9

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

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  • /64

    $1,699,000

    $100K PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 4,102 Sq Ft

    1144 Hull Island Dr, Oakland, FL 34787

    Virtually Staged. Welcome to this exceptional lakefront retreat on the shores of Lake Apopka, where breathtaking water views, luxury upgrades, and exceptional outdoor living come together to create the ultimate Florida lifestyle. Offering 5 bedrooms, 4.5 bathrooms, and over 4,000 square feet of thoughtfully designed living space, including a convenient first-floor bedroom, this beautifully

    Agent Photo

    Tiffany Pantozzi

    ALIGN REAL ESTATE LLC

    1144 Hull Island Dr, Oakland, FL 34787
  • /65

    $1,765,000

    $44K PRICE DROP
    • 5 Beds
    • 4 Baths
    • 3,784 Sq Ft

    906 Allendale Ln, Winter Garden, FL 34787

    Step into a custom residence where calmness, grace, and thoughtful design greet you from the moment you arrive. In the quiet part of community, overlooking peaceful pond views, this luxury home features an open, airy floor plan filled with natural light, upscale laminate planks throughout, large lot. The gourmet kitchen is a true centerpiece here, offering a commercial-grade hood ideal for

    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

    AR Homes Builder
    166 Hammock Preserve Loop, Oakland, FL 34787
  • /71

    $1,509,900

    $78K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 3,613 Sq Ft

    1412 Johns Cove Ln, Oakland, FL 34787

    Virtually Staged. Discover your dream lakefront retreat on Johns Lake! Enjoy 176 feet of waterfront—perfect for skiing, boating, fishing, or relaxing. The oversized boathouse has water, power and accommodates two jet skis plus a boat with a touch-less remote-controlled cover. The home features a desirable floor plan with stunning lake views. The Family Room Over Garage (FROG) serves as a

    Betsey West NEXT RESIDENCE REALTY LLC

    1412 Johns Cove Ln, 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
  • /82

    $1,795,000

    • 4 Beds
    • 3.5 Baths
    • 3,515 Sq Ft

    15717 E Oakland Ave, Oakland, FL 34787

    Welcome to this exceptional ONE-OWNER CUSTOM HOME, sitting on a ONE-ACRE HOMESITE in one of Oakland’s most sought-after locations. Offering 3,515 square feet of living space (4,890 total square feet), this thoughtfully designed 4-bedroom, 3.5-bath residence combines timeless Old Florida charm with OUTSTANDING QUALITY CONSTRUCTION, FEATURING ALL-STEEL CONSTRUCTION—INCLUDING STEEL ROOF TRUSSES—for

    Janelle Conway CARIS REALTY AND INVESTMENTS INC

    15717 E Oakland Ave, 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
$680,000
Median Single Family Sale Price
$785,000
Median Townhouse Sale Price
$386,950
Median 2 Bedroom Sale Price
$384,900
Average Price Per Sq Ft
$310
Number of Homes for Sale
38
Last 12 months Home Sales
115
Months of Supply
4.00
Median List Price
$749,000
Median Change From 1st List Price
4%
Median Home Sale Price YoY Change
5%
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