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View 19 Oakwood Homes for Sale

Below you can view all the homes for sale in the Oakwood subdivision located in Winter Haven Florida. Listings in Oakwood are updated daily from data we receive from the Orlando multiple listing service.

To learn more about any of these homes or to receive custom notifications when a new property is listed for sale in Oakwood, give us a call at (407) 444-0331.

Viewing Homes 1 to 15 of 19

Oakwood | House For Sale $49,900

4218 Cedarwood St, Winter Haven, Florida 33880

Reduced By $5,000

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4218 Cedarwood St. Listed | 353 Days Ago
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    792

  • Year Built

    1981

  • $/SqFt

    $63

Well maintained 2br 2ba home in 5 Star Gated Community. We offer 2 pools, 2 clubhouses, Fishing, Mini Golf, Billiards, Cruises, Darts, Dinners, Dances and so much more. Just minutes to Winter Haven and easy access to Polk Parkway. Application for residency and government issued ID is required. Share price of $23,000 is included in list price. Transfer of share at a cost of $50.00 paid to Oakwood Associates. Buyers to be approved by Board of Directors of Oakwood Associates. 4627898

Heartland Rlty Prop Mgmt & Sal

Oakwood | House For Sale $69,500

4904 Rosewood St, Winter Haven, Florida 33880

Reduced By $3,000

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4904 Rosewood St. Listed | 144 Days Ago
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1080

  • Year Built

    1981

  • $/SqFt

    $64

A RARE FIND.....PERFECTION through out this gorgeous home. From the upgraded kitchen to the beautiful flooring to the exquisite detail this home is perfect. Lovingly maintained every room every detail is magazine perfection. Kitchen features wood cabinets, stone countertops, track lighting beautiful black appliances. Living room, Family Room, Florida Room, and Dining Room, inside laundry with workshop and last but not least a screen-room. Owner has installed new vinyl skirting and upgraded the landscape. Located in Beautiful Oakwood Community just minutes to all manners of entertainment, restaurants, Theme Parks, medical facilities and shopping. Oakwood Community offers any and all amenities imagined for making retirement life a dream come true. 4630903

Heartland Rlty Prop Mgmt & Sal

Oakwood | House For Sale $23,000

4307 Cherrywood St, Winter Haven, Florida 33880

4307 Cherrywood St. Listed | 234 Days Ago
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1080

  • Year Built

    1980

  • $/SqFt

    $21

LOT ONLY....LOT ONLY...NO VALUE IS PLACED ON MOBILE HOME.....MUST BE REMOVED FROM PROPERTY. Great Opportunity to join one of the best retirement communities in Central Florida. Our Community is 5 Star rated and offers anything and everything you will want to make your retirement a great one. We have two pools, 2 clubhouses, arts and crafts, pot luck dinners, line dancing, card nights, planned cruises, shopping trips, theater groups, beautiful lake for fishing...a great opportunity to slow down and enjoy Florida at its best. Application for residency is required. Government issued ID required. Share price of $23,000 is included in list price. Transfer of share at a cost of $50.00 paid to Oakwood Associates. Buyers to be approved by Board Of Directors of Oakwood Associates. 4629550

* Potential Great Value

Heartland Rlty Prop Mgmt & Sal

Oakwood | House For Sale $59,900

4435 Limewood St, Winter Haven, Florida 33880

Reduced By $3,100

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4435 Limewood St. Listed | 307 Days Ago
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1320

  • Year Built

    1983

  • $/SqFt

    $45

Nice 2br 2ba completely furnished home. Window treatments and ceiling fans thru-out. New laminate flooring in livingroom, bedrooms and diningroom. Located in 5 Star Senior Community conveniently located in Central Florida. Our community offers to you so many amenities such as Fishing from our private dock, mini golf, tennis, bocci ball, shuffleboard, dinners, luncheons, planned excursions to Little Theatre, Casinos, Cruises and so much much more. Come join us soon. $25.00 Application for residency is required. Government issued ID required. Share price of $23,000 is included in list price. Transfer of share at a cost of $50.00 paid to Oakwood Associates. Buyers to be approved by Board of Realtors of Oakwood Associates. 4628545

