Trail, Winter Garden, FL 34787
OFF MARKET

Trail
Winter Garden, FL 34787

    $1,876,400

    Trulia Estimate
    as of Aug 23, 2026
    Est. Refi. Payment $13,072/mo*
    Refinance Your Home

    $1,876,400

    Trulia Estimate
    as of Aug 23, 2026
    Est. Refi. Payment $13,072/mo*
    Refinance Your Home

    Home Value

    Trulia Estimate
    $1.88M
    Since last month
    Increased$19K (+1%)
    Since last year
    Increased$785K (+71.6%)
    Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

    Trulia Estimate

    The of this home's value increased by +29% in the last 10 years
    MonthEstimated value
    2026
    August 2026$1.88M
    July 2026$1.86M
    June 2026$1.88M
    May 2026$1.89M
    April 2026$1.9M
    March 2026$1.86M
    February 2026$1.89M
    January 2026$1.74M
    2025
    2024

    Comparable sales

    These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
    Address
    Distance
    Property Type
    Sold Price
    Sold Date
    Bed
    Bath
    Sqft
    1185 WILDER OAKS WAY, Oakland, FL
    0.08
    Single-Family Home
    $999,000
    02/17/26
    4
    3.5
    2,789
    1207 RIDGE LAKE WAY, Oakland, FL
    0.09
    Single-Family Home
    $1,700,000
    04/09/26
    5
    3.5
    3,909
    1108 RIVERWAY DRIVE, Oakland, FL
    0.13
    Single-Family Home
    $1,025,000
    07/15/26
    5
    3
    2,999
    1127 CELADON STREET, Oakland, FL
    0.13
    Single-Family Home
    $1,490,000
    03/05/26
    4
    3.5
    2,730
    1143 BULWARK OAKS LANE, Oakland, FL
    0.14
    Single-Family Home
    $1,159,532
    09/26/25
    5
    4.5
    4,436
    1096 RIVERWAY DRIVE, Winter Garden, FL
    0.14
    Single-Family Home
    $1,575,000
    01/23/26
    4
    3.5
    4,171
    413 MACCHI AVENUE, Oakland, FL
    0.15
    Single-Family Home
    $840,000
    08/29/25
    4
    3
    3,290
    100 DEMENS STREET, Oakland, FL
    0.17
    Single-Family Home
    $950,000
    09/23/25
    4
    3
    3,025
    102 HAMMOCK PRESERVE LOOP, Oakland, FL
    0.18
    Single-Family Home
    $1,660,000
    10/23/25
    6
    5
    3,911
    1219 SADDLEBACK DRIVE, Oakland, FL
    0.20
    Single-Family Home
    $1,040,000
    07/20/26
    4
    3.5
    2,667

    Nearby home prices

    Get a sense of expected prices in the area by checking the value of nearby homes.
    Address
    Distance
    Price
    Bed
    Bath
    Sqft
    Status
    1094 RIDGE LAKE WAY, Oakland, FL 34787
    0.04
    $1,319,800
    5
    4.5
    4,071
    Off Market
    1086 TRAIL, Oakland, FL 34787
    0.00
    $1,782,600
    4
    5
    3,794
    Off Market
    1258 RIDGE LAKE WAY LOT 263, Winter Garden, FL 34787
    0.04
    -
    -
    -
    -
    Off Market
    1142 RIDGE LAKE WAY, Oakland, FL 34787
    0.04
    $978,600
    4
    3.5
    2,683
    Off Market
    1264 RIDGE LAKE WAY LOT 247, Winter Garden, FL 34787
    0.01
    $500,000
    -
    -
    -
    Recently Sold
    1167 WILDER OAKS WAY, Oakland, FL 34787
    0.06
    $844,500
    3
    2.5
    2,254
    Off Market
    1112 Ridge Lake Way, Oakland, FL 34787
    0.06
    $838,200
    4
    3.5
    2,527
    Off Market
    1106 Ridge Lake Way, Oakland, FL 34787
    0.08
    $1,326,200
    5
    4
    3,633
    Off Market
    1082 OAK RIM LANE, Winter Garden, FL 34787
    0.09
    $1,059,400
    4
    3
    2,640
    Off Market
    1221 WILDER OAKS WAY, Winter Garden, FL 34787
    0.06
    $798,600
    4
    3
    2,240
    Off Market
    1197 WILDER OAKS WAY, Oakland, FL 34787
    0.08
    $837,300
    3
    2.5
    2,254
    Off Market
    1203 RIDGE LAKE WAY LOT 244, Winter Garden, FL 34787
    0.05
    $425,000
    -
    -
    -
    Recently Sold

    Local Information

    • Map ViewExplore the area around Trail.
    • Schools1 Preschool School1 Elementary School1 Middle School1 High School
    • Shop & Eat
    -- mins to
    Commute Destination

    About this House

    Trail is in Winter Garden, FL and in ZIP code 34787.
    Trail, Winter Garden, FL 34787 is a unknown. It is currently off market. The Trulia Estimate is $1,876,400, with a rent estimate of $5,659/month.

    Home Details for Trail

    Property Information

    Property Type / Style
    Property Type: Unknown

    Market trends in Oakland

    Last updated July 2026
    Buyer'sMarketSeller'sMarket
    Avg. sale price
    —
    Sale-to-List Price
    —
    Price per sq ft
    —
    Available listings
    28

    Around this home

    What Locals Say about Oakland

    At least 12 Trulia users voted on each feature.

    • 100 % Say yards are well-kept

    • 100 % Say it's dog friendly

    • 93 % Say there's holiday spirit

    • 93 % Say car is needed

    • 92 % Say there are sidewalks

    • 85 % Say kids play outside

    • 84 % Say it's quiet

    • 83 % Say there's wildlife

    • 79 % Say parking is easy

    • 79 % Say they plan to stay for at least 5 years

    • 67 % Say streets are well-lit

    • 63 % Say people would walk alone at night

    • 63 % Say there are community events

    • 57 % Say neighbors are friendly

    • 27 % Say it's walkable to grocery stores

    Sourced by Trulia users. Learn more about our methodology.
    • shatiea mcwhorter
      "Nice quiet neighborhood great neighbors everyone gets alone and we all help each other when needed great place to have a family "
      0
      Flag
    • Matthewckent
      "It’s quiet and nature friendly. I have lived here for over two years and it’s my favorite part of Orlando. "
      0
      Flag
    • Kauffmanlondon
      "Family area and quiet great schools low crime and there own police department. Mostly newer builds and on the exspensive side "
      0
      Flag
    • Karenamiles
      "very close to gas stations restaurants and shopping. just off Florida Turnpike. nearby lake in subdivision. nice walking community "
      0
      Flag
    • Cassyperrin
      "There are quite a few dogs, so if you have an antisocial pet this might not be the best place for your furry friend!!"
      1
      Flag
    • Jayrwingfield
      "the people are unique and its s very quiet and slow. kids play outside and the people of the community are very welcoming"
      1
      Flag
    • Michael G.
      "Easy Access to most things in central fl"
      2
      Flag
    • Anne M.
      "I visit this area frequently. My family members live there as well. It's a great neighborhood where people know one another and look out for each other. Only 69 lots and it's a dead end street so no additional traffic in this gated community of all custom homes"
      3
      Flag

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    Frequently asked questions about Trail

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