Oakwood Estates Homes for Sale in Winter Haven - 23 homes

Remarks: This home is a blank slate with lots of room. Over 1400 sf of living space plus the lanai with over 300 sf. Much of the flooring is removed showing the sturdy plywood floors. The kitchen is very functional with lots of storage space. The laundry is conveniently located just off the kitchen. The split bedroom floor plan offers lots of privacy for guests. The guest bedroom is a large area that could incorporate an office space with a full back conveniently located outside of the room. The shingled roof was installed in 2017, air conditioner has a manufacture date of 2020, and the water heater was installed in December 2025. If that's not enough it is located in the "dog area", so bring those little fur babies and make this home your own. This home is priced to sell quickly. Make your appointment today!!

Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)

Listing Agent: Kathy Devor (573-450-1679)

Remarks: 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. 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. https://www.oakwoodmhp.com/

Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)

Listing Agent: Kathy Devor (573-450-1679)

Remarks: Under contract-accepting backup offers. Move right into this wonderfully furnished home in Oakwood Estates, a 55+ community. The home will be fully furnished less personal items and antiques. The home features new windows adding extra insulation value. The TPO roof was installed in 2011 and the air conditioner was installed in 2018. In 2020 the home was replumbed with CPVC. The kitchen has a reverse osmosis system located under the kitchen sink. The cathedral ceilings providing the feeling of spaciousness. Oakwood Estates offers many amenities including two pools, two clubhouses, shuffleboard, tennis courts, bocci ball, and much, much more. You can be as busy as you like or sit back and just watch the world go by enjoying the quiet and peacefulness of the community. Just pack your bags and move right in!! Make your appointment today.

Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)

Listing Agent: Kathy Devor (573-450-1679)

Remarks: Welcome to this well-maintained 2-bedroom, 2-bath home located in the desirable community of Oakwood Estates in Winter Haven. This home offers a peaceful, well-kept neighborhood with a welcoming atmosphere and a beautiful lake view to enjoy. Recent updates include new kitchen and bathroom flooring, new windows, and new interior and exterior doors, along with a roof that is approximately 5 years old, offering added value and peace of mind. No lot rent—ownership includes the land, with only a low monthly HOA fee. Oakwood Estates is a gated 55+ community offering resort-style amenities including clubhouses, heated pools, fitness center, shuffleboard, tennis courts, and a full calendar of activities. Conveniently located near shopping, dining, medical facilities, and major roadways. Schedule your private showing today and experience easy living in this vibrant community.

Listing is courtesy of: LA ROSA REALTY PRESTIGE (863-940-4850)

Listing Agent: Jody Pagan (863-604-2367)

Remarks: You will fall in love with this home from the time you walk through the front door. Has so much to offer, Has rear screen porch and backs up to drainage ditch. Roof is less than a year old and C/H/A is approximately two years. All main furniture will stay. Located in a 55 plus co op with low maintenance fees. Community is gated and has two club houses, two heated pools, Tennis,fishing pier plus much more. This home want last.

Listing is courtesy of: SOUTHERN BELLE REALTY (863-299-7800)

Listing Agent: Reta Stead (863-299-7800)

Remarks: 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)

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Andi Gamble (954-235-7723)

Remarks: 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.

Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)

Listing Agent: Kathy Devor (573-450-1679)

Remarks: Under contract-accepting backup offers. Move right into this beautiful home, located in Oakwood Estates, a 55+ community. This home will be furnished with what you see. The living area is very spacious with cathedral ceilings which increases the wonderful open feeling. The refrigerator is new and the stove is 3 years old. The home has been repainted with newer fixtures in the kitchen and living room. Both bedrooms are spacious with walk in closets. The air conditioner was installed in 2016, vinyl thermal windows were installed in 2017, and the membrane TPO roof was installed in 2014. If that isn't enough the golf cart is included in the sale of the home. Oakwood Estates is a wonderful 55+ community that offers many opportunities and amenities including tennis courts, 2 pools, 2 clubhouses, miniature golf, and shuffleboard to name a few. Make your appointment to see this home today!!

Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)

Listing Agent: Kathy Devor (573-450-1679)

Remarks: Great home with an open living space ready for it's next owner. This home has a fresh coat of paint and is a blank slate for it's new owners. Sit on the front porch and enjoy your morning coffee. The rooms are nice sized with great closet space. The laundry/shop area has plenty of space for your Do-it-yourself projects. Oakwood Estates, a 55+ community offers 2 pools, 2 clubhouses, shuffleboard, tennis courts, miniature golf, and much more. In addition to the amenities, Oakwood offers many opportunities to meet with new folks. Come to Koffee Klatch on Wednesday morning, enjoy an ice cream social a couple times a month, or get your Boogie on at one of the dances. Call today to view this home that's just waiting for YOU!!

Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)

Listing Agent: Kathy Devor (573-450-1679)

Remarks: Walk right into this well maintained home. The furnishings you see will remain with the home. The kitchen is large and very functional with lots of cabinets and counter space. Enjoy the open and inviting living area, perfect for entertaining. Sit on the screened front porch enjoying your morning coffee with a nice view of the lake. There is no carpet in this home with laminate flooring in all the living areas. Oakwood Estates, a 55+ community offers many amenities and activities. Get your coffee and donuts every Wednesday morning at Koffee Klatch, enjoy an ice cream sundae twice a month or dance to the music at any of the dances held during the winter months. In addition to the many activities, there are two pools and two clubhouses, shuffleboard, miniature golf, bocci ball, tennis courts, and much more. You can be as busy as you would like or just sit back and enjoy the peaceful community.

Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)

Listing Agent: Kathy Devor (573-450-1679)

Remarks: Under contract-accepting backup offers. Fall in love with this 2/2 light and airy, open floor plan home. This home has it all, from its tons of storage , two porches, nice washroom, Home is awaiting its new owners. And located in a beautiful gated community that boost two club houses, two heated pools, fishing, miniature golf, shuffle board plus much more. Call today before it’s gone!

Listing is courtesy of: SOUTHERN BELLE REALTY (863-299-7800)

Listing Agent: Reta Stead (863-299-7800)

Remarks: Come enjoy the beautiful Florida sunsets, In this beautiful, furnished home. You can relax in the enclosed Florida room, Carport is long enough to put two cars in. floors have the beautiful laminate wood flooring, all through out the livingroom,and dining areas. All located in a beautiful gated 55 plus park. Two heated pools, two clubhouses, tennis ,fishing pier, minature golf, shuffle board, plus much more. this home want last, act fast.

Listing is courtesy of: SOUTHERN BELLE REALTY (863-299-7800)

Listing Agent: Reta Stead (863-299-7800)

Remarks: Under contract-accepting backup offers. Pack your bags and move right into this beautiful home. The kitchen was remodeled three years ago. The side porch/lanai adds approximately 200 sf of living space (included in total sf) and is vented with central air. The home features beautiful built ins in the dining area as well as the 2nd bedroom. The primary bathroom has an updated shower and vanity. The shingled roof is 11 years old and the ac is 12 years old. The home comes furnished. Walk through the new sliding door to the front porch which features tinted windows and Berber carpet. This home is located in the Dog area where you can have two pets up to 20lb each. Enjoy Oakwood Estates, a peaceful 55+ community offering many amenities and activities, or just sit on the front porch and watch the world go by. This home is located in the area of Oakwood Estates that allows dogs. There is a 2 pet limit of up to 20 lbs.

Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)

Listing Agent: Kathy Devor (573-450-1679)

Remarks: Welcome to easy, carefree Florida living in the wonderful 55+ community of Oakwood Estates. This warm and welcoming neighborhood offers the perfect blend of relaxation and connection, with amenities designed to make every day feel like a getaway. Enjoy sunny afternoons at the community pool, friendly matches on the tennis courts, quiet moments in the library, or peaceful evenings fishing from the pier. This comfortable and spacious home features 2 bedrooms and 2 bathrooms, giving you plenty of room to relax and enjoy your surroundings. Start your mornings with coffee on the inviting front porch/lanai, or start a project on the side patio. Inside, the dining area showcases beautiful built-ins that add charm and character, while a convenient desk space near the kitchen provides the perfect spot for organizing recipes, paying bills, or planning your next adventure. Even better, a brand-new roof will be included with a full-price offer, giving you added peace of mind. Located in the dog-friendly section of Oakwood Estates, this home allows up to two pets (20 lbs each), so your furry companions can enjoy the lifestyle too. If you’ve been dreaming of a friendly community, warm sunshine, and a relaxed Florida lifestyle, this home is ready to welcome you. Schedule your showing today and start enjoying the retirement lifestyle you deserve.

Listing is courtesy of: KELLER WILLIAMS REALTY SMART (863-577-1234)

Listing Agent: Kelly Fain (863-617-0074)

Remarks: 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. You get all this, plus the golf cart with new batteries is included in the sale of the home. 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.

Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)

Listing Agent: Kathy Devor (573-450-1679)

Remarks: 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.

Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)

Listing Agent: Kathy Devor (573-450-1679)

Remarks: Move right into this very well maintained home. This home comes furnished with most of what you see including dishes, pots and pans, and silverware. There is laminate flooring throughout the entire home. The roof was installed in 2010 and the air conditioner in 2011. The open living space makes the home very comfortable and appealing. The front porch area is incorporated into the living area and is perfect for entertaining. The washer and dryer are just 3 years old. If that isn't enough the golf cart is included. This home is located in Oakwood Estates, a 55+ community offering many amenities and activities. You can be as busy as you want or just sit back and watch the world go by!!

Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)

Listing Agent: Kathy Devor (573-450-1679)

Remarks: 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.

Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)

Listing Agent: Kathy Devor (573-450-1679)

Remarks: Move right into this beautifully remodeled home. The open living area features an awesome kitchen with all a huge bar/work space. This home is perfect for entertaining, or just sit out on the open front porch and watch the world go by. There is no carpeting in this home, it is a vinyl plank throughout the home. The windows are a double pane insulated window adding to the energy efficiency of the home. The stackable washer and dryer is located in the shed. The side porch offers lots of room for storage, plus there is a shed out back. The shingled roof was installed in 2024 and the air conditioner was installed in 2020. There is also a water softener. The home comes furnished with what you see in the home as you are viewing it. Oakwood Estates, a 55+ community, offers many amenities such as shuffleboard, 2 pools and 2 clubhouses, tennis courts, miniature golf and much, much more.

Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)

Listing Agent: Kathy Devor (573-450-1679)

Remarks: Spacious is the best word to describe this home. The home has 1440 sf plus a side porch for additional entertaining space. The home has two living areas and a wonderfully functional kitchen. The primary bedroom and bath allow for lots of space with two closets for his and hers clothes. The main bathroom is directly off the guest bedroom, making it convenient for guests. The hot water heater was replaced in 2024, roof in 2020 and HVAC in 2015. So this home is ready for it's new owners. The windows are a newer double pane for energy efficiency and the sliding patio door is also newer. The furnishings you see when you view the home will remain in the home. Oakwood Estates, a 55+ community, offers many opportunities and amenities. You can be as busy as you want, or just sit back and watch the world go by. Check this home out today!!

Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)

Listing Agent: Kathy Devor (573-450-1679)