Heartland Rlty Prop Mgmt & Sal

Oakwood | House For Sale $54,900

4099 Rolling Oaks Dr, Winter Haven, Florida 33880

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4099 Rolling Oaks Dr. Listed | 161 Days Ago
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1056

  • Year Built

    1987

  • $/SqFt

    $51

Very nice home that backs up to the Nature area. Partially furnished, large Fla Room plus a Den. Inside workshop. Located in 55+ Gated Community of Oakwood Estates just minutes to Downtown Winter Haven. Centrally located, easy access to medical facilities, fine dining, Little Theatre and shopping. Our community features all amenities for keeping busy. Come join our wonderful community you will be glad you did. 4630650

Heartland Rlty Prop Mgmt & Sal

Oakwood | House For Sale $79,900

4176 Rolling Oaks Dr, Winter Haven, Florida 33880

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4176 Rolling Oaks Dr. Listed | 60 Days Ago
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1488

  • Year Built

    1985

  • $/SqFt

    $53

Large hard to find 3 bedroom 2 bath home. Living room and dining room combo, beautiful built ins, brkfst bar, island cook top, inside laundry, tile and carpet flooring. Completely furnished. Located in gorgeous Oakwood Gated Community just minutes to Winter Haven. Community feature all amenities from dinners to cruises...call today and tour our beautiful park. 4701114

Heartland Rlty Prop Mgmt & Sal

Oakwood | House For Sale $49,900

4167 Rolling Oaks Dr, Winter Haven, Florida 33880

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4167 Rolling Oaks Dr. Listed | October 14, 2014
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1176

  • Year Built

    1985

  • $/SqFt

    $42

Welcome to your Florida Home. You will find yourself right at home from the time you enter into this beautiful home. This is a red dot special home stop by office for more info on this. This community I can't say enough about from the horse shoe pits,tennis courts, 2 heated pools, 2 club houses, shuffle board, to much to mention. You can be as active or non-active as you want! They offer bingo, quilting for the sewer, cards. So what are you waiting for!start enjoying your retirement here at Oakwood Estates, with out paying the high price of a lease land home. (Welcome Home) 4700158

Southern Belle Realty

Oakwood | House For Sale $34,900

4325 Cherrywood St, Winter Haven, Florida 33880

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4325 Cherrywood St. Listed | 58 Days Ago
  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    816

  • Year Built

    1984

  • $/SqFt

    $42

Cute and Cuddly...2 bedroom 1.5 bath home with Florida Room. Fully furnished and located in Gated Community of Oakwood Estates. Just minutes to Winter Haven. We offer all types of amenities from arts and crafts to dancing lessons and dinner cruises. 4701137

Heartland Rlty Prop Mgmt & Sal

Oakwood | House For Sale $59,900

4115 Rolling Oaks Dr, Winter Haven, Florida 33880

Reduced By $30,000

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4115 Rolling Oaks Dr. Listed | 38 Days Ago
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1176

  • Year Built

    1981

  • $/SqFt

    $50

Beautiful home in Gated Community of Oakwood Estates....2br 2ba completely furnished...located just minutes to Winter Haven and the Polk Parkway...our community offers so many amenities such as Bingo, Dancing, Diners, Cruises, Card Night, Shufffleboard, Fishing, Mini Golf...stay as active or as relaxed as you want, swim in our Olympic size pool or relax with the family in our family pool. 4701477

Heartland Rlty Prop Mgmt & Sal

Oakwood | House For Sale $64,900

4119 Rolling Oaks Dr, Winter Haven, Florida 33880

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4119 Rolling Oaks Dr. Listed | 289 Days Ago
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1200

  • Year Built

    1984

  • $/SqFt

    $54

A "FIVE STAR" GATED, RESIDENT OWNED COMMUNITY IN WINTER HAVEN, FLORIDA!Own your lot with this spacious two bedroom two bath manufactured home, which offers the finest in carefree living in this 55+ community. It boasts a fabulous floor plan that features a large living room and master bedroom both with cathedral ceilings and the master has a huge walk-in closet, sink vanity, step-in shower. Nice dining area and breakfast nooks with laminate floors, as well as a family/bonus room. All new "tilt-in" insulated glass windows, architectural shingle roof (not aluminum or rubber), vinyl siding and a whole house water softening system. There's also an all-seasons room that has vinyl windows for year-round enjoyment, in addition to a screened lanai, both with an awesome view of the country. Additional features include a carport, a workshop/laundry room and more. Situated in beautiful Oak Wood Estates HOA fees include water/sewer, and park maintenance. This home is one you won't want to miss seeing. This community is a very well maintained "Five Star" 55+ community that has tons of activities & amenities which includes; 2 solar heated swimming pools, shuffleboard courts, two clubhouses, library, fishing dock, a mini golf course, horse shoe pit, card clubs, bingo, golf and much, much more. It offers something for everyone! The park is in the center of everything...Near Tampa, Orlando International Airport, Disney, Universal Studios, Sea World, and Legoland. 5201891

