Oakwood Estates Homes for Sale in Winter Haven - 25 homes

Remarks: Under contract-accepting backup offers. 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. SIGNIFICANT PRICE REDUCTION: Now only $79,900 AND new roof put on prior to closing! 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: Spacious living plan and Luxurious Kitchen just updated for the top Chef status. As you come in through the covered carport you'll notice the Newly installed flooring that really shines. There are 2 Living Room areas one of which you could close off for a 3rd bedroom. Large Master Bedroom and Bath. Skirting around the home has just been replaced for a new look. Not to mention all of the amenities offered with the community swimming pool, pickleball, tennis courts and putt putt golf course. This property is located on the dog approved residence street, so Fido is in luck. New AC unit was replaced in 2026. You're in close proximity to all the Central Florida attractions. Hurricane/ Tie Down Straps Replaced 2023. Ceiling fans have been updated w/ remotes.

Listing is courtesy of: FLORIDA HOMES REALTY & MORTGAGE (904-996-9144)

Listing Agent: Karl Erickson (813-245-6181)

Remarks: Under contract-accepting backup offers. 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: 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: Check out the improvements recently completed!! The home is move in ready!! The flooring has all been replaced with new plush carpet and vinyl plank. The subfloor has been reinforced throughout the home. The home has a fresh coat of paint in soothing colors. The main bathroom has new wallboard to complement the updated vanity. The primary bathroom has a new wall cabinet installed. If you saw the home early in it's listing you must see the improvements. The air conditioner was replaced in 2022 and the roof is a roof over adding extra insulation value. The home is conveniently laid out with a very functional kitchen. The living room offers good space plus the front porch has a window air conditioner increasing the usable square footage. The primary bedroom has a nice sized walk in closet. Oakwood Estates has two pools, two clubhouses, shuffleboard, tennis courts and much, much more. You can be as involved as you would like or just sit back and enjoy the peaceful community. Make your appointment today!!

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

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

Remarks: MAJOR PRICE ADJUSTMENT!!! VERY MOTIVATED SELLER!! 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: 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: Pack your bags and move right into this very well maintained home located in Oakwood Estates, a 55+ community. The floorplan offers two living areas with nice sized bedroom. The cathedral ceilings make the living area feel spacious. The functional kitchen provides lots of storage with the built-in in the dining area offering more storage. The home features all new windows, with acrylic windows in the front porch area. The HVAC is one year old. The roof-over was installed approximately 2017. This home comes furnished right down to the dishes, silverware, pots and pans. Oakwood Estates offers many amenities and activities to keep you as busy as you would like, or just sit on the front porch and enjoy the view of the lake.

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

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

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: Check out this wonderfully maintained home located in Oakwood Estates, a 55+ community. The HVAC has just been replaced and the roof is 3 years old. The living room is spacious and comfortable. Both bedrooms have walk in closets with lots of storage. The side and front porches provide additional living space. The home will be sold furnished less personal items with everything you will need to move right in. The amenities at Oakwood Estates include two clubhouses, two pools, a fishing pier, shuffleboard, tennis courts, miniature golf, and much more. You can join in of the many activities offered or just sit back and enjoy the peaceful community. Call today for your appointment to see this amazing home.

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

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

Remarks: Welcome home to 4420 Limewood St in Winter Haven, located in the desirable 55+ co-op community of Oakwood Estates—a neighborhood known for active living, friendly neighbors, and resort-style amenities that make every day feel like a vacation.This home has been thoughtfully updated so you can move right in with confidence. One of the biggest improvements is the brand-new architectural shingle roof, designed to withstand winds up to 175 MPH—a huge value and peace-of-mind upgrade. Inside, you’ll immediately notice the refreshed, modern feel thanks to new flooring throughout, plus drywall upgrades in the kitchen and living room, replacing traditional paneling for a brighter, cleaner look.The kitchen is both functional and inviting, featuring all-new stainless steel appliances and a convenient drop-leaf table—perfect for morning coffee, casual meals, or entertaining. The home also includes a mini bar, creating the perfect space for hosting friends and family. The primary bedroom is ready for comfort from day one with a brand-new king bed and mattress included.To make ownership even easier, the seller is providing a home warranty to the buyer.Life in Oakwood Estates is all about lifestyle. Residents enjoy an incredible list of amenities including a lake for water activities, a heated community pool, clubhouse, tennis, pickleball, shuffleboard, mini golf, and a full calendar of community events and activities designed to keep you as social—or as laid back—as you’d like.Whether you’re looking for a seasonal getaway or a full-time Florida lifestyle, 4420 Limewood St offers the perfect blend of upgrades, comfort, and community living in one of Winter Haven’s most established 55+ communities.

