14

Oakland, FL Homes for Sale under $500,000

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  • /33

    $500,000

    • 3 Beds
    • 2.5 Baths
    • 1,822 Sq Ft

    2755 Bobcat Chase Blvd, Oakland, FL 34787

    Welcome to 2755 Bobcat Chase Blvd, a modern 3-bedroom, 2.5-bath home with a bonus room, built in 2020 and tucked away on a quiet cul-de-sac in the highly desirable town of Oakland. This home offers a beautifully designed open-concept main level with a spacious living area that flows seamlessly into the dining space and upgraded kitchen featuring quartz countertops, stainless steel appliances, a

    Agent Photo

    Tania Matthews

    KELLER WILLIAMS ELITE PARTNERS III REALTY

    (321) 495-8074

    2755 Bobcat Chase Blvd, Oakland, FL 34787
  • /38

    $499,999

    • 4 Beds
    • 3 Baths
    • 2,352 Sq Ft

    651 Regina Cir, Oakland, FL 34787

    ***SELLER SAYS SELL! BEST priced home in the community!*** Welcome to John’s Landing, a gated lakefront community in the charming town of Oakland, offering private lake access and a community dock on Johns Lake. Step inside this spacious 4-bedroom, 3-bathroom home with a 3-car garage and make it your own. The thoughtfully designed split floor plan includes a family room, formal living room,

    Agent Photo

    Savina Delgado Rodriguez

    THE PROPERTY FIRM

    (321) 495-8335

    651 Regina Cir, Oakland, FL 34787
  • /52

    $410,000

    • 3 Beds
    • 2.5 Baths
    • 1,568 Sq Ft

    13293 Pontoon Rd, Oakland, FL 34787

    Sometimes the right home just feels easy. This 3-bedroom, 3-bath corner unit townhome was built in 2023 and sits in one of Winter Garden’s most sought-after neighborhoods, Waterleigh. From the moment you pull into the driveway, you’ll notice how clean, simple, and ready it feels. No projects. No waiting. Just move in and enjoy.Inside, natural light pours through every room, highlighting

    Mark Raumaker SERHANT

    13293 Pontoon Rd, Oakland, FL 34787
  • /29

    $471,900

    • 4 Beds
    • 2.5 Baths
    • 2,017 Sq Ft

    2435 Standing Rock Cir, Oakland, FL 34787

    Perfectly situated in the desirable Oakland Trails neighborhood this perfectly updated and maintained home is a turnkey away from being yours! 4 bed, 2.5 bath, the primary bed in the second level. The landscape perfectly accentuates your front porch. Step inside your fully upgraded home; complete with luxury upgrades ranging from lighting, designer finishes, and brand-name appliances. Up the

    Celestino De Cicco CENTRAL FLORIDA REALTY

    2435 Standing Rock Cir, Oakland, FL 34787
  • /3

    $407,990 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,715 Sq Ft

    Porter Plan at Serenade at Ovation - Townhomes, Oakland, FL 34787

    The Porter floorplan is an inviting two-story townhome designed with thoughtful spaces throughout. Featuring three bedrooms and two full bathrooms, the layout offers a smooth flow between living spaces. The first floor boasts a bright great room that opens into the dining area and lanai, perfect for entertaining or relaxation. Upstairs, all three bedrooms are thoughtfully arranged alongside a

    Dream Finders Homes Builder
    14229 Lanyard Way Unit 36452383, Oakland, FL 34787
  • /24

    $499,000

    • 3 Beds
    • 2.5 Baths
    • 1,720 Sq Ft

    14099 Lochend Way, Oakland, FL 34787

    Welcome to luxury living at its finest! Nestled in the prestigious West Haven at Ovation community in Winter Garden, this almost brand new 3-bedroom, 2.5-bathroom townhome is the epitome of modern elegance. As you step inside, you're greeted by an inviting open floor plan boasting an abundance of natural light and high-end finishes throughout. The spacious living area is perfect for entertaining

    Anahi C Rosario INTERNATIONAL REAL ESTATE LLC

    14099 Lochend Way, Oakland, FL 34787
  • /3

    $449,900

    • Land
    • 0.23 Acre
    • $1,956,087 per Acre

    1203 Ridge Lake Way, Winter Garden, FL 34787

    LOT 244: Don't miss your final opportunity to build your dream home in Oakland Park, a charming golf cart community along Lake Apopka and the West Orange Trail. These recently released lots are part the final phase of this coveted neighborhood and some of the best lots available. This is your chance to build an estate or lake front home that is only 2 miles for adorable Downtown Winter Garden,

