Oakland, FL 2-Story Homes for Sale

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  $499,990 New Construction

  • 4 Beds
  • 3 Baths
  • 1,847 Sq Ft

  4580 Maple Waltz, Oakland, FL 34787

  Exceptional investment opportunity! This stunning new townhome built by Pulte Homes is located in the desirable Park Side Trails community in Clermont, FL. The property is already leased starting November 28th with a 12-month contract at $2,800/month, offering immediate rental income and a great return potential.Featuring a bright and open floor plan with abundant natural light throughout,

  Marta Faustino DTB FLORIDA REALTY, INC.

  4580 Maple Waltz, Oakland, FL 34787
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  $1,047,790 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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  $465,000 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,730 Sq Ft

  8937 Matriarca Alley, Oakland, FL 34787

  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 gathering room

  Tony Wong, LLC SANCTUM REALTY PROFESSIONALS LLC

  8937 Matriarca Alley, Oakland, FL 34787
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  $799,135 New Construction

  • 6 Beds
  • 4.5 Baths
  • 3,412 Sq Ft

  15093 Tea Tree Dr, Oakland, FL 34787

  One or more photo(s) has been virtually staged. Pre-Construction. To be built. Opportunity in Avalon Woods! Discover the newest community by Dream Finders Homes in highly sought-after Hamlin, Winter Garden. Welcome to the Anna Maria w/ Bonus, an award-winning open-concept home designed for modern living and effortless entertaining. The thoughtfully designed layout flows seamlessly from the great

  Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

  15093 Tea Tree Dr, Oakland, FL 34787
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  $775,000 Open Fri 9AM - 5PM

  • 5 Beds
  • 4.5 Baths
  • 3,101 Sq Ft

  16029 Honey Harvest St, Oakland, FL 34787

  New Construction - Ready Now! Built by Taylor Morrison, America's Most Trusted Homebuilder. Welcome to the Cumberland at 16029 Honey Harvest Street in Harvest at Ovation. This spacious two-story Cumberland offers 5 bedrooms, 4.5 bathrooms, and flexible living for every stage of life. The open-concept great room, dining area, and gourmet kitchen flow effortlessly together and open to an extended

  Michelle Campbell TAYLOR MORRISON REALTY OF FLORIDA INC

  16029 Honey Harvest St, 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, 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, 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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  $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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  $2,295,000 New Construction

  • 6 Beds
  • 5.5 Baths
  • 4,859 Sq Ft

  1244 Water Maple Dr, Oakland, FL 34787

  Pre-Construction. To be built. Introducing the Hamlin model by Element Home Builders—a stunning 4,859 square-foot residence designed for luxurious living and modern comfort. With 6 spacious bedrooms and 5.5 beautifully appointed bathrooms, this home offers ample space for families of all sizes and lifestyles.Step inside and experience an open-concept layout that combines elegance with

  Alexis Anderson REGENCY REAL ESTATE LLC

  1244 Water Maple Dr, Oakland, FL 34787
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  $2,150,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 4,388 Sq Ft

  1238 Water Maple Dr, Oakland, FL 34787

  Pre-Construction. To be built. Welcome to the Blossom home plan by Element Home Builders, where elegance meets functionality in a spacious, open layout. Boasting soaring ceilings and an expansive 12-foot kitchen island with abundant storage, this home is designed for both family living and entertaining. Enjoy seamless transitions between the gourmet kitchen, dining, and living areas, perfect for

  Heather Spirazza REGENCY REAL ESTATE LLC

  1238 Water Maple Dr, Oakland, FL 34787
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  $2,175,000 New Construction

  • 5 Beds
  • 8 Baths
  • 4,433 Sq Ft

  1232 Water Maple Dr, Oakland, FL 34787

  Pre-Construction. To be built. Presenting the Citrus plan by Element Home Builders—a spacious home designed for modern living. With 5 bedrooms and 5 bathrooms, and 3 powder bathrooms, this expansive layout provides the perfect combination of comfort, style, and functionality. Every inch of this home is thoughtfully designed to create ample space for both private retreats and vibrant social

  Alexis Anderson REGENCY REAL ESTATE LLC

  1232 Water Maple Dr, Oakland, FL 34787
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  $1,996,500 New Construction

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

  1258 Ridge Lake Way, Winter Garden, FL 34787

  Pre-Construction. To be built. Welcome 1258 Ridge Lake Way, nestled in the final phase of the sought-after Oakland Park community. This custom-built modern farmhouse by RCB Homes offers a perfect blend of style and comfort. Spanning just under 6,280 square feet, this two-story residence features four spacious bedrooms and four luxurious bathrooms, providing ample space for relaxation and

  Matt McKee COMPASS FLORIDA LLC

  1258 Ridge Lake Way, Winter Garden, FL 34787
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  $773,260 New Construction

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

  15075 Tea Tree Dr, Oakland, FL 34787

  One or more photo(s) has been virtually staged. Pre-Construction. To be built. Opportunity in Avalon Woods! Discover the newest community by Dream Finders Homes in highly sought-after Hamlin, Winter Garden. 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

  Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

  15075 Tea Tree Dr, Oakland, FL 34787
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  $1,975,000 New Construction

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

  1149 Dr, Oakland, FL 34787

  Pre-Construction. To be built. Welcome to the Clementine Floorplan by Element Home Builders – A Stunning New Home in Oakland's Premier Community!Discover your dream home with the Clementine Floorplan, a thoughtfully designed residence nestled in Oakland's newest, most sought-after community. This spacious, modern home combines elegance, functionality, and comfort to create the perfect

  Blaine Dooley REGENCY REAL ESTATE LLC

  1149 Dr, Oakland, 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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  $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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  $1,975,000 New Construction

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

  The Clementine Plan at The Grove, Oakland, FL 34760

  Element Home Builders Builder

  15752 E Oakland Ave St Unit 36498057, Oakland, FL 34760
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  $2,175,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 4,433 Sq Ft

  The Citrus Plan at The Grove, Oakland, FL 34760

  Element Home Builders Builder

  15752 E Oakland Ave St Unit 36480892, Oakland, FL 34760
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  $2,295,000 New Construction

  • 6 Beds
  • 5.5 Baths
  • 4,859 Sq Ft

  The Hamlin Plan at The Grove, Oakland, FL 34760

  Element Home Builders Builder

  15752 E Oakland Ave St Unit 36487597, Oakland, FL 34760
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  $2,150,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 4,388 Sq Ft

  The Blossom Plan at The Grove, Oakland, FL 34760

  Element Home Builders Builder

  15752 E Oakland Ave St Unit 36481095, Oakland, FL 34760
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  $369,900

  • 3 Beds
  • 2.5 Baths
  • 1,638 Sq Ft

  1386 Scarlet Oak Loop, Winter Garden, FL 34787

  Welcome to Maintenance-Free Living in the Gated Community of Tucker Oaks! This Beautifully Maintained END-UNIT Townhome lives like a single family home and features a BRAND-NEW ROOF (April 2025) and thoughtful upgrades throughout. Enjoy Peaceful mornings on the Screened-in Porch overlooking a tranquil pond with No Rear neighbors. This Spacious Floor Plan offers 3 Bedrooms and 2.5 bathrooms,

  Lisa Bennett WINDSOR REALTY GROUP INC

  1386 Scarlet Oak Loop, Winter Garden, FL 34787

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