Oakland, FL Homes

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  $980,000 Sold Mar 17, 2025

  126 Hammock Preserve Loop, Oakland, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 2,811 Sq Ft
  • Built 2023

  Last Sold Summary

  • 1% Below List Price
  • $349/SF
  • 19 Days On Market

  Current Estimated Value $981,109

  Last Listing Agent Jenna Palmero COLDWELL BANKER REALTY

  126 Hammock Preserve Loop, Oakland, FL 34787
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  Est $510,993 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,996 Sq Ft

  14011 Lochend Way, Oakland, FL 34787

  14011 Lochend Way, Oakland, FL 34787
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  $418,900

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

  8167 Mosaic Ln, Oakland, FL 34787

  One or more photo(s) has been virtually staged. Gorgeous Townhouse located in Winter Garden at the great Ravenna Community, just 10 minutes drive from Disney World, close to good Winter Garden restaurants, new shopping malls, supermarkets, banks ext. This 3 bedroom 2/1 bathroom home with stunning features and open floor plan, separated dining room that is fully upgraded floor and cabinets and

  Simon Colak USCO CAPITAL GROUP

  8167 Mosaic Ln, Oakland, FL 34787
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  $1,400,000 Sold Jun 27, 2025

  141 Millholland St, Oakland, FL 34760

  • 4 Beds
  • 3.5 Baths
  • 3,497 Sq Ft
  • Built 2002

  Last Sold Summary

  • 12% Below List Price
  • $400/SF
  • 72 Days On Market

  Current Estimated Value $1,395,761

  Last Listing Agent Matthew Matin CLOCK TOWER REALTY

  141 Millholland St, Oakland, FL 34760
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  Est $499,228 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,996 Sq Ft

  14047 Lochend Way, Oakland, FL 34787

  14047 Lochend Way, Oakland, FL 34787
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  $725,000

  • 5 Beds
  • 4.5 Baths
  • 3,725 Sq Ft

  3294 Hanging Tide St, Oakland, FL 34787

  3.625% VA Assumable Loan! Welcome home to 3294 Hanging Tide, located in the premier community of Lakeview Preserve. This home is known as the Yorkshire model and was built by Pulte Homes in 2021. This is your opportunity to buy a new home, without the wait! The Yorkshire model is known for its space. The Yorkshire plan is highly desired, because of the first floor guest suite, with its on

  Ken Pozek REAL BROKER, LLC.

  3294 Hanging Tide St, Oakland, FL 34787
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  $735,000 Sold Oct 30, 2025

  2340 Standing Rock Cir, Winter Garden, FL 34787

  • 5 Beds
  • 3 Baths
  • 3,493 Sq Ft
  • Built 2019

  Last Sold Summary

  • 3% Below List Price
  • $210/SF
  • 112 Days On Market

  Current Estimated Value $734,327

  Last Listing Agent Jennifer Coon LAKESIDE REALTY WINDERMERE INC

  2340 Standing Rock Cir, Winter Garden, FL 34787
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  Not Listed For Sale

  • 4 Beds
  • 5 Baths
  • 3,794 Sq Ft

  Unlisted Address

  Unlisted Address
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  $789,999

  • 5 Beds
  • 4.5 Baths
  • 3,682 Sq Ft

  3351 Current Ave, Oakland, FL 34787

  Welcome to this stunning two-story Tortola floor plan by Taylor Morrison, ideally located in the gated community of Lakeview Preserve in Winter Garden. Perfectly positioned on an oversized 75-foot-wide corner homesite with no rear neighbors, this home offers exceptional privacy, beautiful rear views, and a welcoming front porch that sets the tone from the moment you arrive. The elegant

  Amy Kidwell PA PREFERRED REAL ESTATE BROKERS

  3351 Current Ave, Oakland, FL 34787
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  $690,000 Sold May 13, 2025

  2157 Bay Line Rd, Oakland, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,274 Sq Ft
  • Built 2020

  Last Sold Summary

  • 10% Below List Price
  • $303/SF
  • 69 Days On Market

  Current Estimated Value $681,883

  Last Listing Agent Jamie Stolinas Crame CENTURY 21 CARIOTI

  2157 Bay Line Rd, Oakland, FL 34787
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  Est $602,317 Not Listed For Sale

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

  13007 Tollcross Way, Oakland, FL 34787

  13007 Tollcross Way, Oakland, FL 34787
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  $815,000

  • 4 Beds
  • 3 Baths
  • 2,909 Sq Ft

  9611 Lost Creek Dr, Oakland, FL 34787

  Seller offering $10,000 toward Buyer’s Closing Costs + Golf Cart AND Furniture INCLUDED with sale!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

