3,195

Oakland, FL Homes

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  • /25

    $645,990 New Construction

    • 5 Beds
    • 3.5 Baths
    • 2,688 Sq Ft

    Anna Maria w/ Bonus Plan at Serenade at Ovation - Single Family Homes, Oakland, FL 34787

    The Anna Maria with Bonus floorplan is an expansive two-story home designed to accommodate a growing family, offering five bedrooms and three and a half bathrooms. On the main floor, you'll find a spacious great room adjacent to a well-appointed dining room and kitchen, creating an ideal space for gatherings. The primary suite, featuring a large walk-in closet and private bath, is thoughtfully

    Dream Finders Homes Builder
    14229 Lanyard Way Unit 36501514, Oakland, FL 34787
  • /20

    $3,150 per month

    • 4 Beds
    • 3 Baths
    • 2,419 Sq Ft
    • House for Rent

    5792 Dancing Willow St, Oakland, FL 34787

    WHY SETTLE FOR A REGULAR HOME WHEN YOU CAN HAVE TWO LIVING SPACES UNDER ONE ROOF?Beautiful Next-Gen style home in one of Clermont’s fastest-growing areas, just minutes from Winter Garden and the highly anticipated Olympus development. This property offers the perfect blend of space, flexibility, and lifestyle. The main living area features an open-concept design ideal for entertaining,

    Jose Vasquez MY LOYALTY GROUP REALTY LLC

    5792 Dancing Willow St, Oakland, FL 34787
  • /2

    $465,597 Sold Dec 22, 2025

    17687 Japonica Bloom Dr Unit 221, Oakland, FL 34787

    • 3 Beds
    • 2.5 Baths
    • 1,696 Sq Ft
    • Built 2025

    Last Sold Summary

    • $275/SF
    • 20 Days On Market

    Last Listing Agent Reed Williams ASHTON WOODS FLORIDA REALTY LLC

    17687 Japonica Bloom Dr Unit 221, Oakland, FL 34787
    • /32

      Est $426,194 Not Listed For Sale

      2289 White Feather Loop, Oakland, FL 34787

      • 3 Beds
      • 2.5 Baths
      • 1,744 Sq Ft
      • Built 2017
      2289 White Feather Loop, Oakland, FL 34787

      Last Sold Summary

      • 3% Below List Price
      • $252/SF
      • 29 Days On Market

      Last Sold Price $440,000

      Last Listing Agent Mandy Morgan TEAM DONOVAN

  • /3

    $649,990 New Construction

    • 4 Beds
    • 3 Baths
    • 2,689 Sq Ft

    Biscayne Plan at Serenade at Ovation - Single Family Homes, Oakland, FL 34787

    The Biscayne floorplan offers a spacious two-story design that perfectly balances functionality and flexibility, ideal for growing families. With four bedrooms and two and a half bathrooms, this layout provides ample space for everyday living and special moments alike. On the first floor, you'll find a flex room that can serve as a home office, gym, or an optional guest bedroom, depending on your

    Dream Finders Homes Builder
    14229 Lanyard Way Unit 36496529, Oakland, FL 34787
  • /42

    $3,600 per month

    • 5 Beds
    • 4 Baths
    • 2,700 Sq Ft
    • House for Rent

    12887 Westhaven Oak Dr, Oakland, FL 34787

    Spacious 5-Bedroom Home in Prime Winter Garden Location Welcome to 12887 Westhaven Oak Drive, a beautifully designed 5-bedroom, 4-bathroom home located in one of Winter Garden’s most desirable areas. This spacious residence offers an ideal layout for families, remote work, and entertaining. The open-concept kitchen seamlessly connects to the main living area, featuring modern finishes, ample

    Maria Elena EXP REALTY LLC

    12887 Westhaven Oak Dr, Oakland, FL 34787
  • /2

    $768,700 Sold Oct 28, 2025

    5780 Dancing Willow St, Oakland, FL 34787

    • 4 Beds
    • 3.5 Baths
    • 3,575 Sq Ft
    • Built 2025

    Last Sold Summary

    • $215/SF

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

    5780 Dancing Willow St, Oakland, FL 34787
    • /2

      Est $468,448 Not Listed For Sale

      1793 White Feather Loop, Oakland, FL 34787

      • 3 Beds
      • 2.5 Baths
      • 2,082 Sq Ft
      • Built 2017
      1793 White Feather Loop, Oakland, FL 34787

