Oakland, FL Homes

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  /2

  $607,690

  Sold Mar 27, 2026

  3088 Namaste Dr, Oakland, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 2,911 Sq Ft
  • Built 2026

  Last Sold Summary

  • 5% Below List Price
  • $209/SF
  • 20 Days On Market

  Current Estimated Value $611,903

  Last Listing Agent Ben Goldstein LENNAR REALTY

  3088 Namaste Dr, Oakland, FL 34787
• 

  

  /2

  Est $605,096

  Not Listed For Sale

  12891 Westhaven Oak Dr, Oakland, FL 34787

  • 3 Beds
  • 3.5 Baths
  • 1,908 Sq Ft
  • Built 2024

  12891 Westhaven Oak Dr, Oakland, FL 34787

  Last Sold Summary

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

  

  

  /18

  $2,380,160

  New Construction $142K PRICE INCREASE

  • 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
• 

  

  /2

  $1,990,000

  Sold Aug 12, 2026

  9014 Morgana Ct, Oakland, FL 34787

  • 5 Beds
  • 4.5 Baths
  • 4,436 Sq Ft
  • Built 2022

  Last Sold Summary

  • 15% Below List Price
  • $449/SF
  • 163 Days On Market

  Current Estimated Value $1,998,976

  Last Listing Agent Jennifer Wemert WEMERT GROUP REALTY LLC

  9014 Morgana Ct, Oakland, FL 34787
• 

  

  

  /21

  Est $425,666

  Not Listed For Sale

  2261 Standing Rock Cir, Oakland, FL 34787

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

  2261 Standing Rock Cir, Oakland, FL 34787

  Last Sold Summary

  • 136 Days On Market

  Last Listing Agent Fernando Orsini CT HOMES REALTY CORPORATION
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  /3

  $411,995

  New Construction $50K PRICE DROP Pending

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

  13873 Easdale Aly, Oakland, FL 34787

  Under Construction. Under Construction. Toll Brothers New Construction in Horizon West – Winter Garden | Estimated Completion Summer 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

  Dayene Grubert ORLANDO TBI REALTY LLC

  13873 Easdale Aly, Oakland, FL 34787
• 

  /2

  $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
• 

  /2

  Est $666,052

  Not Listed For Sale

  2157 Bay Line Rd, Oakland, FL 34787

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

  2157 Bay Line Rd, Oakland, FL 34787

  Last Sold Summary

  • 69 Days On Market

  Last Listing Agent Jamie Stolinas Crame CENTURY 21 CARIOTI
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  /33

  $512,490

  New Construction Pending

  • 4 Beds
  • 3 Baths
  • 2,366 Sq Ft

  5485 Oasis Loop, Oakland, FL 34787

  Under Construction. Check out this amazing new single-story Next Gen®! The McCartney features a private suite with its own entrance, living area, kitchenette, bedroom, bathroom and laundry, perfect for multigenerational households. The main home is host to an inviting open-concept layout with easy access to a covered patio for seamless indoor-outdoor living. Two secondary bedrooms are located off

  Ben Goldstein LENNAR REALTY

  5485 Oasis Loop, Oakland, FL 34787
• 

  /2

  $975,000

  Sold Jul 01, 2026

  9549 Bolero Rd, Oakland, FL 34787

  • 5 Beds
  • 3.5 Baths
  • 3,910 Sq Ft
  • Built 2021

  Last Sold Summary

  • 6% Below List Price
  • $249/SF
  • 255 Days On Market

  Current Estimated Value $927,374

  Last Listing Agent Jacquelyn Voigt KELLER WILLIAMS REALTY AT THE LAKES

  9549 Bolero Rd, Oakland, FL 34787
• 

  /2

  Est $573,294

  Not Listed For Sale

  2050 Standing Rock Cir, Oakland, FL 34787

  • 4 Beds
  • 2.5 Baths
  • 2,596 Sq Ft
  • Built 2019

  2050 Standing Rock Cir, Oakland, FL 34787

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Scott Swinson, Jr CHARLES RUTENBERG REALTY ORLANDO
• 

  

  /25

  $468,000

  $22K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,720 Sq Ft

  14099 Lochend Way, Oakland, FL 34787

  Welcome to luxury living at its finest! Nestled in the prestigious West Haven at Ovation community in Winter Garden, this almost brand new 3-bedroom, 2.5-bathroom townhome is the epitome of modern elegance. As you step inside, you're greeted by an inviting open floor plan boasting an abundance of natural light and high-end finishes throughout. The spacious living area is perfect for entertaining

