Studio to 5 Bedroom Homes for Sale in Oakland, FL

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  $3,575,000 New Construction

  • 5 Beds
  • 7 Baths
  • 5,478 Sq Ft

  510 Briley Ave, Oakland, FL 34787

  Stunning J&J Model Home in Briley Farm – Leaseback Opportunity! Step into unmatched luxury at this impeccably crafted J&J Building model home, perfectly positioned on a premier corner lot in the sought-after Briley Farm community of Oakland, FL. Designed with exceptional attention to detail, this residence offers 4 bedrooms, 4 full baths, 2 powder baths, a loft, bonus room, private office, two

  Alexis Anderson REGENCY REAL ESTATE LLC

  510 Briley Ave, Oakland, FL 34787
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  $1,650,000

  • 6 Beds
  • 7.5 Baths
  • 5,614 Sq Ft

  620 N Tubb St, Oakland, FL 34760

  This exquisite gem has endless opportunities: a wellness center, wedding event venue, and Airbnb. Not looking to own a bed and breakfast? This would also make a fantastic stately residential home! This distinctive 19th-century Oakland Manor House sits on an .8-acre park-like setting in the charming town of Oakland. Carefully restored to preserve and enhance its original beauty with abundant

  Jennifer Wilson OAKSTRAND REALTY

  620 N Tubb St, Oakland, FL 34760
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  $670,000

  • 5 Beds
  • 3 Baths
  • 2,916 Sq Ft

  3318 Current Ave, Oakland, FL 34787

  HOME WARRANTY INCLUDED + APPRAISAL COVERED IF BUYER USES SELLER’S PREFERRED LENDER! Welcome to your dream home in the highly sought-after Lakeview Preserve, a gated community nestled near the shores of Johns Lake in Winter Garden. This beautifully appointed residence offers spacious and flexible living with 5 bedrooms and 3 full bathrooms, including a convenient guest suite or office on the first

  Geoffrey Lopez II RADIUS REALTY GROUP LLC

  3318 Current Ave, Oakland, FL 34787
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  $585,000

  • 3 Beds
  • 2.5 Baths
  • 2,010 Sq Ft

  2090 Standing Rock Cir, Oakland, FL 34787

  Price reduced to $585,000 on this Stunning Home in Oakland Trails!This immaculate 3-bedroom, 2.5 bath home blends thoughtful upgrades with a warm, inviting layout. From the moment you walk in, pride of ownership is evident. The bright, open living area features built-in HEOS speakers, perfect for entertainment. The chef’s kitchen will impress with 42" wood cabinetry, granite countertops,

  Tim Boon CREEGAN GROUP

  2090 Standing Rock Cir, 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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  $569,990 New Construction

  • 4 Beds
  • 3 Baths
  • 2,175 Sq Ft

  2934 Good Vibes Way, Oakland, FL 34787

  Under Construction. This popular new Hendrix is a four-bedroom home with convenient single-story living. Three secondary bedrooms are located near the front of the home off the foyer, near a versatile flex space ready to be used as an office or studio. An open-concept floorplan blends the kitchen, living and dining areas with easy access to a covered patio, while a luxe owner’s suite is nestled

  Ben Goldstein LENNAR REALTY

  2934 Good Vibes Way, Oakland, FL 34787
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  $499,000

  • 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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  $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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  $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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  $800,000 New Construction

  • 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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  $480,000

  • 4 Beds
  • 2 Baths
  • 2,065 Sq Ft

  717 Strihal Loop, Oakland, FL 34787

  Welcome Home to Johns Landing! Discover this beautifully maintained 4-bedroom, 2-bath residence located in the gated community of Johns Landing, offering private boat access to scenic Johns Lake. From the moment you step into the foyer, you’ll appreciate the soaring volume ceilings, tile flooring throughout the main living areas, and an abundance of natural light that creates a bright and

  Erica Sadelfeld THE REAL ESTATE COLLECTION LLC

  717 Strihal Loop, Oakland, FL 34787
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  $399,000

  • 3 Beds
  • 2.5 Baths
  • 1,568 Sq Ft

  12043 Holystone St, Oakland, FL 34787

  “The property is currently active for sale but is rented for $2500 monthly, with a lease valid until February 2026. The lease must be honored, so the property is best suited for investors looking for a rental income opportunity.”Welcome to Waterleigh community! This townhome has 3 bedroom 2.5 bathroom is conveniently located in Waterleigh Phase 4, near the Elementary and Middle School! It

