Oakland, FL Homes

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  $495,000 Sold Feb 18, 2026

  2755 Bobcat Chase Blvd, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,822 Sq Ft
  • Built 2020

  Last Sold Summary

  • 7% Below List Price
  • $272/SF
  • 203 Days On Market

  Current Estimated Value $482,183

  Last Listing Agent Tania Matthews KELLER WILLIAMS ELITE PARTNERS III REALTY

  2755 Bobcat Chase Blvd, Oakland, FL 34787
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  Est $811,978 Not Listed For Sale

  1210 Oak Fort Ln, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 2,247 Sq Ft
  • Built 2024

  1210 Oak Fort Ln, Oakland, FL 34787

  Last Sold Summary

  • 3% Below List Price
  • $372/SF
  • 121 Days On Market

  Last Sold Price $835,000

  Last Listing Agent Abigail Belchick OLYMPUS EXECUTIVE REALTY INC
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  /46

  $898,000

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

  9409 Emerald Berry Dr, Oakland, FL 34787

  Nestled on a premium homesite with no rear neighbors in the exclusive Summerlake Reserve enclave, this beautifully designed home blends comfort, functionality, and thoughtful upgrades throughout. The home offers 4 bedrooms, 3.5 bathrooms, a private office with barn doors, a spacious loft, and an extended covered lanai ideal for indoor-outdoor living. The gourmet kitchen is both elegant and

  Manuella Espinosa LA ROSA REALTY LLC

  9409 Emerald Berry Dr, Oakland, FL 34787
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  $865,000 Sold Jul 25, 2025

  70 Millholland St, Oakland, FL 34760

  • 5 Beds
  • 3 Baths
  • 2,534 Sq Ft
  • Built 2009

  Last Sold Summary

  • 15% Below List Price
  • $341/SF
  • 261 Days On Market

  Current Estimated Value $865,033

  Last Listing Agent Ashley Boyd BHHS FLORIDA REALTY

  70 Millholland St, Oakland, FL 34760
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  Est $537,491 Not Listed For Sale

  Unlisted Address

  • 3 Beds
  • 2.5 Baths
  • 2,148 Sq Ft
  • Built 2023

  Unlisted Address

  Last Sold Summary

  • 4% Below List Price
  • $260/SF

  Last Sold Price $558,040

  Last Listing Agent Ursula Garcia Moraes PRISTINE INTERNATIONAL REALTY LLC
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  /53

  $409,900 Pending

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

  8167 Mosaic Ln, Oakland, FL 34787

  Under contract-accepting backup offers. 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

  Simon Colak USCO CAPITAL GROUP

  8167 Mosaic Ln, Oakland, FL 34787
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  $395,000 Sold Sep 30, 2025

  13298 Pontoon Rd, Oakland, FL 34787

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

  Last Sold Summary

  • 6% Below List Price
  • $252/SF
  • 51 Days On Market

  Current Estimated Value $386,779

  Last Listing Agent Cindy Brads COLDWELL BANKER REALTY

  13298 Pontoon Rd, Oakland, FL 34787
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  Est $807,573 Not Listed For Sale

  1204 Oak Fort Ln, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 2,254 Sq Ft
  • Built 2024

  1204 Oak Fort Ln, Oakland, FL 34787

  Last Sold Summary

  • 3% Below List Price
  • $371/SF
  • 108 Days On Market

  Last Sold Price $836,225

  Last Listing Agent Abigail Belchick OLYMPUS EXECUTIVE REALTY INC
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  /29

  $390,000

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

  2120 Gopher Tortoise Terrace, Oakland, FL 34787

  Welcome to 2120 Gopher Tortoise Terrace in charming Oakland, Florida, a beautifully maintained 3 bedroom, 2.5 bathroom townhome that offers comfort, style, and an incredible opportunity for qualified buyers to assume the seller’s low 2.75 percent mortgage rate, subject to lender approval, potentially providing significant monthly savings compared to today’s interest rates. From the moment you

  Richard Aybar KELLER WILLIAMS ADVANTAGE III

  2120 Gopher Tortoise Terrace, Oakland, FL 34787
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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 $535,749

