Oakland, FL Homes

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  $545,000 Sold Jun 16, 2025

  1757 Standing Rock Cir, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 2,000 Sq Ft
  • Built 2017

  Last Sold Summary

  • 3% Below List Price
  • $272/SF
  • 12 Days On Market

  Current Estimated Value $538,071

  Last Listing Agent Shannon Christian EXP REALTY LLC

  1757 Standing Rock Cir, Oakland, FL 34787
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  Est $530,066 Not Listed For Sale

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

  13025 Tollcross Way, Oakland, FL 34787

  13025 Tollcross Way, Oakland, FL 34787
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  $414,900 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,503 Sq Ft

  1321 Planted Pine St, Oakland, FL 34760

  Under contract-accepting backup offers. Nestled in the highly desirable community of Longleaf at Oakland, this exquisite townhome is a blend of elegance and functionality. The open floor plan bathes the interior in natural light, creating a warm and inviting atmosphere. The kitchen, a modern culinary space, features stainless steel appliances, sleek granite countertops, and ample cabinet space.

  Justin Cabral PROPERTY LOGIC RE

  1321 Planted Pine St, Oakland, FL 34760
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  $446,000 Sold Mar 13, 2025

  2261 Standing Rock Cir, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,753 Sq Ft
  • Built 2019

  Last Sold Summary

  • 4% Below List Price
  • $254/SF
  • 136 Days On Market

  Current Estimated Value $452,833

  Last Listing Agent Fernando Orsini CT HOMES REALTY CORPORATION

  2261 Standing Rock Cir, Oakland, FL 34787
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  Est $752,963 Not Listed For Sale

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

  3410 Buoy Cir, Oakland, FL 34787

  3410 Buoy Cir, Oakland, FL 34787
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  $690,000 Pending

  • 5 Beds
  • 4 Baths
  • 4,030 Sq Ft

  570 Johns Landing Way, Oakland, FL 34787

  Under contract-accepting backup offers. VA Assumable Loan with 2.75% interest rate! Welcome home to the gated community of John’s Landing, where comfort, space, and lifestyle come together with Chain of Lakes access and a thoughtfully designed floor plan, perfect for everyday living. From the moment you step inside this 5 bedroom, 4 bath home, you’ll notice the care and quality found in the

  Ashley Pun DENIZ REALTY PARTNERS LLC

  570 Johns Landing Way, Oakland, FL 34787
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  $420,000 Sold Jul 09, 2025

  709 Strihal Loop, Oakland, FL 34787

  • 3 Beds
  • 2 Baths
  • 1,621 Sq Ft
  • Built 2003

  Last Sold Summary

  • 3% Below List Price
  • $259/SF
  • 24 Days On Market

  Current Estimated Value $424,215

  Last Listing Agent Jessica Stone CENTURY 21 CARIOTI

  709 Strihal Loop, Oakland, FL 34787
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  Est $423,180 Not Listed For Sale

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

  16467 Prairie School Dr, Oakland, FL 34787

  16467 Prairie School Dr, Oakland, FL 34787
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  $875,000

  • 4 Beds
  • 3.5 Baths
  • 3,406 Sq Ft

  607 E Oakland Ave, Winter Garden, FL 34787

  Welcome to this exceptional Winter Garden home with 4 bedrooms, 3.5-bathrooms, PLUS home office PLUS upstairs bonus room, flexible living spaces make this home work for you. This is 607 E. Oakland Ave - where classic Old-Florida charm meets modern luxury and unbeatable location. Tile flooring and refined tray ceilings flow throughout the home, while the gourmet kitchen with premium upgrades is

  Kristine McKinley RE/MAX TOWN & COUNTRY REALTY

  607 E Oakland Ave, Winter Garden, FL 34787
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  $604,000 Sold Sep 19, 2025

  410 E Gulley Ave, Oakland, FL 34760

  • 5 Beds
  • 3 Baths
  • 2,458 Sq Ft
  • Built 1959

  Last Sold Summary

  • 8% Below List Price
  • $246/SF
  • 30 Days On Market

  Current Estimated Value $618,317

  Last Listing Agent Keith Packey RE/MAX TITANIUM GROUP

  410 E Gulley Ave, Oakland, FL 34760
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  Est $568,826 Not Listed For Sale

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

  14103 Lochend Way, Oakland, FL 34787

  14103 Lochend Way, Oakland, FL 34787
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  $1,998,000 New Construction

  • 4 Beds
  • 4 Baths
  • 4,557 Sq Ft

  1258 Ridge Lake Way, Winter Garden, FL 34787

  Pre-Construction. To be built. Pre-Construction. To be built. A Custom home in the Reserve of the sought-after Oakland Park community. This is a RCB Homes custom-built two story, four-bedroom, four-bath floor plan that you will customize with all the luxury finishes you will pick yourself! The floorplan is an open concept design, but you can still make changes to the floorplan if you want! The

  Chris Herlihy NEW HOMES REAL ESTATE, INC.