  Ruth Santos Blystone WRA BUSINESS & REAL ESTATE

  12043 Holystone St, 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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  $1,775,000 Open Mon 12PM - 3PM

  • 5 Beds
  • 4.5 Baths
  • 3,991 Sq Ft

  854 Tilden Oaks Trail, Winter Garden, FL 34787

  This former J & J Building model home has never been lived in and has been carefully cared for. With 3,453 sq. ft. in the main house, it offers 4 bedrooms, 3.5 baths, and an oversized 2.5-car garage with extra space for a golf cart. A detached 538 sq. ft. pool house adds valuable flexibility, offering a fifth bedroom, full bath, wet bar, office, and walk-in closet—an ideal setup for extended

  Tracey McFadden OAK AVENUE REAL ESTATE LLC

  854 Tilden Oaks Trail, Winter Garden, FL 34787
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  $700,000

  • 5 Beds
  • 3.5 Baths
  • 3,381 Sq Ft

  729 Strihal Loop, Oakland, FL 34787

  One or more photo(s) has been virtually staged. Experience the height of Florida luxury in this stunningly renovated 5-bedroom pool home, nestled within an exclusive gated community featuring a private boat ramp and lake access. Boasting soaring ceilings, quartz countertops, and a striking panoramic landing, this residence blends architectural elegance with modern sophistication. Peace of mind is

  Dylan Stanley MARK SPAIN REAL ESTATE

  729 Strihal Loop, Oakland, FL 34787
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  $587,000

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

  16140 Harbor Mist Aly, Oakland, FL 34787

  Welcome to your dream home in Winter Garden! This stunning 2018-built residence offers 2,477 square feet of thoughtfully designed living space with four bedrooms and three and a half bathrooms. The open floor plan creates an inviting atmosphere perfect for both daily living and entertaining guests who might "accidentally" extend their stay. The first floor showcases beautiful tile flooring

  Jeanine Louis-Alcime EXP REALTY LLC

  16140 Harbor Mist Aly, Oakland, FL 34787
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  $599,000

  • 3 Beds
  • 2 Baths
  • 1,857 Sq Ft

  1808 Western Trailway Dr, Oakland, FL 34787

  Welcome to this stunning, like-new 3-bedroom, 2-bath home in the charming Hull Island community of Oakland, just 0.5 miles from the West Orange Trail, 1.5 miles to Costco, and only 10 minutes from historic downtown Winter Garden. Recently updated and truly move-in ready, this split-plan residence shines with beautiful wood-look tile flooring throughout (no carpet anywhere!), fresh backyard turf

  Daniel McGrath UNLOCK REALTY GROUP INC

  1808 Western Trailway Dr, 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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  $800,000

  • 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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  $460,000 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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  $649,000

  • 5 Beds
  • 4 Baths
  • 4,246 Sq Ft

  207 Largovista Dr, Oakland, FL 34787

  ACT FAST! HOMES OF THIS SIZE AND STYLE WITH A PRIVATE POOL RARELY STAY ON THE MARKET. SCHEDULE YOUR SHOWING TODAY BEFORE IT IS GONE. WITH INTEREST RATES DROPPING MORE BUYERS WILL BE ENTERING THE MARKET AND COMPETITION WILL INCREASE. NOW IS THE TIME TO MAKE YOUR MOVE! LISTED UNDER MARKET VALUE!!!!!!!! This impressive 5 bedroom 4 bathroom home features a private pool, a spacious fenced lot, and an

  Lindsay Seibert COLDWELL BANKER REALTY

  207 Largovista Dr, Oakland, FL 34787
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  $958,000

  • 4 Beds
  • 4.5 Baths
  • 3,408 Sq Ft

  9988 Beach Port Dr, Oakland, FL 34787

  Welcome to 9988 Beach Port Drive in the beautiful community Waterleigh in Winter Garden! This stunning property offers the perfect blend ofmodern luxury and serene coastal living. This home provides a peaceful retreat that embodies the essence of relaxation and comfort. With itsspacious layout, stylish design, and picturesque surroundings, 9988 Beach Port Driver is truly a gem waiting to

  Yukey Hoo U KEY REALTY

  9988 Beach Port Dr, Oakland, FL 34787
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  $2,995,000 New Construction

  • 6 Beds
  • 6.5 Baths
  • 5,144 Sq Ft

  312 Briley Ave, Oakland, FL 34760

  Under Construction. Introducing an extraordinary luxury estate by Element Home Builders in the sought after Briley Farm community, where timeless design, exceptional craftsmanship, and modern elegance come together on a beautiful oversized, nearly half acre corner lot. This remarkable 6-bedroom, 6.5-bath custom residence offers an unparalleled living experience with every detail thoughtfully

