Oakland, FL Homes

• 

  

  

  /3

  $655,990

  New Construction

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

  Captiva Plan at Serenade at Ovation - 50' Collection, 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
• 

  

  /2

  $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

  Current Estimated Value $396,665

  Last Listing Agent Denise Gregorie CLOCK TOWER REALTY

  13322 Pontoon Rd, Oakland, FL 34787
• 

  

  /2

  Est $837,832

  Not Listed For Sale

  1102 Eagles Pass Way, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 2,260 Sq Ft
  • Built 2023

  1102 Eagles Pass Way, Oakland, FL 34787

  Last Sold Summary

  • 4 Days On Market
• 

  

  

  /49

  $635,000

  Pending

  • 4 Beds
  • 3.5 Baths
  • 2,741 Sq Ft

  3351 Hanging Tide St, Oakland, FL 34787

  Under contract-accepting backup offers. Virtually Staged. Welcome to this move in ready home newly built in 2021 in the gated Lakeview Preserve community. This single story home is offering 4 bedrooms, 3.5 bathrooms, with split bedroom layout and a spacious open floor plan. Step inside to find a bright and airy living space that seamlessly connects the kitchen, dining, and living areas. The

  Devon Sobers KELLER WILLIAMS ADVANTAGE III

  3351 Hanging Tide St, Oakland, FL 34787
• 

  

  /2

  $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 $1,225,932

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

  1143 Bulwark Oaks Ln, Oakland, FL 34787
• 

  /2

  Est $656,690

  Not Listed For Sale

  13636 Fresh Ivy St, Oakland, FL 34787

  • 2 Beds
  • 2 Baths
  • 1,943 Sq Ft
  • Built 2024

  13636 Fresh Ivy St, Oakland, FL 34787

  Last Sold Summary

  • 3 Days On Market
• 

  

  /50

  $499,000

  $16K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,069 Sq Ft

  1937 Standing Rock Cir, Oakland, FL 34787

  Oakland Trails is located right on the scenic West Orange Trail and just a bike ride away from the vibrant downtown Historic Winter Garden! **This home qualifies for loan options with NO DOWN PAYMENT required, 100% financing available for qualified buyers.** Step into an immaculately maintained three-bedroom, two-and-a-half-bathroom bungalow with updated wood-look plank luxury vinyl flooring

  Ken Pozek REAL BROKER, LLC

  1937 Standing Rock Cir, Oakland, FL 34787
• 

  /2

  $537,000

  Sold Feb 24, 2026

  326 Largovista Dr, Oakland, FL 34787

  • 4 Beds
  • 3 Baths
  • 3,182 Sq Ft
  • Built 2004

  Last Sold Summary

  • 23% Below List Price
  • $169/SF
  • 135 Days On Market

  Current Estimated Value $583,393

  Last Listing Agent Chris Sanford EXP REALTY LLC

  326 Largovista Dr, Oakland, FL 34787
• 

  /2

  Est $608,581

  Not Listed For Sale

  13648 Fresh Ivy St, Oakland, FL 34787

  • 2 Beds
  • 2 Baths
  • 1,707 Sq Ft
  • Built 2024

  13648 Fresh Ivy St, Oakland, FL 34787

  Last Sold Summary

  • 13 Days On Market
• 

  /2

  $617,990

  New Construction

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

  Lexington w/ Bonus Plan at Serenade at Ovation - 50' Collection, 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
• 

  /2

  $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
• 

  

  /20

  Est $675,019

  Not Listed For Sale

  13714 Fresh Ivy St, Oakland, FL 34787

  • 2 Beds
  • 2.5 Baths
  • 2,080 Sq Ft
  • Built 2024

  13714 Fresh Ivy St, Oakland, FL 34787

  Last Sold Summary

  • 65 Days On Market
• 

  /2

  $925,990

  New Construction Pending

  • 4 Beds
  • 3.5 Baths
  • 3,498 Sq Ft

  15184 Tea Tree Dr, Oakland, FL 34787

  One or more photo(s) has been virtually staged. Pre-Construction. To be built. Sample Image The Venice is a two-story home designed for efficient and flexible living. The first floor features an open-concept layout with a centrally located kitchen overlooking the dining area and main living space. The primary bedroom is located on the main level and includes a walk-in closet and en-suite

  Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

  15184 Tea Tree Dr, Oakland, FL 34787
• 

  /2

  $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

  Current Estimated Value $643,577

  Last Listing Agent Matthew Blanco MARK SPAIN REAL ESTATE

  546 Egret Place Dr, Oakland, FL 34787
• 

  /2

  Est $668,579

  Not Listed For Sale

  13672 Fresh Ivy St, Oakland, FL 34787

  • 2 Beds
  • 2 Baths
  • 1,889 Sq Ft
  • Built 2024

  13672 Fresh Ivy St, Oakland, FL 34787

  Last Sold Summary

  • 96 Days On Market
• 

  

