Oakland, FL Homes

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  /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 $421,701

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

  4576 Maple Waltz, Oakland, FL 34787
• 

  

  /2

  Est $435,265

  Not Listed For Sale

  13311 Pontoon Rd, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,814 Sq Ft
  • Built 2023

  13311 Pontoon Rd, Oakland, FL 34787

  Last Sold Summary

  • 12 Days On Market

  Last Listing Agent Ken Pozek REAL BROKER, LLC
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  /39

  $600,000

  $75K PRICE DROP Pending

  • 4 Beds
  • 2.5 Baths
  • 1,811 Sq Ft

  1119 Bobcat Chase Blvd, Oakland, FL 34760

  Prepare to be captivated by this enchanting 4-bedroom, 2.5-bath pool home, nestled amidst mature oaks that lend an air of timeless charm. Located in the idyllic community of Long Leaf, this home boasts the best lot in the neighborhood—complete with a cozy fire pit that begs for evening gatherings under the stars.Step inside to discover a kitchen adorned with tasteful taupe cabinetry,

  Erica Diaz HOMEVEST REALTY

  1119 Bobcat Chase Blvd, Oakland, FL 34760
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  /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 $581,571

  Last Listing Agent Ken Pozek REAL BROKER, LLC

  13732 Fresh Ivy St, Oakland, FL 34787
• 

  

  /2

  Est $1,027,027

  Not Listed For Sale

  210 Hammock Preserve Loop, Oakland, FL 34787

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

  210 Hammock Preserve Loop, Oakland, FL 34787

  Last Sold Summary

  • 47 Days On Market

  Last Listing Agent Matthew Sutton BERGER REALTY & INVESTMENTS
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  /80

  $739,000

  • 4 Beds
  • 3.5 Baths
  • 2,840 Sq Ft

  9152 Sonoma Coast Dr, Oakland, FL 34787

  Welcome to this beautifully maintained 4-bedroom, 3.5-bathroom home in the highly sought-after Winter Garden area! Perfectly positioned on a premium homesite, this home offers breathtaking water and conservation views with NO REAR NEIGHBORS, providing exceptional privacy and a peaceful backdrop. Designed for both comfort and functionality, the open floor plan features a private first-floor guest

  Yujie Jiang INTOP REALTY LLC

  9152 Sonoma Coast Dr, Oakland, 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 $421,672

  Last Listing Agent Deanna Meredith LUXE PROPERTIES LLC

  321 E Gulley Ave, Oakland, FL 34760
• 

  /2

  Est $473,520

  Not Listed For Sale

  16257 Prairie School Dr, Oakland, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,070 Sq Ft
  • Built 2021

  16257 Prairie School Dr, Oakland, FL 34787

  Last Sold Summary

  • 54 Days On Market

  Last Listing Agent Sue Vasquez FLORIDA REALTY RESULTS LLC
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  /4

  $508,990

  New Construction

  • 4 Beds
  • 3 Baths
  • 2,083 Sq Ft

  Newbury Plan at Serenade at Ovation - Bungalows, Oakland, FL 34787

  Discover the Newbury - our largest bungalow! This expansive home is designed to accommodate a variety of lifestyles with its 4 bedrooms, 3 bathrooms, a loft, and a 2-car garage. The extended kitchen is a standout feature, offering more cabinet space than you'll ever need, perfect for those who love to cook and entertain. Each bedroom in the Newbury is generously sized ensuring that everyone in

  Dream Finders Homes Builder

  14229 Lanyard Way Unit 36490206, Oakland, FL 34787
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  /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 $557,295

  Last Listing Agent Rema Perras CORCORAN PREMIER REALTY

  1507 Wild Sweetgrass Way, Oakland, FL 34760
• 

  /2

  Est $828,882

  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

  Last Listing Agent Jayme Taylor SAGE REALTY FLORIDA, INC.
• 

  