    Tracey McFadden OAK AVENUE REAL ESTATE LLC

    1203 Ridge Lake Way, Winter Garden, FL 34787
  • /4

    $498,990 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,836 Sq Ft

    Brantley Plan at Serenade at Ovation, Oakland, FL 34787

    Discover the charm of the Brantley Floor Plan, a bungalow perfect for families and entertaining. This plan features 3 bedrooms, 2.5 bathrooms, a loft, and a 2-car garage. The gourmet kitchen boasts top-end designer finishes and flows seamlessly into the living areas, ideal for gatherings. An extra-large corner pantry provides ample storage for bulk purchases, enhancing functionality. Check out

    Dream Finders Homes Builder
    14229 Lanyard Way Unit 36498626, Oakland, FL 34787
  • /32

    $480,000

    • 4 Beds
    • 2 Baths
    • 2,065 Sq Ft

    717 Strihal Loop, Oakland, FL 34787

    Welcome Home to Johns Landing! Discover this beautifully maintained 4-bedroom, 2-bath residence located in the gated community of Johns Landing, offering private boat access to scenic Johns Lake. From the moment you step into the foyer, you’ll appreciate the soaring volume ceilings, tile flooring throughout the main living areas, and an abundance of natural light that creates a bright and

    Erica Sadelfeld THE REAL ESTATE COLLECTION LLC

    717 Strihal Loop, Oakland, FL 34787
  • /3

    $409,990 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,729 Sq Ft

    Sage Plan at Serenade at Ovation - Townhomes, Oakland, FL 34787

    The Sage floorplan offers a thoughtfully designed two-story layout, ideal for comfortable living and modern convenience. This 3-bedroom, 2.5-bathroom townhome features an open concept on the first floor, highlighted by a spacious great room, a cozy lanai, and a breezeway that connects to a 2-car garage. Upstairs, the second floor boasts all three bedrooms, along with a versatile loft space,

    Dream Finders Homes Builder
    14229 Lanyard Way Unit 36488308, Oakland, FL 34787
  • /17

    $460,000 New Construction

    • 4 Beds
    • 3 Baths
    • 1,847 Sq Ft

    4580 Maple Waltz, Oakland, FL 34787

    Exceptional investment opportunity! This stunning new townhome built by Pulte Homes is located in the desirable Park Side Trails community in Clermont, FL. The property is already leased starting November 28th with a 12-month contract at $2,800/month, offering immediate rental income and a great return potential.Featuring a bright and open floor plan with abundant natural light throughout,

    Marta Faustino DTB FLORIDA REALTY, INC.

    4580 Maple Waltz, Oakland, FL 34787
  • /17

    $459,000 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,730 Sq Ft

    8937 Matriarca Aly, Oakland, FL 34787

    Price adjustment! Move in ready! Freshly painted last year in “North Star” inside, and luxury vinyl plank flooring (no carpets) in this end townhouse just minutes away from theme parks and great shopping at Legado community in Windermere. 3 spacious bedrooms, and 2.5 bathrooms combine with generous living space in this 2-story townhome. Designed for entertaining, the "Minneola" features a large

    Tony Wong, LLC SANCTUM REALTY PROFESSIONALS LLC

    8937 Matriarca Aly, Oakland, FL 34787
  • /14

    $420,000

    • Land
    • 0.26 Acre
    • $1,615,385 per Acre

    1161 Prado Ln, Oakland, FL 34787

    Nestled in the heart of Oakland, Florida, this expansive homesite offers the perfect canvas to build your dream home with custom home builder, Pioneer Builders. Set in an illustrious community, called the Grove, this generously sized lot is ideal for crafting your unique custom home. The Grove is situated within Oakland’s most sought-after neighborhood known for its upscale charm and ideal

    Alexis Anderson REGENCY REAL ESTATE LLC

    1161 Prado Ln, Oakland, FL 34787
  • /3

    $475,000

    • Land
    • 0.51 Acre
    • $931,373 per Acre

    17858 Hither Hills Cir, Winter Garden, FL 34787

    Discover the perfect blend of luxury and natural beauty with these stunning lakefront lots in the Lake Apopka Sound subdivision. Set along the shores of scenic Lake Apopka, these spacious homesites offer breathtaking water views, serene sunsets, and access to one of Central Florida’s most picturesque settings.Lake Apopka Sound provides the ideal backdrop for your custom dream home. With

    Chris Kaminski SMART SOLUTIONS REALTY LLC

    17858 Hither Hills Cir, Winter Garden, FL 34787

Home Trends in Oakland, FL

Housing Trends

Median Sale Price
$651,158
Median Single Family Sale Price
$773,260
Median Townhouse Sale Price
$445,000
Average Price Per Sq Ft
$298
Number of Homes for Sale
40
Last 12 months Home Sales
172
Months of Supply
2.80
Median List Price
$699,999
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
15%
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