Oakwood Estates Real Estate

Oakwood Estates Real Estate

Welcome to Oakwood Estates, a serene and picturesque subdivision nestled in the heart of Florida. This charming community offers the perfect blend of tranquility and modern living, making it an ideal choice for families, retirees, and everyone in between.

As you enter Oakwood Estates, you are greeted by beautifully landscaped streets lined with mature oak trees that provide a natural canopy, creating a peaceful ambiance. The homes here are thoughtfully designed, featuring a variety of architectural styles that cater to diverse tastes. From elegant single-family homes to cozy townhouses, there’s something for everyone in this inviting neighborhood.

One of the standout features of Oakwood Estates is its commitment to community living. Residents enjoy access to well-maintained parks, walking trails, and recreational facilities that encourage an active lifestyle. Whether you prefer a leisurely stroll, a family picnic, or a game of basketball, there’s no shortage of outdoor activities to enjoy.

Location is key, and Oakwood Estates does not disappoint. Situated just a short drive from major highways, residents have easy access to the vibrant cities of Orlando and Tampa, where shopping, dining, and entertainment options abound. Additionally, the nearby beaches offer a perfect escape for sun-seekers and water enthusiasts.

Families will appreciate the quality of education available, with top-rated schools in close proximity. The welcoming atmosphere, combined with the strong sense of community, makes Oakwood Estates a place where neighbors become friends and memories are made.

Discover the charm of Oakwood Estates, where your dream home awaits amidst the beauty of Florida living!

Newest Listings in Oakwood Estates

$433,900
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. An oversized cul-de-sac homesite, 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
$114,995
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 & additional storage, creating the perfect space for showcasing your favorite pieces and hosting family & 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
$434,900
3 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 32043 Zip Code
Great Investment Opportunity. MODEL home offering a sale/leaseback. Welcome to the Drexel model at Oakwood Estates, situated on an oversized cul-de-sac homesite in the Lake Asbury area of Green Cove Springs. Twenty-four-month leaseback at 1% of the sales price per month rental income. This premium waterfront property features peaceful views of a community pond with a water feature. The home showcases impressive curb appeal with lush professional landscaping and a full front and rear irrigation system. Step through the covered entrance into a welcoming foyer highlighted by soaring 9-foot 4-inch ceilings that create an immediate sense of openness. At the heart of the home, the spacious great room is enhanced with LED flush-mount lighting and flows effortlessly into the beautifully appointed kitchen. Granite countertops, upgraded soft-close cabinetry, a decorative kitchen backsplash, a large center island, a generous pantry, and a full line of stainless steel appliances including an eSTAR® side-by-side refrigerator combine style with everyday functionality. An adjoining dining area provides a bright spot for morning coffee, while a flexible bonus room creates endless possibilities as a home office, hobby room, or reading retreat. Sliding glass doors extend the living space to the screened lanai, framing the scenic water backdrop. Privately situated, the primary owner's suite features an expansive walk-in closet and a deluxe bath with dual granite vanities, upgraded soft-close cabinetry, and a spacious tiled shower with a built-in bench. Two secondary bedrooms sit adjacent to a second full bath featuring a tiled tub and shower combination. Luxury vinyl flooring extends continuously throughout the home. A centrally located laundry room with an installed washer and dryer sits just off the two-car garage. Integrated smart home technology includes a Ring video doorbell, a smart thermostat, keyless entry, speakers & tv wall mount in the Great Room and Deako smart switches throughout. Energy-efficient construction highlights include insulated, low-emissive windows and architectural shingles, all backed by a full builder warranty. Beyond the home, the neighborhood provides pavilions, a playground, benches, and green spaces, alongside rapid commuting via the First Coast Expressway and premier boating and fishing on nearby Black Creek. Experience the craftsmanship, modern finishes, and thoughtful design of this exceptional Drexel Model Home. Schedule your private tour today. We can’t wait to welcome you home!

3395 Monarch Way, Green Cove Springs
$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
$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
$120,000
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
$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
$124,900
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
$129,000
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
$133,900
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code
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. UPDATE: New Linoleum flooring has just been professionally installed throughout the entire home to match the kitchen.

4212 Cedarwood Street, Winter Haven
$99,000
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
$74,900
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code
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.

4038 Rolling Oaks Drive, Winter Haven
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