3,150

Oakland, FL Homes

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    • /48

      Est $773,802 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,724 Sq Ft

      5121 Breezy Acres St, Oakland, FL 34787

      5121 Breezy Acres St, Oakland, FL 34787
  • /77

    $489,900 Pending

    • 3 Beds
    • 2.5 Baths
    • 1,909 Sq Ft

    2029 White Feather Loop, Winter Garden, FL 34787

    Under contract-accepting backup offers. Welcome to an exceptional home in the highly sought-after Oakland Trails community! This beautifully designed 3-bed, 2.5-bath residence boasts an open and functional floor plan that truly sets it apart from others in the neighborhood. With approximately 1,909 sq. ft. of thoughtfully laid-out living space, this home offers modern comfort with everyday

    Eric Bress, Jr ERIC BRESS REAL ESTATE LLC

    2029 White Feather Loop, Winter Garden, FL 34787
  • /2

    $460,000 Sold Sep 23, 2025

    17055 Wynford Ln, Oakland, FL 34787

    • 3 Beds
    • 2.5 Baths
    • 2,345 Sq Ft
    • Built 2021

    Last Sold Summary

    • 16% Below List Price
    • $196/SF
    • 160 Days On Market

    Current Estimated Value $479,006

    Last Listing Agent Lori Lucente-Nelson RE/MAX PRIME PROPERTIES

    17055 Wynford Ln, Oakland, FL 34787
    • /55

      Est $485,780 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,705 Sq Ft

      16946 Oakboro St, Oakland, FL 34787

      16946 Oakboro St, 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
  • /2

    $580,109 Sold Dec 23, 2025

    17597 Japonica Bloom Dr, Oakland, FL 34787

    • 3 Beds
    • 2 Baths
    • 1,791 Sq Ft
    • Built 2025

    Last Sold Summary

    • $324/SF

    Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

    17597 Japonica Bloom Dr, Oakland, FL 34787
    • /2

      Est $502,140 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,788 Sq Ft

      14122 Frasier St, Oakland, FL 34787

      14122 Frasier St, Oakland, 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
  • /2

    $500,000 Sold Apr 08, 2025

    16257 Prairie School Dr, Oakland, FL 34787

    • 4 Beds
    • 3 Baths
    • 2,070 Sq Ft
    • Built 2021

    Last Sold Summary

    • 3% Below List Price
    • $242/SF
    • 54 Days On Market

    Current Estimated Value $496,846

    Last Listing Agent Sue Vasquez FLORIDA REALTY RESULTS LLC

    16257 Prairie School Dr, Oakland, FL 34787
    • /2

      Est $491,683 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 1,992 Sq Ft

      11361 Great Rock St, Oakland, FL 34787

      11361 Great Rock St, Oakland, FL 34787
  • /17

    $2,238,120 New Construction

    • 5 Beds
    • 5.5 Baths
    • 4,204 Sq Ft

    1173 Prado Ln, Oakland, FL 34787

    Pre-Construction. To be built. Introducing the Sunburst Model by Davila HomesDiscover the perfect blend of modern luxury and everyday comfort in the Sunburst, a beautifully designed 4,204-square-foot residence by Davila Homes. With 5 spacious bedrooms and 5.5 elegantly finished bathrooms, this home offers the ideal balance of open living and private retreat—crafted to meet the needs of

    Alexis Anderson REGENCY REAL ESTATE LLC

    1173 Prado Ln, Oakland, FL 34787
  • /2

    $785,000 Sold Oct 24, 2025

    16152 Point Rock Dr, Oakland, FL 34787

    • 5 Beds
    • 4 Baths
    • 2,866 Sq Ft
    • Built 2025

    Last Sold Summary

    • 6% Below List Price
    • $274/SF
    • 48 Days On Market

    Current Estimated Value $785,000

    Last Listing Agent Stephen Cline DR HORTON REALTY OF CENTRAL FLORIDA LLC

    16152 Point Rock Dr, Oakland, FL 34787
    • /2

      Est $828,816 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 3,038 Sq Ft

      14211 Lanyard Way, Oakland, FL 34787

      14211 Lanyard Way, Oakland, FL 34787
  • /66

    $2,300,000 Pending

    • 4 Beds
    • 6 Baths
    • 3,902 Sq Ft

    1118 Sarah Mathews Dr, Oakland, FL 34787

    Under contract-accepting backup offers. Situated within the exclusive Grove community, this custom-built La Cascina residence by Pioneer Builders delivers refined luxury and exceptional craftsmanship throughout. Offering 4 bedrooms, 6 bathrooms, and 3,902 square feet of thoughtfully designed living space, this new construction home blends timeless design with modern comfort. The open-concept

