Oakland, FL Homes

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  /57

  $795,000

  $65K 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
• 

  

  /2

  $400,000

  Sold Aug 18, 2025

  5693 Meditation Dr, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,795 Sq Ft
  • Built 2025

  Last Sold Summary

  • 11% Below List Price
  • $223/SF
  • 31 Days On Market

  Last Listing Agent Ben Goldstein LENNAR REALTY

  5693 Meditation Dr, Oakland, FL 34787
• 

  

  /2

  Est $805,832

  Not Listed For Sale

  1204 Oak Fort Ln, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 2,254 Sq Ft
  • Built 2024

  1204 Oak Fort Ln, Oakland, FL 34787

  Last Sold Summary

  • 108 Days On Market
• 

  

  

  /33

  $512,490

  New Construction Pending

  • 4 Beds
  • 3 Baths
  • 2,366 Sq Ft

  5485 Oasis Loop, Oakland, FL 34787

  Under Construction. Check out this amazing new single-story Next Gen®! The McCartney features a private suite with its own entrance, living area, kitchenette, bedroom, bathroom and laundry, perfect for multigenerational households. The main home is host to an inviting open-concept layout with easy access to a covered patio for seamless indoor-outdoor living. Two secondary bedrooms are located off

  Ben Goldstein LENNAR REALTY

  5485 Oasis Loop, Oakland, FL 34787
• 

  

  /2

  $653,240

  Sold Jul 30, 2025

  5664 Vinyasa Rd, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 2,650 Sq Ft
  • Built 2025

  Last Sold Summary

  • $247/SF

  Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

  5664 Vinyasa Rd, Oakland, FL 34787
• 

  /2

  Not Listed For Sale

  6259 Blissful St, Oakland, FL 34787

  • 5 Beds
  • 3 Baths
  • 2,455 Sq Ft
  • Built 2024

  6259 Blissful St, Oakland, FL 34787

  Last Sold Summary

  • 0 Days On Market
• 

  

  /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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  /36

  $751,000

  Sold Oct 03, 2025

  16041 Honey Harvest St, Oakland, FL 34787

  • 4 Beds
  • 4.5 Baths
  • 2,837 Sq Ft
  • Built 2025

  Move in Ready Sold Summary

  • $265/SF
  • 26 Days On Market

  Taylor Morrison Harvest at Ovation

  16041 Honey Harvest St, Oakland, FL 34787
• 

  /2

  Est $404,979

  Not Listed For Sale

  17005 Volume Aly, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,717 Sq Ft
  • Built 2020

  17005 Volume Aly, Oakland, FL 34787

  Last Sold Summary

  • 39 Days On Market
• 

  /2

  $943,160

  New Construction Pending

  • 4 Beds
  • 3 Baths
  • 3,108 Sq Ft

  15166 Tea Tree Dr, Oakland, FL 34787

  Virtually Staged. Pre-Construction. To be built. Opportunity in Avalon Woods! ARLINGTON bonus. Discover the newest community by Dream Finders Homes in the highly sought-after Hamlin, Winter Garden. Welcome to the Arlington, an award-winning single-story open-concept home designed for modern living and effortless entertaining. The layout flows seamlessly from the great room to the dining and

  Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

  15166 Tea Tree Dr, Oakland, FL 34787
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  /2

  $695,000

  Sold Sep 22, 2025

  1281 Ridge Lake Way, Winter Garden, FL 34787

  • Land
  • 16,988 Sq Ft
  • $1,782,051 per Acre

  Last Sold Summary

  • 13% Below List Price
  • 99 Days On Market

  Last Listing Agent Samantha Andrade SERHANT

  1281 Ridge Lake Way, Winter Garden, FL 34787
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  /2

  Not Listed For Sale

  6301 Blissful St, Oakland, FL 34787

  • 5 Beds
  • 3 Baths
  • 3,043 Sq Ft
  • Built 2024

  6301 Blissful St, Oakland, FL 34787

  Last Sold Summary

  • 12 Days On Market
• 

  

  /32

  $510,000

  • 3 Beds
  • 2.5 Baths
  • 1,868 Sq Ft

  15220 Blue Peacock Ln, Oakland, FL 34787

  Welcome to this beautiful home featuring an open floor plan that blends comfort, style, and functionality. Filled with natural light, the spacious layout is perfect for both everyday living and entertaining. The inviting living area offers a warm setting for gatherings, while the modern kitchen boasts stainless steel appliances, abundant cabinetry, and generous counter space for the home chef.

