Oakland, FL 2-Story Homes for Sale

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  $749,000 New Construction

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

  38 S Pollard St, Oakland, FL 34760

  Welcome to this beautifully crafted custom-built two-story home in the highly desirable Town of Oakland—offering the perfect blend of quality construction, modern design, and small-town charm with NO HOA.The thoughtfully designed floor plan features all main living areas on the first floor, including a spacious living room, dining area, and a well-appointed kitchen with high-quality

  Cassia Barros MS LAND & BUILDING LLC

  38 S Pollard St, Oakland, FL 34760
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  $700,000 New Construction

  • 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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  $600,000 New Construction

  • 4 Beds
  • 4.5 Baths
  • 2,149 Sq Ft

  14748 Field Daisy Dr, Oakland, FL 34787

  Welcome to the Newberry at 14748 Field Daisy Drive in Harvest at Ovation. The Newberry Bungalow offers modern living with a layout designed for both everyday comfort and effortless entertaining. Step through the foyer into a spacious great room, passing a secondary bedroom and full bath along the way. The designer kitchen overlooks the main living area and flows seamlessly to the bright, inviting

  Taylor Morrison Builder

  14748 Field Daisy Dr, Oakland, FL 34787
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  $1,949,000 New Construction

  • 5 Beds
  • 4.5 Baths
  • 3,862 Sq Ft

  511 Briley Ave, Oakland, FL 34787

  Welcome to this stunning custom residence by Element Home Builders, located in the highly sought-after community of Briley Farm. Thoughtfully designed with both elegance and functionality in mind, this expansive 5-bedroom, 4.5-bathroom home offers approximately 3,862 square feet of refined living space.Step inside to a dramatic two-story foyer that sets the tone for the home’s open and airy

  Carolina Dumit CORCORAN PREMIER REALTY

  511 Briley Ave, Oakland, FL 34787
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  $596,832 New Construction

  • 3 Beds
  • 3.5 Baths
  • 2,149 Sq Ft

  14736 Field Daisy Dr, Oakland, FL 34787

  Welcome to the Newberry at 14736 Field Daisy Drive in Harvest at Ovation! The Newberry bungalow floor plan is a true representation of modern living and the perfect space for all of your entertainment needs and desires. The 2149 sq. ft. two-story home with 3 bedrooms, 3.5 bathrooms and a 2-car detached garage presents prospective homebuyers with both the basic features and intricate details that

  Taylor Morrison Builder

  14736 Field Daisy Dr, Oakland, FL 34787
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  $693,240 New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,147 Sq Ft

  3120 Namaste Dr, Oakland, FL 34787

  Under Construction. The Summerlin checks all your boxes! This breath taking two-story home features an expansive design with a convenient three-car garage. The first floor features an open-concept family room that complements a chef-ready kitchen and a cozy dining room, plus a private office and a spacious lanai. On the same level is the tranquil owner’s suite with an attached bathroom. Found

  Ben Goldstein LENNAR REALTY

  3120 Namaste Dr, Oakland, FL 34787
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  $1,032,585 New Construction

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

  12904 Westhaven Oak Dr, Oakland, FL 34787

  The Griffin's welcoming extended covered porch, and inviting covered entry and foyer, flow past the lovely dining room to the spacious great room and views of the desirable covered lanai beyond. The well-designed kitchen overlooks a bright casual dining area, and is highlighted by a large center island with breakfast bar, plenty of counter and cabinet space, and roomy walk-in pantry. The graceful

  Toll Brothers, Inc. Builder

  12904 Westhaven Oak Dr, Oakland, FL 34787
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  $674,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,508 Sq Ft

  12919 Westhaven Oak Dr, Oakland, FL 34787

  Under Construction. Toll Brothers New Construction in Horizon West – Winter Garden | Estimated Completion Summer 2026Bungalow featuring a private in-law suite above a detached 2-car garage. A charming covered entry welcomes you into an open and expansive floor plan with seamless flow between the great room, kitchen, and dining area — ideal for both everyday living and entertaining.Enjoy

  Dayene Grubert ORLANDO TBI REALTY LLC

  12919 Westhaven Oak Dr, Oakland, FL 34787
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  $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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  $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 2026. 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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  $548,000 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,062 Sq Ft

  12911 Westhaven Oak Dr, Oakland, FL 34787

  Under Construction. Under Construction. Toll Brothers New Construction in Horizon West – Winter Garden | Estimated Completion Summer 2026. This home is conducive for entertaining with its open floor plan. This home features a covered entry that leads to an open and expansive living space, kitchen, and dining. The home features covered lanai and a spacious courtyard with access to the detached 2

  Dayene Grubert ORLANDO TBI REALTY LLC

  12911 Westhaven Oak Dr, Oakland, 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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  $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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  $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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  $974,300 Open Sat 10AM - 4PM

  • 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
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  $949,790 New Construction

  • 5 Beds
  • 4.5 Baths
  • 4,313 Sq Ft

  4632 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

  4632 Golden Birch Ave, Oakland, 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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  $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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  $655,990 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,843 Sq Ft

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

  The Captiva floorplan offers a spacious two-story design with 4 bedrooms, 2.5 bathrooms, and plenty of extra room for customization. This thoughtfully laid-out home includes a flex space on the first floor, which can be transformed into a guest suite or home office, adding versatility to the design. A bonus room on the second floor provides additional living space, perfect for a media room or

  Dream Finders Homes Builder

  14229 Lanyard Way Unit 36490537, 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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  $508,990 New Construction

  • 4 Beds
  • 3 Baths
  • 2,083 Sq Ft

  Newbury Plan at Serenade at Ovation - Bungalow, Oakland, FL 34787

  Discover the Newbury - our largest bungalow! This expansive home is designed to accommodate a variety of lifestyles with its 4 bedrooms, 3 bathrooms, a loft, and a 2-car garage. The extended kitchen is a standout feature, offering more cabinet space than you'll ever need, perfect for those who love to cook and entertain. Each bedroom in the Newbury is generously sized ensuring that everyone in

  Dream Finders Homes Builder

  14229 Lanyard Way Unit 36490206, 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 - Bungalow, 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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  $829,346 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,718 Sq Ft

  15075 Tea Tree Dr, Oakland, FL 34787

  Opportunity in Avalon Woods! Welcome to the Biscayne, a spacious two-story single-family home designed with both style and functionality in mind. The 20-foot ceiling entryway creates a stunning first impression, leading into a bright and open main living area. A guest bedroom with full bath downstairs provides comfort and flexibility for visitors or multi-generational living. The beautifully

  Dream Finders Homes Builder

  15075 Tea Tree Dr, Oakland, FL 34787
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  $1,675,000 New Construction

  • 5 Beds
  • 5 Baths
  • 3,895 Sq Ft

  Custom Carrabelle Plan at Oakland Park, Winter Garden, FL 34787

  AR Homes Builder

  884 Tilden Oaks Trail Unit 37615294, Winter Garden, FL 34787
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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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