living by sliding open the living room and dinette area sliding glass doors to the screened, covered lanai with 8" aluminum border base. It's the perfect place for entertaining. The primary bedroom with En-Suite bath has been extended 4 ft. to provide additional living space. It's the perfect getaway and you'll enjoy the EXTRA SPACE in the primary suite. The primary bathroom has ample closet space with His/Her Walk In Closets with Organization System, a large walk in shower with double shower heads, a separate water closet and separate His and Her Vanities. Her vanity has an additional make up area. Guests will appreciate the separate bedrooms and bath behind a pocket door. Additional features include: an automatic screen on the garage door, a separate irrigation meter, 18" diagonal tile in home (Bed 2 and Bed 3 are excluded), crown moulding, New A/C modulator, cabinetry in laundry room, Plantation Shutters in the Bedrooms, Upgraded entry light fixture, surround sound in the living room, additional insulation in the attic, new interior paint in Bedroom 1 and Guest Bathroom, new interior paint in the formal dining and dinette areas. Lake Ashton, a Florida Retirement community, has a Clubhouse with large grand ballroom, Outdoor Community Heated Pool, Tennis Courts, Bocce Ball, Shuffleboard, Fitness Center, Movie Theater, Bowling Lanes, Restaurant (Charm City)and More! The Health and Fitness center has indoor basketball, indoor racquetball, indoor heated pool, pickle ball and tennis courts, media center, card, craft and billiard rooms. There are two golf courses located in Lake Ashton. Memberships are optional and not a requirement to reside in Lake Ashton. Residents enjoy the resort style amenities and activities offered in Lake Ashton, a premier Florida Retirement Community. Don't miss this opportunity to own your piece of paradise. Check out the photo gallery and make your appointment to tour this home.

4577 Back Nine Drive, Winter Haven
5197 Pebble Beach Boulevard, Winter Haven
$335,000
2 Beds ⋅ 2 Baths ⋅ Lake Ashton West Ph 01 SubDv. ⋅ 33884 Zip Code
Don't miss out on this opportunity to reside in a home located on the WEST golf course in Lake Ashton. FURNITURE AVAILABLE! GOLF CART INCLUDED! WASHER/DRYER INCLUDED! This Callaway Floor plan with NEW A/C (December 2025) is a "Green" home with 2 Bedrooms, 2 Baths, Plus a FLEX ROOM. This home has over 1,660 sq. ft. of living space. Located on the 17th Fairway of the West Golf Course in Lake Ashton, a guard-gated Florida 55+ community, this home offers a Split Plan. The kitchen package features a spacious dinette area, granite counter tops, stainless steel appliances, 42" cabinets and breakfast bar. The foyer with high ceiling is welcoming and is a passage to the laundry room and 2nd bedroom. The laundry room is directly to your left and to your right is a hallway with 2 linen closets that leads to the 2nd bedroom and Guest Bath. The laundry room is accessible from the foyer and the garage. The living room, kitchen and dinette are centrally located in this home- OPEN & SPACIOUS. The Den/Office is directly off the living room and is currently being used as a bedroom. There are triple sliders in the living room that separate the screened and covered lanai with tile floor. The primary suite with large walk in closet includes a master bath with dual sinks and a comfort height vanity, walk in shower and separate water closet with window. Other upgrades in this home include tile flooring in the Living Areas (Bedrooms are carpeted), water softener, ceiling fans, screened entryway, automatic screen on the garage door. Lake Ashton offers a Main Clubhouse with a theater, bowling lanes, card, craft and billiard rooms, fitness center, restaurant (Charm City), and outdoor heated pool. Residents also enjoy tennis courts, shuffleboard courts, Bocce and planned activities in the community. There is a Health and Fitness Center with an indoor heated lap pool, 1/2 basketball, indoor racquetball, pickle ball courts and MORE... Make an appointment to tour this home and Lake Ashton TODAY!

5197 Pebble Beach Boulevard, Winter Haven
4165 Rolling Oaks Drive, Winter Haven
$84,900
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code
Priced to sell, Home has a new metal roof, CHA is approximately five years old, and you will feel right at home from the moment you walk in. Come enjoy the beautiful Florida sunsets in this 55+ gated, five-star park.