  DENILEY VALDES TALENT REALTY SOLUTIONS

  15220 Blue Peacock Ln, Oakland, FL 34787
• 

  /2

  $860,000

  Sold Jun 08, 2026

  9409 Emerald Berry Dr, Oakland, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 2,923 Sq Ft
  • Built 2024

  Last Sold Summary

  • 4% Below List Price
  • $294/SF
  • 53 Days On Market

  Current Estimated Value $867,815

  Last Listing Agent Manuella Espinosa LA ROSA REALTY LLC

  9409 Emerald Berry Dr, Oakland, FL 34787
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  /2

  Not Listed For Sale

  6253 Blissful St, Oakland, FL 34787

  • 5 Beds
  • 3 Baths
  • 2,455 Sq Ft
  • Built 2024

  6253 Blissful St, Oakland, FL 34787

  Last Sold Summary

  • 35 Days On Market
• 

  

  /24

  $602,990

  New Construction $5K PRICE DROP Pending

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

  3160 Namaste Dr, Oakland, FL 34787

  Under Construction. This lovely Riviera Next Gen® single-story home features an attached private suite with its own living room, kitchenette, bedroom and bathroom. In the main home is an open space layout in the kitchen, nook and family room, which extends to the covered patio through sliding glass doors for outdoor living. There is a flex space to accommodate versatile needs and three bedrooms,

  Ben Goldstein LENNAR REALTY

  3160 Namaste Dr, Oakland, FL 34787
• 

  /2

  $883,656

  Sold Sep 08, 2025

  16089 Honey Harvest St, Oakland, FL 34787

  • 4 Beds
  • 4.5 Baths
  • 2,837 Sq Ft
  • Built 2025

  Last Sold Summary

  • $311/SF

  Current Estimated Value $880,000

  Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

  16089 Honey Harvest St, Oakland, FL 34787
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  /2

  Not Listed For Sale

  6379 Blissful St, Oakland, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,023 Sq Ft
  • Built 2024

  6379 Blissful St, Oakland, FL 34787

  Last Sold Summary

  • 4 Days On Market
• 

  

  /44

  $829,347

  New Construction $56K PRICE INCREASE Pending

  • 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! 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 into a bright and open main living area. A guest bedroom with full bath downstairs provides comfort

  Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

  15075 Tea Tree Dr, Oakland, FL 34787
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  /2

  $385,000

  Sold Mar 31, 2026

  8167 Mosaic Ln, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,860 Sq Ft
  • Built 2020

  Last Sold Summary

  • 8% Below List Price
  • $207/SF
  • 49 Days On Market

  Current Estimated Value $390,767

  Last Listing Agent Simon Colak USCO CAPITAL GROUP

  8167 Mosaic Ln, Oakland, FL 34787
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  /2

  Not Listed For Sale

  6391 Blissful St, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,782 Sq Ft
  • Built 2024

  6391 Blissful St, Oakland, FL 34787

  Last Sold Summary

  • 4 Days On Market
• 

  /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
• 

  /2

  $2,275,000

  Sold Nov 24, 2025

  530 Largovista Dr, Oakland, FL 34787

  • 5 Beds
  • 5 Baths
  • 4,798 Sq Ft
  • Built 2006

  Last Sold Summary

  • 9% Below List Price
  • $474/SF
  • 110 Days On Market

  Current Estimated Value $2,205,214

  Last Listing Agent Dawn Giachetti PREMIER SOTHEBYS INT'L REALTY

  530 Largovista Dr, Oakland, FL 34787
• 

  /2

  Est $424,800

  Not Listed For Sale

  15805 Tollington Aly, Oakland, FL 34787

  • 3 Beds
  • 3.5 Baths
  • 1,688 Sq Ft
  • Built 2024

  15805 Tollington Aly, Oakland, FL 34787

  Last Sold Summary
• 

  

  /18

  $895,000

  • Land
  • 38,768 Sq Ft
  • $1,005,618 per Acre

  537 N Pollard St, Winter Garden, FL 34787

  Welcome to Briley Farm, a picturesque community nestled along the serene shores of Lake Apopka. This premium lot offers the perfect opportunity to design and build your custom dream home in one of Central Florida’s most sought-after lakefront neighborhoods. With plenty of space and stunning views, this homesite is ideal for creating your personal oasis—whether that’s a timeless farmhouse, a

  Blaine Dooley REGENCY REAL ESTATE LLC

  537 N Pollard St, Winter Garden, FL 34787
• 

  /2

  $464,000

  Sold Oct 29, 2025

  2163 White Feather Loop, Winter Garden, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,744 Sq Ft
  • Built 2019

  Last Sold Summary

  • 7% Below List Price
  • $266/SF
  • 65 Days On Market

  Current Estimated Value $465,435

  Last Listing Agent Joshua Earley EQUITY RENTAL MANAGEMENT

  2163 White Feather Loop, Winter Garden, FL 34787
• 

  /2

  Est $436,353

  Not Listed For Sale

  15811 Tollington Aly, Oakland, FL 34787

  • 3 Beds
  • 3 Baths
  • 1,691 Sq Ft
  • Built 2024

  15811 Tollington Aly, Oakland, FL 34787
• 

  

