Oakland, FL Homes

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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 $515,240

  Last Listing Agent Kevin Pribell ACRES INC

  15657 Pelican Cay Dr, Oakland, FL 34787
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  Est $1,311,241 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 4,115 Sq Ft

  15281 Arcadia Bluff Loop, Oakland, FL 34787

  15281 Arcadia Bluff Loop, Oakland, FL 34787
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  $1,850,000

  • 6 Beds
  • 5 Baths
  • 4,104 Sq Ft

  1101 Eagles Pass Way, Oakland, FL 34787

  One or more photo(s) has been virtually staged. Modern Luxury in the Heart of Winter Garden’s Golf Cart District! Welcome to 1101 Eagles Pass Way, an exquisite 6-bedroom, 5-bathroom home situated on a desirable corner lot in the sought-after Oakland Park community—one of the few neighborhoods within Winter Garden’s beloved golf cart district. Just one block from Lake Apopka and less than two

  Kevin Sullivan LAKESIDE REALTY WINDERMERE INC

  1101 Eagles Pass Way, 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

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

  1143 Bulwark Oaks Ln, Oakland, FL 34787
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  Est $430,165 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,755 Sq Ft

  10665 Words Dr, Oakland, FL 34787

  10665 Words Dr, Oakland, FL 34787
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  $899,000

  • 4 Beds
  • 3.5 Baths
  • 3,448 Sq Ft

  501 E Oakland Ave, Winter Garden, FL 34787

  One or more photo(s) has been virtually staged. Welcome to your private retreat in the heart of Oakland! This stunning 4-bedroom, 3.5-bathroom home offers 3,448 sq. ft. of beautifully designed living space on an oversized 0.34-acre lot with no rear neighbors, providing peace and privacy in a serene setting. Enjoy the best of both worlds with a quiet neighborhood just steps from Oakland Avenue

  Erica Diaz HOMEVEST REALTY

  501 E Oakland Ave, Winter Garden, 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 $860,359 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,409 Sq Ft

  1112 Eagles Pass Way, Oakland, FL 34787

  1112 Eagles Pass Way, Oakland, FL 34787
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  $1,675,000 New Construction

  • 5 Beds
  • 5 Baths
  • 3,895 Sq Ft

  Custom Carrabelle Plan at Oakland Park, Winter Garden, FL 34787

  AR Homes Builder

  884 Tilden Oaks Trail Unit 37615294, Winter Garden, 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 $437,256 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,818 Sq Ft

  6519 Glory Bower Dr, Oakland, FL 34787

  6519 Glory Bower Dr, Oakland, FL 34787
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  $515,000

  • 3 Beds
  • 2.5 Baths
  • 1,796 Sq Ft

  13748 Werrington Dr, Oakland, FL 34787

  Seller offering concessions to compete with new construction in the area! 13748 Werrington Drive isn’t just a house — it’s your next chapter waiting to be written. Tucked inside the vibrant, amenity-rich community of Encore at Ovation, this stylish 3-bedroom, 2.5-bath gem offers the perfect mix of comfort, design, and location. From the moment you step through the door, you’ll fall in love with

  Kimberly Ann Zeidner, LLC CHARLES RUTENBERG REALTY ORLANDO

  13748 Werrington Dr, 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 $718,821 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,346 Sq Ft

  13234 Spring Grove Way, Oakland, FL 34787

  13234 Spring Grove Way, Oakland, FL 34787
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  $75,000

  • Land
  • 0.11 Acre
  • $681,818 per Acre

  121 S Nixon St, Oakland, FL 34760

  If you're looking for land in Oakland, you have certainly found it! Located in the most picturesque neighborhood in central Florida, this beautiful lot could be the site of your next home. Oakland is quaintly situated in between Winter Garden and Clermont, blending small town feel with activity brimming everywhere you turn.

