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$139,900
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv.
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
$125,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv.
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
$70,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv.
New Carpet throughout most of the home. Plus many of the windows have been updated to thermal pane insulated windows. If that is not enough the TPO roof was installed in December 2023. The home has a nice layout with a huge primary bedroom with huge walk in closet. Location is convenient in Oakwood Estates, a 55+ community, right across from the office and close proximity to one of the pools. Enjoy the many amenities at Oakwood including two pool, two clubhouses, miniature golf, fishing pier, shuffleboard and much, much more. Join in on the many activities including weekly Koffee Klatch, potluck meals, and dances. The two heated pools offer many hours of relaxation. Or just sit out on the screened front porch and watch the world go by. This home is priced to sell. Check it out today!!

4027 Rolling Oaks Drive, Winter Haven
$110,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv.
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.
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.
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.
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.
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
$99,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv.
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 rocker recliner in the living room and TVs do not convey.

4253 Cedarwood Street, Winter Haven
$74,900
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv.
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
$110,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv.
Check this out!! The home has new vinyl plank and new carpet in the bedrooms and a new roof in 2025. Enjoy the nice sized living room with relaxing cool blue paint and chair rail. Additionally there is a built in for additional storage and display area for your trinkets. The kitchen offers a nice flooring, with upgraded countertops and lots of cabinets and storage. The hall bathroom has been upgraded with vinyl plank and a custom shower. The primary bathroom offers nice space and a walk in closet. All the floors have plywood subfloors with vinyl plank or carpet. The back porch on the home has been framed in and divided into two office spaces. The walls at the back of the house are freestanding and can be easily removed revealing the glass behind them. Step out the back door onto a covered porch area allowing access to the shed that houses the washer and dryer. Oakwood Estates, a 55+ community, offers many activities and amenities. You can be as active as you would like or just sit back and watch the world go by. The Seller is a smoker inside the home. Please beware if you have smoke allergies.

4173 Rolling Oaks Drive, Winter Haven
$120,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv.
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
$125,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv.
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. 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
$125,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv.
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
$119,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv.
Pack your bags and move right into this fully furnished home. This home has many updates!! Although the bedrooms have updated carpets there is nice wood laminate flooring throughout the main living areas with plywood subfloor. The baths and front porch area have updated tile flooring. The kitchen has newer appliances, a beautiful mosaic backsplash and updated counter tops. All the windows are updated with double pane, thermal, tilt in windows. The updated entry door has blinds between the half glass that you can open for the light or close for privacy. Both bathrooms have updated vanities. Enjoy the updated and modern light fixtures. The HVAC was installed in July 2023. The roof is a roof over adding extra insulation value to the home. Oakwood Estates is an active 55+ communities offering many amenities as well as activities. You can be as busy as you would like or just sit back and enjoy the peacefulness of the community.

4056 Rolling Oaks Drive, Winter Haven
$118,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv.
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
$90,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv.
Priced to sell, Home has a new metal roof, CHA is approximately five years old, and you will feel right at home from the moment you walk in. Come enjoy the beautiful Florida sunsets in this 55+ gated, five-star park.

4165 Rolling Oaks Drive, Winter Haven
$106,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv.
What an amazing home just waiting for it's new owner!! The kitchen has been completely updated with new cabinets and flooring. The home offers two additional living spaces. The lanai on the side of the home is vented with the central ac and is included in the total square footage. or you can escape to the front porch which is also vented increasing the square footage by an additional 200 sf bringing the total living area to 1216 sf. The primary bathroom has an updated vanity. The laundry is located behind the side lanai so you don't have to go outside. The air conditioner is brand new in December 2025. This home is located in Oakwood Estates, a 55+ community which offers many amenities and activities. You can stay as busy as you like, or just sit back and enjoy the peaceful community.

4251 Cedarwood Street, Winter Haven
$85,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv.
Great home with an open living space ready for it's next owner. This home has a fresh coat of paint and is a blank slate for it's new owners. Sit on the front porch and enjoy your morning coffee. The rooms are nice sized with great closet space. The laundry/shop area has plenty of space for your Do-it-yourself projects. Oakwood Estates, a 55+ community offers 2 pools, 2 clubhouses, shuffleboard, tennis courts, miniature golf, and much more. In addition to the amenities, Oakwood offers many opportunities to meet with new folks. Come to Koffee Klatch on Wednesday morning, enjoy an ice cream social a couple times a month, or get your Boogie on at one of the dances. Call today to view this home that's just waiting for YOU!!

4127 Sprucewood Street, Winter Haven
$108,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv.
Walk right into this open and spacious home. The kitchen is perfect for entertaining with newer cabinets and cooktop. The cathedral ceilings in the living room give the feel of lots of space. The floorplan offers 2 living areas. The guest bedroom has the main bathroom attached which is perfect for those overnight guests. The primary bedroom is spacious with two separate closets for him and her with a nice sized shower stall in the primary bathroom. The shingle roof was installed in 2021. The vapor barrier was replaced in 2023 and the home has new skirting. The side porch offers more living space and is backed with a great workshop area. The laundry is inside the home. If all that isn't enough there is an EV charging port installed. This home is located in Oakwood Estates, a 55+ community offering many activities or just sit back and enjoy the peaceful community. Make your appointment today!! This home will be sold unfurnished with appliances only.

4321 Cherrywood Street, Winter Haven