Winter Haven Homes with Shuffleboard Court Amenities

2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code

Welcome to 4063 Rolling Oaks in Winter Haven, located in Oakwood Estates, a desirable co-op 55+ community. This well-maintained 2 bedroom, 2 bathroom home offers a spacious and versatile floor plan featuring a bonus room and a Florida room, providing plenty of space for relaxing, entertaining, hobbies or a home office. Laminate flooring flows throughout the main living areas and bedrooms, while the Florida room features tile flooring. The dining room includes a built-in buffet with display cabinets and additional storage, creating the perfect space for showcasing your favorite pieces and hosting family and friends. The kitchen offers a convenient closet pantry for added storage, and both bedrooms feature generous walk-in closets. Exterior features include window awnings and an attached carport. A BRAND NEW ROOF was put on (08/2026). Oakwood Estates offers an affordable Florida lifestyle with low HOA fees that include water and trash service. Residents can also enjoy many amenities of this lakefront community including; two clubhouses, two swimming pools, an activity center with a pool table, tennis & pickleball courts, a mini golf course and a lake with fishing dock. Don’t miss this opportunity to own a home in a welcoming community conveniently located near shopping, dining, and all the great amenities and attractions Winter Haven is known for.

4063 Rolling Oaks Drive, Winter Haven

$149,000

2 Beds ⋅ 2 Baths ⋅ Wellington Pt 01 Bldgs 01 02 & Wellington Pt 02 B SubDv. ⋅ 33880 Zip Code

This is 55+ living at its best! Fully renovated with high-end finishes, a spotless, move-in-ready interior, and a desirable lakeside setting on the world-famous Winter Haven Chain of Lakes. Welcome to 689 Lake Howard Drive, Unit 213, where thoughtful updates, generous living spaces, and an exceptional waterfront community come together at an attractive price point. Located in The Wellington on the shores of Lake Howard, this impressive 2 bedroom, 2 bath condo feels fresh, modern, and remarkably spacious. The expansive living and dining area features beautiful flooring, crown molding, updated lighting and ceiling fans, and plenty of room for comfortable everyday living and entertaining. Sliding glass doors open to a large enclosed Florida room overlooking the beautifully maintained community grounds, providing even more space to relax and enjoy the Florida lifestyle. The remodeled kitchen is a standout, featuring quartz countertops, abundant white soft-close cabinetry, a farmhouse-style sink, herringbone tile backsplash, under-cabinet lighting, and a complete stainless steel LG appliance package including refrigerator, range, microwave, and dishwasher. Both bathrooms have been beautifully remodeled with quartz-topped vanities and impressive custom tile work. Walk-in showers feature frameless glass enclosures, decorative tile accents, niches, and contemporary finishes. An exceptionally large walk-in closet provides outstanding storage, while an interior laundry closet with included washer and dryer and a large private exterior storage room add everyday convenience. The Wellington offers beautifully landscaped grounds, two pool areas including a heated pool for winter use, clubhouse, shuffleboard, community activities, and a private dock on Lake Howard with access to the Winter Haven Chain of Lakes—perfect for fishing and enjoying life on the water. The condo fee includes basic cable and internet, water, garbage pickup, exterior building maintenance, and grounds maintenance. A private covered parking space is also included. Conveniently located near medical facilities, shopping, restaurants, churches, grocery stores, and charming Downtown Winter Haven. Beautifully remodeled, incredibly spacious, and located in a Chain of Lakes waterfront community—this is 55+ living with the updates already done for you!

689 Lake Howard Drive Nw Unit 213, Winter Haven

$164,800

2 Beds ⋅ 2 Baths ⋅ Lakeside Ranch For Mobile Homes SubDv. ⋅ 33881 Zip Code

Meticulously Maintained, beautiful 2/2, move-in ready home in a quiet lake-front community. Pride of Ownership shows throughout! List of Updates attached and include finished walls, Plumbing, downspouts, Heat Pump with UV Light, Newer Appliance, Washer and Dryer (inside laundry), flooring, kitchen cabinets with soft-close, built-in pantry/storage in the Dining Room to name a few. Thoughtfully maintained, offering peace of mind and comfort from day one! BONUS=2024 Evolution C4PRO golf cart is included! The sales price includes the $11,000 share of ownership in this Co-op Community. The low $145/mo HOA fee includes water, sewer, and lawn mowing. Individual mailbox, community laundry and clothesline available. No pets. No motorcycles. Trucks ok. Located near shopping, entertainment, and health care!