  Carolina Dumit CORCORAN PREMIER REALTY

  312 Briley Ave, Oakland, FL 34760
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  $459,000 New Construction

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

  8937 Matriarca Aly, Oakland, FL 34787

  Price adjustment! 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

  Tony Wong, LLC SANCTUM REALTY PROFESSIONALS LLC

  8937 Matriarca Aly, Oakland, FL 34787
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  $607,990 New Construction

  • 4 Beds
  • 3 Baths
  • 2,692 Sq Ft

  2930 Good Vibes Way, Oakland, FL 34787

  Under Construction. The Jagger has it all! This sleek new two-story home features a convenient game room on the second level, perfect for entertaining, relaxation and more. The first floor is host to an inviting open-concept layout shared between a modern kitchen, elegant dining room and comfortable family room. Three secondary bedrooms boast a private space near the front of the home off the

  Ben Goldstein LENNAR REALTY

  2930 Good Vibes Way, Oakland, FL 34787
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  $852,342 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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  $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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  $575,000

  • 5 Beds
  • 4 Baths
  • 3,449 Sq Ft

  229 Largovista Dr, Oakland, FL 34787

  **NEW PRICE – MUST-SEE LUXURY POOL HOME!** Prepare to fall in love with this stunning 5-bedroom, 4-bathroom home located in the exclusive gated community of *Johns Landing*. Offering nearly 3,500 sq. ft. of meticulously designed living space, this home is the perfect blend of elegance, comfort, and Florida living at its finest! From the moment you step inside, you'll be captivated by the beauty

  Richard Lokhnauth RL LUXURY REAL ESTATE

  229 Largovista Dr, Oakland, FL 34787
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  $577,990 New Construction

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

  Lexington Plan at Serenade at Ovation - Single Family Homes, 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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  $830,000

  • 5 Beds
  • 4.5 Baths
  • 4,440 Sq Ft

  3387 Current Ave, Oakland, FL 34787

  Gorgeous home at Winter Garden gated community LakeView Preserve, San Benita model with upgrade of extended lanai and a lot of home improvement, Gourmet Kitchen, open floor plan, engineer wood flooring, NO CARPET in the house, crown molding, study room, dining room, and huge game room in second floor, first floor master bedroom suite, second floor with another bedroom suite. Ceiling fans with

  Li Xue AGENT GROUP REALTY

  3387 Current Ave, Oakland, FL 34787
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  $675,000

  • 4 Beds
  • 3 Baths
  • 2,650 Sq Ft

  529 Johns Landing Way, Oakland, FL 34787

  Welcome to your dream home in a prestigious gated community! This stunning 4-bedroom, 3-bathroom house offers 2,650 square feet of comfortable living space designed for both relaxation and entertainment. The thoughtfully designed layout includes a versatile fourth bedroom that can easily serve as a mother-in-law suite, perfect for multi-generational living or hosting extended guests. The primary

  Denise Pellegrino REAL BROKER, LLC

  529 Johns Landing Way, Oakland, FL 34787
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  $359,900

  • 3 Beds
  • 2.5 Baths
  • 1,592 Sq Ft

  1428 Scarlet Oak Loop, Winter Garden, FL 34787

  Price Improvement! Welcome to 1428 Scarlet Oak Loop, a beautifully updated townhome in one of Winter Garden’s most sought-after gated communities! This well-maintained residence combines comfort, energy efficiency, and modern upgrades throughout. Featuring a brand-new roof, new HVAC system, and spray-foam insulation in the attic, you’ll enjoy lower utility bills and year-round comfort. Inside,

  Eric Bress, Jr ERIC BRESS REAL ESTATE LLC

  1428 Scarlet Oak Loop, Winter Garden, FL 34787
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  $268,900

  • 3 Beds
  • 2 Baths
  • 1,747 Sq Ft

  651 J W Jones Rd, Winter Garden, FL 34787

  *****Sellers motivated! Sellers will consider closing assistance to Buyer(s).***** Welcome Home! Bicyclists and nature lovers will appreciate being just minutes from West Orange Trail. Let the stresses of the day melt away as you step into this beautiful residence in the highly sought-after Winter Garden. Relax on the screened front porch as you soak in the peaceful atmosphere. Inside, the

  David Seeley EXIT REALTY TRI-COUNTY

  651 J W Jones Rd, Winter Garden, FL 34787

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