Oakland, FL Homes

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  /2

  Est $1,669,247

  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

  Last Listing Agent Ronald Ziolkowski RE/MAX PRIME PROPERTIES
• 

  

  /2

  $510,880

  New Construction Pending

  • 3 Beds
  • 2 Baths
  • 1,772 Sq Ft

  Oakland, FL 34787

  One or more photo(s) has been virtually staged. Pre-Construction. To be built. The Amelia floor plan offers the ease of one-story living with a smart and stylish layout featuring three bedrooms, two bathrooms, and a two-car garage. A spacious great room flows effortlessly into the dining and kitchen areas, making entertaining and everyday living a breeze. The private primary suite is tucked away

  Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

  Oakland, FL 34787
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  /2

  $1,654,248

  Sold Apr 14, 2026

  360 Jefferson St, Oakland, FL 34760

  • 4 Beds
  • 4.5 Baths
  • 3,482 Sq Ft
  • Built 2026

  Last Sold Summary

  • $475/SF
  • 0 Days On Market

  Current Estimated Value $1,332,418

  Last Listing Agent Alexis Anderson REGENCY REAL ESTATE LLC

  360 Jefferson St, Oakland, FL 34760
• 

  

  /2

  Est $523,159

  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
• 

  

  

  /24

  $859,500

  • 5 Beds
  • 3.5 Baths
  • 3,631 Sq Ft

  5128 Breezy Acres St, Oakland, FL 34787

  Welcome to your dream home in the highly desirable community of Wincey Groves! This stunning 5-bedroom, 3.5-bath single-family residence, built in 2021, boasts contemporary design and upscale finishes throughout. Enjoy soaring 10-foot ceilings with elegant fascia, and a chef-inspired modern kitchen featuring luxurious quartz countertops and top-of-the-line stainless steel

  Karla Rodriguez EXP REALTY LLC

  5128 Breezy Acres St, Oakland, FL 34787
• 

  /2

  $940,000

  Sold Jun 05, 2026

  8911 Sonoma Coast Dr, Oakland, FL 34787

  • 5 Beds
  • 4.5 Baths
  • 3,227 Sq Ft
  • Built 2021

  Last Sold Summary

  • 1% Below List Price
  • $291/SF
  • 3 Days On Market

  Current Estimated Value $932,510

  Last Listing Agent John Silva JOHN SILVA REALTY & ASSOCIATES

  8911 Sonoma Coast Dr, Oakland, FL 34787
• 

  /2

  Est $645,323

  Not Listed For Sale

  15030 Summer Harvest St, Oakland, FL 34787

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

  15030 Summer Harvest St, Oakland, FL 34787

  Last Sold Summary

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

  

  /15

  $850,000

  New Construction

  • 4 Beds
  • 4 Baths
  • 3,186 Sq Ft

  166 Hammock Preserve Loop, Oakland, FL 34787

  Under Construction. Rare opportunity to finish a custom AR Homes "Carrabelle" build exactly the way you want it - priced to reflect its current stage. 166 Hammock Preserve Loop is roughly three-quarters complete: framing, block construction, roof, windows, and drywall are in, and the home is currently paused at that stage. What's left is the fun part - flooring, cabinetry, fixtures, paint, and

  AJ Lash GOYAL & DECOSTER REALTY

  166 Hammock Preserve Loop, Oakland, FL 34787
• 

  /2

  $1,949,000

  Sold Jun 02, 2026

  511 Briley Ave, Oakland, FL 34787

  • 5 Beds
  • 4.5 Baths
  • 3,862 Sq Ft
  • Built 2026

  Last Sold Summary

  • $505/SF
  • 56 Days On Market

  Last Listing Agent Carolina Dumit CORCORAN PREMIER REALTY

  511 Briley Ave, Oakland, FL 34787
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  /2

  Est $489,896

  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

  Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE
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  /70