  Last Listing Agent Shannon Christian EXP REALTY LLC

  1757 Standing Rock Cir, Oakland, FL 34787
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  Not Listed For Sale

  6259 Blissful St, Oakland, FL 34787

  • 5 Beds
  • 3 Baths
  • 2,455 Sq Ft
  • Built 2024

  6259 Blissful St, Oakland, FL 34787

  Last Sold Summary

  • $197/SF
  • 0 Days On Market

  Last Sold Price $482,675

  Last Listing Agent Ben Goldstein LENNAR REALTY
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  /14

  $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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  $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 $414,749

  Last Listing Agent Jessica Stone CENTURY 21 CARIOTI

  709 Strihal Loop, Oakland, FL 34787
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  Est $408,323 Not Listed For Sale

  17005 Volume Aly, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,717 Sq Ft
  • Built 2020

  17005 Volume Aly, Oakland, FL 34787

  Last Sold Summary

  • 4% Below List Price
  • $248/SF
  • 39 Days On Market

  Last Sold Price $425,000

  Last Listing Agent Abby Anderson Hayes REAL BROKER, LLC
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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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  $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 $628,369

  Last Listing Agent Keith Packey RE/MAX TITANIUM GROUP

  410 E Gulley Ave, Oakland, FL 34760
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  Not Listed For Sale

  6301 Blissful St, Oakland, FL 34787

  • 5 Beds
  • 3 Baths
  • 3,043 Sq Ft
  • Built 2024

  6301 Blissful St, Oakland, FL 34787

  Last Sold Summary

  • $164/SF
  • 12 Days On Market

  Last Sold Price $497,880

  Last Listing Agent Ben Goldstein LENNAR REALTY
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  $2,130,760 New Construction

  • 5 Beds
  • 5.5 Baths
  • 3,992 Sq Ft

  1146 Prado Ln, Oakland, FL 34787

  Pre-Construction. To be built. Introducing the Hearth Stone Model by Davila Homes. Discover the perfect blend of modern luxury and everyday comfort in the Hearth Stone, a beautifully designed 3,992-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

  Heather Spirazza REGENCY REAL ESTATE LLC

  1146 Prado Ln, Oakland, 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

  Current Estimated Value $660,000

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

  16108 Honey Harvest St, Oakland, FL 34787
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  Not Listed For Sale

  6253 Blissful St, Oakland, FL 34787

  • 5 Beds
  • 3 Baths
  • 2,455 Sq Ft
  • Built 2024

  6253 Blissful St, Oakland, FL 34787

  Last Sold Summary

  • $197/SF
  • 35 Days On Market

  Last Sold Price $484,110

  Last Listing Agent Ben Goldstein LENNAR REALTY
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  $1,499,000

  • 6 Beds
  • 7.5 Baths
  • 5,614 Sq Ft

  620 N Tubb St, Oakland, FL 34760

  PRICE IMPROVEMENT! This exquisite gem has endless opportunities: a wellness center, wedding event venue, and Airbnb. Not looking to own a bed and breakfast? This would also make a fantastic stately residential home! This distinctive 19th-century Oakland Manor House sits on an .8-acre park-like setting in the charming town of Oakland. Carefully restored to preserve and enhance its original beauty

  Jennifer Wilson OAKSTRAND REALTY

  620 N Tubb St, Oakland, FL 34760
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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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  Not Listed For Sale

  6379 Blissful St, Oakland, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,023 Sq Ft
  • Built 2024

  6379 Blissful St, Oakland, FL 34787

  Last Sold Summary

  • $222/SF
  • 4 Days On Market

  Last Sold Price $449,999

  Last Listing Agent Ben Goldstein LENNAR REALTY
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  $594,000 New Construction

  • 4 Beds
  • 3 Baths
  • 2,143 Sq Ft

  12915 Westhaven Oak Dr, Oakland, FL 34787

  Under Construction. Toll Brothers New Construction at Winter Garden Horizon West. Estimate completion July 2026. Single family Bungalow. This home features a covered entry that leads to a spacious foyer and an expansive guest suite. The living area includes a dining room, with breakfast bar, great room, and access to the courtyard. The second-floor features 2 bedrooms and a master suite is