    Alexis Anderson REGENCY REAL ESTATE LLC

    1118 Sarah Mathews Dr, Oakland, FL 34787
  • /52

    $580,000 Sold Oct 31, 2025

    2642 Bobcat Chase Blvd, Oakland, FL 34787

    • 3 Beds
    • 2.5 Baths
    • 1,811 Sq Ft
    • Built 2019

    Last Sold Summary

    • 6% Below List Price
    • $320/SF
    • 38 Days On Market

    Current Estimated Value $577,589

    Last Listing Agent Johna Jennings Coastal Life Properties LLC

    2642 Bobcat Chase Blvd, Oakland, FL 34787
    • /2

      Est $743,123 Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 3,065 Sq Ft

      14199 Lanyard Way, Oakland, FL 34787

      14199 Lanyard Way, 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
  • /2

    $900,000 Sold Sep 12, 2025

    619 Largovista Dr, Oakland, FL 34787

    • 5 Beds
    • 3.5 Baths
    • 3,728 Sq Ft
    • Built 2005

    Last Sold Summary

    • 9% Below List Price
    • $241/SF
    • 52 Days On Market

    Current Estimated Value $901,764

    Last Listing Agent Farhad Haniff EXP REALTY LLC

    619 Largovista Dr, Oakland, FL 34787
    • /69

      Est $745,189 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 3,332 Sq Ft

      11168 Robert Frost Dr, Oakland, FL 34787

      11168 Robert Frost Dr, 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
  • /2

    $914,390 Sold Nov 25, 2025

    4649 Golden Birch Ave, Oakland, FL 34787

    • 5 Beds
    • 5 Baths
    • 4,272 Sq Ft
    • Built 2025

    Last Sold Summary

    • $214/SF

    Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

    4649 Golden Birch Ave, Oakland, FL 34787
    • /2

      Est $782,484 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,950 Sq Ft

      16225 Silver Brook Way, Oakland, FL 34787

      16225 Silver Brook Way, Oakland, FL 34787
  • /38

    $395,000

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

    12043 Holystone St, Oakland, FL 34787

    “The property is currently active for sale but is rented for $2500 monthly, with a lease valid until February 2026. The lease must be honored, so the property is best suited for investors looking for a rental income opportunity.” Welcome to Waterleigh community! This townhome has 3 bedroom 2.5 bathroom is conveniently located in Waterleigh Phase 4, near the Elementary and Middle School! It offers

    Ruth Santos Blystone WRA BUSINESS & REAL ESTATE

    12043 Holystone St, Oakland, FL 34787
  • /2

    $400,000 Sold Aug 18, 2025

    5693 Meditation Dr, Oakland, FL 34787

    • 3 Beds
    • 2.5 Baths
    • 1,795 Sq Ft
    • Built 2025

    Last Sold Summary

    • 11% Below List Price
    • $223/SF
    • 31 Days On Market

    Last Listing Agent Ben Goldstein LENNAR REALTY

    5693 Meditation Dr, Oakland, FL 34787
    • /2

      Est $634,857 Not Listed For Sale

      • 4 Beds
      • 4.5 Baths
      • 2,789 Sq Ft

      15022 Summer Harvest St, Oakland, FL 34787

      15022 Summer Harvest St, Oakland, FL 34787
  • /18

    $895,000

    • Land
    • 0.89 Acre
    • $1,005,618 per Acre

    537 N Pollard St, Winter Garden, FL 34787

    Welcome to Briley Farm, a picturesque community nestled along the serene shores of Lake Apopka. This premium lot offers the perfect opportunity to design and build your custom dream home in one of Central Florida’s most sought-after lakefront neighborhoods. With plenty of space and stunning views, this homesite is ideal for creating your personal oasis—whether that’s a timeless farmhouse, a

    Blaine Dooley REGENCY REAL ESTATE LLC

    537 N Pollard St, Winter Garden, FL 34787
  • /2

    $653,240 Sold Jul 30, 2025

    5664 Vinyasa Rd, Oakland, FL 34787

    • 3 Beds
    • 2.5 Baths
    • 2,650 Sq Ft
    • Built 2025

    Last Sold Summary

    • $247/SF

    Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

    5664 Vinyasa Rd, Oakland, FL 34787
    • /2

      Est $602,280 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,450 Sq Ft

      15141 Summer Harvest St, Oakland, FL 34787

      15141 Summer Harvest St, Oakland, FL 34787
  • /7

    $1,700,000 New Construction

    • 5 Beds
    • 3.5 Baths
    • 3,909 Sq Ft

    1207 Ridge Lake Way, Winter Garden, FL 34787

    Pre-Construction. To be built. This is a pre-construction, to be built, custom home located in the final phase (The Reserve) of the Oakland Park community. This two-story custom RCB home can be customized! All finish selections can be made by the buyer; even change/customize the floor plan! This two story floor plan offers 5 bedrooms, 3.5 baths, an office and 3-car garage. This home can be yours

    Chris Herlihy NEW HOMES REAL ESTATE, INC.