  $1,400,000

  • 4 Beds
  • 3.5 Baths
  • 3,562 Sq Ft

  1112 Hull Island Dr, Oakland, FL 34787

  Welcome to this extraordinary custom lakefront estate offering breathtaking views of Lake Apopka and the ultimate Florida waterfront lifestyle. Designed with luxury and functionality in mind, this one-of-a-kind home showcases premium upgrades, exceptional craftsmanship, and direct lake access. The heart of the home is a chef-inspired kitchen featuring a natural gas cooktop, double ovens,

  Kelly Zannini HOMEVEST REALTY

  1112 Hull Island Dr, Oakland, FL 34787
• 

  /2

  $828,296

  Sold Sep 29, 2025

  16146 Point Rock Dr, Oakland, FL 34787

  • 5 Beds
  • 4.5 Baths
  • 3,225 Sq Ft
  • Built 2025

  Last Sold Summary

  • 2% Below List Price
  • $257/SF
  • 48 Days On Market

  Current Estimated Value $873,000

  Last Listing Agent Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

  16146 Point Rock Dr, Oakland, FL 34787
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  /2

  Est $354,052

  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

  Last Listing Agent Cristina Ireland THE SIMON SIMAAN GROUP
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  /83

  $546,990

  $3K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,031 Sq Ft

  14099 Frasier St, Oakland, FL 34787

  Welcome to this bright and inviting 3 BEDROOM and 2 1/2 BATHROOM home in the Highland Ridge community of Winter Garden.It feels open and comfortable the moment you walk in.The beautiful CERAMIC TILE throughout the first floor already gives the perspective of the open floor plan. Right off the entry is a flexible room currently used as a HOME OFFICE — a great spot for work or study

  Fernanda Trein, LLC CHARLES RUTENBERG REALTY ORLANDO

  14099 Frasier St, Oakland, FL 34787
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  /2

  $633,000

  Sold May 05, 2026

  847 Cura Ct, Oakland, FL 34787

  • 4 Beds
  • 3 Baths
  • 3,000 Sq Ft
  • Built 2002

  Last Sold Summary

  • 2% Below List Price
  • $211/SF
  • 104 Days On Market

  Current Estimated Value $628,418

  Last Listing Agent Jose Rojo URBAN-O REAL ESTATE SOLUTIONS

  847 Cura Ct, Oakland, FL 34787
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  /2

  Est $617,221

  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

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

  /2

  $699,970

  New Construction Pending

  • 5 Beds
  • 4.5 Baths
  • 3,122 Sq Ft

  17162 Ingram Hills Aly, Oakland, FL 34787

  One or more photo(s) has been virtually staged. Pre-Construction. To be built. SAMPLE IMAGE PRE DESIGN CENTER PRICING The Carter at Hamlin Meadows: Luxury Living with Unmatched Privacy. Discover the perfect blend of elegance and functionality in the Carter model by Dream Finders Homes. This impressive 2,515 sq. ft. residence features 4 bedrooms, 3.5 bathrooms, and a rear-load 2-car garage,

  Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

  17162 Ingram Hills Aly, Oakland, FL 34787
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  /2

  $389,000

  Sold Dec 23, 2025

  2218 Gopher Tortoise Terrace, Oakland, FL 34760

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

  Last Sold Summary

  • $264/SF
  • 36 Days On Market

  Last Listing Agent Chelsea Eckert LISA REALTY PARTNERS

  2218 Gopher Tortoise Terrace, Oakland, FL 34760
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  /2

  Est $834,590

  Not Listed For Sale

  1073 Sadler Oaks Way, Winter Garden, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 2,246 Sq Ft
  • Built 2023

  1073 Sadler Oaks Way, Winter Garden, FL 34787

  Last Sold Summary

  • 28 Days On Market

  Last Listing Agent Ken Pozek REAL BROKER, LLC
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  /2

