5

Oakland, FL Homes for Sale under $2,000,000

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  • /50

    $1,725,000

    Open Wed 12:30PM - 2:30PM $84K PRICE DROP
    • 5 Beds
    • 4 Baths
    • 3,784 Sq Ft

    906 Allendale Ln, Winter Garden, FL 34787

    Welcome home to calm, light-filled luxury on a peaceful pond in the sought-after golf cart district—just steps from the West Orange Trail and 3 miles to historic Downtown Winter Garden.This 4-bed, 3-bath custom home sits on a large lot and features an open, airy floor plan with upscale laminate flooring throughout. The gourmet kitchen is built to entertain: commercial-grade hood, gas range,

    Jurgita Blake CENTURY 21 CARIOTI

    906 Allendale Ln, Winter Garden, FL 34787
  • /62

    $1,649,999

    $75K PRICE DROP
    • 6 Beds
    • 5 Baths
    • 4,104 Sq Ft

    1101 Eagles Pass Way, Oakland, FL 34787

    Virtually Staged. Modern Luxury in the Heart of Winter Garden’s Golf Cart District! Welcome to 1101 Eagles Pass Way, an exquisite 6-bedroom, 5-bathroom home situated on a desirable corner lot in the sought-after Oakland Park community—one of the few neighborhoods within Winter Garden’s beloved golf cart district. Just one block from Lake Apopka and less than two miles from the historic downtown

    Kevin Sullivan LAKESIDE REALTY WINDERMERE INC

    1101 Eagles Pass Way, Oakland, FL 34787
  • /2

    $1,675,000

    New Construction
    • 5 Beds
    • 5 Baths
    • 4,819 Sq Ft

    166 Hammock Preserve Loop, Oakland, FL 34787

    166 Hammock Preserve Loop, Oakland, FL 34787
  • /4

    $1,975,000

    New Construction
    • 5 Beds
    • 5.5 Baths
    • 3,596 Sq Ft

    1106 Sarah Mathews Dr, Oakland, FL 34787

    Pre-Construction. To be built. Nestled within the exclusive Grove community, the Clementine Plan by Element Home Builders is a bespoke pre-construction offering that showcases timeless architecture, refined luxury, and exceptional craftsmanship. This thoughtfully designed residence features 5 bedrooms, 5 full bathrooms, a powder room, loft across 3,596 square feet of elegantly curated living

    Heather Spirazza REGENCY REAL ESTATE LLC

    1106 Sarah Mathews Dr, Oakland, FL 34787
  • /94

    $1,500,000

    • 5 Beds
    • 4 Baths
    • 3,781 Sq Ft

    2010 Boss Hewett St, Oakland, FL 34787

    Welcome to this stunning, like-new home that perfectly blends luxury, comfort, and modern design in the highly desirable community of Hull Island. Boasting five spacious bedrooms and four full bathrooms, this thoughtfully designed residence offers an ideal layout for both everyday living and entertaining. This home offers two spacious owner’s suites, one conveniently located on the first floor

    Vilmari Caraballo RE/MAX ASSURED

    2010 Boss Hewett St, Oakland, FL 34787

Home Price Trends

Median Sale Price
$683,500
Median Single Family Sale Price
$752,500
Median Townhouse Sale Price
$382,000
Median 2 Bedroom Sale Price
$369,500
Average Price Per Sq Ft
$316
Number of Homes for Sale
29
Last 12 months Home Sales
108
Months of Supply
3.20
Median List Price
$737,000
Median Change From 1st List Price
4%
Median Home Sale Price YoY Change
3%
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