Charles Rutenberg Realty

Oakwood | House For Sale $45,000

4345 Cherrywood St, Winter Haven, Florida 33880

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4345 Cherrywood St. Listed | 38 Days Ago
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    816

  • Year Built

    1984

  • $/SqFt

    $55

Nice 2br 2ba home completely furnished located in beautiful gated community offering all amenities such as Mini Golf, Pot Luck Dinners, Shopping Trips, Bingo, Dancing, great location for day trips to Atlantic Ocean or the sparkling beaches of the Gulf. 4701483

Heartland Rlty Prop Mgmt & Sal

Oakwood | House For Sale $69,900

4097 Rolling Oaks Dr, Winter Haven, Florida 33880

Reduced By $5,000

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4097 Rolling Oaks Dr. Listed | 38 Days Ago
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1080

  • Year Built

    1985

  • $/SqFt

    $64

Beautiful home 2Br 2Ba new air unit, dishwasher, new flooring and new refrigerator and newly resurfaced driveway. Wonderfully maintained and ready for you. Located in Gated Community offering all types of amenities..Dinners, dancing, Mini Golf, Fishing, Tennis, Cards and so much more. Convenient Central Florida location less than 2 hours from the Atlantic Ocean and the beautiful Gulf. 4701479

Heartland Rlty Prop Mgmt & Sal

Oakwood | House For Sale $39,900

4151 Sprucewood St, Winter Haven, Florida 33880

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4151 Sprucewood St. Listed | 375 Days Ago
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    864

  • Year Built

    1982

  • $/SqFt

    $46

SUper nice 2br 2ba home located in great community. Community offers 2 pools, 2 clubhouses, pot luck dinners, Bingo, planned excursions. Convenient Central Florida Location. Just minutes to restaurants, Little Theatre, Shopping, medical facilities and LEGOLAND. Less than 2 hours to the beautiful Atlantic Ocean and to the sparkling waters of the Gulf of Mexico. Call today for your special tour. 4627553

Heartland Rlty Prop Mgmt & Sal

Oakwood | House For Sale $44,900

4076 Rolling Oaks Dr, Winter Haven, Florida 33880

Reduced By $10,000

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4076 Rolling Oaks Dr. Listed | 376 Days Ago
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1056

  • Year Built

    1983

  • $/SqFt

    $42

Nice 2br 2ba furnished home. Located in Beautiful Community offering 2 community pools, fishing on serene Dinner Lake, mini golf, dances, Bingo, planned excursions, pot luck dinners, gorgeous Ladies Luncheons, we have arts and crafts, dances and lots of fun every day. Conveniently located in Central Florida where you are just 2 hours from either the Gorgeous Gulf of Mexico and the beautiful beachs of the Atlantic. Just minutes to medical facilites, restaurants, shopping and much much more. Come join our beautiful 5 Star gated community. 4627534

Heartland Rlty Prop Mgmt & Sal

Oakwood | House For Sale $49,000

4148 Sprucewood St, Winter Haven, Florida 33880

Reduced By $4,000

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4148 Sprucewood St. Listed | 409 Days Ago
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    864

  • Year Built

    1982

  • $/SqFt

    $56

Perfect Retirement Location.5 Star Gated Community. Well maintained home with Laminate Floors, New Sinks, New Faucets,New Medicine Cabinets, Newer Water Heater and new plumbing. Just minutes to access Polk Parkway. Easy drive of 2 hours to either the beautiful Atlantic Ocean to the east and the sparkling Gulf of Mexico to the west. Spend the day at the beach and be home in time for dinner. 4627064

Heartland Rlty Prop Mgmt & Sal

Viewing Homes 1 to 15 of 19