17

Oakland, FL Homes for Sale under $500,000

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  • /55

    $499,990 New Construction

    • 3 Beds
    • 2 Baths
    • 1,791 Sq Ft

    17621 Japonica Bloom Dr, Oakland, FL 34787

    Enjoy comfortable and convenient living in Northlake at Ovation, where this thoughtfully designed home features a private primary suite with a spacious walk-in closet, creating a peaceful retreat at the end of the day. Ideally located, the community offers easy access to everyday conveniences and popular destinations—just 37 minutes from Orlando International Airport, 20 minutes from world-famous

    Ashton Woods Builder
    17621 Japonica Bloom Dr, 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
  • /50

    $409,000

    • 3 Beds
    • 2.5 Baths
    • 1,620 Sq Ft

    2208 Gopher Tortoise Terrace, Oakland, FL 34760

    Welcome to this beautifully appointed townhome in the desirable Longleaf at Oakland community. This charming residence features 3 bedrooms and 2.5 bathrooms with a thoughtfully designed open-concept layout. Stylish Vinyl flooring enhances the spacious living and dining areas, creating a warm and inviting atmosphere.The large open kitchen offers a large island with seating for four, granite

    Fred Mansfield ORLANDO PROP MGMNT RLTY LLC

    2208 Gopher Tortoise Terrace, Oakland, FL 34760
  • /21

    $445,999

    • 3 Beds
    • 2.5 Baths
    • 1,796 Sq Ft

    12748 Brodlove Ln, Oakland, FL 34787

    MOTIVATED SELLER — MUST SELL! — PRICED BELOW MARKET. Exceptionally maintained 2022 M/I Homes Baldwin floorplan in sought-after Encore at Ovation (Horizon West/Winter Garden). 3BD/2.5BA bungalow-style, move-in ready and turnkey with smart-home features (smart appliances/thermostat). Bright open-concept living with abundant natural light. Modern kitchen with quartz countertops, quality cabinetry,

    Mayra Rivas Acevedo CASA SOL REALTY LLC

    12748 Brodlove Ln, Oakland, FL 34787
  • /5

    $455,000

    • Land
    • 0.28 Acre
    • $1,625,000 per Acre

    1227 Ridge Lake Way, Winter Garden, FL 34787

    Lot 249 is located in the final phase of Oakland Park at The Reserve, a highly sought-after golf cart community nestled along the shores of Lake Apopka. Enjoy close proximity to the West Orange Trail and the charming Downtown Winter Garden, known for its local shops, dining, and events. This is a rare opportunity to build your FULLY CUSTOM dream home in one of the area’s most desirable

    Dawn Pickard THE C SMITH REAL ESTATE GROUP LLC

    1227 Ridge Lake Way, Winter Garden, FL 34787
  • /53

    $418,900

    • 3 Beds
    • 2.5 Baths
    • 1,860 Sq Ft

    8167 Mosaic Ln, Oakland, FL 34787

    One or more photo(s) has been virtually staged. Gorgeous Townhouse located in Winter Garden at the great Ravenna Community, just 10 minutes drive from Disney World, close to good Winter Garden restaurants, new shopping malls, supermarkets, banks ext. This 3 bedroom 2/1 bathroom home with stunning features and open floor plan, separated dining room that is fully upgraded floor and cabinets and

    Simon Colak USCO CAPITAL GROUP

    8167 Mosaic Ln, 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
  • /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
  • /3

    $461,995 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,863 Sq Ft

    13873 Easdale Aly, Oakland, FL 34787

    Under Construction. Toll Brothers New Construction at Winter Garden Horizonwest. Estimate completion July 2026. Our Crowley Townhome features a covered entry that leads to an open and expansive living space, kitchen, and dining. The home features a spacious courtyard with access to the detached 2 cars garage. The master bedroom is highlighted by a large walk-in closet and a private bath with dual

    Alicea Salgado ORLANDO TBI REALTY LLC

    13873 Easdale Aly, 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
  • /30

    $474,990

    • 3 Beds
    • 2.5 Baths
    • 2,078 Sq Ft

    2135 Standing Rock Cir, Oakland, FL 34787

    ASSUMABLE 2.4% Interest Rate. Welcome to this beautifully appointed single-family home located in the charming town of Oakland, FL. Offering 3 bedrooms, 2.5 bathrooms, and 2,078 square feet of thoughtfully designed living space, this home features an open floor plan that’s perfect for both everyday living and entertaining. The spacious layout is complemented by an upstairs loft, ideal for a home

    Joseph Sipp KELLER WILLIAMS WINTER PARK

    2135 Standing Rock Cir, Oakland, FL 34787
  • /12

    $473,990 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,186 Sq Ft

    6056 Meditation Dr, Oakland, FL 34787

    Under Construction. The Solana II has the “WOW” factor you have been searching for. There is a beautiful designer kitchen, that features an abundance of counter space that is sure to appeal to your inner-chef. The kitchen looks out to the combination dining and family rooms for the perfect open sight lines. There are a total of 3 bedrooms and 2 and a half bathrooms. The bedrooms are located on

    Ben Goldstein LENNAR REALTY

    6056 Meditation Dr, 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
$645,000
Median Single Family Sale Price
$751,000
Median Townhouse Sale Price
$447,368
Average Price Per Sq Ft
$301
Number of Homes for Sale
43
Last 12 months Home Sales
179
Months of Supply
2.90
Median List Price
$667,500
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
13%
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