Oakland, FL Homes

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  /2

  Est $748,527 Not Listed For Sale

  3410 Buoy Cir, Oakland, FL 34787

  • 5 Beds
  • 4.5 Baths
  • 3,747 Sq Ft
  • Built 2021

  3410 Buoy Cir, Oakland, FL 34787

  Last Sold Summary

  • 1% Below List Price
  • $201/SF
  • 33 Days On Market

  • Last Sold Price $755,000
  • Jul 30, 2024

  Last Listing Agent Kaley Hansen COLDWELL BANKER HUBBARD HANSEN
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  /3

  $411,995 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,863 Sq Ft

  13873 Easdale Aly, Oakland, FL 34787

  Under Construction. Under Construction. Toll Brothers New Construction in Horizon West – Winter Garden | Estimated Completion Summer 2026. Our Crowley Townhome features a covered entry that leads to an open and expansive living space, kitchen, and dining. The home features a spacious courtyard with access to the detached 2 cars garage. The master bedroom is highlighted by a large walk-in closet

  Dayene Grubert ORLANDO TBI REALTY LLC

  13873 Easdale Aly, Oakland, FL 34787
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  /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
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  /2

  Est $416,892 Not Listed For Sale

  16467 Prairie School Dr, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,626 Sq Ft
  • Built 2022

  16467 Prairie School Dr, Oakland, FL 34787

  Last Sold Summary

  • 2% Below List Price
  • $261/SF
  • 6 Days On Market

  • Last Sold Price $425,000
  • Jan 17, 2025

  Last Listing Agent Carlos Machiavello LAKESIDE REALTY
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  /24

  $489,900

  • 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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  $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
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  /2

  Est $467,972 Not Listed For Sale

  14034 Scarlet Aster Aly, Oakland, FL 34787

  • 3 Beds
  • 3 Baths
  • 1,941 Sq Ft
  • Built 2024

  14034 Scarlet Aster Aly, Oakland, FL 34787

  Last Sold Summary

  • $241/SF
  • 256 Days On Market

  • Last Sold Price $467,000
  • Mar 21, 2025

  Last Listing Agent Abigail Belchick OLYMPUS EXECUTIVE REALTY INC
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  /2

  $943,160 Pending

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

  15166 Tea Tree Dr, Oakland, FL 34787

  One or more photo(s) has been 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

  Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

  15166 Tea Tree Dr, 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
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  /2

  Est $572,812 Not Listed For Sale

  14103 Lochend Way, Oakland, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 2,586 Sq Ft
  • Built 2024

  14103 Lochend Way, Oakland, FL 34787

  Last Sold Summary

  • 9% Above List Price
  • $203/SF
  • 5 Days On Market

  • Last Sold Price $526,000
  • Nov 20, 2024

  Last Listing Agent George Weiss CHARLES RUTENBERG REALTY ORLANDO
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  /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
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  $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

  Est $508,240 Not Listed For Sale

  14407 Braemar St, Oakland, FL 34787

  • 4 Beds
  • 2.5 Baths
  • 2,082 Sq Ft
  • Built 2023

  14407 Braemar St, Oakland, FL 34787

  Last Sold Summary

  • $244/SF

  • Last Sold Price $508,000
  • May 15, 2024

  Last Listing Agent Stellar Non-Member Agent FL_MFRMLS
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  /24

  $602,990 New Construction

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

  3160 Namaste Dr, Oakland, FL 34787

  One or more photo(s) has been virtually staged. 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

  Ben Goldstein LENNAR REALTY

  3160 Namaste Dr, Oakland, FL 34787
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  $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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  Not Listed For Sale

  6295 Blissful St, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 2,186 Sq Ft
  • Built 2024

  6295 Blissful St, Oakland, FL 34787

  Last Sold Summary

  • $204/SF
  • 5 Days On Market

  • Last Sold Price $445,415
  • Oct 05, 2024

  Last Listing Agent Ben Goldstein LENNAR REALTY
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  $385,000 Pending

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

  12043 Holystone St, Oakland, FL 34787

  Under contract-accepting backup offers. Motivated Seller MOVE IN READY .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 offers a welcoming open concept as you immediately enter the foyer, with plenty of cabinet, double sink, granite countertops and a long kitchen island

  Ruth Santos Blystone WRA BUSINESS & REAL ESTATE

  12043 Holystone St, Oakland, FL 34787
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  $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 $410,682

  Last Listing Agent Simon Colak USCO CAPITAL GROUP

  8167 Mosaic Ln, Oakland, FL 34787
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  /59

  Est $478,522 Not Listed For Sale

  2071 White Feather Loop, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 2,082 Sq Ft
  • Built 2019

  2071 White Feather Loop, Oakland, FL 34787

  Last Sold Summary

  • 1% Below List Price
  • $233/SF
  • 14 Days On Market

  • Last Sold Price $485,000
  • Jul 15, 2024

  Last Listing Agent Mark Raumaker SERHANT
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  /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
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  /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 $2,208,739

  Last Listing Agent Dawn Giachetti PREMIER SOTHEBYS INT'L REALTY

  530 Largovista Dr, Oakland, FL 34787
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  /2

  Est $452,691 Not Listed For Sale

  2153 Standing Rock Cir, Winter Garden, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,904 Sq Ft
  • Built 2020

  2153 Standing Rock Cir, Winter Garden, FL 34787

  Last Sold Summary

  • 1% Below List Price
  • $239/SF
  • 49 Days On Market

  • Last Sold Price $455,000
  • Aug 02, 2024

  Last Listing Agent Chad Vaughan REAL BROKER, LLC
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  /64

  $599,000

  • 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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  /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 $459,911

  Last Listing Agent Joshua Earley OPTIMA ONE REALTY, INC.

