Oakland, FL Homes

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  Est $618,950 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

  • 5% Above List Price
  • $182/SF
  • 44 Days On Market

  Last Sold Price $590,000

  Last Listing Agent Eric Jia NUMBER 1 BROKER, LLC
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  $416,900

  • 3 Beds
  • 3 Baths
  • 1,809 Sq Ft

  2222 Gopher Tortoise Terrace, Oakland, FL 34787

  YOU Can't miss this Gorgeous 3beds,3 full Bath townhouse in Oakland . near Winter Garden and Clermont..Perfect amenities for you enjoy the best of Florida lifestyle..This Property have absolutely the Best Floor Plan : Open floor concept ,that integrate Living space, Kitchen and Dinner space. Surrounded with sunlight windows. Engineering floor, granite counters, stainless appliances. Perfect for

  Wagner ferreira LPT REALTY, LLC

  2222 Gopher Tortoise Terrace, Oakland, FL 34787
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  $460,000 Sold Sep 23, 2025

  17055 Wynford Ln, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 2,345 Sq Ft
  • Built 2021

  Last Sold Summary

  • 16% Below List Price
  • $196/SF
  • 160 Days On Market

  Current Estimated Value $475,997

  Last Listing Agent Lori Lucente-Nelson RE/MAX PRIME PROPERTIES

  17055 Wynford Ln, Oakland, FL 34787
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  Est $536,570 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

  • $249/SF
  • 189 Days On Market

  Last Sold Price $537,500

  Last Listing Agent Michele Drebes Weiand WRA BUSINESS & REAL ESTATE
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  $1,588,000

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

  1412 Johns Cove Ln, Oakland, FL 34787

  Welcome to your ideal lakeside sanctuary in the highly sought-after gated community of Johns Cove! This home features a split bedroom layout with over 3600 s/f of easy, relaxing living complemented by a pool area that boasts stunning views of Johns Lake. The property has been completely reinvented since the current owners purchased it. Renovations include, a kitchen with all new appliances

  Betsey West NEXT RESIDENCE REALTY LLC

  1412 Johns Cove Ln, Oakland, FL 34787
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  $580,109 Sold Dec 23, 2025

  17597 Japonica Bloom Dr, Oakland, FL 34787

  • 3 Beds
  • 2 Baths
  • 1,791 Sq Ft
  • Built 2025

  Last Sold Summary

  • $324/SF

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

  17597 Japonica Bloom Dr, Oakland, FL 34787
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  Est $506,988 Not Listed For Sale

  13025 Tollcross Way, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,838 Sq Ft
  • Built 2024

  13025 Tollcross Way, Oakland, FL 34787

  Last Sold Summary

  • 6% Below List Price
  • $294/SF
  • 91 Days On Market

  Last Sold Price $540,000

  Last Listing Agent George Weiss CHARLES RUTENBERG REALTY ORLANDO
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  $885,000 Open Sat 11AM - 2PM

  • 4 Beds
  • 3 Baths
  • 2,850 Sq Ft

  8 Winters Landing Dr, Oakland, FL 34787

  One or more photo(s) has been virtually staged. Welcome to your own private retreat in one of West Orange County’s most sought-after areas. This completely renovated 4-bedroom, 3-bathroom home offering 2,850 square feet of beautifully updated living space located in the heart of Oakland is just minutes from downtown Winter Garden.From the moment you step inside, you’ll appreciate the

  Danielle Norvell REGENCY REAL ESTATE LLC

  8 Winters Landing Dr, Oakland, FL 34787
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  $500,000 Sold Apr 08, 2025

  16257 Prairie School Dr, Oakland, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,070 Sq Ft
  • Built 2021

  Last Sold Summary

  • 3% Below List Price
  • $242/SF
  • 54 Days On Market

  Current Estimated Value $489,594

  Last Listing Agent Sue Vasquez FLORIDA REALTY RESULTS LLC

  16257 Prairie School Dr, Oakland, FL 34787
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  Est $757,311 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

  • $201/SF
  • 33 Days On Market

  Last Sold Price $755,000

  Last Listing Agent Kaley Hansen COLDWELL BANKER HUBBARD HANSEN
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  /24