  Anahi C Rosario INTERNATIONAL REAL ESTATE LLC

  14099 Lochend Way, Oakland, FL 34787
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  /2

  $599,990

  Sold May 28, 2026

  2982 Good Vibes Way, Oakland, FL 34787

  • 5 Beds
  • 4 Baths
  • 3,011 Sq Ft
  • Built 2025

  Last Sold Summary

  • 10% Below List Price
  • $199/SF
  • 57 Days On Market

  Current Estimated Value $602,230

  Last Listing Agent Ben Goldstein LENNAR REALTY

  2982 Good Vibes Way, Oakland, FL 34787
• 

  /2

  Est $615,452

  Not Listed For Sale

  2390 Standing Rock Cir, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 2,060 Sq Ft
  • Built 2018

  2390 Standing Rock Cir, Oakland, FL 34787

  Last Sold Summary

  • 39 Days On Market

  Last Listing Agent Francisco Chavez, Jr DENIZ REALTY PARTNERS LLC
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  /7

  $1,195,000

  • Land
  • 35,719 Sq Ft
  • $1,457,317 per Acre

  552 Walker St, Oakland, FL 34760

  Discover an exceptional opportunity to build a custom lakefront residence on Lot 45 in Briley Farm Phase 1B. Located at 552 Walker Street in Oakland, this approximately 0.82-acre homesite offers beautiful Lake Apopka views, direct lake frontage and generous space to create a personalized retreat exclusively with Element Home Builders. With no predetermined floor plan, buyers can collaborate with

  Carolina Dumit CORCORAN PREMIER REALTY

  552 Walker St, Oakland, FL 34760
• 

  /2

  $1,525,000

  Sold Apr 06, 2026

  15722 E Oakland Ave, Oakland, FL 34760

  • 3 Beds
  • 2 Baths
  • 3,340 Sq Ft
  • Built 1952

  Last Sold Summary

  • 2% Above List Price
  • $457/SF
  • 4 Days On Market

  Current Estimated Value $1,372,304

  Last Listing Agent Matt Erickson RE/MAX PRIME PROPERTIES

  15722 E Oakland Ave, Oakland, FL 34760
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  /2

  Est $508,890

  Not Listed For Sale

  1763 White Feather Loop, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 2,152 Sq Ft
  • Built 2017

  1763 White Feather Loop, Oakland, FL 34787

  Last Sold Summary

  • 51 Days On Market

  Last Listing Agent Kim Byerly THE REAL ESTATE COLLECTION LLC
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  /24

  $602,990

  New Construction $5K PRICE DROP Pending

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

  3160 Namaste Dr, Oakland, FL 34787

  Under Construction. 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 versatile needs and three bedrooms,

  Ben Goldstein LENNAR REALTY

  3160 Namaste Dr, Oakland, FL 34787
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  /2

  $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 $958,459

  Last Listing Agent David Dorman CENTURY 21 CARIOTI

  100 Demens St, Oakland, FL 34760
• 

  /2

  Est $443,809

  Not Listed For Sale

  2405 Standing Rock Cir, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,753 Sq Ft
  • Built 2018

  2405 Standing Rock Cir, Oakland, FL 34787

  Last Sold Summary

  • 52 Days On Market

  Last Listing Agent Dan Grieb KELLER WILLIAMS REALTY AT THE PARKS
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  /5

  $595,000

  • Land
  • 22,651 Sq Ft
  • $1,144,231 per Acre

  523 Walker St, Oakland, FL 34787

  Build your custom residence on Lot 21 in Briley Farm Phase 1B, a thoughtfully designed community in Oakland, Florida. Located at 523 Walker Street, this approximately 0.52-acre interior homesite offers the opportunity to create a custom home exclusively with Element Home Builders, with no predetermined floor plan. Enjoy a desirable location near charming downtown Winter Garden, the West Orange

