Oakland, FL Homes for Sale

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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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  /22

  $449,000

  $20K PRICE DROP

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

  14014 Scarlet Aster Aly, Oakland, FL 34787

  ***** PRICE REDUCED *****Rare Dual Owner's Suite Townhome — Priced to Move, Near DisneyThis 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

  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

  $2,380,160

  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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  /25

  $468,000

  $22K 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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  /7

  $1,195,000

  • Land
  • 35,719 Sq Ft
  • $1,457,317 per Acre

  552 Walker St, Oakland, FL 34760

  Discover an exceptional opportunity to build a custom lakefront residence on Lot 45 in Briley Farm Phase 1B. Located at 552 Walker Street in Oakland, this approximately 0.82-acre homesite offers beautiful Lake Apopka views, direct lake frontage and generous space to create a personalized retreat exclusively with Element Home Builders. With no predetermined floor plan, buyers can collaborate with

  Carolina Dumit CORCORAN PREMIER REALTY

  552 Walker St, Oakland, FL 34760
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  /5

  $595,000

  • Land
  • 22,651 Sq Ft
  • $1,144,231 per Acre

  523 Walker St, Oakland, FL 34787

  Build your custom residence on Lot 21 in Briley Farm Phase 1B, a thoughtfully designed community in Oakland, Florida. Located at 523 Walker Street, this approximately 0.52-acre interior homesite offers the opportunity to create a custom home exclusively with Element Home Builders, with no predetermined floor plan. Enjoy a desirable location near charming downtown Winter Garden, the West Orange

  Carolina Dumit CORCORAN PREMIER REALTY

  523 Walker St, 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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  /22

  $645,990

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,688 Sq Ft

  Anna Maria w/ Bonus Plan at Serenade at Ovation - 50' Collection, Oakland, FL 34787

  The Anna Maria with Bonus floorplan is an expansive two-story home designed to accommodate a growing family, offering four bedrooms and three and a half bathrooms. On the main floor, you'll find a spacious great room adjacent to a well-appointed dining room and kitchen, creating an ideal space for gatherings. The primary suite, featuring a large walk-in closet and private bath, is thoughtfully

  Dream Finders Homes Builder

  14229 Lanyard Way Unit 36501514, Oakland, FL 34787
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  /36

  $649,990

  New Construction

  • 4 Beds
  • 3 Baths
  • 2,689 Sq Ft

  Biscayne Plan at Serenade at Ovation - 50' Collection, Oakland, FL 34787

  The Biscayne floorplan offers a spacious two-story design that perfectly balances functionality and flexibility, ideal for growing families. With four bedrooms and two and a half bathrooms, this layout provides ample space for everyday living and special moments alike. On the first floor, you'll find a flex room that can serve as a home office, gym, or an optional guest bedroom, depending on your

  Dream Finders Homes Builder

  14229 Lanyard Way Unit 36496529, Oakland, FL 34787
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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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  /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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  /30

  $653,118

  New Construction $51K 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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  /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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  /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

  $585,000

  $45K 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

  $619,999

  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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  /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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  /31

  $603,990

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,235 Sq Ft

  Anna Maria Plan at Serenade at Ovation - 50' Collection, Oakland, FL 34787

  The Anna Maria floorplan is a thoughtfully designed one-story home featuring four bedrooms and two and a half bathrooms, perfect for comfortable family living. The open-concept layout highlights a spacious great room that flows seamlessly into the kitchen and dining area, making it ideal for gatherings and relaxation. The primary bedroom offers privacy with a well-appointed ensuite and a large

  Dream Finders Homes Builder

  14229 Lanyard Way Unit 36464429, Oakland, FL 34787
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  /31

  $550,000

  • 4 Beds
  • 2.5 Baths
  • 2,082 Sq Ft

  14123 Frasier St, Oakland, FL 34787

  SPECIAL FINANCING AVAILABLE! The seller is offering a promotional 3.875 interest rate through a rate buy-down program, plus ALL closing costs paid when using the preferred lender—creating an incredible opportunity for qualified buyers to significantly reduce their monthly payment and cash needed at closing. Welcome to this stunning newer construction home located in the highly desirable Horizon

  Yornelly Sanchez Manrique LEVO REAL ESTATE LLC

  14123 Frasier St, Oakland, 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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  /45

  $418,500

  $1K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,636 Sq Ft

  10648 Words Dr, Winter Garden, FL 34787

  Storey Grove **YES IT HAS A BACKYARD!!*BACKS TO GREENSPACE!!** 2023 built ** Open floorplan * Beautiful wood ceramic tile entire 1st floor ** Attractive tv wall wood accent inlay in the family room ** White kitchen cabinetry with quartz counters and large cooking island ** All bedrooms are on the 2nd floor ** Nice size +/-16x20 brick paver patio area and 2 car detached garage ** Great RING

  Gabriella Philippone INDEPENDENCE REALTY GROUP LLC

  10648 Words Dr, Winter Garden, 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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  /28

  $433,000

  Open Mon 9AM - 7PM

  • 4 Beds
  • 2 Baths
  • 1,778 Sq Ft

  17802 Jefferson St, Oakland, FL 34787

  Virtually Staged. Step into 17802 Jefferson St, a residence presenting a refreshed exterior appeal from fresh exterior paint and modernized interior amenities. The kitchen is fully equipped with all stainless steel appliances, establishing a contemporary culinary space, while a central fireplace provides warmth and a welcoming ambiance in the living area. Updated style and comfort are ready for

  Karen Albright OPENDOOR BROKERAGE LLC

  17802 Jefferson St, Oakland, FL 34787
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  /54

  $559,000

  • 4 Beds
  • 2.5 Baths
  • 2,854 Sq Ft

  2471 Sky Stone Ct, Oakland, FL 34787

  Welcome to 2471 Skystone Ct, located in the desirable Oakland area! This spacious two-story home offers a thoughtfully designed floor plan with 4 bedrooms, 3.5 bathrooms, a private study, upstairs game room, and a 2-car garage.The main level features a separate living room, a dedicated study perfect for a home office, and an open-concept kitchen overlooking the breakfast nook and

  Eric Jia NUMBER 1 BROKER, LLC

  2471 Sky Stone Ct, Oakland, FL 34787
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  /94

  $1,500,000

  • 5 Beds
  • 4 Baths
  • 3,781 Sq Ft

  2010 Boss Hewett St, Oakland, FL 34787

  Welcome to this stunning, like-new home that perfectly blends luxury, comfort, and modern design in the highly desirable community of Hull Island. Boasting five spacious bedrooms and four full bathrooms, this thoughtfully designed residence offers an ideal layout for both everyday living and entertaining. This home offers two spacious owner’s suites, one conveniently located on the first floor

  Vilmari Caraballo RE/MAX ASSURED

  2010 Boss Hewett St, Oakland, FL 34787
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  /42

  $379,000

  • 3 Beds
  • 2.5 Baths
  • 1,737 Sq Ft

  1424 Scarlet Oak Loop, Winter Garden, FL 34787

  Welcome to your beautifully updated home in the gated community of Winter Garden. This charming residence offers 3 bedrooms, 2.5 baths, 2-car garage, and approximately 1,737 sq. ft. of comfortable living space.In 2025, this home underwent a $53K renovation, featuring a modern kitchen with 42” shaker white cabinets with undermount lighting and quartz counters, stainless steel appliances,

  Paula Hemani TEAMCONNECT REALTY LLC

  1424 Scarlet Oak Loop, Winter Garden, FL 34787

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