Oakland, FL Homes for Sale with Garage

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  /76

  $1,225,000

  $75K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,710 Sq Ft

  1156 Civitas Way, Winter Garden, FL 34787

  Prive Improvement!! Experience luxury in this immaculate 2022 custom RCB home, featuring high-end upgrades and a versatile floor plan. The main-level flex suite with a massive closet is perfect as an office, 4th bedroom, or playroom. The living area features a dramatic two-story fireplace and open staircase flowing into a chef’s kitchen with upgraded GE Cafe Appliances. The oversized 3-car garage

  Heidi Pfeffer-Morgan DALTON WADE INC

  1156 Civitas Way, 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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  /71

  $1,548,000

  $40K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 3,613 Sq Ft

  1412 Johns Cove Ln, Oakland, FL 34787

  Virtually Staged. BACK ON MARKET! And Reimagined to IMPRESS! Gorgeous Lake Front Property on John's Chain with so many NEW UPGRADES! ALL NEW Flooring throughout! NEW Completely Repainted interior! Updated vanities and accents throughout bathrooms. Feels like a brand new home! "Triple-split" bedroom plan is a winner for those who desire 1-story living--all wrapped around those beautiful lake

  Betsey West NEXT RESIDENCE REALTY LLC

  1412 Johns Cove Ln, Oakland, FL 34787
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  /24

  $1,059,000

  $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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  /3

  $409,990

  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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  /4

  $1,975,000

  New Construction Open Tue 11AM - 4PM

  • 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

  $469,000

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

  14014 Scarlet Aster Aly, Oakland, FL 34787

  Rare Dual Owner's Suite Townhome — Priced to Move, Near Disney This 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 out. What sets this home apart is its dual

  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

  $2,238,120

  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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  /57

  $765,000

  $95K PRICE DROP

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

  9611 Lost Creek Dr, Oakland, FL 34787

  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 welcoming front porch. Inside, enjoy wood-look tile throughout the main living areas, a flexible formal

  Patricia Mendonca Garcia Cunha M2M REALTY

  9611 Lost Creek Dr, Oakland, FL 34787
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  /25

  $479,900

  $10K 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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  /64

  $599,000

  $26K PRICE DROP

  • 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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  /9

  $609,990

  New Construction $38K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,911 Sq Ft

  3128 Namaste Dr, Oakland, FL 34787

  Under Construction. The Inverness is an expansive single-story design that exudes luxury and features two extra rooms for versatile needs. An open-concept kitchen merges effortlessly into an intimate dining room and a spacious family room ideal for entertaining, with glass-sliders extending to the lanai for outdoor living. There is a total of four bedrooms, including the luxurious owner’s suite

  Ben Goldstein LENNAR REALTY

  3128 Namaste Dr, Oakland, FL 34787
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  /26

  $674,350

  New Construction

  • 4 Beds
  • 2 Baths
  • 1,882 Sq Ft

  5576 Dr, Oakland, FL 34787

  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.Welcome to your dream home – the Cardinal. This stunning new construction features 4 spacious

  Adrienne Escott PULTE REALTY OF NORTH FLORIDA LLC

  5576 Dr, Oakland, FL 34787
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  /35

  $514,900

  $10K 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

  $700,000

  New Construction $4K 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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  /23

  $595,000

  $20K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,477 Sq Ft

  9360 Mclaren Aly, Oakland, FL 34787

  **SELLER MOTIVATED - NEW PRICE*** Welcome to this beautifully appointed, move-in-ready home located in the highly desirable, resort-style master-planned community of Waterleigh in Winter Garden. This home offers the perfect blend of modern sophistication and everyday functionality across a bright, open-concept design. From the moment you enter through the front door, the airy foyer welcomes you

  Leslie Heimer PREMIER SOTHEBYS INT'L REALTY

  9360 Mclaren Aly, 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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  /30

  $874,900

  • 4 Beds
  • 4.5 Baths
  • 3,134 Sq Ft

  1231 Foltz Loop, Oakland, FL 34787

  Nestled in the serene, lakefront community of Hull Island, this meticulously maintained corner-lot home offers 4 bedrooms, 4.5 bathrooms, and a spacious bonus/game room. The Dorchester floor plan delivers a modern layout designed for both comfort and functionality. Upon entering the elegant foyer, you are welcomed by a formal dining room or flex space that leads into a bright, open-concept living

  Elisabeth Rusnak SOUTHERN REALTY GROUP LLC

  1231 Foltz Loop, 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

  $629,999

  New Construction $119K PRICE DROP

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

  38 S Pollard St, Oakland, FL 34760

  Brand new 2026 construction with Certificate of Occupancy in place and ready for immediate move-in. This 4-bedroom, 2.5-bath home offers 1,872 sqft of modern living space with custom finishes and a functional open layout. Thoughtfully designed with a clean, contemporary style, the home provides low-maintenance living and the flexibility of a non-HOA setting. Now positioned to reflect current

  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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  /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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  /68

  $1,374,990

  • 5 Beds
  • 3.5 Baths
  • 3,910 Sq Ft

  9827 Beach Port Dr, Oakland, FL 34787

  Perfectly positioned on a PREMIER WATERFRONT LOT just under half an acre, this stunning 3,910-square-foot residence delivers luxury living at every turn. Tucked away at the end of a tranquil cul-de-sac and situated on one of the few homesites in the neighborhood with no neighbors in front or behind, the property offers an exceptional sense of privacy with beautiful views of Lake Noah. A grand

  Silvia Kinkela SERHANT

  9827 Beach Port Dr, Oakland, FL 34787
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  /57

  $535,000

  • 4 Beds
  • 3.5 Baths
  • 2,486 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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  /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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  /37

  $649,000

  $26K PRICE DROP

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

  914 Trowman Aly, Winter Garden, FL 34787

  Virtually Staged. Nestled in the highly sought-after Oakland Park community, this beautifully maintained 3-bedroom, 3-bath home is the definition of move-in ready living. Featuring desirable upgrades throughout, including gas appliances, elegant plantation shutters, and a turnkey design, this home offers the perfect blend of comfort, style, and convenience. Enjoy open-concept living spaces filled

  Erica Diaz HOMEVEST REALTY

  914 Trowman Aly, Winter Garden, FL 34787

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