  $1,250,000 Pending

  • Land
  • 0.82 Acre
  • $1,524,390 per Acre

  552 Walker St, Oakland, FL 34760

  Under contract-accepting backup offers. 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

  Alexis Anderson REGENCY REAL ESTATE LLC

  552 Walker St, Oakland, FL 34760
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  $785,000 Sold Oct 24, 2025

  16152 Point Rock Dr, Oakland, FL 34787

  • 5 Beds
  • 4 Baths
  • 2,866 Sq Ft
  • Built 2025

  Last Sold Summary

  • 6% Below List Price
  • $274/SF
  • 48 Days On Market

  Current Estimated Value $803,000

  Last Listing Agent Stephen Cline DR HORTON REALTY OF CENTRAL FLORIDA LLC

  16152 Point Rock Dr, Oakland, FL 34787
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  Est $410,493 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

  • 3% Below List Price
  • $261/SF
  • 6 Days On Market

  Last Sold Price $425,000

  Last Listing Agent Carlos Machiavello LAKESIDE REALTY
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  $550,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,565 Sq Ft

  1148 Bobcat Chase Blvd, Oakland, FL 34787

  Under contract-accepting backup offers. Immaculate three bedroom, two bath home plus an additional dedicated office, located on a premiumpond-front corner lot in Longleaf at Oakland. This single -level residence showcases extensive upgrades throughout.Features include luxury vinyl plank flooring, plantation shutters, custom feature wall with electric fireplace, built in cabinetry in the

  Rema Perras CORCORAN PREMIER REALTY

  1148 Bobcat Chase Blvd, Oakland, FL 34787
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  $580,000 Sold Oct 31, 2025

  2642 Bobcat Chase Blvd, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,811 Sq Ft
  • Built 2019

  Last Sold Summary

  • 6% Below List Price
  • $320/SF
  • 38 Days On Market

  Current Estimated Value $571,607

  Last Listing Agent Johna Jennings Coastal Life Properties LLC

  2642 Bobcat Chase Blvd, Oakland, FL 34787
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  Est $562,275 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

  • 7% Above List Price
  • $203/SF
  • 5 Days On Market

  Last Sold Price $526,000

  Last Listing Agent George Weiss CHARLES RUTENBERG REALTY ORLANDO
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  $1,299,500

  • 5 Beds
  • 3.5 Baths
  • 3,911 Sq Ft

  8978 Sonoma Coast Dr, Oakland, FL 34787

  LUXURY POOL HOME on PREMIUM LAKE FRONT LOT! Unique Opportunity to Enjoy an Outdoor PARADISE with STUNNING LAKE, CONSERVATION & SUNSET Views! The HOA is Allowing Docks on these Special Lots – Relax, Fish or Kayak! Most POPULAR Floor Plan – North Haven – has 5 Bedrooms, 3.5 Baths, Gourmet Kitchen, First Floor Primary Suite, TONS OF STORAGE, Tile Roof and 3 Car Garage. The OUTDOOR LIVING Space is

  JoAnn Best CHARLES RUTENBERG REALTY ORLANDO

  8978 Sonoma Coast Dr, Oakland, FL 34787
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  $900,000 Sold Sep 12, 2025

  619 Largovista Dr, Oakland, FL 34787

  • 5 Beds
  • 3.5 Baths
  • 3,728 Sq Ft
  • Built 2005

  Last Sold Summary

  • 9% Below List Price
  • $241/SF
  • 52 Days On Market

  Current Estimated Value $857,064

  Last Listing Agent Farhad Haniff EXP REALTY LLC

  619 Largovista Dr, Oakland, FL 34787
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  Est $502,962 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

  • 1% Below List Price
  • $244/SF

  Last Sold Price $508,000

  Last Listing Agent Stellar Non-Member Agent FL_MFRMLS
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  $544,990 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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  $1,200,000 Sold Mar 10, 2026

  1120 Civitas Way, Winter Garden, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,563 Sq Ft
  • Built 2022

  Last Sold Summary

  • $468/SF
  • 4 Days On Market

  Current Estimated Value $985,154

  Last Listing Agent Ashlen Hayward THE AGENCY FL

  1120 Civitas Way, Winter Garden, 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

  Last Listing Agent Ben Goldstein LENNAR REALTY
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  $596,832 New Construction

