Oakland, FL Homes

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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 $532,450

  Last Listing Agent Abraham Mendez NONA LEGACY POWERED BY LA ROSA

  9029 Sonoma Coast Dr, Oakland, FL 34787
• 

  

  /2

  Est $867,518

  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
• 

  

  

  /55

  $949,790

  New Construction $98K PRICE DROP Pending

  • 5 Beds
  • 4.5 Baths
  • 4,313 Sq Ft

  4632 Golden Birch Ave, Oakland, FL 34787

  Under Construction. Welcome to Parkside Trails! Explore the charm of this premier Clermont location, offering exclusive amenities and quick access to shopping, dining, and entertainment. With a mix of new construction, single-family and townhomes, plus a variety of exclusive amenities, families will love coming home. Now Selling Onsite with 4 Models Open Daily!Introducing the exquisite

  Adrienne Escott PULTE REALTY OF NORTH FLORIDA LLC

  4632 Golden Birch Ave, Oakland, FL 34787
• 

  

  /2

  $387,900

  Sold Jul 17, 2025

  1509 Sweet Apple St, Oakland, FL 34787

  • 3 Beds
  • 3 Baths
  • 1,809 Sq Ft
  • Built 2019

  Last Sold Summary

  • 8% Below List Price
  • $214/SF
  • 144 Days On Market

  Current Estimated Value $390,766

  Last Listing Agent Robert Jones OFFERPAD BROKERAGE FL, LLC

  1509 Sweet Apple St, Oakland, FL 34787
• 

  

  /2

  Est $481,669

  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
• 

  

  /9

  $599,990

  New Construction Open Sat 11AM - 4PM $110K PRICE DROP

  • 5 Beds
  • 4 Baths
  • 3,195 Sq Ft

  2986 Good Vibes Way, Oakland, FL 34787

  Under Construction. Welcome to the Steely, an innovative two-story Next Gen® home. This home features a private suite with a separate entrance, living area, kitchenette, bedroom, bathroom and laundry, ideal for multigenerational households. The main home is host to an inviting open-concept layout that blends the kitchen, living and dining areas, while a luxe owner’s suite at the back of the home

  Ben Goldstein LENNAR REALTY

  2986 Good Vibes Way, Oakland, FL 34787
• 

  /2

  $585,000

  Sold Aug 20, 2025

  15114 Field Daisy Dr, Oakland, FL 34787

  • 4 Beds
  • 2 Baths
  • 2,142 Sq Ft
  • Built 2025

  Last Sold Summary

  • $273/SF

  Current Estimated Value $585,007

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

  15114 Field Daisy Dr, Oakland, FL 34787
• 

  /2

  Est $494,928

  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
• 

  /2

  $606,440

  New Construction Pending

  • 4 Beds
  • 3 Baths
  • 2,102 Sq Ft

  17156 Ingram Hills Aly, Oakland, FL 34787

  One or more photo(s) has been virtually staged. Pre-Construction. To be built. SAMPLE IMAGES !!!! The Berkley at Hamlin Meadows: Luxury Living with Unmatched Privacy. Discover the perfect blend of elegance and functionality in the Berkley model. This impressive 2,102 sq. ft. residence features 4 bedrooms, 3 bathrooms, and a rear-load 2-car garage, thoughtfully designed for modern lifestyles. The

  Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

  17156 Ingram Hills Aly, Oakland, FL 34787
• 

  /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
• 

  /2

  Not Listed For Sale

  6343 Blissful St, Oakland, FL 34787

  • 3 Beds
  • 3 Baths
  • 1,685 Sq Ft
  • Built 2024

  6343 Blissful St, Oakland, FL 34787
• 

  

  /12

  $799,999

  • 5 Beds
  • 3 Baths
  • 3,413 Sq Ft

  16 Oakland Pointe Cir, Oakland, FL 34760

  Move-in-ready, airy and spacious 3,413-sq-ft home just two blocks from downtown Oakland, West Orange trail and directly across from Lake Apopka. Step into a home where character meets comfort and sophistication. Adorned with vibrant Tabebuia trees and blooming gardens, this property is a true gem. Every detail here tells a story of charm and warmth. Built in 1998 and fully updated with new