Listing is courtesy of: RE/MAX HERITAGE PROFESSIONALS (863-256-2188)

Listing Agent: Chris Loschiavo (863-280-2201)

Remarks: Walk right into this open and spacious home. The kitchen is perfect for entertaining with newer cabinets and cooktop. The cathedral ceilings in the living room give the feel of lots of space. The floorplan offers 2 living areas. The guest bedroom has the main bathroom attached which is perfect for those overnight guests. The primary bedroom is spacious with two separate closets for him and her with a nice sized shower stall in the primary bathroom. The shingle roof was installed in 2021. The vapor barrier was replaced in 2023 and the home has new skirting. The side porch offers more living space and is backed with a great workshop area. The laundry is inside the home. If all that isn't enough there is an EV charging port installed. This home is located in Oakwood Estates, a 55+ community offering many activities or just sit back and enjoy the peaceful community. Make your appointment today!! This home will be sold unfurnished with appliances only.

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

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

Remarks: Welcome to paradise, in this 2/2 with a enclosed front porch, to watch the beautiful Florida sunsets. The gated 55 plus community offers many amenities such as tennis, fishing pier, two heated pools, shuffle board, miniature golf, bocce ball, two club houses, fishing pier, plus many planned activities.

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

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

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.

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 well maintained home. The home comes furnished with everything you see. The cathedral ceilings give you an open and spacious feel to the living area. You will find upgraded kitchen with a nice cooktop stove and built in oven and microwave. The bathrooms have been updated with new vanities. A new HVAC system has just been installed. The roof is a roof-over which adds extra insulation value and has a very long life. The windows have also been upgraded adding even more insulation value to the home. This home is located in Oakwood Estates, a 55+ community which offers many amenities and activities. Enjoy the Florida sun in one of the two pools or join in with water aerobics or volleyball. You can join in with the Koffee Klatch, ice cream socials, or one of the many potlucks, or just sit back, relax and enjoy the beautiful Florida weather. Check this out today!!

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

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

Remarks: Move right into this fully furnished home. This home offers lots of space with walk in closets in both bedrooms and a new vanity in the primary bathroom. Plus the lanai offers extra living space as well as the bonus room on the front of the home. The refrigerator and washer and dryer are newer. The metal roof was installed in 2024. Oakwood Estates, a 55+ community, offers many activities and amenities, so you can be as busy as you would like, or just sit back and enjoy the peaceful community. The rocker recliner in the living room and TVs do not convey.

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: Check out this well maintained home located in Oakwood Estates, a 55+ community, located in Sunny central Florida. The home features a very open and inviting kitchen, perfect for entertaining. The cooktop and built in oven have been updated. Step into the primary bedroom to find plenty of space for a king size bed, then step into the remodeled and updated primary bathroom. The split bedroom floor plan offers privacy to guests with a bathroom conveniently located outside the door. All the flooring is a laminate with no carpeting in the home. Enjoy the peaceful screened side porch. The home is located on a corner lot with a Florida room giving views of both streets, a great place for your morning coffee. The double pane windows and window AC offers additional living space when guests arrive. Oakwood Estates offers many amenities and activities. You can be as busy as you would like or enjoy the peaceful community and watch the world go by.

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

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

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)