The best assisted living facilities in Oakland, FL

    Explore 19 communities near Oakland, FL

    1. Sunny exterior view of The Summit of Winter Garden entrance with columns and palm trees.
      4.8(60)
      $4,182 – $5,436+
      Shared • 1 Bedroom • Studio
      independent living, assisted living

      The Summit of Winter Garden

      420 Roper Rd, Winter Garden, FL 34787
    2. Exterior view of Inspired Living Ocoee, a multi-story senior living facility with a covered entrance, landscaped garden with palm trees, and an American flag on a flagpole in front.
      4.5(213)
      $5,053 – $6,568+
      Shared • 1 Bedroom • Studio
      independent, assisted living, memory care

      Inspired Living Ocoee

      1061 Tomyn Blvd, Ocoee, FL 34761
    3. Exterior view of a senior living facility named Serenades at West Orange, featuring a yellow building with white trim, a covered entrance supported by white columns, palm trees, and a clear blue sky.
      4.7(87)
      $5,400+
      Shared
      assisted living, memory care

      Serenades at West Orange

      720 Roper Rd, Winter Garden, FL 34787
    4. Single-story beige residence with red door, front porch seating, shrubs, and a grassy yard.
      4.3(66)
      $4,540 – $5,902+
      Shared • 1 Bedroom • Studio
      assisted living, memory care

      Hunt Trace Senior Living

      1600 Hunt Trace Blvd, Clermont, FL 34711
    5. Exterior front view of Benton House of Clermont with entrance, parking, and landscaping.
      4.3(82)
      $3,987 – $5,183+
      Shared • 1 Bedroom • Studio
      assisted living, memory care

      Benton House of Clermont

      16401 Good Hearth Blvd, Clermont, FL 34711
    6. Front exterior view of Orchard Heights Gracious Retirement Living building with a covered entrance, palm trees, and landscaped flower beds under a clear blue sky.
      4.4(82)
      $2,295 – $4,235+
      Studio • 1 Bedroom • 2 Bedroom
      continuing care retirement community

      Orchard Heights Gracious Retirement Living

      3650 S Hwy 27, Clermont, FL 34711
    7. Exterior view of Alto Clermont senior living building along a road with landscaping.
      4.0(136)
      $4,827 – $6,275+
      Shared • 1 Bedroom • Studio
      assisted living, memory care

      Alto Clermont – Clermont, FL

      1601 Hooks St, Clermont, FL 34711
    8. Two-story white senior living facility building photographed at dusk with illuminated windows, palm trees, and an adjacent parking lot.
      4.4(103)
      $4,250 – $6,475+
      1 Bedroom • 2 Bedroom
      assisted living, memory care

      The Blake at Hamlin

      4814 Hamlin Groves Tr, Winter Garden, FL 34787
    9. Front entrance of a single-story senior living building with white columns and a green roof lit at dusk.
      4.4(97)
      $4,390 – $5,707+
      Shared • 1 Bedroom • Studio
      assisted living, memory care, skilled nursing

      Golden Pond Communities

      402 Lakeview Rd, Winter Garden, FL 34787
    10. Covered metal-and-fabric walkway ramp leading to the entrance of a brick nursing facility with landscaping on either side.
      4.1(248)
      Pricing on request
      suite
      assisted living, memory care, skilled nursing

      Winter Garden Rehabilitation and Nursing Center

      12751 W Colonial Dr, Winter Garden, FL 34787
    11. Sunlit entrance of The Lakes of Clermont senior living facility with a porte-cochere and palm trees.
      4.4(394)
      Pricing on request
      suite
      assisted living, memory care, skilled nursing, board and care

      The Lakes of Clermont

      1775 Hooks St, Clermont, Florida 34711
    12. $3,546 – $4,255+
      Shared • 1 Bedroom
      assisted living

      Caring Hearts Helping Hands Assisted Living

      215 Pleasant Hill Dr, Clermont, FL 34711
    13. $3,425 – $4,110+
      Shared • 1 Bedroom
      assisted living

      Discovery Practice Management

      14915 Fosgate Rd, Montverde, FL 34756
    14. $3,934 – $4,720+
      Shared • 1 Bedroom
      assisted living

      Supreme Senior Living

      502 Southridge Rd, Clermont, FL 34711
    15. Pricing on request
      suite
      independent, assisted living, memory care

      The Roberson

      11801 Roberson Rd, Ocoee, FL 34787
    16. $3,806 – $4,567+
      Shared • 1 Bedroom
      assisted living, board and care

      The Gardens at Montverde

      15425 Cr 455, Montverde, FL 34756
    17. Front view of a single-story yellow senior living building with palm trees and a green lawn
      4.0(4)
      Pricing on request
      suite
      assisted living

      Gardens at Oakland

      715 Hull Island Dr, Oakland, FL 34787
    18. Exterior view of Vivo Healthcare West Orange with canopies, palms, and manicured landscaping.
      3.9(272)
      Pricing on request
      suite
      assisted living, memory care, skilled nursing

      Vivo Healthcare West Orange

      1556 Maguire Rd, Ocoee, FL 34761
    19. Outdoor sign for Award Care at Colonial Lakes Rehabilitation & Care Center with trees nearby.
      3.4(177)
      Pricing on request
      suite
      assisted living, memory care, skilled nursing

      Aviata at Colonial Lakes

      15204 W Colonial Dr, Winter Garden, FL 34787

    Cost of assisted living in Oakland, Florida

    Studio1 Bd2 BdShared
    Independent Living—$5,541—$4,618
    Assisted Living—$5,002$6,475$4,354
    Memory Care—$5,268$6,475$4,700

    * Prices shown are average monthly costs within a 20-mile radius

    Consider other types of facilities in Oakland, FL

    • Independent Living

      For older adults who want to enjoy a carefree retirement in a community of their peers

    • Memory Care

      A safe, supervised community supporting people living with dementia

    • Skilled Nursing

      For seniors with more serious medical needs who require skilled care following a hospitalization, illness, or surgery.

    • Board And Care Homes

      Homes in residential neighborhoods providing daily care for a small number of residents

    • Continuing Care Retirement Communities

      For seniors who want to age in place as their care needs evolve, offering everything from independent living to full nursing care.

    Nearby Cities

    1. 20 facilities$4,952/mo
    2. 20 facilities$4,952/mo
    3. 15 facilities$4,791/mo
    4. 16 facilities$4,540/mo
    5. 13 facilities$4,750/mo
    6. 35 facilities$4,404/mo
    7. 14 facilities$4,695/mo
    8. 35 facilities$4,672/mo
    9. 28 facilities$4,764/mo
    10. 43 facilities$4,421/mo
    11. 29 facilities$4,293/mo
    12. 4 facilities$4,814/mo
    © 2026 Mirador Living