Newest Homes for Sale in Oakland, FL

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  $679,990

  Open Sat 12PM - 4PM $100K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 3,284 Sq Ft

  8114 Sayings Dr, Winter Garden, FL 34787

  Virtually Staged. Beautifully maintained 5-bedroom, 3-bath home offering approximately 3,300 sq. ft. in the highly sought-after Storey Grove community of Winter Garden. Situated on a premium conservation and water-view lot with no rear neighbors, this home offers exceptional privacy and peaceful views from the screened lanai with an outdoor sink. The bright, open floor plan features a spacious

  Anna Shi LPT REALTY, LLC

  8114 Sayings Dr, Winter Garden, FL 34787
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  /24

  $1,010,000

  $1M PRICE INCREASE

  • 5 Beds
  • 4 Baths
  • 3,951 Sq Ft

  219 Largovista Dr, Oakland, FL 34787

  Beautiful house, fully remodeled luxury residence in the exclusive gated community of John's Landing. Offering nearly 4,000 sq/ft, this impressive 5 bedrooms, 4 bath home features, 2 of the bedrooms is a suite, high-end finishes, and a seamless modern design throughout.Porcelain tile flooring, a stunning gourmet kitchen with island with quartz countertops, custom cabinetry and a premium

  Durval Da Rocha NOVARE REAL ESTATE LLC

  219 Largovista Dr, Oakland, FL 34787
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  $1,049,000

  $246K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,469 Sq Ft

  250 N Walker St, Oakland, FL 34760

  Nestled in the heart of downtown Oakland, FL, this newly renovated two-story home features 4 bedrooms and 2.5 bathrooms. Situated on an oversized lot of nearly 1/2 acre, the property includes a resort-style pool, screened patio, shed, and a 3-car garage. Perfectly positioned between Clermont and Winter Garden, this rare property sits on quiet, charming dirt roads, surrounded by mature LIVE oak

  Alaina DiMare COAST TO COAST REAL ESTATE PRO

  250 N Walker St, Oakland, FL 34760
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  /10

  $3,200,000

  • 41 Beds
  • 75 Baths
  • 17,021 Sq Ft

  15992 W Colonial Dr, Oakland, FL 34787

  15992 W Colonial Dr, Oakland, FL – 32-Unit Income Producing Multifamily OpportunityExceptional opportunity to acquire a 32-unit income-producing asset in the heart of West Orange County, ideally positioned along the high-visibility W Colonial Dr / SR-50 corridor in the Town of Oakland.Situated on approximately 2.15 acres, this unique property offers a diverse mix of duplex-style

  Kyler Moreland REMAX SUNSTATE REALTY

  15992 W Colonial Dr, Oakland, FL 34787
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  $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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  $2,550,000

  $200K PRICE DROP

  • 5 Beds
  • 6 Baths
  • 4,373 Sq Ft

  812 Johns Point Dr, Oakland, FL 34787

  Experience unparalleled lakefront living in this fully renovated Mediterranean-style estate located in the exclusive gated community of John’s Cove on Johns Lake. A grand driveway and manicured landscaping welcome you into a striking modern entry and elegant interior featuring high-end flooring and designer finishes throughout.Designed for effortless entertaining, the open-concept layout

  Any Alves WRA BUSINESS & REAL ESTATE

  812 Johns Point Dr, Oakland, FL 34787
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  $350,000

  $15K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,497 Sq Ft

  2117 Gopher Tortoise Terrace, Oakland, FL 34787

  PRICE Improvement and this home can be purchased with NO INCOME VERIFICATION! Be sure to ask about the details! Skip the projects, this 2020 built home is ready for you! This open-concept layout creates a bright and inviting space perfect for entertaining.The kitchen, where matching marble countertops and cabinetry create a clean and cohesive look. A charming office nook on the first floor

  Mary Herrod De Boer SERHANT

  2117 Gopher Tortoise Terrace, Oakland, FL 34787
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  $515,000

  $30K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,204 Sq Ft

  2259 White Feather Loop, Oakland, FL 34787

  INCREDIBLE OPPORTUNITY to own this stunningly gorgeous 4 bedroom 2.5 bathroom corner lot home in the HIGHLY DESIRABLE community of Oakland Trails! Boasting over 2200 sq. feet of living space this 2017 built gem is amply equipped to meet the needs of families of all sizes and is gushing with stylistic appeal! Enter the home into a bright and positive feeling OPEN CONCEPT GREAT ROOM highlighted by

  Chuck Burt YOUNG REAL ESTATE

  2259 White Feather Loop, Oakland, FL 34787
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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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  /50

  $1,765,000

  $44K PRICE DROP

  • 5 Beds
  • 4 Baths
  • 3,784 Sq Ft

  906 Allendale Ln, Winter Garden, FL 34787

  Welcome home to calm, light-filled luxury on a peaceful pond in the sought-after golf cart district—just steps from the West Orange Trail and 3 miles to historic Downtown Winter Garden.This 4-bed, 3-bath custom home sits on a large lot and features an open, airy floor plan with upscale laminate flooring throughout. The gourmet kitchen is built to entertain: commercial-grade hood, gas range,

  Jurgita Blake CENTURY 21 CARIOTI

  906 Allendale Ln, Winter Garden, FL 34787
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  /3

  $2,098,000

  New Construction $100K PRICE INCREASE

  • 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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  $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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  /17

  $2,310,600

  New Construction $180K PRICE INCREASE

  • 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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  /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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  /2

  $1,675,000

  New Construction

  • 5 Beds
  • 5 Baths
  • 4,819 Sq Ft

  166 Hammock Preserve Loop, Oakland, FL 34787

  166 Hammock Preserve Loop, Oakland, FL 34787
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  /23

  $575,000

  $75K PRICE INCREASE

  • Land
  • 19,602 Sq Ft
  • $1,277,778 per Acre

  514 N Pollard St, Winter Garden, FL 34787

  Briley Farm, Central Florida’s newest custom home community, sits on 111 acres of lush landscape in Oakland, Florida. Here, you’ll have the opportunity to build your dream custom home with Pioneer Builders on a .45-acre corner lot. Pioneer Builders is renowned for their commitment to craftsmanship, attention to detail, and creating homes that reflect each client’s unique style. Every residence is

  Alexis Anderson REGENCY REAL ESTATE LLC

  514 N Pollard St, Winter Garden, FL 34787

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