    1207 Ridge Lake Way, Winter Garden, FL 34787
  • /36

    $751,000 Sold Oct 03, 2025

    16041 Honey Harvest St, Oakland, FL 34787

    • 4 Beds
    • 4.5 Baths
    • 2,837 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $265/SF
    • 26 Days On Market

    Taylor Morrison Harvest at Ovation

    16041 Honey Harvest St, Oakland, FL 34787
    • /2

      Est $852,349 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,247 Sq Ft

      1215 Wilder Oaks Way, Oakland, FL 34787

      1215 Wilder Oaks Way, Oakland, FL 34787
  • /28

    $1,775,000 Pending

    • 5 Beds
    • 4.5 Baths
    • 3,991 Sq Ft

    854 Tilden Oaks Trail, Winter Garden, FL 34787

    This former J & J Building model home has never been lived in and has been carefully cared for. With 3,453 sq. ft. in the main house, it offers 4 bedrooms, 3.5 baths, and an oversized 2.5-car garage with extra space for a golf cart. A detached 538 sq. ft. pool house adds valuable flexibility, offering a fifth bedroom, full bath, wet bar, office, and walk-in closet—an ideal setup for extended

    Tracey McFadden OAK AVENUE REAL ESTATE LLC

    854 Tilden Oaks Trail, Winter Garden, FL 34787
  • /2

    $695,000 Sold Sep 22, 2025

    1281 Ridge Lake Way, Winter Garden, FL 34787

    • Land
    • 0.39 Acre
    • $1,782,051 per Acre

    Last Sold Summary

    • 13% Below List Price
    • 99 Days On Market

    Last Listing Agent Samantha Andrade SERHANT

    1281 Ridge Lake Way, Winter Garden, FL 34787
    • /2

      Est $520,066 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,985 Sq Ft

      14114 Frasier St, Oakland, FL 34787

      14114 Frasier St, Oakland, FL 34787
  • /64

    $625,000

    • 3 Beds
    • 2.5 Baths
    • 1,906 Sq Ft

    13067 Tollcross Way, Oakland, FL 34787

    Located in the heart of Horizon West in Winter Garden, just minutes from the gates of Walt Disney World, this beautiful bungalow is nestled within Westhaven At Ovation, a sought-after residential community by Toll Brothers. The location is truly exceptional, offering quick and easy access to State Road 429, the Flamingo Crossings shopping and dining district, and all the magic Disney has to

    Amy Kidwell PA PREFERRED REAL ESTATE BROKERS

    13067 Tollcross Way, Oakland, FL 34787
  • /2

    $883,656 Sold Sep 08, 2025

    16089 Honey Harvest St, Oakland, FL 34787

    • 4 Beds
    • 4.5 Baths
    • 2,837 Sq Ft
    • Built 2025

    Last Sold Summary

    • $311/SF

    Current Estimated Value $873,000

    Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

    16089 Honey Harvest St, Oakland, FL 34787
    • /2

      Est $525,712 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,114 Sq Ft

      14078 Frasier St, Oakland, FL 34787

      14078 Frasier St, Oakland, FL 34787
  • /60

    $2,160,000 Pending

    • 5 Beds
    • 6 Baths
    • 6,141 Sq Ft

    1017 Johns Point Dr, Oakland, FL 34787

    Under contract-accepting backup offers. A rare lakefront estate on one of Central Florida?s most celebrated lakes, John?s Lake. Positioned on nearly one acre in a private, gated enclave, this custom 5-bedroom, 6-bath residence offers sweeping open-water views, dramatic sunsets, and direct access to boating, jet skiing, and year-round fishing from its private dock. With approximately 250 feet of

    peipei Qiao BAY STREET GROUP FLORIDA LLC

    1017 Johns Point Dr, Oakland, FL 34787
  • /2

    $2,275,000 Sold Nov 24, 2025

    530 Largovista Dr, Oakland, FL 34787

    • 5 Beds
    • 5 Baths
    • 4,798 Sq Ft
    • Built 2006

    Last Sold Summary

    • 9% Below List Price
    • $474/SF
    • 110 Days On Market

    Last Listing Agent Dawn Giachetti PREMIER SOTHEBYS INT'L REALTY

    530 Largovista Dr, Oakland, FL 34787
    • /2

      Est $1,398,565 Not Listed For Sale

      • 5 Beds
      • 5 Baths
      • 3,747 Sq Ft

      100 Millholland St, Oakland, FL 34760

      100 Millholland St, Oakland, FL 34760

Showing Results 241 - 280, Page 7 of 18

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