  /24

  $597,990

  New Construction Pending

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

  3112 Namaste Dr, Oakland, FL 34787

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

  Ben Goldstein LENNAR REALTY

  3112 Namaste Dr, Oakland, FL 34787
• 

  /2

  $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

  Current Estimated Value $827,675

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

  4684 Golden Birch Ave, Oakland, FL 34787
• 

  /2

  Est $621,935

  Not Listed For Sale

  15191 Blue Peacock Ln, Oakland, FL 34787

  • 4 Beds
  • 2.5 Baths
  • 2,584 Sq Ft
  • Built 2023

  15191 Blue Peacock Ln, Oakland, FL 34787

  Last Sold Summary
• 

  /2

  $637,325

  New Construction Pending

  • 4 Beds
  • 3 Baths
  • 2,102 Sq Ft

  17138 Ingram Hills Aly, Oakland, FL 34787

  One or more photo(s) has been virtually staged. Pre-Construction. To be built. The Berkley floorplan by Dream Finders Homes features 2,102 square feet of well-designed living space across two stories. This home includes 4 bedrooms, 3 full bathrooms, and a 2-car garage. The open-concept main floor boasts a spacious family room, dining area, and a modern kitchen with ample counter space—ideal for

  Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

  17138 Ingram Hills Aly, Oakland, FL 34787
• 

  /2

  $787,000

  Sold Feb 23, 2026

  3375 Hanging Tide St, Oakland, FL 34787

  • 4 Beds
  • 4.5 Baths
  • 2,741 Sq Ft
  • Built 2021

  Last Sold Summary

  • 9% Below List Price
  • $287/SF
  • 62 Days On Market

  Current Estimated Value $807,345

  Last Listing Agent Sean Flatley KELLER WILLIAMS REALTY AT THE PARKS

  3375 Hanging Tide St, Oakland, FL 34787
• 

  /2

  Est $663,010

  Not Listed For Sale

  15014 Summer Harvest St, Oakland, FL 34787

  • 5 Beds
  • 4.5 Baths
  • 2,861 Sq Ft
  • Built 2024

  15014 Summer Harvest St, Oakland, FL 34787

  Last Sold Summary
• 

  

  /78

  $2,699,000

  $51K PRICE DROP

  • 5 Beds
  • 6 Baths
  • 4,373 Sq Ft

  812 Johns Point Dr, Oakland, FL 34787

  Experience unparalleled lakefront living in this fully renovated Mediterranean-style estate located in the exclusive gated community of John’s Cove on Johns Lake. A grand driveway and manicured landscaping welcome you into a striking modern entry and elegant interior featuring high-end flooring and designer finishes throughout.Designed for effortless entertaining, the open-concept layout

  Any Alves WRA BUSINESS & REAL ESTATE

  812 Johns Point Dr, Oakland, FL 34787
• 

  /2

  $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

  Current Estimated Value $426,169

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

  4576 Maple Waltz, Oakland, FL 34787
• 

  /2

  Est $630,857

  Not Listed For Sale

  15086 Summer Harvest St, Oakland, FL 34787

  • 3 Beds
  • 2 Baths
  • 1,934 Sq Ft
  • Built 2025

  15086 Summer Harvest St, Oakland, FL 34787

  Last Sold Summary

  • 140 Days On Market
• 

  

  /8

  $432,490

  New Construction $5K PRICE INCREASE

  • 2 Beds
  • 2 Baths
  • 1,580 Sq Ft

  3043 Repose Dr, Oakland, FL 34787

  Under Construction. This dazzling Frey II, two-bedroom home provides convenient single-story living. A secondary bedroom and a study are secluded near the front of the home, leading to an inviting open-concept floorplan that boasts convenient access to a covered patio for seamless indoor-outdoor living. The owner’s suite is nestled into a private rear corner, complete with a full bathroom and

  Ben Goldstein LENNAR REALTY

  3043 Repose Dr, Oakland, FL 34787
• 

  /2

  $575,000

  Sold May 01, 2026

  13732 Fresh Ivy St, Oakland, FL 34787

  • 2 Beds
  • 2 Baths
  • 1,889 Sq Ft
  • Built 2024

  Last Sold Summary

  • 8% Below List Price
  • $304/SF
  • 222 Days On Market

  Current Estimated Value $585,879

  Last Listing Agent Ken Pozek REAL BROKER, LLC

  13732 Fresh Ivy St, Oakland, FL 34787
• 

  /2

  Est $1,672,377

  Not Listed For Sale

  1243 Civitas Way, Winter Garden, FL 34787

  • 5 Beds
  • 4.5 Baths
  • 4,020 Sq Ft
  • Built 2023

  1243 Civitas Way, Winter Garden, FL 34787

  Last Sold Summary

  • 4 Days On Market
• 

  