  1258 Ridge Lake Way, Winter Garden, FL 34787
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  $652,316 Sold Nov 14, 2025

  16108 Honey Harvest St, Oakland, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 2,441 Sq Ft
  • Built 2025

  Last Sold Summary

  • $267/SF

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

  16108 Honey Harvest St, Oakland, FL 34787
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  Est $520,372 Not Listed For Sale

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

  14407 Braemar St, Oakland, FL 34787

  14407 Braemar St, Oakland, FL 34787
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  $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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  $1,100,000 Sold Mar 17, 2025

  111 Millholland St, Oakland, FL 34760

  • 4 Beds
  • 3 Baths
  • 3,333 Sq Ft
  • Built 2001

  Last Sold Summary

  • 8% Below List Price
  • $330/SF
  • 7 Days On Market

  Current Estimated Value $1,096,693

  Last Listing Agent Ashley Boyd BHHS FLORIDA REALTY

  111 Millholland St, Oakland, FL 34760
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  Not Listed For Sale

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

  6295 Blissful St, Oakland, FL 34787

  6295 Blissful St, Oakland, FL 34787
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  $407,990 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,715 Sq Ft

  Porter Plan at Serenade at Ovation - Townhomes, Oakland, FL 34787

  The Porter floorplan is an inviting two-story townhome designed with thoughtful spaces throughout. Featuring three bedrooms and two full bathrooms, the layout offers a smooth flow between living spaces. The first floor boasts a bright great room that opens into the dining area and lanai, perfect for entertaining or relaxation. Upstairs, all three bedrooms are thoughtfully arranged alongside a

  Dream Finders Homes Builder

  14229 Lanyard Way Unit 36452383, Oakland, FL 34787
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  $2,675,000 Sold Oct 30, 2025

  1179 Prado Ln, Oakland, FL 34787

  • 4 Beds
  • 4.5 Baths
  • 4,561 Sq Ft
  • Built 2026

  Last Sold Summary

  • $586/SF

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

  1179 Prado Ln, Oakland, FL 34787
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  Est $482,799 Not Listed For Sale

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

  2071 White Feather Loop, Oakland, FL 34787

  2071 White Feather Loop, Oakland, FL 34787
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  $549,990 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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  $449,990 Sold Nov 07, 2025

  17681 Japonica Bloom Dr, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,577 Sq Ft
  • Built 2025

  Move in Ready Sold Summary

  • $285/SF
  • 9 Days On Market

  Ashton Woods Northlake at Ovation - Townhomes

  17681 Japonica Bloom Dr, Oakland, FL 34787
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  Est $466,315 Not Listed For Sale

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

  2153 Standing Rock Cir, Winter Garden, FL 34787

  2153 Standing Rock Cir, Winter Garden, FL 34787
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  $489,900 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,909 Sq Ft

  2029 White Feather Loop, Winter Garden, FL 34787

  Under contract-accepting backup offers. Welcome to an exceptional home in the highly sought-after Oakland Trails community! This beautifully designed 3-bed, 2.5-bath residence boasts an open and functional floor plan that truly sets it apart from others in the neighborhood. With approximately 1,909 sq. ft. of thoughtfully laid-out living space, this home offers modern comfort with everyday

  Eric Bress, Jr ERIC BRESS REAL ESTATE LLC

  2029 White Feather Loop, Winter Garden, FL 34787
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  $390,000 Sold Jul 31, 2025

  121 W Oakland Ave, Oakland, FL 34760

  • 3 Beds
  • 1 Bath
  • 1,159 Sq Ft
  • Built 1935

  Last Sold Summary

  • $336/SF
  • 7 Days On Market

  Current Estimated Value $382,000

  Last Listing Agent Sheri Loiacono WINDSOR REALTY GROUP INC

  121 W Oakland Ave, Oakland, FL 34760
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  Est $637,761 Not Listed For Sale

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

  15049 Summer Harvest St, Oakland, FL 34787

  15049 Summer Harvest St, Oakland, FL 34787
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  $449,900

  • Land
  • 0.23 Acre
  • $1,956,087 per Acre

  1203 Ridge Lake Way, Winter Garden, FL 34787

  LOT 244: Don't miss your final opportunity to build your dream home in Oakland Park, a charming golf cart community along Lake Apopka and the West Orange Trail. These recently released lots are part the final phase of this coveted neighborhood and some of the best lots available. This is your chance to build an estate or lake front home that is only 2 miles for adorable Downtown Winter Garden,