      Last Sold Summary

      • 1% Below List Price
      • $228/SF
      • 105 Days On Market

      Last Sold Price $475,000

      Last Listing Agent Joseph Doher BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY

  • /69

    $785,000

    • 4 Beds
    • 3 Baths
    • 2,909 Sq Ft

    9062 Sonoma Coast Dr, Oakland, FL 34787

    One or more photo(s) has been virtually staged. Special Financing Available — Ask for Details!Experience resort-style living in the highly desirable Waterleigh community of Winter Garden. This one-of-a-kind home sits on a rare, oversized lot with no rear neighbors, offering ultimate privacy and tranquility — perfect for families or anyone seeking a private retreat in one of Central Florida’s

    Asher Chen AAA GLOBAL VENTURES PA

    9062 Sonoma Coast Dr, Oakland, FL 34787
  • /24

    $3,000 per month

    • 4 Beds
    • 3.5 Baths
    • 2,502 Sq Ft
    • House for Rent

    11422 Great Rock St, Oakland, FL 34787

    Beautiful 4 BR/3.5BA Single Family Home in the desirable Storey Grove Community in Winter Garden. Spacious, modern kitchen with large center island, and stainless steel appliances. Two Master bedrooms, one downstairs and one upstairs. Master bedroom features HUGE walk-in closet and en suite bathroom with double vanity! 2 Car Garage! Washer/dryer included. The home was built in front of a

    Huizi Li MULTI CHOICE REALTY LLC

    11422 Great Rock St, Oakland, FL 34787
  • /2

    $620,000 Sold May 12, 2025

    1215 Johns Cove Ln, Oakland, FL 34787

    • 4 Beds
    • 2 Baths
    • 2,811 Sq Ft
    • Built 2003

    Last Sold Summary

    • 5% Below List Price
    • $221/SF
    • 124 Days On Market

    Current Estimated Value $639,570

    Last Listing Agent Heidi Pfeffer-Morgan DALTON WADE INC

    1215 Johns Cove Ln, Oakland, FL 34787
    • /2

      Not Listed For Sale

      16465 Hamlin View St, Oakland, FL 34787

      • 3 Beds
      • 2.5 Baths
      • 1,836 Sq Ft
      • Built 2025
      16465 Hamlin View St, Oakland, FL 34787

      Last Sold Summary

      • $293/SF
      • 0 Days On Market

      Last Sold Price $538,491

      Last Listing Agent Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

  • /44

    $725,000

    • 4 Beds
    • 3 Baths
    • 2,113 Sq Ft

    17936 Adrift Rd, Oakland, FL 34787

    This is an amazing one-story 4-bedroom, 3 bath lakeview, conservation area home with elegant exteriors and high end features in Waterleigh, Horizon West’s Premier Community! Desirable Horizon West, featuring resort-style amenities and thoughtful design minutes from Disney World Parks and resorts. Elegant 4 bedroom, 3-bath home offers 2,113 sq. ft. of single-story comfort, ideal for families or

    Stephen Hachey FLAT FEE MLS REALTY

    17936 Adrift Rd, Oakland, FL 34787
  • /25

    $3,400 per month

    • 4 Beds
    • 3.5 Baths
    • 2,800 Sq Ft
    • House for Rent

    12736 Brodlove Ln, Oakland, FL 34787

    Encore at Ovation community in Horizon West! Enjoy this approx 2900 sq ft home offering guest bedroom with ensuite bath on first floor. Four bedrooms with three and a half baths. Tiles in living, family and kitchen areas. Open floor plan with 9 ft ceiling height. Gourmet kitchen with convection oven, stone counter top, writing desk, breakfast bar, stainless steel appliances, backsplash, gas

    Alreyas Baksh RIO HOMES AND INVESTMENTS LLC

    12736 Brodlove Ln, Oakland, FL 34787
  • /2

    $430,000 Sold Mar 23, 2026

    2201 Standing Rock Cir, Oakland, FL 34787

    • 3 Beds
    • 2.5 Baths
    • 1,753 Sq Ft
    • Built 2020

    Last Sold Summary

    • 2% Below List Price
    • $245/SF
    • 6 Days On Market

    Current Estimated Value $434,580

    Last Listing Agent Christine Anthony CHARLES RUTENBERG REALTY ORLANDO

    2201 Standing Rock Cir, Oakland, FL 34787
    • /2

      Not Listed For Sale

      3119 Armstrong Ave, Oakland, FL 34787

      • 4 Beds
      • 2.5 Baths
      • 1,867 Sq Ft
      • Built 2025
      3119 Armstrong Ave, Oakland, FL 34787

