Oakwood Estates Real Estate

Oakwood Estates Real Estate

Welcome to Oakwood Estates, a hidden gem nestled in the heart of Florida, where tranquility meets modern living. This charming subdivision offers a perfect blend of natural beauty and contemporary amenities, making it an ideal place for families, retirees, and everyone in between.

As you enter Oakwood Estates, you are greeted by lush landscapes and tree-lined streets that create a warm and inviting atmosphere. The community features a variety of beautiful homes, each thoughtfully designed to cater to diverse lifestyles. From spacious single-family residences to cozy townhomes, there’s a perfect fit for everyone in this close-knit neighborhood.

Residents of Oakwood Estates enjoy access to an array of amenities that enhance the quality of life. Take a leisurely stroll through the scenic parks, where children can play and families can gather for picnics. The community clubhouse serves as a social hub, hosting events and activities that foster connections among neighbors. For those who appreciate an active lifestyle, there are walking trails and recreational facilities that encourage outdoor fun.

Conveniently located, Oakwood Estates is just a short drive from local shopping, dining, and entertainment options. With easy access to major highways, commuting to nearby cities is a breeze, making it an ideal location for those who work in bustling urban areas but prefer the peace of suburban living.

Experience the charm and community spirit of Oakwood Estates, where every day feels like a retreat. Come discover your dream home in this delightful Florida subdivision, and embrace a lifestyle filled with warmth, comfort, and endless possibilities.

Newest Listings in Oakwood Estates

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 and additional storage, creating the perfect space for showcasing your favorite pieces and hosting family and 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

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

2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code

A Home That's Ready When You Are — Oakwood Estates, Winter Haven Some of life's best decisions are also the simplest ones. This lovingly maintained, fully furnished manufactured home in Oakwood Estates invites you to skip the hassle and step straight into the lifestyle you've been looking forward to — because everything has already been taken care of, and everything stays. Fresh interiors, thoughtful updates, and a warm, welcoming layout make this one of the most effortless purchases you'll make. Step inside and you're immediately greeted by natural light pouring through double-pane windows, setting a bright, airy tone throughout. The kitchen shines with stainless steel appliances, wood-look countertops, a newer sink, and crisp white cabinetry — and yes, everything stays, right down to the air fryer. The dining area features beautiful built-in cabinetry and shelving, flowing seamlessly into a spacious living room complete with an electric reclining sofa, flat screen TV, and comfortable seating. Luxury vinyl plank flooring runs throughout, tying it all together with style and ease of maintenance. Both bedrooms are generously sized and fully furnished. The primary suite features a walk-in closet, electric reclining bed, and a quality foam mattress. The Florida room offers updated ceiling fans, a brand-new AC unit, and convenient access to the in-home washer and dryer hookups — a true bonus in this community. Slide open the door to the enclosed lanai and enjoy your morning coffee overlooking lush, manicured landscaping — your own quiet corner of Florida. Additional highlights include hurricane shutters, vinyl siding, a 2017 roof, an irrigation system, and an updated electrical panel for peace of mind. Then there's the community. Oakwood Estates is a gated, beautifully maintained 55+ resident-owned community in the heart of Winter Haven — one of Polk County's most desirable areas. Residents enjoy two heated pools, two clubhouses, tennis and pickleball courts, shuffleboard, bocce ball, a miniature golf course, horseshoes, a fishing lake with pier, RV and boat storage, a library and activities center, pool tables, and a vibrant, active activities committee that keeps the social calendar full year-round. Lighted streets, underground utilities, and security cameras throughout the common areas reflect a community that takes pride in where it lives. This is Florida living, fully loaded and ready to go.

4332 Cherrywood Street, Winter Haven

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

3 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33810 Zip Code

Welcome to this beautifully remodeled 3-bedroom, 2-bath manufactured home offering 1,456 square feet of living space on a spacious 0.54-acre lot that you own! Fully fenced for added privacy, this move-in-ready property offers plenty of room for outdoor living, pets, recreational vehicles, and more. Step inside to a bright, modern interior featuring luxury vinyl plank flooring, recessed lighting throughout, and beautifully updated bathrooms with contemporary tile finishes. The remodeled kitchen is designed for both everyday living and entertaining, featuring quartz countertops, a large cooking island, ample cabinet space, and all kitchen appliances included. The convenient indoor laundry area provides easy access, while the versatile bonus room can be used as a home office, playroom, gym, or additional living space. Major improvements include a TPO membrane roof installed in 2025, a new well installed in November 2024, and the septic tank pumped in May 2026. Enjoy the freedom of country-style living with NO HOA and NO CDD, while remaining conveniently located in North Lakeland near shopping, dining, recreation, and the I-4 corridor connecting Tampa and Orlando. With extensive updates, over half an acre of owned land, a fully fenced yard, and plenty of flexible living space, this home is ready for its next owner. Schedule your private showing today!

3817 Ward Road, Lakeland

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

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

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

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

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

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

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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