  $1,675,000

  New Construction

  • 5 Beds
  • 5 Baths
  • 4,819 Sq Ft

  166 Hammock Preserve Loop, Oakland, FL 34787

  166 Hammock Preserve Loop, Oakland, FL 34787
• 

  /2

  $684,000

  Sold Aug 03, 2026

  2022 Boss Hewett St, Oakland, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,281 Sq Ft
  • Built 2022

  Last Sold Summary

  • 1% Above List Price
  • $300/SF
  • 13 Days On Market

  Current Estimated Value $670,120

  Last Listing Agent Brian Cirillo BALDWIN PARK REALTY LLC

  2022 Boss Hewett St, Oakland, FL 34787
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  /2

  Est $479,911

  Not Listed For Sale

  6672 Juneberry Way, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,846 Sq Ft
  • Built 2025

  6672 Juneberry Way, Oakland, FL 34787

  Last Sold Summary

  • 155 Days On Market

  Last Listing Agent Adam Schott DRB GROUP REALTY, LLC
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  /67

  $2,495,000

  New Construction Open Sat 11AM - 4PM $100K PRICE DROP

  • 5 Beds
  • 8 Baths
  • 4,433 Sq Ft

  1134 Prado Ln, Winter Garden, FL 34787

  Nestled beneath century-old heritage oaks in one of Oakland's most coveted addresses, this stunning 4,433 square foot Citrus floorplan by Element Home Builders delivers an extraordinary standard of luxury estate living. Every detail speaks to a level of craftsmanship and thoughtfulness that simply cannot be replicated.Five generously sized bedrooms, each with its own private ensuite bath,

  Alexis Anderson REGENCY REAL ESTATE LLC

  1134 Prado Ln, Winter Garden, FL 34787
• 

  /2

  $2,050,000

  Sold Apr 09, 2026

  9008 Morgana Ct, Oakland, FL 34787

  • 5 Beds
  • 5 Baths
  • 4,934 Sq Ft
  • Built 2022

  Last Sold Summary

  • 7% Below List Price
  • $415/SF
  • 76 Days On Market

  Current Estimated Value $2,047,568

  Last Listing Agent Bent Danholm DANHOLM COLLECTION

  9008 Morgana Ct, Oakland, FL 34787
• 

  /2

  Est $519,648

  Not Listed For Sale

  14015 Lochend Way, Oakland, FL 34787

  • 4 Beds
  • 3 Baths
  • 1,996 Sq Ft
  • Built 2024

  14015 Lochend Way, Oakland, FL 34787

  Last Sold Summary

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

  

  /30

  $445,000

  • 4 Beds
  • 2.5 Baths
  • 1,992 Sq Ft

  10660 Words Dr, Oakland, FL 34787

  Welcome to 10660 Words Drive, Winter Garden, FL, a beautifully maintained home featuring a spacious and thoughtfully designed floor plan for comfortable everyday living.The open-concept layout includes a bright living area, a modern kitchen with ample cabinetry and countertop space, a dining area, and generously sized bedrooms that provide comfort and privacy.The primary suite serves as a

  Ashley Porto GLASSTONE GROUP INC

  10660 Words Dr, Oakland, FL 34787
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  /2

  $645,000

  Sold Feb 28, 2026

  2139 Bay Line Rd, Oakland, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,281 Sq Ft
  • Built 2020

  Last Sold Summary

  • 1% Below List Price
  • $283/SF
  • 17 Days On Market

  Current Estimated Value $655,491

  Last Listing Agent Ryan Barnett MARKET CONNECT REALTY LLC

  2139 Bay Line Rd, Oakland, FL 34787
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  /2

  Not Listed For Sale

  13437 Princess St, Oakland, FL 34787

  • 2 Beds
  • 2 Baths
  • 1,579 Sq Ft
  • Built 2024

  13437 Princess St, Oakland, FL 34787

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Ellie Hunter PULTE REALTY OF NORTH FLORIDA LLC
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  /17

