Oakland, FL Homes for Sale with Garage

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  /4

  $1,975,000

  New Construction

  • 5 Beds
  • 5.5 Baths
  • 3,596 Sq Ft

  1106 Sarah Mathews Dr, Oakland, FL 34787

  Pre-Construction. To be built. Nestled within the exclusive Grove community, the Clementine Plan by Element Home Builders is a bespoke pre-construction offering that showcases timeless architecture, refined luxury, and exceptional craftsmanship. This thoughtfully designed residence features 5 bedrooms, 5 full bathrooms, a powder room, loft across 3,596 square feet of elegantly curated living

  Heather Spirazza REGENCY REAL ESTATE LLC

  1106 Sarah Mathews Dr, Oakland, FL 34787
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  /22

  $459,000

  $10K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,808 Sq Ft

  14014 Scarlet Aster Aly, Oakland, FL 34787

  ***** PRICE REDUCED *****Rare Dual Owner's Suite Townhome — Priced to Move, Near DisneyThis 3-bedroom, 3-bath, 1,808 sq ft Newton model townhome in Harvest at Ovation is one of the best values in the community right now. Built in 2024 and less than 2 years old, it shows like a model and is ready for immediate move-in, while comparable new construction in the area runs 7+ months

  Jarrett Brown LPT REALTY, LLC

  14014 Scarlet Aster Aly, Oakland, FL 34787
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  /4

  $498,990

  New Construction

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

  Brantley Plan at Serenade at Ovation - Bungalows, 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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  /18

  $2,380,160

  New Construction $142K PRICE INCREASE

  • 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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  /25

  $468,000

  $22K PRICE DROP

  • 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
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  /2

  $541,000

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,908 Sq Ft

  13031 Tollcross Way, Oakland, FL 34787

  Superior contemporary design. The Liston's welcoming covered porch and entry open immediately onto the expansive great room, with views to the lovely dining room and desirable large covered lanai beyond. The well-equipped gourmet kitchen is enhanced by a large center island with breakfast bar, plenty of counter and cabinet space, and generous walk-in pantry. The gorgeous primary bedroom suite is

  Toll Brothers, Inc. Builder

  13031 Tollcross Way, Oakland, FL 34787
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  /35

  $485,000

  $40K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,094 Sq Ft

  12308 Bracco St, Oakland, FL 34787

  Beautiful and nearly new home in the quiet and friendly Highland Ridge community. This home was built only two years ago and is in perfect condition, offering over 2,114 sq. ft. of air-conditioned space. The layout is open and bright, with a modern kitchen that overlooks the large living and dining areas, perfect for family time and hosting friends. A big plus for this property is the oversized

  Diller de Abreu Junior ELITE INTERNATIONAL REALTY INC

  12308 Bracco St, Oakland, FL 34787
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  /30

  $653,118

  New Construction $51K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 2,441 Sq Ft

  14780 Field Daisy Dr, Oakland, FL 34787

  Welcome to the Baldwin at 14780 Field Daisy Drive in Harvest at Ovation! Enter the charming oasis within this thoughtfully designed bungalow floor plan that offers 2,441 sq. ft. of inviting living space. Just past the foyer and formal dining room, the great room opens to the designer kitchen for an easy flow that is perfect for entertaining and relaxation. A first-floor bedroom with a full bath

  Taylor Morrison Builder

  14780 Field Daisy Dr, Oakland, FL 34787
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  /3

  $411,990

  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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  /39

  $796,000

  $4K PRICE DROP

  • 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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  /57

  $610,000

  $20K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,445 Sq Ft

  16186 Honey Harvest St, Oakland, FL 34787

  Move right into one of the most sought-after floor plans in Harvest at Ovation. This just-completed Taylor Morrison Baldwin model offers the rare opportunity to skip the build timeline and step into a never fully lived-in home loaded with designer upgrades and timeless style. Originally purchased as a long-term move, the sellers had a change of plans, creating an incredible opportunity for the

  Ken Pozek REAL BROKER, LLC

  16186 Honey Harvest St, Oakland, FL 34787
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  /56

  $620,000

  New Construction $129K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 1,872 Sq Ft

  38 S Pollard St, Oakland, FL 34760

  NEW PRICE IMPROVEMENT! Seller incentive available!Welcome home to this beautiful 2026 newly built residence in the desirable town of Oakland! This 4-bedroom, 2.5-bath home features modern finishes, an open-concept layout, and a spacious design perfect for today’s lifestyle. Enjoy the benefits of owning a newer construction home with peace of mind, energy-efficient features, and

  Cassia Barros MS LAND & BUILDING LLC

  38 S Pollard St, Oakland, FL 34760
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  /13

  $2,615,320

  New Construction

  • 6 Beds
  • 6.5 Baths
  • 4,658 Sq Ft

  1152 Prado Ln, Winter Garden, FL 34787

  Under Construction. Introducing one of Central Florida's most distinguished new addresses — the Oakshade floor plan by award-winning Davila Homes, nestled within the exclusive, boutique enclave of The Grove at the Harvest District in the charming Town of Oakland, Florida. Spanning an impressive 4,658 square feet, this stunning residence offers six generously sized bedrooms, each with its own