  Carolina Dumit CORCORAN PREMIER REALTY

  523 Walker St, Oakland, FL 34787
• 

  /2

  $605,000

  Sold Aug 28, 2026

  529 Johns Landing Way, Oakland, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,650 Sq Ft
  • Built 2004

  Last Sold Summary

  • 5% Below List Price
  • $228/SF
  • 32 Days On Market

  Current Estimated Value $616,116

  Last Listing Agent Denise Pellegrino REAL BROKER, LLC

  529 Johns Landing Way, Oakland, FL 34787
• 

  /2

  Est $590,369

  Not Listed For Sale

  1219 Foltz Loop, Oakland, FL 34787

  • 3 Beds
  • 2 Baths
  • 1,860 Sq Ft
  • Built 2022

  1219 Foltz Loop, Oakland, FL 34787

  Last Sold Summary

  • 27 Days On Market

  Last Listing Agent Ashley Boyd BHHS FLORIDA REALTY
• 

  /2

  $541,000

  New Construction

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

  13031 Tollcross Way, Oakland, FL 34787

  Superior contemporary design. The Liston's welcoming covered porch and entry open immediately onto the expansive great room, with views to the lovely dining room and desirable large covered lanai beyond. The well-equipped gourmet kitchen is enhanced by a large center island with breakfast bar, plenty of counter and cabinet space, and generous walk-in pantry. The gorgeous primary bedroom suite is

  Toll Brothers, Inc. Builder

  13031 Tollcross Way, Oakland, FL 34787
• 

  /2

  $505,000

  Sold Aug 28, 2026

  2065 White Feather Loop, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 2,089 Sq Ft
  • Built 2019

  Last Sold Summary

  • 10% Below List Price
  • $242/SF
  • 185 Days On Market

  Current Estimated Value $532,492

  Last Listing Agent Denis Bochkov PINK MIAMI REAL ESTATE

  2065 White Feather Loop, Oakland, FL 34787
• 

  /2

  Est $630,309

  Not Listed For Sale

  2214 Bay Line Rd, Oakland, FL 34787

  • 4 Beds
  • 2 Baths
  • 2,278 Sq Ft
  • Built 2020

  2214 Bay Line Rd, Oakland, FL 34787

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Kelly Zannini HOMEVEST REALTY
• 

  /2

  $605,455

  New Construction Pending

  • 4 Beds
  • 3.5 Baths
  • 2,520 Sq Ft

  17144 Ingram Hills Aly, Oakland, FL 34787

  One or more photo(s) has been virtually staged. Pre-Construction. To be built. Sample Image The Carter offers a well-designed living space with 3 bedrooms, 3.5 baths, and a 2-car garage. The open-concept layout features a spacious family room, a gourmet kitchen with a large island and pantry, and a dining area. The primary suite includes a luxurious bath and walk-in closet, while additional

  Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

  17144 Ingram Hills Aly, Oakland, FL 34787
• 

  /2

  $460,000

  Sold Sep 23, 2025

  17055 Wynford Ln, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 2,345 Sq Ft
  • Built 2021

  Last Sold Summary

  • 16% Below List Price
  • $196/SF
  • 160 Days On Market

  Current Estimated Value $514,103

  Last Listing Agent Lori Lucente-Nelson RE/MAX PRIME PROPERTIES

  17055 Wynford Ln, Oakland, FL 34787
• 

  /2

  Est $1,611,320

  Not Listed For Sale

  625 Cheekwood Aly, Winter Garden, FL 34787

  • 6 Beds
  • 4.5 Baths
  • 3,796 Sq Ft
  • Built 2022

  625 Cheekwood Aly, Winter Garden, FL 34787

  Last Sold Summary

  • 17 Days On Market

  Last Listing Agent Ashley Boyd BHHS FLORIDA REALTY
• 

  

  /10

  $3,200,000

  • 41 Beds
  • 75 Baths
  • 17,021 Sq Ft

  15992 W Colonial Dr, Oakland, FL 34787

  15992 W Colonial Dr, Oakland, FL – 32-Unit Income Producing Multifamily OpportunityExceptional opportunity to acquire a 32-unit income-producing asset in the heart of West Orange County, ideally positioned along the high-visibility W Colonial Dr / SR-50 corridor in the Town of Oakland.Situated on approximately 2.15 acres, this unique property offers a diverse mix of duplex-style

  Kyler Moreland REMAX SUNSTATE REALTY

  15992 W Colonial Dr, Oakland, FL 34787
• 

  /2

  $580,109

  Sold Dec 23, 2025

  17597 Japonica Bloom Dr, Oakland, FL 34787

  • 3 Beds
  • 2 Baths
  • 1,791 Sq Ft
  • Built 2025

  Last Sold Summary

  • $324/SF

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

  17597 Japonica Bloom Dr, Oakland, FL 34787
• 

  /2

  Est $464,293

  Not Listed For Sale

  14018 Scarlet Aster Aly, Oakland, FL 34787

  • 2 Beds
  • 2.5 Baths
  • 1,785 Sq Ft
  • Built 2024

  14018 Scarlet Aster Aly, Oakland, FL 34787

  Last Sold Summary

  • 115 Days On Market

  Last Listing Agent Abigail Belchick OLYMPUS EXECUTIVE REALTY INC
• 

  