  /23

  $825,000

  • 4 Beds
  • 3.5 Baths
  • 3,085 Sq Ft

  1016 Catori Rd, Oakland, FL 34787

  Welcome to this beautifully designed 4-bedroom, 3.5-bath home offering stylish upgrades and exceptional indoor-outdoor living in the charming Town of Oakland. From the inviting covered entry and brick-paver driveway to the bright, open interior, every space has been thoughtfully designed for comfortable everyday living and effortless entertaining. The impressive kitchen features abundant

  Kelly Zannini HOMEVEST REALTY

  1016 Catori Rd, Oakland, FL 34787
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  /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 $690,405

  Last Listing Agent Anamaria Marquez KELLER WILLIAMS ELITE PARTNERS III REALTY

  2450 Standing Rock Cir, Oakland, FL 34787
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  /2

  Est $619,822

  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

  Last Listing Agent Ellie Hunter PULTE REALTY OF NORTH FLORIDA LLC
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  /34

  $379,990

  $10K PRICE DROP

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

  16931 Reseda Aly, Oakland, FL 34787

  JUST REDUCED - BEST PRICED TOWNHOME IN WATERLEIGH, WINTER GARDEN! This beautifully maintained 3-bedroom, 2.5-bath townhome features a bright open-concept floor plan designed for comfortable living and entertaining. The spacious kitchen offers granite countertops, stainless steel appliances, ample cabinet space, and A WHOLE-HOUSE WATER FILTRATION SYSTEM IS INCLUDED, providing added value and peace

  Leticia Mena MY REALTY GROUP, LLC.

  16931 Reseda Aly, Oakland, FL 34787
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  /2

  $535,000

  Sold Feb 24, 2026

  9029 Sonoma Coast Dr, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 2,014 Sq Ft
  • Built 2021

  Last Sold Summary

  • $266/SF
  • 64 Days On Market

  Current Estimated Value $537,639

  Last Listing Agent Abraham Mendez NONA LEGACY POWERED BY LA ROSA

  9029 Sonoma Coast Dr, Oakland, FL 34787
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  /2

  Est $619,056

  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

  Last Listing Agent Ellie Hunter PULTE REALTY OF NORTH FLORIDA LLC
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  /62

  $1,644,999

  $80K PRICE DROP

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

  1101 Eagles Pass Way, Oakland, FL 34787

  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 miles from the historic downtown

  Kevin Sullivan LAKESIDE REALTY WINDERMERE INC

  1101 Eagles Pass Way, Oakland, FL 34787
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  /2

  $954,900

  Sold Oct 09, 2025

  4637 Golden Birch Ave, Oakland, FL 34787

  • 5 Beds
  • 5 Baths
  • 4,272 Sq Ft
  • Built 2025

  Last Sold Summary

  • $224/SF
  • 0 Days On Market

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

  4637 Golden Birch Ave, Oakland, FL 34787
• 

  

  /20

  Est $662,476

  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

  Last Listing Agent Adrienne Escott PULTE REALTY OF NORTH FLORIDA LLC
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  /3

  $548,000

  New Construction $20K PRICE DROP Pending

  • 3 Beds
  • 2.5 Baths
  • 2,062 Sq Ft

  12911 Westhaven Oak Dr, Oakland, FL 34787

  Under Construction. Under Construction. Toll Brothers New Construction in Horizon West – Winter Garden | Estimated Completion Summer 2026. This home is conducive for entertaining with its open floor plan. This home features a covered entry that leads to an open and expansive living space, kitchen, and dining. The home features covered lanai and a spacious courtyard with access to the detached 2

  Dayene Grubert ORLANDO TBI REALTY LLC

  12911 Westhaven Oak Dr, Oakland, FL 34787
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  /2

  $694,490

  Sold Mar 16, 2026

  3064 Namaste Dr, Oakland, FL 34787

  • 5 Beds
  • 3.5 Baths
  • 3,385 Sq Ft
  • Built 2026

  Last Sold Summary

  • $205/SF

  Current Estimated Value $697,763

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

  3064 Namaste Dr, Oakland, FL 34787
• 

  /2

  Est $610,766

  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

  Last Listing Agent Adrienne Escott PULTE REALTY OF NORTH FLORIDA LLC
• 

  