  Ramon Morales SANCTUM REALTY PROFESSIONALS LLC

  121 S Nixon St, Oakland, FL 34760
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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 $482,495

  Last Listing Agent Stacie Brown Kelly KELLER WILLIAMS ADVANTAGE REALTY

  9267 Gran Teatro Dr, Oakland, FL 34787
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  Est $537,296 Not Listed For Sale

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

  14086 Frasier St, Oakland, FL 34787

  14086 Frasier St, Oakland, FL 34787
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  $630,000

  • 4 Beds
  • 3.5 Baths
  • 2,743 Sq Ft

  12554 Westhaven Oak Dr, Oakland, FL 34787

  This tenant-occupied home, rented for $3,400/month until June 30, 2026, presents an excellent investment opportunity with immediate income. Located in the desirable Osprey Ranch community of Winter Garden, the property features 4 bedrooms, 3.5 bathrooms, and 2,743 heated square feet of living space. The functional floor plan includes a modern kitchen with all appliances and a laundry room with

  Adriana PL Franzoi WRA BUSINESS & REAL ESTATE

  12554 Westhaven Oak 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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  Est $908,243 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,334 Sq Ft

  9122 Sonoma Coast Dr, Oakland, FL 34787

  9122 Sonoma Coast Dr, Oakland, FL 34787
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  $997,000

  • 5 Beds
  • 3.5 Baths
  • 3,910 Sq Ft

  9549 Bolero Rd, Oakland, FL 34787

  The lakefront life of grandeur awaits you in this stunningly enhanced North Haven model by DR Horton's luxury line, Emerald Homes! Structural enhancements are plentiful and include a Control4 Smart Home Automation System, custom designed closets in nearly every closet throughout the home, security system, technology operated window treatment, entire home water softener, reverse osmosis kitchen

  Jacquelyn Voigt KELLER WILLIAMS REALTY AT THE LAKES

  9549 Bolero Rd, Oakland, FL 34787
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  $444,590 Sold Jul 29, 2025

  6678 Juneberry Way, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,846 Sq Ft
  • Built 2025

  Last Sold Summary

  • $241/SF
  • 39 Days On Market

  Current Estimated Value $449,627

  Last Listing Agent Adam Schott DRB GROUP REALTY, LLC

  6678 Juneberry Way, Oakland, FL 34787
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  Est $432,450 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,579 Sq Ft

  15169 Aqua Sol Ln, Oakland, FL 34787

  15169 Aqua Sol Ln, Oakland, FL 34787
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  $745,000

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

  3294 Hanging Tide St, Oakland, FL 34787

  Step into this stunning two-story home in the popular gated community of Lakeview Preserve, where elegance meets functionality. Sitting on a larger homesite with a 4-foot garage extension, EV car charger, and beautiful stone-accented exterior, this home is as striking on the outside as it is inside. The Yorkshire floorplan by Pulte Homes offers 5 spacious bedrooms, 4.5 bathrooms, a large upstairs

  Amy Kidwell PA PREFERRED REAL ESTATE BROKERS

  3294 Hanging Tide St, Oakland, FL 34787
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  $980,000 Sold Apr 14, 2025

  210 Hammock Preserve Loop, Oakland, FL 34787

  • 5 Beds
  • 4 Baths
  • 3,070 Sq Ft
  • Built 2023

  Last Sold Summary

  • 18% Below List Price
  • $319/SF
  • 47 Days On Market

  Current Estimated Value $1,001,964

  Last Listing Agent Matthew Sutton BERGER REALTY & INVESTMENTS

  210 Hammock Preserve Loop, Oakland, FL 34787
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  /2

  Est $805,110 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 3,076 Sq Ft

  14229 Lanyard Way, Oakland, FL 34787

  14229 Lanyard Way, Oakland, FL 34787
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  $479,990 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,675 Sq Ft

  17526 Northlake Grove Dr, Oakland, FL 34787

  Discover exceptional living in this thoughtfully designed end-unit townhome, perfectly situated in the heart of Winter Garden. Just 37 minutes from Orlando International Airport and 20 minutes from world-famous Disney theme parks, this home offers unbeatable convenience paired with the charm and rich local history the area is known for. Inside, you’ll find a beautifully curated kitchen, living,

  Reed Williams ASHTON WOODS FLORIDA REALTY LLC

  17526 Northlake Grove Dr, Oakland, FL 34787
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  $688,000 Sold Aug 28, 2025

  2901 Haze Rd, Oakland, FL 34787

  • 5 Beds
  • 3.5 Baths
  • 3,385 Sq Ft
  • Built 2025

  Last Sold Summary

  • $203/SF

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

  2901 Haze Rd, Oakland, FL 34787
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  Est $385,418 Not Listed For Sale

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

  9145 Mellow Coral St, Oakland, FL 34787

  9145 Mellow Coral St, Oakland, FL 34787
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  $499,950 Pending

  • 4 Beds
  • 2 Baths
  • 2,094 Sq Ft

  222 Largovista Dr, Oakland, FL 34787

  Under contract-accepting backup offers. Luxury Living in the Gated Community of John’s Landing on Beautiful Johns Lake!This well-maintained, move-in-ready 4-bedroom, 2-bath home offers flexible living in one of Oakland/Winter Garden’s most desirable lakefront communities. Mature landscaping, an oversized driveway, and a 3-car garage provide excellent curb appeal. Inside, abundant natural