  2163 White Feather Loop, Winter Garden, FL 34787
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  /2

  Est $628,988 Not Listed For Sale

  15049 Summer Harvest St, Oakland, FL 34787

  • 4 Beds
  • 4.5 Baths
  • 2,830 Sq Ft
  • Built 2024

  15049 Summer Harvest St, Oakland, FL 34787

  Last Sold Summary

  • $222/SF
  • 10 Days On Market

  • Last Sold Price $628,000
  • Dec 26, 2024

  Last Listing Agent Michelle Campbell TAYLOR MORRISON REALTY OF FLORIDA INC
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  /21

  $642,690 New Construction

  • 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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  /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 $794,305

  Last Listing Agent Kathie Glass BHHS FLORIDA REALTY

  1212 Civitas Way, Winter Garden, FL 34787
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  /2

  Est $572,042 Not Listed For Sale

  15109 Summer Harvest St, Oakland, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 2,441 Sq Ft
  • Built 2024

  15109 Summer Harvest St, Oakland, FL 34787

  Last Sold Summary

  • $233/SF

  • Last Sold Price $569,380
  • May 14, 2024

  Last Listing Agent Antonio Cardoso Desmarais TALENT REALTY SOLUTIONS
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  /2

  $605,455 Pending

  • 4 Beds
  • 3.5 Baths
  • 2,520 Sq Ft

  17144 Ingram Hills Aly, Oakland, FL 34787

  One or more photo(s) has been virtually staged. Pre-Construction. To be built. Sample Image The Carter offers a well-designed living space with 3 bedrooms, 3.5 baths, and a 2-car garage. The open-concept layout features a spacious family room, a gourmet kitchen with a large island and pantry, and a dining area. The primary suite includes a luxurious bath and walk-in closet, while additional

  Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

  17144 Ingram Hills Aly, Oakland, FL 34787
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  /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
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  Est $580,246 Not Listed For Sale

  15101 Summer Harvest St, Oakland, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 2,441 Sq Ft
  • Built 2024

  15101 Summer Harvest St, Oakland, FL 34787

  Last Sold Summary

  • 2% Below List Price
  • $243/SF

  • Last Sold Price $592,830
  • May 06, 2024

  Last Listing Agent Stellar Non-Member Agent FL_MFRMLS
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  /34

  $565,000

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

  16140 Harbor Mist Aly, Oakland, FL 34787

  Priced to sell — don't miss this beautifully maintained 2018-built Clearden model in the highly desirable Waterleigh community. Offering 2,477 sq ft, 4 bedrooms, and 3.5 bathrooms, this home is move-in ready with major updates already done. The open-concept main floor features a chef-ready kitchen with granite countertops, wood cabinetry, and stainless steel appliances, flowing into spacious

  Jeanine Louis-Alcime EXP REALTY LLC

  16140 Harbor Mist Aly, Oakland, FL 34787
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  $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 $938,098

  Last Listing Agent Vivian Saavedra LPT REALTY, LLC

  3179 Sailing Pier Ave, Oakland, FL 34787
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  /2

  Not Listed For Sale

  6271 Blissful St, Oakland, FL 34787

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

  6271 Blissful St, Oakland, FL 34787

  Last Sold Summary

  • $201/SF
  • 11 Days On Market

  • Last Sold Price $493,675
  • Oct 24, 2024

  Last Listing Agent Ben Goldstein LENNAR REALTY
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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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  /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 $671,636

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

  5826 Fabry St, Oakland, FL 34787
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  /2

  Est $797,096 Not Listed For Sale

  1191 Wilder Oaks Way, Oakland, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,240 Sq Ft
  • Built 2024

  1191 Wilder Oaks Way, Oakland, FL 34787

  Last Sold Summary

  • $357/SF
  • 96 Days On Market

  • Last Sold Price $799,000
  • Oct 18, 2024

  Last Listing Agent Abigail Belchick OLYMPUS EXECUTIVE REALTY INC
• 

  

  /23

  $575,000

  • 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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  /2

  $410,000 Sold Jun 04, 2025

  0 N Daniels St, Oakland, FL 34760

  • Land
  • 13,503 Sq Ft
  • $1,322,581 per Acre

  Last Sold Summary

  • 9% Below List Price
  • 9 Days On Market

  Last Listing Agent Roberta Melo SELECTA REALTY LLC

  0 N Daniels St, Oakland, FL 34760
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  Est $790,593 Not Listed For Sale

  5121 Breezy Acres St, Oakland, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 2,724 Sq Ft
  • Built 2021

  5121 Breezy Acres St, Oakland, FL 34787

  Last Sold Summary

  • 6% Below List Price
  • $308/SF
  • 3 Days On Market

  • Last Sold Price $840,000
  • Jun 21, 2024

  Last Listing Agent Teresa White PREMIER SOTHEBYS INT'L REALTY

Showing Results 281 - 320, Page 8 of 18