  /54

  $567,900

  $8K PRICE INCREASE

  • 4 Beds
  • 2.5 Baths
  • 2,216 Sq Ft

  16495 Point Rock Dr, Oakland, FL 34787

  10 minutes from Disney World & theme parks!!! Built in 2023, this beautifully home offers 4 bedrooms, 2.5 bathrooms, a versatile flex room, and a rear-entry two-car garage in the desirable Waterleigh community. The open-concept layout features a spacious kitchen with stainless steel appliances, stone countertops, upgraded wood cabinetry, and a large center island overlooking the living and dining

  Kenia Aliaga LA ROSA REALTY ORLANDO LLC

  16495 Point Rock Dr, Oakland, FL 34787
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  /2

  $3,894,945

  Sold Mar 13, 2026

  517 N Pollard St, Winter Garden, FL 34787

  • 6 Beds
  • 7 Baths
  • 4,636 Sq Ft
  • Built 2026

  Last Sold Summary

  • 26% Above List Price
  • $840/SF

  Current Estimated Value $329,000

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

  517 N Pollard St, Winter Garden, FL 34787
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  /2

  Not Listed For Sale

  13133 Sunny Retreat Ln, Oakland, FL 34787

  • 3 Beds
  • 3.5 Baths
  • 2,808 Sq Ft
  • Built 2024

  13133 Sunny Retreat Ln, Oakland, FL 34787

  Last Sold Summary

  • 47 Days On Market

  Last Listing Agent Roo Klaers COLDWELL BANKER REALTY
• 

  

  /3

  $844,000

  New Construction $20K PRICE DROP Pending

  • 4 Beds
  • 3.5 Baths
  • 3,005 Sq Ft

  12916 Westhaven Oak Dr, Oakland, FL 34787

  Under Construction. Toll Brothers New Construction at Winter Garden Horizonwest. Estimate completion Summer 2026- Welcome home to this beautifully designed open-concept residence featuring a sought-after primary suite on the main level. The light-filled two-story foyer creates an impressive first impression and flows seamlessly into spacious living and entertaining areas. Thoughtful layout,

  Dayene Grubert ORLANDO TBI REALTY LLC

  12916 Westhaven Oak Dr, Oakland, FL 34787
• 

  /2

  $600,000

  Sold Apr 28, 2026

  2606 Bobcat Chase Blvd, Oakland, FL 34787

  • 4 Beds
  • 2.5 Baths
  • 2,473 Sq Ft
  • Built 2019

  Last Sold Summary

  • 10% Below List Price
  • $243/SF
  • 168 Days On Market

  Current Estimated Value $602,969

  Last Listing Agent Ashley Boyd BHHS FLORIDA REALTY

  2606 Bobcat Chase Blvd, Oakland, FL 34787
• 

  /2

  Est $625,162

  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

  Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE
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  /46

  $679,900

  $70K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 2,852 Sq Ft

  2017 Boss Hewett St, Oakland, FL 34787

  Virtually Staged. Enjoy single-level living in lakefront Hull Island in this meticulously maintained 2,852 sq ft home built in 2022, with owned rooftop solar that keeps utility costs well below the Florida norm for a home this size. Four bedrooms, four full baths, and a two-car garage, all just minutes from historic Winter Garden's shops, restaurants, and Saturday farmers market.All four

  Peter Biskup CHARLES RUTENBERG REALTY ORLANDO

  2017 Boss Hewett St, Oakland, FL 34787
• 

  /2

  $672,990

  Sold Aug 28, 2026

  3120 Namaste Dr, Oakland, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 3,147 Sq Ft
  • Built 2026

  Last Sold Summary

  • 2% Below List Price
  • $214/SF
  • 143 Days On Market

  Last Listing Agent Ben Goldstein LENNAR REALTY

  3120 Namaste Dr, Oakland, FL 34787
• 

  /2

  Est $655,211

  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

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

  