      Last Sold Summary

      • $233/SF

      Last Sold Price $435,000

      Last Listing Agent Stellar Non-Member Agent FL_MFRMLS

  • /57

    $990,000 Open Sun 12PM - 3PM

    • 5 Beds
    • 3.5 Baths
    • 3,910 Sq Ft

    9849 Lost Creek Dr, Oakland, FL 34787

    One or more photo(s) has been virtually staged. Big Price Reduction!!!!!! Nestled in the heart of Winter Garden’s prestigious Waterleigh community, this 5-bedroom, 4-bathroom masterpiece redefines modern luxury and family living. Boasting 3,910 sq. ft. of beautifully designed space, this 2021-built home is a perfect blend of timeless charm and contemporary convenience. From the moment you arrive,

    Jennifer Ibarra REAL BROKER, LLC

    9849 Lost Creek Dr, Oakland, FL 34787
  • /35

    $3,100 per month

    • 4 Beds
    • 2.5 Baths
    • 2,114 Sq Ft
    • House for Rent

    14115 Frasier St, Oakland, FL 34787

    Now for rent and available for move in April 1st!! Modern, 4 bed, 2 1/5 bath, beautiful home and full of upgraded features! Quartz counter tops upgraded finishes in all bathrooms and kitchen. Stainless steel modern appliances, cooktop, and range hood. Open first floor, a spacious and bright living and dining area that flows seamlessly into the kitchen. All bedrooms with upgrade carpeting are

    Claudia D'Aquino CENTURY 21 CARIOTI

    14115 Frasier St, Oakland, FL 34787
  • /2

    $710,000 Sold Nov 04, 2025

    1301 Johns Cove Ln, Oakland, FL 34787

    • 4 Beds
    • 2 Baths
    • 2,495 Sq Ft
    • Built 2003

    Last Sold Summary

    • 14% Below List Price
    • $285/SF
    • 124 Days On Market

    Current Estimated Value $678,971

    Last Listing Agent Heidi Pfeffer-Morgan DALTON WADE INC

    1301 Johns Cove Ln, Oakland, FL 34787
    • /2

      Est $858,228 Not Listed For Sale

      1102 Eagles Pass Way, Oakland, FL 34787

      • 3 Beds
      • 2.5 Baths
      • 2,260 Sq Ft
      • Built 2023
      1102 Eagles Pass Way, Oakland, FL 34787

      Last Sold Summary

      • 1% Below List Price
      • $385/SF
      • 4 Days On Market

      Last Sold Price $869,900

      Last Listing Agent Jayme Taylor SAGE REALTY FLORIDA, INC.

  • /3

    $919,000 Pending

    • 5 Beds
    • 4.5 Baths
    • 3,894 Sq Ft

    12940 Westhaven Oak Dr, Oakland, FL 34787

    Under Construction. Under Construction. Toll Brothers New Construction in Horizon West – Winter Garden | Estimated Completion Summer 2026. The wide and elongated foyer create an impressive entry into this home, with large formal dining room and spacious kitchen. The well-equipped kitchen features a walk-in pantry and an open view of the breakfast area and great room. The great room opens out to a

    Dayene Grubert ORLANDO TBI REALTY LLC

    12940 Westhaven Oak Dr, Oakland, FL 34787
  • /40

    $4,200 per month

    • 4 Beds
    • 4.5 Baths
    • 3,426 Sq Ft
    • House for Rent

    9014 Sonoma Coast Dr, Oakland, FL 34787

    This modern, luxury residence offers an exceptional open-concept design featuring five bedrooms and four-and-a-half bathrooms, situated in a highly desirable neighborhood. Located within the Waterleigh community, residents enjoy access to fitness facilities, playgrounds, sports fields, walking and nature trails, and mini golf. The home features a spacious floor plan with a well-appointed kitchen