  Mariana Micheti M2M REALTY

  9611 Lost Creek Dr, Oakland, FL 34787
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  $395,000 Sold Nov 21, 2025

  13322 Pontoon Rd, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,568 Sq Ft
  • Built 2023

  Last Sold Summary

  • 1% Below List Price
  • $252/SF
  • 46 Days On Market

  Last Listing Agent Denise Gregorie CLOCK TOWER REALTY

  13322 Pontoon Rd, Oakland, FL 34787
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  Est $802,687 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,211 Sq Ft

  9462 Emerald Berry Dr, Oakland, FL 34787

  9462 Emerald Berry Dr, Oakland, FL 34787
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  $794,000 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,547 Sq Ft

  4653 Golden Birch Ave, Oakland, FL 34787

  Stunning 3-bedroom, 2.5-bath home with soaring ceilings, a versatile front room, a gourmet kitchen. This is the beautiful Mahogany Estate Floor plan By Pulte, lots of upgrades Slide into this beautiful home, starting with a flexible front room—perfect as an office, study, or formal living space—welcoming you right at the entry. Just beyond, the high-end gourmet kitchen is a showstopper, featuring

  Armando Torres POWERHOUSE REAL ESTATE NETWORK

  4653 Golden Birch Ave, Oakland, FL 34787
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  $855,000 Sold Apr 10, 2025

  234 Hammock Preserve Loop, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 2,255 Sq Ft
  • Built 2023

  Last Sold Summary

  • $379/SF
  • 6 Days On Market

  Current Estimated Value $863,582

  Last Listing Agent Lianna D'Angelo SOTERA LIVING

  234 Hammock Preserve Loop, Oakland, FL 34787
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  Est $834,254 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,853 Sq Ft

  5590 Orange Orchard Dr, Oakland, FL 34787

  5590 Orange Orchard Dr, 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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  $522,000 Sold May 23, 2025

  15657 Pelican Cay Dr, Oakland, FL 34787

  • 3 Beds
  • 2 Baths
  • 1,685 Sq Ft
  • Built 2021

  Last Sold Summary

  • 1% Above List Price
  • $310/SF
  • 5 Days On Market

  Current Estimated Value $513,476

  Last Listing Agent Kevin Pribell ACRES INC

  15657 Pelican Cay Dr, Oakland, FL 34787
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  Est $814,769 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,211 Sq Ft

  9516 Emerald Berry Dr, Oakland, FL 34787

  9516 Emerald Berry Dr, Oakland, FL 34787
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  $765,000

  • 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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  $1,260,826 Sold Sep 26, 2025

  1143 Bulwark Oaks Ln, Oakland, FL 34787

  • 5 Beds
  • 4.5 Baths
  • 3,046 Sq Ft
  • Built 2025

  Last Sold Summary

  • $414/SF

  Current Estimated Value $1,175,808

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

  1143 Bulwark Oaks Ln, Oakland, FL 34787
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  Est $803,902 Not Listed For Sale

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

  9409 Emerald Berry Dr, Oakland, FL 34787

  9409 Emerald Berry Dr, Oakland, FL 34787
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  $655,990 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,843 Sq Ft

  Captiva Plan at Serenade at Ovation - Single Family Homes, Oakland, FL 34787

  The Captiva floorplan offers a spacious two-story design with 4 bedrooms, 2.5 bathrooms, and plenty of extra room for customization. This thoughtfully laid-out home includes a flex space on the first floor, which can be transformed into a guest suite or home office, adding versatility to the design. A bonus room on the second floor provides additional living space, perfect for a media room or

  Dream Finders Homes Builder

  14229 Lanyard Way Unit 36490537, Oakland, FL 34787
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  $895,000 Sold Nov 06, 2025

  521 N Pollard St, Winter Garden, FL 34787

  • Land
  • 1 Acre
  • $895,000 per Acre

  Last Sold Summary

  • 59 Days On Market

  Last Listing Agent Blaine Dooley REGENCY REAL ESTATE LLC

  521 N Pollard St, Winter Garden, FL 34787
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  Est $625,252 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 1,908 Sq Ft

  12891 Westhaven Oak Dr, Oakland, FL 34787

  12891 Westhaven Oak Dr, Oakland, FL 34787
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  $620,000

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

  1490 Stone Arrow Ct, Oakland, FL 34787

  This stunning 5 BEDROOM + LOFT + DEN, 3.5 BATH home is situated on a spacious CONSERVATION LOT in the all-new Oakland Trail community. Once you step inside you will immediately appreciate the modern open first floor feat NEW VINYL PLANK flooring int the living room/ dining room. The spacious kitchen feat stainless steel appliance package, lots of cabinet storage under beautiful granite counters,

  Eric Jia NUMBER 1 BROKER, LLC

  1490 Stone Arrow Ct, Oakland, FL 34787
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  $642,120 Sold Oct 16, 2025

  5810 Fabry St, Oakland, FL 34787

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

  Last Sold Summary

  • $251/SF

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

  5810 Fabry St, Oakland, FL 34787
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  Est $592,174 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,596 Sq Ft