  • 3 Beds
  • 3.5 Baths
  • 2,149 Sq Ft

  14736 Field Daisy Dr, Oakland, FL 34787

  Welcome to the Newberry at 14736 Field Daisy Drive in Harvest at Ovation! The Newberry bungalow floor plan is a true representation of modern living and the perfect space for all of your entertainment needs and desires. The 2149 sq. ft. two-story home with 3 bedrooms, 3.5 bathrooms and a 2-car detached garage presents prospective homebuyers with both the basic features and intricate details that

  Taylor Morrison Builder

  14736 Field Daisy Dr, Oakland, FL 34787
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  $914,390 Sold Nov 25, 2025

  4649 Golden Birch Ave, Oakland, FL 34787

  • 5 Beds
  • 5 Baths
  • 4,272 Sq Ft
  • Built 2025

  Last Sold Summary

  • $214/SF

  Current Estimated Value $904,695

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

  4649 Golden Birch Ave, Oakland, FL 34787
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  /59

  Est $473,292 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

  • 2% Below List Price
  • $233/SF
  • 14 Days On Market

  Last Sold Price $485,000

  Last Listing Agent Mark Raumaker SERHANT
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  /23

  $395,000

  • 3 Beds
  • 2.5 Baths
  • 1,620 Sq Ft

  2228 Gopher Tortoise Terrace, Oakland, FL 34787

  This townhome in Longleaf at Oakland features a bright, open layout with plank vinyl flooring, granite countertops, and recessed lighting. The main level offers seamless flow for everyday living and entertaining. Upstairs, three well-appointed bedrooms provide comfortable and functional space. A private courtyard-style patio adds an inviting outdoor area for relaxing or grilling. Community

  Leslie Anne Campasano ASANO REAL ESTATE LLC

  2228 Gopher Tortoise Terrace, Oakland, FL 34787
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  $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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  Est $450,591 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

  Last Listing Agent Chad Vaughan REAL BROKER, LLC
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  $679,900

  • 4 Beds
  • 3.5 Baths
  • 3,583 Sq Ft

  729 Strihal Loop, Oakland, FL 34787

  Prince drastically reduced for quick sale !!! Luxury, Location, and Lake Access !! This elegant 5 bedrooms, 3.5 baths home is located in an exclusive gated community on Johns Lake, offering privacy and luxury lifestyle. Home boasts vaulted ceilings and designer quartz counter tops. Step outside to your private pool or take advantage of the community's private boat ramp with direct lake access to

  Subhas C Sawh LIBERTY HOME SALES INC

  729 Strihal Loop, 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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  Est $619,610 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

  • 1% Below List Price
  • $222/SF
  • 10 Days On Market

  Last Sold Price $628,000

  Last Listing Agent Michelle Campbell TAYLOR MORRISON REALTY OF FLORIDA INC
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  $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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  $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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  Est $562,199 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

  • 1% Below List Price
  • $233/SF

  Last Sold Price $569,380

  Last Listing Agent Antonio Cardoso Desmarais TALENT REALTY SOLUTIONS
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  $695,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,763 Sq Ft

  310 E Gulley Ave, Oakland, FL 34760

  Under contract-accepting backup offers. Beautifully renovated pool home in the desirable Town of Oakland, within the golf cart district, and no HOA. Located in an area seeing significant growth with nearby luxury new construction and vacant lots selling for a premium, this property offers both charm and long-term value in one of West Orange County’s most sought-after locations. This updated

  Matt Kester THE REAL ESTATE COLLECTION LLC

  310 E Gulley Ave, Oakland, FL 34760
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  $695,000 Sold Sep 22, 2025

  1281 Ridge Lake Way, Winter Garden, FL 34787

  • Land
  • 0.39 Acre
  • $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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  Est $569,415 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

  • 4% Below List Price
  • $243/SF

  Last Sold Price $592,830

  Last Listing Agent Stellar Non-Member Agent FL_MFRMLS
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  $498,990 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,836 Sq Ft

  Brantley Plan at Serenade at Ovation - Bungalow, 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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  $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 $952,000

  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

  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

  Last Listing Agent Ben Goldstein LENNAR REALTY

Showing Results 241 - 280, Page 7 of 18