    Greg Mann BETTER HOMES AND GARDENS REAL ESTATE MANN GLOBAL P

    9014 Sonoma Coast Dr, Oakland, FL 34787
  • /2

    $990,900 Sold Jul 09, 2025

    1180 Riverway Dr, Oakland, FL 34787

    • 4 Beds
    • 3.5 Baths
    • 2,796 Sq Ft
    • Built 2025

    Last Sold Summary

    • $354/SF

    Current Estimated Value $951,085

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

    1180 Riverway Dr, Oakland, FL 34787
    • /2

      Est $617,816 Not Listed For Sale

      15191 Blue Peacock Ln, Oakland, FL 34787

      • 4 Beds
      • 2.5 Baths
      • 2,584 Sq Ft
      • Built 2023
      15191 Blue Peacock Ln, Oakland, FL 34787

      Last Sold Summary

      • 9% Below List Price
      • $262/SF

      Last Sold Price $676,128

      Last Listing Agent Stellar Non-Member Agent FL_MFRMLS

  • /53

    $992,300 New Construction

    • 4 Beds
    • 4 Baths
    • 4,271 Sq Ft

    4608 Golden Birch Ave, Oakland, FL 34787

    Under Construction. Welcome to Parkside Trails! Explore the charm of this premier Clermont location, offering exclusive amenities and quick access to shopping, dining, and entertainment. With a mix of new construction, single-family and townhomes, plus a variety of exclusive amenities, families will love coming home. Now Selling Onsite with 4 Models Open Daily!Introducing the exquisite

    Adrienne Escott PULTE REALTY OF NORTH FLORIDA LLC

    4608 Golden Birch Ave, Oakland, FL 34787
  • /26

    $2,300 per month

    • 3 Beds
    • 2.5 Baths
    • 1,834 Sq Ft
    • Townhouse for Rent

    3127 Mindfullness Dr, Oakland, FL 34787

    A charming front porch warmly welcomes you into this BEAUTIFUL and NEW corner townhome located in the highly desirable WELLNESS Ridge Community, offering modern comfort and everyday convenience. As a corner unit, the home enjoys an additional window that brings in abundant natural light, creating a bright and airy atmosphere throughout the interior. Ideally situated just steps from the community

    Cristiane Carneiro Spfndola Rocha L WRA BUSINESS & REAL ESTATE

    3127 Mindfullness Dr, Oakland, FL 34787
  • /37

    $449,990 Sold Nov 13, 2025

    17687 Japonica Bloom Dr, Oakland, FL 34787

    • 3 Beds
    • 2.5 Baths
    • 1,696 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $265/SF
    • 15 Days On Market

    Ashton Woods Northlake at Ovation - Townhomes

    17687 Japonica Bloom Dr, Oakland, FL 34787
    • /2

      Est $625,336 Not Listed For Sale

      15014 Summer Harvest St, Oakland, FL 34787

      • 5 Beds
      • 4.5 Baths
      • 2,861 Sq Ft
      • Built 2024
      15014 Summer Harvest St, Oakland, FL 34787

      Last Sold Summary

      • 1% Above List Price
      • $216/SF

      Last Sold Price $619,040

      Last Listing Agent Dimerson Almeida TALENT REALTY SOLUTIONS

  • /2

    $925,990 Pending

    • 4 Beds
    • 3.5 Baths
    • 3,498 Sq Ft

    15184 Tea Tree Dr, Oakland, FL 34787

    One or more photo(s) has been virtually staged. Pre-Construction. To be built. Sample Image The Venice is a two-story home designed for efficient and flexible living. The first floor features an open-concept layout with a centrally located kitchen overlooking the dining area and main living space. The primary bedroom is located on the main level and includes a walk-in closet and en-suite

    Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

    15184 Tea Tree Dr, Oakland, FL 34787
  • /17

    $3,050 per month

    • 3 Beds
    • 2.5 Baths
    • 2,014 Sq Ft
    • House for Rent

    9588 Jacques Aly, Oakland, FL 34787

    Welcome to Waterleigh in Horizon West, just minutes from Winter Garden. This popular Cordale bungalow offers 3 bedrooms, 2.5 bathrooms, an attached 2-car garage, and a loft converted into an additional bedroom. Enjoy peaceful water views from the front porch and an open concept layout with granite countertops and stainless steel appliances. The primary bedroom is located on the first floor, with

    Teresa Valdes VALSTAR REALTY LLC

    9588 Jacques Aly, Oakland, FL 34787
  • /2

    $446,340 Sold Feb 25, 2026

    Unlisted Address

    • 3 Beds
    • 2.5 Baths
    • 2,186 Sq Ft
    • Built 2026

    Last Sold Summary

    • $204/SF

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

    Unlisted Address
    • /2

      Est $1,694,864 Not Listed For Sale

      1243 Civitas Way, Winter Garden, FL 34787

      • 5 Beds
      • 4.5 Baths
      • 4,020 Sq Ft
      • Built 2023
      1243 Civitas Way, Winter Garden, FL 34787