628 Lakeside Ranch Lane, Winter Haven

$139,900

2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code

Walk right into this beautiful home located in Oakwood Estates, a 55+ community. You will find the home nicely furnished which all conveys with the sale of the home. The open living area at the front of the home has a beautiful lake view. The kitchen is open to another living space or dining area. The primary bedroom at the rear of the home is nice sized and will accommodate a king sized bed. The guest bedroom is attached to the guest bathroom offering privacy and convenience to your guests. The Lanai which is also air conditioned (vent behind the couch) offers a wonderful area to sit and enjoy your morning coffee where you can watch the world go by. Oakwood Estates offers many activities and amenities including two pools, two clubhouses, tennis courts, shuffle board, miniature golf and much more. You can stay as busy as you like or just sit back and enjoy the peaceful community. The golf cart is included in the sale of the home. The Sellers have a home warranty in place and with a reasonable offer will pay for three month to continue the plan. Make your appointment today to see this beautiful home.

4234 Rolling Oaks Drive, Winter Haven

$229,900

2 Beds ⋅ 2 Baths ⋅ Winterset 01 A Condo 02 Amd SubDv. ⋅ 33884 Zip Code

Completely renovated, ground-floor condo with expansive lake views on the Winter Haven Chain of Lakes! Welcome to Winterset, where this beautifully reimagined 2-bedroom, 2-bath residence combines a spacious interior, private screened porch, exceptional water views, and the amenities of one of Winter Haven's most desirable gated communities. From top to bottom the home feels fresh, bright, and remarkably spacious. New flooring flows throughout, complemented by updated lighting, contemporary ceiling fans, modern fixtures, and a crisp neutral palette. The open living and dining areas provide plenty of room to relax and entertain, while large windows frame the expansive lawn and sparkling waters of Lake Winterset beyond. The redesigned kitchen has been expanded for greater functionality and features granite countertops, soft-close cabinetry with crown molding, black appliances, a gas range, dishwasher, generous breakfast bar, and abundant cabinet and counter space. Open to the dining and living areas, it creates an easy flow throughout the main living space. The oversized primary suite is one of the home's standout features, offering beautiful lake views and direct access to the private screened porch—a peaceful spot for morning coffee, an afternoon book, or simply enjoying the breeze and ever-changing colors of sunsets over the water. An exceptionally large walk-in closet provides impressive storage, while the completely renovated en-suite bath features a double vanity with undermount sinks and granite countertop, updated fixtures, and a frameless glass walk-in shower surrounded by custom tile. Positioned separately from the primary suite, the spacious second bedroom offers two closets and convenient access to the beautifully renovated guest bath, complete with granite-topped vanity and custom-tiled tub and shower. The thoughtful layout also includes an interior laundry area and additional storage. Beyond the residence, Winterset delivers the Florida lifestyle buyers come here to enjoy. Residents have access to a heated lakefront swimming pool and spa, clubhouse, tennis and pickleball courts, shuffleboard, and a private boat ramp with direct access to the Winter Haven Chain of Lakes—opening the door to boating, fishing, water skiing, sunset cruises, and waterfront dining. Shopping, restaurants, medical facilities, LEGOLAND Florida Resort, and downtown Winter Haven are all just minutes away, while convenient routes toward Tampa and Orlando make the location equally appealing for everyday living and weekend adventures. Beautifully renovated, ground-floor living, an unusually spacious primary suite, private screened porch, resort-style amenities, Chain of Lakes access, and a gorgeous water view right outside your windows—this is the kind of Winter Haven condo that's easy to fall in love with.

