Oakland, FL Homes for Sale with Garage

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  $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
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  $2,130,760 New Construction

  • 5 Beds
  • 5.5 Baths
  • 3,992 Sq Ft

  1146 Prado Ln, Oakland, FL 34787

  Pre-Construction. To be built. Introducing the Hearth Stone Model by Davila Homes. Discover the perfect blend of modern luxury and everyday comfort in the Hearth Stone, a beautifully designed 3,992-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

  Heather Spirazza REGENCY REAL ESTATE LLC

  1146 Prado Ln, Oakland, FL 34787
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  $3,575,000 New Construction

  • 5 Beds
  • 7 Baths
  • 5,478 Sq Ft

  510 Briley Ave, Oakland, FL 34787

  Stunning J&J Model Home in Briley Farm – Leaseback Opportunity! Step into unmatched luxury at this impeccably crafted J&J Building model home, perfectly positioned on a premier corner lot in the sought-after Briley Farm community of Oakland, FL. Designed with exceptional attention to detail, this residence offers 4 bedrooms, 4 full baths, 2 powder baths, a loft, bonus room, private office, two

  Alexis Anderson REGENCY REAL ESTATE LLC

  510 Briley Ave, Oakland, FL 34787
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  $594,000 New Construction

  • 4 Beds
  • 3 Baths
  • 2,143 Sq Ft

  12915 Westhaven Oak Dr, Oakland, FL 34787

  Under Construction. Toll Brothers New Construction at Winter Garden Horizon West. Estimate completion July 2024. Single family Bungalow. This home features a covered entry that leads to a spacious foyer and an expansive guest suite. The living area includes a dining room, with breakfast bar, great room, and access to the courtyard. The second-floor features 2 bedrooms and a master suite is

  DeVahn Powell ORLANDO TBI REALTY LLC

  12915 Westhaven Oak Dr, Oakland, FL 34787
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  $875,000

  • 4 Beds
  • 3.5 Baths
  • 3,406 Sq Ft

  607 E Oakland Ave, Winter Garden, FL 34787

  Welcome to this exceptional Winter Garden home with 4 bedrooms, 3.5-bathrooms, PLUS home office PLUS upstairs bonus room, flexible living spaces make this home work for you. This is 607 E. Oakland Ave - where classic Old-Florida charm meets modern luxury and unbeatable location. Tile flooring and refined tray ceilings flow throughout the home, while the gourmet kitchen with premium upgrades is

  Kristine McKinley RE/MAX TOWN & COUNTRY REALTY

  607 E Oakland Ave, Winter Garden, FL 34787
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  $1,998,000 New Construction

  • 4 Beds
  • 4 Baths
  • 4,557 Sq Ft

  1258 Ridge Lake Way, Winter Garden, FL 34787

  Pre-Construction. To be built. Pre-Construction. To be built. A Custom home in the Reserve of the sought-after Oakland Park community. This is a RCB Homes custom-built two story, four-bedroom, four-bath floor plan that you will customize with all the luxury finishes you will pick yourself! The floorplan is an open concept design, but you can still make changes to the floorplan if you want! The

  Chris Herlihy NEW HOMES REAL ESTATE, INC.

  1258 Ridge Lake Way, Winter Garden, FL 34787
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  $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
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  $725,000

  • 5 Beds
  • 4.5 Baths
  • 3,725 Sq Ft

  3294 Hanging Tide St, Oakland, FL 34787

  3.625% VA Assumable Loan! Welcome home to 3294 Hanging Tide, located in the premier community of Lakeview Preserve. This home is known as the Yorkshire model and was built by Pulte Homes in 2021. This is your opportunity to buy a new home, without the wait! The Yorkshire model is known for its space. The Yorkshire plan is highly desired, because of the first floor guest suite, with its on

  Ken Pozek REAL BROKER, LLC

  3294 Hanging Tide St, Oakland, FL 34787
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  $549,990 New Construction

  • 4 Beds
  • 3 Baths
  • 2,175 Sq Ft

  2934 Good Vibes Way, Oakland, FL 34787

  Under Construction. This popular new Hendrix is a four-bedroom home with convenient single-story living. Three secondary bedrooms are located near the front of the home off the foyer, near a versatile flex space ready to be used as an office or studio. An open-concept floorplan blends the kitchen, living and dining areas with easy access to a covered patio, while a luxe owner’s suite is nestled