  $2,310,600

  New Construction $180K PRICE INCREASE

  • 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
• 

  /2

  $850,000

  Sold Apr 06, 2026

  501 E Oakland Ave, Winter Garden, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 3,448 Sq Ft
  • Built 2007

  Last Sold Summary

  • 11% Below List Price
  • $247/SF
  • 104 Days On Market

  Current Estimated Value $856,266

  Last Listing Agent Erica Diaz HOMEVEST REALTY

  501 E Oakland Ave, Winter Garden, FL 34787
• 

  /2

  Not Listed For Sale

  17971 Hither Hills Cir, Winter Garden, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,097 Sq Ft
  • Built 2022

  17971 Hither Hills Cir, Winter Garden, FL 34787

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Jay Love DR HORTON REALTY OF CENTRAL FLORIDA LLC
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  /34

  $350,000

  $15K PRICE DROP Under Contract

  • 2 Beds
  • 2.5 Baths
  • 1,497 Sq Ft

  2117 Gopher Tortoise Terrace, Oakland, FL 34787

  Under contract-accepting backup offers. PRICE Improvement and this home can be purchased with NO INCOME VERIFICATION! Be sure to ask about the details! Skip the projects, this 2020 built home is ready for you! This open-concept layout creates a bright and inviting space perfect for entertaining.The kitchen, where matching marble countertops and cabinetry create a clean and cohesive look. A

  Mary Herrod De Boer SERHANT

  2117 Gopher Tortoise Terrace, Oakland, FL 34787
• 

  /2

  $530,000

  Sold Oct 15, 2025

  8001 Sayings Dr, Winter Garden, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 2,552 Sq Ft
  • Built 2022

  Last Sold Summary

  • 8% Below List Price
  • $208/SF
  • 66 Days On Market

  Current Estimated Value $534,587

  Last Listing Agent Shanta Navarro KELLER WILLIAMS ADVANTAGE III

  8001 Sayings Dr, Winter Garden, FL 34787
• 

  /2

  Est $849,260

  Not Listed For Sale

  14384 Wabasso Loop, Oakland, FL 34787

  • 5 Beds
  • 3 Baths
  • 3,562 Sq Ft
  • Built 2022

  14384 Wabasso Loop, Oakland, FL 34787

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Viviane Rocha WRA BUSINESS & REAL ESTATE
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  /62

  $1,250,000

  $400K PRICE DROP

  • 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
• 

  /2

  $599,200

  Sold Sep 25, 2025

  4727 Forest Haven Way, Oakland, FL 34787

  • 3 Beds
  • 2 Baths
  • 1,935 Sq Ft
  • Built 2025

  Last Sold Summary

  • $310/SF

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

  4727 Forest Haven Way, Oakland, FL 34787
• 

  /2

  Est $496,870

  Not Listed For Sale

  14011 Lochend Way, Oakland, FL 34787

  • 4 Beds
  • 3 Baths
  • 1,996 Sq Ft
  • Built 2024

  14011 Lochend Way, Oakland, FL 34787

  Last Sold Summary

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

  

  /3

  $594,000

  New Construction Pending

  • 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

  Dayene Grubert ORLANDO TBI REALTY LLC

  12915 Westhaven Oak Dr, Oakland, FL 34787
• 

  /2

  $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 $501,393

  Last Listing Agent Tania Matthews KELLER WILLIAMS ELITE PARTNERS III REALTY

  2755 Bobcat Chase Blvd, Oakland, FL 34787
• 

  /2

  Est $1,368,694

  Not Listed For Sale

  10081 Atwater Bay Dr, Oakland, FL 34787

  • 5 Beds
  • 3.5 Baths
  • 3,920 Sq Ft
  • Built 2024

  10081 Atwater Bay Dr, Oakland, FL 34787

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Jay Love DR HORTON REALTY OF CENTRAL FLORIDA LLC

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