4165 Rolling Oaks Drive, Winter Haven
4251 Cedarwood Street, Winter Haven
$106,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code
What an amazing home just waiting for it's new owner!! The kitchen has been completely updated with new cabinets and flooring. The home offers two additional living spaces. The lanai on the side of the home is vented with the central ac and is included in the total square footage. or you can escape to the front porch which is also vented increasing the square footage by an additional 200 sf bringing the total living area to 1216 sf. The primary bathroom has an updated vanity. The laundry is located behind the side lanai so you don't have to go outside. The air conditioner is brand new in December 2025. This home is located in Oakwood Estates, a 55+ community which offers many amenities and activities. You can stay as busy as you like, or just sit back and enjoy the peaceful community.

4251 Cedarwood Street, Winter Haven
21 Casarena Court, Winter Haven
$285,000
2 Beds ⋅ 3 Baths ⋅ Casarena On Lakes SubDv. ⋅ 33881 Zip Code
Move in ready and located on the Winter Haven Chain of Lakes! Welcome to the gated community of Casarena on the Lakes. This well-designed and meticulously maintained home is set up just right for indoor and outdoor living. The first floor is an open design with the fireplace separating the living and dining area. Enjoy granite countertops and updated appliances in the spacious kitchen that provides the perfect setting to create all of your favorite culinary delights. The living area is a versatile space with a cove for a hosting or exercise area. The main floor is also equipped with a half bath. Head upstairs to the loft that overlooks the living area and separates the two bedrooms. The primary bedroom leads to an open balcony on one side and an updated bathroom on the other. Both bedrooms are oversized with plenty of closet space. The new metal roof was installed in October 2023, The HVAC system has been well maintained, there is a new water heater and the home is also equipped with a whole home generator that is tested regularly. Enjoy the community pool, tennis or pickleball court and access to Lake Cannon, which is on the Winter Haven Chain of Lakes. Downtown Winter Haven is only 10 minutes away and you have quick access to Hwy 92 and 27. Call today for your private showing.

21 Casarena Court, Winter Haven
1709 Linz Ct, Winter Haven
$248,000
2 Beds ⋅ 2 Baths ⋅ Vienna Square SubDv. ⋅ 33884 Zip Code
NATURE CALLS, flies, and strolls by this beautiful NEW CONSTRUCTION Villa. Complete, and ready for its 1st happy homeowner. Bright, fresh, and relaxing 2 bedroom 2 bath with 2 car garage. The beautifully finished kitchen comes complete with a full stainless steel appliance package, granite tops, and modern gray cabinets. These lovely cabinets, and countertops also complement both the primary bath, and the guest bathroom. Neutral colors offer a nice finish to this well designed floor plan. Enjoy the privacy from your screened patio with no back door neighbors. Easy living awaits without the big worries. Exterior paint, roof replacement, irrigation water, yard maintenance, and Spectrum Internet/TV package is included in the reasonable monthly fees. Enjoy the social activities with the neighbors, splash in the community pool, or make a hit on the tennis/pickleball courts. The convenient location, and reasonable monthly fees makes this 55+ community an easy choice. Step inside, fall in love. Make it yours!

1709 Linz Ct, Winter Haven
3923 Baldwin Lane, Winter Haven
$253,900
3 Beds ⋅ 2 Baths ⋅ Traditions Ph 1 SubDv. ⋅ 33884 Zip Code
NEW PRICE IMPROVEMENT! WELCOME TO 3923 BALDWIN LANE, NEW ROOF 2023, NEW A/C 2025, FRESHLY PAINTED 2024, RECENT IMPROVEMENTS INCLUDE A NEW GARBAGE DISPOSAL AND THE ADDITION OF A NEW CLOSET IN THE THIRD BEDROOM, ENHANCING BOTH CONVENIENCE AND STORAGE SPACE. LOCATED IN THE HIGHLY SOUGHT-AFTER TRADITIONS GATED COMMUNITY IN WINTER HAVEN! THIS BEAUTIFULLY MAINTAINED HOME OFFERS THE PERFECT BLEND OF COMFORT, STYLE, AND LOW-MAINTENANCE LIVING. FEATURING SPACIOUS LIVING AREAS, A WELL-APPOINTED KITCHEN, AND A SERENE SCREENED-IN LANAI, IT'S IDEAL FOR RELAXING OR ENTERTAINING. ENJOY RESORT-STYLE AMENITIES INCLUDING A CLUBHOUSE, HEATED POOL, FITNESS CENTER, TENNIS COURTS, AND LAKE ACCESS WITH A PRIVATE DOCK-PERFECT FOR ACTIVE ADULTS 55 AND BETTER! WITH 24-HOUR SECURED GATED ENTRANCE AND A VIBRANT, FRIENDLY ATMOSPHERE. TRADITIONS OFFERS THE LIFESTYLE YOU HAVE BEEN LOOKING FOR. SCHEDULE YOUR PRIVATE TOUR TODAY AND EXPERIENCE FLORIDA LIVING AT ITS FINEST.