503 Sweet Bay Circle, Winter Haven

$125,000

2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code

A Home That's Ready When You Are — Oakwood Estates, Winter Haven Some of life's best decisions are also the simplest ones. This lovingly maintained, fully furnished manufactured home in Oakwood Estates invites you to skip the hassle and step straight into the lifestyle you've been looking forward to — because everything has already been taken care of, and everything stays. Fresh interiors, thoughtful updates, and a warm, welcoming layout make this one of the most effortless purchases you'll make. Step inside and you're immediately greeted by natural light pouring through double-pane windows, setting a bright, airy tone throughout. The kitchen shines with stainless steel appliances, wood-look countertops, a newer sink, and crisp white cabinetry — and yes, everything stays, right down to the air fryer. The dining area features beautiful built-in cabinetry and shelving, flowing seamlessly into a spacious living room complete with an electric reclining sofa, flat screen TV, and comfortable seating. Luxury vinyl plank flooring runs throughout, tying it all together with style and ease of maintenance. Both bedrooms are generously sized and fully furnished. The primary suite features a walk-in closet, electric reclining bed, and a quality foam mattress. The Florida room offers updated ceiling fans, a brand-new AC unit, and convenient access to the in-home washer and dryer hookups — a true bonus in this community. Slide open the door to the enclosed lanai and enjoy your morning coffee overlooking lush, manicured landscaping — your own quiet corner of Florida. Additional highlights include hurricane shutters, vinyl siding, a 2017 roof, an irrigation system, and an updated electrical panel for peace of mind. Then there's the community. Oakwood Estates is a gated, beautifully maintained 55+ resident-owned community in the heart of Winter Haven — one of Polk County's most desirable areas. Residents enjoy two heated pools, two clubhouses, tennis and pickleball courts, shuffleboard, bocce ball, a miniature golf course, horseshoes, a fishing lake with pier, RV and boat storage, a library and activities center, pool tables, and a vibrant, active activities committee that keeps the social calendar full year-round. Lighted streets, underground utilities, and security cameras throughout the common areas reflect a community that takes pride in where it lives. This is Florida living, fully loaded and ready to go.

4332 Cherrywood Street, Winter Haven

$115,000

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 1368 Square ft. 2 bedroom 2 bath 1984 with an attached enclosed Florida room and an enclosed carport with ac. The king size master bedroom has a walk-in closet and a private bathroom with a tub shower. It has an inside utility room with washer & dryer. 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.

113 Lake Hazel Drive, Winter Haven

$185,000

2 Beds ⋅ 1 Baths ⋅ Parkland Village SubDv. ⋅ 33880 Zip Code

Welcome home to this well-maintained 2-bedroom, 1-bath patio home located in the 55+ community of Parkland Village. This move-in-ready home offers numerous recent updates, including a new roof (December 2025), new windows (2024–2025), new A/C (2022), and a new refrigerator and stove (2026), providing comfort and peace of mind for years to come. Inside, you'll find thoughtful features such as vertical blinds, mirrored closet doors, and storm doors and shutters. The home also includes a private courtyard, perfect for relaxing or entertaining, along with a 1-car carport and a storage closet with a washer and dryer. Residents enjoy access to a recreation building and shuffleboard courts, while the low monthly HOA fee of just $110 includes grounds maintenance, making for easy, low-maintenance living. Conveniently located near shopping, banks, and restaurants, this home offers the perfect combination of comfort, convenience, and affordability. Don't miss this opportunity—schedule your private showing today!

790 Avenue Q Se, 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

$399,900

4 Beds ⋅ 3 Baths ⋅ Traditions Ph 02 SubDv. ⋅ 33884 Zip Code

Welcome to this beautifully maintained, energy-efficient 4-bedroom, 3-bath home in the highly desirable Traditions at Ruby Lake, a premier 55+ gated community offering the very best of Florida resort-style living. Situated on an oversized lot, this exceptional home features a desirable split floor plan Jack and Jill bathroom w/ walk-in tub and soaring high ceilings that create a bright, open, and spacious feel throughout. Thoughtfully upgraded for both comfort and efficiency, the home offers a spacious, expanded screened lanai with brick pavers—the perfect outdoor retreat for entertaining or enjoying a quiet evening—enhanced by customizable LED lighting to create the ideal ambiance. Energy-saving features include foam-core insulation in the concrete block walls, new Andersen windows, and a freshly painted exterior. Inside, you'll find hardwood flooring in the primary bedroom and front bedroom, which also makes an ideal home office. The kitchen is beautifully appointed with custom cabinetry, granite countertops, slate stainless steel appliances, and abundant storage. Custom maple shelving in the pantry, laundry room, and both linen closets adds both elegance and functionality. The primary bath also features granite countertops, completing the home's high-quality finishes. Designed for comfortable everyday living and effortless entertaining, this home offers generous living spaces that provide both privacy and flexibility for family and guests. HOA dues provide exceptional value and include weekly lawn and landscape maintenance, Spectrum TV service, and exterior house painting every seven years. Residents also enjoy full access to the community's impressive lakefront clubhouse, featuring a resort-style pool and spa, sauna, showers, a fully equipped fitness center, staffed front desk, library, business center, billiards room, craft room, and a spacious ballroom that hosts meetings, dances, entertainment, guest speakers, clubs, and social events. Outdoor amenities are equally impressive and include tennis, basketball, bocce ball, shuffleboard, pickleball, three community boat docks, a picturesque lakeside gazebo, and a paved walking path along the lake—perfect for morning strolls or evening exercise. If you're looking for a move-in-ready home with exceptional upgrades, low-maintenance living, and an active, resort-style lifestyle, this is the one you won't want to miss!