  2050 Standing Rock Cir, Oakland, FL 34787

  2050 Standing Rock Cir, Oakland, FL 34787
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  $617,990 New Construction

  • 3 Beds
  • 2 Baths
  • 2,278 Sq Ft

  Lexington w/ Bonus Plan at Serenade at Ovation - Single Family Homes, Oakland, FL 34787

  The Lexington with Bonus floorplan offers a versatile layout perfect for both comfort and functionality. This one-story design includes 3 bedrooms and 2 bathrooms, complemented by a spacious three-car garage, providing ample storage and parking options. What sets this plan apart is the large bonus room on the second floor, ideal for creating a personalized space, whether it be a media room, home

  Dream Finders Homes Builder

  14229 Lanyard Way Unit 36473362, Oakland, FL 34787
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  $635,000 Sold Dec 01, 2025

  546 Egret Place Dr, Oakland, FL 34787

  • 5 Beds
  • 4 Baths
  • 3,156 Sq Ft
  • Built 2014

  Last Sold Summary

  • 2% Below List Price
  • $201/SF
  • 44 Days On Market

  Last Listing Agent Matthew Blanco MARK SPAIN REAL ESTATE

  546 Egret Place Dr, Oakland, FL 34787
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  Est $476,068 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,785 Sq Ft

  14018 Scarlet Aster Aly, Oakland, FL 34787

  14018 Scarlet Aster Aly, Oakland, FL 34787
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  $410,000

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

  13293 Pontoon Rd, Oakland, FL 34787

  Sometimes the right home just feels easy. This 3-bedroom, 3-bath corner unit townhome was built in 2023 and sits in one of Winter Garden’s most sought-after neighborhoods, Waterleigh. From the moment you pull into the driveway, you’ll notice how clean, simple, and ready it feels. No projects. No waiting. Just move in and enjoy.Inside, natural light pours through every room, highlighting

  Mark Raumaker SERHANT

  13293 Pontoon Rd, Oakland, FL 34787
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  $826,850 Sold Jan 27, 2026

  4684 Golden Birch Ave, Oakland, FL 34787

  • 5 Beds
  • 3.5 Baths
  • 3,810 Sq Ft
  • Built 2026

  Last Sold Summary

  • $217/SF

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

  4684 Golden Birch Ave, Oakland, FL 34787
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  Est $450,354 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,814 Sq Ft

  9030 Wading Walk Ln, Oakland, FL 34787

  9030 Wading Walk Ln, Oakland, FL 34787
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  $1,809,000

  • 4 Beds
  • 4 Baths
  • 3,784 Sq Ft

  906 Allendale Ln, Winter Garden, FL 34787

  Step into a custom residence where calmness, grace, and thoughtful design greet you from the moment you arrive. In the quiet part of community, overlooking peaceful pond views, this luxury home features an open, airy floor plan filled with natural light, upscale laminate planks throughout, large lot. The gourmet kitchen is a true centerpiece here, offering a commercial-grade hood ideal for

  Jurgita Blake CENTURY 21 CARIOTI

  906 Allendale Ln, Winter Garden, FL 34787
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  $484,990 Sold Feb 28, 2025

  9267 Gran Teatro Dr, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,835 Sq Ft
  • Built 2024

  Last Sold Summary

  • 6% Below List Price
  • $264/SF
  • 82 Days On Market

  Current Estimated Value $481,938

  Last Listing Agent Stacie Brown Kelly KELLER WILLIAMS ADVANTAGE REALTY

  9267 Gran Teatro Dr, Oakland, FL 34787
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  Est $822,667 Not Listed For Sale

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

  9517 Emerald Berry Dr, Oakland, FL 34787

  9517 Emerald Berry Dr, Oakland, FL 34787
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  $649,600 Pending

  • 4 Beds
  • 3 Baths
  • 3,182 Sq Ft

  326 Largovista Dr, Oakland, FL 34787

  Under contract-accepting backup offers. Welcome to your dream home in the highly sought-after Johns Landing community! This immaculate 4-bedroom, 3-bathroom residence offers a perfect blend of elegance, comfort, and convenience—nestled in the heart of charming Oakland, FL. From the moment you step inside, you’ll be greeted by soaring ceilings, abundant natural light, and an open-concept layout

  Chris Sanford EXP REALTY LLC

  326 Largovista Dr, Oakland, FL 34787
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  $420,000 Sold Nov 18, 2025

  4576 Maple Waltz, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,652 Sq Ft
  • Built 2025

  Last Sold Summary

  • $254/SF

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

  4576 Maple Waltz, Oakland, FL 34787

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