  Ben Goldstein LENNAR REALTY

  2934 Good Vibes Way, Oakland, FL 34787
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  $789,999

  • 5 Beds
  • 4.5 Baths
  • 3,682 Sq Ft

  3351 Current Ave, Oakland, FL 34787

  Welcome to this stunning two-story Tortola floor plan by Taylor Morrison, ideally located in the gated community of Lakeview Preserve in Winter Garden. Perfectly positioned on an oversized 75-foot-wide corner homesite with no rear neighbors, this home offers exceptional privacy, beautiful rear views, and a welcoming front porch that sets the tone from the moment you arrive. The elegant

  Amy Kidwell PA PREFERRED REAL ESTATE BROKERS

  3351 Current Ave, Oakland, FL 34787
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  $699,900

  • 4 Beds
  • 3.5 Baths
  • 3,583 Sq Ft

  729 Strihal Loop, Oakland, FL 34787

  Luxury, Location, and Lake Access !! This elegant 5 bedrooms, 3.5 baths home is located in an exclusive gated community on Johns Lake, offering privacy and luxury lifestyle. Home boasts vaulted ceilings and designer quartz counter tops. Step outside to your private pool or take advantage of the community's private boat ramp with direct lake access to popular Johns Lake. Home is updated with the

  Subhas Sawh LIBERTY HOME SALES INC

  729 Strihal Loop, Oakland, FL 34787
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  $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
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  $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
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  $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
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  $815,000

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

  9611 Lost Creek Dr, Oakland, FL 34787

  Seller offering $10,000 toward Buyer’s Closing Costs + Golf Cart AND Furniture INCLUDED with sale!No rear neighbors! Situated on a premium conservation lot with lake views, this fully furnished 4-bedroom, 3-bathroom two-story home in the desirable Waterleigh community offers privacy, upgrades, and true move-in-ready convenience. Exceptional curb appeal features a brick paver driveway and

  Mariana Micheti M2M REALTY

  9611 Lost Creek Dr, Oakland, FL 34787
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  $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
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  $794,000 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,547 Sq Ft

  4653 Golden Birch Ave, Oakland, FL 34787

  Stunning 3-bedroom, 2.5-bath home with soaring ceilings, a versatile front room, a gourmet kitchen. This is the beautiful Mahogany Estate Floor plan By Pulte, lots of upgrades Slide into this beautiful home, starting with a flexible front room—perfect as an office, study, or formal living space—welcoming you right at the entry. Just beyond, the high-end gourmet kitchen is a showstopper, featuring

  Armando Torres POWERHOUSE REAL ESTATE NETWORK

  4653 Golden Birch Ave, Oakland, FL 34787
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  $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
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  $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
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  $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
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  $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
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  $715,000

  • 5 Beds
  • 3.5 Baths
  • 3,007 Sq Ft

  2451 Sky Stone Ct, Oakland, FL 34787

  THIS ONE IS A MUST SEE!! UPGRADES ON UPGRADES ON UPGRADES . Welcome to Oakland Trails, a beautiful and well-established community located in the charming, small-town City of Oakland. This spacious 5-bedroom, 3.5-bath home features a thoughtfully designed layout offering flexibility, comfort, and room to grow—perfect for today’s lifestyle.From the moment you enter, you are welcomed by a cozy Great

  Krichely Gonzalez Rodriguez KELLER WILLIAMS ADVANTAGE III

  2451 Sky Stone Ct, Oakland, FL 34787
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  $800,000

  • 5 Beds
  • 3 Baths
  • 3,528 Sq Ft

  1970 Standing Rock Cir, Oakland, FL 34787

  Discover expansive living and modern sophistication in this STUNNING 5-bedroom, 3-bath home with a Spacious, Peaceful backyard in the highly desirable Oakland Trails community, minutes from the West Orange Trail and the Winter Garden Plant Street Market. Offering over 3,500 SQUARE FEET of beautifully designed space and built in 2019, this residence combines contemporary comfort with UPSCALE

  Jennifer Wemert WEMERT GROUP REALTY LLC

  1970 Standing Rock Cir, Oakland, FL 34787
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  $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
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  $999,900

  • 3 Beds
  • 2 Baths
  • 2,214 Sq Ft

  13343 Sunny Retreat Ln, Oakland, FL 34787

  he neighbors call this home the best kept secrets in Oasis. Sip your coffee from from the comfort of your backyard facing due east and enjoy the gorgeous sunrise, every morning!In the evening, you'll find great views of the Disney fireworks! You won't be able to find these beautiful views and gorgeous Pergola/Patio set up anywhere in the community! The seller spared no expense in making the