3923 Baldwin Lane, Winter Haven
2817 Wingfoot Court, Winter Haven
$270,000
3 Beds ⋅ 2 Baths ⋅ Cypresswood Golf Villas Gc-2 SubDv. ⋅ 33884 Zip Code
Welcome to 2817 Wingfoot Ct, located in the desirable Cypresswood Golf Villas. This beautifully maintained villa sits along the 8th fairway of the prestigious Cypresswood Golf & Country Club, a guard-gated community offering both privacy and tranquility. Inside, you'll find three spacious bedrooms and two full bathrooms. The living and dining areas feature vaulted ceilings that enhance the open and airy atmosphere. The eat-in kitchen is a standout with new custom cabinetry, granite countertops, and a convenient closet pantry. Flooring throughout the home includes durable laminate and ceramic tile, with cozy carpeting in the third bedroom. The primary suite offers sliding doors to the patio, a generous walk-in closet, and an updated bathroom. The secondary bedroom also includes a walk-in closet, while the third bedroom features patio access and a European-style A/C unit. Major updates include a roof replacement in 2022, and a new A/C system installed in 2019. Covered parking adds convenience. Enjoy resort-style living with scenic golf course views and access to community amenities, all just minutes from shopping, dining, and major roadways. Whether you're seeking a year-round residence or a seasonal escape, this villa is the perfect place to call home. Community pool, tennis, clubhouse & restaurant.

2817 Wingfoot Court, Winter Haven
4246 Cedarwood Street, Winter Haven
$99,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code
Welcome to your move in ready home in Oakwood Estates, a gated community designed for those aged 55 and older. This beautifully maintained 2-bedroom, 2-bathroom manufactured home comes fully furnished and is being sold as-is, allowing you to move in comfortably without additional expenses. The double panes windows add thermal efficiency, and the 2014 shingle roof is in great condition . Features Include: - Two spacious bedrooms (split bedroom ) and bathrooms - Two attached screened-in porches, perfect for enjoying the Florida sunshine - Utility shed for additional storage (houses washer/dryer) - Parking space for two vehicles - Access to community amenities, including swimming, shuffleboard, fishing pier, and tennis Location: Conveniently located close to shopping centers and restaurants, everything you need is just a short drive away. Enjoy a vibrant community lifestyle with various social activities and events right at your doorstep. This section is a “No Dog” area but other inside pets are acceptable (cat, bird, fish)

4246 Cedarwood Street, Winter Haven
104 Woden Way, Winter Haven
$379,000
3 Beds ⋅ 2 Baths ⋅ Valhalla SubDv. ⋅ 33884 Zip Code
Valhalla - A GATED subdivision with pool, club house and more! 3-bedroom, 2-bath villa home with a connecting property but considered a single family home. This special villa has a functional layout with updated features throughout. A screened entry with leaded glass doors opens to vaulted ceilings and custom architectural touches. The open concept kitchen includes granite countertops, custom cabinetry, a center island with breakfast bar, Bosch dishwasher, stainless oven and range, walk-in pantry, and a passthrough to the living area for open flow. Wood plank flooring runs throughout the main spaces. The living room features large windows and an adjacent flex space for dining, office, or den use. The primary suite includes an ensuite bathroom with slate tile, jacuzzi tub, glass shower, dual sinks, and the laundry room is part of the primary. The guest room features a window seat and recessed lighting. A third room functions well as an office or additional guest space. HOA covers lawn care, water, trash, basic cable, pool, and tennis access.

104 Woden Way, Winter Haven
5850 Cypress Gardens Boulevard Unit 304, Winter Haven
$139,000
2 Beds ⋅ 2 Baths ⋅ Royal Crescent Condo SubDv. ⋅ 33884 Zip Code
Welcome to your new home located directly across the street From Legoland. Home features community pool and tennis court and is ready for a new owner. Located in the central Hub of Winter Haven and close to anything any everything you need. Shopping, restaurants, schools.

5850 Cypress Gardens Boulevard Unit 304, Winter Haven