  Jack Keller JACK KELLER INC

  16 Oakland Pointe Cir, Oakland, FL 34760
• 

  /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 $687,455

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

  3064 Namaste Dr, Oakland, FL 34787
• 

  /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
• 

  

  /59

  $525,000

  $20K PRICE DROP Pending

  • 4 Beds
  • 2.5 Baths
  • 2,204 Sq Ft

  2259 White Feather Loop, Oakland, FL 34787

  Under contract-accepting backup offers. INCREDIBLE OPPORTUNITY to own this stunningly gorgeous 4 bedroom 2.5 bathroom corner lot home in the HIGHLY DESIRABLE community of Oakland Trails! Boasting over 2200 sq. feet of living space this 2017 built gem is amply equipped to meet the needs of families of all sizes and is gushing with stylistic appeal! Enter the home into a bright and positive feeling

  Chuck Burt YOUNG REAL ESTATE

  2259 White Feather Loop, Oakland, FL 34787
• 

  /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

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

  517 N Pollard St, 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
• 

  

  /3

  $674,000

  New Construction Pending

  • 4 Beds
  • 3.5 Baths
  • 2,508 Sq Ft

  12919 Westhaven Oak Dr, Oakland, FL 34787

  Under Construction. Toll Brothers New Construction in Horizon West – Winter Garden | Estimated Completion Summer 2026Bungalow featuring a private in-law suite above a detached 2-car garage. A charming covered entry welcomes you into an open and expansive floor plan with seamless flow between the great room, kitchen, and dining area — ideal for both everyday living and entertaining.Enjoy

  Dayene Grubert ORLANDO TBI REALTY LLC

  12919 Westhaven Oak Dr, Oakland, FL 34787
• 

  /2

  $430,000

  Sold Jul 16, 2025

  1113 Prado Ln, Oakland, FL 34787

  • Land
  • 16,117 Sq Ft
  • $1,162,162 per Acre

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Alexis Anderson REGENCY REAL ESTATE LLC

  1113 Prado Ln, Oakland, FL 34787
• 

  /2

  Est $814,578

  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
• 

  

  /9

  $688,240

  New Construction Pending

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

  3120 Namaste Dr, Oakland, FL 34787

  Under Construction. The Summerlin checks all your boxes! This breath taking two-story home features an expansive design with a convenient three-car garage. The first floor features an open-concept family room that complements a chef-ready kitchen and a cozy dining room, plus a private office and a spacious lanai. On the same level is the tranquil owner’s suite with an attached bathroom. Found

  Ben Goldstein LENNAR REALTY

  3120 Namaste 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 $614,922

  Last Listing Agent Ashley Boyd BHHS FLORIDA REALTY

  2606 Bobcat Chase Blvd, Oakland, FL 34787
• 

  /2

  Est $481,133

  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
• 

  

  /19

  $509,000

  $10K PRICE DROP Pending

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

  1270 Stationside Dr, Oakland, FL 34787

  Under contract-accepting backup offers. Nested right along the scenic West Orange Trail, this spacious 4 bedroom, 2 bath home offers the perfect balance of recreation and relaxation. The open interior flows seamlessly to private pool, creating an ideal oasis for Florida living. Located for ultimate convenience, just 15 mins from Downtown Winter Garden with The Turnpike nearby for an easy commute.