  John Hart ENGEL & VOLKERS ORLANDO DR PHILLIPS

  13343 Sunny Retreat Ln, Oakland, FL 34787
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  $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
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  $2,995,000 New Construction

  • 6 Beds
  • 6.5 Baths
  • 5,144 Sq Ft

  312 Briley Ave, Oakland, FL 34760

  Under Construction. Introducing an extraordinary luxury estate by Element Home Builders in the sought after Briley Farm community, where timeless design, exceptional craftsmanship, and modern elegance come together on a beautiful oversized, nearly half acre corner lot. This remarkable 6-bedroom, 6.5-bath custom residence offers an unparalleled living experience with every detail thoughtfully

  Carolina Dumit CORCORAN PREMIER REALTY

  312 Briley Ave, Oakland, FL 34760
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  $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
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  $399,990 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,644 Sq Ft

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

  The Harbor floor plan offers a smartly designed two-story townhome that caters to both convenience and space. With three bedrooms and two and a half bathrooms, this home ensures comfort on every level. All three bedrooms are located upstairs, providing privacy and quiet from the main living areas. The second floor also features a spacious primary suite with a walk-in closet and private bath,

  Dream Finders Homes Builder

  14229 Lanyard Way Unit 36477638, Oakland, FL 34787
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  $577,990 New Construction

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft

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

  The Lexington floorplan is a spacious one-story design, featuring three comfortable bedrooms and two bathrooms, offering a total of 1,856 square feet. This home includes a versatile three-car garage with tandem space, perfect for extra storage or a workshop area. The open-concept layout connects the great room, cafe, and kitchen, creating a welcoming atmosphere for entertaining and everyday

  Dream Finders Homes Builder

  14229 Lanyard Way Unit 36464864, Oakland, FL 34787
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  $5,000

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

  2228 Gopher Tortoise Terrace, Oakland, FL 34787

  Foreclosure Auction Ends February 17, 2026 at 11:00 AM EST. Discover this inviting 3-bedroom, 2.5-bathroom townhome, offering a wonderful opportunity to live in the desirable Longleaf at Oakland community. The list price is the opening bid for the online auction. Sold As-is.

  Jamie Boone Jaime L Boone LLC

  2228 Gopher Tortoise Terrace, Oakland, FL 34787
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  $530,000

  • 3 Beds
  • 2.5 Baths
  • 2,128 Sq Ft

  6060 Glory Bower Dr, Oakland, FL 34787

  Beautifully maintained home featuring 3 bedrooms plus a versatile flex room that can easily be converted into a 4th bedroom, offering the potential to increase future value. The home includes 2.5 bathrooms and a spacious private front porch, perfect for enjoying sunrise views and outdoor living. The kitchen has been thoughtfully upgraded by an interior designer, showcasing luxury finishes and

  Alexandra Lattuf ANCHOR REAL ESTATE

  6060 Glory Bower Dr, Oakland, FL 34787
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  $765,000

  • 5 Beds
  • 4.5 Baths
  • 4,440 Sq Ft

  3387 Current Ave, Oakland, FL 34787

  Gorgeous home at Winter Garden gated community LakeView Preserve, San Benita model with upgrade of extended lanai and a lot of home improvement, Gourmet Kitchen, open floor plan, engineer wood flooring, NO CARPET in the house, crown molding, study room, dining room, and huge game room in second floor, first floor master bedroom suite, second floor with another bedroom suite. Ceiling fans with

  Li Xue AGENT GROUP REALTY

  3387 Current Ave, Oakland, FL 34787
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  $649,000

  • 4 Beds
  • 3 Baths
  • 2,650 Sq Ft

  529 Johns Landing Way, Oakland, FL 34787

  Welcome to your dream home in a prestigious gated community! This stunning 4-bedroom, 3-bathroom house offers 2,650 square feet of comfortable living space designed for both relaxation and entertainment. The thoughtfully designed layout includes a versatile fourth bedroom that can easily serve as a mother-in-law suite, perfect for multi-generational living or hosting extended guests. The primary

  Denise Pellegrino REAL BROKER, LLC

  529 Johns Landing Way, Oakland, FL 34787

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