Oakwood Estates Real Estate

Oakwood Estates Real Estate

Welcome to Oakwood Estates, a hidden gem nestled in the heart of Florida! This picturesque subdivision offers a perfect blend of tranquility and modern living, making it an ideal choice for families, retirees, and anyone looking to embrace the Sunshine State lifestyle.

Oakwood Estates is characterized by its beautifully landscaped streets, charming homes, and a strong sense of community. Each residence is thoughtfully designed, showcasing a variety of architectural styles that cater to diverse tastes. From cozy single-family homes to spacious properties with lush backyards, there’s something for everyone in this enchanting neighborhood.

One of the standout features of Oakwood Estates is its prime location. Residents enjoy easy access to a wealth of local amenities, including shopping centers, restaurants, and recreational facilities. The nearby parks and nature trails provide ample opportunities for outdoor activities, whether it’s a leisurely stroll, a family picnic, or a weekend hike. For those who love the beach, you’re just a short drive away from Florida's stunning coastline, where you can soak up the sun or enjoy water sports.

Community spirit thrives in Oakwood Estates, with regular neighborhood events and gatherings that foster camaraderie among residents. Families can take advantage of excellent schools in the area, ensuring that children receive a top-notch education.

In Oakwood Estates, you’ll find not just a home, but a vibrant community that embraces the best of Florida living. Come explore this delightful subdivision and discover the perfect place to create lasting memories!

Newest Listings in Oakwood Estates

1737 Oakwood Estates Drive, Plant City
$445,000
4 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33563 Zip Code
Step into a home where pride of ownership is evident throughout and the backyard feels like something straight off a postcard! This beautifully maintained 4-bedroom home offers an exceptional blend of comfort, style, and outdoor living. The oversized primary suite provides plenty of room for additional seating, creating a relaxing private retreat, while the tastefully remodeled primary bathroom adds a touch of elegance. But the real magic happens outside! The spectacular backyard features a 44-foot sports pool, heated with both electric and gas systems, creating the perfect setting for year-round enjoyment. The custom-designed pool nook with a permanently attached table comfortably seats six, making it ideal for cards, conversation, and gatherings with family and friends. With no traditional pool ledges, the pool offers a distinctive design, while the six-person hot tub creates an added touch of luxury with a beautiful waterfall cascading directly into the pool. Two propane fire torches provide a warm, inviting ambiance after sunset, and the covered patio offers a comfortable space to relax and enjoy the outdoor surroundings. This is more than a beautifully kept home; it's a place to enjoy, entertain, and make lasting memories.

1737 Oakwood Estates Drive, Plant City
4157 Rolling Oaks Drive, Winter Haven
$118,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code
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. The roof 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.

4157 Rolling Oaks Drive, Winter Haven
1703 Oakwood Estates Drive, Plant City
$375,000
4 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33563 Zip Code
Welcome to 1703 Oakwood Estates Dr! Located in a gated community in the heart of Plant City, this 4-bedroom, 2-bath home features a desirable split-bedroom floor plan and a versatile bonus room offering additional space to suit your needs. The home also includes solar panels, offering the potential for energy savings. Enjoy the privacy of a fenced backyard, perfect for outdoor relaxation, entertaining, or creating your own private retreat. Conveniently situated between Tampa and Lakeland, this home provides convenient access to both cities for commuting, shopping, dining, and everyday essentials. With a functional layout, added flexibility, and a convenient location, this home is a fantastic opportunity and is priced to sell! Don’t miss your chance to make it yours!

1703 Oakwood Estates Drive, Plant City
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
3422 Monarch Way, Green Cove Springs
$389,900
4 Beds ⋅ 3 Baths ⋅ Oakwood Estates SubDv. ⋅ 32043 Zip Code
Pre-Construction. To be built. Discover the Miramar at Oakwood Estates, a premier new-home community in Green Cove Springs featuring quality construction, modern smart home technology, and oversized cul-de-sac homesites. The Miramar showcases an open-concept design with 9’4” ceilings, a deluxe interior trim package, and a distinctive stone exterior accent. The spacious Great Room features triple sliding glass doors leading to a covered lanai, while the kitchen impresses with quartz countertops, a large center island, soft-close cabinetry, stainless steel appliances, and a generous pantry. The private primary suite includes a walk-in closet and an en-suite bath with an oversized tiled shower, separate tub, and linen closet. Three additional bedrooms, including one with a private bath, provide versatile space, complemented by a secondary bathroom with a tile shower and tub combination and a centrally located laundry room. Smart Home features include a Kwikset Keyless Door Entry, Honeywell Thermostat, and Deako Switches. A two-car garage, architectural shingles, insulated low-emissivity windows, landscaping, front and rear irrigation, and a full builder warranty complete the home. Oakwood Estates features flexible multi-generational floor plans, a community playground, pavilions, and green spaces. Located near the First Coast Expressway, the community also provides commuting options and access to boating and fishing opportunities at Black Creek and in Jacksonville. Schedule your private tour of the Miramar at Oakwood Estates today! We can’t wait to welcome you home!

3422 Monarch Way, Green Cove Springs
3418 Monarch Way, Green Cove Springs
$443,900
4 Beds ⋅ 3 Baths ⋅ Oakwood Estates SubDv. ⋅ 32043 Zip Code
Under Construction. Set within Oakwood Estates in Green Cove Springs, the Carlisle showcases an expansive two-story layout filled with refined finishes, upgraded features, smart home technology, and inviting indoor-outdoor living. Professional landscaping, irrigation system, community playground, pavilions, and green spaces add to the appeal, while a full new home warranty provides added peace of mind. From the moment you arrive, the stone-accent exterior, covered front porch, and architectural shingles create an impressive first impression. Step through the elegant foyer and into a thoughtfully designed interior where natural light, additional windows, and upgraded LED lighting enhance the spacious living areas. A versatile Flex Space just off the foyer provides added room for work, hobbies, or everyday activities. A convenient half bath is also located on the main level near the stairs, with additional storage tucked beneath the staircase. The open-concept great room flows seamlessly into the chef-inspired kitchen, creating a spacious central gathering area. The kitchen features quartz countertops, a large island, tile backsplash, upgraded soft-close cabinetry, a walk-in pantry, and stainless steel appliances. A bright breakfast nook just off the kitchen adds a cheerful dining space, while the great room extends outdoors to a screened-in lanai overlooking the beautifully landscaped backyard. Upstairs, a spacious loft provides additional living space alongside four well-appointed bedrooms. Bedrooms 3 and 4 share a Jack and Jill bathroom featuring a tile tub and shower combination with dual vanities. The impressive primary suite creates a private retreat with a spacious walk-in closet and spa-inspired bathroom featuring an oversized ceramic tile shower wall surround, separate tub, quartz countertops, and upgraded soft-close cabinetry. The upstairs laundry room adds convenience to the second level. Smart home features include a Ring Video Doorbell, Smart Thermostat, Keyless Entry Smart Door Lock, and DEAKO Smart Switches. Combined with the upgraded finishes, thoughtful storage, enhanced lighting, screened-in lanai, landscaping, and irrigation system, every detail contributes to a polished and functional living experience. Backed by a full builder warranty, this exceptional new construction home brings together spacious living, elevated finishes, and thoughtful design in Oakwood Estates. Enjoy the scenic setting and recreational opportunities of Green Cove Springs in the Lake Asbury area, along with the attractions and conveniences throughout Jacksonville. Schedule your private tour today and experience the Carlisle firsthand. We can’t wait to welcome you home!

3418 Monarch Way, Green Cove Springs
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
$99,000
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
$135,000
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
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