  /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
• 

  /2

  $785,000

  Sold Oct 24, 2025

  1212 Civitas Way, Winter Garden, FL 34787

  • 4 Beds
  • 2 Baths
  • 2,260 Sq Ft
  • Built 2022

  Last Sold Summary

  • 10% Below List Price
  • $347/SF
  • 128 Days On Market

  Current Estimated Value $813,354

  Last Listing Agent Kathie Glass BHHS FLORIDA REALTY

  1212 Civitas Way, Winter Garden, FL 34787
• 

  /2

  Est $606,403

  Not Listed For Sale

  15153 Summer Harvest St, Oakland, FL 34787

  • 3 Beds
  • 4 Baths
  • 2,149 Sq Ft
  • Built 2024

  15153 Summer Harvest St, Oakland, FL 34787
• 

  

  /89

  $1,799,000

  Pending

  • 4 Beds
  • 4 Baths
  • 4,085 Sq Ft

  902 Johns Point Dr, Oakland, FL 34787

  Under contract-accepting backup offers. Seller financing available! Discover an extraordinary waterfront retreat where luxury, privacy, and breathtaking lake views come together in perfect harmony. This exceptional 4-bedroom, 4-bath custom residence offers over 4,000 square feet of thoughtfully designed living space on the shores of highly sought-after Johns Lake, delivering an unparalleled

  Heidi Pfeffer-Morgan DALTON WADE INC

  902 Johns Point Dr, Oakland, FL 34787
• 

  /2

  $4,383,239

  Sold Dec 15, 2025

  548 Walker St, Oakland, FL 34760

  • 5 Beds
  • 8 Baths
  • 6,203 Sq Ft
  • Built 2026

  Last Sold Summary

  • $707/SF
  • 0 Days On Market

  Last Listing Agent Matthew Burks CORCORAN PREMIER REALTY

  548 Walker St, Oakland, FL 34760
• 

  /2

  Est $419,111

  Not Listed For Sale

  2315 Standing Rock Cir, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,663 Sq Ft
  • Built 2018

  2315 Standing Rock Cir, Oakland, FL 34787

  Last Sold Summary

  • 35 Days On Market
• 

  

  /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
• 

  /2

  $925,000

  Sold Oct 15, 2025

  3179 Sailing Pier Ave, Oakland, FL 34787

  • 5 Beds
  • 5 Baths
  • 4,272 Sq Ft
  • Built 2023

  Last Sold Summary

  • 7% Below List Price
  • $217/SF
  • 70 Days On Market

  Current Estimated Value $929,192

  Last Listing Agent Vivian Saavedra LPT REALTY, LLC

  3179 Sailing Pier Ave, Oakland, FL 34787
• 

  /2

  Est $676,505

  Not Listed For Sale

  1540 Stone Arrow Ct, Winter Garden, FL 34787

  • 5 Beds
  • 3.5 Baths
  • 3,248 Sq Ft
  • Built 2018

  1540 Stone Arrow Ct, Winter Garden, FL 34787

  Last Sold Summary

  • 44 Days On Market
• 

  

  /60

  $675,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 1,772 Sq Ft

  936 Kylee Aly, Winter Garden, FL 34787

  Move-in ready 3-bedroom, 2.5-bathroom single-family home in the Oakland Park community of Winter Garden, Florida. Built in 2022, turnkey condition, full appliance package included, and a low-maintenance 0.05-acre homesite designed for connected daily living without the upkeep. Oakland Park is one of those Winter Garden communities people move to on purpose. Tree-lined streets, walkable sidewalks,

  Nelson Cruz REAL BROKER, LLC

  936 Kylee Aly, Winter Garden, FL 34787
• 

  /2

  $616,150

  Sold Nov 01, 2025

  5826 Fabry St, Oakland, FL 34787

  • 5 Beds
  • 3.5 Baths
  • 2,563 Sq Ft
  • Built 2025

  Last Sold Summary

  • $240/SF

  Current Estimated Value $691,608

  Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

  5826 Fabry St, Oakland, FL 34787
• 

  /2

  Est $546,442

  Not Listed For Sale

  13037 Tollcross Way, Oakland, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,160 Sq Ft
  • Built 2024

  13037 Tollcross Way, Oakland, FL 34787

  Last Sold Summary

  • 189 Days On Market
• 

  

  /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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