  /55

  $510,000

  Open Sat 1PM - 3PM $15K PRICE DROP

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

  2241 White Feather Loop, Oakland, FL 34787

  Welcome to Oakland Trails, one of Oakland’s most desirable communities! This beautifully maintained 3-bedroom, 2.5-bath home offers the perfect blend of comfort, style, and location. Built in 2018, the home features a bright, open-concept floor plan with spacious living areas, a modern kitchen, and plenty of room for both everyday living and entertaining.Step outside and enjoy all the

  Brynn Munro CORCORAN PREMIER REALTY

  2241 White Feather Loop, Oakland, FL 34787
• 

  /2

  $3,375,000

  Sold Jul 20, 2026

  510 Briley Ave, Oakland, FL 34787

  • 5 Beds
  • 7 Baths
  • 5,478 Sq Ft
  • Built 2025

  Last Sold Summary

  • 6% Below List Price
  • $616/SF
  • 0 Days On Market

  Current Estimated Value $2,313,667

  Last Listing Agent Alexis Anderson REGENCY REAL ESTATE LLC

  510 Briley Ave, Oakland, FL 34787
• 

  /2

  Est $587,848

  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

  Last Listing Agent Jasmine Martz OLYMPUS EXECUTIVE REALTY INC
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  /37

  $415,000

  New Construction $40K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,170 Sq Ft

  521 W Herriott Ave, Oakland, FL 34760

  PRICE REDUCED - Accepting Offers! The home has recently been entirely staged on the inside of the property - come tour this BEAUTY!NOTE: to add extra storage, a (large shed) can be added onto the property within the purchase of the home. NO HOA!Welcome to this brand-new construction home in the heart of Oakland! This thoughtfully designed 3-bedroom, 2-bathroom residence offers

  Adam DeVito REAL BROKER, LLC

  521 W Herriott Ave, Oakland, FL 34760
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  /2

  $525,000

  Sold Oct 22, 2025

  233 Largovista Dr, Oakland, FL 34787

  • 4 Beds
  • 2 Baths
  • 2,176 Sq Ft
  • Built 2004

  Last Sold Summary

  • 2% Below List Price
  • $241/SF
  • 93 Days On Market

  Current Estimated Value $515,190

  Last Listing Agent Rachael Segarra EXP REALTY LLC

  233 Largovista Dr, Oakland, FL 34787
• 

  /2

  Est $425,275

  Not Listed For Sale

  9109 Legado Dr, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,687 Sq Ft
  • Built 2020

  9109 Legado Dr, Oakland, FL 34787

  Last Sold Summary

  • 126 Days On Market

  Last Listing Agent Jay Stewart SOUTHERN REALTY GROUP LLC
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  /63

  $3,495,000

  New Construction Pending

  • 5 Beds
  • 5.5 Baths
  • 5,001 Sq Ft

  402 N Pollard St, Oakland, FL 34787

  Luxury new construction model home by Element Home Builders located in the exclusive custom home community of Briley Farm in Oakland. This thoughtfully designed residence offers approximately 4,900 square feet of elevated living space with 5 bedrooms, 5.5 bathrooms, and a spacious 3-car garage. Designed for both everyday living and entertaining, the home features soaring ceilings, expansive

  Carolina Dumit CORCORAN PREMIER REALTY

  402 N Pollard St, Oakland, FL 34787
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  /2

  $500,000

  Sold Aug 14, 2026

  1270 Stationside Dr, Oakland, FL 34787

  • 4 Beds
  • 2 Baths
  • 2,046 Sq Ft
  • Built 2002

  Last Sold Summary

  • 4% Below List Price
  • $244/SF
  • 124 Days On Market

  Current Estimated Value $508,810

  Last Listing Agent Ky Lam HOME INVEST REALTY INC

  1270 Stationside Dr, Oakland, FL 34787

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