  Alexis Anderson REGENCY REAL ESTATE LLC

  1152 Prado Ln, Winter Garden, FL 34787
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  /31

  $550,000

  • 4 Beds
  • 2.5 Baths
  • 2,082 Sq Ft

  14123 Frasier St, Oakland, FL 34787

  SPECIAL FINANCING AVAILABLE! The seller is offering a promotional 3.875 interest rate through a rate buy-down program, plus ALL closing costs paid when using the preferred lender—creating an incredible opportunity for qualified buyers to significantly reduce their monthly payment and cash needed at closing. Welcome to this stunning newer construction home located in the highly desirable Horizon

  Yornelly Sanchez Manrique LEVO REAL ESTATE LLC

  14123 Frasier St, Oakland, FL 34787
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  /78

  $2,850,000

  • 7 Beds
  • 6.5 Baths
  • 6,400 Sq Ft

  15522 Shorebird Ln, Oakland, FL 34787

  Welcome to an extraordinary estate in Lakeshore Preserve, this exceptional lakefront estate represents a rare convergence of scale, sophistication, and resort-inspired living. Crafted by Toll Brothers, this expanded Santa Bella model stands as one of the largest and most distinguished residences in the community, offering over 6,400 square feet, 7 bedrooms, and 6.5 bathrooms. A stately tile roof

  Jack Zhao EAST PEARL REALTY

  15522 Shorebird Ln, Oakland, FL 34787
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  /57

  $535,000

  Open Sat 11AM - 2PM

  • 4 Beds
  • 3.5 Baths
  • 2,502 Sq Ft

  17167 Writing Aly, Oakland, FL 34787

  Located in the heart of Horizon West, 17167 Writing Aly offers the space, flexibility, and location buyers are looking for in Winter Garden. Just minutes from Hamlin Town Center, the 429, Disney, and Downtown Winter Garden, this home is positioned in one of Central Florida’s fastest-growing areas while still offering a true neighborhood feel with community green spaces, walking paths, and

  Ken Pozek REAL BROKER, LLC

  17167 Writing Aly, Oakland, FL 34787
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  /45

  $419,999

  • 3 Beds
  • 2.5 Baths
  • 1,636 Sq Ft

  10648 Words Dr, Winter Garden, FL 34787

  Storey Grove ** 2023 built ** Open floorplan **BACKS TO GREENSPACE!!** Beautiful wood ceramic tile entire 1st floor ** Attractive tv wall wood accent inlay in the family room ** White kitchen cabinetry with quartz counters and large cooking island ** All bedrooms are on the 2nd floor ** Nice size +/-16x20 brick paver patio area and 2 car detached garage ** Great RING security system, RING

  Gabriella Philippone INDEPENDENCE REALTY GROUP LLC

  10648 Words Dr, Winter Garden, FL 34787
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  /17

  $401,990

  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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  /3

  $577,990

  New Construction

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

  Lexington Plan at Serenade at Ovation - 50' Collection, 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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  /28

  $433,000

  • 4 Beds
  • 2 Baths
  • 1,778 Sq Ft

  17802 Jefferson St, Oakland, FL 34787

  Virtually Staged. Step into 17802 Jefferson St, a residence presenting a refreshed exterior appeal from fresh exterior paint and modernized interior amenities. The kitchen is fully equipped with all stainless steel appliances, establishing a contemporary culinary space, while a central fireplace provides warmth and a welcoming ambiance in the living area. Updated style and comfort are ready for

  Karen Albright OPENDOOR BROKERAGE LLC

  17802 Jefferson St, Oakland, FL 34787
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  /94

  $1,500,000

  • 5 Beds
  • 4 Baths
  • 3,781 Sq Ft

  2010 Boss Hewett St, Oakland, FL 34787

  Welcome to this stunning, like-new home that perfectly blends luxury, comfort, and modern design in the highly desirable community of Hull Island. Boasting five spacious bedrooms and four full bathrooms, this thoughtfully designed residence offers an ideal layout for both everyday living and entertaining. This home offers two spacious owner’s suites, one conveniently located on the first floor

  Vilmari Caraballo RE/MAX ASSURED

  2010 Boss Hewett St, Oakland, FL 34787
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  /37

  $595,000

  Open Thu 5PM - 7PM $80K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,642 Sq Ft

  914 Trowman Aly, Winter Garden, FL 34787

  Welcome to this beautifully maintained, move-in ready 3-bedroom, 3-bathroom home in Oakland Park, one of Winter Garden’s most desirable communities. Offering a blend of classic architecture, modern updates, and an exceptional location, this turnkey Winter Garden home is designed for comfortable Florida living.Step inside to a bright and spacious open-concept floor plan featuring abundant

  Erica Diaz HOMEVEST REALTY

  914 Trowman Aly, Winter Garden, FL 34787

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