Oakwood Estates Homes with Pool Community Features

Oakwood Estates Homes with Pool Community Features

Welcome to Oakwood Estates, a hidden gem nestled in the heart of Winter Haven, Florida, within beautiful Polk County. This charming subdivision offers a perfect blend of serene suburban living and vibrant community spirit, making it an ideal place for families, retirees, and anyone looking to embrace the Florida lifestyle.

Oakwood Estates is renowned for its stunning homes, many of which feature private pools, providing the perfect oasis for relaxation and recreation. Imagine stepping out into your backyard on a warm Florida day, diving into your sparkling pool, or hosting delightful gatherings with friends and family under the sun. The community’s emphasis on outdoor living ensures that you can enjoy the sunshine year-round.

Beyond the beautiful homes and inviting pools, Oakwood Estates boasts an array of community features designed to enhance your living experience. Residents enjoy access to well-maintained parks, walking trails, and recreational areas, promoting an active and healthy lifestyle. The friendly atmosphere fosters a sense of belonging, where neighbors become friends, and community events create lasting memories.

Situated conveniently near shopping, dining, and entertainment options, Oakwood Estates offers the perfect balance of tranquility and accessibility. With its prime location in Winter Haven, you’re never far from the stunning lakes and natural beauty that Florida is famous for.

Discover your dream home in Oakwood Estates, where every day feels like a vacation. Come explore this vibrant community and see why it’s the perfect place to call home!

Newest Oakwood Estates Homes with Pool Community Features

4235 Cedarwood Street, Winter Haven
$109,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code
Walk right into this beautifully maintained home located in Oakwood Estates, a 55+ community. The metal roof is only 6 years old. The home has newer windows and a new vapor barrier. The lanai has all new windows. The home also has a water filtration system. The furnishings you see will stay with the home. The living and dining room give a very open and inviting feel. The kitchen bar offers additional eating space for when the whole family comes to visit. The ample kitchen cabinetry has been updated. The only carpet remaining in the home is in the guest bedroom, but it is in very good condition. Sit on the front porch or side lanai for your morning coffee. Enjoy the peaceful community or join in to the many activities available year round. The community offers two pools, two clubhouses, shuffleboard, tennis courts, bocci ball, miniature golf, and much, much more. Make your appointment today.

4235 Cedarwood Street, Winter Haven
4171 Rolling Oaks Drive, Winter Haven
$190,000
3 Beds ⋅ 3 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code
Welcome to this beautifully maintained 3-bedroom, 3-bath home located in the desirable Oakwood Estates, a gated 55+ community in Winter Haven, Florida! This spacious home offers an inviting open floor plan with comfortable living and dining areas, perfect for everyday living and entertaining. The kitchen features ample cabinetry, generous countertop space, and a functional layout. Each of the three bedrooms offers its own bathroom and walk-in closet, providing comfort, privacy, and convenience for family and guests. Enjoy the enclosed patio, ideal for relaxing or entertaining year-round. Additional features include a covered carport, a spacious workshop, and a dedicated laundry area. This home has numerous upgrades throughout and has been lovingly maintained! BEST OF ALL, YOU OWN THE LAND — NO LOT RENT! Enjoy the benefits of ownership with only a low monthly community fee. CO-OP COMMUNITY Oakwood Estates offers an active lifestyle with exceptional amenities, including a clubhouse, two swimming pools, fitness center, shuffleboard, tennis courts, and a full calendar of social activities. Conveniently located near shopping, dining, medical facilities, and major roadways, this home offers the perfect combination of comfort, convenience, and community living. Don’t miss this wonderful opportunity to enjoy Florida living at its finest! Schedule your private showing today! Watch the short video and explore the 360° Interactive Aerial Virtual Tour for an even closer look at this home and its surroundings. Enjoy the freedom to zoom in and out, explore the property from every angle, and see as far as the eye can see!

4171 Rolling Oaks Drive, Winter Haven
4234 Rolling Oaks Drive, 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
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
4242 Cedarwood Street, Winter Haven
$110,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code
Pack your bags and move right into this fully furnished home. You won't find any carpet in this well maintained home with new vinyl plank flooring in the living room, dining room, and kitchen. The refrigerator, dishwasher, and washer and dryer have been updated in the last few years. Sit on the bright and inviting front porch with your morning coffee. Oakwood Estates, a 55+ community offers many activities and amenities including 2 pools, 2 clubhouses, shuffleboard, tennis courts, miniature golf and bocci ball. Make your appointment to see this lovely home today!!

4242 Cedarwood Street, 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
4158 Rolling Oaks Drive, Winter Haven
$119,900
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
$124,000
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
4253 Cedarwood Street, Winter Haven
$97,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code
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 home is sold furnished with the items you see in the home when you tour it.

4253 Cedarwood Street, Winter Haven
4155 Sprucewood Street, Winter Haven
$115,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code
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.

4155 Sprucewood Street, Winter Haven
4918 Rosewood Street, Winter Haven
$125,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code
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. A new refrigerator was installed in Sept 2026. 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.

4918 Rosewood Street, Winter Haven
4239 Cedarwood Street, Winter Haven
$125,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code
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.

4239 Cedarwood Street, Winter Haven
Start Your Search

How much is your home worth?

Get instant property value now!