  DeVahn Powell ORLANDO TBI REALTY LLC

  12915 Westhaven Oak Dr, 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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  Not Listed For Sale

  6391 Blissful St, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,782 Sq Ft
  • Built 2024

  6391 Blissful St, Oakland, FL 34787

  Last Sold Summary

  • $241/SF
  • 4 Days On Market

  Last Sold Price $429,099

  Last Listing Agent Ben Goldstein LENNAR REALTY
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  /31

  $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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  $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 $382,468

  Last Listing Agent Sheri Loiacono WINDSOR REALTY GROUP INC

  121 W Oakland Ave, Oakland, FL 34760
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  Est $409,002 Not Listed For Sale

  15805 Tollington Aly, Oakland, FL 34787

  • 3 Beds
  • 3.5 Baths
  • 1,688 Sq Ft
  • Built 2024

  15805 Tollington Aly, Oakland, FL 34787

  Last Sold Summary

  • 4% Above List Price
  • $234/SF

  Last Sold Price $394,810

  Last Listing Agent Stellar Non-Member Agent FL_MFRMLS
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  $1,850,000 Pending

  • 4 Beds
  • 4 Baths
  • 3,616 Sq Ft

  15198 E Oakland Ave, Winter Garden, FL 34787

  Under contract-accepting backup offers. Welcome to this stunning farmhouse-style home nestled on a premium corner lot in one of the most sought-after communities near Historic Winter Garden. Thoughtfully designed and beautifully maintained, this home offers modern comfort with timeless charm. This is part of one of only 17 exclusive oversized luxury custom residences. Set in a thriving,

  Melody Niederst IAD FLORIDA LLC

  15198 E Oakland Ave, Winter Garden, 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 $414,119 Not Listed For Sale

  15811 Tollington Aly, Oakland, FL 34787

  • 3 Beds
  • 3 Baths
  • 1,691 Sq Ft
  • Built 2024

  15811 Tollington Aly, Oakland, FL 34787

  Last Sold Summary

  Last Listing Agent Carlinhos Fregonezi TALENT REALTY SOLUTIONS
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  $1,275,000

  • 4 Beds
  • 2.5 Baths
  • 2,710 Sq Ft

  1156 Civitas Way, Winter Garden, FL 34787

  Welcome to this exceptional 2022 RCB custom home in Oakland Park, one of Central Florida's most desirable communities. Ideally positioned on a premium corner lot with a view of Apopka Lake, from the second story balcony and no onward facing front neighbors, this residence embodies the front-porch lifestyle that defines Oakland Park's appeal. Located near the scenic West Orange Trail and minutes

  Heidi Pfeffer-Morgan DALTON WADE INC

  1156 Civitas Way, Winter Garden, 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 $835,159

  Last Listing Agent Sophia Ferrara COLDWELL BANKER REALTY

  413 MacChi Ave, Oakland, FL 34787
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  Est $561,673 Not Listed For Sale

  15153 Summer Harvest St, Oakland, FL 34787

  • 3 Beds
  • 4 Baths
  • 2,149 Sq Ft
  • Built 2024

  15153 Summer Harvest St, Oakland, FL 34787

  Last Sold Summary

  Last Listing Agent Carlinhos Fregonezi TALENT REALTY SOLUTIONS
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  $865,000

  • 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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  $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 $639,587

  Last Listing Agent Adrienne Escott PULTE REALTY OF NORTH FLORIDA LLC

  13672 Fresh Ivy St, Oakland, FL 34787
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  Est $415,620 Not Listed For Sale

  2315 Standing Rock Cir, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,663 Sq Ft
  • Built 2018

  2315 Standing Rock Cir, Oakland, FL 34787

  Last Sold Summary

  • 1% Below List Price
  • $253/SF
  • 35 Days On Market

  Last Sold Price $420,000

  Last Listing Agent Dana Gold RE/MAX
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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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  $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 $946,121

  Last Listing Agent David Dorman CENTURY 21 CARIOTI

  100 Demens St, Oakland, FL 34760

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