  Sonia Jenkins ORANGE REALTY PROFESSIONALS LLC

  222 Largovista Dr, Oakland, FL 34787
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  $387,900 Sold Jul 17, 2025

  1509 Sweet Apple St, Oakland, FL 34787

  • 3 Beds
  • 3 Baths
  • 1,809 Sq Ft
  • Built 2019

  Last Sold Summary

  • 8% Below List Price
  • $214/SF
  • 144 Days On Market

  Current Estimated Value $385,606

  Last Listing Agent Robert Jones OFFERPAD BROKERAGE FL, LLC

  1509 Sweet Apple St, Oakland, FL 34787
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  Est $541,837 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,114 Sq Ft

  14115 Frasier St, Oakland, FL 34787

  14115 Frasier St, Oakland, FL 34787
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  $415,000 Pending

  • Land
  • 0.27 Acre
  • $1,537,037 per Acre

  15738 E Oakland Ave, Oakland, FL 34787

  Under contract-accepting backup offers. Nestled in the heart of Oakland, Florida, this expansive homesite offers the perfect canvas to build your dream home with custom home builder, Pioneer Builders. Set in an illustrious community, called the Grove, this generously sized lot is ideal for crafting your unique custom home. The Grove is situated within Oakland’s most sought-after neighborhood

  Alexis Anderson REGENCY REAL ESTATE LLC

  15738 E Oakland Ave, Oakland, FL 34787
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  $585,000 Sold Aug 20, 2025

  15114 Field Daisy Dr, Oakland, FL 34787

  • 4 Beds
  • 2 Baths
  • 2,142 Sq Ft
  • Built 2025

  Last Sold Summary

  • $273/SF

  Current Estimated Value $584,856

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

  15114 Field Daisy Dr, Oakland, FL 34787
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  Est $455,017 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,032 Sq Ft

  8149 Mosaic Ln, Oakland, FL 34787

  8149 Mosaic Ln, Oakland, FL 34787
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  $1,675,000 New Construction

  • 5 Beds
  • 5 Baths
  • 4,819 Sq Ft

  166 Hammock Preserve Loop, Oakland, FL 34787

  AR Homes Builder

  166 Hammock Preserve Loop, Oakland, FL 34787
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  $800,000 Sold Feb 24, 2025

  16261 Point Rock Dr, Oakland, FL 34787

  • 5 Beds
  • 3.5 Baths
  • 2,587 Sq Ft
  • Built 2023

  Last Sold Summary

  • 11% Below List Price
  • $309/SF
  • 229 Days On Market

  Current Estimated Value $788,432

  Last Listing Agent Jose Fernandes CELEBRITY GLOBAL REALTY LLC

  16261 Point Rock Dr, Oakland, FL 34787
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  Est $824,723 Not Listed For Sale

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

  1197 Wilder Oaks Way, Oakland, FL 34787

  1197 Wilder Oaks Way, Oakland, FL 34787
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  $471,900

  • 4 Beds
  • 2.5 Baths
  • 2,017 Sq Ft

  2435 Standing Rock Cir, Oakland, FL 34787

  Perfectly situated in the desirable Oakland Trails neighborhood this perfectly updated and maintained home is a turnkey away from being yours! 4 bed, 2.5 bath, the primary bed in the second level. The landscape perfectly accentuates your front porch. Step inside your fully upgraded home; complete with luxury upgrades ranging from lighting, designer finishes, and brand-name appliances. Up the

  Celestino De Cicco CENTRAL FLORIDA REALTY

  2435 Standing Rock Cir, Oakland, FL 34787
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  $455,000 Sold Jun 11, 2025

  13418 Princess St, Oakland, FL 34787

  • 2 Beds
  • 2 Baths
  • 1,579 Sq Ft
  • Built 2024

  Last Sold Summary

  • 1% Above List Price
  • $288/SF
  • 185 Days On Market

  Current Estimated Value $457,052

  Last Listing Agent Adrienne Escott PULTE REALTY OF NORTH FLORIDA LLC

  13418 Princess St, Oakland, FL 34787

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