  Tracey McFadden OAK AVENUE REAL ESTATE LLC

  1203 Ridge Lake Way, Winter Garden, FL 34787
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  $620,000 Sold Mar 24, 2025

  13648 Fresh Ivy St, Oakland, FL 34787

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

  Last Sold Summary

  • 6% Below List Price
  • $363/SF
  • 13 Days On Market

  Current Estimated Value $621,282

  Last Listing Agent Ellie Hunter PULTE REALTY OF NORTH FLORIDA LLC

  13648 Fresh Ivy St, Oakland, FL 34787
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  Est $594,754 Not Listed For Sale

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

  15109 Summer Harvest St, Oakland, FL 34787

  15109 Summer Harvest St, Oakland, FL 34787
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  $498,990 New Construction

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

  Brantley Plan at Serenade at Ovation, 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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  $583,380 Sold Nov 18, 2025

  4652 Golden Birch Ave, Oakland, FL 34787

  • 3 Beds
  • 2 Baths
  • 2,199 Sq Ft
  • Built 2025

  Last Sold Summary

  • 2% Below List Price
  • $265/SF
  • 7 Days On Market

  Last Listing Agent Adrienne Escott PULTE REALTY OF NORTH FLORIDA LLC

  4652 Golden Birch Ave, Oakland, FL 34787
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  Est $603,626 Not Listed For Sale

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

  15101 Summer Harvest St, Oakland, FL 34787

  15101 Summer Harvest St, Oakland, FL 34787
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  $2,238,120 New Construction

  • 5 Beds
  • 5.5 Baths
  • 4,204 Sq Ft

  1173 Prado Ln, Oakland, FL 34787

  Pre-Construction. To be built. Introducing the Sunburst Model by Davila HomesDiscover the perfect blend of modern luxury and everyday comfort in the Sunburst, a beautifully designed 4,204-square-foot residence by Davila Homes. With 5 spacious bedrooms and 5.5 elegantly finished bathrooms, this home offers the ideal balance of open living and private retreat—crafted to meet the needs of

  Alexis Anderson REGENCY REAL ESTATE LLC

  1173 Prado Ln, Oakland, FL 34787
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  $840,000 Sold Aug 29, 2025

  413 MacChi Ave, Oakland, FL 34787

  • 4 Beds
  • 3 Baths
  • 3,290 Sq Ft
  • Built 2006

  Last Sold Summary

  • 7% Below List Price
  • $255/SF
  • 80 Days On Market

  Current Estimated Value $822,162

  Last Listing Agent Sophia Ferrara COLDWELL BANKER REALTY

  413 MacChi Ave, Oakland, FL 34787
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  Not Listed For Sale

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

  6271 Blissful St, Oakland, FL 34787

  6271 Blissful St, Oakland, FL 34787
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  $2,300,000 Pending

  • 4 Beds
  • 6 Baths
  • 3,902 Sq Ft

  1118 Sarah Mathews Dr, Oakland, FL 34787

  Under contract-accepting backup offers. Situated within the exclusive Grove community, this custom-built La Cascina residence by Pioneer Builders delivers refined luxury and exceptional craftsmanship throughout. Offering 4 bedrooms, 6 bathrooms, and 3,902 square feet of thoughtfully designed living space, this new construction home blends timeless design with modern comfort. The open-concept

  Alexis Anderson REGENCY REAL ESTATE LLC

  1118 Sarah Mathews Dr, Oakland, FL 34787
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  $950,000 Sold Sep 23, 2025

  100 Demens St, Oakland, FL 34760

  • 4 Beds
  • 3 Baths
  • 3,025 Sq Ft
  • Built 1999

  Last Sold Summary

  • 14% Below List Price
  • $314/SF
  • 100 Days On Market

  Current Estimated Value $946,861

  Last Listing Agent David Dorman CENTURY 21 CARIOTI

  100 Demens St, Oakland, FL 34760
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  Est $891,199 Not Listed For Sale

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

  1191 Wilder Oaks Way, Oakland, FL 34787

  1191 Wilder Oaks Way, Oakland, FL 34787
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  $461,995 New Construction

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

  13873 Easdale Aly, Oakland, FL 34787

  Under Construction. Toll Brothers New Construction at Winter Garden Horizonwest. Estimate completion July 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 and a private bath with dual

  Alicea Salgado ORLANDO TBI REALTY LLC

  13873 Easdale Aly, Oakland, FL 34787
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  $660,000 Sold Jun 12, 2025

  13672 Fresh Ivy St, Oakland, FL 34787

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

  Last Sold Summary

  • 8% Below List Price
  • $349/SF
  • 96 Days On Market

  Current Estimated Value $660,494

  Last Listing Agent Adrienne Escott PULTE REALTY OF NORTH FLORIDA LLC

  13672 Fresh Ivy St, Oakland, FL 34787

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