  /23

  $575,000

  $75K PRICE INCREASE

  • Land
  • 19,602 Sq Ft
  • $1,277,778 per Acre

  514 N Pollard St, Winter Garden, FL 34787

  Briley Farm, Central Florida’s newest custom home community, sits on 111 acres of lush landscape in Oakland, Florida. Here, you’ll have the opportunity to build your dream custom home with Pioneer Builders on a .45-acre corner lot. Pioneer Builders is renowned for their commitment to craftsmanship, attention to detail, and creating homes that reflect each client’s unique style. Every residence is

  Alexis Anderson REGENCY REAL ESTATE LLC

  514 N Pollard St, Winter Garden, FL 34787
• 

  /2

  $1,040,000

  Sold Jul 20, 2026

  1219 Saddleback Dr, Winter Garden, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 2,667 Sq Ft
  • Built 2022

  Last Sold Summary

  • 1% Below List Price
  • $390/SF
  • 13 Days On Market

  Current Estimated Value $1,035,802

  Last Listing Agent Lynette Piontek CENTRAL FLORIDA PRIME REAL ESTATE LLC

  1219 Saddleback Dr, Winter Garden, FL 34787
• 

  

  /11

  Est $892,259

  Not Listed For Sale

  13259 Tollcross Way, Oakland, FL 34787

  • 5 Beds
  • 4 Baths
  • 3,318 Sq Ft
  • Built 2025

  13259 Tollcross Way, Oakland, FL 34787

  Last Sold Summary

  • 25 Days On Market

  Last Listing Agent Dayene Grubert ORLANDO TBI REALTY LLC
• 

  

  /35

  $485,000

  $40K PRICE DROP Under Contract

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

  12308 Bracco St, Oakland, FL 34787

  Under contract-accepting backup offers. Beautiful and nearly new home in the quiet and friendly Highland Ridge community. This home was built only two years ago and is in perfect condition, offering over 2,114 sq. ft. of air-conditioned space. The layout is open and bright, with a modern kitchen that overlooks the large living and dining areas, perfect for family time and hosting friends. A big

  Diller de Abreu Junior ELITE INTERNATIONAL REALTY INC

  12308 Bracco St, Oakland, FL 34787
• 

  /2

  $860,990

  Sold Apr 20, 2026

  4628 Golden Birch Ave, Oakland, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,379 Sq Ft
  • Built 2026

  Last Sold Summary

  • $362/SF

  Current Estimated Value $861,844

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

  4628 Golden Birch Ave, Oakland, FL 34787
• 

  /2

  Est $437,513

  Not Listed For Sale

  9030 Wading Walk Ln, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,814 Sq Ft
  • Built 2020

  9030 Wading Walk Ln, Oakland, FL 34787

  Last Sold Summary

  • 23 Days On Market

  Last Listing Agent Brooke Barlow REAL ESTATE HOUSE FL INC
• 

  

  /30

  $653,118

  New Construction $51K PRICE DROP

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

  14780 Field Daisy Dr, Oakland, FL 34787

  Welcome to the Baldwin at 14780 Field Daisy Drive in Harvest at Ovation! Enter the charming oasis within this thoughtfully designed bungalow floor plan that offers 2,441 sq. ft. of inviting living space. Just past the foyer and formal dining room, the great room opens to the designer kitchen for an easy flow that is perfect for entertaining and relaxation. A first-floor bedroom with a full bath

  Taylor Morrison Builder

  14780 Field Daisy Dr, Oakland, FL 34787
• 

  /2

  $88,000

  Sold Apr 29, 2026

  406 W Herriott Ave, Oakland, FL 34760

  • Land
  • 3,920 Sq Ft
  • $977,778 per Acre

  Last Sold Summary

  • 9% Below List Price
  • 36 Days On Market

  Current Estimated Value $89,058

  Last Listing Agent Migdalia Ramos V PROPERTIES INC

  406 W Herriott Ave, Oakland, FL 34760

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