4132 Martindale Loop, Winter Haven

$99,000

2 Beds ⋅ 1 Baths ⋅ Winter Haven Harbour Apts Condo SubDv. ⋅ 33881 Zip Code

Peaceful oasis in a premier 55+ community! This lovely 2 bedroom, 1 bath second-floor condo in Winter Haven Harbour Apartments offers a perfect blend of comfort, functionality, and an active, low-maintenance lifestyle. Inside, you will find a spacious living room that flows effortlessly into a dedicated dining room, and a galley-style kitchen that maximizes counter space and storage, making meal preparation a breeze. Step onto your private balcony, where you can enjoy your morning coffee, read a book, or soak in the serene views. This wonderful active community offers fantastic resort-style perks, including a sparkling heated community pool, an active community center, and shuffleboard courts for fun with friends and neighbors. This home provides the ideal setting for your next chapter. Don't miss out, schedule your appointment today.

1700 6th St Nw Unit C24, Winter Haven

$409,000

3 Beds ⋅ 2 Baths ⋅ Lake Ashton West Ph I SubDv. ⋅ 33884 Zip Code

HOME FOR SALE IN LAKE ASHTON! Is 4052 Phoenician Way, Winter Haven, Florida YOUR next address? This 3 Bedroom, 2 Bath home with Golf Cart Entry is located on a large premium lot that abuts to the 13th Fairway of Lake Ashton's West Golf Course. The view from the wrap around covered and screened lanai includes a large pond that borders the 13th Hole with a farm pasture beyond. Home Highlights: CDD Debt Balance Paid in Full; Roof Replaced 2022; Water Heater Replaced 2022; A/C Heat Pump Replaced 2019. This home offers excellent curb appeal with a Widened Drive Way, Poured Curbing, Well Maintained Mature Landscape with Landscape Rock, Quoined Corners, Bay Window on the Front Bedroom, and arched Screened Entry. A paver walkway on the right side of the home connects the access door of the golf cart garage to the rear lanai. The interior of this home is warm and inviting with an Open and Spacious Living area. The Foyer, Dining, LR and Kitchen flow seamlessly together making entertaining a "breeze" in this home. The beautiful Bruce interlocking Engineered natural oak floors and the Plantation Shutters on the Side Lights of the Front Entry Door, Double Sliding Glass Doors in the Living Room, Bedroom 2 and Primary Bedroom accent the interior of this home- adding a touch of class. Crown molding gives definition to the Open Living area. The kitchen upgrades include: Granite counter tops, Maple Cabinets with raised panels, 3 banks of drawers, crown molding and a pantry. The refrigerator, microwave and disposal were replaced in 2026 and the range was replaced in 2023. A breakfast bar/snack bar and Dining areas are perfect for entertaining friends and family. Enter thru the 8' Front entry door with Eyebrow window above. To the left of the foyer are Bedrooms 2 and 3, a Linen Closet in the Hallway and a Guest Bathroom with shower/tub combo, accent window and comfort height vanity. A pocket door provides privacy to the Guest Bedroom area. The EXTENDED Primary Suite is located on the back on the home. It's the perfect place to relax after a long day in the sun. The Primary Suite offers a spacious sitting area and En-Suite with His/Her Walk in Closets, His/Her Separate Vanities, a large corner Soaking tub, a separate water room with a walk in shower with glass doors and linen closet. The laundry room is easily accessible from the garage and kitchen. It has cabinets for storage, a wash tub and the washer/dryer will be included in the sale of the home. The double car garage has hang down storage racks, attic access, storage cabinets, and an access door to the outside. There is a motorized screen on the garage door and a separate entry for the golf cart. The outdoor living space is a destination location in this home. The view is peaceful and the space is cozy with paver floor, ceiling fans and TV hook up. Make an appointment to tour this home today! Lake Ashton is a gated and guarded Florida Active Community with resort style amenities (2 Clubhouses with Movie Theater, Restaurant, Outdoor/Indoor Pools, Fitness Centers and More! Residents enjoy activities like Karaoke, Trivia, Dances, Entertainment Series, Holiday Events and so much more. You can stay busy living the Florida Retirement Dream every single day. For those that love the game of golf, there are (2) 18-Hole Golf Courses, a Pro Shop, Driving Range, Putting Green and the Eagles Nest (Hole 19). Don't wait to tour this home; tour it today!

4052 Phoenician Way, Winter Haven

Winter Haven Homes with Shuffleboard Court Amenities

Newest Winter Haven Homes with Shuffleboard Court Amenities