Oakwood Estates Homes with Shingle Roof

Oakwood Estates Homes with Shingle Roof

Welcome to Oakwood Estates, a hidden gem nestled in the heart of Florida, where charm meets modern living. This picturesque subdivision is renowned for its serene ambiance and beautiful landscapes, making it the perfect place for families, retirees, and everyone in between. With tree-lined streets and meticulously manicured lawns, Oakwood Estates offers a sense of community that is both inviting and warm.

One of the standout features of the homes in Oakwood Estates is their stunning shingle roofs, which not only enhance the aesthetic appeal of each residence but also provide durability and protection against Florida’s unique weather patterns. These homes are designed with both style and functionality in mind, featuring spacious layouts, modern amenities, and plenty of natural light. Whether you’re looking for a cozy single-family home or a larger property to accommodate your growing family, Oakwood Estates has something to suit every lifestyle.

Residents of Oakwood Estates enjoy easy access to a variety of local attractions, including parks, shopping centers, and dining options that cater to every palate. The community is also conveniently located near major highways, providing quick access to nearby cities and the beautiful Florida coastline.

Join a vibrant community where neighbors become friends, and create lasting memories in your dream home at Oakwood Estates. Discover the perfect blend of comfort, style, and community in this enchanting subdivision, where the beauty of Florida living awaits you!

Newest Oakwood Estates Homes with Shingle Roof

2 Beds ⋅ 2 Baths ⋅ L4964514 MLS

OVER $19,000 IN RECENT UPGRADES MEANS THE BIG-TICKET WORK HAS ALREADY BEEN DONE! This fully furnished Oakwood Estates home features a new roof (2023), plus new HVAC, electric water heater, rain gutters, and exterior porch tile (2024). Step inside to a bright, welcoming interior filled with natural light from double-pane windows. Luxury vinyl plank flooring flows throughout. The kitchen features stainless steel appliances, white cabinetry, wood-look countertops, and a newer sink. Built-in cabinetry adds charm and storage to the dining area, which opens to a spacious living room. Both bedrooms are generously sized, with a walk-in closet in the primary. A separate laundry room includes the washer and dryer. Enjoy additional living space in the Florida room and enclosed lanai, perfect for relaxing and enjoying the Florida lifestyle. Hurricane shutters, vinyl siding, and an updated electrical panel add even more value. Oakwood Estates is a gated, resident-owned 55+ community with two heated pools, two clubhouses, pickleball and tennis courts, shuffleboard, bocce ball, miniature golf, a fishing lake and pier, RV and boat storage, library, activities center, and an active social calendar. Major updates done, furnishings included, and ready for you to move in and enjoy!

4332 Cherrywood Street, Winter Haven

4 Beds ⋅ 3 Baths ⋅ O6433473 MLS

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

2 Beds ⋅ 2 Baths ⋅ P4939511 MLS

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

2 Beds ⋅ 2 Baths ⋅ P4939139 MLS

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

2 Beds ⋅ 2 Baths ⋅ P4939076 MLS

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

2 Beds ⋅ 2 Baths ⋅ P4938951 MLS

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

2 Beds ⋅ 2 Baths ⋅ A4692973 MLS

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, along with new baseboards.

4212 Cedarwood Street, Winter Haven

2 Beds ⋅ 2 Baths ⋅ P4938247 MLS

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

2 Beds ⋅ 2 Baths ⋅ P4937684 MLS

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.

4228 Cedarwood Street, Winter Haven

2 Beds ⋅ 2 Baths ⋅ B4902100 MLS

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.

4179 Rolling Oaks Drive, Winter Haven

2 Beds ⋅ 2 Baths ⋅ O6325757 MLS

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)

4246 Cedarwood Street, Winter Haven

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