  /67

  $1,765,000

  $44K PRICE DROP

  • 5 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
• 

  /2

  $395,000

  Sold Feb 19, 2026

  321 E Gulley Ave, Oakland, FL 34760

  • Land
  • 12,196 Sq Ft
  • $1,410,714 per Acre

  Last Sold Summary

  • 8 Days On Market

  Current Estimated Value $427,310

  Last Listing Agent Deanna Meredith LUXE PROPERTIES LLC

  321 E Gulley Ave, Oakland, FL 34760
• 

  /2

  Est $508,497

  Not Listed For Sale

  14091 Frasier St, Oakland, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,112 Sq Ft
  • Built 2024

  14091 Frasier St, Oakland, FL 34787
• 

  

  /56

  $729,000

  $51K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 3,284 Sq Ft

  8114 Sayings Dr, Winter Garden, FL 34787

  Virtually Staged. Welcome to this beautifully maintained 5-bedroom, 3-bathroom home in the highly sought-after Storey Grove community of Winter Garden, one of Horizon West's most desirable neighborhoods. Offering approximately 3,300 square feet of thoughtfully designed living space, this exceptional home combines comfort, functionality, and an unbeatable location. Perfectly positioned on a

  Anna Shi LPT REALTY, LLC

  8114 Sayings Dr, Winter Garden, FL 34787
• 

  /2

  $565,000

  Sold Jun 12, 2026

  1507 Wild Sweetgrass Way, Oakland, FL 34760

  • 3 Beds
  • 2 Baths
  • 1,975 Sq Ft
  • Built 2019

  Last Sold Summary

  • $286/SF
  • 3 Days On Market

  Current Estimated Value $568,083

  Last Listing Agent Rema Perras CORCORAN PREMIER REALTY

  1507 Wild Sweetgrass Way, Oakland, FL 34760
• 

  /2

  Est $491,108

  Not Listed For Sale

  9231 Gran Teatro Dr, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,833 Sq Ft
  • Built 2024

  9231 Gran Teatro Dr, Oakland, FL 34787

  Last Sold Summary
• 

  

  /41

  $457,900

  Open Sat 11AM - 3PM

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

  2247 White Feather Loop, Oakland, FL 34787

  Welcome to this exceptional home in the highly sought-after Oakland Trails community! This beautifully designed 3-bedroom, 2.5-bath residence offers approximately 1,838 square feet of thoughtfully designed living space with an open and functional floor plan that truly stands out in the neighborhood. From the moment you arrive, you’ll notice the extended brick paver driveway, providing additional

  Carolina Cote Munoz LPT REALTY, LLC

  2247 White Feather Loop, Oakland, FL 34787
• 

  /2

  $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
• 

  /2

  Est $358,326

  Not Listed For Sale

  2226 Gopher Tortoise Terrace, Oakland, FL 34760

  • 2 Beds
  • 2.5 Baths
  • 1,472 Sq Ft
  • Built 2020

  2226 Gopher Tortoise Terrace, Oakland, FL 34760

  Last Sold Summary

  • 1 Day On Market
• 

  

  /10

  $2,575,000

  New Construction

  • 5 Beds
  • 7 Baths
  • 4,210 Sq Ft

  1155 Prado Ln, Winter Garden, FL 34787

  Pre-Construction. To be built. Welcome home to The Wildflower, an exquisitely crafted new construction estate nestled within the exclusive community of The Grove in charming Oakland, Florida. Masterfully built by the renowned Justice & Wood Builders — whose principals each bring over 25 years of custom homebuilding experience — this stunning residence delivers the perfect blend of timeless

  Alexis Anderson REGENCY REAL ESTATE LLC

  1155 Prado Ln, Winter Garden, FL 34787
• 

  /2

  $680,000

  Sold Mar 31, 2026

  2450 Standing Rock Cir, Oakland, FL 34787

  • 5 Beds
  • 4 Baths
  • 3,163 Sq Ft
  • Built 2019

  Last Sold Summary

  • 5% Below List Price
  • $215/SF
  • 120 Days On Market

  Current Estimated Value $681,976

  Last Listing Agent Anamaria Marquez PREMIER SOTHEBYS INT'L REALTY

  2450 Standing Rock Cir, Oakland, FL 34787
• 

  /2

  Est $626,882

  Not Listed For Sale

  12742 Lavender Bloom Aly, Oakland, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 2,743 Sq Ft
  • Built 2024

  12742 Lavender Bloom Aly, Oakland, FL 34787

  Last Sold Summary
• 

  

  /59

  $415,000

  $10K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 1,768 Sq Ft

  16461 Prairie School Dr, Oakland, FL 34787

  PRICE REDUCED Welcome to your future home in the highly desirable, sought-after Hawksmoor community of Horizon West / Winter Garden.This beautifully maintained, move-in ready 4-bedroom, 2.5-bathroom townhome offers the perfect blend of modern comfort, functional design, and a low-maintenance lifestyle. The main level features an inviting open-concept layout filled with abundant natural light,

  Jhoana Loyo Urrutia LA ROSA REALTY LLC

  16461 Prairie School Dr, Oakland, FL 34787

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