      Last Sold Summary

      • 8% Below List Price
      • $460/SF
      • 4 Days On Market

      Last Sold Price $1,850,000

      Last Listing Agent Ronald Ziolkowski RE/MAX

  • /51

    $824,950

    • 3 Beds
    • 2.5 Baths
    • 2,348 Sq Ft

    9008 Sonoma Coast Dr, Oakland, FL 34787

    Welcome to your dream home! This beautifully decorated 3 Bedroom + Office, 2 1/2 Bath home where comfort meets style offers stunning lake views and a sleek tile roof. Upon entering you'll be greeted by architectural arches and a wide foyer entry. To your left, you will be greeted by architectural arches and a wide foyer entry. On your left you will find a Den/Study/Office with glass entry doors &

    Gary Berkson RE/MAX CENTRAL REALTY

    9008 Sonoma Coast Dr, Oakland, FL 34787
  • /19

    $3,500 per month

    • 4 Beds
    • 3 Baths
    • 2,100 Sq Ft
    • House for Rent

    17727 Sharp Pummelo Aly, Oakland, FL 34787

    This stunning new home features premium upgrades throughout. The first floor boasts 8-foot exterior and interior doors, a gourmet kitchen, and a private bedroom with a full bathroom featuring an upgraded walk-in shower. The kitchen, family room, and dining area flow seamlessly together and open onto an extended lanai. Upstairs, you'll find the remaining bedrooms, including a primary suite with a

    Angela Magac THE PROPERTY STOP LLC

    17727 Sharp Pummelo Aly, Oakland, FL 34787
  • /2

    $1,400,000 Sold Jun 27, 2025

    141 Millholland St, Oakland, FL 34760

    • 4 Beds
    • 3.5 Baths
    • 3,497 Sq Ft
    • Built 2002

    Last Sold Summary

    • 12% Below List Price
    • $400/SF
    • 72 Days On Market

    Current Estimated Value $1,375,445

    Last Listing Agent Matthew Matin CLOCK TOWER REALTY

    141 Millholland St, Oakland, FL 34760
    • /2

      Est $507,696 Not Listed For Sale

      14091 Frasier St, Oakland, FL 34787

      • 4 Beds
      • 3 Baths
      • 2,112 Sq Ft
      • Built 2024
      14091 Frasier St, Oakland, FL 34787

      Last Sold Summary

      Last Listing Agent Erika Gao RC GROUP REALTY LLC

  • /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
  • /16

    $3,200 per month

    • 3 Beds
    • 2.5 Baths
    • 2,103 Sq Ft
    • House for Rent

    17609 Japonica Bloom Dr, Oakland, FL 34787

    Welcome to 17609 Japonica Bloom Drive—a brand new home designed for modern living and effortless entertaining. Soaring 8-foot doors throughout the first floor create an impressive, open atmosphere. The gourmet kitchen flows seamlessly into the dining area, making it easy to host while you cook. Step outside to the extended lanai, perfect for outdoor gatherings and relaxation. Upstairs, you'll

    Angela Magac THE PROPERTY STOP LLC

    17609 Japonica Bloom Dr, Oakland, FL 34787
  • /2

    $735,000 Sold Oct 30, 2025

    2340 Standing Rock Cir, Winter Garden, FL 34787

    • 5 Beds
    • 3 Baths
    • 3,493 Sq Ft
    • Built 2019

    Last Sold Summary

    • 3% Below List Price
    • $210/SF
    • 112 Days On Market

    Current Estimated Value $726,813

    Last Listing Agent Jennifer Coon LAKESIDE REALTY WINDERMERE INC

    2340 Standing Rock Cir, Winter Garden, FL 34787
    • /2

      Est $613,826 Not Listed For Sale

      15030 Summer Harvest St, Oakland, FL 34787

      • 5 Beds
      • 4.5 Baths
      • 2,861 Sq Ft
      • Built 2024
      15030 Summer Harvest St, Oakland, FL 34787

      Last Sold Summary

      • 4% Above List Price
      • $206/SF

      Last Sold Price $588,332

      Last Listing Agent Elio Serpa AUTHENTIC REAL ESTATE TEAM

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