  Ky Lam HOME INVEST REALTY INC

  1270 Stationside Dr, Oakland, FL 34787
• 

  /2

  $449,490

  Sold Jul 22, 2025

  2915 Transformation Way, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,795 Sq Ft
  • Built 2025

  Last Sold Summary

  • $250/SF
  • 4 Days On Market

  Last Listing Agent Ben Goldstein LENNAR REALTY

  2915 Transformation Way, Oakland, FL 34787
• 

  /2

  Est $1,372,126

  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
• 

  

  /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
• 

  /2

  $380,000

  Sold Jul 25, 2025

  2203 Gopher Tortoise Terrace, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,620 Sq Ft
  • Built 2020

  Last Sold Summary

  • 8% Below List Price
  • $235/SF
  • 57 Days On Market

  Current Estimated Value $379,331

  Last Listing Agent Dawn Thomas KELLER WILLIAMS REALTY AT THE LAKES

  2203 Gopher Tortoise Terrace, Oakland, FL 34787
• 

  /2

  Est $485,564

  Not Listed For Sale

  14047 Lochend Way, Oakland, FL 34787

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

  14047 Lochend Way, Oakland, FL 34787

  Last Sold Summary
• 

  

  /20

  $554,990

  New Construction $78K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,532 Sq Ft

  3108 Namaste Dr, Oakland, FL 34787

  Under Construction. It’s what you have been waiting for, the Estero. This exquisite home emphasizes elegance and ease of living. Heading down the foyer there is a formal dining room that compliments a chef-ready kitchen, casual breakfast nook and spacious family room, plus an beautiful lanai. Framing the sides of the home are three secondary bedrooms and a luxurious owner’s suite with a

  Ben Goldstein LENNAR REALTY

  3108 Namaste Dr, Oakland, FL 34787
• 

  /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 $524,530

  Last Listing Agent Rachael Segarra EXP REALTY LLC

  233 Largovista Dr, Oakland, FL 34787
• 

  /2

  Est $461,370

  Not Listed For Sale

  9267 Gran Teatro Dr, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,835 Sq Ft
  • Built 2024

  9267 Gran Teatro Dr, Oakland, FL 34787

  Last Sold Summary

  • 82 Days On Market
• 

  

  /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
• 

  /2

  $852,105

  Sold Jul 02, 2025

  5307 Citrus Leaf Blvd, Oakland, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 3,300 Sq Ft
  • Built 2025

  Last Sold Summary

  • 1% Below List Price
  • $258/SF
  • 33 Days On Market

  Last Listing Agent Tatiana Souza FLORIDA CONNEXION PROPERTIES

  5307 Citrus Leaf Blvd, Oakland, FL 34787
• 

  

  /8

  Est $1,217,875

  Not Listed For Sale

  1080 Canyon Creek Trail, Oakland, FL 34787

  • 5 Beds
  • 4.5 Baths
  • 3,852 Sq Ft
  • Built 2024

  1080 Canyon Creek Trail, Oakland, FL 34787

  Last Sold Summary

  • 15 Days On Market
• 

  

  /36

  $679,000

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

  2022 Boss Hewett St, Oakland, FL 34787

  This turnkey, better-than-new single-story home offers an elegant and modern retreat within Oakland’s highly desirable waterfront community of Hull Island. Nestled in a friendly neighborhood surrounded by nature, the property immediately welcomes you with tasteful customizations, upgraded lighting, and stylish accent walls that bring warmth and character to the entire layout. The thoughtfully

  Brian Cirillo BALDWIN PARK REALTY LLC

  2022 Boss Hewett St, Oakland, FL 34787
• 

  /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 $1,338,676

  Last Listing Agent Alexis Anderson REGENCY REAL ESTATE LLC

  360 Jefferson St, Oakland, FL 34760
• 

  /2

  Est $1,023,943

  Not Listed For Sale

  1056 Sadler Oaks Way, Oakland, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,711 Sq Ft
  • Built 2024

  1056 Sadler Oaks Way, Oakland, FL 34787

  Last Sold Summary

  • 129 Days On Market
• 

  $1,675,000

  New Construction

  • 5 Beds
  • 5 Baths
  • 3,895 Sq Ft

  Custom Carrabelle Plan at Oakland Park, Winter Garden, FL 34787

  AR Homes Builder

  884 Tilden Oaks Trail Unit 37615294, Winter Garden, 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 $927,745

  Last Listing Agent John Silva JOHN SILVA REALTY & ASSOCIATES

  8911 Sonoma Coast Dr, Oakland, FL 34787

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